BG103757A - N-хидрокси-2-/алкил,арил или хетероарил сулфанил,сулфинил или сулфонил/-3-заместени алкил, арил или хетероариламиди като инхибитори на матрична металопротеиназа - Google Patents
N-хидрокси-2-/алкил,арил или хетероарил сулфанил,сулфинил или сулфонил/-3-заместени алкил, арил или хетероариламиди като инхибитори на матрична металопротеиназа Download PDFInfo
- Publication number
- BG103757A BG103757A BG103757A BG10375799A BG103757A BG 103757 A BG103757 A BG 103757A BG 103757 A BG103757 A BG 103757A BG 10375799 A BG10375799 A BG 10375799A BG 103757 A BG103757 A BG 103757A
- Authority
- BG
- Bulgaria
- Prior art keywords
- alkyl
- optionally substituted
- selected independently
- groups selected
- aryl
- Prior art date
Links
- -1 sulphanyl- Chemical group 0.000 title claims description 371
- 125000001072 heteroaryl group Chemical group 0.000 title claims description 91
- 239000003771 matrix metalloproteinase inhibitor Substances 0.000 title description 4
- 229940121386 matrix metalloproteinase inhibitor Drugs 0.000 title description 4
- 125000005418 aryl aryl group Chemical group 0.000 title 1
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 77
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 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 abstract description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 6
- 201000010099 disease Diseases 0.000 claims abstract description 6
- 208000031886 HIV Infections Diseases 0.000 claims abstract description 4
- 206010027476 Metastases Diseases 0.000 claims abstract description 4
- 230000029663 wound healing Effects 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 234
- 125000004432 carbon atom Chemical group C* 0.000 claims description 137
- 125000003118 aryl group Chemical group 0.000 claims description 101
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 95
- 229910052760 oxygen Inorganic materials 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- 125000005842 heteroatom Chemical group 0.000 claims description 64
- 125000001624 naphthyl group Chemical group 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 125000003342 alkenyl group Chemical group 0.000 claims description 35
- 125000000304 alkynyl group Chemical group 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 229920006395 saturated elastomer Polymers 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 125000002619 bicyclic group Chemical group 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- 102100031111 Disintegrin and metalloproteinase domain-containing protein 17 Human genes 0.000 claims description 27
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 102000002274 Matrix Metalloproteinases Human genes 0.000 claims description 17
- 108010000684 Matrix Metalloproteinases Proteins 0.000 claims description 17
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
- 125000005530 alkylenedioxy 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
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 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
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 239000004305 biphenyl Substances 0.000 claims description 7
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 6
- 125000003435 aroyl group Chemical group 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 239000012528 membrane Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 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 claims description 5
- 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 claims description 5
- 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
- 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 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 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 5
- 125000006663 (C1-C6) perfluoroalkyl group Chemical group 0.000 claims description 4
- 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 claims description 4
- 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 claims description 4
- 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 claims description 4
- 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 claims description 4
- 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 claims description 4
- 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 claims description 4
- 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 claims description 4
- 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 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 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 claims 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 claims description 3
- 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 claims description 3
- 208000037357 HIV infectious disease Diseases 0.000 claims description 3
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 206010022489 Insulin Resistance Diseases 0.000 claims description 3
- 230000002159 abnormal effect Effects 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 230000006378 damage Effects 0.000 claims description 3
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 208000028169 periodontal disease Diseases 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 3
- 230000004614 tumor growth Effects 0.000 claims description 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 3
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 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 claims description 2
- NQFCYHRSEIIXDN-UHFFFAOYSA-N 4-(2-methoxyphenyl)sulfonyl-1-[(4-phenylphenyl)methyl]piperidine-4-carboxylic acid Chemical compound COC1=CC=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 NQFCYHRSEIIXDN-UHFFFAOYSA-N 0.000 claims description 2
- WBTLASDHZWDFMT-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonyl-2-methyl-1-naphthalen-2-ylpiperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(O)=O)CC(C)N(C=2C=C3C=CC=CC3=CC=2)CC1 WBTLASDHZWDFMT-UHFFFAOYSA-N 0.000 claims description 2
- 108091007505 ADAM17 Proteins 0.000 claims description 2
- 206010053555 Arthritis bacterial Diseases 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000020084 Bone disease Diseases 0.000 claims description 2
- 208000016192 Demyelinating disease Diseases 0.000 claims description 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 2
- 206010016654 Fibrosis Diseases 0.000 claims description 2
- 208000004575 Infectious Arthritis Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 201000002287 Keratoconus Diseases 0.000 claims description 2
- 208000029725 Metabolic bone disease Diseases 0.000 claims description 2
- 206010049088 Osteopenia Diseases 0.000 claims description 2
- 208000002158 Proliferative Vitreoretinopathy Diseases 0.000 claims description 2
- 206010038934 Retinopathy proliferative Diseases 0.000 claims description 2
- 206010040070 Septic Shock Diseases 0.000 claims description 2
- 206010064996 Ulcerative keratitis Diseases 0.000 claims description 2
- 230000033115 angiogenesis Effects 0.000 claims description 2
- 208000007474 aortic aneurysm Diseases 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 210000000845 cartilage Anatomy 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- 230000007882 cirrhosis Effects 0.000 claims description 2
- 208000019425 cirrhosis of liver 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
- 210000001503 joint Anatomy 0.000 claims description 2
- 208000017169 kidney disease Diseases 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 208000002780 macular degeneration Diseases 0.000 claims description 2
- 208000021971 neovascular inflammatory vitreoretinopathy Diseases 0.000 claims description 2
- 210000000653 nervous system Anatomy 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 230000002028 premature Effects 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
- 230000005070 ripening Effects 0.000 claims description 2
- 201000001223 septic arthritis Diseases 0.000 claims description 2
- 230000036303 septic shock Effects 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 230000000472 traumatic effect Effects 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 208000037260 Atherosclerotic Plaque Diseases 0.000 claims 2
- 231100000915 pathological change Toxicity 0.000 claims 2
- 230000036285 pathological change Effects 0.000 claims 2
- LMWYBBCWFRLALS-UHFFFAOYSA-N 3-methoxy-7-thiabicyclo[4.1.0]hepta-2,4-diene Chemical compound COC1=CC2C(C=C1)S2 LMWYBBCWFRLALS-UHFFFAOYSA-N 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000025985 Central nervous system inflammatory disease Diseases 0.000 claims 1
- 206010011017 Corneal graft rejection Diseases 0.000 claims 1
- 206010011091 Coronary artery thrombosis Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010029113 Neovascularisation Diseases 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 1
- 208000022531 anorexia Diseases 0.000 claims 1
- 208000002528 coronary thrombosis Diseases 0.000 claims 1
- 206010061428 decreased appetite Diseases 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 208000001491 myopia Diseases 0.000 claims 1
- 230000004379 myopia Effects 0.000 claims 1
- 201000001474 proteinuria Diseases 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 25
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract description 10
- 108090000765 processed proteins & peptides Proteins 0.000 abstract description 7
- 102000004190 Enzymes Human genes 0.000 abstract description 6
- 108090000790 Enzymes Proteins 0.000 abstract description 6
- 239000003112 inhibitor Substances 0.000 abstract description 4
- 206010003246 arthritis Diseases 0.000 abstract description 3
- 208000025865 Ulcer Diseases 0.000 abstract description 2
- 206010012601 diabetes mellitus Diseases 0.000 abstract description 2
- 230000036269 ulceration Effects 0.000 abstract description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 abstract 2
- 102000004877 Insulin Human genes 0.000 abstract 1
- 108090001061 Insulin Proteins 0.000 abstract 1
- 102000005741 Metalloproteases Human genes 0.000 abstract 1
- 108010006035 Metalloproteases Proteins 0.000 abstract 1
- HPNSNYBUADCFDR-UHFFFAOYSA-N chromafenozide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3CCCOC3=CC=2)C)C(C)(C)C)=C1 HPNSNYBUADCFDR-UHFFFAOYSA-N 0.000 abstract 1
- 229940125396 insulin Drugs 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 366
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 240
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 237
- 239000007787 solid Substances 0.000 description 210
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 186
- 239000011541 reaction mixture Substances 0.000 description 168
- 239000011347 resin Substances 0.000 description 132
- 229920005989 resin Polymers 0.000 description 132
- 238000007429 general method Methods 0.000 description 95
- 239000003921 oil Substances 0.000 description 91
- 235000019198 oils Nutrition 0.000 description 90
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 76
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 75
- 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 61
- 239000000047 product Substances 0.000 description 56
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 54
- 239000000203 mixture Substances 0.000 description 50
- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 43
- 239000012230 colorless oil Substances 0.000 description 41
- 239000000243 solution Substances 0.000 description 41
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 39
- 239000002253 acid Substances 0.000 description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 34
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 33
- 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 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 26
- 239000000843 powder Substances 0.000 description 26
- 230000005764 inhibitory process Effects 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 24
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 23
- 229940092714 benzenesulfonic acid Drugs 0.000 description 23
- 238000002844 melting Methods 0.000 description 23
- 101000777461 Homo sapiens Disintegrin and metalloproteinase domain-containing protein 17 Proteins 0.000 description 22
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 22
- 229940080818 propionamide Drugs 0.000 description 22
- 102100027995 Collagenase 3 Human genes 0.000 description 21
- 101000577887 Homo sapiens Collagenase 3 Proteins 0.000 description 21
- RGUVUPQQFXCJFC-UHFFFAOYSA-N n-hydroxyoctanamide Chemical compound CCCCCCCC(=O)NO RGUVUPQQFXCJFC-UHFFFAOYSA-N 0.000 description 21
- 239000004743 Polypropylene Substances 0.000 description 20
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 20
- 229920001155 polypropylene Polymers 0.000 description 20
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 19
- 235000019260 propionic acid Nutrition 0.000 description 19
- 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 19
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 18
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 18
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 18
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 18
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 18
- 235000009518 sodium iodide Nutrition 0.000 description 18
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 17
- 229940043237 diethanolamine Drugs 0.000 description 17
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- 230000003647 oxidation Effects 0.000 description 15
- 238000007254 oxidation reaction Methods 0.000 description 15
- 239000007858 starting material Substances 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 13
- 238000010647 peptide synthesis reaction Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 150000001649 bromium compounds Chemical class 0.000 description 12
- 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 12
- 239000007788 liquid Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 238000006467 substitution reaction Methods 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 150000003462 sulfoxides Chemical class 0.000 description 12
- NIFAOMSJMGEFTQ-UHFFFAOYSA-N 4-methoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1 NIFAOMSJMGEFTQ-UHFFFAOYSA-N 0.000 description 11
- 102000000380 Matrix Metalloproteinase 1 Human genes 0.000 description 11
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 102100030412 Matrix metalloproteinase-9 Human genes 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 229940073608 benzyl chloride Drugs 0.000 description 10
- 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 10
- 150000003840 hydrochlorides Chemical class 0.000 description 10
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 102000013382 Gelatinases Human genes 0.000 description 9
- 108010026132 Gelatinases Proteins 0.000 description 9
- 101000990902 Homo sapiens Matrix metalloproteinase-9 Proteins 0.000 description 9
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 9
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 9
- 239000012442 inert solvent Substances 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 8
- 101001013150 Homo sapiens Interstitial collagenase Proteins 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 238000003756 stirring Methods 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
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 102000029816 Collagenase Human genes 0.000 description 6
- 108060005980 Collagenase Proteins 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- CVXCWPZVOYBWOJ-UHFFFAOYSA-N 1-[2-[4-(chloromethyl)phenoxy]ethyl]piperidine Chemical compound C1=CC(CCl)=CC=C1OCCN1CCCCC1 CVXCWPZVOYBWOJ-UHFFFAOYSA-N 0.000 description 5
- JVDWKJQBWSKJOJ-UHFFFAOYSA-N 1-bromo-3-methylbuta-1,3-diene Chemical compound CC(=C)C=CBr JVDWKJQBWSKJOJ-UHFFFAOYSA-N 0.000 description 5
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 5
- 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 5
- OKIHXNKYYGUVTE-UHFFFAOYSA-N 4-Fluorothiophenol Chemical compound FC1=CC=C(S)C=C1 OKIHXNKYYGUVTE-UHFFFAOYSA-N 0.000 description 5
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 5
- BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 5
- 102100040247 Tumor necrosis factor Human genes 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 229960002424 collagenase Drugs 0.000 description 5
- 229940088598 enzyme Drugs 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 159000000001 potassium salts Chemical class 0.000 description 5
- 239000012261 resinous substance Substances 0.000 description 5
- 239000011734 sodium Substances 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
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
- 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 4
- KYMOWQQIZINTJZ-UHFFFAOYSA-N 4-methylsulfanylbenzenethiol Chemical compound CSC1=CC=C(S)C=C1 KYMOWQQIZINTJZ-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- JIQJOKSCSVMZAN-UHFFFAOYSA-N ethyl 2-bromooctanoate Chemical compound CCCCCCC(Br)C(=O)OCC JIQJOKSCSVMZAN-UHFFFAOYSA-N 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-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
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 4
- SRJOCJYGOFTFLH-UHFFFAOYSA-M piperidine-4-carboxylate Chemical compound [O-]C(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 150000003457 sulfones Chemical class 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 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
- YLRBJYMANQKEAW-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)benzene Chemical compound BrCC1=CC=C(Br)C=C1 YLRBJYMANQKEAW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- 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 3
- 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 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
- RUHJZSZTSCSTCC-UHFFFAOYSA-N 2-(bromomethyl)naphthalene Chemical compound C1=CC=CC2=CC(CBr)=CC=C21 RUHJZSZTSCSTCC-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
- 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
- UEBARDWJXBGYEJ-UHFFFAOYSA-N 2-bromo-3-methylbutanoic acid Chemical compound CC(C)C(Br)C(O)=O UEBARDWJXBGYEJ-UHFFFAOYSA-N 0.000 description 3
- FBSPHFKZJKWNEC-UHFFFAOYSA-N 2-bromoethyl propanoate Chemical compound CCC(=O)OCCBr FBSPHFKZJKWNEC-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
- 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 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
- CNQCWYFDIQSALX-UHFFFAOYSA-N 3-(chloromethyl)pyridine Chemical compound ClCC1=CC=CN=C1 CNQCWYFDIQSALX-UHFFFAOYSA-N 0.000 description 3
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- FTBCOQFMQSTCQQ-UHFFFAOYSA-N 4-bromobenzenethiol Chemical compound SC1=CC=C(Br)C=C1 FTBCOQFMQSTCQQ-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- 108010016113 Matrix Metalloproteinase 1 Proteins 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- 239000012131 assay buffer Substances 0.000 description 3
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 231100000673 dose–response relationship Toxicity 0.000 description 3
- 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 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
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-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
- 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 3
- QLMPWDWLVIWORW-UHFFFAOYSA-N n-hydroxyheptanamide Chemical compound CCCCCCC(=O)NO QLMPWDWLVIWORW-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
- AVMHMVJVHYGDOO-NSCUHMNNSA-N (e)-1-bromobut-2-ene Chemical compound C\C=C\CBr AVMHMVJVHYGDOO-NSCUHMNNSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-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
- 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 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
- FGCIQSBZGOVNLI-UHFFFAOYSA-N 1-[2-[4-(chloromethyl)phenoxy]ethyl]azepane Chemical compound C1=CC(CCl)=CC=C1OCCN1CCCCCC1 FGCIQSBZGOVNLI-UHFFFAOYSA-N 0.000 description 2
- 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 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
- 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 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
- 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
- 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
- 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 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
- 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 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
- 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 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
- CXFWSWIRMRLQNV-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-[4-(2-morpholin-4-ylethoxy)phenyl]propanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(O)=O)CC(C=C1)=CC=C1OCCN1CCOCC1 CXFWSWIRMRLQNV-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
- 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 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
- 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 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
- 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 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
- 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 2
- 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 2
- 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 2
- RFCQDOVPMUSZMN-UHFFFAOYSA-N 2-Naphthalenethiol Chemical compound C1=CC=CC2=CC(S)=CC=C21 RFCQDOVPMUSZMN-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
- 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 2
- 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 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
- 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 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
- 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
- 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
- KNLOTZNPRIFUAR-UHFFFAOYSA-N 2-bromodecanoic acid Chemical compound CCCCCCCCC(Br)C(O)=O KNLOTZNPRIFUAR-UHFFFAOYSA-N 0.000 description 2
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 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
- 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
- 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 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
- 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 2
- MCIIDRLDHRQKPH-UHFFFAOYSA-N 2-methyl-3-phenylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=CC=C1 MCIIDRLDHRQKPH-UHFFFAOYSA-N 0.000 description 2
- DKVIPUUJSKIQFZ-UHFFFAOYSA-N 2-naphthalen-2-ylpropanoic acid Chemical compound C1=CC=CC2=CC(C(C(O)=O)C)=CC=C21 DKVIPUUJSKIQFZ-UHFFFAOYSA-N 0.000 description 2
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- 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 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
- 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 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
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-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
- IZMWJUPSQXIVDN-UHFFFAOYSA-N 4-bromo-2-methylbut-1-ene Chemical compound CC(=C)CCBr IZMWJUPSQXIVDN-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 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
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 239000004097 EU approved flavor enhancer Substances 0.000 description 2
- 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 2
- 108010015302 Matrix metalloproteinase-9 Proteins 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
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 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
- 150000001543 aryl boronic acids Chemical class 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
- VDEUYMSGMPQMIK-UHFFFAOYSA-N benzhydroxamic acid Chemical compound ONC(=O)C1=CC=CC=C1 VDEUYMSGMPQMIK-UHFFFAOYSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 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 2
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound 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 2
- 239000011230 binding agent Substances 0.000 description 2
- 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 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
- 235000014121 butter Nutrition 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
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 239000000839 emulsion Substances 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
- 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 2
- KISAIXBGYVAYSS-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-5-methyl-2-(pyridin-3-ylmethyl)hex-4-enoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CC=C(C)C)(C(=O)OCC)CC1=CC=CN=C1 KISAIXBGYVAYSS-UHFFFAOYSA-N 0.000 description 2
- 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 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
- KOUAQOCYMAENKN-UHFFFAOYSA-N ethyl 2-bromohexanoate Chemical compound CCCCC(Br)C(=O)OCC KOUAQOCYMAENKN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DZGIKPCXSQVRCZ-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-(naphthalen-2-ylmethyl)piperidine-4-carboxylate Chemical compound C1CN(CC=2C=C3C=CC=CC3=CC=2)CCC1(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 DZGIKPCXSQVRCZ-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
- 235000019264 food flavour enhancer Nutrition 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- 238000012417 linear regression Methods 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
- 239000000314 lubricant Substances 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
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- URLYFRDHCDGEPS-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-2-phenoxyethanamine Chemical compound ClCCN(CCCl)CCOC1=CC=CC=C1 URLYFRDHCDGEPS-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
- QZXOLBPUAUOQFB-UHFFFAOYSA-N n-decanohydroxamic acid Chemical compound CCCCCCCCCC(=O)NO QZXOLBPUAUOQFB-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
- 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
- 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 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
- 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 2
- 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 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
- 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 2
- 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 description 2
- CCBCHURBDSNSTJ-UHFFFAOYSA-N n-hydroxybutanamide Chemical compound CCCC(=O)NO CCBCHURBDSNSTJ-UHFFFAOYSA-N 0.000 description 2
- RSIPQHOWTCNEBI-UHFFFAOYSA-N n-hydroxypropanamide Chemical compound CCC(=O)NO RSIPQHOWTCNEBI-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229940049953 phenylacetate Drugs 0.000 description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 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
- 125000006308 propyl amino group Chemical group 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229910052708 sodium 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
- 238000010186 staining Methods 0.000 description 2
- 239000008174 sterile 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
- 150000003573 thiols Chemical class 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 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
- 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
- FFMRYQDCKMYEDS-UHFFFAOYSA-N (4-methoxyphenyl)sulfanyl propanoate Chemical compound C(CC)(=O)OSC1=CC=C(C=C1)OC FFMRYQDCKMYEDS-UHFFFAOYSA-N 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
- XCSWWTGQHOOLAE-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CCC(C(O)=O)CC1 XCSWWTGQHOOLAE-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
- 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
- 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
- GPTWTWDXTBTXHZ-UHFFFAOYSA-N 1-[2-[chloro(phenyl)methoxy]ethyl]piperidine Chemical compound C=1C=CC=CC=1C(Cl)OCCN1CCCCC1 GPTWTWDXTBTXHZ-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
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- IIASCQBFNHWZBE-UHFFFAOYSA-N 1-bromoethyl acetate Chemical compound CC(Br)OC(C)=O IIASCQBFNHWZBE-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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 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
- 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 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
- RHOVEHOUFDXMJJ-UHFFFAOYSA-N 2,5-dimethylhex-4-enoic acid Chemical compound OC(=O)C(C)CC=C(C)C RHOVEHOUFDXMJJ-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
- 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
- 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
- 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
- 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 1
- 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 1
- 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 1
- 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 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
- CFFQSZZIBNIDOI-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonyl-3-methylbutanamide Chemical compound COC1=CC=C(C=C1)S(=O)(=O)C(C(=O)N)C(C)C CFFQSZZIBNIDOI-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
- 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 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
- 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 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
- JRWLVBLPQBCRRW-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonylpropanoic acid Chemical compound COC1=CC=C(S(=O)(=O)C(C)C(O)=O)C=C1 JRWLVBLPQBCRRW-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
- 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 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
- DSCJETUEDFKYGN-UHFFFAOYSA-N 2-Methoxybenzenethiol Chemical compound COC1=CC=CC=C1S DSCJETUEDFKYGN-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
- 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
- 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 1
- RWZGZCZQOCWIFZ-UHFFFAOYSA-N 2-[2-(4-methoxyphenyl)sulfanylphenyl]acetic acid Chemical compound C1=CC(OC)=CC=C1SC1=CC=CC=C1CC(O)=O RWZGZCZQOCWIFZ-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
- 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 1
- 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 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
- 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
- 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 1
- 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 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
- XHJGXOOOMKCJPP-UHFFFAOYSA-N 2-[tert-butyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(C(C)(C)C)CCO XHJGXOOOMKCJPP-UHFFFAOYSA-N 0.000 description 1
- FDIPPUOQYAJMOI-UHFFFAOYSA-N 2-benzyl-n-hydroxy-2-(4-methoxyphenyl)sulfonyl-3-phenylpropanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(=O)NO)(CC=1C=CC=CC=1)CC1=CC=CC=C1 FDIPPUOQYAJMOI-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
- LMDKWAOLUKQGPQ-UHFFFAOYSA-N 2-bromo-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCCC(Br)C(O)=O LMDKWAOLUKQGPQ-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
- YUQUNWNSQDULTI-UHFFFAOYSA-N 2-bromobenzenethiol Chemical compound SC1=CC=CC=C1Br YUQUNWNSQDULTI-UHFFFAOYSA-N 0.000 description 1
- YAQLSKVCTLCIIE-UHFFFAOYSA-N 2-bromobutyric acid Chemical compound CCC(Br)C(O)=O YAQLSKVCTLCIIE-UHFFFAOYSA-N 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
- UQZPGHOJMQTOHB-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)-n-ethylethanamine Chemical compound ClCCN(CC)CCCl UQZPGHOJMQTOHB-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GDLGGKYOPIKBLB-UHFFFAOYSA-N 2-methyl-3-naphthalen-2-ylpropanoic acid Chemical compound C1=CC=CC2=CC(CC(C)C(O)=O)=CC=C21 GDLGGKYOPIKBLB-UHFFFAOYSA-N 0.000 description 1
- DZRWATJWDHWPJW-UHFFFAOYSA-N 2-methyl-3-pyridin-3-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=CN=C1 DZRWATJWDHWPJW-UHFFFAOYSA-N 0.000 description 1
- WKVHDECXFMVPRJ-UHFFFAOYSA-N 2-methyl-3-quinolin-6-ylpropanoic acid Chemical compound N1=CC=CC2=CC(CC(C)C(O)=O)=CC=C21 WKVHDECXFMVPRJ-UHFFFAOYSA-N 0.000 description 1
- CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- JHKCYGGFYUKYEG-UHFFFAOYSA-N 2-octylsulfonylpropanoic acid Chemical compound CCCCCCCCS(=O)(=O)C(C)C(O)=O JHKCYGGFYUKYEG-UHFFFAOYSA-N 0.000 description 1
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 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
- 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
- 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
- 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 1
- 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 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
- RUROFEVDCUGKHD-UHFFFAOYSA-N 3-bromoprop-1-enylbenzene Chemical compound BrCC=CC1=CC=CC=C1 RUROFEVDCUGKHD-UHFFFAOYSA-N 0.000 description 1
- NIDWUZTTXGJFNN-UHFFFAOYSA-N 3-bromopropoxybenzene Chemical compound BrCCCOC1=CC=CC=C1 NIDWUZTTXGJFNN-UHFFFAOYSA-N 0.000 description 1
- XMZQWZJMTBCUFT-UHFFFAOYSA-N 3-bromopropylbenzene Chemical compound BrCCCC1=CC=CC=C1 XMZQWZJMTBCUFT-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 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 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
- 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 1
- JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-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
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 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
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 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
- AHWZZYPVZPMZSG-UHFFFAOYSA-N 5-(diaminomethylideneamino)-2-(3-fluorophenyl)sulfinyl-n-hydroxypentanamide Chemical compound NC(=N)NCCCC(C(=O)NO)S(=O)C1=CC=CC(F)=C1 AHWZZYPVZPMZSG-UHFFFAOYSA-N 0.000 description 1
- KYWQKZZFEDWVJW-UHFFFAOYSA-N 5-bromo-5-propylcyclohexa-1,3-diene Chemical compound CCCC1(Br)CC=CC=C1 KYWQKZZFEDWVJW-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
- 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
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- MJBPUQUGJNAPAZ-AWEZNQCLSA-N Butin Natural products C1([C@@H]2CC(=O)C3=CC=C(C=C3O2)O)=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-AWEZNQCLSA-N 0.000 description 1
- MJBPUQUGJNAPAZ-UHFFFAOYSA-N Butine Natural products O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-UHFFFAOYSA-N 0.000 description 1
- BGLLELCBVOEEBR-UHFFFAOYSA-N C1=CC=C(C=C1)OCCCCC(CC2=CN=CC=C2)C(=O)O Chemical compound C1=CC=C(C=C1)OCCCCC(CC2=CN=CC=C2)C(=O)O BGLLELCBVOEEBR-UHFFFAOYSA-N 0.000 description 1
- DKFRVJZZSFPCIS-UHFFFAOYSA-N CC(=O)OS(=O)(=O)C1=CC=C(C=C1)OC Chemical compound CC(=O)OS(=O)(=O)C1=CC=C(C=C1)OC DKFRVJZZSFPCIS-UHFFFAOYSA-N 0.000 description 1
- NIUYFWJDRVIXKF-UHFFFAOYSA-N CC(C)CCC(CC1=CN=CC=C1)C(=O)O Chemical compound CC(C)CCC(CC1=CN=CC=C1)C(=O)O NIUYFWJDRVIXKF-UHFFFAOYSA-N 0.000 description 1
- MMKDWXAWJIRYNY-UHFFFAOYSA-N CCCCCC(C(O)=O)S(=O)C1=CC=C(OC)C=C1 Chemical compound CCCCCC(C(O)=O)S(=O)C1=CC=C(OC)C=C1 MMKDWXAWJIRYNY-UHFFFAOYSA-N 0.000 description 1
- HEOZPPPMQULWOM-UHFFFAOYSA-N CCOC(=O)C(CC1=CC=CC=C1)S(=O)(=O)C2=C(OC=C2)C Chemical compound CCOC(=O)C(CC1=CC=CC=C1)S(=O)(=O)C2=C(OC=C2)C HEOZPPPMQULWOM-UHFFFAOYSA-N 0.000 description 1
- QFRKIYOEPHSNON-UHFFFAOYSA-N COC1=CC=C(S(=O)(=O)C(CC=C(C)CCC=C(C)C)C(O)=O)C=C1 Chemical compound COC1=CC=C(S(=O)(=O)C(CC=C(C)CCC=C(C)C)C(O)=O)C=C1 QFRKIYOEPHSNON-UHFFFAOYSA-N 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 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
- 102000005593 Endopeptidases Human genes 0.000 description 1
- 108010059378 Endopeptidases Proteins 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- XMDZWPHRCURDSK-UHFFFAOYSA-N FC1=CC=C(C=C1)S(=O)(=O)C(C(=O)O)(C(C#CC)C)C=1C=NC=CC1 Chemical compound FC1=CC=C(C=C1)S(=O)(=O)C(C(=O)O)(C(C#CC)C)C=1C=NC=CC1 XMDZWPHRCURDSK-UHFFFAOYSA-N 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 241001465754 Metazoa Species 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical class SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- YKMMKYIUONOWOD-UHFFFAOYSA-N N-[4-(2-piperidin-1-ylethoxy)phenyl]propanamide Chemical compound C(CC)(=O)NC1=CC=C(C=C1)OCCN1CCCCC1 YKMMKYIUONOWOD-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
- QDEKTHCPSCGUQA-UHFFFAOYSA-N N-hydroxy-4-(4-methoxyphenyl)sulfonyl-2-methyl-1-naphthalen-2-ylpiperidine-4-carboxamide Chemical compound ONC(=O)C1(CC(N(CC1)C1=CC2=CC=CC=C2C=C1)C)S(=O)(=O)C1=CC=C(C=C1)OC QDEKTHCPSCGUQA-UHFFFAOYSA-N 0.000 description 1
- 241001274216 Naso Species 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
- GEHJHDIWXQAIOS-UHFFFAOYSA-N O[S+]1C2=CC=CC=C2N=C1.O Chemical compound O[S+]1C2=CC=CC=C2N=C1.O GEHJHDIWXQAIOS-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000269980 Pleuronectidae Species 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
- 229920002472 Starch Polymers 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 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
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 206010064930 age-related macular degeneration Diseases 0.000 description 1
- 150000001350 alkyl halides Chemical class 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- VERMEZLHWFHDLK-UHFFFAOYSA-N benzene-1,2,3,4-tetrol Chemical compound OC1=CC=C(O)C(O)=C1O VERMEZLHWFHDLK-UHFFFAOYSA-N 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-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
- 230000004071 biological effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000006278 bromobenzyl group Chemical group 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 150000001732 carboxylic acid derivatives 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
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- KQHLPMCNDYYZMB-UHFFFAOYSA-N chloromethylbenzene;hydrochloride Chemical compound Cl.ClCC1=CC=CC=C1 KQHLPMCNDYYZMB-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 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
- 210000002808 connective tissue Anatomy 0.000 description 1
- 229920001577 copolymer Chemical compound 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 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
- 230000003412 degenerative effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 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
- 239000008393 encapsulating agent Substances 0.000 description 1
- 229940066758 endopeptidases Drugs 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- NHTMHJRDGNELFN-UHFFFAOYSA-N ethyl 1-[(3,4-dichlorophenyl)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(Cl)C(Cl)=C1 NHTMHJRDGNELFN-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 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
- 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 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
- CEQYOMJOECADQK-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-4-methylpentanoate Chemical compound CCOC(=O)C(CC(C)C)S(=O)(=O)C1=CC=C(OC)C=C1 CEQYOMJOECADQK-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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
- 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
- VDXYJUBMHZEPOQ-UHFFFAOYSA-N ethyl 2-(4-methylphenyl)sulfonylacetate Chemical compound CCOC(=O)CS(=O)(=O)C1=CC=C(C)C=C1 VDXYJUBMHZEPOQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BKTKLDMYHTUESO-UHFFFAOYSA-N ethyl 2-bromo-2-phenylacetate Chemical compound CCOC(=O)C(Br)C1=CC=CC=C1 BKTKLDMYHTUESO-UHFFFAOYSA-N 0.000 description 1
- WNFUWONOILPKNX-UHFFFAOYSA-N ethyl 2-bromo-3-methylbutanoate Chemical compound CCOC(=O)C(Br)C(C)C WNFUWONOILPKNX-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
- JQQZIRFEGUUJBP-UHFFFAOYSA-N ethyl 2-bromotetradecanoate Chemical compound CCCCCCCCCCCCC(Br)C(=O)OCC JQQZIRFEGUUJBP-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
- ZQHXCTLYCWWBDB-UHFFFAOYSA-N ethyl 2-sulfonylacetate Chemical class CCOC(=O)C=S(=O)=O ZQHXCTLYCWWBDB-UHFFFAOYSA-N 0.000 description 1
- ZRFSFNRGMBEKDH-UHFFFAOYSA-N ethyl 3-(2-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=CC=C1Br ZRFSFNRGMBEKDH-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
- 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
- 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
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 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
- 201000005884 exanthem Diseases 0.000 description 1
- 239000003925 fat Substances 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
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 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
- 125000001475 halogen functional group Chemical group 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- AVZRFVZXXPLVEF-UHFFFAOYSA-N hydroxylamine octane Chemical compound ON.CCCCCCCC AVZRFVZXXPLVEF-UHFFFAOYSA-N 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
- 238000007918 intramuscular administration Methods 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
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 230000036210 malignancy Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 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
- 238000002156 mixing Methods 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
- SXPGFJZLDDFUHA-UHFFFAOYSA-N n,n-bis(2-chloroethyl)butan-1-amine Chemical compound CCCCN(CCCl)CCCl SXPGFJZLDDFUHA-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
- 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
- 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 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JOASPLCDBDCRJJ-UHFFFAOYSA-N n-cyclooctylhydroxylamine Chemical compound ONC1CCCCCCC1 JOASPLCDBDCRJJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 description 1
- 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 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
- 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 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
- 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
- ICLCFPBPJLPVBT-UHFFFAOYSA-N n-hydroxy-2-(4-hydroxyphenyl)sulfinyl-3-phenylpropanamide Chemical compound C=1C=C(O)C=CC=1S(=O)C(C(=O)NO)CC1=CC=CC=C1 ICLCFPBPJLPVBT-UHFFFAOYSA-N 0.000 description 1
- MSAYGAYDDGZTEL-UHFFFAOYSA-N n-hydroxy-2-(4-hydroxyphenyl)sulfonyl-3-phenylpropanamide Chemical compound C=1C=C(O)C=CC=1S(=O)(=O)C(C(=O)NO)CC1=CC=CC=C1 MSAYGAYDDGZTEL-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
- 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
- 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 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
- 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 1
- 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 1
- KDJZFDKCOPXERM-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfonyl-2-methyl-3-[4-(2-morpholin-4-ylethoxy)phenyl]propanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C)(C(=O)NO)CC(C=C1)=CC=C1OCCN1CCOCC1 KDJZFDKCOPXERM-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 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
- 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
- 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
- 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
- UCMFHMLHBVQPFT-UHFFFAOYSA-N n-hydroxy-2-[4-(2-piperazin-1-ylethoxy)phenyl]sulfinyloctanamide Chemical compound C1=CC(S(=O)C(C(=O)NO)CCCCCC)=CC=C1OCCN1CCNCC1 UCMFHMLHBVQPFT-UHFFFAOYSA-N 0.000 description 1
- PDCLXDAYFLVLAM-UHFFFAOYSA-N n-hydroxy-2-[4-(2-piperazin-1-ylethoxy)phenyl]sulfonyloctanamide Chemical compound C1=CC(S(=O)(=O)C(C(=O)NO)CCCCCC)=CC=C1OCCN1CCNCC1 PDCLXDAYFLVLAM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ATEQRTDCFBEHOS-UHFFFAOYSA-N n-hydroxy-2-[4-(3-pyridin-2-ylpropoxy)phenyl]sulfinyloctanamide Chemical compound C1=CC(S(=O)C(C(=O)NO)CCCCCC)=CC=C1OCCCC1=CC=CC=N1 ATEQRTDCFBEHOS-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
- 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
- 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
- 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 1
- 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 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
- QUKJNGDEQKDQGY-UHFFFAOYSA-N n-hydroxy-2-sulfonylacetamide Chemical class ONC(=O)C=S(=O)=O QUKJNGDEQKDQGY-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
- ZGVWJEXIZOWVAY-UHFFFAOYSA-N n-hydroxy-3-methyl-2-(2-phenylethylsulfonyl)butanamide Chemical compound ONC(=O)C(C(C)C)S(=O)(=O)CCC1=CC=CC=C1 ZGVWJEXIZOWVAY-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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 description 1
- 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 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 1
- 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 description 1
- 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 1
- ODHYIQOBTIWVRZ-UHFFFAOYSA-N n-propan-2-ylhydroxylamine Chemical compound CC(C)NO ODHYIQOBTIWVRZ-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012663 orally bioavailable inhibitor Substances 0.000 description 1
- 229940044205 orally bioavailable inhibitor Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000012057 packaged powder Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 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
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- YYFIGOPUHPDIBO-UHFFFAOYSA-N propanoic acid;hydrochloride Chemical compound Cl.CCC(O)=O YYFIGOPUHPDIBO-UHFFFAOYSA-N 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 230000009759 skin aging Effects 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 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
- 239000011550 stock solution Substances 0.000 description 1
- 108091007196 stromelysin Proteins 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000446 sulfanediyl group Chemical class *S* 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
- 230000009885 systemic 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
- IQFHYOGPJXGBLE-UHFFFAOYSA-N tert-butyl 2-(4-fluorophenyl)sulfonyl-2-(pyridin-3-ylmethyl)hex-4-ynoate Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)C(CC#CC)(C(=O)OC(C)(C)C)CC1=CC=CN=C1 IQFHYOGPJXGBLE-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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 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
- 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 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 210000001519 tissue Anatomy 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
- 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
- 239000002447 tumor necrosis factor alpha converting enzyme inhibitor Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 210000004885 white matter Anatomy 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
- 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
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
-
- 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
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/12—Oxygen or 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
- C07D211/66—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 having a hetero atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/84—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/28—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/70—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/70—Sulfur atoms
- C07D277/74—Sulfur atoms substituted by carbon atoms
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Endocrinology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Biotechnology (AREA)
- Hospice & Palliative Care (AREA)
- Transplantation (AREA)
- Biomedical Technology (AREA)
- Dermatology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80672897A | 1997-02-27 | 1997-02-27 | |
| PCT/US1998/002987 WO1998037877A1 (en) | 1997-02-27 | 1998-02-17 | 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 |
|---|---|
| BG103757A true BG103757A (bg) | 2000-04-28 |
Family
ID=25194722
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG103757A BG103757A (bg) | 1997-02-27 | 1999-09-24 | N-хидрокси-2-/алкил,арил или хетероарил сулфанил,сулфинил или сулфонил/-3-заместени алкил, арил или хетероариламиди като инхибитори на матрична металопротеиназа |
| BG103760A BG103760A (bg) | 1997-02-27 | 1999-09-27 | N-хидрокси-2-/алкил, арил или хетероарил сулфанил, сулфинил или сулфонил/-3-заместени алкил, арил или хетероариламиди като инхибитори на матрична металопротеиназа |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG103760A BG103760A (bg) | 1997-02-27 | 1999-09-27 | N-хидрокси-2-/алкил, арил или хетероарил сулфанил, сулфинил или сулфонил/-3-заместени алкил, арил или хетероариламиди като инхибитори на матрична металопротеиназа |
Country Status (30)
| Country | Link |
|---|---|
| EP (2) | EP0970046B1 (de) |
| JP (2) | JP2001519777A (de) |
| KR (2) | KR20000075808A (de) |
| CN (2) | CN1252790A (de) |
| AR (1) | AR011451A1 (de) |
| AT (2) | ATE263554T1 (de) |
| AU (2) | AU748998B2 (de) |
| BG (2) | BG103757A (de) |
| BR (2) | BR9807803A (de) |
| CA (2) | CA2282656A1 (de) |
| CY (1) | CY2477B1 (de) |
| DE (2) | DE69820424T2 (de) |
| DK (2) | DK0970046T3 (de) |
| EA (2) | EA003836B1 (de) |
| EE (2) | EE04150B1 (de) |
| ES (2) | ES2217540T3 (de) |
| GE (2) | GEP20022627B (de) |
| HU (2) | HUP0002092A3 (de) |
| IL (2) | IL131257A0 (de) |
| NO (2) | NO314258B1 (de) |
| NZ (2) | NZ337336A (de) |
| PL (2) | PL335401A1 (de) |
| PT (2) | PT973512E (de) |
| SK (2) | SK115799A3 (de) |
| TR (2) | TR199901901T2 (de) |
| TW (1) | TW568900B (de) |
| UA (1) | UA58543C2 (de) |
| WO (2) | WO1998038163A1 (de) |
| YU (2) | YU40999A (de) |
| ZA (2) | ZA981628B (de) |
Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2209122T3 (es) * | 1997-03-04 | 2004-06-16 | Pharmacia Corporation | Compuestos de acido sulfonil alfa-hidroxi hidroxamico aromatico. |
| US7115632B1 (en) | 1999-05-12 | 2006-10-03 | G. D. Searle & Co. | Sulfonyl aryl or heteroaryl hydroxamic acid compounds |
| US6696449B2 (en) | 1997-03-04 | 2004-02-24 | Pharmacia Corporation | Sulfonyl aryl hydroxamates and their use as matrix metalloprotease inhibitors |
| WO1998039315A1 (en) * | 1997-03-04 | 1998-09-11 | Monsanto Company | Aromatic sulfonyl alpha-cycloamino hydroxamic acid compounds |
| US6794511B2 (en) | 1997-03-04 | 2004-09-21 | G. D. Searle | Sulfonyl aryl or heteroaryl hydroxamic acid compounds |
| EA003937B1 (ru) * | 1997-10-15 | 2003-10-30 | Уайт | Новые арилоксиалкилдиалкиламины |
| US6005102A (en) | 1997-10-15 | 1999-12-21 | American Home Products Corporation | Aryloxy-alkyl-dialkylamines |
| US6750228B1 (en) | 1997-11-14 | 2004-06-15 | Pharmacia Corporation | Aromatic sulfone hydroxamic acid metalloprotease inhibitor |
| US20010039287A1 (en) * | 1997-11-14 | 2001-11-08 | Thomas E Barta | Aromatic sulfone hydroxamic acid metalloprotease inhibitor |
| JP2001523662A (ja) * | 1997-11-14 | 2001-11-27 | ジー・ディー・サール・アンド・カンパニー | 芳香族スルホンヒドロキサム酸メタロプロテアーゼ阻害剤 |
| GB9725782D0 (en) | 1997-12-05 | 1998-02-04 | Pfizer Ltd | Therapeutic agents |
| EA003283B1 (ru) * | 1998-02-19 | 2003-04-24 | Американ Цианамид Компани | N-гидрокси-2-(алкил-, арил- или гетероарилсульфанил-, сульфинил- или сульфонил)-3-замещенный алкил-, арил- или гетероариламиды в качестве ингибиторов матричных металлопротеиназ |
| US7045519B2 (en) | 1998-06-19 | 2006-05-16 | Chiron Corporation | Inhibitors of glycogen synthase kinase 3 |
| US6114361A (en) * | 1998-11-05 | 2000-09-05 | Pfizer Inc. | 5-oxo-pyrrolidine-2-carboxylic acid hydroxamide derivatives |
| 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 |
| US6358980B1 (en) * | 1999-01-27 | 2002-03-19 | American Cyanamid Company | Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase/tace inhibitors |
| US6946473B2 (en) | 1999-01-27 | 2005-09-20 | Wyeth Holdings Corporation | Preparation and use of acetylenic ortho-sulfonamido and phosphinic acid amido bicyclic heteroaryl hydroxamic acids as TACE inhibitors |
| US6340691B1 (en) | 1999-01-27 | 2002-01-22 | American Cyanamid Company | Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase and tace inhibitors |
| US6753337B2 (en) | 1999-01-27 | 2004-06-22 | Wyeth Holdings Corporation | Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase/tace inhibitors |
| AR035311A1 (es) * | 1999-01-27 | 2004-05-12 | Wyeth Corp | Derivados de acido hidroxamico que contienen alquinilo, como inhibidores de las metalloproteinasas de matriz y de la tace, composicion farmaceutica y el uso de los mismos para la manufactura de un medicamento |
| US6800646B1 (en) | 1999-02-08 | 2004-10-05 | Pharmacia Corporation | Sulfamato hydroxamic acid metalloprotease inhibitor |
| GEP20043238B (en) | 1999-02-08 | 2004-05-25 | Searle & Co | Sulfamato Hydroxamic Acid Metalloprotease Inhibitor, its Use in Preparation of Pharmaceutical Composition for Treatment of Conditions Associated with Pathological Matrix Metalloprotease Activity |
| SE9901572D0 (sv) | 1999-05-03 | 1999-05-03 | Astra Ab | New compounds |
| US6511993B1 (en) | 1999-06-03 | 2003-01-28 | Kevin Neil Dack | Metalloprotease inhibitors |
| WO2001055112A1 (en) * | 2000-01-27 | 2001-08-02 | American Cyanamid Company | Method for preparing alpha-sulfonyl hydroxamic acid derivatives |
| US6683093B2 (en) | 2000-05-12 | 2004-01-27 | Pharmacia Corporation | Aromatic sulfone hydroxamic acids and their use as protease inhibitors |
| HUP0304069A2 (hu) | 2001-05-11 | 2004-04-28 | Pharmacia Corp. | Aromás szulfon-hidroxamátok és proteázgátlókként való alkalmazásuk |
| US6683078B2 (en) | 2001-07-19 | 2004-01-27 | Pharmacia Corporation | Use of sulfonyl aryl or heteroaryl hydroxamic acids and derivatives thereof as aggrecanase inhibitors |
| PE20030701A1 (es) | 2001-12-20 | 2003-08-21 | Schering Corp | Compuestos para el tratamiento de trastornos inflamatorios |
| EP2324830A1 (de) | 2002-03-05 | 2011-05-25 | TransTech Pharma Inc. | Verfahren zur Herstellung von einem monozylische Azolderivat das die Interaktion von Liganden mit Rage hemmt |
| CA2483314A1 (en) | 2002-04-25 | 2003-11-06 | Pharmacia Corporation | Piperidinyl-and piperazinyl-sulfonylmethyl hydroxamic acids and their use as protease inhibitors |
| CA2490646A1 (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 |
| US7423176B2 (en) | 2004-04-13 | 2008-09-09 | Cephalon, Inc. | Bicyclic aromatic sulfinyl derivatives |
| WO2007070760A2 (en) | 2005-12-15 | 2007-06-21 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| EP2081905B1 (de) | 2006-07-28 | 2012-09-12 | Boehringer Ingelheim International GmbH | Sulfonyl verbindungen als cb2 rezeptor modulatoren |
| MX2009002888A (es) | 2006-09-25 | 2009-03-31 | Boehringer Ingelheim Int | Compuestos que modulan el receptor cb2. |
| US7803793B2 (en) | 2006-10-05 | 2010-09-28 | Janssen Pharmaceutica Nv | Heterocyclic derived metalloprotease inhibitors |
| US7879911B2 (en) | 2007-02-01 | 2011-02-01 | Johnson Alan T | Hydroxamic acid derivatives of phenoxy-acetic acids and analogs useful as therapeutic agents for treating anthrax poisoning |
| US8546563B2 (en) | 2007-11-07 | 2013-10-01 | Boehringer Ingelheim International Gmbh | Compounds which modulate the CB2 receptor |
| EP2326629B1 (de) | 2008-07-10 | 2013-10-02 | Boehringer Ingelheim International GmbH | Den cb2-rezeptor modulierende sulfonverbindungen |
| AP2011005674A0 (en) | 2008-09-25 | 2011-04-30 | Boehringer Ingelheim Int | Sulfonyl compounds which selectively modulate the CB2 receptor. |
| US8299103B2 (en) | 2009-06-15 | 2012-10-30 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the CB2 receptor |
| JP5756800B2 (ja) | 2009-06-16 | 2015-07-29 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Cb2受容体を調節するアゼチジン2−カルボキサミド誘導体 |
| WO2011037795A1 (en) | 2009-09-22 | 2011-03-31 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the cb2 receptor |
| CA2772797C (en) | 2009-09-30 | 2018-09-25 | Transtech Pharma, Inc. | Substituted imidazole derivatives |
| WO2011045703A2 (en) * | 2009-10-13 | 2011-04-21 | Pfizer Inc. | C-linked hydroxamic acid derivatives useful as antibacterial agents |
| US9315454B2 (en) | 2010-01-15 | 2016-04-19 | Boehringer Ingelheim International Gmbh | Compounds which modulate the CB2 receptor |
| US8329735B2 (en) | 2010-03-05 | 2012-12-11 | Boehringer Ingelheim International Gmbh | Tetrazole compounds which selectively modulate the CB2 receptor |
| WO2012012307A1 (en) | 2010-07-22 | 2012-01-26 | Boehringer Ingelheim International Gmbh | Sulfonyl compounds which modulate the cb2 rece |
| WO2012036257A1 (ja) * | 2010-09-17 | 2012-03-22 | 国立大学法人東京大学 | 血小板の機能を維持するための組成物 |
| CA2917604C (en) * | 2012-07-18 | 2021-08-10 | Josune Orbe Lopategui | New antifibrinolytic compounds |
| EP2803668A1 (de) | 2013-05-17 | 2014-11-19 | Boehringer Ingelheim International Gmbh | Neuartige (Cyano-dimethyl-methyl)-isoxazole und -[1,3,4]-thiadiazole |
| AU2015261540A1 (en) | 2014-05-16 | 2017-01-12 | Idorsia Pharmaceuticals Ltd | Antibacterial quinazoline-4(3h)-one derivatives |
| 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 |
| US12491186B2 (en) | 2018-10-04 | 2025-12-09 | INSERM (Institut National de la Santé et de la Recherche Médicale) | EGFR inhibitors for treating keratodermas |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50121218A (de) * | 1974-03-01 | 1975-09-23 | ||
| DE2424742C3 (de) * | 1974-05-21 | 1982-04-22 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Thiophenderivate Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| US3994997A (en) * | 1975-05-09 | 1976-11-30 | Gulf Oil Corporation | O,O-diethyl-O-carboxamidophosphate esters |
| GB1520812A (en) * | 1975-10-02 | 1978-08-09 | Lafon Labor | Benzhydrylsulphinyl derivatives |
| GB1574822A (en) * | 1976-03-23 | 1980-09-10 | Lafon Labor | Acetohydroxamic acid derivatives and pharmaceutical compositions thereof |
| FR2528041A1 (fr) * | 1982-06-04 | 1983-12-09 | Lafon Labor | Acides halogenobenzhydrylsulfinylacetohydroxamiques, procede de preparation et utilisation en therapeutique |
| FR2561646B1 (fr) * | 1984-03-23 | 1987-10-09 | Lafon Labor | Derives d'acide (a-(alkylaminomethyl)-benzyl)-thioacetique, procede de preparation et utilisation en therapeutique |
| IL92915A0 (en) * | 1989-01-05 | 1990-09-17 | Ciba Geigy Ag | Certain pyrrolylphenyl-substituted hydroxamic acid derivatives |
| WO1993020047A1 (en) * | 1992-04-07 | 1993-10-14 | British Bio-Technology Limited | Hydroxamic acid based collagenase and cytokine inhibitors |
| US5455258A (en) * | 1993-01-06 | 1995-10-03 | Ciba-Geigy Corporation | Arylsulfonamido-substituted hydroxamic acids |
| FR2708201B1 (fr) * | 1993-06-30 | 1995-10-20 | Lafon Labor | Utilisation de dérivés d'acétamide pour la fabrication de médicaments. |
| GB9416897D0 (en) * | 1994-08-20 | 1994-10-12 | British Biotech Pharm | Metalloproteinase inhibitors |
| CA2217857A1 (en) * | 1995-05-10 | 1996-11-14 | Darwin Discovery Limited | Peptide compounds which inhibit metalloproteinase and tnf liberation and their therapeutic uses |
| US5665777A (en) * | 1995-11-14 | 1997-09-09 | Abbott Laboratories | Biphenyl hydroxamate inhibitors of matrix metalloproteinases |
| DK0871439T3 (da) * | 1996-01-02 | 2004-08-02 | Aventis Pharma Inc | Substituerede (aryl, heteroaryl, arylmethyl eller heteroarylmethyl) hydroxamsyreforbindelser |
-
1998
- 1998-02-17 UA UA99095311A patent/UA58543C2/uk unknown
- 1998-02-17 EA EA199900768A patent/EA003836B1/ru not_active IP Right Cessation
- 1998-02-17 AU AU64368/98A patent/AU748998B2/en not_active Ceased
- 1998-02-17 KR KR1019997007881A patent/KR20000075808A/ko not_active Ceased
- 1998-02-17 ES ES98906468T patent/ES2217540T3/es not_active Expired - Lifetime
- 1998-02-17 KR KR1019997007882A patent/KR20000075809A/ko not_active Ceased
- 1998-02-17 GE GEAP19985007A patent/GEP20022627B/en unknown
- 1998-02-17 PT PT98906468T patent/PT973512E/pt unknown
- 1998-02-17 DE DE69820424T patent/DE69820424T2/de not_active Expired - Fee Related
- 1998-02-17 BR BR9807803-8A patent/BR9807803A/pt not_active IP Right Cessation
- 1998-02-17 EE EEP199900369A patent/EE04150B1/xx not_active IP Right Cessation
- 1998-02-17 YU YU40999A patent/YU40999A/sh unknown
- 1998-02-17 WO PCT/US1998/003291 patent/WO1998038163A1/en not_active Ceased
- 1998-02-17 NZ NZ337336A patent/NZ337336A/en unknown
- 1998-02-17 NZ NZ337298A patent/NZ337298A/xx unknown
- 1998-02-17 AT AT98906468T patent/ATE263554T1/de not_active IP Right Cessation
- 1998-02-17 EP EP98910022A patent/EP0970046B1/de not_active Expired - Lifetime
- 1998-02-17 SK SK1157-99A patent/SK115799A3/sk unknown
- 1998-02-17 HU HU0002092A patent/HUP0002092A3/hu unknown
- 1998-02-17 CN CN98804329A patent/CN1252790A/zh active Pending
- 1998-02-17 WO PCT/US1998/002987 patent/WO1998037877A1/en not_active Ceased
- 1998-02-17 IL IL13125798A patent/IL131257A0/xx unknown
- 1998-02-17 DK DK98910022T patent/DK0970046T3/da active
- 1998-02-17 EA EA199900769A patent/EA001742B1/ru not_active IP Right Cessation
- 1998-02-17 TR TR1999/01901T patent/TR199901901T2/xx unknown
- 1998-02-17 SK SK1158-99A patent/SK115899A3/sk unknown
- 1998-02-17 JP JP53770698A patent/JP2001519777A/ja not_active Withdrawn
- 1998-02-17 ES ES98910022T patent/ES2212274T3/es not_active Expired - Lifetime
- 1998-02-17 BR BR9807802A patent/BR9807802A/pt not_active IP Right Cessation
- 1998-02-17 DE DE69823019T patent/DE69823019T2/de not_active Expired - Fee Related
- 1998-02-17 PL PL98335401A patent/PL335401A1/xx unknown
- 1998-02-17 IL IL13125898A patent/IL131258A0/xx not_active IP Right Cessation
- 1998-02-17 YU YU41099A patent/YU41099A/sh unknown
- 1998-02-17 PT PT98910022T patent/PT970046E/pt unknown
- 1998-02-17 CA CA002282656A patent/CA2282656A1/en not_active Abandoned
- 1998-02-17 AT AT98910022T patent/ATE256107T1/de not_active IP Right Cessation
- 1998-02-17 TR TR1999/02095T patent/TR199902095T2/xx unknown
- 1998-02-17 EE EEP199900371A patent/EE04295B1/xx not_active IP Right Cessation
- 1998-02-17 CN CNB988043335A patent/CN1210263C/zh not_active Expired - Fee Related
- 1998-02-17 HU HU0001463A patent/HUP0001463A3/hu unknown
- 1998-02-17 DK DK98906468T patent/DK0973512T3/da active
- 1998-02-17 AU AU61686/98A patent/AU726204B2/en not_active Ceased
- 1998-02-17 PL PL98335286A patent/PL335286A1/xx unknown
- 1998-02-17 JP JP53772498A patent/JP2001513771A/ja not_active Withdrawn
- 1998-02-17 GE GEAP19985008A patent/GEP20022626B/en unknown
- 1998-02-17 CA CA002282655A patent/CA2282655A1/en not_active Abandoned
- 1998-02-17 EP EP98906468A patent/EP0973512B1/de not_active Expired - Lifetime
- 1998-02-26 ZA ZA9801628A patent/ZA981628B/xx unknown
- 1998-02-26 ZA ZA9801625A patent/ZA981625B/xx unknown
- 1998-02-27 AR ARP980100909A patent/AR011451A1/es not_active Application Discontinuation
- 1998-03-17 TW TW087102853A patent/TW568900B/zh active
-
1999
- 1999-08-26 NO NO19994124A patent/NO314258B1/no not_active IP Right Cessation
- 1999-08-26 NO NO19994125A patent/NO314302B1/no unknown
- 1999-09-24 BG BG103757A patent/BG103757A/bg unknown
- 1999-09-27 BG BG103760A patent/BG103760A/bg unknown
-
2004
- 2004-09-08 CY CY0400069A patent/CY2477B1/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BG103757A (bg) | N-хидрокси-2-/алкил,арил или хетероарил сулфанил,сулфинил или сулфонил/-3-заместени алкил, арил или хетероариламиди като инхибитори на матрична металопротеиназа | |
| US6288086B1 (en) | N-hydroxy-2-(alkyl, aryl, or heteroaryl, sulfanyl, sulfinyl or sulfonyl)-3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors | |
| BG104782A (bg) | N-хидрокси-2-(алкил, арил или хетероарил сулфанил, сулфинил или сулфонил) -3-заместени алкил, арил или хетероариламиди като матрични металопротеиназни инхибитори | |
| US6342508B1 (en) | N-hydroxy-2-(Alkyl,Aryl or Heteroaryl sulfanyl, sulfinyl or sulfonyl) 3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors | |
| CZ20003036A3 (cs) | Inhibitory metaloproteinázy matrice | |
| CZ306099A3 (cs) | Inhibitory metalloproteinázy | |
| CZ305999A3 (cs) | Inhibitory metalloproteinázy | |
| MXPA00008095A (en) | N-hydroxy-2-(alkyl, aryl, or heteroaryl sulfanyl, sulfinyl or sulfonyl)-3-substituted-alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors |