JP2021501219A5 - - Google Patents
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- Publication number
- JP2021501219A5 JP2021501219A5 JP2020544332A JP2020544332A JP2021501219A5 JP 2021501219 A5 JP2021501219 A5 JP 2021501219A5 JP 2020544332 A JP2020544332 A JP 2020544332A JP 2020544332 A JP2020544332 A JP 2020544332A JP 2021501219 A5 JP2021501219 A5 JP 2021501219A5
- Authority
- JP
- Japan
- Prior art keywords
- vinyl
- cyclopropyl
- heptane
- isoxazole
- carboxylic acid
- 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 cyano, hydroxyl Chemical group 0.000 claims 58
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 25
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 239000012453 solvate Substances 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims 12
- 125000003003 spiro group Chemical group 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000001188 haloalkyl group Chemical group 0.000 claims 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 9
- 125000004103 aminoalkyl group Chemical group 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims 9
- 125000004452 carbocyclyl group Chemical group 0.000 claims 8
- 125000003282 alkyl amino group Chemical group 0.000 claims 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000002947 alkylene group Chemical group 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 4
- 206010016654 Fibrosis Diseases 0.000 claims 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 4
- BLFJCJKTSCOLEY-UHFFFAOYSA-N cinnoline-3-carboxylic acid Chemical compound C1=CC=C2N=NC(C(=O)O)=CC2=C1 BLFJCJKTSCOLEY-UHFFFAOYSA-N 0.000 claims 4
- 230000004761 fibrosis Effects 0.000 claims 4
- 125000004474 heteroalkylene group Chemical group 0.000 claims 4
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- JFCRJZKKQUORFE-DAFODLJHSA-N 2-[6-[(E)-2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)/C=C/C1CC2(CN(C2)C=2SC3=C(N=2)C(=CC(=C3)C(=O)O)F)C1 JFCRJZKKQUORFE-DAFODLJHSA-N 0.000 claims 3
- CLIRDNHKZBZHCB-XVNBXDOJSA-N 6-[6-[(E)-2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-4-propan-2-yloxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)/C=C/C1CC2(CN(C2)C=2C=C3C(=CC(=NC3=CC=2)C(=O)O)OC(C)C)C1 CLIRDNHKZBZHCB-XVNBXDOJSA-N 0.000 claims 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 3
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 3
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 2
- WJZWXMFQFCERCP-GORDUTHDSA-N 3-[6-[(E)-2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-5-methoxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)/C=C/C1CC2(CN(C2)C=2C=C(C(=O)O)C=C(C=2)OC)C1 WJZWXMFQFCERCP-GORDUTHDSA-N 0.000 claims 2
- ZLKXIPKSHPYWRS-BJMVGYQFSA-N 3-cyclopropyloxy-5-[[2-[(E)-2-[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]ethenyl]spiro[3.3]heptan-6-yl]methoxy]pyridine-2-carboxylic acid Chemical compound C1(CC1)OC=1C(=NC=C(C=1)OCC1CC2(C1)CC(C2)\C=C\C=1C(=NOC=1C1CC1)C1=C(C=CC=C1)C(F)(F)F)C(=O)O ZLKXIPKSHPYWRS-BJMVGYQFSA-N 0.000 claims 2
- ZSXDLRGKKCQMFH-NYYWCZLTSA-N 4-[6-[(E)-2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)/C=C/C1CC2(CN(C2)C2=CC=C(C(=O)O)C=C2)C1 ZSXDLRGKKCQMFH-NYYWCZLTSA-N 0.000 claims 2
