CA2526204A1 - Carbamates de pyridinyle utilises en tant qu'inhibiteurs de la lipase hormono-sensible - Google Patents
Carbamates de pyridinyle utilises en tant qu'inhibiteurs de la lipase hormono-sensible Download PDFInfo
- Publication number
- CA2526204A1 CA2526204A1 CA002526204A CA2526204A CA2526204A1 CA 2526204 A1 CA2526204 A1 CA 2526204A1 CA 002526204 A CA002526204 A CA 002526204A CA 2526204 A CA2526204 A CA 2526204A CA 2526204 A1 CA2526204 A1 CA 2526204A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- phenyl
- ester
- pyridin
- carbamic acid
- 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.)
- Abandoned
Links
- 102000000019 Sterol Esterase Human genes 0.000 title claims abstract description 40
- 108010055297 Sterol Esterase Proteins 0.000 title claims abstract description 40
- CYVBUBORVHPEGF-UHFFFAOYSA-N pyridin-2-yl carbamate Chemical class NC(=O)OC1=CC=CC=N1 CYVBUBORVHPEGF-UHFFFAOYSA-N 0.000 title abstract description 4
- 229940127470 Lipase Inhibitors Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 366
- 238000011282 treatment Methods 0.000 claims abstract description 52
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 47
- 230000000694 effects Effects 0.000 claims abstract description 10
- -1 hydroxy, sulfanyl Chemical group 0.000 claims description 331
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 186
- 125000003118 aryl group Chemical group 0.000 claims description 159
- 125000001072 heteroaryl group Chemical group 0.000 claims description 159
- 238000000034 method Methods 0.000 claims description 148
- 229910052736 halogen Inorganic materials 0.000 claims description 132
- 150000002367 halogens Chemical group 0.000 claims description 122
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 109
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 96
- GAUSUDNBBOZKSB-UHFFFAOYSA-N methyl(phenyl)carbamic acid Chemical compound OC(=O)N(C)C1=CC=CC=C1 GAUSUDNBBOZKSB-UHFFFAOYSA-N 0.000 claims description 96
- 125000001424 substituent group Chemical group 0.000 claims description 69
- 125000004043 oxo group Chemical group O=* 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 239000001257 hydrogen Substances 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 54
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 53
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 42
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 41
- 150000002431 hydrogen Chemical group 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 39
- OODYQULVZRKOPC-UHFFFAOYSA-N (5-aminopyridin-2-yl) n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC1=CC=C(N)C=N1 OODYQULVZRKOPC-UHFFFAOYSA-N 0.000 claims description 37
- 239000002904 solvent Substances 0.000 claims description 37
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 36
- 238000002360 preparation method Methods 0.000 claims description 35
- 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 34
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 29
- 230000002265 prevention Effects 0.000 claims description 28
- 208000035475 disorder Diseases 0.000 claims description 27
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical group NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 239000012453 solvate Substances 0.000 claims description 19
