AU2006241125B2 - Polymorph Form II of tanaproget - Google Patents
Polymorph Form II of tanaproget Download PDFInfo
- Publication number
- AU2006241125B2 AU2006241125B2 AU2006241125A AU2006241125A AU2006241125B2 AU 2006241125 B2 AU2006241125 B2 AU 2006241125B2 AU 2006241125 A AU2006241125 A AU 2006241125A AU 2006241125 A AU2006241125 A AU 2006241125A AU 2006241125 B2 AU2006241125 B2 AU 2006241125B2
- Authority
- AU
- Australia
- Prior art keywords
- tanaproget
- polymorph form
- polymorph
- solution
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
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- 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
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- 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
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Obesity (AREA)
- Nutrition Science (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67573705P | 2005-04-28 | 2005-04-28 | |
| US60/675,737 | 2005-04-28 | ||
| PCT/US2006/015852 WO2006116526A2 (en) | 2005-04-28 | 2006-04-26 | Polymorph form ii of tanaproget |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2006241125A1 AU2006241125A1 (en) | 2006-11-02 |
| AU2006241125B2 true AU2006241125B2 (en) | 2012-07-05 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006241125A Ceased AU2006241125B2 (en) | 2005-04-28 | 2006-04-26 | Polymorph Form II of tanaproget |
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| Country | Link |
|---|---|
| US (4) | US7759341B2 (enExample) |
| EP (1) | EP1874763A2 (enExample) |
| JP (2) | JP2008539258A (enExample) |
| CN (1) | CN101166736B (enExample) |
| AR (1) | AR053596A1 (enExample) |
| AU (1) | AU2006241125B2 (enExample) |
| BR (1) | BRPI0610433A2 (enExample) |
| CA (1) | CA2603807A1 (enExample) |
| MX (1) | MX2007013469A (enExample) |
| TW (1) | TW200716621A (enExample) |
| WO (1) | WO2006116526A2 (enExample) |
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| CA2544678C (en) | 2003-11-05 | 2013-12-31 | Sunesis Pharmaceuticals, Inc. | Modulators of cellular adhesion |
| SI1896034T1 (sl) | 2005-04-28 | 2010-07-30 | Wyeth Llc | Mikronizirani sestavki tanaprogeta in postopki priprave le-tega |
| EP1877059B8 (en) * | 2005-04-28 | 2010-05-19 | Wyeth a Corporation of the State of Delaware | Micronized tanaproget and compostions containing same |
| BRPI0610433A2 (pt) * | 2005-04-28 | 2010-11-23 | Wyeth Corp | forma polimórfica ii de tanaproget, processos para preparar a mesma, e para preparar forma micronizada de um composto, composição farmacêutica, método de preparação de uma composição farmacêutica, e, uso da forma polimórfica ii de tanaproget ou da forma micronizada |
| WO2007030153A2 (en) * | 2005-04-28 | 2007-03-15 | Wyeth | Compositions containing micronized tanaproget |
| CN103989687A (zh) | 2005-06-09 | 2014-08-20 | 惠氏公司 | 含有炔雌醇的tanaproget组合物 |
| BRPI0819571A2 (pt) | 2007-12-20 | 2019-09-24 | Teva Womenss Health Inc | "método para contracepção de emergência, pacote farmacêutico para contracepção de emergência e composição farmacêutica" |
| US20110237605A1 (en) * | 2010-03-26 | 2011-09-29 | Eric Phillips | Molecular Crystal of (4-(1,8-Naphthyridin-2-YL)Piperidin-1-YL)Pyrimidine Derivative |
| CN104364239B (zh) | 2012-06-13 | 2017-08-25 | 霍夫曼-拉罗奇有限公司 | 二氮杂螺环烷烃和氮杂螺环烷烃 |
| KR20200108932A (ko) * | 2012-07-25 | 2020-09-21 | 에스에이알코드 바이오사이언스 인코포레이티드 | Lfa-1 저해제 및 그의 다형체 |
| MX368615B (es) | 2012-09-25 | 2019-10-09 | Hoffmann La Roche | Derivados bicíclicos como inhibidores de la autotaxina (atx) que son inhibidores de la producción de ácido lisofosfatídico (lpa) y el uso de los mismos. |
| AR095079A1 (es) | 2013-03-12 | 2015-09-16 | Hoffmann La Roche | Derivados de octahidro-pirrolo[3,4-c]-pirrol y piridina-fenilo |
| DK3074400T3 (en) | 2013-11-26 | 2018-01-15 | Hoffmann La Roche | Octahydro-cyclobuta [1,2-c; 3,4-c '] dipyrrole derivatives as autotaxin inhibitors |
| CA2937616A1 (en) | 2014-03-26 | 2015-10-01 | F. Hoffmann-La Roche Ag | Bicyclic compounds as autotaxin (atx) and lysophosphatidic acid (lpa) production inhibitors |
| EA032357B1 (ru) | 2014-03-26 | 2019-05-31 | Ф. Хоффманн-Ля Рош Аг | Конденсированные [1,4]диазепиновые соединения в качестве ингибиторов продукции аутотаксина (atx) и лизофосфатидиловой кислоты (lpa) |
| MA41898A (fr) | 2015-04-10 | 2018-02-13 | Hoffmann La Roche | Dérivés de quinazolinone bicyclique |
| CA2992889A1 (en) | 2015-09-04 | 2017-03-09 | F. Hoffmann-La Roche Ag | Phenoxymethyl derivatives |
| JP6876685B2 (ja) | 2015-09-24 | 2021-05-26 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | Ａｔｘ阻害剤としての二環式化合物 |
| WO2017050732A1 (en) | 2015-09-24 | 2017-03-30 | F. Hoffmann-La Roche Ag | Bicyclic compounds as atx inhibitors |
| BR112017026682A2 (pt) | 2015-09-24 | 2018-08-14 | Hoffmann La Roche | novos compostos bicíclicos como inibidores de dupla ação de atx/ca |
| AU2016328436B2 (en) | 2015-09-24 | 2020-05-14 | F. Hoffmann-La Roche Ag | New bicyclic compounds as dual ATX/CA inhibitors |
| RU2019132254A (ru) | 2017-03-16 | 2021-04-16 | Ф. Хоффманн-Ля Рош Аг | Гетероциклические соединения, пригодные в качестве дуальных ингибиторов atx/ca |
| JP7090099B2 (ja) | 2017-03-16 | 2022-06-23 | エフ．ホフマン－ラ ロシュ アーゲー | Ａｔｘインヒビターとしての新規二環式化合物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6436929B1 (en) * | 1999-05-04 | 2002-08-20 | Wyeth | Cyclothiocarbamate derivatives as progesterone receptor modulators |
Family Cites Families (13)
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|---|---|---|---|---|
| ATE386729T1 (de) * | 1999-05-04 | 2008-03-15 | Wyeth Corp | Cyclothiocarbamatderivate als progesteron- rezeptormodulatoren |
| RU2005101638A (ru) * | 2002-06-25 | 2006-01-20 | Уайт (Us) | Использование циклокарбаматных производных для лечения гормонзависимых состояний |
| US7268149B2 (en) * | 2002-06-25 | 2007-09-11 | Wyeth | Cyclothiocarbamate derivatives as progesterone receptor modulators and methods of treating skin disorders |
| US8399013B2 (en) * | 2003-06-26 | 2013-03-19 | Poly-Med, Inc. | Partially absorbable fiber-reinforced composites for controlled drug delivery |
| TW200604137A (en) | 2004-04-27 | 2006-02-01 | Wyeth Corp | Coupling process for generating reactive boron-containing derivatives of n-substituted pyrrole-2-carbonitriles to produce biaryls |
| EP1756072A2 (en) * | 2004-04-27 | 2007-02-28 | Wyeth | Purification of progesterone receptor modulators |
| SI1778710T1 (sl) * | 2004-08-13 | 2012-05-31 | Wyeth Llc | Derivati tanaprogeta metaboliti in njihove uporabe |
| SI1896034T1 (sl) * | 2005-04-28 | 2010-07-30 | Wyeth Llc | Mikronizirani sestavki tanaprogeta in postopki priprave le-tega |
| JP2008539254A (ja) * | 2005-04-28 | 2008-11-13 | ワイス | タナプロゲットの精製形態 |
| EP1877059B8 (en) | 2005-04-28 | 2010-05-19 | Wyeth a Corporation of the State of Delaware | Micronized tanaproget and compostions containing same |
| WO2007030153A2 (en) * | 2005-04-28 | 2007-03-15 | Wyeth | Compositions containing micronized tanaproget |
| BRPI0610433A2 (pt) | 2005-04-28 | 2010-11-23 | Wyeth Corp | forma polimórfica ii de tanaproget, processos para preparar a mesma, e para preparar forma micronizada de um composto, composição farmacêutica, método de preparação de uma composição farmacêutica, e, uso da forma polimórfica ii de tanaproget ou da forma micronizada |
| CN103989687A (zh) * | 2005-06-09 | 2014-08-20 | 惠氏公司 | 含有炔雌醇的tanaproget组合物 |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6436929B1 (en) * | 1999-05-04 | 2002-08-20 | Wyeth | Cyclothiocarbamate derivatives as progesterone receptor modulators |
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| AU2006241125A1 (en) | 2006-11-02 |
| US7759341B2 (en) | 2010-07-20 |
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| JP2008539258A (ja) | 2008-11-13 |
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| US8114869B2 (en) | 2012-02-14 |
| BRPI0610433A2 (pt) | 2010-11-23 |
| EP1874763A2 (en) | 2008-01-09 |
| US20060247235A1 (en) | 2006-11-02 |
| CN101166736B (zh) | 2013-02-06 |
| US20100267715A1 (en) | 2010-10-21 |
| JP2014088385A (ja) | 2014-05-15 |
| US20110212953A1 (en) | 2011-09-01 |
| TW200716621A (en) | 2007-05-01 |
| CA2603807A1 (en) | 2006-11-02 |
| WO2006116526A2 (en) | 2006-11-02 |
| US7968709B2 (en) | 2011-06-28 |
| WO2006116526A3 (en) | 2007-06-28 |
| AR053596A1 (es) | 2007-05-09 |
| WO2006116526A8 (en) | 2007-08-16 |
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