JP2010515734A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010515734A5 JP2010515734A5 JP2009545580A JP2009545580A JP2010515734A5 JP 2010515734 A5 JP2010515734 A5 JP 2010515734A5 JP 2009545580 A JP2009545580 A JP 2009545580A JP 2009545580 A JP2009545580 A JP 2009545580A JP 2010515734 A5 JP2010515734 A5 JP 2010515734A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- chroman
- carbonyl
- methyl
- spiro
- 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 59
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 29
- 125000005843 halogen group Chemical group 0.000 claims 29
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims 23
- 125000001424 substituent group Chemical group 0.000 claims 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 13
- -1 2-methyl-3-pyrazolylamino group Chemical group 0.000 claims 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 12
- 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 11
- 239000011734 sodium Substances 0.000 claims 11
- 229910052708 sodium Inorganic materials 0.000 claims 11
- 125000002252 acyl group Chemical group 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- 150000002148 esters Chemical class 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 7
- 125000000623 heterocyclic 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims 5
- 125000004434 sulfur atom Chemical group 0.000 claims 5
- 125000000464 thioxo group Chemical group S=* 0.000 claims 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 2
- 125000006773 (C2-C7) alkylcarbonyl group Chemical group 0.000 claims 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims 2
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 2
- VGALJTWZFCSONV-UHFFFAOYSA-N 1h-furo[2,3-c]pyrazole Chemical compound C1=NNC2=C1C=CO2 VGALJTWZFCSONV-UHFFFAOYSA-N 0.000 claims 2
- GVLRTOYGRNLSDW-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine Chemical compound C1=CC=C2C=NNC2=N1 GVLRTOYGRNLSDW-UHFFFAOYSA-N 0.000 claims 2
- FKWUPVHNVKGGSD-UHFFFAOYSA-N 1h-thieno[2,3-c]pyrazole Chemical compound C1=NNC2=C1C=CS2 FKWUPVHNVKGGSD-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
- 206010019708 Hepatic steatosis Diseases 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 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
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 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 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 2
- 125000005605 benzo group Chemical group 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
- 125000002541 furyl group Chemical group 0.000 claims 2
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 2
- JMANUKZDKDKBJP-UHFFFAOYSA-N imidazo[1,5-a]pyridine Chemical compound C1=CC=CC2=CN=CN21 JMANUKZDKDKBJP-UHFFFAOYSA-N 0.000 claims 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 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
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- JOQXHUFABDZIEE-UHFFFAOYSA-N 1'-(1,3-diphenylindazole-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C=1C=C2C(C=3C=CC=CC=3)=NN(C=3C=CC=CC=3)C2=CC=1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=NN=NN1 JOQXHUFABDZIEE-UHFFFAOYSA-N 0.000 claims 1
- QPKWOIXMADDDNM-UHFFFAOYSA-N 1'-(1,3-diphenylthieno[2,3-c]pyrazole-5-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C=1C=2C(C=3C=CC=CC=3)=NN(C=3C=CC=CC=3)C=2SC=1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=NN=NN1 QPKWOIXMADDDNM-UHFFFAOYSA-N 0.000 claims 1
- QWJMTYAKFBDVPI-UHFFFAOYSA-N 1'-(1-ethyl-3-phenylthieno[2,3-c]pyrazole-5-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=2C=C(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)SC=2N(CC)N=C1C1=CC=CC=C1 QWJMTYAKFBDVPI-UHFFFAOYSA-N 0.000 claims 1
- CREQHCOHPJARDZ-UHFFFAOYSA-N 1'-(1-methyl-3-phenylindazole-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C12=CC=C(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)C=C2N(C)N=C1C1=CC=CC=C1 CREQHCOHPJARDZ-UHFFFAOYSA-N 0.000 claims 1
- YJEMUGADUTYXEI-UHFFFAOYSA-N 1'-(1-methyl-3-phenylindole-6-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C12=CC=C(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)C=C2N(C)C=C1C1=CC=CC=C1 YJEMUGADUTYXEI-UHFFFAOYSA-N 0.000 claims 1
- XNUPUQBKOAWVOL-UHFFFAOYSA-N 1'-(2-cyclopropyl-1-phenylbenzimidazole-5-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C=1C=C2N(C=3C=CC=CC=3)C(C3CC3)=NC2=CC=1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=NN=NN1 XNUPUQBKOAWVOL-UHFFFAOYSA-N 0.000 claims 1
- OTIASALIHOUFAX-UHFFFAOYSA-N 1'-(2-methoxy-6-phenylpyridine-4-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound N=1C(OC)=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2NN=NN=2)=CC=1C1=CC=CC=C1 OTIASALIHOUFAX-UHFFFAOYSA-N 0.000 claims 1
- ZZRPBDYUPRLEGJ-UHFFFAOYSA-N 1'-(3,5-dimethoxy-4-phenylbenzoyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound COC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2NN=NN=2)=CC(OC)=C1C1=CC=CC=C1 ZZRPBDYUPRLEGJ-UHFFFAOYSA-N 0.000 claims 1
- NWNLMNPDZLYRFT-UHFFFAOYSA-N 1'-(3,5-dimethoxy-4-phenylbenzoyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one;sodium Chemical compound [Na].COC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C2=NNN=N2)=CC(OC)=C1C1=CC=CC=C1 NWNLMNPDZLYRFT-UHFFFAOYSA-N 0.000 claims 1
- XHMDBCVOQHDSTL-UHFFFAOYSA-N 1'-(3-chloro-1-phenylindole-5-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C12=CC=C(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)C=C2C(Cl)=CN1C1=CC=CC=C1 XHMDBCVOQHDSTL-UHFFFAOYSA-N 0.000 claims 1
- YGQAKYWAVXKJBL-UHFFFAOYSA-N 1'-(3-cyclopropyl-1-pyridin-2-ylthieno[2,3-c]pyrazole-5-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C=1C=2C(C3CC3)=NN(C=3N=CC=CC=3)C=2SC=1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=NN=NN1 YGQAKYWAVXKJBL-UHFFFAOYSA-N 0.000 claims 1
- BBXOKUDYPALPQO-UHFFFAOYSA-N 1'-(3-methyl-1-phenylfuro[2,3-c]pyrazole-5-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=2OC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)=CC=2C(C)=NN1C1=CC=CC=C1 BBXOKUDYPALPQO-UHFFFAOYSA-N 0.000 claims 1
- BHRPQDZZQGCSKE-UHFFFAOYSA-N 1'-(3-methyl-1-phenylindazole-5-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C12=CC=C(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)C=C2C(C)=NN1C1=CC=CC=C1 BHRPQDZZQGCSKE-UHFFFAOYSA-N 0.000 claims 1
- IDYRXMQYBHAIJE-UHFFFAOYSA-N 1'-(3-methyl-1-pyridin-2-ylthieno[2,3-c]pyrazole-5-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=2SC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)=CC=2C(C)=NN1C1=CC=CC=N1 IDYRXMQYBHAIJE-UHFFFAOYSA-N 0.000 claims 1
- SCOSTDNTFGECOQ-UHFFFAOYSA-N 1'-(3-methyl-1-pyridin-2-ylthieno[2,3-c]pyrazole-5-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one;sodium Chemical compound [Na].C1=2SC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C3=NNN=N3)=CC=2C(C)=NN1C1=CC=CC=N1 SCOSTDNTFGECOQ-UHFFFAOYSA-N 0.000 claims 1
- BAKFJDOXVIINNL-UHFFFAOYSA-N 1'-(4-methoxy-1-phenylindole-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=2N1C1=CC=CC=C1 BAKFJDOXVIINNL-UHFFFAOYSA-N 0.000 claims 1
- LQFYRSGSQRPXTM-UHFFFAOYSA-N 1'-(6-phenyl-1-propan-2-ylpyrazolo[3,4-b]pyridine-4-carbonyl)-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound N1=C2N(C(C)C)N=CC2=C(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2NN=NN=2)C=C1C1=CC=CC=C1 LQFYRSGSQRPXTM-UHFFFAOYSA-N 0.000 claims 1
- XFBXWELPCGILHK-UHFFFAOYSA-N 1'-[1-cyclopropyl-4-(2h-tetrazol-5-yl)indole-6-carbonyl]-6-(1-methylpyrazol-4-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=NN(C)C=C1C1=CC=C(OC2(CCN(CC2)C(=O)C=2C=C3N(C4CC4)C=CC3=C(C=3NN=NN=3)C=2)CC2=O)C2=C1 XFBXWELPCGILHK-UHFFFAOYSA-N 0.000 claims 1
- KCIYVLKFSKLEOA-UHFFFAOYSA-N 1'-[1-cyclopropyl-4-(2h-tetrazol-5-yl)indole-6-carbonyl]-6-(6-methoxypyridin-3-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=NC(OC)=CC=C1C1=CC=C(OC2(CCN(CC2)C(=O)C=2C=C3N(C4CC4)C=CC3=C(C=3NN=NN=3)C=2)CC2=O)C2=C1 KCIYVLKFSKLEOA-UHFFFAOYSA-N 0.000 claims 1
- DSLUDZVWIWIQND-UHFFFAOYSA-N 1'-[1-cyclopropyl-4-(2h-tetrazol-5-yl)indole-6-carbonyl]-6-(6-oxo-1h-pyridin-3-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C=1C(C=2NN=NN=2)=C2C=CN(C3CC3)C2=CC=1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C=1C=CC(=O)NC=1 DSLUDZVWIWIQND-UHFFFAOYSA-N 0.000 claims 1
- DIBMBGQPUDXTJF-UHFFFAOYSA-N 1'-[1-cyclopropyl-4-(2h-tetrazol-5-yl)indole-6-carbonyl]-6-[(2-methylpyrazol-3-yl)amino]spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound CN1N=CC=C1NC1=CC=C(OC2(CCN(CC2)C(=O)C=2C=C3N(C4CC4)C=CC3=C(C=3NN=NN=3)C=2)CC2=O)C2=C1 DIBMBGQPUDXTJF-UHFFFAOYSA-N 0.000 claims 1
- BHGPOCUNDWMDCP-UHFFFAOYSA-N 1'-[1-cyclopropyl-4-(2h-tetrazol-5-yl)indole-6-carbonyl]-6-propan-2-ylspiro[3h-pyrano[2,3-c]pyridine-2,4'-piperidine]-4-one Chemical compound O1C=2C=NC(C(C)C)=CC=2C(=O)CC1(CC1)CCN1C(=O)C(C=C1N(C2CC2)C=CC1=1)=CC=1C1=NN=NN1 BHGPOCUNDWMDCP-UHFFFAOYSA-N 0.000 claims 1
- MSBZZDSSFRNASZ-UHFFFAOYSA-N 1'-[2,6-bis(4-fluorophenyl)pyridine-4-carbonyl]-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=CC(F)=CC=C1C1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2NN=NN=2)=CC(C=2C=CC(F)=CC=2)=N1 MSBZZDSSFRNASZ-UHFFFAOYSA-N 0.000 claims 1
- NTGUKGWUQOXNPE-UHFFFAOYSA-N 1'-[3,5-diethoxy-4-(1-methylpyrazol-4-yl)benzoyl]-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2NN=NN=2)=CC(OCC)=C1C=1C=NN(C)C=1 NTGUKGWUQOXNPE-UHFFFAOYSA-N 0.000 claims 1
- AETSPOYGZBRHOG-UHFFFAOYSA-N 1'-[3,5-diethoxy-4-(1-methylpyrazol-4-yl)benzoyl]-6-(5-oxo-1,2-dihydro-1,2,4-triazol-3-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2NC(=O)NN=2)=CC(OCC)=C1C=1C=NN(C)C=1 AETSPOYGZBRHOG-UHFFFAOYSA-N 0.000 claims 1
- JKMKCOHTOJVKTF-UHFFFAOYSA-N 1'-[3,5-diethoxy-4-(1-methylpyrazol-4-yl)benzoyl]-6-(5-oxo-2h-1,2,4-oxadiazol-3-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2NC(=O)ON=2)=CC(OCC)=C1C=1C=NN(C)C=1 JKMKCOHTOJVKTF-UHFFFAOYSA-N 0.000 claims 1
- OYIYKLGZKCHHPY-UHFFFAOYSA-N 1'-[3,5-diethoxy-4-(1h-pyrazol-4-yl)benzoyl]-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2NN=NN=2)=CC(OCC)=C1C=1C=NNC=1 OYIYKLGZKCHHPY-UHFFFAOYSA-N 0.000 claims 1
- RMGMHHTZYRJPDJ-UHFFFAOYSA-N 1'-[3,5-diethoxy-4-(1h-pyrazol-4-yl)benzoyl]-6-(5-oxo-2h-1,2,4-oxadiazol-3-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2NC(=O)ON=2)=CC(OCC)=C1C=1C=NNC=1 RMGMHHTZYRJPDJ-UHFFFAOYSA-N 0.000 claims 1
- VWMWXDGKVMXGAH-UHFFFAOYSA-N 1'-[3,5-diethoxy-4-(2-fluoropyridin-4-yl)benzoyl]-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2NN=NN=2)=CC(OCC)=C1C1=CC=NC(F)=C1 VWMWXDGKVMXGAH-UHFFFAOYSA-N 0.000 claims 1
- INQYMBDDIIINHB-UHFFFAOYSA-N 1'-[3,5-diethoxy-4-(6-fluoropyridin-3-yl)benzoyl]-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2NN=NN=2)=CC(OCC)=C1C1=CC=C(F)N=C1 INQYMBDDIIINHB-UHFFFAOYSA-N 0.000 claims 1
- JOFHDAYQBBKOCM-UHFFFAOYSA-N 1'-[3,5-dimethoxy-4-(2-methyl-1,3-oxazol-5-yl)benzoyl]-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound COC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2NN=NN=2)=CC(OC)=C1C1=CN=C(C)O1 JOFHDAYQBBKOCM-UHFFFAOYSA-N 0.000 claims 1
- XVTOWXMESZWGLM-UHFFFAOYSA-N 1'-[3-(1h-indol-5-yl)-5-methoxybenzoyl]-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C=1C(C=2C=C3C=CNC3=CC=2)=CC(OC)=CC=1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=NN=NN1 XVTOWXMESZWGLM-UHFFFAOYSA-N 0.000 claims 1
- FWQLQPZBCDJOCW-UHFFFAOYSA-N 1'-[3-(difluoromethyl)-1-pyridin-2-ylthieno[2,3-c]pyrazole-5-carbonyl]-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=2SC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3NN=NN=3)=CC=2C(C(F)F)=NN1C1=CC=CC=N1 FWQLQPZBCDJOCW-UHFFFAOYSA-N 0.000 claims 1
- UBEUCFLASRITNG-UHFFFAOYSA-N 1'-[3-ethoxy-4-(1-methylpyrazol-4-yl)benzoyl]-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2NN=NN=2)=CC=C1C=1C=NN(C)C=1 UBEUCFLASRITNG-UHFFFAOYSA-N 0.000 claims 1
- QNQHWTBEBUALRK-UHFFFAOYSA-N 1'-[3-ethoxy-5-(2h-tetrazol-5-yl)benzoyl]-6-[(2-methylpyrazol-3-yl)amino]spiro[3h-chromene-2,4'-piperidine]-4-one;sodium Chemical compound [Na].C=1C(OCC)=CC(C(=O)N2CCC3(CC2)OC2=CC=C(NC=4N(N=CC=4)C)C=C2C(=O)C3)=CC=1C=1N=NNN=1 QNQHWTBEBUALRK-UHFFFAOYSA-N 0.000 claims 1
- FIUHUXQEYFLRJY-UHFFFAOYSA-N 1'-[3-ethoxy-5-methoxy-4-(1-methylpyrazol-4-yl)benzoyl]-6-(1-methylpyrazol-4-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C2=CN(C)N=C2)=CC(OC)=C1C=1C=NN(C)C=1 FIUHUXQEYFLRJY-UHFFFAOYSA-N 0.000 claims 1
- HXVLIMJAZLCQCF-UHFFFAOYSA-N 1'-[3-ethoxy-5-methoxy-4-(1-methylpyrazol-4-yl)benzoyl]-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2NN=NN=2)=CC(OC)=C1C=1C=NN(C)C=1 HXVLIMJAZLCQCF-UHFFFAOYSA-N 0.000 claims 1
- YJFGKPZYOJRMNU-UHFFFAOYSA-N 1'-[3-ethoxy-5-methoxy-4-(1-methylpyrazol-4-yl)benzoyl]-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one;sodium Chemical compound [Na].CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C2=NNN=N2)=CC(OC)=C1C=1C=NN(C)C=1 YJFGKPZYOJRMNU-UHFFFAOYSA-N 0.000 claims 1
- WXAJEKDIVXXWMS-UHFFFAOYSA-N 1'-[3-phenyl-5-(2h-tetrazol-5-yl)benzoyl]-6-propan-2-ylspiro[3h-pyrano[2,3-c]pyridine-2,4'-piperidine]-4-one Chemical compound O1C=2C=NC(C(C)C)=CC=2C(=O)CC1(CC1)CCN1C(=O)C(C=1)=CC(C=2NN=NN=2)=CC=1C1=CC=CC=C1 WXAJEKDIVXXWMS-UHFFFAOYSA-N 0.000 claims 1
- VXOOFFRLYNCNJO-UHFFFAOYSA-N 1'-[3-pyrrolidin-1-yl-5-(1h-1,2,4-triazol-5-yl)benzoyl]-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one;sodium Chemical compound [Na].C=1C(N2CCCC2)=CC(C=2NN=CN=2)=CC=1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C=1N=NNN=1 VXOOFFRLYNCNJO-UHFFFAOYSA-N 0.000 claims 1
- GGONPXIOBLFLMP-UHFFFAOYSA-N 1'-[4-(1-benzothiophen-2-yl)benzoyl]-6-(2h-tetrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C=1C=C(C=2SC3=CC=CC=C3C=2)C=CC=1C(=O)N(CC1)CCC1(OC1=CC=2)CC(=O)C1=CC=2C1=NN=NN1 GGONPXIOBLFLMP-UHFFFAOYSA-N 0.000 claims 1
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims 1
- YYHABXFICKLXEF-UHFFFAOYSA-N 4-[1'-(3-methyl-1-phenylindazole-5-carbonyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-2-carboxylic acid Chemical compound C12=CC=C(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C=3C=C(N=CC=3)C(O)=O)C=C2C(C)=NN1C1=CC=CC=C1 YYHABXFICKLXEF-UHFFFAOYSA-N 0.000 claims 1
- VYZAGHAVFBOITA-UHFFFAOYSA-N 5-[1'-(3,5-dimethoxy-4-phenylbenzoyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-3-carboxylic acid Chemical compound COC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2C=C(C=NC=2)C(O)=O)=CC(OC)=C1C1=CC=CC=C1 VYZAGHAVFBOITA-UHFFFAOYSA-N 0.000 claims 1
- SXEHRGJOJYMIAA-UHFFFAOYSA-N 5-[1'-[3,5-diethoxy-4-(1-methylpyrazol-4-yl)benzoyl]-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]-2-fluorobenzoic acid Chemical group CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2C=C(C(F)=CC=2)C(O)=O)=CC(OCC)=C1C=1C=NN(C)C=1 SXEHRGJOJYMIAA-UHFFFAOYSA-N 0.000 claims 1
- YFQWXGLAOVNDBA-UHFFFAOYSA-N 5-[1'-[3-ethoxy-5-methoxy-4-(1-methylpyrazol-4-yl)benzoyl]-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-3-carboxylic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2C=C(C=NC=2)C(O)=O)=CC(OC)=C1C=1C=NN(C)C=1 YFQWXGLAOVNDBA-UHFFFAOYSA-N 0.000 claims 1
- RAJZIUGTGOIFFH-UHFFFAOYSA-N 5-[1'-[4-(1-cyclopropylpyrazol-4-yl)-3,5-diethoxybenzoyl]-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridin-1-ium-3-carboxylic acid;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2C=C(C=[NH+]C=2)C(O)=O)=CC(OCC)=C1C(=C1)C=NN1C1CC1 RAJZIUGTGOIFFH-UHFFFAOYSA-N 0.000 claims 1
- LEWFQNFGAKCHOQ-UHFFFAOYSA-N 5-[1'-[4-[1-(difluoromethyl)pyrazol-4-yl]-3,5-diethoxybenzoyl]-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-3-carboxylic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2C=C(C=NC=2)C(O)=O)=CC(OCC)=C1C=1C=NN(C(F)F)C=1 LEWFQNFGAKCHOQ-UHFFFAOYSA-N 0.000 claims 1
- RTMKBBLTIFECLE-UHFFFAOYSA-N 6-(1-methylpyrazol-4-yl)-1'-[3-phenyl-5-(2h-tetrazol-5-yl)benzoyl]spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound C1=NN(C)C=C1C1=CC=C(OC2(CCN(CC2)C(=O)C=2C=C(C=C(C=2)C=2NN=NN=2)C=2C=CC=CC=2)CC2=O)C2=C1 RTMKBBLTIFECLE-UHFFFAOYSA-N 0.000 claims 1
- HPYMKVBRBVBPQU-UHFFFAOYSA-N 6-(4-acetylpiperazin-1-yl)-1'-[3-ethoxy-5-methoxy-4-(1-methylpyrazol-4-yl)benzoyl]spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)N2CCN(CC2)C(C)=O)=CC(OC)=C1C=1C=NN(C)C=1 HPYMKVBRBVBPQU-UHFFFAOYSA-N 0.000 claims 1
- YGMLSTYESWUYFU-UHFFFAOYSA-N 6-[(2-methylpyrazol-3-yl)amino]-1'-[2-phenyl-6-(2h-tetrazol-5-yl)pyridine-4-carbonyl]spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound CN1N=CC=C1NC1=CC=C(OC2(CCN(CC2)C(=O)C=2C=C(N=C(C=2)C=2NN=NN=2)C=2C=CC=CC=2)CC2=O)C2=C1 YGMLSTYESWUYFU-UHFFFAOYSA-N 0.000 claims 1
- FOQMVXRVJZTNBM-UHFFFAOYSA-N 6-[(2-methylpyrazol-3-yl)amino]-1'-[3-pyrrolidin-1-yl-5-(2h-tetrazol-5-yl)benzoyl]spiro[3h-chromene-2,4'-piperidine]-4-one Chemical compound CN1N=CC=C1NC1=CC=C(OC2(CCN(CC2)C(=O)C=2C=C(C=C(C=2)N2CCCC2)C=2NN=NN=2)CC2=O)C2=C1 FOQMVXRVJZTNBM-UHFFFAOYSA-N 0.000 claims 1
- SDMAZQFNMALARI-UHFFFAOYSA-N C(C)OC=1C=C(C=C(C1C=1C=NN(C1)C)OCC)C(=O)N1CCC2(CC1)OC1=CC=C(C=C1C(C2)=O)C2(CC=NC=C2)C(=O)O Chemical compound C(C)OC=1C=C(C=C(C1C=1C=NN(C1)C)OCC)C(=O)N1CCC2(CC1)OC1=CC=C(C=C1C(C2)=O)C2(CC=NC=C2)C(=O)O SDMAZQFNMALARI-UHFFFAOYSA-N 0.000 claims 1
- OCDGWVQPWSOIRC-UHFFFAOYSA-N C1(CC1)C1=CN(C2=CC=C(C=C12)C(=O)N1CCC2(CC1)OC1=CC=C(C=C1C(C2)=O)NC1=CC=NN1C)[C-]1N=NN=N1 Chemical group C1(CC1)C1=CN(C2=CC=C(C=C12)C(=O)N1CCC2(CC1)OC1=CC=C(C=C1C(C2)=O)NC1=CC=NN1C)[C-]1N=NN=N1 OCDGWVQPWSOIRC-UHFFFAOYSA-N 0.000 claims 1
- MPDYMRCAYNRCGJ-UHFFFAOYSA-N CCOC1=CC(=CC(=C1C2=CN(N=C2)C)OC)C(=O)N3CCC4(CC3)CC(=O)C5=C(O4)C=CC(=C5)OC(=O)N Chemical compound CCOC1=CC(=CC(=C1C2=CN(N=C2)C)OC)C(=O)N3CCC4(CC3)CC(=O)C5=C(O4)C=CC(=C5)OC(=O)N MPDYMRCAYNRCGJ-UHFFFAOYSA-N 0.000 claims 1
- KJWCWRPAAHRIJV-UHFFFAOYSA-N O=C1CC2(CCN(CC2)C(=O)C=2C=C(C=C(C2)C2=NN=NN2)C2=CC=CC=C2)OC2=CC=C(C=C12)C=1C=CC=NC1 Chemical compound O=C1CC2(CCN(CC2)C(=O)C=2C=C(C=C(C2)C2=NN=NN2)C2=CC=CC=C2)OC2=CC=C(C=C12)C=1C=CC=NC1 KJWCWRPAAHRIJV-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims 1
- GKIFWNRZJGAKCF-UHFFFAOYSA-N n-(2,2-difluoroethyl)-1'-[3-ethoxy-5-methoxy-4-(1-methylpyrazol-4-yl)benzoyl]-4-oxospiro[3h-chromene-2,4'-piperidine]-6-carboxamide Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C(=O)NCC(F)F)=CC(OC)=C1C=1C=NN(C)C=1 GKIFWNRZJGAKCF-UHFFFAOYSA-N 0.000 claims 1
- COABAOXQGBOTMK-UHFFFAOYSA-N n-(2-amino-2-oxoethyl)-1'-[3,5-diethoxy-4-(1-methylpyrazol-4-yl)benzoyl]-4-oxospiro[3h-chromene-2,4'-piperidine]-6-carboxamide Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C(=O)NCC(N)=O)=CC(OCC)=C1C=1C=NN(C)C=1 COABAOXQGBOTMK-UHFFFAOYSA-N 0.000 claims 1
- 235000005152 nicotinamide Nutrition 0.000 claims 1
- 239000011570 nicotinamide Substances 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 229950010765 pivalate Drugs 0.000 claims 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- ZKWWFJUOFBORHU-UHFFFAOYSA-M sodium;5-[1'-[3,5-diethoxy-4-(1-methylpyrazol-4-yl)benzoyl]-4-oxospiro[3h-chromene-2,4'-piperidine]-6-yl]pyridine-3-carboxylate Chemical compound [Na+].CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2C=C(C=NC=2)C([O-])=O)=CC(OCC)=C1C=1C=NN(C)C=1 ZKWWFJUOFBORHU-UHFFFAOYSA-M 0.000 claims 1
- 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 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88030307P | 2007-01-12 | 2007-01-12 | |
| US60/880,303 | 2007-01-12 | ||
| PCT/US2008/000247 WO2008088692A2 (en) | 2007-01-12 | 2008-01-08 | Spirochromanon derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010515734A JP2010515734A (ja) | 2010-05-13 |
| JP2010515734A5 true JP2010515734A5 (enExample) | 2011-02-10 |
| JP5271917B2 JP5271917B2 (ja) | 2013-08-21 |
Family
ID=39636552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009545580A Expired - Fee Related JP5271917B2 (ja) | 2007-01-12 | 2008-01-08 | スピロクロマノン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8138197B2 (enExample) |
| EP (1) | EP2120569B1 (enExample) |
| JP (1) | JP5271917B2 (enExample) |
| AU (1) | AU2008205642B2 (enExample) |
| CA (1) | CA2674530C (enExample) |
| WO (1) | WO2008088692A2 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007011811A1 (en) * | 2005-07-19 | 2007-01-25 | Merck & Co., Inc. | Spirochromanone derivatives as acetyl coenzyme a carboxylase (acc) inhibitors |
| PE20081559A1 (es) * | 2007-01-12 | 2008-11-20 | Merck & Co Inc | DERIVADOS DE ESPIROCROMANONA SUSTITUIDOS COMO INHIBIDORES DE ACETIL CoA CARBOXILASA |
| WO2010002010A1 (en) | 2008-07-04 | 2010-01-07 | Banyu Pharmaceutical Co.,Ltd. | Novel spirochromanone carboxylic acids |
| JP2011528034A (ja) | 2008-07-14 | 2011-11-10 | クロップソリューション，インコーポレイテッド | アセチル−補酵素カルボキシラーゼの修飾因子およびその使用方法 |
| CN102186809A (zh) * | 2008-08-14 | 2011-09-14 | 拜尔农作物科学股份公司 | 杀虫性的4-苯基-1h-吡唑 |
| US8653098B2 (en) | 2008-11-20 | 2014-02-18 | Genentech, Inc. | Pyrazolopyridine PI3K inhibitor compounds and methods of use |
| EP2308866A1 (de) | 2009-10-09 | 2011-04-13 | Bayer CropScience AG | Phenylpyri(mi)dinylpyrazole und ihre Verwendung als Fungizide |
| EP2493889B1 (en) | 2009-10-30 | 2017-09-06 | Janssen Pharmaceutica, N.V. | IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES AND THEIR USE AS PDE10 INHIBITORS |
| AR079545A1 (es) | 2009-12-21 | 2012-02-01 | Bayer Cropscience Ag | Tienilpiri(mi)dinilazol |
| AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
| WO2011140425A1 (en) | 2010-05-06 | 2011-11-10 | Vertex Pharmaceuticals Incorporated | Heterocyclic chromene-spirocyclic piperidine amides as modulators of ion channels |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| PT2621493T (pt) * | 2010-09-30 | 2016-11-14 | Pfizer | Inibidores de n1-pirazolospirocetona acetil-coa carboxilase |
