RU2004133811A - Новые соединения - Google Patents
Новые соединения Download PDFInfo
- Publication number
- RU2004133811A RU2004133811A RU2004133811/04A RU2004133811A RU2004133811A RU 2004133811 A RU2004133811 A RU 2004133811A RU 2004133811/04 A RU2004133811/04 A RU 2004133811/04A RU 2004133811 A RU2004133811 A RU 2004133811A RU 2004133811 A RU2004133811 A RU 2004133811A
- Authority
- RU
- Russia
- Prior art keywords
- difluorophenyl
- pyrido
- pyrimidin
- methylsulfanylpyrimidine
- carbaldehyde
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 6
- 102100023482 Mitogen-activated protein kinase 14 Human genes 0.000 claims abstract 4
- 108010084680 Heterogeneous-Nuclear Ribonucleoprotein K Proteins 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims 4
- 206010062106 Respiratory tract infection viral Diseases 0.000 claims 3
- 206010040070 Septic Shock Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 210000004072 lung Anatomy 0.000 claims 3
- JCLDTGONWQOHTP-UHFFFAOYSA-N 4-(2,4-difluoroanilino)-6-(2,4-difluorophenyl)-2-methylsulfanylpyrimidine-5-carbaldehyde Chemical compound O=CC=1C(C=2C(=CC(F)=CC=2)F)=NC(SC)=NC=1NC1=CC=C(F)C=C1F JCLDTGONWQOHTP-UHFFFAOYSA-N 0.000 claims 2
- 208000017667 Chronic Disease Diseases 0.000 claims 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 2
- 201000005569 Gout Diseases 0.000 claims 2
- 241000430519 Human rhinovirus sp. Species 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 206010033078 Otitis media Diseases 0.000 claims 2
- 206010035664 Pneumonia Diseases 0.000 claims 2
- 206010040047 Sepsis Diseases 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 208000002780 macular degeneration Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims 2
- 201000009890 sinusitis Diseases 0.000 claims 2
- LPAWYEYFSNWBHC-UHFFFAOYSA-N 2-(1,3-dihydroxypropan-2-ylamino)-4-(2-fluorophenyl)-8-(2,4,6-trifluorophenyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C=12C=CC(=O)N(C=3C(=CC(F)=CC=3F)F)C2=NC(NC(CO)CO)=NC=1C1=CC=CC=C1F LPAWYEYFSNWBHC-UHFFFAOYSA-N 0.000 claims 1
- BHLGLVOFWRMAQD-UHFFFAOYSA-N 2-(1,3-dihydroxypropan-2-ylamino)-4-(4-fluorophenyl)-8-(2,4,6-trifluorophenyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C=12C=CC(=O)N(C=3C(=CC(F)=CC=3F)F)C2=NC(NC(CO)CO)=NC=1C1=CC=C(F)C=C1 BHLGLVOFWRMAQD-UHFFFAOYSA-N 0.000 claims 1
- QWSRSVMAHMEJSH-UHFFFAOYSA-N 4,8-bis(2,4-difluorophenyl)-2-(1,3-dihydroxypropan-2-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C=12C=CC(=O)N(C=3C(=CC(F)=CC=3)F)C2=NC(NC(CO)CO)=NC=1C1=CC=C(F)C=C1F QWSRSVMAHMEJSH-UHFFFAOYSA-N 0.000 claims 1
- XDDQTWANQIWCKF-UHFFFAOYSA-N 4,8-bis(2,4-difluorophenyl)-2-(1-hydroxypropan-2-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C=12C=CC(=O)N(C=3C(=CC(F)=CC=3)F)C2=NC(NC(CO)C)=NC=1C1=CC=C(F)C=C1F XDDQTWANQIWCKF-UHFFFAOYSA-N 0.000 claims 1
- KCROWODVCUUNFN-UHFFFAOYSA-N 4-(2,3-difluoroanilino)-6-(2,4-difluorophenyl)-2-methylsulfanylpyrimidine-5-carbaldehyde Chemical compound O=CC=1C(C=2C(=CC(F)=CC=2)F)=NC(SC)=NC=1NC1=CC=CC(F)=C1F KCROWODVCUUNFN-UHFFFAOYSA-N 0.000 claims 1
- CHGZPDZHRQVHIM-UHFFFAOYSA-N 4-(2,4-difluoroanilino)-2-methylsulfanyl-6-(2,4,6-trifluoroanilino)pyrimidine-5-carbaldehyde Chemical compound O=CC=1C(NC=2C(=CC(F)=CC=2F)F)=NC(SC)=NC=1NC1=CC=C(F)C=C1F CHGZPDZHRQVHIM-UHFFFAOYSA-N 0.000 claims 1
