KR20050100711A - 3,3-디페닐-프로필아민의 신규한 유도체의 안정한 염 - Google Patents
3,3-디페닐-프로필아민의 신규한 유도체의 안정한 염 Download PDFInfo
- Publication number
- KR20050100711A KR20050100711A KR1020057018318A KR20057018318A KR20050100711A KR 20050100711 A KR20050100711 A KR 20050100711A KR 1020057018318 A KR1020057018318 A KR 1020057018318A KR 20057018318 A KR20057018318 A KR 20057018318A KR 20050100711 A KR20050100711 A KR 20050100711A
- Authority
- KR
- South Korea
- Prior art keywords
- acid
- formula
- compound
- phenyl
- diisopropylamino
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/26—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/06—Anti-spasmodics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/26—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C219/28—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- 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
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Luminescent Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Detergent Compositions (AREA)
Abstract
Description
Claims (15)
- 하기 화학식 Ⅰ의 화합물들의 제조방법으로서,(상기 R은 C1-C6 알킬기, C3-C10 사이클로알킬기 또는 치환 또는 비치환의 페닐기를 나타내며, X-는 생리학적으로 허용되는 무기산 또는 유기산의 산 잔기(acid residue)를 나타낸다.)하기의 과정을 포함하는 것을 특징으로 하는 제조방법:a)하기 화학식 Ⅲ의 화합물을 수소화제(hydrogenation agent)에 의하여 분할(split)시켜, 하기 화학식 Ⅴ의 화합물로 변환시키는 단계;b) 상기 화학식 Ⅴ의 화합물을 환원제에 의하여 변환시켜, 하기 화학식 Ⅵ의 화합물을 얻는 단계;c) 상기 화학식 Ⅵ의 화합물을 아실화제(acylation agent)에 의하여 변환시켜, 하기 화학식 A의 화합물을 얻는 단계(상기 R은 상기에서 언급한 바와 같다.); 및d) 상기 화학식 A의 화합물은 생리학적으로 허용되는 무기산 또는 유기산에 의하여 하기 화학식 Ⅰ의 화합물로 변환시키는 단계:(상기 R은 C1-C6 알킬기, C3-C10 사이클로알킬기 또는 치환되거나 치환되지 아니한 페닐기를 나타내며, X-는 생리학적으로 허용되는 무기산 또는 유기산의 산 잔기(acid residue)를 나타낸다.).
- 제 1항에 있어서, 상기 d)과정에 사용되는 상기 무기산 또는 유기산이 염산, 브롬화수소산, 인산, 황산, 질산, 초산, 프로피온산, 팔미트산, 스테아르산, 말레산, 퓨마르산, 옥살산, 숙신산, DL-말산, L-(-)-말산, D-(+)-말산, DL-타르타르산, L-(+)-타르타르산, D-(-)-타르타르산, 시트르산, L-아스파트산, L-(+)-아스코르브산, D-(+)-글루쿠론산, 2-옥소프로피온산(피루브산), 퓨란-2-카르복실산(뮤식산), 벤조산, 4-하이드로벤조산, 살리실산, 바닐산, 4-하이드록시신남산, 간산(gallic acid), 마뇨산(hipurric acid : N-benzoyl-glycine), 아세투릭산(aceturic acid : N-acetylglycine), 프로레티닉산(phloretinic acid : (3-(4-hydroxyphenyl)propionic acid), 프탈산, 메탄설폰산 및 오로트산(orotic acid)로 구성된 군에서 선택된 1종의 화합물인 것을 특징으로 하는 화학식 Ⅰ의 화합물의 제조 방법.
- 하기 화학식 2의 화합물들의 제조방법으로서,(상기 R은 C1-C6 알킬기, C3-C10 사이클로알킬기 또는 치환되거나 치환되지 아니한 페닐기를 나타내며, X-는 생리학적으로 허용되는 무기산 또는 유기산의 산 잔기(acid residue)를 나타낸다.)하기의 과정을 포함하는 것을 특징으로 하는 제조방법:a)하기 화학식 3의 화합물을 수소화제(hydrogenation agent)에 의하여 분할시켜, 하기 화학식 5의 화합물로 변환시키는 단계;b) 상기 화학식 5의 화합물을 환원제에 의하여 변환시켜, 하기 화학식 6의 화합물을 얻는 단계;c) 상기 화학식 6의 화합물을 아실화제(acylation agent)에 의하여 변환시켜, 하기화학식 1의 화합물을 얻는 단계(상기 R은 상기에서 언급한 바와 같다.); 및d) 상기 화학식 1의 화합물은 생리학적으로 허용되는 무기산 또는 유기산에 의하여 하기 화학식 2의 화합물로 변환시키는 단계(상기 R은 C1-C6 알킬기, C3-C10 사이클로알킬기 또는 치환되거나 치환되지 아니한 페닐기를 나타내며, X-는 생리학적으로 허용되는 무기산 또는 유기산의 산 잔기(acid residue)를 나타낸다.).
- 제 3항에 있어서, 상기 d)과정에 사용되는 상기 무기산 또는 유기산이 염산, 브롬화수소산, 인산, 황산, 질산, 초산, 프로피온산, 팔미트산, 스테아르산, 말레산, 퓨마르산, 옥살산, 숙신산, DL-말산, L-(-)-말산, D-(+)-말산, DL-타르타르산, L-(+)-타르타르산, D-(-)-타르타르산, 시트르산, L-아스파트산, L-(+)-아스코르브산, D-(+)-글루쿠론산, 2-옥소프로피온산(피루브산), 퓨란-2-카르복실산(뮤식산), 벤조산, 4-하이드로벤조산, 살리실산, 바닐산, 4-하이드록시신남산, 간산(gallic acid), 마뇨산(hipurric acid : N-benzoyl-glycine), 아세투릭산(aceturic acid : N-acetylglycine), 프로레티닉산(phloretinic acid : 3-(4-hydroxyphenyl) propionic acid), 프탈산, 메탄설폰산 및 오로트산(orotic acid)로 구성된 군에서 선택된 1종의 화합물인 것을 특징으로 하는 화학식 2의 화합물의 제조 방법.
- 제 1항 내지 제 4항 중 어느 하나의 항에 있어서, 상기 수소화제가 메탄올 용매 하의 라니 니켈(Raney nickel)/H2인 것을 특징으로 하는 제조 방법.
- 제 1항 내지 제 4항 중 어느 하나의 항에 있어서, 상기 환원제가 NaBH4/EtOH 이며, 바람직하게는 LiAlH4/THF인 것을 특징으로 하는 제조 방법.
- 제 1항 내지 제 4항 중 어느 하나의 항에 있어서, 상기 아실화제로는 트리에틸아민 염기하에서, 이소부티릴 클로라이드를 사용하는 것을 특징으로 하는 제조 방법.
- 제 3항 또는 제 4항에 있어서, 에틸 아세테이트, 디클로로메탄, 테트라하이드로퓨란, 아세토나이트릴 및 톨루엔으로 구성된 군에서 선택된 1 종의 용매를 사용하고, 트리에틸아민의 존재하에 화학식 6의 화합물을 동일한 당량의 이소부티릴 클로라이드와 위치선택적이고, 화학선택적으로 반응시켜, R-(+)-2-(3-디이소프로필아미노-1-페닐-프로필)-4-하이드록시-메틸페닐-이소부티레이트 에스테르로 변환하는 것을 특징으로 하는 제조 방법.
- 제 3항 또는 제 4항에 있어서, 상기 R-(+)-2-(3-디이소프로필아미노-1-페닐프로필)-4-하이드록시메틸페닐이소부티레이트 에스테르가 퓨마르산 또는 염산과 반응하여 그 각각의 염을 형성하는 것을 특징으로 하는 제조방법.
