SI2793883T1 - Trpm8 antagonists - Google Patents
Trpm8 antagonists Download PDFInfo
- Publication number
- SI2793883T1 SI2793883T1 SI201231328T SI201231328T SI2793883T1 SI 2793883 T1 SI2793883 T1 SI 2793883T1 SI 201231328 T SI201231328 T SI 201231328T SI 201231328 T SI201231328 T SI 201231328T SI 2793883 T1 SI2793883 T1 SI 2793883T1
- Authority
- SI
- Slovenia
- Prior art keywords
- thiazole
- carboxylate
- ethyl
- oxy
- fluorophenyl
- Prior art date
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- 102000003610 TRPM8 Human genes 0.000 title claims abstract 5
- 101150111302 Trpm8 gene Proteins 0.000 title claims abstract 5
- 239000005557 antagonist Substances 0.000 title claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract 17
- 208000002193 Pain Diseases 0.000 claims abstract 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 4
- 208000003251 Pruritus Diseases 0.000 claims abstract 3
- 201000010099 disease Diseases 0.000 claims abstract 3
- 230000000694 effects Effects 0.000 claims abstract 2
- 208000028867 ischemia Diseases 0.000 claims abstract 2
- 230000004770 neurodegeneration Effects 0.000 claims abstract 2
- 208000020016 psychiatric disease Diseases 0.000 claims abstract 2
- 208000023504 respiratory system disease Diseases 0.000 claims abstract 2
- -1 (trifluoromethyl) benzyl Chemical group 0.000 claims 112
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 64
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 26
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 21
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 18
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 15
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 14
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000002999 4-(trifluoromethyl)benzoyl group Chemical group FC(C1=CC=C(C(=O)*)C=C1)(F)F 0.000 claims 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 11
- 229910052708 sodium Inorganic materials 0.000 claims 10
- 239000011734 sodium Substances 0.000 claims 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 9
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 8
- 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 claims 8
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 7
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 7
- TVKXJECNMMOPNE-UHFFFAOYSA-N 2-(3-fluorophenyl)-4-hydroxy-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)c1sc(nc1O)-c1cccc(F)c1 TVKXJECNMMOPNE-UHFFFAOYSA-N 0.000 claims 6
- QCLLVUJFJHPWKW-UHFFFAOYSA-N 2-(3-fluorophenyl)-5-(5-methyl-1,2,4-oxadiazol-3-yl)-1,3-oxazol-4-ol Chemical compound Cc1nc(no1)-c1oc(nc1O)-c1cccc(F)c1 QCLLVUJFJHPWKW-UHFFFAOYSA-N 0.000 claims 6
- YTBXQOVLYUPQLG-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-hydroxy-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)c1sc(nc1O)-c1ccc(Cl)cc1 YTBXQOVLYUPQLG-UHFFFAOYSA-N 0.000 claims 6
- AFKVXQZTPWAINO-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-(5-methyl-1H-1,2,4-triazol-3-yl)-1,3-thiazol-4-ol Chemical compound Cc1nnc([nH]1)-c1sc(nc1O)-c1ccc(Cl)cc1 AFKVXQZTPWAINO-UHFFFAOYSA-N 0.000 claims 6
- JRCDCBRTKJWGPP-UHFFFAOYSA-N 3-[4-[(4-chlorophenyl)methoxy]-2-(3-fluorophenyl)-1,3-thiazol-5-yl]-5-methyl-1,2,4-oxadiazole Chemical compound O1C(C)=NC(C2=C(N=C(S2)C=2C=C(F)C=CC=2)OCC=2C=CC(Cl)=CC=2)=N1 JRCDCBRTKJWGPP-UHFFFAOYSA-N 0.000 claims 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 6
- FOYAGDWGDGPIJQ-UHFFFAOYSA-N 4-[(4-chlorophenyl)methoxy]-2-(4-methylphenyl)-1,3-oxazole-5-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=NC(OCC=2C=CC(Cl)=CC=2)=C(C(O)=O)O1 FOYAGDWGDGPIJQ-UHFFFAOYSA-N 0.000 claims 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 6
- YKGZUJNWHSCMEJ-UHFFFAOYSA-N 4-methoxy-2-(4-methylphenyl)-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(OC)N=C1C1=CC=C(C)C=C1 YKGZUJNWHSCMEJ-UHFFFAOYSA-N 0.000 claims 6
- VGICXJJOUFTOBV-UFBFVWGQSA-N CC(C)[C@H](CC[C@@H](C)C1)[C@@H]1[S+]1C(C2=CC=C(C)C=C2)=NC(O)=C1C([O-])=O Chemical compound CC(C)[C@H](CC[C@@H](C)C1)[C@@H]1[S+]1C(C2=CC=C(C)C=C2)=NC(O)=C1C([O-])=O VGICXJJOUFTOBV-UFBFVWGQSA-N 0.000 claims 6
- SHVRAFGUKKOKIO-UHFFFAOYSA-N chembl3261228 Chemical compound OC1=C(C(=O)OCC)SC(C=2C=CN=CC=2)=N1 SHVRAFGUKKOKIO-UHFFFAOYSA-N 0.000 claims 6
- PRIPNLJZMWEWRE-UHFFFAOYSA-N ethyl 2-[4-[(2-fluorophenyl)methoxy]phenyl]-4-hydroxy-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)c1sc(nc1O)-c1ccc(OCc2ccccc2F)cc1 PRIPNLJZMWEWRE-UHFFFAOYSA-N 0.000 claims 6
- AEMHIGYVMJFQMU-UHFFFAOYSA-N ethyl 2-[4-[(4-fluorophenyl)methoxy]phenyl]-4-hydroxy-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)c1sc(nc1O)-c1ccc(OCc2ccc(F)cc2)cc1 AEMHIGYVMJFQMU-UHFFFAOYSA-N 0.000 claims 6
- OTMJBFXMCKZHDP-UHFFFAOYSA-N ethyl 2-phenyl-4-(2-pyrrolidin-1-ylethylamino)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC=CC=2)=NC=1NCCN1CCCC1 OTMJBFXMCKZHDP-UHFFFAOYSA-N 0.000 claims 6
- UHECOXPCGQYXBE-UHFFFAOYSA-N ethyl 4-(2-aminoethoxy)-2-(4-chlorophenyl)-1,3-thiazole-5-carboxylate Chemical compound NCCOC1=C(C(=O)OCC)SC(C=2C=CC(Cl)=CC=2)=N1 UHECOXPCGQYXBE-UHFFFAOYSA-N 0.000 claims 6
- AQUOSENVZNZRMV-UHFFFAOYSA-N ethyl 4-(benzylamino)-2-(3-fluorophenyl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=C(F)C=CC=2)=NC=1NCC1=CC=CC=C1 AQUOSENVZNZRMV-UHFFFAOYSA-N 0.000 claims 6
- QBMYWQPVJMZBLO-UHFFFAOYSA-N ethyl 4-[(4-chlorophenyl)methoxy]-2-phenyl-1,3-oxazole-5-carboxylate Chemical compound CCOC(=O)C=1OC(C=2C=CC=CC=2)=NC=1OCC1=CC=C(Cl)C=C1 QBMYWQPVJMZBLO-UHFFFAOYSA-N 0.000 claims 6
- FRKLLEYVAMRCNV-UHFFFAOYSA-N ethyl 4-hydroxy-2-(4-methylphenyl)-1,3-oxazole-5-carboxylate Chemical compound CCOC(=O)c1oc(nc1O)-c1ccc(C)cc1 FRKLLEYVAMRCNV-UHFFFAOYSA-N 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 208000013403 hyperactivity Diseases 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- FPLQXRZLRODTMM-UHFFFAOYSA-N ethyl 2-(4-fluorophenyl)-4-hydroxy-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)c1sc(nc1O)-c1ccc(F)cc1 FPLQXRZLRODTMM-UHFFFAOYSA-N 0.000 claims 5
- BDPWIJQLVXPZML-UHFFFAOYSA-N ethyl 2-(4-methylphenyl)-4-[[4-(trifluoromethyl)benzoyl]amino]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC(C)=CC=2)=NC=1NC(=O)C1=CC=C(C(F)(F)F)C=C1 BDPWIJQLVXPZML-UHFFFAOYSA-N 0.000 claims 5
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 5
- LCEWMKKEBKMJMD-UHFFFAOYSA-N 2-(3-fluorophenyl)-5-(5-methyl-1,2,4-oxadiazol-3-yl)-1,3-thiazol-4-ol Chemical compound Cc1nc(no1)-c1sc(nc1O)-c1cccc(F)c1 LCEWMKKEBKMJMD-UHFFFAOYSA-N 0.000 claims 4
- FVWOOMDCHNGWNY-UHFFFAOYSA-N 2-(3-fluorophenyl)-5-(5-methyl-1H-1,2,4-triazol-3-yl)-1,3-thiazol-4-ol Chemical compound Cc1nnc([nH]1)-c1sc(nc1O)-c1cccc(F)c1 FVWOOMDCHNGWNY-UHFFFAOYSA-N 0.000 claims 4
- VSTOXGIORCTKQC-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(methoxymethoxy)-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(OCOC)N=C1C1=CC=C(Cl)C=C1 VSTOXGIORCTKQC-UHFFFAOYSA-N 0.000 claims 4
- LHIYFYBPQCTBSB-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-[(2-chlorophenyl)methoxy]-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC(Cl)=CC=2)=NC=1OCC1=CC=CC=C1Cl LHIYFYBPQCTBSB-UHFFFAOYSA-N 0.000 claims 4
- IBWIODBONDUNGG-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-(5-methyl-1,2,4-oxadiazol-3-yl)-1,3-thiazol-4-ol Chemical compound Cc1nc(no1)-c1sc(nc1O)-c1ccc(Cl)cc1 IBWIODBONDUNGG-UHFFFAOYSA-N 0.000 claims 4
- OVRBITSOHARNPZ-UHFFFAOYSA-N 2-phenyl-4-[4-(trifluoromethyl)benzoyl]oxy-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=NC=1OC(=O)C1=CC=C(C(F)(F)F)C=C1 OVRBITSOHARNPZ-UHFFFAOYSA-N 0.000 claims 4
- OBPZBZRLFJAFAB-UHFFFAOYSA-N 3-[4-[(4-chlorophenyl)methoxy]-2-(3-fluorophenyl)-1,3-oxazol-5-yl]-5-methyl-1,2,4-oxadiazole Chemical compound O1C(C)=NC(C2=C(N=C(O2)C=2C=C(F)C=CC=2)OCC=2C=CC(Cl)=CC=2)=N1 OBPZBZRLFJAFAB-UHFFFAOYSA-N 0.000 claims 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- MCAYASKMFOXJEE-UHFFFAOYSA-N 4-(2-aminoethylamino)-2-(3-fluorophenyl)-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(NCCN)N=C1C1=CC=CC(F)=C1 MCAYASKMFOXJEE-UHFFFAOYSA-N 0.000 claims 4
- WCTHAEUXJNZZHZ-UHFFFAOYSA-N 4-[(2-chlorophenyl)methoxy]-2-(3-fluorophenyl)-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=C(F)C=CC=2)=NC=1OCC1=CC=CC=C1Cl WCTHAEUXJNZZHZ-UHFFFAOYSA-N 0.000 claims 4
- QGFFUALUHPYUGQ-UHFFFAOYSA-N 4-hydroxy-2-(4-methylphenyl)-1,3-thiazole-5-carboxylic acid Chemical compound Cc1ccc(cc1)-c1nc(O)c(s1)C(O)=O QGFFUALUHPYUGQ-UHFFFAOYSA-N 0.000 claims 4
- CPFUQOHMVGJEHK-UHFFFAOYSA-N ethyl 2-(3-fluorophenyl)-5-hydroxy-1,3-thiazole-4-carboxylate Chemical compound S1C(O)=C(C(=O)OCC)N=C1C1=CC=CC(F)=C1 CPFUQOHMVGJEHK-UHFFFAOYSA-N 0.000 claims 4
- TVZQRYJIBOLLHJ-UHFFFAOYSA-N ethyl 2-(4-fluorophenyl)-4-(trifluoromethylsulfonyloxy)-1,3-thiazole-5-carboxylate Chemical compound FC(F)(F)S(=O)(=O)OC1=C(C(=O)OCC)SC(C=2C=CC(F)=CC=2)=N1 TVZQRYJIBOLLHJ-UHFFFAOYSA-N 0.000 claims 4
- OZAQRBPRKKUZCR-UHFFFAOYSA-N ethyl 2-[4-(2-fluorophenyl)phenyl]-4-hydroxy-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)c1sc(nc1O)-c1ccc(cc1)-c1ccccc1F OZAQRBPRKKUZCR-UHFFFAOYSA-N 0.000 claims 4
