JP2008520737A5 - - Google Patents
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- Publication number
- JP2008520737A5 JP2008520737A5 JP2007543434A JP2007543434A JP2008520737A5 JP 2008520737 A5 JP2008520737 A5 JP 2008520737A5 JP 2007543434 A JP2007543434 A JP 2007543434A JP 2007543434 A JP2007543434 A JP 2007543434A JP 2008520737 A5 JP2008520737 A5 JP 2008520737A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclopentylsulfanyl
- propylsulfanyl
- enyl
- oxo
- hydroxy
- 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 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 239000000651 prodrug Substances 0.000 claims 9
- 229940002612 prodrug Drugs 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 5
- 150000001408 amides Chemical class 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 125000000524 functional group Chemical group 0.000 claims 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- -1 {3-[(1R, 2R) -2-((E) -3-Hydroxy-5-naphthalen-2-yl-pent-1-enyl) -5-oxo-cyclopentylsulfanyl] -propylsulfanyl} -methyl acetate ester Chemical class 0.000 claims 3
- CSTDWEFVWPVKKW-JXJVIVMZSA-N 2-[3-[(1r,2r)-2-[(e)-3-hydroxy-3-methyl-5-naphthalen-2-ylpent-1-enyl]-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CCC(O)(C)\C=C\[C@H]1CCC(=O)[C@@H]1SCCCSCC(O)=O CSTDWEFVWPVKKW-JXJVIVMZSA-N 0.000 claims 2
- HCQYVBZGBLNOFI-VRKUCDCTSA-N 2-[3-[(1r,2r)-2-[(e)-3-hydroxy-5-naphthalen-2-ylpent-1-enyl]-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CCC(O)\C=C\[C@H]1CCC(=O)[C@@H]1SCCCSCC(O)=O HCQYVBZGBLNOFI-VRKUCDCTSA-N 0.000 claims 2
- UTZZXFGMUNYLMU-PWSNHNADSA-N 2-[3-[(1r,2r)-2-[(e)-5-(1-benzothiophen-2-yl)-3-hydroxypent-1-enyl]-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetic acid Chemical compound C=1C2=CC=CC=C2SC=1CCC(O)\C=C\[C@H]1CCC(=O)[C@@H]1SCCCSCC(O)=O UTZZXFGMUNYLMU-PWSNHNADSA-N 0.000 claims 2
- LQGTVMVTYDAGHV-AEMGLWRSSA-N 2-[3-[(1r,2s,3r)-2-[(e)-5-(1-benzothiophen-2-yl)-3-hydroxypent-1-enyl]-3-(hydroxymethyl)-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetic acid Chemical compound OC[C@@H]1CC(=O)[C@H](SCCCSCC(O)=O)[C@H]1\C=C\C(O)CCC1=CC2=CC=CC=C2S1 LQGTVMVTYDAGHV-AEMGLWRSSA-N 0.000 claims 2
- VTRHQXISIGUPRC-MBZJWXPASA-N 2-[3-[(1r,2s,3r)-3-(hydroxymethyl)-2-[(e)-3-hydroxy-4-phenylbut-1-enyl]-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetic acid Chemical compound OC[C@@H]1CC(=O)[C@H](SCCCSCC(O)=O)[C@H]1\C=C\C(O)CC1=CC=CC=C1 VTRHQXISIGUPRC-MBZJWXPASA-N 0.000 claims 2
- XPHYVUTUWAEEBG-NIPNWSTISA-N 2-[3-[(1r,2s,3r)-3-(hydroxymethyl)-2-[(e)-3-hydroxy-5-naphthalen-2-ylpent-1-enyl]-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetic acid Chemical compound OC[C@@H]1CC(=O)[C@H](SCCCSCC(O)=O)[C@H]1\C=C\C(O)CCC1=CC=C(C=CC=C2)C2=C1 XPHYVUTUWAEEBG-NIPNWSTISA-N 0.000 claims 2
