GB1236091A - N-DISUBSTITUTED DERIVATIVES OF alpha-AMINO ACIDS - Google Patents
N-DISUBSTITUTED DERIVATIVES OF alpha-AMINO ACIDSInfo
- Publication number
- GB1236091A GB1236091A GB1673968A GB1673968A GB1236091A GB 1236091 A GB1236091 A GB 1236091A GB 1673968 A GB1673968 A GB 1673968A GB 1673968 A GB1673968 A GB 1673968A GB 1236091 A GB1236091 A GB 1236091A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- prepared
- compound
- reaction
- methoxyphenyl
- 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
- 235000008206 alpha-amino acids Nutrition 0.000 title abstract 2
- 150000001371 alpha-amino acids Chemical class 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- -1 sulphonamido Chemical group 0.000 abstract 4
- 235000004279 alanine Nutrition 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 abstract 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000004471 Glycine Substances 0.000 abstract 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- FNPYHTQMJZVFRJ-UHFFFAOYSA-N 4-chloro-n-(4-ethoxyphenyl)benzamide Chemical compound C1=CC(OCC)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 FNPYHTQMJZVFRJ-UHFFFAOYSA-N 0.000 abstract 1
- UVGPQLMHIRNFEE-UHFFFAOYSA-N 4-chloro-n-(4-methoxyphenyl)benzamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 UVGPQLMHIRNFEE-UHFFFAOYSA-N 0.000 abstract 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 abstract 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- WLTCKEHCTUYJGI-UHFFFAOYSA-N Diethyl aminomalonate Chemical compound CCOC(=O)C(N)C(=O)OCC WLTCKEHCTUYJGI-UHFFFAOYSA-N 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
- WRUZLCLJULHLEY-UHFFFAOYSA-N N-(p-hydroxyphenyl)glycine Chemical compound OC(=O)CNC1=CC=C(O)C=C1 WRUZLCLJULHLEY-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 150000003978 alpha-halocarboxylic acids Chemical class 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 abstract 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 235000019256 formaldehyde Nutrition 0.000 abstract 1
- 229960004279 formaldehyde Drugs 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/006—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length of peptides containing derivatised side chain amino acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
- C07K1/063—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups for alpha-amino functions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
- C07K1/064—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups for omega-amino or -guanidino functions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,236,091. N-Benzoyl-N-phenyl-α-aminoacid derivatives. SOGESPAR S.A. 8 April, 1968 [11 April, 1967; 26 April, 1967], No. 16739/68. Heading C2C. Novel N - phenyl - N - benzoyl - α - aminoacids, particularly of Formula I wherein R 1 is H, alkyl, aryl, alkylaryl, aralkyl, hydroxyalkyl, cycloalkyl, or heterocyclic or carboxylic group or a salified or esterified carboxylic group; R 2 is OH, O-alkyl, O-aryl, O-alkylaryl, O-cycloalkyl, O-aralkyl, heterocyclic, amino, dialkylamino, or OM, where M is an alkali metal or an alkaline earth metal; X and Y are each H, OH, OR 1 , alkyl, aryl, halogen, amino, nitro, sulphonic or sulphonamido; and the d- and l-isomers, and racemic mixtures thereof, are prepared by one of the following methods: (a) reaction of a compound of Formula II where B is -CH(R 1 )COR 2 with the required derivative of benzoic acid; (b) by reaction of a compound of Formula III where A is H with a compound of formula X-CH(R 1 )COR 2 , where X is for example halogen; (c) by saponification and/or degredation of a compound of Formula III above, wherein A is -C(R 1 )(COOR) 2 , where R is alkyl, where Z is halogen, quaternary ammonium, nitro, a sulphonic group, an aryl or alkyl sulphone where R is H or alkyl, and P is COOR, CONH 2 , CON 3 or CN, or (d) by introduction or modification of a substituent X or Y above. N - (p - methoxyphenyl) glycine, N - (p - ethoxy - phenyl) glycine, N-(p-methoxyphenyl) alanine and N-(p-ethoxyphenyl) alanine are prepared by reacting the appropriate alkoxyanaline with the appropriate α-halo-carboxylic acid optionally via the iminodialkanoic acid which is decarboxylated. The ethyl ester of an above compound is isolated when ethanol is used as the solvent. N-(p-chlorobenzoyl)-p-anisidine is prepared by reacting p-chlorobenzoic acid chloride and panisidine; with p-phenetidine, the said acid chloride gives N-(p-chlorobenzoyl)-p-phenetidine. N-(p-hydroxyphenyl) glycine and alanine ethyl esters are prepared from p-aminophenol and the α-chloro alkanoic acid esters. N - (p - methozyphenyl) amino - malonic acid diethyl ester is prepared by reaction of p-anisidine and ethyl α-bromo-malonate. N - (p - methoxyphenyl) - N - (p - chlorobenzoyl)- amino-acetonitrile is prepared by reaction of pchlorobenzoyl chloride and N-(p-methoxyphenyl) - aminoacetonitrile (obtained by reaction of p-anisidine formol and KCN). Pharmaceutical compositions in conventional forms for oral, rectal or parenteral administration and having anti-inflammatory activity comprise an above novel compound and a pharmaceutically acceptable liquid or solid carrier.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR102195A FR6340M (en) | 1967-04-11 | 1967-04-11 | |
| CH595067A CH480299A (en) | 1967-04-11 | 1967-04-26 | Process for the preparation of N-disubstituted α-amino acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1236091A true GB1236091A (en) | 1971-06-16 |
Family
ID=25698719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1673968A Expired GB1236091A (en) | 1967-04-11 | 1968-04-08 | N-DISUBSTITUTED DERIVATIVES OF alpha-AMINO ACIDS |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE713438A (en) |
| CH (1) | CH480299A (en) |
| DE (1) | DE1768173A1 (en) |
| FR (1) | FR330F (en) |
| GB (1) | GB1236091A (en) |
| NL (1) | NL6805246A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0246849A1 (en) * | 1986-05-19 | 1987-11-25 | Minnesota Mining And Manufacturing Company | Method of preparing N-acryloyl-alpha-amino acids |
| EP1713465A4 (en) * | 2004-02-11 | 2009-04-22 | Irm Llc | Compounds and compositions as lxr modulators |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8806223D0 (en) * | 1988-03-16 | 1988-04-13 | Shell Int Research | Preparation of optically active n-substituted alanine herbicides |
-
1967
- 1967-04-26 CH CH595067A patent/CH480299A/en not_active IP Right Cessation
-
1968
- 1968-04-08 GB GB1673968A patent/GB1236091A/en not_active Expired
- 1968-04-09 DE DE19681768173 patent/DE1768173A1/en active Pending
- 1968-04-09 BE BE713438D patent/BE713438A/xx unknown
- 1968-04-11 NL NL6805246A patent/NL6805246A/xx unknown
- 1968-12-24 FR FR330D patent/FR330F/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0246849A1 (en) * | 1986-05-19 | 1987-11-25 | Minnesota Mining And Manufacturing Company | Method of preparing N-acryloyl-alpha-amino acids |
| EP1713465A4 (en) * | 2004-02-11 | 2009-04-22 | Irm Llc | Compounds and compositions as lxr modulators |
| US7846949B2 (en) | 2004-02-11 | 2010-12-07 | Irm Llc | Compounds and compositions as LXR modulators |
Also Published As
| Publication number | Publication date |
|---|---|
| BE713438A (en) | 1968-08-16 |
| CH480299A (en) | 1969-10-31 |
| FR330F (en) | 1970-10-12 |
| DE1768173A1 (en) | 1972-03-09 |
| NL6805246A (en) | 1968-10-14 |
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