- 제 3항 또는 제 4항에 있어서, 상기 R-(+)-2-(3-디이소프로필아미노-1-페닐-프로필)-4-하이드록시메틸페놀(화학식 6)을 외부에서 염기 (external base)를 추가적으로 투입하지 아니하고, 페놀성 에스테르화(phenolic esterification)하여 R-(+)-2-(3-디이소프로필아미노-1-페닐-프로필)-4-하이드록시메틸페놀 이소부티레이트 에스테르 하이드로클로라이드 하이드레이트(화학식 2b)를 제조하는 방법으로서, 화학식 6의 화합물의 용액을 최소한 1몰당량의 물을 포함하고 있는 이소부티레이트 클로라이드 용액에 적하(drop)하여, 직접적으로(directly) 안정한 화학식 2b의 화합물을 수득하는 것을 특징으로 하는 제조 방법.
- 약리학적으로 유용한 하기 화학식 Ι로 표시되는 화합물을 제조함에 있어서, 고순도이고 결정질이며 안정한 중간 생성물로서 하기 화학식 Ⅲ, Ⅴ 및 Ⅵ으로 표시되는 화합물들 중 어느 하나의 화합물을 사용하는 방법.(상기 R은 C1-C6 알킬기, C3-C10 사이클로알킬기 또는 치환 또는 비치환의 페닐기를 나타내며, X-는 생리학적으로 허용되는 무기산 또는 유기산의 산 잔기(acid residue)를 나타낸다.)
- 하기 화학식 A로 표시되는 페놀성 모노에스테르를 제조함에 있어서, 하기 화학식 Ⅲ, Ⅴ 및 Ⅵ으로 표시되는 화합물들 중 어느 하나의 화합물을 중간 생성물로서 사용하는 방법:(상기 R은 C1-C6 알킬기, C3-C10 사이클로알킬기 또는 치환되거나 치환되지 아니한 페닐기를 나타낸다.)
- 하기 화학식 1로 표현되는 페놀성 모노에스테르를 제조함에 있어서, 하기 화학식 3, 5 및 6으로 표시되는 화합물들 중 어느 하나의 화합물을 중간 생성물로서 사용하는 방법.
- 하기 화학식 2로 표현되는 페놀성 모노에스테르의 염을 제조함에 있어서, 하기 화학식 3, 5 및 6으로 표시되는 화합물들 중 어느 하나의 화합물을 중간 생성물로서 사용하는 방법:(상기 R은 C1-C6 알킬기, C3-C10 사이클로알킬기 또는 치환되거나 치환되지 아니한 페닐기를 나타내며, X-는 생리학적으로 허용되는 무기산 또는 유기산의 산 잔기(acid residue)를 나타낸다.)
- R-(+)-2-(3-디이소프로필아미노-1-페닐-프로필)-4-하이드록시-메틸-페닐-이소부티레이트 에스테르 하이드로젠 퓨마레이트 또는 R-(+)-2-(3-디이소프로필아미노-1-페닐-프로필)-4-하이드록시-메틸페닐-이소부티레이트 에스테르 하이드로클로라이드 하이드레이트의 제조에 있어서, 하기 화학식 3, 5 및 6으로 표시되는 화합물들 중 어느 하나의 화합물을 중간 생성물로서 사용하는 방법.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19955190.1 | 1999-11-16 | ||
DE19955190A DE19955190A1 (de) | 1999-11-16 | 1999-11-16 | Stabile Salze neuartiger Derivate von 3,3-Diphenylpropylaminen |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR10-2002-7006306A Division KR100536095B1 (ko) | 1999-11-16 | 2000-11-15 | 3,3-디페닐-프로필아민의 신규한 유도체의 안정한 염 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20050100711A true KR20050100711A (ko) | 2005-10-19 |
KR100563149B1 KR100563149B1 (ko) | 2006-03-21 |
Family
ID=7929277
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR10-2002-7006306A KR100536095B1 (ko) | 1999-11-16 | 2000-11-15 | 3,3-디페닐-프로필아민의 신규한 유도체의 안정한 염 |
KR1020057018318A KR100563149B1 (ko) | 1999-11-16 | 2000-11-15 | 3,3-디페닐-프로필아민의 신규한 유도체의 안정한 염 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR10-2002-7006306A KR100536095B1 (ko) | 1999-11-16 | 2000-11-15 | 3,3-디페닐-프로필아민의 신규한 유도체의 안정한 염 |
Country Status (30)
Country | Link |
---|---|
US (1) | US6858650B1 (ko) |
EP (3) | EP1481964B1 (ko) |
JP (6) | JP4083431B2 (ko) |
KR (2) | KR100536095B1 (ko) |
CN (1) | CN1215045C (ko) |
AT (3) | ATE337293T1 (ko) |
AU (1) | AU778132B2 (ko) |
BR (1) | BRPI0015610C1 (ko) |
CA (1) | CA2389749C (ko) |
CY (2) | CY1106204T1 (ko) |
CZ (2) | CZ302967B6 (ko) |
DE (5) | DE29923134U1 (ko) |
DK (3) | DK1481964T3 (ko) |
EA (1) | EA005588B1 (ko) |
ES (3) | ES2303708T3 (ko) |
GE (1) | GEP20084430B (ko) |
HK (3) | HK1067114A1 (ko) |
HU (2) | HU227608B1 (ko) |
IL (2) | IL149567A0 (ko) |
IS (2) | IS2124B (ko) |
MX (1) | MXPA02004603A (ko) |
NO (2) | NO323920B1 (ko) |
NZ (1) | NZ519230A (ko) |
PL (1) | PL201422B1 (ko) |
PT (3) | PT1481964E (ko) |
SI (3) | SI1481964T1 (ko) |
SK (3) | SK287430B6 (ko) |
UA (2) | UA73324C2 (ko) |
WO (1) | WO2001035957A1 (ko) |
ZA (1) | ZA200203315B (ko) |
Families Citing this family (48)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0957073A1 (en) * | 1998-05-12 | 1999-11-17 | Schwarz Pharma Ag | Novel derivatives of 3,3-diphenylpropylamines |
DE29923134U1 (de) * | 1999-11-16 | 2000-06-29 | Sanol Arznei Schwarz Gmbh | Stabile Salze neuartiger Derviate von 3,3-Diphenylpropylaminen |
DE10028443C1 (de) * | 2000-06-14 | 2002-05-29 | Sanol Arznei Schwarz Gmbh | Verfahren zur Herstellung von 3,3-Diarylpropylaminen, (R,S)- und (R)-4-Phenyl-2-chromanon-6-carbonsäure sowie (R)-4-Phenyl-2-chromanon-carbonsäure-cinchonidinsalz und deren Verwendung zur Herstellung eines rechtsdrehenden Hydroxybenzylalkohols und von pharmazeutischen Zusammensetzungen |
DE10315878B4 (de) | 2003-04-08 | 2009-06-04 | Schwarz Pharma Ag | Vorrichtung zur transdermalen Verabreichung von Fesoterodin und Verwendung |
DE10315917A1 (de) * | 2003-04-08 | 2004-11-18 | Schwarz Pharma Ag | Hochreine Basen von 3,3-Diphenylpropylaminmonoestern |
WO2005012227A2 (en) * | 2003-08-05 | 2005-02-10 | Ranbaxy Laboratories Limited | Process for preparation of 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethyl-phenol, a metabolite of tolterodine |
ES2235648B1 (es) * | 2003-12-22 | 2006-11-01 | Ragactives, S.L. | Procedimiento para la obtencion de tolterodina. |
US8034823B2 (en) * | 2005-02-22 | 2011-10-11 | Savvipharm Inc | Method of increasing drug oral bioavailability and compositions of less toxic orotate salts |
KR100647068B1 (ko) | 2005-09-15 | 2006-11-23 | 하나제약 주식회사 | 라세믹n,n-디이소프로필-3-(2-히드록시-5-메틸페닐)-3-페닐프로판아민의 제조방법 |
US8067594B2 (en) * | 2006-05-24 | 2011-11-29 | Pfizer Inc. | Process for the production of benzopyran-2-ol derivatives |
EP1862449A1 (en) * | 2006-05-31 | 2007-12-05 | Schwarz Pharma Ltd. | A shortened synthesis of substituted hydroxymethyl phenols |
EP1940774B1 (en) * | 2006-05-31 | 2014-03-05 | Schwarz Pharma Ltd. | New synthesis of substituted hydroxymethyl phenols |
IES20060424A2 (en) | 2006-06-08 | 2007-10-31 | Schwarz Pharma Ltd | Accelerated synthesis of (3-Diisopropylamino-1-phenylpropyl)-4-(hydroxymethyl)phenol and its phenolic monoesters |
US7807715B2 (en) | 2006-06-09 | 2010-10-05 | Ucb Pharma Gmbh | Pharmaceutical compositions comprising fesoterodine |
EP2004592B1 (en) | 2006-06-09 | 2010-08-11 | Schwarz Pharma Ltd. | Synthesis of phenolic esters of hydroxymethyl phenols |
AU2007255408B2 (en) | 2006-06-09 | 2013-03-14 | Ucb Pharma Gmbh | Stabilized pharmaceutical compositions comprising fesoterodine |
IES20060435A2 (en) * | 2006-06-12 | 2007-12-12 | Schwarz Pharma Ltd | Shortened synthesis using paraformaldehyde or trioxane |
