JP2011526584A5 - - Google Patents
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- JP2011526584A5 JP2011526584A5 JP2010550957A JP2010550957A JP2011526584A5 JP 2011526584 A5 JP2011526584 A5 JP 2011526584A5 JP 2010550957 A JP2010550957 A JP 2010550957A JP 2010550957 A JP2010550957 A JP 2010550957A JP 2011526584 A5 JP2011526584 A5 JP 2011526584A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- ring
- alkyl
- oxospiro
- chroman
- 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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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 40
- 125000005843 halogen group Chemical group 0.000 claims 17
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 16
- 125000001424 substituent group Chemical group 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- 150000002148 esters Chemical class 0.000 claims 13
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 125000005647 linker group Chemical group 0.000 claims 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 9
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000002252 acyl group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000001041 indolyl group Chemical group 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 3
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 3
- -1 Group Chemical group 0.000 claims 3
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- 125000000464 thioxo group Chemical group S=* 0.000 claims 3
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 2
- 208000032841 Bulimia Diseases 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- 208000004930 Fatty Liver Diseases 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 206010019708 Hepatic steatosis Diseases 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000010706 fatty liver disease Diseases 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical group C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical group C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 claims 1
- VSOSXKMEQPYESP-UHFFFAOYSA-N 1,6-naphthyridine Chemical group C1=CN=CC2=CC=CN=C21 VSOSXKMEQPYESP-UHFFFAOYSA-N 0.000 claims 1
- MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical group C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 claims 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 1
- YYWVRTPENAIUKN-UHFFFAOYSA-N 1-[1-cyclopropyl-6-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indol-4-yl]piperidine-4-carboxylic acid Chemical compound C1=NN(C)C=C1C1=CC=C(OC2(CCN(CC2)C(=O)C=2C=C3N(C4CC4)C=CC3=C(N3CCC(CC3)C(O)=O)C=2)CC2=O)C2=C1 YYWVRTPENAIUKN-UHFFFAOYSA-N 0.000 claims 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 1
- VGALJTWZFCSONV-UHFFFAOYSA-N 1h-furo[2,3-c]pyrazole Chemical group C1=NNC2=C1C=CO2 VGALJTWZFCSONV-UHFFFAOYSA-N 0.000 claims 1
- GVLRTOYGRNLSDW-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine Chemical group C1=CC=C2C=NNC2=N1 GVLRTOYGRNLSDW-UHFFFAOYSA-N 0.000 claims 1
- FKWUPVHNVKGGSD-UHFFFAOYSA-N 1h-thieno[2,3-c]pyrazole Chemical group C1=NNC2=C1C=CS2 FKWUPVHNVKGGSD-UHFFFAOYSA-N 0.000 claims 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical group N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 claims 1
- SSNMISUJOQAFRR-UHFFFAOYSA-N 2,6-naphthyridine Chemical group N1=CC=C2C=NC=CC2=C1 SSNMISUJOQAFRR-UHFFFAOYSA-N 0.000 claims 1
- HCMMECMKVPHMDE-UHFFFAOYSA-N 2,7-naphthyridine Chemical group C1=NC=C2C=NC=CC2=C1 HCMMECMKVPHMDE-UHFFFAOYSA-N 0.000 claims 1
- RPGUOTFDTHAZGZ-UHFFFAOYSA-N 2-[1-cyclopropyl-6-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indol-4-yl]benzoic acid Chemical compound C1=NN(C)C=C1C1=CC=C(OC2(CCN(CC2)C(=O)C=2C=C3N(C4CC4)C=CC3=C(C=3C(=CC=CC=3)C(O)=O)C=2)CC2=O)C2=C1 RPGUOTFDTHAZGZ-UHFFFAOYSA-N 0.000 claims 1
- DINMYSLVSVQBBA-UHFFFAOYSA-N 2-[1-cyclopropyl-6-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indol-4-yl]oxyacetic acid Chemical compound C1=NN(C)C=C1C1=CC=C(OC2(CCN(CC2)C(=O)C=2C=C3N(C4CC4)C=CC3=C(OCC(O)=O)C=2)CC2=O)C2=C1 DINMYSLVSVQBBA-UHFFFAOYSA-N 0.000 claims 1
- RIYBBKHBXOJHCO-UHFFFAOYSA-N 3-[1-cyclopropyl-6-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indol-4-yl]benzoic acid Chemical compound C1=NN(C)C=C1C1=CC=C(OC2(CCN(CC2)C(=O)C=2C=C3N(C4CC4)C=CC3=C(C=3C=C(C=CC=3)C(O)=O)C=2)CC2=O)C2=C1 RIYBBKHBXOJHCO-UHFFFAOYSA-N 0.000 claims 1
- AYEBUJMKYQXOSE-UHFFFAOYSA-N 3-[2,6-diethoxy-4-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]phenyl]benzoic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C2=CN(C)N=C2)=CC(OCC)=C1C1=CC=CC(C(O)=O)=C1 AYEBUJMKYQXOSE-UHFFFAOYSA-N 0.000 claims 1
- QBNMFGKAJVVWLF-UHFFFAOYSA-N 3-[3-methyl-5-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indazol-1-yl]benzoic acid Chemical compound C12=CC=C(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C3=CN(C)N=C3)C=C2C(C)=NN1C1=CC=CC(C(O)=O)=C1 QBNMFGKAJVVWLF-UHFFFAOYSA-N 0.000 claims 1
- ZHUGFFNVTFZWFT-UHFFFAOYSA-N 3-[3-methyl-6-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indazol-1-yl]benzoic acid Chemical compound C12=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C3=CN(C)N=C3)=CC=C2C(C)=NN1C1=CC=CC(C(O)=O)=C1 ZHUGFFNVTFZWFT-UHFFFAOYSA-N 0.000 claims 1
- QAVDIZMXLQQANA-UHFFFAOYSA-N 3-[4-[6-(5-carbamoylpyridin-2-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]-2,6-diethoxyphenyl]benzoic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2N=CC(=CC=2)C(N)=O)=CC(OCC)=C1C1=CC=CC(C(O)=O)=C1 QAVDIZMXLQQANA-UHFFFAOYSA-N 0.000 claims 1
- XKDIWNWAQOIGJT-UHFFFAOYSA-N 3-[4-[6-(5-carbamoylpyridin-3-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]-2,6-diethoxyphenyl]benzoic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2C=C(C=NC=2)C(N)=O)=CC(OCC)=C1C1=CC=CC(C(O)=O)=C1 XKDIWNWAQOIGJT-UHFFFAOYSA-N 0.000 claims 1
