DE69714023T2 - Cyclopentane heptan(ene)säure, 2-heteroarylalkenylderivate als therapeutisches mittel - Google Patents
Cyclopentane heptan(ene)säure, 2-heteroarylalkenylderivate als therapeutisches mittelInfo
- Publication number
- DE69714023T2 DE69714023T2 DE69714023T DE69714023T DE69714023T2 DE 69714023 T2 DE69714023 T2 DE 69714023T2 DE 69714023 T DE69714023 T DE 69714023T DE 69714023 T DE69714023 T DE 69714023T DE 69714023 T2 DE69714023 T2 DE 69714023T2
- Authority
- DE
- Germany
- Prior art keywords
- pentenyl
- dihydroxy
- cyclopentyl
- hydroxy
- thienyl
- 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.)
- Expired - Fee Related
Links
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- 229940124597 therapeutic agent Drugs 0.000 title description 3
- DSFMCIXPJDRPRU-UHFFFAOYSA-N cyclopentane heptane Chemical compound C1CCCC1.CCCCCCC DSFMCIXPJDRPRU-UHFFFAOYSA-N 0.000 title 1
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
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Classifications
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
- A61K31/559—Eicosanoids, e.g. leukotrienes or prostaglandins having heterocyclic rings containing hetero atoms other than oxygen
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
- A61K31/558—Eicosanoids, e.g. leukotrienes or prostaglandins having heterocyclic rings containing oxygen as the only ring hetero atom, e.g. thromboxanes
- A61K31/5585—Eicosanoids, e.g. leukotrienes or prostaglandins having heterocyclic rings containing oxygen as the only ring hetero atom, e.g. thromboxanes having five-membered rings containing oxygen as the only ring hetero atom, e.g. prostacyclin
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
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- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Physical Education & Sports Medicine (AREA)
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- Heart & Thoracic Surgery (AREA)
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- Orthopedic Medicine & Surgery (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/608,794 US5741810A (en) | 1996-02-29 | 1996-02-29 | Cyclopentane heptan(ene)oic acid, 2- heteroarylalkenyl derivatives as therapeutic agents |
| PCT/US1997/002313 WO1997031895A2 (en) | 1996-02-29 | 1997-02-20 | Cyclopentane heptan(ene)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69714023D1 DE69714023D1 (en) | 2002-08-22 |
| DE69714023T2 true DE69714023T2 (de) | 2003-03-13 |
Family
ID=24438034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69714023T Expired - Fee Related DE69714023T2 (de) | 1996-02-29 | 1997-02-20 | Cyclopentane heptan(ene)säure, 2-heteroarylalkenylderivate als therapeutisches mittel |
Country Status (12)
| Country | Link |
|---|---|
| US (4) | US5741810A (enExample) |
| EP (1) | EP0888298B1 (enExample) |
| JP (1) | JP4226650B2 (enExample) |
| KR (1) | KR19990087352A (enExample) |
| CN (1) | CN1133434C (enExample) |
| AT (1) | ATE220664T1 (enExample) |
| AU (1) | AU725145B2 (enExample) |
| BR (1) | BR9707892A (enExample) |
| CA (1) | CA2247208A1 (enExample) |
| DE (1) | DE69714023T2 (enExample) |
| ES (1) | ES2178756T3 (enExample) |
| WO (1) | WO1997031895A2 (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6124344A (en) * | 1993-12-28 | 2000-09-26 | Allergan Sales, Inc. | Cyclopentane heptan(ene)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
| US6169111B1 (en) * | 1995-06-07 | 2001-01-02 | Alcon Laboratories, Inc. | Conformationally rigid aryl prostaglandins for use in glaucoma therapy |
| US5741810A (en) | 1996-02-29 | 1998-04-21 | Allergan | Cyclopentane heptan(ene)oic acid, 2- heteroarylalkenyl derivatives as therapeutic agents |
| DK1012137T3 (da) * | 1997-09-09 | 2003-03-10 | Procter & Gamble | Aromatiske C-16-C-20-substituerede tetrahydro-prostaglandiner og deres anvendelse som prostaglandin FP-agonister |
| IL134839A0 (en) * | 1997-09-09 | 2001-05-20 | Procter & Gamble | Aromatic c16-c20-substituted tetrahydro prostaglandins useful as fp agonists |
| ES2253826T3 (es) * | 1997-09-09 | 2006-06-01 | Duke University | Prostaglandinas aromaticas tetrahidro sustituidas por c16-c20 utilizadas como agonistas fp. |
| AU2183900A (en) | 1998-12-24 | 2000-07-31 | Alcon Laboratories, Inc. | Ep4 receptor agonists for treatment of dry eye |
| WO2000051980A1 (en) | 1999-03-05 | 2000-09-08 | The Procter & Gamble Company | C16 unsaturated fp-selective prostaglandins analogs |
| AU3385900A (en) * | 1999-03-05 | 2000-09-21 | Procter & Gamble Company, The | Method of increasing bone volume using non-naturally-occurring selective fp agonist and dito ep1 agonist prostaglandin derivatives |
| US6826874B2 (en) * | 1999-06-30 | 2004-12-07 | Nippon Steel Corporation | Buckling restrained braces and damping steel structures |
| JP4000505B2 (ja) | 1999-12-01 | 2007-10-31 | 第一三共株式会社 | 緑内障を治療するための併用剤 |
| US20020037914A1 (en) * | 2000-03-31 | 2002-03-28 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
| US20020146439A1 (en) * | 2000-03-31 | 2002-10-10 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using oximyl and hydroxylamino prostaglandins |
| US20020013294A1 (en) | 2000-03-31 | 2002-01-31 | Delong Mitchell Anthony | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
| US20020172693A1 (en) | 2000-03-31 | 2002-11-21 | Delong Michell Anthony | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
| US6248783B1 (en) * | 2000-09-20 | 2001-06-19 | Allergan Sales, Inc. | Cyclopentane 1-hydroxy alkyl or alkenyl-2-one or 2-hydroxy derivatives as therapeutic agents |
| US6531504B2 (en) * | 2001-05-17 | 2003-03-11 | Allergan, Inc. | Prostanoic acid derivatives as agents for lowering intraocular pressure |
| US6476064B1 (en) * | 2001-06-13 | 2002-11-05 | Allergan, Inc. | Cyclopentane heptan(ene) acyl sulfonamide, 2-alkyl or 2-arylalkyl, or 2-heteroarylalkenyl derivatives as therapeutic agents |
| US20040254230A1 (en) * | 2001-12-03 | 2004-12-16 | Ogidigben Miller J. | Method for treating ocular hypertension |
| US7351404B2 (en) | 2002-02-04 | 2008-04-01 | Allergan, Inc. | Method of enhancing hair growth |
| US9216183B2 (en) | 2002-02-04 | 2015-12-22 | Allergan, Inc. | Topical treatment for chemotherapy induced eyelash loss or hypotrichosis using prostamide F2 alpha agonists |
| US8758733B2 (en) | 2002-02-04 | 2014-06-24 | Allergan, Inc. | Topical treatment for chemotherapy induced eyelash loss or hypotrichosis using prostamide F2 alpha agonists |
| BR0202157A (pt) * | 2002-06-07 | 2005-04-12 | Univ Minas Gerais | Peptìdeo obtido de veneno escorpião para uso como agente hipotensivo |
| US7179820B2 (en) * | 2003-06-06 | 2007-02-20 | Allergan, Inc. | Piperidinyl prostaglandin E analogs |
| JP2005511607A (ja) * | 2003-07-10 | 2005-04-28 | アラーガン、インコーポレイテッド | ＥＰ２受容体作動剤としてのω−シクロアルキル１７−ヘテロアリールプロスタグランジンＥ２類似体 |
| US8076060B2 (en) * | 2003-08-04 | 2011-12-13 | Emil William Chynn | Vaccination and immunotherapy as new therapeutic modalities in the treatment of glaucoma |
| US7906552B2 (en) | 2004-08-10 | 2011-03-15 | Allergan, Inc. | Cyclopentane heptan(ENE)OIC acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
| US7101904B2 (en) * | 2004-08-10 | 2006-09-05 | Allergan, Inc. | Cyclopentane heptan(ENE)OIC acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
| EP2628725A1 (en) | 2005-11-03 | 2013-08-21 | Allergan, Inc. | Prostaglandins and analogues as agents for lowering intraocular pressure |
| JP4851467B2 (ja) | 2006-02-07 | 2012-01-11 | 株式会社アールテック・ウエノ | プロスタグランジン誘導体の製造法 |
| US8722739B2 (en) | 2008-10-29 | 2014-05-13 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| US8623918B2 (en) * | 2008-10-29 | 2014-01-07 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| US20110293549A1 (en) | 2009-02-03 | 2011-12-01 | Athena Cosmetics, Inc. | Composition, method and kit for enhancing hair |
| NZ628266A (en) | 2009-11-09 | 2016-02-26 | Allergan Inc | Compositions and methods for stimulating hair growth |
| US9149484B2 (en) | 2009-11-09 | 2015-10-06 | Allergan, Inc. | Compositions and methods for stimulating hair growth |
| US8783923B2 (en) * | 2010-03-18 | 2014-07-22 | Chung Yuan Christian University | Auto lamp structure |
| US8859616B2 (en) | 2011-01-21 | 2014-10-14 | Allergan, Inc. | Compounds and methods for enhancing hair growth |
| BR112015022161B1 (pt) | 2013-03-15 | 2020-11-24 | Allergan, Inc | Implante intraocular biodegradavel, uso do mesmo e metodo para fazer o mesmo |
| RU2015146211A (ru) | 2013-04-01 | 2017-05-19 | Аллерган, Инк. | Микросферная система доставки лекарственного средства для замедленного внутриглазного высвобождения |
| SG11201603383VA (en) | 2013-10-31 | 2016-05-30 | Allergan Inc | Prostamide-containing intraocular implants and methods of use thereof |
| CA2983942A1 (en) | 2015-04-30 | 2016-11-03 | Allergan, Inc. | Cosmetic method and therapeutic use for fat reduction |
| EP4185299A1 (en) | 2020-07-21 | 2023-05-31 | Allergan, Inc. | Intraocular implant with high loading of a prostamide |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3781325A (en) * | 1971-05-04 | 1973-12-25 | Upjohn Co | 15-methoxy-pgf2a |
| US3845115A (en) * | 1971-05-04 | 1974-10-29 | Upjohn Co | 15-lower alkoxy pgf compounds |
| BE786251A (fr) * | 1971-07-14 | 1973-01-15 | Ici Ltd | Nouveaux derives du cyclopentane |
| US3974213A (en) * | 1972-07-13 | 1976-08-10 | Pfizer Inc. | 13,14-Dihydro-15-substituted-ω-pentanorprostaglandins |
| DE2365767A1 (de) * | 1972-07-13 | 1976-04-15 | Pfizer | Neue prostaglandinanaloge und verfahren zu deren herstellung |
| US3956284A (en) * | 1972-07-13 | 1976-05-11 | Pfizer Inc. | Heterocyclic 15-substituted-ω-pentanorprostoglandins |
| US4102894A (en) * | 1975-11-19 | 1978-07-25 | Pfizer Inc. | 15-Substituted-ω-pentanorprostaglandins |
| US3980642A (en) * | 1972-07-13 | 1976-09-14 | Pfizer Inc. | 15-Substitute D-ω-pentanorprostaglandins |
| US4143051A (en) * | 1972-07-13 | 1979-03-06 | Pfizer Inc. | 15-Substituted-ω-pentanorprostaglandins |
| US3984424A (en) * | 1972-11-08 | 1976-10-05 | Pfizer Inc. | P-biphenyl esters of 15-substituted-ω-pentanorprostaglandins |
| US4036832A (en) * | 1974-07-03 | 1977-07-19 | Pfizer Inc. | 15-Substituted-ω-pentanorprostaglandins |
| IT1053781B (it) * | 1974-09-25 | 1981-10-10 | Erba C S P A Ora Farmitalia | Omega nor cicloalcil 13.14 deidro prostaglandine |
| IT1088966B (it) * | 1977-11-15 | 1985-06-10 | Erba Carlo Spa | 13,14-dideidro-prostaglandine |
| DE3125271A1 (de) * | 1981-06-24 | 1983-01-13 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | (delta)(pfeil hoch)8(pfeil hoch),(pfeil hoch)9(pfeil hoch)-prostaglandinderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| GB8329559D0 (en) * | 1983-11-04 | 1983-12-07 | Erba Farmitalia | Furyl derivatives of 16-substituted prostaglandins preparations |
