FR2351125A1 - Antibacterial phosphonic acid peptide derivs. - prepd. e.g. by removing protecting groups from corresponding protected peptides - Google Patents

Antibacterial phosphonic acid peptide derivs. - prepd. e.g. by removing protecting groups from corresponding protected peptides

Info

Publication number
FR2351125A1
FR2351125A1 FR7714551A FR7714551A FR2351125A1 FR 2351125 A1 FR2351125 A1 FR 2351125A1 FR 7714551 A FR7714551 A FR 7714551A FR 7714551 A FR7714551 A FR 7714551A FR 2351125 A1 FR2351125 A1 FR 2351125A1
Authority
FR
France
Prior art keywords
prepd
antibacterial
protecting groups
phosphonic acid
alanyl
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.)
Withdrawn
Application number
FR7714551A
Other languages
French (fr)
Inventor
Frank Ratcliffe Atherton
Michael John Hall
Cedric Herbert Hassall
Robert Wilson Lambert
Peter Stuart Ringrose
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of FR2351125A1 publication Critical patent/FR2351125A1/en
Withdrawn legal-status Critical Current

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
    • C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Communicable Diseases (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oncology (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Peptide derivs. of formula (I) and their pharmaceutically acceptable salts are new. In the formula, n is 1,2 or 3; and R1-3 are each residues of alpha-amino acids normally occurring in protein; provided that R1 is not = H and R4 is OH or CH3; the configuration at C-atoms (a) and (b) being L (when R2 and R3 are other than H), and the configuration at C-atom (c) being S. (I) have antibacterial activity against organisms such as Streptococcus faecalis and Haemophilus influenzae. Specific cpds. (I) include (1S)-1-(L-alanyl-L-alanylamino)-ethylphosphonic acid. In an example, this was prepd. by converting (1S)-1-/N-benzyloxycarbonyl-L-alanyl-L-alanyl)amino/ethylphosphon- ic acid monobenzylamide salt (obtained in 5 stages from (1R,S)-1-(benzyloxycarbonylamino)ethylphosphonic acid) into the free acid and hydrogenating in the presence of Pd/C.
FR7714551A 1976-05-14 1977-05-12 Antibacterial phosphonic acid peptide derivs. - prepd. e.g. by removing protecting groups from corresponding protected peptides Withdrawn FR2351125A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2001376 1976-05-14

Publications (1)

Publication Number Publication Date
FR2351125A1 true FR2351125A1 (en) 1977-12-09

Family

ID=10138906

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7714551A Withdrawn FR2351125A1 (en) 1976-05-14 1977-05-12 Antibacterial phosphonic acid peptide derivs. - prepd. e.g. by removing protecting groups from corresponding protected peptides

Country Status (3)

Country Link
JP (1) JPS52139022A (en)
DE (1) DE2721761A1 (en)
FR (1) FR2351125A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0010067A2 (en) * 1978-10-05 1980-04-16 Ciba-Geigy Ag Process for influencing plant growth

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4331591A (en) * 1978-10-05 1982-05-25 Ciba-Geigy Corporation Chemical process for the production of α-aminophosphonic acids and peptide derivatives
EP0103867B1 (en) * 1982-09-17 1986-12-17 Kyowa Hakko Kogyo Co., Ltd. Phosphorus-containing peptide derivative

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2298335A1 (en) * 1975-01-27 1976-08-20 Hoffmann La Roche NEW DERIVATIVES OF PHOSPHONIC AND PHOSPHINIC ACID PEPTIDES

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2298335A1 (en) * 1975-01-27 1976-08-20 Hoffmann La Roche NEW DERIVATIVES OF PHOSPHONIC AND PHOSPHINIC ACID PEPTIDES

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
EXBK/72 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0010067A2 (en) * 1978-10-05 1980-04-16 Ciba-Geigy Ag Process for influencing plant growth
EP0010067A3 (en) * 1978-10-05 1980-04-30 Ciba-Geigy Ag Agent and process for influencing plant growth
US4431438A (en) * 1978-10-05 1984-02-14 Ciba-Geigy Corporation Aminoethane-methylphosphinic acid derivatives for influencing plant growth

Also Published As

Publication number Publication date
JPS52139022A (en) 1977-11-19
DE2721761A1 (en) 1977-12-01

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Legal Events

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ST Notification of lapse