- GEVPVZRXWSVVMY-UHFFFAOYSA-N 4-[1-cyclopropyl-3-methyl-6-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indol-4-yl]benzoic acid Chemical compound C12=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C3=CN(C)N=C3)=CC(C=3C=CC(=CC=3)C(O)=O)=C2C(C)=CN1C1CC1 GEVPVZRXWSVVMY-UHFFFAOYSA-N 0.000 claims 1
- ATPHQKDTAWCVJB-UHFFFAOYSA-N 4-[1-cyclopropyl-6-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indol-4-yl]benzoic acid Chemical compound C1=NN(C)C=C1C1=CC=C(OC2(CCN(CC2)C(=O)C=2C=C3N(C4CC4)C=CC3=C(C=3C=CC(=CC=3)C(O)=O)C=2)CC2=O)C2=C1 ATPHQKDTAWCVJB-UHFFFAOYSA-N 0.000 claims 1
- BXSZEGCHOFMLTE-UHFFFAOYSA-N 4-[2,6-diethoxy-4-[4-oxo-6-(1h-pyrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]phenyl]benzoic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2NN=CC=2)=CC(OCC)=C1C1=CC=C(C(O)=O)C=C1 BXSZEGCHOFMLTE-UHFFFAOYSA-N 0.000 claims 1
- YYLXNNDOTVAVPQ-UHFFFAOYSA-N 4-[2,6-diethoxy-4-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]phenyl]-2-fluorobenzoic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C2=CN(C)N=C2)=CC(OCC)=C1C1=CC=C(C(O)=O)C(F)=C1 YYLXNNDOTVAVPQ-UHFFFAOYSA-N 0.000 claims 1
- UFEOVVIQNNPRKL-UHFFFAOYSA-N 4-[2,6-diethoxy-4-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]phenyl]benzoic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C2=CN(C)N=C2)=CC(OCC)=C1C1=CC=C(C(O)=O)C=C1 UFEOVVIQNNPRKL-UHFFFAOYSA-N 0.000 claims 1
- KUAQKYFWNGPOOJ-UHFFFAOYSA-N 4-[3-methyl-5-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indazol-1-yl]benzoic acid Chemical compound C12=CC=C(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C3=CN(C)N=C3)C=C2C(C)=NN1C1=CC=C(C(O)=O)C=C1 KUAQKYFWNGPOOJ-UHFFFAOYSA-N 0.000 claims 1
- RFFNQUCMTARUDN-UHFFFAOYSA-N 4-[3-methyl-6-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indazol-1-yl]benzoic acid Chemical compound C12=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C3=CN(C)N=C3)=CC=C2C(C)=NN1C1=CC=C(C(O)=O)C=C1 RFFNQUCMTARUDN-UHFFFAOYSA-N 0.000 claims 1
- KOFXRJJZZLORNM-UHFFFAOYSA-N 4-[4-[6-(5-carbamoylpyridin-2-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]-2,6-diethoxyphenyl]benzoic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2N=CC(=CC=2)C(N)=O)=CC(OCC)=C1C1=CC=C(C(O)=O)C=C1 KOFXRJJZZLORNM-UHFFFAOYSA-N 0.000 claims 1
- BWOWFRSWPGTPRJ-UHFFFAOYSA-N 4-[4-[6-(5-carbamoylpyridin-3-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]-2,6-diethoxyphenyl]benzoic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2C=C(C=NC=2)C(N)=O)=CC(OCC)=C1C1=CC=C(C(O)=O)C=C1 BWOWFRSWPGTPRJ-UHFFFAOYSA-N 0.000 claims 1
- VTVVHLRLIQMBJM-UHFFFAOYSA-N 4-[8-cyclopropyl-2-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]quinolin-4-yl]benzoic acid Chemical compound C1=NN(C)C=C1C1=CC=C(OC2(CCN(CC2)C(=O)C=2N=C3C(C4CC4)=CC=CC3=C(C=3C=CC(=CC=3)C(O)=O)C=2)CC2=O)C2=C1 VTVVHLRLIQMBJM-UHFFFAOYSA-N 0.000 claims 1
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims 1
- FCTRNZBHYXMXRM-UHFFFAOYSA-N 5-[2,6-diethoxy-4-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]phenyl]pyridine-3-carboxylic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C2=CN(C)N=C2)=CC(OCC)=C1C1=CN=CC(C(O)=O)=C1 FCTRNZBHYXMXRM-UHFFFAOYSA-N 0.000 claims 1
