RU2505530C2 - Замещенные циклопентаны, обладающие простагландиновой активностью - Google Patents
Замещенные циклопентаны, обладающие простагландиновой активностью Download PDFInfo
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- RU2505530C2 RU2505530C2 RU2010135795/04A RU2010135795A RU2505530C2 RU 2505530 C2 RU2505530 C2 RU 2505530C2 RU 2010135795/04 A RU2010135795/04 A RU 2010135795/04A RU 2010135795 A RU2010135795 A RU 2010135795A RU 2505530 C2 RU2505530 C2 RU 2505530C2
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
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- 206010030348 Open-Angle Glaucoma Diseases 0.000 description 3
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- 125000000304 alkynyl group Chemical group 0.000 description 2
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- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
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- XAEKNFHALOLRCQ-RBTJGNDVSA-N propyl 7-[(1r,2s,3r,5r)-5-chloro-2-(hydroxymethyl)-3-(oxan-2-yloxy)cyclopentyl]heptanoate Chemical compound OC[C@@H]1[C@@H](CCCCCCC(=O)OCCC)[C@H](Cl)C[C@H]1OC1OCCCC1 XAEKNFHALOLRCQ-RBTJGNDVSA-N 0.000 description 2
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- PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 1
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- PBXKZBRQCQEENQ-UZMOGYDDSA-N 7-[(1r,2r,3r,5r)-5-chloro-2-[(e,3s,7r)-3,7-dihydroxyoct-1-enyl]-3-hydroxycyclopentyl]heptanoic acid Chemical compound C[C@@H](O)CCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H](Cl)[C@@H]1CCCCCCC(O)=O PBXKZBRQCQEENQ-UZMOGYDDSA-N 0.000 description 1
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- 125000002723 alicyclic group Chemical group 0.000 description 1
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
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- 125000004051 hexyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- VOPZEYMGVHOKLJ-RSNHYIQPSA-N prop-2-enyl (z)-7-[(1r,2r,3r,5r)-2-[(e,3s,7r)-7-[tert-butyl(dimethyl)silyl]oxy-3-hydroxyoct-1-enyl]-5-chloro-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoate Chemical compound C1[C@@H](Cl)[C@H](C\C=C/CCCC(=O)OCC=C)[C@@H](/C=C/[C@@H](O)CCC[C@@H](C)O[Si](C)(C)C(C)(C)C)[C@@H]1OC1OCCCC1 VOPZEYMGVHOKLJ-RSNHYIQPSA-N 0.000 description 1
- SWNGWFQRKMJAJE-XEXOEKHYSA-N prop-2-enyl (z)-7-[(1r,2r,3r,5r)-5-chloro-2-[(e,3s,7r)-3,7-dihydroxyoct-1-enyl]-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoate Chemical compound C1[C@@H](Cl)[C@H](C\C=C/CCCC(=O)OCC=C)[C@@H](/C=C/[C@@H](O)CCC[C@H](O)C)[C@@H]1OC1OCCCC1 SWNGWFQRKMJAJE-XEXOEKHYSA-N 0.000 description 1
- WNTPGAPNVFVILN-QZSFTUMGSA-N prop-2-enyl (z)-7-[(1r,2r,3r,5r)-5-chloro-2-[(e,3s,7r)-3,7-dihydroxyoct-1-enyl]-3-hydroxycyclopentyl]hept-5-enoate Chemical compound C[C@@H](O)CCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H](Cl)[C@@H]1C\C=C/CCCC(=O)OCC=C WNTPGAPNVFVILN-QZSFTUMGSA-N 0.000 description 1
- AFVSLSAKWTXVFU-PZURGIOQSA-N prop-2-enyl (z)-7-[(1r,2r,3r,5r)-5-chloro-2-formyl-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoate Chemical compound O=C[C@@H]1[C@@H](C\C=C/CCCC(=O)OCC=C)[C@H](Cl)C[C@H]1OC1OCCCC1 AFVSLSAKWTXVFU-PZURGIOQSA-N 0.000 description 1
- QYVCENQTPVNJRU-HDVDXKJFSA-N propyl 7-[(1r,2r,3r,5r)-2-[(e,3s,7r)-7-[tert-butyl(dimethyl)silyl]oxy-3-hydroxyoct-1-enyl]-5-chloro-3-(oxan-2-yloxy)cyclopentyl]heptanoate Chemical compound CC(C)(C)[Si](C)(C)O[C@H](C)CCC[C@H](O)/C=C/[C@@H]1[C@@H](CCCCCCC(=O)OCCC)[C@H](Cl)C[C@H]1OC1OCCCC1 QYVCENQTPVNJRU-HDVDXKJFSA-N 0.000 description 1
- SGTBTXSZWVGSDS-LDMLUASCSA-N propyl 7-[(1r,2r,3r,5r)-5-chloro-2-[(e,3s,7r)-3,7-dihydroxyoct-1-enyl]-3-(oxan-2-yloxy)cyclopentyl]heptanoate Chemical compound C[C@@H](O)CCC[C@H](O)/C=C/[C@@H]1[C@@H](CCCCCCC(=O)OCCC)[C@H](Cl)C[C@H]1OC1OCCCC1 SGTBTXSZWVGSDS-LDMLUASCSA-N 0.000 description 1
