JP2010532387A5 - - Google Patents
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- JP2010532387A5 JP2010532387A5 JP2010515270A JP2010515270A JP2010532387A5 JP 2010532387 A5 JP2010532387 A5 JP 2010532387A5 JP 2010515270 A JP2010515270 A JP 2010515270A JP 2010515270 A JP2010515270 A JP 2010515270A JP 2010532387 A5 JP2010532387 A5 JP 2010532387A5
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- Prior art keywords
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- 150000001875 compounds Chemical class 0.000 claims description 103
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- -1 CH 2 F Chemical compound 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 6
- 238000010511 deprotection reaction Methods 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 238000007306 functionalization reaction Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 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 description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003566 oxetanyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 2
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 claims description 2
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 230000003463 hyperproliferative effect Effects 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 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 group 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 description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 5
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 description 12
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94814707P | 2007-07-05 | 2007-07-05 | |
| US60/948,147 | 2007-07-05 | ||
| PCT/US2008/069147 WO2009006569A1 (en) | 2007-07-05 | 2008-07-03 | Pyrimidyl cyclopentanes as akt protein kinase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013249824A Division JP2014040489A (ja) | 2007-07-05 | 2013-12-03 | Ａｋｔプロテインキナーゼ阻害剤としてのピリミジルシクロペンタン |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010532387A JP2010532387A (ja) | 2010-10-07 |
| JP2010532387A5 true JP2010532387A5 (en:Method) | 2012-07-26 |
| JP5542282B2 JP5542282B2 (ja) | 2014-07-09 |
Family
ID=39830222
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010515270A Active JP5542282B2 (ja) | 2007-07-05 | 2008-07-03 | Ａｋｔプロテインキナーゼ阻害剤としてのピリミジルシクロペンタン |
| JP2013249824A Withdrawn JP2014040489A (ja) | 2007-07-05 | 2013-12-03 | Ａｋｔプロテインキナーゼ阻害剤としてのピリミジルシクロペンタン |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013249824A Withdrawn JP2014040489A (ja) | 2007-07-05 | 2013-12-03 | Ａｋｔプロテインキナーゼ阻害剤としてのピリミジルシクロペンタン |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8377937B2 (en:Method) |
| EP (2) | EP2404907B1 (en:Method) |
| JP (2) | JP5542282B2 (en:Method) |
| KR (2) | KR101624361B1 (en:Method) |
| CN (1) | CN101918373B (en:Method) |
| AT (1) | ATE522509T1 (en:Method) |
| AU (1) | AU2008272832B2 (en:Method) |
| BR (1) | BRPI0813993A2 (en:Method) |
| CA (1) | CA2692506C (en:Method) |
| ES (1) | ES2533557T3 (en:Method) |
| IL (1) | IL202617A0 (en:Method) |
| MX (1) | MX2009014013A (en:Method) |
| SI (1) | SI2173723T1 (en:Method) |
| WO (1) | WO2009006569A1 (en:Method) |
| ZA (1) | ZA200908901B (en:Method) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| SG185274A1 (en) * | 2007-07-05 | 2012-11-29 | Array Biopharma Inc | Pyrimidyl cyclopentanes as akt protein kinase inhibitors |
| CN101959887B (zh) | 2008-01-08 | 2013-07-31 | 阵列生物制药公司 | 作为激酶抑制剂的吡咯并吡啶 |
