KR100827503B1 - 이바브라딘 히드로클로라이드의 γd-결정형, 이의 제조 방법 및 이를 함유하는 약제학적 조성물 - Google Patents
이바브라딘 히드로클로라이드의 γd-결정형, 이의 제조 방법 및 이를 함유하는 약제학적 조성물 Download PDFInfo
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- KR100827503B1 KR100827503B1 KR1020060018727A KR20060018727A KR100827503B1 KR 100827503 B1 KR100827503 B1 KR 100827503B1 KR 1020060018727 A KR1020060018727 A KR 1020060018727A KR 20060018727 A KR20060018727 A KR 20060018727A KR 100827503 B1 KR100827503 B1 KR 100827503B1
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- hydrochloride
- expressed
- crystalline form
- ivabradin
- line
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Analysing Materials By The Use Of Radiation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
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Abstract
Description
선 번호 | 각 2 θ(°) | 높이(계수) | 영역(계수 × °) | FWHM(°) | 결정면간 거리(Å) |
1 | 4.3 | 1077 | 124 | 0.1171 | 20.633 |
2 | 6.9 | 132 | 70 | 0.5353 | 12.787 |
3 | 8.4 | 269 | 35 | 0.1338 | 10.482 |
4 | 10.6 | 322 | 26 | 0.0836 | 8.310 |
5 | 11.9 | 733 | 97 | 0.1338 | 7.414 |
6 | 12.5 | 1406 | 278 | 0.2007 | 7.069 |
7 | 13.4 | 2975 | 442 | 0.1506 | 6.619 |
8 | 14.4 | 825 | 122 | 0.1506 | 6.134 |
9 | 15.8 | 1036 | 205 | 0.2007 | 5.598 |
10 | 16.3 | 540 | 107 | 0.2007 | 5.450 |
11 | 16.9 | 1007 | 183 | 0.184 | 5.233 |
12 | 17.8 | 499 | 58 | 0.1171 | 4.978 |
13 | 18.9 | 1062 | 140 | 0.1338 | 4.686 |
14 | 19.8 | 570 | 85 | 0.1506 | 4.485 |
15 | 20.2 | 549 | 63 | 0.1171 | 4.399 |
16 | 20.9 | 2565 | 635 | 0.2509 | 4.241 |
17 | 21.6 | 531 | 105 | 0.2007 | 4.104 |
18 | 22.3 | 213 | 35 | 0.1673 | 3.981 |
19 | 23.4 | 278 | 27 | 0.1004 | 3.807 |
20 | 24.1 | 1404 | 185 | 0.1338 | 3.694 |
21 | 24.4 | 1526 | 176 | 0.1171 | 3.650 |
22 | 24.8 | 676 | 100 | 0.1506 | 3.591 |
23 | 25.4 | 702 | 139 | 0.2007 | 3.504 |
24 | 26.2 | 1737 | 401 | 0.2342 | 3.403 |
25 | 26.8 | 258 | 51 | 0.2007 | 3.331 |
26 | 27.2 | 182 | 24 | 0.1338 | 3.282 |
27 | 27.9 | 838 | 249 | 0.3011 | 3.193 |
28 | 29.1 | 152 | 20 | 0.1338 | 3.071 |
선 번호 | 각 2 θ(°) | 높이(계수) | 영역(계수 × °) | FWHM(°) | 결정면간 거리(Å) |
1 | 4.3 | 1077 | 124 | 0.1171 | 20.633 |
2 | 6.9 | 132 | 70 | 0.5353 | 12.787 |
3 | 8.4 | 269 | 35 | 0.1338 | 10.482 |
4 | 10.6 | 322 | 26 | 0.0836 | 8.310 |
5 | 11.9 | 733 | 97 | 0.1338 | 7.414 |
6 | 12.5 | 1406 | 278 | 0.2007 | 7.069 |
7 | 13.4 | 2975 | 442 | 0.1506 | 6.619 |
8 | 14.4 | 825 | 122 | 0.1506 | 6.134 |
9 | 15.8 | 1036 | 205 | 0.2007 | 5.598 |
10 | 16.3 | 540 | 107 | 0.2007 | 5.450 |
11 | 16.9 | 1007 | 183 | 0.184 | 5.233 |
12 | 17.8 | 499 | 58 | 0.1171 | 4.978 |
13 | 18.9 | 1062 | 140 | 0.1338 | 4.686 |
14 | 19.8 | 570 | 85 | 0.1506 | 4.485 |
15 | 20.2 | 549 | 63 | 0.1171 | 4.399 |
16 | 20.9 | 2565 | 635 | 0.2509 | 4.241 |
17 | 21.6 | 531 | 105 | 0.2007 | 4.104 |
18 | 22.3 | 213 | 35 | 0.1673 | 3.981 |
19 | 23.4 | 278 | 27 | 0.1004 | 3.807 |
20 | 24.1 | 1404 | 185 | 0.1338 | 3.694 |
21 | 24.4 | 1526 | 176 | 0.1171 | 3.650 |
22 | 24.8 | 676 | 100 | 0.1506 | 3.591 |
23 | 25.4 | 702 | 139 | 0.2007 | 3.504 |
24 | 26.2 | 1737 | 401 | 0.2342 | 3.403 |
25 | 26.8 | 258 | 51 | 0.2007 | 3.331 |
26 | 27.2 | 182 | 24 | 0.1338 | 3.282 |
27 | 27.9 | 838 | 249 | 0.3011 | 3.193 |
28 | 29.1 | 152 | 20 | 0.1338 | 3.071 |
Claims (7)
- 패널리티컬 엑스퍼트 프로(PANalytical X'Pert Pro) 회절분석기와 엑스셀러레이터(X'Celerator) 검출기를 사용하여 측정되고, 선 위치(브래그 각(Bragg's angle) 2 θ, °로 표시됨), 선 높이(계수로 표시됨), 선 영역(계수 × °로 표시됨), 반높이에서의 선 폭("FWHM", °로 표시됨) 및 결정면간 거리 d(Å으로 표시됨)로 표현된 하기의 분말 X-선 회절(powder X-ray diffraction) 도표를 특징으로 하는, 하기 화학식(Ⅰ)의 γd-결정형의 이바브라딘 히드로클로라이드:
선 번호 각 2 θ(°) 높이(계수) 영역(계수 × °) FWHM(°) 결정면간 거리(Å) 1 4.3 1077 124 0.1171 20.633 2 6.9 132 70 0.5353 12.787 3 8.4 269 35 0.1338 10.482 4 10.6 322 26 0.0836 8.310 5 11.9 733 97 0.1338 7.414 6 12.5 1406 278 0.2007 7.069 7 13.4 2975 442 0.1506 6.619 8 14.4 825 122 0.1506 6.134 9 15.8 1036 205 0.2007 5.598 10 16.3 540 107 0.2007 5.450 11 16.9 1007 183 0.184 5.233 12 17.8 499 58 0.1171 4.978 13 18.9 1062 140 0.1338 4.686 14 19.8 570 85 0.1506 4.485 15 20.2 549 63 0.1171 4.399 16 20.9 2565 635 0.2509 4.241 17 21.6 531 105 0.2007 4.104 18 22.3 213 35 0.1673 3.981 19 23.4 278 27 0.1004 3.807 20 24.1 1404 185 0.1338 3.694 21 24.4 1526 176 0.1171 3.650 22 24.8 676 100 0.1506 3.591 23 25.4 702 139 0.2007 3.504 24 26.2 1737 401 0.2342 3.403 25 26.8 258 51 0.2007 3.331 26 27.2 182 24 0.1338 3.282 27 27.9 838 249 0.3011 3.193 28 29.1 152 20 0.1338 3.071 - 이바브라딘 히드로클로라이드 및 2-에톡시에탄올의 혼합물, 이바브라딘 히드로클로라이드, 2-에톡시에탄올 및 물의 혼합물, 또는 이바브라딘 히드로클로라이드, 에탄올 및 물의 혼합물을 용해가 완결될 때까지 가열한 후, 결정화가 완결될 때까지 냉각시키고, 수득된 결정을 여과하여 수거하고, 탈수시킴을 특징으로 하는, γd-결정형의 이바브라딘 히드로클로라이드를 제조하는 방법.
- 제 2 항에 있어서, 이바브라딘 히드로클로라이드 용액이 냉각 단계 동안 시딩(seeding)됨을 특징으로 하는 방법.
- 활성 성분으로서 제 1 항에 따른 γd-결정형의 이바브라딘 히드로클로라이드와 하나 이상의 약제학적으로 허용되는 비활성의 무독성 담체를 포함하는 서맥제(bradycardics)로 사용되는 약제학적 조성물.