- 125000001436 propyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- 210000001957 retinal vein Anatomy 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- 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
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Ophthalmology & Optometry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (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)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2617908P | 2008-02-05 | 2008-02-05 | |
| US61/026,179 | 2008-02-05 | ||
| US12/363,996 US8455547B2 (en) | 2008-02-05 | 2009-02-02 | Substituted cyclopentanes having prostaglandin activity |
| US12/363,996 | 2009-02-02 | ||
| PCT/US2009/032943 WO2009100057A1 (en) | 2008-02-05 | 2009-02-03 | Substituted cyclopentanes having prostaglandin activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2010135795A RU2010135795A (ru) | 2012-03-20 |
| RU2505530C2 true RU2505530C2 (ru) | 2014-01-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010135795/04A RU2505530C2 (ru) | 2008-02-05 | 2009-02-03 | Замещенные циклопентаны, обладающие простагландиновой активностью |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8455547B2 (https=) |
| EP (2) | EP2245005A1 (https=) |
| JP (1) | JP5566912B2 (https=) |
| KR (1) | KR20100119787A (https=) |
| CN (1) | CN101959854A (https=) |
| AU (1) | AU2009212570B2 (https=) |
| BR (1) | BRPI0907913A2 (https=) |
| CA (1) | CA2713958A1 (https=) |
| IL (1) | IL207354A0 (https=) |
| MX (1) | MX2010008589A (https=) |
| RU (1) | RU2505530C2 (https=) |
| WO (1) | WO2009100057A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2418592C1 (ru) * | 2010-04-19 | 2011-05-20 | Геннадий Васильевич Порядин | Способ лечения артериальной гипертонии |
| US9315486B2 (en) | 2013-10-29 | 2016-04-19 | Allergan, Inc. | Therapeutic cyclopentanols, compositions thereof, and methods for use thereof |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2228154A1 (de) * | 1971-06-11 | 1972-12-28 | G.D. Searle & Co., Skokie, 111. (V.StA.) | Verfahren zur Reduktion von Ketoprostaglandinen |
| EP0116358A1 (de) * | 1983-02-12 | 1984-08-22 | Bayer Ag | Komplexe von Prostaglandinen |
| US6410591B1 (en) * | 2001-05-08 | 2002-06-25 | Allergan Sales, Inc. | 3,7 or 3 and 7 thia or oxa prostanoic acid derivatives as agents for lowering intraocular pressure |
| WO2005013928A1 (en) * | 2003-08-12 | 2005-02-17 | Sucampo Ag | Composition and method for promoting hair growth |
| US20050070516A1 (en) * | 1997-10-28 | 2005-03-31 | Vivus Inc. | As-needed administration of an androgenic agent to enhance female desire and responsiveness |
| RU2005129072A (ru) * | 2003-02-11 | 2006-02-27 | Аллерган, Инк. (Us) | Производные 10,10-диалкилпростановой кислоты для снижения внутриглазного давления |
| WO2006063179A1 (en) * | 2004-12-10 | 2006-06-15 | Allergan, Inc. | 12-aryl prostaglandin analogs |
| WO2007060453A1 (en) * | 2005-11-26 | 2007-05-31 | Medical Research Council | Promoting wound healing by administering a prostaglandin e and granulocyte-macrophage colony stimulating factor |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55133354A (en) * | 1979-04-02 | 1980-10-17 | Upjohn Co | Prostaglandin derivatives |
| US4259516A (en) * | 1979-04-02 | 1981-03-31 | The Upjohn Company | 19-Hydroxy-inter-oxa-13,14-dihydro-PG1 compounds |
| DE3304864A1 (de) * | 1983-02-12 | 1984-08-16 | Bayer Ag, 5090 Leverkusen | Adsorbate von prostaglandinen |
| ATE266397T1 (de) | 1997-02-04 | 2004-05-15 | Murray A Johnstone | Verfahren zur förderung des haarwuchses und entwicklung des haarsystems |
| SE9702681D0 (sv) * | 1997-07-10 | 1997-07-10 | Pharmacia & Upjohn Ab | Method and composition for treatment of impotence |
| US5877211A (en) * | 1997-11-21 | 1999-03-02 | Allergan | EP2 receptor agonists as neuroprotective agents for the eye |
| US20020037914A1 (en) | 2000-03-31 | 2002-03-28 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
| PL1759702T3 (pl) | 2004-05-26 | 2009-06-30 | Bayardo Arturo Jimenez | Sposób wytwarzania roztworu latanoprostu do oczu oraz roztwór otrzymany tym sposobem |
| US7476755B2 (en) * | 2006-05-04 | 2009-01-13 | Allergan, Inc. | Therapeutic compounds |
| EP2037967B1 (en) | 2006-06-16 | 2016-12-07 | The Trustees Of The University Of Pennsylvania | Prostaglandin d2 receptor antagonists for treating androgenetic alopecia |
-
2009
- 2009-02-02 US US12/363,996 patent/US8455547B2/en active Active
- 2009-02-03 KR KR1020107019695A patent/KR20100119787A/ko not_active Ceased
- 2009-02-03 JP JP2010545948A patent/JP5566912B2/ja not_active Expired - Fee Related
- 2009-02-03 EP EP09708693A patent/EP2245005A1/en not_active Withdrawn
- 2009-02-03 WO PCT/US2009/032943 patent/WO2009100057A1/en not_active Ceased
- 2009-02-03 AU AU2009212570A patent/AU2009212570B2/en not_active Ceased
- 2009-02-03 CN CN2009801079234A patent/CN101959854A/zh active Pending
- 2009-02-03 BR BRPI0907913-0A patent/BRPI0907913A2/pt not_active IP Right Cessation
- 2009-02-03 CA CA2713958A patent/CA2713958A1/en not_active Abandoned
- 2009-02-03 EP EP12167472A patent/EP2487153A1/en not_active Withdrawn
- 2009-02-03 RU RU2010135795/04A patent/RU2505530C2/ru not_active IP Right Cessation
- 2009-02-03 MX MX2010008589A patent/MX2010008589A/es active IP Right Grant
-
2010
- 2010-08-02 IL IL207354A patent/IL207354A0/en unknown
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2228154A1 (de) * | 1971-06-11 | 1972-12-28 | G.D. Searle & Co., Skokie, 111. (V.StA.) | Verfahren zur Reduktion von Ketoprostaglandinen |
| EP0116358A1 (de) * | 1983-02-12 | 1984-08-22 | Bayer Ag | Komplexe von Prostaglandinen |
| US20050070516A1 (en) * | 1997-10-28 | 2005-03-31 | Vivus Inc. | As-needed administration of an androgenic agent to enhance female desire and responsiveness |
| US6410591B1 (en) * | 2001-05-08 | 2002-06-25 | Allergan Sales, Inc. | 3,7 or 3 and 7 thia or oxa prostanoic acid derivatives as agents for lowering intraocular pressure |
| RU2005129072A (ru) * | 2003-02-11 | 2006-02-27 | Аллерган, Инк. (Us) | Производные 10,10-диалкилпростановой кислоты для снижения внутриглазного давления |
| WO2005013928A1 (en) * | 2003-08-12 | 2005-02-17 | Sucampo Ag | Composition and method for promoting hair growth |
| WO2006063179A1 (en) * | 2004-12-10 | 2006-06-15 | Allergan, Inc. | 12-aryl prostaglandin analogs |
| WO2007060453A1 (en) * | 2005-11-26 | 2007-05-31 | Medical Research Council | Promoting wound healing by administering a prostaglandin e and granulocyte-macrophage colony stimulating factor |
Non-Patent Citations (1)
| Title |
|---|
| DATABASE CAS on STN, реферат статьи Steffenrud S. et al. "Metabolism of prostaglandin E analogs in the guinea pig liver mitochondrial fraction", "Biochemical Medicine", 1984, 32, p.161-180, RN 93800-38-5. * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2009212570B2 (en) | 2014-04-10 |
| IL207354A0 (en) | 2010-12-30 |
| EP2245005A1 (en) | 2010-11-03 |
| RU2010135795A (ru) | 2012-03-20 |
| AU2009212570A1 (en) | 2009-08-13 |
| WO2009100057A1 (en) | 2009-08-13 |
| EP2487153A1 (en) | 2012-08-15 |
| MX2010008589A (es) | 2010-08-23 |
| CN101959854A (zh) | 2011-01-26 |
| US8455547B2 (en) | 2013-06-04 |
| JP5566912B2 (ja) | 2014-08-06 |
| BRPI0907913A2 (pt) | 2015-07-28 |
| US20090197962A1 (en) | 2009-08-06 |
| JP2011511081A (ja) | 2011-04-07 |
| KR20100119787A (ko) | 2010-11-10 |
| CA2713958A1 (en) | 2009-08-13 |
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| Date | Code | Title | Description |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20150204 |