RU2016147508A - Способ получения AZD5363 (варианты) и применяемое в нем новое промежуточное соединение - Google Patents
Способ получения AZD5363 (варианты) и применяемое в нем новое промежуточное соединение Download PDFInfo
- Publication number
- RU2016147508A RU2016147508A RU2016147508A RU2016147508A RU2016147508A RU 2016147508 A RU2016147508 A RU 2016147508A RU 2016147508 A RU2016147508 A RU 2016147508A RU 2016147508 A RU2016147508 A RU 2016147508A RU 2016147508 A RU2016147508 A RU 2016147508A
- Authority
- RU
- Russia
- Prior art keywords
- azd5363
- salt
- pyrrolo
- pyrimidin
- diazaspiro
- Prior art date
Links
- JDUBGYFRJFOXQC-KRWDZBQOSA-N 4-amino-n-[(1s)-1-(4-chlorophenyl)-3-hydroxypropyl]-1-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide Chemical compound C1([C@H](CCO)NC(=O)C2(CCN(CC2)C=2C=3C=CNC=3N=CN=2)N)=CC=C(Cl)C=C1 JDUBGYFRJFOXQC-KRWDZBQOSA-N 0.000 title claims 9
- 238000000034 method Methods 0.000 title claims 7
- 150000001875 compounds Chemical class 0.000 title claims 2
- 150000003839 salts Chemical class 0.000 claims 10
- MCVJPGUKMSRBRG-UHFFFAOYSA-N 8-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-3-oxa-1,8-diazaspiro[4.5]decane-2,4-dione Chemical compound O=C1NC2(CCN(CC2)C2=NC=NC3=C2C=CN3)C(=O)O1 MCVJPGUKMSRBRG-UHFFFAOYSA-N 0.000 claims 5
- JGNACDMQJLVKIU-VIFPVBQESA-N (3s)-3-amino-3-(4-chlorophenyl)propan-1-ol Chemical compound OCC[C@H](N)C1=CC=C(Cl)C=C1 JGNACDMQJLVKIU-VIFPVBQESA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims 1
- 235000015497 potassium bicarbonate Nutrition 0.000 claims 1
- 239000011736 potassium bicarbonate Substances 0.000 claims 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical group [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/438—The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Claims (15)
1. Способ получения AZD5363 или соли AZD5363, включающий
(a) реакцию 8-(7H-пирроло[2,3-d]пиримидин-4-ил)-3-окса-1,8-диазаспиро[4.5]декан-2,4-диона:
или его соли с (S)-3-амино-3-(4-хлорфенил)пропан-1-олом или его солью в присутствии основания и
(b) выделение AZD5363 или AZD5363 в виде соли.
2. Способ получения AZD5363 или соли AZD5363, включающий
(a) реакцию соединения 4-(алкилоксикарбониламино)-1-(7Н-пирроло[2,3-d]пиримидин-4-ил)пиперидин-4-карбоновой кислоты или его соли с циклизующим агентом с получением 8-(7H-пирроло[2,3-d]пиримидин-4-ил)-3-окса-1,8-диазаспиро[4.5]декан-2,4-диона,
(b) взаимодействие 8-(7H-пирроло[2,3-d]пиримидин-4-ил)-3-окса-1,8-диазаспиро[4.5]декан-2,4-диона с (S)-3-амино-3-(4-хлорфенил)пропан-1-олом или его солью в присутствии основания и затем
(c) выделение AZD5363 или AZD5363 в виде соли.
3. Способ по пп. 1 или 2, в котором основание представляет собой одно или более неорганических оснований.
4. Способ по п. 3, в котором основанием является бикарбонат калия.
5. Способ по любому из .п. 1-4, в котором реакция 8-(7Н-пирроло[2,3-d]пиримидин-4-ил)-3-окса-1,8-диазаспиро[4.5]декан-2,4-диона
или его соли с (S)-3-амино-3-(4-хлорфенил)пропан-1-олом проходит в присутствии растворителя.
6. Способ по п. 5, в котором растворитель представляет собой смесь ацетонитрила и воды.
7. 8-(7Н-пирроло[2,3-d]пиримидин-4-ил)-3-окса-1,8-диазаспиро[4.5]-декан-2,4-дион или его соль.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462003593P | 2014-05-28 | 2014-05-28 | |
| US62/003,593 | 2014-05-28 | ||
| PCT/GB2015/051525 WO2015181532A1 (en) | 2014-05-28 | 2015-05-26 | Processes for the preparation of azd5363 and novel intermediate used therein |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2016147508A true RU2016147508A (ru) | 2018-06-28 |
| RU2016147508A3 RU2016147508A3 (ru) | 2018-10-29 |
| RU2674027C2 RU2674027C2 (ru) | 2018-12-04 |
Family
ID=53268840
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2016147508A RU2674027C2 (ru) | 2014-05-28 | 2015-05-26 | Способ получения AZD5363 (варианты) и применяемое в нем новое промежуточное соединение |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US9879017B2 (ru) |
| EP (1) | EP3148998B1 (ru) |
| JP (1) | JP6538725B2 (ru) |
| KR (1) | KR102518994B1 (ru) |
| CN (1) | CN106661033B (ru) |
| AR (1) | AR100648A1 (ru) |
| AU (1) | AU2015265696B2 (ru) |
| BR (1) | BR112016026641B1 (ru) |
| CA (1) | CA2948444C (ru) |
| ES (1) | ES2691223T3 (ru) |
| IL (1) | IL248848B (ru) |
| MX (1) | MX2016015613A (ru) |
| MY (1) | MY173661A (ru) |
| RU (1) | RU2674027C2 (ru) |
| TW (1) | TWI687421B (ru) |
| WO (1) | WO2015181532A1 (ru) |
| ZA (1) | ZA201608823B (ru) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6948345B2 (ja) * | 2016-04-29 | 2021-10-13 | イオメット ファーマ リミテッド | インドールアミン２，３−ジオキシゲナーゼ及び／又はトリプトファン−２，３−ジオキシゲナーゼの阻害薬としての新規置換イミダゾピリジン化合物 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4179569A (en) * | 1975-03-14 | 1979-12-18 | Janssen Pharmaceutica N.V. | N-(4-piperidinyl)-N-phenylamides |
| ZA842658B (en) * | 1983-04-11 | 1985-11-27 | Janssen Pharmaceutica Nv | N-aryl-alpha-amino-carboxamides |
| US4675403A (en) * | 1985-10-16 | 1987-06-23 | American Home Products Corporation | 3-Aminoalkyl derivatives of 5,5-disubstituted hydantoins with psychotropic activity |
| MX2007014619A (es) * | 2005-05-20 | 2009-02-13 | Vertex Pharma | Pirrolopiridinas de utilidad como inhibidores de proteina quinasa. |
| GB0608184D0 (en) * | 2006-04-25 | 2006-06-07 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| FR2913978B1 (fr) * | 2007-03-21 | 2009-07-03 | Centre Nat Rech Scient | Procede de synthese de peptides sans solvant |
| SI2201012T1 (sl) * | 2007-10-11 | 2014-10-30 | Astrazeneca Ab | Derivati pirolo(2,3-D)pirimidina kot inhibitorji proteina kinaze B |
| US8349899B1 (en) * | 2008-12-03 | 2013-01-08 | Arrowhead Center, Inc. | Selective inhibitors of EG5 motors and methods of use |
| TWI466885B (zh) * | 2009-07-31 | 2015-01-01 | Japan Tobacco Inc | 含氮螺環化合物及其醫藥用途 |
| ES2646759T3 (es) | 2011-09-12 | 2017-12-15 | Merck Patent Gmbh | Derivados de aminopirimidina para uso como moduladores de la actividad de la quinasa |
| AU2013204533B2 (en) * | 2012-04-17 | 2017-02-02 | Astrazeneca Ab | Crystalline forms |
-
2015
- 2015-05-26 ES ES15725113.3T patent/ES2691223T3/es active Active
- 2015-05-26 MX MX2016015613A patent/MX2016015613A/es active IP Right Grant
- 2015-05-26 BR BR112016026641-2A patent/BR112016026641B1/pt active IP Right Grant
- 2015-05-26 US US15/313,631 patent/US9879017B2/en active Active
- 2015-05-26 AU AU2015265696A patent/AU2015265696B2/en active Active
- 2015-05-26 CN CN201580034606.XA patent/CN106661033B/zh active Active
- 2015-05-26 CA CA2948444A patent/CA2948444C/en active Active
- 2015-05-26 EP EP15725113.3A patent/EP3148998B1/en active Active
- 2015-05-26 JP JP2016569688A patent/JP6538725B2/ja active Active
- 2015-05-26 MY MYPI2016704347A patent/MY173661A/en unknown
- 2015-05-26 WO PCT/GB2015/051525 patent/WO2015181532A1/en active Application Filing
- 2015-05-26 KR KR1020167032702A patent/KR102518994B1/ko active IP Right Grant
- 2015-05-26 RU RU2016147508A patent/RU2674027C2/ru active
- 2015-05-27 TW TW104117034A patent/TWI687421B/zh active
- 2015-05-28 AR ARP150101689A patent/AR100648A1/es unknown
-
2016
- 2016-11-09 IL IL248848A patent/IL248848B/en active IP Right Grant
- 2016-12-21 ZA ZA2016/08823A patent/ZA201608823B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2015265696B2 (en) | 2018-01-18 |
| US20170210745A1 (en) | 2017-07-27 |
| AR100648A1 (es) | 2016-10-19 |
| ZA201608823B (en) | 2018-11-28 |
| RU2674027C2 (ru) | 2018-12-04 |
| ES2691223T3 (es) | 2018-11-26 |
| WO2015181532A1 (en) | 2015-12-03 |
| MX2016015613A (es) | 2017-04-13 |
| BR112016026641A2 (pt) | 2017-08-15 |
| CA2948444C (en) | 2022-07-26 |
| KR20170012250A (ko) | 2017-02-02 |
| IL248848A0 (en) | 2017-01-31 |
| CN106661033A (zh) | 2017-05-10 |
| EP3148998A1 (en) | 2017-04-05 |
| BR112016026641B1 (pt) | 2023-03-14 |
| CA2948444A1 (en) | 2015-12-03 |
| KR102518994B1 (ko) | 2023-04-05 |
| JP2017516790A (ja) | 2017-06-22 |
| MY173661A (en) | 2020-02-14 |
| IL248848B (en) | 2020-01-30 |
| TW201609739A (zh) | 2016-03-16 |
| CN106661033B (zh) | 2018-11-06 |
| US9879017B2 (en) | 2018-01-30 |
| JP6538725B2 (ja) | 2019-07-03 |
| TWI687421B (zh) | 2020-03-11 |
| AU2015265696A1 (en) | 2016-11-24 |
| EP3148998B1 (en) | 2018-07-11 |
| RU2016147508A3 (ru) | 2018-10-29 |
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