SK12332000A3 - N-hydroxy-2-(alkyl, aryl alebo heteroaryl sulfanyl, sulfinyl alebo sulfonyl)-3-substituované-alkyl, aryl alebo heteroarylamidy, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents

N-hydroxy-2-(alkyl, aryl alebo heteroaryl sulfanyl, sulfinyl alebo sulfonyl)-3-substituované-alkyl, aryl alebo heteroarylamidy, farmaceutický prostriedok s ich obsahom a ich použitie Download PDF

Info

Publication number: SK12332000A3
Authority: SK; Slovakia
Prior art keywords: alkyl; optionally substituted; selected independently; groups selected; aryl
Prior art date: 1998-02-19

Application number

SK1233-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Aranapakam Mudumbai Venkatesan

George Theodore Grosu

Jamie Marie Davis

Jannie Lea Baker

Jeremy Ian Levin

Original Assignee

American Cyanamid Company

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-02-19

Filing date

1998-08-26

Publication date

2001-02-12

1998-08-26 Application filed by American Cyanamid Company filed Critical American Cyanamid Company

2001-02-12 Publication of SK12332000A3 publication Critical patent/SK12332000A3/sk

Links

125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 title claims abstract description 12
125000003118 aryl group Chemical group 0.000 title claims description 149
239000003771 matrix metalloproteinase inhibitor Substances 0.000 title description 2
229940121386 matrix metalloproteinase inhibitor Drugs 0.000 title description 2
229910052717 sulfur Inorganic materials 0.000 claims abstract description 80
102000002274 Matrix Metalloproteinases Human genes 0.000 claims abstract description 35
108010000684 Matrix Metalloproteinases Proteins 0.000 claims abstract description 35
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 11
102000004190 Enzymes Human genes 0.000 claims abstract description 7
108090000790 Enzymes Proteins 0.000 claims abstract description 7
201000010099 disease Diseases 0.000 claims abstract description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
208000020084 Bone disease Diseases 0.000 claims abstract description 5
206010028980 Neoplasm Diseases 0.000 claims abstract description 5
230000002159 abnormal effect Effects 0.000 claims abstract description 5
230000029663 wound healing Effects 0.000 claims abstract description 5
206010022489 Insulin Resistance Diseases 0.000 claims abstract description 4
206010027476 Metastases Diseases 0.000 claims abstract description 4
208000028169 periodontal disease Diseases 0.000 claims abstract description 4
208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 4
208000031886 HIV Infections Diseases 0.000 claims abstract description 3
208000037357 HIV infectious disease Diseases 0.000 claims abstract description 3
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims abstract description 3
230000009401 metastasis Effects 0.000 claims abstract description 3
-1 cyano, amino Chemical group 0.000 claims description 253
125000004432 carbon atom Chemical group C* 0.000 claims description 114
125000001072 heteroaryl group Chemical group 0.000 claims description 98
125000000217 alkyl group Chemical group 0.000 claims description 96
229910052760 oxygen Inorganic materials 0.000 claims description 80
150000001875 compounds Chemical class 0.000 claims description 77
125000005842 heteroatom Chemical group 0.000 claims description 73
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
125000001624 naphthyl group Chemical group 0.000 claims description 48
150000003839 salts Chemical class 0.000 claims description 44
ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 39
229920006395 saturated elastomer Polymers 0.000 claims description 35
229910052736 halogen Inorganic materials 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 31
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 30
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 30
229910052757 nitrogen Inorganic materials 0.000 claims description 30
150000002367 halogens Chemical class 0.000 claims description 29
125000003342 alkenyl group Chemical group 0.000 claims description 26
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
125000000304 alkynyl group Chemical group 0.000 claims description 25
125000002619 bicyclic group Chemical group 0.000 claims description 25
125000002950 monocyclic group Chemical group 0.000 claims description 23
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 22
125000003545 alkoxy group Chemical group 0.000 claims description 20
229910052799 carbon Inorganic materials 0.000 claims description 20
150000001602 bicycloalkyls Chemical group 0.000 claims description 18
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 18
125000000753 cycloalkyl group Chemical group 0.000 claims description 16
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 15
125000003435 aroyl group Chemical group 0.000 claims description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
BFPSDSIWYFKGBC-UHFFFAOYSA-N chlorotrianisene Chemical compound C1=CC(OC)=CC=C1C(Cl)=C(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 BFPSDSIWYFKGBC-UHFFFAOYSA-N 0.000 claims description 14
SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 12
125000004104 aryloxy group Chemical group 0.000 claims description 10
125000005553 heteroaryloxy group Chemical group 0.000 claims description 10
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 9
125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 9
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 9
125000005018 aryl alkenyl group Chemical group 0.000 claims description 9
125000003710 aryl alkyl group Chemical group 0.000 claims description 9
239000004305 biphenyl Substances 0.000 claims description 9
235000010290 biphenyl Nutrition 0.000 claims description 9
229910052794 bromium Inorganic materials 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
229910052740 iodine Inorganic materials 0.000 claims description 9
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
125000004430 oxygen atom Chemical group O* 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 8
125000005530 alkylenedioxy group Chemical group 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 7
NIAJIVRYYJLXRC-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonyl-1-(2-phenylethyl)piperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CCC=2C=CC=CC=2)CC1 NIAJIVRYYJLXRC-UHFFFAOYSA-N 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
208000027866 inflammatory disease Diseases 0.000 claims description 5
YMQWZRPLMNNHEU-UHFFFAOYSA-N 1-[(4-bromophenyl)methyl]-n-hydroxy-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(Br)=CC=2)CC1 YMQWZRPLMNNHEU-UHFFFAOYSA-N 0.000 claims description 4
NZSGHPOSLLMCJS-UHFFFAOYSA-N 1-benzyl-n-hydroxy-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC=CC=2)CC1 NZSGHPOSLLMCJS-UHFFFAOYSA-N 0.000 claims description 4
GQEYBNSJJQDDLY-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-n-hydroxy-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]piperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(OCCN3CCCCC3)=CC=2)CC1 GQEYBNSJJQDDLY-UHFFFAOYSA-N 0.000 claims description 4
125000004171 alkoxy aryl group Chemical group 0.000 claims description 4
150000003973 alkyl amines Chemical class 0.000 claims description 4
125000001589 carboacyl group Chemical group 0.000 claims description 4
210000003169 central nervous system Anatomy 0.000 claims description 4
230000001404 mediated effect Effects 0.000 claims description 4
VUXKPYYMTYYYCJ-UHFFFAOYSA-N n-hydroxy-1-[2-(4-methoxyphenyl)ethyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1CCN1CCC(S(=O)(=O)C=2C=CC(OC)=CC=2)(C(=O)NO)CC1 VUXKPYYMTYYYCJ-UHFFFAOYSA-N 0.000 claims description 4
UYOSMJLYSRXRLI-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-[(4-pyridin-2-ylphenyl)methyl]piperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(=CC=2)C=2N=CC=CC=2)CC1 UYOSMJLYSRXRLI-UHFFFAOYSA-N 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
NPFGSGCFKYSLPI-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-n-hydroxy-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 NPFGSGCFKYSLPI-UHFFFAOYSA-N 0.000 claims description 3
VAMOVZICEXQQGW-UHFFFAOYSA-N 1-benzyl-4-[4-(2-ethylbutoxy)phenyl]sulfonyl-n-hydroxypiperidine-4-carboxamide Chemical compound C1=CC(OCC(CC)CC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC=CC=2)CC1 VAMOVZICEXQQGW-UHFFFAOYSA-N 0.000 claims description 3
CXFQYPXLXLPGNM-UHFFFAOYSA-N 1-benzyl-n-hydroxy-4-[4-(3-methylbutoxy)phenyl]sulfonylpiperidine-4-carboxamide Chemical compound C1=CC(OCCC(C)C)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC=CC=2)CC1 CXFQYPXLXLPGNM-UHFFFAOYSA-N 0.000 claims description 3
UZVVYDVVOHQVFV-UHFFFAOYSA-N 1-butyl-n-hydroxy-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1CN(CCCC)CCC1(C(=O)NO)S(=O)(=O)C1=CC=C(OC)C=C1 UZVVYDVVOHQVFV-UHFFFAOYSA-N 0.000 claims description 3
MLJSRWALBCZDCB-UHFFFAOYSA-N 1-tert-butyl-n-hydroxy-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(C(C)(C)C)CC1 MLJSRWALBCZDCB-UHFFFAOYSA-N 0.000 claims description 3
DIBVWAWXUHMLDF-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methoxy]phenyl]sulfonyl-n-hydroxy-1-methylpiperidine-4-carboxamide Chemical compound CN1CCC(C(=O)NO)CC1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=C(Cl)C=C1 DIBVWAWXUHMLDF-UHFFFAOYSA-N 0.000 claims description 3
NYBGUTIMRHCTPX-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-[(3,4-dichlorophenyl)methyl]-n-hydroxypiperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 NYBGUTIMRHCTPX-UHFFFAOYSA-N 0.000 claims description 3
ZQYGWQMHDWUTQF-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-[(4-cyanophenyl)methyl]-n-hydroxypiperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(=CC=2)C#N)CC1 ZQYGWQMHDWUTQF-UHFFFAOYSA-N 0.000 claims description 3
GMRJGTBNERTZIB-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-n-hydroxy-1-(2-phenoxyethyl)piperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CCOC=2C=CC=CC=2)CC1 GMRJGTBNERTZIB-UHFFFAOYSA-N 0.000 claims description 3
WWVKBGIBCFSFOJ-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-n-hydroxy-1-(3-phenoxypropyl)piperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CCCOC=2C=CC=CC=2)CC1 WWVKBGIBCFSFOJ-UHFFFAOYSA-N 0.000 claims description 3
NAXMTMYDSBOGMZ-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-n-hydroxy-1-[(4-methoxyphenyl)methyl]piperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(OC)=CC=2)CC1 NAXMTMYDSBOGMZ-UHFFFAOYSA-N 0.000 claims description 3
AUWOIDNULNLPBA-UHFFFAOYSA-N 4-[4-(4-chlorophenoxy)phenyl]sulfonyl-1-ethyl-n-hydroxypiperidine-4-carboxamide Chemical compound C1CN(CC)CCC1(C(=O)NO)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 AUWOIDNULNLPBA-UHFFFAOYSA-N 0.000 claims description 3
230000033115 angiogenesis Effects 0.000 claims description 3
LCQNQVIUMDNDJS-UHFFFAOYSA-N n-hydroxy-1-[(3-methoxyphenyl)methyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=C(OC)C=CC=2)CC1 LCQNQVIUMDNDJS-UHFFFAOYSA-N 0.000 claims description 3
FJXZBLKBEVSCAB-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-(3-methylbut-2-enyl)piperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=C(C)C)CC1 FJXZBLKBEVSCAB-UHFFFAOYSA-N 0.000 claims description 3
FTWZRZIOCFAVKU-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-(3-phenylpropyl)piperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CCCC=2C=CC=CC=2)CC1 FTWZRZIOCFAVKU-UHFFFAOYSA-N 0.000 claims description 3
GNNAXEPAOIUDTH-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-(naphthalen-2-ylmethyl)piperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=C3C=CC=CC3=CC=2)CC1 GNNAXEPAOIUDTH-UHFFFAOYSA-N 0.000 claims description 3
CWVWYGJTCDBSIW-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-[(4-methylphenyl)methyl]piperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(C)=CC=2)CC1 CWVWYGJTCDBSIW-UHFFFAOYSA-N 0.000 claims description 3
UTDYWIPXAVCYCE-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-[(4-phenylphenyl)methyl]piperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 UTDYWIPXAVCYCE-UHFFFAOYSA-N 0.000 claims description 3
RHTOEITZKIINCY-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-[(4-thiophen-2-ylphenyl)methyl]piperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(=CC=2)C=2SC=CC=2)CC1 RHTOEITZKIINCY-UHFFFAOYSA-N 0.000 claims description 3
DKGZULAWTBQCOO-UHFFFAOYSA-N n-hydroxypiperidine-4-carboxamide Chemical compound ONC(=O)C1CCNCC1 DKGZULAWTBQCOO-UHFFFAOYSA-N 0.000 claims description 3
230000004614 tumor growth Effects 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
IMKDKHQDFFLOKK-UHFFFAOYSA-N 1-benzyl-4-[4-(4-chlorophenoxy)phenyl]sulfonyl-n-hydroxypiperidine-4-carboxamide Chemical compound C1CC(C(=O)NO)(S(=O)(=O)C=2C=CC(OC=3C=CC(Cl)=CC=3)=CC=2)CCN1CC1=CC=CC=C1 IMKDKHQDFFLOKK-UHFFFAOYSA-N 0.000 claims description 2
ATFPFLNWBZIBTJ-UHFFFAOYSA-N 1-benzyl-n-hydroxy-4-(4-phenylmethoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NO)(S(=O)(=O)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)CCN1CC1=CC=CC=C1 ATFPFLNWBZIBTJ-UHFFFAOYSA-N 0.000 claims description 2
DTPBPOWGEIFZGM-UHFFFAOYSA-N 1-butyl-4-[4-(4-chlorophenoxy)phenyl]sulfonyl-n-hydroxypiperidine-4-carboxamide Chemical compound C1CN(CCCC)CCC1(C(=O)NO)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 DTPBPOWGEIFZGM-UHFFFAOYSA-N 0.000 claims description 2
WUEIXXXLLWDJHC-UHFFFAOYSA-N 1-butyl-n-hydroxy-4-[4-(3-methylbutoxy)phenyl]sulfonylpiperidine-4-carboxamide Chemical compound C1CN(CCCC)CCC1(C(=O)NO)S(=O)(=O)C1=CC=C(OCCC(C)C)C=C1 WUEIXXXLLWDJHC-UHFFFAOYSA-N 0.000 claims description 2
HFGTXSVDSMTFIN-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methoxy]phenyl]sulfonyl-n-hydroxy-1-[(4-methylphenyl)methyl]piperidine-4-carboxamide Chemical compound C1=CC(C)=CC=C1CN1C(S(=O)(=O)C=2C=CC(OCC=3C=CC(Cl)=CC=3)=CC=2)CC(C(=O)NO)CC1 HFGTXSVDSMTFIN-UHFFFAOYSA-N 0.000 claims description 2
HUTRBECWDORHKF-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-butyl-n-hydroxypiperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CCCC)CC1 HUTRBECWDORHKF-UHFFFAOYSA-N 0.000 claims description 2
WRYYVCSFLUPFIQ-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-ethyl-n-hydroxypiperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC)CC1 WRYYVCSFLUPFIQ-UHFFFAOYSA-N 0.000 claims description 2
WYISEDIVNLCBRU-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-n-hydroxy-1-(pyridin-4-ylmethyl)piperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CN=CC=2)CC1 WYISEDIVNLCBRU-UHFFFAOYSA-N 0.000 claims description 2
ZBDXZEGIXHCDMC-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-n-hydroxy-1-[(3-methoxyphenyl)methyl]piperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=C(OC)C=CC=2)CC1 ZBDXZEGIXHCDMC-UHFFFAOYSA-N 0.000 claims description 2
QJHUVPANTSNARI-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-n-hydroxy-1-[(3-phenoxyphenyl)methyl]piperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)CC1 QJHUVPANTSNARI-UHFFFAOYSA-N 0.000 claims description 2
DZBQEKPCHHIFND-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-n-hydroxy-1-[(4-methylphenyl)methyl]piperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(C)=CC=2)CC1 DZBQEKPCHHIFND-UHFFFAOYSA-N 0.000 claims description 2
NLPICQLAIKGJBE-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-n-hydroxy-1-methylpiperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(C)CC1 NLPICQLAIKGJBE-UHFFFAOYSA-N 0.000 claims description 2
WUWBMHSDQYCLTI-UHFFFAOYSA-N 4-[4-(4-chlorophenoxy)phenyl]sulfonyl-n-hydroxy-1-methylpiperidine-4-carboxamide Chemical compound C1CN(C)CCC1(C(=O)NO)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 WUWBMHSDQYCLTI-UHFFFAOYSA-N 0.000 claims description 2
206010053555 Arthritis bacterial Diseases 0.000 claims description 2
201000001320 Atherosclerosis Diseases 0.000 claims description 2
206010006895 Cachexia Diseases 0.000 claims description 2
206010007559 Cardiac failure congestive Diseases 0.000 claims description 2
206010012689 Diabetic retinopathy Diseases 0.000 claims description 2
206010015943 Eye inflammation Diseases 0.000 claims description 2
206010019280 Heart failures Diseases 0.000 claims description 2
208000004575 Infectious Arthritis Diseases 0.000 claims description 2
206010061218 Inflammation Diseases 0.000 claims description 2
206010060820 Joint injury Diseases 0.000 claims description 2
201000002287 Keratoconus Diseases 0.000 claims description 2
208000029725 Metabolic bone disease Diseases 0.000 claims description 2
206010029113 Neovascularisation Diseases 0.000 claims description 2
206010049088 Osteopenia Diseases 0.000 claims description 2
208000002158 Proliferative Vitreoretinopathy Diseases 0.000 claims description 2
206010038933 Retinopathy of prematurity Diseases 0.000 claims description 2
206010038934 Retinopathy proliferative Diseases 0.000 claims description 2
206010040070 Septic Shock Diseases 0.000 claims description 2
208000021386 Sjogren Syndrome Diseases 0.000 claims description 2
206010052779 Transplant rejections Diseases 0.000 claims description 2
206010064996 Ulcerative keratitis Diseases 0.000 claims description 2
206010064930 age-related macular degeneration Diseases 0.000 claims description 2
208000022531 anorexia Diseases 0.000 claims description 2
210000000845 cartilage Anatomy 0.000 claims description 2
208000019425 cirrhosis of liver Diseases 0.000 claims description 2
210000001072 colon Anatomy 0.000 claims description 2
206010061428 decreased appetite Diseases 0.000 claims description 2
230000003412 degenerative effect Effects 0.000 claims description 2
208000024519 eye neoplasm Diseases 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
230000001434 glomerular Effects 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
230000004054 inflammatory process Effects 0.000 claims description 2
208000002780 macular degeneration Diseases 0.000 claims description 2
208000001491 myopia Diseases 0.000 claims description 2
230000004379 myopia Effects 0.000 claims description 2
IEGOFALJZJPJJD-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-propan-2-ylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(C(C)C)CC1 IEGOFALJZJPJJD-UHFFFAOYSA-N 0.000 claims description 2
208000021971 neovascular inflammatory vitreoretinopathy Diseases 0.000 claims description 2
230000006785 proliferative vitreoretinopathy Effects 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
208000037803 restenosis Diseases 0.000 claims description 2
201000001223 septic arthritis Diseases 0.000 claims description 2
230000036303 septic shock Effects 0.000 claims description 2
230000009759 skin aging Effects 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
238000002054 transplantation Methods 0.000 claims description 2
230000000472 traumatic effect Effects 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 4
241000124008 Mammalia Species 0.000 claims 3
208000037260 Atherosclerotic Plaque Diseases 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
231100000915 pathological change Toxicity 0.000 claims 2
230000036285 pathological change Effects 0.000 claims 2
OACMZQSSORWURZ-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCNCC1 OACMZQSSORWURZ-UHFFFAOYSA-N 0.000 claims 1
206010011091 Coronary artery thrombosis Diseases 0.000 claims 1
206010016654 Fibrosis Diseases 0.000 claims 1
208000012902 Nervous system disease Diseases 0.000 claims 1
206010037660 Pyrexia Diseases 0.000 claims 1
229910004298 SiO 2 Inorganic materials 0.000 claims 1
229910004283 SiO 4 Inorganic materials 0.000 claims 1
230000007882 cirrhosis Effects 0.000 claims 1
208000002528 coronary thrombosis Diseases 0.000 claims 1
230000003210 demyelinating effect Effects 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 claims 1
208000028774 intestinal disease Diseases 0.000 claims 1
210000000936 intestine Anatomy 0.000 claims 1
210000004185 liver Anatomy 0.000 claims 1
IRGXGFPSYHAJER-UHFFFAOYSA-N n,3-dihydroxybenzamide Chemical compound ONC(=O)C1=CC=CC(O)=C1 IRGXGFPSYHAJER-UHFFFAOYSA-N 0.000 claims 1
230000007505 plaque formation Effects 0.000 claims 1
201000001474 proteinuria Diseases 0.000 claims 1
230000001823 pruritic effect Effects 0.000 claims 1
108091007505 ADAM17 Proteins 0.000 abstract description 8
102000029816 Collagenase Human genes 0.000 abstract description 7
108060005980 Collagenase Proteins 0.000 abstract description 7
108010026132 Gelatinases Proteins 0.000 abstract description 7
102000013382 Gelatinases Human genes 0.000 abstract description 7
108090000765 processed proteins & peptides Proteins 0.000 abstract description 7
229940088598 enzyme Drugs 0.000 abstract description 6
239000003112 inhibitor Substances 0.000 abstract description 6
230000015572 biosynthetic process Effects 0.000 abstract description 4
210000004379 membrane Anatomy 0.000 abstract description 4
239000012528 membrane Substances 0.000 abstract description 4
206010003246 arthritis Diseases 0.000 abstract description 3
210000002469 basement membrane Anatomy 0.000 abstract description 3
102000004127 Cytokines Human genes 0.000 abstract description 2
108090000695 Cytokines Proteins 0.000 abstract description 2
208000025865 Ulcer Diseases 0.000 abstract description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract description 2
210000002808 connective tissue Anatomy 0.000 abstract description 2
230000006378 damage Effects 0.000 abstract description 2
206010012601 diabetes mellitus Diseases 0.000 abstract description 2
230000001575 pathological effect Effects 0.000 abstract description 2
239000002243 precursor Substances 0.000 abstract description 2
230000000770 proinflammatory effect Effects 0.000 abstract description 2
102000004169 proteins and genes Human genes 0.000 abstract description 2
108090000623 proteins and genes Proteins 0.000 abstract description 2
150000003384 small molecules Chemical class 0.000 abstract description 2
108091007196 stromelysin Proteins 0.000 abstract description 2
210000001519 tissue Anatomy 0.000 abstract description 2
230000036269 ulceration Effects 0.000 abstract description 2
239000011701 zinc Substances 0.000 abstract description 2
229910052725 zinc Inorganic materials 0.000 abstract description 2
102000043279 ADAM17 Human genes 0.000 abstract 5
GOZMBJCYMQQACI-UHFFFAOYSA-N 6,7-dimethyl-3-[[methyl-[2-[methyl-[[1-[3-(trifluoromethyl)phenyl]indol-3-yl]methyl]amino]ethyl]amino]methyl]chromen-4-one;dihydrochloride Chemical compound Cl.Cl.C=1OC2=CC(C)=C(C)C=C2C(=O)C=1CN(C)CCN(C)CC(C1=CC=CC=C11)=CN1C1=CC=CC(C(F)(F)F)=C1 GOZMBJCYMQQACI-UHFFFAOYSA-N 0.000 abstract 2
102000005593 Endopeptidases Human genes 0.000 abstract 1
108010059378 Endopeptidases Proteins 0.000 abstract 1
229940066758 endopeptidases Drugs 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 432
239000007858 starting material Substances 0.000 description 365
239000007787 solid Substances 0.000 description 257
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 255
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 233
238000000034 method Methods 0.000 description 160
239000011347 resin Substances 0.000 description 144
229920005989 resin Polymers 0.000 description 144
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 140
239000011541 reaction mixture Substances 0.000 description 139
239000003921 oil Substances 0.000 description 120
235000019198 oils Nutrition 0.000 description 119
238000006243 chemical reaction Methods 0.000 description 95
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 90
239000008186 active pharmaceutical agent Substances 0.000 description 74
238000007429 general method Methods 0.000 description 73
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 73
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 72
239000000047 product Substances 0.000 description 60
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
239000000203 mixture Substances 0.000 description 49
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 48
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 43
239000002253 acid Substances 0.000 description 39
239000000243 solution Substances 0.000 description 39
239000012230 colorless oil Substances 0.000 description 37
238000002844 melting Methods 0.000 description 36
230000008018 melting Effects 0.000 description 36
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 36
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 33
239000000843 powder Substances 0.000 description 32
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 30
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 28
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
RGUVUPQQFXCJFC-UHFFFAOYSA-N n-hydroxyoctanamide Chemical compound CCCCCCCC(=O)NO RGUVUPQQFXCJFC-UHFFFAOYSA-N 0.000 description 24
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 21
229910000041 hydrogen chloride Inorganic materials 0.000 description 21
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 20
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 20
239000004743 Polypropylene Substances 0.000 description 19
YWNFFKQOXAXHQC-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfanylpropanoate Chemical compound CCOC(=O)C(C)SC1=CC=C(OC)C=C1 YWNFFKQOXAXHQC-UHFFFAOYSA-N 0.000 description 19
BCEKNASVQCZWFZ-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonylpropanoate Chemical compound CCOC(=O)C(C)S(=O)(=O)C1=CC=C(OC)C=C1 BCEKNASVQCZWFZ-UHFFFAOYSA-N 0.000 description 19
150000003840 hydrochlorides Chemical class 0.000 description 19
229920001155 polypropylene Polymers 0.000 description 19
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 18
229940092714 benzenesulfonic acid Drugs 0.000 description 18
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 18
235000009518 sodium iodide Nutrition 0.000 description 18
NIFAOMSJMGEFTQ-UHFFFAOYSA-N 4-methoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1 NIFAOMSJMGEFTQ-UHFFFAOYSA-N 0.000 description 17
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 17
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 17
239000012044 organic layer Substances 0.000 description 17
230000003647 oxidation Effects 0.000 description 17
238000007254 oxidation reaction Methods 0.000 description 17
102100031111 Disintegrin and metalloproteinase domain-containing protein 17 Human genes 0.000 description 16
150000001412 amines Chemical class 0.000 description 16
HJUXYQLTIVYHIN-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonylacetate Chemical compound CCOC(=O)CS(=O)(=O)C1=CC=C(OC)C=C1 HJUXYQLTIVYHIN-UHFFFAOYSA-N 0.000 description 16
235000019439 ethyl acetate Nutrition 0.000 description 16
125000004494 ethyl ester group Chemical group 0.000 description 16
229940080818 propionamide Drugs 0.000 description 16
238000010898 silica gel chromatography Methods 0.000 description 16
238000003556 assay Methods 0.000 description 15
239000013078 crystal Substances 0.000 description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
238000010992 reflux Methods 0.000 description 15
150000003462 sulfoxides Chemical class 0.000 description 15
238000012360 testing method Methods 0.000 description 15
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 14
238000006073 displacement reaction Methods 0.000 description 13
230000005764 inhibitory process Effects 0.000 description 13
239000007788 liquid Substances 0.000 description 13
238000010647 peptide synthesis reaction Methods 0.000 description 13
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
238000005859 coupling reaction Methods 0.000 description 11
150000002148 esters Chemical class 0.000 description 11
235000019260 propionic acid Nutrition 0.000 description 11
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 11
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 10
229940073608 benzyl chloride Drugs 0.000 description 10
239000002904 solvent Substances 0.000 description 10
239000000758 substrate Substances 0.000 description 10
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 9
239000012043 crude product Substances 0.000 description 9
239000012442 inert solvent Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
CVXCWPZVOYBWOJ-UHFFFAOYSA-N 1-[2-[4-(chloromethyl)phenoxy]ethyl]piperidine Chemical compound C1=CC(CCl)=CC=C1OCCN1CCCCC1 CVXCWPZVOYBWOJ-UHFFFAOYSA-N 0.000 description 8
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 8
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 8
229940116441 divinylbenzene Drugs 0.000 description 8
MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 8
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000000463 material Substances 0.000 description 7
159000000001 potassium salts Chemical class 0.000 description 7
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 6
PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
MFDBJTGAQFVAEB-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfanylacetate Chemical compound CCOC(=O)CSC1=CC=C(OC)C=C1 MFDBJTGAQFVAEB-UHFFFAOYSA-N 0.000 description 6
NZOOJCYLZZNIMG-UHFFFAOYSA-N ethyl 2-[4-(4-chlorophenoxy)phenyl]sulfonylacetate Chemical compound C1=CC(S(=O)(=O)CC(=O)OCC)=CC=C1OC1=CC=C(Cl)C=C1 NZOOJCYLZZNIMG-UHFFFAOYSA-N 0.000 description 6
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 6
238000000746 purification Methods 0.000 description 6
239000011734 sodium Substances 0.000 description 6
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
JVDWKJQBWSKJOJ-UHFFFAOYSA-N 1-bromo-3-methylbuta-1,3-diene Chemical compound CC(=C)C=CBr JVDWKJQBWSKJOJ-UHFFFAOYSA-N 0.000 description 5
OKIHXNKYYGUVTE-UHFFFAOYSA-N 4-Fluorothiophenol Chemical compound FC1=CC=C(S)C=C1 OKIHXNKYYGUVTE-UHFFFAOYSA-N 0.000 description 5
FTBCOQFMQSTCQQ-UHFFFAOYSA-N 4-bromobenzenethiol Chemical compound SC1=CC=C(Br)C=C1 FTBCOQFMQSTCQQ-UHFFFAOYSA-N 0.000 description 5
PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 5
239000000872 buffer Substances 0.000 description 5
239000000969 carrier Substances 0.000 description 5
229960002424 collagenase Drugs 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
IITLAVWWXSLDPS-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfanyl-3-methylbutanoate Chemical compound CCOC(=O)C(C(C)C)SC1=CC=C(OC)C=C1 IITLAVWWXSLDPS-UHFFFAOYSA-N 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
239000010410 layer Substances 0.000 description 5
SXPGFJZLDDFUHA-UHFFFAOYSA-N n,n-bis(2-chloroethyl)butan-1-amine Chemical compound CCCCN(CCCl)CCCl SXPGFJZLDDFUHA-UHFFFAOYSA-N 0.000 description 5
239000002245 particle Substances 0.000 description 5
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 5
238000004007 reversed phase HPLC Methods 0.000 description 5
MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 4
DUWMUQJJAWJMKE-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=C(OC)C=CC=2)CC1 DUWMUQJJAWJMKE-UHFFFAOYSA-N 0.000 description 4
XBPCFCUTHYHQPE-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-4-methyl-2-(pyridin-3-ylmethyl)pentanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CC(C)C)(C(O)=O)CC1=CC=CN=C1 XBPCFCUTHYHQPE-UHFFFAOYSA-N 0.000 description 4
YUQUNWNSQDULTI-UHFFFAOYSA-N 2-bromobenzenethiol Chemical compound SC1=CC=CC=C1Br YUQUNWNSQDULTI-UHFFFAOYSA-N 0.000 description 4
UZGLOGCJCWBBIV-UHFFFAOYSA-N 3-(chloromethyl)pyridin-1-ium;chloride Chemical compound Cl.ClCC1=CC=CN=C1 UZGLOGCJCWBBIV-UHFFFAOYSA-N 0.000 description 4
OHLBVSVGJUFQFR-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-butylpiperidine-4-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CCCC)CC1 OHLBVSVGJUFQFR-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
108060008682 Tumor Necrosis Factor Proteins 0.000 description 4
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 4
239000013543 active substance Substances 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
ALRJVTSNENAPAF-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-3-phenylpropanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C(=O)OCC)CC1=CC=CC=C1 ALRJVTSNENAPAF-UHFFFAOYSA-N 0.000 description 4
VVAVHRKZPPSACJ-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonylbutanoate Chemical compound CCOC(=O)C(CC)S(=O)(=O)C1=CC=C(OC)C=C1 VVAVHRKZPPSACJ-UHFFFAOYSA-N 0.000 description 4
JRUKMFPZCYNGSQ-UHFFFAOYSA-N ethyl 2-[4-(3-methylbutoxy)phenyl]sulfonylacetate Chemical compound CCOC(=O)CS(=O)(=O)C1=CC=C(OCCC(C)C)C=C1 JRUKMFPZCYNGSQ-UHFFFAOYSA-N 0.000 description 4
JIQJOKSCSVMZAN-UHFFFAOYSA-N ethyl 2-bromooctanoate Chemical compound CCCCCCC(Br)C(=O)OCC JIQJOKSCSVMZAN-UHFFFAOYSA-N 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000000314 lubricant Substances 0.000 description 4
VLWJKVNMRMHPCC-UHFFFAOYSA-N n-benzyl-2-chloro-n-(2-chloroethyl)ethanamine Chemical compound ClCCN(CCCl)CC1=CC=CC=C1 VLWJKVNMRMHPCC-UHFFFAOYSA-N 0.000 description 4
QLMPWDWLVIWORW-UHFFFAOYSA-N n-hydroxyheptanamide Chemical compound CCCCCCC(=O)NO QLMPWDWLVIWORW-UHFFFAOYSA-N 0.000 description 4
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
238000007911 parenteral administration Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
150000003457 sulfones Chemical class 0.000 description 4
SPRJURFMUJOYPE-UHFFFAOYSA-N tert-butyl 2-(4-methoxyphenyl)sulfonylacetate Chemical compound COC1=CC=C(S(=O)(=O)CC(=O)OC(C)(C)C)C=C1 SPRJURFMUJOYPE-UHFFFAOYSA-N 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
HLQZCRVEEQKNMS-UHFFFAOYSA-N 1-(chloromethyl)-4-phenylbenzene Chemical group C1=CC(CCl)=CC=C1C1=CC=CC=C1 HLQZCRVEEQKNMS-UHFFFAOYSA-N 0.000 description 3
CYUGJLVHBZRKNV-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC(F)=CC=2)CC1 CYUGJLVHBZRKNV-UHFFFAOYSA-N 0.000 description 3
BZJNHCZGKWQZOC-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)ethyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1CCN1CCC(S(=O)(=O)C=2C=CC(OC)=CC=2)(C(O)=O)CC1 BZJNHCZGKWQZOC-UHFFFAOYSA-N 0.000 description 3
FGCIQSBZGOVNLI-UHFFFAOYSA-N 1-[2-[4-(chloromethyl)phenoxy]ethyl]azepane Chemical compound C1=CC(CCl)=CC=C1OCCN1CCCCCC1 FGCIQSBZGOVNLI-UHFFFAOYSA-N 0.000 description 3
ADRRXAFFNTWBBO-UHFFFAOYSA-N 1-benzyl-4-(4-phenylmethoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)(S(=O)(=O)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)CCN1CC1=CC=CC=C1 ADRRXAFFNTWBBO-UHFFFAOYSA-N 0.000 description 3
IIASCQBFNHWZBE-UHFFFAOYSA-N 1-bromoethyl acetate Chemical compound CC(Br)OC(C)=O IIASCQBFNHWZBE-UHFFFAOYSA-N 0.000 description 3
PILFJHVWMWVHFY-UHFFFAOYSA-N 1-butyl-4-[4-(3-methylbutoxy)phenyl]sulfonylpiperidine-4-carboxylic acid Chemical compound C1CN(CCCC)CCC1(C(O)=O)S(=O)(=O)C1=CC=C(OCCC(C)C)C=C1 PILFJHVWMWVHFY-UHFFFAOYSA-N 0.000 description 3
ONISCRSNMIBMNV-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-5-methyl-2-(pyridin-3-ylmethyl)hexanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CCC(C)C)(C(O)=O)CC1=CC=CN=C1 ONISCRSNMIBMNV-UHFFFAOYSA-N 0.000 description 3
STVRITLNCCASTG-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-5-phenyl-2-(3-phenylpropyl)pentanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(O)=O)(CCCC=1C=CC=CC=1)CCCC1=CC=CC=C1 STVRITLNCCASTG-UHFFFAOYSA-N 0.000 description 3
VGKGWLPVHNOMJY-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-6-phenoxy-2-(pyridin-3-ylmethyl)hexanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(O)=O)(CC=1C=NC=CC=1)CCCCOC1=CC=CC=C1 VGKGWLPVHNOMJY-UHFFFAOYSA-N 0.000 description 3
HKWWUKAZJSTKBL-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonylbutanoic acid Chemical compound CCC(C(O)=O)S(=O)(=O)C1=CC=C(OC)C=C1 HKWWUKAZJSTKBL-UHFFFAOYSA-N 0.000 description 3
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
UMTSYCNTTIEZHN-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methoxy]phenyl]sulfonyl-1-[(4-methylphenyl)methyl]piperidine-4-carboxylic acid Chemical compound C1=CC(C)=CC=C1CN1C(S(=O)(=O)C=2C=CC(OCC=3C=CC(Cl)=CC=3)=CC=2)CC(C(O)=O)CC1 UMTSYCNTTIEZHN-UHFFFAOYSA-N 0.000 description 3
FZNZKCOQKMSOMM-UHFFFAOYSA-N 2-[8-(1-carboxyethylsulfonyl)octylsulfonyl]propanoic acid Chemical compound OC(=O)C(C)S(=O)(=O)CCCCCCCCS(=O)(=O)C(C)C(O)=O FZNZKCOQKMSOMM-UHFFFAOYSA-N 0.000 description 3
ZBHPCZBBKDUTLS-UHFFFAOYSA-N 2-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-methoxyphenyl)sulfonylpentanoic acid Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCC)(C(O)=O)CC(C=C1)=CC=C1OCCN1CCCCCC1 ZBHPCZBBKDUTLS-UHFFFAOYSA-N 0.000 description 3
GTGTXZRPJHDASG-UHFFFAOYSA-N 2-bromooctanoic acid Chemical compound CCCCCCC(Br)C(O)=O GTGTXZRPJHDASG-UHFFFAOYSA-N 0.000 description 3
UQZPGHOJMQTOHB-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)-n-ethylethanamine Chemical compound ClCCN(CC)CCCl UQZPGHOJMQTOHB-UHFFFAOYSA-N 0.000 description 3
ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 3
BCEFUVMHRCZDSG-UHFFFAOYSA-N 2-methyl-2-(2-methylfuran-3-yl)sulfonyl-3-phenylpropanoic acid Chemical compound O1C=CC(S(=O)(=O)C(C)(CC=2C=CC=CC=2)C(O)=O)=C1C BCEFUVMHRCZDSG-UHFFFAOYSA-N 0.000 description 3
HFXGXVWHWKOWDM-UHFFFAOYSA-N 2-octylsulfonyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanoic acid Chemical compound C1=CC(CC(S(=O)(=O)CCCCCCCC)C(O)=O)=CC=C1OCCN1CCCCC1 HFXGXVWHWKOWDM-UHFFFAOYSA-N 0.000 description 3
KIUMMUBSPKGMOY-UHFFFAOYSA-N 3,3'-Dithiobis(6-nitrobenzoic acid) Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(SSC=2C=C(C(=CC=2)[N+]([O-])=O)C(O)=O)=C1 KIUMMUBSPKGMOY-UHFFFAOYSA-N 0.000 description 3
125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 3
CDGGWNAXLPMQNX-UHFFFAOYSA-N 3-(2-bromophenyl)-2-(4-methoxyphenyl)sulfonyl-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(O)=O)CC1=CC=CC=C1Br CDGGWNAXLPMQNX-UHFFFAOYSA-N 0.000 description 3
CNQCWYFDIQSALX-UHFFFAOYSA-N 3-(chloromethyl)pyridine Chemical compound ClCC1=CC=CN=C1 CNQCWYFDIQSALX-UHFFFAOYSA-N 0.000 description 3
BUPXDXGYFXDDAA-UHFFFAOYSA-N 3-bromo-2-methylpropanoic acid Chemical compound BrCC(C)C(O)=O BUPXDXGYFXDDAA-UHFFFAOYSA-N 0.000 description 3
DDPGQCHQLTZAEW-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-(2-phenoxyethyl)piperidine-4-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CCOC=2C=CC=CC=2)CC1 DDPGQCHQLTZAEW-UHFFFAOYSA-N 0.000 description 3
WNMXWPBLGZBPEV-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-[(4-fluorophenyl)methyl]piperidine-4-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC(F)=CC=2)CC1 WNMXWPBLGZBPEV-UHFFFAOYSA-N 0.000 description 3
JFIVFYLTKPBGFD-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC(OCCN3CCCCC3)=CC=2)CC1 JFIVFYLTKPBGFD-UHFFFAOYSA-N 0.000 description 3
SJYNJHXAKQAKSE-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-ethylpiperidine-4-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC)CC1 SJYNJHXAKQAKSE-UHFFFAOYSA-N 0.000 description 3
UKVVESCCFWSMGT-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-methylpiperidine-4-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(C)CC1 UKVVESCCFWSMGT-UHFFFAOYSA-N 0.000 description 3
JBQHDBBLSWCKPO-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonyl-1-(3-methylbut-2-enyl)piperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=C(C)C)CC1 JBQHDBBLSWCKPO-UHFFFAOYSA-N 0.000 description 3
NYHPMECKFOYWAL-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonyl-1-[(4-thiophen-2-ylphenyl)methyl]piperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC(=CC=2)C=2SC=CC=2)CC1 NYHPMECKFOYWAL-UHFFFAOYSA-N 0.000 description 3
FJKQZMAMXQZOFD-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonyl-1-methylpiperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(C)CC1 FJKQZMAMXQZOFD-UHFFFAOYSA-N 0.000 description 3
KYMOWQQIZINTJZ-UHFFFAOYSA-N 4-methylsulfanylbenzenethiol Chemical compound CSC1=CC=C(S)C=C1 KYMOWQQIZINTJZ-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
239000007995 HEPES buffer Substances 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
AZRWNJFEUSHORT-UHFFFAOYSA-N benzyl-bis(2-chloroethyl)azanium;chloride Chemical compound [Cl-].ClCC[NH+](CCCl)CC1=CC=CC=C1 AZRWNJFEUSHORT-UHFFFAOYSA-N 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
231100000673 dose–response relationship Toxicity 0.000 description 3
229940079593 drug Drugs 0.000 description 3
ONYPOOPLTKMOLC-UHFFFAOYSA-N ethyl 2-(4-hydroxyphenyl)sulfanylacetate Chemical compound CCOC(=O)CSC1=CC=C(O)C=C1 ONYPOOPLTKMOLC-UHFFFAOYSA-N 0.000 description 3
MBJJVXODYFHLGZ-UHFFFAOYSA-N ethyl 2-(4-hydroxyphenyl)sulfanylpropanoate Chemical compound CCOC(=O)C(C)SC1=CC=C(O)C=C1 MBJJVXODYFHLGZ-UHFFFAOYSA-N 0.000 description 3
XCRAFQJNGCCKRA-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfanyloctanoate Chemical compound CCCCCCC(C(=O)OCC)SC1=CC=C(OC)C=C1 XCRAFQJNGCCKRA-UHFFFAOYSA-N 0.000 description 3
SDQMOLKJDNTYHL-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-5-methylhex-4-enoate Chemical compound CCOC(=O)C(CC=C(C)C)S(=O)(=O)C1=CC=C(OC)C=C1 SDQMOLKJDNTYHL-UHFFFAOYSA-N 0.000 description 3
UGHBKEGUPUWREF-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonylhexanoate Chemical compound CCCCC(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 UGHBKEGUPUWREF-UHFFFAOYSA-N 0.000 description 3
QRAOPMMLCUYDLB-UHFFFAOYSA-N ethyl 2-[4-(2-ethylbutoxy)phenyl]sulfonylacetate Chemical compound CCOC(=O)CS(=O)(=O)C1=CC=C(OCC(CC)CC)C=C1 QRAOPMMLCUYDLB-UHFFFAOYSA-N 0.000 description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
238000012417 linear regression Methods 0.000 description 3
URLYFRDHCDGEPS-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-2-phenoxyethanamine Chemical compound ClCCN(CCCl)CCOC1=CC=CC=C1 URLYFRDHCDGEPS-UHFFFAOYSA-N 0.000 description 3
GFRCWRSTRSRSJM-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfanyl-2-methyl-3-phenylpropanamide Chemical compound C1=CC(OC)=CC=C1SC(C)(C(=O)NO)CC1=CC=CC=C1 GFRCWRSTRSRSJM-UHFFFAOYSA-N 0.000 description 3
QRSXURBIIUBKMR-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfanyl-3-methylbutanamide Chemical compound COC1=CC=C(SC(C(C)C)C(=O)NO)C=C1 QRSXURBIIUBKMR-UHFFFAOYSA-N 0.000 description 3
COMDPQPBGQXLMK-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-prop-2-enylpent-4-enamide Chemical compound COC1=CC=C(S(=O)(=O)C(CC=C)(CC=C)C(=O)NO)C=C1 COMDPQPBGQXLMK-UHFFFAOYSA-N 0.000 description 3
SCPSERPFEJAOII-UHFFFAOYSA-N n-hydroxy-2-(4-phenylmethoxyphenyl)sulfanyloctanamide Chemical compound C1=CC(SC(CCCCCC)C(=O)NO)=CC=C1OCC1=CC=CC=C1 SCPSERPFEJAOII-UHFFFAOYSA-N 0.000 description 3
FDYIEPMHFWCFEO-UHFFFAOYSA-N n-hydroxy-2-[4-(3-morpholin-4-ylpropylamino)phenyl]sulfanyloctanamide Chemical compound C1=CC(SC(CCCCCC)C(=O)NO)=CC=C1NCCCN1CCOCC1 FDYIEPMHFWCFEO-UHFFFAOYSA-N 0.000 description 3
YJOSMOCGEMCNLK-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-(2-phenoxyethyl)piperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CCOC=2C=CC=CC=2)CC1 YJOSMOCGEMCNLK-UHFFFAOYSA-N 0.000 description 3
FBLQAKOTTHGGBJ-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-(3-phenoxypropyl)piperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CCCOC=2C=CC=CC=2)CC1 FBLQAKOTTHGGBJ-UHFFFAOYSA-N 0.000 description 3
238000011160 research Methods 0.000 description 3
230000007017 scission Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
RXZKGZVHEPIEQB-UHFFFAOYSA-N tert-butyl 2-[2-(4-methoxyphenyl)sulfonylpyridin-3-yl]propanoate Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1=NC=CC=C1C(C)C(=O)OC(C)(C)C RXZKGZVHEPIEQB-UHFFFAOYSA-N 0.000 description 3
