CA2681560A1 - Pteridinone derivatives for use as stearoyl coa desaturase inhibitors - Google Patents
Pteridinone derivatives for use as stearoyl coa desaturase inhibitors Download PDFInfo
- Publication number
- CA2681560A1 CA2681560A1 CA002681560A CA2681560A CA2681560A1 CA 2681560 A1 CA2681560 A1 CA 2681560A1 CA 002681560 A CA002681560 A CA 002681560A CA 2681560 A CA2681560 A CA 2681560A CA 2681560 A1 CA2681560 A1 CA 2681560A1
- Authority
- CA
- Canada
- Prior art keywords
- amino
- methyl
- ethyl
- hydropteridin
- oxo
- 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
- 108010087894 Fatty acid desaturases Proteins 0.000 title claims abstract description 64
- 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 title claims abstract description 63
- 239000003112 inhibitor Substances 0.000 title claims abstract description 14
- VWXIHLCLIOQWRA-UHFFFAOYSA-N 1h-pteridin-2-one Chemical class N1=CC=NC2=NC(O)=NC=C21 VWXIHLCLIOQWRA-UHFFFAOYSA-N 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 182
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 53
- 201000010099 disease Diseases 0.000 claims abstract description 40
- 208000008589 Obesity Diseases 0.000 claims abstract description 13
- 235000020824 obesity Nutrition 0.000 claims abstract description 13
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 216
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 205
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 199
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 174
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 147
- -1 2-thiazolyl Chemical group 0.000 claims description 91
- 125000000217 alkyl group Chemical group 0.000 claims description 77
- 125000003118 aryl group Chemical group 0.000 claims description 61
- 125000001072 heteroaryl group Chemical group 0.000 claims description 61
- 125000001424 substituent group Chemical group 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 42
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 150000003857 carboxamides Chemical class 0.000 claims description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 125000000304 alkynyl group Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 19
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 7
- 206010022489 Insulin Resistance Diseases 0.000 claims description 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
- 208000032109 Transient ischaemic attack Diseases 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 201000010875 transient cerebral ischemia Diseases 0.000 claims description 6
- 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 5
- 230000003247 decreasing effect Effects 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 239000008103 glucose Substances 0.000 claims description 4
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- NQQRXZOPZBKCNF-NSCUHMNNSA-N (e)-but-2-enamide Chemical compound C\C=C\C(N)=O NQQRXZOPZBKCNF-NSCUHMNNSA-N 0.000 claims description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 101100240528 Caenorhabditis elegans nhr-23 gene Proteins 0.000 claims description 3
- 208000002249 Diabetes Complications Diseases 0.000 claims description 3
- 206010012655 Diabetic complications Diseases 0.000 claims description 3
- 208000032382 Ischaemic stroke Diseases 0.000 claims description 3
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 3
- 208000017442 Retinal disease Diseases 0.000 claims description 3
- 206010038923 Retinopathy Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 3
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 3
- 208000029078 coronary artery disease Diseases 0.000 claims description 3
- 208000019622 heart disease Diseases 0.000 claims description 3
- 230000000302 ischemic effect Effects 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- XZOWIJDBQIHMFC-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O.CCCC(N)=O XZOWIJDBQIHMFC-UHFFFAOYSA-N 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 abstract description 14
- 230000001404 mediated effect Effects 0.000 abstract description 14
- 208000001145 Metabolic Syndrome Diseases 0.000 abstract description 7
- 208000024172 Cardiovascular disease Diseases 0.000 abstract description 6
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 abstract description 6
- 102000004190 Enzymes Human genes 0.000 abstract description 4
- 108090000790 Enzymes Proteins 0.000 abstract description 4
- 230000002159 abnormal effect Effects 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 description 44
- 239000000203 mixture Substances 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 125000003545 alkoxy group Chemical group 0.000 description 26
- 150000001412 amines Chemical class 0.000 description 25
- 150000002367 halogens Chemical class 0.000 description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 22
- 125000004181 carboxyalkyl group Chemical group 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
- 125000004093 cyano group Chemical group *C#N 0.000 description 22
- 230000000694 effects Effects 0.000 description 20
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 125000000392 cycloalkenyl group Chemical group 0.000 description 17
- 101100513046 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) eth-1 gene Proteins 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 13
- 208000035475 disorder Diseases 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 11
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- 125000004414 alkyl thio group Chemical group 0.000 description 10
- 238000003556 assay Methods 0.000 description 10
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound 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 description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 229930194542 Keto Natural products 0.000 description 9
- 125000002252 acyl group Chemical group 0.000 description 9
- 125000004442 acylamino group Chemical group 0.000 description 9
- 125000004423 acyloxy group Chemical group 0.000 description 9
- 125000005110 aryl thio group Chemical group 0.000 description 9
- 125000004104 aryloxy group Chemical group 0.000 description 9
- 125000005553 heteroaryloxy group Chemical group 0.000 description 9
- 125000000468 ketone group Chemical group 0.000 description 9
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 9
- 150000003573 thiols Chemical class 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- 125000000033 alkoxyamino group Chemical group 0.000 description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 8
- 125000006598 aminocarbonylamino group Chemical group 0.000 description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 8
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 125000005368 heteroarylthio group Chemical group 0.000 description 8
- 125000004470 heterocyclooxy group Chemical group 0.000 description 8
- 125000004468 heterocyclylthio group Chemical group 0.000 description 8
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 8
- 210000004185 liver Anatomy 0.000 description 8
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 210000001589 microsome Anatomy 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- SIARJEKBADXQJG-LFZQUHGESA-N stearoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 SIARJEKBADXQJG-LFZQUHGESA-N 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- IXHNFOOSLAWRBQ-UHFFFAOYSA-N (3,4-dichlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C(Cl)=C1 IXHNFOOSLAWRBQ-UHFFFAOYSA-N 0.000 description 5
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- 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 description 4
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
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- 125000003710 aryl alkyl group Chemical group 0.000 description 3
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- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
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- 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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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91075007P | 2007-04-09 | 2007-04-09 | |
| US60/910,750 | 2007-04-09 | ||
| PCT/US2007/080629 WO2008123891A1 (en) | 2007-04-09 | 2007-10-05 | PTERIDINONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2681560A1 true CA2681560A1 (en) | 2008-10-16 |
Family
ID=39047496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002681560A Abandoned CA2681560A1 (en) | 2007-04-09 | 2007-10-05 | Pteridinone derivatives for use as stearoyl coa desaturase inhibitors |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US7662819B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2131844A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2010523653A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2681560A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2008123891A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US20050119251A1 (en) * | 2001-12-21 | 2005-06-02 | Jian-Min Fu | Nicotinamide derivatives and their use as therapeutic agents |
| EP1799664A1 (en) * | 2004-09-20 | 2007-06-27 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| EP1804792A1 (en) * | 2004-09-20 | 2007-07-11 | Xenon Pharmaceuticals Inc. | Bicyclic heterocyclic derivatives and their use as inhibitors of stearoyl-coa-desaturase (scd) |
| WO2006101521A2 (en) * | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| AU2005286728A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase |
| CA2618646A1 (en) * | 2005-06-03 | 2007-11-15 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
| US7893066B2 (en) * | 2006-10-05 | 2011-02-22 | Gilead Palo Alto, Inc. | Pyridol[2,3-B]pyrazinones for use as stearoyl CoA desaturase inhibitors |
| EP2066665A2 (en) * | 2006-10-05 | 2009-06-10 | Cv Therapeutics, Inc. | Bicyclic nitrogen-containing heterocyclic compounds for use as stearoyl coa desaturase inhibitors |
| EP2131844A1 (en) * | 2007-04-09 | 2009-12-16 | CV Therapeutics Inc. | PTERIDINONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
| US20090105283A1 (en) * | 2007-04-11 | 2009-04-23 | Dmitry Koltun | 3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
| US20080255161A1 (en) * | 2007-04-11 | 2008-10-16 | Dmitry Koltun | 3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
| EP2242745A1 (de) * | 2008-02-07 | 2010-10-27 | Sanofi-Aventis | Neue phenyl-substituierte imidazolidine, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2274308A1 (en) * | 2008-04-04 | 2011-01-19 | Gilead Sciences, Inc. | Pyrrolotriazinone derivatives for use as stearoyl coa desaturase inhibitors |
| KR20100132999A (ko) * | 2008-04-04 | 2010-12-20 | 길리애드 사이언시즈, 인코포레이티드 | 스테아로일 ＣｏＡ 불포화 효소 억제제로서 사용하기 위한 트리아졸로피리디논 유도체 |
| EP2276748A1 (en) * | 2008-04-10 | 2011-01-26 | Gilead Sciences, Inc. | Bicyclic nitrogen containing heterocyclic compounds for use as stearoyl coa desaturase inhibitors |
| WO2010045371A1 (en) * | 2008-10-15 | 2010-04-22 | Gilead Palo Alto, Inc. | Pyrido- and pyrimido (1, 2-a) pyrimidine compounds useful as stearoyl coa desaturase inhibitors |
| US20100267752A1 (en) * | 2008-10-15 | 2010-10-21 | Gilead Palo Alto, Inc. | 3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
| CA2850836A1 (en) | 2011-10-15 | 2013-04-18 | Genentech, Inc. | Methods of using scd1 antagonists |
| CN117777121A (zh) | 2016-10-24 | 2024-03-29 | 詹森药业有限公司 | 化合物及其用途 |
| MA47212A (fr) | 2017-01-06 | 2019-11-13 | Yumanity Therapeutics Inc | Méthodes de traitement de troubles neurologiques |
| EP3700934A4 (en) | 2017-10-24 | 2021-10-27 | Yumanity Therapeutics, Inc. | COMPOUNDS AND USES OF THESE COMPOUNDS |
| CN112312913B (zh) | 2018-03-23 | 2024-03-08 | 詹森药业有限公司 | 化合物和其用途 |
| SG11202108079RA (en) | 2019-01-24 | 2021-08-30 | Yumanity Therapeutics Inc | Compounds and uses thereof |
| EA202192047A1 (ru) | 2019-11-13 | 2021-12-08 | Юманити Терапьютикс, Инк. | Соединения и их применение |
| JP2023549540A (ja) | 2020-11-18 | 2023-11-27 | デシフェラ・ファーマシューティカルズ，エルエルシー | Ｇｃｎ２およびｐｅｒｋキナーゼ阻害剤およびその使用方法 |
| CN115010711B (zh) * | 2022-07-12 | 2024-12-03 | 江南大学 | 一种蝶啶7（8h）-酮类化合物及其在药学上的应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3845770A (en) * | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US4326525A (en) * | 1980-10-14 | 1982-04-27 | Alza Corporation | Osmotic device that improves delivery properties of agent in situ |
| US5364620A (en) * | 1983-12-22 | 1994-11-15 | Elan Corporation, Plc | Controlled absorption diltiazem formulation for once daily administration |
| US5023252A (en) * | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US4992445A (en) * | 1987-06-12 | 1991-02-12 | American Cyanamid Co. | Transdermal delivery of pharmaceuticals |
| US5001139A (en) * | 1987-06-12 | 1991-03-19 | American Cyanamid Company | Enchancers for the transdermal flux of nivadipine |
| BR9815785A (pt) | 1998-03-31 | 2000-12-05 | Warner Lambert Co | Quinoxalinonas como inibidores de protease de serina tal como fator xa e trombina |
| JP2003509425A (ja) * | 1999-09-15 | 2003-03-11 | ワーナー−ランバート・カンパニー | キナーゼ阻害剤としてのプテリジノン |
| US7196090B2 (en) | 2002-07-25 | 2007-03-27 | Warner-Lambert Company | Kinase inhibitors |
| US7946750B2 (en) * | 2005-08-23 | 2011-05-24 | Innovative Concrete Solutions, Inc. | Composition for and method of pumping concrete |
| US7893066B2 (en) * | 2006-10-05 | 2011-02-22 | Gilead Palo Alto, Inc. | Pyridol[2,3-B]pyrazinones for use as stearoyl CoA desaturase inhibitors |
| EP2066665A2 (en) * | 2006-10-05 | 2009-06-10 | Cv Therapeutics, Inc. | Bicyclic nitrogen-containing heterocyclic compounds for use as stearoyl coa desaturase inhibitors |
| EP2131844A1 (en) * | 2007-04-09 | 2009-12-16 | CV Therapeutics Inc. | PTERIDINONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
| US20080255161A1 (en) * | 2007-04-11 | 2008-10-16 | Dmitry Koltun | 3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
| US20090105283A1 (en) * | 2007-04-11 | 2009-04-23 | Dmitry Koltun | 3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
| KR20100132999A (ko) * | 2008-04-04 | 2010-12-20 | 길리애드 사이언시즈, 인코포레이티드 | 스테아로일 ＣｏＡ 불포화 효소 억제제로서 사용하기 위한 트리아졸로피리디논 유도체 |
| EP2274308A1 (en) * | 2008-04-04 | 2011-01-19 | Gilead Sciences, Inc. | Pyrrolotriazinone derivatives for use as stearoyl coa desaturase inhibitors |
-
2007
- 2007-10-05 EP EP07853822A patent/EP2131844A1/en not_active Withdrawn
- 2007-10-05 JP JP2010502995A patent/JP2010523653A/ja not_active Withdrawn
- 2007-10-05 US US11/868,407 patent/US7662819B2/en not_active Expired - Fee Related
- 2007-10-05 CA CA002681560A patent/CA2681560A1/en not_active Abandoned
- 2007-10-05 WO PCT/US2007/080629 patent/WO2008123891A1/en not_active Ceased
-
2010
- 2010-01-07 US US12/684,007 patent/US20100113463A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US7662819B2 (en) | 2010-02-16 |
| EP2131844A1 (en) | 2009-12-16 |
| US20100113463A1 (en) | 2010-05-06 |
| WO2008123891A1 (en) | 2008-10-16 |
| US20080249100A1 (en) | 2008-10-09 |
| JP2010523653A (ja) | 2010-07-15 |
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