ES2666918T3 - Derivado de pirazol - Google Patents
Derivado de pirazol Download PDFInfo
- Publication number
- ES2666918T3 ES2666918T3 ES14775913.8T ES14775913T ES2666918T3 ES 2666918 T3 ES2666918 T3 ES 2666918T3 ES 14775913 T ES14775913 T ES 14775913T ES 2666918 T3 ES2666918 T3 ES 2666918T3
- Authority
- ES
- Spain
- Prior art keywords
- group
- cyano
- pyrazol
- carboxylic acid
- pyridin
- 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.)
- Active
Links
- 150000003217 pyrazoles Chemical class 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 219
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 41
- 125000005843 halogen group Chemical group 0.000 claims abstract description 40
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 24
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 6
- -1 2,3-dimethylphenyl Chemical group 0.000 claims description 96
- 125000006239 protecting group Chemical group 0.000 claims description 36
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims description 26
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 201000001431 Hyperuricemia Diseases 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
- 201000005569 Gout Diseases 0.000 claims description 13
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 11
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 10
- 206010020772 Hypertension Diseases 0.000 claims description 10
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 206010012601 diabetes mellitus Diseases 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 9
- 208000023275 Autoimmune disease Diseases 0.000 claims description 9
- 206010007027 Calculus urinary Diseases 0.000 claims description 9
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 9
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 9
- 206010019280 Heart failures Diseases 0.000 claims description 9
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 9
- 208000009911 Urinary Calculi Diseases 0.000 claims description 9
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 9
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 9
- 208000017169 kidney disease Diseases 0.000 claims description 9
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 9
- 208000023504 respiratory system disease Diseases 0.000 claims description 9
- 239000003064 xanthine oxidase inhibitor Substances 0.000 claims description 9
- 206010045170 Tumour lysis syndrome Diseases 0.000 claims description 8
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 208000010380 tumor lysis syndrome Diseases 0.000 claims description 8
- 229940123769 Xanthine oxidase inhibitor Drugs 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- RAPVLNZHTPYTMP-UHFFFAOYSA-N 1-(4-cyano-5-phenylpyridin-2-yl)pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC(C#N)=C(C=2C=CC=CC=2)C=N1 RAPVLNZHTPYTMP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
- MTELBVIMHZQCIC-UHFFFAOYSA-N 1-[4-cyano-5-(3-propan-2-ylphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound CC(C)C1=CC=CC(C=2C(=CC(=NC=2)N2N=CC(=C2)C(O)=O)C#N)=C1 MTELBVIMHZQCIC-UHFFFAOYSA-N 0.000 claims description 3
- JCIPKHUMPUGFHU-UHFFFAOYSA-N 1-[4-cyano-5-(2,3-difluorophenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC(C#N)=C(C=2C(=C(F)C=CC=2)F)C=N1 JCIPKHUMPUGFHU-UHFFFAOYSA-N 0.000 claims description 2
- XFJHCKZMURTIRM-UHFFFAOYSA-N 1-[4-cyano-5-(2,4-difluorophenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC(C#N)=C(C=2C(=CC(F)=CC=2)F)C=N1 XFJHCKZMURTIRM-UHFFFAOYSA-N 0.000 claims description 2
- PHDRBNNZXMXAAP-UHFFFAOYSA-N 1-[4-cyano-5-(2,5-difluorophenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC(C#N)=C(C=2C(=CC=C(F)C=2)F)C=N1 PHDRBNNZXMXAAP-UHFFFAOYSA-N 0.000 claims description 2
- QINRRSHKHQEUSV-UHFFFAOYSA-N 1-[4-cyano-5-(2-ethoxyphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound CCOC1=CC=CC=C1C1=CN=C(N2N=CC(=C2)C(O)=O)C=C1C#N QINRRSHKHQEUSV-UHFFFAOYSA-N 0.000 claims description 2
- KPAQZPHTFZXFFN-UHFFFAOYSA-N 1-[4-cyano-5-(2-fluoro-3-methoxyphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound COC1=CC=CC(C=2C(=CC(=NC=2)N2N=CC(=C2)C(O)=O)C#N)=C1F KPAQZPHTFZXFFN-UHFFFAOYSA-N 0.000 claims description 2
- CACZMSPNDKJKAP-UHFFFAOYSA-N 1-[4-cyano-5-(2-fluoro-3-methylphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound CC1=CC=CC(C=2C(=CC(=NC=2)N2N=CC(=C2)C(O)=O)C#N)=C1F CACZMSPNDKJKAP-UHFFFAOYSA-N 0.000 claims description 2
- MYIJMCWUVOESSN-UHFFFAOYSA-N 1-[4-cyano-5-(2-fluoro-4-methylphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound FC1=CC(C)=CC=C1C1=CN=C(N2N=CC(=C2)C(O)=O)C=C1C#N MYIJMCWUVOESSN-UHFFFAOYSA-N 0.000 claims description 2
- MWBPIPDCWZOLBQ-UHFFFAOYSA-N 1-[4-cyano-5-(2-fluoro-5-methylphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound CC1=CC=C(F)C(C=2C(=CC(=NC=2)N2N=CC(=C2)C(O)=O)C#N)=C1 MWBPIPDCWZOLBQ-UHFFFAOYSA-N 0.000 claims description 2
- LGGFKSXIIMMFJW-UHFFFAOYSA-N 1-[4-cyano-5-(2-fluoro-6-methoxyphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound COC1=CC=CC(F)=C1C1=CN=C(N2N=CC(=C2)C(O)=O)C=C1C#N LGGFKSXIIMMFJW-UHFFFAOYSA-N 0.000 claims description 2
- UVGSEHHOSDMXDZ-UHFFFAOYSA-N 1-[4-cyano-5-(2-fluorophenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC(C#N)=C(C=2C(=CC=CC=2)F)C=N1 UVGSEHHOSDMXDZ-UHFFFAOYSA-N 0.000 claims description 2
- WSDOWTTWOMPRAN-UHFFFAOYSA-N 1-[4-cyano-5-(2-methoxyphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound COC1=CC=CC=C1C1=CN=C(N2N=CC(=C2)C(O)=O)C=C1C#N WSDOWTTWOMPRAN-UHFFFAOYSA-N 0.000 claims description 2
- UCYPXVZYGPSGDF-UHFFFAOYSA-N 1-[4-cyano-5-(2-methylphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound CC1=CC=CC=C1C1=CN=C(N2N=CC(=C2)C(O)=O)C=C1C#N UCYPXVZYGPSGDF-UHFFFAOYSA-N 0.000 claims description 2
- ZWNJWMZLFOKNIM-UHFFFAOYSA-N 1-[4-cyano-5-(3-ethoxyphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound CCOC1=CC=CC(C=2C(=CC(=NC=2)N2N=CC(=C2)C(O)=O)C#N)=C1 ZWNJWMZLFOKNIM-UHFFFAOYSA-N 0.000 claims description 2
- OSAVMJIVIWEVBM-UHFFFAOYSA-N 1-[4-cyano-5-(3-fluorophenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC(C#N)=C(C=2C=C(F)C=CC=2)C=N1 OSAVMJIVIWEVBM-UHFFFAOYSA-N 0.000 claims description 2
- QVPIWSPOPLXCIE-UHFFFAOYSA-N 1-[4-cyano-5-(3-methoxyphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound COC1=CC=CC(C=2C(=CC(=NC=2)N2N=CC(=C2)C(O)=O)C#N)=C1 QVPIWSPOPLXCIE-UHFFFAOYSA-N 0.000 claims description 2
- NPSHRJMYWREVNM-UHFFFAOYSA-N 1-[4-cyano-5-(3-methylphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound CC1=CC=CC(C=2C(=CC(=NC=2)N2N=CC(=C2)C(O)=O)C#N)=C1 NPSHRJMYWREVNM-UHFFFAOYSA-N 0.000 claims description 2
- ONSYZMQTGJUIAY-UHFFFAOYSA-N 1-[4-cyano-5-(3-propoxyphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound CCCOC1=CC=CC(C=2C(=CC(=NC=2)N2N=CC(=C2)C(O)=O)C#N)=C1 ONSYZMQTGJUIAY-UHFFFAOYSA-N 0.000 claims description 2
- VSOASNIJFVVEOW-UHFFFAOYSA-N 1-[4-cyano-5-(4-fluoro-2-methoxyphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound COC1=CC(F)=CC=C1C1=CN=C(N2N=CC(=C2)C(O)=O)C=C1C#N VSOASNIJFVVEOW-UHFFFAOYSA-N 0.000 claims description 2
- YWIQFXTWPIJIEQ-UHFFFAOYSA-N 1-[4-cyano-5-(4-fluoro-2-methylphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound CC1=CC(F)=CC=C1C1=CN=C(N2N=CC(=C2)C(O)=O)C=C1C#N YWIQFXTWPIJIEQ-UHFFFAOYSA-N 0.000 claims description 2
- MHSYSZOMHGTVKF-UHFFFAOYSA-N 1-[4-cyano-5-(4-fluoro-3-methylphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(F)C(C)=CC(C=2C(=CC(=NC=2)N2N=CC(=C2)C(O)=O)C#N)=C1 MHSYSZOMHGTVKF-UHFFFAOYSA-N 0.000 claims description 2
- PLMLCIYYUZFZIP-UHFFFAOYSA-N 1-[4-cyano-5-(4-fluorophenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC(C#N)=C(C=2C=CC(F)=CC=2)C=N1 PLMLCIYYUZFZIP-UHFFFAOYSA-N 0.000 claims description 2
- FQMIMGDTOWYRRR-UHFFFAOYSA-N 1-[4-cyano-5-(4-hydroxyphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC(C#N)=C(C=2C=CC(O)=CC=2)C=N1 FQMIMGDTOWYRRR-UHFFFAOYSA-N 0.000 claims description 2
- OIJOSRAQKQYLNX-UHFFFAOYSA-N 1-[4-cyano-5-(4-methoxyphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=CN=C(N2N=CC(=C2)C(O)=O)C=C1C#N OIJOSRAQKQYLNX-UHFFFAOYSA-N 0.000 claims description 2
- UMPREEGSIWDSRI-UHFFFAOYSA-N 1-[4-cyano-5-(4-methylphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=CN=C(N2N=CC(=C2)C(O)=O)C=C1C#N UMPREEGSIWDSRI-UHFFFAOYSA-N 0.000 claims description 2
- NAXMTMWPAMGEGJ-UHFFFAOYSA-N 1-[4-cyano-5-(4-phenoxyphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC(C#N)=C(C=2C=CC(OC=3C=CC=CC=3)=CC=2)C=N1 NAXMTMWPAMGEGJ-UHFFFAOYSA-N 0.000 claims description 2
- OPCJRCUGERFJKI-UHFFFAOYSA-N 1-[4-cyano-5-(4-propan-2-ylphenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=CC(C(C)C)=CC=C1C1=CN=C(N2N=CC(=C2)C(O)=O)C=C1C#N OPCJRCUGERFJKI-UHFFFAOYSA-N 0.000 claims description 2
- PCCUAEAPOATXCO-UHFFFAOYSA-N 1-[4-cyano-5-[3-(difluoromethoxy)phenyl]pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC(C#N)=C(C=2C=C(OC(F)F)C=CC=2)C=N1 PCCUAEAPOATXCO-UHFFFAOYSA-N 0.000 claims description 2
- NSXROVPHRYSSII-UHFFFAOYSA-N 1-[4-cyano-5-[3-(trifluoromethyl)phenyl]pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC(C#N)=C(C=2C=C(C=CC=2)C(F)(F)F)C=N1 NSXROVPHRYSSII-UHFFFAOYSA-N 0.000 claims description 2
- CJWIXBKKDQQZPG-UHFFFAOYSA-N 1-[4-cyano-5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC(C#N)=C(C=2C=CC(OC(F)(F)F)=CC=2)C=N1 CJWIXBKKDQQZPG-UHFFFAOYSA-N 0.000 claims description 2
- BZZNPSULFPWTIP-UHFFFAOYSA-N 1-[5-(2-chlorophenyl)-4-cyanopyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC(C#N)=C(C=2C(=CC=CC=2)Cl)C=N1 BZZNPSULFPWTIP-UHFFFAOYSA-N 0.000 claims description 2
- KTVPUEORKGCLEV-UHFFFAOYSA-N 1-[5-(4-chloro-3-methylphenyl)-4-cyanopyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC(C=2C(=CC(=NC=2)N2N=CC(=C2)C(O)=O)C#N)=C1 KTVPUEORKGCLEV-UHFFFAOYSA-N 0.000 claims description 2
- HSFKDPKMYZYIFB-UHFFFAOYSA-N 1-[5-(4-chlorophenyl)-4-cyanopyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC(C#N)=C(C=2C=CC(Cl)=CC=2)C=N1 HSFKDPKMYZYIFB-UHFFFAOYSA-N 0.000 claims description 2
- MYAMSYXIJVQPEV-UHFFFAOYSA-N 1-[5-(4-tert-butylphenyl)-4-cyanopyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CN=C(N2N=CC(=C2)C(O)=O)C=C1C#N MYAMSYXIJVQPEV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 2
- KUCBFBWPUPNGQJ-UHFFFAOYSA-N 1-[4-cyano-5-(2-ethoxy-6-fluorophenyl)pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound CCOC1=CC=CC(F)=C1C1=CN=C(N2N=CC(=C2)C(O)=O)C=C1C#N KUCBFBWPUPNGQJ-UHFFFAOYSA-N 0.000 claims 1
- SPIUGOMVBRCRQH-UHFFFAOYSA-N 1-[5-(3-chloro-4-fluorophenyl)-4-cyanopyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC(C#N)=C(C=2C=C(Cl)C(F)=CC=2)C=N1 SPIUGOMVBRCRQH-UHFFFAOYSA-N 0.000 claims 1
- AVYVGKGNCSXAAH-UHFFFAOYSA-N 1-[5-(3-chlorophenyl)-4-cyanopyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC(C#N)=C(C=2C=C(Cl)C=CC=2)C=N1 AVYVGKGNCSXAAH-UHFFFAOYSA-N 0.000 claims 1
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 212
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 90
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 89
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 64
- 238000006243 chemical reaction Methods 0.000 description 61
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 57
- 239000002585 base Substances 0.000 description 49
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 46
- 239000002904 solvent Substances 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 45
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 42
- 238000000034 method Methods 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 39
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 108010093894 Xanthine oxidase Proteins 0.000 description 34
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 33
- 239000002253 acid Substances 0.000 description 33
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 32
- 102100033220 Xanthine oxidase Human genes 0.000 description 32
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 30
- 229940116269 uric acid Drugs 0.000 description 30
- 230000000694 effects Effects 0.000 description 28
- 230000002401 inhibitory effect Effects 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 28
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- Health & Medical Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013072788 | 2013-03-29 | ||
| JP2013072788 | 2013-03-29 | ||
| PCT/JP2014/059912 WO2014157740A1 (ja) | 2013-03-29 | 2014-03-28 | ピラゾール誘導体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2666918T3 true ES2666918T3 (es) | 2018-05-08 |
Family
ID=51624694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14775913.8T Active ES2666918T3 (es) | 2013-03-29 | 2014-03-28 | Derivado de pirazol |
Country Status (31)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2018126349A (ru) | 2015-12-18 | 2020-01-20 | Новартис Аг | Индановые производные и их применение в качестве активаторов растворимой гуанилатциклазы |
| US11344539B2 (en) | 2016-02-19 | 2022-05-31 | National University Corporation Tottori University | Therapeutic or prophylactic drug for dementia |
| EP4516781A1 (en) * | 2022-04-27 | 2025-03-05 | Atom Therapeutics Co., Ltd. | Compound for reducing uric acid |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4346094A (en) * | 1980-09-22 | 1982-08-24 | Eli Lilly And Company | 3-Aryl-5-isothiazolecarboxylic acids and related compounds used to lower uric acid levels |
| US4495195A (en) | 1982-11-01 | 1985-01-22 | Eli Lilly And Company | Xanthine oxidase inhibiting 3(5)-phenyl-substituted-5(3)-pyrazole-carboxylic acid derivatives, compositions, and methods of use |
| ID21775A (id) | 1996-10-25 | 1999-07-22 | Yoshitomi Pharmaceutical | Senyawa-senyawa 1-fenilpirazol dan penggunaan farmasinya |
| JPH10310578A (ja) | 1996-11-13 | 1998-11-24 | Yoshitomi Pharmaceut Ind Ltd | ３−フェニルピラゾール化合物 |
| BR9910578A (pt) * | 1998-04-28 | 2001-01-09 | Novartis Ag | Derivados de piridina substituìda por n-heteroarila e seu uso como herbicidas |
| PT1020454E (pt) * | 1998-06-19 | 2009-12-21 | Teijin Pharma Ltd | Modificações polimórficas do ácido 2-(3-ciano-4-isobutiloxifenil)-4-metil-5-tiazole-carboxílico e processos para a sua preparação |
| WO2005111003A1 (en) | 2004-04-29 | 2005-11-24 | Abbott Laboratories | Amino-tetrazoles analogues and methods of use |
| JP2007043457A (ja) | 2005-08-03 | 2007-02-15 | Masamichi Mochizuki | 携帯電話 |
| JP4849594B2 (ja) | 2005-09-30 | 2012-01-11 | フマキラー株式会社 | 送風式薬剤放散装置 |
| EP1932833B1 (en) * | 2005-10-07 | 2012-08-01 | Kissei Pharmaceutical Co., Ltd. | Nitrogenated heterocyclic compound and pharmaceutical composition comprising the same |
| ES2355068T3 (es) * | 2005-10-07 | 2011-03-22 | Astellas Pharma Inc. | Derivado del ácido triarilcarboxílico. |
| CA2643272A1 (en) | 2006-02-24 | 2007-08-30 | Astellas Pharma Inc. | Gent for treating or preventing digestive ulcer |
| CA2644963A1 (en) * | 2006-03-31 | 2007-10-11 | Novartis Ag | Organic compounds |
| JP2008126770A (ja) | 2006-11-17 | 2008-06-05 | Big Tool Co Ltd | 自動車用窓ガラスの取り外し方法 |
| JP5132132B2 (ja) | 2006-11-17 | 2013-01-30 | ヤマハ発動機株式会社 | 船舶用操舵装置及び船舶 |
| WO2008126772A1 (ja) | 2007-04-05 | 2008-10-23 | Astellas Pharma Inc. | 高血圧治療剤 |
| WO2008126770A1 (ja) | 2007-04-05 | 2008-10-23 | Astellas Pharma Inc. | トリアリールカルボン酸誘導体の製造方法 |
| WO2010044403A1 (ja) | 2008-10-15 | 2010-04-22 | キッセイ薬品工業株式会社 | ５員環ヘテロアリール誘導体及びその医薬用途 |
| WO2011011712A1 (en) * | 2009-07-24 | 2011-01-27 | Concert Pharmaceuticals, Inc. | Substituted imidazotriazines |
| EP2464647B1 (en) * | 2009-08-11 | 2016-09-21 | Bristol-Myers Squibb Company | Azaindazoles as btk kinase modulators and use thereof |
| JP4939578B2 (ja) | 2009-08-19 | 2012-05-30 | 株式会社沖データ | 現像剤搬送装置、現像剤収容器、及び画像形成装置 |
| TWI423962B (zh) | 2009-10-07 | 2014-01-21 | Lg Life Sciences Ltd | 有效作為黃嘌呤氧化酶抑制劑之新穎化合物、其製備方法及含該化合物之醫藥組成物 |
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2014
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- 2014-03-28 CN CN201480018955.8A patent/CN105189476B/zh not_active Expired - Fee Related
- 2014-03-28 SI SI201430658T patent/SI2980085T1/en unknown
- 2014-03-28 ME MEP-2018-105A patent/ME03055B/me unknown
- 2014-03-28 SM SM20180387T patent/SMT201800387T1/it unknown
- 2014-03-28 MY MYPI2015703292A patent/MY176149A/en unknown
- 2014-03-28 LT LTEP14775913.8T patent/LT2980085T/lt unknown
- 2014-03-28 PL PL14775913T patent/PL2980085T3/pl unknown
- 2014-03-28 MX MX2015013333A patent/MX363191B/es unknown
- 2014-03-28 HR HRP20180644TT patent/HRP20180644T1/hr unknown
- 2014-03-28 PT PT147759138T patent/PT2980085T/pt unknown
- 2014-03-28 BR BR112015024462A patent/BR112015024462A2/pt active Search and Examination
- 2014-03-28 DK DK14775913.8T patent/DK2980085T3/en active
- 2014-03-28 ES ES14775913.8T patent/ES2666918T3/es active Active
- 2014-03-28 RU RU2015141274A patent/RU2632884C2/ru active
- 2014-03-28 JP JP2015508836A patent/JP6091603B2/ja not_active Expired - Fee Related
- 2014-03-28 AU AU2014244855A patent/AU2014244855B2/en not_active Ceased
- 2014-03-28 SG SG11201507939XA patent/SG11201507939XA/en unknown
- 2014-03-28 RS RS20180453A patent/RS57154B1/sr unknown
- 2014-03-28 EP EP14775913.8A patent/EP2980085B1/en active Active
- 2014-03-28 KR KR1020157026553A patent/KR20150138212A/ko not_active Abandoned
- 2014-03-28 WO PCT/JP2014/059912 patent/WO2014157740A1/ja active Application Filing
- 2014-03-28 CA CA2904142A patent/CA2904142A1/en not_active Abandoned
- 2014-03-28 NZ NZ712680A patent/NZ712680A/en not_active IP Right Cessation
- 2014-03-28 US US14/774,517 patent/US9617240B2/en not_active Expired - Fee Related
- 2014-03-28 HU HUE14775913A patent/HUE037813T2/hu unknown
-
2015
- 2015-09-21 IL IL241772A patent/IL241772B/en active IP Right Grant
- 2015-09-28 SA SA515361238A patent/SA515361238B1/ar unknown
- 2015-09-28 ZA ZA2015/07146A patent/ZA201507146B/en unknown
- 2015-09-29 PH PH12015502264A patent/PH12015502264B1/en unknown
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2018
- 2018-04-30 CY CY181100450T patent/CY1120672T1/el unknown
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