JP2010515733A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010515733A5 JP2010515733A5 JP2009545577A JP2009545577A JP2010515733A5 JP 2010515733 A5 JP2010515733 A5 JP 2010515733A5 JP 2009545577 A JP2009545577 A JP 2009545577A JP 2009545577 A JP2009545577 A JP 2009545577A JP 2010515733 A5 JP2010515733 A5 JP 2010515733A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbonyl
- alkyl
- cyclo
- 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
Links
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 78
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 36
- 125000005843 halogen group Chemical group 0.000 claims 35
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims 27
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 23
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 22
- 125000001424 substituent group Chemical group 0.000 claims 21
- 150000002148 esters Chemical class 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 17
- 125000002252 acyl group Chemical group 0.000 claims 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000004043 oxo group Chemical group O=* 0.000 claims 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 12
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 10
- 125000004414 alkyl thio group Chemical group 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000004434 sulfur atom Chemical group 0.000 claims 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 125000000464 thioxo group Chemical group S=* 0.000 claims 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 6
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 6
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 6
- -1 1-Ethyl-4-methoxy-1H-benzimidazol-6-yl Chemical group 0.000 claims 5
- 125000004423 acyloxy group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 3
- GVLRTOYGRNLSDW-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine Chemical compound C1=CC=C2C=NNC2=N1 GVLRTOYGRNLSDW-UHFFFAOYSA-N 0.000 claims 3
- FKWUPVHNVKGGSD-UHFFFAOYSA-N 1h-thieno[2,3-c]pyrazole Chemical compound C1=NNC2=C1C=CS2 FKWUPVHNVKGGSD-UHFFFAOYSA-N 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- KZOWNALBTMILAP-JBMRGDGGSA-N ancitabine hydrochloride Chemical compound Cl.N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 KZOWNALBTMILAP-JBMRGDGGSA-N 0.000 claims 3
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 3
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 3
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 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
- 206010019708 Hepatic steatosis Diseases 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000010706 fatty liver disease Diseases 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- OEOFWVOLIASGRM-UHFFFAOYSA-N (1-cyclopropyl-4-methoxyindol-6-yl)-[6-(2H-tetrazol-5-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]methanone Chemical compound C1(CC1)N1C=CC2=C(C=C(C=C12)C(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C1=NN=NN1)OC OEOFWVOLIASGRM-UHFFFAOYSA-N 0.000 claims 1
- 125000006773 (C2-C7) alkylcarbonyl group Chemical group 0.000 claims 1
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims 1
- AWNDPNWXFGRJQI-UHFFFAOYSA-N 1'-(1,3-diethyl-7-methoxy-2-oxobenzimidazole-5-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C=1C(OC)=C2N(CC)C(=O)N(CC)C2=CC=1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=NN=NN1 AWNDPNWXFGRJQI-UHFFFAOYSA-N 0.000 claims 1
- JHWHHWDHRLPXLG-UHFFFAOYSA-N 1'-(1,4-diethoxyindazole-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C=1C=2N(OCC)N=CC=2C(OCC)=CC=1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=NN=NN1 JHWHHWDHRLPXLG-UHFFFAOYSA-N 0.000 claims 1
- OAMOWQJTVYLHGK-UHFFFAOYSA-N 1'-(1,4-dimethoxyindole-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C=1C=2N(OC)C=CC=2C(OC)=CC=1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=NN=NN1 OAMOWQJTVYLHGK-UHFFFAOYSA-N 0.000 claims 1
- YPJUVNXGAKFASN-UHFFFAOYSA-N 1'-(1,4-dimethoxyindole-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one;sodium Chemical compound [Na].C=1C=2N(OC)C=CC=2C(OC)=CC=1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C=1N=NNN=1 YPJUVNXGAKFASN-UHFFFAOYSA-N 0.000 claims 1
- JFAWMIWDSQSOMV-UHFFFAOYSA-N 1'-(1-cyclopropyl-4-ethoxy-3-methylindole-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=C(C)C=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)=CC=2N1C1CC1 JFAWMIWDSQSOMV-UHFFFAOYSA-N 0.000 claims 1
- LPWKEJNQEJOLNF-UHFFFAOYSA-N 1'-(1-cyclopropyl-4-ethoxyindole-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=CC=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)=CC=2N1C1CC1 LPWKEJNQEJOLNF-UHFFFAOYSA-N 0.000 claims 1
- OJQNMRDPSKTWSY-UHFFFAOYSA-N 1'-(1-cyclopropyl-4-ethoxyindole-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one;sodium Chemical compound [Na].C1=CC=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C3=NNN=N3)=CC=2N1C1CC1 OJQNMRDPSKTWSY-UHFFFAOYSA-N 0.000 claims 1
- MWOXXNTYIFYXJQ-UHFFFAOYSA-N 1'-(1-cyclopropyl-4-methoxy-3-methylindole-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=C(C)C=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)=CC=2N1C1CC1 MWOXXNTYIFYXJQ-UHFFFAOYSA-N 0.000 claims 1
- JQKVGZANRSXPOU-UHFFFAOYSA-N 1'-(1-cyclopropyl-4-methoxyindole-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=CC=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)=CC=2N1C1CC1 JQKVGZANRSXPOU-UHFFFAOYSA-N 0.000 claims 1
- DZCHXXJDTKQUOA-UHFFFAOYSA-N 1'-(1-cyclopropyl-4-methoxyindole-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one;sodium Chemical compound [Na].C1=CC=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C3=NNN=N3)=CC=2N1C1CC1 DZCHXXJDTKQUOA-UHFFFAOYSA-N 0.000 claims 1
- AJUCBKYSAOERCP-UHFFFAOYSA-N 1'-(1-cyclopropyl-4-methoxyindole-6-carbonyl)-6-(5-oxo-1,2-dihydro-1,2,4-triazol-3-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=CC=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NC(=O)NN=3)=CC=2N1C1CC1 AJUCBKYSAOERCP-UHFFFAOYSA-N 0.000 claims 1
- VXOXUMFIISPGSV-UHFFFAOYSA-N 1'-(1-cyclopropyl-4-methoxyindole-6-carbonyl)-6-(5-oxo-2h-1,2,4-oxadiazol-3-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=CC=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NC(=O)ON=3)=CC=2N1C1CC1 VXOXUMFIISPGSV-UHFFFAOYSA-N 0.000 claims 1
- OYZMUGLPMDQPDV-UHFFFAOYSA-N 1'-(1-ethyl-3-methylthieno[2,3-c]pyrazole-5-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound S1C=2N(CC)N=C(C)C=2C=C1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=NN=NN1 OYZMUGLPMDQPDV-UHFFFAOYSA-N 0.000 claims 1
- NKDMEHKUJITRJR-UHFFFAOYSA-N 1'-(1-ethyl-4-methoxyindazole-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=C2N(CC)N=CC2=C(OC)C=C1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=NN=NN1 NKDMEHKUJITRJR-UHFFFAOYSA-N 0.000 claims 1
- ZMELGQVAMKHNGD-UHFFFAOYSA-N 1'-(1-ethyl-4-methoxyindole-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=C2N(CC)C=CC2=C(OC)C=C1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=NN=NN1 ZMELGQVAMKHNGD-UHFFFAOYSA-N 0.000 claims 1
- AWKUNWUUMKOYCI-UHFFFAOYSA-N 1'-(1-ethyl-4-morpholin-4-ylindole-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=C2N(CC)C=CC2=C(N2CCOCC2)C=C1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=NN=NN1 AWKUNWUUMKOYCI-UHFFFAOYSA-N 0.000 claims 1
- BQDDEWPJPSWXRR-UHFFFAOYSA-N 1'-(2-cyclopropyl-7-ethoxy-1,3-benzoxazole-5-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound O1C=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)=CC=2N=C1C1CC1 BQDDEWPJPSWXRR-UHFFFAOYSA-N 0.000 claims 1
- XUYLEIKOZAMWOE-UHFFFAOYSA-N 1'-(3-chloro-1-cyclopropyl-4-ethoxyindole-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=C(Cl)C=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)=CC=2N1C1CC1 XUYLEIKOZAMWOE-UHFFFAOYSA-N 0.000 claims 1
