GB2001309A - alpha -Halomethyl beta -(3-indolyl) amino acids and derivatives - Google Patents

alpha -Halomethyl beta -(3-indolyl) amino acids and derivatives

Info

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
Application number
GB787827971A
Other versions
GB2001309B (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merrell Toraude et Cie
Original Assignee
Merrell Toraude et Cie
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Merrell Toraude et Cie filed Critical Merrell Toraude et Cie
Publication of GB2001309A publication Critical patent/GB2001309A/en
Application granted granted Critical
Publication of GB2001309B publication Critical patent/GB2001309B/en
Expired legal-status Critical Current

Links

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)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General 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>
GB787827971A 1977-07-21 1978-06-27 Alpha-halomethyl amino acid derivatives Expired GB2001309B (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (9)

* Cited by examiner, † Cited by third party
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 Chiral alpha-difluoromethyl amino acid compound and preparation method thereof

Also Published As

Publication number Publication date
NZ187545A (en) 1982-06-29
GB2001309B (en) 1982-03-03
BE869177A (en) 1978-11-16
IT7850355A0 (en) 1978-07-18
AU518251B2 (en) 1981-09-24
FR2398057B1 (en) 1981-07-31
FR2398057A1 (en) 1979-02-16
AU3731378A (en) 1980-01-03
IT1106106B (en) 1985-11-11
ZA783356B (en) 1979-06-27

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Legal Events

Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19940627