GB1321161A - Process for the manufacture of phenylalanine derivatives - Google Patents
Process for the manufacture of phenylalanine derivativesInfo
- Publication number
- GB1321161A GB1321161A GB5033371A GB5033371A GB1321161A GB 1321161 A GB1321161 A GB 1321161A GB 5033371 A GB5033371 A GB 5033371A GB 5033371 A GB5033371 A GB 5033371A GB 1321161 A GB1321161 A GB 1321161A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- boric acid
- salt
- phenyl
- compounds
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 150000002993 phenylalanine derivatives Chemical class 0.000 title 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 239000004327 boric acid Substances 0.000 abstract 3
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 abstract 2
- OFSAJYZMIPNPHE-UHFFFAOYSA-N N-acetyldopamine Chemical compound CC(=O)NCCC1=CC=C(O)C(O)=C1 OFSAJYZMIPNPHE-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000002071 phenylalkoxy group Chemical group 0.000 abstract 2
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 abstract 1
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- JDWYRSDDJVCWPB-UHFFFAOYSA-N Cyclodopa Natural products OC1=C(O)C=C2NC(C(=O)O)CC2=C1 JDWYRSDDJVCWPB-UHFFFAOYSA-N 0.000 abstract 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 abstract 1
- -1 R 8 is H Chemical group 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- XEVWDUMEFJXJOU-UHFFFAOYSA-N benzyl n-[2-(3,4-dihydroxyphenyl)ethyl]carbamate Chemical compound C1=C(O)C(O)=CC=C1CCNC(=O)OCC1=CC=CC=C1 XEVWDUMEFJXJOU-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000005265 dialkylamine group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1321161 Preparation of N-acyl dihydroxyphenylalanine derivatives and boric acid complexes thereof F HOFFMANN-LA ROCHE & CO AG 29 Oct 1971 [30 Oct 1970] 50333/71 Headings C2B and C2C Solutions of boric acid complexes of compounds of the general formula or salts thereof, where R 1 -R 3 are H or alkyl or two of the symbols together are alkylene, A is H or -COR 4 where R 4 is -OH; alkoxy which may be substituted by alkenyl, alkynyl or phenyl; or amino which may be alkyl-substituted, R 5 -R 7 are H, halogen, alkyl, alkoxy, nitro or dialkylamino, R 8 is H, alkyl, phenyl or phenylalkyl and R 9 is alkyl, phenylalkyl, phenyl or phenylalkoxy and where (a) the aliphatic groups, or portions of, R 1 -R 9 are C 1-18 , (b) the phenolic OH groups are ortho to each other, (c) when R 1 is H, A is -COR 4 and R 9 is alkyl, the N atom can (minus R 7 and R 8 ) be joined to the 2- or 6-carbon of the phenyl ring and (d) when R 1 -R 3 and R 5 -R 7 are H, A is carboxy and R 9 is phenylalkoxy, the compounds are in DL- or D-form, the phenolic OH groups being esterified with boric acid, are prepared by treating a compound of formula or a salt thereof, with boric acid or a borate at a pH of at least 7 and reacting the complex obtained with an agent furnishing a -COR 9 group while maintaining the pH of at least 7. The compounds of general Formula (I) are prepared from the solutions of the boric acid complexes by subjecting them to acidic hydrolysis and, if desired, (a) esterifying an acid of Formula I obtained or a salt thereof, (b) subjecting an ester of Formula I obtained or a salt thereof to a mild basic hydrolysis or to treatment with NH 3 , an alkylamine or a dialkylamine or (c) converting a product obtained into a salt. In the Examples the following compounds, and also solutions containing the corresponding boric acid complex starting material, are prepared: N - acetyl - L - dopa (where L - dopa is L - 3 - (3,4 - dihydroxyphenyl) - alanine); N - acetyl - DL - α - methyldopa; N-benzoyl- L - dopa; N - benzyloxycarbonyldopamine; N - acetyl - L - cyclodopa which is subsequently converted into the methyl ester, and N-acetyldopamine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1604670A CH545280A (en) | 1970-10-30 | 1970-10-30 | Process for the preparation of phenylalanine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1321161A true GB1321161A (en) | 1973-06-20 |
Family
ID=4414042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5033371A Expired GB1321161A (en) | 1970-10-30 | 1971-10-29 | Process for the manufacture of phenylalanine derivatives |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE774676A (en) |
| CA (1) | CA921929A (en) |
| CH (1) | CH545280A (en) |
| DE (1) | DE2153823A1 (en) |
| FR (1) | FR2111951B1 (en) |
| GB (1) | GB1321161A (en) |
| NL (1) | NL7113514A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987004154A1 (en) * | 1986-01-03 | 1987-07-16 | The University Of Melbourne | Melphalan derivatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU195424B (en) * | 1986-01-21 | 1988-05-30 | Egyt Gyogyszervegyeszeti Gyar | Process for the production of medical solutions containing l-3,4-dihydroxi-phenil-alpha-methil-alanine |
-
1970
- 1970-10-30 CH CH1604670A patent/CH545280A/en not_active IP Right Cessation
-
1971
- 1971-10-01 NL NL7113514A patent/NL7113514A/xx unknown
- 1971-10-27 CA CA126212A patent/CA921929A/en not_active Expired
- 1971-10-28 FR FR7138783A patent/FR2111951B1/fr not_active Expired
- 1971-10-28 DE DE19712153823 patent/DE2153823A1/en active Pending
- 1971-10-29 BE BE774676A patent/BE774676A/en unknown
- 1971-10-29 GB GB5033371A patent/GB1321161A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987004154A1 (en) * | 1986-01-03 | 1987-07-16 | The University Of Melbourne | Melphalan derivatives |
| US5075108A (en) * | 1986-01-03 | 1991-12-24 | Consolidated Pharmaceuticals, Limited | Melphalan derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2111951B1 (en) | 1973-06-29 |
| DE2153823A1 (en) | 1972-05-10 |
| CA921929A (en) | 1973-02-27 |
| BE774676A (en) | 1972-05-02 |
| FR2111951A1 (en) | 1972-06-09 |
| NL7113514A (en) | 1972-05-03 |
| CH545280A (en) | 1973-12-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |