ZA200610415B - Pyrimidine derivatives as 11?-HSD1 inhibitors - Google Patents
Pyrimidine derivatives as 11?-HSD1 inhibitors Download PDFInfo
- Publication number
- ZA200610415B ZA200610415B ZA200610415A ZA200610415A ZA200610415B ZA 200610415 B ZA200610415 B ZA 200610415B ZA 200610415 A ZA200610415 A ZA 200610415A ZA 200610415 A ZA200610415 A ZA 200610415A ZA 200610415 B ZA200610415 B ZA 200610415B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyrimidin
- benzenesulfonamide
- methyl
- isopropyl
- chloro
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title description 12
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 3
- 150000003230 pyrimidines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 102
- -1 cyclopropylmethoxymethyl Chemical group 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- AREOKSGFWPUZLH-UHFFFAOYSA-N 2-propan-2-ylpyrimidin-4-amine Chemical compound CC(C)C1=NC=CC(N)=N1 AREOKSGFWPUZLH-UHFFFAOYSA-N 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 206010012601 diabetes mellitus Diseases 0.000 claims description 17
- 125000001544 thienyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 238000011321 prophylaxis Methods 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000005936 piperidyl group Chemical group 0.000 claims description 13
- 125000005493 quinolyl group Chemical group 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 125000002971 oxazolyl group Chemical group 0.000 claims description 11
- 208000008589 Obesity Diseases 0.000 claims description 10
- 235000020824 obesity Nutrition 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- JISNIQNOVMHUPR-UHFFFAOYSA-N 2-cyclobutylpyrimidin-4-amine Chemical compound NC1=CC=NC(C2CCC2)=N1 JISNIQNOVMHUPR-UHFFFAOYSA-N 0.000 claims description 8
- 206010020772 Hypertension Diseases 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 102000004190 Enzymes Human genes 0.000 claims description 6
- 108090000790 Enzymes Proteins 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- IJCDVZFQQXVIOM-UHFFFAOYSA-N 2,3-dichloro-n-(2-propan-2-ylpyrimidin-4-yl)benzenesulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)Cl)=N1 IJCDVZFQQXVIOM-UHFFFAOYSA-N 0.000 claims description 5
- SHUZMSGZCKQUSJ-UHFFFAOYSA-N 3-chloro-2-methyl-n-(2-methylpyrimidin-4-yl)benzenesulfonamide Chemical compound CC1=NC=CC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 SHUZMSGZCKQUSJ-UHFFFAOYSA-N 0.000 claims description 5
- SOWDIFYDWBRCDV-UHFFFAOYSA-N 3-chloro-n-(2-cyclobutylpyrimidin-4-yl)-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=CC=NC(C2CCC2)=N1 SOWDIFYDWBRCDV-UHFFFAOYSA-N 0.000 claims description 5
- 208000030814 Eating disease Diseases 0.000 claims description 5
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 5
- 235000014632 disordered eating Nutrition 0.000 claims description 5
- MNLSOXADHQENOR-UHFFFAOYSA-N n-(2-cyclobutylpyrimidin-4-yl)naphthalene-2-sulfonamide Chemical compound C=1C=C2C=CC=CC2=CC=1S(=O)(=O)NC(N=1)=CC=NC=1C1CCC1 MNLSOXADHQENOR-UHFFFAOYSA-N 0.000 claims description 5
- CSSYVAVOAJDRIY-UHFFFAOYSA-N n-(2-cyclopropylpyrimidin-4-yl)naphthalene-2-sulfonamide Chemical compound C=1C=C2C=CC=CC2=CC=1S(=O)(=O)NC(N=1)=CC=NC=1C1CC1 CSSYVAVOAJDRIY-UHFFFAOYSA-N 0.000 claims description 5
- XKSMTDGGOOQORG-UHFFFAOYSA-N n-(2-propan-2-ylpyrimidin-4-yl)naphthalene-2-sulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)=N1 XKSMTDGGOOQORG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- MTXBCTZEXLCAEI-UHFFFAOYSA-N 3,4-dimethoxy-n-(2-propan-2-ylpyrimidin-4-yl)benzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC1=CC=NC(C(C)C)=N1 MTXBCTZEXLCAEI-UHFFFAOYSA-N 0.000 claims description 4
- NXEKPEOQCJNULZ-UHFFFAOYSA-N 3-chloro-2-methyl-n-(2-propan-2-ylpyrimidin-4-yl)benzenesulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 NXEKPEOQCJNULZ-UHFFFAOYSA-N 0.000 claims description 4
- LCPLJAVSFNXOCD-UHFFFAOYSA-N 3-chloro-n-(2-cyclopropylpyrimidin-4-yl)-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=CC=NC(C2CC2)=N1 LCPLJAVSFNXOCD-UHFFFAOYSA-N 0.000 claims description 4
- VXDNMGLZXBVMER-UHFFFAOYSA-N 5-chloro-n-(2-propan-2-ylpyrimidin-4-yl)thiophene-2-sulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)C=2SC(Cl)=CC=2)=N1 VXDNMGLZXBVMER-UHFFFAOYSA-N 0.000 claims description 4
- QMLXVXIEMCANHU-UHFFFAOYSA-N 5-fluoro-2-methyl-n-(2-propan-2-ylpyrimidin-4-yl)benzenesulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)C=2C(=CC=C(F)C=2)C)=N1 QMLXVXIEMCANHU-UHFFFAOYSA-N 0.000 claims description 4
- QWZZUZAIHNZLEN-UHFFFAOYSA-N 5-pyridin-2-ylthiophene-2-sulfonic acid Chemical compound S1C(S(=O)(=O)O)=CC=C1C1=CC=CC=N1 QWZZUZAIHNZLEN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- OBAHUBCBAZTGER-UHFFFAOYSA-N n-(2,5,6-trimethylpyrimidin-4-yl)naphthalene-2-sulfonamide Chemical compound CC1=NC(C)=C(C)C(NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)=N1 OBAHUBCBAZTGER-UHFFFAOYSA-N 0.000 claims description 4
- IKBKTVNAVSSDAJ-UHFFFAOYSA-N n-(2-cyclopropylpyrimidin-4-yl)-4-phenylbenzenesulfonamide Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1S(=O)(=O)NC(N=1)=CC=NC=1C1CC1 IKBKTVNAVSSDAJ-UHFFFAOYSA-N 0.000 claims description 4
- PYBDULOHPUJPCT-UHFFFAOYSA-N n-(2-propan-2-ylpyrimidin-4-yl)-2-(trifluoromethyl)benzenesulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 PYBDULOHPUJPCT-UHFFFAOYSA-N 0.000 claims description 4
- DFJQQKRTMIUKRM-UHFFFAOYSA-N 2,4-difluoro-n-(2-propan-2-ylpyrimidin-4-yl)benzenesulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)C=2C(=CC(F)=CC=2)F)=N1 DFJQQKRTMIUKRM-UHFFFAOYSA-N 0.000 claims description 3
- HOHCCDFSNGRUID-UHFFFAOYSA-N 2-chloro-n-(2-propan-2-ylpyrimidin-4-yl)benzenesulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 HOHCCDFSNGRUID-UHFFFAOYSA-N 0.000 claims description 3
- KCHISDKSKSRCTD-UHFFFAOYSA-N 3-chloro-4-methyl-n-(2-methylpyrimidin-4-yl)benzenesulfonamide Chemical compound CC1=NC=CC(NS(=O)(=O)C=2C=C(Cl)C(C)=CC=2)=N1 KCHISDKSKSRCTD-UHFFFAOYSA-N 0.000 claims description 3
- VPPVJHUPCODYKH-UHFFFAOYSA-N 3-chloro-n-(2-cyclopentylpyrimidin-4-yl)-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=CC=NC(C2CCCC2)=N1 VPPVJHUPCODYKH-UHFFFAOYSA-N 0.000 claims description 3
- XVXDIEUUWMRPMU-UHFFFAOYSA-N 3-chloro-n-(2-cyclopropylpyrimidin-4-yl)-4-methoxybenzenesulfonamide Chemical compound C1=C(Cl)C(OC)=CC=C1S(=O)(=O)NC1=CC=NC(C2CC2)=N1 XVXDIEUUWMRPMU-UHFFFAOYSA-N 0.000 claims description 3
- DZHFLSLZKLSRED-UHFFFAOYSA-N 3-chloro-n-(2-propan-2-ylpyrimidin-4-yl)benzenesulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)C=2C=C(Cl)C=CC=2)=N1 DZHFLSLZKLSRED-UHFFFAOYSA-N 0.000 claims description 3
- WEWPRGZLONDXCN-UHFFFAOYSA-N 3-chloro-n-[2-(cyclopropylmethoxymethyl)pyrimidin-4-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=CC=NC(COCC2CC2)=N1 WEWPRGZLONDXCN-UHFFFAOYSA-N 0.000 claims description 3
- ITXFPBUPXFAXDC-UHFFFAOYSA-N 4,5-dichloro-n-(2-propan-2-ylpyrimidin-4-yl)thiophene-2-sulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)C=2SC(Cl)=C(Cl)C=2)=N1 ITXFPBUPXFAXDC-UHFFFAOYSA-N 0.000 claims description 3
- CULFBEIFZZCSIX-UHFFFAOYSA-N 4-(1,3-oxazol-5-yl)-n-(2-propan-2-ylpyrimidin-4-yl)benzenesulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)C=2C=CC(=CC=2)C=2OC=NC=2)=N1 CULFBEIFZZCSIX-UHFFFAOYSA-N 0.000 claims description 3
- DXLINYYEFHFEQX-UHFFFAOYSA-N 4-chloro-n-(2-ethylpyrimidin-4-yl)-2,5-dimethylbenzenesulfonamide Chemical compound CCC1=NC=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(C)C=2)C)=N1 DXLINYYEFHFEQX-UHFFFAOYSA-N 0.000 claims description 3
- UFGUZPCPBBUYQZ-UHFFFAOYSA-N 4-phenyl-n-(2-propan-2-ylpyrimidin-4-yl)benzenesulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 UFGUZPCPBBUYQZ-UHFFFAOYSA-N 0.000 claims description 3
- XDTYUYVIGLIFCW-UHFFFAOYSA-N 4-phenylbenzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1C1=CC=CC=C1 XDTYUYVIGLIFCW-UHFFFAOYSA-N 0.000 claims description 3
- FFCHCAKFWDYMMB-UHFFFAOYSA-N 5-chloro-n-(2-cyclopropylpyrimidin-4-yl)-2-methoxybenzenesulfonamide Chemical compound COC1=CC=C(Cl)C=C1S(=O)(=O)NC1=CC=NC(C2CC2)=N1 FFCHCAKFWDYMMB-UHFFFAOYSA-N 0.000 claims description 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- KCOVASABLTVILA-UHFFFAOYSA-N n-(2,6-dimethylpyrimidin-4-yl)benzenesulfonamide Chemical compound CC1=NC(C)=CC(NS(=O)(=O)C=2C=CC=CC=2)=N1 KCOVASABLTVILA-UHFFFAOYSA-N 0.000 claims description 3
- SYFAUQHDGYQBKZ-UHFFFAOYSA-N n-(2-cyclopropylpyrimidin-4-yl)-3-methoxybenzenesulfonamide Chemical compound COC1=CC=CC(S(=O)(=O)NC=2N=C(N=CC=2)C2CC2)=C1 SYFAUQHDGYQBKZ-UHFFFAOYSA-N 0.000 claims description 3
- AFQCVOKNLJMPAF-UHFFFAOYSA-N n-(2-cyclopropylpyrimidin-4-yl)-5-phenylthiophene-2-sulfonamide Chemical compound C=1C=C(C=2C=CC=CC=2)SC=1S(=O)(=O)NC(N=1)=CC=NC=1C1CC1 AFQCVOKNLJMPAF-UHFFFAOYSA-N 0.000 claims description 3
- KXJSKPBZJPKUFZ-UHFFFAOYSA-N n-(2-cyclopropylpyrimidin-4-yl)quinoline-8-sulfonamide Chemical compound C=1C=CC2=CC=CN=C2C=1S(=O)(=O)NC(N=1)=CC=NC=1C1CC1 KXJSKPBZJPKUFZ-UHFFFAOYSA-N 0.000 claims description 3
- MEYLLJKGMQJUDE-UHFFFAOYSA-N n-(2-propan-2-ylpyrimidin-4-yl)-5-pyridin-2-ylthiophene-2-sulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)C=2SC(=CC=2)C=2N=CC=CC=2)=N1 MEYLLJKGMQJUDE-UHFFFAOYSA-N 0.000 claims description 3
- IFNJIFNNGPCCCH-UHFFFAOYSA-N n-(2-propan-2-ylpyrimidin-4-yl)piperidine-1-sulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)N2CCCCC2)=N1 IFNJIFNNGPCCCH-UHFFFAOYSA-N 0.000 claims description 3
- FFNKRDHGXCTZFB-UHFFFAOYSA-N n-(2-tert-butylpyrimidin-4-yl)-4-(1,3-oxazol-5-yl)benzenesulfonamide Chemical compound CC(C)(C)C1=NC=CC(NS(=O)(=O)C=2C=CC(=CC=2)C=2OC=NC=2)=N1 FFNKRDHGXCTZFB-UHFFFAOYSA-N 0.000 claims description 3
- FSMXQAJSVGAKPC-UHFFFAOYSA-N n-(2-tert-butylpyrimidin-4-yl)naphthalene-2-sulfonamide Chemical compound CC(C)(C)C1=NC=CC(NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)=N1 FSMXQAJSVGAKPC-UHFFFAOYSA-N 0.000 claims description 3
- CYGPAHFMMDHMEG-UHFFFAOYSA-N n-[2-(dimethylamino)-6-methyl-5-propylpyrimidin-4-yl]benzenesulfonamide Chemical compound CCCC1=C(C)N=C(N(C)C)N=C1NS(=O)(=O)C1=CC=CC=C1 CYGPAHFMMDHMEG-UHFFFAOYSA-N 0.000 claims description 3
- FPHCKTAZGFAGCM-UHFFFAOYSA-N n-benzyl-3-chloro-n-(2-cyclopropylpyrimidin-4-yl)-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N(C=1N=C(N=CC=1)C1CC1)CC1=CC=CC=C1 FPHCKTAZGFAGCM-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- CLVUJGQYWKRSEL-UHFFFAOYSA-N 2,4-dichloro-6-methyl-n-(2-propan-2-ylpyrimidin-4-yl)benzenesulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 CLVUJGQYWKRSEL-UHFFFAOYSA-N 0.000 claims description 2
- BOMZXAGADWBXGS-UHFFFAOYSA-N 2,4-dichloro-n-(2-cyclobutylpyrimidin-4-yl)-6-methylbenzenesulfonamide Chemical compound CC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=CC=NC(C2CCC2)=N1 BOMZXAGADWBXGS-UHFFFAOYSA-N 0.000 claims description 2
- MQRXIMFLLLLFPC-UHFFFAOYSA-N 2,4-dichloro-n-(2-ethylpyrimidin-4-yl)-6-methylbenzenesulfonamide Chemical compound CCC1=NC=CC(NS(=O)(=O)C=2C(=CC(Cl)=CC=2C)Cl)=N1 MQRXIMFLLLLFPC-UHFFFAOYSA-N 0.000 claims description 2
- ODNALKGRMFACHM-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)sulfonyl-(2-propan-2-ylpyrimidin-4-yl)amino]-n,n-dimethylacetamide Chemical compound CC(C)C1=NC=CC(N(CC(=O)N(C)C)S(=O)(=O)C=2C=C(Cl)C(Cl)=CC=2)=N1 ODNALKGRMFACHM-UHFFFAOYSA-N 0.000 claims description 2
- BJUMIULGJPMIKL-UHFFFAOYSA-N 3-bromo-5-chloro-n-(2-propan-2-ylpyrimidin-4-yl)thiophene-2-sulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)C2=C(C=C(Cl)S2)Br)=N1 BJUMIULGJPMIKL-UHFFFAOYSA-N 0.000 claims description 2
- KTGZTFRAUHJLKA-UHFFFAOYSA-N 3-chloro-2-methyl-n-(2-phenylpyrimidin-4-yl)benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=CC=NC(C=2C=CC=CC=2)=N1 KTGZTFRAUHJLKA-UHFFFAOYSA-N 0.000 claims description 2
- OXWYRMCMKXNUEX-UHFFFAOYSA-N 3-chloro-2-methyl-n-(6-phenylpyrimidin-4-yl)benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=CC(C=2C=CC=CC=2)=NC=N1 OXWYRMCMKXNUEX-UHFFFAOYSA-N 0.000 claims description 2
- FTMHVYGKPMZDQT-UHFFFAOYSA-N 3-chloro-n-[2-(methoxymethyl)pyrimidin-4-yl]-2-methylbenzenesulfonamide Chemical compound COCC1=NC=CC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 FTMHVYGKPMZDQT-UHFFFAOYSA-N 0.000 claims description 2
- MMRIFGUGQHABNP-UHFFFAOYSA-N 4,5-dichloro-2-fluoro-n-(2-propan-2-ylpyrimidin-4-yl)benzenesulfonamide Chemical compound CC(C)C1=NC=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)F)=N1 MMRIFGUGQHABNP-UHFFFAOYSA-N 0.000 claims description 2
- XPXBXPSFASBEMB-UHFFFAOYSA-N 4-chloro-n-(2-cyclopropylpyrimidin-4-yl)-2,5-dimethylbenzenesulfonamide Chemical compound C1=C(Cl)C(C)=CC(S(=O)(=O)NC=2N=C(N=CC=2)C2CC2)=C1C XPXBXPSFASBEMB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- AAUQBTFEBIMNHZ-UHFFFAOYSA-N n-(2-cyclobutylpyrimidin-4-yl)-5-pyridin-2-ylthiophene-2-sulfonamide Chemical compound C=1C=C(C=2N=CC=CC=2)SC=1S(=O)(=O)NC(N=1)=CC=NC=1C1CCC1 AAUQBTFEBIMNHZ-UHFFFAOYSA-N 0.000 claims description 2
- JQMFTNHDXPLEPA-UHFFFAOYSA-N n-(2-cyclopropylpyrimidin-4-yl)-2,5-difluorobenzenesulfonamide Chemical compound FC1=CC=C(F)C(S(=O)(=O)NC=2N=C(N=CC=2)C2CC2)=C1 JQMFTNHDXPLEPA-UHFFFAOYSA-N 0.000 claims description 2
- PSPKUOXBXCOFMO-UHFFFAOYSA-N n-(2-cyclopropylpyrimidin-4-yl)-5-fluoro-2-methylbenzenesulfonamide Chemical compound CC1=CC=C(F)C=C1S(=O)(=O)NC1=CC=NC(C2CC2)=N1 PSPKUOXBXCOFMO-UHFFFAOYSA-N 0.000 claims description 2
- SRSNCYVEBHOCCG-UHFFFAOYSA-N n-(2-cyclopropylpyrimidin-4-yl)benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(N=1)=CC=NC=1C1CC1 SRSNCYVEBHOCCG-UHFFFAOYSA-N 0.000 claims description 2
- OHWDDVYKSWMVNO-UHFFFAOYSA-N n-(2-tert-butylpyrimidin-4-yl)-2,5-difluorobenzenesulfonamide Chemical compound CC(C)(C)C1=NC=CC(NS(=O)(=O)C=2C(=CC=C(F)C=2)F)=N1 OHWDDVYKSWMVNO-UHFFFAOYSA-N 0.000 claims description 2
- ATHCAFQWRBPHSF-UHFFFAOYSA-N n-(2-tert-butylpyrimidin-4-yl)-5-fluoro-2-methylbenzenesulfonamide Chemical compound CC1=CC=C(F)C=C1S(=O)(=O)NC1=CC=NC(C(C)(C)C)=N1 ATHCAFQWRBPHSF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims 1
- XOLCFSBHGQRTPG-UHFFFAOYSA-N n-(2,6-dimethylpyrimidin-4-yl)naphthalene-2-sulfonamide Chemical compound CC1=NC(C)=CC(NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)=N1 XOLCFSBHGQRTPG-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 239000006260 foam Substances 0.000 description 33
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Child & Adolescent Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04102999 | 2004-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200610415B true ZA200610415B (en) | 2008-06-25 |
Family
ID=35478760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200610415A ZA200610415B (en) | 2004-06-28 | 2006-12-12 | Pyrimidine derivatives as 11?-HSD1 inhibitors |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7507733B2 (fr) |
| EP (1) | EP1763517B1 (fr) |
| JP (1) | JP4809339B2 (fr) |
| CN (1) | CN1972918B (fr) |
| AR (1) | AR049699A1 (fr) |
| AT (1) | ATE509011T1 (fr) |
| AU (1) | AU2005256442B2 (fr) |
| BR (1) | BRPI0512705A (fr) |
| CA (1) | CA2571361C (fr) |
| DK (1) | DK1763517T3 (fr) |
| ES (1) | ES2362884T3 (fr) |
| HK (1) | HK1104553A1 (fr) |
| IL (1) | IL179914A0 (fr) |
| MX (1) | MXPA06014892A (fr) |
| MY (1) | MY143568A (fr) |
| NO (1) | NO20070445L (fr) |
| NZ (1) | NZ551859A (fr) |
| PL (1) | PL1763517T3 (fr) |
| PT (1) | PT1763517E (fr) |
| RU (1) | RU2375351C2 (fr) |
| TW (1) | TWI299040B (fr) |
| WO (1) | WO2006000371A2 (fr) |
| ZA (1) | ZA200610415B (fr) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1866298A2 (fr) * | 2005-03-31 | 2007-12-19 | Takeda San Diego, Inc. | Inhibiteurs de l'hydroxysteroide deshydrogenase |
| AU2007212429A1 (en) * | 2006-02-07 | 2007-08-16 | Wyeth | 11-beta HSD1 inhibitors |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| US8318941B2 (en) | 2006-07-06 | 2012-11-27 | Bristol-Myers Squibb Company | Pyridone/hydroxypyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| TW200827346A (en) | 2006-11-03 | 2008-07-01 | Astrazeneca Ab | Chemical compounds |
| TW200836719A (en) | 2007-02-12 | 2008-09-16 | Astrazeneca Ab | Chemical compounds |
| CL2008001839A1 (es) | 2007-06-21 | 2009-01-16 | Incyte Holdings Corp | Compuestos derivados de 2,7-diazaespirociclos, inhibidores de 11-beta hidroxil esteroide deshidrogenasa tipo 1; composicion farmaceutica que comprende a dichos compuestos; utiles para tratar la obesidad, diabetes, intolerancia a la glucosa, diabetes tipo ii, entre otras enfermedades. |
| US20100022572A1 (en) | 2008-07-18 | 2010-01-28 | Kowa Company, Ltd. | Novel spiro compound and medicine comprising the same |
| AU2009279787B2 (en) * | 2008-08-04 | 2014-05-29 | Chdi Foundation, Inc. | Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| WO2010023931A1 (fr) | 2008-08-29 | 2010-03-04 | 興和株式会社 | Dérivé 1-adamantylazétidine-2-one et préparation pharmaceutique comprenant ce dérivé |
| JP5477973B2 (ja) | 2008-10-29 | 2014-04-23 | 興和株式会社 | １，２−ジアゼチジン−３−オン誘導体及びこれを含有する医薬 |
| MX2012008346A (es) | 2010-01-25 | 2012-11-12 | Chdi Foundation Inc | Determinados inhibidores de cinurenina-3-monooxigenasa, composiciones farmceuticas y metodos de uso de los mismos. |
| US20130310431A1 (en) * | 2010-10-15 | 2013-11-21 | Amgen Inc | Uses for substituted 2-amino-thiazolones in treating alzheimer's disease |
| WO2012102366A1 (fr) * | 2011-01-28 | 2012-08-02 | 日本たばこ産業株式会社 | Procédé de production d'un nouveau composé de pipérazine |
| AU2012300246A1 (en) | 2011-08-30 | 2014-03-06 | Chdi Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| SG2014012926A (en) | 2011-08-30 | 2014-06-27 | Chdi Foundation Inc | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| TW201512171A (zh) | 2013-04-19 | 2015-04-01 | Pfizer Ltd | 化學化合物 |
| US10258621B2 (en) | 2014-07-17 | 2019-04-16 | Chdi Foundation, Inc. | Methods and compositions for treating HIV-related disorders |
| US10653681B2 (en) | 2016-03-16 | 2020-05-19 | Recurium Ip Holdings, Llc | Analgesic compounds |
| EP3235813A1 (fr) | 2016-04-19 | 2017-10-25 | Cidqo 2012, S.L. | Dérivés aza-tétra-cycliques |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1229413A (fr) * | 1967-06-14 | 1971-04-21 | ||
| HU206337B (en) * | 1988-12-29 | 1992-10-28 | Mitsui Petrochemical Ind | Process for producing pyrimidine derivatives and pharmaceutical compositions |
| JP2744663B2 (ja) * | 1988-12-29 | 1998-04-28 | 三井化学株式会社 | ピリミジン類及びその薬学的に許容される塩類 |
| TW287160B (fr) * | 1992-12-10 | 1996-10-01 | Hoffmann La Roche | |
| TW394761B (en) * | 1993-06-28 | 2000-06-21 | Hoffmann La Roche | Novel Sulfonylamino Pyrimidines |
| SE0001899D0 (sv) * | 2000-05-22 | 2000-05-22 | Pharmacia & Upjohn Ab | New compounds |
| WO2003099773A1 (fr) * | 2002-05-24 | 2003-12-04 | Millennium Pharmaceuticals, Inc. | Inhibiteurs de ccr9 et utilisation de ceux-ci |
| CN1946703A (zh) * | 2004-04-20 | 2007-04-11 | 特兰斯泰克制药公司 | 取代的噻唑和嘧啶衍生物作为黑素细胞皮质激素受体调节剂 |
-
2005
- 2005-06-20 PT PT05755629T patent/PT1763517E/pt unknown
- 2005-06-20 AU AU2005256442A patent/AU2005256442B2/en not_active Ceased
- 2005-06-20 CA CA2571361A patent/CA2571361C/fr not_active Expired - Fee Related
- 2005-06-20 EP EP05755629A patent/EP1763517B1/fr active Active
- 2005-06-20 CN CN2005800209571A patent/CN1972918B/zh not_active Expired - Fee Related
- 2005-06-20 JP JP2007518500A patent/JP4809339B2/ja not_active Expired - Fee Related
- 2005-06-20 DK DK05755629.2T patent/DK1763517T3/da active
- 2005-06-20 MX MXPA06014892A patent/MXPA06014892A/es active IP Right Grant
- 2005-06-20 BR BRPI0512705-0A patent/BRPI0512705A/pt not_active IP Right Cessation
- 2005-06-20 NZ NZ551859A patent/NZ551859A/en not_active IP Right Cessation
- 2005-06-20 RU RU2007103303/04A patent/RU2375351C2/ru not_active IP Right Cessation
- 2005-06-20 ES ES05755629T patent/ES2362884T3/es active Active
- 2005-06-20 WO PCT/EP2005/006649 patent/WO2006000371A2/fr active Application Filing
- 2005-06-20 PL PL05755629T patent/PL1763517T3/pl unknown
- 2005-06-20 AT AT05755629T patent/ATE509011T1/de active
- 2005-06-24 TW TW094121333A patent/TWI299040B/zh not_active IP Right Cessation
- 2005-06-24 AR ARP050102606A patent/AR049699A1/es unknown
- 2005-06-27 MY MYPI20053011A patent/MY143568A/en unknown
- 2005-06-27 US US11/168,031 patent/US7507733B2/en not_active Expired - Fee Related
-
2006
- 2006-12-07 IL IL179914A patent/IL179914A0/en unknown
- 2006-12-12 ZA ZA200610415A patent/ZA200610415B/en unknown
-
2007
- 2007-01-24 NO NO20070445A patent/NO20070445L/no not_active Application Discontinuation
- 2007-11-26 HK HK07112870.3A patent/HK1104553A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2375351C2 (ru) | 2009-12-10 |
| IL179914A0 (en) | 2007-05-15 |
| CN1972918B (zh) | 2010-10-13 |
| MXPA06014892A (es) | 2007-02-28 |
| MY143568A (en) | 2011-05-31 |
| ATE509011T1 (de) | 2011-05-15 |
| TWI299040B (en) | 2008-07-21 |
| BRPI0512705A (pt) | 2008-04-01 |
| NZ551859A (en) | 2010-05-28 |
| AU2005256442A1 (en) | 2006-01-05 |
| AR049699A1 (es) | 2006-08-30 |
| NO20070445L (no) | 2007-01-24 |
| ES2362884T3 (es) | 2011-07-14 |
| CA2571361C (fr) | 2011-07-26 |
| DK1763517T3 (da) | 2011-06-06 |
| WO2006000371A3 (fr) | 2006-04-27 |
| JP4809339B2 (ja) | 2011-11-09 |
| HK1104553A1 (en) | 2008-01-18 |
| EP1763517A2 (fr) | 2007-03-21 |
| WO2006000371A2 (fr) | 2006-01-05 |
| US7507733B2 (en) | 2009-03-24 |
| EP1763517B1 (fr) | 2011-05-11 |
| PT1763517E (pt) | 2011-07-01 |
| JP2008504321A (ja) | 2008-02-14 |
| CA2571361A1 (fr) | 2006-01-05 |
| CN1972918A (zh) | 2007-05-30 |
| RU2007103303A (ru) | 2008-08-10 |
| PL1763517T3 (pl) | 2011-10-31 |
| TW200616976A (en) | 2006-06-01 |
| AU2005256442B2 (en) | 2009-02-12 |
| US20050288308A1 (en) | 2005-12-29 |
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