- OCRONEAVJHGACD-UHFFFAOYSA-N 1'-(3-chloro-1-cyclopropyl-7-ethoxyindole-5-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)=CC=2C(Cl)=CN1C1CC1 OCRONEAVJHGACD-UHFFFAOYSA-N 0.000 claims 1
- ZLDRXVSQRSQAOV-UHFFFAOYSA-N 1'-(3-cyclopropyl-7-ethoxy-1,2-benzoxazole-5-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound N=1OC=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)=CC=2C=1C1CC1 ZLDRXVSQRSQAOV-UHFFFAOYSA-N 0.000 claims 1
- JHCULCUEXUZDTM-UHFFFAOYSA-N 1'-(3-cyclopropyl-7-methoxybenzimidazole-5-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=NC=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)=CC=2N1C1CC1 JHCULCUEXUZDTM-UHFFFAOYSA-N 0.000 claims 1
- GKXFKKPTSSQZNU-UHFFFAOYSA-N 1'-(3-cyclopropyl-8-methoxyimidazo[1,2-a]pyridine-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C=1N=C2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)=CN2C=1C1CC1 GKXFKKPTSSQZNU-UHFFFAOYSA-N 0.000 claims 1
- AFKBHASOWVCPBV-UHFFFAOYSA-N 1'-(4-acetyl-7-methoxy-1-benzofuran-2-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound O1C=2C(OC)=CC=C(C(C)=O)C=2C=C1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=NN=NN1 AFKBHASOWVCPBV-UHFFFAOYSA-N 0.000 claims 1
- OQZSPIHVLNEMOM-UHFFFAOYSA-N 1'-(4-methoxy-1-methylpyrazolo[3,4-b]pyridine-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound N=1C=2N(C)N=CC=2C(OC)=CC=1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=NN=NN1 OQZSPIHVLNEMOM-UHFFFAOYSA-N 0.000 claims 1
- YWEBYUIRXNXPKJ-UHFFFAOYSA-N 1'-[1-cyclopropyl-4-(2-hydroxyethoxy)indole-6-carbonyl]-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=CC=2C(OCCO)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)=CC=2N1C1CC1 YWEBYUIRXNXPKJ-UHFFFAOYSA-N 0.000 claims 1
- VIINMHDSRKGUSP-UHFFFAOYSA-N 1'-[1-ethyl-4-(2-hydroxyethoxy)indole-6-carbonyl]-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=C2N(CC)C=CC2=C(OCCO)C=C1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=NN=NN1 VIINMHDSRKGUSP-UHFFFAOYSA-N 0.000 claims 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- MMOGEKMWSXYDNU-UHFFFAOYSA-N 1-cyclopropyl-4-ethoxy-6-[4-oxo-6-(1h-pyrazol-4-yl)spiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indole-3-carboxylic acid Chemical compound C1=C(C(O)=O)C=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C3=CNN=C3)=CC=2N1C1CC1 MMOGEKMWSXYDNU-UHFFFAOYSA-N 0.000 claims 1
- VYYLYKNBTKXAJC-UHFFFAOYSA-N 1-cyclopropyl-4-ethoxy-6-[4-oxo-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indole-3-carboxamide Chemical compound C1=C(C(N)=O)C=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)=CC=2N1C1CC1 VYYLYKNBTKXAJC-UHFFFAOYSA-N 0.000 claims 1
- BPNDISJEGZBLQJ-UHFFFAOYSA-N 1-cyclopropyl-4-ethoxy-6-[6-[(2-methylpyrazol-3-yl)amino]-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indole-3-carboxylic acid Chemical compound C1=C(C(O)=O)C=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(NC=5N(N=CC=5)C)C=C3C(=O)C4)=CC=2N1C1CC1 BPNDISJEGZBLQJ-UHFFFAOYSA-N 0.000 claims 1
- WTFVNBJKZFCVHC-UHFFFAOYSA-N 1-cyclopropyl-4-ethoxy-n-methyl-6-[4-oxo-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indole-3-carboxamide Chemical compound C1=C(C(=O)NC)C=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)=CC=2N1C1CC1 WTFVNBJKZFCVHC-UHFFFAOYSA-N 0.000 claims 1
- USCXFVCAIMZLJL-UHFFFAOYSA-N 3-[1'-(1-cyclopropyl-4-methoxyindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]-1h-1,2,4-triazole-5-carboxamide Chemical compound C1=CC=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NC(=NN=3)C(N)=O)=CC=2N1C1CC1 USCXFVCAIMZLJL-UHFFFAOYSA-N 0.000 claims 1
- PDAJKOILZCBVGF-UHFFFAOYSA-N 3-[1'-(1-cyclopropyl-4-methoxyindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]benzoic acid Chemical compound C1=CC=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=C(C=CC=3)C(O)=O)=CC=2N1C1CC1 PDAJKOILZCBVGF-UHFFFAOYSA-N 0.000 claims 1
