JP2010515734A5 - - Google Patents
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 229950010765 pivalate Drugs 0.000 claims 1
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- 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
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| PE20081559A1 (es) * | 2007-01-12 | 2008-11-20 | Merck & Co Inc | DERIVADOS DE ESPIROCROMANONA SUSTITUIDOS COMO INHIBIDORES DE ACETIL CoA CARBOXILASA |
| US8524730B2 (en) | 2008-07-04 | 2013-09-03 | Msd K.K. | Spirochromanone carboxylic acids |
| WO2010008521A1 (en) | 2008-07-14 | 2010-01-21 | Cropsolution, Inc. | Modulators of acetyl-coenzyme a carboxylase and methods of use thereof |
| US20110190365A1 (en) * | 2008-08-14 | 2011-08-04 | Bayer Crop Science Ag | Insecticidal 4-phenyl-1H-pyrazoles |
| CA2744154A1 (en) | 2008-11-20 | 2010-05-27 | 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 |
| CA2778949C (en) | 2009-10-30 | 2018-02-27 | Janssen Pharmaceutica Nv | Imidazo[1,2-b]pyridazine derivatives and their use as pde10 inhibitors |
| BR112012018358A2 (pt) | 2009-12-21 | 2016-08-09 | Bayer Cropscience Ag | tienilpiri(mi)dinilazol e seu uso para controlar fungos fitopatogênicos |
| 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 |
| CA2812526A1 (en) | 2010-05-06 | 2011-11-10 | Vertex Pharmaceuticals Incorporated | Heterocyclic chromene-spirocyclic piperidine amides as modulators of ion channels |
| US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| HRP20161178T1 (hr) * | 2010-09-30 | 2016-11-04 | Pfizer Inc. | N1-PIRAZOLOSPIROKETONSKI INHIBITORI ACETIL-CoA-KARBOKSILAZE |
| JP2013542960A (ja) * | 2010-11-08 | 2013-11-28 | グラクソスミスクライン、インテレクチュアル、プロパティー、ナンバー２、リミテッド | 脂肪酸シンターゼ阻害剤 |
| BR112013019211A2 (pt) | 2011-02-02 | 2021-07-06 | Vertex Pharma | amidas de piperidina espirocíclicas de pirrolopirazina como moduladores de canais de íon |
| CN103443105A (zh) | 2011-02-18 | 2013-12-11 | 沃泰克斯药物股份有限公司 | 作为离子通道调节剂的苯并二氢吡喃-螺环哌啶酰胺 |
| US8828996B2 (en) | 2011-03-14 | 2014-09-09 | Vertex Pharmaceuticals Incorporated | Morpholine-spirocyclic piperidine amides as modulators of ion channels |
| WO2012161119A1 (ja) * | 2011-05-20 | 2012-11-29 | 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 |
| BR112013033375B1 (pt) | 2011-06-27 | 2022-05-10 | Janssen Pharmaceutica N.V | Derivados de 1-aril-4-metil-[1,2,4]triazolo[4,3-a]quinoxa-lina, seu uso, composição farmacêutica que os compreende, processo de preparação dos mesmos, solução estéril e composto intermediário |
| CN104321311A (zh) * | 2012-05-22 | 2015-01-28 | 埃科特莱茵药品有限公司 | 制备2-环戊基-6-甲氧基-异烟酸的新颖方法 |
| RU2657540C2 (ru) | 2012-06-26 | 2018-06-14 | Янссен Фармацевтика Нв | Комбинации, содержащие ингибиторы pde 2, такие как 1-арил-4-метил-[1,2,4]триазоло[4,3-а]хиноксалиновые соединения, и ингибиторы pde 10, для применения в лечении неврологических или метаболических расстройств |
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- 2008-01-08 AU AU2008205642A patent/AU2008205642B2/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 WO PCT/US2008/000247 patent/WO2008088692A2/en not_active Ceased
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