JP2010532379A5 - - Google Patents
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- Publication number
- JP2010532379A5 JP2010532379A5 JP2010515212A JP2010515212A JP2010532379A5 JP 2010532379 A5 JP2010532379 A5 JP 2010532379A5 JP 2010515212 A JP2010515212 A JP 2010515212A JP 2010515212 A JP2010515212 A JP 2010515212A JP 2010532379 A5 JP2010532379 A5 JP 2010532379A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- chloro
- thiophene
- propyl
- cyclopentyl
- 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
- 150000001875 compounds Chemical class 0.000 claims 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 8
- 150000001408 amides Chemical class 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 125000000524 functional group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 4
- 150000007524 organic acids Chemical group 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- MAOFDTVJZGIUOB-XGNHVKOBSA-N 5-[3-[(1r,2s,3r)-3-hydroxy-2-(2-phenylethynyl)-5-(trifluoromethyl)cyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1C(C[C@H]([C@@H]1C#CC=1C=CC=CC=1)O)C(F)(F)F)CCC1=CC=C(C(O)=O)S1 MAOFDTVJZGIUOB-XGNHVKOBSA-N 0.000 claims 2
- 238000004128 high performance liquid chromatography Methods 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- -1 (3-((1R, 2S, 3R, 5R) -5-chloro-2-((3-ethylphenyl) ethynyl) -3-hydroxycyclopentyl) propyl) thiophene-2-carboxylic acid Chemical compound 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- PJGFZUBLJSMVLV-JKOPJJFASA-N 2-[2-[(1r,2r,3r,5r)-2-[(e)-2-(3-but-3-enyl-5-chlorophenyl)ethenyl]-5-chloro-3-hydroxycyclopentyl]ethylsulfanyl]-1,3-thiazole-4-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1\C=C\C=1C=C(CCC=C)C=C(Cl)C=1)O)CSC1=NC(C(O)=O)=CS1 PJGFZUBLJSMVLV-JKOPJJFASA-N 0.000 claims 1
- PJGFZUBLJSMVLV-DLSAWSQDSA-N 2-[2-[(1r,2r,3r,5r)-2-[(z)-2-(3-but-3-enyl-5-chlorophenyl)ethenyl]-5-chloro-3-hydroxycyclopentyl]ethylsulfanyl]-1,3-thiazole-4-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1\C=C/C=1C=C(CCC=C)C=C(Cl)C=1)O)CSC1=NC(C(O)=O)=CS1 PJGFZUBLJSMVLV-DLSAWSQDSA-N 0.000 claims 1
- ABGOBDXEJASGNN-KCYZZUKISA-N 2-[2-[(1r,2r,3r,5r)-5-chloro-2-[2-(3,5-dichlorophenyl)ethenyl]-3-hydroxycyclopentyl]ethylsulfanyl]-1,3-thiazole-4-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1C=CC=1C=C(Cl)C=C(Cl)C=1)O)CSC1=NC(C(O)=O)=CS1 ABGOBDXEJASGNN-KCYZZUKISA-N 0.000 claims 1
- BWDSOQITEOCJPE-KCYZZUKISA-N 2-[2-[(1r,2s,3r,5r)-5-chloro-2-[2-(3,5-dichlorophenyl)ethynyl]-3-hydroxycyclopentyl]ethylsulfanyl]-1,3-thiazole-4-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1C#CC=1C=C(Cl)C=C(Cl)C=1)O)CSC1=NC(C(O)=O)=CS1 BWDSOQITEOCJPE-KCYZZUKISA-N 0.000 claims 1
- VGQVVKIOZYQLPT-KCYZZUKISA-N 2-[2-[(1r,2s,3r,5r)-5-chloro-3-hydroxy-2-(2-phenylethynyl)cyclopentyl]ethylsulfanyl]-1,3-thiazole-4-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1C#CC=1C=CC=CC=1)O)CSC1=NC(C(O)=O)=CS1 VGQVVKIOZYQLPT-KCYZZUKISA-N 0.000 claims 1
- LASWCVMLRMFKLM-SSGKUCQKSA-N 5-[3-[(1r,2r,3r,5r)-2-[2-(3-but-3-enylphenyl)ethenyl]-5-chloro-3-hydroxycyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1C=CC=1C=C(CCC=C)C=CC=1)O)CCC1=CC=C(C(O)=O)S1 LASWCVMLRMFKLM-SSGKUCQKSA-N 0.000 claims 1
- SOPHKEPUTWPCEL-FQRLNYBZSA-N 5-[3-[(1r,2r,3r,5r)-5-chloro-2-[(e)-2-(2,6-dichloropyridin-4-yl)ethenyl]-3-hydroxycyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1\C=C\C=1C=C(Cl)N=C(Cl)C=1)O)CCC1=CC=C(C(O)=O)S1 SOPHKEPUTWPCEL-FQRLNYBZSA-N 0.000 claims 1
- PEBZVFPSFALNKS-AQWMBLLYSA-N 5-[3-[(1r,2r,3r,5r)-5-chloro-2-[(e)-2-(3,5-difluorophenyl)ethenyl]-3-hydroxycyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1\C=C\C=1C=C(F)C=C(F)C=1)O)CCC1=CC=C(C(O)=O)S1 PEBZVFPSFALNKS-AQWMBLLYSA-N 0.000 claims 1
- CZHYKYWDRJHXPF-OLMDXKKMSA-N 5-[3-[(1r,2r,3r,5r)-5-chloro-2-[(e)-2-(5-chloropyridin-3-yl)ethenyl]-3-hydroxycyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1\C=C\C=1C=C(Cl)C=NC=1)O)CCC1=CC=C(C(O)=O)S1 CZHYKYWDRJHXPF-OLMDXKKMSA-N 0.000 claims 1
- LFMZZLKLKPJYQR-CXEXCLRBSA-N 5-[3-[(1r,2r,3r,5r)-5-chloro-2-[(e)-2-[3-chloro-5-[(e)-prop-1-enyl]phenyl]ethenyl]-3-hydroxycyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C\C=C\C1=CC(Cl)=CC(\C=C\[C@@H]2[C@H]([C@H](Cl)C[C@H]2O)CCCC=2SC(=CC=2)C(O)=O)=C1 LFMZZLKLKPJYQR-CXEXCLRBSA-N 0.000 claims 1
- SOPHKEPUTWPCEL-ASAKMOIOSA-N 5-[3-[(1r,2r,3r,5r)-5-chloro-2-[(z)-2-(2,6-dichloropyridin-4-yl)ethenyl]-3-hydroxycyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1\C=C/C=1C=C(Cl)N=C(Cl)C=1)O)CCC1=CC=C(C(O)=O)S1 SOPHKEPUTWPCEL-ASAKMOIOSA-N 0.000 claims 1
- PEBZVFPSFALNKS-CLCQPTCASA-N 5-[3-[(1r,2r,3r,5r)-5-chloro-2-[(z)-2-(3,5-difluorophenyl)ethenyl]-3-hydroxycyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1\C=C/C=1C=C(F)C=C(F)C=1)O)CCC1=CC=C(C(O)=O)S1 PEBZVFPSFALNKS-CLCQPTCASA-N 0.000 claims 1
- LFMZZLKLKPJYQR-OQYPPDPBSA-N 5-[3-[(1r,2r,3r,5r)-5-chloro-2-[(z)-2-[3-chloro-5-[(e)-prop-1-enyl]phenyl]ethenyl]-3-hydroxycyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C\C=C\C1=CC(Cl)=CC(\C=C/[C@@H]2[C@H]([C@H](Cl)C[C@H]2O)CCCC=2SC(=CC=2)C(O)=O)=C1 LFMZZLKLKPJYQR-OQYPPDPBSA-N 0.000 claims 1
- AFYXHGFPTHLXOO-NCXUSEDFSA-N 5-[3-[(1r,2r,3r,5r)-5-chloro-2-[2-(3,5-dichlorophenyl)ethenyl]-3-hydroxycyclopentyl]prop-1-enyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1C=CC=1C=C(Cl)C=C(Cl)C=1)O)C=CC1=CC=C(C(O)=O)S1 AFYXHGFPTHLXOO-NCXUSEDFSA-N 0.000 claims 1
- QHCLGDFRJRXXHG-XRXFAXGQSA-N 5-[3-[(1r,2r,3r,5r)-5-chloro-2-[2-(3,5-dimethylphenyl)ethenyl]-3-hydroxycyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound CC1=CC(C)=CC(C=C[C@@H]2[C@H]([C@H](Cl)C[C@H]2O)CCCC=2SC(=CC=2)C(O)=O)=C1 QHCLGDFRJRXXHG-XRXFAXGQSA-N 0.000 claims 1
- KUOBGHVIANMHER-UAFMIMERSA-N 5-[3-[(1r,2r,3r,5r)-5-chloro-2-[2-[3-chloro-5-(hydroxymethyl)phenyl]ethenyl]-3-hydroxycyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound OCC1=CC(Cl)=CC(C=C[C@@H]2[C@H]([C@H](Cl)C[C@H]2O)CCCC=2SC(=CC=2)C(O)=O)=C1 KUOBGHVIANMHER-UAFMIMERSA-N 0.000 claims 1
- UXVFOUCAAHXZKV-ZLTFGEGPSA-N 5-[3-[(1r,2r,3r,5r)-5-chloro-3-hydroxy-2-[(e)-2-(2-propylpyridin-4-yl)ethenyl]cyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C1=NC(CCC)=CC(\C=C\[C@@H]2[C@H]([C@H](Cl)C[C@H]2O)CCCC=2SC(=CC=2)C(O)=O)=C1 UXVFOUCAAHXZKV-ZLTFGEGPSA-N 0.000 claims 1
- QNFADXKJITUROP-UAFMIMERSA-N 5-[3-[(1r,2r,3r,5r)-5-chloro-3-hydroxy-2-[2-(3-methylphenyl)ethenyl]cyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound CC1=CC=CC(C=C[C@@H]2[C@H]([C@H](Cl)C[C@H]2O)CCCC=2SC(=CC=2)C(O)=O)=C1 QNFADXKJITUROP-UAFMIMERSA-N 0.000 claims 1
- FIVUYQLAXMGLDM-ZHALLVOQSA-N 5-[3-[(1r,2s,3r)-3-hydroxy-5-oxo-2-(2-phenylethynyl)cyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1C(=O)C[C@H]([C@@H]1C#CC=1C=CC=CC=1)O)CCC1=CC=C(C(O)=O)S1 FIVUYQLAXMGLDM-ZHALLVOQSA-N 0.000 claims 1
- RXGDMTUMEHYFIW-SSGKUCQKSA-N 5-[3-[(1r,2s,3r,5r)-2-[2-(3-but-3-enylphenyl)ethynyl]-5-chloro-3-hydroxycyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1C#CC=1C=C(CCC=C)C=CC=1)O)CCC1=CC=C(C(O)=O)S1 RXGDMTUMEHYFIW-SSGKUCQKSA-N 0.000 claims 1
- VDGLHJDYWSNCPH-NCXUSEDFSA-N 5-[3-[(1r,2s,3r,5r)-5-chloro-2-[2-(3,5-dichlorophenyl)ethynyl]-3-hydroxycyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1C#CC=1C=C(Cl)C=C(Cl)C=1)O)CCC1=CC=C(C(O)=O)S1 VDGLHJDYWSNCPH-NCXUSEDFSA-N 0.000 claims 1
- ZHNPIGCMDFFPSX-NCXUSEDFSA-N 5-[3-[(1r,2s,3r,5r)-5-chloro-3-hydroxy-2-(2-phenylethynyl)cyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1C#CC=1C=CC=CC=1)O)CCC1=CC=C(C(O)=O)S1 ZHNPIGCMDFFPSX-NCXUSEDFSA-N 0.000 claims 1
- JGJUWDVADPDGBR-BRSBDYLESA-N 5-[3-[(1r,2s,3r,5r)-5-chloro-3-hydroxy-2-(2-pyridin-2-ylethynyl)cyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1C#CC=1N=CC=CC=1)O)CCC1=CC=C(C(O)=O)S1 JGJUWDVADPDGBR-BRSBDYLESA-N 0.000 claims 1
- KCIQLMFPXGVODC-BRSBDYLESA-N 5-[3-[(1r,2s,3r,5r)-5-chloro-3-hydroxy-2-(2-pyridin-3-ylethynyl)cyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1C#CC=1C=NC=CC=1)O)CCC1=CC=C(C(O)=O)S1 KCIQLMFPXGVODC-BRSBDYLESA-N 0.000 claims 1
- VZACPPDKNVXDRD-BRSBDYLESA-N 5-[3-[(1r,2s,3r,5r)-5-chloro-3-hydroxy-2-(2-pyridin-4-ylethynyl)cyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1C#CC=1C=CN=CC=1)O)CCC1=CC=C(C(O)=O)S1 VZACPPDKNVXDRD-BRSBDYLESA-N 0.000 claims 1
- PVDNYUSNELXNOS-QBPKDAKJSA-N 5-[3-[(1r,2s,3r,5r)-5-chloro-3-hydroxy-2-(2-thiophen-2-ylethynyl)cyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1C#CC=1SC=CC=1)O)CCC1=CC=C(C(O)=O)S1 PVDNYUSNELXNOS-QBPKDAKJSA-N 0.000 claims 1
- TUZDLGRNKRUHGC-QBPKDAKJSA-N 5-[3-[(1r,2s,3r,5r)-5-chloro-3-hydroxy-2-(2-thiophen-3-ylethynyl)cyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1C#CC1=CSC=C1)O)CCC1=CC=C(C(O)=O)S1 TUZDLGRNKRUHGC-QBPKDAKJSA-N 0.000 claims 1
- XYTWIQSLLRKJRM-GXRSIYKFSA-N 5-[3-[(1r,2s,3r,5r)-5-chloro-3-hydroxy-2-[2-[3-(3-hydroxypropyl)phenyl]ethynyl]cyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound OCCCC1=CC=CC(C#C[C@@H]2[C@H]([C@H](Cl)C[C@H]2O)CCCC=2SC(=CC=2)C(O)=O)=C1 XYTWIQSLLRKJRM-GXRSIYKFSA-N 0.000 claims 1
- HIPOZNRDSBNERQ-NCXUSEDFSA-N 5-[3-[(1r,2s,3r,5r)-5-fluoro-3-hydroxy-2-(2-phenylethynyl)cyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](F)C[C@H]([C@@H]1C#CC=1C=CC=CC=1)O)CCC1=CC=C(C(O)=O)S1 HIPOZNRDSBNERQ-NCXUSEDFSA-N 0.000 claims 1
- FIVUYQLAXMGLDM-YQVWRLOYSA-N 5-[3-[(1s,2s,3r)-3-hydroxy-5-oxo-2-(2-phenylethynyl)cyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@@H]1C(=O)C[C@H]([C@@H]1C#CC=1C=CC=CC=1)O)CCC1=CC=C(C(O)=O)S1 FIVUYQLAXMGLDM-YQVWRLOYSA-N 0.000 claims 1
- UDJNEXIKFLPQPN-IJXRJRJASA-N 5-[3-[(1s,2s,3r,5r)-5-cyano-3-hydroxy-2-(2-phenylethynyl)cyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](C#N)C[C@H]([C@@H]1C#CC=1C=CC=CC=1)O)CCC1=CC=C(C(O)=O)S1 UDJNEXIKFLPQPN-IJXRJRJASA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 230000004410 intraocular pressure Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- YDWDIWNFBPTJFF-GXRSIYKFSA-N propan-2-yl 5-[3-[(1r,2s,3r,5r)-5-chloro-3-hydroxy-2-(2-phenylethynyl)cyclopentyl]propyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC(C)C)=CC=C1CCC[C@@H]1[C@@H](C#CC=2C=CC=CC=2)[C@H](O)C[C@H]1Cl YDWDIWNFBPTJFF-GXRSIYKFSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94790407P | 2007-07-03 | 2007-07-03 | |
| US60/947,904 | 2007-07-03 | ||
| PCT/US2008/068716 WO2009006370A1 (en) | 2007-07-03 | 2008-06-30 | Therapeutic substituted cyclopentanes for reducing intraocular pressure |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010532379A JP2010532379A (ja) | 2010-10-07 |
| JP2010532379A5 true JP2010532379A5 (enExample) | 2011-08-18 |
| JP5453254B2 JP5453254B2 (ja) | 2014-03-26 |
Family
ID=39941423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010515212A Expired - Fee Related JP5453254B2 (ja) | 2007-07-03 | 2008-06-30 | 眼圧降下用の治療用置換シクロペンタン類 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US9591935B2 (enExample) |
| EP (1) | EP2170345B1 (enExample) |
| JP (1) | JP5453254B2 (enExample) |
| KR (1) | KR20100051803A (enExample) |
| CN (1) | CN101795692B (enExample) |
| AU (2) | AU2008269965A1 (enExample) |
| CA (1) | CA2692572A1 (enExample) |
| DK (1) | DK2170345T3 (enExample) |
| ES (1) | ES2401920T3 (enExample) |
| NZ (1) | NZ582705A (enExample) |
| RU (2) | RU2010103149A (enExample) |
| WO (1) | WO2009006370A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010093945A2 (en) | 2009-02-13 | 2010-08-19 | Glaukos Corporation | Uveoscleral drug delivery implant and methods for implanting the same |
| US12478503B2 (en) | 2009-05-18 | 2025-11-25 | Glaukos Corporation | Implants with controlled drug delivery features and methods of using same |
| US10206813B2 (en) | 2009-05-18 | 2019-02-19 | Dose Medical Corporation | Implants with controlled drug delivery features and methods of using same |
| JP5937004B2 (ja) | 2009-05-18 | 2016-06-22 | ドーズ メディカル コーポレーションＤｏｓｅ Ｍｅｄｉｃａｌ Ｃｏｒｐｏｒａｔｉｏｎ | 薬剤溶出眼内インプラント |
| US8299068B2 (en) * | 2010-01-29 | 2012-10-30 | Allergan, Inc. | Therapeutically active cyclopentanes |
| US9668915B2 (en) | 2010-11-24 | 2017-06-06 | Dose Medical Corporation | Drug eluting ocular implant |
| US10245178B1 (en) | 2011-06-07 | 2019-04-02 | Glaukos Corporation | Anterior chamber drug-eluting ocular implant |
| ES2693255T3 (es) * | 2014-02-27 | 2018-12-10 | Ono Pharmaceutical Co., Ltd. | Compuesto que presenta actividad agonista de EP2 selectiva |
| JP6773035B2 (ja) * | 2015-07-23 | 2020-10-21 | 小野薬品工業株式会社 | Ｅｐ２アゴニスト活性を有する化合物 |
| CA3083487A1 (en) | 2017-12-01 | 2019-06-06 | Lunella Biotech, Inc. | Repurposcins: targeted inhibitors of mitochondrial biogenesis for eradicating cancer stem cells |
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| US3980700A (en) * | 1971-10-07 | 1976-09-14 | G. D. Searle & Co. | Prostaglandin intermediates and optically active isomers thereof |
| US4149007A (en) * | 1977-06-23 | 1979-04-10 | Miles Laboratories, Inc. | C14 Phenyl-substituted derivatives of prostaglandin analogues |
| US5390798A (en) * | 1991-11-07 | 1995-02-21 | G'-Ka International, Inc. | Food and beverage support tray with beverage vessel cutout |
| US5323910A (en) * | 1992-08-07 | 1994-06-28 | Van De Graaf Jr Pieter A | Party plate |
| US5352708A (en) * | 1992-09-21 | 1994-10-04 | Allergan, Inc. | Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents |
| US5688819A (en) * | 1992-09-21 | 1997-11-18 | Allergan | Cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents |
| US5536725A (en) | 1993-08-25 | 1996-07-16 | Fmc Corporation | Insecticidal substituted-2,4-diamino-5,6,7,8-tetrahydroquinazolines |
| US5593062A (en) * | 1995-10-10 | 1997-01-14 | Martin; Melvin E. | Social serving plate |
| US5727678A (en) * | 1996-06-12 | 1998-03-17 | Chen; Chin Chen | Two-in-one paper dish and cup holder |
| US6264026B1 (en) * | 1997-04-15 | 2001-07-24 | Vincent H. Bradley | Food, beverage and utility tray |
| US5950856A (en) * | 1997-04-15 | 1999-09-14 | Cinque; Richard | Plate and cup holder |
| US6531485B2 (en) * | 1997-06-23 | 2003-03-11 | Pfizer Inc. | Prostaglandin agonists |
| EP1108426A3 (en) | 1999-12-02 | 2002-10-02 | Pfizer Products Inc. | Use of prostaglandin agonists to treat erectile dysfunction or impotence |
| BR0211545A (pt) * | 2001-07-31 | 2004-07-13 | Sucampo Ag | Método e composição para tratamento de hipertensão ocular e glaucoma |
| US6651836B1 (en) * | 2002-07-03 | 2003-11-25 | Leonard L. Hofheins | Hand-held plate for holding a beverage container and food |
| ATE465986T1 (de) * | 2005-01-14 | 2010-05-15 | Allergan Inc | Substituierte cyclopentane oder cyclopentanone zur behandlung von augenhochdruck |
| BRPI0713587A2 (pt) | 2006-06-20 | 2012-10-23 | Allergan Inc | descrição de compostos terapêuticos da invenção |
| AU2007272683B2 (en) * | 2006-07-10 | 2012-08-23 | Allergan, Inc. | Substituted cyclopentane derivatives as therapeutic agents |
| US20080015219A1 (en) * | 2006-07-11 | 2008-01-17 | Allergan, Inc. | Therapeutic compounds |
| AU2007272617B2 (en) * | 2006-07-11 | 2012-11-01 | Allergan, Inc. | Cyclopentane derivatives as antiglaucoma agents |
-
2008
- 2008-06-30 JP JP2010515212A patent/JP5453254B2/ja not_active Expired - Fee Related
- 2008-06-30 WO PCT/US2008/068716 patent/WO2009006370A1/en not_active Ceased
- 2008-06-30 DK DK08781152.7T patent/DK2170345T3/da active
- 2008-06-30 NZ NZ582705A patent/NZ582705A/en not_active IP Right Cessation
- 2008-06-30 AU AU2008269965A patent/AU2008269965A1/en not_active Abandoned
- 2008-06-30 EP EP08781152A patent/EP2170345B1/en not_active Not-in-force
- 2008-06-30 RU RU2010103149/15A patent/RU2010103149A/ru unknown
- 2008-06-30 ES ES08781152T patent/ES2401920T3/es active Active
- 2008-06-30 CN CN2008801052735A patent/CN101795692B/zh not_active Expired - Fee Related
- 2008-06-30 KR KR1020107002370A patent/KR20100051803A/ko not_active Ceased
- 2008-06-30 CA CA 2692572 patent/CA2692572A1/en not_active Abandoned
- 2008-06-30 US US12/667,197 patent/US9591935B2/en active Active
-
2014
- 2014-02-19 RU RU2014105895/15A patent/RU2014105895A/ru not_active Application Discontinuation
- 2014-07-01 AU AU2014203599A patent/AU2014203599A1/en not_active Abandoned
-
2017
- 2017-02-06 US US15/425,470 patent/US9765065B2/en not_active Expired - Fee Related
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