AU2007260267B2 (en) | 2006-06-12 | 2012-09-06 | Ucb Pharma Gmbh | New chiral intermediate, process for producing the same and its use in the manufacture of tolterodine, fesoterodine, or the active metabolite thereof |
WO2009037569A2 (en) * | 2007-09-21 | 2009-03-26 | Actavis Group Ptc Ehf | An improved process for the preparation of fesoterodine |
WO2009044278A1 (en) * | 2007-10-01 | 2009-04-09 | Actavis Group Ptc Ehf | Amorphous fesoterodine fumarate |
EP2294047A2 (en) * | 2008-04-04 | 2011-03-16 | Actavis Group PTC EHF | Novel mandelate salt of fesoterodine |
US20110171274A1 (en) * | 2008-07-21 | 2011-07-14 | Actavis Group Ptc Ehf | Fesoterodine Substantially Free of Dehydroxy Impurity |
IT1392082B1 (it) * | 2008-12-10 | 2012-02-09 | Chemi Spa | Nuove forme solide della fesoterodina fumarato |
PL2416761T3 (pl) | 2009-05-11 | 2015-07-31 | Ratiopharm Gmbh | Desfezoterodyna w postaci soli kwasu winowego |
IT1394219B1 (it) * | 2009-05-15 | 2012-06-01 | Chemi Spa | Metodo di preparazione di fesoterodina fumarato di elevata purezza. |
IT1394217B1 (it) * | 2009-05-15 | 2012-06-01 | Chemi Spa | Metodo di preparazione di fesoterodina e/o fesoterodina fumarato. |
US20120220655A1 (en) | 2009-09-03 | 2012-08-30 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Crystalline forms of fesoterodine fumarate and fesoterodine base |
IT1396373B1 (it) * | 2009-10-29 | 2012-11-19 | Dipharma Francis Srl | Procedimento per la preparazione di fesoterodina. |
EP2316432A1 (de) | 2009-10-30 | 2011-05-04 | ratiopharm GmbH | Zusammensetzung enthaltend Fesoterodin und Ballaststoffe |
US20110124903A1 (en) * | 2009-11-20 | 2011-05-26 | Actavis Group Ptc Ehf | Solid state forms of fesoterodine intermediates |
IT1397521B1 (it) * | 2009-12-21 | 2013-01-16 | Dipharma Francis Srl | Procedimento per la preparazione di fesoterodina con un basso contenuto di impurezze. |
IT1397920B1 (it) * | 2010-02-08 | 2013-02-04 | Dipharma Francis Srl | Forma cristallina di fesoterodina fumarato e procedimento per la sua preparazione |
US20130172411A1 (en) | 2010-03-22 | 2013-07-04 | Cadila Healthcare Limited | Stable pharmaceutical compositions comprising fesoterodine |
JP5812500B2 (ja) | 2010-04-30 | 2015-11-17 | メルク・シャープ・エンド・ドーム・コーポレイション | 新規なβ3アドレナリン作動性受容体アゴニスト |
WO2011141932A2 (en) | 2010-05-11 | 2011-11-17 | Intas Pharmaceuticals Limited | Process for preparation of phenolic monoesters of hydroxymethyl phenols |
WO2011145019A1 (en) * | 2010-05-17 | 2011-11-24 | Orchid Chemicals And Pharmaceuticals Limited | Improved process for diphenylpropylamine derivatives |
IT1401451B1 (it) * | 2010-06-10 | 2013-07-26 | Chemi Spa | Nuovo processo di preparazione di 2-idrossi-4-fenil-3,4-diidro-2h-cromen-6-il-metanolo e (r)-2-[3-(diisopropilammino)-1-fenilpropil]-4-(idrossimetil)fenolo. |
