RU2310648C2 - 5-замещенные пиразиновые или пиридиновые активаторы глюкокиназы - Google Patents
5-замещенные пиразиновые или пиридиновые активаторы глюкокиназы Download PDFInfo
- Publication number
- RU2310648C2 RU2310648C2 RU2005121667/04A RU2005121667A RU2310648C2 RU 2310648 C2 RU2310648 C2 RU 2310648C2 RU 2005121667/04 A RU2005121667/04 A RU 2005121667/04A RU 2005121667 A RU2005121667 A RU 2005121667A RU 2310648 C2 RU2310648 C2 RU 2310648C2
- Authority
- RU
- Russia
- Prior art keywords
- methanesulfonylphenyl
- cyclopentyl
- chloro
- propionamide
- pyrazin
- Prior art date
Links
- -1 5-substituted pyrazine Chemical class 0.000 title claims abstract 54
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims abstract 4
- 102000030595 Glucokinase Human genes 0.000 title abstract 2
- 108010021582 Glucokinase Proteins 0.000 title abstract 2
- 239000012190 activator Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract 82
- 150000003839 salts Chemical class 0.000 claims abstract 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 4
- 239000003814 drug Substances 0.000 claims abstract 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims 15
- 150000001721 carbon Chemical group 0.000 claims 14
- 229940080818 propionamide Drugs 0.000 claims 12
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 11
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- BFPODEUMNZELOT-GOSISDBHSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(3-hydroxyprop-1-ynyl)pyrazin-2-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(=NC=1)C#CCO)CC1CCCC1 BFPODEUMNZELOT-GOSISDBHSA-N 0.000 claims 5
- FKOMCYQVYFWGPV-IERDGZPVSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-[(1s)-1,2-dihydroxy-2-methylpropyl]pyrazin-2-yl]propanamide Chemical compound C1=NC([C@H](O)C(C)(O)C)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 FKOMCYQVYFWGPV-IERDGZPVSA-N 0.000 claims 5
- NESMGVQBWDEZAO-CQSZACIVSA-N chembl2337925 Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(=NC=1)C(\N)=N/O)CC1CCCC1 NESMGVQBWDEZAO-CQSZACIVSA-N 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- XHGUXJHPFQFDCQ-OAHLLOKOSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-(5-methylsulfanylpyrazin-2-yl)propanamide Chemical compound C1=NC(SC)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 XHGUXJHPFQFDCQ-OAHLLOKOSA-N 0.000 claims 4
- SXHFVJNXGCUJRL-YHVXIASJSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-(5-methylsulfinylpyrazin-2-yl)propanamide Chemical compound C1=NC(S(=O)C)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 SXHFVJNXGCUJRL-YHVXIASJSA-N 0.000 claims 4
- UILCYGKPSXGBPC-MRXNPFEDSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(2-hydroxyethylsulfanyl)pyrazin-2-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(SCCO)=NC=1)CC1CCCC1 UILCYGKPSXGBPC-MRXNPFEDSA-N 0.000 claims 4
- ZRXYEXRHPSYMDY-MRXNPFEDSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(dimethoxymethyl)pyrazin-2-yl]propanamide Chemical compound C1=NC(C(OC)OC)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 ZRXYEXRHPSYMDY-MRXNPFEDSA-N 0.000 claims 4
- KFAOCUVRWMNQHM-QGZVFWFLSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(methanesulfonamido)pyridin-2-yl]propanamide Chemical compound N1=CC(NS(=O)(=O)C)=CC=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 KFAOCUVRWMNQHM-QGZVFWFLSA-N 0.000 claims 4
- OJWKFRQGNQMXJY-HXUWFJFHSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-[3-(dimethylamino)prop-1-ynyl]pyrazin-2-yl]propanamide Chemical compound C1=NC(C#CCN(C)C)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 OJWKFRQGNQMXJY-HXUWFJFHSA-N 0.000 claims 4
- BMOGJRFSZYYMPK-HXUWFJFHSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-[3-(dimethylamino)propyl]pyrazin-2-yl]propanamide Chemical compound C1=NC(CCCN(C)C)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 BMOGJRFSZYYMPK-HXUWFJFHSA-N 0.000 claims 4
- BCTONCKQOYIUPK-CQSZACIVSA-N (2r)-n-[5-(5-amino-1,2,4-oxadiazol-3-yl)pyrazin-2-yl]-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(=NC=1)C=1N=C(N)ON=1)CC1CCCC1 BCTONCKQOYIUPK-CQSZACIVSA-N 0.000 claims 4
- DVSOMGQPQXDSTH-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-(5-formylpyrazin-2-yl)propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC(C=O)=NC=1)CC1CCCC1 DVSOMGQPQXDSTH-UHFFFAOYSA-N 0.000 claims 4
- MLHOQMZPSCAVOH-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]pyrazin-2-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC(CC2C(NC(=O)S2)=O)=NC=1)CC1CCCC1 MLHOQMZPSCAVOH-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- BPUNDRVIOJADLI-UHFFFAOYSA-N n-(5-acetylpyrazin-2-yl)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentylpropanamide Chemical compound C1=NC(C(=O)C)=CN=C1NC(=O)C(C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 BPUNDRVIOJADLI-UHFFFAOYSA-N 0.000 claims 4
- MGXHZTQMLYFNMR-CRAIPNDOSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-[(1s)-1,2-dihydroxyethyl]pyrazin-2-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(=NC=1)[C@H](O)CO)CC1CCCC1 MGXHZTQMLYFNMR-CRAIPNDOSA-N 0.000 claims 3
- RSWSKYSBRPWBFL-NNJIEVJOSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-n-[5-[cyano(hydroxy)methyl]pyrazin-2-yl]-3-cyclopentylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(=NC=1)C(O)C#N)CC1CCCC1 RSWSKYSBRPWBFL-NNJIEVJOSA-N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 229910052717 sulfur Chemical group 0.000 claims 3
- PIBVOMAOFIPNJU-OAHLLOKOSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(methanesulfonamido)pyrazin-2-yl]propanamide Chemical compound C1=NC(NS(=O)(=O)C)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 PIBVOMAOFIPNJU-OAHLLOKOSA-N 0.000 claims 2
- BPMWWFLXYFMFCH-MRXNPFEDSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(n'-hydroxycarbamimidoyl)pyridin-2-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(=CC=1)C(\N)=N/O)CC1CCCC1 BPMWWFLXYFMFCH-MRXNPFEDSA-N 0.000 claims 2
- DHTQDLARMJZTRI-MJTSIZKDSA-N (2r)-n-[5-(2-amino-1-hydroxy-2-oxoethyl)pyrazin-2-yl]-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(=NC=1)C(O)C(N)=O)CC1CCCC1 DHTQDLARMJZTRI-MJTSIZKDSA-N 0.000 claims 2
- LPTXOARRBIFFCR-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(1-hydroxyethyl)pyrazin-2-yl]propanamide Chemical compound C1=NC(C(O)C)=CN=C1NC(=O)C(C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 LPTXOARRBIFFCR-UHFFFAOYSA-N 0.000 claims 2
- LKHZSMIUTBLQBD-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-[(2,5-dioxoimidazolidin-4-yl)methyl]pyrazin-2-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC(CC2C(NC(=O)N2)=O)=NC=1)CC1CCCC1 LKHZSMIUTBLQBD-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 229940124828 glucokinase activator Drugs 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- BNAMDSLGAAEBSX-GOSISDBHSA-N (2R)-3-cyclopentyl-N-[5-(N-hydroxy-C-methylcarbonimidoyl)pyrazin-2-yl]-2-(4-methylsulfonylphenyl)propanamide Chemical compound C1=NC(C(=NO)C)=CN=C1NC(=O)[C@@H](C=1C=CC(=CC=1)S(C)(=O)=O)CC1CCCC1 BNAMDSLGAAEBSX-GOSISDBHSA-N 0.000 claims 1
- TZQZTAAKWYSXKV-OAQYLSRUSA-N (2r)-2-(3-chloro-2-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(3-methoxyphenyl)pyrazin-2-yl]propanamide Chemical compound COC1=CC=CC(C=2N=CC(NC(=O)[C@H](CC3CCCC3)C=3C(=C(Cl)C=CC=3)S(C)(=O)=O)=NC=2)=C1 TZQZTAAKWYSXKV-OAQYLSRUSA-N 0.000 claims 1
- MGXHZTQMLYFNMR-NNJIEVJOSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(1,2-dihydroxyethyl)pyrazin-2-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(=NC=1)C(O)CO)CC1CCCC1 MGXHZTQMLYFNMR-NNJIEVJOSA-N 0.000 claims 1
- XMKXCMYYWZBXNC-QGZVFWFLSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(1,3-dihydroxypropan-2-yl)pyrazin-2-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(=NC=1)C(CO)CO)CC1CCCC1 XMKXCMYYWZBXNC-QGZVFWFLSA-N 0.000 claims 1
- GLYXTTNIZPZZJQ-GOSISDBHSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(1,3-dioxolan-2-ylmethyl)pyrazin-2-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(CC2OCCO2)=NC=1)CC1CCCC1 GLYXTTNIZPZZJQ-GOSISDBHSA-N 0.000 claims 1
- NSCFSRADOKMZBF-GOSISDBHSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(2,2-dimethoxyethyl)pyrazin-2-yl]propanamide Chemical compound C1=NC(CC(OC)OC)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 NSCFSRADOKMZBF-GOSISDBHSA-N 0.000 claims 1
- QBHPRPNEIQLVPP-MRXNPFEDSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(2-hydroxyethylamino)pyrazin-2-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(NCCO)=NC=1)CC1CCCC1 QBHPRPNEIQLVPP-MRXNPFEDSA-N 0.000 claims 1
- CNVAJAVRHFZQPJ-QGZVFWFLSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(2-methoxyethylamino)pyrazin-2-yl]propanamide Chemical compound C1=NC(NCCOC)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 CNVAJAVRHFZQPJ-QGZVFWFLSA-N 0.000 claims 1
- KHJVZSPWNIRVSV-GOSISDBHSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(3,4-dihydro-2h-pyran-6-yl)pyrazin-2-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(=NC=1)C=1OCCCC=1)CC1CCCC1 KHJVZSPWNIRVSV-GOSISDBHSA-N 0.000 claims 1
- UPRQDMBDVXJVEB-LJQANCHMSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(3-hydroxy-3-methylbut-1-ynyl)pyrazin-2-yl]propanamide Chemical compound C1=NC(C#CC(C)(O)C)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 UPRQDMBDVXJVEB-LJQANCHMSA-N 0.000 claims 1
- MLELNNISKJTUDF-LJQANCHMSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(3-methoxyprop-1-ynyl)pyrazin-2-yl]propanamide Chemical compound C1=NC(C#CCOC)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 MLELNNISKJTUDF-LJQANCHMSA-N 0.000 claims 1
- HSLLSJONPLQLGR-MRXNPFEDSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(3-methyl-1,2,4-oxadiazol-5-yl)pyrazin-2-yl]propanamide Chemical compound CC1=NOC(C=2N=CC(NC(=O)[C@H](CC3CCCC3)C=3C=C(Cl)C(=CC=3)S(C)(=O)=O)=NC=2)=N1 HSLLSJONPLQLGR-MRXNPFEDSA-N 0.000 claims 1
- NDEHTNOQBFTMCS-LJQANCHMSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(4-hydroxybut-1-ynyl)pyrazin-2-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(=NC=1)C#CCCO)CC1CCCC1 NDEHTNOQBFTMCS-LJQANCHMSA-N 0.000 claims 1
- AJIOFORGXXYNQT-NKTHEXPSSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(4-methyl-2,5-dioxoimidazolidin-4-yl)pyrazin-2-yl]propanamide Chemical compound C=1N=C(NC(=O)[C@H](CC2CCCC2)C=2C=C(Cl)C(=CC=2)S(C)(=O)=O)C=NC=1C1(C)NC(=O)NC1=O AJIOFORGXXYNQT-NKTHEXPSSA-N 0.000 claims 1
- BMVVPZTYFXDVBE-QGZVFWFLSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(furan-2-yl)pyrazin-2-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(=NC=1)C=1OC=CC=1)CC1CCCC1 BMVVPZTYFXDVBE-QGZVFWFLSA-N 0.000 claims 1
- MHHLRNDLIDHPMN-QGZVFWFLSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(methylsulfanylmethyl)pyrazin-2-yl]propanamide Chemical compound C1=NC(CSC)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 MHHLRNDLIDHPMN-QGZVFWFLSA-N 0.000 claims 1
- WUBYGXHOAJQAQK-OYGDXLDBSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(methylsulfinylmethyl)pyrazin-2-yl]propanamide Chemical compound C1=NC(CS(=O)C)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 WUBYGXHOAJQAQK-OYGDXLDBSA-N 0.000 claims 1
- QOJCHOUNEOJSGO-QGZVFWFLSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(methylsulfonylmethyl)pyrazin-2-yl]propanamide Chemical compound C1=NC(CS(=O)(=O)C)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 QOJCHOUNEOJSGO-QGZVFWFLSA-N 0.000 claims 1
- BNPHFJXHGASNCQ-YMBRHYMPSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(oxolan-2-yl)pyridin-2-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(=CC=1)C1OCCC1)CC1CCCC1 BNPHFJXHGASNCQ-YMBRHYMPSA-N 0.000 claims 1
- FKOMCYQVYFWGPV-IIBYNOLFSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-[(1r)-1,2-dihydroxy-2-methylpropyl]pyrazin-2-yl]propanamide Chemical compound C1=NC([C@@H](O)C(C)(O)C)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 FKOMCYQVYFWGPV-IIBYNOLFSA-N 0.000 claims 1
- AREATSLFYVZJHZ-QZTJIDSGSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-[(2r)-2,3-dihydroxypropyl]pyrazin-2-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(C[C@@H](O)CO)=NC=1)CC1CCCC1 AREATSLFYVZJHZ-QZTJIDSGSA-N 0.000 claims 1
- VFRFXGJYDITECZ-GOSISDBHSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-[(dimethylamino)methyl]pyrazin-2-yl]propanamide Chemical compound C1=NC(CN(C)C)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 VFRFXGJYDITECZ-GOSISDBHSA-N 0.000 claims 1
- OQYHMFLYTKMGJW-OAQYLSRUSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-[2-(4-hydroxyoxan-4-yl)ethyl]pyrazin-2-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(CCC2(O)CCOCC2)=NC=1)CC1CCCC1 OQYHMFLYTKMGJW-OAQYLSRUSA-N 0.000 claims 1
- NEWXAIVVAQRVLU-GOSISDBHSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-n-[5-(5-cyanothiophen-2-yl)pyrazin-2-yl]-3-cyclopentylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(=NC=1)C=1SC(=CC=1)C#N)CC1CCCC1 NEWXAIVVAQRVLU-GOSISDBHSA-N 0.000 claims 1
- ZYABJVQMTAQRIB-QGZVFWFLSA-N (2r)-3-cyclopentyl-n-(5-methylsulfanylpyrazin-2-yl)-2-(4-methylsulfonylphenyl)propanamide Chemical compound C1=NC(SC)=CN=C1NC(=O)[C@@H](C=1C=CC(=CC=1)S(C)(=O)=O)CC1CCCC1 ZYABJVQMTAQRIB-QGZVFWFLSA-N 0.000 claims 1
- SQTLGFHTKAZHEB-OAQYLSRUSA-N (2r)-3-cyclopentyl-n-[5-(3-hydroxy-3-methylbut-1-ynyl)pyrazin-2-yl]-2-(3-methyl-4-methylsulfonylphenyl)propanamide Chemical compound C1=C(S(C)(=O)=O)C(C)=CC([C@@H](CC2CCCC2)C(=O)NC=2N=CC(=NC=2)C#CC(C)(C)O)=C1 SQTLGFHTKAZHEB-OAQYLSRUSA-N 0.000 claims 1
- KWJVACCSWSWVRJ-HSZRJFAPSA-N (2r)-3-cyclopentyl-n-[5-[2-(4-hydroxyoxan-4-yl)ethynyl]pyrazin-2-yl]-2-(3-methyl-4-methylsulfonylphenyl)propanamide Chemical compound C1=C(S(C)(=O)=O)C(C)=CC([C@@H](CC2CCCC2)C(=O)NC=2N=CC(=NC=2)C#CC2(O)CCOCC2)=C1 KWJVACCSWSWVRJ-HSZRJFAPSA-N 0.000 claims 1
- BPUNDRVIOJADLI-MRXNPFEDSA-N (2r)-n-(5-acetylpyrazin-2-yl)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentylpropanamide Chemical compound C1=NC(C(=O)C)=CN=C1NC(=O)[C@@H](C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 BPUNDRVIOJADLI-MRXNPFEDSA-N 0.000 claims 1
- IVDXEORRVXFJAW-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(5-methyl-1,2,4-oxadiazol-3-yl)pyrazin-2-yl]propanamide Chemical compound O1C(C)=NC(C=2N=CC(NC(=O)C(CC3CCCC3)C=3C=C(Cl)C(=CC=3)S(C)(=O)=O)=NC=2)=N1 IVDXEORRVXFJAW-UHFFFAOYSA-N 0.000 claims 1
- MHHLRNDLIDHPMN-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(methylsulfanylmethyl)pyrazin-2-yl]propanamide Chemical compound C1=NC(CSC)=CN=C1NC(=O)C(C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 MHHLRNDLIDHPMN-UHFFFAOYSA-N 0.000 claims 1
- FVQKGQNSCKJPIJ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCN2C(OCC2)=O)C=CC=1 FVQKGQNSCKJPIJ-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- CWABTKLTGPCPGM-UHFFFAOYSA-N C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC(=NC=1)C(=NO)C#N)CC1CCCC1 Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC(=NC=1)C(=NO)C#N)CC1CCCC1 CWABTKLTGPCPGM-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical group [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- CCXZTCBMMQQVHU-CQSZACIVSA-N chembl2338349 Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(=NC=1)C(=O)NO)CC1CCCC1 CCXZTCBMMQQVHU-CQSZACIVSA-N 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007721 medicinal effect Effects 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000003222 pyridines Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- QGTAFNSUDGNGRJ-UHFFFAOYSA-N CCC(C(N1)=O)SC1=O Chemical compound CCC(C(N1)=O)SC1=O QGTAFNSUDGNGRJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43280602P | 2002-12-12 | 2002-12-12 | |
| US60/432,806 | 2002-12-12 | ||
| US60/432.806 | 2002-12-12 | ||
| US52453103P | 2003-11-24 | 2003-11-24 | |
| US60/524,531 | 2003-11-24 | ||
| US60/524.531 | 2004-11-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2005121667A RU2005121667A (ru) | 2006-02-27 |
| RU2310648C2 true RU2310648C2 (ru) | 2007-11-20 |
Family
ID=32511672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2005121667/04A RU2310648C2 (ru) | 2002-12-12 | 2003-12-11 | 5-замещенные пиразиновые или пиридиновые активаторы глюкокиназы |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US7132425B2 (enExample) |
| EP (1) | EP1572670B1 (enExample) |
| JP (1) | JP4490285B2 (enExample) |
| KR (1) | KR100743890B1 (enExample) |
| AR (1) | AR046244A1 (enExample) |
| AT (1) | ATE370936T1 (enExample) |
| AU (1) | AU2003292229B2 (enExample) |
| BR (1) | BR0317268A (enExample) |
| CA (1) | CA2506441C (enExample) |
| CY (1) | CY1106989T1 (enExample) |
| DE (1) | DE60315886T2 (enExample) |
| DK (1) | DK1572670T3 (enExample) |
| ES (1) | ES2291697T3 (enExample) |
| HR (1) | HRP20050512A2 (enExample) |
| MX (1) | MXPA05006250A (enExample) |
| MY (1) | MY141521A (enExample) |
| NO (1) | NO330139B1 (enExample) |
| NZ (1) | NZ540298A (enExample) |
| PA (1) | PA8592001A1 (enExample) |
| PE (1) | PE20040801A1 (enExample) |
| PL (1) | PL377551A1 (enExample) |
| PT (1) | PT1572670E (enExample) |
| RU (1) | RU2310648C2 (enExample) |
| TW (1) | TW200426139A (enExample) |
| UY (1) | UY28121A1 (enExample) |
| WO (1) | WO2004052869A1 (enExample) |
Families Citing this family (90)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0102299D0 (sv) | 2001-06-26 | 2001-06-26 | Astrazeneca Ab | Compounds |
| SE0102764D0 (sv) | 2001-08-17 | 2001-08-17 | Astrazeneca Ab | Compounds |
| RU2005113713A (ru) | 2002-10-03 | 2006-01-20 | Новартис АГ (CH) | Замещенные (тиазол-2-ил)амиды или сульфонамиды в качестве активаторов глюкокиназы, которые могут применяться при лечении диабета типа 2 |
| GB0226930D0 (en) | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
| GB0226931D0 (en) | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
| JP4621198B2 (ja) * | 2003-02-11 | 2011-01-26 | プロシディオン・リミテッド | トリ(シクロ)置換アミドグルコキナーゼ活性化化合物 |
| ATE524479T1 (de) | 2004-04-02 | 2011-09-15 | Novartis Ag | Sulfonamidthiazolpyridinderivate als zur behandlung von typ-2-diabetes geeignete glucokinaseaktivatoren |
| WO2005095417A1 (en) | 2004-04-02 | 2005-10-13 | Novartis Ag | Thiazolopyridine derivates, pharmaceutical conditions containing them and methods of treating glucokinase mediated conditions |
| US8148412B2 (en) * | 2004-12-03 | 2012-04-03 | Novo Nordisk A/S | Heteroaromatic glucokinase activators |
| BRPI0622261A2 (pt) | 2005-07-09 | 2011-08-09 | Astrazeneca Ab | composto, composição farmacêutica, uso de um composto ou um sal farmaceuticamente aceitável do mesmo, e, processo para a preparação de um composto |
| BRPI0615236A2 (pt) * | 2005-08-31 | 2011-05-10 | Astellas Pharma Inc | derivado de tiazol |
| JP2007063225A (ja) * | 2005-09-01 | 2007-03-15 | Takeda Chem Ind Ltd | イミダゾピリジン化合物 |
| RU2008112198A (ru) | 2005-09-29 | 2009-10-10 | Санофи-Авентис (Fr) | Производные фенил-1,2,4-оксадиазолона, способы их получения и их применение в качестве фармацевтических средств |
| GT200600429A (es) * | 2005-09-30 | 2007-04-30 | Compuestos organicos | |
| GT200600428A (es) * | 2005-09-30 | 2007-05-21 | Compuestos organicos | |
| EP1948614A2 (en) * | 2005-11-18 | 2008-07-30 | Takeda San Diego, Inc. | Glucokinase activators |
| EP2001875A2 (en) | 2006-03-08 | 2008-12-17 | Takeda San Diego, Inc. | Glucokinase activators |
| US8211925B2 (en) * | 2006-04-28 | 2012-07-03 | Transtech Pharma, Inc. | Benzamide glucokinase activators |
| PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
| ATE522518T1 (de) | 2006-05-31 | 2011-09-15 | Takeda San Diego Inc | Indazol- und isoindolderivate als glucokinaseaktivierende stoffe |
| FR2903985B1 (fr) | 2006-07-24 | 2008-09-05 | Sanofi Aventis Sa | Derives de n-(amino-heteroaryl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique |
| BRPI0715531A2 (pt) | 2006-07-24 | 2014-06-24 | Hoffmann La Roche | Composto, composição farmacêutica, método para o tratamento de uma enfermidade e/ou distúrbio metabólico, processo para a preparação de compostos e uso do composto |
| FR2904316B1 (fr) | 2006-07-31 | 2008-09-05 | Sanofi Aventis Sa | Derives de n-(amino-heteroaryl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique. |
| US20080107725A1 (en) * | 2006-10-13 | 2008-05-08 | Albano Antonio A | Pharmaceutical Solid Dosage Forms Comprising Amorphous Compounds Micro-Embedded in Ionic Water-Insoluble Polymers |
| US7902248B2 (en) * | 2006-12-14 | 2011-03-08 | Hoffmann-La Roche Inc. | Oxime glucokinase activators |
| WO2008074694A1 (en) * | 2006-12-20 | 2008-06-26 | F. Hoffmann-La Roche Ag | Crystallization of glucokinase activators |
| US8163779B2 (en) | 2006-12-20 | 2012-04-24 | Takeda San Diego, Inc. | Glucokinase activators |
| TW200831081A (en) * | 2006-12-25 | 2008-08-01 | Kyorin Seiyaku Kk | Glucokinase activator |
| FR2910473B1 (fr) | 2006-12-26 | 2009-02-13 | Sanofi Aventis Sa | Derives de n-(amino-heteroaryl)-1h-pyrrolopyridine-2- carboxamides, leur preparation et leur application en therapeutique. |
| WO2008084872A1 (ja) | 2007-01-10 | 2008-07-17 | Mitsubishi Tanabe Pharma Corporation | ヒドラゾン誘導体 |
| DK2129654T3 (da) | 2007-02-09 | 2014-08-25 | Metabasis Therapeutics Inc | Antagonister af glucagonreceptoren |
| WO2008111473A1 (ja) * | 2007-03-07 | 2008-09-18 | Kyorin Pharmaceutical Co., Ltd. | グルコキナーゼ活性化物質 |
| WO2008116107A2 (en) * | 2007-03-21 | 2008-09-25 | Takeda San Diego, Inc. | Piperazine derivatives as glucokinase activators |
| CN101641447A (zh) | 2007-04-04 | 2010-02-03 | 霍夫曼-拉罗奇有限公司 | 乙酰氧基酮的微生物还原 |
| EP2148878A4 (en) * | 2007-04-20 | 2011-08-10 | Merck Canada Inc | NEW HETEROAROMATIC COMPOUNDS AS INHIBITORS OF STEAROYL-COENZYME-A-DELTA-9-DESATURASE |
| WO2009022179A2 (en) * | 2007-08-14 | 2009-02-19 | Astrazeneca Ab | Glucokinase activators in the treatment of osteoarthritis |
| CA2700783C (en) * | 2007-10-08 | 2015-03-17 | Advinus Therapeutics Private Limited | Acetamide derivatives as glucokinase activators, their process and medicinal applications |
| KR20100113518A (ko) | 2008-01-18 | 2010-10-21 | 아스텔라스세이야쿠 가부시키가이샤 | 페닐아세트아미드 유도체 |
| US8258134B2 (en) * | 2008-04-16 | 2012-09-04 | Hoffmann-La Roche Inc. | Pyridazinone glucokinase activators |
| US7741327B2 (en) * | 2008-04-16 | 2010-06-22 | Hoffmann-La Roche Inc. | Pyrrolidinone glucokinase activators |
| SI2275414T1 (sl) | 2008-04-28 | 2015-10-30 | Kyorin Pharmaceutical Co., Ltd., | Ciklopentilakrilamidni derivat |
| PL2799428T3 (pl) | 2008-08-13 | 2017-05-31 | Metabasis Therapeutics, Inc. | Antagoniści glukagonu |
| UA104742C2 (uk) * | 2008-12-19 | 2014-03-11 | Эли Лилли Энд Компани | Похідні арилциклопропілацетаміду, застосовні як активатори глюкокінази |
| US20110021570A1 (en) * | 2009-07-23 | 2011-01-27 | Nancy-Ellen Haynes | Pyridone glucokinase activators |
| US20110040091A1 (en) | 2009-08-13 | 2011-02-17 | Stephan Bachmann | Process for the preparation of (r)-2-phenyl propionic acid derivatives |
| US20110054174A1 (en) | 2009-08-28 | 2011-03-03 | Stephan Bachmann | Process for the preparation of a glucokinase activator compound |
| WO2011051478A1 (en) | 2009-10-30 | 2011-05-05 | Domain Therapeutics | Novel oxime derivatives and their use as allosteric modulators of metabotropic glutamate receptors |
| US8222416B2 (en) | 2009-12-14 | 2012-07-17 | Hoffmann-La Roche Inc. | Azaindole glucokinase activators |
| ES2893699T3 (es) | 2010-03-31 | 2022-02-09 | Scripps Research Inst | Reprogramación de células |
| JP2013523894A (ja) | 2010-04-14 | 2013-06-17 | ブリストル−マイヤーズ スクイブ カンパニー | 新規グルコキナーゼアクチベーターおよびその使用方法 |
| US8178689B2 (en) | 2010-06-17 | 2012-05-15 | Hoffman-La Roche Inc. | Tricyclic compounds |
| AR082590A1 (es) | 2010-08-12 | 2012-12-19 | Hoffmann La Roche | Inhibidores de la tirosina-quinasa de bruton |
| JP6041808B2 (ja) * | 2010-11-16 | 2016-12-14 | アセチロン ファーマシューティカルズ インコーポレイテッドAcetylon Pharmaceuticals,Inc. | 蛋白質脱アセチル化酵素抑制剤としてのピリミジン水酸基アミド化合物およびその利用方法 |
| US8470866B2 (en) | 2011-05-03 | 2013-06-25 | Hoffmann-La Roche Inc. | Isoindolinone derivatives |
| CA2853439A1 (en) | 2011-10-31 | 2013-05-10 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| CA2855019A1 (en) | 2011-10-31 | 2013-05-10 | Xenon Pharmaceuticals Inc. | Biaryl ether sulfonamides and their use as therapeutic agents |
| WO2013177224A1 (en) | 2012-05-22 | 2013-11-28 | Genentech, Inc. | N-substituted benzamides and their use in the treatment of pain |
| BR112015000187A2 (pt) * | 2012-07-06 | 2017-06-27 | Genentech Inc | benzamidas substituídas com n e métodos de uso das mesmas |
| BR112015022488A2 (pt) | 2013-03-14 | 2017-07-18 | Genentech Inc | triazolopiridinas substituídas e métodos de uso das mesmas |
| EP2970156B1 (en) | 2013-03-15 | 2018-07-25 | Genentech, Inc. | Substituted benzoxazoles and methods of use thereof |
| AU2014309251B2 (en) | 2013-08-23 | 2018-05-24 | Parion Sciences, Inc. | Dithiol mucolytic agents |
| US9403779B2 (en) | 2013-10-08 | 2016-08-02 | Acetylon Pharmaceuticals, Inc. | Combinations of histone deacetylase inhibitors and either Her2 inhibitors or PI3K inhibitors |
| EP3055299B1 (en) | 2013-10-10 | 2021-01-06 | Acetylon Pharmaceuticals, Inc. | Pyrimidine hydroxy amide compounds as histone deacetylase inhibitors |
| JP2016534069A (ja) | 2013-10-24 | 2016-11-04 | メイヨ・ファウンデーション・フォー・メディカル・エデュケーション・アンド・リサーチ | Hdac6阻害剤での多嚢胞性疾患の治療 |
| JP6383418B2 (ja) | 2013-11-27 | 2018-08-29 | ジェネンテック, インコーポレイテッド | 置換ベンズアミド及びその使用方法 |
| EP2878339A1 (en) | 2013-12-02 | 2015-06-03 | Siena Biotech S.p.A. | SIP3 antagonists |
| US9949972B2 (en) | 2013-12-03 | 2018-04-24 | Acetylon Pharmaceuticals, Inc | Combinations of histone deacetylase inhibitors and immunomodulatory drugs |
| US9464073B2 (en) | 2014-02-26 | 2016-10-11 | Acetylon Pharmaceuticals, Inc. | Pyrimidine hydroxy amide compounds as HDAC6 selective inhibitors |
| JP2017519000A (ja) | 2014-06-12 | 2017-07-13 | リガンド・ファーマシューティカルズ・インコーポレイテッド | グルカゴンアンタゴニスト |
| EP3166939B1 (en) | 2014-07-07 | 2019-06-05 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| EP3166603B1 (en) | 2014-07-07 | 2020-02-12 | Acetylon Pharmaceuticals, Inc. | Treatment of leukemia with histone deacetylase inhibitors |
| EP3186257B1 (en) | 2014-08-27 | 2019-02-06 | Prexton Therapeutics SA | Novel chromone oxime derivative and its use as allosteric modulator of metabotropic glutamate receptors |
| CA2969790A1 (en) | 2014-12-05 | 2016-06-09 | University of Modena and Reggio Emilia | Combinations of histone deacetylase inhibitors and bendamustine |
| CA2974210A1 (en) * | 2015-01-30 | 2016-08-04 | Parion Sciences, Inc. | Novel monothiol mucolytic agents |
| CA2984424A1 (en) | 2015-04-30 | 2016-11-03 | Parion Sciences, Inc. | Novel prodrugs of dithiol mucolytic agents |
| CR20170591A (es) | 2015-05-22 | 2018-05-07 | Genentech Inc | Benzamidas sustituidas y métodos para utilizarlas |
| US10272084B2 (en) | 2015-06-01 | 2019-04-30 | Regenacy Pharmaceuticals, Llc | Histone deacetylase 6 selective inhibitors for the treatment of cisplatin-induced peripheral neuropathy |
| EP3341353A1 (en) | 2015-08-27 | 2018-07-04 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| HRP20192250T1 (hr) | 2015-08-27 | 2020-05-15 | Prexton Therapeutics Sa | Derivat kromon oksima koji prodire u mozak za liječenje diskinezije uzrokovane levodopom |
| PE20181003A1 (es) | 2015-09-28 | 2018-06-26 | Genentech Inc | Compuestos terapeuticos y sus metodos de uso |
| WO2017091592A1 (en) | 2015-11-25 | 2017-06-01 | Genentech, Inc. | Substituted benzamides useful as sodium channel blockers |
| EP3436432B1 (en) | 2016-03-30 | 2021-01-27 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| JP2019515909A (ja) | 2016-04-19 | 2019-06-13 | アセチロン ファーマシューティカルズ インコーポレイテッドAcetylon Pharmaceuticals,Inc. | 慢性リンパ性白血病の治療を目的とするhdac阻害剤単独またはbtk阻害剤との配合物 |
| JP7072557B2 (ja) | 2016-07-22 | 2022-05-20 | ブリストル-マイヤーズ スクイブ カンパニー | グルコキナーゼ活性化剤およびその使用方法 |
| MA46546A (fr) | 2016-10-17 | 2021-05-05 | Genentech Inc | Composés thérapeutiques et leurs procédés d'utilisation |
| EP3601273B1 (en) | 2017-03-24 | 2021-12-01 | Genentech, Inc. | 4-piperidin-n-(pyrimidin-4-yl)chroman-7-sulfonamide derivatives as sodium channel inhibitors |
| WO2019160940A1 (en) | 2018-02-13 | 2019-08-22 | Ligand Pharmaceuticals Incorporated | Glucagon receptor antagonists |
| WO2019165290A1 (en) | 2018-02-26 | 2019-08-29 | Genentech, Inc. | Pyridine-sulfonamide compounds and their use against pain and related conditions |
| CN111936494A (zh) | 2018-03-30 | 2020-11-13 | 豪夫迈·罗氏有限公司 | 作为钠通道抑制剂的取代的氢-吡啶并-吖嗪 |
| TW202003490A (zh) | 2018-05-22 | 2020-01-16 | 瑞士商赫孚孟拉羅股份公司 | 治療性化合物及其使用方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2186773C2 (ru) * | 1997-07-17 | 2002-08-10 | Рон-Пуленк Роре С.А. | Гипогликемическое лекарственное средство, содержащее полигидроксибутилпиразины, новые полигидроксибутилпиразины и способы их получения |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE249241C (enExample) | 1910-05-01 | 1912-07-13 | ||
| US3431301A (en) | 1966-03-24 | 1969-03-04 | Hoffmann La Roche | Process for producing methylhydrazine derivatives |
| US3776917A (en) | 1972-06-05 | 1973-12-04 | Schering Corp | 2-amino-6-phenalkyl-aminopyridines and derivatives thereof |
| ES419319A1 (es) | 1973-10-04 | 1976-03-01 | Gallardo Antonio Sa | Un procedimiento para la obtencion de derivados de acidos 3-benzoilfenilalcanoicos. |
| GB8909574D0 (en) | 1989-04-26 | 1989-06-14 | Ici Plc | Chemical process |
| US5169951A (en) | 1990-04-23 | 1992-12-08 | Ciba-Geigy Corporation | Process for preparing nematicidal compositions |
| DE69322118T2 (de) | 1992-04-17 | 1999-05-20 | Hodogaya Chemical Co., Ltd., Tokio/Tokyo | Amino-Thiazolderivate und ihre Anwendung als Fungizide |
| US5556859A (en) | 1994-12-22 | 1996-09-17 | Dowelanco | N-(4-pyrimidinyl)amide pesticides |
| GB9823871D0 (en) | 1998-10-30 | 1998-12-23 | Pharmacia & Upjohn Spa | 2-Amino-thiazole derivatives, process for their preparation, and their use as antitumour agents |
| RU2242469C2 (ru) | 1999-03-29 | 2004-12-20 | Ф.Хоффманн-Ля Рош Аг | Активаторы глюкокиназы |
| US6320050B1 (en) | 1999-03-29 | 2001-11-20 | Hoffmann-La Roche Inc. | Heteroaromatic glucokinase activators |
| CN1151140C (zh) * | 1999-03-29 | 2004-05-26 | 霍夫曼-拉罗奇有限公司 | 葡糖激酶活化剂 |
| US6610846B1 (en) | 1999-03-29 | 2003-08-26 | Hoffman-La Roche Inc. | Heteroaromatic glucokinase activators |
| US6353111B1 (en) | 1999-12-15 | 2002-03-05 | Hoffmann-La Roche Inc. | Trans olefinic glucokinase activators |
| CA2407416C (en) | 2000-05-03 | 2006-07-18 | Paige Erin Mahaney | Alkynyl phenyl heteroaromatic glucokinase activators |
| EP1280801B1 (en) * | 2000-05-03 | 2005-09-07 | F. Hoffmann-La Roche Ag | Hydantoin-containing glucokinase activators |
| EP1282611B1 (en) | 2000-05-08 | 2004-10-20 | F. Hoffmann-La Roche Ag | Substituted phenylacetamides and their use as glucokinase activators |
| US6489485B2 (en) | 2000-05-08 | 2002-12-03 | Hoffmann-La Roche Inc. | Para-amine substituted phenylamide glucokinase activators |
| ATE297907T1 (de) | 2000-07-20 | 2005-07-15 | Hoffmann La Roche | Alpha-acyl- und alpha-heteroatom-substituierte benzenacetamide verwendbar als glucokinase- aktivatoren |
| US6369232B1 (en) | 2000-08-15 | 2002-04-09 | Hoffmann-La Roche Inc. | Tetrazolyl-phenyl acetamide glucokinase activators |
| US6433188B1 (en) | 2000-12-06 | 2002-08-13 | Wendy Lea Corbett | Fused heteroaromatic glucokinase activators |
| JP4109111B2 (ja) | 2000-12-06 | 2008-07-02 | エフ.ホフマン−ラ ロシュ アーゲー | 縮合複素環式芳香族グルコキナーゼアクチベーター |
-
2003
- 2003-12-10 US US10/732,838 patent/US7132425B2/en not_active Expired - Fee Related
- 2003-12-10 MY MYPI20034740A patent/MY141521A/en unknown
- 2003-12-10 PE PE2003001259A patent/PE20040801A1/es not_active Application Discontinuation
- 2003-12-11 PA PA20038592001A patent/PA8592001A1/es unknown
- 2003-12-11 ES ES03767788T patent/ES2291697T3/es not_active Expired - Lifetime
- 2003-12-11 RU RU2005121667/04A patent/RU2310648C2/ru not_active IP Right Cessation
- 2003-12-11 AT AT03767788T patent/ATE370936T1/de active
- 2003-12-11 EP EP03767788A patent/EP1572670B1/en not_active Expired - Lifetime
- 2003-12-11 DK DK03767788T patent/DK1572670T3/da active
- 2003-12-11 AR ARP030104577A patent/AR046244A1/es unknown
- 2003-12-11 TW TW092135035A patent/TW200426139A/zh unknown
- 2003-12-11 UY UY28121A patent/UY28121A1/es not_active Application Discontinuation
- 2003-12-11 KR KR1020057010528A patent/KR100743890B1/ko not_active Expired - Fee Related
- 2003-12-11 DE DE60315886T patent/DE60315886T2/de not_active Expired - Lifetime
- 2003-12-11 JP JP2004558065A patent/JP4490285B2/ja not_active Expired - Fee Related
- 2003-12-11 PL PL377551A patent/PL377551A1/pl not_active Application Discontinuation
- 2003-12-11 HR HR20050512A patent/HRP20050512A2/hr not_active Application Discontinuation
- 2003-12-11 AU AU2003292229A patent/AU2003292229B2/en not_active Ceased
- 2003-12-11 CA CA002506441A patent/CA2506441C/en not_active Expired - Fee Related
- 2003-12-11 MX MXPA05006250A patent/MXPA05006250A/es active IP Right Grant
- 2003-12-11 BR BR0317268-6A patent/BR0317268A/pt not_active IP Right Cessation
- 2003-12-11 WO PCT/EP2003/014055 patent/WO2004052869A1/en not_active Ceased
- 2003-12-11 NZ NZ540298A patent/NZ540298A/en not_active IP Right Cessation
- 2003-12-11 PT PT03767788T patent/PT1572670E/pt unknown
-
2005
- 2005-05-26 NO NO20052555A patent/NO330139B1/no not_active IP Right Cessation
-
2007
- 2007-11-08 CY CY20071101430T patent/CY1106989T1/el unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2186773C2 (ru) * | 1997-07-17 | 2002-08-10 | Рон-Пуленк Роре С.А. | Гипогликемическое лекарственное средство, содержащее полигидроксибутилпиразины, новые полигидроксибутилпиразины и способы их получения |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2310648C2 (ru) | 5-замещенные пиразиновые или пиридиновые активаторы глюкокиназы | |
| RU2419624C2 (ru) | Сульфонамидные производные как активаторы гликокиназы, применимые для лечения диабета типа 2 | |
| EP3740481B1 (en) | Dihydrobenzofuran and inden analogs as cardiac sarcomere inhibitors | |
| ES2534392T3 (es) | Inhibidores de la proteína tirosina fosfatasa humana y métodos de uso | |
| US11634395B2 (en) | Sulfonamide compound or salt thereof | |
| KR890005095A (ko) | 신규 화합물들 | |
| KR102564925B1 (ko) | 안드로겐 수용체의 표적화된 분해를 위한 화합물 및 방법 | |
| RU2203897C2 (ru) | Производные бензамидина, способ их получения, фармацевтическая композиция, способ ее получения и лекарственное средство | |
| RU2218337C2 (ru) | Производные тиазола, способ их получения и фармацевтическая композиция на их основе | |
| RU2001130169A (ru) | Производные карбаминовой кислоты и их применение в качестве лигандов метаботропных глутаматных рецепторов | |
| CN1152870A (zh) | 杂环化合物作为多巴胺d3配位体的用途 | |
| KR920002586A (ko) | 신규 인돌 유도체 | |
| RU95118133A (ru) | Гетероциклические соединения, способы их получения и фармацевтическая композиция | |
| BRPI0718895A2 (pt) | Composto de sulfoximina e uso do referido composto | |
| US20060089353A1 (en) | Indole derivative compounds and drugs containing the compounds as the active ingredient | |
| JP2005513026A5 (enExample) | ||
| JP2013516415A5 (enExample) | ||
| RU2006138433A (ru) | Сульфонамидтиазолпиридиновые производные как активаторы глюкокиназы, пригодные для лечения диабета типа 2 | |
| RU96111018A (ru) | Амиды терапевтического назначения | |
| KR910014373A (ko) | 인돌-치환된 5원 헤테로방향족 화합물 | |
| EA022458B1 (ru) | 1,3,4-оксадиазол-2-карбоксамидное соединение | |
| BR112012000370B1 (pt) | Compostos úteis como medicamentos | |
| JP2007519695A5 (enExample) | ||
| US10889555B2 (en) | Sulfonamide compound or salt thereof | |
| CA2617991A1 (en) | N-phenyl-2-pyrimidine-amine derivatives and process for the preparation thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20111212 |