| EP2637660A4 (en) * | 2010-11-08 | 2014-04-09 | Glaxosmithkline Ip No 2 Ltd | GRAS SYNTHASE ACID INHIBITORS |
| TW201604196A (zh) | 2011-02-02 | 2016-02-01 | 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 |
| US10385070B2 (en) | 2011-02-18 | 2019-08-20 | Vertex Pharmaceuticals Incorporated | Chroman-spirocyclic piperidine amides as modulators of ion channels |
| EP2686325B1 (en) | 2011-03-14 | 2016-12-14 | Vertex Pharmaceuticals Incorporated | Morpholine-spirocyclic piperidine amides as modulators of ion channels |
| JPWO2012161119A1 (ja) * | 2011-05-20 | 2014-07-31 | 興和株式会社 | 新規なスピロピペリジン誘導体及びこれを含有する医薬 |
| MX344600B (es) | 2011-06-27 | 2016-12-20 | Janssen Pharmaceutica Nv | Derivados de 1-aril-4-metil-[1,2,4]triazolo[4,3-a]quinoxalina. |
| KR20150021056A (ko) * | 2012-05-22 | 2015-02-27 | 액테리온 파마슈티칼 리미티드 | ２-시클로펜틸-６-메톡시-이소니코틴산의 신규한 제조 방법 |
| HK1206250A1 (en) | 2012-06-26 | 2016-01-08 | Janssen Pharmaceutica Nv | Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl-[1,2,4] triazolo [4,3-a] quinoxaline compounds and ped 10 inhibitors for use in the treatment of neurological or metabolic disorders |
| CN104411314B (zh) | 2012-07-09 | 2017-10-20 | 詹森药业有限公司 | 磷酸二酯酶10的抑制剂 |
| WO2014060381A1 (de) | 2012-10-18 | 2014-04-24 | Bayer Cropscience Ag | Heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| US20150284380A1 (en) | 2012-10-31 | 2015-10-08 | Bayer Cropscience Ag | Novel heterocyclic compounds as pest control agents |
| CN105102448B (zh) | 2013-02-28 | 2018-03-06 | 百时美施贵宝公司 | 作为rock1和rock2抑制剂的苯基吡唑衍生物 |
| AR094929A1 (es) | 2013-02-28 | 2015-09-09 | Bristol Myers Squibb Co | Derivados de fenilpirazol como inhibidores potentes de rock1 y rock2 |
| EP3188732B1 (en) | 2014-09-05 | 2019-07-24 | Merck Sharp & Dohme Corp. | Tetrahydroisoquinoline derivatives useful as inhibitors of diacylglyceride o-acyltransferase 2 |
| EP3188731B1 (en) | 2014-09-05 | 2019-04-03 | Merck Sharp & Dohme Corp. | Isoquinoline derivatives useful as inhibitors of diacylglyceride o-acyltransferase 2 |
| EP3188730B1 (en) | 2014-09-05 | 2019-05-01 | Merck Sharp & Dohme Corp. | Tetrahydroisoquinoline derivatives useful as inhibitors of diacylglyceride o-acyltransferase 2 |
| MX2019005679A (es) | 2016-11-18 | 2019-08-14 | Merck Sharp & Dohme | Derivados de indol de utilidad como inhibidores de diacilglicerido o-aciltransferasa 2. |
| US11104690B2 (en) | 2016-11-18 | 2021-08-31 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as inhibitors of diacylglyceride O-acyltransferase 2 |
| JP7162591B2 (ja) | 2016-12-14 | 2022-10-28 | エイティナイン バイオ リミテッド | スピロピペリジン誘導体 |
| BR112020006780A2 (pt) * | 2017-10-05 | 2020-10-06 | Glaxosmithkline Intellectual Property Development Limited | moduladores do estimulador de genes do interferon (sting) |
| CN114437096B (zh) * | 2020-11-06 | 2025-09-12 | 上海医药集团股份有限公司 | 一种螺杂环类化合物、其制备方法及应用 |
| US20240066027A1 (en) * | 2020-12-03 | 2024-02-29 | Domain Therapeutics | Novel par-2 inhibitors |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2814983A1 (de) * | 1978-04-07 | 1979-10-18 | Bayer Ag | Neue chromanon-derivate |
| 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 |
| US5206240A (en) * | 1989-12-08 | 1993-04-27 | Merck & Co., Inc. | Nitrogen-containing spirocycles |
| NZ243065A (en) | 1991-06-13 | 1995-07-26 | Lundbeck & Co As H | Piperidine derivatives and pharmaceutical compositions |
| IL107836A (en) * | 1992-12-11 | 1998-01-04 | Merck & Co Inc | Spiro piperidines and homologues, their preparation and pharmaceutical preparations containing them |
