JP2020514334A5 - - Google Patents
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- JP2020514334A5 JP2020514334A5 JP2019547663A JP2019547663A JP2020514334A5 JP 2020514334 A5 JP2020514334 A5 JP 2020514334A5 JP 2019547663 A JP2019547663 A JP 2019547663A JP 2019547663 A JP2019547663 A JP 2019547663A JP 2020514334 A5 JP2020514334 A5 JP 2020514334A5
- Authority
- JP
- Japan
- Prior art keywords
- trans
- cyclohexyl
- methyl
- phenyl
- methoxy
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
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- -1 full Ranil Chemical group 0.000 claims 90
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims 28
- 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 28
- 150000001875 compounds Chemical class 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 24
- 239000012453 solvate Substances 0.000 claims 24
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 229910052805 deuterium Inorganic materials 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 17
- JTNNVONTXCBLEJ-UHFFFAOYSA-N cyclohexylmethyl carbamate Chemical compound NC(=O)OCC1CCCCC1 JTNNVONTXCBLEJ-UHFFFAOYSA-N 0.000 claims 16
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 12
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 9
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 241000124008 Mammalia Species 0.000 claims 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 5
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 4
- MQGJTSVKWXWUEJ-UHFFFAOYSA-N 4-N-[3-(2-methoxy-1,3-thiazol-5-yl)phenyl]cyclohexane-1,4-dicarboxamide Chemical compound COC1=NC=C(S1)C2=CC(=CC=C2)NC(=O)C3CCC(CC3)C(=O)N MQGJTSVKWXWUEJ-UHFFFAOYSA-N 0.000 claims 4
- 208000007082 Alcoholic Fatty Liver Diseases 0.000 claims 4
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 4
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 4
- 241000711549 Hepacivirus C Species 0.000 claims 4
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 4
- 208000026594 alcoholic fatty liver disease Diseases 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 210000004185 liver Anatomy 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 4
- 125000003944 tolyl group Chemical group 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 3
- 208000019425 cirrhosis of liver Diseases 0.000 claims 3
- XSJOKZKOSJKFOQ-UHFFFAOYSA-N cyclohexyl 3-hydroxyazetidine-1-carboxylate Chemical compound OC1CN(C1)C(=O)OC1CCCCC1 XSJOKZKOSJKFOQ-UHFFFAOYSA-N 0.000 claims 3
- 208000006454 hepatitis Diseases 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 208000010157 sclerosing cholangitis Diseases 0.000 claims 3
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- INNWRDCESBMSQK-UHFFFAOYSA-N 2-(2-hydroxyethoxy)acetamide Chemical compound NC(=O)COCCO INNWRDCESBMSQK-UHFFFAOYSA-N 0.000 claims 2
- 206010004659 Biliary cirrhosis Diseases 0.000 claims 2