- UTQXRZKZRGGHMB-UXBLZVDNSA-N 4-cyclobutyloxy-6-[6-[(E)-2-[5-cyclopropyl-3-[2-(trifluoromethyl)pyridin-3-yl]-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]quinoline-2-carboxylic acid Chemical compound C1(CCC1)OC1=CC(=NC2=CC=C(C=C12)N1CC2(C1)CC(C2)\C=C\C=1C(=NOC=1C1CC1)C=1C(=NC=CC=1)C(F)(F)F)C(=O)O UTQXRZKZRGGHMB-UXBLZVDNSA-N 0.000 claims 2
- XAMDTJXPTLVUOE-ORCRQEGFSA-N 6-[6-[(E)-2-[3-(3-chloropyridin-4-yl)-5-cyclopropyl-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound ClC=1C=NC=CC=1C1=NOC(=C1/C=C/C1CC2(CN(C2)C=2C=C3C(=CC(=NC3=CC=2)C(=O)O)C(F)(F)F)C1)C1CC1 XAMDTJXPTLVUOE-ORCRQEGFSA-N 0.000 claims 2
- LGMCSXDMAVCYQF-QHHAFSJGSA-N 6-[6-[(E)-2-[3-(3-chloropyridin-4-yl)-5-cyclopropyl-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-4-methoxyquinoline-2-carboxylic acid Chemical compound ClC=1C=NC=CC=1C1=NOC(=C1/C=C/C1CC2(CN(C2)C=2C=C3C(=CC(=NC3=CC=2)C(=O)O)OC)C1)C1CC1 LGMCSXDMAVCYQF-QHHAFSJGSA-N 0.000 claims 2
- ZISPHBKLQKZRJA-XBXARRHUSA-N 6-[6-[(E)-2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)/C=C/C1CC2(CN(C2)C=2C=C3C(=CC(=NC3=CC=2)C(=O)O)C(F)(F)F)C1 ZISPHBKLQKZRJA-XBXARRHUSA-N 0.000 claims 2
- KCVYFCALNTVLHO-QHHAFSJGSA-N 6-[6-[(E)-2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-4-(methoxymethyl)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)/C=C/C1CC2(CN(C2)C=2C=C3C(=CC(=NC3=CC=2)C(=O)O)COC)C1 KCVYFCALNTVLHO-QHHAFSJGSA-N 0.000 claims 2
- XYEOJNRSZNZCOU-ORCRQEGFSA-N 6-[6-[(E)-2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-4-(oxetan-3-yloxy)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)/C=C/C1CC2(CN(C2)C=2C=C3C(=CC(=NC3=CC=2)C(=O)O)OC2COC2)C1 XYEOJNRSZNZCOU-ORCRQEGFSA-N 0.000 claims 2
- UJCOFMCTWDSIMX-DQTQVHTCSA-N 6-[6-[(E)-2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-4-(trideuteriomethoxy)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)/C=C/C1CC2(CN(C2)C=2C=C3C(=CC(=NC3=CC=2)C(=O)O)OC([2H])([2H])[2H])C1 UJCOFMCTWDSIMX-DQTQVHTCSA-N 0.000 claims 2
- NUVFQIVGZUGRSR-ORCRQEGFSA-N 6-[6-[(E)-2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)/C=C/C1CC2(CN(C2)C=2C=C3C(=CC(=NC3=CC=2)C(=O)O)C(F)(F)F)C1 NUVFQIVGZUGRSR-ORCRQEGFSA-N 0.000 claims 2
- XNRBZKOQCVVISY-LREOWRDNSA-N 6-[6-[(E)-2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-4-cyclopropyloxyquinoline-2-carboxylic acid Chemical compound C1(CC1)OC1=CC(=NC2=CC=C(C=C12)N1CC2(C1)CC(C2)\C=C\C=1C(=NOC=1C1CC1)C1=C(C=NC=C1Cl)Cl)C(=O)O XNRBZKOQCVVISY-LREOWRDNSA-N 0.000 claims 2
- UJCOFMCTWDSIMX-QHHAFSJGSA-N 6-[6-[(E)-2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-4-methoxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)/C=C/C1CC2(CN(C2)C=2C=C3C(=CC(=NC3=CC=2)C(=O)O)OC)C1 UJCOFMCTWDSIMX-QHHAFSJGSA-N 0.000 claims 2
- PMJSWWXKKKSBOM-GORDUTHDSA-N 6-[6-[(E)-2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-8-fluoro-4-methoxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)/C=C/C1CC2(CN(C2)C=2C=C3C(=CC(=NC3=C(C=2)F)C(=O)O)OC)C1 PMJSWWXKKKSBOM-GORDUTHDSA-N 0.000 claims 2
- AAKQZQQSRIQZOR-XVNBXDOJSA-N 6-[6-[(E)-2-[5-cyclopropyl-3-[2-(trifluoromethyl)pyridin-3-yl]-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-4-(oxetan-3-yloxy)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C=1C(=NC=CC=1)C(F)(F)F)/C=C/C1CC2(CN(C2)C=2C=C3C(=CC(=NC3=CC=2)C(=O)O)OC2COC2)C1 AAKQZQQSRIQZOR-XVNBXDOJSA-N 0.000 claims 2
- MBRRRDSCTDULHU-WEVVVXLNSA-N 6-[6-[(E)-2-[5-cyclopropyl-3-[2-(trifluoromethyl)pyridin-3-yl]-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-4-ethoxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C=1C(=NC=CC=1)C(F)(F)F)/C=C/C1CC2(CN(C2)C=2C=C3C(=CC(=NC3=CC=2)C(=O)O)OCC)C1 MBRRRDSCTDULHU-WEVVVXLNSA-N 0.000 claims 2
- QXHCMBYMNPSDPG-XBXARRHUSA-N 6-[6-[(E)-2-[5-cyclopropyl-3-[2-(trifluoromethyl)pyridin-3-yl]-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-4-methoxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C=1C(=NC=CC=1)C(F)(F)F)/C=C/C1CC2(CN(C2)C=2C=C3C(=CC(=NC3=CC=2)C(=O)O)OC)C1 QXHCMBYMNPSDPG-XBXARRHUSA-N 0.000 claims 2
- ICKYCMYDPMHLJD-WEVVVXLNSA-N 6-[6-[(E)-2-[5-cyclopropyl-3-[3-(trifluoromethyl)pyridin-2-yl]-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-4-propan-2-yloxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=NC=CC=C1C(F)(F)F)/C=C/C1CC2(CN(C2)C=2C=C3C(=CC(=NC3=CC=2)C(=O)O)OC(C)C)C1 ICKYCMYDPMHLJD-WEVVVXLNSA-N 0.000 claims 2
- ZBCUINQGTPZHAX-QHHAFSJGSA-N 6-[6-[(E)-2-[5-cyclopropyl-3-[4-(trifluoromethyl)pyridin-3-yl]-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-4-methoxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C=1C=NC=CC=1C(F)(F)F)/C=C/C1CC2(CN(C2)C=2C=C3C(=CC(=NC3=CC=2)C(=O)O)OC)C1 ZBCUINQGTPZHAX-QHHAFSJGSA-N 0.000 claims 2
- SMXAMVLLVRPDBJ-FPYGCLRLSA-N 7-[6-[(E)-2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-1-ethylisoquinoline-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)/C=C/C1CC2(CN(C2)C2=CC=C3C=C(N=C(C3=C2)CC)C(=O)O)C1 SMXAMVLLVRPDBJ-FPYGCLRLSA-N 0.000 claims 2
- HKRDHNSWHQNBJK-FARCUNLSSA-N 7-[6-[(E)-2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]ethenyl]-2-azaspiro[3.3]heptan-2-yl]-1-methylisoquinoline-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)/C=C/C1CC2(CN(C2)C2=CC=C3C=C(N=C(C3=C2)C)C(=O)O)C1 HKRDHNSWHQNBJK-FARCUNLSSA-N 0.000 claims 2
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 2
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 2
- PKEDPRFVUCLJEW-LREOWRDNSA-N C1(CC1)OC1=CC(=NC2=CC=C(C=C12)N1CC2(C1)CC(C2)\C=C\C=1C(=NOC=1C1CC1)C=1C=NC=CC=1C(F)(F)F)C(=O)O Chemical compound C1(CC1)OC1=CC(=NC2=CC=C(C=C12)N1CC2(C1)CC(C2)\C=C\C=1C(=NOC=1C1CC1)C=1C=NC=CC=1C(F)(F)F)C(=O)O PKEDPRFVUCLJEW-LREOWRDNSA-N 0.000 claims 2
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 2
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 125000001769 aryl amino group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000005873 benzo[d]thiazolyl group Chemical group 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 210000000013 bile duct Anatomy 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 230000001587 cholestatic effect Effects 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000003147 glycosyl group Chemical group 0.000 claims 1
- 125000004992 haloalkylamino group Chemical group 0.000 claims 1
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 230000002503 metabolic effect Effects 0.000 claims 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 229940081066 picolinic acid Drugs 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 201000002793 renal fibrosis Diseases 0.000 claims 1
- 208000010157 sclerosing cholangitis Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- WTFUOXJGOHRVGB-UHFFFAOYSA-N CC(C)C(N/N=N\C)=N Chemical compound CC(C)C(N/N=N\C)=N WTFUOXJGOHRVGB-UHFFFAOYSA-N 0.000 description 1
- UECQTHNSSVOEQB-UHFFFAOYSA-N CC(C)C(NCC([Re])=O)=O Chemical compound CC(C)C(NCC([Re])=O)=O UECQTHNSSVOEQB-UHFFFAOYSA-N 0.000 description 1
- RAYSJWMJMSNCAE-UHFFFAOYSA-N CC(C)CC(N/N=N\C)=N Chemical compound CC(C)CC(N/N=N\C)=N RAYSJWMJMSNCAE-UHFFFAOYSA-N 0.000 description 1
- UCHZWQUZQJNDKL-UHFFFAOYSA-N CC(C)CC(NCS([Re])(=O)=O)=O Chemical compound CC(C)CC(NCS([Re])(=O)=O)=O UCHZWQUZQJNDKL-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762580073P | 2017-11-01 | 2017-11-01 | |
| US62/580,073 | 2017-11-01 | ||
| PCT/US2018/058313 WO2019089665A1 (en) | 2017-11-01 | 2018-10-31 | Alkene spirocyclic compounds as farnesoid x receptor modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021501219A JP2021501219A (ja) | 2021-01-14 |
| JP2021501219A5 true JP2021501219A5 (enExample) | 2021-11-11 |
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| CN110128432B (zh) | 2018-02-02 | 2021-03-02 | 广东东阳光药业有限公司 | 含氮三环化合物及其在药物中的应用 |
| CA3159163A1 (en) | 2020-01-15 | 2021-07-22 | Raphael Darteil | Use of fxr agonists for treating an infection by hepatitis d virus |
| CN111592490B (zh) * | 2020-07-02 | 2022-04-22 | 浙江工业大学 | 一种罗沙司他关键中间体的制备方法 |
| CN112083113B (zh) * | 2020-07-09 | 2021-06-15 | 苏州旭辉检测有限公司 | 一种螺环化合物的生物样品分析方法 |
| CA3204800A1 (en) | 2021-01-14 | 2022-07-21 | Raphael Darteil | Synergistic effect of a fxr agonist and ifn for the treatment of hbv infection |
| US20240216364A1 (en) | 2021-04-28 | 2024-07-04 | Enyo Pharma | Strong potentiation of tlr3 agonists effects using fxr agonists as a combined treatment |
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-
2018
- 2018-10-31 CN CN201880071420.5A patent/CN111630051B/zh active Active
- 2018-10-31 US US16/760,810 patent/US11286252B2/en active Active
- 2018-10-31 WO PCT/US2018/058313 patent/WO2019089665A1/en not_active Ceased
- 2018-10-31 AU AU2018360575A patent/AU2018360575A1/en not_active Abandoned
- 2018-10-31 MX MX2020004102A patent/MX2020004102A/es unknown
- 2018-10-31 BR BR112020008121-3A patent/BR112020008121A2/pt not_active Application Discontinuation
- 2018-10-31 EA EA202091084A patent/EA202091084A1/ru unknown
- 2018-10-31 CA CA3080893A patent/CA3080893A1/en not_active Abandoned
- 2018-10-31 EP EP18804185.9A patent/EP3704112B1/en active Active
- 2018-10-31 JP JP2020544332A patent/JP7223016B2/ja active Active
- 2018-10-31 ES ES18804185T patent/ES2963652T3/es active Active
- 2018-10-31 KR KR1020207015278A patent/KR102732405B1/ko active Active
- 2018-10-31 SG SG11202003830SA patent/SG11202003830SA/en unknown
-
2020
- 2020-04-28 IL IL274320A patent/IL274320A/en unknown
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