ZA200406685B - Heterocyclic amide derivatives having glycogen phosphorylase inhibitory activity. - Google Patents
Heterocyclic amide derivatives having glycogen phosphorylase inhibitory activity. Download PDFInfo
- Publication number
- ZA200406685B ZA200406685B ZA200406685A ZA200406685A ZA200406685B ZA 200406685 B ZA200406685 B ZA 200406685B ZA 200406685 A ZA200406685 A ZA 200406685A ZA 200406685 A ZA200406685 A ZA 200406685A ZA 200406685 B ZA200406685 B ZA 200406685B
- Authority
- ZA
- South Africa
- Prior art keywords
- thieno
- pyrrole
- amino
- inden
- dihydro
- Prior art date
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- -1 Heterocyclic amide Chemical class 0.000 title claims description 206
- 108010046163 Glycogen Phosphorylase Proteins 0.000 title description 13
- 102000007390 Glycogen Phosphorylase Human genes 0.000 title description 13
- 230000002401 inhibitory effect Effects 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 92
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 49
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 39
- 150000002148 esters Chemical class 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 31
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 238000001727 in vivo Methods 0.000 claims description 26
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229940002612 prodrug Drugs 0.000 claims description 11
- 239000000651 prodrug Substances 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 3
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 3
- 206010051161 Hyperglucagonaemia Diseases 0.000 claims description 3
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 3
- 206010022489 Insulin Resistance Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
- 230000035879 hyperinsulinaemia Effects 0.000 claims description 3
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 208000031225 myocardial ischemia Diseases 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 3
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- LUXLMNNGEKJWCH-UHFFFAOYSA-N tert-butyl n-[2-[(2,3-dichloro-4h-thieno[3,2-b]pyrrole-5-carbonyl)amino]-2,3-dihydro-1h-inden-1-yl]carbamate Chemical compound C1=CC=C2C(NC(=O)OC(C)(C)C)C(NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 LUXLMNNGEKJWCH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 3
- UYGMKKAFEMEBKS-UHFFFAOYSA-N 2,3-dichloro-n-(1-hydroxy-2,3-dihydro-1h-inden-2-yl)-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2C(O)C(NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 UYGMKKAFEMEBKS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- KYMXBGUBBFKNRL-UHFFFAOYSA-N n-(1-acetamido-2,3-dihydro-1h-inden-2-yl)-2,3-dichloro-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2C(NC(=O)C)C(NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 KYMXBGUBBFKNRL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 2
- 125000001441 L-beta-aspartyl group Chemical group N[C@@H](CC(=O)*)C(=O)O 0.000 claims 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 2
- XCBSAJSSBZHGPD-GLKRBJQHSA-N (2r)-2-amino-n'-[(1r,2r)-2-[(2,3-dichloro-4h-thieno[3,2-b]pyrrole-5-carbonyl)amino]-2,3-dihydro-1h-inden-1-yl]butanediamide Chemical compound C1=CC=C2[C@@H](NC(=O)C[C@@H](N)C(N)=O)[C@H](NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 XCBSAJSSBZHGPD-GLKRBJQHSA-N 0.000 claims 1
- ZFNOIXQHQDVNRZ-PBFPGSCMSA-N (2r)-2-amino-n'-[(1r,2r)-2-[(2-chloro-6h-thieno[2,3-b]pyrrole-5-carbonyl)amino]-2,3-dihydro-1h-inden-1-yl]butanediamide Chemical compound C1=CC=C2[C@@H](NC(=O)C[C@@H](N)C(N)=O)[C@H](NC(=O)C=3NC=4SC(Cl)=CC=4C=3)CC2=C1 ZFNOIXQHQDVNRZ-PBFPGSCMSA-N 0.000 claims 1
- OSKSLASJZCOWHQ-UHFFFAOYSA-N 2,3-dichloro-n-(1-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2C(O)C(NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CCC2=C1 OSKSLASJZCOWHQ-UHFFFAOYSA-N 0.000 claims 1
- XSFLJXAKVFBADZ-QMTHXVAHSA-N 2,3-dichloro-n-[(1r,2r)-1-(methanesulfonamido)-2,3-dihydro-1h-inden-2-yl]-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2[C@@H](NS(=O)(=O)C)[C@H](NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 XSFLJXAKVFBADZ-QMTHXVAHSA-N 0.000 claims 1
- ZFZVUFBCQMZCBZ-MEBBXXQBSA-N 2,3-dichloro-n-[(1r,2r)-1-[(2-chloroacetyl)amino]-2,3-dihydro-1h-inden-2-yl]-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2[C@@H](NC(=O)CCl)[C@H](NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 ZFZVUFBCQMZCBZ-MEBBXXQBSA-N 0.000 claims 1
- AJRXUFWVFCGJPC-MEBBXXQBSA-N 2,3-dichloro-n-[(1r,2r)-1-[(2-hydroxyacetyl)amino]-2,3-dihydro-1h-inden-2-yl]-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2[C@@H](NC(=O)CO)[C@H](NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 AJRXUFWVFCGJPC-MEBBXXQBSA-N 0.000 claims 1
- SRWVKGWFTHLWPD-NHYWBVRUSA-N 2,3-dichloro-n-[(1s,2s)-1-(dimethylcarbamoylamino)-2,3-dihydro-1h-inden-2-yl]-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2[C@H](NC(=O)N(C)C)[C@@H](NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 SRWVKGWFTHLWPD-NHYWBVRUSA-N 0.000 claims 1
- XSFLJXAKVFBADZ-HZMBPMFUSA-N 2,3-dichloro-n-[(1s,2s)-1-(methanesulfonamido)-2,3-dihydro-1h-inden-2-yl]-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2[C@H](NS(=O)(=O)C)[C@@H](NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 XSFLJXAKVFBADZ-HZMBPMFUSA-N 0.000 claims 1
- ROWSPRSFDUIEAD-ZBEGNZNMSA-N 2,3-dichloro-n-[(1s,2s)-1-(prop-2-enoylamino)-2,3-dihydro-1h-inden-2-yl]-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1C2=CC=CC=C2[C@H](NC(=O)C=C)[C@H]1NC(=O)C1=CC(SC(=C2Cl)Cl)=C2N1 ROWSPRSFDUIEAD-ZBEGNZNMSA-N 0.000 claims 1
- YTHSJIQCAGVWTI-KXBFYZLASA-N 2,3-dichloro-n-[(1s,2s)-1-[(3,5-dinitrophenyl)carbamoylamino]-2,3-dihydro-1h-inden-2-yl]-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC(NC(=O)N[C@H]2C3=CC=CC=C3C[C@@H]2NC(=O)C=2NC=3C(Cl)=C(Cl)SC=3C=2)=C1 YTHSJIQCAGVWTI-KXBFYZLASA-N 0.000 claims 1
- QDICTEPBHCXXLB-BTYIYWSLSA-N 2,3-dichloro-n-[(1s,2s)-1-[methyl-(2-morpholin-4-ylacetyl)amino]-2,3-dihydro-1h-inden-2-yl]-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound CN([C@H]1C2=CC=CC=C2C[C@@H]1NC(=O)C=1NC=2C(Cl)=C(Cl)SC=2C=1)C(=O)CN1CCOCC1 QDICTEPBHCXXLB-BTYIYWSLSA-N 0.000 claims 1
- IYYDMYCKWVOWAX-HZMBPMFUSA-N 2,3-dichloro-n-[(1s,2s)-1-formamido-2,3-dihydro-1h-inden-2-yl]-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1C2=CC=CC=C2[C@H](NC=O)[C@H]1NC(=O)C1=CC(SC(=C2Cl)Cl)=C2N1 IYYDMYCKWVOWAX-HZMBPMFUSA-N 0.000 claims 1
- XLQVFNKGWXIGIT-ADLMAVQZSA-N 2-[[(1r,2r)-2-[(2,3-dichloro-4h-thieno[3,2-b]pyrrole-5-carbonyl)amino]-2,3-dihydro-1h-inden-1-yl]-(2-hydroxyacetyl)amino]acetic acid Chemical compound C1=CC=C2[C@@H](N(CC(O)=O)C(=O)CO)[C@H](NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 XLQVFNKGWXIGIT-ADLMAVQZSA-N 0.000 claims 1
- BGMGXDMSAJJBOZ-MEBBXXQBSA-N 2-[[(1r,2r)-2-[(2,3-dichloro-4h-thieno[3,2-b]pyrrole-5-carbonyl)amino]-2,3-dihydro-1h-inden-1-yl]amino]acetic acid Chemical compound C1=CC=C2[C@@H](NCC(=O)O)[C@H](NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 BGMGXDMSAJJBOZ-MEBBXXQBSA-N 0.000 claims 1
- QHSQXULNOLARAB-QIIPPGSGSA-N 2-chloro-n-[(1r,2r)-1-[[(2s)-5-oxooxolane-2-carbonyl]amino]-2,3-dihydro-1h-inden-2-yl]-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound N([C@@H]1C2=CC=CC=C2C[C@H]1NC(=O)C1=CC=2C=C(SC=2N1)Cl)C(=O)[C@@H]1CCC(=O)O1 QHSQXULNOLARAB-QIIPPGSGSA-N 0.000 claims 1
- GPHKVNOYJPWARY-ANGYQSCVSA-N 2-chloro-n-[(1r,2r)-1-[[2-[2,3-dihydroxypropyl(methyl)amino]acetyl]amino]-2,3-dihydro-1h-inden-2-yl]-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2[C@@H](NC(=O)CN(CC(O)CO)C)[C@H](NC(=O)C=3NC=4SC(Cl)=CC=4C=3)CC2=C1 GPHKVNOYJPWARY-ANGYQSCVSA-N 0.000 claims 1
- ZMQTZJCMHGGLGL-DNVCBOLYSA-N 2-chloro-n-[(1r,2r)-1-[[2-[2-hydroxyethyl(methyl)amino]acetyl]amino]-2,3-dihydro-1h-inden-2-yl]-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2[C@@H](NC(=O)CN(CCO)C)[C@H](NC(=O)C=3NC=4SC(Cl)=CC=4C=3)CC2=C1 ZMQTZJCMHGGLGL-DNVCBOLYSA-N 0.000 claims 1
- XBBVIBNAZFKPBK-RHSMWYFYSA-N 2-chloro-n-[(1r,2r)-1-[[3-hydroxy-2-(hydroxymethyl)propanoyl]amino]-2,3-dihydro-1h-inden-2-yl]-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2[C@@H](NC(=O)C(CO)CO)[C@H](NC(=O)C=3NC=4SC(Cl)=CC=4C=3)CC2=C1 XBBVIBNAZFKPBK-RHSMWYFYSA-N 0.000 claims 1
- ABSBPDLMQGHOJQ-QFYYESIMSA-N 3-[[(1s,2s)-2-[(2,3-dichloro-4h-thieno[3,2-b]pyrrole-5-carbonyl)amino]-2,3-dihydro-1h-inden-1-yl]amino]-3-oxopropanoic acid Chemical compound C1=CC=C2[C@H](NC(=O)CC(=O)O)[C@@H](NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 ABSBPDLMQGHOJQ-QFYYESIMSA-N 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- CPVXCWYWGMSLGA-SJKOYZFVSA-N [2-[[(1r,2r)-2-[(2,3-dichloro-4h-thieno[3,2-b]pyrrole-5-carbonyl)amino]-2,3-dihydro-1h-inden-1-yl]amino]-2-oxoethyl] acetate Chemical compound C1=CC=C2[C@@H](NC(=O)COC(=O)C)[C@H](NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 CPVXCWYWGMSLGA-SJKOYZFVSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 1
- BMPQTOZEDDKBBV-UHFFFAOYSA-N n-(1-amino-2,3-dihydro-1h-inden-2-yl)-2,3-dichloro-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2C(N)C(NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 BMPQTOZEDDKBBV-UHFFFAOYSA-N 0.000 claims 1
- NSMZDHNBTSNNHA-MEBBXXQBSA-N n-[(1r,2r)-1-[(2-amino-2-oxoethyl)amino]-2,3-dihydro-1h-inden-2-yl]-2,3-dichloro-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2[C@@H](NCC(=O)N)[C@H](NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 NSMZDHNBTSNNHA-MEBBXXQBSA-N 0.000 claims 1
- PPUVAFUXOYLTFQ-MLGOLLRUSA-N n-[(1r,2r)-1-[(2-amino-2-oxoethyl)amino]-2,3-dihydro-1h-inden-2-yl]-2-chloro-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2[C@@H](NCC(=O)N)[C@H](NC(=O)C=3NC=4SC(Cl)=CC=4C=3)CC2=C1 PPUVAFUXOYLTFQ-MLGOLLRUSA-N 0.000 claims 1
- UISVWKQBNRVNBS-OXQOHEQNSA-N n-[(1r,2r)-1-[[2-[bis(2-hydroxyethyl)amino]acetyl]amino]-2,3-dihydro-1h-inden-2-yl]-2-chloro-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2[C@@H](NC(=O)CN(CCO)CCO)[C@H](NC(=O)C=3NC=4SC(Cl)=CC=4C=3)CC2=C1 UISVWKQBNRVNBS-OXQOHEQNSA-N 0.000 claims 1
- FKBKMHSZJVGODH-KZULUSFZSA-N n-[(1r,2r)-1-[acetyl-(2-amino-2-oxoethyl)amino]-2,3-dihydro-1h-inden-2-yl]-2,3-dichloro-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2[C@@H](N(CC(N)=O)C(=O)C)[C@H](NC(=O)C=3NC=4C(Cl)=C(Cl)SC=4C=3)CC2=C1 FKBKMHSZJVGODH-KZULUSFZSA-N 0.000 claims 1
- JCSCCJAPNICJOS-CZUORRHYSA-N n-[(1r,2r)-1-acetamido-2,3-dihydro-1h-inden-2-yl]-2-chloro-6h-thieno[2,3-b]pyrrole-5-carboxamide Chemical compound C1=CC=C2[C@@H](NC(=O)C)[C@H](NC(=O)C=3NC=4SC(Cl)=CC=4C=3)CC2=C1 JCSCCJAPNICJOS-CZUORRHYSA-N 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
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- 206010012601 diabetes mellitus Diseases 0.000 description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 4
- 102000051325 Glucagon Human genes 0.000 description 4
- 108060003199 Glucagon Proteins 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
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- 238000011005 laboratory method Methods 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
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- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
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- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical group O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 150000003890 succinate salts Chemical class 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000003419 tautomerization reaction Methods 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
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Child & Adolescent Psychology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0205170.4A GB0205170D0 (en) | 2002-03-06 | 2002-03-06 | Chemical compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200406685B true ZA200406685B (en) | 2005-10-31 |
Family
ID=9932334
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200406685A ZA200406685B (en) | 2002-03-06 | 2004-08-23 | Heterocyclic amide derivatives having glycogen phosphorylase inhibitory activity. |
Country Status (26)
Country | Link |
---|---|
US (1) | US7122567B2 (de) |
EP (1) | EP1483271B1 (de) |
JP (1) | JP2005524669A (de) |
KR (1) | KR20040091101A (de) |
CN (1) | CN1307183C (de) |
AR (1) | AR038886A1 (de) |
AT (1) | ATE346072T1 (de) |
AU (1) | AU2003209445A1 (de) |
BR (1) | BR0308145A (de) |
CA (1) | CA2477125A1 (de) |
DE (1) | DE60309849T2 (de) |
DK (1) | DK1483271T3 (de) |
ES (1) | ES2276092T3 (de) |
GB (1) | GB0205170D0 (de) |
HK (1) | HK1070365A1 (de) |
IL (1) | IL163802A0 (de) |
IS (1) | IS7433A (de) |
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NO (1) | NO20044033L (de) |
NZ (1) | NZ534684A (de) |
PL (1) | PL372772A1 (de) |
PT (1) | PT1483271E (de) |
RU (1) | RU2004125145A (de) |
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GB0205176D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
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2002
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- 2003-03-04 EP EP03743418A patent/EP1483271B1/de not_active Expired - Lifetime
- 2003-03-04 CN CNB038051249A patent/CN1307183C/zh not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
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CN1639167A (zh) | 2005-07-13 |
US20050131052A1 (en) | 2005-06-16 |
AR038886A1 (es) | 2005-02-02 |
GB0205170D0 (en) | 2002-04-17 |
TW200306176A (en) | 2003-11-16 |
PT1483271E (pt) | 2007-02-28 |
EP1483271B1 (de) | 2006-11-22 |
KR20040091101A (ko) | 2004-10-27 |
PL372772A1 (en) | 2005-08-08 |
RU2004125145A (ru) | 2005-06-10 |
WO2003074531A1 (en) | 2003-09-12 |
JP2005524669A (ja) | 2005-08-18 |
BR0308145A (pt) | 2004-12-07 |
CN1307183C (zh) | 2007-03-28 |
EP1483271A1 (de) | 2004-12-08 |
DE60309849T2 (de) | 2007-06-14 |
MXPA04008611A (es) | 2004-12-06 |
IS7433A (is) | 2004-09-01 |
HK1070365A1 (en) | 2005-06-17 |
ATE346072T1 (de) | 2006-12-15 |
NZ534684A (en) | 2006-02-24 |
NO20044033L (no) | 2004-11-25 |
ES2276092T3 (es) | 2007-06-16 |
DK1483271T3 (da) | 2007-02-19 |
IL163802A0 (en) | 2005-12-18 |
CA2477125A1 (en) | 2003-09-12 |
AU2003209445A1 (en) | 2003-09-16 |
DE60309849D1 (de) | 2007-01-04 |
US7122567B2 (en) | 2006-10-17 |
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