JP2021501806A5 - - Google Patents
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- JP2021501806A5 JP2021501806A5 JP2020544335A JP2020544335A JP2021501806A5 JP 2021501806 A5 JP2021501806 A5 JP 2021501806A5 JP 2020544335 A JP2020544335 A JP 2020544335A JP 2020544335 A JP2020544335 A JP 2020544335A JP 2021501806 A5 JP2021501806 A5 JP 2021501806A5
- Authority
- JP
- Japan
- Prior art keywords
- azaspiro
- cyclopropyl
- isoxazole
- carboxylic acid
- trifluoromethyl
- 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 95
- 239000002253 acid Substances 0.000 claims 19
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000000623 heterocyclic group Chemical group 0.000 claims 15
- 125000002947 alkylene group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 13
- 229910052760 oxygen Inorganic materials 0.000 claims 13
- 239000012453 solvate Substances 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000004452 carbocyclyl group Chemical group 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 125000001188 haloalkyl group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 8
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims 7
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- HSWCABTYQVCNCT-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F HSWCABTYQVCNCT-UHFFFAOYSA-N 0.000 claims 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- SUOMEPOKHNAXGW-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1-methylindole-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C1=CC=C2C(=CN(C2=C1)C)C(=O)O SUOMEPOKHNAXGW-UHFFFAOYSA-N 0.000 claims 5
- 235000001968 nicotinic acid Nutrition 0.000 claims 5
- 239000011664 nicotinic acid Substances 0.000 claims 5
- 229960003512 nicotinic acid Drugs 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- LIISZMRTGKWIFN-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-1,3-dioxa-8-azaspiro[4.5]decan-8-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1OC2(CO1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F LIISZMRTGKWIFN-UHFFFAOYSA-N 0.000 claims 4
- WMKYKQWKLILFBM-UHFFFAOYSA-N 2h-pyridine-1-carboxylic acid Chemical compound OC(=O)N1CC=CC=C1 WMKYKQWKLILFBM-UHFFFAOYSA-N 0.000 claims 4
- FSJONNQIJMENSS-UHFFFAOYSA-N 4-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C1=CC=C(C(=O)O)C=C1 FSJONNQIJMENSS-UHFFFAOYSA-N 0.000 claims 4
- SDPRBFSOTHXFGV-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1-methylindazole-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)C1=CC2(C1)CCN(CC2)C1=CC=C2C(=NN(C2=C1)C)C(=O)O SDPRBFSOTHXFGV-UHFFFAOYSA-N 0.000 claims 4
- 206010016654 Fibrosis Diseases 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 4
- 230000004761 fibrosis Effects 0.000 claims 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 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
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- QFDHYWGYDUSMOX-UHFFFAOYSA-N 2-[3-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-1-oxa-8-azaspiro[4.5]dec-3-en-8-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C=1COC2(C=1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F QFDHYWGYDUSMOX-UHFFFAOYSA-N 0.000 claims 3
- UWAUOLUWECSAFZ-UHFFFAOYSA-N 3-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1C=C(C(=O)O)C=CC=1 UWAUOLUWECSAFZ-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- GERSIKCSWYDFSJ-UHFFFAOYSA-N 1,2,4-triazine-5-carboxylic acid Chemical compound OC(=O)C1=CN=NC=N1 GERSIKCSWYDFSJ-UHFFFAOYSA-N 0.000 claims 2
- NDMFETHQFUOIQX-UHFFFAOYSA-N 1-(3-chloropropyl)imidazolidin-2-one Chemical compound ClCCCN1CCNC1=O NDMFETHQFUOIQX-UHFFFAOYSA-N 0.000 claims 2
- OPKSRSICFGPFJR-NNCDRQEWSA-N 2-[(1'R,5'S)-2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]spiro[1,3-dioxolane-4,3'-8-azabicyclo[3.2.1]octane]-8'-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1OCC2(O1)C[C@H]1CC[C@@H](C2)N1C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F OPKSRSICFGPFJR-NNCDRQEWSA-N 0.000 claims 2
- AZFSXHXCSHYXTJ-UHFFFAOYSA-N 2-[2-[2-(3,5-dichloropyridin-4-yl)-4-(difluoromethyl)pyrazol-3-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound ClC=1C=NC=C(C=1N1N=CC(=C1C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F)C(F)F)Cl AZFSXHXCSHYXTJ-UHFFFAOYSA-N 0.000 claims 2
- UWRCWLXYNLAUAI-UHFFFAOYSA-N 2-[2-[3-(2,6-dichlorophenyl)-5-propan-2-yl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F)C(C)C UWRCWLXYNLAUAI-UHFFFAOYSA-N 0.000 claims 2
- LYVPDXCHQNZONE-UHFFFAOYSA-N 2-[2-[3-(2-chloro-6-fluorophenyl)-5-cyclopropyl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)F)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F)C1CC1 LYVPDXCHQNZONE-UHFFFAOYSA-N 0.000 claims 2
- QEPOHZWOLPXQMZ-UHFFFAOYSA-N 2-[2-[3-(2-chloro-6-methylphenyl)-5-cyclopropyl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)C)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F)C1CC1 QEPOHZWOLPXQMZ-UHFFFAOYSA-N 0.000 claims 2
- OLQSHPAFFXHZHZ-UHFFFAOYSA-N 2-[2-[3-(3,5-dichloropyridin-4-yl)-5-propan-2-yl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound ClC=1C=NC=C(C=1C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F)C(C)C)Cl OLQSHPAFFXHZHZ-UHFFFAOYSA-N 0.000 claims 2
- WWRFHHWIFULLSF-UHFFFAOYSA-N 2-[2-[3-(3-chloropyridin-2-yl)-5-cyclopropyl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound ClC=1C(=NC=CC=1)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F)C1CC1 WWRFHHWIFULLSF-UHFFFAOYSA-N 0.000 claims 2
- UTZCPVCTWPUNHY-UHFFFAOYSA-N 2-[2-[4-(difluoromethyl)-2-[2-(trifluoromethyl)phenyl]pyrazol-3-yl]-7-azaspiro[3.5]nonan-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound FC(C=1C=NN(C=1C1CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F)C1=C(C=CC=C1)C(F)(F)F)F UTZCPVCTWPUNHY-UHFFFAOYSA-N 0.000 claims 2
- ZNHPXUVBWZQRFH-UHFFFAOYSA-N 2-[2-[4-(difluoromethyl)-2-[2-(trifluoromethyl)phenyl]pyrazol-3-yl]-7-azaspiro[3.5]nonan-7-yl]-4-methyl-1,3-benzothiazole-6-carboxylic acid Chemical compound FC(C=1C=NN(C=1C1CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)C)C1=C(C=CC=C1)C(F)(F)F)F ZNHPXUVBWZQRFH-UHFFFAOYSA-N 0.000 claims 2
- MYZPXNREXDHGIQ-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichloro-4-fluorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=C(C=C1Cl)F)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F MYZPXNREXDHGIQ-UHFFFAOYSA-N 0.000 claims 2
- TTWBXUXKEORCTA-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-2-hydroxy-7-azaspiro[3.5]nonan-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1(CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F)O TTWBXUXKEORCTA-UHFFFAOYSA-N 0.000 claims 2
- LUPWLIXDLUZHQX-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-2-hydroxyspiro[3.5]nonan-7-yl]oxy-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1(CC2(C1)CCC(CC2)OC=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F)O LUPWLIXDLUZHQX-UHFFFAOYSA-N 0.000 claims 2
- ZIWDUYVXURUKBR-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C=CC(=C2)C(=O)O ZIWDUYVXURUKBR-UHFFFAOYSA-N 0.000 claims 2
- ZOUZHZUQFXBCFZ-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1,3-benzoxazole-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1OC2=C(N=1)C=C(C=C2)C(=O)O ZOUZHZUQFXBCFZ-UHFFFAOYSA-N 0.000 claims 2
- SHIZQXZRYCJGMX-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1,3-benzoxazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1OC2=C(N=1)C=CC(=C2)C(=O)O SHIZQXZRYCJGMX-UHFFFAOYSA-N 0.000 claims 2
- BSLDHPKNJLYGFT-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1-methylbenzimidazole-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C1=NC2=C(N1C)C=CC(=C2)C(=O)O BSLDHPKNJLYGFT-UHFFFAOYSA-N 0.000 claims 2
- ZYJBEGYNUPPPFA-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-6-methylpyrimidine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C1=NC(=CC(=N1)C(=O)O)C ZYJBEGYNUPPPFA-UHFFFAOYSA-N 0.000 claims 2
- KDWAQUZOLNXTKG-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-7-methylpyrrolo[2,3-d]pyrimidine-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1N=CC2=C(N=1)N(C=C2C(=O)O)C KDWAQUZOLNXTKG-UHFFFAOYSA-N 0.000 claims 2
- RRGATMQOHYKZSX-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-N-cyclopropylsulfonyl-4-fluoro-1,3-benzothiazole-6-carboxamide Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)NS(=O)(=O)C1CC1)F RRGATMQOHYKZSX-UHFFFAOYSA-N 0.000 claims 2
- GRXIUVFREHQJNT-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-[1,3]thiazolo[4,5-b]pyridine-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC=2C(=NC=C(C=2)C(=O)O)N=1 GRXIUVFREHQJNT-UHFFFAOYSA-N 0.000 claims 2
- RBBJHCYUAQPSCM-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]pyrimidine-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C1=NC=C(C=N1)C(=O)O RBBJHCYUAQPSCM-UHFFFAOYSA-N 0.000 claims 2
- SRVWJMQQFOTYMZ-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]nonan-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F SRVWJMQQFOTYMZ-UHFFFAOYSA-N 0.000 claims 2
- KYWLJQVWQCNDKU-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]spiro[3.5]non-2-en-7-yl]oxy-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCC(CC2)OC=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F KYWLJQVWQCNDKU-UHFFFAOYSA-N 0.000 claims 2
- IQJYMTOLMAUPLN-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)triazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C=1N=NN(C=1C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F)C1=C(C=CC=C1Cl)Cl IQJYMTOLMAUPLN-UHFFFAOYSA-N 0.000 claims 2
- DWEUKVKIBLPATL-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(2,6-difluorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1F)F)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F DWEUKVKIBLPATL-UHFFFAOYSA-N 0.000 claims 2
- XKMCMGOHWRBXSK-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C=CC(=C2)C(=O)O XKMCMGOHWRBXSK-UHFFFAOYSA-N 0.000 claims 2
- OKQCZNGBKUMOQU-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-(trifluoromethoxy)-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)OC(F)(F)F OKQCZNGBKUMOQU-UHFFFAOYSA-N 0.000 claims 2
- OKGCUSLQEZKNIG-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxamide Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)N)F OKGCUSLQEZKNIG-UHFFFAOYSA-N 0.000 claims 2
- AWMVITFYNBJOTG-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F AWMVITFYNBJOTG-UHFFFAOYSA-N 0.000 claims 2
- JTPWRAMENPUBLY-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-N-methyl-1,3-benzothiazole-6-carboxamide Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)NC)F JTPWRAMENPUBLY-UHFFFAOYSA-N 0.000 claims 2
- WJZIUTAYTYKRHK-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-N-propan-2-yl-1,3-benzothiazole-6-carboxamide Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)NC(C)C)F WJZIUTAYTYKRHK-UHFFFAOYSA-N 0.000 claims 2
- VSSRJYHXEFICFJ-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-N-sulfamoyl-1,3-benzothiazole-6-carboxamide Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)NS(N)(=O)=O)F VSSRJYHXEFICFJ-UHFFFAOYSA-N 0.000 claims 2
- RLYHIMDAXHMJPE-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-methoxy-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)OC RLYHIMDAXHMJPE-UHFFFAOYSA-N 0.000 claims 2
- HZFPOWLMPFSUOB-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-methyl-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)C HZFPOWLMPFSUOB-UHFFFAOYSA-N 0.000 claims 2
- JIBVIIUUPKEJRZ-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-5-methoxy-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C=C(C(=C2)C(=O)O)OC JIBVIIUUPKEJRZ-UHFFFAOYSA-N 0.000 claims 2
- AVSAGQFUILFWFR-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-6-methoxy-1,3-benzothiazole-4-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC=2C(N=1)=C(C=C(C=2)OC)C(=O)O AVSAGQFUILFWFR-UHFFFAOYSA-N 0.000 claims 2
- JEHUKZVMXJYQAA-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-7-(trifluoromethyl)quinoline-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C1=NC=2C=C(C=C(C=2C=C1)C(=O)O)C(F)(F)F JEHUKZVMXJYQAA-UHFFFAOYSA-N 0.000 claims 2
- AXZGMIBDRYHJGG-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-8-methoxyquinoline-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C1=NC=2C(=CC=C(C=2C=C1)C(=O)O)OC AXZGMIBDRYHJGG-UHFFFAOYSA-N 0.000 claims 2
- OLUCEJHCIDASIR-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-N-cyclopropylsulfonyl-4-fluoro-1,3-benzothiazole-6-carboxamide Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)NS(=O)(=O)C1CC1)F OLUCEJHCIDASIR-UHFFFAOYSA-N 0.000 claims 2
- UUSDSGBPWJJVMZ-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-N-ethyl-4-fluoro-1,3-benzothiazole-6-carboxamide Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)NCC)F UUSDSGBPWJJVMZ-UHFFFAOYSA-N 0.000 claims 2
- XKVTUDWQLKQMDX-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-[1,3]thiazolo[5,4-b]pyridine-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1SC2=NC(=CC=C2N=1)C(=O)O XKVTUDWQLKQMDX-UHFFFAOYSA-N 0.000 claims 2
- DLGUEYSYYUGGQZ-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]quinoline-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C1=NC=2C=CC=C(C=2C=C1)C(=O)O DLGUEYSYYUGGQZ-UHFFFAOYSA-N 0.000 claims 2
- FAYMBBNLAXCTGK-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-(3,5-difluoropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1F)F)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F FAYMBBNLAXCTGK-UHFFFAOYSA-N 0.000 claims 2
- YZDUXZWPRUQLIL-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]-1,3-dioxa-8-azaspiro[4.5]decan-8-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)C1OC2(CO1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F YZDUXZWPRUQLIL-UHFFFAOYSA-N 0.000 claims 2
- AHBXJXIQDITTRI-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)C1=CC2(C1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F AHBXJXIQDITTRI-UHFFFAOYSA-N 0.000 claims 2
- UISPRMNEZHHHKK-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]quinoline-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)C1=CC2(C1)CCN(CC2)C1=NC2=CC=C(C=C2C=C1)C(=O)O UISPRMNEZHHHKK-UHFFFAOYSA-N 0.000 claims 2
- ZRMNEGMKVZOPDP-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-6-methylpyrimidine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)C(F)(F)F)C1=CC2(C1)CCN(CC2)C1=NC(=CC(=N1)C(=O)O)C ZRMNEGMKVZOPDP-UHFFFAOYSA-N 0.000 claims 2
- VZAPQGMVTYZJLN-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-[1,3]thiazolo[5,4-b]pyridine-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)C(F)(F)F)C1=CC2(C1)CCN(CC2)C=1SC2=NC(=CC=C2N=1)C(=O)O VZAPQGMVTYZJLN-UHFFFAOYSA-N 0.000 claims 2
- BPVDVJQTDDXUMD-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]pyrrolo[2,1-f][1,2,4]triazine-5-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)C(F)(F)F)C1=CC2(C1)CCN(CC2)C1=NN2C(C=N1)=C(C=C2)C(=O)O BPVDVJQTDDXUMD-UHFFFAOYSA-N 0.000 claims 2
- HXXVVZXBTYPWJS-UHFFFAOYSA-N 2-[2-[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]quinoxaline-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)C(F)(F)F)C1=CC2(C1)CCN(CC2)C1=NC2=CC=C(C=C2N=C1)C(=O)O HXXVVZXBTYPWJS-UHFFFAOYSA-N 0.000 claims 2
- CYHXRQJQWYSXQQ-UHFFFAOYSA-N 2-[3'-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]spiro[8-azabicyclo[3.2.1]octane-3,1'-cyclobutane]-8-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1CC2(C1)CC1CCC(C2)N1C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F CYHXRQJQWYSXQQ-UHFFFAOYSA-N 0.000 claims 2
- YAQKEYXGXVYKFQ-UHFFFAOYSA-N 2-[3-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-1,4-dioxa-8-azaspiro[4.5]decan-8-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1OC2(OC1)CCN(CC2)C=1SC2=C(N=1)C(=CC(=C2)C(=O)O)F YAQKEYXGXVYKFQ-UHFFFAOYSA-N 0.000 claims 2
- BHDJUAFZNIWISJ-UHFFFAOYSA-N 2-[6-[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]-2-azaspiro[3.3]hept-6-en-2-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)C(F)(F)F)C1=CC2(CN(C2)C=2SC3=C(N=2)C(=CC(=C3)C(=O)O)F)C1 BHDJUAFZNIWISJ-UHFFFAOYSA-N 0.000 claims 2
- SXTJHIPACWRISC-UHFFFAOYSA-N 2-hydroxyoxane-2-carboxylic acid Chemical compound OC(=O)C1(O)CCCCO1 SXTJHIPACWRISC-UHFFFAOYSA-N 0.000 claims 2
- XQRBBNBJCFYTDX-UHFFFAOYSA-N 3-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-2-hydroxyspiro[3.5]nonan-7-yl]oxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1(CC2(C1)CCC(CC2)OC=1C=C(C(=O)O)C=CC=1)O XQRBBNBJCFYTDX-UHFFFAOYSA-N 0.000 claims 2
- UHDSCTIGBYQNSV-UHFFFAOYSA-N 3-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1-methylindazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C1=NN(C2=CC(=CC=C12)C(=O)O)C UHDSCTIGBYQNSV-UHFFFAOYSA-N 0.000 claims 2
- REIQTABSJJZWOQ-UHFFFAOYSA-N 3-[2-[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1-methylpyrazolo[4,3-b]pyridine-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)C1=CC2(C1)CCN(CC2)C1=NN(C=2C1=NC=C(C=2)C(=O)O)C REIQTABSJJZWOQ-UHFFFAOYSA-N 0.000 claims 2
- YAXCQRUOIDBASP-UHFFFAOYSA-N 3-[2-[5-cyclopropyl-3-[2-(trifluoromethyl)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1-methylindazole-6-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)C(F)(F)F)C1=CC2(C1)CCN(CC2)C1=NN(C2=CC(=CC=C12)C(=O)O)C YAXCQRUOIDBASP-UHFFFAOYSA-N 0.000 claims 2
- AKJRHNHVTAAUQL-UHFFFAOYSA-N 3-[[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-2-hydroxyspiro[3.5]nonan-7-yl]oxymethyl]benzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1(CC2(C1)CCC(CC2)OCC=1C=C(C(=O)O)C=CC=1)O AKJRHNHVTAAUQL-UHFFFAOYSA-N 0.000 claims 2