- IKAWJOGYPWTEQL-UHFFFAOYSA-N 4-(2,4-difluoroanilino)-6-(2-fluorophenyl)-2-methylsulfanylpyrimidine-5-carbaldehyde Chemical compound O=CC=1C(C=2C(=CC=CC=2)F)=NC(SC)=NC=1NC1=CC=C(F)C=C1F IKAWJOGYPWTEQL-UHFFFAOYSA-N 0.000 claims 1
- UMNPZIKRPVBEDR-UHFFFAOYSA-N 4-(2,4-difluorophenyl)-2-(1,3-dihydroxypropan-2-ylamino)-8-(2,4,6-trifluorophenyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C=12C=CC(=O)N(C=3C(=CC(F)=CC=3F)F)C2=NC(NC(CO)CO)=NC=1C1=CC=C(F)C=C1F UMNPZIKRPVBEDR-UHFFFAOYSA-N 0.000 claims 1
- MMQJPIULOQFIMJ-UHFFFAOYSA-N 4-(2,4-difluorophenyl)-6-(4-fluoroanilino)-2-methylsulfanylpyrimidine-5-carbaldehyde Chemical compound O=CC=1C(C=2C(=CC(F)=CC=2)F)=NC(SC)=NC=1NC1=CC=C(F)C=C1 MMQJPIULOQFIMJ-UHFFFAOYSA-N 0.000 claims 1
- YURMQSYOIRGDHG-LBPRGKRZSA-N 4-(2,4-difluorophenyl)-8-(4-fluorophenyl)-2-[[(2s)-1-hydroxypropan-2-yl]amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C=12C=CC(=O)N(C=3C=CC(F)=CC=3)C2=NC(N[C@H](CO)C)=NC=1C1=CC=C(F)C=C1F YURMQSYOIRGDHG-LBPRGKRZSA-N 0.000 claims 1
- HWOVAYJUKBWPEE-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenyl)-6-(2,4-difluoroanilino)-2-methylsulfanylpyrimidine-5-carbaldehyde Chemical compound O=CC=1C(C=2C(=CC(F)=CC=2)Cl)=NC(SC)=NC=1NC1=CC=C(F)C=C1F HWOVAYJUKBWPEE-UHFFFAOYSA-N 0.000 claims 1
- WJLJTZCRKSSROJ-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenyl)-8-(2,4-difluorophenyl)-2-(1,3-dihydroxypropan-2-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C=12C=CC(=O)N(C=3C(=CC(F)=CC=3)F)C2=NC(NC(CO)CO)=NC=1C1=CC=C(F)C=C1Cl WJLJTZCRKSSROJ-UHFFFAOYSA-N 0.000 claims 1
- OTQQIAYCYKIMLV-UHFFFAOYSA-N 4-(2-fluorophenyl)-2-methylsulfanyl-6-(2,4,6-trifluoroanilino)pyrimidine-5-carbaldehyde Chemical compound O=CC=1C(C=2C(=CC=CC=2)F)=NC(SC)=NC=1NC1=C(F)C=C(F)C=C1F OTQQIAYCYKIMLV-UHFFFAOYSA-N 0.000 claims 1
- QHKYQXJKCRVSHV-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-methylsulfanyl-6-(2,4,6-trifluoroanilino)pyrimidine-5-carbaldehyde Chemical compound O=CC=1C(C=2C=CC(F)=CC=2)=NC(SC)=NC=1NC1=C(F)C=C(F)C=C1F QHKYQXJKCRVSHV-UHFFFAOYSA-N 0.000 claims 1
- CEQWGAOJJSBLAJ-UHFFFAOYSA-N 8-(2,3-difluorophenyl)-4-(2,4-difluorophenyl)-2-(1,3-dihydroxypropan-2-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C=12C=CC(=O)N(C=3C(=C(F)C=CC=3)F)C2=NC(NC(CO)CO)=NC=1C1=CC=C(F)C=C1F CEQWGAOJJSBLAJ-UHFFFAOYSA-N 0.000 claims 1
- XIDKYJHGKBVRDL-LBPRGKRZSA-N 8-(2,4-difluorophenyl)-4-(2-fluorophenyl)-2-[[(2s)-1-hydroxypropan-2-yl]amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C=12C=CC(=O)N(C=3C(=CC(F)=CC=3)F)C2=NC(N[C@H](CO)C)=NC=1C1=CC=CC=C1F XIDKYJHGKBVRDL-LBPRGKRZSA-N 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 208000006386 Bone Resorption Diseases 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 206010063094 Cerebral malaria Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 241000711573 Coronaviridae Species 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- 206010014824 Endotoxic shock Diseases 0.000 claims 1
- 241000709661 Enterovirus Species 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 206010018634 Gouty Arthritis Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 201000005505 Measles Diseases 0.000 claims 1