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 claims 2
- 208000015943 Coeliac disease Diseases 0.000 claims 2
- 206010012735 Diarrhoea Diseases 0.000 claims 2
- 208000004232 Enteritis Diseases 0.000 claims 2
- 241000700721 Hepatitis B virus Species 0.000 claims 2
- 206010019799 Hepatitis viral Diseases 0.000 claims 2
- 208000002972 Hepatolenticular Degeneration Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 208000025865 Ulcer Diseases 0.000 claims 2
- 208000018839 Wilson disease Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 2
- 231100000283 hepatitis Toxicity 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 201000001862 viral hepatitis Diseases 0.000 claims 2
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 1
- ASTRWPOSIDFRGD-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)acetamide Chemical compound NC(=O)CC1=NC=CN1 ASTRWPOSIDFRGD-UHFFFAOYSA-N 0.000 claims 1
- BRTQKGICBJYPER-UHFFFAOYSA-N 2-(1h-imidazol-5-yl)acetamide Chemical compound NC(=O)CC1=CNC=N1 BRTQKGICBJYPER-UHFFFAOYSA-N 0.000 claims 1
- XRVGAZQKAXSYSB-UHFFFAOYSA-N 2-(2-aminoethoxy)acetamide Chemical compound NCCOCC(N)=O XRVGAZQKAXSYSB-UHFFFAOYSA-N 0.000 claims 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- WKJOQYHMXRVQDK-UHFFFAOYSA-N 2-(dimethylamino)acetamide Chemical compound CN(C)CC(N)=O WKJOQYHMXRVQDK-UHFFFAOYSA-N 0.000 claims 1
- ILISJYDKHMRJLS-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]acetamide Chemical compound CN(C)CCOCC(N)=O ILISJYDKHMRJLS-UHFFFAOYSA-N 0.000 claims 1
- WQELDIQOHGAHEM-UHFFFAOYSA-N 2-acetamidoacetamide Chemical compound CC(=O)NCC(N)=O WQELDIQOHGAHEM-UHFFFAOYSA-N 0.000 claims 1
- DRYMMXUBDRJPDS-UHFFFAOYSA-N 2-hydroxy-2-methylpropanamide Chemical compound CC(C)(O)C(N)=O DRYMMXUBDRJPDS-UHFFFAOYSA-N 0.000 claims 1
- TZGPACAKMCUCKX-UHFFFAOYSA-N 2-hydroxyacetamide Chemical compound NC(=O)CO TZGPACAKMCUCKX-UHFFFAOYSA-N 0.000 claims 1
- MEAVLRNBGURMFI-UHFFFAOYSA-N 2-imidazol-1-ylacetamide Chemical compound NC(=O)CN1C=CN=C1 MEAVLRNBGURMFI-UHFFFAOYSA-N 0.000 claims 1
- 125000001137 3-hydroxypropoxy group Chemical group [H]OC([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- AHWKKJBPRHKEAZ-BBHPTNJDSA-N C(C)(=O)OCC(=O)N[C@@H]1CC[C@H](CC1)C(N(C[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)OC)C)C1=CC(=CC=C1)C1=CN=C(S1)C1CC1)=O Chemical compound C(C)(=O)OCC(=O)N[C@@H]1CC[C@H](CC1)C(N(C[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)OC)C)C1=CC(=CC=C1)C1=CN=C(S1)C1CC1)=O AHWKKJBPRHKEAZ-BBHPTNJDSA-N 0.000 claims 1
- VMDKSZYJGUQOTM-GJIFKWMDSA-N C1(CC1)C=1OC=C(N=1)C=1C=C(C=CC=1)N(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C[C@@H]1CC[C@H](CC1)C1=NC(=C(C=C1)OC)C Chemical compound C1(CC1)C=1OC=C(N=1)C=1C=C(C=CC=1)N(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C[C@@H]1CC[C@H](CC1)C1=NC(=C(C=C1)OC)C VMDKSZYJGUQOTM-GJIFKWMDSA-N 0.000 claims 1
- ZLSKXUNGURIOPO-PJMRXRQGSA-N C1(CC1)C=1SC(=CN=1)C=1C=C(C=CC=1)N(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)OC)C Chemical compound C1(CC1)C=1SC(=CN=1)C=1C=C(C=CC=1)N(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)OC)C ZLSKXUNGURIOPO-PJMRXRQGSA-N 0.000 claims 1
- JGCVCDZUKPGRJH-GJIFKWMDSA-N C1(CC1)C=1SC(=CN=1)C=1C=C(C=CC=1)N(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C[C@@H]1CC[C@H](CC1)C1=NC(=C(C=C1)OC)C Chemical compound C1(CC1)C=1SC(=CN=1)C=1C=C(C=CC=1)N(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C[C@@H]1CC[C@H](CC1)C1=NC(=C(C=C1)OC)C JGCVCDZUKPGRJH-GJIFKWMDSA-N 0.000 claims 1
- DUYVQFALZIQYEW-ZKHCSVRISA-N C1(CC1)C=1SC(=CN=1)C=1C=C(C=CC=1)N(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C[C@@H]1CC[C@H](CC1)C=1C=C2C(=NN(C2=CC=1)C)F Chemical compound C1(CC1)C=1SC(=CN=1)C=1C=C(C=CC=1)N(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C[C@@H]1CC[C@H](CC1)C=1C=C2C(=NN(C2=CC=1)C)F DUYVQFALZIQYEW-ZKHCSVRISA-N 0.000 claims 1
- KEHLVXSDNNLLBB-GJIFKWMDSA-N C1(CC1)C=1SC(=CN=1)C=1C=C(C=CC=1)N(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C[C@@H]1CC[C@H](CC1)C=1C=NC(=CC=1)N(C)C Chemical compound C1(CC1)C=1SC(=CN=1)C=1C=C(C=CC=1)N(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C[C@@H]1CC[C@H](CC1)C=1C=NC(=CC=1)N(C)C KEHLVXSDNNLLBB-GJIFKWMDSA-N 0.000 claims 1
- FZVABQMKLCITEZ-DUOCIXOMSA-N C1(CC1)N1N=CC(=C1)C=1C=C(C=CC=1)N(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)OC)C Chemical compound C1(CC1)N1N=CC(=C1)C=1C=C(C=CC=1)N(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)OC)C FZVABQMKLCITEZ-DUOCIXOMSA-N 0.000 claims 1
- BHJPSCZFVRKCKA-KKLUKGEUSA-N C1(CC1)N1N=CC(=C1)C=1C=C(C=CC=1)N(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C[C@@H]1CC[C@H](CC1)C1=NC(=C(C=C1)OC)C Chemical compound C1(CC1)N1N=CC(=C1)C=1C=C(C=CC=1)N(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C[C@@H]1CC[C@H](CC1)C1=NC(=C(C=C1)OC)C BHJPSCZFVRKCKA-KKLUKGEUSA-N 0.000 claims 1
- HEKPYFGSPLCSCQ-KKLUKGEUSA-N C1(CC1)N1N=CC(=C1)C=1C=C(C=CC=1)N(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C[C@@H]1CC[C@H](CC1)C=1C=NC(=CC=1)N(C)C Chemical compound C1(CC1)N1N=CC(=C1)C=1C=C(C=CC=1)N(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C[C@@H]1CC[C@H](CC1)C=1C=NC(=CC=1)N(C)C HEKPYFGSPLCSCQ-KKLUKGEUSA-N 0.000 claims 1
- WWPBGRFNTNUPJL-UHFFFAOYSA-N CNC(=O)C1CCC(CC1)(C2=CC=CC(=C2)C3=CN=C(S3)OC)C(=O)N Chemical compound CNC(=O)C1CCC(CC1)(C2=CC=CC(=C2)C3=CN=C(S3)OC)C(=O)N WWPBGRFNTNUPJL-UHFFFAOYSA-N 0.000 claims 1
- IFXXQWHPKYXHBF-NGUIPBPISA-N CNC(OCC(=O)N[C@@H]1CC[C@H](CC1)C(N(C[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)OC)C)C1=CC(=CC=C1)C1=CN=C(S1)C1CC1)=O)=O Chemical compound CNC(OCC(=O)N[C@@H]1CC[C@H](CC1)C(N(C[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)OC)C)C1=CC(=CC=C1)C1=CN=C(S1)C1CC1)=O)=O IFXXQWHPKYXHBF-NGUIPBPISA-N 0.000 claims 1