- AQFAKTHAOLWCDG-UHFFFAOYSA-N 4-[2-[3-(2-chlorophenyl)-5-cyclopropyl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]benzoic acid Chemical compound ClC1=C(C=CC=C1)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C1=CC=C(C(=O)O)C=C1)C1CC1 AQFAKTHAOLWCDG-UHFFFAOYSA-N 0.000 claims 2
- WHVKNPGPTFPWEQ-UHFFFAOYSA-N 4-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-2-hydroxyspiro[3.5]nonan-7-yl]oxybenzoic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1(CC2(C1)CCC(CC2)OC1=CC=C(C(=O)O)C=C1)O WHVKNPGPTFPWEQ-UHFFFAOYSA-N 0.000 claims 2
- DVMXXSLSGKLUKP-UHFFFAOYSA-N 5-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]pyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1C=CC(=NC=1)C(=O)O DVMXXSLSGKLUKP-UHFFFAOYSA-N 0.000 claims 2
- VPJJJVTYBPWFBR-UHFFFAOYSA-N 5-[2-[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1-methylindazole-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)C1=CC2(C1)CCN(CC2)C=1C=C2C(=NN(C2=CC=1)C)C(=O)O VPJJJVTYBPWFBR-UHFFFAOYSA-N 0.000 claims 2
- BLZHNGJZBLBXEX-UHFFFAOYSA-N 5-[2-[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1-methylpyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)C1=CC2(C1)CCN(CC2)C=1C=C2C(=CN=1)N(C(=C2)C(=O)O)C BLZHNGJZBLBXEX-UHFFFAOYSA-N 0.000 claims 2
- CEMCQYVNKVSQTD-UHFFFAOYSA-N 6-[2-(3-cyclohexyl-5-cyclopropyl-1,2-oxazol-4-yl)-7-azaspiro[3.5]non-2-en-7-yl]-1-methylindole-3-carboxylic acid Chemical compound C1(CCCCC1)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C1=CC=C2C(=CN(C2=C1)C)C(=O)O)C1CC1 CEMCQYVNKVSQTD-UHFFFAOYSA-N 0.000 claims 2
- GKJRHBGSJYIOLZ-UHFFFAOYSA-N 6-[2-(3-cyclohexyl-5-cyclopropyl-1,2-oxazol-4-yl)-7-azaspiro[3.5]non-2-en-7-yl]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound C1(CCCCC1)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)C(F)(F)F)C1CC1 GKJRHBGSJYIOLZ-UHFFFAOYSA-N 0.000 claims 2
- MOFPIIUDBMDJSN-UHFFFAOYSA-N 6-[2-[3-(2,6-dichlorophenyl)-5-propan-2-yl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)Cl)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)C(F)(F)F)C(C)C MOFPIIUDBMDJSN-UHFFFAOYSA-N 0.000 claims 2
- LFYXCXFOZYAZGI-UHFFFAOYSA-N 6-[2-[3-(2-chloro-4-fluorophenyl)-5-cyclopropyl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound ClC1=C(C=CC(=C1)F)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)C(F)(F)F)C1CC1 LFYXCXFOZYAZGI-UHFFFAOYSA-N 0.000 claims 2
- JNHCLLGYVWBUIT-UHFFFAOYSA-N 6-[2-[3-(2-chloro-6-fluorophenyl)-5-cyclopropyl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)F)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)C(F)(F)F)C1CC1 JNHCLLGYVWBUIT-UHFFFAOYSA-N 0.000 claims 2
- UJYCBZKDVGIEPD-UHFFFAOYSA-N 6-[2-[3-(2-chloro-6-fluorophenyl)-5-cyclopropyl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]quinoline-2-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)F)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1C=C2C=CC(=NC2=CC=1)C(=O)O)C1CC1 UJYCBZKDVGIEPD-UHFFFAOYSA-N 0.000 claims 2
- OCPSXWOMCOFBGV-UHFFFAOYSA-N 6-[2-[3-(2-chloro-6-methylphenyl)-5-cyclopropyl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)C)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)C(F)(F)F)C1CC1 OCPSXWOMCOFBGV-UHFFFAOYSA-N 0.000 claims 2
- BLKIDVGDNKMSMJ-UHFFFAOYSA-N 6-[2-[3-(2-chloro-6-methylphenyl)-5-cyclopropyl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]quinoline-2-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)C)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1C=C2C=CC(=NC2=CC=1)C(=O)O)C1CC1 BLKIDVGDNKMSMJ-UHFFFAOYSA-N 0.000 claims 2
- AFOOMDKFFNXGIW-UHFFFAOYSA-N 6-[2-[3-(3,5-dichloropyridin-4-yl)-5-propan-2-yl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound ClC=1C=NC=C(C=1C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)C(F)(F)F)C(C)C)Cl AFOOMDKFFNXGIW-UHFFFAOYSA-N 0.000 claims 2
- ZHLIDCKSNLBMRJ-UHFFFAOYSA-N 6-[2-[3-(3-chloropyridin-2-yl)-5-cyclopropyl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-(difluoromethoxy)quinoline-2-carboxylic acid Chemical compound ClC=1C(=NC=CC=1)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OC(F)F)C1CC1 ZHLIDCKSNLBMRJ-UHFFFAOYSA-N 0.000 claims 2
- KQBATTWANJDQJT-UHFFFAOYSA-N 6-[2-[3-(3-chloropyridin-2-yl)-5-cyclopropyl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound ClC=1C(=NC=CC=1)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)C(F)(F)F)C1CC1 KQBATTWANJDQJT-UHFFFAOYSA-N 0.000 claims 2
