ME02456B - Kristalni oblik argininske soli perindoprila, postupak njene proizvodnje i farmaceutske smeše koje je sadrže - Google Patents
Kristalni oblik argininske soli perindoprila, postupak njene proizvodnje i farmaceutske smeše koje je sadržeInfo
- Publication number
- ME02456B ME02456B MEP-2016-140A MEP14016A ME02456B ME 02456 B ME02456 B ME 02456B ME P14016 A MEP14016 A ME P14016A ME 02456 B ME02456 B ME 02456B
- Authority
- ME
- Montenegro
- Prior art keywords
- polar solvent
- compound
- crystalline form
- theta
- expressed
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 3
- IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 title claims 3
- 229960002582 perindopril Drugs 0.000 title claims 3
- 125000000637 arginyl group Chemical class N[C@@H](CCCNC(N)=N)C(=O)* 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 6
- 238000000034 method Methods 0.000 claims 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical group CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 229910052802 copper Inorganic materials 0.000 claims 3
- 239000010949 copper Substances 0.000 claims 3
- 239000012454 non-polar solvent Substances 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 239000002798 polar solvent Substances 0.000 claims 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 239000002934 diuretic Substances 0.000 claims 2
- 230000001882 diuretic effect Effects 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 239000005541 ACE inhibitor Substances 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims 1
- 229930064664 L-arginine Natural products 0.000 claims 1
- 235000014852 L-arginine Nutrition 0.000 claims 1
- 125000002059 L-arginyl group Chemical class O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- NDDAHWYSQHTHNT-UHFFFAOYSA-N indapamide Chemical compound CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 NDDAHWYSQHTHNT-UHFFFAOYSA-N 0.000 claims 1
- 229960004569 indapamide Drugs 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
-
- 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
- A61P9/10—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
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (12)
1.α-Kristalni oblik L-argininske soli perindoprila formule (I):naznačen time, da su vrhovi rendgenske difrakcije u prahu mjereni korištenjem difraktometra s bakarnom antikatodom i Kβ (Ni) filtrom te je izražena putem Braggovog kuta 2 theta (°): 4.5, 7.9 i 13.5.
2.α Kristalni oblik spoja formule (I) u skladu s patentnim zahtjevom 1, naznačen time, da su vrhovi rendgenske difrakcije u prahu mjereni difraktometrom s bakrenom antikatodom i Kβ (Ni) filtrom te je izražena putem Braggovog kuta 2 theta (°): 4.5, 7.9, 13.5, 17.5 i 20.6.
3. α Kristalni oblik spoja formule (I) u skladu s patentnim zahtjevom 1, naznačen time, da je dijagram rendgenske difrakcije u prahu mjeren difraktometrom (bakarna antikatoda i Kβ (Ni) filtar) te je izražen putem interplanarne udaljenosti d, Braggovim kutom 2 theta, intenzitetom i relativnim intenzitetom (izraženo kao postotak najintenzivnije crte): Ugao 2 theta (°) Interplanarna udaljenost d (Å) Intenzitet Relativni intenzitet (%) 4.52 19.53 2211 88.7 7.94 11.12 2080 83.5 12.152 7.277 682 27.4 13.480 6.563 2492 100.0 14.029 6.308 422 16.9 14.948 5.922 552 22.1 15.873 5.579 493 19.8 17.531 5.055 1600 64.2 18.787 4.719 363 14.5 19.579 4.530 1078 43.3 20.635 4.301 1794 72.0 22.616 3.928 798 32.0 23.367 3.804 473 19.0 23.807 3.735 362 14.5 24.434 3.640 409 16.4 27.148 3.282 450 18.1 28.214 3.160 417 16.7
4.Postupak za pripravu α kristalnog oblika spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time, da je perindopril otopljen u vodi s L-argininom, a potom su dodani polarno i nepolarno otapalo a dobiveni kristali se pročišćavaju, peru i potom suše.
5.Postupak u skladu s patentnim zahtjevom 4, naznačen time, da je nepolarno otapalo odabrano od metilcikloheksana, cikloheksana i toluena.
6.Postupak u skladu bilo s patentnim zahtjevom 4 ili patentnim zahtjevom 5, naznačen time, da je polarno otapalo odabrano od dimetil sulfoksida, N,N-dimetilformamida, N,N-dimetilacetamida i N-metil-2-pirolidinona.
