FR2347336A1 - Polypeptide enkephalin analogues - for use as analgesics by intravenous injection - Google Patents

Polypeptide enkephalin analogues - for use as analgesics by intravenous injection

Info

Publication number
FR2347336A1
FR2347336A1 FR7710668A FR7710668A FR2347336A1 FR 2347336 A1 FR2347336 A1 FR 2347336A1 FR 7710668 A FR7710668 A FR 7710668A FR 7710668 A FR7710668 A FR 7710668A FR 2347336 A1 FR2347336 A1 FR 2347336A1
Authority
FR
France
Prior art keywords
opt
alkyl
ala
substd
lys
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
FR7710668A
Other languages
French (fr)
Other versions
FR2347336B1 (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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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
Priority claimed from GB14362/76A external-priority patent/GB1523812A/en
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Publication of FR2347336A1 publication Critical patent/FR2347336A1/en
Application granted granted Critical
Publication of FR2347336B1 publication Critical patent/FR2347336B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/665—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
    • C07K14/70—Enkephalins
    • C07K14/702—Enkephalins with at least 1 amino acid in D-form
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Neurosurgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biomedical Technology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biophysics (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biochemistry (AREA)
  • Pain & Pain Management (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)

Abstract

New polypeptides of formula (I) and their salts: Where R1 is H or 1-4C alkyl. R2 is H, 1-3C alkonoyl, 2-6C alkyxycarbonyl, an Arg, Gly, Glu, Asp, Phe or beta-Ala residue, a Lys or D-Lys residue opt. NE-substd. by 2-6C alkoxycarbonyl, or a 2- to 6- membered peptide chain consisting of Gly, Lys, Pro, Phe, Gln, Glu, Leu, Arg and/or Asp units in which the Lys and Arg residues are opt. linked via their E-amino or E-guanidino radicals and the Asp and Glu residues are opt. linked via their alpha-or gamma-COOH radicals. B is D-Ser or D-Thr (or their alpha-alkoxy analogues) or is D-Ala, D-Leu, D-Asp, D-Lys, D-Trp, D-Met, Beta-Ala or Azala. E is opt. N-substd. Gly or Azgly, or opt. N-alkyl substd. beta-Ala. F is opt N-alkyl substd. Phe, hexahydro-Phe, Azphe or hexahydro-Azphe G is opt. N-alkyl substd. Leu, D-Leu, Met, D-Met, Nle, D-Nle, Ile or D-Ile, or is Pro, Azleu or Azpro. K is OH, NH2, OR3, NHR5, Gly-OR5, D-Thr, OR8, Thr-OR8, D-Ala-OR8, Ala-OR8 or 1-6C alkyl, or K+G represents the D or L form of a radical of formula (II), (III) or (IV) (where n=1-4): R3 is 1-6C alkyl, alkenyl of hydroxyalkyl, 1-6C aminoalkyl or 2-10C alkylaminoalkyl (both opt. N-substd. by benzyloxycarbonyl), phenyl, or a gp. of formula CH(CH2OR4)2 (V), CH2CH(OR4)CH2OR4 (VI) or CH2CH2OR4 (VII). R4 is 1-20C alkanoyl. R5 is 1-20C alkanoyl. R5 is 1-6C alkyl or cycloalkyl, NR6R7, NHCH2CH2OR4, 1-6C hydroxyalkylamino or 2-10C (alkylamino)alkylamino or (dialkylamino)alkylamino. R6 and R7 are 1-6C alkyl or NR6R7 is a 5- or 6- membered ring opt. contg. another heteroatom. R8 is H, 1-6C alkyl or a gp. of formula (V), (VI), or (VII). (I) Unlike natural enkephalines, exhibit analgesic activity when administered intravenously. Exemplified cpds. are effective at doses of 10-100 mg/kg (mouse, hot-plate test) and have LD50 values of 90-464 mg/kg (I.V., mouse).
FR7710668A 1976-04-08 1977-04-07 Polypeptide enkephalin analogues - for use as analgesics by intravenous injection Granted FR2347336A1 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB14362/76A GB1523812A (en) 1976-04-08 1976-04-08 Polypeptide
GB2106376 1976-05-21
GB2205576 1976-05-27
GB2929876 1976-07-14
GB4483776 1976-10-28
GB4483876 1976-10-28

