RU2009130736A - Замещенные производные спирохроманона - Google Patents
Замещенные производные спирохроманона Download PDFInfo
- Publication number
- RU2009130736A RU2009130736A RU2009130736/04A RU2009130736A RU2009130736A RU 2009130736 A RU2009130736 A RU 2009130736A RU 2009130736/04 A RU2009130736/04 A RU 2009130736/04A RU 2009130736 A RU2009130736 A RU 2009130736A RU 2009130736 A RU2009130736 A RU 2009130736A
- Authority
- RU
- Russia
- Prior art keywords
- group
- chroman
- carbonyl
- piperidine
- alkoxy
- Prior art date
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 69
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 40
- 125000005843 halogen group Chemical group 0.000 claims abstract 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 36
- 229910052736 halogen Inorganic materials 0.000 claims abstract 35
- -1 carboxyloxy Chemical group 0.000 claims abstract 27
- 125000001424 substituent group Chemical group 0.000 claims abstract 27
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 26
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 26
- 150000001875 compounds Chemical class 0.000 claims abstract 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 17
- 125000003118 aryl group Chemical group 0.000 claims abstract 15
- 125000004423 acyloxy group Chemical group 0.000 claims abstract 13
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 10
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract 8
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims abstract 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 7
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract 5
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims abstract 4
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims abstract 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims abstract 4
- FKWUPVHNVKGGSD-UHFFFAOYSA-N 1h-thieno[2,3-c]pyrazole Chemical compound C1=NNC2=C1C=CS2 FKWUPVHNVKGGSD-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 4
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims abstract 4
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims abstract 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims abstract 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims abstract 4
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 18
- 150000002148 esters Chemical class 0.000 claims 18
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims 13
- 125000004043 oxo group Chemical group O=* 0.000 claims 13
- 159000000000 sodium salts Chemical class 0.000 claims 11
- 125000002252 acyl group Chemical group 0.000 claims 10
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 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
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 7
- 235000001968 nicotinic acid Nutrition 0.000 claims 7
- 239000011664 nicotinic acid Substances 0.000 claims 7
- 229960003512 nicotinic acid Drugs 0.000 claims 7
- 125000000464 thioxo group Chemical group S=* 0.000 claims 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 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 3
- 239000005711 Benzoic acid Substances 0.000 claims 3
- 208000032841 Bulimia Diseases 0.000 claims 3
- 206010006550 Bulimia nervosa Diseases 0.000 claims 3
- 208000035473 Communicable disease Diseases 0.000 claims 3
- 208000004930 Fatty Liver Diseases 0.000 claims 3
- 206010019708 Hepatic steatosis Diseases 0.000 claims 3
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 3
- 235000010233 benzoic acid Nutrition 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 201000005577 familial hyperlipidemia Diseases 0.000 claims 3
- 208000010706 fatty liver disease Diseases 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- QHNDQKSXDVVXIB-UHFFFAOYSA-N spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound O1C2=CC=CC=C2C(=O)CC21CCNCC2 QHNDQKSXDVVXIB-UHFFFAOYSA-N 0.000 claims 3
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 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 2
- 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 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 2
- XAMGRYMUSBHENQ-UHFFFAOYSA-N 2-[1'-(1-cyclopropyl-4-methoxyindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-4-carboxylic acid Chemical compound C1=CC=2C(OC)=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3N=CC=C(C=3)C(O)=O)=CC=2N1C1CC1 XAMGRYMUSBHENQ-UHFFFAOYSA-N 0.000 claims 2
- NDNZESXOYGRKNN-UHFFFAOYSA-N 5-[1'-(1-cyclopropyl-4-ethoxyindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-3-carboxylic acid Chemical compound 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 NDNZESXOYGRKNN-UHFFFAOYSA-N 0.000 claims 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Natural products OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 2
- 230000036210 malignancy Effects 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
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 239000010802 sludge Substances 0.000 claims 2
- RTJLRYUCFLGLNI-UHFFFAOYSA-N (2-cyclopropyl-7-ethoxy-1,3-benzoxazol-5-yl)-[6-(2H-tetrazol-5-yl)spiro[3,4-dihydrochromene-2,4'-piperidine]-1'-yl]methanone Chemical compound C1(CC1)C=1OC2=C(N=1)C=C(C=C2OCC)C(=O)N1CCC2(CC1)OC1=CC=C(C=C1CC2)C1=NN=NN1 RTJLRYUCFLGLNI-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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- MSNPQZDMJFEICG-UHFFFAOYSA-N 4-[1'-(1-cyclopropyl-4-methoxyindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-2-carboxylic acid Chemical compound 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 MSNPQZDMJFEICG-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
- 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
- JAGJZOKJPRLLAZ-UHFFFAOYSA-N 5-[1'-(1-cyclopropyl-4-methoxyindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-2-carboxylic acid Chemical compound 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 JAGJZOKJPRLLAZ-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
- YXKFLPLCWYYKRO-UHFFFAOYSA-N 5-[1'-(3-chloro-1-cyclopropyl-4-methoxyindole-6-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-3-carboxylic acid Chemical compound 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 YXKFLPLCWYYKRO-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 229960001238 methylnicotinate Drugs 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
- 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
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 abstract 2
- GVLRTOYGRNLSDW-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine Chemical compound C1=CC=C2C=NNC2=N1 GVLRTOYGRNLSDW-UHFFFAOYSA-N 0.000 abstract 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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| WO2007011811A1 (en) * | 2005-07-19 | 2007-01-25 | Merck & Co., Inc. | Spirochromanone derivatives as acetyl coenzyme a carboxylase (acc) inhibitors |
| CN101541809A (zh) * | 2006-11-29 | 2009-09-23 | 辉瑞产品公司 | 螺环酮乙酰基-CoA羧化酶抑制剂 |
| WO2008088692A2 (en) * | 2007-01-12 | 2008-07-24 | Merck & Co., Inc. | Spirochromanon derivatives |
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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 KR KR1020097014377A patent/KR20090108022A/ko not_active Withdrawn
- 2008-01-08 WO PCT/US2008/000223 patent/WO2008088689A1/en not_active Ceased
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- 2008-01-08 CN CN2008800021443A patent/CN101631791B/zh not_active Expired - Fee Related
- 2008-01-08 EP EP08713050A patent/EP2111406B1/en active Active
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