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- FWOMRZPIXSYBES-UHFFFAOYSA-N (5-benzamidopyridin-2-yl) n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1NC(=O)C1=CC=CC=C1 FWOMRZPIXSYBES-UHFFFAOYSA-N 0.000 claims description 17
- 102000004877 Insulin Human genes 0.000 claims description 17
- 108090001061 Insulin Proteins 0.000 claims description 17
- AYHDHCJHCUQUSA-UHFFFAOYSA-N [5-[(4-chlorobenzoyl)amino]pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 AYHDHCJHCUQUSA-UHFFFAOYSA-N 0.000 claims description 17
- QLSPDIBLJUWLNT-UHFFFAOYSA-N [5-[[4-(trifluoromethyl)benzoyl]amino]pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 QLSPDIBLJUWLNT-UHFFFAOYSA-N 0.000 claims description 17
- 229940125396 insulin Drugs 0.000 claims description 17
- YEIJNDQPDAHANR-UHFFFAOYSA-N [5-[(4-methoxybenzoyl)amino]pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C1=CC(OC)=CC=C1C(=O)NC(C=N1)=CC=C1OC(=O)N(C)C1=CC=CC=C1 YEIJNDQPDAHANR-UHFFFAOYSA-N 0.000 claims description 16
- 235000021588 free fatty acids Nutrition 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 16
- ORJJTNOPOUPVQG-UHFFFAOYSA-N [5-[[4-(chloromethyl)benzoyl]amino]pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1NC(=O)C1=CC=C(CCl)C=C1 ORJJTNOPOUPVQG-UHFFFAOYSA-N 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- CJLVTVBCRLVKTO-UHFFFAOYSA-N (5-isothiocyanatopyridin-2-yl) n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC1=CC=C(N=C=S)C=N1 CJLVTVBCRLVKTO-UHFFFAOYSA-N 0.000 claims description 14
- 206010022489 Insulin Resistance Diseases 0.000 claims description 14
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 12
- 239000004202 carbamide Chemical group 0.000 claims description 12
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 12
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 10
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 239000000194 fatty acid Substances 0.000 claims description 10
- 229930195729 fatty acid Natural products 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 9
- 201000010390 abdominal obesity-metabolic syndrome 1 Diseases 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 208000011661 metabolic syndrome X Diseases 0.000 claims description 9
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 9
- MIMUBMFBXTWCJB-UHFFFAOYSA-N 2-[[6-[methyl(phenyl)carbamoyl]oxypyridin-3-yl]amino]acetic acid Chemical compound C=1C=CC=CC=1N(C)C(=O)OC1=CC=C(NCC(O)=O)C=N1 MIMUBMFBXTWCJB-UHFFFAOYSA-N 0.000 claims description 8
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical group NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000008103 glucose Substances 0.000 claims description 8
- 230000005764 inhibitory process Effects 0.000 claims description 8
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 8
- 229960003105 metformin Drugs 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 208000008589 Obesity Diseases 0.000 claims description 7
- 239000000370 acceptor Substances 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 230000001105 regulatory effect Effects 0.000 claims description 7
- 150000003626 triacylglycerols Chemical class 0.000 claims description 7
- JAVDXUXPTJIYFU-UHFFFAOYSA-N [5-[[3-(dimethylamino)benzoyl]amino]pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound CN(C)C1=CC=CC(C(=O)NC=2C=NC(OC(=O)N(C)C=3C=CC=CC=3)=CC=2)=C1 JAVDXUXPTJIYFU-UHFFFAOYSA-N 0.000 claims description 6
- VSMPTDOSTZNCMF-UHFFFAOYSA-N [5-[[4-(pyrrolidin-1-ylmethyl)benzoyl]amino]pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1NC(=O)C(C=C1)=CC=C1CN1CCCC1 VSMPTDOSTZNCMF-UHFFFAOYSA-N 0.000 claims description 6
- 230000005856 abnormality Effects 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 230000003178 anti-diabetic effect Effects 0.000 claims description 6
- 230000036528 appetite Effects 0.000 claims description 6
- 235000019789 appetite Nutrition 0.000 claims description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Natural products C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 6
- 150000001982 diacylglycerols Chemical class 0.000 claims description 6
- 239000002552 dosage form Substances 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 201000001421 hyperglycemia Diseases 0.000 claims description 6
- 230000002366 lipolytic effect Effects 0.000 claims description 6
- 230000008604 lipoprotein metabolism Effects 0.000 claims description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
- MTBAAJSFYAYINP-UHFFFAOYSA-N (5-chloropyridin-2-yl) n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC1=CC=C(Cl)C=N1 MTBAAJSFYAYINP-UHFFFAOYSA-N 0.000 claims description 5
- AGMRFVYCHOXWPC-UHFFFAOYSA-N 2,2-dimethyl-4-[[6-[methyl(phenyl)carbamoyl]oxypyridin-3-yl]amino]-4-oxobutanoic acid Chemical compound C=1C=CC=CC=1N(C)C(=O)OC1=CC=C(NC(=O)CC(C)(C)C(O)=O)C=N1 AGMRFVYCHOXWPC-UHFFFAOYSA-N 0.000 claims description 5
- HMUPZDIBGDNGOM-UHFFFAOYSA-N 3,3-dimethyl-5-[[6-[methyl(phenyl)carbamoyl]oxypyridin-3-yl]amino]-5-oxopentanoic acid Chemical compound C=1C=CC=CC=1N(C)C(=O)OC1=CC=C(NC(=O)CC(C)(C)CC(O)=O)C=N1 HMUPZDIBGDNGOM-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 5
- ADNCXKFLHSCQFE-UHFFFAOYSA-N [3-chloro-5-(trifluoromethyl)pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC1=NC=C(C(F)(F)F)C=C1Cl ADNCXKFLHSCQFE-UHFFFAOYSA-N 0.000 claims description 5
- SVJGGSYMZFXXPA-UHFFFAOYSA-N [5-(2,2-dimethylpropanoylamino)pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC1=CC=C(NC(=O)C(C)(C)C)C=N1 SVJGGSYMZFXXPA-UHFFFAOYSA-N 0.000 claims description 5
- SYKCOLHKOJIPRT-UHFFFAOYSA-N [5-(2,2-dimethylpropylcarbamoyl)pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC1=CC=C(C(=O)NCC(C)(C)C)C=N1 SYKCOLHKOJIPRT-UHFFFAOYSA-N 0.000 claims description 5
- ILMIZADURHBSDS-UHFFFAOYSA-N [5-(2,5-dioxopyrrolidin-1-yl)pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1N1C(=O)CCC1=O ILMIZADURHBSDS-UHFFFAOYSA-N 0.000 claims description 5
- QLGUQWDGBBDIJU-UHFFFAOYSA-N [5-(2,6-dioxopiperidin-1-yl)pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1N1C(=O)CCCC1=O QLGUQWDGBBDIJU-UHFFFAOYSA-N 0.000 claims description 5
- GSVVIHFQHXHDNR-UHFFFAOYSA-N [5-(3,3-dimethyl-2,5-dioxopyrrolidin-1-yl)pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1N1C(=O)CC(C)(C)C1=O GSVVIHFQHXHDNR-UHFFFAOYSA-N 0.000 claims description 5
- CKNUWEFCKLNOQG-UHFFFAOYSA-N [5-(3,3-dimethylbutanoylamino)pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC1=CC=C(NC(=O)CC(C)(C)C)C=N1 CKNUWEFCKLNOQG-UHFFFAOYSA-N 0.000 claims description 5
- OYQGNRVZOCQJJY-UHFFFAOYSA-N [5-(4,4-dimethyl-2,6-dioxopiperidin-1-yl)pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1N1C(=O)CC(C)(C)CC1=O OYQGNRVZOCQJJY-UHFFFAOYSA-N 0.000 claims description 5
- NVLCNTSUCOOMRE-UHFFFAOYSA-N [5-(4,4-dimethylpiperidin-1-yl)pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1N1CCC(C)(C)CC1 NVLCNTSUCOOMRE-UHFFFAOYSA-N 0.000 claims description 5
- IRQYNMOTKZDEEO-UHFFFAOYSA-N [5-(benzenesulfonamido)pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1NS(=O)(=O)C1=CC=CC=C1 IRQYNMOTKZDEEO-UHFFFAOYSA-N 0.000 claims description 5
- FBVDOKAWBHUIMP-UHFFFAOYSA-N [5-(cyclohexanecarbonylamino)pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1NC(=O)C1CCCCC1 FBVDOKAWBHUIMP-UHFFFAOYSA-N 0.000 claims description 5
- IWHAIIZXJODOJG-UHFFFAOYSA-N [5-(pyridine-2-carbonylamino)pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1NC(=O)C1=CC=CC=N1 IWHAIIZXJODOJG-UHFFFAOYSA-N 0.000 claims description 5
- MMURDNLOOPRHOX-UHFFFAOYSA-N [5-(trifluoromethyl)pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC1=CC=C(C(F)(F)F)C=N1 MMURDNLOOPRHOX-UHFFFAOYSA-N 0.000 claims description 5
- KPKRIOIHVTVZFU-UHFFFAOYSA-N [5-[(2-cyclohexylacetyl)amino]pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1NC(=O)CC1CCCCC1 KPKRIOIHVTVZFU-UHFFFAOYSA-N 0.000 claims description 5
- JOFVWCNGGBADKA-UHFFFAOYSA-N [5-[(3,3-dimethyl-5-morpholin-4-yl-5-oxopentanoyl)amino]pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1NC(=O)CC(C)(C)CC(=O)N1CCOCC1 JOFVWCNGGBADKA-UHFFFAOYSA-N 0.000 claims description 5
- ULIPPHNMMSPFRU-UHFFFAOYSA-N [5-[[3,3-dimethyl-5-(4-methylpiperazin-1-yl)-5-oxopentanoyl]amino]pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1NC(=O)CC(C)(C)CC(=O)N1CCN(C)CC1 ULIPPHNMMSPFRU-UHFFFAOYSA-N 0.000 claims description 5
- HNQPMDUKTYSWKY-UHFFFAOYSA-N [5-[[3,3-dimethyl-5-oxo-5-(pyridin-3-ylamino)pentanoyl]amino]pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1NC(=O)CC(C)(C)CC(=O)NC1=CC=CN=C1 HNQPMDUKTYSWKY-UHFFFAOYSA-N 0.000 claims description 5
- RNFUDILWURPDQJ-UHFFFAOYSA-N [5-[[5-[2-(dimethylamino)ethylamino]-3,3-dimethyl-5-oxopentanoyl]amino]pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound N1=CC(NC(=O)CC(C)(C)CC(=O)NCCN(C)C)=CC=C1OC(=O)N(C)C1=CC=CC=C1 RNFUDILWURPDQJ-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000003472 antidiabetic agent Substances 0.000 claims description 5
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 5
- 235000012000 cholesterol Nutrition 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 238000007911 parenteral administration Methods 0.000 claims description 5
- JWGUZZSQJMTLKF-UHFFFAOYSA-N pyridin-2-yl n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC1=CC=CC=N1 JWGUZZSQJMTLKF-UHFFFAOYSA-N 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 4
- SPDGVUKIHUOYTG-UHFFFAOYSA-N [5-[(4-formylbenzoyl)amino]pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1NC(=O)C1=CC=C(C=O)C=C1 SPDGVUKIHUOYTG-UHFFFAOYSA-N 0.000 claims description 4
- HJYAKXNMMNTEAD-UHFFFAOYSA-N [5-[(4-nitrobenzoyl)amino]pyridin-2-yl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(N=C1)=CC=C1NC(=O)C1=CC=C([N+]([O-])=O)C=C1 HJYAKXNMMNTEAD-UHFFFAOYSA-N 0.000 claims description 4
- 210000000577 adipose tissue Anatomy 0.000 claims description 4
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Classifications
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- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
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- A—HUMAN NECESSITIES
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- 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
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- 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
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200300879 | 2003-06-12 | ||
| DKPA200300879 | 2003-06-12 | ||
| US47852603P | 2003-06-13 | 2003-06-13 | |
| US60/478,526 | 2003-06-13 | ||
| PCT/DK2004/000391 WO2004111031A1 (fr) | 2003-06-12 | 2004-06-08 | Carbamates de pyridinyle utilises en tant qu'inhibiteurs de la lipase hormono-sensible |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2526204A1 true CA2526204A1 (fr) | 2004-12-23 |
Family
ID=33553690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002526204A Abandoned CA2526204A1 (fr) | 2003-06-12 | 2004-06-08 | Carbamates de pyridinyle utilises en tant qu'inhibiteurs de la lipase hormono-sensible |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1636205A1 (fr) |
| JP (1) | JP2006527210A (fr) |
| KR (1) | KR20060017791A (fr) |
| AU (1) | AU2004247319A1 (fr) |
| BR (1) | BRPI0411255A (fr) |
| CA (1) | CA2526204A1 (fr) |
| MX (1) | MXPA05013224A (fr) |
| NO (1) | NO20060168L (fr) |
| RU (1) | RU2337908C2 (fr) |
| WO (1) | WO2004111031A1 (fr) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050026844A1 (en) | 2003-04-03 | 2005-02-03 | Regents Of The University Of California | Inhibitors for the soluble epoxide hydrolase |
| EP1765311A4 (fr) | 2004-03-16 | 2009-04-29 | Univ California | Reduction de la nephropathie au moyen d'inhibiteurs d'hydrolase d'epoxyde soluble et d'epoxyeicosanoides |
| CA2584342C (fr) | 2004-10-20 | 2013-04-30 | The Regents Of The University Of California | Inhibiteurs ameliores de l'epoxyde hydrolase soluble |
| WO2006087308A1 (fr) * | 2005-02-15 | 2006-08-24 | Novo Nordisk A/S | Ester et sels d'acide methylphenylcarbamique 5-(4-isobutyl-2,6,-dioxopiperazine-l-yl) pyridinyle-2-yl comme inhibiteurs de lipase hormonosensible |
| US7709517B2 (en) | 2005-05-13 | 2010-05-04 | The Regents Of The University Of California | Diarylhydantoin compounds |
| KR20080090381A (ko) * | 2005-08-29 | 2008-10-08 | 제라드 엠. 하우지 | 테라뮤틴 조절물질 |
| AR059826A1 (es) * | 2006-03-13 | 2008-04-30 | Univ California | Inhibidores de urea conformacionalmente restringidos de epoxido hidrolasa soluble |
| LT2656841T (lt) | 2006-03-27 | 2016-09-26 | The Regents Of The University Of California | Androgeno receptoriaus moduliatorius, skirtas prostatos vėžio ir su androgeno receptoriumi susijusių ligų gydymui |
| AU2013205325B2 (en) * | 2006-03-27 | 2016-03-24 | The Regents Of The University Of California | Androgen receptor modulator for the treatment of prostate cancer and androgen receptor-associated diseases |
| AU2016201061B2 (en) * | 2006-03-27 | 2017-03-02 | The Regents Of The University Of California | Androgen receptor modulator for the treatment of prostate cancer and androgen receptor-associated diseases |
| MX2008012492A (es) | 2006-03-29 | 2008-12-12 | Univ California | Compuestos de diariltiohidantoina. |
| TW200820970A (en) * | 2006-09-21 | 2008-05-16 | Nicholas Piramal India Ltd | Compounds for the treatment of metabolic disorders |
| FR2912404B1 (fr) | 2007-02-09 | 2009-04-10 | Sanofi Aventis Sa | Derives d'azabicycloalkane,leur preparation et leur application en therapeutique. |
| US8680291B2 (en) | 2007-10-26 | 2014-03-25 | The Regents Of The University Of California | Diarylhydantoin compounds |
| CN102439008B (zh) | 2009-05-12 | 2015-04-29 | 杨森制药有限公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其用于治疗或预防神经和精神病症的用途 |
| EP2528604B1 (fr) | 2010-01-29 | 2017-11-22 | The Regents of the University of California | Inhibiteurs d'acyl pipéridine d'époxyde hydrolase soluble |
| AU2011218173C1 (en) | 2010-02-16 | 2015-04-16 | Aragon Pharmaceuticals, Inc. | Androgen receptor modulators and uses thereof |
| HRP20171665T1 (hr) | 2011-12-28 | 2017-12-15 | Global Blood Therapeutics, Inc. | Supstituirani spojevi benzaldehida i metode za njihovu primjenu u povećanju oksigenacije tkiva |
| HK1203412A1 (en) | 2011-12-28 | 2015-10-30 | Global Blood Therapeutics, Inc. | Substituted heteroaryl aldehyde compounds and methods for their use in increasing tissue oxygenation |
| UA117663C2 (uk) | 2012-09-26 | 2018-09-10 | Арагон Фармасьютікалз, Інк. | Антиандроген для лікування неметастатичного кастраційно-резистентного раку передміхурової залози |
| JOP20200097A1 (ar) | 2013-01-15 | 2017-06-16 | Aragon Pharmaceuticals Inc | معدل مستقبل أندروجين واستخداماته |
| US10100043B2 (en) | 2013-03-15 | 2018-10-16 | Global Blood Therapeutics, Inc. | Substituted aldehyde compounds and methods for their use in increasing tissue oxygenation |
| EP2970308B1 (fr) | 2013-03-15 | 2021-07-14 | Global Blood Therapeutics, Inc. | Composés et leurs utilisations pour la modulation de l'hémoglobine |
| US9422279B2 (en) | 2013-03-15 | 2016-08-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US8952171B2 (en) | 2013-03-15 | 2015-02-10 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| CA2902711C (fr) | 2013-03-15 | 2021-07-06 | Global Blood Therapeutics, Inc. | Derives de pyridinyl-6-methoxy-2-hydroxybenzaldehyde substitues et compositions pharmaceutiques de ceux-ci pour utilisation dans la modulation de l'hemoglobine |
| US9458139B2 (en) | 2013-03-15 | 2016-10-04 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| PE20161035A1 (es) | 2013-03-15 | 2016-11-13 | Global Blood Therapeutics Inc | Compuestos y usos de estos para la modulacion de la hemoglobina |
| US10266551B2 (en) | 2013-03-15 | 2019-04-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| IL266301B2 (en) * | 2013-04-12 | 2023-03-01 | Obschestvo S Ogranichennoi Otvetstvennostiyu Pharmenterprises | History of glutarimide, their use, pharmaceutical preparation based on them and methods for producing history of glutarimide |
| UA119247C2 (uk) | 2013-09-06 | 2019-05-27 | РОЙВЕНТ САЙЕНСИЗ ҐмбГ | Спіроциклічні сполуки як інгібітори триптофангідроксилази |
| EA201992707A1 (ru) | 2013-11-18 | 2020-06-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| WO2015089137A1 (fr) | 2013-12-11 | 2015-06-18 | Karos Pharmaceuticals, Inc. | Acylguanidines comme inhibiteurs de la tryptophan hydroxylase |
| AP2016009261A0 (en) | 2014-02-07 | 2016-06-30 | Global Blood Therapeutics Inc | Crystalline polymorphs of the free base of 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde |
| WO2016109501A1 (fr) | 2014-12-30 | 2016-07-07 | Karos Pharmaceuticals, Inc. | Composés amides utilisés en tant qu'inhibiteurs de la tryptophane hydroxylase |
| US9611201B2 (en) | 2015-03-05 | 2017-04-04 | Karos Pharmaceuticals, Inc. | Processes for preparing (R)-1-(5-chloro-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethanol and 1-(5-chloro-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethanone |
| DK3383392T3 (da) | 2015-12-04 | 2025-08-18 | Global Blood Therapeutics Inc | Doseringsskema for 2.HYDROXY.6.((2.(1.ISOPROPYL.1H.PYRAZOL.5.YL)PYRIDIN.3.YL)METHOXY)BENZALDEHYD |
| TWI726969B (zh) | 2016-01-11 | 2021-05-11 | 比利時商健生藥品公司 | 用作雄性激素受體拮抗劑之經取代之硫尿囊素衍生物 |
| TWI752307B (zh) | 2016-05-12 | 2022-01-11 | 美商全球血液治療公司 | 新穎化合物及製造化合物之方法 |
| TW202332423A (zh) | 2016-10-12 | 2023-08-16 | 美商全球血液治療公司 | 包含2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)-苯甲醛之片劑 |
| US10702508B2 (en) | 2017-10-16 | 2020-07-07 | Aragon Pharmaceuticals, Inc. | Anti-androgens for the treatment of non-metastatic castration-resistant prostate cancer |
| US11014884B2 (en) | 2018-10-01 | 2021-05-25 | Global Blood Therapeutics, Inc. | Modulators of hemoglobin |
| EP3880680A1 (fr) | 2018-11-14 | 2021-09-22 | Altavant Sciences GmbH | Inhibiteur de composé spirocyclique cristallin de tryptophane hydroxylase 1 (tph1) pour le traitement de maladies ou de troubles associés à la sérotonine périphérique |
| PT3880654T (pt) | 2018-11-19 | 2022-04-08 | Global Blood Therapeutics Inc | Compostos de 2-formil-3-hidroxifeniloximetil capazes de modular hemoglobina |
| CN117120436A (zh) * | 2021-03-30 | 2023-11-24 | 苏州开拓药业股份有限公司 | 一种一步法合成乙内酰硫脲衍生物的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10010968A1 (de) * | 2000-03-07 | 2001-09-13 | Aventis Pharma Gmbh | Substituierte 3-Phenyl-5-alkoxi-1,3,4-oxdiazol-2-one, ihre Herstellung und Verwendung in Arzneistoffen |
| WO2001087843A1 (fr) * | 2000-05-15 | 2001-11-22 | Novo Nordisk A/S | Composes destines au traitement de troubles dans lesquels une diminution du niveau d'agl du plasma est voulue |
| DE10063008A1 (de) * | 2000-12-16 | 2002-06-20 | Merck Patent Gmbh | Carbonsäureamidderivate |
| JP2005518376A (ja) * | 2001-12-14 | 2005-06-23 | ノボ ノルディスク アクティーゼルスカブ | 化合物およびホルモン感受性リパーゼの活性を低下させるためのその使用 |
-
2004
- 2004-06-08 CA CA002526204A patent/CA2526204A1/fr not_active Abandoned
- 2004-06-08 MX MXPA05013224A patent/MXPA05013224A/es not_active Application Discontinuation
- 2004-06-08 BR BRPI0411255-5A patent/BRPI0411255A/pt not_active IP Right Cessation
- 2004-06-08 JP JP2006515703A patent/JP2006527210A/ja not_active Withdrawn
- 2004-06-08 RU RU2005137716/04A patent/RU2337908C2/ru not_active IP Right Cessation
- 2004-06-08 WO PCT/DK2004/000391 patent/WO2004111031A1/fr not_active Ceased
- 2004-06-08 KR KR1020057021923A patent/KR20060017791A/ko not_active Withdrawn
- 2004-06-08 AU AU2004247319A patent/AU2004247319A1/en not_active Abandoned
- 2004-06-08 EP EP04736303A patent/EP1636205A1/fr not_active Withdrawn
-
2006
- 2006-01-12 NO NO20060168A patent/NO20060168L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20060017791A (ko) | 2006-02-27 |
| JP2006527210A (ja) | 2006-11-30 |
| RU2005137716A (ru) | 2006-05-27 |
| NO20060168L (no) | 2006-03-10 |
| WO2004111031A1 (fr) | 2004-12-23 |
| BRPI0411255A (pt) | 2006-08-01 |
| MXPA05013224A (es) | 2006-03-09 |
| EP1636205A1 (fr) | 2006-03-22 |
| RU2337908C2 (ru) | 2008-11-10 |
| AU2004247319A1 (en) | 2004-12-23 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |