RU2014151017A - Способ получения гидроксилированных циклопентилпиримидинов - Google Patents
Способ получения гидроксилированных циклопентилпиримидинов Download PDFInfo
- Publication number
- RU2014151017A RU2014151017A RU2014151017A RU2014151017A RU2014151017A RU 2014151017 A RU2014151017 A RU 2014151017A RU 2014151017 A RU2014151017 A RU 2014151017A RU 2014151017 A RU2014151017 A RU 2014151017A RU 2014151017 A RU2014151017 A RU 2014151017A
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- Russia
- Prior art keywords
- compound
- formula
- salt
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- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- 238000000034 method Methods 0.000 claims abstract 30
- 150000001875 compounds Chemical class 0.000 claims abstract 21
- 150000003839 salts Chemical class 0.000 claims abstract 20
- 239000003054 catalyst Substances 0.000 claims abstract 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 6
- 230000006315 carbonylation Effects 0.000 claims abstract 4
- 238000005810 carbonylation reaction Methods 0.000 claims abstract 4
- 238000006114 decarboxylation reaction Methods 0.000 claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract 4
- -1 Boc group Chemical group 0.000 claims abstract 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 2
- 102000004882 Lipase Human genes 0.000 claims abstract 2
- 108090001060 Lipase Proteins 0.000 claims abstract 2
- 239000004367 Lipase Substances 0.000 claims abstract 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract 2
- 235000019421 lipase Nutrition 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- 125000006239 protecting group Chemical group 0.000 claims abstract 2
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261648421P | 2012-05-17 | 2012-05-17 | |
| US61/648,421 | 2012-05-17 | ||
| US201361785281P | 2013-03-14 | 2013-03-14 | |
| US61/785,281 | 2013-03-14 | ||
| PCT/US2013/041624 WO2013173736A1 (en) | 2012-05-17 | 2013-05-17 | Process for making hydroxylated cyclopentylpyrimidine compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2014151017A true RU2014151017A (ru) | 2016-07-10 |
Family
ID=48534507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2014151017A RU2014151017A (ru) | 2012-05-17 | 2013-05-17 | Способ получения гидроксилированных циклопентилпиримидинов |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US9309204B2 (enExample) |
| EP (1) | EP2861583B1 (enExample) |
| JP (1) | JP6214636B2 (enExample) |
| KR (1) | KR20150020211A (enExample) |
| CN (1) | CN104487430B (enExample) |
| AU (1) | AU2013262568B2 (enExample) |
| BR (1) | BR112014028570A2 (enExample) |
| CA (1) | CA2873653A1 (enExample) |
| DK (1) | DK2861583T3 (enExample) |
| ES (1) | ES2588878T3 (enExample) |
| IL (1) | IL235714A0 (enExample) |
| MA (1) | MA37649B1 (enExample) |
| MX (1) | MX2014013865A (enExample) |
| PL (1) | PL2861583T3 (enExample) |
| RU (1) | RU2014151017A (enExample) |
| SG (1) | SG11201407613RA (enExample) |
| SI (1) | SI2861583T1 (enExample) |
| WO (1) | WO2013173736A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2688193C1 (ru) * | 2013-11-27 | 2019-05-21 | Саншайн Лейк Фарма Ко., Лтд. | Процессы приготовления производных дигидропиримидина и их промежуточных соединений |
| RU2712224C2 (ru) * | 2014-09-26 | 2020-01-27 | Ф. Хоффманн-Ля Рош Аг | Способы получения (циклопентил[d]пиримидин-4-ил)пиперазиновых соединений |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS60417B9 (sr) | 2012-05-17 | 2021-07-30 | Genentech Inc | Amorfni oblik aktivnog jedinjenja koje inhibira pirimidinil-ciklopentansko jedinjenje, smeše i njegove metode |