- IMNGKACLQXZBGK-UHFFFAOYSA-N 3-[1'-(3-carbamoyl-1-cyclopropyl-4-ethoxyindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]benzoic acid Chemical compound C1=C(C(N)=O)C=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=C(C=CC=3)C(O)=O)=CC=2N1C1CC1 IMNGKACLQXZBGK-UHFFFAOYSA-N 0.000 claims 1
- YWTADLQQMJMIFQ-UHFFFAOYSA-N 4-[1'-(1-cyclopropyl-4-ethoxy-3-methylindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-2-carboxylic acid Chemical compound C1=C(C)C=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=C(N=CC=3)C(O)=O)=CC=2N1C1CC1 YWTADLQQMJMIFQ-UHFFFAOYSA-N 0.000 claims 1
- OIZHPXQONHLOHM-UHFFFAOYSA-N 4-[1'-(1-cyclopropyl-4-methoxy-3-methylindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-2-carboxylic acid Chemical compound C1=C(C)C=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=C(N=CC=3)C(O)=O)=CC=2N1C1CC1 OIZHPXQONHLOHM-UHFFFAOYSA-N 0.000 claims 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims 1
- RUEOSAFLJXCAIN-UHFFFAOYSA-N 5-[1'-(1,4-dimethoxy-3-methylindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-3-carboxylic acid Chemical compound C=1C=2N(OC)C=C(C)C=2C(OC)=CC=1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=CN=CC(C(O)=O)=C1 RUEOSAFLJXCAIN-UHFFFAOYSA-N 0.000 claims 1
- APPNDGWGOXONSC-UHFFFAOYSA-N 5-[1'-(1-cyclopropyl-4-ethoxy-3-methylindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]-2-methylpyridine-3-carboxylic acid Chemical group C1=C(C)C=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=C(C(C)=NC=3)C(O)=O)=CC=2N1C1CC1 APPNDGWGOXONSC-UHFFFAOYSA-N 0.000 claims 1
- WFWSTFMGVNHXSR-UHFFFAOYSA-N 5-[1'-(1-cyclopropyl-4-ethoxy-3-methylindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-3-carboxylic acid Chemical compound C1=C(C)C=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=C(C=NC=3)C(O)=O)=CC=2N1C1CC1 WFWSTFMGVNHXSR-UHFFFAOYSA-N 0.000 claims 1
- JNQADECYZCNJMH-UHFFFAOYSA-N 5-[1'-(1-cyclopropyl-4-methoxy-3-methylindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]-2-methylpyridine-3-carboxylic acid Chemical compound C1=C(C)C=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=C(C(C)=NC=3)C(O)=O)=CC=2N1C1CC1 JNQADECYZCNJMH-UHFFFAOYSA-N 0.000 claims 1
- WDBNGXLHMZSUEI-UHFFFAOYSA-N 5-[1'-(1-cyclopropyl-4-methoxy-3-methylindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-3-carboxylic acid Chemical compound C1=C(C)C=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=C(C=NC=3)C(O)=O)=CC=2N1C1CC1 WDBNGXLHMZSUEI-UHFFFAOYSA-N 0.000 claims 1
- JOIYYAUZXKGMEN-UHFFFAOYSA-N 5-[1'-(1-cyclopropyl-4-methoxyindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-3-carboxylic acid Chemical compound C1=CC=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=C(C=NC=3)C(O)=O)=CC=2N1C1CC1 JOIYYAUZXKGMEN-UHFFFAOYSA-N 0.000 claims 1
- ROSMZCLZFCCOAR-UHFFFAOYSA-N 5-[1'-(6-cyclopropyl-1-propan-2-ylpyrazolo[3,4-b]pyridine-4-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-3-carboxylic acid Chemical compound N1=C2N(C(C)C)N=CC2=C(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2C=C(C=NC=2)C(O)=O)C=C1C1CC1 ROSMZCLZFCCOAR-UHFFFAOYSA-N 0.000 claims 1
- KAZDJFUSKMFXBV-UHFFFAOYSA-N 6-(5-bromopyridin-3-yl)-1'-(1-cyclopropyl-4-methoxy-3-methylindole-6-carbonyl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=C(C)C=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=C(Br)C=NC=3)=CC=2N1C1CC1 KAZDJFUSKMFXBV-UHFFFAOYSA-N 0.000 claims 1
- CAXIHAPXMMNCES-UHFFFAOYSA-N 6-[1'-(1-cyclopropyl-4-methoxy-3-methylindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-3-carboxylic acid Chemical compound C1=C(C)C=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3N=CC(=CC=3)C(O)=O)=CC=2N1C1CC1 CAXIHAPXMMNCES-UHFFFAOYSA-N 0.000 claims 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
