GB1364505A - F phenylalanine amide derivatives - Google Patents
F phenylalanine amide derivativesInfo
- Publication number
- GB1364505A GB1364505A GB5037771A GB5037771A GB1364505A GB 1364505 A GB1364505 A GB 1364505A GB 5037771 A GB5037771 A GB 5037771A GB 5037771 A GB5037771 A GB 5037771A GB 1364505 A GB1364505 A GB 1364505A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzyloxycarbonyl
- formula
- tyrosine
- compounds
- dopa
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06086—Dipeptides with the first amino acid being basic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06173—Dipeptides with the first amino acid being heterocyclic and Glp-amino acid; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
Abstract
1364505 3,4 - Dihydroxyphenylalanine derivatives F HOFFMANN-LA ROCHE & CO AG 29 Oct 1971 [30 Oct 1970] 50377/71 Heading C2C The invention comprises 3,4-dihydroxyphenylalanine derivatives of the Formula I in the L-form or, where the carbon atom marked * in the above formula is asymmetric, in the L 1 L-form, wherein R 1 is 3,4-dihydroxybenzyl and R 2 is 3,4-dihydroxybenzyl, the group of the formula or the residue R in a natural α-amino acid of the formula R 3 is H or COOH and R 4 is C 1 -C 6 alkyl, provided that the symbol R 2 is 3,4-dihydroxybenzyl when R 3 is H, the pharmaceutically acceptable salts thereof, derivative thereof in which amino, hydroxy and carboxy groups may be protected and compounds in the L-form of the Formula VIa wherein R 50 and R 7 are aryl-C 2 -C 7 alkoxycarbonyl. The compounds of Formula I are prepared by subjecting the protected derivatives thereof to hydrogenolysis or hydrolysis or to hydrolysis or hydrogenolysis. The protected derivatives are obtained by any conventional peptide coupling using the appropriate starting materials. Compounds of Formula VIa are prepared by reacting 1 mole of L-dopa with at least 3 moles of the corresponding aralkoxycarbonyl halide. The following starting materials and intermediates were also prepared L - Dopa benzyl and ethyl esters and their hydrochlorides, N - benzyloxycarbonyl - L- dopa, and its ethyl ester N,O - bis - benzyloxycarbonyl - L - tyrosine, N,O - bis - benzyloxycarbonyl - 3 - methoxy - L - tyrosine. O - benzyloxycarbonyl - L - tyrosine benzyl ester hydrochloride, the N-carboxy anhydride of O-benzyloxycarbonyl - L - tyrosine, 3 - methoxy O - benzyloxycarbonyl - L - tyrosine benzyl ester hydrochloride, the N-carboxy anhydride of 3 - methoxy - O - benzyloxycarbonyl - L- tyrosine, O,O<SP>1</SP> - bis - benzyloxy - L - dopa benzyl ester hydrochloride, and the N-carboxy anhydride of O 1 O<SP>1</SP>-bis-benzyloxycarbonyl-L- dopa. Pharmaceutical compositions, suitable for oral or parenteral administration, contain the compounds of Formula I above or salts thereof in association with compatible carriers. The compounds are used an anti-Parkinson agents.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8571370A | 1970-10-30 | 1970-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1364505A true GB1364505A (en) | 1974-08-21 |
Family
ID=22193467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5037771A Expired GB1364505A (en) | 1970-10-30 | 1971-10-29 | F phenylalanine amide derivatives |
Country Status (10)
| Country | Link |
|---|---|
| AU (1) | AU3486971A (en) |
| BE (1) | BE774683A (en) |
| BR (1) | BR7107234D0 (en) |
| DE (1) | DE2153813A1 (en) |
| FR (1) | FR2111947A1 (en) |
| GB (1) | GB1364505A (en) |
| IL (1) | IL38002A0 (en) |
| NL (1) | NL7114701A (en) |
| RO (1) | RO68988A (en) |
| ZA (1) | ZA716958B (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0610595A2 (en) * | 1992-12-24 | 1994-08-17 | Teva Pharmaceutical Industries, Ltd. | Composition of l-dopa esters |
| US5607969A (en) * | 1992-12-24 | 1997-03-04 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | L-DOPA ethyl ester to treat Parkinson's disease |
| US6218566B1 (en) | 1998-11-10 | 2001-04-17 | Teva Pharmaceutical Industries, Ltd. | Process for manufacturing of L-DOPA ethyl ester |
| US6376545B1 (en) | 1998-11-10 | 2002-04-23 | Teva Pharmaceutical Industries, Ltd. | Dispersible compositions containing L-DOPA ethyl ester |
| US6696600B2 (en) | 2001-11-13 | 2004-02-24 | Teva Pharmaceutical Industries, Ltd. | L-DOPA ethyl ester salts and uses thereof |
| US8263520B2 (en) | 2009-12-02 | 2012-09-11 | Dow Global Technologies Llc | Two atom bridged dicarbonate compounds as internal donors in catalysts for polypropylene manufacture |
| US8633126B2 (en) | 2009-12-02 | 2014-01-21 | Dow Global Technologies Llc | Three and four atom bridged dicarbonate compounds as internal donors in catalysts for polypropylene manufacture |
| WO2014191997A1 (en) * | 2013-05-28 | 2014-12-04 | Ramot At Tel-Aviv University Ltd. | Self-assembled micro- and nano-structures |
| US9045570B2 (en) | 2008-12-31 | 2015-06-02 | W.R. Grace & Co. - Conn. | Procatalyst composition with substituted 1,2-phenylene aromatic diester internal donor and method |
| US9464144B2 (en) | 2008-12-31 | 2016-10-11 | W. R. Grace & Co.—Conn. | Enhanced procatalyst composition and process |
| WO2023175623A1 (en) * | 2022-03-18 | 2023-09-21 | Neuroderm, Ltd. | Levodopa tyrosine polymorphs |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3212170A1 (en) | 2013-03-15 | 2014-09-18 | Techfields Pharma Co., Ltd. | Novel high penetration drugs and their compositions thereof for treatment of parkinson diseases |
-
1971
- 1971-10-18 ZA ZA716958A patent/ZA716958B/en unknown
- 1971-10-21 AU AU34869/71A patent/AU3486971A/en not_active Expired
- 1971-10-25 IL IL38002A patent/IL38002A0/en unknown
- 1971-10-26 NL NL7114701A patent/NL7114701A/xx unknown
- 1971-10-28 DE DE19712153813 patent/DE2153813A1/en active Pending
- 1971-10-28 FR FR7138778A patent/FR2111947A1/fr not_active Withdrawn
- 1971-10-29 GB GB5037771A patent/GB1364505A/en not_active Expired
- 1971-10-29 BR BR007234/71A patent/BR7107234D0/en unknown
- 1971-10-29 BE BE774683A patent/BE774683A/en unknown
- 1971-10-30 RO RO7168609A patent/RO68988A/en unknown
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0610595A2 (en) * | 1992-12-24 | 1994-08-17 | Teva Pharmaceutical Industries, Ltd. | Composition of l-dopa esters |
| US5354885A (en) * | 1992-12-24 | 1994-10-11 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Process for preparing ethyl ester of L-DOPA |
| US5525631A (en) * | 1992-12-24 | 1996-06-11 | The Yissum Research Development Company Of The Hebrew University Of Jerusalem | Compositions of the ethyl ester of L-DOPA |
| US5607969A (en) * | 1992-12-24 | 1997-03-04 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | L-DOPA ethyl ester to treat Parkinson's disease |
| EP0610595B1 (en) * | 1992-12-24 | 1999-04-14 | Teva Pharmaceutical Industries, Ltd. | Composition of l-dopa esters |
| US6703424B2 (en) | 1998-11-10 | 2004-03-09 | Teva Pharmaceutical Industries, Ltgd. | Dispersible compositions containing L-DOPA ethyl ester |
| US6376545B1 (en) | 1998-11-10 | 2002-04-23 | Teva Pharmaceutical Industries, Ltd. | Dispersible compositions containing L-DOPA ethyl ester |
| US6218566B1 (en) | 1998-11-10 | 2001-04-17 | Teva Pharmaceutical Industries, Ltd. | Process for manufacturing of L-DOPA ethyl ester |
| US6696600B2 (en) | 2001-11-13 | 2004-02-24 | Teva Pharmaceutical Industries, Ltd. | L-DOPA ethyl ester salts and uses thereof |
| US9045570B2 (en) | 2008-12-31 | 2015-06-02 | W.R. Grace & Co. - Conn. | Procatalyst composition with substituted 1,2-phenylene aromatic diester internal donor and method |
| US9464144B2 (en) | 2008-12-31 | 2016-10-11 | W. R. Grace & Co.—Conn. | Enhanced procatalyst composition and process |
| US9534063B2 (en) | 2008-12-31 | 2017-01-03 | W. R. Grace & Co.—Conn | Procatalyst composition with substituted 1,2-phenylene aromatic diester internal donor and method |
| US8263520B2 (en) | 2009-12-02 | 2012-09-11 | Dow Global Technologies Llc | Two atom bridged dicarbonate compounds as internal donors in catalysts for polypropylene manufacture |
| US8633126B2 (en) | 2009-12-02 | 2014-01-21 | Dow Global Technologies Llc | Three and four atom bridged dicarbonate compounds as internal donors in catalysts for polypropylene manufacture |
| WO2014191997A1 (en) * | 2013-05-28 | 2014-12-04 | Ramot At Tel-Aviv University Ltd. | Self-assembled micro- and nano-structures |
| WO2023175623A1 (en) * | 2022-03-18 | 2023-09-21 | Neuroderm, Ltd. | Levodopa tyrosine polymorphs |
Also Published As
| Publication number | Publication date |
|---|---|
| IL38002A0 (en) | 1971-12-29 |
| BE774683A (en) | 1972-05-02 |
| RO68988A (en) | 1980-03-15 |
| FR2111947A1 (en) | 1972-06-09 |
| DE2153813A1 (en) | 1972-05-10 |
| AU3486971A (en) | 1973-05-03 |
| NL7114701A (en) | 1972-05-03 |
| BR7107234D0 (en) | 1973-08-16 |
| ZA716958B (en) | 1973-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |