CA2039420A1 - Treatment of cataract with 15-keto-prostaglandin compounds - Google Patents
Treatment of cataract with 15-keto-prostaglandin compoundsInfo
- Publication number
- CA2039420A1 CA2039420A1 CA2039420A CA2039420A CA2039420A1 CA 2039420 A1 CA2039420 A1 CA 2039420A1 CA 2039420 A CA2039420 A CA 2039420A CA 2039420 A CA2039420 A CA 2039420A CA 2039420 A1 CA2039420 A1 CA 2039420A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- hydrogen atom
- unsubstituted
- substituted
- halogen
- 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.)
- Granted
Links
- 208000002177 Cataract Diseases 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- 125000005843 halogen group Chemical group 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- 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
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
Abstract
A pharmaceutical composition for treatment of cataract comprising a 15-ketoprostaglandin compound in association with a pharmaceutically acceptable carrier, diluent or excipient, of the general formula:
(I) wherein L and M are hydrogen atom, hydroxy, lower alkyl, hydroxy(lower)alkyl or oxo, provided that at least one of L
and M is not hydrogen atom and that the five-membered ring may have one or two doubl.e bonds, Q1 and Q2 are hydrogen atom, halogen atom or lower alkyl, D is -CH2-CH2-, -CH=CH-, -CC-or -CO-CH2-, E is -CH2-CH2- or -CH=CH-, W is -CH2-CH2-CH2-, -CH=CH-CH2 or -CH2-CH=CH-, Ra is hydrogen atom, lower alkyl, lower cycloalkyl, monocyclic aryl, monocyclic aryl(lower)alkyl or monocyclic aroyl(lower)alkyl, Rb is single bond or lower alkylene, Rc is lower alkyl which is unsubstituted or substituted with halogen, lower cycloalkyl which is unsubstituted or substituted with lower alkyl, monocyclic aryl which is unsubstituted or substituted with halogen or halo(lower)alkyl, or monocyclic aryloxy which is unsubstituted or substituted with halogen or halo(lower)alkyl, or a pharmaceutically acceptable salt when Ra is hydrogen atom.
(I) wherein L and M are hydrogen atom, hydroxy, lower alkyl, hydroxy(lower)alkyl or oxo, provided that at least one of L
and M is not hydrogen atom and that the five-membered ring may have one or two doubl.e bonds, Q1 and Q2 are hydrogen atom, halogen atom or lower alkyl, D is -CH2-CH2-, -CH=CH-, -CC-or -CO-CH2-, E is -CH2-CH2- or -CH=CH-, W is -CH2-CH2-CH2-, -CH=CH-CH2 or -CH2-CH=CH-, Ra is hydrogen atom, lower alkyl, lower cycloalkyl, monocyclic aryl, monocyclic aryl(lower)alkyl or monocyclic aroyl(lower)alkyl, Rb is single bond or lower alkylene, Rc is lower alkyl which is unsubstituted or substituted with halogen, lower cycloalkyl which is unsubstituted or substituted with lower alkyl, monocyclic aryl which is unsubstituted or substituted with halogen or halo(lower)alkyl, or monocyclic aryloxy which is unsubstituted or substituted with halogen or halo(lower)alkyl, or a pharmaceutically acceptable salt when Ra is hydrogen atom.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9089590 | 1990-04-04 | ||
JP90895/1990 | 1990-04-04 | ||
JP221646/1990 | 1990-08-22 | ||
JP22164690 | 1990-08-22 | ||
JP2931091 | 1991-01-29 | ||
JP29310/1991 | 1991-01-29 |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2039420A1 true CA2039420A1 (en) | 1991-10-05 |
CA2039420C CA2039420C (en) | 1996-12-10 |
Family
ID=27286510
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002039420A Expired - Lifetime CA2039420C (en) | 1990-04-04 | 1991-03-28 | Treatment of cataract with 15-keto-prostaglandin compounds |
Country Status (11)
Country | Link |
---|---|
US (2) | US5212324A (en) |
EP (1) | EP0453127B1 (en) |
KR (1) | KR970005172B1 (en) |
AT (1) | ATE169219T1 (en) |
AU (1) | AU644148B2 (en) |
CA (1) | CA2039420C (en) |
DE (1) | DE69129921T2 (en) |
DK (1) | DK0453127T3 (en) |
ES (1) | ES2119762T3 (en) |
GR (1) | GR3027666T3 (en) |
TW (2) | TW224942B (en) |
Families Citing this family (54)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW205508B (en) * | 1990-08-02 | 1993-05-11 | Kabushikaisha Ueno Seiyaku Oyo Kenkyujo | |
US5688819A (en) * | 1992-09-21 | 1997-11-18 | Allergan | Cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents |
US5972991A (en) | 1992-09-21 | 1999-10-26 | Allergan | Cyclopentane heptan(ene) oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
US5352708A (en) * | 1992-09-21 | 1994-10-04 | Allergan, Inc. | Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents |
US5328933A (en) * | 1992-10-28 | 1994-07-12 | Allergan, Inc. | Cyclopentane heptenylnitro and heptanylnitro-2-aliphatic or aryl aliphatic derivatives and homologues |
SE9303627D0 (en) * | 1993-11-03 | 1993-11-03 | Kabi Pharmacia Ab | Method and means for the prevention of cataract |
EP0735895B1 (en) * | 1993-11-19 | 2006-01-18 | The University Of Sydney | A method for preventing or controlling cataract |
SE9403160D0 (en) * | 1994-09-21 | 1994-09-21 | Pharmacia Ab | Method and means for prevention and treatment of secondary cataract |
WO1997047595A1 (en) * | 1996-06-10 | 1997-12-18 | R-Tech Ueno, Ltd. | Endothelin antagonist |
SK3382000A3 (en) * | 1997-09-09 | 2000-10-09 | Procter & Gamble | A compound having structure of aromatic substituted prostaglandins and its use for the treatment of bone disorders |
ID23971A (en) * | 1997-09-09 | 2000-06-14 | Procter & Gamble | PROSTAGLANDIN TETRAHIDRO SUBSTITUTEDIC C <16> -C <20> AROMATICS USING AS FP AGONISTS |
CN1206997C (en) * | 1997-11-28 | 2005-06-22 | 株式会社·R-技术上野 | Endothelin antagonist |
CZ20013174A3 (en) | 1999-03-05 | 2002-02-13 | The Procter & Gamble Company | C 16 unsaturated FP-selective prostaglandin analogs |
TWI225398B (en) | 1999-07-14 | 2004-12-21 | R Tech Ueno Ltd | Composition for treatment of external secretion disorders |
CA2402597C (en) * | 2000-03-16 | 2011-04-26 | Sucampo Ag | Composition for use in treatment of ocular hypertension and glaucoma |
US6458836B1 (en) | 2000-03-16 | 2002-10-01 | Sucampo, A.G. | Treatment of ocular hypertension and glaucoma |
CA2403086C (en) | 2000-03-24 | 2010-08-17 | Sucampo Ag | Apoptosis inhibiting composition comprising a 15-keto-prostaglandin or derivative thereof |
US20020037914A1 (en) * | 2000-03-31 | 2002-03-28 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
US20020013294A1 (en) * | 2000-03-31 | 2002-01-31 | Delong Mitchell Anthony | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
US20020146439A1 (en) * | 2000-03-31 | 2002-10-10 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using oximyl and hydroxylamino prostaglandins |
US20020172693A1 (en) | 2000-03-31 | 2002-11-21 | Delong Michell Anthony | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
AU4472701A (en) * | 2000-04-06 | 2001-10-23 | Sucampo Ag | Bile secretion promoting composition |
TWI302100B (en) | 2001-05-02 | 2008-10-21 | Sucampo Ag | Composition for treating drug-induced constipation |
MXPA04001604A (en) * | 2001-08-23 | 2004-07-08 | Sucampo Ag | Method and composition for treatment of ocular hypertension and glaucoma. |
CA2458471C (en) | 2001-08-31 | 2012-07-31 | Sucampo Ag | Prostaglandin analogs as chloride channel opener |
US8580851B2 (en) | 2002-08-21 | 2013-11-12 | Sucampo Ag | Ophthalmic solution |
EP1562604B1 (en) * | 2002-10-23 | 2012-01-04 | Sucampo AG | Prostaglandin compounds for the treatment of obesity |
JP4889219B2 (en) | 2002-12-27 | 2012-03-07 | スキャンポ・アーゲー | Prostaglandin derivatives for the treatment of abdominal discomfort |
WO2005002588A1 (en) * | 2003-07-03 | 2005-01-13 | Sucampo Ag | Enteric coated composition comprising prostaglandin analogs as chloride channel opener |
TWI495471B (en) * | 2003-08-12 | 2015-08-11 | R Tech Ueno Ltd | Composition and method for promoting hair growth |
EP2404606A1 (en) | 2003-08-21 | 2012-01-11 | Sucampo AG | Ophthalmic compositions comprising a prostaglandin and a viscosity agent |
SE0303179D0 (en) * | 2003-11-26 | 2003-11-26 | Astrazeneca Ab | Novel compounds |
JP4690814B2 (en) * | 2004-08-02 | 2011-06-01 | 株式会社アールテック・ウエノ | Method for producing prostaglandin derivatives |
CN101146541B (en) | 2005-01-27 | 2012-04-11 | 苏坎波公司 | Method and composition for treating central nervous system disorders |
EP2329825B1 (en) | 2005-03-04 | 2015-10-07 | Sucampo AG | Method and composition for treating peripheral vascular diseases |
WO2010102078A1 (en) | 2009-03-04 | 2010-09-10 | Allergan, Inc. | Enhanced bimatoprost ophthalmic solution |
US7851504B2 (en) | 2005-03-16 | 2010-12-14 | Allergan, Inc. | Enhanced bimatoprost ophthalmic solution |
US20060281818A1 (en) | 2005-03-21 | 2006-12-14 | Sucampo Ag, North Carolina State University | Method for treating mucosal disorders |
BRPI0610557A2 (en) * | 2005-04-12 | 2010-06-29 | Sucampo Ag | combined use of prostaglandin compound and proton pump inhibitor for the treatment of gastrointestinal disorders and pharmaceutical composition |
MX2008009650A (en) | 2006-01-24 | 2008-11-06 | R Tech Ueno Ltd | Soft-gelatin capsule formulation. |
JP5265369B2 (en) * | 2006-01-24 | 2013-08-14 | 株式会社アールテック・ウエノ | Pharmaceutical composition comprising a bicyclic compound and method for stabilizing the bicyclic compound |
CA2645311C (en) | 2006-03-13 | 2014-11-18 | R-Tech Ueno, Ltd. | Aqueous composition comprising 15-keto-prostaglandin for ophthalmic use |
US8871752B2 (en) * | 2008-02-19 | 2014-10-28 | Sucampo Ag | Method for modulating stem cell growth |
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 |
US8609729B2 (en) | 2009-04-15 | 2013-12-17 | Sucampo Ag | Method for treating macular degeneration |
US8569279B2 (en) * | 2009-05-27 | 2013-10-29 | Sucampo Ag | Method for modulating claudin mediated functions |
US9084815B2 (en) * | 2009-09-16 | 2015-07-21 | Sucampo Ag | Method for treating damage induced by an anti-tumor agent, treating mucositis and treating tumor |
US9522153B2 (en) | 2009-12-22 | 2016-12-20 | Allergan, Inc. | Compositions and methods for lowering intraocular pressure |
CA2830626A1 (en) | 2011-04-07 | 2012-10-11 | Sucampo Ag | Method for treating asthenopia |
NZ620300A (en) | 2011-08-05 | 2015-09-25 | Sucampo Ag | Method for treating schizophrenia |
AR092821A1 (en) | 2012-04-20 | 2015-05-06 | Sucampo Ag | CONJUGATE OF GRASO-POLYMER ACID DERIVATIVE |
US20150057351A1 (en) | 2013-08-22 | 2015-02-26 | Sucampo Ag | Method for treating neuropathic pain |
WO2016203317A1 (en) | 2015-06-19 | 2016-12-22 | Sucampo Ag | Pharmaceutical compositions comprising fatty acid derivative |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3505386A (en) * | 1965-12-29 | 1970-04-07 | Upjohn Co | Compounds related to prostaglandins |
US3974195A (en) * | 1974-10-02 | 1976-08-10 | The Upjohn Company | 2A,2B-Dihomo-15-alkyl-PGF2.sub.α analogs |
EP0153858A3 (en) * | 1984-02-29 | 1985-12-11 | The Upjohn Company | The therapeutic use of prostaglandins |
CA1322749C (en) * | 1987-01-28 | 1993-10-05 | Ryuzo Ueno | Prostaglandins of the d series, and tranquilizers and soporifics containing the same |
CA1323364C (en) * | 1987-01-28 | 1993-10-19 | Ryuzo Ueno | Prostaglandins e and anti ulcer agents containing same |
CA1324129C (en) * | 1987-04-30 | 1993-11-09 | Ryuzo Ueno | Prostaglandins of the f series |
ES2038289T3 (en) * | 1987-05-15 | 1993-07-16 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | USE OF 15-CETO-PGES FOR THE MANUFACTURE OF A MEDICINAL PRODUCT TO INCREASE BODY TEMPERATURE. |
GB2209939B (en) * | 1987-09-18 | 1992-01-02 | R Tech Ueno Ltd | The use of 13,14-dihydro-15-keto-prostaglandins as ocular hypotensive agents |
ATE78465T1 (en) * | 1987-10-02 | 1992-08-15 | Ueno Seiyaku Oyo Kenkyujo Kk | KATHARTICA. |
JP2597629B2 (en) * | 1988-02-26 | 1997-04-09 | 株式会社 上野製薬応用研究所 | Stabilization of 13,14-dihydro-15-ketoprostaglandins |
JP2597649B2 (en) * | 1988-05-11 | 1997-04-09 | 株式会社上野製薬応用研究所 | Trachea / bronchodilator |
AU619543B2 (en) * | 1988-05-11 | 1992-01-30 | Sucampo Ag | Use of 15-ketoprostaglandin e or f compounds for uterine contraction |
ES2055051T3 (en) * | 1988-05-23 | 1994-08-16 | Ueno Seiyaku Oyo Kenkyujo Kk | A METHOD FOR THE MANUFACTURE OF AN EFFECTIVE MEDICINE TO INCREASE BLOOD PRESSURE. |
AU604156B2 (en) * | 1988-09-14 | 1990-12-06 | R-Tech Ueno, Ltd. | Prostaglandins of the F series |
DE68928551T2 (en) * | 1988-10-01 | 1998-04-23 | R Tech Ueno Ltd | Ocular hypotensive means |
TW205508B (en) * | 1990-08-02 | 1993-05-11 | Kabushikaisha Ueno Seiyaku Oyo Kenkyujo |
-
1991
- 1991-03-28 TW TW080102419A patent/TW224942B/zh not_active IP Right Cessation
- 1991-03-28 CA CA002039420A patent/CA2039420C/en not_active Expired - Lifetime
- 1991-03-28 TW TW081106617A patent/TW249226B/zh not_active IP Right Cessation
- 1991-04-03 AU AU74047/91A patent/AU644148B2/en not_active Expired
- 1991-04-03 EP EP91302925A patent/EP0453127B1/en not_active Expired - Lifetime
- 1991-04-03 AT AT91302925T patent/ATE169219T1/en not_active IP Right Cessation
- 1991-04-03 DE DE69129921T patent/DE69129921T2/en not_active Expired - Lifetime
- 1991-04-03 DK DK91302925T patent/DK0453127T3/en active
- 1991-04-03 ES ES91302925T patent/ES2119762T3/en not_active Expired - Lifetime
- 1991-04-03 US US07/680,187 patent/US5212324A/en not_active Expired - Lifetime
- 1991-04-04 KR KR1019910005502A patent/KR970005172B1/en not_active IP Right Cessation
-
1994
- 1994-09-06 US US08/300,541 patent/US5686487A/en not_active Expired - Lifetime
-
1998
- 1998-08-19 GR GR980400874T patent/GR3027666T3/en unknown
Also Published As
Publication number | Publication date |
---|---|
AU7404791A (en) | 1991-10-10 |
US5686487A (en) | 1997-11-11 |
KR970005172B1 (en) | 1997-04-14 |
DE69129921T2 (en) | 1999-01-14 |
TW249226B (en) | 1995-06-11 |
GR3027666T3 (en) | 1998-11-30 |
EP0453127A3 (en) | 1992-12-09 |
ES2119762T3 (en) | 1998-10-16 |
KR910018027A (en) | 1991-11-30 |
US5212324A (en) | 1993-05-18 |
AU644148B2 (en) | 1993-12-02 |
ATE169219T1 (en) | 1998-08-15 |
EP0453127B1 (en) | 1998-08-05 |
EP0453127A2 (en) | 1991-10-23 |
DE69129921D1 (en) | 1998-09-10 |
DK0453127T3 (en) | 1998-10-26 |
TW224942B (en) | 1994-06-11 |
CA2039420C (en) | 1996-12-10 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKEX | Expiry |