HRP20161163T1 - Postupak priprave 6-(7-((1-aminociklopropil)metoksi)-6-metoksikinolin-4-iloksi)-n-metil-1-naftamida i njegovih sintetičkih međuprodukata - Google Patents
Postupak priprave 6-(7-((1-aminociklopropil)metoksi)-6-metoksikinolin-4-iloksi)-n-metil-1-naftamida i njegovih sintetičkih međuprodukata Download PDFInfo
- Publication number
- HRP20161163T1 HRP20161163T1 HRP20161163TT HRP20161163T HRP20161163T1 HR P20161163 T1 HRP20161163 T1 HR P20161163T1 HR P20161163T T HRP20161163T T HR P20161163TT HR P20161163 T HRP20161163 T HR P20161163T HR P20161163 T1 HRP20161163 T1 HR P20161163T1
- Authority
- HR
- Croatia
- Prior art keywords
- methoxyquinolin
- yloxy
- methyl
- following
- benzyloxycarbonyl
- Prior art date
Links
- CUDVHEFYRIWYQD-UHFFFAOYSA-N E-3810 free base Chemical compound C=1C=C2C(C(=O)NC)=CC=CC2=CC=1OC(C1=CC=2OC)=CC=NC1=CC=2OCC1(N)CC1 CUDVHEFYRIWYQD-UHFFFAOYSA-N 0.000 title claims 2
- 239000000543 intermediate Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- -1 p-toluenesulfonyl Chemical group 0.000 claims 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- 125000005544 phthalimido group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- PWWQCOYZBLBSKL-UHFFFAOYSA-N benzyl n-[1-[(4-chloro-6-methoxyquinolin-7-yl)oxymethyl]cyclopropyl]carbamate Chemical compound COC1=CC2=C(Cl)C=CN=C2C=C1OCC1(NC(=O)OCC=2C=CC=CC=2)CC1 PWWQCOYZBLBSKL-UHFFFAOYSA-N 0.000 claims 1
- MFSAVFQBIAXKOA-UHFFFAOYSA-N benzyl n-[1-[(6-methoxy-4-oxo-1h-quinolin-7-yl)oxymethyl]cyclopropyl]carbamate Chemical compound COC1=CC2=C(O)C=CN=C2C=C1OCC1(NC(=O)OCC=2C=CC=CC=2)CC1 MFSAVFQBIAXKOA-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/44—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (4)
1. Spoj formule (XI) ili (XIa)
[image]
naznačen time da R’ jest vodik, a R je odabran od sljedećih: benzil, acetil, benzoil, trifluormetanesulfonil, benzenesulfonil, p-toluenesulfonil, metoksikarbonil, etoksikarbonil, tert-butoksikarbonil, aliloksikarbonil i benziloksikarbonil koji može biti supstituiran na aromatskom prstenu s do trima supstituentima odabrani od sljedećih: halogen, cijano i trifluorometil; ili R’ jest trimetilsilil, a R jest tert-butoksikarbonil; ili R i R’ uzeti zajedno s dušikovim atomom za koji su vezani tvore ftalimido-skupinu.
2. Spoj formule (XII)
[image]
u kojoj je X odabran od sljedećih: Cl, Br ili I te naznačen time da R’ jest vodik i R je odabran od sljedećih: benzil, acetil, benzoil, trifluormetanesulfonil, benzenesulfonil, p-toluenesulfonil, metoksikarbonil, etoksikarbonil, tert-butoksikarbonil, aliloksikarbonil i benziloksikarbonil koji može biti supstituiran na aromatskom prstenu s do trima supstituentima odabrani od sljedećih: halogen, cijano i trifluorometil; ili R’ jest trimetilsilil i R jest tert-butoksikarbonil; ili R i R’ uzeti zajedno s dušikovim atomom za koji su vezani tvore ftalimido-skupinu.
3. Spoj kako je prijavljen u bilo kojem od patentnih zahtjeva 1 ili 2 odabran od sljedećih:
1-[(4-hidroksi-6-metoksikinolin-7-iloksi)metil]-N-benziloksikarbonil-1-aminociklopropan,
1-[(4-klor-6-metoksikinolin-7-iloksi)metil]-N-benziloksikarbonil-1-aminociklopropan.