| CA2873658C (en) | 2012-05-17 | 2021-01-26 | Genentech, Inc. | Process for making amino acid compounds |
| AU2013262505B2 (en) | 2012-05-17 | 2017-09-21 | Array Biopharma Inc. | Process for making hydroxylated cyclopentylpyrimidine compounds |
| KR102123131B1 (ko) | 2012-05-17 | 2020-06-15 | 제넨테크, 인크. | 하이드록실화 사이클로펜타피리미딘 화합물 및 이의 염의 제조 방법 |
| CN105899492B (zh) | 2013-11-15 | 2021-08-24 | 豪夫迈·罗氏有限公司 | 用于制备嘧啶基环戊烷化合物的方法 |
| AU2021294219B2 (en) | 2020-06-16 | 2024-05-30 | F. Hoffmann-La Roche Ag | Process for making hydroxylated cyclopentylpyrimidine compounds |
| KR102689151B1 (ko) * | 2021-09-06 | 2024-07-29 | 연세대학교 산학협력단 | Akt 신호경로 억제제를 유효성분으로 포함하는 아토피피부염의 예방 또는 치료용 조성물 |
Family Cites Families (27)
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| WO1995015684A1 (en) | 1993-12-12 | 1995-06-15 | Agrogene, Ltd. | A novel method to protect plants from fungal infection |
| JP2001524079A (ja) | 1997-04-07 | 2001-11-27 | メルク エンド カンパニー インコーポレーテッド | ガンの治療方法 |
| US6201023B1 (en) | 1997-06-10 | 2001-03-13 | Agrogene Ltd. | Methods and compositions to protect crops against plant parasitic nematodes |
| EP0982300A3 (en) | 1998-07-29 | 2000-03-08 | Societe Civile Bioprojet | Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications |
| EP1158982A4 (en) | 1999-03-03 | 2002-06-12 | Merck & Co Inc | Prenyl protein transferase inhibitors |
| ES2239596T3 (es) * | 1999-06-03 | 2005-10-01 | Teikoku Hormone Mfg. Co., Ltd. | Compuestos de pirazol sustituidos. |
| AU7715300A (en) | 1999-09-27 | 2001-04-30 | Merck & Co., Inc. | Method of preventing osteoporosis |
| PE20050630A1 (es) | 2003-06-09 | 2005-09-22 | Boehringer Ingelheim Int | Compuestos heterociclicos como inhibidores del papiloma virus |
| BRPI0416852A (pt) | 2003-11-21 | 2007-02-27 | Array Biopharma Inc | inibidores da quinase akt |
| US8927546B2 (en) | 2006-02-28 | 2015-01-06 | Dart Neuroscience (Cayman) Ltd. | Therapeutic piperazines |
| UA95641C2 (xx) * | 2006-07-06 | 2011-08-25 | Эррей Биофарма Инк. | Гідроксильовані піримідильні циклопентани як інгібітори акт протеїнкінази$гидроксилированные пиримидильные циклопентаны как ингибиторы акт протеинкиназы |
| US8063050B2 (en) * | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| JP5157576B2 (ja) | 2007-05-14 | 2013-03-06 | 住友化学株式会社 | 光学活性２−アルキル−１，１，３−トリアルコキシカルボニルプロパンの製造方法 |
| EP2404907B1 (en) * | 2007-07-05 | 2015-01-14 | Array Biopharma, Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| US20100298289A1 (en) | 2007-10-09 | 2010-11-25 | Ucb Pharma, S.A. | Heterobicyclic compounds as histamine h4-receptor antagonists |
| KR101624753B1 (ko) * | 2008-01-09 | 2016-05-26 | 어레이 바이오파마 인크. | Ａｋｔ 단백질 키나제 저해물질로서의 수산화된 피리미딜 시클로펜탄 |
| ES2450567T3 (es) * | 2008-10-15 | 2014-03-25 | Amgen, Inc | Moduladores de GPR40 espirocíclicos |
| EP2419404B1 (en) | 2009-04-15 | 2015-11-04 | AbbVie Inc. | Anti-viral compounds |
| CN102574852B (zh) * | 2009-10-23 | 2014-06-25 | 伊莱利利公司 | Akt抑制剂 |
| PT2592933T (pt) | 2010-07-16 | 2017-05-23 | Gaweco Anderson | Inibidores de mif e suas utilizações |
| WO2012177925A1 (en) | 2011-06-21 | 2012-12-27 | The Board Institute, Inc. | Akt inhibitors for treating cancer expressing a magi3 - akt3 fusion gene |
| CA2873658C (en) | 2012-05-17 | 2021-01-26 | Genentech, Inc. | Process for making amino acid compounds |
| AU2013262505B2 (en) | 2012-05-17 | 2017-09-21 | Array Biopharma Inc. | Process for making hydroxylated cyclopentylpyrimidine compounds |
| KR102123131B1 (ko) | 2012-05-17 | 2020-06-15 | 제넨테크, 인크. | 하이드록실화 사이클로펜타피리미딘 화합물 및 이의 염의 제조 방법 |
| CA2889855A1 (en) | 2012-11-01 | 2014-05-08 | Robert S. Katz | Methods for treating fibromyalgia |
| EP2956441A4 (en) | 2013-02-18 | 2016-11-02 | Scripps Research Inst | MODULATORS OF VASOPRESSIN RECEPTORS WITH THERAPEUTIC POTENTIAL |
| US10131637B2 (en) | 2013-03-15 | 2018-11-20 | Shifa Biomedical Corporation | Anti-PCSK9 compounds and methods for the treatment and/or prevention of cardiovascular diseases |
-
2013
- 2013-05-17 ES ES13725533.7T patent/ES2588878T3/es active Active
- 2013-05-17 EP EP13725533.7A patent/EP2861583B1/en active Active
- 2013-05-17 BR BR112014028570A patent/BR112014028570A2/pt not_active IP Right Cessation
- 2013-05-17 PL PL13725533.7T patent/PL2861583T3/pl unknown
- 2013-05-17 RU RU2014151017A patent/RU2014151017A/ru not_active Application Discontinuation
- 2013-05-17 JP JP2015512890A patent/JP6214636B2/ja active Active
- 2013-05-17 MX MX2014013865A patent/MX2014013865A/es unknown
- 2013-05-17 CA CA2873653A patent/CA2873653A1/en not_active Abandoned
- 2013-05-17 CN CN201380037994.8A patent/CN104487430B/zh active Active
- 2013-05-17 SI SI201330302A patent/SI2861583T1/sl unknown
- 2013-05-17 WO PCT/US2013/041624 patent/WO2013173736A1/en not_active Ceased
- 2013-05-17 SG SG11201407613RA patent/SG11201407613RA/en unknown
- 2013-05-17 DK DK13725533.7T patent/DK2861583T3/en active
- 2013-05-17 AU AU2013262568A patent/AU2013262568B2/en not_active Ceased
- 2013-05-17 KR KR20147035262A patent/KR20150020211A/ko not_active Withdrawn
- 2013-05-17 MA MA37649A patent/MA37649B1/fr unknown
- 2013-05-17 US US14/401,091 patent/US9309204B2/en active Active
-
2014
- 2014-11-13 IL IL235714A patent/IL235714A0/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2688193C1 (ru) * | 2013-11-27 | 2019-05-21 | Саншайн Лейк Фарма Ко., Лтд. | Процессы приготовления производных дигидропиримидина и их промежуточных соединений |
| RU2697707C1 (ru) * | 2013-11-27 | 2019-08-19 | Саншайн Лейк Фарма Ко., Лтд. | Процессы приготовления производных соединений дигидропиримидина и их промежуточных продуктов |
| RU2697707C9 (ru) * | 2013-11-27 | 2019-10-03 | Саншайн Лейк Фарма Ко., Лтд. | Процессы приготовления производных соединений дигидропиримидина и их промежуточных продуктов |
| RU2712224C2 (ru) * | 2014-09-26 | 2020-01-27 | Ф. Хоффманн-Ля Рош Аг | Способы получения (циклопентил[d]пиримидин-4-ил)пиперазиновых соединений |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2861583B1 (en) | 2016-06-29 |
| EP2861583A1 (en) | 2015-04-22 |
| MA37649A1 (fr) | 2016-06-30 |
| BR112014028570A2 (pt) | 2018-04-24 |
| IL235714A0 (en) | 2015-02-01 |
| PL2861583T3 (pl) | 2016-12-30 |
| AU2013262568A1 (en) | 2015-01-22 |
| AU2013262568B2 (en) | 2017-08-31 |
| MX2014013865A (es) | 2015-05-07 |
| US20150099881A1 (en) | 2015-04-09 |
| JP6214636B2 (ja) | 2017-10-18 |
| DK2861583T3 (en) | 2016-10-03 |
| HK1208673A1 (en) | 2016-03-11 |
| SG11201407613RA (en) | 2015-01-29 |
| KR20150020211A (ko) | 2015-02-25 |
| CA2873653A1 (en) | 2013-11-21 |
| WO2013173736A1 (en) | 2013-11-21 |
| ES2588878T3 (es) | 2016-11-07 |
| MA37649B1 (fr) | 2017-03-31 |
| US9309204B2 (en) | 2016-04-12 |
| JP2015518837A (ja) | 2015-07-06 |
| CN104487430B (zh) | 2016-08-24 |
| SI2861583T1 (sl) | 2016-10-28 |
| CN104487430A (zh) | 2015-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20170817 |