HRP20201501T1 - Kristalni oblici 6-((6, 7-dimetoksikinazolin-4-il)oksi)-n,2-dimetilbenzofuran-3-karboksamida - Google Patents
Kristalni oblici 6-((6, 7-dimetoksikinazolin-4-il)oksi)-n,2-dimetilbenzofuran-3-karboksamida Download PDFInfo
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- HRP20201501T1 HRP20201501T1 HRP20201501TT HRP20201501T HRP20201501T1 HR P20201501 T1 HRP20201501 T1 HR P20201501T1 HR P20201501T T HRP20201501T T HR P20201501TT HR P20201501 T HRP20201501 T HR P20201501T HR P20201501 T1 HRP20201501 T1 HR P20201501T1
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- dimethoxyquinazolin
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- 102000004245 Proteasome Endopeptidase Complex Human genes 0.000 claims 1
- 108090000708 Proteasome Endopeptidase Complex Proteins 0.000 claims 1
- 229940079156 Proteasome inhibitor Drugs 0.000 claims 1
- 102000001253 Protein Kinase Human genes 0.000 claims 1
- 239000000365 Topoisomerase I Inhibitor Substances 0.000 claims 1
- 206010064930 age-related macular degeneration Diseases 0.000 claims 1
- 239000012296 anti-solvent Substances 0.000 claims 1
- 208000037976 chronic inflammation Diseases 0.000 claims 1
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000003207 proteasome inhibitor Substances 0.000 claims 1
- 108060006633 protein kinase Proteins 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 claims 1
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- 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
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- 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
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- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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Claims (15)
1. Oblik 6-((6,7-dimetoksikinazolin-4-il)oksi)-N,2-dimetilbenzofuran-3-karboksamida,
naznačen time što rendgenski difraktogram praha za Oblik I obuhvaća kutove difrakcije izražene u stupnjevima 2-theta (2θ) kod: 5,3, 10,7, 13,9, i 14,6, svaki od kutova difrakcije ima pogrešku od oko ± 0,2 stupnjeva (2θ).
2. Oblik I prema patentnom zahtjevu 1, naznačen time što rendgenski difraktogram praha za Oblik I obuhvaća kutove difrakcije izražene u stupnjevima 2-theta (2θ) kod: 5,3, 7,3, 10,7, 13,9, 14,6, i 19,9, svaki od kutova difrakcije ima pogrešku od oko ± 0,2 stupnjeva (2θ).
3. Oblik I prema patentnom zahtjevu 1, naznačen time što rendgenski difraktogram praha za Oblik I obuhvaća kutove difrakcije izražene u stupnjevima 2-theta (2θ) kod: 5,3, 7,3, 10,7, 13,9, 14,6, 16,3, i 19,9, svaki od kutova difrakcije ima pogrešku od oko ± 0,2 stupnjeva (2θ).
4. Oblik I prema patentnom zahtjevu 1, naznačen time što rendgenski difraktogram praha za Oblik I obuhvaća kutove difrakcije izražene u stupnjevima 2-theta (2θ) kod: 5,3, 7,3, 10,7, 13,9, 14,6, 16,3, 19,9, 21,1, 21,3, i 25,8, svaki od kutova difrakcije ima pogrešku od oko ± 0,2 stupnjeva (2θ).
5. Oblik I prema patentnom zahtjevu 1, naznačen time što rendgenski difraktogram praha za Oblik I obuhvaća kutove difrakcije izražene u stupnjevima 2-theta (2θ) kod: 5,3, 7,3, 10,7, 13,9, 14,6, 15,2, 16,3, 19,9, 21,1, 21,3, 23,1, 23,3, i 25,8, svaki od kutova difrakcije ima pogrešku od oko ± 0,2 stupnjeva (2θ).
6. Oblik I prema patentnom zahtjevu 1, naznačen time što Oblik I može imati rendgenski difraktogram praha kako je prikazano na Slici 1, svaki od kutova difrakcije ima pogrešku od oko ± 0,2 stupnjeva (2θ).
7. Oblik I prema bilo kojem od patentnih zahtjeva 1 do 6, naznačen time što je udio drugih kristalnih oblika 6-((6,7-dimetoksikinazolin-4-il)oksi)-N,2-dimetilbenzofuran-3-karboksamida manji od 40 masenih %, poželjno manji od 30 masenih %, poželjnije manji od 20 masenih %, poželjnije manji od 10 masenih %, poželjnije manji od 5 masenih %, ili još poželjnije manji od 1 masenih %.