| US5321128A (en) * | 1988-09-06 | 1994-06-14 | Kabi Pharmacia Ab | Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
| US5028624A (en) * | 1989-07-27 | 1991-07-02 | Allergan, Inc. | Intraocular pressure reducing 9,15-diacyl prostaglandins |
| US4994274A (en) * | 1989-07-27 | 1991-02-19 | Allergan, Inc. | Intraocular pressure reducing 11,15-diacyl prostaglandins and method of using |
| CA2021316C (en) * | 1989-07-27 | 2000-10-24 | Ming Fai Chan | Intraocular pressure reducing 11-acyl prostaglandins |
| US5034413A (en) * | 1989-07-27 | 1991-07-23 | Allergan, Inc. | Intraocular pressure reducing 9,11-diacyl prostaglandins |
| US5352708A (en) * | 1992-09-21 | 1994-10-04 | Allergan, Inc. | Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents |
| US5834498A (en) | 1992-09-21 | 1998-11-10 | Allergan | Cyclopentane heptan(ene)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
| AU665287B2 (en) * | 1992-12-21 | 1995-12-21 | Alcon Laboratories, Inc. | Prostaglandin combinations in glaucoma therapy |
| US5545665A (en) * | 1993-12-28 | 1996-08-13 | Allergan | Cyclopentane(ene) heptenoic or heptanoic acids and derivatives thereof useful as therapeutic agents |
| CA2221110C (en) * | 1995-05-18 | 2009-08-04 | Allergan | Cyclopentane heptan(ene)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents for the treatment of ocular hypertension |
| US5741810A (en) * | 1996-02-29 | 1998-04-21 | Allergan | Cyclopentane heptan(ene)oic acid, 2- heteroarylalkenyl derivatives as therapeutic agents |
-
1996
- 1996-02-29 US US08/608,794 patent/US5741810A/en not_active Expired - Lifetime
-
1997
- 1997-02-20 DE DE69714023T patent/DE69714023T2/de not_active Expired - Fee Related
- 1997-02-20 AT AT97907627T patent/ATE220664T1/de not_active IP Right Cessation
- 1997-02-20 EP EP97907627A patent/EP0888298B1/en not_active Expired - Lifetime
- 1997-02-20 BR BR9707892A patent/BR9707892A/pt not_active Application Discontinuation
- 1997-02-20 ES ES97907627T patent/ES2178756T3/es not_active Expired - Lifetime
- 1997-02-20 WO PCT/US1997/002313 patent/WO1997031895A2/en not_active Ceased
- 1997-02-20 AU AU19585/97A patent/AU725145B2/en not_active Ceased
- 1997-02-20 CN CNB971941122A patent/CN1133434C/zh not_active Expired - Fee Related
- 1997-02-20 KR KR1019980706761A patent/KR19990087352A/ko not_active Withdrawn
- 1997-02-20 JP JP53097697A patent/JP4226650B2/ja not_active Expired - Lifetime
- 1997-02-20 CA CA002247208A patent/CA2247208A1/en not_active Abandoned
- 1997-12-19 US US08/994,810 patent/US6096902A/en not_active Expired - Lifetime
-
2001
- 2001-01-05 US US09/755,393 patent/US6573390B2/en not_active Expired - Lifetime
-
2003
- 2003-03-07 US US10/383,896 patent/US6680337B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2178756T3 (es) | 2003-01-01 |
| BR9707892A (pt) | 1999-07-27 |
| JP2000506139A (ja) | 2000-05-23 |
| US6680337B2 (en) | 2004-01-20 |
| US20010029304A1 (en) | 2001-10-11 |
| AU1958597A (en) | 1997-09-16 |
| HK1017671A1 (en) | 1999-11-26 |
| EP0888298B1 (en) | 2002-07-17 |
| WO1997031895A3 (en) | 1997-12-18 |
| US6096902A (en) | 2000-08-01 |
| DE69714023D1 (en) | 2002-08-22 |
| ATE220664T1 (de) | 2002-08-15 |
| WO1997031895A2 (en) | 1997-09-04 |
| EP0888298A2 (en) | 1999-01-07 |
| CN1218400A (zh) | 1999-06-02 |
| KR19990087352A (ko) | 1999-12-27 |
| US5741810A (en) | 1998-04-21 |
| JP4226650B2 (ja) | 2009-02-18 |
| CA2247208A1 (en) | 1997-09-04 |
| CN1133434C (zh) | 2004-01-07 |
| US6573390B2 (en) | 2003-06-03 |
| AU725145B2 (en) | 2000-10-05 |
| US20030191178A1 (en) | 2003-10-09 |
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