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
Application number
PCT/FR1990/000197
Other languages
French (fr)
Other versions
WO1990011292A2 (en
Inventor
Serge Raynal
Maryse Grousset
Alain Rancurel
Original Assignee
Poudres & Explosifs Ste Nale
Pharmascience Lab
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 Poudres & Explosifs Ste Nale, Pharmascience Lab filed Critical Poudres & Explosifs Ste Nale
Publication of WO1990011292A2 publication Critical patent/WO1990011292A2/en
Publication of WO1990011292A3 publication Critical patent/WO1990011292A3/en

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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)
  • 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)
  • 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 WO1990011292A2 (en)

Applications Claiming Priority (2)

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

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

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