- XRWWXTOKESTVJJ-UHFFFAOYSA-N 2-[3-[2-[4-(1-benzothiophen-3-yl)-3-hydroxybut-1-enyl]-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetic acid Chemical compound C=1SC2=CC=CC=C2C=1CC(O)C=CC1CCC(=O)C1SCCCSCC(O)=O XRWWXTOKESTVJJ-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- FXWCPYPIZSKLQO-SSOKGKCHSA-N methyl 2-[3-[(1r,2r)-2-[(e)-3-hydroxy-4-phenylbut-1-enyl]-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetate Chemical compound C1CC(=O)[C@H](SCCCSCC(=O)OC)[C@H]1\C=C\C(O)CC1=CC=CC=C1 FXWCPYPIZSKLQO-SSOKGKCHSA-N 0.000 claims 2
- IALJCGVTOBBLGA-WRPLSTKMSA-N methyl 2-[3-[(1r,2r)-2-[(e)-5-(1-benzothiophen-2-yl)-3-hydroxypent-1-enyl]-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetate Chemical compound C1CC(=O)[C@H](SCCCSCC(=O)OC)[C@H]1\C=C\C(O)CCC1=CC2=CC=CC=C2S1 IALJCGVTOBBLGA-WRPLSTKMSA-N 0.000 claims 2
- WMJFIBVWWIVJQX-YEWAFCEJSA-N methyl 2-[3-[(1r,2s,3r)-2-[(e)-5-(1-benzothiophen-2-yl)-3-hydroxypent-1-enyl]-3-(hydroxymethyl)-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetate Chemical compound OC[C@@H]1CC(=O)[C@H](SCCCSCC(=O)OC)[C@H]1\C=C\C(O)CCC1=CC2=CC=CC=C2S1 WMJFIBVWWIVJQX-YEWAFCEJSA-N 0.000 claims 2
- ZDXKQFWKCIJTLI-CXPVECNQSA-N methyl 2-[3-[(1r,2s,3r)-3-(hydroxymethyl)-2-[(e)-3-hydroxy-4-phenylbut-1-enyl]-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetate Chemical compound OC[C@@H]1CC(=O)[C@H](SCCCSCC(=O)OC)[C@H]1\C=C\C(O)CC1=CC=CC=C1 ZDXKQFWKCIJTLI-CXPVECNQSA-N 0.000 claims 2
- NUYKQQQYOFAPFF-FSZOWFHXSA-N methyl 2-[3-[(1r,2s,3r)-3-(hydroxymethyl)-2-[(e)-3-hydroxy-5-naphthalen-2-ylpent-1-enyl]-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetate Chemical compound OC[C@@H]1CC(=O)[C@H](SCCCSCC(=O)OC)[C@H]1\C=C\C(O)CCC1=CC=C(C=CC=C2)C2=C1 NUYKQQQYOFAPFF-FSZOWFHXSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- VQUZHZXOQNRGHQ-NKBGECGLSA-N 2-[3-[(1r,2r)-2-[(e)-3-hydroxy-4-naphthalen-2-ylbut-1-enyl]-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CC(O)\C=C\[C@H]1CCC(=O)[C@@H]1SCCCSCC(O)=O VQUZHZXOQNRGHQ-NKBGECGLSA-N 0.000 claims 1
- ZYTPJUFYGBRIFE-DAJOFENFSA-N 2-[3-[(1r,2r)-2-[(e)-3-hydroxy-4-phenylbut-1-enyl]-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetic acid Chemical compound C(\[C@@H]1[C@H](C(=O)CC1)SCCCSCC(O)=O)=C/C(O)CC1=CC=CC=C1 ZYTPJUFYGBRIFE-DAJOFENFSA-N 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010030043 Ocular hypertension Diseases 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000003889 eye drop Substances 0.000 claims 1
- 229940012356 eye drops Drugs 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- YFNKZVHJIGQFKU-AXZZJDROSA-N methyl 2-[3-[(1r,2r)-2-[(e)-3-hydroxy-3-methyl-5-naphthalen-2-ylpent-1-enyl]-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetate Chemical compound C1CC(=O)[C@H](SCCCSCC(=O)OC)[C@H]1\C=C\C(C)(O)CCC1=CC=C(C=CC=C2)C2=C1 YFNKZVHJIGQFKU-AXZZJDROSA-N 0.000 claims 1
- XOAHPLJCRDVTCP-MIDQYHJNSA-N methyl 2-[3-[(1r,3r)-2-[(e)-5-(3-chloro-1-benzothiophen-2-yl)-3-hydroxypent-1-enyl]-3-methyl-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetate Chemical compound C[C@@H]1CC(=O)[C@H](SCCCSCC(=O)OC)C1\C=C\C(O)CCC1=C(Cl)C2=CC=CC=C2S1 XOAHPLJCRDVTCP-MIDQYHJNSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- QLFQYZVQVVSDTB-UHFFFAOYSA-N propan-2-yl 2-[3-[3-(hydroxymethyl)-2-(3-hydroxy-4-phenylbut-1-enyl)-5-oxocyclopentyl]sulfanylpropylsulfanyl]acetate Chemical compound OCC1CC(=O)C(SCCCSCC(=O)OC(C)C)C1C=CC(O)CC1=CC=CC=C1 QLFQYZVQVVSDTB-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 BC(CC1=O)[C@]([C@@](C)CC(C)(C*)O)[C@@]1SCCCSC* Chemical compound BC(CC1=O)[C@]([C@@](C)CC(C)(C*)O)[C@@]1SCCCSC* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/997,039 US7183324B2 (en) | 2004-11-23 | 2004-11-23 | 2,3,4-substituted cyclopentanones as therapeutic agents |
| US10/997,039 | 2004-11-23 | ||
| PCT/US2005/042428 WO2006058063A1 (en) | 2004-11-23 | 2005-11-21 | 2,3,4-substituted-cyclopentanones as therapeutic agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008520737A JP2008520737A (ja) | 2008-06-19 |
| JP2008520737A5 true JP2008520737A5 (OSRAM) | 2009-01-15 |
| JP5114205B2 JP5114205B2 (ja) | 2013-01-09 |
Family
ID=36087629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007543434A Expired - Fee Related JP5114205B2 (ja) | 2004-11-23 | 2005-11-21 | 治療薬としての２，３，４−置換シクロペンタノン |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7183324B2 (OSRAM) |
| EP (1) | EP1814848B9 (OSRAM) |
| JP (1) | JP5114205B2 (OSRAM) |
| AT (1) | ATE475643T1 (OSRAM) |
| AU (1) | AU2005309605B2 (OSRAM) |
| BR (1) | BRPI0518299A2 (OSRAM) |
| CA (1) | CA2588599A1 (OSRAM) |
| DE (1) | DE602005022613D1 (OSRAM) |
| DK (1) | DK1814848T3 (OSRAM) |
| ES (1) | ES2347808T3 (OSRAM) |
| WO (1) | WO2006058063A1 (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050222094A1 (en) * | 2001-06-14 | 2005-10-06 | Burk Robert M | Treatment of inflammatory bowel disease |
| US7872045B2 (en) | 2001-06-14 | 2011-01-18 | Allergan, Inc. | Combination therapy for glaucoma treatment |
| US7799336B2 (en) | 2004-04-30 | 2010-09-21 | Allergan, Inc. | Hypotensive lipid-containing biodegradable intraocular implants and related methods |
| TWI386208B (zh) * | 2005-04-18 | 2013-02-21 | Allergan Inc | 治療性的經取代環戊酮 |
| US20070232660A1 (en) * | 2006-04-04 | 2007-10-04 | Allergan, Inc. | Therapeutic and delivery methods of prostaglandin ep4 agonists |
| EP2147672A4 (en) | 2007-05-08 | 2011-11-02 | Nat University Corp Hamamatsu University School Of Medicine | CYTOTOXIC T CELL ACTIVATOR WITH AN EP4 AGONIST |
| US7781465B2 (en) * | 2007-08-21 | 2010-08-24 | Allergan, Inc. | Therapeutic oxazolidinones and thiazolidinones |
| US20110293549A1 (en) | 2009-02-03 | 2011-12-01 | Athena Cosmetics, Inc. | Composition, method and kit for enhancing hair |
| NZ599128A (en) | 2009-10-14 | 2014-02-28 | Gemmus Pharma Inc | Combination therapy treatment for viral infections |
| EP2605777A1 (en) * | 2010-08-17 | 2013-06-26 | Allergan, Inc. | Ep2 or ep4 agonists for treating corneal haze |
| JP6694385B2 (ja) | 2013-08-09 | 2020-05-13 | アーデリクス，インコーポレーテッド | リン酸塩輸送阻害のための化合物及び方法 |
| EP3351239B1 (en) | 2013-10-31 | 2020-04-01 | Allergan, Inc. | Prostamide-containing intraocular implants and methods of use thereof |
| CN106928121B (zh) * | 2015-12-29 | 2020-05-12 | 暨南大学 | 3-取代-苯并五元杂环-2-羰基化合物的高效制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166452A (en) | 1976-05-03 | 1979-09-04 | Generales Constantine D J Jr | Apparatus for testing human responses to stimuli |
| DE2715838A1 (de) | 1977-04-05 | 1978-10-19 | Schering Ag | Neue prostanderivate und verfahren zu ihrer herstellung |
| US4256108A (en) | 1977-04-07 | 1981-03-17 | Alza Corporation | Microporous-semipermeable laminated osmotic system |
| US4131738A (en) | 1977-07-05 | 1978-12-26 | The Upjohn Company | 6-Hydroxy-PGE1 compounds |
| US4265874A (en) | 1980-04-25 | 1981-05-05 | Alza Corporation | Method of delivering drug with aid of effervescent activity generated in environment of use |
| US6043275A (en) | 1998-04-16 | 2000-03-28 | Ono Pharmaceutical Co., Ltd. | 3,7-dithiaprostanoic acid derivative |
| WO2000015608A1 (fr) | 1998-09-14 | 2000-03-23 | Ono Pharmaceutical Co., Ltd. | Derives e de phenyl-prostaglandine a substitution-φ et medicaments les contenant comme ingredient actif |
| MXPA03004623A (es) | 2000-11-27 | 2003-09-05 | Pfizer Prod Inc | Agonistas selectivos del receptor ep4 en el tratamiento de la osteoporosis. |
| 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 |
| EP1395263B1 (en) | 2001-06-14 | 2009-12-30 | Allergan, Inc. | 3, 7 or 3 and 7 thia or oxa prostanoic acid derivatives as agents for lowering intraocular pressure |
| US20030027853A1 (en) | 2001-06-14 | 2003-02-06 | Allergan Sales, Inc. | 3, 7or3 and 7 thia or oxa prostanoic acid derivatives as agents for lowering intraocular pressure |
| US7101906B2 (en) * | 2004-11-16 | 2006-09-05 | Allergan, Inc. | 2,3,4-substituted cyclopentanones as therapeutic agents |
-
2004
- 2004-11-23 US US10/997,039 patent/US7183324B2/en not_active Expired - Lifetime
-
2005
- 2005-11-21 EP EP05852061A patent/EP1814848B9/en not_active Expired - Lifetime
- 2005-11-21 DE DE602005022613T patent/DE602005022613D1/de not_active Expired - Lifetime
- 2005-11-21 AU AU2005309605A patent/AU2005309605B2/en not_active Ceased
- 2005-11-21 ES ES05852061T patent/ES2347808T3/es not_active Expired - Lifetime
- 2005-11-21 AT AT05852061T patent/ATE475643T1/de not_active IP Right Cessation
- 2005-11-21 DK DK05852061.0T patent/DK1814848T3/da active
- 2005-11-21 CA CA002588599A patent/CA2588599A1/en not_active Abandoned
- 2005-11-21 BR BRPI0518299-9A patent/BRPI0518299A2/pt not_active Application Discontinuation
- 2005-11-21 JP JP2007543434A patent/JP5114205B2/ja not_active Expired - Fee Related
- 2005-11-21 WO PCT/US2005/042428 patent/WO2006058063A1/en not_active Ceased
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