CA2675642A1 - Process for the preparation of 4-(6-chloro-2,3-methylenedioxyanilino)-7-[2-(4-methyl piperazin-1-yl)ethoxy]-5-tetrahydropyran-4-yloxyquinazoline, their intermediates and crystalline salts thereof - Google Patents
Process for the preparation of 4-(6-chloro-2,3-methylenedioxyanilino)-7-[2-(4-methyl piperazin-1-yl)ethoxy]-5-tetrahydropyran-4-yloxyquinazoline, their intermediates and crystalline salts thereof Download PDFInfo
- Publication number
- CA2675642A1 CA2675642A1 CA002675642A CA2675642A CA2675642A1 CA 2675642 A1 CA2675642 A1 CA 2675642A1 CA 002675642 A CA002675642 A CA 002675642A CA 2675642 A CA2675642 A CA 2675642A CA 2675642 A1 CA2675642 A1 CA 2675642A1
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- CA
- Canada
- Prior art keywords
- formula
- compound
- azd0530
- salt
- converted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 150
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
- 229960000303 topotecan Drugs 0.000 description 1
- XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 description 1
- 229960005026 toremifene Drugs 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 239000003558 transferase inhibitor Substances 0.000 description 1
- 229960000575 trastuzumab Drugs 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229960000241 vandetanib Drugs 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
- 229960002066 vinorelbine Drugs 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0427697.8 | 2004-12-17 | ||
| GBGB0427697.8A GB0427697D0 (en) | 2004-12-17 | 2004-12-17 | Chemical process |
| CA002590735A CA2590735C (en) | 2004-12-17 | 2005-12-14 | Process for the preparation of 4-(6-chloro-2,3-methylenedioxyanilino)-7-[2-(4-methylpiperazin-1-yl) ethoxy}-5-tetrahydropyran-4-yloxyquinazoline, their intermediates and crystalline salts thereof |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002590735A Division CA2590735C (en) | 2004-12-17 | 2005-12-14 | Process for the preparation of 4-(6-chloro-2,3-methylenedioxyanilino)-7-[2-(4-methylpiperazin-1-yl) ethoxy}-5-tetrahydropyran-4-yloxyquinazoline, their intermediates and crystalline salts thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2675642A1 true CA2675642A1 (en) | 2006-06-22 |
Family
ID=34090249
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002675642A Abandoned CA2675642A1 (en) | 2004-12-17 | 2005-12-14 | Process for the preparation of 4-(6-chloro-2,3-methylenedioxyanilino)-7-[2-(4-methyl piperazin-1-yl)ethoxy]-5-tetrahydropyran-4-yloxyquinazoline, their intermediates and crystalline salts thereof |
| CA002590735A Expired - Lifetime CA2590735C (en) | 2004-12-17 | 2005-12-14 | Process for the preparation of 4-(6-chloro-2,3-methylenedioxyanilino)-7-[2-(4-methylpiperazin-1-yl) ethoxy}-5-tetrahydropyran-4-yloxyquinazoline, their intermediates and crystalline salts thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002590735A Expired - Lifetime CA2590735C (en) | 2004-12-17 | 2005-12-14 | Process for the preparation of 4-(6-chloro-2,3-methylenedioxyanilino)-7-[2-(4-methylpiperazin-1-yl) ethoxy}-5-tetrahydropyran-4-yloxyquinazoline, their intermediates and crystalline salts thereof |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8304417B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1871769B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP5161584B2 (cg-RX-API-DMAC7.html) |
| KR (6) | KR20080094849A (cg-RX-API-DMAC7.html) |
| CN (1) | CN101115744B (cg-RX-API-DMAC7.html) |
| AU (2) | AU2005315458B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BRPI0519085A2 (cg-RX-API-DMAC7.html) |
| CA (2) | CA2675642A1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2622480T3 (cg-RX-API-DMAC7.html) |
| GB (1) | GB0427697D0 (cg-RX-API-DMAC7.html) |
| IL (1) | IL183525A0 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2007007210A (cg-RX-API-DMAC7.html) |
| NO (1) | NO20072755L (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ555468A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2006064217A2 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA200704532B (cg-RX-API-DMAC7.html) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0412074D0 (en) * | 2004-05-29 | 2004-06-30 | Astrazeneca Ab | Combination product |
| WO2009068906A2 (en) * | 2007-11-26 | 2009-06-04 | Astrazeneca Ab | Combinations comprising zd4054 and a src family kinase inhibitor 172 |
| CN103275072B (zh) * | 2013-05-22 | 2016-01-20 | 苏州明锐医药科技有限公司 | 塞卡替尼的制备方法 |
| US10660957B2 (en) * | 2013-06-13 | 2020-05-26 | Yale University | Compositions and methods for treating an Aβ-modulated disease or disorder or improving cognition in a subject |
| US11241434B2 (en) | 2013-06-13 | 2022-02-08 | Yale Uninversity | Compositions and methods for improving cognition in a subject |
| US10369152B2 (en) | 2015-02-13 | 2019-08-06 | The Brigham And Women's Hospital, Inc. | Methods and compositions for the treatment or prevention of abnormal bone formation in a soft tissue |
| EP3930715B1 (en) | 2019-02-27 | 2024-05-08 | Astrazeneca AB | Saracatinib for use in the treatment of idiopathic pulmonary fibrosis |
| CN116332789A (zh) * | 2023-03-10 | 2023-06-27 | 上海康鹏科技股份有限公司 | 一种4-氨基-2-氟苯甲酰胺的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA73993C2 (uk) * | 2000-06-06 | 2005-10-17 | Астразенека Аб | Хіназолінові похідні для лікування пухлин та фармацевтична композиція |
| WO2002016352A1 (en) | 2000-08-21 | 2002-02-28 | Astrazeneca Ab | Quinazoline derivatives |
| JP4307843B2 (ja) | 2001-04-19 | 2009-08-05 | アストラゼネカ アクチボラグ | キナゾリン誘導体 |
| AU2003278383B2 (en) * | 2002-11-04 | 2007-06-14 | Astrazeneca Ab | Quinazoline derivatives as Src tyrosine kinase inhibitors |
| GB0226434D0 (en) | 2002-11-13 | 2002-12-18 | Astrazeneca Ab | Combination product |
| GB0307333D0 (en) | 2003-03-29 | 2003-05-07 | Astrazeneca Ab | Therapeutic agent |
| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| GB0310401D0 (en) | 2003-05-07 | 2003-06-11 | Astrazeneca Ab | Therapeutic agent |
-
2004
- 2004-12-17 GB GBGB0427697.8A patent/GB0427697D0/en not_active Ceased
-
2005
- 2005-12-14 US US11/793,064 patent/US8304417B2/en active Active
- 2005-12-14 BR BRPI0519085-1A patent/BRPI0519085A2/pt not_active IP Right Cessation
- 2005-12-14 KR KR1020087023973A patent/KR20080094849A/ko not_active Withdrawn
- 2005-12-14 CN CN2005800476248A patent/CN101115744B/zh not_active Expired - Lifetime
- 2005-12-14 NZ NZ555468A patent/NZ555468A/en not_active IP Right Cessation
- 2005-12-14 CA CA002675642A patent/CA2675642A1/en not_active Abandoned
- 2005-12-14 ES ES05818127.2T patent/ES2622480T3/es not_active Expired - Lifetime
- 2005-12-14 AU AU2005315458A patent/AU2005315458B2/en not_active Expired
- 2005-12-14 KR KR1020077015972A patent/KR20070090004A/ko not_active Ceased
- 2005-12-14 KR KR1020087023971A patent/KR20080094847A/ko not_active Withdrawn
- 2005-12-14 KR KR1020087023972A patent/KR20080094848A/ko not_active Withdrawn
- 2005-12-14 KR KR1020117022793A patent/KR20110114727A/ko not_active Ceased
- 2005-12-14 KR KR1020087023969A patent/KR20080094846A/ko not_active Withdrawn
- 2005-12-14 EP EP05818127.2A patent/EP1871769B1/en not_active Expired - Lifetime
- 2005-12-14 WO PCT/GB2005/004807 patent/WO2006064217A2/en not_active Ceased
- 2005-12-14 JP JP2007546172A patent/JP5161584B2/ja not_active Expired - Lifetime
- 2005-12-14 MX MX2007007210A patent/MX2007007210A/es not_active Application Discontinuation
- 2005-12-14 CA CA002590735A patent/CA2590735C/en not_active Expired - Lifetime
-
2007
- 2007-05-29 IL IL183525A patent/IL183525A0/en unknown
- 2007-05-30 NO NO20072755A patent/NO20072755L/no not_active Application Discontinuation
- 2007-05-31 ZA ZA200704532A patent/ZA200704532B/en unknown
-
2008
- 2008-12-15 JP JP2008318186A patent/JP2009143920A/ja active Pending
-
2009
- 2009-02-18 AU AU2009200622A patent/AU2009200622A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1871769A2 (en) | 2008-01-02 |
| CA2590735C (en) | 2009-11-10 |
| KR20080094848A (ko) | 2008-10-24 |
| JP2009143920A (ja) | 2009-07-02 |
| NZ555468A (en) | 2010-12-24 |
| AU2009200622A1 (en) | 2009-03-12 |
| MX2007007210A (es) | 2007-11-07 |
| CA2590735A1 (en) | 2006-06-22 |
| JP5161584B2 (ja) | 2013-03-13 |
| AU2005315458A1 (en) | 2006-06-22 |
| ZA200704532B (en) | 2008-07-30 |
| GB0427697D0 (en) | 2005-01-19 |
| IL183525A0 (en) | 2007-09-20 |
| US20090099196A1 (en) | 2009-04-16 |
| WO2006064217A3 (en) | 2006-12-21 |
| CN101115744A (zh) | 2008-01-30 |
| WO2006064217A2 (en) | 2006-06-22 |
| CN101115744B (zh) | 2012-02-01 |
| KR20110114727A (ko) | 2011-10-19 |
| KR20080094846A (ko) | 2008-10-24 |
| AU2005315458B2 (en) | 2009-03-12 |
| NO20072755L (no) | 2007-07-02 |
| WO2006064217A8 (en) | 2007-07-05 |
| KR20070090004A (ko) | 2007-09-04 |
| EP1871769B1 (en) | 2017-02-22 |
| US8304417B2 (en) | 2012-11-06 |
| KR20080094849A (ko) | 2008-10-24 |
| KR20080094847A (ko) | 2008-10-24 |
| ES2622480T3 (es) | 2017-07-06 |
| JP2008524183A (ja) | 2008-07-10 |
| BRPI0519085A2 (pt) | 2008-12-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20121109 |