RU2017128308A - Синтез ингибитора тирозинкиназы брутона - Google Patents
Синтез ингибитора тирозинкиназы брутона Download PDFInfo
- Publication number
- RU2017128308A RU2017128308A RU2017128308A RU2017128308A RU2017128308A RU 2017128308 A RU2017128308 A RU 2017128308A RU 2017128308 A RU2017128308 A RU 2017128308A RU 2017128308 A RU2017128308 A RU 2017128308A RU 2017128308 A RU2017128308 A RU 2017128308A
- Authority
- RU
- Russia
- Prior art keywords
- compound
- formula
- ibrutinib
- phenoxyphenyl
- pyrazolo
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 65
- XYFPWWZEPKGCCK-GOSISDBHSA-N ibrutinib Chemical compound C1=2C(N)=NC=NC=2N([C@H]2CN(CCC2)C(=O)C=C)N=C1C(C=C1)=CC=C1OC1=CC=CC=C1 XYFPWWZEPKGCCK-GOSISDBHSA-N 0.000 claims 62
- 238000000034 method Methods 0.000 claims 50
- 239000002177 L01XE27 - Ibrutinib Substances 0.000 claims 42
- 229960001507 ibrutinib Drugs 0.000 claims 42
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 9
- 239000002904 solvent Substances 0.000 claims 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- 238000007068 beta-elimination reaction Methods 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 3
- 230000010933 acylation Effects 0.000 claims 3
- 238000005917 acylation reaction Methods 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 150000001879 copper Chemical class 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- VSTXCZGEEVFJES-UHFFFAOYSA-N 1-cycloundecyl-1,5-diazacycloundec-5-ene Chemical group C1CCCCCC(CCCC1)N1CCCCCC=NCCC1 VSTXCZGEEVFJES-UHFFFAOYSA-N 0.000 claims 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical group CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 159000000021 acetate salts Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- -1 alkyl tin Chemical group 0.000 claims 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 229960004217 benzyl alcohol Drugs 0.000 claims 1
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000005620 boronic acid group Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical group [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 claims 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 claims 1
- 238000005406 washing Methods 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
- A61K31/495—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562103507P | 2015-01-14 | 2015-01-14 | |
| US62/103,507 | 2015-01-14 | ||
| PCT/US2016/013424 WO2016115356A1 (en) | 2015-01-14 | 2016-01-14 | Synthesis of a bruton's tyrosine kinase inhibitor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2017128308A true RU2017128308A (ru) | 2019-02-14 |
| RU2017128308A3 RU2017128308A3 (https=) | 2019-10-24 |
Family
ID=56406389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2017128308A RU2017128308A (ru) | 2015-01-14 | 2016-01-14 | Синтез ингибитора тирозинкиназы брутона |
Country Status (16)
| Country | Link |
|---|---|
| US (6) | US20180009814A1 (https=) |
| EP (1) | EP3245208A4 (https=) |
| JP (2) | JP2018502077A (https=) |
| KR (1) | KR20170102887A (https=) |
| CN (2) | CN107108640A (https=) |
| AU (2) | AU2016206693A1 (https=) |
| BR (1) | BR112017015206B1 (https=) |
| CA (2) | CA3210320A1 (https=) |
| HK (1) | HK1246293A1 (https=) |
| IL (4) | IL322449A (https=) |
| MA (1) | MA41350A (https=) |
| MX (2) | MX394327B (https=) |
| RU (1) | RU2017128308A (https=) |
| SG (2) | SG10201906517VA (https=) |
| WO (1) | WO2016115356A1 (https=) |
| ZA (1) | ZA201704338B (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2712440C2 (ru) * | 2015-02-12 | 2020-01-29 | Шанхай Дьюд Медикал Сайенс Энд Текнолоджи Ко., Лтд | Способ получения ибрутиниба |
| RU2818458C2 (ru) * | 2019-05-21 | 2024-05-02 | Янссен Фармацевтика Нв | Способы и промежуточные соединения для получения ингибитора btk |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3424505A4 (en) | 2016-03-04 | 2019-10-16 | Taiho Pharmaceutical Co., Ltd. | PREPARATION AND COMPOSITION FOR THE TREATMENT OF MALIGNANT TUMORS |
| US11883404B2 (en) | 2016-03-04 | 2024-01-30 | Taiho Pharmaceuticals Co., Ltd. | Preparation and composition for treatment of malignant tumors |
| CN109206426B (zh) * | 2017-07-06 | 2021-10-08 | 上海复星星泰医药科技有限公司 | 吡唑并嘧啶类化合物的制备方法 |
| WO2019027860A1 (en) | 2017-08-01 | 2019-02-07 | Boehringer Ingelheim International Gmbh | INTERMEDIATE COMPOUNDS AND METHODS |
| CN107814804A (zh) * | 2017-10-27 | 2018-03-20 | 广州科锐特生物科技有限公司 | 依鲁替尼的制备方法 |
| JP6918204B2 (ja) | 2018-03-19 | 2021-08-11 | 大鵬薬品工業株式会社 | アルキル硫酸ナトリウムを含む医薬組成物 |
| KR20210044736A (ko) | 2018-05-03 | 2021-04-23 | 주노 쎄러퓨티크스 인코퍼레이티드 | 키메라 항원 수용체(ｃａｒ) ｔ세포 요법과 키나제 억제제의 조합요법 |
| JP6944496B2 (ja) * | 2018-10-22 | 2021-10-06 | ファイザー・インク | ピロロ［２，３−ｄ］ピリミジントシル酸塩、その結晶形態、ならびにその製造方法および中間体 |
| KR102742083B1 (ko) | 2018-11-09 | 2024-12-16 | 다이호야쿠힌고교 가부시키가이샤 | 디메톡시벤젠 화합물의 제조 방법 |
| CN109988175A (zh) * | 2019-04-28 | 2019-07-09 | 梯尔希（南京）药物研发有限公司 | 一种依鲁替尼-d5的制备方法 |
| KR20220011669A (ko) | 2019-05-21 | 2022-01-28 | 얀센 파마슈티카 엔.브이. | Btk 억제제 제조를 위한 방법 및 중간체 |
| WO2020234381A1 (en) | 2019-05-21 | 2020-11-26 | Janssen Pharmaceutica Nv | Processes and intermediates for preparing a btk inhibitor |
| US20240092785A1 (en) | 2021-01-21 | 2024-03-21 | Synthon B.V. | Process for making ibrutinib |
| CN114853662B (zh) * | 2021-02-05 | 2024-01-12 | 四川青木制药有限公司 | 手性肼基哌啶衍生物的制备方法 |
| WO2023220655A1 (en) | 2022-05-11 | 2023-11-16 | Celgene Corporation | Methods to overcome drug resistance by re-sensitizing cancer cells to treatment with a prior therapy via treatment with a t cell therapy |
| WO2023242384A1 (en) | 2022-06-17 | 2023-12-21 | Krka, D.D., Novo Mesto | Crystalline form of ibrutinib |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4550214A (en) * | 1981-01-05 | 1985-10-29 | Polaroid Corporation | Blocked vinyl biphenyl compounds |
| US4874822A (en) * | 1988-04-07 | 1989-10-17 | Minnesota Mining And Manufacturing Company | Process for the acrylamidoacylation of alcohols |
| MXPA06007326A (es) * | 2003-12-23 | 2007-01-26 | Astex Therapeutics Ltd | Derivados de pirazol como moduladores de proteina cinasa. |
| DK2526933T3 (en) * | 2006-09-22 | 2015-05-18 | Pharmacyclics Inc | Inhibitors of Bruton's tyrosine kinase |
| SG10202107066WA (en) * | 2007-03-28 | 2021-07-29 | Pharmacyclics Llc | Inhibitors of bruton's tyrosine kinase |
| US7718662B1 (en) * | 2009-10-12 | 2010-05-18 | Pharmacyclics, Inc. | Pyrazolo-pyrimidine inhibitors of bruton's tyrosine kinase |
| JP6261580B2 (ja) * | 2012-07-30 | 2018-01-17 | コンサート ファーマシューティカルズ インコーポレイテッド | 重水素化イブルチニブ |
| CN103121999A (zh) * | 2012-08-29 | 2013-05-29 | 苏州迪飞医药科技有限公司 | 一种酪氨酸激酶抑制剂pci-32765的合成方法 |
| US9156847B2 (en) * | 2013-03-15 | 2015-10-13 | Janssen Pharmaceutica Nv | Processes and intermediates for preparing a medicament |
| US8957080B2 (en) * | 2013-04-09 | 2015-02-17 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| CN103626774B (zh) * | 2013-11-20 | 2015-11-04 | 苏州明锐医药科技有限公司 | 伊鲁替尼的制备方法 |
| CN105471823B (zh) * | 2014-09-03 | 2018-10-26 | 阿里巴巴集团控股有限公司 | 一种敏感信息处理方法、装置、服务器及安全判定系统 |
| US10266535B2 (en) * | 2015-01-21 | 2019-04-23 | Hefei Institutes Of Physical Science, Chinese Academy Of Sciences | Inhibitor of FLT3 kinase and use thereof |
-
2016
- 2016-01-13 MA MA041350A patent/MA41350A/fr unknown
- 2016-01-14 JP JP2017532649A patent/JP2018502077A/ja active Pending
- 2016-01-14 MX MX2019008815A patent/MX394327B/es unknown
- 2016-01-14 SG SG10201906517VA patent/SG10201906517VA/en unknown
- 2016-01-14 RU RU2017128308A patent/RU2017128308A/ru not_active Application Discontinuation
- 2016-01-14 CN CN201680005456.4A patent/CN107108640A/zh active Pending
- 2016-01-14 CA CA3210320A patent/CA3210320A1/en active Pending
- 2016-01-14 IL IL322449A patent/IL322449A/en unknown
- 2016-01-14 IL IL308276A patent/IL308276A/en unknown
- 2016-01-14 SG SG11201705678YA patent/SG11201705678YA/en unknown
- 2016-01-14 US US15/542,848 patent/US20180009814A1/en not_active Abandoned
- 2016-01-14 CN CN202110485400.6A patent/CN113816962A/zh active Pending
- 2016-01-14 CA CA2971460A patent/CA2971460C/en active Active
- 2016-01-14 MX MX2017009154A patent/MX366827B/es active IP Right Grant
- 2016-01-14 KR KR1020177019206A patent/KR20170102887A/ko not_active Ceased
- 2016-01-14 BR BR112017015206-1A patent/BR112017015206B1/pt active IP Right Grant
- 2016-01-14 WO PCT/US2016/013424 patent/WO2016115356A1/en not_active Ceased
- 2016-01-14 AU AU2016206693A patent/AU2016206693A1/en not_active Abandoned
- 2016-01-14 HK HK18105861.5A patent/HK1246293A1/zh unknown
- 2016-01-14 EP EP16737886.8A patent/EP3245208A4/en not_active Withdrawn
-
2017
- 2017-06-19 IL IL253020A patent/IL253020A0/en unknown
- 2017-06-26 ZA ZA2017/04338A patent/ZA201704338B/en unknown
-
2018
- 2018-12-18 US US16/224,425 patent/US20190367518A1/en not_active Abandoned
-
2019
- 2019-12-04 US US16/703,344 patent/US20200347064A1/en not_active Abandoned
-
2020
- 2020-05-17 IL IL274716A patent/IL274716A/en unknown
- 2020-09-11 AU AU2020230323A patent/AU2020230323A1/en not_active Abandoned
- 2020-10-09 JP JP2020171454A patent/JP2021035947A/ja active Pending
-
2021
- 2021-02-17 US US17/177,852 patent/US20220098200A1/en not_active Abandoned
-
2023
- 2023-06-14 US US18/209,939 patent/US20240158400A1/en not_active Abandoned
-
2024
- 2024-07-24 US US18/782,878 patent/US20250197404A1/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2712440C2 (ru) * | 2015-02-12 | 2020-01-29 | Шанхай Дьюд Медикал Сайенс Энд Текнолоджи Ко., Лтд | Способ получения ибрутиниба |
| RU2818458C2 (ru) * | 2019-05-21 | 2024-05-02 | Янссен Фармацевтика Нв | Способы и промежуточные соединения для получения ингибитора btk |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20220111 |