JP5566912B2 - プロスタグランジン活性を有する置換シクロペンタン類 - Google Patents
プロスタグランジン活性を有する置換シクロペンタン類 Download PDFInfo
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- JP5566912B2 JP5566912B2 JP2010545948A JP2010545948A JP5566912B2 JP 5566912 B2 JP5566912 B2 JP 5566912B2 JP 2010545948 A JP2010545948 A JP 2010545948A JP 2010545948 A JP2010545948 A JP 2010545948A JP 5566912 B2 JP5566912 B2 JP 5566912B2
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- glaucoma
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- 150000003180 prostaglandins Chemical class 0.000 title description 6
- 150000001940 cyclopentanes Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 208000010412 Glaucoma Diseases 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 5
- 206010030043 Ocular hypertension Diseases 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 230000004410 intraocular pressure Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000003779 hair growth Effects 0.000 claims description 4
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- 125000001475 halogen functional group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 235000019439 ethyl acetate Nutrition 0.000 description 27
- 239000000203 mixture Substances 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
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- 239000000047 product Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 125000001183 hydrocarbyl group Chemical group 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 10
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
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- 125000000524 functional group Chemical group 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- AQPNWGCQODYKER-RBTJGNDVSA-N propyl 7-[(1r,2r,3r,5r)-5-chloro-2-formyl-3-(oxan-2-yloxy)cyclopentyl]heptanoate Chemical compound O=C[C@@H]1[C@@H](CCCCCCC(=O)OCCC)[C@H](Cl)C[C@H]1OC1OCCCC1 AQPNWGCQODYKER-RBTJGNDVSA-N 0.000 description 4
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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 3
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- 125000004429 atom Chemical group 0.000 description 3
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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 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 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 3
- 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 3
- 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 3
- 238000000746 purification Methods 0.000 description 3
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 201000004569 Blindness Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 208000002177 Cataract Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
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- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- 201000001326 acute closed-angle glaucoma Diseases 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- -1 hydroxide ions Chemical class 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
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- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
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- 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 2
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- QSYBMZSGWULJGH-VWRKCHAESA-N propyl 7-[(1r,2r,3r,5r)-5-chloro-2-[(e,3s,7r)-3,7-dihydroxyoct-1-enyl]-3-hydroxycyclopentyl]heptanoate Chemical compound CCCOC(=O)CCCCCC[C@H]1[C@H](Cl)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC[C@@H](C)O QSYBMZSGWULJGH-VWRKCHAESA-N 0.000 description 2
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- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
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- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
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- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
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- 0 CC(CCCC(CCC(C(CC[C@@](C)CCC*)C(C1)Cl)C1O)O)O Chemical compound CC(CCCC(CCC(C(CC[C@@](C)CCC*)C(C1)Cl)C1O)O)O 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 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
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- 238000003745 diagnosis Methods 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
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 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
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- UPVNEPLEKYTKSC-PZURGIOQSA-N prop-2-enyl (z)-7-[(1r,2s,3r,5r)-5-chloro-2-(hydroxymethyl)-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](CO)[C@@H]1OC1OCCCC1 UPVNEPLEKYTKSC-PZURGIOQSA-N 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
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- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- 210000001585 trabecular meshwork Anatomy 0.000 description 1
- 230000008733 trauma Effects 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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2011511081A JP2011511081A (ja) | 2011-04-07 |
| JP2011511081A5 JP2011511081A5 (https=) | 2012-03-22 |
| JP5566912B2 true JP5566912B2 (ja) | 2014-08-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010545948A Expired - Fee Related JP5566912B2 (ja) | 2008-02-05 | 2009-02-03 | プロスタグランジン活性を有する置換シクロペンタン類 |
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 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1388443A (en) * | 1971-06-11 | 1975-03-26 | Searle & Co | Selective reduction of 9,15-dioxoprostanoic acids |
| 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 |
| US4675182A (en) | 1983-02-12 | 1987-06-23 | Bayer Aktiengesellschaft | Complexes of prostaglandins |
| 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 |
| US20050070516A1 (en) * | 1997-10-28 | 2005-03-31 | Vivus Inc. | As-needed administration of an androgenic agent to enhance female desire and responsiveness |
| 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 |
| 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 |
| AU2004211936B2 (en) * | 2003-02-11 | 2008-09-11 | Allergan, Inc. | 10,10-dialkyl prostanoic acid derivatives as agents for lowering intraocular pressure |
| TWI495471B (zh) | 2003-08-12 | 2015-08-11 | R Tech Ueno Ltd | 促進毛髮生長之組成物及方法 |
| PL1759702T3 (pl) | 2004-05-26 | 2009-06-30 | Bayardo Arturo Jimenez | Sposób wytwarzania roztworu latanoprostu do oczu oraz roztwór otrzymany tym sposobem |
| US7091231B2 (en) | 2004-12-10 | 2006-08-15 | Allergan, Inc. | 12-Aryl prostaglandin analogs |
| GB0524103D0 (en) | 2005-11-26 | 2006-01-04 | Medical Res Council | Healing |
| 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
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2010
- 2010-08-02 IL IL207354A patent/IL207354A0/en unknown
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 |
| BRPI0907913A2 (pt) | 2015-07-28 |
| RU2505530C2 (ru) | 2014-01-27 |
| US20090197962A1 (en) | 2009-08-06 |
| JP2011511081A (ja) | 2011-04-07 |
| KR20100119787A (ko) | 2010-11-10 |
| CA2713958A1 (en) | 2009-08-13 |
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