RU2421445C1 - Новые кристаллические формы производных пирролилгептановой кислоты - Google Patents
Новые кристаллические формы производных пирролилгептановой кислоты Download PDFInfo
- Publication number
- RU2421445C1 RU2421445C1 RU2009136427/04A RU2009136427A RU2421445C1 RU 2421445 C1 RU2421445 C1 RU 2421445C1 RU 2009136427/04 A RU2009136427/04 A RU 2009136427/04A RU 2009136427 A RU2009136427 A RU 2009136427A RU 2421445 C1 RU2421445 C1 RU 2421445C1
- Authority
- RU
- Russia
- Prior art keywords
- crystalline form
- formula
- alcohol
- compound
- hydrate
- Prior art date
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- RMFCNASGODHYAI-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)heptanoic acid Chemical class CCCCCC(C(O)=O)C1=CC=CN1 RMFCNASGODHYAI-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 102000007330 LDL Lipoproteins Human genes 0.000 claims description 18
- 108010007622 LDL Lipoproteins Proteins 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000000843 powder Substances 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 6
- 238000000634 powder X-ray diffraction Methods 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000003860 storage Methods 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 102100029077 3-hydroxy-3-methylglutaryl-coenzyme A reductase Human genes 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 5
- OCHRNWWUOQPIGD-UHFFFAOYSA-N 7-(1h-pyrrol-2-yl)heptanoic acid Chemical class OC(=O)CCCCCCC1=CC=CN1 OCHRNWWUOQPIGD-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 208000035150 Hypercholesterolemia Diseases 0.000 description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 description 4
- 208000001132 Osteoporosis Diseases 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 208000020346 hyperlipoproteinemia Diseases 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 101710158485 3-hydroxy-3-methylglutaryl-coenzyme A reductase Proteins 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 150000004684 trihydrates Chemical class 0.000 description 3
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- LMLSTUCUPVCKEU-UHFFFAOYSA-N O.O.O.O.O.O.[Ca] Chemical compound O.O.O.O.O.O.[Ca] LMLSTUCUPVCKEU-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000000185 intracerebroventricular administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001304 sample melting Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20070020999 | 2007-03-02 | ||
| KR10-2007-0020999 | 2007-03-02 | ||
| KR1020080019764A KR101012917B1 (ko) | 2007-03-02 | 2008-03-03 | 피롤 헵탄산 화합물의 신규한 결정형 |
| KR10-2008-0019764 | 2008-03-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2009136427A RU2009136427A (ru) | 2011-04-10 |
| RU2421445C1 true RU2421445C1 (ru) | 2011-06-20 |
Family
ID=40020978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009136427/04A RU2421445C1 (ru) | 2007-03-02 | 2008-03-03 | Новые кристаллические формы производных пирролилгептановой кислоты |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7915302B2 (enExample) |
| EP (1) | EP2132171A4 (enExample) |
| JP (1) | JP2010520273A (enExample) |
| KR (1) | KR101012917B1 (enExample) |
| CN (1) | CN101657419A (enExample) |
| CA (1) | CA2679317A1 (enExample) |
| RU (1) | RU2421445C1 (enExample) |
| WO (1) | WO2008108572A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2555360C2 (ru) * | 2012-11-06 | 2015-07-10 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Волгоградский государственный медицинский университет" Министерства здравоохранения Российской Федерации | Способ определения воды в координационных соединениях |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011219437A (ja) * | 2010-04-14 | 2011-11-04 | Towa Yakuhin Kk | 結晶性形態tw−1のアトルバスタチンヘミカルシウム水和物とその製造方法 |
| KR20120011249A (ko) | 2010-07-28 | 2012-02-07 | 주식회사 경보제약 | 아토바스타틴 헤미칼슘염의 신규한 결정형, 이의 수화물, 및 그의 제조방법 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002036384A1 (de) * | 1999-10-23 | 2002-05-10 | Zf Friedrichshafen Ag | Steuerung eines automatgetriebes eines kraftfahrzeuges |
| WO2003070702A1 (en) * | 2002-02-15 | 2003-08-28 | Teva Pharmaceutical Industries Ltd. | Novel crystal forms of atorvastatin hemi-calcium and processes for their preparation, as well as novel processes for preparing atorvastatin hemi-calcium forms i, viii and ix |
| WO2004043918A2 (en) * | 2002-11-12 | 2004-05-27 | Teva Pharmaceutical Industries Ltd. | Novel crystal forms of atorvastatin hemi-calcium and processes for their preparation as well as novel processes for preparing other forms |
| RU2247113C2 (ru) * | 1999-12-10 | 2005-02-27 | Лек Фармасьютикал Энд Кемикал Компани Д.Д. | Способ получения аморфного аторвастатина |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI94339C (fi) * | 1989-07-21 | 1995-08-25 | Warner Lambert Co | Menetelmä farmaseuttisesti käyttökelpoisen /R-(R*,R*)/-2-(4-fluorifenyyli)- , -dihydroksi-5-(1-metyylietyyli)-3-fenyyli-4-/(fenyyliamino)karbonyyli/-1H-pyrroli-1-heptaanihapon ja sen farmaseuttisesti hyväksyttävien suolojen valmistamiseksi |
| DE69634054T2 (de) * | 1995-07-17 | 2005-12-08 | Warner-Lambert Co. | Kristalline (R-(R*, R*))-2-(4-Fluorophenyl)-β, δ-Dihydroxy-5-(1-Methylethyl)-3-Phenyl-4-((Phenylamino)Carbonyl)-1H-Pyrrol-1-Heptancarbonsäure Hemi Calcium Salz (Atorvastatin) |
| SI1535613T1 (sl) * | 1999-11-17 | 2010-12-31 | Teva Pharma | Postopek za pripravo polimorfne oblike atorvastatin kalcija |
| IL156055A0 (en) | 2000-11-30 | 2003-12-23 | Teva Pharma | Novel crystal forms of atorvastatin hemi calcium and processes for their preparation as well as novel processes for preparing other forms |
| EP1423364B1 (en) * | 2001-06-29 | 2015-11-04 | Warner-Lambert Company LLC | Crystalline forms of [r-(r*,r*)]-2-(4-fluorophenyl)-beta, delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-phenylamino)carbonyl]-1h-pyrrole-1-heptanoic acid calcium salt (2:1) (atorvastatin) |
| EP1562583A1 (en) * | 2002-09-03 | 2005-08-17 | Morepen Laboratories Ltd. | Atorvastatin calcium form vi or hydrates thereof |
| CA2508871C (en) * | 2002-11-28 | 2008-09-09 | Teva Pharmaceutical Industries Ltd. | Crystalline form f of atorvastatin hemi-calcium salt |
| WO2005090301A1 (en) * | 2004-03-17 | 2005-09-29 | Ranbaxy Laboratories Limited | Crystalline form of atorvastatin hemi calcium |
| WO2006048894A1 (en) * | 2004-11-05 | 2006-05-11 | Morepen Laboratories Limited | Novel crystalline forms of atorvastatin calcium and processes for preparing them. |
-
2008
- 2008-03-03 KR KR1020080019764A patent/KR101012917B1/ko active Active
- 2008-03-03 JP JP2009552583A patent/JP2010520273A/ja active Pending
- 2008-03-03 CA CA002679317A patent/CA2679317A1/en not_active Abandoned
- 2008-03-03 CN CN200880006877A patent/CN101657419A/zh active Pending
- 2008-03-03 WO PCT/KR2008/001218 patent/WO2008108572A1/en not_active Ceased
- 2008-03-03 RU RU2009136427/04A patent/RU2421445C1/ru not_active IP Right Cessation
- 2008-03-03 EP EP08723256A patent/EP2132171A4/en not_active Withdrawn
- 2008-03-03 US US12/449,867 patent/US7915302B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002036384A1 (de) * | 1999-10-23 | 2002-05-10 | Zf Friedrichshafen Ag | Steuerung eines automatgetriebes eines kraftfahrzeuges |
| RU2247113C2 (ru) * | 1999-12-10 | 2005-02-27 | Лек Фармасьютикал Энд Кемикал Компани Д.Д. | Способ получения аморфного аторвастатина |
| WO2003070702A1 (en) * | 2002-02-15 | 2003-08-28 | Teva Pharmaceutical Industries Ltd. | Novel crystal forms of atorvastatin hemi-calcium and processes for their preparation, as well as novel processes for preparing atorvastatin hemi-calcium forms i, viii and ix |
| WO2004043918A2 (en) * | 2002-11-12 | 2004-05-27 | Teva Pharmaceutical Industries Ltd. | Novel crystal forms of atorvastatin hemi-calcium and processes for their preparation as well as novel processes for preparing other forms |
Non-Patent Citations (2)
| Title |
|---|
| RU 2304139 c2, 10.08.2007. * |
| WO 2002/043732 a1, 06.06.2002. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2555360C2 (ru) * | 2012-11-06 | 2015-07-10 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Волгоградский государственный медицинский университет" Министерства здравоохранения Российской Федерации | Способ определения воды в координационных соединениях |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2132171A1 (en) | 2009-12-16 |
| KR20080080959A (ko) | 2008-09-05 |
| KR101012917B1 (ko) | 2011-02-08 |
| US20100113556A1 (en) | 2010-05-06 |
| US7915302B2 (en) | 2011-03-29 |
| EP2132171A4 (en) | 2010-11-17 |
| CA2679317A1 (en) | 2008-09-12 |
| CN101657419A (zh) | 2010-02-24 |
| WO2008108572A1 (en) | 2008-09-12 |
| RU2009136427A (ru) | 2011-04-10 |
| JP2010520273A (ja) | 2010-06-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20150304 |