WO2011158257A1 (en) | 2010-06-18 | 2011-12-22 | Panacea Biotec Ltd | Preparation process of fesoterodine and intermediates |
US9012678B2 (en) * | 2010-08-25 | 2015-04-21 | Cadila Healthcare Limited | Processes for the preparation of fesoterodine |
IT1403094B1 (it) * | 2010-12-09 | 2013-10-04 | Dipharma Francis Srl | Procedimento per la preparazione di fesoterodina o un suo sale |
WO2012098560A2 (en) * | 2011-01-17 | 2012-07-26 | Msn Laboratories Limited | Process for the preparation of muscarinic receptor antagonist |
TWI590821B (zh) | 2011-01-18 | 2017-07-11 | 輝瑞有限公司 | 固體分子分散液 |
EP2508173A1 (en) | 2011-04-08 | 2012-10-10 | LEK Pharmaceuticals d.d. | Stabilized pharmaceutical composition comprising fesoterodine |
EP2508175A1 (en) | 2011-04-08 | 2012-10-10 | LEK Pharmaceuticals d.d. | Pharmaceutical composition comprising fesoterodine or a salt or a solvate thereof |
WO2013113946A2 (en) | 2012-05-04 | 2013-08-08 | Crystal Pharma, S.A.U. | Process for the preparation of optically active 3,3-diphenylpropylamines |
ITMI20121232A1 (it) | 2012-07-16 | 2014-01-17 | Cambrex Profarmaco Milano Srl | Procedimento per la preparazione di 2-(3-n,n-diisopropilamino-1-fenilpropil)-4-idrossimetil-fenolo e suoi derivati |
TR201721437A2 (tr) | 2017-12-25 | 2019-07-22 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | Fesoterodi̇ni̇n modi̇fi̇ye salim sağlayan formülasyonlari |
WO2022090235A1 (en) * | 2020-10-27 | 2022-05-05 | Wella Germany Gmbh | 2-methoxymethyl-p-phenylenediamine in cosmetic grade quality |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI77018C (fi) * | 1980-11-14 | 1989-01-10 | Lilly Co Eli | Analogifoerfarande foer framstaellning av antidepressivt aktiv (-)-enantiomer av n-metyl-n-/3-(2-metylfenoxi) -3-fenylpropyl/amin och dess farmaceutiskt godtagbara salt. |
IL66831A0 (en) * | 1981-10-05 | 1982-12-31 | Kefalas As | Indane derivatives |
SE8800207D0 (sv) * | 1988-01-22 | 1988-01-22 | Kabivitrum Ab | Nya aminer, deras anvendning och framstellning |
EP0445749B1 (en) * | 1990-03-08 | 1996-07-10 | Fujisawa Pharmaceutical Co., Ltd. | N-Monosubstituted cyclopentenylamines, a process for their preparation and their use as medicaments |
JPH0483431A (ja) * | 1990-07-26 | 1992-03-17 | Seiko Epson Corp | 選択呼出受信機 |
SE9203318D0 (sv) * | 1992-11-06 | 1992-11-06 | Kabi Pharmacia Ab | Novel 3,3-diphenylpropylamines, their use and preparation |
SE9701144D0 (sv) * | 1997-03-27 | 1997-03-27 | Pharmacia & Upjohn Ab | Novel compounds, their use and preparation |
EP0957073A1 (en) | 1998-05-12 | 1999-11-17 | Schwarz Pharma Ag | Novel derivatives of 3,3-diphenylpropylamines |
DE29923134U1 (de) * | 1999-11-16 | 2000-06-29 | Sanol Arznei Schwarz Gmbh | Stabile Salze neuartiger Derviate von 3,3-Diphenylpropylaminen |
-
1999
- 1999-11-16 DE DE29923134U patent/DE29923134U1/de not_active Expired - Lifetime
- 1999-11-16 DE DE19955190A patent/DE19955190A1/de not_active Ceased
-
2000
- 2000-11-15 DE DE50015163T patent/DE50015163D1/de not_active Expired - Lifetime
- 2000-11-15 KR KR10-2002-7006306A patent/KR100536095B1/ko not_active IP Right Cessation
- 2000-11-15 DE DE50013365T patent/DE50013365D1/de not_active Expired - Lifetime
- 2000-11-15 AU AU26667/01A patent/AU778132B2/en not_active Expired
- 2000-11-15 CA CA002389749A patent/CA2389749C/en not_active Expired - Lifetime
- 2000-11-15 ES ES06011207T patent/ES2303708T3/es not_active Expired - Lifetime
- 2000-11-15 SK SK657-2002A patent/SK287430B6/sk not_active IP Right Cessation
- 2000-11-15 PT PT04018487T patent/PT1481964E/pt unknown
- 2000-11-15 DE DE50009239T patent/DE50009239D1/de not_active Expired - Lifetime
- 2000-11-15 NZ NZ519230A patent/NZ519230A/en not_active IP Right Cessation
- 2000-11-15 EP EP04018487A patent/EP1481964B1/de not_active Expired - Lifetime
- 2000-11-15 CZ CZ20021343A patent/CZ302967B6/cs not_active IP Right Cessation
- 2000-11-15 PT PT06011207T patent/PT1690536E/pt unknown
- 2000-11-15 PT PT00989857T patent/PT1230209E/pt unknown
- 2000-11-15 SK SK5027-2010A patent/SK288185B6/sk not_active IP Right Cessation
- 2000-11-15 BR BRPI0015610A patent/BRPI0015610C1/pt not_active IP Right Cessation
- 2000-11-15 JP JP2001537950A patent/JP4083431B2/ja not_active Expired - Lifetime
- 2000-11-15 DK DK04018487T patent/DK1481964T3/da active
- 2000-11-15 CZ CZ20060247A patent/CZ302497B6/cs not_active IP Right Cessation
- 2000-11-15 IL IL14956700A patent/IL149567A0/xx unknown
- 2000-11-15 HU HU0900587A patent/HU227608B1/hu unknown
- 2000-11-15 ES ES04018487T patent/ES2270240T3/es not_active Expired - Lifetime
- 2000-11-15 ES ES00989857T patent/ES2236032T7/es active Active
- 2000-11-15 EP EP06011207A patent/EP1690536B1/de not_active Expired - Lifetime
- 2000-11-15 MX MXPA02004603A patent/MXPA02004603A/es active IP Right Grant
- 2000-11-15 DK DK00989857T patent/DK1230209T3/da active
- 2000-11-15 UA UA2002043609A patent/UA73324C2/uk unknown
- 2000-11-15 AT AT04018487T patent/ATE337293T1/de active
- 2000-11-15 HU HU0204034A patent/HU228197B1/hu unknown
- 2000-11-15 KR KR1020057018318A patent/KR100563149B1/ko active IP Right Grant
- 2000-11-15 DK DK06011207T patent/DK1690536T3/da active
- 2000-11-15 AT AT06011207T patent/ATE395056T1/de active
- 2000-11-15 EA EA200200511A patent/EA005588B1/ru not_active IP Right Cessation
- 2000-11-15 SI SI200030890T patent/SI1481964T1/sl unknown
- 2000-11-15 WO PCT/EP2000/011309 patent/WO2001035957A1/de active Application Filing
- 2000-11-15 SI SI200030617T patent/SI1230209T1/xx unknown
- 2000-11-15 US US10/130,214 patent/US6858650B1/en not_active Expired - Lifetime
- 2000-11-15 EP EP00989857A patent/EP1230209B3/de not_active Expired - Lifetime
- 2000-11-15 AT AT00989857T patent/ATE286872T1/de active
- 2000-11-15 SI SI200030998T patent/SI1690536T1/sl unknown
- 2000-11-15 SK SK5024-2013A patent/SK288384B6/sk not_active IP Right Cessation
- 2000-11-15 CN CNB008157057A patent/CN1215045C/zh not_active Expired - Lifetime
- 2000-11-15 PL PL356766A patent/PL201422B1/pl unknown
-
2002
- 2002-04-19 IS IS6351A patent/IS2124B/xx unknown
- 2002-04-25 ZA ZA200203315A patent/ZA200203315B/xx unknown
- 2002-05-09 IL IL149567A patent/IL149567A/en active IP Right Grant
- 2002-05-15 NO NO20022314A patent/NO323920B1/no not_active IP Right Cessation
- 2002-09-05 HK HK04110231A patent/HK1067114A1/xx not_active IP Right Cessation
- 2002-09-05 HK HK02106545.5A patent/HK1045148B/zh not_active IP Right Cessation
-
2005
- 2005-01-17 UA UAA200500434A patent/UA77322C2/uk unknown
-
2006
- 2006-03-29 IS IS8382A patent/IS2673B/is unknown
- 2006-10-18 CY CY20061101493T patent/CY1106204T1/el unknown
- 2006-11-22 NO NO20065380A patent/NO332637B1/no not_active IP Right Cessation
-
2007
- 2007-01-31 HK HK07101097.3A patent/HK1095736A1/xx not_active IP Right Cessation
- 2007-02-22 JP JP2007042774A patent/JP2007137895A/ja active Pending
- 2007-11-07 GE GEAP200710360A patent/GEP20084430B/en unknown
-
2008
- 2008-07-08 CY CY20081100712T patent/CY1110389T1/el unknown
-
2010
- 2010-04-22 JP JP2010098844A patent/JP5650924B2/ja not_active Expired - Lifetime
- 2010-04-22 JP JP2010098845A patent/JP5503393B2/ja not_active Expired - Lifetime
-
2011
- 2011-04-25 JP JP2011096911A patent/JP5290351B2/ja not_active Expired - Lifetime
-
2013
- 2013-11-05 JP JP2013229622A patent/JP5717824B2/ja not_active Expired - Lifetime
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR100563149B1 (ko) | 3,3-디페닐-프로필아민의 신규한 유도체의 안정한 염 | |
SK283663B6 (sk) | Spôsob prípravy kyseliny (S)-3-(aminometyl)-5-metylhexánovej | |
HU226475B1 (en) | Process for producing (1r,4s)- and (1s,4r)-1-amino-4-hydroxymethyl-2-cyclopentene and the new intermediates | |
KR100486394B1 (ko) | 3,3-디페닐-프로필아민의 신규한 유도체의 안정한 염 | |
AU2004266247A1 (en) | 1-carbamoylcycloalkylcarboxylic acid compounds, processes for making and uses thereof | |
WO2010020719A1 (fr) | Procede de preparation de l'ester ethylique de l'acide 4- [trans-4-[(phenylmethyl)-amino]cyclohexyl] benzoïque et de son sel hemifumarate |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A107 | Divisional application of patent | ||
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: 20130221 Year of fee payment: 8 |
|
FPAY | Annual fee payment |
Payment date: 20140220 Year of fee payment: 9 |
|
FPAY | Annual fee payment |
Payment date: 20150226 Year of fee payment: 10 |
|
FPAY | Annual fee payment |
Payment date: 20160218 Year of fee payment: 11 |
|
FPAY | Annual fee payment |
Payment date: 20170220 Year of fee payment: 12 |
|
FPAY | Annual fee payment |
Payment date: 20180219 Year of fee payment: 13 |
|
FPAY | Annual fee payment |
Payment date: 20200218 Year of fee payment: 15 |