- HKGYUWFDBUZZGY-UHFFFAOYSA-N C1(CC1)N1C=C(C2=C(C=C(C=C12)C(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C2=NN=NN2)OCC)C Chemical compound C1(CC1)N1C=C(C2=C(C=C(C=C12)C(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C2=NN=NN2)OCC)C HKGYUWFDBUZZGY-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims 1
- LFEQZYUGJYUYIE-UHFFFAOYSA-N n-(2-amino-2-oxoethyl)-1'-(1,4-diethoxyindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-carboxamide Chemical compound C1C(=O)C2=CC(C(=O)NCC(N)=O)=CC=C2OC1(CC1)CCN1C(=O)C(C=C1OCC)=CC2=C1C=CN2OCC LFEQZYUGJYUYIE-UHFFFAOYSA-N 0.000 claims 1
- CTQOCKWNBNCZNJ-UHFFFAOYSA-N n-(2-amino-2-oxoethyl)-1'-(1-cyclopropyl-4-ethoxy-3-methylindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-carboxamide Chemical compound C1=C(C)C=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C(=O)NCC(N)=O)=CC=2N1C1CC1 CTQOCKWNBNCZNJ-UHFFFAOYSA-N 0.000 claims 1
- MBDZVTFWDBQDGE-UHFFFAOYSA-N n-(2-amino-2-oxoethyl)-1'-(1-cyclopropyl-4-ethoxyindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-carboxamide Chemical compound C1=CC=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C(=O)NCC(N)=O)=CC=2N1C1CC1 MBDZVTFWDBQDGE-UHFFFAOYSA-N 0.000 claims 1
- FVTARXCMBGNOLF-UHFFFAOYSA-N n-(2-amino-2-oxoethyl)-1'-(1-cyclopropyl-4-methoxyindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-carboxamide Chemical compound C1=CC=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C(=O)NCC(N)=O)=CC=2N1C1CC1 FVTARXCMBGNOLF-UHFFFAOYSA-N 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- PHRGTBNTADHMBH-UHFFFAOYSA-M sodium;4-[1'-(1-cyclopropyl-4-methoxyindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-2-carboxylate Chemical compound [Na+].C1=CC=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=C(N=CC=3)C([O-])=O)=CC=2N1C1CC1 PHRGTBNTADHMBH-UHFFFAOYSA-M 0.000 claims 1
- ZCYIWEKNLXHNGV-UHFFFAOYSA-M sodium;5-[1'-(1-cyclopropyl-4-ethoxy-3-methylindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-3-carboxylate Chemical compound [Na+].C1=C(C)C=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=C(C=NC=3)C([O-])=O)=CC=2N1C1CC1 ZCYIWEKNLXHNGV-UHFFFAOYSA-M 0.000 claims 1
- WZGQQJLIKGPVMH-UHFFFAOYSA-M sodium;5-[1'-(1-cyclopropyl-4-ethoxyindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-3-carboxylate Chemical compound [Na+].C1=CC=2C(OCC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=C(C=NC=3)C([O-])=O)=CC=2N1C1CC1 WZGQQJLIKGPVMH-UHFFFAOYSA-M 0.000 claims 1
- GGRZUOUSTJCEBC-UHFFFAOYSA-M sodium;5-[1'-(1-cyclopropyl-4-methoxy-3-methylindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-3-carboxylate Chemical compound [Na+].C1=C(C)C=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=C(C=NC=3)C([O-])=O)=CC=2N1C1CC1 GGRZUOUSTJCEBC-UHFFFAOYSA-M 0.000 claims 1
- SUDMSXKBZWSKPJ-UHFFFAOYSA-M sodium;5-[1'-(1-cyclopropyl-4-methoxyindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-2-carboxylate Chemical compound [Na+].C1=CC=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=NC(=CC=3)C([O-])=O)=CC=2N1C1CC1 SUDMSXKBZWSKPJ-UHFFFAOYSA-M 0.000 claims 1
- FOTRFPZDSUQERC-UHFFFAOYSA-M sodium;5-[1'-(3-chloro-1-cyclopropyl-4-methoxyindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-3-carboxylate Chemical compound [Na+].C1=C(Cl)C=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=C(C=NC=3)C([O-])=O)=CC=2N1C1CC1 FOTRFPZDSUQERC-UHFFFAOYSA-M 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88030207P | 2007-01-12 | 2007-01-12 | |
| US60/880,302 | 2007-01-12 | ||
| PCT/US2008/000221 WO2008088688A1 (en) | 2007-01-12 | 2008-01-08 | Substituted spirochromanone derivatives as acc inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010515733A JP2010515733A (ja) | 2010-05-13 |
| JP2010515733A5 true JP2010515733A5 (https=) | 2011-02-03 |
| JP5319550B2 JP5319550B2 (ja) | 2013-10-16 |
Family
ID=39297859
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009545577A Expired - Fee Related JP5319550B2 (ja) | 2007-01-12 | 2008-01-08 | 置換スピロクロマノン誘導体 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US8093389B2 (https=) |
