RU2018109979A - Способ получения бензоксазепиновых соединений - Google Patents
Способ получения бензоксазепиновых соединений Download PDFInfo
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- RU2018109979A RU2018109979A RU2018109979A RU2018109979A RU2018109979A RU 2018109979 A RU2018109979 A RU 2018109979A RU 2018109979 A RU2018109979 A RU 2018109979A RU 2018109979 A RU2018109979 A RU 2018109979A RU 2018109979 A RU2018109979 A RU 2018109979A
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- ZCXLTWVZYXBHJS-UHFFFAOYSA-N 1,2-benzoxazepine Chemical class O1N=CC=CC2=CC=CC=C12 ZCXLTWVZYXBHJS-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 28
- 239000003153 chemical reaction reagent Substances 0.000 claims 7
- 229910052763 palladium Inorganic materials 0.000 claims 5
- 101150003085 Pdcl gene Proteins 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims 1
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 claims 1
- BEUQXVWXFDOSAQ-UHFFFAOYSA-N 2-methyl-2-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]propanamide Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(N=C2)C(C)(C)C(N)=O)C3=N1 BEUQXVWXFDOSAQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 239000004793 Polystyrene Substances 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 239000012445 acidic reagent Substances 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- FMVJYQGSRWVMQV-UHFFFAOYSA-N ethyl propiolate Chemical compound CCOC(=O)C#C FMVJYQGSRWVMQV-UHFFFAOYSA-N 0.000 claims 1
- 239000011521 glass Substances 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- KMZGTOZTSHNTTM-UHFFFAOYSA-N n'-(propan-2-ylamino)ethanimidamide Chemical compound CC(C)NN=C(C)N KMZGTOZTSHNTTM-UHFFFAOYSA-N 0.000 claims 1
- 229920002223 polystyrene Polymers 0.000 claims 1
- 239000011148 porous material Substances 0.000 claims 1
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical compound CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Classifications
-
- 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
- C07D498/04—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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4162—1,2-Diazoles condensed with 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (47)
1. Способ получения (2-(4-(2-(1-изопропил-3-метил-1H-1,2,4-триазол-5-ил)-5,6-дигидробензо[f]имидазо[1,2-d][1,4]оксазепин-9-ил)-1H-пиразол-1-ил)-2-метилпропанамида I, имеющего структуру:
и его стереоизомеров, геометрических изомеров, таутомеров и фармацевтически приемлемых солей, согласно которому:
(a) подвергают взаимодействию IV и 4,4,4',4',5,5,5',5'-октаметил-2,2'-би(1,3,2-диоксаборолан) с образованием 22:
(b) подвергают взаимодействию 22, палладиевый катализатор и III с образованием 23:
(c) подвергают взаимодействию 23 с водным основным реагентом с образованием II:
(d) подвергают взаимодействию II с ацил-активирующим реагентом, затем с аммиаком с образованием I.
2. Способ по п. 1, где IV получают в ходе взаимодействия 17:
с бромирующим реагентом.
3. Способ по п. 1 или 2, где палладиевый катализатор выбран из PdCl2(PPh3)2, Pd(t-Bu)3, PdCl2 dppf CH2Cl2, Pd(PPh3)4, Pd(OAc)/PPh3, Cl2Pd[(Pet3)]2, Pd(DIPHOS)2, Cl2Pd(Bipy), [PdCl(Ph2PCH2PPh2)]2, Cl2Pd[P(o-толил)3]2, Pd2(dba)3/P(o-толил)3, Pd2(dba)/P(фурил)3, Cl2Pd[P(фурил)3]2, Cl2Pd(PMePh2)2, Cl2Pd[P(4-F-Ph)3]2, Cl2Pd[P(C6F6)3]2, Cl2Pd[P(2-COOH-Ph)(Ph)2]2, Cl2Pd[P(4-COOH-Ph)(Ph)2]2, и инкапсулированных катализаторов Pd EnCat™ 30, Pd EnCat™ TPP30 и Pd(II)EnCat™ BINAP30.
4. Способ по любому из пп. 1-3, где палладий отделяют от I с помощью твердого адсорбирующего акцептора палладия.
5. Способ по п. 4, где твердый адсорбирующий акцептор палладия выбран из силикагеля, стекла с контролируемым размером пор и слабосшитого полистирола.
6. Способ по любому из пп. 1-5, где получают III, согласно которому:
(a) подвергают взаимодействию V с 2-гидроксиэтилирующим реагентом с образованием 14:
(b) подвергают взаимодействию 14 с водным основным реагентом с образованием V.
7. Способ по любому из пп. 1-5, где получают III, согласно которому:
(a) подвергают взаимодействию 28 с ацетамидином с образованием 29:
(b) подвергают взаимодействию 29 с изопропилгидразином и кислотным реагентом с образованием III.
8. Способ по любому из пп. 1-5, где получают III, согласно которому подвергают взаимодействию 28 с N'-изопропилацетогидразонамидом 6 с образованием III:
9. Способ по п. 7, где получают 28, согласно которому:
(a) подвергают взаимодействию 11 с гидроксиламином с образованием 24:
(b) подвергают взаимодействию 24 с этилпропиолатом с образованием 25:
(c) нагревают 25 с образованием 26:
(d) подвергают взаимодействию 26 с 2-гидроксиэтилирующим реагентом с образованием 27:
и
(e) подвергают взаимодействию 27 с водным основным реагентом с образованием 28.
10. Соединение, выбранное из структур:
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361779619P | 2013-03-13 | 2013-03-13 | |
| US61/779,619 | 2013-03-13 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015138488A Division RU2649976C2 (ru) | 2013-03-13 | 2014-03-12 | Способ получения бензоксазепиновых соединений |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2018109979A true RU2018109979A (ru) | 2019-02-28 |
Family
ID=50241450
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015138488A RU2649976C2 (ru) | 2013-03-13 | 2014-03-12 | Способ получения бензоксазепиновых соединений |
| RU2018109979A RU2018109979A (ru) | 2013-03-13 | 2014-03-12 | Способ получения бензоксазепиновых соединений |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015138488A RU2649976C2 (ru) | 2013-03-13 | 2014-03-12 | Способ получения бензоксазепиновых соединений |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US9303043B2 (ru) |
| EP (3) | EP3404032A3 (ru) |
| JP (6) | JP6363120B2 (ru) |
| KR (3) | KR20180070715A (ru) |
| CN (2) | CN105377856B (ru) |
| AR (1) | AR095365A1 (ru) |
| AU (3) | AU2014230812B2 (ru) |
| BR (1) | BR112015020716A2 (ru) |
| CA (6) | CA2897618A1 (ru) |
| HK (1) | HK1215433A1 (ru) |
| IL (1) | IL240793A0 (ru) |
| MX (1) | MX2015011438A (ru) |
| NZ (1) | NZ711192A (ru) |
| RU (2) | RU2649976C2 (ru) |
| SG (2) | SG11201507394RA (ru) |
| WO (1) | WO2014140073A1 (ru) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015091305A1 (en) * | 2013-12-16 | 2015-06-25 | F. Hoffmann-La Roche Ag | Polymorphs of 2-(4-(2-(1-isopropyl-3-methyl-1h-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)-1h-pyrazol-1-yl)-2-methylpropanamide, methods of production, and pharmaceutical uses thereof |
| TW202108592A (zh) * | 2015-07-02 | 2021-03-01 | 瑞士商赫孚孟拉羅股份公司 | 苯并氧氮呯噁唑啶酮化合物及其用途 |
| CN107995911B (zh) | 2015-07-02 | 2020-08-04 | 豪夫迈·罗氏有限公司 | 苯并氧氮杂*噁唑烷酮化合物及其使用方法 |
| CN105906635A (zh) * | 2016-06-08 | 2016-08-31 | 上海大学 | 全氟烷基苯并氮杂*并喹喔啉衍生物及其合成方法 |
| MX2019001228A (es) * | 2016-07-29 | 2019-06-03 | Japan Tobacco Inc | Metodo de produccion del compuesto de pirazol-amida. |
| TW201813963A (zh) | 2016-09-23 | 2018-04-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201825465A (zh) | 2016-09-23 | 2018-07-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201815787A (zh) | 2016-09-23 | 2018-05-01 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| SI3555107T1 (sl) | 2016-12-15 | 2021-07-30 | F. Hoffmann-La Roche Ag | Postopek za pripravo (S)-2-((2-((S)-4(difluorometil)-2-oksooksazolidin-3-il)-5,6-dihidrobenzo (f)imidazo(1,2-d)(1,4)oksazepin-9-il)amino) propanamida |
| CN108752237A (zh) * | 2018-07-05 | 2018-11-06 | 四川青木制药有限公司 | 一种对氨基苯甲脒盐酸盐的新制备方法 |
| US20220040324A1 (en) | 2018-12-21 | 2022-02-10 | Daiichi Sankyo Company, Limited | Combination of antibody-drug conjugate and kinase inhibitor |
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| GB9208135D0 (en) | 1992-04-13 | 1992-05-27 | Ludwig Inst Cancer Res | Polypeptides having kinase activity,their preparation and use |
| US5846824A (en) | 1994-02-07 | 1998-12-08 | Ludwig Institute For Cancer Research | Polypeptides having kinase activity, their preparation and use |
| US6274327B1 (en) | 1992-04-13 | 2001-08-14 | Ludwig Institute For Cancer Research | Polypeptides having kinase activity, their preparation and use |
| EP1123281B1 (en) * | 1998-10-23 | 2003-10-22 | Dow AgroSciences LLC | 3-(substituted phenyl)-5-(substituted cyclopropyl)-1,2,4-triazole compounds |
| KR20040024564A (ko) | 2001-07-12 | 2004-03-20 | 아베시아 리미티드 | 마이크로캡슐화된 촉매, 이의 제조 방법 및 이의 사용 방법 |
| DE60208815T2 (de) * | 2001-10-12 | 2006-07-20 | Bayer Pharmaceuticals Corp., West Haven | Phenyl substituierte 5-gliedrige stickstoff enthaltende heterocyclen zur behandlung von fettleibigkeit |
| WO2007056170A2 (en) | 2005-11-02 | 2007-05-18 | Bayer Healthcare Ag | Pyrrolo[2,1-f] [1,2,4] triazin-4-ylamines igf-1r kinase inhibitors for the treatment of cancer and other hyperproliferative diseases |
| KR101083177B1 (ko) | 2006-10-23 | 2011-11-11 | 에스지엑스 파마슈티컬스, 인코포레이티드 | 트리아졸로-피리다진 단백질 키나제 조정제 |
| DK2084162T3 (da) * | 2006-10-23 | 2012-10-01 | Sgx Pharmaceuticals Inc | Bicykliske triazoler som proteinkinasemodulatorer |
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| US8354528B2 (en) * | 2007-10-25 | 2013-01-15 | Genentech, Inc. | Process for making thienopyrimidine compounds |
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| KR101626996B1 (ko) | 2008-03-31 | 2016-06-02 | 제넨테크, 인크. | 벤조피란 및 벤족세핀 ｐｉ３ｋ 저해제 화합물 및 이의 사용 방법 |
| GB0810902D0 (en) | 2008-06-13 | 2008-07-23 | Astex Therapeutics Ltd | New compounds |
| US8263633B2 (en) | 2009-09-28 | 2012-09-11 | F. Hoffman-La Roche Ag | Benzoxepin PI3K inhibitor compounds and methods of use |
| ES2444779T3 (es) | 2009-09-28 | 2014-02-26 | F. Hoffmann-La Roche Ag | Compuestos de benzoxazepina inhibidores de la PI3K y su utilización en el tratamiento de cáncer |
| AU2010313469A1 (en) * | 2009-10-29 | 2012-06-07 | Merck Sharp & Dohme Corp. | Bridged Bicyclic Piperidine Derivatives and methods of use thereof |
| CN102558167A (zh) * | 2010-12-29 | 2012-07-11 | 中国医学科学院药物研究所 | Gk和ppar双重激动活性的噻唑烷二酮衍生物 |
| EP2688891B1 (en) * | 2011-03-21 | 2017-11-15 | F. Hoffmann-La Roche AG | Benzoxazepin compounds selective for pi3k p110 delta and methods of use |
| NO3175985T3 (ru) * | 2011-07-01 | 2018-04-28 | ||
| NZ702244A (en) * | 2012-06-08 | 2017-06-30 | Hoffmann La Roche | Mutant selectivity and combinations of a phosphoinositide 3 kinase inhibitor compound and chemotherapeutic agents for the treatment of cancer |
-
2014
- 2014-03-12 AU AU2014230812A patent/AU2014230812B2/en not_active Ceased
- 2014-03-12 CA CA2897618A patent/CA2897618A1/en not_active Abandoned
- 2014-03-12 KR KR1020187016976A patent/KR20180070715A/ko not_active Application Discontinuation
- 2014-03-12 BR BR112015020716A patent/BR112015020716A2/pt not_active Application Discontinuation
- 2014-03-12 WO PCT/EP2014/054786 patent/WO2014140073A1/en active Application Filing
- 2014-03-12 US US14/205,634 patent/US9303043B2/en active Active
- 2014-03-12 RU RU2015138488A patent/RU2649976C2/ru not_active IP Right Cessation
- 2014-03-12 RU RU2018109979A patent/RU2018109979A/ru not_active Application Discontinuation
- 2014-03-12 CA CA3005103A patent/CA3005103A1/en not_active Abandoned
- 2014-03-12 CA CA2948765A patent/CA2948765A1/en not_active Abandoned
- 2014-03-12 AR ARP140100904A patent/AR095365A1/es unknown
- 2014-03-12 EP EP18173513.5A patent/EP3404032A3/en active Pending
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