- DJXXLZXDFIZYAV-UHFFFAOYSA-N ethyl 2-phenyl-4-phenylmethoxy-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=CC=CC=2)=NC=1OCC1=CC=CC=C1 DJXXLZXDFIZYAV-UHFFFAOYSA-N 0.000 claims 4
- JSJVUQCYPHREEV-UHFFFAOYSA-N ethyl 4-acetamido-2-(4-methylphenyl)-1,3-thiazole-5-carboxylate Chemical compound CC(=O)NC1=C(C(=O)OCC)SC(C=2C=CC(C)=CC=2)=N1 JSJVUQCYPHREEV-UHFFFAOYSA-N 0.000 claims 4
- ZLIFVJLZPUYPTQ-UHFFFAOYSA-N ethyl 4-amino-2-(4-fluorophenyl)-1,3-thiazole-5-carboxylate;hydrochloride Chemical compound Cl.NC1=C(C(=O)OCC)SC(C=2C=CC(F)=CC=2)=N1 ZLIFVJLZPUYPTQ-UHFFFAOYSA-N 0.000 claims 4
- JMCFJZLLEDXUBF-UHFFFAOYSA-N ethyl 4-hydroxy-2-[4-[2-(trifluoromethyl)phenyl]phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)c1sc(nc1O)-c1ccc(cc1)-c1ccccc1C(F)(F)F JMCFJZLLEDXUBF-UHFFFAOYSA-N 0.000 claims 4
- YYDRFBXEISLYAR-UHFFFAOYSA-N ethyl 4-hydroxy-2-phenyl-1,3-oxazole-5-carboxylate Chemical compound CCOC(=O)c1oc(nc1O)-c1ccccc1 YYDRFBXEISLYAR-UHFFFAOYSA-N 0.000 claims 4
- HNFMHECDJPDLJL-UHFFFAOYSA-N ethyl 4-methoxy-2-(4-methylphenyl)-1,3-thiazole-5-carboxylate Chemical compound COC1=C(C(=O)OCC)SC(C=2C=CC(C)=CC=2)=N1 HNFMHECDJPDLJL-UHFFFAOYSA-N 0.000 claims 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 4
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims 3
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims 3
- OKEASJIKYMBOPX-UHFFFAOYSA-N 2-(3-fluorophenyl)-4-[4-(trifluoromethyl)benzoyl]oxy-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=C(F)C=CC=2)=NC=1OC(=O)C1=CC=C(C(F)(F)F)C=C1 OKEASJIKYMBOPX-UHFFFAOYSA-N 0.000 claims 3
- BWJCGZISWJGCQH-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(methoxymethoxy)-1,3-thiazole-5-carboxamide Chemical compound S1C(C(N)=O)=C(OCOC)N=C1C1=CC=C(Cl)C=C1 BWJCGZISWJGCQH-UHFFFAOYSA-N 0.000 claims 3
- RWZMAPPEUKYVHM-UHFFFAOYSA-N 2-(4-methylphenyl)-4-[4-(trifluoromethyl)benzoyl]oxy-1,3-thiazole-5-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=NC(OC(=O)C=2C=CC(=CC=2)C(F)(F)F)=C(C(O)=O)S1 RWZMAPPEUKYVHM-UHFFFAOYSA-N 0.000 claims 3
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims 3
- 208000005615 Interstitial Cystitis Diseases 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000005605 benzo group Chemical group 0.000 claims 3
- 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 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- UOXAZQMUZQVFJK-UHFFFAOYSA-N ethyl 2-(3-fluorophenyl)-4-(pyridin-3-ylmethylamino)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=C(F)C=CC=2)=NC=1NCC1=CC=CN=C1 UOXAZQMUZQVFJK-UHFFFAOYSA-N 0.000 claims 3
- JWOAWAWCNCDTIP-UHFFFAOYSA-N ethyl 2-(4-chlorophenyl)-4-(methoxymethoxy)-1,3-thiazole-5-carboxylate Chemical compound COCOC1=C(C(=O)OCC)SC(C=2C=CC(Cl)=CC=2)=N1 JWOAWAWCNCDTIP-UHFFFAOYSA-N 0.000 claims 3
- UUCPUPJGRDKFIY-UHFFFAOYSA-N ethyl 4-(2-aminoethylamino)-2-[3-[2-(trifluoromethyl)phenyl]phenyl]-1,3-thiazole-5-carboxylate Chemical compound NCCNC1=C(C(=O)OCC)SC(C=2C=C(C=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=N1 UUCPUPJGRDKFIY-UHFFFAOYSA-N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- GEXKJFVGFXYQSX-UHFFFAOYSA-N methyl 2-(2,4-difluorophenyl)-4-hydroxy-1,3-thiazole-5-carboxylate Chemical compound COC(=O)c1sc(nc1O)-c1ccc(F)cc1F GEXKJFVGFXYQSX-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000006308 propyl amino group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- LXRMRAFGUVWYBV-UHFFFAOYSA-M sodium;4-[(2-chlorophenyl)methoxy]-2-(3-fluorophenyl)-1,3-thiazole-5-carboxylate Chemical compound [Na+].[O-]C(=O)C=1SC(C=2C=C(F)C=CC=2)=NC=1OCC1=CC=CC=C1Cl LXRMRAFGUVWYBV-UHFFFAOYSA-M 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims 2
- YZVFSQQHQPPKNX-UHFFFAOYSA-N 1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C1=CN=CS1 YZVFSQQHQPPKNX-UHFFFAOYSA-N 0.000 claims 2
- GMTASVFGLFONMF-UHFFFAOYSA-N 2-(3-chlorophenyl)-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(=O)O)=CN=C1C1=CC=CC(Cl)=C1 GMTASVFGLFONMF-UHFFFAOYSA-N 0.000 claims 2
- IBVOCILLCZTWKT-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(methoxymethoxy)-1,3-thiazole-5-carbonitrile Chemical compound S1C(C#N)=C(OCOC)N=C1C1=CC=C(Cl)C=C1 IBVOCILLCZTWKT-UHFFFAOYSA-N 0.000 claims 2
- VXESVNMXBWMVDG-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-(1-methyltetrazol-5-yl)-1,3-thiazol-4-ol Chemical compound Cn1nnnc1-c1sc(nc1O)-c1ccc(Cl)cc1 VXESVNMXBWMVDG-UHFFFAOYSA-N 0.000 claims 2
- MOXAICOPIPZILF-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-(2H-tetrazol-5-yl)-1,3-thiazol-4-ol Chemical compound Oc1nc(sc1-c1nnn[nH]1)-c1ccc(Cl)cc1 MOXAICOPIPZILF-UHFFFAOYSA-N 0.000 claims 2
- PNWAABHVBOSNJO-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)-1,3-thiazol-4-ol Chemical compound Cc1nnc(o1)-c1sc(nc1O)-c1ccc(Cl)cc1 PNWAABHVBOSNJO-UHFFFAOYSA-N 0.000 claims 2
- YXGKFMQTYYVJNM-UHFFFAOYSA-N 2-(4-methylphenyl)-4-(2-methylpropoxy)-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(OCC(C)C)N=C1C1=CC=C(C)C=C1 YXGKFMQTYYVJNM-UHFFFAOYSA-N 0.000 claims 2
- ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 claims 2
- OIOLMYRKDIDFFD-UHFFFAOYSA-N 2-phenyl-4-[[4-(trifluoromethyl)phenyl]methoxy]-1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C=1SC(C=2C=CC=CC=2)=NC=1OCC1=CC=C(C(F)(F)F)C=C1 OIOLMYRKDIDFFD-UHFFFAOYSA-N 0.000 claims 2
- ACBXRLZLZZXFJY-UHFFFAOYSA-N 4-(2-aminoethylamino)-2-(4-methylphenyl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=NC(NCCN)=C(C(O)=O)S1 ACBXRLZLZZXFJY-UHFFFAOYSA-N 0.000 claims 2
- FPHXJPFLWMNHBE-UHFFFAOYSA-N 4-(4-chlorophenyl)-1,3-thiazole-5-carboxylic acid Chemical compound S1C=NC(C=2C=CC(Cl)=CC=2)=C1C(=O)O FPHXJPFLWMNHBE-UHFFFAOYSA-N 0.000 claims 2
- HPCDMKKZYVBIBD-UHFFFAOYSA-N 4-[(2-chlorophenyl)methoxy]-2-(4-methylphenyl)-1,3-thiazole-5-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=NC(OCC=2C(=CC=CC=2)Cl)=C(C(O)=O)S1 HPCDMKKZYVBIBD-UHFFFAOYSA-N 0.000 claims 2
- MTXWXPXFKOBTLF-UHFFFAOYSA-N 4-[(4-chlorophenyl)methoxy]-2-(3-fluorophenyl)-1,3-oxazole-5-carboxylic acid Chemical compound OC(=O)C=1OC(C=2C=C(F)C=CC=2)=NC=1OCC1=CC=C(Cl)C=C1 MTXWXPXFKOBTLF-UHFFFAOYSA-N 0.000 claims 2
- GPUAEKWIJYOWFX-UHFFFAOYSA-N 4-[(4-chlorophenyl)methoxy]-2-phenyl-1,3-oxazole-5-carboxylic acid Chemical compound OC(=O)C=1OC(C=2C=CC=CC=2)=NC=1OCC1=CC=C(Cl)C=C1 GPUAEKWIJYOWFX-UHFFFAOYSA-N 0.000 claims 2
- HOVUYEIYKRUBIF-UHFFFAOYSA-N 5-(2-ethyltetrazol-5-yl)-2-(3-fluorophenyl)-1,3-thiazol-4-ol Chemical compound CCn1nnc(n1)-c1sc(nc1O)-c1cccc(F)c1 HOVUYEIYKRUBIF-UHFFFAOYSA-N 0.000 claims 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 2
- WZARKCXULWTXCZ-NMTGCUOTSA-N CC(C)[C@H](CC[C@@H](C)C1)[C@@H]1[S+]1C(C2=CC=C(C)C=C2)=NC(OCC2=CC=CC=C2)=C1C([O-])=O Chemical compound CC(C)[C@H](CC[C@@H](C)C1)[C@@H]1[S+]1C(C2=CC=C(C)C=C2)=NC(OCC2=CC=CC=C2)=C1C([O-])=O WZARKCXULWTXCZ-NMTGCUOTSA-N 0.000 claims 2
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- OQIQSTLJSLGHID-WNWIJWBNSA-N aflatoxin B1 Chemical compound C=1([C@@H]2C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O OQIQSTLJSLGHID-WNWIJWBNSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
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- LIAYXXMJRCMHIW-UHFFFAOYSA-N ethyl 2-(3-fluorophenyl)-4-[4-(trifluoromethyl)benzoyl]oxy-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=C(F)C=CC=2)=NC=1OC(=O)C1=CC=C(C(F)(F)F)C=C1 LIAYXXMJRCMHIW-UHFFFAOYSA-N 0.000 claims 2
- JVTYXNJWURWOLV-UHFFFAOYSA-N ethyl 2-(3-fluorophenyl)-4-hydroxy-1,3-oxazole-5-carboxylate Chemical compound CCOC(=O)c1oc(nc1O)-c1cccc(F)c1 JVTYXNJWURWOLV-UHFFFAOYSA-N 0.000 claims 2
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- HAWGINGHSGYHJO-UHFFFAOYSA-N ethyl 2-(4-fluorophenyl)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazole-5-carboxylate Chemical compound CC(C)(C)OC(=O)NC1=C(C(=O)OCC)SC(C=2C=CC(F)=CC=2)=N1 HAWGINGHSGYHJO-UHFFFAOYSA-N 0.000 claims 2
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- RJWSCGGRYXRAMT-UHFFFAOYSA-N ethyl 4-[(3-chlorophenyl)methoxy]-2-(3-fluorophenyl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(C=2C=C(F)C=CC=2)=NC=1OCC1=CC=CC(Cl)=C1 RJWSCGGRYXRAMT-UHFFFAOYSA-N 0.000 claims 2
- WRTHLFGZMSTFER-UHFFFAOYSA-N ethyl 4-[2-(methylamino)ethylamino]-2-(4-methylphenyl)-1,3-thiazole-5-carboxylate Chemical compound CNCCNC1=C(C(=O)OCC)SC(C=2C=CC(C)=CC=2)=N1 WRTHLFGZMSTFER-UHFFFAOYSA-N 0.000 claims 2
- HTQNUGGPEURDFS-UHFFFAOYSA-N ethyl 4-hydroxy-2-(4-methylphenyl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)c1sc(nc1O)-c1ccc(C)cc1 HTQNUGGPEURDFS-UHFFFAOYSA-N 0.000 claims 2
- SZDKWQDAJJRAPG-UHFFFAOYSA-N ethyl 4-hydroxy-2-[3-[2-(trifluoromethyl)phenyl]phenyl]-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)c1sc(nc1O)-c1cccc(c1)-c1ccccc1C(F)(F)F SZDKWQDAJJRAPG-UHFFFAOYSA-N 0.000 claims 2
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- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims 1
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- GTTLQUWXZGMKGX-UHFFFAOYSA-N chembl1377190 Chemical compound OC1=C(C(=O)OCC)SC(C=2C=CC(Cl)=CC=2)=N1 GTTLQUWXZGMKGX-UHFFFAOYSA-N 0.000 claims 1
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- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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Classifications
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- 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]
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- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
- C07D263/36—One oxygen atom
- C07D263/40—One oxygen atom attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
- C07D263/36—One oxygen atom
- C07D263/42—One oxygen atom attached in position 5
-
- 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
- C07D277/56—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pulmonology (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Dermatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11194365.0A EP2606888A1 (en) | 2011-12-19 | 2011-12-19 | Trpm8 antagonists |
| EP12178327 | 2012-07-27 | ||
| PCT/EP2012/076147 WO2013092711A1 (en) | 2011-12-19 | 2012-12-19 | Trpm8 antagonists |
| EP12812229.8A EP2793883B1 (en) | 2011-12-19 | 2012-12-19 | Trpm8 antagonists |
Publications (1)
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| SI2793883T1 true SI2793883T1 (en) | 2018-08-31 |
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Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2481727A1 (en) * | 2011-01-28 | 2012-08-01 | Dompe S.p.A. | TRPM8 receptor antagonists |
| SMT201800351T1 (it) | 2011-12-19 | 2018-09-13 | Dompe Farm Spa | Antagonisti trpm8 |
| CA2908365C (en) | 2013-05-24 | 2023-02-28 | Nestec S.A. | Treatment or prevention of non-inflammatory neuronal damage from brain trauma and strokes using linalool |
| US10294243B2 (en) | 2014-06-05 | 2019-05-21 | Bayer Cropscience Aktiengesellschaft | Bicyclic compounds as pesticides |
| SI3157918T1 (sl) | 2014-06-23 | 2019-05-31 | Dompe Farmaceutici S.P.A. | 2-aril-4-hidroksi-1,3-tiazolni derivati, uporabni kot inhibitorji TRPM8 pri zdravljenju nevralgije, bolečine, KOPB in astme |
| JP6865743B2 (ja) | 2015-10-01 | 2021-04-28 | フィルメニッヒ インコーポレイテッドＦｉｒｍｅｎｉｃｈ Ｉｎｃｏｒｐｏｒａｔｅｄ | Ｔｒｐｍ８の活性調節因子として有用な化合物 |
| EP3184524A1 (en) * | 2015-12-21 | 2017-06-28 | Dompé farmaceutici S.p.A. | 4-hydroxy-2-phenyl-1,3-thiazol-5-yl methanone derivatives as trpm8 antagonists |
| JP6943887B2 (ja) | 2016-06-13 | 2021-10-06 | 田辺三菱製薬株式会社 | 血管運動症状を治療または予防するための組成物および方法 |
| WO2018117166A1 (ja) * | 2016-12-21 | 2018-06-28 | キッセイ薬品工業株式会社 | チアゾール誘導体、またはその薬理学的に許容される塩 |
Family Cites Families (17)
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| DE2713573A1 (de) * | 1977-03-28 | 1978-10-05 | Basf Ag | 4,5-disubstituierte thiazole und verfahren zu ihrer herstellung |
| JPS59220687A (ja) * | 1983-05-30 | 1984-12-12 | 株式会社日立製作所 | 直接サイクル型軽水原子炉一次冷却系の腐食環境抑制設備 |
| SG86971A1 (en) * | 1990-11-30 | 2002-03-19 | Teijin Ltd | 2-arylthiazole derivatives and pharmaceutical composition thereof |
| EP1321463B1 (en) * | 2001-12-21 | 2007-08-08 | Virochem Pharma Inc. | Thiazole derivatives and their use for the treatment or prevention of Flavivirus infections |
| US20080214654A1 (en) | 2004-10-13 | 2008-09-04 | Bayer Healthcare Ag | Substituted Benzyloxy-Phenylmethylamide Derivatives |
| WO2007017094A1 (en) | 2005-08-04 | 2007-02-15 | Bayer Healthcare Ag | Substituted benzyloxy-phenylmethylcarbamate derivatives |
| WO2007017092A1 (en) | 2005-08-04 | 2007-02-15 | Bayer Healthcare Ag | Substituted 4-benzyloxy-benzoic acid amide derivatives |
| WO2007017093A1 (en) | 2005-08-04 | 2007-02-15 | Bayer Healthcare Ag | Substituted 2-benzyloxy-benzoic acid amide derivatives |
| WO2007080109A1 (en) | 2006-01-16 | 2007-07-19 | Bayer Healthcare Ag | Substituded benzyloxy-phenylmethylurea derivatives |
| WO2007089031A1 (en) * | 2006-02-01 | 2007-08-09 | Takeda Pharmaceutical Company Limited | Piperidine derivatives as tachykinin receptor antagonists |
| CA2651865C (en) | 2006-05-10 | 2015-11-24 | Janssen Pharmaceutica N.V. | Cold menthol receptor-1 antagonists |
| EP2183239B1 (en) | 2007-07-18 | 2012-08-22 | Janssen Pharmaceutica, N.V. | Sulfonamides as trpm8 modulators |
| US8148422B2 (en) * | 2008-12-18 | 2012-04-03 | Janssen Pharmaceutica, Nv | Sulfonamides as TRPM8 modulators |
| WO2010103381A1 (en) | 2009-03-13 | 2010-09-16 | Glenmark Pharmaceuticals S.A. | Spirocyclic piperidine derivatives as trpm 8 modulators |
| US20120094964A1 (en) * | 2009-05-01 | 2012-04-19 | Tadashi Inoue | Sulfamoyl benzoic acid derivatives as trpm8 antagonists |
| WO2012036233A1 (ja) * | 2010-09-17 | 2012-03-22 | 塩野義製薬株式会社 | メラニン凝集ホルモン受容体アンタゴニスト活性を有する縮合へテロ環誘導体 |
| SMT201800351T1 (it) | 2011-12-19 | 2018-09-13 | Dompe Farm Spa | Antagonisti trpm8 |
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2012
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- 2012-12-19 SI SI201231328T patent/SI2793883T1/en unknown
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- 2012-12-19 HR HRP20181086TT patent/HRP20181086T1/hr unknown
- 2012-12-19 DK DK12812229.8T patent/DK2793883T3/en active
- 2012-12-19 HU HUE12812229A patent/HUE038407T2/hu unknown
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- 2012-12-19 JP JP2014547975A patent/JP6238906B2/ja active Active
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- 2012-12-19 ME MEP-2018-177A patent/ME03038B/me unknown
- 2012-12-19 US US14/366,796 patent/US9585875B2/en active Active
- 2012-12-19 CN CN201280069993.7A patent/CN104220069B/zh active Active
- 2012-12-19 TR TR2018/08861T patent/TR201808861T4/tr unknown
- 2012-12-19 RS RS20180793A patent/RS57389B1/sr unknown
- 2012-12-19 PT PT128122298T patent/PT2793883T/pt unknown
- 2012-12-19 EA EA201491213A patent/EA025356B1/ru unknown
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2014
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2017
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- 2017-06-19 JP JP2017119493A patent/JP2017197564A/ja not_active Withdrawn
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2018
- 2018-07-10 CY CY20181100717T patent/CY1120403T1/el unknown
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