7.Postupak u skladu s patentnim zahtjevom 4, naznačen time, da je nepolarno otapalo metilcikloheksan a polarno otapalo je dimetil sulfoksid.
8.Farmaceutski pripravak, naznačen time, da kao djelatni sastojak sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 3 u kombinaciji s jednim ili više farmaceutski prihvatljivih, inertnih, netoksičnih nosača.
9.Farmaceutski pripravak u skladu s patentnim zahtjevom 8, naznačen time, da također sadrži diuretik.
10.Farmaceutski pripravak u skladu s patentnim zahtjevom 9, naznačen time, da je diuretik indapamid.
11.Uporaba spoja u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačena time, da je za proizvodnju lijekova za uporabu kao inhibitora enzima za prevođenje angiotenzina I.
12.Uporaba spoja u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačena time, da je za proizvodnju lijekova za uporabu u liječenju srčanožilnih bolesti.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0601748A FR2897866B1 (fr) | 2006-02-28 | 2006-02-28 | Forme cristalline alpha du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| PCT/FR2007/000335 WO2007099217A1 (fr) | 2006-02-28 | 2007-02-26 | FORME CRISTALLINE α DU SEL D'ARGININE DU PERINDOPRIL, SON PROCEDE DE PREPARATION, ET LES COMPOSITIONS PHARMACEUTIQUES QUI LA CONTIENNENT |
| EP07731039.9A EP1989182B1 (fr) | 2006-02-28 | 2007-02-26 | Forme cristalline du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ME02456B true ME02456B (me) | 2017-02-20 |
Family
ID=37022969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2016-140A ME02456B (me) | 2006-02-28 | 2007-02-26 | Kristalni oblik argininske soli perindoprila, postupak njene proizvodnje i farmaceutske smeše koje je sadrže |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7846961B2 (me) |
| EP (1) | EP1989182B1 (me) |
| JP (1) | JP5255454B2 (me) |
| KR (2) | KR20120001818A (me) |
| CN (1) | CN101389603B (me) |
| AU (1) | AU2007220435B2 (me) |
| BR (1) | BRPI0708278B8 (me) |
| CA (1) | CA2644467C (me) |
| CY (1) | CY1117753T1 (me) |
| DK (1) | DK1989182T3 (me) |
| EA (1) | EA014716B1 (me) |
| ES (1) | ES2581982T3 (me) |
| FR (1) | FR2897866B1 (me) |
| GE (1) | GEP20125433B (me) |
| HR (1) | HRP20160644T1 (me) |
| HU (1) | HUE027898T2 (me) |
| MA (1) | MA30276B1 (me) |
| ME (1) | ME02456B (me) |
| MY (1) | MY151035A (me) |
| NO (1) | NO20083535L (me) |
| NZ (1) | NZ570367A (me) |
| PL (1) | PL1989182T3 (me) |
| RS (1) | RS54754B1 (me) |
| SI (1) | SI1989182T1 (me) |
| UA (1) | UA89905C2 (me) |
| WO (1) | WO2007099217A1 (me) |
| ZA (1) | ZA200807024B (me) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8686161B2 (en) | 2008-06-24 | 2014-04-01 | Mylan Laboratories Limited | Polymorphic forms of perindopril (L)-arginine and process for the preparation thereof |
| AU2009212902A1 (en) | 2008-09-03 | 2010-03-18 | Apotex Pharmachem Inc. | Amorphous form of an L-arginine salt of perindopril and processes of preparation thereof |
| SI23149A (sl) | 2009-09-21 | 2011-03-31 | Silverstone Pharma | Nove benzatinske soli ACE inhibitorjev, postopek za njihovo pripravo in njihova uporaba za zdravljenje kardiovaskularnih bolezni |
| FR2985512B1 (fr) | 2012-01-05 | 2014-06-20 | Servier Lab | Procede de preparation du sel de l-arginine du perindopril |
| FR2985511B1 (fr) | 2012-01-05 | 2014-01-03 | Servier Lab | Forme cristalline delta du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| CN103172696B (zh) * | 2012-12-19 | 2014-12-17 | 宁波美诺华药业股份有限公司 | 一种γ晶型的培哚普利精氨酸盐的制备方法 |
