KR101120408B1 - 에이형 다형의4-[6-아세틸-3-[3-(4-아세틸-3-하이드록시-2-프로필페닐티오)프로폭시]-2-프로필페녹시]부티르산 - Google Patents
에이형 다형의4-[6-아세틸-3-[3-(4-아세틸-3-하이드록시-2-프로필페닐티오)프로폭시]-2-프로필페녹시]부티르산 Download PDFInfo
- Publication number
- KR101120408B1 KR101120408B1 KR1020057024889A KR20057024889A KR101120408B1 KR 101120408 B1 KR101120408 B1 KR 101120408B1 KR 1020057024889 A KR1020057024889 A KR 1020057024889A KR 20057024889 A KR20057024889 A KR 20057024889A KR 101120408 B1 KR101120408 B1 KR 101120408B1
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- acetyl
- tablet
- composition
- Prior art date
Links
- 0 C*c(c(*)ccc1C(C)=O)c1O Chemical compound C*c(c(*)ccc1C(C)=O)c1O 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
결정형 | 제조공정 | 용해도(mg/mL) |
I | 화학식 1의 화합물을 가열하고 4배량의 이소프로필에테르에 용해한 후, 얻은 용액을 실온에서 냉각하였다 (결정화가 약 40℃에서 일어났다). 또는 화합물을 가열하고 5배량의 아세토니트릴에 용해한 후, 얻은 용액을 40℃ 배양기에서 유지하였다. | 36.7 |
II | 화학식 1의 화합물을 가열하고 10배량의 아세토니트릴에 용해한 후, 얻은 용액을 냉각하고 빙수욕에서 교반하였다. | 40.5 |
III | 화학식 1의 화합물을 가열하고 10배량의 아세토니트릴에 용해한 후, 얻은 용액을 25℃ 배양기에서 유지하였다. | 35.3 |
IV | 화학식 1의 화합물을 가열하고 5배량의 에탄올에 용해한 후, 2.5배량의 물을 가열상태에서 첨가하고 실온에서 냉각하였다. | 45.8 |
V | 화학식 1의 화합물을 가열하고 5배량의 에탄올에 용해한 후, 얻은 용액을 냉각하고 빙수욕에서 교반하고 2.5배량의 물을 냉각상태에서 첨가하였다. 또는 화학식 1의 화합물을 가열하고 3.5배량의 이소프로판올에 용해한 후, 얻은 용액을 0℃ 냉장기에서 유지하였다. |
47.6 |
온도 | 원하는 V형 (A형) 다형 | 원하지않는 단사 다형 |
22℃ | 6.7 g/L | 3.4 g/L |
30℃ | 15.7 g/L | 6.1 g/L |
40℃ | 46 g/L | 17.2 g/L |
No. | 성분 | 프로토타입 1 (mg/정제) |
프로토타입 2 (mg/정제) |
||
1 | 화합물 (1), V형 (A형) | 250 | 250 | ||
2 | 락토스 레귤러/페스트 플로우 | 7.5 | - | ||
3 | 미소결정성 셀룰로스 PH101 | 31 | 31 | ||
4 | 크로스카멜로스 나트륨 | 20 | 20 | ||
5 | 하이드록시프로필셀룰로스 | 80 | - | ||
6 | 스테아르산마그네슘 | 2.0 | - | ||
7 | 하이드록시프로필메틸셀룰로스 2910 | 8.0 | - | ||
8 | 이산화티탄 | 1.0 | - | ||
9 | 카르나우바왁스 | 0.5 | 0.5 | ||
10 | 폴리비닐피롤리돈 | - | 85 | ||
11 | 만니톨 | - | 3.5 | ||
12 | 글리세릴 베헤네이트 | - | 2.0 | ||
13 | 오파드리 II (화이트) | - | 8.0 | ||
총 합계 | 400 mg | 400 mg |
No. | 성분 | 프로토타입 1 (mg/정제) |
프로토타입 2 (mg/정제) |
1 | 화합물 (1), V형 (A형) | 250 | 250 |
2 | 락토스 레귤러/페스트 플로우 | 7.5 | - |
3 | 미소결정성 셀룰로스 PH101 | 32 | 32 |
4 | 크로스카멜로스 나트륨 | 25 | 25 |
5 | 하이드록시프로필셀룰로스 | 25 | - |
6 | 스테아르산마그네슘 | 2.0 | - |
7 | 하이드록시프로필메틸셀룰로스 2910 | 7.0 | - |
8 | 이산화티탄 | 1.0 | - |
9 | 카르나우바왁스 | 0.5 | 0.5 |
10 | 폴리비닐피롤리돈 | - | 30 |
11 | 만니톨 | - | 3.5 |
12 | 글리세릴 베헤네이트 | - | 2.0 |
13 | 오파드리 II (화이트) | - | 7.0 |
총 합계 | 350 mg | 350 mg |
Claims (12)
- 삭제
- 제 1 항에 있어서, 조성물은 정제 또는 캡슐 형태인 것을 특징으로 하는 조성물.
- 제 3 항에 있어서, 정제 또는 캡슐은 도 6에서 A형 다형에 대해 나타낸 바와 같이 PXRD 패턴을 나타내는 것을 특징으로 하는 정제 또는 캡슐.
- 제 1 항에 있어서, 90% 이상의 화학식 1의 화합물은 2-θ의 9°부근에서 PXRD 피크높이로 결정된 A형 다형인 것을 특징으로 하는 조성물.
- 제 1 항에 있어서, 락토스 및 미소결정성 셀룰로스를 더 포함하는 것을 특징으로 하는 조성물.
- 제 3 항에 있어서, 정제 중량은 250 내지 500 mg인 것을 특징으로 하는 정제.
- 삭제
- 삭제
- 삭제
- 삭제
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/601,862 US7064146B2 (en) | 2003-06-24 | 2003-06-24 | Pharmaceutical compositions of isolated orthorhombic crystalline 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid and methods of use |
US10/601,862 | 2003-06-24 | ||
PCT/US2004/020154 WO2005000243A2 (en) | 2003-06-24 | 2004-06-24 | The polymorphic form a of 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butryric acid |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20060030484A KR20060030484A (ko) | 2006-04-10 |
KR101120408B1 true KR101120408B1 (ko) | 2012-03-15 |
Family
ID=33539463
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020057024889A KR101120408B1 (ko) | 2003-06-24 | 2004-06-24 | 에이형 다형의4-[6-아세틸-3-[3-(4-아세틸-3-하이드록시-2-프로필페닐티오)프로폭시]-2-프로필페녹시]부티르산 |
Country Status (11)
Country | Link |
---|---|
US (3) | US7064146B2 (ko) |
EP (1) | EP1636176A4 (ko) |
JP (2) | JP5518280B2 (ko) |
KR (1) | KR101120408B1 (ko) |
CN (1) | CN1812968B (ko) |
BR (1) | BRPI0411973A (ko) |
CA (1) | CA2530583C (ko) |
NO (1) | NO20060379L (ko) |
NZ (1) | NZ544319A (ko) |
RU (1) | RU2317979C2 (ko) |
WO (1) | WO2005000243A2 (ko) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7064146B2 (en) * | 2003-06-24 | 2006-06-20 | Medicinova, Inc. | Pharmaceutical compositions of isolated orthorhombic crystalline 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid and methods of use |
US7060854B2 (en) * | 2003-06-24 | 2006-06-13 | Medicinova, Inc. | Process for making polymorphic form A of 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid |
MXPA06012564A (es) | 2004-04-27 | 2007-01-31 | Medicinova Inc | Derivados de acido fenoxialquilcarboxilico en el tratamiento de enfermedades inflamatorias. |
US8962687B2 (en) | 2012-12-05 | 2015-02-24 | Medicinova, Inc. | Method of treating liver disorders |
US8835499B2 (en) * | 2011-12-08 | 2014-09-16 | Medicinova, Inc. | Method of treating non-alcoholic fatty liver disease and steatohepatitis |
WO2015013395A1 (en) | 2013-07-25 | 2015-01-29 | Medicinova, Inc. | Methods for reducing triglyceride, total cholesterol and low density lipoprotein blood levels |
US9346754B2 (en) | 2014-05-08 | 2016-05-24 | Medicinova, Inc. | Method of treating advanced non-alcoholic steatohepatitis |
US20150321989A1 (en) | 2014-05-08 | 2015-11-12 | Medicinova, Inc. | Method of treating idiopathic pulmonary fibrosis |
CA2950909C (en) | 2014-06-02 | 2023-03-28 | Medicinova, Inc. | Method of inhibiting or treating fibrosis |