- WZBZVGAYGYZBQT-UHFFFAOYSA-N 5-[4-[6-(3-carbamoylphenyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]-2,6-diethoxyphenyl]pyridine-3-carboxylic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2C=C(C=CC=2)C(N)=O)=CC(OCC)=C1C1=CN=CC(C(O)=O)=C1 WZBZVGAYGYZBQT-UHFFFAOYSA-N 0.000 claims 1
- 241000156724 Antirhea Species 0.000 claims 1
- ZVTRWPJJQREMAS-UHFFFAOYSA-N C(N)(=O)C=1C=CC(=NC1)C=1C=C2C(CC3(CCN(CC3)C(=O)C3=CC(=C(C(=C3)OCC)C3=CC=CC=C3)OCC)OC2=CC1)=O.[Na] Chemical group C(N)(=O)C=1C=CC(=NC1)C=1C=C2C(CC3(CCN(CC3)C(=O)C3=CC(=C(C(=C3)OCC)C3=CC=CC=C3)OCC)OC2=CC1)=O.[Na] ZVTRWPJJQREMAS-UHFFFAOYSA-N 0.000 claims 1
- PFHMRFPCXMUWEJ-UHFFFAOYSA-N CC1=C(C=CC=C1)C1=C(C=C(C=C1OCC)C(=O)N1CCC2(CC1)OC1=CC=C(C=C1C(C2)=O)C2=NC=C(C=C2)C(N)=O)OCC Chemical group CC1=C(C=CC=C1)C1=C(C=C(C=C1OCC)C(=O)N1CCC2(CC1)OC1=CC=C(C=C1C(C2)=O)C2=NC=C(C=C2)C(N)=O)OCC PFHMRFPCXMUWEJ-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical group 0.000 claims 1
- 125000002009 alkene group Chemical group 0.000 claims 1
- 150000001345 alkine derivatives Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical group C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 1
- JMANUKZDKDKBJP-UHFFFAOYSA-N imidazo[1,5-a]pyridine Chemical group C1=CC=CC2=CN=CN21 JMANUKZDKDKBJP-UHFFFAOYSA-N 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
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| JP2010550957A JP5501256B2 (ja) | 2008-07-04 | 2009-06-29 | 新規スピロクロマノンカルボン酸 |
Applications Claiming Priority (6)
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| JP2009108704 | 2009-04-28 | ||
| PCT/JP2009/062237 WO2010002010A1 (en) | 2008-07-04 | 2009-06-29 | Novel spirochromanone carboxylic acids |
| JP2010550957A JP5501256B2 (ja) | 2008-07-04 | 2009-06-29 | 新規スピロクロマノンカルボン酸 |
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| US8318762B2 (en) | 2008-05-28 | 2012-11-27 | Pfizer Inc. | Pyrazolospiroketone acetyl-CoA carboxylase inhibitors |
| CN102695708B (zh) | 2009-11-10 | 2014-10-15 | 辉瑞大药厂 | N1-吡唑并螺酮乙酰辅酶a羧化酶抑制剂 |
| KR101486387B1 (ko) | 2010-04-01 | 2015-01-26 | 엘지전자 주식회사 | 무선 접속 시스템에서 채널상태정보 전송 방법 |
| US8598164B2 (en) | 2010-05-06 | 2013-12-03 | Vertex Pharmaceuticals Incorporated | Heterocyclic chromene-spirocyclic piperidine amides as modulators of ion channels |
| RS55224B1 (sr) | 2010-09-30 | 2017-02-28 | Pfizer | N1-pirazolospiroketon acetil-coa karboksilaza inhibitori |
| PT2632925E (pt) | 2010-10-29 | 2015-09-01 | Pfizer | Inibidores de n1/n2-lactama da acetil-coa carboxilase |
| TWI520964B (zh) | 2011-02-02 | 2016-02-11 | 維泰克斯製藥公司 | 作為離子通道調節劑之吡咯并吡－螺環哌啶醯胺 |
| AU2012217616B2 (en) | 2011-02-18 | 2017-03-02 | Vertex Pharmaceuticals Incorporated | Chroman - spirocyclic piperidine amides as modulators of ion channels |