- 삭제
- 삭제
- 활성 성분으로서 제 1 항에 따른 γd-결정형의 이바브라딘 히드로클로라이드와 하나 이상의 약제학적으로 허용되는 비활성의 무독성 담체를 포함하는 심근 허혈, 협심증, 심근경색증, 리듬 장애, 심실위 리듬 장애 또는 심부전을 치료 또는 예방하기 위한 약제학적 조성물.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0501990A FR2882556B1 (fr) | 2005-02-28 | 2005-02-28 | Forme cristalline gamma d du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
FR05.01990 | 2005-02-28 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20060095503A KR20060095503A (ko) | 2006-08-31 |
KR100827503B1 true KR100827503B1 (ko) | 2008-05-06 |
Family
ID=34954879
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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KR1020060018727A KR100827503B1 (ko) | 2005-02-28 | 2006-02-27 | 이바브라딘 히드로클로라이드의 γd-결정형, 이의 제조 방법 및 이를 함유하는 약제학적 조성물 |
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Families Citing this family (29)
Publication number | Priority date | Publication date | Assignee | Title |
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FR2868777B1 (fr) * | 2004-04-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
FR2882553B1 (fr) * | 2005-02-28 | 2007-05-04 | Servier Lab | Forme cristalline beta du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
FR2882554B1 (fr) * | 2005-02-28 | 2007-05-04 | Servier Lab | Forme critalline beta d du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
FR2882556B1 (fr) * | 2005-02-28 | 2007-05-04 | Servier Lab | Forme cristalline gamma d du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
FR2882555B1 (fr) * | 2005-02-28 | 2007-05-04 | Servier Lab | Forme cristalline gamma du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
FR2891827B1 (fr) * | 2005-10-11 | 2007-12-28 | Servier Lab | Forme cristalline deltad du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
FR2891826B1 (fr) * | 2005-10-11 | 2007-12-28 | Servier Lab | Forme cristalline 6 du chlorhydrate de l'ivabradine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
FR2894825B1 (fr) * | 2005-12-21 | 2010-12-03 | Servier Lab | Nouvelle association d'un inhibiteur du courant if sinusal et d'un inhibiteur de l'enzyme de conversion et les compositions pharmaceutiques qui la contiennent |
EP2460797A3 (en) | 2006-11-30 | 2012-12-05 | Cadila Healthcare Limited | Process for preparation of ivabradine hydrochloride |
CN101353325B (zh) * | 2007-07-27 | 2011-11-09 | 上海优拓医药科技有限公司 | 稳定型盐酸伊伐布雷定结晶及其制备方法 |
US8212026B2 (en) | 2007-05-30 | 2012-07-03 | Ind-Swift Laboratories Limited | Process for the preparation of ivabradine hydrochloride and polymorph thereof |
ES2402765T3 (es) | 2008-12-22 | 2013-05-08 | Krka, D.D., Novo Mesto | Procedimiento de preparación de ivabradina |
CN101774969B (zh) | 2009-01-13 | 2012-07-04 | 江苏恒瑞医药股份有限公司 | 硫酸伊伐布雷定及其i型结晶的制备方法 |
SI23290A (sl) | 2010-02-12 | 2011-08-31 | Krka D.D., Novo Mesto | Nove oblike ivabradin hidroklorida |
HUP1000245A2 (en) | 2010-05-07 | 2011-11-28 | Richter Gedeon Nyrt | Industrial process for the production ivabradin salts |
WO2012025940A1 (en) | 2010-08-25 | 2012-03-01 | Cadila Healthcare Limited | Polymorphic form of ivabradine hydrochloride and process for preparation thereof |
WO2013017582A1 (en) | 2011-08-02 | 2013-02-07 | Sandoz Ag | Acetone solvate of ivabradine hydrochloride |
EP2589594A1 (en) | 2011-11-04 | 2013-05-08 | Urquima S.A. | Ivabradine hydrochloride Form IV |
EP2773621B1 (en) | 2011-11-04 | 2015-12-30 | Synthon BV | A process for making crystalline delta-form of ivabradine hydrochloride |
US9120755B2 (en) | 2011-11-14 | 2015-09-01 | Cadila Healthcare Limited | Polymorphic forms of ivabradine hydrochloride |