WO2016033094A1 (en) * | 2014-08-25 | 2016-03-03 | Aimmune Therapeutics, Inc. | Egg protein formulations and methods of manufacture thereof |
WO2016123530A1 (en) * | 2015-01-30 | 2016-08-04 | The Regents Of The University Of Michigan | Compositions and methods for delivering pharmaceutical agents |
CN117320701A (zh) | 2021-05-28 | 2023-12-29 | 美迪诺亚公司 | 一种降低肝脏中甘油三酯合成的方法 |
JP7478895B1 (ja) | 2022-11-30 | 2024-05-07 | 花王株式会社 | 痒みの予防又は改善剤 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5858146A (ja) | 1981-10-05 | 1983-04-06 | Tanabe Seiyaku Co Ltd | 速放性マイクロカプセル |
US4710384A (en) | 1986-07-28 | 1987-12-01 | Avner Rotman | Sustained release tablets made from microcapsules |
JPH07116125B2 (ja) * | 1988-03-07 | 1995-12-13 | 杏林製薬株式会社 | フェノキシアルキルカルボン酸誘導体及びその製造法 |
US4985585A (en) * | 1988-03-07 | 1991-01-15 | Kyorin Pharmaceutical Co., Ltd. | Phenoxyalkylcarboxylic acid derivatives and process for their preparations |
US5178878A (en) | 1989-10-02 | 1993-01-12 | Cima Labs, Inc. | Effervescent dosage form with microparticles |
JPH06345682A (ja) * | 1993-06-11 | 1994-12-20 | Kyorin Pharmaceut Co Ltd | カルボン酸誘導体 |
JP3773064B2 (ja) * | 1994-09-13 | 2006-05-10 | 杏林製薬株式会社 | フェノキシアルキルカルボン酸誘導体の製造法 |
US5639475A (en) | 1995-02-03 | 1997-06-17 | Eurand America, Incorporated | Effervescent microcapsules |
JPH1179985A (ja) | 1997-09-01 | 1999-03-23 | Kyorin Pharmaceut Co Ltd | 喘息治療用の粉末吸入剤 |
US7060854B2 (en) | 2003-06-24 | 2006-06-13 | Medicinova, Inc. | Process for making polymorphic form A of 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid |
US7064146B2 (en) * | 2003-06-24 | 2006-06-20 | Medicinova, Inc. | Pharmaceutical compositions of isolated orthorhombic crystalline 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid and methods of use |
-
2003
- 2003-06-24 US US10/601,862 patent/US7064146B2/en not_active Expired - Lifetime
-
2004
- 2004-06-24 CN CN200480017934.0A patent/CN1812968B/zh active Active
- 2004-06-24 BR BRPI0411973-8A patent/BRPI0411973A/pt not_active IP Right Cessation
- 2004-06-24 NZ NZ544319A patent/NZ544319A/en not_active IP Right Cessation
- 2004-06-24 EP EP04776980A patent/EP1636176A4/en not_active Withdrawn
- 2004-06-24 RU RU2006101871/04A patent/RU2317979C2/ru not_active IP Right Cessation
- 2004-06-24 KR KR1020057024889A patent/KR101120408B1/ko active IP Right Grant
- 2004-06-24 JP JP2006517585A patent/JP5518280B2/ja active Active
- 2004-06-24 CA CA2530583A patent/CA2530583C/en not_active Expired - Fee Related
- 2004-06-24 WO PCT/US2004/020154 patent/WO2005000243A2/en active Application Filing
-
2005
- 2005-12-29 US US11/319,272 patent/US7365224B2/en not_active Expired - Lifetime
-
2006
- 2006-01-24 NO NO20060379A patent/NO20060379L/no not_active Application Discontinuation
-
2008
- 2008-04-21 US US12/106,939 patent/US7728169B2/en not_active Expired - Lifetime