| US8828996B2 (en) | 2011-03-14 | 2014-09-09 | Vertex Pharmaceuticals Incorporated | Morpholine-spirocyclic piperidine amides as modulators of ion channels |
| RS54526B1 (sr) * | 2011-04-22 | 2016-06-30 | Pfizer Inc. | Upotreba derivata pirazolospiroketona kao inhibitora acetil-coa karboksilaze |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| CN102715920B (zh) * | 2012-07-06 | 2013-10-16 | 电子科技大学 | 人体目标生命特征检测方法 |
| BR112016004118A2 (pt) | 2013-09-12 | 2017-10-17 | Pfizer | uso de inibidores da acetil-coa carboxilase para tratamento de acne vulgar |
| EP3554637A4 (en) | 2016-12-14 | 2020-05-20 | 89Bio Ltd. | SPIROPIPERID DERIVATIVES |
| WO2018118670A1 (en) | 2016-12-20 | 2018-06-28 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
| CN107827887B (zh) * | 2017-11-21 | 2019-01-08 | 上海博栋化学科技有限公司 | 具有抗细菌活性的三氮唑甲酯链接螺环类化合物及其制备方法和应用 |
| EP4255904A2 (en) * | 2020-12-03 | 2023-10-11 | Domain Therapeutics | Novel par-2 inhibitors |
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| CA2189634A1 (en) | 1994-05-06 | 1995-11-16 | John J. Baldwin | Combinatorial dihydrobenzopyran library |
| JP2005162612A (ja) | 2002-01-09 | 2005-06-23 | Ajinomoto Co Inc | アシルスルホンアミド誘導体 |
| JP2005170790A (ja) | 2002-01-09 | 2005-06-30 | Ajinomoto Co Inc | Ｎ−アルキルスルフォニル置換アミド誘導体 |
| EP1478437B1 (en) | 2002-02-27 | 2005-08-31 | Pfizer Products Inc. | Acc inhibitors |
| JP2005320250A (ja) | 2002-05-09 | 2005-11-17 | Ajinomoto Co Inc | ビスラクトン誘導体及びその医薬組成物としての使用 |
| WO2004092179A1 (ja) | 2003-04-14 | 2004-10-28 | Nippon Soda Co. Ltd. | スピロ誘導体、製造法および抗酸化薬 |
| BRPI0613427A2 (pt) | 2005-07-19 | 2012-10-30 | Merck & Co Inc | composto ou seu sal ou éster, composição farmacêutica, agente terapêutico, e , uso do composto ou seu sal ou éster |
| US20100160255A1 (en) | 2005-07-29 | 2010-06-24 | Takeda Pharmaceutical Company Limited | Spiro-cyclic compound |
| AU2007326950B2 (en) | 2006-11-29 | 2010-10-14 | Pfizer Products Inc. | Spiroketone acetyl-CoA carboxylase inhibitors |
| AR064010A1 (es) | 2006-12-06 | 2009-03-04 | Merck & Co Inc | Inhibidores de la actividad de la akt |
| AU2007327992A1 (en) | 2006-12-06 | 2008-06-12 | Merck Sharp & Dohme Corp. | Inhibitors of Akt activity |
| AU2008205642B2 (en) | 2007-01-12 | 2013-06-06 | Msd K.K. | Spirochromanon derivatives |
| PE20081559A1 (es) | 2007-01-12 | 2008-11-20 | Merck & Co Inc | DERIVADOS DE ESPIROCROMANONA SUSTITUIDOS COMO INHIBIDORES DE ACETIL CoA CARBOXILASA |
| JPWO2008102749A1 (ja) | 2007-02-20 | 2010-05-27 | 武田薬品工業株式会社 | 複素環化合物 |
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- 2009-06-29 US US12/997,263 patent/US8524730B2/en active Active
- 2009-06-29 CA CA2729412A patent/CA2729412A1/en not_active Abandoned
- 2009-06-29 EP EP09773588.0A patent/EP2307422B1/en not_active Not-in-force
- 2009-06-29 AU AU2009266730A patent/AU2009266730B2/en not_active Ceased
- 2009-06-29 WO PCT/JP2009/062237 patent/WO2010002010A1/en not_active Ceased
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