ZA200603829B - Hydroxyalkyl substituted pyrido-7-pyrimidin-7-ones - Google Patents
Hydroxyalkyl substituted pyrido-7-pyrimidin-7-ones Download PDFInfo
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- ZA200603829B ZA200603829B ZA200603829A ZA200603829A ZA200603829B ZA 200603829 B ZA200603829 B ZA 200603829B ZA 200603829 A ZA200603829 A ZA 200603829A ZA 200603829 A ZA200603829 A ZA 200603829A ZA 200603829 B ZA200603829 B ZA 200603829B
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- ZA
- South Africa
- Prior art keywords
- formula
- hydroxy
- compound
- hydroxypropyl
- propyl
- Prior art date
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- 125000002768 hydroxyalkyl group Chemical group 0.000 title claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 74
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
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- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- -1 3-methoxypropyl Chemical group 0.000 description 157
- 238000006243 chemical reaction Methods 0.000 description 23
- 150000003839 salts Chemical class 0.000 description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- 201000010099 disease Diseases 0.000 description 16
- 125000005843 halogen group Chemical group 0.000 description 16
- 239000002904 solvent Substances 0.000 description 12
- 230000003647 oxidation Effects 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- 229940002612 prodrug Drugs 0.000 description 8
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- 108090000695 Cytokines Proteins 0.000 description 7
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- 239000002585 base Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- 125000004663 dialkyl amino group Chemical group 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 6
- WDHAAJIGSXNPFO-UHFFFAOYSA-N 8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CN=C2NC(=O)C=CC2=C1 WDHAAJIGSXNPFO-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
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- 125000006413 ring segment Chemical group 0.000 description 5
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- 125000002947 alkylene group Chemical group 0.000 description 4
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- 208000024891 symptom Diseases 0.000 description 4
- IAAQUOVTPAMQCR-UHFFFAOYSA-N 1h-pyrido[3,2-d]pyrimidin-2-one Chemical compound C1=CC=C2NC(=O)N=CC2=N1 IAAQUOVTPAMQCR-UHFFFAOYSA-N 0.000 description 3
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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- 125000005493 quinolyl group Chemical group 0.000 description 1
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- 230000009257 reactivity Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
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- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
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- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 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
- 125000005270 trialkylamine group Chemical group 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Neurology (AREA)
- Immunology (AREA)
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- Biomedical Technology (AREA)
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- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
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US51978903P | 2003-11-13 | 2003-11-13 |
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ZA200603829A ZA200603829B (en) | 2003-11-13 | 2006-05-12 | Hydroxyalkyl substituted pyrido-7-pyrimidin-7-ones |
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US (2) | US7348331B2 (da) |
EP (1) | EP1685131B1 (da) |
JP (1) | JP4616839B2 (da) |
KR (1) | KR100816321B1 (da) |
CN (1) | CN100455582C (da) |
AR (1) | AR046705A1 (da) |
AT (1) | ATE356124T1 (da) |
AU (1) | AU2004289428B2 (da) |
BR (1) | BRPI0416030A (da) |
CA (1) | CA2544247A1 (da) |
CO (1) | CO5690600A2 (da) |
DE (1) | DE602004005238T2 (da) |
DK (1) | DK1685131T3 (da) |
ES (1) | ES2281843T3 (da) |
HK (1) | HK1099021A1 (da) |
HR (1) | HRP20070132T3 (da) |
IL (1) | IL175284A0 (da) |
MY (1) | MY141011A (da) |
NO (1) | NO20062256L (da) |
NZ (1) | NZ546634A (da) |
PL (1) | PL1685131T3 (da) |
PT (1) | PT1685131E (da) |
RU (1) | RU2348632C2 (da) |
SI (1) | SI1685131T1 (da) |
TW (1) | TWI349670B (da) |
WO (1) | WO2005047284A1 (da) |
ZA (1) | ZA200603829B (da) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2008011032A1 (en) | 2006-07-17 | 2008-01-24 | Amgen Inc. | Quinazoline and pyridopyrimidine derivatives as p38 kinase inhibitors |
CA2672848A1 (en) * | 2006-12-22 | 2008-07-03 | F. Hoffmann-La Roche Ag | Compounds and methods for amino-alkylenediol synthesis |
EP2158182A2 (en) * | 2007-06-15 | 2010-03-03 | F. Hoffmann-Roche AG | A novel process for the preparation of 3-amino-pentan-1,5-diol |
KR101754664B1 (ko) * | 2009-12-18 | 2017-07-06 | 템플 유니버시티-오브 더 커먼웰쓰 시스템 오브 하이어 에듀케이션 | 치환된 피리도〔2,3-d〕피리미딘-7(8h)-온스 및 이의 치료 용도 |
JP6553629B2 (ja) | 2014-02-07 | 2019-07-31 | プリンシピア バイオファーマ インコーポレイテッド | 線維芽細胞増殖因子受容体阻害剤としてのキノロン誘導体 |
JP6940480B2 (ja) | 2015-08-11 | 2021-09-29 | プリンシピア バイオファーマ インコーポレイテッド | Fgfr阻害剤の合成方法 |
CN105418609B (zh) * | 2015-12-31 | 2017-06-23 | 山东大学 | 4‑(1,2,3‑三氮唑取代苯胺基)‑吡啶骈嘧啶酮衍生物及其制备方法与应用 |
WO2017151409A1 (en) | 2016-02-29 | 2017-09-08 | University Of Florida Research Foundation, Incorporated | Chemotherapeutic methods |
KR20220119529A (ko) | 2016-06-02 | 2022-08-29 | 애브비 인코포레이티드 | 글루코코르티코이드 수용체 작용제 및 이의 면역접합체 |
PE20190376A1 (es) | 2016-06-08 | 2019-03-08 | Support Venture Gmbh | Combinaciones farmaceuticas para el tratamiento del cancer |
EA201990220A1 (ru) | 2016-08-17 | 2019-08-30 | Суппорт-Венче Гмбх | Способ предотвращения или лечения потери слуха |
US11576916B2 (en) * | 2017-04-04 | 2023-02-14 | Kinarus Ag | Methods of preventing or treating ophthalmic diseases |
WO2019071147A1 (en) | 2017-10-05 | 2019-04-11 | Fulcrum Therapeutics, Inc. | INHIBITORS OF KINASE P38 REDUCING EXPRESSION OF DUX4 GENE AND DOWNSTREAM GENES FOR THE TREATMENT OF FSHD |
US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
WO2019106609A1 (en) | 2017-12-01 | 2019-06-06 | Abbvie Inc. | Glucocorticoid receptor agonist and immunoconjugates thereof |
WO2019224096A1 (en) | 2018-05-21 | 2019-11-28 | Nerviano Medical Sciences S.R.L. | Heterocondensed pyridones compounds and their use as idh inhibitors |
WO2020011661A1 (en) | 2018-07-13 | 2020-01-16 | Kinarus Ag | Combinations of ppar agonists and p38 kinase inhibitors for preventing or treating fibrotic diseases |
EP4055015A1 (en) | 2019-11-08 | 2022-09-14 | Nerviano Medical Sciences S.r.l. | Gem-disubstituted heterocyclic compounds and their use as idh inhibitors |
US20230263803A1 (en) | 2020-08-11 | 2023-08-24 | Kinarus Ag | Methods of preventing or treating covid-19 and related viral diseases or disorders |
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US4215216A (en) * | 1979-04-18 | 1980-07-29 | American Home Products Corporation | 7,8-Dihydro-2,5,8-trisubstituted-7-oxo-pyrido[2,3-d]pyrimidine-6-carboxylic acid derivatives |
US5037826A (en) * | 1986-10-15 | 1991-08-06 | Schering Corporation | 1-substituted naphthyridine and pyridopyrazine derivatives |
EP0278686A1 (en) | 1987-02-07 | 1988-08-17 | The Wellcome Foundation Limited | Pyridopyrimidines methods for their preparation and pharmaceutical formulations thereof |
WO1993017682A1 (en) | 1992-03-04 | 1993-09-16 | Abbott Laboratories | Angiotensin ii receptor antagonists |
MD1861G2 (ro) | 1994-11-14 | 2002-09-30 | Уорнер-Ламберт Кампэни | Derivaţi ai 6-arilpirido[2,3-d]pirimidinelor şi naftiridinelor, compoziţie farmaceutică pe baza lor, metode de tratament şi de inhibare a proliferării şi migraţiei celulei receptorului tirozinkinazei |
IL115256A0 (en) * | 1994-11-14 | 1995-12-31 | Warner Lambert Co | 6-Aryl pyrido (2,3-d) pyrimidines and naphthyridines and their use |
IL117923A (en) | 1995-05-03 | 2000-06-01 | Warner Lambert Co | Anti-cancer pharmaceutical compositions containing polysubstituted pyrido¬2,3-d¾pyrimidine derivatives and certain such novel compounds |
US5620981A (en) * | 1995-05-03 | 1997-04-15 | Warner-Lambert Company | Pyrido [2,3-D]pyrimidines for inhibiting protein tyrosine kinase mediated cellular proliferation |
WO1998033798A2 (en) | 1997-02-05 | 1998-08-06 | Warner Lambert Company | Pyrido[2,3-d]pyrimidines and 4-amino-pyrimidines as inhibitors of cell proliferation |
US5945422A (en) * | 1997-02-05 | 1999-08-31 | Warner-Lambert Company | N-oxides of amino containing pyrido 2,3-D! pyrimidines |
BR9911590A (pt) | 1998-05-26 | 2001-02-13 | Warner Lambert Co | Pirimidinas bicìclicas e 3,4-diidropirimidinas bicìclicas como inibidores da proliferação celular |
US7053070B2 (en) * | 2000-01-25 | 2006-05-30 | Warner-Lambert Company | Pyrido[2,3-d]pyrimidine-2,7-diamine kinase inhibitors |
SK10772002A3 (sk) | 2000-01-27 | 2004-01-08 | Warner-Lambert Company | Pyridopyrimidinónové deriváty na liečbu neurodegeneratívnych ochorení |
AP2002002643A0 (en) | 2000-03-06 | 2002-12-31 | Warner Lambert Co | 5-alkylpyrido[2,3-d]pyrimidines tyrosine kinase inhibitors |
US6518276B2 (en) * | 2000-08-31 | 2003-02-11 | Syntex (U.S.A.) Llc | 7-oxo-pyridopyrimidines (II) |
CN1275964C (zh) * | 2000-08-31 | 2006-09-20 | 霍夫曼-拉罗奇有限公司 | 作为细胞增殖抑制剂的7-氧代吡啶并嘧啶 |
WO2002064594A2 (en) * | 2001-02-12 | 2002-08-22 | F. Hoffmann-La Roche Ag | 6-substituted pyrido-pyrimidines |
GEP20063909B (en) * | 2002-01-22 | 2006-08-25 | Warner Lambert Co | 2-(PYRIDIN-2-YLAMINO)-PYRIDO[2,3d] PYRIMIDIN-7-ONES |
FR2897336B1 (fr) | 2006-02-10 | 2010-07-30 | Ranger France | Support d'aile pour vehicule automobile |
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- 2004-11-04 EP EP04797601A patent/EP1685131B1/en active Active
- 2004-11-04 RU RU2006120486/04A patent/RU2348632C2/ru not_active IP Right Cessation
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- 2004-11-04 JP JP2006538744A patent/JP4616839B2/ja not_active Expired - Fee Related
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- 2004-11-04 BR BRPI0416030-4A patent/BRPI0416030A/pt not_active IP Right Cessation
- 2004-11-04 CN CNB2004800337221A patent/CN100455582C/zh not_active Expired - Fee Related
- 2004-11-04 WO PCT/EP2004/012475 patent/WO2005047284A1/en active IP Right Grant
- 2004-11-04 KR KR1020067009146A patent/KR100816321B1/ko not_active IP Right Cessation
- 2004-11-09 MY MYPI20044668A patent/MY141011A/en unknown
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- 2004-11-10 AR ARP040104138A patent/AR046705A1/es not_active Application Discontinuation
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