8. Farmaceutski pripravak, naznačen time što sadrži učinkovitu količinu Oblika I kako je definiran u bilo kojem od patentnih zahtjeva 1 do 7, te najmanje jedan farmaceutski prihvatljiv nosač.
9. Farmaceutski pripravak prema patentnom zahtjevu 8, naznačen time što nadalje sadrži jedan ili više drugih aktivnih sastojaka;
pri čemu su navedeni jedan ili više drugih aktivnih sastojaka poželjno odabrani od anti-neoplastičnih sredstava;
poželjnije pri čemu su navedeni jedan ili više drugih aktivnih sastojaka odabrani od kemoterapijskih sredstava koja oštećuju DNK, inhibitora topoizomeraze, irinotekana, topotekana, kamptotecina, doksorubicina, inhibitora topoizomeraze II, etopozida, tenipozida, daunorubicina, alkilirajućih sredstava, melfalana, klorambucila, busulfana, tiotepa, ifosfamida, karmustina, lomustina, semustina, streptozocina, dekarbazina, metotreksata, mitomicina C, ciklofosfamida, interkalatora DNK, cisplatina, oksaliplatina, karboplatina, interkalatora DNK i generatora slobodnih radikala, bleomicina, nukleozidnih mimetika, 5-fluorouracila, kapecitibina, gemcitabina, fludarabina, citarabina, merkaptopurina, tiogvanina, pentostatina, hidroksiuree, kemoterapijskih sredstava koja ometaju staničnu replikaciju, paklitaksela, docetaksela, vinkristina, vinblastina, talidomida, CC-5013, CC-4047, inhibitora protein tirozin kinaze, imatinib mesilata, gefitiniba, inhibitora proteazoma, bortezomiba, inhibitora NF-kapa B, kinaze, protutijela koja se vežu na proteine prekomjerno eksprimirane u karcinomima i time smanjuju replikaciju stanica, rituksimab, cetuksimab i bevacizumab.
10. Oblik I kako je definiran u bilo kojem od patentnih zahtjeva 1 do 7 ili farmaceutski pripravak prema patentnom zahtjevu 8 ili 9 naznačen time što je za uporabu za liječenje bolesti povezane s inhibicijom KDR.
11. Oblik I kako je definiran u bilo kojem od patentnih zahtjeva 1 do 7 ili farmaceutski pripravak prema patentnom zahtjevu 8 ili 9 naznačen time što je za uporabu za liječenje poremećaja povezanog s angiogenezom, pri čemu je navedeni poremećaj povezan s angiogenezom poželjno izabran od karcinoma, makularne degeneracije povezane sa starenjem i kronične upalne bolesti.
12. Oblik I kako je definiran u bilo kojem od patentnih zahtjeva 1 do 7 ili farmaceutski pripravak prema patentnom zahtjevu 8 ili 9 naznačen time što je za uporabu za liječenje karcinoma koji je odabran od karcinoma pluća, raka glave i vrata, kolorektalnog karcinoma, karcinoma gušterače, karcinoma debelog crijeva, karcinoma dojke, karcinoma jajnika, karcinoma prostate, karcinoma želuca, karcinoma bubrega, karcinoma jetre, raka mozga, raka kostiju, sarkoma i leukemije, poželjno pri čemu je navedeni karcinom odabran od kolorektalnog karcinoma, karcinoma pluća, karcinoma želuca ili karcinoma bubrega.
13. Oblik I kako je definiran u bilo kojem od patentnih zahtjeva 1 do 7 naznačen time što je za uporabu za liječenje karcinoma,
pri čemu se navedeni Oblik I daje u kombinaciji sa jednim ili više drugih aktivnih sastojaka,
pri čemu su navedeni Oblik I i navedeni jedan ili više drugih aktivnih sastojaka formulirani kao zasebni pripravci ili su formulirani u istom farmaceutskom pripravku,
pri čemu su navedeni jedan ili više drugih aktivnih sastojaka poželjno odabrani od antineoplastičnih sredstava, poželjnije od kemoterapijskih sredstava koja oštećuju DNK, inhibitora topoizomeraze I, irinotekana, topotekana, kamptotecina, doksorubicina, inhibitora topoizomeraze II, etopozida, tenipozida, daunorubicina, alkilirajućih sredstava, melfalana, klorambucila, busulfana, tiotepa, ifosfamida, karmustina, lomustina, semustina, streptozocina, dekarbazina, metotreksata, mitomicina C, ciklofosfamida, interkalatora DNK, cisplatina, oksaliplatina, karboplatina, interkalatora DNK i generatora slobodnih radikala, bleomicina, nukleozidnih mimetika, 5-fluorouracila, kapecitibina, gemcitabina, fludarabina, citarabina, merkaptopurina, tiogvanina, pentostatina, hidroksiuree, kemoterapijskih sredstava koja ometaju staničnu replikaciju, paklitaksela, docetaksela, vinkristina, vinblastina, talidomida, CC-5013, CC-4047, inhibitora protein tirozin kinaze, imatinib mesilata, gefitiniba, inhibitora proteazoma, bortezomiba, inhibitora NF-kapa B, inhibitora I kapa B kinaze, protutijela koja se vežu na proteine prekomjerno eksprimirane u karcinomima i time smanjuju replikaciju stanica, rituksimab, cetuksimab i bevacizumab,
pri čemu je navedeni karcinom poželjno odabran od karcinoma pluća, raka glave i vrata, kolorektalnog karcinoma, karcinoma gušterače, karcinoma debelog crijeva, karcinoma dojke, karcinoma jajnika, karcinoma prostate, karcinoma želuca, karcinoma bubrega, karcinoma jetre, karcinoma mozga, raka kostiju, sarkoma i leukemije, poželjnije pri čemu je navedeni karcinom odabran od kolorektalnog karcinoma, karcinoma pluća, karcinoma želuca i karcinoma bubrega.