| PH12018502155B1 (en) | 2016-04-20 | 2024-03-27 | Servier Lab | Pharmaceutical composition comprising a beta blocker, a converting enzyme inhibitor and an antihypertensive or an nsaid |
| EP3842035A1 (en) | 2019-12-23 | 2021-06-30 | KRKA, d.d., Novo mesto | Composition for the preparation of perindopril arginine granules, a method for their preparation and pharmaceutical composition comprising the granules |
| SI26268A (sl) | 2021-11-18 | 2023-05-31 | Zupet Rok | Postopek za pripravo hidratirane oblike perindopril l-arginina |
| CN114149357B (zh) * | 2021-12-29 | 2024-06-25 | 江苏嘉逸医药有限公司 | 一种γ晶型培哚普利精氨酸盐的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2503155A2 (fr) * | 1980-10-02 | 1982-10-08 | Science Union & Cie | Nouveaux imino diacides substitues, leurs procedes de preparation et leur emploi comme inhibiteur d'enzyme |
| FR2811319B1 (fr) * | 2000-07-06 | 2002-08-23 | Adir | Nouvelle forme cristalline beta du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2811320B1 (fr) * | 2000-07-06 | 2002-08-23 | Adir | Nouvelle forme cristalline alpha du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2811318B1 (fr) * | 2000-07-06 | 2002-08-23 | Adir | Nouvelle forme cristalline gamma du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2838648B1 (fr) * | 2002-04-18 | 2004-05-21 | Servier Lab | Nouveau sel de perindopril et les compositions pharmaceutiques qui le contiennent |
| FR2897865B1 (fr) | 2006-02-28 | 2008-04-18 | Servier Lab | Forme cristalline beta du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| US8686161B2 (en) | 2008-06-24 | 2014-04-01 | Mylan Laboratories Limited | Polymorphic forms of perindopril (L)-arginine and process for the preparation thereof |
-
2006
- 2006-02-28 FR FR0601748A patent/FR2897866B1/fr active Active
-
2007
- 2007-02-26 CA CA2644467A patent/CA2644467C/fr not_active Expired - Fee Related
- 2007-02-26 JP JP2008556812A patent/JP5255454B2/ja active Active
- 2007-02-26 RS RS20160321A patent/RS54754B1/sr unknown
- 2007-02-26 ZA ZA200807024A patent/ZA200807024B/xx unknown
- 2007-02-26 AU AU2007220435A patent/AU2007220435B2/en active Active
- 2007-02-26 BR BRPI0708278A patent/BRPI0708278B8/pt active IP Right Grant
- 2007-02-26 ME MEP-2016-140A patent/ME02456B/me unknown
- 2007-02-26 PL PL07731039.9T patent/PL1989182T3/pl unknown
- 2007-02-26 EP EP07731039.9A patent/EP1989182B1/fr not_active Revoked
- 2007-02-26 WO PCT/FR2007/000335 patent/WO2007099217A1/fr not_active Ceased
- 2007-02-26 KR KR1020117028452A patent/KR20120001818A/ko not_active Ceased
- 2007-02-26 CN CN2007800061889A patent/CN101389603B/zh active Active
- 2007-02-26 MY MYPI20082991 patent/MY151035A/en unknown
- 2007-02-26 KR KR1020087023638A patent/KR20080106948A/ko not_active Ceased
- 2007-02-26 US US12/224,369 patent/US7846961B2/en active Active
- 2007-02-26 HR HRP20160644TT patent/HRP20160644T1/hr unknown
- 2007-02-26 DK DK07731039.9T patent/DK1989182T3/en active
- 2007-02-26 NZ NZ570367A patent/NZ570367A/en unknown
- 2007-02-26 EA EA200801777A patent/EA014716B1/ru unknown
- 2007-02-26 GE GEAP200710918A patent/GEP20125433B/en unknown
- 2007-02-26 SI SI200731781A patent/SI1989182T1/sl unknown
- 2007-02-26 UA UAA200811436A patent/UA89905C2/ru unknown
- 2007-02-26 ES ES07731039.9T patent/ES2581982T3/es active Active
- 2007-02-26 HU HUE07731039A patent/HUE027898T2/en unknown
-
2008
- 2008-08-14 NO NO20083535A patent/NO20083535L/no not_active Application Discontinuation
- 2008-09-11 MA MA31232A patent/MA30276B1/fr unknown
-
2016
- 2016-07-11 CY CY20161100654T patent/CY1117753T1/el unknown
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