GB2001309A - alpha -Halomethyl beta -(3-indolyl) amino acids and derivatives - Google Patents
alpha -Halomethyl beta -(3-indolyl) amino acids and derivativesInfo
- Publication number
- GB2001309A GB2001309A GB787827971A GB7827971A GB2001309A GB 2001309 A GB2001309 A GB 2001309A GB 787827971 A GB787827971 A GB 787827971A GB 7827971 A GB7827971 A GB 7827971A GB 2001309 A GB2001309 A GB 2001309A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- carbon atoms
- carbonyl
- alkyl
- 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.)
- Granted
Links
- 229940093740 amino acid and derivative Drugs 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 150000002431 hydrogen Chemical group 0.000 abstract 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 abstract 1
- 102000003823 Aromatic-L-amino-acid decarboxylases Human genes 0.000 abstract 1
- 108090000121 Aromatic-L-amino-acid decarboxylases Proteins 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000001041 indolyl group Chemical group 0.000 abstract 1
- -1 p-hydroxyphenyl Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07K5/08—Tripeptides
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
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)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Compounds of the formula <IMAGE> wherein Y is -CH2F, -CHF2, -CF3, -CH2Cl or -CHCl2; R1 is hydroxy, alkoxy of 1 to 8 carbon atoms, -NY1Y2 wherein Y1 and Y2 are the same or different and are each hydrogen or alkyl of 1 to 4 carbon atoms, or -NH-CHR8-COOH wherein R8 is hydrogen, alkyl of 1 to 4 carbon atoms, benzyl or p-hydroxyphenyl; R2 is hydrogen, (C1-4alkyl)carbonyl, (C1- 4alkoxy)carbonyl or -CO-CHNH2-R9 wherein R9 is hydrogen, alkyl of 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R3 is hydrogen or methyl; and R4, R5, R6 and R7 are certain combinations of hydrogen, methyl, halogen, trifluoromethyl and OR10 wherein R10 is hydrogen, alkyl of 1 to 8 carbon atoms, (C1-6alkyl)carbonyl, benzoyl or phenyl(C1-6alkylene) carbonyl may be prepared by formation of the indole ring. The compounds irreversibly inhibit aromatic amino acid decarboxylase. The compounds may be converted to pharmaceutically active compounds of the formula II. <IMAGE>
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81759377A | 1977-07-21 | 1977-07-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2001309A true GB2001309A (en) | 1979-01-31 |
| GB2001309B GB2001309B (en) | 1982-03-03 |
Family
ID=25223426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB787827971A Expired GB2001309B (en) | 1977-07-21 | 1978-06-27 | Alpha-halomethyl amino acid derivatives |
Country Status (7)
| Country | Link |
|---|---|
| AU (1) | AU518251B2 (en) |
| BE (1) | BE869177A (en) |
| FR (1) | FR2398057A1 (en) |
| GB (1) | GB2001309B (en) |
| IT (1) | IT1106106B (en) |
| NZ (1) | NZ187545A (en) |
| ZA (1) | ZA783356B (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0052200A1 (en) * | 1980-11-15 | 1982-05-26 | Degussa Aktiengesellschaft | Cyclic acetals of N-acylated glutamic acid gamma-semialdehydes, process for their preparation and their use |
| FR2499072A1 (en) * | 1981-02-04 | 1982-08-06 | Stago Laboratoire | 5-ACETYLOXY-L-TRYPTOPHAN AND ITS ADDITIONAL SALTS, PREPARATION METHOD AND THERAPEUTIC USE |
| JPS59231054A (en) * | 1983-05-24 | 1984-12-25 | ソシエテ・アノニム・パンメデイカ | Novel dipeptides of l-5-hydroxytryptophan, manufacture and drug containing them |
| US4491590A (en) * | 1982-02-18 | 1985-01-01 | Merck & Co., Inc. | Allylsulfoxide enzyme inhibitors |
| CN104803865A (en) * | 2004-12-22 | 2015-07-29 | Ambrx公司 | Compositions containing, methods involving, and uses of non-natural amino acids and polypeptides |
| CN108047086A (en) * | 2004-12-22 | 2018-05-18 | Ambrx公司 | Composition containing alpha-non-natural amino acid and polypeptide, be related to the method for alpha-non-natural amino acid and polypeptide with and application thereof |
| CN113072456A (en) * | 2021-04-12 | 2021-07-06 | 中国科学技术大学 | Chiral alpha-difluoromethyl amino acid compound and preparation method thereof |
-
1978
- 1978-06-12 ZA ZA00783356A patent/ZA783356B/en unknown
- 1978-06-13 NZ NZ187545A patent/NZ187545A/en unknown
- 1978-06-21 AU AU37313/78A patent/AU518251B2/en not_active Expired
- 1978-06-27 GB GB787827971A patent/GB2001309B/en not_active Expired
- 1978-07-18 IT IT50355/78A patent/IT1106106B/en active
- 1978-07-20 BE BE189423A patent/BE869177A/en not_active IP Right Cessation
- 1978-07-20 FR FR7821553A patent/FR2398057A1/en active Granted
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0052200A1 (en) * | 1980-11-15 | 1982-05-26 | Degussa Aktiengesellschaft | Cyclic acetals of N-acylated glutamic acid gamma-semialdehydes, process for their preparation and their use |
| FR2499072A1 (en) * | 1981-02-04 | 1982-08-06 | Stago Laboratoire | 5-ACETYLOXY-L-TRYPTOPHAN AND ITS ADDITIONAL SALTS, PREPARATION METHOD AND THERAPEUTIC USE |
| EP0058111A1 (en) * | 1981-02-04 | 1982-08-18 | Laboratoires Merck-Clévenot | 5-Acetyloxy-L-tryptophane and its salts, process for their preparation and their therapeutical uses |
| US4491590A (en) * | 1982-02-18 | 1985-01-01 | Merck & Co., Inc. | Allylsulfoxide enzyme inhibitors |
| JPS59231054A (en) * | 1983-05-24 | 1984-12-25 | ソシエテ・アノニム・パンメデイカ | Novel dipeptides of l-5-hydroxytryptophan, manufacture and drug containing them |
| CN104803865A (en) * | 2004-12-22 | 2015-07-29 | Ambrx公司 | Compositions containing, methods involving, and uses of non-natural amino acids and polypeptides |
| CN108047086A (en) * | 2004-12-22 | 2018-05-18 | Ambrx公司 | Composition containing alpha-non-natural amino acid and polypeptide, be related to the method for alpha-non-natural amino acid and polypeptide with and application thereof |
| CN113072456A (en) * | 2021-04-12 | 2021-07-06 | 中国科学技术大学 | Chiral alpha-difluoromethyl amino acid compound and preparation method thereof |
| CN113072456B (en) * | 2021-04-12 | 2022-04-19 | 中国科学技术大学 | A kind of chiral α-difluoromethyl amino acid compound and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2001309B (en) | 1982-03-03 |
| ZA783356B (en) | 1979-06-27 |
| NZ187545A (en) | 1982-06-29 |
| IT1106106B (en) | 1985-11-11 |
| FR2398057A1 (en) | 1979-02-16 |
| BE869177A (en) | 1978-11-16 |
| FR2398057B1 (en) | 1981-07-31 |
| AU3731378A (en) | 1980-01-03 |
| IT7850355A0 (en) | 1978-07-18 |
| AU518251B2 (en) | 1981-09-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19940627 |