RU2486181C2 - Пиримидилциклопентаны как ингибиторы акт-протеинкиназ - Google Patents
Пиримидилциклопентаны как ингибиторы акт-протеинкиназ Download PDFInfo
- Publication number
- RU2486181C2 RU2486181C2 RU2010103813/04A RU2010103813A RU2486181C2 RU 2486181 C2 RU2486181 C2 RU 2486181C2 RU 2010103813/04 A RU2010103813/04 A RU 2010103813/04A RU 2010103813 A RU2010103813 A RU 2010103813A RU 2486181 C2 RU2486181 C2 RU 2486181C2
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- RU
- Russia
- Prior art keywords
- compound according
- alkyl
- phenyl
- paragraph
- fluoro
- Prior art date
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- -1 Pyrimidyl cyclopentanes Chemical class 0.000 title claims 22
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title abstract 2
- 239000003197 protein kinase B inhibitor Substances 0.000 title abstract 2
- 239000003909 protein kinase inhibitor Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract 37
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract 6
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract 5
- 125000004429 atom Chemical group 0.000 claims abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 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 abstract 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 2
- 125000001041 indolyl group Chemical group 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- MOZRQQTUYAYCQT-FQEVSTJZSA-N n-[[(3s)-3-amino-1-(5-ethyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl]methyl]-2,4-difluorobenzamide Chemical compound C([C@]1(CCN(C1)C=1N=CN=C2NC=C(C=12)CC)N)NC(=O)C1=CC=C(F)C=C1F MOZRQQTUYAYCQT-FQEVSTJZSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 abstract 2
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000003463 hyperproliferative effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 0 CC(C1)c2c(N(CC3)CCN3C(C(CCCCN)c3cc(*)c(*)cc3)=O)ncnc2C1O Chemical compound CC(C1)c2c(N(CC3)CCN3C(C(CCCCN)c3cc(*)c(*)cc3)=O)ncnc2C1O 0.000 description 6
- FSRSVUZZWCRRDS-UHFFFAOYSA-N CC(C1)c2c(N(CC3)CCN3C(C(CNCCOC)c(cc3)ccc3Cl)=O)ncnc2C1O Chemical compound CC(C1)c2c(N(CC3)CCN3C(C(CNCCOC)c(cc3)ccc3Cl)=O)ncnc2C1O FSRSVUZZWCRRDS-UHFFFAOYSA-N 0.000 description 1
- RZAGAOSSFREPSR-UHFFFAOYSA-N CCCNCC(C(N(CC1)CCN1c1c(C(C)CC2O)c2ncn1)=O)c([s]1)ccc1Cl Chemical compound CCCNCC(C(N(CC1)CCN1c1c(C(C)CC2O)c2ncn1)=O)c([s]1)ccc1Cl RZAGAOSSFREPSR-UHFFFAOYSA-N 0.000 description 1
- LQQYZKBYMLCQFF-HZPDHXFCSA-N CCCNC[C@@H](C(N(CC1)CCN1c1c([C@H](C)CC2)c2ncn1)=O)c([s]1)ccc1Br Chemical compound CCCNC[C@@H](C(N(CC1)CCN1c1c([C@H](C)CC2)c2ncn1)=O)c([s]1)ccc1Br LQQYZKBYMLCQFF-HZPDHXFCSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- A61P25/00—Drugs for disorders of the nervous system
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- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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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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- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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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
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- A—HUMAN NECESSITIES
- 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
-
- A—HUMAN NECESSITIES
- 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
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Communicable Diseases (AREA)
- Dermatology (AREA)
- Oncology (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Child & Adolescent Psychology (AREA)
- Psychology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94813807P | 2007-07-05 | 2007-07-05 | |
| US60/948,138 | 2007-07-05 | ||
| US2008808P | 2008-01-09 | 2008-01-09 | |
| US61/020,088 | 2008-01-09 | ||
| PCT/US2008/069144 WO2009006567A2 (en) | 2007-07-05 | 2008-07-03 | Pyrimidyl cyclopentanes as akt protein kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2010103813A RU2010103813A (ru) | 2011-08-10 |
| RU2486181C2 true RU2486181C2 (ru) | 2013-06-27 |
Family
ID=40076864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010103813/04A RU2486181C2 (ru) | 2007-07-05 | 2008-07-03 | Пиримидилциклопентаны как ингибиторы акт-протеинкиназ |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8618097B2 (OSRAM) |
| EP (1) | EP2170863B1 (OSRAM) |
| JP (2) | JP5628028B2 (OSRAM) |
| KR (2) | KR101650956B1 (OSRAM) |
| CN (2) | CN103396409B (OSRAM) |
| AR (1) | AR067413A1 (OSRAM) |
| AU (1) | AU2008272830B8 (OSRAM) |
| BR (1) | BRPI0813999A2 (OSRAM) |
| CA (1) | CA2692502C (OSRAM) |
| CO (1) | CO6251283A2 (OSRAM) |
| CR (1) | CR11229A (OSRAM) |
| EC (1) | ECSP109937A (OSRAM) |
| ES (1) | ES2551352T3 (OSRAM) |
| MA (1) | MA31679B1 (OSRAM) |
| NZ (1) | NZ582692A (OSRAM) |
| RU (1) | RU2486181C2 (OSRAM) |
| SG (1) | SG185274A1 (OSRAM) |
| TW (1) | TWI450720B (OSRAM) |
| WO (1) | WO2009006567A2 (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2805511C2 (ru) * | 2018-04-04 | 2023-10-18 | Эрвинэс Оперейшнс, Инк. | Модуляторы протеолиза и соответствующие способы применения |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5235887B2 (ja) | 2006-09-20 | 2013-07-10 | アエリー ファーマシューティカルズ インコーポレイテッド | Ｒｈｏキナーゼ阻害剤 |
| US8455513B2 (en) | 2007-01-10 | 2013-06-04 | Aerie Pharmaceuticals, Inc. | 6-aminoisoquinoline compounds |
| US9409886B2 (en) | 2007-07-05 | 2016-08-09 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| US8846683B2 (en) | 2007-07-05 | 2014-09-30 | Array Biopharma, Inc. | Pyrimidyl cyclopentanes as Akt protein kinase inhibitors |
| JP5608097B2 (ja) | 2008-01-08 | 2014-10-15 | アレイ バイオファーマ、インコーポレイテッド | キナーゼ阻害薬としてのピロロピリジン |
| PE20091315A1 (es) * | 2008-01-09 | 2009-09-21 | Array Biopharma Inc | Ciclopentanos de pirimidilo como inhibidores de la proteina cinasa akt |
| US8372842B2 (en) | 2008-01-09 | 2013-02-12 | Array Biopharma Inc. | Pyrazolopyridines as kinase inhibitors |
| AU2009204019B2 (en) | 2008-01-09 | 2014-02-20 | Array Biopharma Inc. | Hydroxylated pyrimidyl cyclopentane as AKT protein kinase inhibitor |
| EP2250155B1 (en) | 2008-01-09 | 2013-07-03 | Array Biopharma, Inc. | 5h-cyclopenta[d]pyrimidines as akt protein kinase inhibitors |
| KR101624753B1 (ko) | 2008-01-09 | 2016-05-26 | 어레이 바이오파마 인크. | Ａｋｔ 단백질 키나제 저해물질로서의 수산화된 피리미딜 시클로펜탄 |
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