AU2006268589B2 - Urea glucokinase activators - Google Patents
Urea glucokinase activators Download PDFInfo
- Publication number
- AU2006268589B2 AU2006268589B2 AU2006268589A AU2006268589A AU2006268589B2 AU 2006268589 B2 AU2006268589 B2 AU 2006268589B2 AU 2006268589 A AU2006268589 A AU 2006268589A AU 2006268589 A AU2006268589 A AU 2006268589A AU 2006268589 B2 AU2006268589 B2 AU 2006268589B2
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- thiazol
- ureido
- cyclohexyl
- trans
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 102000030595 Glucokinase Human genes 0.000 title description 39
- 108010021582 Glucokinase Proteins 0.000 title description 39
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 7
- 239000012190 activator Substances 0.000 title description 7
- 239000004202 carbamide Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 241
- 238000011282 treatment Methods 0.000 claims abstract description 117
- 238000002360 preparation method Methods 0.000 claims abstract description 52
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 43
- 239000003814 drug Substances 0.000 claims abstract description 15
- -1 methoxy, methylthio, ethoxy, cyclopropyl-methoxy Chemical group 0.000 claims description 304
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 106
- 125000001424 substituent group Chemical group 0.000 claims description 102
- 238000000034 method Methods 0.000 claims description 90
- 239000000203 mixture Substances 0.000 claims description 67
- 108090001061 Insulin Proteins 0.000 claims description 50
- 102000004877 Insulin Human genes 0.000 claims description 50
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 50
- 229940125396 insulin Drugs 0.000 claims description 50
- 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 claims description 47
- 239000008103 glucose Substances 0.000 claims description 47
- 239000008194 pharmaceutical composition Substances 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 30
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 26
- 206010020772 Hypertension Diseases 0.000 claims description 26
- 239000008280 blood Substances 0.000 claims description 26
- 210000004369 blood Anatomy 0.000 claims description 26
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 25
- 208000008589 Obesity Diseases 0.000 claims description 23
- 235000020824 obesity Nutrition 0.000 claims description 23
- 206010012601 diabetes mellitus Diseases 0.000 claims description 22
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 21
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- 201000001421 hyperglycemia Diseases 0.000 claims description 13
- 206010056997 Impaired fasting glucose Diseases 0.000 claims description 12
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 11
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 208000011580 syndromic disease Diseases 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 230000001105 regulatory effect Effects 0.000 claims description 9
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 239000002552 dosage form Substances 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 230000037406 food intake Effects 0.000 claims description 8
- 235000012631 food intake Nutrition 0.000 claims description 8
- 235000021229 appetite regulation Nutrition 0.000 claims description 7
- 230000004634 feeding behavior Effects 0.000 claims description 7
- 230000028327 secretion Effects 0.000 claims description 7
- 230000002708 enhancing effect Effects 0.000 claims description 6
- 208000030159 metabolic disease Diseases 0.000 claims description 5
- 125000004710 2-methylpropylthio group Chemical group CC(CS*)C 0.000 claims description 4
- 208000031773 Insulin resistance syndrome Diseases 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 230000010030 glucose lowering effect Effects 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 230000000052 comparative effect Effects 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 28
- 201000010099 disease Diseases 0.000 abstract description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 514
- 229960000583 acetic acid Drugs 0.000 description 383
- 230000015572 biosynthetic process Effects 0.000 description 156
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 156
- 238000003786 synthesis reaction Methods 0.000 description 151
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 131
- 238000005481 NMR spectroscopy Methods 0.000 description 109
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 107
- QRIYTBYTQBRMNL-UHFFFAOYSA-N ethyl 2-[(2-amino-1,3-thiazol-5-yl)sulfanyl]acetate Chemical compound CCOC(=O)CSC1=CN=C(N)S1 QRIYTBYTQBRMNL-UHFFFAOYSA-N 0.000 description 77
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 67
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 65
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 57
- KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 description 56
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 46
- 229960001031 glucose Drugs 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 40
- 125000003118 aryl group Chemical group 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 35
- GDKRHCIXCFSWKN-UHFFFAOYSA-N 2-[[2-[[cyclohexyl(2-phenylethyl)carbamoyl]amino]-1,3-thiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=CN=C1NC(=O)N(C1CCCCC1)CCC1=CC=CC=C1 GDKRHCIXCFSWKN-UHFFFAOYSA-N 0.000 description 34
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
- 235000019260 propionic acid Nutrition 0.000 description 32
- 239000002904 solvent Substances 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 30
- 125000000217 alkyl group Chemical group 0.000 description 29
- 125000001072 heteroaryl group Chemical group 0.000 description 29
- 235000001727 glucose Nutrition 0.000 description 27
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- 239000012074 organic phase Substances 0.000 description 26
- 150000003254 radicals Chemical class 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- 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 23
- 239000002253 acid Substances 0.000 description 22
- 229910052736 halogen Inorganic materials 0.000 description 22
- 150000002367 halogens Chemical class 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
- VMLUPVHSIYWRJB-UHFFFAOYSA-N ethyl 2-[(2-amino-1,3-thiazol-5-yl)sulfanyl]propanoate Chemical compound CCOC(=O)C(C)SC1=CN=C(N)S1 VMLUPVHSIYWRJB-UHFFFAOYSA-N 0.000 description 20
- 235000019439 ethyl acetate Nutrition 0.000 description 20
- 235000013350 formula milk Nutrition 0.000 description 20
- 239000000460 chlorine Substances 0.000 description 19
- 230000002473 insulinotropic effect Effects 0.000 description 19
- 208000013016 Hypoglycemia Diseases 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 239000000556 agonist Substances 0.000 description 17
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- 230000001965 increasing effect Effects 0.000 description 16
- PBGKTOXHQIOBKM-FHFVDXKLSA-N insulin (human) Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3NC=NC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 PBGKTOXHQIOBKM-FHFVDXKLSA-N 0.000 description 16
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 16
- 235000019341 magnesium sulphate Nutrition 0.000 description 16
- MKCGLXWQSUNOCI-UHFFFAOYSA-N tert-butyl n-(3-hydroxypropyl)-n-(4-methylcyclohexyl)carbamate Chemical compound CC1CCC(N(CCCO)C(=O)OC(C)(C)C)CC1 MKCGLXWQSUNOCI-UHFFFAOYSA-N 0.000 description 16
- 101000976075 Homo sapiens Insulin Proteins 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 125000000623 heterocyclic group Chemical group 0.000 description 15
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- 238000003556 assay Methods 0.000 description 14
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- 150000002148 esters Chemical class 0.000 description 14
- 230000002218 hypoglycaemic effect Effects 0.000 description 14
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 14
- 229960003105 metformin Drugs 0.000 description 14
- 229960005419 nitrogen Drugs 0.000 description 14
- 238000010606 normalization Methods 0.000 description 14
- 125000004429 atom Chemical group 0.000 description 13
- 239000012043 crude product Substances 0.000 description 13
- 125000000753 cycloalkyl group Chemical group 0.000 description 13
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- 229960001519 exenatide Drugs 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
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- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 230000007062 hydrolysis Effects 0.000 description 11
- 238000006460 hydrolysis reaction Methods 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 11
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- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 10
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- PSKHNOASLUSHEP-UHFFFAOYSA-N ethyl 2-[(2-amino-1,3-thiazol-5-yl)sulfanyl]-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)SC1=CN=C(N)S1 PSKHNOASLUSHEP-UHFFFAOYSA-N 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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Classifications
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or 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
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
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- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2011265421A AU2011265421A1 (en) | 2005-07-14 | 2011-12-21 | Urea glucokinase activators |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05106449.1 | 2005-07-14 | ||
| EP05106449 | 2005-07-14 | ||
| PCT/EP2006/064289 WO2007006814A1 (en) | 2005-07-14 | 2006-07-14 | Urea glucokinase activators |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2011265421A Division AU2011265421A1 (en) | 2005-07-14 | 2011-12-21 | Urea glucokinase activators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2006268589A1 AU2006268589A1 (en) | 2007-01-18 |
| AU2006268589B2 true AU2006268589B2 (en) | 2011-09-29 |
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- 2006-07-14 RU RU2007147046/04A patent/RU2443691C2/ru not_active IP Right Cessation
- 2006-07-14 WO PCT/EP2006/064289 patent/WO2007006814A1/en not_active Ceased
- 2006-07-14 BR BRPI0612996-0A patent/BRPI0612996A2/pt not_active Application Discontinuation
- 2006-07-14 CA CA2615938A patent/CA2615938C/en not_active Expired - Fee Related
- 2006-07-14 EP EP11164386A patent/EP2377856A1/en not_active Withdrawn
- 2006-07-14 ES ES06777796T patent/ES2422383T3/es active Active
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- 2006-07-14 EP EP06777796.1A patent/EP1904467B1/en not_active Not-in-force
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- 2008-01-11 ZA ZA200800341A patent/ZA200800341B/xx unknown
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2010
- 2010-12-07 US US12/961,867 patent/US8586614B2/en active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2007006814A1 (en) | 2007-01-18 |
| MX2008000255A (es) | 2008-04-02 |
| JP2009501198A (ja) | 2009-01-15 |
| EP2377856A1 (en) | 2011-10-19 |
| KR101446973B1 (ko) | 2014-10-07 |
| CN101263131B (zh) | 2013-04-24 |
| CA2615938A1 (en) | 2007-01-18 |
| RU2443691C2 (ru) | 2012-02-27 |
| ZA200800341B (en) | 2008-12-31 |
| US20090105482A1 (en) | 2009-04-23 |
| US20110077234A1 (en) | 2011-03-31 |
| HK1121744A1 (en) | 2009-04-30 |
| RU2011144438A (ru) | 2013-05-10 |
| BRPI0612996A2 (pt) | 2010-12-14 |
| IL188244A0 (en) | 2008-04-13 |
| IL188244A (en) | 2012-12-31 |
| JP4960355B2 (ja) | 2012-06-27 |
| EP1904467B1 (en) | 2013-05-01 |
| ES2422383T3 (es) | 2013-09-11 |
| CA2615938C (en) | 2014-04-29 |
| NO20080746L (no) | 2008-03-26 |
| US7884210B2 (en) | 2011-02-08 |
| EP1904467A1 (en) | 2008-04-02 |
| AU2006268589A1 (en) | 2007-01-18 |
| US8586614B2 (en) | 2013-11-19 |
| RU2007147046A (ru) | 2009-08-20 |
| CN101263131A (zh) | 2008-09-10 |
| KR20080031047A (ko) | 2008-04-07 |
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