-
2013
- 2013-12-24 JP JP2013265114A patent/JP2014097989A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
US20060135604A1 (en) | 2006-06-22 |
NZ544319A (en) | 2008-12-24 |
US20040266878A1 (en) | 2004-12-30 |
RU2006101871A (ru) | 2006-07-27 |
RU2317979C2 (ru) | 2008-02-27 |
US7365224B2 (en) | 2008-04-29 |
US7728169B2 (en) | 2010-06-01 |
JP2014097989A (ja) | 2014-05-29 |
US20080292698A1 (en) | 2008-11-27 |
KR20060030484A (ko) | 2006-04-10 |
WO2005000243A2 (en) | 2005-01-06 |
NO20060379L (no) | 2006-03-24 |
JP5518280B2 (ja) | 2014-06-11 |
BRPI0411973A (pt) | 2006-08-29 |
EP1636176A4 (en) | 2010-03-31 |
CA2530583C (en) | 2010-08-10 |
JP2007524624A (ja) | 2007-08-30 |
WO2005000243A3 (en) | 2005-04-28 |
CN1812968B (zh) | 2016-07-27 |
CA2530583A1 (en) | 2005-01-06 |
CN1812968A (zh) | 2006-08-02 |
EP1636176A2 (en) | 2006-03-22 |
US7064146B2 (en) | 2006-06-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7728169B2 (en) | Pharmaceutical compositions of isolated orthorhombic crystalline 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid and methods of use | |
US7153993B2 (en) | Process for making polymorphic form A of 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyric acid | |
US8865722B2 (en) | Wet formulations of aripiprazole | |
US10214553B2 (en) | Solid state forms of sofosbuvir | |
JP2013209419A (ja) | 酢酸バゼドキシフェン製剤 | |
US20170226119A1 (en) | Solid salt form of alpha-6-mpeg6-o-hydroxycodone as opioid agonists and uses thereof | |
AU2004251744B2 (en) | The polymorphic Form A of 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butryric acid | |
MXPA06000083A (en) | The polymorphic form a of 4-[6 -acetyl -3-[3-(4-acetyl -3-hydroxy-2 -propylphenylthio) propoxy]-2- propylphenoxy]butryric acid | |
CA3213159A1 (en) | Salts of viloxazine | |
WO2024000060A1 (en) | Salts of belumosudil, crystalline forms and pharmaceutical compositions thereof and their use in the treatment of chronic graft-versus-host disease | |
US20030022921A1 (en) | Stable pharmaceutical formulation comprising torsemide modification II | |
AU2012275036B2 (en) | Bazedoxifene acetate formulations and manufacturing process thereof | |
JPH0745404B2 (ja) | 骨粗鬆症治療剤 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
E902 | Notification of reason for refusal | ||
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant | ||
FPAY | Annual fee payment |
Payment date: 20150120 Year of fee payment: 4 |
|
FPAY | Annual fee payment |
Payment date: 20160119 Year of fee payment: 5 |
|
FPAY | Annual fee payment |
Payment date: 20170119 Year of fee payment: 6 |
|
FPAY | Annual fee payment |
Payment date: 20180118 Year of fee payment: 7 |
|
FPAY | Annual fee payment |
Payment date: 20190116 Year of fee payment: 8 |
|
FPAY | Annual fee payment |
Payment date: 20200115 Year of fee payment: 9 |