| US5578593A (en) * | 1992-12-11 | 1996-11-26 | Merck & Co., Inc. | Spiro piperidines and homologs promote release of growth hormone |
| AU693087B2 (en) | 1993-01-28 | 1998-06-25 | Merck & Co., Inc. | Spiro-substituted azacycles as tachykinin receptor antagonists |
| US6017768A (en) | 1994-05-06 | 2000-01-25 | Pharmacopeia, Inc. | Combinatorial dihydrobenzopyran library |
| US5688997A (en) * | 1994-05-06 | 1997-11-18 | Pharmacopeia, Inc. | Process for preparing intermediates for a combinatorial dihydrobenzopyran library |
| CA2189634A1 (en) | 1994-05-06 | 1995-11-16 | John J. Baldwin | 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 |
| 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 |
| 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 |
| JP2005162612A (ja) | 2002-01-09 | 2005-06-23 | Ajinomoto Co Inc | アシルスルホンアミド誘導体 |
| 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 |
| AU2003299791A1 (en) | 2002-12-20 | 2004-07-22 | Bayer Pharmaceuticals Corporation | Substituted 3,5-dihydro-4h-imidazol-4-ones for the treatment of obesity |
| 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 |
| 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 |
| CA2587153A1 (en) | 2004-11-18 | 2006-05-26 | Incyte Corporation | Inhibitors of 11-.beta. hydroxyl steroid dehydrogenase type 1 and methods of using the same |
| WO2006117669A1 (en) * | 2005-05-03 | 2006-11-09 | Pfizer Inc. | Amide resorcinol compounds |
| 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 |
| PE20081559A1 (es) * | 2007-01-12 | 2008-11-20 | Merck & Co Inc | DERIVADOS DE ESPIROCROMANONA SUSTITUIDOS COMO INHIBIDORES DE ACETIL CoA CARBOXILASA |
| WO2008102749A1 (ja) * | 2007-02-20 | 2008-08-28 | Takeda Pharmaceutical Company Limited | 複素環化合物 |
-
2008
- 2008-01-08 WO PCT/US2008/000247 patent/WO2008088692A2/en not_active Ceased
- 2008-01-08 JP JP2009545580A patent/JP5271917B2/ja not_active Expired - Fee Related
- 2008-01-08 EP EP08705516.6A patent/EP2120569B1/en not_active Not-in-force
- 2008-01-08 CA CA2674530A patent/CA2674530C/en not_active Expired - Fee Related
- 2008-01-08 AU AU2008205642A patent/AU2008205642B2/en not_active Ceased
- 2008-01-08 US US12/518,466 patent/US8138197B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010515734A5 (enExample) | ||
| JP2010515733A5 (enExample) | ||
| RU2009130736A (ru) | Замещенные производные спирохроманона | |
| TWI719078B (zh) | 做為pge2受體調節劑之n-取代吲哚衍生物 | |
| JP5331693B2 (ja) | 新規置換ビピリジン誘導体およびアデノシン受容体リガンドとしてのそれらの使用 | |
| RU2457207C2 (ru) | Активаторы глюкокиназы | |
| AU2007307679B2 (en) | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases | |
| JP6759100B2 (ja) | 治療用阻害化合物 | |
| JP5512707B2 (ja) | ブルトン型チロシンキナーゼの阻害剤 | |
| JP5444365B2 (ja) | 抗癌活性および抗増殖活性を示すシクロプロパンアミドおよび類似物質 | |
| JP2013540119A5 (enExample) | ||
| AU2005301608B2 (en) | Aryloxy-substituted benzimidazole derivatives | |
| JP2011526584A5 (enExample) | ||
| RU2016140338A (ru) | Азаспиро производные в качестве антагонистов trpm8 | |
| JP2021501220A5 (enExample) | ||
| RU2008106243A (ru) | Производные спирохроманона в качестве ингибиторов ацетил коэнзим а карбоксилазы (асс) | |
| JP2013527173A5 (enExample) | ||
| JP7264906B2 (ja) | ファルネソイドｘ受容体モジュレーターとしてのアルケン化合物 | |
| JP2013528591A5 (enExample) | ||
| JP2012500215A5 (enExample) | ||
| SG185330A1 (en) | Novel kinase inhibitors | |
| CN105764514A (zh) | 作为tam族激酶抑制剂的氨基吡啶衍生物 | |
| JP2014525444A5 (enExample) | ||
| ME02416B (me) | Trpv4 antagonisтi | |
| RU2008141511A (ru) | Конденсированные гетероциклические соединения и их применение в качестве модуляторов mglur5 |