| EP (1) | EP2111406B1 (https=) |
| JP (1) | JP5319550B2 (https=) |
| KR (1) | KR20090108022A (https=) |
| CN (1) | CN101631791B (https=) |
| AR (1) | AR064824A1 (https=) |
| AU (1) | AU2008205638B2 (https=) |
| BR (1) | BRPI0806531A2 (https=) |
| CA (1) | CA2674573C (https=) |
| CL (1) | CL2008000067A1 (https=) |
| CO (1) | CO6190611A2 (https=) |
| CR (1) | CR10944A (https=) |
| DO (1) | DOP2009000176A (https=) |
| EC (1) | ECSP099503A (https=) |
| GT (1) | GT200900194A (https=) |
| HN (1) | HN2009001276A (https=) |
| MA (1) | MA31108B1 (https=) |
| MX (1) | MX2009007502A (https=) |
| NI (1) | NI200900139A (https=) |
| NZ (1) | NZ577825A (https=) |
| PE (1) | PE20081559A1 (https=) |
| RU (1) | RU2009130736A (https=) |
| SG (1) | SG177977A1 (https=) |
| TW (1) | TW200836727A (https=) |
| UA (1) | UA103990C2 (https=) |
| WO (2) | WO2008088688A1 (https=) |
| ZA (1) | ZA200904138B (https=) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2008000966A (es) * | 2005-07-19 | 2008-03-26 | Merck & Co Inc | Nuevos derivados de espirocromanona. |
| WO2008088692A2 (en) * | 2007-01-12 | 2008-07-24 | Merck & Co., Inc. | Spirochromanon derivatives |
| US7946800B2 (en) | 2007-04-06 | 2011-05-24 | Brooks Automation, Inc. | Substrate transport apparatus with multiple independently movable articulated arms |
| US8752449B2 (en) | 2007-05-08 | 2014-06-17 | Brooks Automation, Inc. | Substrate transport apparatus with multiple movable arms utilizing a mechanical switch mechanism |
| EP2242745A1 (de) * | 2008-02-07 | 2010-10-27 | Sanofi-Aventis | Neue phenyl-substituierte imidazolidine, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2009144554A1 (en) * | 2008-05-28 | 2009-12-03 | Pfizer, Inc. | Pyrazolospiroketone acetyl-c0a carboxylase inhibitors |
| CA2729412A1 (en) | 2008-07-04 | 2010-01-07 | Banyu Pharmaceutical Co., Ltd. | Novel spirochromanone carboxylic acids |
| US8110570B2 (en) * | 2008-07-14 | 2012-02-07 | Cropsolution, Inc. | Modulators of acetyl-coenzyme A carboxylase and methods of use thereof |
| US8653098B2 (en) | 2008-11-20 | 2014-02-18 | Genentech, Inc. | Pyrazolopyridine PI3K inhibitor compounds and methods of use |
| WO2011058474A1 (en) * | 2009-11-10 | 2011-05-19 | Pfizer Inc. | N1-pyrazolospiroketone acetyl-coa carboxylase inhibitors |
| CA2786258C (en) * | 2009-12-31 | 2018-10-23 | Deka Products Limited Partnership | Infusion pump assembly |
| US8598164B2 (en) | 2010-05-06 | 2013-12-03 | Vertex Pharmaceuticals Incorporated | Heterocyclic chromene-spirocyclic piperidine amides as modulators of ion channels |
| WO2011157827A1 (de) | 2010-06-18 | 2011-12-22 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| CN101851237B (zh) * | 2010-06-18 | 2012-10-17 | 南方医科大学 | 一种螺环化合物及其制备方法和应用 |
| HRP20161178T1 (hr) | 2010-09-30 | 2016-11-04 | Pfizer Inc. | N1-PIRAZOLOSPIROKETONSKI INHIBITORI ACETIL-CoA-KARBOKSILAZE |
| BR112013010310A2 (pt) | 2010-10-29 | 2016-11-29 | Pfizer | inibidores de acetil-coa carboxilase de lactama n1/n2 |
| WO2012077655A1 (ja) * | 2010-12-07 | 2012-06-14 | 塩野義製薬株式会社 | Ｇｐｒ１１９アゴニスト活性を有するスピロ誘導体 |
| MX355907B (es) | 2011-02-02 | 2018-05-04 | Vertex Pharma | Pirrolopirazina-piperidina espirociclica-amidas como moduladores de canales de ionicos. |
| JP5940562B2 (ja) | 2011-02-18 | 2016-06-29 | 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クロマン−スピロ環式ピペリジンアミド |
| MX347982B (es) | 2011-03-14 | 2017-05-22 | Vertex Pharma | Morfolina-piperidina espirociclica-amidas como moduladores de canales ionicos. |
| MY162167A (en) | 2011-04-22 | 2017-05-31 | Pfizer | Substituted acetyl-coa carboxylase inhibitors |
| TW201300393A (zh) * | 2011-05-20 | 2013-01-01 | Kowa Co | 新穎之螺哌啶衍生物及含有其之醫藥 |
| WO2013113773A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
| WO2013113776A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
| WO2013113787A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
