JP2009520690A5 - - Google Patents
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- Publication number
- JP2009520690A5 JP2009520690A5 JP2008543539A JP2008543539A JP2009520690A5 JP 2009520690 A5 JP2009520690 A5 JP 2009520690A5 JP 2008543539 A JP2008543539 A JP 2008543539A JP 2008543539 A JP2008543539 A JP 2008543539A JP 2009520690 A5 JP2009520690 A5 JP 2009520690A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- dihydroxyphenyl
- phenylcarbonyloxypropyl
- propanoate
- propanoate mesylate
- 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
- BFGJJGIBNQKBIQ-YLCXCWDSSA-N [(2r)-1-[(2s)-2-amino-3-(3,4-dihydroxyphenyl)propanoyl]oxypropan-2-yl] benzoate;methanesulfonic acid Chemical compound CS(O)(=O)=O.C([C@H](N)C(=O)OC[C@@H](C)OC(=O)C=1C=CC=CC=1)C1=CC=C(O)C(O)=C1 BFGJJGIBNQKBIQ-YLCXCWDSSA-N 0.000 claims 31
- 239000002904 solvent Substances 0.000 claims 17
- 239000008194 pharmaceutical composition Substances 0.000 claims 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 12
- 238000000034 method Methods 0.000 claims 12
- -1 (2R) -2-phenylcarbonyloxypropyl Chemical group 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 11
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 10
- 229940099362 Catechol O methyltransferase inhibitor Drugs 0.000 claims 8
- 229940123736 Decarboxylase inhibitor Drugs 0.000 claims 8
- AKUWZLYXAADOTQ-DOMZBBRYSA-N [(2r)-1-[(2s)-2-amino-3-(3,4-dihydroxyphenyl)propanoyl]oxypropan-2-yl] benzoate Chemical compound C([C@H](N)C(=O)OC[C@@H](C)OC(=O)C=1C=CC=CC=1)C1=CC=C(O)C(O)=C1 AKUWZLYXAADOTQ-DOMZBBRYSA-N 0.000 claims 8
- 239000003543 catechol methyltransferase inhibitor Substances 0.000 claims 8
- 239000003954 decarboxylase inhibitor Substances 0.000 claims 8
- 238000004519 manufacturing process Methods 0.000 claims 8
- 239000003795 chemical substances by application Substances 0.000 claims 7
- LRVPEOXGGVAVBS-QAPCUYQASA-N [(2r)-1-[(2s)-3-(3,4-dihydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]oxypropan-2-yl] benzoate Chemical compound C([C@@H](C(=O)OC[C@@H](C)OC(=O)C=1C=CC=CC=1)NC(=O)OC(C)(C)C)C1=CC=C(O)C(O)=C1 LRVPEOXGGVAVBS-QAPCUYQASA-N 0.000 claims 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 4
- 238000000113 differential scanning calorimetry Methods 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 238000002844 melting Methods 0.000 claims 4
- 230000008018 melting Effects 0.000 claims 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims 4
- 230000005855 radiation Effects 0.000 claims 4
- 238000013268 sustained release Methods 0.000 claims 4
- 239000012730 sustained-release form Substances 0.000 claims 4
- 238000001757 thermogravimetry curve Methods 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 2
- 206010012335 Dependence Diseases 0.000 claims 2
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims 2
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 208000008705 Nocturnal Myoclonus Syndrome Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000005793 Restless legs syndrome Diseases 0.000 claims 2
- 206010041349 Somnolence Diseases 0.000 claims 2
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 2
- 208000000323 Tourette Syndrome Diseases 0.000 claims 2
- 208000016620 Tourette disease Diseases 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 208000028683 bipolar I disease Diseases 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N dopa Chemical compound OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 2
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 2
- UANOJLOYSTZABR-UHFFFAOYSA-N methanesulfonic acid;propanoic acid Chemical compound CCC(O)=O.CS(O)(=O)=O UANOJLOYSTZABR-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 230000003472 neutralizing effect Effects 0.000 claims 2
- 208000023515 periodic limb movement disease Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74187605P | 2005-12-05 | 2005-12-05 | |
| US60/741,876 | 2005-12-05 | ||
| PCT/US2006/046273 WO2007067495A2 (en) | 2005-12-05 | 2006-12-04 | Levodopa prodrug mesylate, compositions thereof, and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009520690A JP2009520690A (ja) | 2009-05-28 |
| JP2009520690A5 true JP2009520690A5 (enExample) | 2010-01-21 |
| JP5153641B2 JP5153641B2 (ja) | 2013-02-27 |
Family
ID=38123406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008543539A Expired - Fee Related JP5153641B2 (ja) | 2005-12-05 | 2006-12-04 | レボドパプロドラッグメシラート、その組成物、およびその使用法 |
Country Status (20)
| Country | Link |
|---|---|
| US (5) | US7563821B2 (enExample) |
| EP (1) | EP1959948B1 (enExample) |
| JP (1) | JP5153641B2 (enExample) |
| KR (1) | KR101396639B1 (enExample) |
| CN (1) | CN101365439B (enExample) |
| AU (1) | AU2006322051B2 (enExample) |
| BR (1) | BRPI0619425A2 (enExample) |
| CA (1) | CA2631643C (enExample) |
| CY (1) | CY1113108T1 (enExample) |
| DK (1) | DK1959948T3 (enExample) |
| ES (1) | ES2391575T3 (enExample) |
| IL (1) | IL191937A (enExample) |
| NO (1) | NO20082768L (enExample) |
| NZ (1) | NZ569485A (enExample) |
| PL (1) | PL1959948T3 (enExample) |
| PT (1) | PT1959948E (enExample) |
| RU (1) | RU2429223C2 (enExample) |
| TW (1) | TWI403493B (enExample) |
| WO (1) | WO2007067495A2 (enExample) |
| ZA (1) | ZA200805511B (enExample) |
Families Citing this family (38)
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| WO2005121070A1 (en) | 2004-06-04 | 2005-12-22 | Xenoport, Inc. | Levodopa prodrugs, and compositions and uses thereof |
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| CN101365439B (zh) | 2005-12-05 | 2012-12-26 | 克塞诺波特公司 | 左旋多巴前体药物甲磺酸盐、其组合物及其用途 |
| US20080070984A1 (en) * | 2006-09-15 | 2008-03-20 | Tran Pierre V | Compositions and Methods of Treating Schizophrenia |
| US7709527B2 (en) * | 2006-12-21 | 2010-05-04 | Xenoport, Inc. | Levodopa dimethyl-substituted diester prodrugs compositions, and methods of use |
| TW200843731A (en) | 2006-12-21 | 2008-11-16 | Xenoport Inc | Catechol protected levodopa diester prodrugs, compositions, and methods of use |
| JP5706825B2 (ja) | 2008-10-17 | 2015-04-22 | シグネーチャー セラピューティクス, インク.Signature Therapeutics, Inc. | フェノール性オピオイドの放出が減弱された医薬組成物 |
| US8399513B2 (en) * | 2008-10-20 | 2013-03-19 | Xenoport, Inc. | Levodopa prodrug mesylate hydrate |
| JP2012505885A (ja) * | 2008-10-20 | 2012-03-08 | ゼノポート，インコーポレーテッド | レボドパエステルプロドラッグを合成する方法 |
| US8784847B2 (en) | 2009-04-17 | 2014-07-22 | Merz Pharma Gmbh & Co. Kgaa | Synthesis of 1-amino-1,3,3,5,5,-cyclohexane mesylate |
| BR112012005124B1 (pt) | 2009-09-08 | 2021-11-09 | Signature Therapeutics, Inc. | Pro-fármaco de opioide modificado por cetona, seu método de preparação, sua composição farmacêutica, sua unidade de dose, métodos e usos |
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| JP7457391B2 (ja) | 2018-09-13 | 2024-03-28 | ユニバーシティ・オブ・キャンベラ | 阻害の方法 |
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| US20080070984A1 (en) | 2006-09-15 | 2008-03-20 | Tran Pierre V | Compositions and Methods of Treating Schizophrenia |
| US7709527B2 (en) * | 2006-12-21 | 2010-05-04 | Xenoport, Inc. | Levodopa dimethyl-substituted diester prodrugs compositions, and methods of use |
| TW200843731A (en) | 2006-12-21 | 2008-11-16 | Xenoport Inc | Catechol protected levodopa diester prodrugs, compositions, and methods of use |
| JP2012505885A (ja) * | 2008-10-20 | 2012-03-08 | ゼノポート，インコーポレーテッド | レボドパエステルプロドラッグを合成する方法 |
| US8399513B2 (en) * | 2008-10-20 | 2013-03-19 | Xenoport, Inc. | Levodopa prodrug mesylate hydrate |
| WO2011056240A2 (en) * | 2009-11-09 | 2011-05-12 | Xenoport, Inc. | Pharmaceutical compositions and oral dosage forms of a levodopa prodrug and methods of use |
-
2006
- 2006-12-04 CN CN200680045534XA patent/CN101365439B/zh not_active Expired - Fee Related
- 2006-12-04 PT PT06844799T patent/PT1959948E/pt unknown
- 2006-12-04 WO PCT/US2006/046273 patent/WO2007067495A2/en not_active Ceased
- 2006-12-04 AU AU2006322051A patent/AU2006322051B2/en not_active Ceased
- 2006-12-04 NZ NZ569485A patent/NZ569485A/en not_active IP Right Cessation
- 2006-12-04 DK DK06844799.4T patent/DK1959948T3/da active
- 2006-12-04 JP JP2008543539A patent/JP5153641B2/ja not_active Expired - Fee Related
- 2006-12-04 TW TW095144993A patent/TWI403493B/zh not_active IP Right Cessation
- 2006-12-04 RU RU2008127312/04A patent/RU2429223C2/ru not_active IP Right Cessation
- 2006-12-04 CA CA2631643A patent/CA2631643C/en not_active Expired - Fee Related
- 2006-12-04 PL PL06844799T patent/PL1959948T3/pl unknown
- 2006-12-04 BR BRPI0619425-7A patent/BRPI0619425A2/pt not_active IP Right Cessation
- 2006-12-04 US US11/634,354 patent/US7563821B2/en not_active Expired - Fee Related
- 2006-12-04 ZA ZA200805511A patent/ZA200805511B/xx unknown
- 2006-12-04 KR KR1020087016252A patent/KR101396639B1/ko not_active Expired - Fee Related
- 2006-12-04 ES ES06844799T patent/ES2391575T3/es active Active
- 2006-12-04 EP EP06844799A patent/EP1959948B1/en not_active Not-in-force
-
2008
- 2008-06-04 IL IL191937A patent/IL191937A/en not_active IP Right Cessation
- 2008-06-16 NO NO20082768A patent/NO20082768L/no not_active Application Discontinuation
- 2008-12-31 US US12/347,807 patent/US7968597B2/en not_active Expired - Fee Related
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2009
- 2009-06-22 US US12/489,146 patent/US7893105B2/en not_active Expired - Fee Related
-
2011
- 2011-01-20 US US13/010,419 patent/US8193242B2/en not_active Expired - Fee Related
-
2012
- 2012-05-16 US US13/473,503 patent/US20120296109A1/en not_active Abandoned
- 2012-09-12 CY CY20121100822T patent/CY1113108T1/el unknown
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