| WO2009089462A1 (en) | 2008-01-09 | 2009-07-16 | Array Biopharma Inc. | 5h-cyclopenta[d]pyrimidines as akt protein kinase inhibitors |
| CN101965347B (zh) | 2008-01-09 | 2013-01-02 | 阵列生物制药公司 | 作为激酶抑制剂的吡唑并吡啶 |
| KR101624752B1 (ko) | 2008-01-09 | 2016-05-26 | 어레이 바이오파마 인크. | Ａｋｔ 단백질 키나제 저해물질로써의 수산화된 피리미딜 시클로펜탄 |
| GB201110546D0 (en) * | 2011-06-22 | 2011-08-03 | Imp Innovations Ltd | Compositions |
| PL2861583T3 (pl) * | 2012-05-17 | 2016-12-30 | Sposób wytwarzania hydroksylowanych związków cyklopentylopirymidyny | |
| WO2017156350A1 (en) | 2016-03-09 | 2017-09-14 | K-Gen, Inc. | Methods of cancer treatment |
| EP3532464A4 (en) | 2016-10-28 | 2020-07-08 | Icahn School of Medicine at Mount Sinai | COMPOSITIONS AND METHODS FOR THE TREATMENT OF EZH2 MEDIATION CANCER |
| WO2018106870A1 (en) | 2016-12-08 | 2018-06-14 | Icahn School Of Medicine At Mount Sinai | Compositions and methods for treating cdk4/6-mediated cancer |
| JP2021515013A (ja) * | 2018-03-06 | 2021-06-17 | アイカーン スクール オブ メディスン アット マウント シナイ | セリンスレオニンキナーゼ（ａｋｔ）分解／破壊化合物および使用方法 |
| EP3810145A4 (en) | 2018-06-21 | 2022-06-01 | Icahn School of Medicine at Mount Sinai | Wd40 repeat domain protein 5 (wdr5) degradation / disruption compounds and methods of use |
| US12465648B2 (en) | 2019-05-06 | 2025-11-11 | Icahn School Of Medicine At Mount Sinai | Heterobifunctional compounds as degraders of HPK1 |
| MX2022011188A (es) | 2020-03-17 | 2022-11-08 | Jiangsu Hengrui Pharmaceuticals Co Ltd | Derivado biciclico fusionado, metodo de preparacion y uso farmaceutico del mismo. |
| CN113444110B (zh) * | 2020-03-25 | 2023-05-12 | 江苏恒瑞医药股份有限公司 | 四氢吡咯并吡唑类衍生物、其制备方法及其在医药上的应用 |
| US12103924B2 (en) | 2020-06-01 | 2024-10-01 | Icahn School Of Medicine At Mount Sinai | Mitogen-activated protein kinase kinase (MEK) degradation compounds and methods of use |
| JP2024535857A (ja) | 2021-09-17 | 2024-10-02 | 江▲蘇▼恒瑞医▲薬▼股▲フン▼有限公司 | 縮合二環系誘導体の薬学的に許容される塩、結晶及びそれらの調製方法 |
| CN116514739B (zh) * | 2023-05-09 | 2025-07-22 | 天津绿菱气体股份有限公司 | 一种1,4-二甲基哌嗪及其制备方法 |
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-
2008
- 2008-07-03 KR KR1020107002547A patent/KR101624361B1/ko not_active Expired - Fee Related
- 2008-07-03 SI SI200830441T patent/SI2173723T1/sl unknown
- 2008-07-03 JP JP2010515270A patent/JP5542282B2/ja active Active
- 2008-07-03 ES ES11169324.8T patent/ES2533557T3/es active Active
- 2008-07-03 US US12/667,850 patent/US8377937B2/en active Active
- 2008-07-03 MX MX2009014013A patent/MX2009014013A/es not_active Application Discontinuation
- 2008-07-03 WO PCT/US2008/069147 patent/WO2009006569A1/en not_active Ceased
- 2008-07-03 CN CN2008801058708A patent/CN101918373B/zh active Active
- 2008-07-03 BR BRPI0813993-8A patent/BRPI0813993A2/pt not_active Application Discontinuation
- 2008-07-03 EP EP11169324.8A patent/EP2404907B1/en active Active
- 2008-07-03 EP EP08781340.8A patent/EP2173723B3/en active Active
- 2008-07-03 CA CA2692506A patent/CA2692506C/en not_active Expired - Fee Related
- 2008-07-03 KR KR1020157020348A patent/KR20150091196A/ko not_active Ceased
- 2008-07-03 AU AU2008272832A patent/AU2008272832B2/en not_active Ceased
- 2008-07-03 AT AT08781340T patent/ATE522509T1/de not_active IP Right Cessation
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2009
- 2009-12-09 IL IL202617A patent/IL202617A0/en unknown
- 2009-12-14 ZA ZA2009/08901A patent/ZA200908901B/en unknown
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2013
- 2013-12-03 JP JP2013249824A patent/JP2014040489A/ja not_active Withdrawn
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