| WO2013113715A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
| WO2013113716A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
| JP2015511940A (ja) | 2012-02-03 | 2015-04-23 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 殺菌性ピリミジン化合物 |
| WO2013113720A1 (en) | 2012-02-03 | 2013-08-08 | Basf Se | Fungicidal pyrimidine compounds |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| JP6064062B2 (ja) | 2013-03-15 | 2017-01-18 | ファイザー・インク | Ａｍｐｋを活性化させるインダゾール化合物 |
| AU2014262547A1 (en) | 2013-05-10 | 2015-11-26 | Gilead Apollo, Llc | ACC inhibitors and uses thereof |
| MX2015015422A (es) * | 2013-05-10 | 2016-06-21 | Nimbus Apollo Inc | Inhibidores de acetil-coa carboxilasa (acc) y usos de los mismos. |
| HK1217448A1 (zh) | 2013-09-12 | 2017-01-13 | 辉瑞大药厂 | 乙酰辅酶a羧化酶抑制剂用於治疗寻常痤疮的用途 |
| WO2018112204A1 (en) | 2016-12-14 | 2018-06-21 | Cephalon, Inc. | Spiropiperidine derivatives |
| US11541046B2 (en) * | 2017-06-30 | 2023-01-03 | Quixgen, Inc. | Spirolactone compounds |
| AU2023316863A1 (en) * | 2022-07-29 | 2025-02-13 | Pfizer Inc. | Novel acc inhibitors |
| CN119798270B (zh) * | 2025-01-06 | 2026-02-24 | 中国海洋大学 | 靶向egfr的小分子化合物及其应用 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2814983A1 (de) * | 1978-04-07 | 1979-10-18 | Bayer Ag | Neue chromanon-derivate |
| US5206240A (en) * | 1989-12-08 | 1993-04-27 | Merck & Co., Inc. | Nitrogen-containing spirocycles |
| JPH03182725A (ja) | 1989-12-08 | 1991-08-08 | Internatl Business Mach Corp <Ibm> | 非線形光学素子及びその製造方法 |
| IL96507A0 (en) | 1989-12-08 | 1991-08-16 | Merck & Co Inc | Nitrogen-containing spirocycles and pharmaceutical compositions containing them |
| NZ243065A (en) | 1991-06-13 | 1995-07-26 | Lundbeck & Co As H | Piperidine derivatives and pharmaceutical compositions |
| DE69412067T2 (de) | 1993-01-28 | 1999-03-25 | Merck & Co., Inc., Rahway, N.J. | Substituierte spiro-azaringen als tachykinine rezeptor antagonisten |
| US5688997A (en) * | 1994-05-06 | 1997-11-18 | Pharmacopeia, Inc. | Process for preparing intermediates for a combinatorial dihydrobenzopyran library |
| US5856083A (en) | 1994-05-06 | 1999-01-05 | Pharmacopeia, Inc. | Lawn assay for compounds that affect enzyme activity or bind to target molecules |
| JPH10500112A (ja) | 1994-05-06 | 1998-01-06 | ファーマコピーア，インコーポレイテッド | 組合せ ジヒドロベンゾピラン ライブラリー |
| US6017768A (en) | 1994-05-06 | 2000-01-25 | Pharmacopeia, Inc. | Combinatorial dihydrobenzopyran library |
| CA2221842A1 (en) | 1995-06-06 | 1996-12-12 | Merck & Co., Inc. | Alpha 1a adrenergic receptor antagonists |
| GB9601724D0 (en) * | 1996-01-29 | 1996-03-27 | Merck Sharp & Dohme | Therapeutic agents |
| GB0003397D0 (en) * | 2000-02-14 | 2000-04-05 | Merck Sharp & Dohme | Therapeutic agents |
| AU2001289831A1 (en) | 2000-09-06 | 2002-03-22 | Bayer Aktiengesellschaft | Medicaments against viral infections |
| 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 |
| NZ534582A (en) | 2002-02-27 | 2006-03-31 | Pfizer Prod 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 |
| WO2004058727A1 (en) | 2002-12-20 | 2004-07-15 | Bayer Pharmaceuticals Corporation | Substituted 3,5-dihydro-4h-imidazol-4-ones for the treatment of obesity |
| JPWO2004092179A1 (ja) * | 2003-04-14 | 2006-07-06 | 日本曹達株式会社 | スピロ誘導体、製造法および抗酸化薬 |
| FR2856685B1 (fr) | 2003-06-25 | 2005-09-23 | Merck Sante Sas | Derives de thiazolylpiperidine, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| JP2005119987A (ja) * | 2003-10-15 | 2005-05-12 | Ajinomoto Co Inc | アシルスルホンアミド誘導体 |
| WO2006040329A1 (en) * | 2004-10-12 | 2006-04-20 | Novo Nordisk A/S | 1 ibeta- hydroxysteroid dehydrogenase type 1 active spiro compounds |
| JP2008520700A (ja) | 2004-11-18 | 2008-06-19 | インサイト・コーポレイション | １１−βヒドロキシルステロイドデヒドロゲナーゼタイプＩの阻害剤およびその使用方法 |
| JP2008540395A (ja) * | 2005-05-03 | 2008-11-20 | ファイザー・インク | アミドレソルシノール化合物 |
| MX2008000966A (es) * | 2005-07-19 | 2008-03-26 | Merck & Co Inc | Nuevos derivados de espirocromanona. |
| EA200900613A1 (ru) * | 2006-11-29 | 2009-10-30 | Пфайзер Продактс Инк. | Спирокетоновые ингибиторы ацетил-коа-карбоксилаз |
| WO2008088692A2 (en) * | 2007-01-12 | 2008-07-24 | Merck & Co., Inc. | Spirochromanon derivatives |
-
2008
- 2008-01-04 PE PE2008000089A patent/PE20081559A1/es not_active Application Discontinuation
- 2008-01-07 TW TW097100608A patent/TW200836727A/zh unknown
- 2008-01-08 EP EP08713050A patent/EP2111406B1/en active Active
- 2008-01-08 SG SG2012002739A patent/SG177977A1/en unknown
- 2008-01-08 RU RU2009130736/04A patent/RU2009130736A/ru not_active Application Discontinuation
- 2008-01-08 CA CA2674573A patent/CA2674573C/en not_active Expired - Fee Related
- 2008-01-08 JP JP2009545577A patent/JP5319550B2/ja not_active Expired - Fee Related
- 2008-01-08 KR KR1020097014377A patent/KR20090108022A/ko not_active Withdrawn
- 2008-01-08 WO PCT/US2008/000221 patent/WO2008088688A1/en not_active Ceased
- 2008-01-08 US US12/007,000 patent/US8093389B2/en active Active
- 2008-01-08 AU AU2008205638A patent/AU2008205638B2/en not_active Ceased
- 2008-01-08 BR BRPI0806531-4A2A patent/BRPI0806531A2/pt not_active IP Right Cessation
- 2008-01-08 WO PCT/US2008/000223 patent/WO2008088689A1/en not_active Ceased
- 2008-01-08 MX MX2009007502A patent/MX2009007502A/es unknown
- 2008-01-08 CN CN2008800021443A patent/CN101631791B/zh not_active Expired - Fee Related
- 2008-01-08 NZ NZ577825A patent/NZ577825A/en not_active IP Right Cessation
- 2008-01-08 UA UAA200908468A patent/UA103990C2/ru unknown
- 2008-01-09 AR ARP080100081A patent/AR064824A1/es not_active Application Discontinuation
- 2008-01-10 CL CL200800067A patent/CL2008000067A1/es unknown
-
2009
- 2009-06-12 ZA ZA200904138A patent/ZA200904138B/xx unknown
- 2009-07-06 HN HN2009001276A patent/HN2009001276A/es unknown
- 2009-07-06 GT GT200900194A patent/GT200900194A/es unknown
- 2009-07-08 NI NI200900139A patent/NI200900139A/es unknown
- 2009-07-09 EC EC2009009503A patent/ECSP099503A/es unknown
- 2009-07-09 DO DO2009000176A patent/DOP2009000176A/es unknown
- 2009-07-13 CO CO09072490A patent/CO6190611A2/es active IP Right Grant
- 2009-07-20 CR CR10944A patent/CR10944A/es unknown
- 2009-07-23 MA MA32114A patent/MA31108B1/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010515733A5 (https=) | ||
| JP2010515734A5 (https=) | ||
| RU2009130736A (ru) | Замещенные производные спирохроманона | |
| AU2016358242B2 (en) | N-substituted indole derivatives as PGE2 receptor modulators | |
| RU2016140338A (ru) | Азаспиро производные в качестве антагонистов trpm8 | |
| JP5271917B2 (ja) | スピロクロマノン誘導体 | |
| HRP20231310T1 (hr) | Heteroarilaminopirimidin amidni inhibitori autofagije i postupci njihove primjene | |
| BG107899A (bg) | Б...нзимидазолови и пиридилимидазолови производни ка'о лиганди на gaba р...-...п'ори | |
| HRP20120174T1 (hr) | Derivat policikličnog cinamida | |
| JPWO2020231808A5 (https=) | ||
| JP2012532931A5 (https=) | ||
| ES2550201T3 (es) | Moduladores de la PDE10 | |
| JP2013540119A5 (https=) | ||
| CA2959501A1 (en) | Probes for imaging huntingtin protein | |
| AU2013286894A1 (en) | Heterocyclic modulators of lipid synthesis | |
| RU2008106243A (ru) | Производные спирохроманона в качестве ингибиторов ацетил коэнзим а карбоксилазы (асс) | |
| JP2021501220A5 (https=) | ||
| JP2018534328A5 (https=) | ||
| SI2763982T1 (en) | Substituted benzylindazoles for use as inhibitors of Bub kinase in the treatment of hyperproliferative diseases | |
| JP2011516512A5 (ja) | 新規な置換スピロ[シクロアルキル−１,３'−インドール]−２'(１'Ｈ)−オン誘導体およびｐ３８マイトジェン活性化タンパク質キナーゼ阻害剤としてのそれらの使用 | |
| JP2014513112A5 (https=) | ||
| JP2017518348A (ja) | Ｉｒａｋ４阻害剤としての置換インダゾール化合物 | |
| AU2005301608B2 (en) | Aryloxy-substituted benzimidazole derivatives | |
| JP2014504300A5 (https=) | ||
| JP2011520915A5 (https=) |