Publications (2)

Publication Number Publication Date
FR2347336A1 true FR2347336A1 (en) 1977-11-04
FR2347336B1 FR2347336B1 (en) 1980-07-18

Family

ID=27546664

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7710668A Granted FR2347336A1 (en) 1976-04-08 1977-04-07 Polypeptide enkephalin analogues - for use as analgesics by intravenous injection

Country Status (13)

Country Link
JP (1) JPS52139039A (en)
AU (1) AU510760B2 (en)
CS (1) CS202568B2 (en)
DD (1) DD130348A5 (en)
DE (1) DE2715803A1 (en)
DK (1) DK158077A (en)
FI (1) FI771049A (en)
FR (1) FR2347336A1 (en)
HU (1) HU176260B (en)
NZ (1) NZ183712A (en)
PL (1) PL106210B1 (en)
SE (1) SE7704043L (en)
SU (1) SU904518A3 (en)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2359120A1 (en) * 1976-07-19 1978-02-17 Sandoz Sa NEW POLYPEPTIDIC COMPOUNDS, THEIR PREPARATION AND THEIR APPLICATION AS MEDICINAL PRODUCTS
FR2359817A1 (en) * 1976-07-27 1978-02-24 Reckitt & Colmann Prod Ltd Peptide cpds. contg. tyrosine, glycine, phenylalanine and d-amino acid - local anaesthetics, smooth muscle relaxants, adrenergic neutron blockers, beta-stimulants etc.
FR2364890A1 (en) * 1976-09-16 1978-04-14 Richter Gedeon Vegyeszet NEW PENTAPEPTIDES AND PROCESS FOR THEIR PREPARATION
FR2365553A1 (en) * 1976-09-27 1978-04-21 Lilly Co Eli AMID DERIVATIVES OF PENTAPEPTIDES AND TETRAPEPTIDES AND THEIR USE AS MEDICINAL PRODUCTS
FR2371422A1 (en) * 1976-11-23 1978-06-16 Wellcome Found NEW PEPTIDES AND MEDICINAL PRODUCTS CONTAINING THESE SUBSTANCES
FR2381746A1 (en) * 1976-09-01 1978-09-22 Coy David NEW ENCEPHALINIC DERIVATIVES OF METHIONINE
EP0000559A1 (en) * 1977-07-22 1979-02-07 The Wellcome Foundation Limited Pentapeptide-N-alkylamides and their acid addition salts, methods for preparation of these compounds and pharmaceutical formulations containing them
EP0002236A1 (en) * 1977-11-24 1979-06-13 The Wellcome Foundation Limited Peptides, their salts, their acid addition salts, pharmaceutical formulations containing them and their use as morphine antagonists and anaesthetics
FR2411829A1 (en) * 1977-12-15 1979-07-13 Reckitt & Colmann Prod Ltd DERIVATIVES OF TETRAPEPTIDES, THEIR METHODS OF OBTAINING THEM AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
FR2424253A1 (en) * 1978-04-27 1979-11-23 Brun Lab Sa Le NEW DERIVATIVES OF PEPTIDES ANALOGUES OF ENKEPHALINS, THEIR METHOD OF PREPARATION AND THEIR THERAPEUTIC APPLICATION
EP0008196A1 (en) * 1978-08-08 1980-02-20 American Home Products Corporation Pentapeptides, processes for their preparation, intermediates used in such processes, use in pharmaceutical compositions and compositions containing them
EP0018072A1 (en) * 1979-03-30 1980-10-29 Beckman Instruments, Inc. Synthetic peptides having pituitary growth hormone releasing activity
FR2488253A1 (en) * 1980-08-08 1982-02-12 Roques Bernard NEW PEPTIDES AND THEIR THERAPEUTIC APPLICATION
EP0451763A2 (en) * 1990-04-09 1991-10-16 Fuji Photo Film Co., Ltd. Peptide derivatives with amphiphatic properties, intermediates thereof and liposomes and films comprising said derivatives
EP3710467A4 (en) * 2017-11-17 2021-08-04 Cytogel Pharma, LLC Polymer agonists of mu opioid receptors
US12037416B2 (en) 2018-11-19 2024-07-16 Cytogel Pharma, Llc Polymer agonists of mu opioid receptors