EP2948432B1 (en) | 2013-01-24 | 2018-09-19 | Synthon BV | Process for making ivabradine |
CZ305096B6 (cs) | 2013-10-02 | 2015-04-29 | Zentiva, K.S. | Pevná forma Ivabradin hydrochloridu a (S)-mandlové kyseliny a její farmaceutická kompozice |
ES2672472T3 (es) | 2013-12-12 | 2018-06-14 | Synthon Bv | Composición farmacéutica que comprende ivabradina amorfa |
EP2774606B1 (en) | 2014-02-14 | 2019-01-30 | Synthon B.V. | Pharmaceutical composition comprising ivabradine hydrochloride polymorph IV |
CZ305436B6 (cs) | 2014-07-10 | 2015-09-16 | Zentiva, K.S. | Pevná forma Ivabradin hydrochloridu a (R)-mandlové kyseliny a její farmaceutická kompozice |
TWI598360B (zh) * | 2016-12-19 | 2017-09-11 | 義守大學 | Fsbm重組蛋白及其用途 |
TR201703066A2 (tr) | 2017-02-28 | 2018-09-21 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | İvabradi̇ni̇n kati oral farmasöti̇k kompozi̇syonlari |
EP3366282A1 (en) | 2017-02-28 | 2018-08-29 | Sanovel Ilac Sanayi ve Ticaret A.S. | Solid oral pharmaceutical compositions of ivabradine |
IT202000025312A1 (it) | 2020-10-26 | 2022-04-26 | Cambrex Profarmaco Milano S R L | Processi per la preparazione di polimorfi di ivabradina hcl |
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US5296481A (en) | 1990-08-29 | 1994-03-22 | Humanetics Corporation | Treatment process for promoting weight loss employing a substituted Δ5 |
KR100542472B1 (ko) | 2000-12-26 | 2006-01-11 | 르 라보레또레 쎄르비에르 | 이바브라딘의 조절 방출을 위한 열성형가능한 고체 약제조성물 |
KR20060042116A (ko) * | 2004-04-13 | 2006-05-12 | 르 라보레또레 쎄르비에르 | 이바브라딘 및 이와 약제학적으로 허용되는 산과의 부가염을 합성하는 방법 |
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US534859A (en) * | 1895-02-26 | Condenser for ice-machines | ||
DE3119874A1 (de) * | 1981-05-19 | 1982-12-09 | Dr. Karl Thomae Gmbh, 7950 Biberach | "benzazepinderivate, ihre herstellung und ihre verwendung als arzneimittel" |
DE3418270A1 (de) * | 1984-05-17 | 1985-11-21 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue aminotetralinderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
FR2681862B1 (fr) * | 1991-09-27 | 1993-11-12 | Adir Cie | Nouvelles (benzocycloalkyl)alkylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent. |
FR2882553B1 (fr) * | 2005-02-28 | 2007-05-04 | Servier Lab | Forme cristalline beta du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
FR2882555B1 (fr) * | 2005-02-28 | 2007-05-04 | Servier Lab | Forme cristalline gamma du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
FR2882554B1 (fr) * | 2005-02-28 | 2007-05-04 | Servier Lab | Forme critalline beta d du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
FR2882556B1 (fr) * | 2005-02-28 | 2007-05-04 | Servier Lab | Forme cristalline gamma d du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
FR2891826B1 (fr) * | 2005-10-11 | 2007-12-28 | Servier Lab | Forme cristalline 6 du chlorhydrate de l'ivabradine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
FR2891827B1 (fr) * | 2005-10-11 | 2007-12-28 | Servier Lab | Forme cristalline deltad du chlorhydrate de l'ivabradine, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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US5296481A (en) | 1990-08-29 | 1994-03-22 | Humanetics Corporation | Treatment process for promoting weight loss employing a substituted Δ5 |
KR100542472B1 (ko) | 2000-12-26 | 2006-01-11 | 르 라보레또레 쎄르비에르 | 이바브라딘의 조절 방출을 위한 열성형가능한 고체 약제조성물 |
KR20060042116A (ko) * | 2004-04-13 | 2006-05-12 | 르 라보레또레 쎄르비에르 | 이바브라딘 및 이와 약제학적으로 허용되는 산과의 부가염을 합성하는 방법 |
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