- RUZBEQCLWXMRMX-OLJJXAFESA-N CNC(OCC(=O)N[C@@H]1CC[C@H](CC1)C(N(C[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)OC)C)C1=CC(=CC=C1)C=1C=NN(C=1)C1CC1)=O)=O Chemical compound CNC(OCC(=O)N[C@@H]1CC[C@H](CC1)C(N(C[C@@H]1CC[C@H](CC1)C1=CC(=C(C=C1)OC)C)C1=CC(=CC=C1)C=1C=NN(C=1)C1CC1)=O)=O RUZBEQCLWXMRMX-OLJJXAFESA-N 0.000 claims 1
- OQZOFICNCLYFHN-VJODKUTPSA-N COC1=C(C=C(C=C1)[C@@H]1CC[C@H](CC1)CN(C(=O)C12CCC(CC1)(CC2)C(=O)O)C1=CC(=CC=C1)C1=CN=C(S1)OC)C Chemical compound COC1=C(C=C(C=C1)[C@@H]1CC[C@H](CC1)CN(C(=O)C12CCC(CC1)(CC2)C(=O)O)C1=CC(=CC=C1)C1=CN=C(S1)OC)C OQZOFICNCLYFHN-VJODKUTPSA-N 0.000 claims 1
- DSPZSZBYTKYIOA-YROJFRDXSA-N COC1=C(C=C(C=C1)[C@@H]1CC[C@H](CC1)CN(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C1=CC(=CC=C1)C1=CN=C(S1)OC)C Chemical compound COC1=C(C=C(C=C1)[C@@H]1CC[C@H](CC1)CN(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C1=CC(=CC=C1)C1=CN=C(S1)OC)C DSPZSZBYTKYIOA-YROJFRDXSA-N 0.000 claims 1
- MJCLTXDNEBGPNR-UHFFFAOYSA-N CS(=O)(=O)NC(=O)C1CCC(CC1)C(=O)N Chemical compound CS(=O)(=O)NC(=O)C1CCC(CC1)C(=O)N MJCLTXDNEBGPNR-UHFFFAOYSA-N 0.000 claims 1
- 208000005623 Carcinogenesis Diseases 0.000 claims 1
- 206010008609 Cholangitis sclerosing Diseases 0.000 claims 1
- 206010008635 Cholestasis Diseases 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- MJOSTMRKWHDCPT-ZKHCSVRISA-N ClC=1C=C(C=CC=1OC)[C@@H]1CC[C@H](CC1)CN(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C1=CC(=CC=C1)C1=CN=C(S1)C1CC1 Chemical compound ClC=1C=C(C=CC=1OC)[C@@H]1CC[C@H](CC1)CN(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C1=CC(=CC=C1)C1=CN=C(S1)C1CC1 MJOSTMRKWHDCPT-ZKHCSVRISA-N 0.000 claims 1
- ZALXWVHAFNQXAE-YROJFRDXSA-N ClC=1C=C(C=CC=1OC)[C@@H]1CC[C@H](CC1)CN(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C1=CC(=CC=C1)C=1C=NN(C=1)C1CC1 Chemical compound ClC=1C=C(C=CC=1OC)[C@@H]1CC[C@H](CC1)CN(C(=O)[C@@H]1CC[C@H](CC1)C(=O)O)C1=CC(=CC=C1)C=1C=NN(C=1)C1CC1 ZALXWVHAFNQXAE-YROJFRDXSA-N 0.000 claims 1
- 206010009657 Clostridium difficile colitis Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010010774 Constipation Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 208000004930 Fatty Liver Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 208000005577 Gastroenteritis Diseases 0.000 claims 1
- 206010064147 Gastrointestinal inflammation Diseases 0.000 claims 1
- 206010019708 Hepatic steatosis Diseases 0.000 claims 1
- 206010019728 Hepatitis alcoholic Diseases 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 208000003100 Pseudomembranous Enterocolitis Diseases 0.000 claims 1
- 206010037128 Pseudomembranous colitis Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
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-
2019
- 2019-09-10 PH PH12019502058A patent/PH12019502058A1/en unknown
-
2021
- 2021-11-30 US US17/538,394 patent/US20220089575A1/en not_active Abandoned
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