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2933947A1 (en) * 1979-08-22 1981-03-12 Hoechst Ag, 6000 Frankfurt NEW PEPTIDAMIDES AND METHOD FOR THEIR PRODUCTION.
JPS5692846A (en) * 1979-12-27 1981-07-27 Takeda Chem Ind Ltd Tetrapeptide derivative and its preparation
US4495178A (en) * 1983-10-06 1985-01-22 G. D. Searle & Co. Enkephalin analogs
EP1975153A3 (en) * 2003-05-30 2010-03-31 Prozymex A/S Protease inhibitors
KR102016961B1 (en) * 2011-02-09 2019-09-02 노보자임스 에이/에스 Peptide for use in the treatment of skin conditions
JP2013043885A (en) * 2011-08-26 2013-03-04 Kansai Bunri Sogo Gakuen Dehydroamino acid-containing glycerol derivative
CZ2012313A3 (en) * 2012-05-11 2013-05-29 Zetor Tractors A.S. Arrangement of reversing transmission, especially for motor vehicles and construction machinery, with two branches of power flow l

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2359120A1 (en) * 1976-07-19 1978-02-17 Sandoz Sa NEW POLYPEPTIDIC COMPOUNDS, THEIR PREPARATION AND THEIR APPLICATION AS MEDICINAL PRODUCTS
FR2359817A1 (en) * 1976-07-27 1978-02-24 Reckitt & Colmann Prod Ltd Peptide cpds. contg. tyrosine, glycine, phenylalanine and d-amino acid - local anaesthetics, smooth muscle relaxants, adrenergic neutron blockers, beta-stimulants etc.
FR2381746A1 (en) * 1976-09-01 1978-09-22 Coy David NEW ENCEPHALINIC DERIVATIVES OF METHIONINE
FR2364890A1 (en) * 1976-09-16 1978-04-14 Richter Gedeon Vegyeszet NEW PENTAPEPTIDES AND PROCESS FOR THEIR PREPARATION
FR2365553A1 (en) * 1976-09-27 1978-04-21 Lilly Co Eli AMID DERIVATIVES OF PENTAPEPTIDES AND TETRAPEPTIDES AND THEIR USE AS MEDICINAL PRODUCTS
FR2371422A1 (en) * 1976-11-23 1978-06-16 Wellcome Found NEW PEPTIDES AND MEDICINAL PRODUCTS CONTAINING THESE SUBSTANCES
EP0000559A1 (en) * 1977-07-22 1979-02-07 The Wellcome Foundation Limited Pentapeptide-N-alkylamides and their acid addition salts, methods for preparation of these compounds and pharmaceutical formulations containing them
EP0002236A1 (en) * 1977-11-24 1979-06-13 The Wellcome Foundation Limited Peptides, their salts, their acid addition salts, pharmaceutical formulations containing them and their use as morphine antagonists and anaesthetics
FR2411829A1 (en) * 1977-12-15 1979-07-13 Reckitt & Colmann Prod Ltd DERIVATIVES OF TETRAPEPTIDES, THEIR METHODS OF OBTAINING THEM AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
EP0005658A1 (en) * 1978-04-27 1979-11-28 Laboratoire le Brun S.A. Société dite: Peptide derivatives analogue to encephalines, process for their preparation and their therapeutical application
FR2424253A1 (en) * 1978-04-27 1979-11-23 Brun Lab Sa Le NEW DERIVATIVES OF PEPTIDES ANALOGUES OF ENKEPHALINS, THEIR METHOD OF PREPARATION AND THEIR THERAPEUTIC APPLICATION
EP0008196A1 (en) * 1978-08-08 1980-02-20 American Home Products Corporation Pentapeptides, processes for their preparation, intermediates used in such processes, use in pharmaceutical compositions and compositions containing them
EP0018072A1 (en) * 1979-03-30 1980-10-29 Beckman Instruments, Inc. Synthetic peptides having pituitary growth hormone releasing activity
FR2488253A1 (en) * 1980-08-08 1982-02-12 Roques Bernard NEW PEPTIDES AND THEIR THERAPEUTIC APPLICATION
EP0046113A1 (en) * 1980-08-08 1982-02-17 Etablissement Public dit: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS) Peptides and their therapeutic use
EP0451763A2 (en) * 1990-04-09 1991-10-16 Fuji Photo Film Co., Ltd. Peptide derivatives with amphiphatic properties, intermediates thereof and liposomes and films comprising said derivatives
EP0451763A3 (en) * 1990-04-09 1991-12-04 Fuji Photo Film Co., Ltd. Peptide derivatives with amphiphatic properties, intermediates thereof and liposomes and films comprising said derivatives
US5252706A (en) * 1990-04-09 1993-10-12 Fuji Photo Film Co., Ltd. Peptide derivative amphiphatic compound, intermediate thereof and liposome and film comprising peptide derivative amphiphatic compound
EP3710467A4 (en) * 2017-11-17 2021-08-04 Cytogel Pharma, LLC Polymer agonists of mu opioid receptors
US12037416B2 (en) 2018-11-19 2024-07-16 Cytogel Pharma, Llc Polymer agonists of mu opioid receptors

Also Published As

Publication number Publication date
NZ183712A (en) 1979-10-25
SU904518A3 (en) 1982-02-07
SE7704043L (en) 1977-10-09
HU176260B (en) 1981-01-28
DE2715803A1 (en) 1977-10-27
JPS52139039A (en) 1977-11-19
FI771049A (en) 1977-10-09
PL197302A1 (en) 1978-02-13
DD130348A5 (en) 1978-03-22
CS202568B2 (en) 1981-01-30
AU2381977A (en) 1978-10-05
PL106210B1 (en) 1979-12-31
DK158077A (en) 1977-10-09
AU510760B2 (en) 1980-07-10
FR2347336B1 (en) 1980-07-18

Similar Documents

Publication Publication Date Title
FR2347336A1 (en) Polypeptide enkephalin analogues - for use as analgesics by intravenous injection
DE3881592D1 (en) LHRH ANTAGONISTS, THEIR PRODUCTION AND RELATED PHARMACEUTICAL PREPARATIONS.
SE7412140L (en)
SE7502520L (en)
KR850001230A (en) Method for preparing octapeptide vazopressin antagonist
ATE4452T1 (en) TRIPEPTIDES, PROCESSES FOR THEIR PRODUCTION, THERAPEUTIC COMPOSITIONS CONTAINING THEM AND METHODS OF THEIR ADMINISTRATION.
Malin et al. Subcutaneous injection of an analog of neuropeptide FF prevents naloxone-precipitated morphine abstinence syndrome
NL7703851A (en) Polypeptide enkephalin analogues - for use as analgesics by intravenous injection
FR2359817A1 (en) Peptide cpds. contg. tyrosine, glycine, phenylalanine and d-amino acid - local anaesthetics, smooth muscle relaxants, adrenergic neutron blockers, beta-stimulants etc.
ATE6504T1 (en) POLYPEPTIDES.
KR890014579A (en) Polypeptide
ES462221A1 (en) Pharmaceutical composition
GB1523812A (en) Polypeptide
HUT36142A (en) Process for preparing basic peptides with vasopressine antagonist activity
NO801061L (en) PEPTIDES WITH TYMOPOIETIN-LIKE ACTIVITY
Lin et al. Stimulation of gastric acid secretion in the dog by the C-terminal penta-, tetra-, and tripeptides of gastrin and their O-methyl esters
ES8707740A1 (en) Vasopressin antagonists.
EP0307662A3 (en) Enkephalin analogs
WAN EFFECT OF UNSATURATED FATTY ACIDS ON
Weaver et al. Morphine antagonism with amiphenazole (2, 4-diamino-5-phenyl-thiazole hydrochloride)

Legal Events

Date Code Title Description
ST Notification of lapse