239000002447 tumor necrosis factor alpha converting enzyme inhibitor Substances 0.000 description 3
239000001993 wax Substances 0.000 description 3
CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
JSCUZAYKVZXKQE-JXMROGBWSA-N (2e)-1-bromo-3,7-dimethylocta-2,6-diene Chemical compound CC(C)=CCC\C(C)=C\CBr JSCUZAYKVZXKQE-JXMROGBWSA-N 0.000 description 2
YWCXYJOMPQZDDA-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonylcyclopentane-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCCC1 YWCXYJOMPQZDDA-UHFFFAOYSA-N 0.000 description 2
RZJGKPNCYQZFGR-UHFFFAOYSA-N 1-(bromomethyl)naphthalene Chemical compound C1=CC=C2C(CBr)=CC=CC2=C1 RZJGKPNCYQZFGR-UHFFFAOYSA-N 0.000 description 2
JSWNZVXGNOTJIM-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 JSWNZVXGNOTJIM-UHFFFAOYSA-N 0.000 description 2
IWSJFFNNOGLAOF-UHFFFAOYSA-N 1-[(4-bromophenyl)methyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC(Br)=CC=2)CC1 IWSJFFNNOGLAOF-UHFFFAOYSA-N 0.000 description 2
HQAGKFIGCAJZKE-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1CN1CCC(S(=O)(=O)C=2C=CC(OC)=CC=2)(C(O)=O)CC1 HQAGKFIGCAJZKE-UHFFFAOYSA-N 0.000 description 2
SRPXVKQVZQEPFT-UHFFFAOYSA-N 1-benzyl-4-(4-butoxyphenyl)sulfonyl-n-hydroxypiperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC=CC=2)CC1 SRPXVKQVZQEPFT-UHFFFAOYSA-N 0.000 description 2
XRTDXBYJYXOWDU-UHFFFAOYSA-N 1-benzyl-4-(4-butoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC=CC=2)CC1 XRTDXBYJYXOWDU-UHFFFAOYSA-N 0.000 description 2
FECLWRWFWSXYKU-UHFFFAOYSA-N 1-benzyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC=CC=2)CC1 FECLWRWFWSXYKU-UHFFFAOYSA-N 0.000 description 2
SKFTZIAPNOOQKF-UHFFFAOYSA-N 1-benzyl-4-[4-(2-ethylbutoxy)phenyl]sulfonylpiperidine-4-carboxylic acid Chemical compound C1=CC(OCC(CC)CC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC=CC=2)CC1 SKFTZIAPNOOQKF-UHFFFAOYSA-N 0.000 description 2
QFRHOCVZCYMDSH-UHFFFAOYSA-N 1-benzyl-4-[4-(3-methylbutoxy)phenyl]sulfonylpiperidine-4-carboxylic acid Chemical compound C1=CC(OCCC(C)C)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC=CC=2)CC1 QFRHOCVZCYMDSH-UHFFFAOYSA-N 0.000 description 2
AVSQSJYNWVNYCA-UHFFFAOYSA-N 1-benzyl-4-[4-(4-chlorophenoxy)phenyl]sulfonylpiperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)(S(=O)(=O)C=2C=CC(OC=3C=CC(Cl)=CC=3)=CC=2)CCN1CC1=CC=CC=C1 AVSQSJYNWVNYCA-UHFFFAOYSA-N 0.000 description 2
YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 2
YLRBJYMANQKEAW-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)benzene Chemical compound BrCC1=CC=C(Br)C=C1 YLRBJYMANQKEAW-UHFFFAOYSA-N 0.000 description 2
LNNXOEHOXSYWLD-UHFFFAOYSA-N 1-bromobut-2-yne Chemical compound CC#CCBr LNNXOEHOXSYWLD-UHFFFAOYSA-N 0.000 description 2
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
BSCVECPSZUDOGB-UHFFFAOYSA-N 1-butyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C1CN(CCCC)CCC1(C(O)=O)S(=O)(=O)C1=CC=C(OC)C=C1 BSCVECPSZUDOGB-UHFFFAOYSA-N 0.000 description 2
RILLPINUEAYIFF-UHFFFAOYSA-N 1-butyl-4-[4-(4-chlorophenoxy)phenyl]sulfonylpiperidine-4-carboxylic acid Chemical compound C1CN(CCCC)CCC1(C(O)=O)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 RILLPINUEAYIFF-UHFFFAOYSA-N 0.000 description 2
IRJDDGBEDQOZOG-UHFFFAOYSA-N 1-cyclooctyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(C2CCCCCCC2)CC1 IRJDDGBEDQOZOG-UHFFFAOYSA-N 0.000 description 2
DWPQQYLEUVZYGC-UHFFFAOYSA-N 1-ethyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C1CN(CC)CCC1(C(O)=O)S(=O)(=O)C1=CC=C(OC)C=C1 DWPQQYLEUVZYGC-UHFFFAOYSA-N 0.000 description 2
MWFBMGWABXFCCK-UHFFFAOYSA-N 1-ethyl-n-hydroxy-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1CN(CC)CCC1(C(=O)NO)S(=O)(=O)C1=CC=C(OC)C=C1 MWFBMGWABXFCCK-UHFFFAOYSA-N 0.000 description 2
DGPTVADDIGLETM-UHFFFAOYSA-N 1-tert-butyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(C(C)(C)C)CC1 DGPTVADDIGLETM-UHFFFAOYSA-N 0.000 description 2
QIULLHZMZMGGFH-UHFFFAOYSA-N 2,5-dichlorobenzenethiol Chemical compound SC1=CC(Cl)=CC=C1Cl QIULLHZMZMGGFH-UHFFFAOYSA-N 0.000 description 2
UMQSLMSNBMTPJY-UHFFFAOYSA-N 2,5-dichlorothiophene-3-sulfonic acid Chemical compound OS(=O)(=O)C=1C=C(Cl)SC=1Cl UMQSLMSNBMTPJY-UHFFFAOYSA-N 0.000 description 2
ZCBGQRNLKIGKIZ-UHFFFAOYSA-N 2-(4-bromophenyl)sulfonyl-2-methyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanoic acid Chemical compound C=1C=C(Br)C=CC=1S(=O)(=O)C(C)(C(O)=O)CC(C=C1)=CC=C1OCCN1CCCCC1 ZCBGQRNLKIGKIZ-UHFFFAOYSA-N 0.000 description 2
OTNOFLDVSHPHCS-UHFFFAOYSA-N 2-(4-bromophenyl)sulfonyl-n-hydroxy-2-methyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanamide Chemical compound C=1C=C(Br)C=CC=1S(=O)(=O)C(C)(C(=O)NO)CC(C=C1)=CC=C1OCCN1CCCCC1 OTNOFLDVSHPHCS-UHFFFAOYSA-N 0.000 description 2
RCJVCVZVNXSICC-UHFFFAOYSA-N 2-(4-butoxyphenyl)sulfonyl-2-methyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanoic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C(C)(C(O)=O)CC(C=C1)=CC=C1OCCN1CCCCC1 RCJVCVZVNXSICC-UHFFFAOYSA-N 0.000 description 2
DPCFSURNKHMIOL-UHFFFAOYSA-N 2-(4-fluorophenyl)sulfonyl-n-hydroxy-2-(pyridin-3-ylmethyl)dec-4-ynamide Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)C(CC#CCCCCC)(C(=O)NO)CC1=CC=CN=C1 DPCFSURNKHMIOL-UHFFFAOYSA-N 0.000 description 2
DZYXUFKENHKMSN-UHFFFAOYSA-N 2-(4-fluorophenyl)sulfonyl-n-hydroxy-2-(pyridin-3-ylmethyl)hex-4-ynamide Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)C(CC#CC)(C(=O)NO)CC1=CC=CN=C1 DZYXUFKENHKMSN-UHFFFAOYSA-N 0.000 description 2
RBYTVIRSOXCRJN-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfanyl-2,5-dimethylhex-4-enoic acid Chemical compound COC1=CC=C(SC(C)(CC=C(C)C)C(O)=O)C=C1 RBYTVIRSOXCRJN-UHFFFAOYSA-N 0.000 description 2
IEHDYPLWIKFOMQ-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfanyl-2-methyl-3-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1SC(C)(C(O)=O)CC1=CC=CC=C1 IEHDYPLWIKFOMQ-UHFFFAOYSA-N 0.000 description 2
SBIDELDUSFIWTF-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfanyl-2-phenylacetic acid Chemical compound C1=CC(OC)=CC=C1SC(C(O)=O)C1=CC=CC=C1 SBIDELDUSFIWTF-UHFFFAOYSA-N 0.000 description 2
JKMBHXSFDMCWRP-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfanyl-3-methylbutanoic acid Chemical compound COC1=CC=C(SC(C(C)C)C(O)=O)C=C1 JKMBHXSFDMCWRP-UHFFFAOYSA-N 0.000 description 2
SBTIESKERYATJP-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfanylheptanoic acid Chemical compound CCCCCC(C(O)=O)SC1=CC=C(OC)C=C1 SBTIESKERYATJP-UHFFFAOYSA-N 0.000 description 2
GBSKGJBWVQILOR-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2,5,9-trimethyldeca-4,8-dienoic acid Chemical compound COC1=CC=C(S(=O)(=O)C(C)(CC=C(C)CCC=C(C)C)C(O)=O)C=C1 GBSKGJBWVQILOR-UHFFFAOYSA-N 0.000 description 2
GNICTIBGBYQSLN-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-(pyridin-3-ylmethyl)decanoic acid Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCCCCCCC)(C(O)=O)CC1=CC=CN=C1 GNICTIBGBYQSLN-UHFFFAOYSA-N 0.000 description 2
VOJBXLPQAOXZOO-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-(pyridin-3-ylmethyl)hexanoic acid Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCCC)(C(O)=O)CC1=CC=CN=C1 VOJBXLPQAOXZOO-UHFFFAOYSA-N 0.000 description 2
ZQEDBUCXIRFLEZ-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-[[4-(2-morpholin-4-ylethoxy)phenyl]methyl]butanoic acid Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CC)(C(O)=O)CC(C=C1)=CC=C1OCCN1CCOCC1 ZQEDBUCXIRFLEZ-UHFFFAOYSA-N 0.000 description 2
YJXCVQRTOVXIOF-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-[[4-(2-morpholin-4-ylethoxy)phenyl]methyl]pentanoic acid Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCC)(C(O)=O)CC(C=C1)=CC=C1OCCN1CCOCC1 YJXCVQRTOVXIOF-UHFFFAOYSA-N 0.000 description 2
NBZZWKWOMHLJKT-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]butanoic acid Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CC)(C(O)=O)CC(C=C1)=CC=C1OCCN1CCCCC1 NBZZWKWOMHLJKT-UHFFFAOYSA-N 0.000 description 2
KPSFEBWHOSQOJI-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-[3-(2-piperidin-1-ylethoxy)phenyl]propanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(O)=O)CC1=CC=CC(OCCN2CCCCC2)=C1 KPSFEBWHOSQOJI-UHFFFAOYSA-N 0.000 description 2
UDLSZMDBXJJBHT-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(O)=O)CC(C=C1)=CC=C1OCCN1CCCCC1 UDLSZMDBXJJBHT-UHFFFAOYSA-N 0.000 description 2
CJXJTIFIYTUWFI-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-naphthalen-2-ylpropanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(O)=O)CC1=CC=C(C=CC=C2)C2=C1 CJXJTIFIYTUWFI-UHFFFAOYSA-N 0.000 description 2
DTCQWHKRAIBGLZ-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-pyridin-3-ylpropanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(O)=O)CC1=CC=CN=C1 DTCQWHKRAIBGLZ-UHFFFAOYSA-N 0.000 description 2
QKMJMKSZOBHGNA-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-quinolin-6-ylpropanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(O)=O)CC1=CC=C(N=CC=C2)C2=C1 QKMJMKSZOBHGNA-UHFFFAOYSA-N 0.000 description 2
GBARSGZCQMHSPT-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-methyl-5-phenylpent-4-enoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(O)=O)CC=CC1=CC=CC=C1 GBARSGZCQMHSPT-UHFFFAOYSA-N 0.000 description 2
UYJKEESLTNDEHM-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-3-naphthalen-2-ylpropanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(O)=O)CC1=CC=C(C=CC=C2)C2=C1 UYJKEESLTNDEHM-UHFFFAOYSA-N 0.000 description 2
SPDVTRLYGCBLQZ-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-3-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(O)=O)CC1=CC=CC=C1 SPDVTRLYGCBLQZ-UHFFFAOYSA-N 0.000 description 2
CKVTXSIFQDJUDL-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-5-methyl-2-(pyridin-3-ylmethyl)hex-4-enoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CC=C(C)C)(C(O)=O)CC1=CC=CN=C1 CKVTXSIFQDJUDL-UHFFFAOYSA-N 0.000 description 2
DAHWERGLAUPNAC-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonylhexanoic acid Chemical compound CCCCC(C(O)=O)S(=O)(=O)C1=CC=C(OC)C=C1 DAHWERGLAUPNAC-UHFFFAOYSA-N 0.000 description 2
FNQWFNOLTTYSMR-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyltetradecanoic acid Chemical compound CCCCCCCCCCCCC(C(O)=O)S(=O)(=O)C1=CC=C(OC)C=C1 FNQWFNOLTTYSMR-UHFFFAOYSA-N 0.000 description 2
NFMWQEXDGGQAMJ-UHFFFAOYSA-N 2-(cyclohexylmethyl)-2-(4-methoxyphenyl)sulfonyl-3-pyridin-3-ylpropanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(O)=O)(CC=1C=NC=CC=1)CC1CCCCC1 NFMWQEXDGGQAMJ-UHFFFAOYSA-N 0.000 description 2
RFCQDOVPMUSZMN-UHFFFAOYSA-N 2-Naphthalenethiol Chemical compound C1=CC=CC2=CC(S)=CC=C21 RFCQDOVPMUSZMN-UHFFFAOYSA-N 0.000 description 2
YXYOXGSDQLJFDP-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)methyl-(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)CC1=CC=C(Cl)C(Cl)=C1 YXYOXGSDQLJFDP-UHFFFAOYSA-N 0.000 description 2
YOYHVMIRZKMMPG-UHFFFAOYSA-N 2-[(4-bromophenyl)methyl-(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)CC1=CC=C(Br)C=C1 YOYHVMIRZKMMPG-UHFFFAOYSA-N 0.000 description 2
ISVCVMYCDGQMMH-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methylsulfonyl]-2-methyl-3-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1CS(=O)(=O)C(C)(C(O)=O)CC1=CC=CC=C1 ISVCVMYCDGQMMH-UHFFFAOYSA-N 0.000 description 2
VOUWIXZCTHZNEH-UHFFFAOYSA-N 2-[2-hydroxyethyl(2-phenoxyethyl)amino]ethanol Chemical compound OCCN(CCO)CCOC1=CC=CC=C1 VOUWIXZCTHZNEH-UHFFFAOYSA-N 0.000 description 2
DPSFVRWDVCJXKC-UHFFFAOYSA-N 2-[2-hydroxyethyl(3-phenoxypropyl)amino]ethanol Chemical compound OCCN(CCO)CCCOC1=CC=CC=C1 DPSFVRWDVCJXKC-UHFFFAOYSA-N 0.000 description 2
VDVWWRRBJNNKQD-UHFFFAOYSA-N 2-[2-hydroxyethyl(3-phenylpropyl)amino]ethanol Chemical compound OCCN(CCO)CCCC1=CC=CC=C1 VDVWWRRBJNNKQD-UHFFFAOYSA-N 0.000 description 2
KORPIWRPEFDZPH-UHFFFAOYSA-N 2-[2-hydroxyethyl-[(3-methoxyphenyl)methyl]amino]ethanol Chemical compound COC1=CC=CC(CN(CCO)CCO)=C1 KORPIWRPEFDZPH-UHFFFAOYSA-N 0.000 description 2
BRKVKGWERTXEKT-UHFFFAOYSA-N 2-[2-hydroxyethyl-[(4-methoxyphenyl)methyl]amino]ethanol Chemical compound COC1=CC=C(CN(CCO)CCO)C=C1 BRKVKGWERTXEKT-UHFFFAOYSA-N 0.000 description 2
DUUFGGOWUAPNDI-UHFFFAOYSA-N 2-[2-hydroxyethyl-[(4-methylphenyl)methyl]amino]ethanol Chemical compound CC1=CC=C(CN(CCO)CCO)C=C1 DUUFGGOWUAPNDI-UHFFFAOYSA-N 0.000 description 2
VNJOKTJIQQUWPE-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methoxy]phenyl]sulfonyl-1-methylpiperidine-4-carboxylic acid Chemical compound CN1CCC(C(O)=O)CC1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=C(Cl)C=C1 VNJOKTJIQQUWPE-UHFFFAOYSA-N 0.000 description 2
WPTIRRUWRQWLSI-UHFFFAOYSA-N 2-[8-(1-ethoxy-1-oxopropan-2-yl)sulfonyloctylsulfonyl]propanoic acid Chemical compound CCOC(=O)C(C)S(=O)(=O)CCCCCCCCS(=O)(=O)C(C)C(O)=O WPTIRRUWRQWLSI-UHFFFAOYSA-N 0.000 description 2
XXIUBUHCQXKGSS-UHFFFAOYSA-N 2-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-methoxyphenyl)sulfonyloctanoic acid Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCCCCC)(C(O)=O)CC(C=C1)=CC=C1OCCN1CCCCCC1 XXIUBUHCQXKGSS-UHFFFAOYSA-N 0.000 description 2
FTPFETHIKQTFMJ-UHFFFAOYSA-N 2-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-n-hydroxy-2-(4-methoxyphenyl)sulfonyloctanamide Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCCCCC)(C(=O)NO)CC(C=C1)=CC=C1OCCN1CCCCCC1 FTPFETHIKQTFMJ-UHFFFAOYSA-N 0.000 description 2
FVXPJNCWSHTUHW-UHFFFAOYSA-N 2-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-n-hydroxy-2-(4-methoxyphenyl)sulfonylpentanamide Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCC)(C(=O)NO)CC(C=C1)=CC=C1OCCN1CCCCCC1 FVXPJNCWSHTUHW-UHFFFAOYSA-N 0.000 description 2
NJOUXZVOERQPTN-UHFFFAOYSA-N 2-[[4-[2-(diethylamino)ethoxy]phenyl]methyl]-2-(4-methoxyphenyl)sulfonylhexanoic acid Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCCC)(C(O)=O)CC1=CC=C(OCCN(CC)CC)C=C1 NJOUXZVOERQPTN-UHFFFAOYSA-N 0.000 description 2
XVOIZAUCJLKSSL-UHFFFAOYSA-N 2-[[4-[2-(diethylamino)ethoxy]phenyl]methyl]-n-hydroxy-2-(4-methoxyphenyl)sulfonylhexanamide Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCCC)(C(=O)NO)CC1=CC=C(OCCN(CC)CC)C=C1 XVOIZAUCJLKSSL-UHFFFAOYSA-N 0.000 description 2
MHXDUXISCHJMGT-UHFFFAOYSA-N 2-benzyl-2-(4-methoxyphenyl)sulfonyl-3-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(O)=O)(CC=1C=CC=CC=1)CC1=CC=CC=C1 MHXDUXISCHJMGT-UHFFFAOYSA-N 0.000 description 2
NRUVUIJEPPKHSP-UHFFFAOYSA-N 2-benzyl-4-[di(propan-2-yl)amino]-2-(4-methoxyphenyl)sulfonylbutanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CCN(C(C)C)C(C)C)(C(O)=O)CC1=CC=CC=C1 NRUVUIJEPPKHSP-UHFFFAOYSA-N 0.000 description 2
UEBARDWJXBGYEJ-UHFFFAOYSA-N 2-bromo-3-methylbutanoic acid Chemical compound CC(C)C(Br)C(O)=O UEBARDWJXBGYEJ-UHFFFAOYSA-N 0.000 description 2
WDRSCFNERFONKU-UHFFFAOYSA-N 2-bromo-3-phenylpropanoic acid Chemical compound OC(=O)C(Br)CC1=CC=CC=C1 WDRSCFNERFONKU-UHFFFAOYSA-N 0.000 description 2
YAQLSKVCTLCIIE-UHFFFAOYSA-N 2-bromobutyric acid Chemical compound CCC(Br)C(O)=O YAQLSKVCTLCIIE-UHFFFAOYSA-N 0.000 description 2
KNLOTZNPRIFUAR-UHFFFAOYSA-N 2-bromodecanoic acid Chemical compound CCCCCCCCC(Br)C(O)=O KNLOTZNPRIFUAR-UHFFFAOYSA-N 0.000 description 2
MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 2
WKHPQNUBULPJBR-UHFFFAOYSA-N 2-but-2-ynyl-2-(4-fluorophenyl)sulfonyl-n-hydroxyhex-4-ynamide Chemical compound CC#CCC(CC#CC)(C(=O)NO)S(=O)(=O)C1=CC=C(F)C=C1 WKHPQNUBULPJBR-UHFFFAOYSA-N 0.000 description 2
QZBHSTFXNXNMBI-UHFFFAOYSA-N 2-but-2-ynyl-n-hydroxy-2-(4-methoxyphenyl)sulfonylhex-4-ynamide Chemical compound COC1=CC=C(S(=O)(=O)C(CC#CC)(CC#CC)C(=O)NO)C=C1 QZBHSTFXNXNMBI-UHFFFAOYSA-N 0.000 description 2
XTUZOBLXVGEQEU-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)-n-[(3-methoxyphenyl)methyl]ethanamine Chemical compound COC1=CC=CC(CN(CCCl)CCCl)=C1 XTUZOBLXVGEQEU-UHFFFAOYSA-N 0.000 description 2
XFYLJTALUWPUEI-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)-n-[(4-fluorophenyl)methyl]ethanamine Chemical compound FC1=CC=C(CN(CCCl)CCCl)C=C1 XFYLJTALUWPUEI-UHFFFAOYSA-N 0.000 description 2
XVEHBTQWYNXBED-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)-n-[(4-methoxyphenyl)methyl]ethanamine Chemical compound COC1=CC=C(CN(CCCl)CCCl)C=C1 XVEHBTQWYNXBED-UHFFFAOYSA-N 0.000 description 2
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
MGFFSFXUXCGTSF-UHFFFAOYSA-N 2-hydroxy-3-phenylpropanamide Chemical compound NC(=O)C(O)CC1=CC=CC=C1 MGFFSFXUXCGTSF-UHFFFAOYSA-N 0.000 description 2
ZMMUTGJWLOBIPH-UHFFFAOYSA-N 2-methyl-2-(1-methylimidazol-2-yl)sulfonyl-3-(4-phenylphenyl)propanoic acid Chemical compound CN1C=CN=C1S(=O)(=O)C(C)(C(O)=O)CC1=CC=C(C=2C=CC=CC=2)C=C1 ZMMUTGJWLOBIPH-UHFFFAOYSA-N 0.000 description 2
WBLQYEHWIXEIHR-UHFFFAOYSA-N 2-methyl-2-(2-methylfuran-3-yl)sulfonyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanoic acid Chemical compound O1C=CC(S(=O)(=O)C(C)(CC=2C=CC(OCCN3CCCCC3)=CC=2)C(O)=O)=C1C WBLQYEHWIXEIHR-UHFFFAOYSA-N 0.000 description 2
NGDBWXSGDLWPCK-UHFFFAOYSA-N 2-methyl-3-phenyl-2-thiophen-2-ylsulfonylpropanoic acid Chemical compound C=1C=CSC=1S(=O)(=O)C(C)(C(O)=O)CC1=CC=CC=C1 NGDBWXSGDLWPCK-UHFFFAOYSA-N 0.000 description 2
QLYBZTQQDZECJI-UHFFFAOYSA-N 3-(4-bromophenyl)-2-(4-methoxyphenyl)sulfonyl-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(O)=O)CC1=CC=C(Br)C=C1 QLYBZTQQDZECJI-UHFFFAOYSA-N 0.000 description 2
BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 2
JZYKIVMXIBVHMI-UHFFFAOYSA-N 3-[4-[2-(azepan-1-yl)ethoxy]phenyl]-2-(4-methoxyphenyl)sulfonyl-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(O)=O)CC(C=C1)=CC=C1OCCN1CCCCCC1 JZYKIVMXIBVHMI-UHFFFAOYSA-N 0.000 description 2
VKCIBOBTIOCYLR-UHFFFAOYSA-N 3-[4-[2-(azepan-1-yl)ethoxy]phenyl]-n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-methylpropanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(=O)NO)CC(C=C1)=CC=C1OCCN1CCCCCC1 VKCIBOBTIOCYLR-UHFFFAOYSA-N 0.000 description 2
XMZQWZJMTBCUFT-UHFFFAOYSA-N 3-bromopropylbenzene Chemical compound BrCCCC1=CC=CC=C1 XMZQWZJMTBCUFT-UHFFFAOYSA-N 0.000 description 2
UERUQGBXUDZNOJ-UHFFFAOYSA-N 3-cyclohexyl-2-(4-methoxyphenyl)sulfonyl-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(O)=O)CC1CCCCC1 UERUQGBXUDZNOJ-UHFFFAOYSA-N 0.000 description 2
ZDEUGINAVLMAET-UHFFFAOYSA-N 3-fluorobenzenethiol Chemical compound FC1=CC=CC(S)=C1 ZDEUGINAVLMAET-UHFFFAOYSA-N 0.000 description 2
QMVAZEHZOPDGHA-UHFFFAOYSA-N 3-methoxybenzenethiol Chemical compound COC1=CC=CC(S)=C1 QMVAZEHZOPDGHA-UHFFFAOYSA-N 0.000 description 2
125000001331 3-methylbutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 2
UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 2
AIZQGRMSEBXCNI-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-(3-phenoxypropyl)piperidine-4-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CCCOC=2C=CC=CC=2)CC1 AIZQGRMSEBXCNI-UHFFFAOYSA-N 0.000 description 2
AJCQFWNWCGARNQ-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-(pyridin-4-ylmethyl)piperidine-4-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CN=CC=2)CC1 AJCQFWNWCGARNQ-UHFFFAOYSA-N 0.000 description 2
ZEWRRUMNNGEOBM-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-[(3,4-dichlorophenyl)methyl]piperidine-4-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 ZEWRRUMNNGEOBM-UHFFFAOYSA-N 0.000 description 2
BMSJRRAZNLUPNG-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-[(3-methoxyphenyl)methyl]piperidine-4-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=C(OC)C=CC=2)CC1 BMSJRRAZNLUPNG-UHFFFAOYSA-N 0.000 description 2
JPADYGNJCITETC-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-[(3-phenoxyphenyl)methyl]piperidine-4-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)CC1 JPADYGNJCITETC-UHFFFAOYSA-N 0.000 description 2
QDIPSBNRXKLDEI-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-[(4-cyanophenyl)methyl]piperidine-4-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC(=CC=2)C#N)CC1 QDIPSBNRXKLDEI-UHFFFAOYSA-N 0.000 description 2
QZAKHVZDCIZWMH-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-[(4-fluorophenyl)methyl]-n-hydroxypiperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(F)=CC=2)CC1 QZAKHVZDCIZWMH-UHFFFAOYSA-N 0.000 description 2
RLIOBDUNWLJVRN-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-[(4-methoxyphenyl)methyl]piperidine-4-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC(OC)=CC=2)CC1 RLIOBDUNWLJVRN-UHFFFAOYSA-N 0.000 description 2
OCKNGMKXMMZGCZ-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-[(4-methylphenyl)methyl]piperidine-4-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC(C)=CC=2)CC1 OCKNGMKXMMZGCZ-UHFFFAOYSA-N 0.000 description 2
AEMURECWAJLPNX-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonyl-1-(2-phenoxyethyl)piperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CCOC=2C=CC=CC=2)CC1 AEMURECWAJLPNX-UHFFFAOYSA-N 0.000 description 2
ZONWCAFXWCFRRI-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonyl-1-(3-phenoxypropyl)piperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CCCOC=2C=CC=CC=2)CC1 ZONWCAFXWCFRRI-UHFFFAOYSA-N 0.000 description 2
YENBIMVFSZPGNF-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonyl-1-(3-phenylpropyl)piperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CCCC=2C=CC=CC=2)CC1 YENBIMVFSZPGNF-UHFFFAOYSA-N 0.000 description 2
HKMTZJUWMOYMCB-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonyl-1-[(4-methylphenyl)methyl]piperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC(C)=CC=2)CC1 HKMTZJUWMOYMCB-UHFFFAOYSA-N 0.000 description 2
JXNPCFNODXHENK-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonyl-1-[(4-phenylphenyl)methyl]piperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 JXNPCFNODXHENK-UHFFFAOYSA-N 0.000 description 2
FXULTEZWTSEQLZ-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonyl-1-[(4-pyridin-2-ylphenyl)methyl]piperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC(=CC=2)C=2N=CC=CC=2)CC1 FXULTEZWTSEQLZ-UHFFFAOYSA-N 0.000 description 2
UZZOWBRNVGRWPV-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC(OCCN3CCCCC3)=CC=2)CC1 UZZOWBRNVGRWPV-UHFFFAOYSA-N 0.000 description 2
ZPYAYNWVYRRKRN-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonyl-1-propan-2-ylpiperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(C(C)C)CC1 ZPYAYNWVYRRKRN-UHFFFAOYSA-N 0.000 description 2
DUQJAUMBABDBKM-UHFFFAOYSA-N 4-[2-[2-(chloromethyl)phenoxy]ethyl]morpholine Chemical compound ClCC1=CC=CC=C1OCCN1CCOCC1 DUQJAUMBABDBKM-UHFFFAOYSA-N 0.000 description 2
YQJKECADJKTGJJ-UHFFFAOYSA-N 4-[4-(4-chlorophenoxy)phenyl]sulfonyl-1-ethylpiperidine-4-carboxylic acid Chemical compound C1CN(CC)CCC1(C(O)=O)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 YQJKECADJKTGJJ-UHFFFAOYSA-N 0.000 description 2
LOXSIIURNKSILF-UHFFFAOYSA-N 4-[4-(4-chlorophenoxy)phenyl]sulfonyl-1-methylpiperidine-4-carboxylic acid Chemical compound C1CN(C)CCC1(C(O)=O)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 LOXSIIURNKSILF-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
IZMWJUPSQXIVDN-UHFFFAOYSA-N 4-bromo-2-methylbut-1-ene Chemical compound CC(=C)CCBr IZMWJUPSQXIVDN-UHFFFAOYSA-N 0.000 description 2
125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 2
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 2
IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 2
WYHZUCLANNYBTN-UHFFFAOYSA-N 5-methyl-2-(3-methylbut-2-enyl)-2-(4-methylphenyl)sulfonylhex-4-enoic acid Chemical compound CC(C)=CCC(CC=C(C)C)(C(O)=O)S(=O)(=O)C1=CC=C(C)C=C1 WYHZUCLANNYBTN-UHFFFAOYSA-N 0.000 description 2
CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
238000006418 Brown reaction Methods 0.000 description 2
DTMZZXKJZIOMKV-UHFFFAOYSA-N COC1=CC=C(C=C1)S(=O)(=O)C(C)(CC=C(C)C)C Chemical compound COC1=CC=C(C=C1)S(=O)(=O)C(C)(CC=C(C)C)C DTMZZXKJZIOMKV-UHFFFAOYSA-N 0.000 description 2
102000000380 Matrix Metalloproteinase 1 Human genes 0.000 description 2
108010016113 Matrix Metalloproteinase 1 Proteins 0.000 description 2
108010015302 Matrix metalloproteinase-9 Proteins 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
150000001543 aryl boronic acids Chemical class 0.000 description 2
239000012131 assay buffer Substances 0.000 description 2
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical compound BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
230000006835 compression Effects 0.000 description 2
238000007906 compression Methods 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
239000006071 cream Substances 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
XEJCSTMVEXRYCL-UHFFFAOYSA-N ethyl 1-(4-methoxyphenyl)sulfonylcyclopentane-1-carboxylate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C1(C(=O)OCC)CCCC1 XEJCSTMVEXRYCL-UHFFFAOYSA-N 0.000 description 2
YRIRCZNJTKIDMG-UHFFFAOYSA-N ethyl 1-benzyl-4-(4-butoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CC=2C=CC=CC=2)CC1 YRIRCZNJTKIDMG-UHFFFAOYSA-N 0.000 description 2
GNWSAGQKHSUVLT-UHFFFAOYSA-N ethyl 1-benzyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CC1=CC=CC=C1 GNWSAGQKHSUVLT-UHFFFAOYSA-N 0.000 description 2
NUXWDBFBHPVLBS-UHFFFAOYSA-N ethyl 1-cyclooctyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1C1CCCCCCC1 NUXWDBFBHPVLBS-UHFFFAOYSA-N 0.000 description 2
YJKSGYFKCIWOGH-UHFFFAOYSA-N ethyl 1-ethyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C1(C(=O)OCC)CCN(CC)CC1 YJKSGYFKCIWOGH-UHFFFAOYSA-N 0.000 description 2
MSZXFLPUTGBOCD-UHFFFAOYSA-N ethyl 1-tert-butyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C1(C(=O)OCC)CCN(C(C)(C)C)CC1 MSZXFLPUTGBOCD-UHFFFAOYSA-N 0.000 description 2
RXARYKXIADEHEH-UHFFFAOYSA-N ethyl 2-(1-methylimidazol-2-yl)sulfanyloctanoate Chemical compound CCCCCCC(C(=O)OCC)SC1=NC=CN1C RXARYKXIADEHEH-UHFFFAOYSA-N 0.000 description 2
MBEDSSKRMUFORK-UHFFFAOYSA-N ethyl 2-(4-bromophenyl)sulfanylpropanoate Chemical compound CCOC(=O)C(C)SC1=CC=C(Br)C=C1 MBEDSSKRMUFORK-UHFFFAOYSA-N 0.000 description 2
FGXNKLBJPRPHRS-UHFFFAOYSA-N ethyl 2-(4-bromophenyl)sulfonylpropanoate Chemical compound CCOC(=O)C(C)S(=O)(=O)C1=CC=C(Br)C=C1 FGXNKLBJPRPHRS-UHFFFAOYSA-N 0.000 description 2
QDQNVZGZMOJXTJ-UHFFFAOYSA-N ethyl 2-(4-ethoxyphenyl)sulfonylpropanoate Chemical compound CCOC(=O)C(C)S(=O)(=O)C1=CC=C(OCC)C=C1 QDQNVZGZMOJXTJ-UHFFFAOYSA-N 0.000 description 2
PFPUODQZTDRKHA-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfanyl-2,5-dimethylhex-4-enoate Chemical compound CCOC(=O)C(C)(CC=C(C)C)SC1=CC=C(OC)C=C1 PFPUODQZTDRKHA-UHFFFAOYSA-N 0.000 description 2
UJYUVVUMIMWXGN-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfanylheptanoate Chemical compound CCCCCC(C(=O)OCC)SC1=CC=C(OC)C=C1 UJYUVVUMIMWXGN-UHFFFAOYSA-N 0.000 description 2
BYQBUXDCDMGKGE-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfanylhexanoate Chemical compound CCCCC(C(=O)OCC)SC1=CC=C(OC)C=C1 BYQBUXDCDMGKGE-UHFFFAOYSA-N 0.000 description 2
ZXEMOHZODGJZRR-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfanylpentanoate Chemical compound CCOC(=O)C(CCC)SC1=CC=C(OC)C=C1 ZXEMOHZODGJZRR-UHFFFAOYSA-N 0.000 description 2
HKBAKJPOGVGKQT-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfanyltetradecanoate Chemical compound CCCCCCCCCCCCC(C(=O)OCC)SC1=CC=C(OC)C=C1 HKBAKJPOGVGKQT-UHFFFAOYSA-N 0.000 description 2
HSOHVBFCNPZNTB-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2,5-dimethylhex-4-enoate Chemical compound CCOC(=O)C(C)(CC=C(C)C)S(=O)(=O)C1=CC=C(OC)C=C1 HSOHVBFCNPZNTB-UHFFFAOYSA-N 0.000 description 2
DSYJMXBZORREPG-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-(pyridin-3-ylmethyl)decanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCCCCCCC)(C(=O)OCC)CC1=CC=CN=C1 DSYJMXBZORREPG-UHFFFAOYSA-N 0.000 description 2
NIQZLABYWOQQQW-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-[[4-(2-morpholin-4-ylethoxy)phenyl]methyl]pentanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCC)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCOCC1 NIQZLABYWOQQQW-UHFFFAOYSA-N 0.000 description 2
BJOBVVNAABSPRV-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-(4-phenylphenyl)propanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC(C=C1)=CC=C1C1=CC=CC=C1 BJOBVVNAABSPRV-UHFFFAOYSA-N 0.000 description 2
SWIDUBMDSRKUOF-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-[3-(2-piperidin-1-ylethoxy)phenyl]propanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC(C=1)=CC=CC=1OCCN1CCCCC1 SWIDUBMDSRKUOF-UHFFFAOYSA-N 0.000 description 2
CWAFAZWMPYPCLU-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCCCC1 CWAFAZWMPYPCLU-UHFFFAOYSA-N 0.000 description 2
VAILMDDBHWCDBB-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-naphthalen-2-ylpropanoate Chemical compound C=1C=C2C=CC=CC2=CC=1CC(C)(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 VAILMDDBHWCDBB-UHFFFAOYSA-N 0.000 description 2
HRBLYZSWZKHYRS-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-phenylpropanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC1=CC=CC=C1 HRBLYZSWZKHYRS-UHFFFAOYSA-N 0.000 description 2
DVQKRPPWXYFHKP-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-pyridin-3-ylpropanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC1=CC=CN=C1 DVQKRPPWXYFHKP-UHFFFAOYSA-N 0.000 description 2
YKKSGDSVVLJFRV-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-3-naphthalen-2-ylpropanoate Chemical compound C=1C=C2C=CC=CC2=CC=1CC(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 YKKSGDSVVLJFRV-UHFFFAOYSA-N 0.000 description 2
GZEXMJCTLYCWDA-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-5,9-dimethyldeca-4,8-dienoate Chemical compound CC(C)=CCCC(C)=CCC(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 GZEXMJCTLYCWDA-UHFFFAOYSA-N 0.000 description 2
RYUMOQZQWYMLME-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyloctanoate Chemical compound CCCCCCC(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 RYUMOQZQWYMLME-UHFFFAOYSA-N 0.000 description 2
NTIGGVGLYWZAOU-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonylpentanoate Chemical compound CCOC(=O)C(CCC)S(=O)(=O)C1=CC=C(OC)C=C1 NTIGGVGLYWZAOU-UHFFFAOYSA-N 0.000 description 2
HBRDJIHAZDFRMA-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyltetradecanoate Chemical compound CCCCCCCCCCCCC(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 HBRDJIHAZDFRMA-UHFFFAOYSA-N 0.000 description 2
UJSPUGKQHPIXDV-UHFFFAOYSA-N ethyl 2-(4-phenylmethoxyphenyl)sulfonylacetate Chemical compound C1=CC(S(=O)(=O)CC(=O)OCC)=CC=C1OCC1=CC=CC=C1 UJSPUGKQHPIXDV-UHFFFAOYSA-N 0.000 description 2
UXJFKHKHUREURW-UHFFFAOYSA-N ethyl 2-(cyclohexylmethyl)-2-(4-methoxyphenyl)sulfonyl-3-pyridin-3-ylpropanoate Chemical compound C=1C=CN=CC=1CC(S(=O)(=O)C=1C=CC(OC)=CC=1)(C(=O)OCC)CC1CCCCC1 UXJFKHKHUREURW-UHFFFAOYSA-N 0.000 description 2
OGCZFGRUVNFOFU-UHFFFAOYSA-N ethyl 2-[(4-methoxyphenyl)methylsulfonyl]-2-methyl-3-phenylpropanoate Chemical compound C=1C=C(OC)C=CC=1CS(=O)(=O)C(C)(C(=O)OCC)CC1=CC=CC=C1 OGCZFGRUVNFOFU-UHFFFAOYSA-N 0.000 description 2
ZTIGBUWNNZCRJQ-UHFFFAOYSA-N ethyl 2-[2-(4-methoxyphenyl)sulfanylphenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC=C1SC1=CC=C(OC)C=C1 ZTIGBUWNNZCRJQ-UHFFFAOYSA-N 0.000 description 2
CMLJYJOADGIECP-UHFFFAOYSA-N ethyl 2-[4-(2-ethylbutoxy)phenyl]sulfanylacetate Chemical compound CCOC(=O)CSC1=CC=C(OCC(CC)CC)C=C1 CMLJYJOADGIECP-UHFFFAOYSA-N 0.000 description 2
YPSKGXCMXOMOLG-UHFFFAOYSA-N ethyl 2-[4-(3-methylbutoxy)phenyl]sulfanylacetate Chemical compound CCOC(=O)CSC1=CC=C(OCCC(C)C)C=C1 YPSKGXCMXOMOLG-UHFFFAOYSA-N 0.000 description 2
HGOADIBTJSEIAQ-UHFFFAOYSA-N ethyl 2-[4-[(4-chlorophenyl)methoxy]phenyl]sulfonyl-1-methylpiperidine-4-carboxylate Chemical compound C1C(C(=O)OCC)CCN(C)C1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=C(Cl)C=C1 HGOADIBTJSEIAQ-UHFFFAOYSA-N 0.000 description 2
VBYHDMCZQKMCFS-UHFFFAOYSA-N ethyl 2-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-methoxyphenyl)sulfonyloctanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCCCCC)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCCCCC1 VBYHDMCZQKMCFS-UHFFFAOYSA-N 0.000 description 2
HOYVBNPMQUOTOH-UHFFFAOYSA-N ethyl 2-benzyl-2-(4-methoxyphenyl)sulfonyl-3-phenylpropanoate Chemical compound C=1C=CC=CC=1CC(S(=O)(=O)C=1C=CC(OC)=CC=1)(C(=O)OCC)CC1=CC=CC=C1 HOYVBNPMQUOTOH-UHFFFAOYSA-N 0.000 description 2
OWFFBQYWNMOPCF-UHFFFAOYSA-N ethyl 2-benzyl-4-[di(propan-2-yl)amino]-2-(4-methoxyphenyl)sulfonylbutanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCN(C(C)C)C(C)C)(C(=O)OCC)CC1=CC=CC=C1 OWFFBQYWNMOPCF-UHFFFAOYSA-N 0.000 description 2
WNFUWONOILPKNX-UHFFFAOYSA-N ethyl 2-bromo-3-methylbutanoate Chemical compound CCOC(=O)C(Br)C(C)C WNFUWONOILPKNX-UHFFFAOYSA-N 0.000 description 2
KOUAQOCYMAENKN-UHFFFAOYSA-N ethyl 2-bromohexanoate Chemical compound CCCCC(Br)C(=O)OCC KOUAQOCYMAENKN-UHFFFAOYSA-N 0.000 description 2
ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 2
XSHVMARUOTUDOM-UHFFFAOYSA-N ethyl 2-methyl-3-phenyl-2-thiophen-2-ylsulfonylpropanoate Chemical compound C=1C=CSC=1S(=O)(=O)C(C)(C(=O)OCC)CC1=CC=CC=C1 XSHVMARUOTUDOM-UHFFFAOYSA-N 0.000 description 2
ZLAAGNCOJROERS-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-[(4-methylphenyl)methyl]piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CC=2C=CC(C)=CC=2)CC1 ZLAAGNCOJROERS-UHFFFAOYSA-N 0.000 description 2
IFGSAVPFPMXDIQ-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-butylpiperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CCCC)CC1 IFGSAVPFPMXDIQ-UHFFFAOYSA-N 0.000 description 2
GZBSOQZXQQQEHJ-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-ethylpiperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CC)CC1 GZBSOQZXQQQEHJ-UHFFFAOYSA-N 0.000 description 2
JPLKAYSUFIYVRB-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-methylpiperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(C)CC1 JPLKAYSUFIYVRB-UHFFFAOYSA-N 0.000 description 2
ZOCIWLKGUFBEST-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-methylpiperidine-4-carboxylate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C1(C(=O)OCC)CCN(C)CC1 ZOCIWLKGUFBEST-UHFFFAOYSA-N 0.000 description 2
URNMBYWPWHBBHU-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-propan-2-ylpiperidine-4-carboxylate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C1(C(=O)OCC)CCN(C(C)C)CC1 URNMBYWPWHBBHU-UHFFFAOYSA-N 0.000 description 2
MHLHXNFBOSJAFV-UHFFFAOYSA-N ethyl 6-(1,3-dioxoisoindol-2-yl)-2-(4-methoxyphenyl)sulfonyl-2-methylhexanoate Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCCC(C)(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 MHLHXNFBOSJAFV-UHFFFAOYSA-N 0.000 description 2
230000005284 excitation Effects 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
239000003350 kerosene Substances 0.000 description 2
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000011159 matrix material Substances 0.000 description 2
HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 2
PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 2
MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 2
SFQOTBMYWKTJKF-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-3-phenoxypropan-1-amine Chemical compound ClCCN(CCCl)CCCOC1=CC=CC=C1 SFQOTBMYWKTJKF-UHFFFAOYSA-N 0.000 description 2
APMORDWSEGHCAQ-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-3-phenylpropan-1-amine Chemical compound ClCCN(CCCl)CCCC1=CC=CC=C1 APMORDWSEGHCAQ-UHFFFAOYSA-N 0.000 description 2
OABJAIADVRIARX-UHFFFAOYSA-N n-[(4-bromophenyl)methyl]-2-chloro-n-(2-chloroethyl)ethanamine Chemical compound ClCCN(CCCl)CC1=CC=C(Br)C=C1 OABJAIADVRIARX-UHFFFAOYSA-N 0.000 description 2
SWTFBLUIBHXOAH-UHFFFAOYSA-N n-butylhydroxylamine Chemical compound CCCCNO SWTFBLUIBHXOAH-UHFFFAOYSA-N 0.000 description 2
ULKWNWCMBKLDEO-UHFFFAOYSA-N n-hydroxy-1-(4-methoxyphenyl)sulfonylcyclopentane-1-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCCC1 ULKWNWCMBKLDEO-UHFFFAOYSA-N 0.000 description 2
KLYIBVBIKFMTRO-UHFFFAOYSA-N n-hydroxy-1-[(4-methoxyphenyl)methyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1CN1CCC(S(=O)(=O)C=2C=CC(OC)=CC=2)(C(=O)NO)CC1 KLYIBVBIKFMTRO-UHFFFAOYSA-N 0.000 description 2
BSIZUMJRKYHEBR-QGZVFWFLSA-N n-hydroxy-2(r)-[[(4-methoxyphenyl)sulfonyl](3-picolyl)amino]-3-methylbutanamide hydrochloride Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N([C@H](C(C)C)C(=O)NO)CC1=CC=CN=C1 BSIZUMJRKYHEBR-QGZVFWFLSA-N 0.000 description 2
MAAQMEJONCVFHE-UHFFFAOYSA-N n-hydroxy-2-(1-methylimidazol-2-yl)sulfanyloctanamide Chemical compound CCCCCCC(C(=O)NO)SC1=NC=CN1C MAAQMEJONCVFHE-UHFFFAOYSA-N 0.000 description 2
RXGUVEPZEYQOMY-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfanyl-2,5-dimethylhex-4-enamide Chemical compound COC1=CC=C(SC(C)(CC=C(C)C)C(=O)NO)C=C1 RXGUVEPZEYQOMY-UHFFFAOYSA-N 0.000 description 2
DPIRTDXQUMBHTC-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfanyl-2-phenylacetamide Chemical compound C1=CC(OC)=CC=C1SC(C(=O)NO)C1=CC=CC=C1 DPIRTDXQUMBHTC-UHFFFAOYSA-N 0.000 description 2
VCFVKTXYJRRMDY-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfanylheptanamide Chemical compound CCCCCC(C(=O)NO)SC1=CC=C(OC)C=C1 VCFVKTXYJRRMDY-UHFFFAOYSA-N 0.000 description 2
WEBZGXZPLFJJPD-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfanyloctanamide Chemical compound CCCCCCC(C(=O)NO)SC1=CC=C(OC)C=C1 WEBZGXZPLFJJPD-UHFFFAOYSA-N 0.000 description 2
DPJTWMTUWFZRHC-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2,5,9-trimethyldeca-4,8-dienamide Chemical compound COC1=CC=C(S(=O)(=O)C(C)(CC=C(C)CCC=C(C)C)C(=O)NO)C=C1 DPJTWMTUWFZRHC-UHFFFAOYSA-N 0.000 description 2
OBAPHLFTXDIRHP-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-(pyridin-3-ylmethyl)dec-4-ynamide Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CC#CCCCCC)(C(=O)NO)CC1=CC=CN=C1 OBAPHLFTXDIRHP-UHFFFAOYSA-N 0.000 description 2
KDSNJNDUIRTNNR-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-(pyridin-3-ylmethyl)hexanamide Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCCC)(C(=O)NO)CC1=CC=CN=C1 KDSNJNDUIRTNNR-UHFFFAOYSA-N 0.000 description 2
FVYBFRCALRJYHO-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-(pyridin-3-ylmethyl)pent-4-ynamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CC#C)(C(=O)NO)CC1=CC=CN=C1 FVYBFRCALRJYHO-UHFFFAOYSA-N 0.000 description 2
GVQNLPGZSSRAFQ-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-[[4-(2-morpholin-4-ylethoxy)phenyl]methyl]pentanamide Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCC)(C(=O)NO)CC(C=C1)=CC=C1OCCN1CCOCC1 GVQNLPGZSSRAFQ-UHFFFAOYSA-N 0.000 description 2
ZBIYSEFCPUXCRC-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-methyl-3-naphthalen-2-ylpropanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(=O)NO)CC1=CC=C(C=CC=C2)C2=C1 ZBIYSEFCPUXCRC-UHFFFAOYSA-N 0.000 description 2
VWUZZGFUJBCIML-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-oct-2-ynyldec-4-ynamide Chemical compound CCCCCC#CCC(CC#CCCCCC)(C(=O)NO)S(=O)(=O)C1=CC=C(OC)C=C1 VWUZZGFUJBCIML-UHFFFAOYSA-N 0.000 description 2
AUCTYKZCPSWUEL-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-prop-2-ynylpent-4-ynamide Chemical compound COC1=CC=C(S(=O)(=O)C(CC#C)(CC#C)C(=O)NO)C=C1 AUCTYKZCPSWUEL-UHFFFAOYSA-N 0.000 description 2
ZUJXLCINYDKZGV-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-3-methylbutanamide Chemical compound COC1=CC=C(S(=O)(=O)C(C(C)C)C(=O)NO)C=C1 ZUJXLCINYDKZGV-UHFFFAOYSA-N 0.000 description 2
HBIQJOZNDMPMAG-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-3-phenylpropanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(=O)NO)CC1=CC=CC=C1 HBIQJOZNDMPMAG-UHFFFAOYSA-N 0.000 description 2
XGMBTNMILCXDFB-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-5-methyl-2-(3-methylbut-2-enyl)hex-4-enamide Chemical compound COC1=CC=C(S(=O)(=O)C(CC=C(C)C)(CC=C(C)C)C(=O)NO)C=C1 XGMBTNMILCXDFB-UHFFFAOYSA-N 0.000 description 2
QDJTVBZWIYKRMZ-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-5-methyl-2-(pyridin-3-ylmethyl)hex-4-enamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CC=C(C)C)(C(=O)NO)CC1=CC=CN=C1 QDJTVBZWIYKRMZ-UHFFFAOYSA-N 0.000 description 2
BIRCQLGEHYKLHU-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-5-methyl-2-[[4-(2-morpholin-4-ylethoxy)phenyl]methyl]hex-4-enamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CC=C(C)C)(C(=O)NO)CC(C=C1)=CC=C1OCCN1CCOCC1 BIRCQLGEHYKLHU-UHFFFAOYSA-N 0.000 description 2
GITDAELUDOBLOT-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-6-phenoxy-2-(pyridin-3-ylmethyl)hexanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(=O)NO)(CC=1C=NC=CC=1)CCCCOC1=CC=CC=C1 GITDAELUDOBLOT-UHFFFAOYSA-N 0.000 description 2
UVYWXUJXEFVRIM-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonylhexanamide Chemical compound CCCCC(C(=O)NO)S(=O)(=O)C1=CC=C(OC)C=C1 UVYWXUJXEFVRIM-UHFFFAOYSA-N 0.000 description 2
ZGEUEQMPAIUHSM-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyltetradecanamide Chemical compound CCCCCCCCCCCCC(C(=O)NO)S(=O)(=O)C1=CC=C(OC)C=C1 ZGEUEQMPAIUHSM-UHFFFAOYSA-N 0.000 description 2
QZXZIFMHZPCPPN-UHFFFAOYSA-N n-hydroxy-2-methyl-2-(1-methylimidazol-2-yl)sulfonyl-3-(4-phenylphenyl)propanamide Chemical compound CN1C=CN=C1S(=O)(=O)C(C)(C(=O)NO)CC1=CC=C(C=2C=CC=CC=2)C=C1 QZXZIFMHZPCPPN-UHFFFAOYSA-N 0.000 description 2
PRLGEFXGCXSHFM-UHFFFAOYSA-N n-hydroxy-2-octylsulfonyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanamide Chemical compound C1=CC(CC(S(=O)(=O)CCCCCCCC)C(=O)NO)=CC=C1OCCN1CCCCC1 PRLGEFXGCXSHFM-UHFFFAOYSA-N 0.000 description 2
PRBMKJZQAUSBQV-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]piperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(OCCN3CCCCC3)=CC=2)CC1 PRBMKJZQAUSBQV-UHFFFAOYSA-N 0.000 description 2
RBRSAOMOZVVQSQ-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-methylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(C)CC1 RBRSAOMOZVVQSQ-UHFFFAOYSA-N 0.000 description 2
PPTJZFSGDMWVFF-UHFFFAOYSA-N n-hydroxy-5-methyl-2-(3-methylbut-2-enyl)-2-(4-methylphenyl)sulfonylhex-4-enamide Chemical compound CC(C)=CCC(CC=C(C)C)(C(=O)NO)S(=O)(=O)C1=CC=C(C)C=C1 PPTJZFSGDMWVFF-UHFFFAOYSA-N 0.000 description 2
CCBCHURBDSNSTJ-UHFFFAOYSA-N n-hydroxybutanamide Chemical compound CCCC(=O)NO CCBCHURBDSNSTJ-UHFFFAOYSA-N 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000008569 process Effects 0.000 description 2
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
239000008174 sterile solution Substances 0.000 description 2
239000011550 stock solution Substances 0.000 description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
QFODAAXHJKPOGZ-UHFFFAOYSA-N tert-butyl 2-(4-fluorophenyl)sulfonyl-3-pyridin-3-ylpropanoate Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)C(C(=O)OC(C)(C)C)CC1=CC=CN=C1 QFODAAXHJKPOGZ-UHFFFAOYSA-N 0.000 description 2
KAEOFVPILQCLRC-UHFFFAOYSA-N tert-butyl 2-(4-fluorophenyl)sulfonylacetate Chemical compound CC(C)(C)OC(=O)CS(=O)(=O)C1=CC=C(F)C=C1 KAEOFVPILQCLRC-UHFFFAOYSA-N 0.000 description 2
NSXGUGZMZDDNOF-UHFFFAOYSA-N tert-butyl 2-(4-methoxyphenyl)sulfonyl-2-(pyridin-3-ylmethyl)hexanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCCC)(C(=O)OC(C)(C)C)CC1=CC=CN=C1 NSXGUGZMZDDNOF-UHFFFAOYSA-N 0.000 description 2
150000003568 thioethers Chemical class 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 1
DOMQFIFVDIAOOT-ROUUACIJSA-N (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NN=C1C=1C=NC=C(C=1)C)NS(=O)(=O)[C@@H](C)[C@H](C)C1=NC=C(C=N1)C DOMQFIFVDIAOOT-ROUUACIJSA-N 0.000 description 1
MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
PTDVPWWJRCOIIO-UHFFFAOYSA-N (4-methoxyphenyl)methanethiol Chemical compound COC1=CC=C(CS)C=C1 PTDVPWWJRCOIIO-UHFFFAOYSA-N 0.000 description 1
UOAJUPONZOXFNX-UHFFFAOYSA-N (4-methylphenyl)sulfonyl acetate Chemical compound CC(=O)OS(=O)(=O)C1=CC=C(C)C=C1 UOAJUPONZOXFNX-UHFFFAOYSA-N 0.000 description 1
ZHIJJVWURAHCNB-WGOQTCKBSA-N (4e)-2-(4-methoxyphenyl)sulfonyl-5,9-dimethyl-2-[[4-(2-morpholin-4-ylethoxy)phenyl]methyl]deca-4,8-dienoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C\C=C(/C)CCC=C(C)C)(C(O)=O)CC(C=C1)=CC=C1OCCN1CCOCC1 ZHIJJVWURAHCNB-WGOQTCKBSA-N 0.000 description 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 1
UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
YZIFVWOCPGPNHB-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C(Cl)=C1 YZIFVWOCPGPNHB-UHFFFAOYSA-N 0.000 description 1
ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
PMIAMRAWHYEPNH-UHFFFAOYSA-N 1-(2-chloroethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCCl)C=C1 PMIAMRAWHYEPNH-UHFFFAOYSA-N 0.000 description 1
GGHYOLDNCQVRLQ-UHFFFAOYSA-N 1-(4-butoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C(CCC)OC1=CC=C(C=C1)S(=O)(=O)N1CCC(CC1)C(=O)O GGHYOLDNCQVRLQ-UHFFFAOYSA-N 0.000 description 1
VGISFWWEOGVMED-UHFFFAOYSA-N 1-(chloromethyl)-3-methoxybenzene Chemical compound COC1=CC=CC(CCl)=C1 VGISFWWEOGVMED-UHFFFAOYSA-N 0.000 description 1
MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 1
HYZDHISHDZBYBQ-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-n-hydroxy-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(F)=CC=2)CC1 HYZDHISHDZBYBQ-UHFFFAOYSA-N 0.000 description 1
ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
UVPYYSQOUYOQJF-UHFFFAOYSA-N 1-[2-[3-(chloromethyl)phenoxy]ethyl]piperidine Chemical compound ClCC1=CC=CC(OCCN2CCCCC2)=C1 UVPYYSQOUYOQJF-UHFFFAOYSA-N 0.000 description 1
GKUHXMBRACSNCN-UHFFFAOYSA-N 1-[2-[4-(chloromethyl)phenoxy]ethyl]-4-(3-chlorophenyl)piperazine Chemical compound C1=CC(CCl)=CC=C1OCCN1CCN(C=2C=C(Cl)C=CC=2)CC1 GKUHXMBRACSNCN-UHFFFAOYSA-N 0.000 description 1
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
LZSYGJNFCREHMD-UHFFFAOYSA-N 1-bromo-2-(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1Br LZSYGJNFCREHMD-UHFFFAOYSA-N 0.000 description 1
HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
IRYSAAMKXPLGAM-UHFFFAOYSA-N 1-chloro-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1Cl IRYSAAMKXPLGAM-UHFFFAOYSA-N 0.000 description 1
GJICTISPMDMSQH-UHFFFAOYSA-N 1-cyclooctyl-n-hydroxy-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(C2CCCCCCC2)CC1 GJICTISPMDMSQH-UHFFFAOYSA-N 0.000 description 1
ZYRWJHQOGSXLDQ-UHFFFAOYSA-N 1-methoxy-4-(9-methylheptadeca-6,11-diyn-9-ylsulfonyl)benzene Chemical compound COC1=CC=C(C=C1)S(=O)(=O)C(C)(CC#CCCCCC)CC#CCCCCC ZYRWJHQOGSXLDQ-UHFFFAOYSA-N 0.000 description 1
NJERVIAZLFHHCZ-UHFFFAOYSA-N 2,1,3-benzothiadiazole-4-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=NSN=C12 NJERVIAZLFHHCZ-UHFFFAOYSA-N 0.000 description 1
PSUFBJZOUDUNPE-UHFFFAOYSA-N 2-(1-methylimidazol-2-yl)sulfanyloctanoic acid Chemical compound CCCCCCC(C(O)=O)SC1=NC=CN1C PSUFBJZOUDUNPE-UHFFFAOYSA-N 0.000 description 1
UWRMEACHQDRDAY-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)sulfonyl-n-hydroxyoctanamide Chemical compound CCCCCCC(C(=O)NO)S(=O)(=O)C1=CC(Cl)=CC=C1Cl UWRMEACHQDRDAY-UHFFFAOYSA-N 0.000 description 1
SGFFAYUOWYWLGI-UHFFFAOYSA-N 2-(2-methylfuran-3-yl)sulfanylpropanoic acid Chemical compound OC(=O)C(C)SC=1C=COC=1C SGFFAYUOWYWLGI-UHFFFAOYSA-N 0.000 description 1
ODHMCSXKHMVNIG-UHFFFAOYSA-N 2-(2-methylfuran-3-yl)sulfonylpropanoic acid Chemical compound OC(=O)C(C)S(=O)(=O)C=1C=COC=1C ODHMCSXKHMVNIG-UHFFFAOYSA-N 0.000 description 1
MHCKEKCCGVDLME-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)sulfinyl-n-hydroxyoctanamide Chemical compound CCCCCCC(C(=O)NO)S(=O)C1=CC=C(OC)C(OC)=C1 MHCKEKCCGVDLME-UHFFFAOYSA-N 0.000 description 1
CLHLGWKJCGFOOX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)sulfonyl-n-hydroxyoctanamide Chemical compound CCCCCCC(C(=O)NO)S(=O)(=O)C1=CC=C(OC)C(OC)=C1 CLHLGWKJCGFOOX-UHFFFAOYSA-N 0.000 description 1
LPYLDWZGZSUVFC-UHFFFAOYSA-N 2-(4-acetamidophenyl)sulfinyl-n-hydroxy-3-phenylpropanamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)C(C(=O)NO)CC1=CC=CC=C1 LPYLDWZGZSUVFC-UHFFFAOYSA-N 0.000 description 1
GMBQLXCNIVXUQI-UHFFFAOYSA-N 2-(4-acetamidophenyl)sulfonyl-n-hydroxy-3-phenylpropanamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)C(C(=O)NO)CC1=CC=CC=C1 GMBQLXCNIVXUQI-UHFFFAOYSA-N 0.000 description 1
UXFWTIGUWHJKDD-UHFFFAOYSA-N 2-(4-bromobutyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCBr)C(=O)C2=C1 UXFWTIGUWHJKDD-UHFFFAOYSA-N 0.000 description 1
PMASRWNUZSPNGW-UHFFFAOYSA-N 2-(4-bromophenyl)sulfinyl-n,n'-dihydroxypentanediamide Chemical compound ONC(=O)CCC(C(=O)NO)S(=O)C1=CC=C(Br)C=C1 PMASRWNUZSPNGW-UHFFFAOYSA-N 0.000 description 1
SARGBONDXLLOMP-UHFFFAOYSA-N 2-(4-bromophenyl)sulfonyl-n,n'-dihydroxypentanediamide Chemical compound ONC(=O)CCC(C(=O)NO)S(=O)(=O)C1=CC=C(Br)C=C1 SARGBONDXLLOMP-UHFFFAOYSA-N 0.000 description 1
CGBJLDBRKBYMDG-UHFFFAOYSA-N 2-(4-butoxyphenyl)sulfinyl-n-hydroxyoctanamide Chemical compound CCCCCCC(C(=O)NO)S(=O)C1=CC=C(OCCCC)C=C1 CGBJLDBRKBYMDG-UHFFFAOYSA-N 0.000 description 1
LLKIMCGTHFTTDN-UHFFFAOYSA-N 2-(4-butoxyphenyl)sulfonyl-n-hydroxyoctanamide Chemical compound CCCCCCC(C(=O)NO)S(=O)(=O)C1=CC=C(OCCCC)C=C1 LLKIMCGTHFTTDN-UHFFFAOYSA-N 0.000 description 1
VEOFIHCSEZTRDB-UHFFFAOYSA-N 2-(4-fluorophenyl)sulfanyl-n-hydroxyoctanamide Chemical compound CCCCCCC(C(=O)NO)SC1=CC=C(F)C=C1 VEOFIHCSEZTRDB-UHFFFAOYSA-N 0.000 description 1
NVMMVQCIAOHAAX-UHFFFAOYSA-N 2-(4-fluorophenyl)sulfonyl-2-(pyridin-3-ylmethyl)dec-4-ynoic acid Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)C(CC#CCCCCC)(C(O)=O)CC1=CC=CN=C1 NVMMVQCIAOHAAX-UHFFFAOYSA-N 0.000 description 1
VNDOHDAODONNJS-UHFFFAOYSA-N 2-(4-fluorophenyl)sulfonyl-2-(pyridin-3-ylmethyl)hex-4-ynoic acid Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)C(CC#CC)(C(O)=O)CC1=CC=CN=C1 VNDOHDAODONNJS-UHFFFAOYSA-N 0.000 description 1
MWHHLZIXPLVDSD-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfinyl-2,5-dimethylhex-4-enoic acid Chemical compound COC1=CC=C(S(=O)C(C)(CC=C(C)C)C(O)=O)C=C1 MWHHLZIXPLVDSD-UHFFFAOYSA-N 0.000 description 1
WTGHZVHCDIHHCL-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2,5-dimethylhex-4-enoic acid Chemical compound COC1=CC=C(S(=O)(=O)C(C)(CC=C(C)C)C(O)=O)C=C1 WTGHZVHCDIHHCL-UHFFFAOYSA-N 0.000 description 1
OYAKMCDAJLJIPR-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-(pyridin-3-ylmethyl)dec-4-ynoic acid Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CC#CCCCCC)(C(O)=O)CC1=CC=CN=C1 OYAKMCDAJLJIPR-UHFFFAOYSA-N 0.000 description 1
BOBGFOWVZNMSSD-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-(pyridin-3-ylmethyl)pent-4-ynoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CC#C)(C(O)=O)CC1=CC=CN=C1 BOBGFOWVZNMSSD-UHFFFAOYSA-N 0.000 description 1
MMKAFLYMPYTLAJ-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-(4-phenylphenyl)propanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(O)=O)CC1=CC=C(C=2C=CC=CC=2)C=C1 MMKAFLYMPYTLAJ-UHFFFAOYSA-N 0.000 description 1
NQIVAZLRVBPGBV-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-[3-(2-piperidin-1-ylethoxy)phenyl]propanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(N)=O)CC1=CC=CC(OCCN2CCCCC2)=C1 NQIVAZLRVBPGBV-UHFFFAOYSA-N 0.000 description 1
ZPJKXHCENJWATP-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(O)=O)CC1=CC=CC=C1 ZPJKXHCENJWATP-UHFFFAOYSA-N 0.000 description 1
OHEWZGZQMFOESI-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-methylpropanoic acid Chemical compound COC1=CC=C(S(=O)(=O)C(C)(C)C(O)=O)C=C1 OHEWZGZQMFOESI-UHFFFAOYSA-N 0.000 description 1
PJORXDHBIQPZIM-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-oct-2-ynyldec-4-ynoic acid Chemical compound CCCCCC#CCC(CC#CCCCCC)(C(O)=O)S(=O)(=O)C1=CC=C(OC)C=C1 PJORXDHBIQPZIM-UHFFFAOYSA-N 0.000 description 1
BBNHJVXRRNHZTK-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-prop-2-ynylpent-4-ynoic acid Chemical compound COC1=CC=C(S(=O)(=O)C(CC#C)(CC#C)C(O)=O)C=C1 BBNHJVXRRNHZTK-UHFFFAOYSA-N 0.000 description 1
FHRSRACHKWFWRX-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-3-methylbutanoic acid Chemical compound COC1=CC=C(S(=O)(=O)C(C(C)C)C(O)=O)C=C1 FHRSRACHKWFWRX-UHFFFAOYSA-N 0.000 description 1
RUDBKWWQIOVCKI-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-3-naphthalen-2-ylpropanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(N)=O)CC1=CC=C(C=CC=C2)C2=C1 RUDBKWWQIOVCKI-UHFFFAOYSA-N 0.000 description 1
UCFISKSCDSTZJC-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-3-phenylpropanamide Chemical compound COC1=CC=C(C=C1)S(=O)(=O)C(C(=O)N)CC1=CC=CC=C1 UCFISKSCDSTZJC-UHFFFAOYSA-N 0.000 description 1
ZHIJJVWURAHCNB-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-5,9-dimethyl-2-[[4-(2-morpholin-4-ylethoxy)phenyl]methyl]deca-4,8-dienoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CC=C(C)CCC=C(C)C)(C(O)=O)CC(C=C1)=CC=C1OCCN1CCOCC1 ZHIJJVWURAHCNB-UHFFFAOYSA-N 0.000 description 1
ANYLSSXXZWLYBN-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-5-methyl-2-(3-methylbut-2-enyl)hex-4-enoic acid Chemical compound COC1=CC=C(S(=O)(=O)C(CC=C(C)C)(CC=C(C)C)C(O)=O)C=C1 ANYLSSXXZWLYBN-UHFFFAOYSA-N 0.000 description 1
MTLAOAMTMRAMIC-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-5-methyl-2-[[4-(2-morpholin-4-ylethoxy)phenyl]methyl]hex-4-enoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CC=C(C)C)(C(O)=O)CC(C=C1)=CC=C1OCCN1CCOCC1 MTLAOAMTMRAMIC-UHFFFAOYSA-N 0.000 description 1
CRWKHOSIPSVVGS-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-6-phenoxyhexanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(O)=O)CCCCOC1=CC=CC=C1 CRWKHOSIPSVVGS-UHFFFAOYSA-N 0.000 description 1
ULPRUSMQMAGYSC-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonylacetic acid Chemical compound COC1=CC=C(S(=O)(=O)CC(O)=O)C=C1 ULPRUSMQMAGYSC-UHFFFAOYSA-N 0.000 description 1
CBBAHBOTQLDRMV-UHFFFAOYSA-N 2-(benzenesulfonyl)-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)S(=O)(=O)C1=CC=CC=C1 CBBAHBOTQLDRMV-UHFFFAOYSA-N 0.000 description 1
RUHJZSZTSCSTCC-UHFFFAOYSA-N 2-(bromomethyl)naphthalene Chemical compound C1=CC=CC2=CC(CBr)=CC=C21 RUHJZSZTSCSTCC-UHFFFAOYSA-N 0.000 description 1
JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 description 1
BSRJZWBKKVMMRD-UHFFFAOYSA-N 2-(cyclohexylmethyl)-n-hydroxy-2-(4-methoxyphenyl)sulfonyl-3-pyridin-3-ylpropanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(=O)NO)(CC=1C=NC=CC=1)CC1CCCCC1 BSRJZWBKKVMMRD-UHFFFAOYSA-N 0.000 description 1
RUYNUXHHUVUINQ-UHFFFAOYSA-N 2-Methyl-3-furanthiol Chemical compound CC=1OC=CC=1S RUYNUXHHUVUINQ-UHFFFAOYSA-N 0.000 description 1
LWRIMGTXNOUVAF-UHFFFAOYSA-N 2-[(2,5-dioxoimidazolidin-4-yl)methylsulfanyl]-n-hydroxyoctanamide Chemical compound CCCCCCC(C(=O)NO)SCC1NC(=O)NC1=O LWRIMGTXNOUVAF-UHFFFAOYSA-N 0.000 description 1
IMKCELAULRWAOG-UHFFFAOYSA-N 2-[(2,5-dioxoimidazolidin-4-yl)methylsulfonyl]-n-hydroxyoctanamide Chemical compound CCCCCCC(C(=O)NO)S(=O)(=O)CC1NC(=O)NC1=O IMKCELAULRWAOG-UHFFFAOYSA-N 0.000 description 1
RMLOQPUPBVVMCO-UHFFFAOYSA-N 2-[2-hydroxyethyl(2-phenylethyl)amino]ethanol Chemical compound OCCN(CCO)CCC1=CC=CC=C1 RMLOQPUPBVVMCO-UHFFFAOYSA-N 0.000 description 1
XAJXIDCDLGBZFI-UHFFFAOYSA-N 2-[2-hydroxyethyl-[(4-phenylphenyl)methyl]amino]ethanol Chemical compound C1=CC(CN(CCO)CCO)=CC=C1C1=CC=CC=C1 XAJXIDCDLGBZFI-UHFFFAOYSA-N 0.000 description 1
YAUGGMXSAKUVKA-UHFFFAOYSA-N 2-[2-hydroxyethyl-[2-(4-methoxyphenyl)ethyl]amino]ethanol Chemical compound COC1=CC=C(CCN(CCO)CCO)C=C1 YAUGGMXSAKUVKA-UHFFFAOYSA-N 0.000 description 1
YDVHSWJMXHWUCG-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)phenyl]sulfinyl-n-hydroxyoctanamide Chemical compound C1=CC(S(=O)C(C(=O)NO)CCCCCC)=CC=C1C1=CC=C(Cl)C=C1 YDVHSWJMXHWUCG-UHFFFAOYSA-N 0.000 description 1
OWPHGBRIKDMSSG-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)phenyl]sulfonyl-n-hydroxyoctanamide Chemical compound C1=CC(S(=O)(=O)C(C(=O)NO)CCCCCC)=CC=C1C1=CC=C(Cl)C=C1 OWPHGBRIKDMSSG-UHFFFAOYSA-N 0.000 description 1
SWNALBJLNGFPPD-UHFFFAOYSA-N 2-[4-(5-chlorothiophen-2-yl)phenyl]sulfinyl-n-hydroxyoctanamide Chemical compound C1=CC(S(=O)C(C(=O)NO)CCCCCC)=CC=C1C1=CC=C(Cl)S1 SWNALBJLNGFPPD-UHFFFAOYSA-N 0.000 description 1
PQWPKFKLHWBJHS-UHFFFAOYSA-N 2-[4-(5-chlorothiophen-2-yl)phenyl]sulfonyl-n-hydroxyoctanamide Chemical compound C1=CC(S(=O)(=O)C(C(=O)NO)CCCCCC)=CC=C1C1=CC=C(Cl)S1 PQWPKFKLHWBJHS-UHFFFAOYSA-N 0.000 description 1
SXRGONXLOGEUEJ-UHFFFAOYSA-N 2-[4-(chloromethyl)phenoxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC=C(CCl)C=C1 SXRGONXLOGEUEJ-UHFFFAOYSA-N 0.000 description 1
SFLBWAHPLPUEEH-UHFFFAOYSA-N 2-[4-(cyclopentylamino)phenyl]sulfanyl-n-hydroxyoctanamide Chemical compound C1=CC(SC(CCCCCC)C(=O)NO)=CC=C1NC1CCCC1 SFLBWAHPLPUEEH-UHFFFAOYSA-N 0.000 description 1
PNTJNAKGRJRKAJ-UHFFFAOYSA-N 2-[8-[1-(hydroxyamino)-1-oxopropan-2-yl]sulfonyloctylsulfonyl]propanoic acid Chemical compound OC(=O)C(C)S(=O)(=O)CCCCCCCCS(=O)(=O)C(C)C(=O)NO PNTJNAKGRJRKAJ-UHFFFAOYSA-N 0.000 description 1
MIZIOHLLYXVEHJ-UHFFFAOYSA-N 2-[benzyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)CC1=CC=CC=C1 MIZIOHLLYXVEHJ-UHFFFAOYSA-N 0.000 description 1
GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 description 1
UTOSHYLAYAOIJO-UHFFFAOYSA-N 2-[cyclooctyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)C1CCCCCCC1 UTOSHYLAYAOIJO-UHFFFAOYSA-N 0.000 description 1
IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
WAKFRZBXTKUFIW-UHFFFAOYSA-N 2-bromo-2-phenylacetic acid Chemical compound OC(=O)C(Br)C1=CC=CC=C1 WAKFRZBXTKUFIW-UHFFFAOYSA-N 0.000 description 1
CRTWOYOCILXSSX-UHFFFAOYSA-N 2-bromo-3-(1h-imidazol-5-yl)propanoic acid Chemical compound OC(=O)C(Br)CC1=CN=CN1 CRTWOYOCILXSSX-UHFFFAOYSA-N 0.000 description 1
VKJQJNVYWGDEQN-UHFFFAOYSA-N 2-bromo-3-phenylmethoxypropanoic acid Chemical compound OC(=O)C(Br)COCC1=CC=CC=C1 VKJQJNVYWGDEQN-UHFFFAOYSA-N 0.000 description 1
QEGZIUWWRSPQNR-UHFFFAOYSA-N 2-bromo-n-hydroxypropanamide Chemical compound CC(Br)C(=O)NO QEGZIUWWRSPQNR-UHFFFAOYSA-N 0.000 description 1
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
MONMFXREYOKQTI-UHFFFAOYSA-M 2-bromopropanoate Chemical compound CC(Br)C([O-])=O MONMFXREYOKQTI-UHFFFAOYSA-M 0.000 description 1
OSPOQAOLEWBBCB-UHFFFAOYSA-N 2-but-2-ynyl-2-(4-fluorophenyl)sulfonylhex-4-ynoic acid Chemical compound CC#CCC(CC#CC)(C(O)=O)S(=O)(=O)C1=CC=C(F)C=C1 OSPOQAOLEWBBCB-UHFFFAOYSA-N 0.000 description 1
TWKKCSYRCHZRKF-UHFFFAOYSA-N 2-but-2-ynyl-2-(4-methoxyphenyl)sulfonylhex-4-ynoic acid Chemical compound COC1=CC=C(S(=O)(=O)C(CC#CC)(CC#CC)C(O)=O)C=C1 TWKKCSYRCHZRKF-UHFFFAOYSA-N 0.000 description 1
UAAFWKTUBLOUQJ-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)-n-(pyridin-4-ylmethyl)ethanamine Chemical compound ClCCN(CCCl)CC1=CC=NC=C1 UAAFWKTUBLOUQJ-UHFFFAOYSA-N 0.000 description 1
AIIOOPQZGJBUBD-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)-n-[(3,4-dichlorophenyl)methyl]ethanamine Chemical compound ClCCN(CCCl)CC1=CC=C(Cl)C(Cl)=C1 AIIOOPQZGJBUBD-UHFFFAOYSA-N 0.000 description 1
NNBBBGITTCDWNO-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)-n-[(4-phenylphenyl)methyl]ethanamine Chemical compound C1=CC(CN(CCCl)CCCl)=CC=C1C1=CC=CC=C1 NNBBBGITTCDWNO-UHFFFAOYSA-N 0.000 description 1
125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
125000003858 2-ethylbutoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])O*)C([H])([H])C([H])([H])[H] 0.000 description 1
WJTZZPVVTSDNJJ-UHFFFAOYSA-N 2-fluorobenzenethiol Chemical compound FC1=CC=CC=C1S WJTZZPVVTSDNJJ-UHFFFAOYSA-N 0.000 description 1
SXGRNWLQHSCTJF-UHFFFAOYSA-N 2-hydroxy-3-methyl-2-(2-phenylethylsulfonyl)butanamide Chemical compound OC(C(=O)N)(C(C)C)S(=O)(=O)CCC1=CC=CC=C1 SXGRNWLQHSCTJF-UHFFFAOYSA-N 0.000 description 1
KIFPIAKBYOIOCS-UHFFFAOYSA-N 2-methyl-2-(trioxidanyl)propane Chemical compound CC(C)(C)OOO KIFPIAKBYOIOCS-UHFFFAOYSA-N 0.000 description 1
WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000005975 2-phenylethyloxy group Chemical group 0.000 description 1
VMKYTRPNOVFCGZ-UHFFFAOYSA-N 2-sulfanylphenol Chemical compound OC1=CC=CC=C1S VMKYTRPNOVFCGZ-UHFFFAOYSA-N 0.000 description 1
HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
UBCMNEHVLIOKGX-UHFFFAOYSA-N 3-(2-bromophenyl)-n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-methylpropanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(=O)NO)CC1=CC=CC=C1Br UBCMNEHVLIOKGX-UHFFFAOYSA-N 0.000 description 1
NNTUBMAVSSKQFE-UHFFFAOYSA-N 3-(4-bromophenyl)-n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-methylpropanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(=O)NO)CC1=CC=C(Br)C=C1 NNTUBMAVSSKQFE-UHFFFAOYSA-N 0.000 description 1
KKGUMGWNFARLSL-UHFFFAOYSA-N 3-(bromomethyl)pentane Chemical compound CCC(CC)CBr KKGUMGWNFARLSL-UHFFFAOYSA-N 0.000 description 1
YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
JHNIDEWPASZNEO-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)sulfonyl-2-methyldec-4-ynyl]pyridine Chemical compound FC1=CC=C(C=C1)S(=O)(=O)C(C)(CC#CCCCCC)CC=1C=NC=CC1 JHNIDEWPASZNEO-UHFFFAOYSA-N 0.000 description 1
LQQYSSZLIIRCCG-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)sulfonyl-2-methylhex-4-ynyl]pyridine Chemical compound CC#CCC(C)(CC1=CN=CC=C1)S(=O)(=O)C2=CC=C(C=C2)F LQQYSSZLIIRCCG-UHFFFAOYSA-N 0.000 description 1
WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
RZVCWKJZFNLOES-UHFFFAOYSA-N 3-[4-[3-[4-(3-chlorophenyl)piperazin-1-yl]propoxy]phenyl]-2-(4-methoxyphenyl)sulfonyl-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(O)=O)CC(C=C1)=CC=C1OCCCN1CCN(C=2C=C(Cl)C=CC=2)CC1 RZVCWKJZFNLOES-UHFFFAOYSA-N 0.000 description 1
NIDWUZTTXGJFNN-UHFFFAOYSA-N 3-bromopropoxybenzene Chemical compound BrCCCOC1=CC=CC=C1 NIDWUZTTXGJFNN-UHFFFAOYSA-N 0.000 description 1
VEUYFZWVWBJLBT-UHFFFAOYSA-N 3-cyclohexyl-n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-methylpropanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(=O)NO)CC1CCCCC1 VEUYFZWVWBJLBT-UHFFFAOYSA-N 0.000 description 1
125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
OFTGEOWUHYLWAW-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C(CCC)OC1=CC=C(C=C1)S(=O)(=O)C1(CCNCC1)C(=O)O OFTGEOWUHYLWAW-UHFFFAOYSA-N 0.000 description 1
AFXSLKKTDUYDIR-UHFFFAOYSA-N 4-(4-chlorophenoxy)benzenethiol Chemical compound C1=CC(S)=CC=C1OC1=CC=C(Cl)C=C1 AFXSLKKTDUYDIR-UHFFFAOYSA-N 0.000 description 1
ZHAJAVCIVZKBNX-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonyl-1-(naphthalen-1-ylmethyl)piperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C3=CC=CC=C3C=CC=2)CC1 ZHAJAVCIVZKBNX-UHFFFAOYSA-N 0.000 description 1
HEPMMSZVZIUOLG-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonyl-1-(naphthalen-2-ylmethyl)piperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=C3C=CC=CC3=CC=2)CC1 HEPMMSZVZIUOLG-UHFFFAOYSA-N 0.000 description 1
VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
XYWIPYBIIRTJMM-IBGZPJMESA-N 4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1-yl]butanoyl]amino]-2-fluorobenzamide Chemical compound CC[C@H](N1C=C(OC)C(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(N=N1)C(F)(F)F)C(=O)NC1=CC(F)=C(C=C1)C(N)=O XYWIPYBIIRTJMM-IBGZPJMESA-N 0.000 description 1
KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
QBLISOIWPZSVIK-UHFFFAOYSA-N 4-bromobutoxybenzene Chemical compound BrCCCCOC1=CC=CC=C1 QBLISOIWPZSVIK-UHFFFAOYSA-N 0.000 description 1
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
GUCPYIYFQVTFSI-UHFFFAOYSA-N 4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1 GUCPYIYFQVTFSI-UHFFFAOYSA-N 0.000 description 1
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
IKENFTDBHOMGEC-UHFFFAOYSA-N 5-(diaminomethylideneamino)-2-(3-fluorophenyl)sulfanyl-n-hydroxypentanamide Chemical compound NC(=N)NCCCC(C(=O)NO)SC1=CC=CC(F)=C1 IKENFTDBHOMGEC-UHFFFAOYSA-N 0.000 description 1
XSGVEJDBLQQXST-UHFFFAOYSA-N 5-chloro-1,3-dimethylpyrazole-4-sulfonic acid Chemical compound CC1=NN(C)C(Cl)=C1S(O)(=O)=O XSGVEJDBLQQXST-UHFFFAOYSA-N 0.000 description 1
QWZZUZAIHNZLEN-UHFFFAOYSA-N 5-pyridin-2-ylthiophene-2-sulfonic acid Chemical compound S1C(S(=O)(=O)O)=CC=C1C1=CC=CC=N1 QWZZUZAIHNZLEN-UHFFFAOYSA-N 0.000 description 1
IKRFDIBFCNTVCT-UHFFFAOYSA-N 6-(1,3-dioxoisoindol-2-yl)-2-(4-methoxyphenyl)sulfonyl-2-methylhexanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(O)=O)CCCCN1C(=O)C2=CC=CC=C2C1=O IKRFDIBFCNTVCT-UHFFFAOYSA-N 0.000 description 1
GAOHITDOPWCKCU-UHFFFAOYSA-N 6-(1,3-dioxoisoindol-2-yl)-n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-methylhexanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(=O)NO)CCCCN1C(=O)C2=CC=CC=C2C1=O GAOHITDOPWCKCU-UHFFFAOYSA-N 0.000 description 1
KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
WBDJYELCKVSSGT-UHFFFAOYSA-N 7-(bromomethyl)quinoline Chemical compound C1=CC=NC2=CC(CBr)=CC=C21 WBDJYELCKVSSGT-UHFFFAOYSA-N 0.000 description 1
HWTDMFJYBAURQR-UHFFFAOYSA-N 80-82-0 Chemical compound OS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O HWTDMFJYBAURQR-UHFFFAOYSA-N 0.000 description 1
ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
ZXMWDBUCKMTPFF-UHFFFAOYSA-N C(C)C(C(C(=O)O)(C)S(=O)(=O)C1=CC=C(C=C1)Br)C1=CC=C(C=C1)OCCN1CCCCC1 Chemical compound C(C)C(C(C(=O)O)(C)S(=O)(=O)C1=CC=C(C=C1)Br)C1=CC=C(C=C1)OCCN1CCCCC1 ZXMWDBUCKMTPFF-UHFFFAOYSA-N 0.000 description 1
HWLLNAPXEGQKJQ-UHFFFAOYSA-N C(C)C(C(C(=O)O)(CC1=CC=C(C=C1)OCCN1CCCCC1)S(=O)(=O)C1=CC=C(C=C1)OC)C Chemical compound C(C)C(C(C(=O)O)(CC1=CC=C(C=C1)OCCN1CCCCC1)S(=O)(=O)C1=CC=C(C=C1)OC)C HWLLNAPXEGQKJQ-UHFFFAOYSA-N 0.000 description 1
SWJJGNQVGDXXIF-UHFFFAOYSA-N C(C)C(C(C(=O)O)(CC=1C=NC=CC1)S(=O)(=O)C1=CC=C(C=C1)OC)C=C(C)C Chemical compound C(C)C(C(C(=O)O)(CC=1C=NC=CC1)S(=O)(=O)C1=CC=C(C=C1)OC)C=C(C)C SWJJGNQVGDXXIF-UHFFFAOYSA-N 0.000 description 1
DLAXBSCAAZQKFD-UHFFFAOYSA-N C(C)OC(C(C(C1=CC=C(C=C1)OCCN1CCCCC1)CC)(C)S(=O)(=O)C1=CC=C(C=C1)OCCCC)=O Chemical compound C(C)OC(C(C(C1=CC=C(C=C1)OCCN1CCCCC1)CC)(C)S(=O)(=O)C1=CC=C(C=C1)OCCCC)=O DLAXBSCAAZQKFD-UHFFFAOYSA-N 0.000 description 1
OIOTWEZJCVGELT-UHFFFAOYSA-N C(CCC)OC1=CC=C(C=C1)S(=O)(=O)C1(CCN(CC1)OCCC1=CC=CC=C1)C(=O)O Chemical compound C(CCC)OC1=CC=C(C=C1)S(=O)(=O)C1(CCN(CC1)OCCC1=CC=CC=C1)C(=O)O OIOTWEZJCVGELT-UHFFFAOYSA-N 0.000 description 1
VYOSEOZFDNAXHI-UHFFFAOYSA-N C(CCC)OC1=CC=C(C=C1)S(=O)(=O)C1N(CCC(C1)C(=O)O)CC1=CC=C(C=C1)C Chemical compound C(CCC)OC1=CC=C(C=C1)S(=O)(=O)C1N(CCC(C1)C(=O)O)CC1=CC=C(C=C1)C VYOSEOZFDNAXHI-UHFFFAOYSA-N 0.000 description 1
CJQCQJOMZFZDTK-UHFFFAOYSA-N CC(C(=O)O)(C)S(=O)(=O)C=1N(C=CN=1)C Chemical compound CC(C(=O)O)(C)S(=O)(=O)C=1N(C=CN=1)C CJQCQJOMZFZDTK-UHFFFAOYSA-N 0.000 description 1
HYWPYGJSNLWWBU-UHFFFAOYSA-N CC(C)N(CC1)CCC1S(C(C=C1)=CC=C1OC)(=O)=O.NO Chemical compound CC(C)N(CC1)CCC1S(C(C=C1)=CC=C1OC)(=O)=O.NO HYWPYGJSNLWWBU-UHFFFAOYSA-N 0.000 description 1
JZKMZGSPHZDIOD-UHFFFAOYSA-N CCC(C)(N)S(=O)(=O)C1=CC=C(C=C1)F Chemical compound CCC(C)(N)S(=O)(=O)C1=CC=C(C=C1)F JZKMZGSPHZDIOD-UHFFFAOYSA-N 0.000 description 1
IGDYDERGXQAPAD-UHFFFAOYSA-N CCOC(=O)C1CCN(Cc2ccccc2)C(C1)S(=O)(=O)c1ccc(OCc2ccccc2)cc1 Chemical compound CCOC(=O)C1CCN(Cc2ccccc2)C(C1)S(=O)(=O)c1ccc(OCc2ccccc2)cc1 IGDYDERGXQAPAD-UHFFFAOYSA-N 0.000 description 1
ZTJJLYPAQFQYKJ-UHFFFAOYSA-N COC(C=C1)=CC=C1S(N(CC1)CCC1C(O)=O)(=O)=O.NO Chemical compound COC(C=C1)=CC=C1S(N(CC1)CCC1C(O)=O)(=O)=O.NO ZTJJLYPAQFQYKJ-UHFFFAOYSA-N 0.000 description 1
PHLFQRUDPCQRJD-UHFFFAOYSA-N COC1=CC=C(C=C1)S(=O)(=O)C(C)(CCCC1=CC=CC=C1)CCCC1=CC=CC=C1 Chemical compound COC1=CC=C(C=C1)S(=O)(=O)C(C)(CCCC1=CC=CC=C1)CCCC1=CC=CC=C1 PHLFQRUDPCQRJD-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
RQXDAYJLMXDAST-UHFFFAOYSA-N ClC1=CC=C(OC2=CC=C(C=C2)S(=O)(=O)C2N(CCC(C2)C(=O)O)CC)C=C1 Chemical compound ClC1=CC=C(OC2=CC=C(C=C2)S(=O)(=O)C2N(CCC(C2)C(=O)O)CC)C=C1 RQXDAYJLMXDAST-UHFFFAOYSA-N 0.000 description 1
208000019399 Colonic disease Diseases 0.000 description 1
229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
208000016192 Demyelinating disease Diseases 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
241000282412 Homo Species 0.000 description 1
241000725303 Human immunodeficiency virus Species 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
238000006683 Mannich reaction Methods 0.000 description 1
102000001776 Matrix metalloproteinase-9 Human genes 0.000 description 1
102100030412 Matrix metalloproteinase-9 Human genes 0.000 description 1
102000010750 Metalloproteins Human genes 0.000 description 1
108010063312 Metalloproteins Proteins 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical class SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
FEYNFHSRETUBEM-UHFFFAOYSA-N N-[3-(1,1-difluoroethyl)phenyl]-1-(4-methoxyphenyl)-3-methyl-5-oxo-4H-pyrazole-4-carboxamide Chemical compound COc1ccc(cc1)N1N=C(C)C(C(=O)Nc2cccc(c2)C(C)(F)F)C1=O FEYNFHSRETUBEM-UHFFFAOYSA-N 0.000 description 1
ZHIVFCBUNVHQGA-UHFFFAOYSA-N N-hydroxy-2-(3-methoxyphenyl)sulfinyldecanamide Chemical compound ONC(C(CCCCCCCC)S(=O)C1=CC(=CC=C1)OC)=O ZHIVFCBUNVHQGA-UHFFFAOYSA-N 0.000 description 1
UWRAMUADPXEDFD-UHFFFAOYSA-N N-hydroxy-2-(3-methoxyphenyl)sulfonyldecanamide Chemical compound ONC(C(CCCCCCCC)S(=O)(=O)C1=CC(=CC=C1)OC)=O UWRAMUADPXEDFD-UHFFFAOYSA-N 0.000 description 1
FVYATVQAWXJQMB-UHFFFAOYSA-N N-hydroxy-2-(4-methylsulfinylphenyl)sulfinyldecanamide Chemical compound ONC(C(CCCCCCCC)S(=O)C1=CC=C(C=C1)S(=O)C)=O FVYATVQAWXJQMB-UHFFFAOYSA-N 0.000 description 1
LZEVNCVTUAHOMO-UHFFFAOYSA-N N-hydroxy-2-(4-methylsulfonylphenyl)sulfonyldecanamide Chemical compound ONC(C(CCCCCCCC)S(=O)(=O)C1=CC=C(C=C1)S(=O)(=O)C)=O LZEVNCVTUAHOMO-UHFFFAOYSA-N 0.000 description 1
IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
AGCRNGOXVMVADH-UHFFFAOYSA-N OS(=O)(=O)C1(Cl)SC=CC1Br Chemical compound OS(=O)(=O)C1(Cl)SC=CC1Br AGCRNGOXVMVADH-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
208000037062 Polyps Diseases 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
239000004902 Softening Agent Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 description 1
SWEDAZLCYJDAGW-UHFFFAOYSA-N Thiophene-2-thiol Chemical compound SC1=CC=CS1 SWEDAZLCYJDAGW-UHFFFAOYSA-N 0.000 description 1
241000251539 Vertebrata <Metazoa> Species 0.000 description 1
LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
WVEWJGGCDDKWIM-UHFFFAOYSA-N [4-[1-(hydroxyamino)-1-oxooctan-2-yl]sulfanylphenyl] benzenesulfonate Chemical compound C1=CC(SC(CCCCCC)C(=O)NO)=CC=C1OS(=O)(=O)C1=CC=CC=C1 WVEWJGGCDDKWIM-UHFFFAOYSA-N 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 description 1
229960001171 acetohydroxamic acid Drugs 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000003302 alkenyloxy group Chemical group 0.000 description 1
125000005133 alkynyloxy group Chemical group 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004421 aryl sulphonamide group Chemical group 0.000 description 1
AMEDKBHURXXSQO-UHFFFAOYSA-N azonous acid Chemical compound ONO AMEDKBHURXXSQO-UHFFFAOYSA-N 0.000 description 1
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 0.000 description 1
KQHLPMCNDYYZMB-UHFFFAOYSA-N chloromethylbenzene;hydrochloride Chemical compound Cl.ClCC1=CC=CC=C1 KQHLPMCNDYYZMB-UHFFFAOYSA-N 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
210000004087 cornea Anatomy 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
MYUWZTRYQGERCY-UHFFFAOYSA-N deca-2,6-diene Chemical compound CCCC=CCCC=CC MYUWZTRYQGERCY-UHFFFAOYSA-N 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
CXQRZKIIGJLWPJ-UHFFFAOYSA-N diphenylphosphane;1-naphthalen-1-ylnaphthalene Chemical group C=1C=CC=CC=1PC1=CC=CC=C1.C1=CC=C2C(C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 CXQRZKIIGJLWPJ-UHFFFAOYSA-N 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
230000004064 dysfunction Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
VYSOLLIIQRANQY-UHFFFAOYSA-N ethyl 1-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1S(=O)(=O)C1=CC=C(OC)C=C1 VYSOLLIIQRANQY-UHFFFAOYSA-N 0.000 description 1
RGPVWHXPNBITTA-UHFFFAOYSA-N ethyl 1-[(3-methoxyphenyl)methyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CC1=CC=CC(OC)=C1 RGPVWHXPNBITTA-UHFFFAOYSA-N 0.000 description 1
LYLYNHJJCZKNAF-UHFFFAOYSA-N ethyl 1-[(4-bromophenyl)methyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CC1=CC=C(Br)C=C1 LYLYNHJJCZKNAF-UHFFFAOYSA-N 0.000 description 1
JAVMYQBDIKNJKN-UHFFFAOYSA-N ethyl 1-[(4-fluorophenyl)methyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CC1=CC=C(F)C=C1 JAVMYQBDIKNJKN-UHFFFAOYSA-N 0.000 description 1
YRXBNIRWFMHAMS-UHFFFAOYSA-N ethyl 1-[(4-methoxyphenyl)methyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CC1=CC=C(OC)C=C1 YRXBNIRWFMHAMS-UHFFFAOYSA-N 0.000 description 1
RNUGWNKLIKCKOV-UHFFFAOYSA-N ethyl 1-[2-(4-methoxyphenyl)ethyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CCC1=CC=C(OC)C=C1 RNUGWNKLIKCKOV-UHFFFAOYSA-N 0.000 description 1
MVWUKKXTCAGNNJ-UHFFFAOYSA-N ethyl 1-[[4-(4-methoxyphenyl)sulfonylnaphthalen-1-yl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1=CC=C(S(=O)(=O)C=2C=CC(OC)=CC=2)C2=CC=CC=C12 MVWUKKXTCAGNNJ-UHFFFAOYSA-N 0.000 description 1
TXQUFLGNWCZQMN-UHFFFAOYSA-N ethyl 1-benzyl-4-(4-phenylmethoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)CCN1CC1=CC=CC=C1 TXQUFLGNWCZQMN-UHFFFAOYSA-N 0.000 description 1
RWOMYWIVLFLSRW-UHFFFAOYSA-N ethyl 1-benzyl-4-[4-(2-ethylbutoxy)phenyl]sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OCC(CC)CC)=CC=2)CCN1CC1=CC=CC=C1 RWOMYWIVLFLSRW-UHFFFAOYSA-N 0.000 description 1
FLHXAGJEFNGPIJ-UHFFFAOYSA-N ethyl 1-benzyl-4-[4-(3-methylbutoxy)phenyl]sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OCCC(C)C)=CC=2)CCN1CC1=CC=CC=C1 FLHXAGJEFNGPIJ-UHFFFAOYSA-N 0.000 description 1
ZHXQPJIOBXPJAI-UHFFFAOYSA-N ethyl 1-benzyl-4-[4-(4-chlorophenoxy)phenyl]sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC=3C=CC(Cl)=CC=3)=CC=2)CCN1CC1=CC=CC=C1 ZHXQPJIOBXPJAI-UHFFFAOYSA-N 0.000 description 1
FVNQRHTZLGYVPB-UHFFFAOYSA-N ethyl 1-butyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C1CN(CCCC)CCC1(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 FVNQRHTZLGYVPB-UHFFFAOYSA-N 0.000 description 1
MJTSJHUOKOJUMA-UHFFFAOYSA-N ethyl 1-butyl-4-[4-(3-methylbutoxy)phenyl]sulfonylpiperidine-4-carboxylate Chemical compound C1CN(CCCC)CCC1(C(=O)OCC)S(=O)(=O)C1=CC=C(OCCC(C)C)C=C1 MJTSJHUOKOJUMA-UHFFFAOYSA-N 0.000 description 1
YGXWWBWXUAITAS-UHFFFAOYSA-N ethyl 1-butyl-4-[4-(4-chlorophenoxy)phenyl]sulfonylpiperidine-4-carboxylate Chemical compound C1CN(CCCC)CCC1(C(=O)OCC)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 YGXWWBWXUAITAS-UHFFFAOYSA-N 0.000 description 1
DLPWYTBVPJZYDY-UHFFFAOYSA-N ethyl 2-(2-methylfuran-3-yl)sulfanylpropanoate Chemical compound CCOC(=O)C(C)SC=1C=COC=1C DLPWYTBVPJZYDY-UHFFFAOYSA-N 0.000 description 1
DVTWAYDUKSKNND-UHFFFAOYSA-N ethyl 2-(4-bromophenyl)sulfonyl-2-methyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanoate Chemical compound C=1C=C(Br)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCCCC1 DVTWAYDUKSKNND-UHFFFAOYSA-N 0.000 description 1
XGGLBNSAOMPWEP-UHFFFAOYSA-N ethyl 2-(4-butoxyphenyl)sulfonyl-2-methyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanoate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCCCC1 XGGLBNSAOMPWEP-UHFFFAOYSA-N 0.000 description 1
WWMRWDDKNBRMSU-UHFFFAOYSA-N ethyl 2-(4-butoxyphenyl)sulfonylacetate Chemical compound CCCCOC1=CC=C(S(=O)(=O)CC(=O)OCC)C=C1 WWMRWDDKNBRMSU-UHFFFAOYSA-N 0.000 description 1
NTORWPCYEHSJES-UHFFFAOYSA-N ethyl 2-(4-ethoxyphenyl)sulfanylpropanoate Chemical compound CCOC(=O)C(C)SC1=CC=C(OCC)C=C1 NTORWPCYEHSJES-UHFFFAOYSA-N 0.000 description 1
GBNSJAOQMFHMGD-UHFFFAOYSA-N ethyl 2-(4-fluorophenyl)sulfanyloctanoate Chemical compound CCCCCCC(C(=O)OCC)SC1=CC=C(F)C=C1 GBNSJAOQMFHMGD-UHFFFAOYSA-N 0.000 description 1
ORJYHHCCMHGXMH-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfanyl-2-methyl-3-phenylpropanoate Chemical compound C=1C=C(OC)C=CC=1SC(C)(C(=O)OCC)CC1=CC=CC=C1 ORJYHHCCMHGXMH-UHFFFAOYSA-N 0.000 description 1
PYQGMWISPUMMGX-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfanylbutanoate Chemical compound CCOC(=O)C(CC)SC1=CC=C(OC)C=C1 PYQGMWISPUMMGX-UHFFFAOYSA-N 0.000 description 1
ZNGFQHMFLDYWDH-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-1-[(4-phenylphenyl)methyl]piperidine-4-carboxylate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C1CC(C(=O)OCC)CCN1CC(C=C1)=CC=C1C1=CC=CC=C1 ZNGFQHMFLDYWDH-UHFFFAOYSA-N 0.000 description 1
TVEDWNPEBHXGTP-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2,5,9-trimethyldeca-4,8-dienoate Chemical compound CC(C)=CCCC(C)=CCC(C)(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 TVEDWNPEBHXGTP-UHFFFAOYSA-N 0.000 description 1
VGCXAPCFWLAJSG-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-[[4-(2-morpholin-4-ylethoxy)phenyl]methyl]butanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CC)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCOCC1 VGCXAPCFWLAJSG-UHFFFAOYSA-N 0.000 description 1
HGRJJLCHBYPBJH-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]butanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CC)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCCCC1 HGRJJLCHBYPBJH-UHFFFAOYSA-N 0.000 description 1
KPLAHYNVDLMTEM-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-quinolin-6-ylpropanoate Chemical compound C=1C=C2N=CC=CC2=CC=1CC(C)(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 KPLAHYNVDLMTEM-UHFFFAOYSA-N 0.000 description 1
LGIKDVVXIPXGCQ-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-methyl-5-phenylpent-4-enoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC=CC1=CC=CC=C1 LGIKDVVXIPXGCQ-UHFFFAOYSA-N 0.000 description 1
UCUDPTXNCBOBMW-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-3-methylbutanoate Chemical compound CCOC(=O)C(C(C)C)S(=O)(=O)C1=CC=C(OC)C=C1 UCUDPTXNCBOBMW-UHFFFAOYSA-N 0.000 description 1
FHBZHQBXIAQDPX-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-4-methyl-2-(pyridin-3-ylmethyl)pentanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CC(C)C)(C(=O)OCC)CC1=CC=CN=C1 FHBZHQBXIAQDPX-UHFFFAOYSA-N 0.000 description 1
GJIDIAMNHVTXST-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-5,9-dimethyl-2-[[4-(2-morpholin-4-ylethoxy)phenyl]methyl]deca-4,8-dienoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CC=C(C)CCC=C(C)C)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCOCC1 GJIDIAMNHVTXST-UHFFFAOYSA-N 0.000 description 1
JOMQHYMCOSSKMB-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-5-methyl-2-(3-methylbut-2-enyl)hex-4-enoate Chemical compound CCOC(=O)C(CC=C(C)C)(CC=C(C)C)S(=O)(=O)C1=CC=C(OC)C=C1 JOMQHYMCOSSKMB-UHFFFAOYSA-N 0.000 description 1
QFTQYBHPTTWRHL-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-5-methyl-2-(pyridin-3-ylmethyl)hexanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCC(C)C)(C(=O)OCC)CC1=CC=CN=C1 QFTQYBHPTTWRHL-UHFFFAOYSA-N 0.000 description 1
CVMMCZUHOVXNPK-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-5-methyl-2-[[4-(2-morpholin-4-ylethoxy)phenyl]methyl]hex-4-enoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CC=C(C)C)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCOCC1 CVMMCZUHOVXNPK-UHFFFAOYSA-N 0.000 description 1
GOSIRUVUSZAKHO-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-5-methylhexanoate Chemical compound CCOC(=O)C(CCC(C)C)S(=O)(=O)C1=CC=C(OC)C=C1 GOSIRUVUSZAKHO-UHFFFAOYSA-N 0.000 description 1
BNBVHXOVBNUHIU-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-5-phenyl-2-(3-phenylpropyl)pentanoate Chemical compound C=1C=CC=CC=1CCCC(S(=O)(=O)C=1C=CC(OC)=CC=1)(C(=O)OCC)CCCC1=CC=CC=C1 BNBVHXOVBNUHIU-UHFFFAOYSA-N 0.000 description 1
BWLSVHPFJJBRND-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-6-phenoxy-2-(pyridin-3-ylmethyl)hexanoate Chemical compound C=1C=CN=CC=1CC(S(=O)(=O)C=1C=CC(OC)=CC=1)(C(=O)OCC)CCCCOC1=CC=CC=C1 BWLSVHPFJJBRND-UHFFFAOYSA-N 0.000 description 1
UKTUZPXOLAKKJJ-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-6-phenoxyhexanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C(=O)OCC)CCCCOC1=CC=CC=C1 UKTUZPXOLAKKJJ-UHFFFAOYSA-N 0.000 description 1
QHHSTBCZKQFZRZ-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyldecanoate Chemical compound CCCCCCCCC(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 QHHSTBCZKQFZRZ-UHFFFAOYSA-N 0.000 description 1
VGSSBAYWKDGORZ-UHFFFAOYSA-N ethyl 2-[(4-methoxyphenyl)methylsulfonyl]propanoate Chemical compound CCOC(=O)C(C)S(=O)(=O)CC1=CC=C(OC)C=C1 VGSSBAYWKDGORZ-UHFFFAOYSA-N 0.000 description 1
LAKFTOVKYBHAHH-UHFFFAOYSA-N ethyl 2-[4-(4-chlorophenoxy)phenyl]sulfanylacetate Chemical compound C1=CC(SCC(=O)OCC)=CC=C1OC1=CC=C(Cl)C=C1 LAKFTOVKYBHAHH-UHFFFAOYSA-N 0.000 description 1
QKVULLBGMGCRRD-UHFFFAOYSA-N ethyl 2-[4-[(4-chlorophenyl)methoxy]phenyl]sulfonyl-1-[(4-methylphenyl)methyl]piperidine-4-carboxylate Chemical compound C=1C=C(OCC=2C=CC(Cl)=CC=2)C=CC=1S(=O)(=O)C1CC(C(=O)OCC)CCN1CC1=CC=C(C)C=C1 QKVULLBGMGCRRD-UHFFFAOYSA-N 0.000 description 1
MKPZXYFDALRGFA-UHFFFAOYSA-N ethyl 2-[4-[(4-chlorophenyl)methoxy]phenyl]sulfonylacetate Chemical compound C1=CC(S(=O)(=O)CC(=O)OCC)=CC=C1OCC1=CC=C(Cl)C=C1 MKPZXYFDALRGFA-UHFFFAOYSA-N 0.000 description 1
SNDUBMHWPXSPDW-UHFFFAOYSA-N ethyl 2-[8-(1-ethoxy-1-oxopropan-2-yl)sulfanyloctylsulfanyl]propanoate Chemical compound CCOC(=O)C(C)SCCCCCCCCSC(C)C(=O)OCC SNDUBMHWPXSPDW-UHFFFAOYSA-N 0.000 description 1
XWEJKPRYBSCRRP-UHFFFAOYSA-N ethyl 2-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-methoxyphenyl)sulfonylpentanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCC)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCCCCC1 XWEJKPRYBSCRRP-UHFFFAOYSA-N 0.000 description 1
DFDQUBGZZSOJCX-UHFFFAOYSA-N ethyl 2-[[4-[2-(diethylamino)ethoxy]phenyl]methyl]-2-(4-methoxyphenyl)sulfonylhexanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCCC)(C(=O)OCC)CC1=CC=C(OCCN(CC)CC)C=C1 DFDQUBGZZSOJCX-UHFFFAOYSA-N 0.000 description 1
XIMFCGSNSKXPBO-UHFFFAOYSA-N ethyl 2-bromobutanoate Chemical compound CCOC(=O)C(Br)CC XIMFCGSNSKXPBO-UHFFFAOYSA-N 0.000 description 1
GNCLPIAYAPQPOU-UHFFFAOYSA-N ethyl 2-bromoheptanoate Chemical compound CCCCCC(Br)C(=O)OCC GNCLPIAYAPQPOU-UHFFFAOYSA-N 0.000 description 1
ORSIRXYHFPHWTN-UHFFFAOYSA-N ethyl 2-bromopentanoate Chemical compound CCCC(Br)C(=O)OCC ORSIRXYHFPHWTN-UHFFFAOYSA-N 0.000 description 1
QGTKTXXIQKTTAO-UHFFFAOYSA-N ethyl 2-methyl-2-(1-methylimidazol-2-yl)sulfonyl-3-(4-phenylphenyl)propanoate Chemical compound N=1C=CN(C)C=1S(=O)(=O)C(C)(C(=O)OCC)CC(C=C1)=CC=C1C1=CC=CC=C1 QGTKTXXIQKTTAO-UHFFFAOYSA-N 0.000 description 1
ARXUZBQWANCFJB-UHFFFAOYSA-N ethyl 2-methyl-2-(2-methylfuran-3-yl)sulfonyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanoate Chemical compound C1=COC(C)=C1S(=O)(=O)C(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCCCC1 ARXUZBQWANCFJB-UHFFFAOYSA-N 0.000 description 1
XHIALPQJCIQCDL-UHFFFAOYSA-N ethyl 2-methyl-2-(2-methylfuran-3-yl)sulfonyl-3-phenylpropanoate Chemical compound C1=COC(C)=C1S(=O)(=O)C(C)(C(=O)OCC)CC1=CC=CC=C1 XHIALPQJCIQCDL-UHFFFAOYSA-N 0.000 description 1
JTSIFOFUGUMYKR-UHFFFAOYSA-N ethyl 2-octylsulfonyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanoate Chemical compound C1=CC(CC(S(=O)(=O)CCCCCCCC)C(=O)OCC)=CC=C1OCCN1CCCCC1 JTSIFOFUGUMYKR-UHFFFAOYSA-N 0.000 description 1
KVZUGUQIGQCTCH-UHFFFAOYSA-N ethyl 3-(4-bromophenyl)-2-(4-methoxyphenyl)sulfonyl-2-methylpropanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC1=CC=C(Br)C=C1 KVZUGUQIGQCTCH-UHFFFAOYSA-N 0.000 description 1
JHICSPPRRKHAAV-UHFFFAOYSA-N ethyl 3-[3-[2-(diethylamino)ethoxy]phenyl]-2-(4-methoxyphenyl)sulfonyl-2-methylpropanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC1=CC=CC(OCCN(CC)CC)=C1 JHICSPPRRKHAAV-UHFFFAOYSA-N 0.000 description 1
WNLFBMUVOBRWNX-UHFFFAOYSA-N ethyl 3-[4-[2-(azepan-1-yl)ethoxy]phenyl]-2-(4-methoxyphenyl)sulfonyl-2-methylpropanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCCCCC1 WNLFBMUVOBRWNX-UHFFFAOYSA-N 0.000 description 1
KSTIMHXGNFREQT-UHFFFAOYSA-N ethyl 3-[4-[3-[4-(3-chlorophenyl)piperazin-1-yl]propoxy]phenyl]-2-(4-methoxyphenyl)sulfonyl-2-methylpropanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCCN(CC1)CCN1C1=CC=CC(Cl)=C1 KSTIMHXGNFREQT-UHFFFAOYSA-N 0.000 description 1
CDQJTGRQQLBDSY-UHFFFAOYSA-N ethyl 3-cyclohexyl-2-(4-methoxyphenyl)sulfonyl-2-methylpropanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC1CCCCC1 CDQJTGRQQLBDSY-UHFFFAOYSA-N 0.000 description 1
GXRFWWPEFWDKPA-UHFFFAOYSA-N ethyl 3-cyclohexyl-2-(4-methoxyphenyl)sulfonylpropanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C(=O)OCC)CC1CCCCC1 GXRFWWPEFWDKPA-UHFFFAOYSA-N 0.000 description 1
KHHADIVHVMPMRM-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-(2-phenoxyethyl)piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CCOC=2C=CC=CC=2)CC1 KHHADIVHVMPMRM-UHFFFAOYSA-N 0.000 description 1
QQUKJPDPCXYTIS-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-(3-phenoxypropyl)piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CCCOC=2C=CC=CC=2)CC1 QQUKJPDPCXYTIS-UHFFFAOYSA-N 0.000 description 1
YHDSNDITVWJYJG-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-(pyridin-4-ylmethyl)piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CC=2C=CN=CC=2)CC1 YHDSNDITVWJYJG-UHFFFAOYSA-N 0.000 description 1
XPZYVFUYGHGSBW-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-[(3,4-dichlorophenyl)methyl]piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 XPZYVFUYGHGSBW-UHFFFAOYSA-N 0.000 description 1
NPVGYDOJJJMTIL-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-[(3-phenoxyphenyl)methyl]piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)CC1 NPVGYDOJJJMTIL-UHFFFAOYSA-N 0.000 description 1
BOZRNWRFPVETEO-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-[(4-cyanophenyl)methyl]piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CC=2C=CC(=CC=2)C#N)CC1 BOZRNWRFPVETEO-UHFFFAOYSA-N 0.000 description 1
CGTUSHQZZDHNDJ-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-[(4-fluorophenyl)methyl]piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CC=2C=CC(F)=CC=2)CC1 CGTUSHQZZDHNDJ-UHFFFAOYSA-N 0.000 description 1
HSTSPDIMHZEZDT-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-[(4-methoxyphenyl)methyl]piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CC=2C=CC(OC)=CC=2)CC1 HSTSPDIMHZEZDT-UHFFFAOYSA-N 0.000 description 1
RKGXYKXFAZIFTJ-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-(2-phenoxyethyl)piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CCOC1=CC=CC=C1 RKGXYKXFAZIFTJ-UHFFFAOYSA-N 0.000 description 1
ILOBLRACMDRJCE-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-(2-phenylethyl)piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CCC1=CC=CC=C1 ILOBLRACMDRJCE-UHFFFAOYSA-N 0.000 description 1
OBLAEDSPDBRSER-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-(3-methylbut-2-enyl)piperidine-4-carboxylate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C1(C(=O)OCC)CCN(CC=C(C)C)CC1 OBLAEDSPDBRSER-UHFFFAOYSA-N 0.000 description 1
XVOZQUFANNBYBM-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-(3-phenoxypropyl)piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CCCOC1=CC=CC=C1 XVOZQUFANNBYBM-UHFFFAOYSA-N 0.000 description 1
QJEGYSPYCYGEQL-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-(3-phenylpropyl)piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CCCC1=CC=CC=C1 QJEGYSPYCYGEQL-UHFFFAOYSA-N 0.000 description 1
QYDUOYPHBLLXOS-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-(naphthalen-1-ylmethyl)piperidine-4-carboxylate Chemical compound C1CN(CC=2C3=CC=CC=C3C=CC=2)CCC1(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 QYDUOYPHBLLXOS-UHFFFAOYSA-N 0.000 description 1
QXGVVHCUURXJMC-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-[(4-methylphenyl)methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CC1=CC=C(C)C=C1 QXGVVHCUURXJMC-UHFFFAOYSA-N 0.000 description 1
MFMDAOMSCGOFGX-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-[(4-phenylphenyl)methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CC(C=C1)=CC=C1C1=CC=CC=C1 MFMDAOMSCGOFGX-UHFFFAOYSA-N 0.000 description 1
HDAYJPWWFGOVSP-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-[(4-pyridin-2-ylphenyl)methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CC(C=C1)=CC=C1C1=CC=CC=N1 HDAYJPWWFGOVSP-UHFFFAOYSA-N 0.000 description 1
UZNSDBALZKRRBK-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-[(4-thiophen-2-ylphenyl)methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CC(C=C1)=CC=C1C1=CC=CS1 UZNSDBALZKRRBK-UHFFFAOYSA-N 0.000 description 1
VERVFCODAACEKU-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CC(C=C1)=CC=C1OCCN1CCCCC1 VERVFCODAACEKU-UHFFFAOYSA-N 0.000 description 1
AFNKMWNGHGDSID-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C1(C(=O)OCC)CCNCC1 AFNKMWNGHGDSID-UHFFFAOYSA-N 0.000 description 1
FXKFEHRDNSCQFF-UHFFFAOYSA-N ethyl 4-[4-(4-chlorophenoxy)phenyl]sulfonyl-1-ethylpiperidine-4-carboxylate Chemical compound C=1C=C(OC=2C=CC(Cl)=CC=2)C=CC=1S(=O)(=O)C1(C(=O)OCC)CCN(CC)CC1 FXKFEHRDNSCQFF-UHFFFAOYSA-N 0.000 description 1
RGZDGUMYXHVEJX-UHFFFAOYSA-N ethyl 4-[4-(4-chlorophenoxy)phenyl]sulfonyl-1-methylpiperidine-4-carboxylate Chemical compound C=1C=C(OC=2C=CC(Cl)=CC=2)C=CC=1S(=O)(=O)C1(C(=O)OCC)CCN(C)CC1 RGZDGUMYXHVEJX-UHFFFAOYSA-N 0.000 description 1
VIKWZSNGLQSSJM-UHFFFAOYSA-N ethyl 5-methyl-2-(3-methylbut-2-enyl)-2-(4-methylphenyl)sulfonylhex-4-enoate Chemical compound CCOC(=O)C(CC=C(C)C)(CC=C(C)C)S(=O)(=O)C1=CC=C(C)C=C1 VIKWZSNGLQSSJM-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
RUJPPJYDHHAEEK-UHFFFAOYSA-N ethyl piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCNCC1 RUJPPJYDHHAEEK-UHFFFAOYSA-N 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007850 fluorescent dye Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000005558 fluorometry Methods 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
230000012010 growth Effects 0.000 description 1
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
208000017169 kidney disease Diseases 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000003446 ligand Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
ZAHQPTJLOCWVPG-UHFFFAOYSA-N mitoxantrone dihydrochloride Chemical compound Cl.Cl.O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO ZAHQPTJLOCWVPG-UHFFFAOYSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
MGVAVXGWLUOGLG-UHFFFAOYSA-N n,n'-dihydroxy-2-(4-methylsulfinylphenyl)sulfinylpentanediamide Chemical compound CS(=O)C1=CC=C(S(=O)C(CCC(=O)NO)C(=O)NO)C=C1 MGVAVXGWLUOGLG-UHFFFAOYSA-N 0.000 description 1
XRWPKBLJNUBIFB-UHFFFAOYSA-N n,n'-dihydroxy-2-(4-methylsulfonylphenyl)sulfonylpentanediamide Chemical compound CS(=O)(=O)C1=CC=C(S(=O)(=O)C(CCC(=O)NO)C(=O)NO)C=C1 XRWPKBLJNUBIFB-UHFFFAOYSA-N 0.000 description 1
XPBUQQUWTDGVHD-UHFFFAOYSA-N n,n'-dihydroxy-2-[2-(trifluoromethyl)phenyl]sulfinylpentanediamide Chemical compound ONC(=O)CCC(C(=O)NO)S(=O)C1=CC=CC=C1C(F)(F)F XPBUQQUWTDGVHD-UHFFFAOYSA-N 0.000 description 1
OJCMONYVYWSBNZ-UHFFFAOYSA-N n,n'-dihydroxy-2-[2-(trifluoromethyl)phenyl]sulfonylpentanediamide Chemical compound ONC(=O)CCC(C(=O)NO)S(=O)(=O)C1=CC=CC=C1C(F)(F)F OJCMONYVYWSBNZ-UHFFFAOYSA-N 0.000 description 1
BSXSSXPCEVBUSF-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-2-methylpropan-2-amine Chemical compound ClCCN(C(C)(C)C)CCCl BSXSSXPCEVBUSF-UHFFFAOYSA-N 0.000 description 1
WAEDMQMDOHQPFL-UHFFFAOYSA-N n,n-bis(2-chloroethyl)propan-2-amine Chemical compound ClCCN(C(C)C)CCCl WAEDMQMDOHQPFL-UHFFFAOYSA-N 0.000 description 1
WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
IUSXYVRFJVAVOB-UHFFFAOYSA-N n-(2-chloroethyl)-n-propan-2-ylpropan-2-amine;hydron;chloride Chemical compound Cl.CC(C)N(C(C)C)CCCl IUSXYVRFJVAVOB-UHFFFAOYSA-N 0.000 description 1
FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
UPSFMJHZUCSEHU-JYGUBCOQSA-N n-[(2s,3r,4r,5s,6r)-2-[(2r,3s,4r,5r,6s)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-(4-methyl-2-oxochromen-7-yl)oxyoxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide Chemical compound CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](O)[C@@H](NC(C)=O)[C@H](OC=2C=C3OC(=O)C=C(C)C3=CC=2)O[C@@H]1CO UPSFMJHZUCSEHU-JYGUBCOQSA-N 0.000 description 1
NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
QZXOLBPUAUOQFB-UHFFFAOYSA-N n-decanohydroxamic acid Chemical compound CCCCCCCCCC(=O)NO QZXOLBPUAUOQFB-UHFFFAOYSA-N 0.000 description 1
VDUIPQNXOQMTBF-UHFFFAOYSA-N n-ethylhydroxylamine Chemical compound CCNO VDUIPQNXOQMTBF-UHFFFAOYSA-N 0.000 description 1
JDBZPFDHILZVMS-UHFFFAOYSA-N n-hydroxy-2-(1,3-thiazol-2-ylsulfanyl)octanamide Chemical compound CCCCCCC(C(=O)NO)SC1=NC=CS1 JDBZPFDHILZVMS-UHFFFAOYSA-N 0.000 description 1
DDFSFSDYLWXPAF-UHFFFAOYSA-N n-hydroxy-2-(1,3-thiazol-2-ylsulfonyl)octanamide Chemical compound CCCCCCC(C(=O)NO)S(=O)(=O)C1=NC=CS1 DDFSFSDYLWXPAF-UHFFFAOYSA-N 0.000 description 1
RSUOYSNSNOUQFB-UHFFFAOYSA-N n-hydroxy-2-(1-methyltetrazol-5-yl)sulfanyloctanamide Chemical compound CCCCCCC(C(=O)NO)SC1=NN=NN1C RSUOYSNSNOUQFB-UHFFFAOYSA-N 0.000 description 1
NWZFKMCHAJILHU-UHFFFAOYSA-N n-hydroxy-2-(1h-imidazol-2-ylsulfonyl)octanamide Chemical compound CCCCCCC(C(=O)NO)S(=O)(=O)C1=NC=CN1 NWZFKMCHAJILHU-UHFFFAOYSA-N 0.000 description 1
HLPBCUXWMIRHSQ-UHFFFAOYSA-N n-hydroxy-2-(2-methoxyphenyl)sulfonyl-2-methyl-3-quinolin-6-ylpropanamide Chemical compound COC1=CC=CC=C1S(=O)(=O)C(C)(C(=O)NO)CC1=CC=C(N=CC=C2)C2=C1 HLPBCUXWMIRHSQ-UHFFFAOYSA-N 0.000 description 1
UYRKQYNGYQFLJL-UHFFFAOYSA-N n-hydroxy-2-(2-pyrazin-2-ylethylsulfanyl)octanamide Chemical compound CCCCCCC(C(=O)NO)SCCC1=CN=CC=N1 UYRKQYNGYQFLJL-UHFFFAOYSA-N 0.000 description 1
JPRIDKAVKYIEIP-UHFFFAOYSA-N n-hydroxy-2-(2-pyrazin-2-ylethylsulfinyl)octanamide Chemical compound CCCCCCC(C(=O)NO)S(=O)CCC1=CN=CC=N1 JPRIDKAVKYIEIP-UHFFFAOYSA-N 0.000 description 1
ZYDUHOCHTWXDPX-UHFFFAOYSA-N n-hydroxy-2-(2-pyridin-2-ylethylsulfanyl)octanamide Chemical compound CCCCCCC(C(=O)NO)SCCC1=CC=CC=N1 ZYDUHOCHTWXDPX-UHFFFAOYSA-N 0.000 description 1
YUSIUFHLYNRBEB-UHFFFAOYSA-N n-hydroxy-2-(3-methoxyphenyl)sulfinyloctanamide Chemical compound CCCCCCC(C(=O)NO)S(=O)C1=CC=CC(OC)=C1 YUSIUFHLYNRBEB-UHFFFAOYSA-N 0.000 description 1
CRJSUIVJUVYXCX-UHFFFAOYSA-N n-hydroxy-2-(3-methoxyphenyl)sulfonyloctanamide Chemical compound CCCCCCC(C(=O)NO)S(=O)(=O)C1=CC=CC(OC)=C1 CRJSUIVJUVYXCX-UHFFFAOYSA-N 0.000 description 1
DFWBWMNHDXAVAH-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfinyl-2,5-dimethylhex-4-enamide Chemical compound COC1=CC=C(S(=O)C(C)(CC=C(C)C)C(=O)NO)C=C1 DFWBWMNHDXAVAH-UHFFFAOYSA-N 0.000 description 1
MTEROOWGBSMTDB-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfinyl-2-methyl-3-phenylpropanamide Chemical compound C1=CC(OC)=CC=C1S(=O)C(C)(C(=O)NO)CC1=CC=CC=C1 MTEROOWGBSMTDB-UHFFFAOYSA-N 0.000 description 1
QUGKMHUIONNUMG-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfinyl-2-phenylacetamide Chemical compound C1=CC(OC)=CC=C1S(=O)C(C(=O)NO)C1=CC=CC=C1 QUGKMHUIONNUMG-UHFFFAOYSA-N 0.000 description 1
YTDUUOPZJXARAS-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfinyl-3-methylbutanamide Chemical compound COC1=CC=C(S(=O)C(C(C)C)C(=O)NO)C=C1 YTDUUOPZJXARAS-UHFFFAOYSA-N 0.000 description 1
RIVOYEWDLKWMKH-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfinylheptanamide Chemical compound CCCCCC(C(=O)NO)S(=O)C1=CC=C(OC)C=C1 RIVOYEWDLKWMKH-UHFFFAOYSA-N 0.000 description 1
COEXRWHXVMMHEF-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2,5-dimethylhex-4-enamide Chemical compound COC1=CC=C(S(=O)(=O)C(C)(CC=C(C)C)C(=O)NO)C=C1 COEXRWHXVMMHEF-UHFFFAOYSA-N 0.000 description 1
IQNGGJYKFADFHE-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-(pyridin-3-ylmethyl)decanamide Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCCCCCCC)(C(=O)NO)CC1=CC=CN=C1 IQNGGJYKFADFHE-UHFFFAOYSA-N 0.000 description 1
RKPWDSLUQARCLB-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-methyl-3-(4-phenylphenyl)propanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(=O)NO)CC1=CC=C(C=2C=CC=CC=2)C=C1 RKPWDSLUQARCLB-UHFFFAOYSA-N 0.000 description 1
NWDBGCMSHBZFFJ-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-methyl-3-[4-(2-morpholin-4-ylethoxy)phenyl]propanamide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(=O)NO)CC(C=C1)=CC=C1OCCN1CCOCC1 NWDBGCMSHBZFFJ-UHFFFAOYSA-N 0.000 description 1
FLIOXLIZONFFSH-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-methyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(=O)NO)CC(C=C1)=CC=C1OCCN1CCCCC1 FLIOXLIZONFFSH-UHFFFAOYSA-N 0.000 description 1
XBLZKAPRZBJHCZ-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-methyl-3-phenylpropanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(=O)NO)CC1=CC=CC=C1 XBLZKAPRZBJHCZ-UHFFFAOYSA-N 0.000 description 1
BCVFMUCILNFXOC-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-methyl-3-pyridin-3-ylpropanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(=O)NO)CC1=CC=CN=C1 BCVFMUCILNFXOC-UHFFFAOYSA-N 0.000 description 1
GKWXVMYDVAXVEF-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-methyl-3-quinolin-6-ylpropanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(=O)NO)CC1=CC=C(N=CC=C2)C2=C1 GKWXVMYDVAXVEF-UHFFFAOYSA-N 0.000 description 1
BKJCTJQMBGJOHN-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-methyl-5-phenylpent-4-enamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(=O)NO)CC=CC1=CC=CC=C1 BKJCTJQMBGJOHN-UHFFFAOYSA-N 0.000 description 1
FQZUGHBEAWJYRZ-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-propylpentanamide Chemical compound CCCC(CCC)(C(=O)NO)S(=O)(=O)C1=CC=C(OC)C=C1 FQZUGHBEAWJYRZ-UHFFFAOYSA-N 0.000 description 1
JRBJMWFZOMECPK-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-3-naphthalen-2-ylpropanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(=O)NO)CC1=CC=C(C=CC=C2)C2=C1 JRBJMWFZOMECPK-UHFFFAOYSA-N 0.000 description 1
OQOVBCVMAHMMFY-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-4-methyl-2-(pyridin-3-ylmethyl)pentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CC(C)C)(C(=O)NO)CC1=CC=CN=C1 OQOVBCVMAHMMFY-UHFFFAOYSA-N 0.000 description 1
JGDVFBCMNUSQQW-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-5-methyl-2-(pyridin-3-ylmethyl)hexanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CCC(C)C)(C(=O)NO)CC1=CC=CN=C1 JGDVFBCMNUSQQW-UHFFFAOYSA-N 0.000 description 1
DODOCMXWIUOVJX-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-5-phenyl-2-(3-phenylpropyl)pentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(=O)NO)(CCCC=1C=CC=CC=1)CCCC1=CC=CC=C1 DODOCMXWIUOVJX-UHFFFAOYSA-N 0.000 description 1
CVQGLQDQQVXYAT-UHFFFAOYSA-N n-hydroxy-2-(4-methylsulfonylphenyl)sulfonyl-3-phenylmethoxypropanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1S(=O)(=O)C(C(=O)NO)COCC1=CC=CC=C1 CVQGLQDQQVXYAT-UHFFFAOYSA-N 0.000 description 1
JFAFATACGNKIJM-UHFFFAOYSA-N n-hydroxy-2-(4-pentan-3-yloxyphenyl)sulfinyloctanamide Chemical compound CCCCCCC(C(=O)NO)S(=O)C1=CC=C(OC(CC)CC)C=C1 JFAFATACGNKIJM-UHFFFAOYSA-N 0.000 description 1
YITBEBNXOHDRAM-UHFFFAOYSA-N n-hydroxy-2-(4-pentan-3-yloxyphenyl)sulfonyloctanamide Chemical compound CCCCCCC(C(=O)NO)S(=O)(=O)C1=CC=C(OC(CC)CC)C=C1 YITBEBNXOHDRAM-UHFFFAOYSA-N 0.000 description 1
ATDVPCQYGXTQBN-UHFFFAOYSA-N n-hydroxy-2-(4-phenylmethoxyphenyl)sulfinyloctanamide Chemical compound C1=CC(S(=O)C(C(=O)NO)CCCCCC)=CC=C1OCC1=CC=CC=C1 ATDVPCQYGXTQBN-UHFFFAOYSA-N 0.000 description 1
XUWJGANKJSKJAH-UHFFFAOYSA-N n-hydroxy-2-(4-phenylmethoxyphenyl)sulfonyloctanamide Chemical compound C1=CC(S(=O)(=O)C(C(=O)NO)CCCCCC)=CC=C1OCC1=CC=CC=C1 XUWJGANKJSKJAH-UHFFFAOYSA-N 0.000 description 1
RVGRIAWOPGUMKO-UHFFFAOYSA-N n-hydroxy-2-(4-piperazin-1-ylphenyl)sulfanyloctanamide Chemical compound C1=CC(SC(CCCCCC)C(=O)NO)=CC=C1N1CCNCC1 RVGRIAWOPGUMKO-UHFFFAOYSA-N 0.000 description 1
GHTHIVSFWAUUSM-UHFFFAOYSA-N n-hydroxy-2-(4-piperidin-1-ylphenyl)sulfanyloctanamide Chemical compound C1=CC(SC(CCCCCC)C(=O)NO)=CC=C1N1CCCCC1 GHTHIVSFWAUUSM-UHFFFAOYSA-N 0.000 description 1
ZJVIWJCJWJGELB-UHFFFAOYSA-N n-hydroxy-2-[(2-phenyl-1,5-dihydrotetrazol-5-yl)sulfanyl]octanamide Chemical compound N1=NC(SC(CCCCCC)C(=O)NO)NN1C1=CC=CC=C1 ZJVIWJCJWJGELB-UHFFFAOYSA-N 0.000 description 1
BMICLZKZJLHGMA-UHFFFAOYSA-N n-hydroxy-2-[(4-phenyl-1,3-thiazol-2-yl)sulfinyl]octanamide Chemical compound S1C(S(=O)C(C(=O)NO)CCCCCC)=NC(C=2C=CC=CC=2)=C1 BMICLZKZJLHGMA-UHFFFAOYSA-N 0.000 description 1
ORCYENKSKPIJKT-UHFFFAOYSA-N n-hydroxy-2-[(4-phenyl-1,3-thiazol-2-yl)sulfonyl]octanamide Chemical compound S1C(S(=O)(=O)C(C(=O)NO)CCCCCC)=NC(C=2C=CC=CC=2)=C1 ORCYENKSKPIJKT-UHFFFAOYSA-N 0.000 description 1
XUEMDSZUAOKJNU-UHFFFAOYSA-N n-hydroxy-2-[1-(hydroxyamino)-1-oxopropan-2-yl]sulfinylbutanamide Chemical compound ONC(=O)C(CC)S(=O)C(C)C(=O)NO XUEMDSZUAOKJNU-UHFFFAOYSA-N 0.000 description 1
SCNASWNOMZFWFR-UHFFFAOYSA-N n-hydroxy-2-[1-(hydroxyamino)-1-oxopropan-2-yl]sulfonylbutanamide Chemical compound ONC(=O)C(CC)S(=O)(=O)C(C)C(=O)NO SCNASWNOMZFWFR-UHFFFAOYSA-N 0.000 description 1
BRDFQWVNHICTCA-UHFFFAOYSA-N n-hydroxy-2-[2-(hydroxyamino)-2-oxoethyl]sulfinylbutanamide Chemical compound ONC(=O)C(CC)S(=O)CC(=O)NO BRDFQWVNHICTCA-UHFFFAOYSA-N 0.000 description 1
DSQIGWHUCNZAKE-UHFFFAOYSA-N n-hydroxy-2-[2-(hydroxyamino)-2-oxoethyl]sulfonylbutanamide Chemical compound ONC(=O)C(CC)S(=O)(=O)CC(=O)NO DSQIGWHUCNZAKE-UHFFFAOYSA-N 0.000 description 1
NZJCWCZQXSFQQA-UHFFFAOYSA-N n-hydroxy-2-[2-(naphthalen-2-ylamino)-2-oxoethyl]sulfinyloctanamide Chemical compound C1=CC=CC2=CC(NC(=O)CS(=O)C(C(=O)NO)CCCCCC)=CC=C21 NZJCWCZQXSFQQA-UHFFFAOYSA-N 0.000 description 1
FBMCJNUHXKCSCJ-UHFFFAOYSA-N n-hydroxy-2-[2-(naphthalen-2-ylamino)-2-oxoethyl]sulfonyloctanamide Chemical compound C1=CC=CC2=CC(NC(=O)CS(=O)(=O)C(C(=O)NO)CCCCCC)=CC=C21 FBMCJNUHXKCSCJ-UHFFFAOYSA-N 0.000 description 1
AAOVCBAIZQUXKD-UHFFFAOYSA-N n-hydroxy-2-[4-(1-methylpyrrolidin-3-yl)oxyphenyl]sulfinyloctanamide Chemical compound C1=CC(S(=O)C(C(=O)NO)CCCCCC)=CC=C1OC1CN(C)CC1 AAOVCBAIZQUXKD-UHFFFAOYSA-N 0.000 description 1
YLASBSNUPYVMEQ-UHFFFAOYSA-N n-hydroxy-2-[4-(1-methylpyrrolidin-3-yl)oxyphenyl]sulfonyloctanamide Chemical compound C1=CC(S(=O)(=O)C(C(=O)NO)CCCCCC)=CC=C1OC1CN(C)CC1 YLASBSNUPYVMEQ-UHFFFAOYSA-N 0.000 description 1
LJPNTVGHOBFGHR-UHFFFAOYSA-N n-hydroxy-2-[4-(4-phenylanilino)phenyl]sulfanyloctanamide Chemical compound C1=CC(SC(CCCCCC)C(=O)NO)=CC=C1NC1=CC=C(C=2C=CC=CC=2)C=C1 LJPNTVGHOBFGHR-UHFFFAOYSA-N 0.000 description 1
CAMCEGLCWROVFX-UHFFFAOYSA-N n-hydroxy-2-[4-(5-hydroxypentoxy)phenyl]sulfanyloctanamide Chemical compound CCCCCCC(C(=O)NO)SC1=CC=C(OCCCCCO)C=C1 CAMCEGLCWROVFX-UHFFFAOYSA-N 0.000 description 1
QIFULEGINIBOAT-UHFFFAOYSA-N n-hydroxy-2-[4-(methylamino)phenyl]sulfanyloctanamide Chemical compound CCCCCCC(C(=O)NO)SC1=CC=C(NC)C=C1 QIFULEGINIBOAT-UHFFFAOYSA-N 0.000 description 1
ZODMYSMYLISANM-UHFFFAOYSA-N n-hydroxy-2-[4-(oxan-4-yloxy)phenyl]sulfinyloctanamide Chemical compound C1=CC(S(=O)C(C(=O)NO)CCCCCC)=CC=C1OC1CCOCC1 ZODMYSMYLISANM-UHFFFAOYSA-N 0.000 description 1
BJXDDLJFSHASCD-UHFFFAOYSA-N n-hydroxy-2-[4-(oxan-4-yloxy)phenyl]sulfonyloctanamide Chemical compound C1=CC(S(=O)(=O)C(C(=O)NO)CCCCCC)=CC=C1OC1CCOCC1 BJXDDLJFSHASCD-UHFFFAOYSA-N 0.000 description 1
TUZMTMXICDZUAB-UHFFFAOYSA-N n-hydroxy-2-[4-(pyridin-4-ylamino)phenyl]sulfanyloctanamide Chemical compound C1=CC(SC(CCCCCC)C(=O)NO)=CC=C1NC1=CC=NC=C1 TUZMTMXICDZUAB-UHFFFAOYSA-N 0.000 description 1
OHNPXPQCDVYDOB-UHFFFAOYSA-N n-hydroxy-2-[4-[3-(hydroxyamino)-3-oxopropyl]phenyl]sulfanyloctanamide Chemical compound CCCCCCC(C(=O)NO)SC1=CC=C(CCC(=O)NO)C=C1 OHNPXPQCDVYDOB-UHFFFAOYSA-N 0.000 description 1
AUUDHKOJTVCXGR-UHFFFAOYSA-N n-hydroxy-2-[4-[3-(hydroxyamino)-3-oxopropyl]phenyl]sulfinyloctanamide Chemical compound CCCCCCC(C(=O)NO)S(=O)C1=CC=C(CCC(=O)NO)C=C1 AUUDHKOJTVCXGR-UHFFFAOYSA-N 0.000 description 1
RGFDHMCFPXELKG-UHFFFAOYSA-N n-hydroxy-2-[4-[3-(hydroxyamino)-3-oxopropyl]phenyl]sulfonyloctanamide Chemical compound CCCCCCC(C(=O)NO)S(=O)(=O)C1=CC=C(CCC(=O)NO)C=C1 RGFDHMCFPXELKG-UHFFFAOYSA-N 0.000 description 1
PUMCJYPQOYYIEI-UHFFFAOYSA-N n-hydroxy-2-methyl-2-(2-methylfuran-3-yl)sulfonyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanamide Chemical compound O1C=CC(S(=O)(=O)C(C)(CC=2C=CC(OCCN3CCCCC3)=CC=2)C(=O)NO)=C1C PUMCJYPQOYYIEI-UHFFFAOYSA-N 0.000 description 1
RKIZMUFFMJZJRN-UHFFFAOYSA-N n-hydroxy-2-methyl-2-(2-methylfuran-3-yl)sulfonyl-3-phenylpropanamide Chemical compound O1C=CC(S(=O)(=O)C(C)(CC=2C=CC=CC=2)C(=O)NO)=C1C RKIZMUFFMJZJRN-UHFFFAOYSA-N 0.000 description 1
UQRFKNRXERPSMG-UHFFFAOYSA-N n-hydroxy-2-methyl-3-phenyl-2-thiophen-2-ylsulfonylpropanamide Chemical compound C=1C=CSC=1S(=O)(=O)C(C)(C(=O)NO)CC1=CC=CC=C1 UQRFKNRXERPSMG-UHFFFAOYSA-N 0.000 description 1
CWXNXJRSSOOPNY-UHFFFAOYSA-N n-hydroxy-2-quinolin-8-ylsulfinyloctanamide Chemical compound C1=CN=C2C(S(=O)C(C(=O)NO)CCCCCC)=CC=CC2=C1 CWXNXJRSSOOPNY-UHFFFAOYSA-N 0.000 description 1
ISTRJSYDFPPITG-UHFFFAOYSA-N n-hydroxy-2-quinolin-8-ylsulfonyloctanamide Chemical compound C1=CN=C2C(S(=O)(=O)C(C(=O)NO)CCCCCC)=CC=CC2=C1 ISTRJSYDFPPITG-UHFFFAOYSA-N 0.000 description 1
AOGGDPHYERJBGZ-UHFFFAOYSA-N n-hydroxy-3-[1-(hydroxyamino)-1-oxooctan-2-yl]sulfanylbenzamide Chemical compound CCCCCCC(C(=O)NO)SC1=CC=CC(C(=O)NO)=C1 AOGGDPHYERJBGZ-UHFFFAOYSA-N 0.000 description 1
SOLFZTBOKBMGDD-UHFFFAOYSA-N n-hydroxy-3-[1-(hydroxyamino)-1-oxooctan-2-yl]sulfinylbenzamide Chemical compound CCCCCCC(C(=O)NO)S(=O)C1=CC=CC(C(=O)NO)=C1 SOLFZTBOKBMGDD-UHFFFAOYSA-N 0.000 description 1
GGHCMTJYXVEWQW-UHFFFAOYSA-N n-hydroxy-3-[1-(hydroxyamino)-1-oxooctan-2-yl]sulfonylbenzamide Chemical compound CCCCCCC(C(=O)NO)S(=O)(=O)C1=CC=CC(C(=O)NO)=C1 GGHCMTJYXVEWQW-UHFFFAOYSA-N 0.000 description 1
XRWYYNZMAFDZQC-UHFFFAOYSA-N n-hydroxy-3-methyl-2-(2-phenylethylsulfinyl)butanamide Chemical compound ONC(=O)C(C(C)C)S(=O)CCC1=CC=CC=C1 XRWYYNZMAFDZQC-UHFFFAOYSA-N 0.000 description 1
KASLMAICRUMQME-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-(2-phenylethyl)piperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CCC=2C=CC=CC=2)CC1 KASLMAICRUMQME-UHFFFAOYSA-N 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
210000000440 neutrophil Anatomy 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
239000012057 packaged powder Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000007170 pathology Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
MLBYLEUJXUBIJJ-UHFFFAOYSA-N pent-4-ynoic acid Chemical compound OC(=O)CCC#C MLBYLEUJXUBIJJ-UHFFFAOYSA-N 0.000 description 1
125000001151 peptidyl group Chemical group 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
230000002028 premature Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
230000004044 response Effects 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000010532 solid phase synthesis reaction Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
JTWYSFPLDMDKPI-UHFFFAOYSA-N tert-butyl 2-(4-methoxyphenyl)sulfanylacetate Chemical compound COC1=CC=C(SCC(=O)OC(C)(C)C)C=C1 JTWYSFPLDMDKPI-UHFFFAOYSA-N 0.000 description 1
GCTZGHQUKIXIIW-UHFFFAOYSA-N tert-butyl 2-(4-methoxyphenyl)sulfonyl-2-(pyridin-3-ylmethyl)dec-4-ynoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CC#CCCCCC)(C(=O)OC(C)(C)C)CC1=CC=CN=C1 GCTZGHQUKIXIIW-UHFFFAOYSA-N 0.000 description 1
KKRUUXQZHGTFAQ-UHFFFAOYSA-N tert-butyl 2-(4-methoxyphenyl)sulfonyl-2-(pyridin-3-ylmethyl)pent-4-ynoate Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CC#C)(C(=O)OC(C)(C)C)CC1=CC=CN=C1 KKRUUXQZHGTFAQ-UHFFFAOYSA-N 0.000 description 1
AAHCHGSSMIHBBV-UHFFFAOYSA-N tert-butyl 2-(4-methoxyphenyl)sulfonyl-2-prop-2-ynylpent-4-ynoate Chemical compound COC1=CC=C(S(=O)(=O)C(CC#C)(CC#C)C(=O)OC(C)(C)C)C=C1 AAHCHGSSMIHBBV-UHFFFAOYSA-N 0.000 description 1
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
VYAWPZHEABFHTG-UHFFFAOYSA-N tert-butyl 2-but-2-ynyl-2-(4-fluorophenyl)sulfonylhex-4-ynoate Chemical compound CC#CCC(CC#CC)(C(=O)OC(C)(C)C)S(=O)(=O)C1=CC=C(F)C=C1 VYAWPZHEABFHTG-UHFFFAOYSA-N 0.000 description 1
DZXVGGJGUXNTTB-UHFFFAOYSA-N tert-butyl 2-but-2-ynyl-2-(4-methoxyphenyl)sulfonylhex-4-ynoate Chemical compound COC1=CC=C(S(=O)(=O)C(CC#CC)(CC#CC)C(=O)OC(C)(C)C)C=C1 DZXVGGJGUXNTTB-UHFFFAOYSA-N 0.000 description 1
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000009261 transgenic effect Effects 0.000 description 1
SANWDQJIWZEKOD-UHFFFAOYSA-N tributyl(furan-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CO1 SANWDQJIWZEKOD-UHFFFAOYSA-N 0.000 description 1
GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
- C07C239/14—Hydroxylamino compounds or their ethers or esters having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/54—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Endocrinology (AREA)
Oncology (AREA)
Hematology (AREA)
Heart & Thoracic Surgery (AREA)
Dermatology (AREA)
Cardiology (AREA)
Orthopedic Medicine & Surgery (AREA)
Urology & Nephrology (AREA)
Virology (AREA)
Tropical Medicine & Parasitology (AREA)
Gastroenterology & Hepatology (AREA)
Communicable Diseases (AREA)
Pain & Pain Management (AREA)
AIDS & HIV (AREA)
Ophthalmology & Optometry (AREA)
Obesity (AREA)
Emergency Medicine (AREA)
Immunology (AREA)
Vascular Medicine (AREA)
Gynecology & Obstetrics (AREA)
Pregnancy & Childbirth (AREA)
Reproductive Health (AREA)

SK1233-2000A 1998-02-19 1998-08-26 N-hydroxy-2-(alkyl, aryl alebo heteroaryl sulfanyl, sulfinyl alebo sulfonyl)-3-substituované-alkyl, aryl alebo heteroarylamidy, farmaceutický prostriedok s ich obsahom a ich použitie SK12332000A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US2637298A	1998-02-19	1998-02-19
PCT/US1998/017633 WO1999042436A1 (en)	1998-02-19	1998-08-26	N-hydroxy-2-(alkyl, aryl, or heteroaryl sulfanyl, sulfinyl or sulfonyl)-3-substituted-alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors

Publications (1)

Publication Number	Publication Date
SK12332000A3 true SK12332000A3 (sk)	2001-02-12

Family

ID=21831431

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1233-2000A SK12332000A3 (sk)	1998-02-19	1998-08-26	N-hydroxy-2-(alkyl, aryl alebo heteroaryl sulfanyl, sulfinyl alebo sulfonyl)-3-substituované-alkyl, aryl alebo heteroarylamidy, farmaceutický prostriedok s ich obsahom a ich použitie

Country Status (21)

Country	Link
EP (1)	EP1054858A1 (id)
JP (1)	JP2002503717A (id)
KR (1)	KR20010041089A (id)
CN (1)	CN1213021C (id)
AU (1)	AU757719B2 (id)
BG (1)	BG104782A (id)
BR (1)	BR9815781A (id)
CA (1)	CA2320469A1 (id)
EA (1)	EA003283B1 (id)
EE (1)	EE200000471A (id)
GE (1)	GEP20022797B (id)
HR (1)	HRP20000543A2 (id)
HU (1)	HUP0101837A3 (id)
ID (1)	ID25639A (id)
IL (1)	IL137566A0 (id)
NO (1)	NO20004093L (id)
NZ (1)	NZ506184A (id)
PL (1)	PL342548A1 (id)
SK (1)	SK12332000A3 (id)
TR (1)	TR200002423T2 (id)
WO (1)	WO1999042436A1 (id)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1042290A1 (en)	1997-11-14	2000-10-11	G.D. SEARLE & CO.	Aromatic sulfone hydroxamic acid metalloprotease inhibitor
US20010039287A1 (en)	1997-11-14	2001-11-08	Thomas E Barta	Aromatic sulfone hydroxamic acid metalloprotease inhibitor
US6750228B1 (en) *	1997-11-14	2004-06-15	Pharmacia Corporation	Aromatic sulfone hydroxamic acid metalloprotease inhibitor
US7045519B2 (en)	1998-06-19	2006-05-16	Chiron Corporation	Inhibitors of glycogen synthase kinase 3
AR035312A1 (es) *	1999-01-27	2004-05-12	Wyeth Corp	Compuestos de acido hidroxamico que contienen alquinilo como inhibidores de metaloproteinasa de matriz/tace, composicion farmaceutica que los comprenden y el uso de los mismos para la manufactura de un medicamento
CN1178915C (zh) *	1999-01-27	2004-12-08	惠氏控股有限公司	含有炔基的异羟肟酸衍生物、其制备及其作为基质金属蛋白酶抑制剂/TNF-α转变酶抑制剂的用途
PL350193A1 (en)	1999-02-08	2002-11-18	Searle & Co	Sulfamato hydroxamic acid metalloprotease inhibitor
US6800646B1 (en)	1999-02-08	2004-10-05	Pharmacia Corporation	Sulfamato hydroxamic acid metalloprotease inhibitor
WO2001055112A1 (en) *	2000-01-27	2001-08-02	American Cyanamid Company	Method for preparing alpha-sulfonyl hydroxamic acid derivatives
US20020002152A1 (en)	2000-04-14	2002-01-03	Craig Richard A.	Hydrazide and alkoxyamide angiogenesis inhibitors
UY26664A1 (es) *	2000-04-14	2001-11-30	Abbott Lab	Hidrazidas y alcoxiamidas inhibidoras de la angiogénesis.
US6683093B2 (en)	2000-05-12	2004-01-27	Pharmacia Corporation	Aromatic sulfone hydroxamic acids and their use as protease inhibitors
US6689794B2 (en)	2001-05-11	2004-02-10	Pharmacia Corporation	Aromatic sulfone hydroxamates and their use as protease inhibitors
PE20030701A1 (es)	2001-12-20	2003-08-21	Schering Corp	Compuestos para el tratamiento de trastornos inflamatorios
AU2003221786A1 (en)	2002-04-25	2003-11-10	Pharmacia Corporation	Piperidinyl-and piperazinyl-sulfonylmethyl hydroxamic acids and their use as protease inhibitors
WO2004000811A1 (en) *	2002-06-25	2003-12-31	Pharmacia Corporation	Arylsulfonylhydroxamic acid and amide derivatives and their use as protease inhibitors
TW200418825A (en)	2002-12-16	2004-10-01	Hoffmann La Roche	Novel (R)-and (S) enantiomers of thiophene hydroxamic acid derivatives
WO2006050053A2 (en) *	2004-11-01	2006-05-11	Nuada, Llc	Compounds and methods of use thereof
FR2917427B1 (fr) *	2007-06-18	2009-08-21	Galderma Res & Dev	Inhibiteurs de tace dans le traitement de l'acne
FR2947268B1 (fr) *	2009-06-30	2011-08-26	Galderma Res & Dev	Nouveaux composes benzene-sulfonamides, leur procede de synthese et leur utilisation en medecine ainsi qu'en cosmetique
AU2013292076B2 (en) *	2012-07-18	2017-02-23	Proyecto De Biomedicina Cima, S.L.	New antifibrinolytic compounds
KR101641023B1 (ko) *	2014-08-27	2016-07-20	씨제이헬스케어 주식회사	신규한 아미노-페닐-설포닐-아세테이트 유도체 및 이의 용도
WO2016032120A1 (ko) *	2014-08-27	2016-03-03	씨제이헬스케어 주식회사	신규한 아미노-페닐-설포닐-아세테이트 유도체 및 이의 용도
CN107188837B (zh) *	2017-06-06	2019-05-28	温州大学	一种α-酰基高烯丙基硫醚类化合物的合成方法
AU2019352741A1 (en)	2018-10-04	2021-05-06	Assistance Publique-Hôpitaux De Paris (Aphp)	EGFR inhibitors for treating keratodermas

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8827305D0 (en) *	1988-11-23	1988-12-29	British Bio Technology	Compounds
US5455258A (en) *	1993-01-06	1995-10-03	Ciba-Geigy Corporation	Arylsulfonamido-substituted hydroxamic acids
US5506242A (en) *	1993-01-06	1996-04-09	Ciba-Geigy Corporation	Arylsufonamido-substituted hydroxamic acids
US5902791A (en) *	1994-01-22	1999-05-11	British Biotech Pharmaceuticals Limited	Metalloproteinase inhibitors
JPH10501806A (ja) *	1994-06-22	1998-02-17	ブリティッシュバイオテックファーマシューティカルズリミテッド	金属タンパク質分解酵素阻害剤
EE04295B1 (et) *	1997-02-27	2004-06-15	American Cyanamid Company	N-hüdroksü-2-(alküül-, arüül- või heteroarüülsulfanüül-, -sulfinüül- või-sulfonüül-)-3-asendatud-alküülamiidid, -arüülamiidid või -heteroarüülamiididkui maatriksmetalloproteinaasi inhibiitorid
JPH11199512A (ja) *	1997-10-24	1999-07-27	Pfizer Prod Inc	変形性関節症および他のｍｍｐ媒介疾患の治療のためのｍｍｐ−１３選択的阻害剤の使用
EP1042290A1 (en) *	1997-11-14	2000-10-11	G.D. SEARLE & CO.	Aromatic sulfone hydroxamic acid metalloprotease inhibitor

1998
- 1998-08-26 BR BR9815781-7A patent/BR9815781A/pt not_active Application Discontinuation
- 1998-08-26 HU HU0101837A patent/HUP0101837A3/hu unknown
- 1998-08-26 KR KR1020007009128A patent/KR20010041089A/ko not_active Withdrawn
- 1998-08-26 CN CNB988139669A patent/CN1213021C/zh not_active Expired - Fee Related
- 1998-08-26 ID IDW20001549A patent/ID25639A/id unknown
- 1998-08-26 WO PCT/US1998/017633 patent/WO1999042436A1/en not_active Ceased
- 1998-08-26 NZ NZ506184A patent/NZ506184A/en unknown
- 1998-08-26 AU AU91201/98A patent/AU757719B2/en not_active Ceased
- 1998-08-26 JP JP2000532389A patent/JP2002503717A/ja active Pending
- 1998-08-26 HR HR20000543A patent/HRP20000543A2/hr not_active Application Discontinuation
- 1998-08-26 GE GEAP19985554A patent/GEP20022797B/en unknown
- 1998-08-26 IL IL13756698A patent/IL137566A0/xx unknown
- 1998-08-26 TR TR2000/02423T patent/TR200002423T2/xx unknown
- 1998-08-26 EA EA200000849A patent/EA003283B1/ru not_active IP Right Cessation
- 1998-08-26 SK SK1233-2000A patent/SK12332000A3/sk unknown
- 1998-08-26 PL PL98342548A patent/PL342548A1/xx unknown
- 1998-08-26 EE EEP200000471A patent/EE200000471A/xx unknown
- 1998-08-26 CA CA002320469A patent/CA2320469A1/en not_active Abandoned
- 1998-08-26 EP EP98943392A patent/EP1054858A1/en not_active Withdrawn
2000
- 2000-08-16 NO NO20004093A patent/NO20004093L/no unknown
- 2000-09-19 BG BG104782A patent/BG104782A/bg unknown

Also Published As

Publication number	Publication date
AU9120198A (en)	1999-09-06
NZ506184A (en)	2003-05-30
HUP0101837A2 (hu)	2001-10-28
BR9815781A (pt)	2000-11-07
IL137566A0 (en)	2001-07-24
TR200002423T2 (tr)	2001-01-22
HRP20000543A2 (en)	2001-08-31
GEP20022797B (en)	2002-09-25
NO20004093L (no)	2000-10-03
WO1999042436A1 (en)	1999-08-26
KR20010041089A (ko)	2001-05-15
JP2002503717A (ja)	2002-02-05
EA200000849A1 (ru)	2001-04-23
EE200000471A (et)	2002-02-15
CN1213021C (zh)	2005-08-03
ID25639A (id)	2000-10-19
AU757719B2 (en)	2003-03-06
BG104782A (bg)	2001-08-31
EA003283B1 (ru)	2003-04-24
NO20004093D0 (no)	2000-08-16
PL342548A1 (en)	2001-06-18
EP1054858A1 (en)	2000-11-29
CA2320469A1 (en)	1999-08-26
CN1291183A (zh)	2001-04-11
HUP0101837A3 (en)	2001-11-28

Publication	Publication Date	Title
SK12332000A3 (sk)	2001-02-12	N-hydroxy-2-(alkyl, aryl alebo heteroaryl sulfanyl, sulfinyl alebo sulfonyl)-3-substituované-alkyl, aryl alebo heteroarylamidy, farmaceutický prostriedok s ich obsahom a ich použitie
EP0970046B1 (en)	2003-12-10	N-hydroxy-2-(alkyl, aryl, or heteroaryl sulfanyl, sulfinyl or sulfonyl)-3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors
US6288086B1 (en)	2001-09-11	N-hydroxy-2-(alkyl, aryl, or heteroaryl, sulfanyl, sulfinyl or sulfonyl)-3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors
US6342508B1 (en)	2002-01-29	N-hydroxy-2-(Alkyl,Aryl or Heteroaryl sulfanyl, sulfinyl or sulfonyl) 3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors
CZ306099A3 (cs)	2000-04-12	Inhibitory metalloproteinázy
CZ20003036A3 (cs)	2001-03-14	Inhibitory metaloproteinázy matrice
CZ305999A3 (cs)	2000-03-15	Inhibitory metalloproteinázy
MXPA00008095A (en)	2002-03-26	N-hydroxy-2-(alkyl, aryl, or heteroaryl sulfanyl, sulfinyl or sulfonyl)-3-substituted-alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors