SK6942002A3 - Sulfonyl oxazole amine derivative, process for the preparation thereof, its use and pharmaceutical composition containing same - Google Patents

Sulfonyl oxazole amine derivative, process for the preparation thereof, its use and pharmaceutical composition containing same Download PDF

Info

Publication number: SK6942002A3
Authority: SK; Slovakia
Prior art keywords: ethyl; fluorophenyl; hydrochloride; piperidine hydrochloride; piperidine
Prior art date: 1999-11-25

Application number

SK694-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Rolf Gericke

Henning Bottcher

Michael Gassen

Hartmut Greiner

Original Assignee

Merck Patent Gmbh

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

1999-11-25

Filing date

2000-11-24

Publication date

2002-12-03

2000-11-24 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2002-12-03 Publication of SK6942002A3 publication Critical patent/SK6942002A3/sk

Links

-1 Sulfonyl oxazole amine Chemical class 0.000 title claims description 135
238000002360 preparation method Methods 0.000 title claims description 17
238000000034 method Methods 0.000 title claims description 10
239000008194 pharmaceutical composition Substances 0.000 title claims description 9
150000001875 compounds Chemical class 0.000 claims abstract description 71
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 27
150000003839 salts Chemical class 0.000 claims abstract description 26
239000012453 solvate Substances 0.000 claims abstract description 20
239000003814 drug Substances 0.000 claims abstract description 17
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
239000001301 oxygen Substances 0.000 claims abstract description 13
229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
239000000243 solution Substances 0.000 claims description 17
HVISAPYMDYXBIV-UHFFFAOYSA-N 2-(sulfonylamino)-1,3-oxazole Chemical compound O=S(=O)=NC1=NC=CO1 HVISAPYMDYXBIV-UHFFFAOYSA-N 0.000 claims description 15
239000004480 active ingredient Substances 0.000 claims description 14
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000004434 sulfur atom Chemical group 0.000 claims description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
201000000980 schizophrenia Diseases 0.000 claims description 8
208000024827 Alzheimer disease Diseases 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
208000012902 Nervous system disease Diseases 0.000 claims description 6
208000025966 Neurological disease Diseases 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
239000002775 capsule Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
231100000867 compulsive behavior Toxicity 0.000 claims description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
208000000103 Anorexia Nervosa Diseases 0.000 claims description 5
208000032841 Bulimia Diseases 0.000 claims description 5
206010006550 Bulimia nervosa Diseases 0.000 claims description 5
208000023105 Huntington disease Diseases 0.000 claims description 5
208000026139 Memory disease Diseases 0.000 claims description 5
206010036618 Premenstrual syndrome Diseases 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
150000004683 dihydrates Chemical class 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
239000000454 talc Substances 0.000 claims description 5
229910052623 talc Inorganic materials 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
229920001592 potato starch Polymers 0.000 claims description 4
235000012222 talc Nutrition 0.000 claims description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
208000030814 Eating disease Diseases 0.000 claims description 3
208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
208000018737 Parkinson disease Diseases 0.000 claims description 3
208000028017 Psychotic disease Diseases 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
239000002585 base Substances 0.000 claims description 3
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
210000003169 central nervous system Anatomy 0.000 claims description 3
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 3
235000014632 disordered eating Nutrition 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000007924 injection Substances 0.000 claims description 3
238000002347 injection Methods 0.000 claims description 3
239000008101 lactose Substances 0.000 claims description 3
235000019359 magnesium stearate Nutrition 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
230000001575 pathological effect Effects 0.000 claims description 3
235000019271 petrolatum Nutrition 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
239000000829 suppository Substances 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 claims description 3
OOSZCNKVJAVHJI-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]piperazine Chemical compound C1=CC(F)=CC=C1CN1CCNCC1 OOSZCNKVJAVHJI-UHFFFAOYSA-N 0.000 claims description 2
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
241000416162 Astragalus gummifer Species 0.000 claims description 2
208000012895 Gastric disease Diseases 0.000 claims description 2
229930006000 Sucrose Natural products 0.000 claims description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
229920001615 Tragacanth Polymers 0.000 claims description 2
239000013543 active substance Substances 0.000 claims description 2
239000003708 ampul Substances 0.000 claims description 2
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 2
229940125681 anticonvulsant agent Drugs 0.000 claims description 2
239000001961 anticonvulsive agent Substances 0.000 claims description 2
229960000686 benzalkonium chloride Drugs 0.000 claims description 2
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 2
208000015114 central nervous system disease Diseases 0.000 claims description 2
239000011248 coating agent Substances 0.000 claims description 2
238000000576 coating method Methods 0.000 claims description 2
229940110456 cocoa butter Drugs 0.000 claims description 2
235000019868 cocoa butter Nutrition 0.000 claims description 2
239000003086 colorant Substances 0.000 claims description 2
239000008298 dragée Substances 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
230000000694 effects Effects 0.000 claims description 2
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 2
239000003889 eye drop Substances 0.000 claims description 2
229940012356 eye drops Drugs 0.000 claims description 2
210000001035 gastrointestinal tract Anatomy 0.000 claims description 2
229920000159 gelatin Polymers 0.000 claims description 2
235000019322 gelatine Nutrition 0.000 claims description 2
208000002551 irritable bowel syndrome Diseases 0.000 claims description 2
238000002844 melting Methods 0.000 claims description 2
230000008018 melting Effects 0.000 claims description 2
239000004090 neuroprotective agent Substances 0.000 claims description 2
239000002664 nootropic agent Substances 0.000 claims description 2
230000001777 nootropic effect Effects 0.000 claims description 2
239000000575 pesticide Substances 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 claims description 2
239000008347 soybean phospholipid Substances 0.000 claims description 2
208000018556 stomach disease Diseases 0.000 claims description 2
239000005720 sucrose Substances 0.000 claims description 2
239000000196 tragacanth Substances 0.000 claims description 2
235000010487 tragacanth Nutrition 0.000 claims description 2
229940116362 tragacanth Drugs 0.000 claims description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 24
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims 10
ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 claims 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 4
125000002252 acyl group Chemical group 0.000 claims 4
229910052740 iodine Inorganic materials 0.000 claims 4
DRTZAIDVOGUYSP-UHFFFAOYSA-N pyridin-1-ium;chloride;hydrochloride Chemical compound Cl.Cl.C1=CC=NC=C1 DRTZAIDVOGUYSP-UHFFFAOYSA-N 0.000 claims 4
229910052717 sulfur Chemical group 0.000 claims 4
208000035475 disorder Diseases 0.000 claims 3
239000012154 double-distilled water Substances 0.000 claims 3
150000004885 piperazines Chemical class 0.000 claims 3
239000011593 sulfur Chemical group 0.000 claims 3
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 claims 3
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
XBTPCUWXQJXEGE-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-methoxyphenyl)sulfanylpiperidine Chemical compound COC1=CC=CC=C1SC1CCN(CCC=2C=CC(F)=CC=2)CC1 XBTPCUWXQJXEGE-UHFFFAOYSA-N 0.000 claims 2
PWCXGDJFAIRPEO-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylquinoline hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)(=O)C1=NC2=CC=CC=C2C=C1 PWCXGDJFAIRPEO-UHFFFAOYSA-N 0.000 claims 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
125000005842 heteroatom Chemical group 0.000 claims 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
201000010901 lateral sclerosis Diseases 0.000 claims 2
208000005264 motor neuron disease Diseases 0.000 claims 2
125000001624 naphthyl group Chemical group 0.000 claims 2
IXHWPHKAIWPAKX-UHFFFAOYSA-N pyridine;trihydrochloride Chemical compound Cl.Cl.Cl.C1=CC=NC=C1 IXHWPHKAIWPAKX-UHFFFAOYSA-N 0.000 claims 2
GPVVBCKMCIOPMN-UHFFFAOYSA-N quinolin-1-ium;hydroxide Chemical compound O.N1=CC=CC2=CC=CC=C21 GPVVBCKMCIOPMN-UHFFFAOYSA-N 0.000 claims 2
239000002400 serotonin 2A antagonist Substances 0.000 claims 2
PZNMJEJGRMIZOO-UHFFFAOYSA-N 1-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylisoquinoline hydrochloride Chemical compound Cl.C1(=NC=CC2=CC=CC=C12)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F PZNMJEJGRMIZOO-UHFFFAOYSA-N 0.000 claims 1
NYHGBDYSZKKZLT-UHFFFAOYSA-N 1-[2-(2,4-difluorophenyl)ethyl]-4-(2-fluorophenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.FC1=C(C=CC=C1)S(=O)(=O)C1CCN(CC1)CCC1=C(C=C(C=C1)F)F NYHGBDYSZKKZLT-UHFFFAOYSA-N 0.000 claims 1
ZMMKUFNZZOXWHM-UHFFFAOYSA-N 1-[2-(2,4-difluorophenyl)ethyl]-4-(2-methoxyphenyl)sulfonylpiperidine hydrochloride Chemical compound COC1=CC=CC=C1S(=O)(=O)C2CCN(CC2)CCC3=C(C=C(C=C3)F)F.Cl ZMMKUFNZZOXWHM-UHFFFAOYSA-N 0.000 claims 1
IOKOUKSRJWEGNW-UHFFFAOYSA-N 1-[2-(2,4-difluorophenyl)ethyl]-4-(2-methylphenyl)sulfonylpiperidine hydrochloride Chemical compound CC1=CC=CC=C1S(=O)(=O)C2CCN(CC2)CCC3=C(C=C(C=C3)F)F.Cl IOKOUKSRJWEGNW-UHFFFAOYSA-N 0.000 claims 1
VUGIULCWVDEFEF-UHFFFAOYSA-N 1-[2-(2,4-difluorophenyl)ethyl]-4-(4-fluorophenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)SC1CCN(CC1)CCC1=C(C=C(C=C1)F)F VUGIULCWVDEFEF-UHFFFAOYSA-N 0.000 claims 1
DOCJTNVMETXMJI-UHFFFAOYSA-N 1-[2-(2,4-difluorophenyl)ethyl]-4-(4-fluorophenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)S(=O)(=O)C1CCN(CC1)CCC1=C(C=C(C=C1)F)F DOCJTNVMETXMJI-UHFFFAOYSA-N 0.000 claims 1
MMHAHUXPBPSYHZ-UHFFFAOYSA-N 1-[2-(2-fluorophenyl)ethyl]-4-(2-methylphenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.C1(=C(C=CC=C1)SC1CCN(CC1)CCC1=C(C=CC=C1)F)C MMHAHUXPBPSYHZ-UHFFFAOYSA-N 0.000 claims 1
LYKLILOKUIMVSZ-UHFFFAOYSA-N 1-[2-(2-fluorophenyl)ethyl]-4-(4-fluorophenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)SC1CCN(CC1)CCC1=C(C=CC=C1)F LYKLILOKUIMVSZ-UHFFFAOYSA-N 0.000 claims 1
SZXHABQDSKZVKI-UHFFFAOYSA-N 1-[2-(2-fluorophenyl)ethyl]-4-(4-fluorophenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)S(=O)(=O)C1CCN(CC1)CCC1=C(C=CC=C1)F SZXHABQDSKZVKI-UHFFFAOYSA-N 0.000 claims 1
JDHSDDZLYCTAJF-UHFFFAOYSA-N 1-[2-(3,4-difluorophenyl)ethyl]-4-(2-fluorophenyl)sulfonylpiperidine hydrochloride Chemical compound C1CN(CCC1S(=O)(=O)C2=CC=CC=C2F)CCC3=CC(=C(C=C3)F)F.Cl JDHSDDZLYCTAJF-UHFFFAOYSA-N 0.000 claims 1
AMOMGUYPXKNABL-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2,4,6-trimethylphenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.CC1=C(C(=CC(=C1)C)C)SC1CCN(CC1)CCC1=CC=C(C=C1)F AMOMGUYPXKNABL-UHFFFAOYSA-N 0.000 claims 1
KYJOIFGVJQNUDR-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2,4,6-trimethylphenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)(=O)C1=C(C=C(C=C1C)C)C KYJOIFGVJQNUDR-UHFFFAOYSA-N 0.000 claims 1
SGWGKNOSVXXNJG-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-fluorophenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.FC1=C(C=CC=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F SGWGKNOSVXXNJG-UHFFFAOYSA-N 0.000 claims 1
DRVKYHPBDOXVKN-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-methoxyphenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.COC1=C(C=CC=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F DRVKYHPBDOXVKN-UHFFFAOYSA-N 0.000 claims 1
VKOBHBKRAGJMAX-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-methoxyphenyl)sulfinylpiperidine hydrochloride Chemical compound Cl.COC1=C(C=CC=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F VKOBHBKRAGJMAX-UHFFFAOYSA-N 0.000 claims 1
FWXQTBWENSXSMV-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-methoxyphenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.COC1=C(C=CC=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F FWXQTBWENSXSMV-UHFFFAOYSA-N 0.000 claims 1
IHTSYYVNJHENFJ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-methylphenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.C1(=C(C=CC=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F)C IHTSYYVNJHENFJ-UHFFFAOYSA-N 0.000 claims 1
SRPHBSKLOVTFFH-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-propan-2-ylphenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.C(C)(C)C1=C(C=CC=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F SRPHBSKLOVTFFH-UHFFFAOYSA-N 0.000 claims 1
SFADWGAXLXDXMX-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(2-propan-2-ylphenyl)sulfinylpiperidine hydrochloride Chemical compound CC(C)C1=CC=CC=C1S(=O)C2CCN(CC2)CCC3=CC=C(C=C3)F.Cl SFADWGAXLXDXMX-UHFFFAOYSA-N 0.000 claims 1
OYYKBPLEOWIIKJ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-fluorophenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F OYYKBPLEOWIIKJ-UHFFFAOYSA-N 0.000 claims 1
CKRMUDRDAWRJRH-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-fluorophenyl)sulfinylpiperidine Chemical compound C1=CC(F)=CC=C1CCN1CCC(S(=O)C=2C=CC(F)=CC=2)CC1 CKRMUDRDAWRJRH-UHFFFAOYSA-N 0.000 claims 1
LMYWKVOVJZTPHG-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-fluorophenyl)sulfonylpiperidine Chemical compound C1=CC(F)=CC=C1CCN1CCC(S(=O)(=O)C=2C=CC(F)=CC=2)CC1 LMYWKVOVJZTPHG-UHFFFAOYSA-N 0.000 claims 1
ISPRGISEAPTUCJ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-fluorophenyl)sulfonylpiperidine hydrochloride Chemical compound C1CN(CCC1S(=O)(=O)C2=CC=C(C=C2)F)CCC3=CC=C(C=C3)F.Cl ISPRGISEAPTUCJ-UHFFFAOYSA-N 0.000 claims 1
GAGIVQRSLZTRRZ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-methoxyphenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.COC1=CC=C(C=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F GAGIVQRSLZTRRZ-UHFFFAOYSA-N 0.000 claims 1
SNBDASOMTZYWQR-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-methoxyphenyl)sulfinylpiperidine hydrochloride Chemical compound Cl.COC1=CC=C(C=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F SNBDASOMTZYWQR-UHFFFAOYSA-N 0.000 claims 1
CIMWGXCDTMKAFL-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-methylphenyl)sulfinylpiperidine Chemical compound C1=CC(C)=CC=C1S(=O)C1CCN(CCC=2C=CC(F)=CC=2)CC1 CIMWGXCDTMKAFL-UHFFFAOYSA-N 0.000 claims 1
XIVPHUDHXJWUOM-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-methylphenyl)sulfinylpiperidine hydrochloride Chemical compound Cl.C1(=CC=C(C=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F)C XIVPHUDHXJWUOM-UHFFFAOYSA-N 0.000 claims 1
KDUYNDJMQQVEAG-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-methylphenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.C1(=CC=C(C=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F)C KDUYNDJMQQVEAG-UHFFFAOYSA-N 0.000 claims 1
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ZTNVNGAHIMRZQM-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-(4-methylsulfinylphenyl)sulfonylpiperidine hydrochloride Chemical compound Cl.CS(=O)C1=CC=C(C=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F ZTNVNGAHIMRZQM-UHFFFAOYSA-N 0.000 claims 1
IXMDFPSKGMIBQQ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-[4-(trifluoromethoxy)phenyl]sulfonylpiperidine hydrochloride Chemical compound Cl.FC(OC1=CC=C(C=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F)(F)F IXMDFPSKGMIBQQ-UHFFFAOYSA-N 0.000 claims 1
KBPYBKNQGMYYJN-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-[4-(trifluoromethyl)phenyl]sulfanylpiperidine hydrochloride Chemical compound Cl.FC(C1=CC=C(C=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F)(F)F KBPYBKNQGMYYJN-UHFFFAOYSA-N 0.000 claims 1
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WKTGIFGYHASLPN-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-[4-(trifluoromethyl)phenyl]sulfonylpiperidine hydrochloride Chemical compound Cl.FC(C1=CC=C(C=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F)(F)F WKTGIFGYHASLPN-UHFFFAOYSA-N 0.000 claims 1
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VVQHLYGFPBCQKR-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-thiophen-2-ylsulfonylpiperidine hydrochloride Chemical compound C1CN(CCC1S(=O)(=O)C2=CC=CS2)CCC3=CC=C(C=C3)F.Cl VVQHLYGFPBCQKR-UHFFFAOYSA-N 0.000 claims 1
NLXTVNBGKKZNGS-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)ethyl]-4-(2-methoxyphenyl)sulfanylpiperidine hydrochloride Chemical compound Cl.COC1=C(C=CC=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)OC NLXTVNBGKKZNGS-UHFFFAOYSA-N 0.000 claims 1
BZASUYKKGCQFBT-UHFFFAOYSA-N 1-[2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanylphenyl]ethanone hydrochloride Chemical compound Cl.C(C)(=O)C1=C(C=CC=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F BZASUYKKGCQFBT-UHFFFAOYSA-N 0.000 claims 1
MTHVQXPMLUTZKL-UHFFFAOYSA-N 1-[4-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanylphenyl]ethanone hydrochloride Chemical compound Cl.C(C)(=O)C1=CC=C(C=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F MTHVQXPMLUTZKL-UHFFFAOYSA-N 0.000 claims 1
OHHRXZBEJQLZOR-UHFFFAOYSA-N 1-[4-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfinylphenyl]ethanone hydrochloride Chemical compound Cl.C(C)(=O)C1=CC=C(C=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F OHHRXZBEJQLZOR-UHFFFAOYSA-N 0.000 claims 1
PTBGZESVAJXTHX-UHFFFAOYSA-N 1h-benzimidazole;hydrate Chemical compound O.C1=CC=C2NC=NC2=C1 PTBGZESVAJXTHX-UHFFFAOYSA-N 0.000 claims 1
CHIFTAQVXHNVRW-UHFFFAOYSA-N 1h-indole-3-carbonitrile Chemical compound C1=CC=C2C(C#N)=CNC2=C1 CHIFTAQVXHNVRW-UHFFFAOYSA-N 0.000 claims 1
AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 claims 1
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
ZLWUHKGDLQOHDE-UHFFFAOYSA-N 2-[1-[2-(2,4-difluorophenyl)ethyl]piperidin-4-yl]sulfanylphenol hydrochloride Chemical compound Cl.FC1=C(C=CC(=C1)F)CCN1CCC(CC1)SC1=C(C=CC=C1)O ZLWUHKGDLQOHDE-UHFFFAOYSA-N 0.000 claims 1
MKHBRKZCSSKSCR-UHFFFAOYSA-N 2-[1-[2-(2,4-difluorophenyl)ethyl]piperidin-4-yl]sulfonylphenol hydrochloride Chemical compound Cl.FC1=C(C=CC(=C1)F)CCN1CCC(CC1)S(=O)(=O)C1=C(C=CC=C1)O MKHBRKZCSSKSCR-UHFFFAOYSA-N 0.000 claims 1
XEPSCRQHSQBIRK-UHFFFAOYSA-N 2-[1-[2-(2-fluorophenyl)ethyl]piperidin-4-yl]sulfanylphenol Chemical compound OC1=CC=CC=C1SC1CCN(CCC=2C(=CC=CC=2)F)CC1 XEPSCRQHSQBIRK-UHFFFAOYSA-N 0.000 claims 1
UUKKGDSYADVGSL-UHFFFAOYSA-N 2-[1-[2-(3,4-difluorophenyl)ethyl]piperidin-4-yl]sulfanylphenol Chemical compound OC1=CC=CC=C1SC1CCN(CCC=2C=C(F)C(F)=CC=2)CC1 UUKKGDSYADVGSL-UHFFFAOYSA-N 0.000 claims 1
YKRLMTIDVDTLEP-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanyl-1,3-benzothiazole hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)SC=1SC2=C(N1)C=CC=C2 YKRLMTIDVDTLEP-UHFFFAOYSA-N 0.000 claims 1
YEMPZPQMOFOTOT-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanyl-1,3-thiazole hydrochloride Chemical compound Cl.S1C(=NC=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F YEMPZPQMOFOTOT-UHFFFAOYSA-N 0.000 claims 1
ZAPIAFGFYRUTNP-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanyl-1H-benzimidazole hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)SC1=NC2=C(N1)C=CC=C2 ZAPIAFGFYRUTNP-UHFFFAOYSA-N 0.000 claims 1
HBFZMJJHODHPEJ-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanylphenol hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)SC1=C(C=CC=C1)O HBFZMJJHODHPEJ-UHFFFAOYSA-N 0.000 claims 1
ZIWASQCQKWGHMV-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanylpyridine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)SC1=NC=CC=C1 ZIWASQCQKWGHMV-UHFFFAOYSA-N 0.000 claims 1
VVLDBVSQAYUKRW-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanylpyrimidine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)SC1=NC=CC=N1 VVLDBVSQAYUKRW-UHFFFAOYSA-N 0.000 claims 1
DWCMNEJKCMQYBP-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanylquinoline hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)SC1=NC2=CC=CC=C2C=C1 DWCMNEJKCMQYBP-UHFFFAOYSA-N 0.000 claims 1
GGIVKJCWSXWAHT-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfinylphenol hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)C1=C(C=CC=C1)O GGIVKJCWSXWAHT-UHFFFAOYSA-N 0.000 claims 1
BPLBZFRNBNNOIU-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfinylpyrimidine hydrochloride Chemical compound C1CN(CCC1S(=O)C2=NC=CC=N2)CCC3=CC=C(C=C3)F.Cl BPLBZFRNBNNOIU-UHFFFAOYSA-N 0.000 claims 1
KYTCCYXFRRLEAV-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonyl-1,3-benzothiazole hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)(=O)C=1SC2=C(N1)C=CC=C2 KYTCCYXFRRLEAV-UHFFFAOYSA-N 0.000 claims 1
NLHQQWVIEAAPMB-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonyl-1,3-thiazole hydrochloride Chemical compound C1CN(CCC1S(=O)(=O)C2=NC=CS2)CCC3=CC=C(C=C3)F.Cl NLHQQWVIEAAPMB-UHFFFAOYSA-N 0.000 claims 1
MPNWIAAXNVURTF-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonyl-6-methoxypyridine hydrochloride Chemical compound Cl.COC1=CC=CC(=N1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F MPNWIAAXNVURTF-UHFFFAOYSA-N 0.000 claims 1
GNQIOPSDOQAKIV-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylphenol hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)(=O)C1=C(C=CC=C1)O GNQIOPSDOQAKIV-UHFFFAOYSA-N 0.000 claims 1
PPVFWWPACYVQKE-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylpyridine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)(=O)C1=NC=CC=C1 PPVFWWPACYVQKE-UHFFFAOYSA-N 0.000 claims 1
APHCXDRBCIUTIF-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylpyrimidine hydrochloride Chemical compound C1CN(CCC1S(=O)(=O)C2=NC=CC=N2)CCC3=CC=C(C=C3)F.Cl APHCXDRBCIUTIF-UHFFFAOYSA-N 0.000 claims 1
RXSJYCBBADSOGD-UHFFFAOYSA-N 2-chloro-6-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfinylpyridine hydrochloride Chemical compound Cl.ClC1=NC(=CC=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F RXSJYCBBADSOGD-UHFFFAOYSA-N 0.000 claims 1
PYCGESBPLWWWGR-UHFFFAOYSA-N 2-chloro-6-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylpyridine Chemical compound C1=CC(F)=CC=C1CCN1CCC(S(=O)(=O)C=2N=C(Cl)C=CC=2)CC1 PYCGESBPLWWWGR-UHFFFAOYSA-N 0.000 claims 1
SEUMFTZWUNHUAY-UHFFFAOYSA-N 2-chloro-6-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylpyridine hydrochloride Chemical compound Cl.ClC1=NC(=CC=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F SEUMFTZWUNHUAY-UHFFFAOYSA-N 0.000 claims 1
GRXDJABVNGUGCW-UHFFFAOYSA-N 2-chloro-6-piperidin-4-ylsulfanylpyridine;hydrochloride Chemical compound Cl.ClC1=CC=CC(SC2CCNCC2)=N1 GRXDJABVNGUGCW-UHFFFAOYSA-N 0.000 claims 1
YRNVVCKAZGTRKX-UHFFFAOYSA-N 3-[1-[2-(2,4-difluorophenyl)ethyl]piperidin-4-yl]sulfonyl-1H-indole hydrochloride Chemical compound Cl.N1C=C(C2=CC=CC=C12)S(=O)(=O)C1CCN(CC1)CCC1=C(C=C(C=C1)F)F YRNVVCKAZGTRKX-UHFFFAOYSA-N 0.000 claims 1
YRZLGNJXTPRKSS-UHFFFAOYSA-N 3-[1-[2-(2-fluorophenyl)ethyl]piperidin-4-yl]sulfanyl-1H-indole hydrochloride Chemical compound Cl.N1C=C(C2=CC=CC=C12)SC1CCN(CC1)CCC1=C(C=CC=C1)F YRZLGNJXTPRKSS-UHFFFAOYSA-N 0.000 claims 1
IIOQEQFWPNPJEG-UHFFFAOYSA-N 3-[1-[2-(2-methylphenyl)ethyl]piperidin-4-yl]sulfanyl-1H-indole hydrochloride Chemical compound Cl.N1C=C(C2=CC=CC=C12)SC1CCN(CC1)CCC1=C(C=CC=C1)C IIOQEQFWPNPJEG-UHFFFAOYSA-N 0.000 claims 1
VYFJZHJFVXYQCJ-UHFFFAOYSA-N 3-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanyl-1H-indole hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)SC1=CNC2=CC=CC=C12 VYFJZHJFVXYQCJ-UHFFFAOYSA-N 0.000 claims 1
LFMHDGQPTJZHSO-UHFFFAOYSA-N 3-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonyl-1H-indole hydrochloride Chemical compound Cl.N1C=C(C2=CC=CC=C12)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F LFMHDGQPTJZHSO-UHFFFAOYSA-N 0.000 claims 1
FJECARWTSYXFDL-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)sulfanyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.ClC1=C(C=CC=C1Cl)SC1CCN(CC1)CCC1=CC=C(C=C1)F FJECARWTSYXFDL-UHFFFAOYSA-N 0.000 claims 1
KNCZNTXLPHHAEL-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)sulfinyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.ClC1=C(C=CC=C1Cl)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F KNCZNTXLPHHAEL-UHFFFAOYSA-N 0.000 claims 1
BOSQMPVXIPTWNO-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)sulfonyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.ClC1=C(C=CC=C1Cl)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F BOSQMPVXIPTWNO-UHFFFAOYSA-N 0.000 claims 1
NVAXRWWKLXHHNT-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)sulfanyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.ClC1=C(C=CC(=C1)Cl)SC1CCN(CC1)CCC1=CC=C(C=C1)F NVAXRWWKLXHHNT-UHFFFAOYSA-N 0.000 claims 1
BAPFMLZNFOKSOI-UHFFFAOYSA-N 4-(2,4-difluorophenyl)sulfinyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.FC1=C(C=CC(=C1)F)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F BAPFMLZNFOKSOI-UHFFFAOYSA-N 0.000 claims 1
WXMTZGJUCVZZNV-UHFFFAOYSA-N 4-(2,4-dimethoxyphenyl)sulfonyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.COC1=C(C=CC(=C1)OC)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F WXMTZGJUCVZZNV-UHFFFAOYSA-N 0.000 claims 1
FMLMOPSRTRPILA-UHFFFAOYSA-N 4-(2,4-dimethylphenyl)sulfanyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.CC1=C(C=CC(=C1)C)SC1CCN(CC1)CCC1=CC=C(C=C1)F FMLMOPSRTRPILA-UHFFFAOYSA-N 0.000 claims 1
TYFPDOLMNCEERB-UHFFFAOYSA-N 4-(2,4-dimethylphenyl)sulfinyl-1-[2-(2-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.FC1=C(C=CC=C1)CCN1CCC(CC1)S(=O)C1=C(C=C(C=C1)C)C TYFPDOLMNCEERB-UHFFFAOYSA-N 0.000 claims 1
ITDOUFIBTWCKGD-UHFFFAOYSA-N 4-(2-chlorophenyl)sulfanyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.ClC1=C(C=CC=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F ITDOUFIBTWCKGD-UHFFFAOYSA-N 0.000 claims 1
VTZRYVYNSZDVFV-UHFFFAOYSA-N 4-(2-chlorophenyl)sulfonyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound C1CN(CCC1S(=O)(=O)C2=CC=CC=C2Cl)CCC3=CC=C(C=C3)F.Cl VTZRYVYNSZDVFV-UHFFFAOYSA-N 0.000 claims 1
BFJNBULNMSZKDS-UHFFFAOYSA-N 4-(2-ethylphenyl)sulfanyl-1-[2-(4-fluorophenyl)ethyl]piperidine Chemical compound CCC1=CC=CC=C1SC1CCN(CCC=2C=CC(F)=CC=2)CC1 BFJNBULNMSZKDS-UHFFFAOYSA-N 0.000 claims 1
VSBTUHUTKWCQMX-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfanyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.ClC1=CC=C(C=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F VSBTUHUTKWCQMX-UHFFFAOYSA-N 0.000 claims 1
AIVPBNAVFZREPX-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfonyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound C1CN(CCC1S(=O)(=O)C2=CC=C(C=C2)Cl)CCC3=CC=C(C=C3)F.Cl AIVPBNAVFZREPX-UHFFFAOYSA-N 0.000 claims 1
UKFYELLYJRVBHI-UHFFFAOYSA-N 4-(4-tert-butylphenyl)sulfanyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.C(C)(C)(C)C1=CC=C(C=C1)SC1CCN(CC1)CCC1=CC=C(C=C1)F UKFYELLYJRVBHI-UHFFFAOYSA-N 0.000 claims 1
AFDZRSQBXBVTOJ-UHFFFAOYSA-N 4-(4-tert-butylphenyl)sulfinyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.C(C)(C)(C)C1=CC=C(C=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F AFDZRSQBXBVTOJ-UHFFFAOYSA-N 0.000 claims 1
CQCVOAKYPXEZPH-UHFFFAOYSA-N 4-(4-tert-butylphenyl)sulfonyl-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F CQCVOAKYPXEZPH-UHFFFAOYSA-N 0.000 claims 1
CSYQIIIFIGQBJD-UHFFFAOYSA-N 4-(benzenesulfinyl)-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.C1(=CC=CC=C1)S(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F CSYQIIIFIGQBJD-UHFFFAOYSA-N 0.000 claims 1
KXFOIKITNHSIFV-UHFFFAOYSA-N 4-(benzenesulfonyl)-1-[2-(4-fluorophenyl)ethyl]piperidine hydrochloride Chemical compound Cl.C1(=CC=CC=C1)S(=O)(=O)C1CCN(CC1)CCC1=CC=C(C=C1)F KXFOIKITNHSIFV-UHFFFAOYSA-N 0.000 claims 1
RMPRMZDUTXSHSS-UHFFFAOYSA-N 4-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfanylphenol hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)SC1=CC=C(C=C1)O RMPRMZDUTXSHSS-UHFFFAOYSA-N 0.000 claims 1
VLGHXWKAHKGOIO-UHFFFAOYSA-N 4-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfinylphenol hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)C1=CC=C(C=C1)O VLGHXWKAHKGOIO-UHFFFAOYSA-N 0.000 claims 1
NEGYEAVJKDEUFR-UHFFFAOYSA-N 4-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfinylpyridine dihydrochloride Chemical compound Cl.Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)C1=CC=NC=C1 NEGYEAVJKDEUFR-UHFFFAOYSA-N 0.000 claims 1
JBEOOYKLQDCTQV-UHFFFAOYSA-N 4-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylphenol hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)(=O)C1=CC=C(C=C1)O JBEOOYKLQDCTQV-UHFFFAOYSA-N 0.000 claims 1
PMSWKOVWENXTPW-UHFFFAOYSA-N 4-[1-[2-(4-fluorophenyl)ethyl]piperidin-4-yl]sulfonylpyridine dihydrochloride Chemical compound Cl.Cl.FC1=CC=C(C=C1)CCN1CCC(CC1)S(=O)(=O)C1=CC=NC=C1 PMSWKOVWENXTPW-UHFFFAOYSA-N 0.000 claims 1
PEJMCXKIVQXEBO-UHFFFAOYSA-N 4-[1-[2-(5-chlorothiophen-2-yl)ethyl]piperidin-4-yl]sulfanylbenzonitrile hydrochloride Chemical compound Cl.ClC1=CC=C(S1)CCN1CCC(CC1)SC1=CC=C(C#N)C=C1 PEJMCXKIVQXEBO-UHFFFAOYSA-N 0.000 claims 1
ATZJXHWAMNYNCU-UHFFFAOYSA-N 4-[1-[2-(5-chlorothiophen-2-yl)ethyl]piperidin-4-yl]sulfinylbenzonitrile hydrochloride Chemical compound Cl.ClC1=CC=C(S1)CCN1CCC(CC1)S(=O)C1=CC=C(C#N)C=C1 ATZJXHWAMNYNCU-UHFFFAOYSA-N 0.000 claims 1
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239000007943 implant Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
BNKLRYPCKHKVII-UHFFFAOYSA-N n-[1-(benzenesulfonyl)-2,2,2-trichloroethyl]thiophene-2-carboxamide Chemical compound C=1C=CC=CC=1S(=O)(=O)C(C(Cl)(Cl)Cl)NC(=O)C1=CC=CS1 BNKLRYPCKHKVII-UHFFFAOYSA-N 0.000 description 1
ZLZNCOXBJTYTGW-UHFFFAOYSA-N n-[1-(benzenesulfonyl)-2,2-dichloroethenyl]pyridine-3-carboxamide Chemical compound C=1C=CC=CC=1S(=O)(=O)C(=C(Cl)Cl)NC(=O)C1=CC=CN=C1 ZLZNCOXBJTYTGW-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
210000001577 neostriatum Anatomy 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
210000001009 nucleus accumben Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000003751 serotonin 6 antagonist Substances 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical class [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000016978 synaptic transmission, cholinergic Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
239000003029 tricyclic antidepressant agent Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

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- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- 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
- 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
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
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- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
- A—HUMAN NECESSITIES
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
- 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
- C07D307/56—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 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
- C07D307/68—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
- 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
- C07D333/38—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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Addiction (AREA)
Rheumatology (AREA)
Anesthesiology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Surgery (AREA)
Psychology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

SK694-2002A 1999-11-25 2000-11-24 Sulfonyl oxazole amine derivative, process for the preparation thereof, its use and pharmaceutical composition containing same SK6942002A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19956791A DE19956791A1 (de)	1999-11-25	1999-11-25	Neue Sulfonyloxazolamine
PCT/EP2000/011734 WO2001038316A2 (de)	1999-11-25	2000-11-24	Sulfonyloxazolamine und deren verwendung als 5-ht6 rezeptorliganden

Publications (1)

Publication Number	Publication Date
SK6942002A3 true SK6942002A3 (en)	2002-12-03

Family

ID=7930321

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK694-2002A SK6942002A3 (en)	1999-11-25	2000-11-24	Sulfonyl oxazole amine derivative, process for the preparation thereof, its use and pharmaceutical composition containing same

Country Status (18)

Country	Link
US (1)	US6737426B1 (de)
EP (1)	EP1233963A2 (de)
JP (1)	JP2003514902A (de)
KR (1)	KR20020058020A (de)
CN (1)	CN1423649A (de)
AR (1)	AR026589A1 (de)
AU (1)	AU3004201A (de)
BR (1)	BR0015814A (de)
CA (1)	CA2389679A1 (de)
CZ (1)	CZ20021687A3 (de)
DE (1)	DE19956791A1 (de)
HU (1)	HUP0204149A3 (de)
MX (1)	MXPA02005092A (de)
NO (1)	NO20022455D0 (de)
PL (1)	PL355152A1 (de)
SK (1)	SK6942002A3 (de)
WO (1)	WO2001038316A2 (de)
ZA (1)	ZA200203365B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10129940A1 (de) *	2001-06-13	2002-12-19	Merck Patent Gmbh	Sulfonyloxazolamine als therapeutische Wirkstoffe
WO2008061248A2 (en) *	2006-11-16	2008-05-22	The Regents Of The University Of California	Phenylsulfoxyoxazole compound inhibitors of urea transporters
DE602007012683D1 (de) *	2007-07-19	2011-04-07	Esteve Labor Dr	Substituierte Tetrahydro-Chinolinsulfonamidverbindungen, ihre Herstellung und ihre Verwendung als Medikamente
RU2443697C1 (ru) *	2010-12-21	2012-02-27	Александр Васильевич Иващенко	Замещенные метил-амины, антагонисты серотониновых 5-ht6 рецепторов, способы получения и применения
KR102533605B1 (ko) *	2018-01-10	2023-05-17	주식회사 라이조테크	신규한 페닐설포닐 옥사졸 유도체 및 이의 용도

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0930302B1 (de)	1998-01-16	2003-04-02	F.Hoffmann-La Roche Ag	Benzosulfonderivate
US6194410B1 (en) *	1998-03-11	2001-02-27	Hoffman-La Roche Inc.	Pyrazolopyrimidine and pyrazolines and process for preparation thereof
DE19858593A1 (de)	1998-12-18	2000-06-21	Merck Patent Gmbh	Sulfonyloxazolamine als therapeutische Wirkstoffe

1999
- 1999-11-25 DE DE19956791A patent/DE19956791A1/de not_active Withdrawn
2000
- 2000-11-23 AR ARP000106186A patent/AR026589A1/es unknown
- 2000-11-24 CZ CZ20021687A patent/CZ20021687A3/cs unknown
- 2000-11-24 JP JP2001540079A patent/JP2003514902A/ja active Pending
- 2000-11-24 BR BR0015814-3A patent/BR0015814A/pt not_active Application Discontinuation
- 2000-11-24 MX MXPA02005092A patent/MXPA02005092A/es unknown
- 2000-11-24 CN CN00816010A patent/CN1423649A/zh active Pending
- 2000-11-24 PL PL00355152A patent/PL355152A1/xx unknown
- 2000-11-24 AU AU30042/01A patent/AU3004201A/en not_active Abandoned
- 2000-11-24 KR KR1020027006349A patent/KR20020058020A/ko not_active Withdrawn
- 2000-11-24 SK SK694-2002A patent/SK6942002A3/sk unknown
- 2000-11-24 US US10/148,078 patent/US6737426B1/en not_active Expired - Fee Related
- 2000-11-24 HU HU0204149A patent/HUP0204149A3/hu unknown
- 2000-11-24 EP EP00990614A patent/EP1233963A2/de not_active Withdrawn
- 2000-11-24 CA CA002389679A patent/CA2389679A1/en not_active Abandoned
- 2000-11-24 WO PCT/EP2000/011734 patent/WO2001038316A2/de not_active Ceased
2002
- 2002-04-26 ZA ZA200203365A patent/ZA200203365B/en unknown
- 2002-05-24 NO NO20022455A patent/NO20022455D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
ZA200203365B (en)	2003-10-07
CZ20021687A3 (cs)	2002-08-14
US6737426B1 (en)	2004-05-18
DE19956791A1 (de)	2001-05-31
BR0015814A (pt)	2002-07-23
PL355152A1 (en)	2004-04-05
HUP0204149A3 (en)	2005-04-28
NO20022455L (no)	2002-05-24
NO20022455D0 (no)	2002-05-24
EP1233963A2 (de)	2002-08-28
CN1423649A (zh)	2003-06-11
CA2389679A1 (en)	2001-05-31
MXPA02005092A (es)	2002-11-07
WO2001038316A2 (de)	2001-05-31
WO2001038316A3 (de)	2001-10-18
AR026589A1 (es)	2003-02-19
KR20020058020A (ko)	2002-07-12
JP2003514902A (ja)	2003-04-22
HUP0204149A2 (hu)	2003-04-28
AU3004201A (en)	2001-06-04

Publication	Publication Date	Title
DK2505586T3 (en)	2016-05-30	INDOLIC COMPOUND AND PHARMACEUTICAL APPLICATION THEREOF
EP2555768B1 (de)	2018-08-29	Ire-1-inhibitoren
AU2007256708B2 (en)	2011-12-15	Organic compounds
KR101551313B1 (ko)	2015-09-09	신규한 인덴 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 망막 질환의 예방 또는 치료용 약학적 조성물
CZ237094A3 (en)	1995-04-12	Derivatives of piperidine and piperazine, process of their preparation, pharmaceutical compositions based thereon and process of their preparation as well as use of said derivatives in the preparation of medicaments
WO2011038579A1 (en)	2011-04-07	Compounds and compositions as protein kinase inhibitors
KR20020073492A (ko)	2002-09-26	5-ｈｔ2ａ 수용체 길항제로 작용하는 피페리딘 및피페라진 유도체
CZ281566B6 (cs)	1996-11-13	Derivát indolu, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje
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