- 201000009906 Meningitis Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 208000002606 Paramyxoviridae Infections Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 1
- 208000033464 Reiter syndrome Diseases 0.000 claims 1
- 241000725643 Respiratory syncytial virus Species 0.000 claims 1
- 201000010001 Silicosis Diseases 0.000 claims 1
- 206010042496 Sunburn Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 206010044248 Toxic shock syndrome Diseases 0.000 claims 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 1
- 206010048873 Traumatic arthritis Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 206010052428 Wound Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 230000024279 bone resorption Effects 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 208000037976 chronic inflammation Diseases 0.000 claims 1
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 208000022831 chronic renal failure syndrome Diseases 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- 210000004351 coronary vessel Anatomy 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 210000002216 heart Anatomy 0.000 claims 1
- 230000002008 hemorrhagic effect Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 206010022000 influenza Diseases 0.000 claims 1
- 230000000968 intestinal effect Effects 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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- 208000037803 restenosis Diseases 0.000 claims 1
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- 150000003839 salts Chemical class 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 201000004595 synovitis Diseases 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
- 241000701161 unidentified adenovirus Species 0.000 claims 1
- 241000712461 unidentified influenza virus Species 0.000 claims 1
- -1 2,4,8-trisubstituted-8H-pyrido[2,3-d]pyrimidin-7-one compounds Chemical class 0.000 abstract 1
- 229940043355 kinase inhibitor Drugs 0.000 abstract 1
- 239000000203 mixture Chemical class 0.000 abstract 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
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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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
Claims (7)
1. Соединение, которое представляет собой
8-(2,4,6-трифторфенил)-4-(2,4-дифторфенил)-2-(2-гидрокси-1-гидроксиметилэтиламино)-8Н-пиридо[2,3-d]пиримидин-7-он;
4,8-бис(2,4-дифторфенил)-2-(2-гидрокси-1-гидроксиметилэтиламино)-8Н-пиридо[2,3-d]пиримидин-7-он;
8-(2,4,6-трифторфенил)-4-(2-фторфенил)-2-(2-гидрокси-1-гидроксиметилэтиламино)-8Н-пиридо[2,3-d]пиримидин-7-он;
8-(2,4,6-трифторфенил)-4-(4-фторфенил)-2-(2-гидрокси-1-гидроксиметилэтиламино)-8Н-пиридо[2,3-d]пиримидин-7-он;
4-(2-фторфенил)-8-(2,4-дифторфенил)-2-((S)-2-гидрокси-1-метилэтиламино)-8Н-пиридо[2,3-d]пиримидин-7-он;
4-(2,4-дифторфенил)-8-(4-фторфенил)-2-((S)-2-гидрокси-1-метилэтиламино)-8Н-пиридо[2,3-d]пиримидин-7-он;
4,8-бис(2,4-дифторфенил)-2-(2-гидрокси-1-метилэтиламино)-8Н-пиридо[2,3-d]пиримидин-7-он;
8-(2,4-дифторфенил)-4-(2-хлор-4-фторфенил)-2-(2-гидрокси-1-гидроксиметилэтиламино)-8Н-пиридо[2,3-d]пиримидин-7-он; или
8-(2,3-дифторфенил)-4-(2,4-дифторфенил)-2-(2-гидрокси-1-гидроксиметилэтиламино)-8Н-пиридо[2,3-d]пиримидин-7-он; или его фармацевтически приемлемая соль.
2. Фармацевтическая композиция, включающая эффективное количество соединения по п.1 и фармацевтически приемлемый носитель или разбавитель.
3. Способ лечения заболевания, опосредованного CSBP/RK/p38-киназой, у нуждающегося в этом млекопитающего, включающий введение указанному млекопитающему эффективного количества соединения по п.1.
4. Способ по п.3, где заболеванием, опосредованным CSBP/RK/p38-киназой, является псориатический артрит, синдром Рейтера, подагра, травматический артрит, коревый артрит, острый синовиит, ревматоидный артрит, ревматоидный спондилит, остеоартрит, подагрический артрит и другие связанные с артритом состояния, сепсис, септический шок, эндотоксический шок, грамотрицательный сепсис, синдром токсического шока, церебральная малярия, менингит, ишемический и геморрагический приступ, нейротравма/закрытая рана головы, астма, респираторный дистресс-синдром у взрослых, хронические воспалительные заболевания легких, хронические заболевания, связанные с закупоркой легких, силикоз, легочный саркоидоз, болезни, вызванные резорбцией костей, остеопороз, рестеноз, вызванное реперфузией поражение сердца, мозга и почек, застойная сердечная недостаточность, хирургия шунтированием коронарных артерий (CABG), тромбоз, атеросклероз, гломерулонефрит, хроническая почечная недостаточность, диабет, диабетическая ретинопатия, макулодистрофия, реакция “трансплантат против хозяина”, отторжение аллотрансплантата, воспаление кишечника, болезнь Крона, язвенный колит, нейродегенеративные заболевания, дистрофия мышц, диабетическая ретинопатия, макулодистрофия, рост и метастазирование опухолей, болезнь, связанная с ангиогенезом, вызываемое гриппом воспаление легких, экзема, контактный дерматит, псориаз, солнечный ожог или конъюнктивит.
5. Способ лечения простуды или респираторной вирусной инфекции, вызываемой риновирусом человека (HRV), другими энтеровирусами, коронавирусом, вирусом гриппа, вирусом парагриппа, респираторным синцитиальным вирусом или аденовирусом у нуждающегося в таком лечении человека, включающий введение указанному человеку эффективного количества соединения по п. 1.
6. Способ по п.5, где респираторная вирусная инфекция обостряет астму, обостряет хронический бронхит, обостряет хроническое заболевание, связанное с закупоркой легких, обостряет средний отит, обостряет синусит, или где респираторная вирусная инфекция связана с вторичной бактериальной инфекцией, средним отитом, синуситом или воспалением легких.
7. Соединение, которое представляет собой
4-(2,4-дифторфениламино)-6-(2,4,6-трифторфениламино)-2-метилсульфанилпиримидин-5-карбальдегид;
4-(2,4-дифторфенил)-6-(2,4-дифторфениламино)-2-метилсульфанилпиримидин-5-карбальдегид;
4-(2-фторфенил)-6-(2,4,6-трифторфениламино)-2-метилсульфанилпиримидин-5-карбальдегид;
4-(4-фторфенил)-6-(2,4,6-трифторфениламино)-2-метилсульфанилпиримидин-5-карбальдегид;
4-(2-фторфенил)-6-(2,4-дифторфениламино)-2-метилсульфанилпиримидин-5-карбальдегид;
4-(2,4-дифторфенил)-6-(4-фторфениламино)-2-метилсульфанилпиримидин-5-карбальдегид;
4-(2,4-дифторфенил)-6-(2,4-дифторфениламино)-2-метилсульфанилпиримидин-5-карбальдегид;
4-(2-хлор-4-фторфенил)-6-(2,4-дифторфениламино)-2-метилсульфанилпиримидин-5-карбальдегид; или
4-(2,4-дифторфенил)-6-(2,3-дифторфениламино)-2-метилсульфанилпиримидин-5-карбальдегид.
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PE20100741A1 (es) | 2005-03-25 | 2010-11-25 | Glaxo Group Ltd | COMPUESTOS DERIVADOS DE 3,4-DIHIDROPIRIMIDO[4,5-d]PIRIMIDIN-2(1H)-ONA COMO INHIBIDORES DE QUINASA p38 |
WO2006104917A2 (en) | 2005-03-25 | 2006-10-05 | Glaxo Group Limited | Process for preparing pyrido[2,3-d]pyrimidin-7-one and 3,4-dihydropyrimido[4,5-d]pyrimidin-2(1h)-one derivatives |
-
2003
- 2003-04-18 PL PL03373339A patent/PL373339A1/xx unknown
- 2003-04-18 CN CNA038087936A patent/CN1646131A/zh active Pending
- 2003-04-18 MX MXPA04010267A patent/MXPA04010267A/es unknown
- 2003-04-18 US US10/511,770 patent/US7629350B2/en not_active Expired - Fee Related
- 2003-04-18 AU AU2003225072A patent/AU2003225072A1/en not_active Abandoned
- 2003-04-18 CA CA002482022A patent/CA2482022A1/en not_active Abandoned
- 2003-04-18 RU RU2004133811/04A patent/RU2004133811A/ru not_active Application Discontinuation
- 2003-04-18 BR BR0309053-1A patent/BR0309053A/pt not_active IP Right Cessation
- 2003-04-18 JP JP2003585724A patent/JP4603268B2/ja not_active Expired - Fee Related
- 2003-04-18 AT AT03721779T patent/ATE370952T1/de not_active IP Right Cessation
- 2003-04-18 DE DE60315826T patent/DE60315826T2/de not_active Expired - Lifetime
- 2003-04-18 KR KR10-2004-7016716A patent/KR20040103972A/ko not_active Application Discontinuation
- 2003-04-18 ES ES03721779T patent/ES2291630T3/es not_active Expired - Lifetime
- 2003-04-18 WO PCT/US2003/012127 patent/WO2003088972A1/en active IP Right Grant
- 2003-04-18 EP EP03721779A patent/EP1499320B1/en not_active Expired - Lifetime
-
2004
- 2004-10-14 IL IL16460604A patent/IL164606A0/xx unknown
- 2004-10-15 IS IS7507A patent/IS7507A/is unknown
- 2004-11-18 NO NO20045025A patent/NO20045025L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
KR20040103972A (ko) | 2004-12-09 |
BR0309053A (pt) | 2005-02-22 |
PL373339A1 (en) | 2005-08-22 |
US7629350B2 (en) | 2009-12-08 |
MXPA04010267A (es) | 2005-02-03 |
CN1646131A (zh) | 2005-07-27 |
JP4603268B2 (ja) | 2010-12-22 |
EP1499320A4 (en) | 2006-05-17 |
EP1499320B1 (en) | 2007-08-22 |
AU2003225072A1 (en) | 2003-11-03 |
ATE370952T1 (de) | 2007-09-15 |
DE60315826T2 (de) | 2008-05-21 |
NO20045025L (no) | 2004-11-18 |
US20060293348A1 (en) | 2006-12-28 |
IS7507A (is) | 2004-10-15 |
EP1499320A1 (en) | 2005-01-26 |
CA2482022A1 (en) | 2003-10-30 |
JP2005529877A (ja) | 2005-10-06 |
DE60315826D1 (de) | 2007-10-04 |
ES2291630T3 (es) | 2008-03-01 |
WO2003088972A1 (en) | 2003-10-30 |
IL164606A0 (en) | 2005-12-18 |
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