EA005852B1 - ПИРРОЛО[2,3-d]ПИРИМИДИНЫ - Google Patents
ПИРРОЛО[2,3-d]ПИРИМИДИНЫ Download PDFInfo
- Publication number
- EA005852B1 EA005852B1 EA200001203A EA200001203A EA005852B1 EA 005852 B1 EA005852 B1 EA 005852B1 EA 200001203 A EA200001203 A EA 200001203A EA 200001203 A EA200001203 A EA 200001203A EA 005852 B1 EA005852 B1 EA 005852B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- pyrrolo
- pyrimidin
- group
- amino
- methyl
- Prior art date
Links
- 150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 101
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 9
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 9
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 9
- 208000006673 asthma Diseases 0.000 claims abstract description 9
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 9
- 206010009900 Colitis ulcerative Diseases 0.000 claims abstract description 8
- 206010012438 Dermatitis atopic Diseases 0.000 claims abstract description 8
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 8
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 8
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims abstract description 8
- 201000006704 Ulcerative Colitis Diseases 0.000 claims abstract description 8
- 201000008937 atopic dermatitis Diseases 0.000 claims abstract description 8
- 201000011510 cancer Diseases 0.000 claims abstract description 8
- 206010025135 lupus erythematosus Diseases 0.000 claims abstract description 8
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 8
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 7
- 208000011231 Crohn disease Diseases 0.000 claims abstract description 7
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 7
- 208000032839 leukemia Diseases 0.000 claims abstract description 7
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 126
- -1 5-isopropenyl- 2-methylcyclohexyl Chemical group 0.000 claims description 88
- 150000001412 amines Chemical class 0.000 claims description 82
- 238000000034 method Methods 0.000 claims description 69
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 57
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 35
- 241000124008 Mammalia Species 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 7
- 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 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 108091000080 Phosphotransferase Proteins 0.000 claims description 6
- 206010052779 Transplant rejections Diseases 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 102000020233 phosphotransferase Human genes 0.000 claims description 6
- 241000282412 Homo Species 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 5
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 210000000987 immune system Anatomy 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- 229940124599 anti-inflammatory drug Drugs 0.000 claims description 3
- 208000010928 autoimmune thyroid disease Diseases 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- 210000003437 trachea Anatomy 0.000 claims 1
- 210000000056 organ Anatomy 0.000 abstract description 6
- 239000003018 immunosuppressive agent Substances 0.000 abstract description 5
- 208000024799 Thyroid disease Diseases 0.000 abstract description 4
- 230000001363 autoimmune Effects 0.000 abstract description 4
- 239000003112 inhibitor Substances 0.000 abstract description 3
- 229940125721 immunosuppressive agent Drugs 0.000 abstract description 2
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- 102000015617 Janus Kinases Human genes 0.000 abstract 1
- 108010024121 Janus Kinases Proteins 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 55
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- 239000000203 mixture Substances 0.000 description 44
- 239000000243 solution Substances 0.000 description 38
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 235000019441 ethanol Nutrition 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
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- 210000004027 cell Anatomy 0.000 description 17
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 150000003230 pyrimidines Chemical class 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 10
- 108010036949 Cyclosporine Proteins 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 210000001744 T-lymphocyte Anatomy 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
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- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 231100000252 nontoxic Toxicity 0.000 description 5
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- 108060001084 Luciferase Proteins 0.000 description 4
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- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 239000003880 polar aprotic solvent Substances 0.000 description 4
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- FSVVROHVIVQDEA-UHFFFAOYSA-N 2-(cyclohexylamino)-1-methylcyclohexan-1-ol Chemical compound C1(CCCCC1)NC1C(CCCC1)(O)C FSVVROHVIVQDEA-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- FLDSMVTWEZKONL-AWEZNQCLSA-N 5,5-dimethyl-N-[(3S)-5-methyl-4-oxo-2,3-dihydro-1,5-benzoxazepin-3-yl]-1,4,7,8-tetrahydrooxepino[4,5-c]pyrazole-3-carboxamide Chemical compound CC1(CC2=C(NN=C2C(=O)N[C@@H]2C(N(C3=C(OC2)C=CC=C3)C)=O)CCO1)C FLDSMVTWEZKONL-AWEZNQCLSA-N 0.000 description 2
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- A61P5/16—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4 for decreasing, blocking or antagonising the activity of the thyroid hormones
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Neurosurgery (AREA)
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- Pulmonology (AREA)
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- Biomedical Technology (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8986698P | 1998-06-19 | 1998-06-19 | |
| US10478798P | 1998-10-19 | 1998-10-19 | |
| PCT/IB1999/001100 WO1999065908A1 (en) | 1998-06-19 | 1999-06-14 | PYRROLO[2,3-d]PYRIMIDINE COMPOUNDS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200001203A1 EA200001203A1 (ru) | 2001-06-25 |
| EA005852B1 true EA005852B1 (ru) | 2005-06-30 |
Family
ID=26781018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200001203A EA005852B1 (ru) | 1998-06-19 | 1999-06-14 | ПИРРОЛО[2,3-d]ПИРИМИДИНЫ |
Country Status (40)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2503676C2 (ru) * | 2008-02-25 | 2014-01-10 | Ф.Хоффманн-Ля Рош Аг | Пирролопиразиновые ингибиторы киназы |
| RU2630694C2 (ru) * | 2009-07-31 | 2017-09-12 | Джапан Тобакко Инк. | Азотсодержащее спироциклическое соединение и его применение в медицине |
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| CZ303875B6 (cs) * | 1999-12-10 | 2013-06-05 | Pfizer Products Inc. | Pyrrolo[2,3-d]pyrimidinová sloucenina a farmaceutická kompozice s jejím obsahem |
| EA006153B1 (ru) * | 2000-06-26 | 2005-10-27 | Пфайзер Продактс Инк. | СОЕДИНЕНИЯ ПИРРОЛО[2,3-d]ПИРИМИДИНА В КАЧЕСТВЕ ИММУНОДЕПРЕССАНТОВ |
| JP2004509876A (ja) | 2000-09-20 | 2004-04-02 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | ４−アミノ−キナゾリン |
| US7067550B2 (en) * | 2000-11-03 | 2006-06-27 | Massachusetts Institute Of Technology | Treatments for neurotoxicity in Alzheimer's Disease |
| DE10063294A1 (de) * | 2000-12-19 | 2002-07-04 | Aventis Pharma Gmbh | Substituierte Heterocyclo-Norbornylamino-Derivate, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| WO2002060492A1 (en) * | 2001-01-30 | 2002-08-08 | Cytopia Pty Ltd | Methods of inhibiting kinases |
| AU2002256615B2 (en) | 2001-02-12 | 2007-09-13 | F. Hoffmann-La Roche Ag | 6-substituted pyrido-pyrimidines |
| US7301023B2 (en) | 2001-05-31 | 2007-11-27 | Pfizer Inc. | Chiral salt resolution |
| GB0115393D0 (en) * | 2001-06-23 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| ATE401079T1 (de) * | 2001-06-29 | 2008-08-15 | Ab Science | Die verwendung von c-kithemmern zur behandlung von autoimmunerkrankungen |
| WO2003004007A2 (en) * | 2001-06-29 | 2003-01-16 | Ab Science | Use of tyrosine kinase inhibitors for treating inflammatory bowel diseases (ibd) |
| CA2452368A1 (en) | 2001-06-29 | 2003-01-09 | Ab Science | New potent, selective and non toxic c-kit inhibitors |
| DK1401413T3 (da) | 2001-06-29 | 2007-03-26 | Ab Science | Anvendelse af tyrosinkinaseinhibitorer til behandling af allergiske sygdomme |
| EP1401415B1 (en) | 2001-06-29 | 2006-06-21 | AB Science | Use of n-phenyl-2-pyrimidine-amine derivatives for treating inflammatory diseases |
| GB0119249D0 (en) | 2001-08-07 | 2001-10-03 | Novartis Ag | Organic compounds |
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| US7829566B2 (en) | 2001-09-17 | 2010-11-09 | Werner Mederski | 4-amino-quinazolines |
| GT200200234A (es) | 2001-12-06 | 2003-06-27 | Compuestos cristalinos novedosos | |
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| US6924290B2 (en) | 2002-01-23 | 2005-08-02 | Bayer Pharmaceuticals Corporation | Rho-kinase inhibitors |
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| GB0202679D0 (en) * | 2002-02-05 | 2002-03-20 | Glaxo Group Ltd | Novel compounds |
| EP1388541A1 (en) * | 2002-08-09 | 2004-02-11 | Centre National De La Recherche Scientifique (Cnrs) | Pyrrolopyrazines as kinase inhibitors |
| CA2507392A1 (en) * | 2002-11-26 | 2004-06-10 | Pfizer Products Inc. | Method of treatment of transplant rejection |
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| WO2005051393A1 (en) * | 2003-11-25 | 2005-06-09 | Pfizer Products Inc. | Method of treatment of atherosclerosis |
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| RU2630694C2 (ru) * | 2009-07-31 | 2017-09-12 | Джапан Тобакко Инк. | Азотсодержащее спироциклическое соединение и его применение в медицине |
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