ZA200504474B - 5-Substituted-pyrazine or pyridine glucokinase activators. - Google Patents
5-Substituted-pyrazine or pyridine glucokinase activators. Download PDFInfo
- Publication number
- ZA200504474B ZA200504474B ZA200504474A ZA200504474A ZA200504474B ZA 200504474 B ZA200504474 B ZA 200504474B ZA 200504474 A ZA200504474 A ZA 200504474A ZA 200504474 A ZA200504474 A ZA 200504474A ZA 200504474 B ZA200504474 B ZA 200504474B
- Authority
- ZA
- South Africa
- Prior art keywords
- cyclopentyl
- phenyl
- propionamide
- methanesulfonyl
- chloro
- Prior art date
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- -1 5-Substituted-pyrazine Chemical class 0.000 title claims description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 24
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims description 12
- 102000030595 Glucokinase Human genes 0.000 title description 21
- 108010021582 Glucokinase Proteins 0.000 title description 21
- 239000012190 activator Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 101
- 229940080818 propionamide Drugs 0.000 claims description 64
- 229910052799 carbon Inorganic materials 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 150000001721 carbon Chemical group 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- 229910052760 oxygen Chemical group 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 239000001301 oxygen Chemical group 0.000 claims description 13
- 239000011593 sulfur Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 8
- 101150065749 Churc1 gene Proteins 0.000 claims description 8
- 102100038239 Protein Churchill Human genes 0.000 claims description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 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 description 4
- 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 description 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 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 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
- 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
- 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 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 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 3
- 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 2
- 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 2
- 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 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
- 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 2
- RGCOLBLUBXBSDY-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(2-methylpropanoyl)pyrazin-2-yl]propanamide Chemical compound C1=NC(C(=O)C(C)C)=CN=C1NC(=O)C(C=1C=C(Cl)C(=CC=1)S(C)(=O)=O)CC1CCCC1 RGCOLBLUBXBSDY-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
- 229940125782 compound 2 Drugs 0.000 claims 2
- 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 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
- LKRYWWFJGDPNAI-QGZVFWFLSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-(5-thiophen-2-ylpyrazin-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=1SC=CC=1)CC1CCCC1 LKRYWWFJGDPNAI-QGZVFWFLSA-N 0.000 claims 1
- VAHRJRSQYMEOGT-GOSISDBHSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-(5-thiophen-3-ylpyrazin-2-yl)propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(=NC=1)C1=CSC=C1)CC1CCCC1 VAHRJRSQYMEOGT-GOSISDBHSA-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
- XNEHGKJPSHBDRO-MRXNPFEDSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(1,3-dioxolan-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)C1OCCO1)CC1CCCC1 XNEHGKJPSHBDRO-MRXNPFEDSA-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
- 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
- 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
- GJKVAFLVPCJHNN-GOSISDBHSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[5-(furan-3-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)C1=COC=C1)CC1CCCC1 GJKVAFLVPCJHNN-GOSISDBHSA-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
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 210000004738 parenchymal cell Anatomy 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 230000000291 postprandial effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000029964 regulation of glucose metabolic process Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43280602P | 2002-12-12 | 2002-12-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200504474B true ZA200504474B (en) | 2006-02-22 |
Family
ID=35925145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200504474A ZA200504474B (en) | 2002-12-12 | 2005-05-31 | 5-Substituted-pyrazine or pyridine glucokinase activators. |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN100469770C (zh) |
| GT (1) | GT200300283A (zh) |
| ZA (1) | ZA200504474B (zh) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8258134B2 (en) * | 2008-04-16 | 2012-09-04 | Hoffmann-La Roche Inc. | Pyridazinone glucokinase activators |
| BR112015000187A2 (pt) * | 2012-07-06 | 2017-06-27 | Genentech Inc | benzamidas substituídas com n e métodos de uso das mesmas |
| EP3101007A1 (en) * | 2015-06-05 | 2016-12-07 | Lead Pharma Cel Models IP B.V. | Ror gamma (rory) modulators |
| EP3101005A1 (en) * | 2015-06-05 | 2016-12-07 | Lead Pharma Cel Models IP B.V. | Ror gamma (rory) modulators |
| CN106187838B (zh) * | 2016-07-13 | 2018-05-01 | 广东东阳光药业有限公司 | 芳基炔烃类化合物及其制备方法和用途 |
-
2003
- 2003-12-11 GT GT200300283A patent/GT200300283A/es unknown
- 2003-12-11 CN CNB2003801058705A patent/CN100469770C/zh not_active Expired - Fee Related
-
2005
- 2005-05-31 ZA ZA200504474A patent/ZA200504474B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GT200300283A (es) | 2004-07-14 |
| CN100469770C (zh) | 2009-03-18 |
| CN1726197A (zh) | 2006-01-25 |
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