AU2010321831B2 - 7-[3,5-dihydroxy-2- (3-hydroxy-5-phenyl-pent-1-enyl)- cyclopentyl]-N-ethyl-hept-5-enamide (bimatoprost) in crystalline form II, methods for preparation, and methods for use thereof - Google Patents

7-[3,5-dihydroxy-2- (3-hydroxy-5-phenyl-pent-1-enyl)- cyclopentyl]-N-ethyl-hept-5-enamide (bimatoprost) in crystalline form II, methods for preparation, and methods for use thereof Download PDF

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Publication number
AU2010321831B2
AU2010321831B2 AU2010321831A AU2010321831A AU2010321831B2 AU 2010321831 B2 AU2010321831 B2 AU 2010321831B2 AU 2010321831 A AU2010321831 A AU 2010321831A AU 2010321831 A AU2010321831 A AU 2010321831A AU 2010321831 B2 AU2010321831 B2 AU 2010321831B2
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AU
Australia
Prior art keywords
crystalline form
dihydroxy
hydroxy
phenyl
enyl
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Ceased
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AU2010321831A
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AU2010321831A1 (en
Inventor
Gyorgy F. Ambrus
Kiomars Karami
Ke Wu
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Allergan Inc
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Allergan Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
    • C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
    • C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • 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
    • A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
    • A61K31/5575—Eicosanoids, e.g. leukotrienes or prostaglandins having a cyclopentane, e.g. prostaglandin E2, prostaglandin F2-alpha
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/22—Separation; Purification; Stabilisation; Use of additives
    • C07C231/24—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/39—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of an unsaturated carbon skeleton containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being unsaturated and containing rings other than six-membered aromatic rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Ophthalmology & Optometry (AREA)
  • Epidemiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
AU2010321831A 2009-11-23 2010-11-19 7-[3,5-dihydroxy-2- (3-hydroxy-5-phenyl-pent-1-enyl)- cyclopentyl]-N-ethyl-hept-5-enamide (bimatoprost) in crystalline form II, methods for preparation, and methods for use thereof Ceased AU2010321831B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US26347109P 2009-11-23 2009-11-23
US61/263,471 2009-11-23
PCT/US2010/057494 WO2011063276A1 (en) 2009-11-23 2010-11-19 7-[3,5-dihydroxy-2- (3-hydroxy-5-phenyl-pent-1-enyl)- cyclopentyl]-n-ethyl-hept-5-enamide (bimatoprost) in crystalline form ii, methods for preparation, and methods for use thereof

Publications (2)

Publication Number Publication Date
AU2010321831A1 AU2010321831A1 (en) 2012-06-21
AU2010321831B2 true AU2010321831B2 (en) 2016-07-07

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ID=43639099

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AU2010321831A Ceased AU2010321831B2 (en) 2009-11-23 2010-11-19 7-[3,5-dihydroxy-2- (3-hydroxy-5-phenyl-pent-1-enyl)- cyclopentyl]-N-ethyl-hept-5-enamide (bimatoprost) in crystalline form II, methods for preparation, and methods for use thereof

Country Status (20)

Country Link
US (2) US8629185B2 (enExample)
EP (1) EP2504313A1 (enExample)
JP (2) JP5921439B2 (enExample)
KR (1) KR20120085330A (enExample)
CN (2) CN102712584B (enExample)
AU (1) AU2010321831B2 (enExample)
BR (1) BR112012012387A2 (enExample)
CA (1) CA2781698A1 (enExample)
CL (1) CL2012001339A1 (enExample)
CO (1) CO6551754A2 (enExample)
HK (1) HK1207570A1 (enExample)
IL (2) IL219959A (enExample)
IN (1) IN2012DN05209A (enExample)
MX (1) MX2012005968A (enExample)
NZ (1) NZ600263A (enExample)
PH (1) PH12012501098A1 (enExample)
RU (1) RU2577546C2 (enExample)
UA (1) UA110696C2 (enExample)
WO (1) WO2011063276A1 (enExample)
ZA (1) ZA201203883B (enExample)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120085330A (ko) * 2009-11-23 2012-07-31 알러간, 인코포레이티드 결정형 ｉｉ의 ７?〔３,５?다이하이드록시?２?(３?하이드록시?５?페닐?펜트?１?에닐)?사이클로펜틸〕?ｎ?에틸?헵트?５?엔아마이드(비마토프로스트), 그의 제조방법 및 이용방법
CN106349138A (zh) * 2011-06-02 2017-01-25 奇诺因私人有限公司 用于制备前列腺素酰胺的新的方法
WO2014066775A1 (en) 2012-10-26 2014-05-01 Forsight Vision5, Inc. Ophthalmic system for sustained release of drug to eye
EP3827823A1 (en) * 2012-12-19 2021-06-02 Novartis AG Lfa-1 inhibitor formulations
US9447014B2 (en) 2012-12-28 2016-09-20 Allergan, Inc. Tromethamine salt of bimatoprost acid in crystalline form, methods for preparation, and methods for use thereof
US9120738B2 (en) * 2012-12-28 2015-09-01 Allergan, Inc. Crystalline forms of bimatoprost acid, methods for preparation, and methods for use thereof
US10273206B2 (en) 2014-06-27 2019-04-30 Allergan, Inc. Tromethamine salt of bimatoprost acid in crystalline form 1, methods for preparation, and methods for use thereof
EP3283004A4 (en) 2015-04-13 2018-12-05 Forsight Vision5, Inc. Ocular insert composition of semi-crystalline or crystalline pharmaceutically active agent
WO2022251710A2 (en) 2021-05-28 2022-12-01 Sight Sciences, Inc. Intraocular devices, systems, and methods
CN115677549A (zh) * 2022-10-27 2023-02-03 神隆医药（常熟）有限公司 一种贝美前列素手性异构体的制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050209377A1 (en) * 2003-12-30 2005-09-22 Padwa Allen R Nucleating agents
US20090163596A1 (en) * 2006-08-29 2009-06-25 Arie Gutman Bimatoprost crystalline form I

Family Cites Families (4)

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Publication number Priority date Publication date Assignee Title
IL143477A (en) * 2001-05-31 2009-07-20 Finetech Pharmaceutical Ltd Process for the preparation of 17-phenyl-18,19,20-trinor-pgf2?? and its derivatives
US7166730B2 (en) * 2000-01-27 2007-01-23 Fine Tech Laboratories, Ltd Process for the preparation of prostaglandin derivatives
EP1307191A2 (en) * 2000-07-28 2003-05-07 Inspire Pharmaceuticals, Inc. Use of indole derivatives for the manufacture of a medicament for reducing intracular pressure
KR20120085330A (ko) * 2009-11-23 2012-07-31 알러간, 인코포레이티드 결정형 ｉｉ의 ７?〔３,５?다이하이드록시?２?(３?하이드록시?５?페닐?펜트?１?에닐)?사이클로펜틸〕?ｎ?에틸?헵트?５?엔아마이드(비마토프로스트), 그의 제조방법 및 이용방법

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050209377A1 (en) * 2003-12-30 2005-09-22 Padwa Allen R Nucleating agents
US20090163596A1 (en) * 2006-08-29 2009-06-25 Arie Gutman Bimatoprost crystalline form I

Also Published As

Publication number Publication date
ZA201203883B (en) 2013-01-31
PH12012501098A1 (en) 2014-10-14
AU2010321831A1 (en) 2012-06-21
US20110152376A1 (en) 2011-06-23
RU2012125185A (ru) 2013-12-27
JP5921439B2 (ja) 2016-05-24
EP2504313A1 (en) 2012-10-03
NZ600263A (en) 2014-08-29
JP2013511573A (ja) 2013-04-04
CN104367580A (zh) 2015-02-25
CL2012001339A1 (es) 2012-08-10
CN102712584A (zh) 2012-10-03
US9181176B2 (en) 2015-11-10
IL219959A0 (en) 2012-07-31
US8629185B2 (en) 2014-01-14
RU2577546C2 (ru) 2016-03-20
JP2016094471A (ja) 2016-05-26
HK1207570A1 (en) 2016-02-05
MX2012005968A (es) 2012-08-15
US20140113974A1 (en) 2014-04-24
IL219959A (en) 2015-07-30
UA110696C2 (uk) 2016-02-10
KR20120085330A (ko) 2012-07-31
CO6551754A2 (es) 2012-10-31
IN2012DN05209A (enExample) 2015-10-23
CN102712584B (zh) 2014-10-29
WO2011063276A1 (en) 2011-05-26
CA2781698A1 (en) 2011-05-26
BR112012012387A2 (pt) 2019-09-24
IL239892A0 (en) 2015-08-31

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