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WO1990011292A3 - Controlled-action anesthetic compounds and pharmaceutical compositions containing same - Google Patents

Controlled-action anesthetic compounds and pharmaceutical compositions containing same Download PDF

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Publication number
WO1990011292A3
WO1990011292A3 PCT/FR1990/000197 FR9000197W WO9011292A3 WO 1990011292 A3 WO1990011292 A3 WO 1990011292A3 FR 9000197 W FR9000197 W FR 9000197W WO 9011292 A3 WO9011292 A3 WO 9011292A3
Authority
WO
WIPO (PCT)
Prior art keywords
amino acids
alpha amino
pharmaceutical compositions
controlled
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.)
Ceased
Application number
PCT/FR1990/000197
Other languages
French (fr)
Other versions
WO1990011292A2 (en
Inventor
Serge Raynal
Maryse Grousset
Alain Rancurel
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.)
Laboratoires Pharmascience SA
Societe Nationale des Poudres et Explosifs
Original Assignee
Laboratoires Pharmascience SA
Societe Nationale des Poudres et Explosifs
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 Laboratoires Pharmascience SA, Societe Nationale des Poudres et Explosifs filed Critical Laboratoires Pharmascience SA
Publication of WO1990011292A2 publication Critical patent/WO1990011292A2/en
Publication of WO1990011292A3 publication Critical patent/WO1990011292A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0207—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)4-C(=0), e.g. 'isosters', replacing two amino acids
    • 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
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • 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
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/0606—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr
    • C07K5/06069—Ser-amino acid
    • 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
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • 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
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • 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
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
    • 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
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
    • C07K5/1008—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)

Abstract

The present invention concerns the application of compounds having formula (I), wherein B is such that R-NH-B is an aminobenzoic acid-derived anesthetic: wherein R represents H or an alkyl C1-C5 radical, preferably linear, possibly functionalized in position 2 to 5; wherein AAn is an oligopeptide group consisting of 1 to 10 alpha amino acids, preferably 2 to 6, i.e. in which n is a whole number from 1 to 10 and AA represents natural amino acids or synthetic alpha amino acids in the form of D or or D, L, whereby said alpha amino acids in the form of D or L or D,L, whereby said alpha amino acids may be different, bearing in mind that when R-NH-B represents benzocaine, the first C-terminal acid is L phenylalanine when n = 1 and L, D or D,L pehnylalanine when n is greater than 1 and their pharmaceutically acceptable salts, to the preparation of pharmaceutical compositions useful as anesthetics. The invention also concerns compounds for anesthetic use and a process for increasing the potency of anesthetics having an aromatic amine group.
PCT/FR1990/000197 1989-03-24 1990-03-23 Controlled-action anesthetic compounds and pharmaceutical compositions containing same Ceased WO1990011292A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8903909A FR2644697B1 (en) 1989-03-24 1989-03-24 ANESTHETIC COMPOUNDS WITH CONTROLLED DURATION OF ACTION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
FR89/03909 1989-03-24

Publications (2)

Publication Number Publication Date
WO1990011292A2 WO1990011292A2 (en) 1990-10-04
WO1990011292A3 true WO1990011292A3 (en) 1990-11-15

Family

ID=9380039

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR1990/000197 Ceased WO1990011292A2 (en) 1989-03-24 1990-03-23 Controlled-action anesthetic compounds and pharmaceutical compositions containing same

Country Status (3)

Country Link
EP (1) EP0418365A1 (en)
FR (1) FR2644697B1 (en)
WO (1) WO1990011292A2 (en)

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB665675A (en) * 1948-12-02 1952-01-30 Ward Blenkinsop & Co Ltd Process for the manufacture of derivatives of hydroxy acids
US2891091A (en) * 1957-06-03 1959-06-16 Canadian Patents Dev Derivatives of para-aminosalicylic acid
FR1553098A (en) * 1967-11-30 1969-01-10
FR2208886A1 (en) * 1972-12-05 1974-06-28 Boehringer Mannheim Gmbh
FR2399663A1 (en) * 1977-08-05 1979-03-02 American Hospital Supply Corp COMPOSITION AND METHOD FOR DETERMINING TRANSFERASE AND PROTEASE ACTIVITY
GB2022079A (en) * 1978-06-01 1979-12-12 Nitto Boseki Co Ltd L-leucyl-4-hydroxyanilide derivatives
GB2034690A (en) * 1978-11-16 1980-06-11 Nitto Boseki Co Ltd L - y - glutamyl - 3 - carboxy - 4-hydroxyanilide and salts thereof
EP0110306A2 (en) * 1982-11-27 1984-06-13 BEHRINGWERKE Aktiengesellschaft Chromogene compounds, process for their preparation and their use
EP0117089A1 (en) * 1983-02-03 1984-08-29 The Regents Of The University Of California Beta-adrenergic antagonist compounds and derivatives of beta-adrenergic antagonists
WO1986001209A2 (en) * 1984-08-02 1986-02-27 Boehringer Mannheim Gmbh NEW p-PHENYLENEDIAMINE PEPTIDES AND REACTANCE CONTAINING THEM FOR THE DETERMINATION OF PROTEASES OF THE BLOOD COAGULATION SYSTEM
EP0195582A1 (en) * 1985-03-14 1986-09-24 SMITH KLINE DAUELSBERG GmbH 5-Aminosalicylic acid derivatives of non-steroidal antiinflammatory acids

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58172354A (en) * 1982-04-05 1983-10-11 Dai Ichi Pure Chem Co Ltd Peptide derivative

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB665675A (en) * 1948-12-02 1952-01-30 Ward Blenkinsop & Co Ltd Process for the manufacture of derivatives of hydroxy acids
US2891091A (en) * 1957-06-03 1959-06-16 Canadian Patents Dev Derivatives of para-aminosalicylic acid
FR1553098A (en) * 1967-11-30 1969-01-10
FR2208886A1 (en) * 1972-12-05 1974-06-28 Boehringer Mannheim Gmbh
FR2399663A1 (en) * 1977-08-05 1979-03-02 American Hospital Supply Corp COMPOSITION AND METHOD FOR DETERMINING TRANSFERASE AND PROTEASE ACTIVITY
GB2022079A (en) * 1978-06-01 1979-12-12 Nitto Boseki Co Ltd L-leucyl-4-hydroxyanilide derivatives
GB2034690A (en) * 1978-11-16 1980-06-11 Nitto Boseki Co Ltd L - y - glutamyl - 3 - carboxy - 4-hydroxyanilide and salts thereof
EP0110306A2 (en) * 1982-11-27 1984-06-13 BEHRINGWERKE Aktiengesellschaft Chromogene compounds, process for their preparation and their use
EP0117089A1 (en) * 1983-02-03 1984-08-29 The Regents Of The University Of California Beta-adrenergic antagonist compounds and derivatives of beta-adrenergic antagonists
WO1986001209A2 (en) * 1984-08-02 1986-02-27 Boehringer Mannheim Gmbh NEW p-PHENYLENEDIAMINE PEPTIDES AND REACTANCE CONTAINING THEM FOR THE DETERMINATION OF PROTEASES OF THE BLOOD COAGULATION SYSTEM
EP0195582A1 (en) * 1985-03-14 1986-09-24 SMITH KLINE DAUELSBERG GmbH 5-Aminosalicylic acid derivatives of non-steroidal antiinflammatory acids

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
Biochemical and Biophysical Research Communications, Volume 146, No. 1, 15 July 1987, Academic Press, Inc., J.R. McDERMOTT et al.: "Involvement of Endopeptidase 24.15 in the Inactivation of Bradykinin by Rat Brain Slices", pages 154-158 *
Biochemistry, Volume 22, 1983, American Chemical Society, J. ALMENOFF et al.: "Membrane-Bound Kidney Neutral Metalloendopeptidase: Interaction with Synthetic Substrates, Natural Peptides, and Inhibitors", pages 590-599 *
Biochemistry, Volume 25, 1986, American Chemical Society, M. POZSGAY et al.: "Substrate and Inhibitor Studies of Thermolysin-Like Neutral Metalloendopeptidase from Kidney Membrane Fractions. Comparison with Bacterial Thermolysin", pages 1292-1299 *
Biochemistry, Volume 27, 1988, American Chemical Society, M. ORLOWSKI et al.: "Substrate-Related Potent Inhibitors of Brain Metalloendopeptidase", pages 597-602 *
CHEMICAL ABSTRACTS, Volume 100, 1984, (Columbus, Ohio, US), voir page 645* Resume 121624y, & JP-A-58172354 (Daiichi Kagaku Yakuhin K.K.) 11 October 1983* *
CHEMICAL ABSTRACTS, Volume 102, 1985, (Columbus, Ohio, US), M. POZSGAY et al.: "The Active site of Endopeptidase-24.11: Substrate and Inhibitor Studies", voir page 261* Resume 145296k, & Biochem. Soc. Trans. 1985, 13(1), 44-7* *
CHEMICAL ABSTRACTS, Volume 109, 1988, (Columbus, Ohio, US), C.J. MOLINEAUX et al.: "Endopeptidase- 24.15 is the Primary Enzme that Degrades Luteinizing Hormone Releasing Hormone Both in Vitro and in Vivo", voir page 96* Resume 142840s, & J. Neurochem. 1988, 51(2), 624-33* *

Also Published As

Publication number Publication date
FR2644697A1 (en) 1990-09-28
WO1990011292A2 (en) 1990-10-04
FR2644697B1 (en) 1992-05-15
EP0418365A1 (en) 1991-03-27

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