- FJEGASLQTFTAPW-UHFFFAOYSA-N 6-[2-[3-(3-chloropyridin-2-yl)-5-cyclopropyl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-methoxyquinoline-2-carboxylic acid Chemical compound ClC=1C(=NC=CC=1)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OC)C1CC1 FJEGASLQTFTAPW-UHFFFAOYSA-N 0.000 claims 2
- VRLNJABARCNNFT-UHFFFAOYSA-N 6-[2-[3-(3-chloropyridin-2-yl)-5-cyclopropyl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]quinoline-2-carboxylic acid Chemical compound ClC=1C(=NC=CC=1)C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1C=C2C=CC(=NC2=CC=1)C(=O)O)C1CC1 VRLNJABARCNNFT-UHFFFAOYSA-N 0.000 claims 2
- CILKRDHHPWGVPC-UHFFFAOYSA-N 6-[2-[3-(3-chloropyridin-4-yl)-5-cyclopropyl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-(difluoromethoxy)quinoline-2-carboxylic acid Chemical compound ClC=1C=NC=CC=1C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OC(F)F)C1CC1 CILKRDHHPWGVPC-UHFFFAOYSA-N 0.000 claims 2
- LRKCLTZXYNXEIZ-UHFFFAOYSA-N 6-[2-[3-(3-chloropyridin-4-yl)-5-cyclopropyl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-methoxyquinoline-2-carboxylic acid Chemical compound ClC=1C=NC=CC=1C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OC)C1CC1 LRKCLTZXYNXEIZ-UHFFFAOYSA-N 0.000 claims 2
- XGCFMWFNEYKHMZ-UHFFFAOYSA-N 6-[2-[3-(3-chloropyridin-4-yl)-5-cyclopropyl-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]quinoline-2-carboxylic acid Chemical compound ClC=1C=NC=CC=1C1=NOC(=C1C1=CC2(C1)CCN(CC2)C=1C=C2C=CC(=NC2=CC=1)C(=O)O)C1CC1 XGCFMWFNEYKHMZ-UHFFFAOYSA-N 0.000 claims 2
- DTCQHSJFLJZNNW-UHFFFAOYSA-N 6-[2-[4-(difluoromethyl)-2-[2-(trifluoromethyl)phenyl]pyrazol-3-yl]-7-azaspiro[3.5]nonan-7-yl]-1-methylindole-3-carboxylic acid Chemical compound FC(C=1C=NN(C=1C1CC2(C1)CCN(CC2)C1=CC=C2C(=CN(C2=C1)C)C(=O)O)C1=C(C=CC=C1)C(F)(F)F)F DTCQHSJFLJZNNW-UHFFFAOYSA-N 0.000 claims 2
- AZVNKEPVQILRDX-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(2,6-dichloro-4-fluorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=C(C=C1Cl)F)Cl)C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)C(F)(F)F AZVNKEPVQILRDX-UHFFFAOYSA-N 0.000 claims 2
- VRFMOSIMQZRRPA-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(2,6-dichloro-4-fluorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-methoxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=C(C=C1Cl)F)Cl)C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OC VRFMOSIMQZRRPA-UHFFFAOYSA-N 0.000 claims 2
- HDWKXTMKQRXZSE-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(2,6-dichloro-4-fluorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-propan-2-yloxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=C(C=C1Cl)F)Cl)C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OC(C)C HDWKXTMKQRXZSE-UHFFFAOYSA-N 0.000 claims 2
- DNHONPYJPUPDJP-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(2,6-dichloro-4-fluorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=C(C=C1Cl)F)Cl)C1=CC2(C1)CCN(CC2)C=1C=C2C=CC(=NC2=CC=1)C(=O)O DNHONPYJPUPDJP-UHFFFAOYSA-N 0.000 claims 2
- ZRSOFPIYYNLSDC-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1-(2-trimethylsilylethoxymethyl)indole-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C1=CC=C2C(=CN(C2=C1)COCC[Si](C)(C)C)C(=O)O ZRSOFPIYYNLSDC-UHFFFAOYSA-N 0.000 claims 2
- ABEUFSGCMAZWCF-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1-methylindazole-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C1=CC=C2C(=NN(C2=C1)C)C(=O)O ABEUFSGCMAZWCF-UHFFFAOYSA-N 0.000 claims 2
- DDERFKUXIPUURA-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1-methylindole-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C1=CC=C2C=C(N(C2=C1)C)C(=O)O DDERFKUXIPUURA-UHFFFAOYSA-N 0.000 claims 2
- DMEXKGDWMCFTLU-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1-methylpyrrolo[2,3-b]pyridine-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C1=CC=C2C(=N1)N(C=C2C(=O)O)C DMEXKGDWMCFTLU-UHFFFAOYSA-N 0.000 claims 2
- RZXAEHFPVGAJRG-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]pyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C1=CC=CC(=N1)C(=O)O RZXAEHFPVGAJRG-UHFFFAOYSA-N 0.000 claims 2
- KWEDVRBXRXNSQB-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(2,6-difluorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1F)F)C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)C(F)(F)F KWEDVRBXRXNSQB-UHFFFAOYSA-N 0.000 claims 2
- YIMJXCNDELXBMU-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(2,6-difluorophenyl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1F)F)C1=CC2(C1)CCN(CC2)C=1C=C2C=CC(=NC2=CC=1)C(=O)O YIMJXCNDELXBMU-UHFFFAOYSA-N 0.000 claims 2
- SMXCWZQTGSMHFQ-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-(2-hydroxyethoxy)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OCCO SMXCWZQTGSMHFQ-UHFFFAOYSA-N 0.000 claims 2
- YIRPELGNXFSRBN-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-(difluoromethoxy)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OC(F)F YIRPELGNXFSRBN-UHFFFAOYSA-N 0.000 claims 2
- WPGAVSDZYIRUGE-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)C(F)(F)F WPGAVSDZYIRUGE-UHFFFAOYSA-N 0.000 claims 2
- LAHZVBUOKWIPNU-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-ethoxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OCC LAHZVBUOKWIPNU-UHFFFAOYSA-N 0.000 claims 2
- GCLRCFQQGUPZBQ-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-methoxypyridine-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C1=NC=C(C(=O)O)C(=C1)OC GCLRCFQQGUPZBQ-UHFFFAOYSA-N 0.000 claims 2
- AUKUERAKBLFUKO-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-methoxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OC AUKUERAKBLFUKO-UHFFFAOYSA-N 0.000 claims 2
- TVAUJLNXTLXMOE-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-methylquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)C TVAUJLNXTLXMOE-UHFFFAOYSA-N 0.000 claims 2
- LZSXRQCQUMGJBV-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-propan-2-yloxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OC(C)C LZSXRQCQUMGJBV-UHFFFAOYSA-N 0.000 claims 2
- GVLBROJHBALOBD-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1Cl)Cl)C1=CC2(C1)CCN(CC2)C=1C=C2C=CC(=NC2=CC=1)C(=O)O GVLBROJHBALOBD-UHFFFAOYSA-N 0.000 claims 2
- HJWIWPYFOCMHJY-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-(3,5-difluoropyridin-4-yl)-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-(trifluoromethyl)quinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=NC=C1F)F)C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)C(F)(F)F HJWIWPYFOCMHJY-UHFFFAOYSA-N 0.000 claims 2
- HZOVZLUVBURGHY-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]-1,3-dioxa-8-azaspiro[4.5]decan-8-yl]pyridine-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)C1OC2(CO1)CCN(CC2)C1=CC=CC(=N1)C(=O)O HZOVZLUVBURGHY-UHFFFAOYSA-N 0.000 claims 2
- FOKYWJFRYPLJJP-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-1-methylindazole-3-carbonitrile Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)C1=CC2(C1)CCN(CC2)C1=CC=C2C(=NN(C2=C1)C)C#N FOKYWJFRYPLJJP-UHFFFAOYSA-N 0.000 claims 2
- NGWJWIVLKRWULX-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-3-(trifluoromethyl)imidazo[1,5-a]pyridine-1-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)C1=CC2(C1)CCN(CC2)C=1C=CC=2N(C=1)C(=NC=2C(=O)O)C(F)(F)F NGWJWIVLKRWULX-UHFFFAOYSA-N 0.000 claims 2
- RXGBUMPSDSTQLN-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-ethoxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OCC RXGBUMPSDSTQLN-UHFFFAOYSA-N 0.000 claims 2
- ZDOHBTSUKXSISZ-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-4-propan-2-yloxyquinoline-2-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)C1=CC2(C1)CCN(CC2)C=1C=C2C(=CC(=NC2=CC=1)C(=O)O)OC(C)C ZDOHBTSUKXSISZ-UHFFFAOYSA-N 0.000 claims 2
- MJLCYGLEBHWUTA-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]-5-fluoropyridine-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)C1=CC2(C1)CCN(CC2)C1=NC=C(C(=O)O)C=C1F MJLCYGLEBHWUTA-UHFFFAOYSA-N 0.000 claims 2
- UAPNPCJVWAFKNB-UHFFFAOYSA-N 6-[2-[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]-7-azaspiro[3.5]non-2-en-7-yl]pyridazine-3-carboxylic acid Chemical compound C1(CC1)C1=C(C(=NO1)C1=C(C=CC=C1)OC(F)(F)F)C1=CC2(C1)CCN(CC2)C1=CC=C(N=N1)C(=O)O UAPNPCJVWAFKNB-UHFFFAOYSA-N 0.000 claims 2
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| IL293892A (en) | 2020-01-15 | 2022-08-01 | Inserm Institut National De La Sant? Et De La Rech M?Dicale | Use of fxr agonists for treating an infection by hepatitis d virus |
| CN111592557A (zh) * | 2020-05-09 | 2020-08-28 | 河北合佳医药科技集团股份有限公司 | 一种7-氨基-3-乙烯基头孢烷酸的一步法环保制备方法 |
| JP2024502673A (ja) | 2021-01-14 | 2024-01-22 | ウエヌイグレックオ・ファーマ | Ｈｂｖ感染の処置のためのｆｘｒアゴニストとｉｆｎの相乗効果 |
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| KR102682408B1 (ko) * | 2021-05-12 | 2024-07-05 | 에이치케이이노엔 주식회사 | 신규한 벤조티아졸 유도체, 이의 제조방법 및 이의 간질환 예방 또는 치료 용도 |
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Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993013101A1 (fr) | 1991-12-27 | 1993-07-08 | Yoshitomi Pharmaceutical Industries, Ltd. | Compose de pyridonecarboxylate, son utilisation pharmaceutique et compose spiro |
| WO1998017276A1 (en) | 1996-10-25 | 1998-04-30 | Merck & Co., Inc. | Heteroaryl spiroethercycloalkyl tachykinin receptor antagonists |
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| WO2009009059A1 (en) | 2007-07-09 | 2009-01-15 | Biogen Idec Ma Inc. | Spiro compounds as antagonists of tgf-beta |
| TW200906823A (en) | 2007-07-16 | 2009-02-16 | Lilly Co Eli | Compounds and methods for modulating FXR |
| CN101910151A (zh) | 2007-10-22 | 2010-12-08 | 先灵公司 | 双环杂环衍生物及其作为gpr119活性调节剂的用途 |
| US20110230493A1 (en) | 2008-11-21 | 2011-09-22 | Pfizer Inc. | 1-OXA-8-Azaspiro [4,5] Decabe-8-Carboxamide Compounds as FAAH Inhibitors |
| US8440710B2 (en) | 2009-10-15 | 2013-05-14 | Hoffmann-La Roche Inc. | HSL inhibitors useful in the treatment of diabetes |
| CU24152B1 (es) * | 2010-12-20 | 2016-02-29 | Irm Llc | 1,2 oxazol-8-azabiciclo[3,2,1]octano 8 il como moduladores de fxr |
| JO3154B1 (ar) | 2011-06-17 | 2017-09-20 | Glaxosmithkline Llc | عوامل مضادة لـ trpv4 |
| EP2545964A1 (en) | 2011-07-13 | 2013-01-16 | Phenex Pharmaceuticals AG | Novel FXR (NR1H4) binding and activity modulating compounds |
| JP6215230B2 (ja) | 2012-01-16 | 2017-10-18 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | イオンチャネルのモジュレーターとしてのピラン−スピロ環式ピペリジンアミド |
| IN2014DN09346A (https=) | 2012-06-13 | 2015-07-17 | Hoffmann La Roche | |
| EP2903985A1 (en) | 2012-10-03 | 2015-08-12 | Advinus Therapeutics Limited | Spirocyclic compounds, compositions and medicinal applications thereof |
| TWI714528B (zh) * | 2014-05-14 | 2021-01-01 | 瑞士商諾華公司 | 甲醯胺衍生物 |
| WO2015172747A1 (en) | 2014-05-16 | 2015-11-19 | Zhaoyin Wang | Spirocyclic molecules as mth1 inhibitors |
| EP3034501A1 (en) * | 2014-12-17 | 2016-06-22 | Gilead Sciences, Inc. | Hydroxy containing FXR (NR1H4) modulating compounds |
| EP3034499A1 (en) | 2014-12-17 | 2016-06-22 | Gilead Sciences, Inc. | Novel FXR (NR1H4) modulating compounds |
| MX2017008057A (es) | 2014-12-18 | 2017-09-28 | Novartis Ag | Derivados de azabiciclooctano como agonistas de fxr para el uso en el tratamiento de enfermedades hepaticas y gastrointestinales. |
| CN106146483A (zh) | 2015-04-23 | 2016-11-23 | 上海迪诺医药科技有限公司 | 杂环类法尼酯衍生物x受体调节剂 |
| CN106946867B (zh) * | 2016-01-06 | 2019-11-12 | 广州市恒诺康医药科技有限公司 | Fxr受体调节剂及其制备方法和用途 |
| CN107021958A (zh) | 2016-02-01 | 2017-08-08 | 山东轩竹医药科技有限公司 | Fxr受体激动剂 |
| WO2017133521A1 (zh) | 2016-02-01 | 2017-08-10 | 山东轩竹医药科技有限公司 | Fxr受体激动剂 |
| MX384205B (es) | 2016-02-22 | 2025-03-14 | Novartis Ag | Metodos para usar agonistas de fxr. |
| ES2862194T3 (es) | 2016-02-22 | 2021-10-07 | Novartis Ag | Métodos para usar agonistas del FXR |
| US10080741B2 (en) | 2016-04-26 | 2018-09-25 | Enanta Pharmaceuticals, Inc. | Isoxazole derivatives as FXR agonists and methods of use thereof |
| WO2017189663A1 (en) | 2016-04-26 | 2017-11-02 | Enanta Pharmaceuticals, Inc. | Isoxazole derivatives as fxr agonists and methods of use thereof |
| WO2017189651A1 (en) | 2016-04-26 | 2017-11-02 | Enanta Pharmaceuticals, Inc. | Isoxazole derivatives as fxr agonists and methods of use thereof |
| WO2017201155A1 (en) | 2016-05-18 | 2017-11-23 | Enanta Pharmaceuticals, Inc. | lSOXAZOLE DERIVATIVES AS FXR AGONISTS AND METHODS OF USE THEREOF |
| AR108711A1 (es) | 2016-06-13 | 2018-09-19 | Gilead Sciences Inc | Compuestos moduladores de fxr (nr1h4) |
| MX385718B (es) | 2016-06-13 | 2025-03-18 | Gilead Sciences Inc | Compuestos moduladores de fxr (nr1h4). |
| CN108430998B (zh) | 2016-09-28 | 2021-07-09 | 四川科伦博泰生物医药股份有限公司 | 氮杂双环衍生物及其制备方法和用途 |
| CN106632294A (zh) | 2016-12-15 | 2017-05-10 | 宁波百纳西药业有限公司 | 一种螺环化合物及其药物用途 |
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2018
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- 2018-10-31 US US16/175,910 patent/US11078198B2/en active Active
- 2018-10-31 TW TW107138488A patent/TW201922737A/zh unknown
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2020
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