4. Upotreba spoja kako je prijavljen u patentnim zahtjevima 1 – 3 kao međuprodukt u sintezi 6-(7-((1-aminociklopropil)metoksi)-6-metoksikinolin-4-iloksi)-N-metil-1-naftamida (I) ili odgovarajuće farmaceutski prihvatljive soli.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2009A000397A IT1393351B1 (it) | 2009-03-16 | 2009-03-16 | Procedimento per la preparazione della 6-(7-((1-amminociclopropil)metossi)-6-metossichinolin-4-ilossi)-n-metil-1-naftammide e suoi intermedi di sintesi |
| EP13172499.9A EP2641897B1 (en) | 2009-03-16 | 2010-03-11 | A process for the preparation of 6-(7-((1-aminocyclopropyl)methoxy)-6-methoxyquinolin-4-yloxy)-N-methyl-1-naphthamide and synthetic intermediates thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20161163T1 true HRP20161163T1 (hr) | 2016-11-04 |
Family
ID=41210541
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20130978AT HRP20130978T1 (hr) | 2009-03-16 | 2013-10-16 | Postupak priprave 6-(7-((1-aminociklopropil)metoksi)-6-metoksikinolin-4-iloksi)-n-metil-1-naftamid i odgovarajućih sintetičkih međuprodukata |
| HRP20161163TT HRP20161163T1 (hr) | 2009-03-16 | 2016-09-12 | Postupak priprave 6-(7-((1-aminociklopropil)metoksi)-6-metoksikinolin-4-iloksi)-n-metil-1-naftamida i njegovih sintetičkih međuprodukata |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20130978AT HRP20130978T1 (hr) | 2009-03-16 | 2013-10-16 | Postupak priprave 6-(7-((1-aminociklopropil)metoksi)-6-metoksikinolin-4-iloksi)-n-metil-1-naftamid i odgovarajućih sintetičkih međuprodukata |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US8642767B2 (hr) |
| EP (3) | EP2641897B1 (hr) |
| JP (2) | JP5817079B2 (hr) |
| CN (3) | CN104193676B (hr) |
| CY (2) | CY1114503T1 (hr) |
| DK (2) | DK2641897T3 (hr) |
| ES (2) | ES2431618T3 (hr) |
| HK (2) | HK1167136A1 (hr) |
| HR (2) | HRP20130978T1 (hr) |
| HU (1) | HUE029528T2 (hr) |
| IT (1) | IT1393351B1 (hr) |
| PL (2) | PL2641897T3 (hr) |
| PT (2) | PT2641897T (hr) |
| SI (2) | SI2408739T1 (hr) |
| SM (1) | SMT201600356B (hr) |
| WO (1) | WO2010105761A1 (hr) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1393351B1 (it) | 2009-03-16 | 2012-04-20 | Eos Ethical Oncology Science Spa In Forma Abbreviata Eos Spa | Procedimento per la preparazione della 6-(7-((1-amminociclopropil)metossi)-6-metossichinolin-4-ilossi)-n-metil-1-naftammide e suoi intermedi di sintesi |
| KR102275034B1 (ko) | 2013-01-18 | 2021-07-12 | 어드밴첸 파마수티컬스, 엘엘씨 | 항-종양제 6-(7-((1-아미노시클로프로필)메톡시)-6-메톡시퀴놀린-4-일옥시)-n-메틸-1-나프타미드 및 그의 결정형을 제조하는 공정 |
| CN105311029A (zh) | 2014-06-06 | 2016-02-10 | 正大天晴药业集团股份有限公司 | 抗肿瘤活性的喹啉衍生物 |
| CN105311030B (zh) | 2014-06-06 | 2020-03-24 | 正大天晴药业集团股份有限公司 | 用于抗肿瘤的螺取代化合物 |
| WO2016010869A2 (en) | 2014-07-14 | 2016-01-21 | Advenchen Pharmaceuticals, LLC | FUSED QUINOLINE COMPUNDS AS PI3K, mTOR INHIBITORS |
| AU2015360095B2 (en) | 2014-12-09 | 2020-02-27 | Advenchen Laboratories Nanjing Ltd | Quinoline derivative against non-small cell lung cancer |
| US9751859B2 (en) | 2015-05-04 | 2017-09-05 | Advenchen Pharmaceuticals, LLC | Process for preparing an anti-cancer agent, 1-((4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxyquinolin-7-yloxy)methyl)cyclopropanamine, its crystalline form and its salts |
| AU2016293841B2 (en) | 2015-07-11 | 2020-10-08 | Advenchen Pharmaceuticals, LLC | Fused quinoline compunds as pi3k/mTor inhibitors |
| KR20180086187A (ko) | 2015-10-05 | 2018-07-30 | 더 트러스티이스 오브 콜롬비아 유니버시티 인 더 시티 오브 뉴욕 | 자가포식 유동의 활성체 및 포스포리파제 d 및 타우를 포함하는 단백질 응집물의 클리어런스 및 단백질질환의 치료 |
| CN107296811B (zh) | 2016-04-15 | 2022-12-30 | 正大天晴药业集团股份有限公司 | 一种用于治疗胃癌的喹啉衍生物 |
| CN109748902B (zh) * | 2017-11-02 | 2020-11-06 | 杭州科巢生物科技有限公司 | 一种盐酸安罗替尼的制备方法 |
| EP3766870B1 (en) | 2018-03-02 | 2023-09-27 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Crystal of compound as c-met kinase inhibitor and preparation method therefor and use thereof |
| JP2021515767A (ja) | 2018-03-07 | 2021-06-24 | バイエル・アクチエンゲゼルシヤフト | Ｅｒｋ５阻害剤の同定及び使用 |
| CN110483392A (zh) * | 2018-05-14 | 2019-11-22 | 上海海和药物研究开发有限公司 | 合成n-保护的喹啉-7-基氧基甲基环丙基胺衍生物的方法及合成中间体 |
| CN110483393A (zh) * | 2018-05-14 | 2019-11-22 | 上海海和药物研究开发有限公司 | 德立替尼的晶型 |
| CN109705093A (zh) * | 2018-12-29 | 2019-05-03 | 正大天晴药业集团股份有限公司 | 喹啉衍生物及其制备方法和用途 |
| CN115160221A (zh) * | 2022-07-26 | 2022-10-11 | 上海歆贻医药科技有限公司 | 德立替尼晶型化合物和用途 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9714432A (pt) * | 1996-12-23 | 2000-05-02 | Hoeschst Marion Roussel Inc | Derivados de 3-aril-2-(1-substituìdo-4-piperidinil)-1(1-di(oxo-3h-bezo [d]-isoatiazol, sua preparação e seu uso como moduladores de função neurotransmissora |
| EE05345B1 (et) * | 1999-02-10 | 2010-10-15 | Astrazeneca Ab | Kinasoliini derivaadid angiogeneesi inhibiitoritena |
| AU2003257666A1 (en) * | 2002-08-23 | 2004-03-11 | Kirin Beer Kabushiki Kaisha | COMPOUND HAVING TGFss INHIBITORY ACTIVITY AND MEDICINAL COMPOSITION CONTAINING THE SAME |
| BRPI0418102A (pt) * | 2003-12-23 | 2007-04-27 | Pfizer | derivados de quinolina |
| US8163923B2 (en) * | 2007-03-14 | 2012-04-24 | Advenchen Laboratories, Llc | Spiro substituted compounds as angiogenesis inhibitors |
| IT1393351B1 (it) | 2009-03-16 | 2012-04-20 | Eos Ethical Oncology Science Spa In Forma Abbreviata Eos Spa | Procedimento per la preparazione della 6-(7-((1-amminociclopropil)metossi)-6-metossichinolin-4-ilossi)-n-metil-1-naftammide e suoi intermedi di sintesi |
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2009
- 2009-03-16 IT ITMI2009A000397A patent/IT1393351B1/it active
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2010
- 2010-03-11 ES ES10712320T patent/ES2431618T3/es active Active
- 2010-03-11 PL PL13172499T patent/PL2641897T3/pl unknown
- 2010-03-11 PT PT131724999T patent/PT2641897T/pt unknown
- 2010-03-11 US US13/256,722 patent/US8642767B2/en active Active
- 2010-03-11 CN CN201410380387.8A patent/CN104193676B/zh not_active Expired - Fee Related
- 2010-03-11 PT PT10712320T patent/PT2408739E/pt unknown
- 2010-03-11 ES ES13172499.9T patent/ES2585221T3/es active Active
- 2010-03-11 EP EP13172499.9A patent/EP2641897B1/en active Active
- 2010-03-11 WO PCT/EP2010/001519 patent/WO2010105761A1/en active Application Filing
- 2010-03-11 EP EP16171791.3A patent/EP3103792A1/en not_active Withdrawn
- 2010-03-11 JP JP2012500115A patent/JP5817079B2/ja not_active Expired - Fee Related
- 2010-03-11 DK DK13172499.9T patent/DK2641897T3/en active
- 2010-03-11 HU HUE13172499A patent/HUE029528T2/en unknown
- 2010-03-11 SI SI201030383T patent/SI2408739T1/sl unknown
- 2010-03-11 EP EP10712320.0A patent/EP2408739B1/en active Active
- 2010-03-11 SI SI201031256A patent/SI2641897T1/sl unknown
- 2010-03-11 DK DK10712320.0T patent/DK2408739T3/da active
- 2010-03-11 CN CN201610565855.8A patent/CN106187882A/zh active Pending
- 2010-03-11 PL PL10712320T patent/PL2408739T3/pl unknown
- 2010-03-11 CN CN201080011948.7A patent/CN102356063B/zh not_active Expired - Fee Related
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2012
- 2012-08-14 HK HK12107948.4A patent/HK1167136A1/xx not_active IP Right Cessation
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2013
- 2013-10-16 CY CY20131100907T patent/CY1114503T1/el unknown
- 2013-10-16 HR HRP20130978AT patent/HRP20130978T1/hr unknown
- 2013-12-23 US US14/138,302 patent/US9012645B2/en not_active Expired - Fee Related
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2015
- 2015-03-18 US US14/661,105 patent/US9340508B2/en not_active Expired - Fee Related
- 2015-05-22 JP JP2015104974A patent/JP6061158B2/ja not_active Expired - Fee Related
- 2015-06-08 HK HK15105438.2A patent/HK1205105A1/xx not_active IP Right Cessation
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2016
- 2016-07-29 CY CY20161100749T patent/CY1117871T1/el unknown
- 2016-09-12 HR HRP20161163TT patent/HRP20161163T1/hr unknown
- 2016-10-06 SM SM201600356T patent/SMT201600356B/it unknown
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