14. Postupak koji je:
(i) postupak dobivanja Oblika I prema bilo kojem od patentnih zahtjeva 1 do 7, koji sadrži:
(1) miješanje spoja 6-((6,7-dimetoksikinazolin-4-il)oksi)-N,2-dimetilbenzofuran-3-karboksamida s najmanje jednim otapalom za otapanje ili smjesom otapala za otapanje, i zagrijavanje smjese do refluksa da se dobije otopina;
pri čemu, navedeno najmanje jedno otapalo za otapanje je odabrano iz niza koji sadrži metanol, C3-6 alkanol, octenu kiselinu, i aprotonsko otapalo; navedena smjesa otapala za otapanje je odabrana od smjese dva ili više aprotonskih otapala, ili smjese organskog otapala koje se miješa s vodom i vode, u kojem je volumenski postotak organskog otapala koje se miješa s vodom u navedenoj smjesi otapala za otapanje manji od oko 50%;
(2) polagano hlađenje otopine dobivene u koraku (1) na temperaturu okoline; zatim
(3) izoliranje da se dobije krutina Oblika I 6-((6,7-dimetoksikinazolin-4-il)oksi)-N,2-dimetilbenzofuran-3-karboksamida;
(4) sušenje krutine dobivene u koraku (3); ili
(ii) postupak dobivanja Oblika I prema bilo kojem od patentnih zahtjeva 1 do 7, koji sadrži:
(1) miješanje spoja 6-((6,7-dimetoksikinazolin-4-il)oksi)-N,2-dimetilbenzofuran-3-karboksamida s najmanje jednim otapalom za otapanje, zatim zagrijavanje smjese do refluksa da se dobije prva otopina; pri čemu je navedeno otapalo za otapanje odabrano od etanola, izopropanola, acetona, diklorometana, dimetil sulfoksida, i N,N-dimetilformamida;
(2) dodavanje najmanje jednog otapala protiv otapanja u navedenu prvu otopinu da se dobije druga otopina;
(3) ostavljanje navedene druge otopine da se spontano polako ohladi na temperaturu okoline; zatim
(4) izoliranje da se dobije krutina Oblika I 6-((6,7-dimetoksikinazolin-4-il)oksi)-N,2-dimetilbenzofuran-3-karboksamida;
(5) sušenje krutine dobivene u koraku (4); ili
(iii) postupak dobivanja Oblika I prema bilo kojem od patentnih zahtjeva 1 do 7, koji sadrži:
(1) suspendiranje krutine spoja 6-((6,7-dimetoksikinazolin-4-il)oksi)-N,2-dimetilbenzofuran-3-karboksamida u odgovarajućoj količini sustava otapala; pri čemu je navedeni sustav otapala odabran između otapala za otapanje ili smjese otapala organskog otapala koje se miješa s vodom i vode, u kojem je volumni postotak organskog otapala koje se miješa s vodom u smjesi otapala manji od oko 80%;
(2) miješanje suspenzije dobivene u koraku (1) tijekom perioda vremena;
(3) izoliranje da se dobije krutina Oblika I 6-((6,7-dimetoksikinazolin-4-il)oksi)-N,2-dimetilbenzofuran-3-karboksamida;
(4) sušenje krutine dobivene u koraku (3).
15. Postupak prema patentnom zahtjevu 14, naznačen time što je otapalo za otapanje koje se koristi u koraku (1) postupka (iii) aceton.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410456350.9A CN105461702A (zh) | 2014-09-10 | 2014-09-10 | 6-(6,7-二甲氧基喹唑啉-4-基氧基)-n,2-二甲基苯并呋喃-3-甲酰胺晶型 |
| PCT/CN2015/089035 WO2016037550A1 (en) | 2014-09-10 | 2015-09-07 | Crystalline forms of 6- ( (6, 7-dimethoxyquinazolin-4-yl) oxy) -n,2-dimethylbenzofuran-3-carboxamide |
| EP15839519.4A EP3191475B1 (en) | 2014-09-10 | 2015-09-07 | Crystalline forms of 6-((6, 7-dimethoxyquinazolin-4-yl)oxy) -n,2-dimethylbenzofuran-3-carboxamide |
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| HRP20201501T1 true HRP20201501T1 (hr) | 2020-12-25 |
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| HRP20201501TT HRP20201501T1 (hr) | 2014-09-10 | 2020-09-21 | Kristalni oblici 6-((6, 7-dimetoksikinazolin-4-il)oksi)-n,2-dimetilbenzofuran-3-karboksamida |
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| US (3) | US10519142B2 (hr) |
| EP (1) | EP3191475B1 (hr) |
| JP (2) | JP6655608B2 (hr) |
| KR (2) | KR102221722B1 (hr) |
| CN (3) | CN105461702A (hr) |
| AU (1) | AU2015316010B2 (hr) |
| BR (1) | BR112017004000B1 (hr) |
| CA (1) | CA2958666C (hr) |
| CL (1) | CL2017000540A1 (hr) |
| CY (1) | CY1123892T1 (hr) |
| DK (1) | DK3191475T3 (hr) |
| EA (1) | EA034730B1 (hr) |
| ES (1) | ES2819242T3 (hr) |
| HK (1) | HK1231479A1 (hr) |
| HR (1) | HRP20201501T1 (hr) |
| HU (1) | HUE050580T2 (hr) |
| IL (1) | IL250647B (hr) |
| LT (1) | LT3191475T (hr) |
| MX (1) | MX370791B (hr) |
| MY (1) | MY176618A (hr) |
| PE (1) | PE20170661A1 (hr) |
| PH (1) | PH12017500451A1 (hr) |
| PL (1) | PL3191475T3 (hr) |
| PT (1) | PT3191475T (hr) |
| RS (1) | RS60829B1 (hr) |
| SG (1) | SG11201701544UA (hr) |
| SI (1) | SI3191475T1 (hr) |
| TW (1) | TWI718105B (hr) |
| UA (1) | UA120371C2 (hr) |
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| CN105461702A (zh) * | 2014-09-10 | 2016-04-06 | 和记黄埔医药（上海）有限公司 | 6-(6,7-二甲氧基喹唑啉-4-基氧基)-n,2-二甲基苯并呋喃-3-甲酰胺晶型 |
| WO2019062854A1 (zh) | 2017-09-29 | 2019-04-04 | 杭州领业医药科技有限公司 | 瑞博西林的共晶和瑞博西林单琥珀酸盐的共晶、其制备方法、组合物和用途 |
| CN111868054B (zh) * | 2018-03-30 | 2023-09-15 | 杭州领业医药科技有限公司 | 呋喹替尼的共晶、其制备方法、组合物和用途 |
| CN111184698A (zh) | 2018-11-15 | 2020-05-22 | 和记黄埔医药（上海）有限公司 | 呋喹替尼制剂及其应用 |
| CN113330166B (zh) | 2019-03-28 | 2023-05-05 | 住友重机械工业株式会社 | 挖土机 |
| CN113200966B (zh) * | 2021-04-06 | 2022-07-22 | 深圳大学 | 一种呋喹替尼衍生物、药物组合物和用途 |
| GB202211142D0 (en) * | 2022-07-29 | 2022-09-14 | Macfarlan Smith Ltd | Polymorphs, co-crystals and solvates of fruquintinib, processes for the preparation and use thereof |
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| US7829574B2 (en) * | 2008-05-09 | 2010-11-09 | Hutchison Medipharma Enterprises Limited | Substituted quinazoline compounds and their use in treating angiogenesis-related diseases |
| CN101575333B (zh) * | 2008-05-09 | 2011-06-22 | 和记黄埔医药（上海）有限公司 | 一种喹唑啉衍生物及其医药用途 |
| CN105461702A (zh) * | 2014-09-10 | 2016-04-06 | 和记黄埔医药（上海）有限公司 | 6-(6,7-二甲氧基喹唑啉-4-基氧基)-n,2-二甲基苯并呋喃-3-甲酰胺晶型 |
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2017
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2018
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