GB1323362A - Cyclopeptides derived from polymyxins and their preparation - Google Patents

Cyclopeptides derived from polymyxins and their preparation

Info

Publication number
GB1323362A
GB1323362A GB3763270A GB3763270A GB1323362A GB 1323362 A GB1323362 A GB 1323362A GB 3763270 A GB3763270 A GB 3763270A GB 3763270 A GB3763270 A GB 3763270A GB 1323362 A GB1323362 A GB 1323362A
Authority
GB
United Kingdom
Prior art keywords
leu
dab
formula
pyridyl
polymyxin
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.)
Expired
Application number
GB3763270A
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.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
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 Rhone Poulenc SA filed Critical Rhone Poulenc SA
Publication of GB1323362A publication Critical patent/GB1323362A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
    • C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
    • C07K1/063—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups for alpha-amino functions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
    • C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
    • C07K1/064—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups for omega-amino or -guanidino functions
    • 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
    • C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/50—Cyclic peptides containing at least one abnormal peptide link
    • C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
    • C07K7/60—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation occurring through the 4-amino group of 2,4-diamino-butanoic acid
    • C07K7/62—Polymyxins; Related peptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • 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)
  • 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)
  • Analytical Chemistry (AREA)
  • Peptides Or Proteins (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)

Abstract

1323362 Polymyxin derivatives RHONEPOULENC SA 4 Aug 1970 [5 Aug 1969] 37632/70 Headings C2A and C2C Novel cyclic polypeptides having the general Formula I wherein Y-Z represents one of the amino acid chains D-Leu-Thr, D-Phe-Leu, D-Leu- Leu and D-Leu-Ileu ; G is a radical of Formula II: Py-CH 9 -O-CO- in which Py is pyridyl or pyridyl-N-oxide optionally substituted by a methyl group, Dab represents α,γ-diaminobutyric acid, Thr is threonine, Phe is phenylalanine, Leu is leucine and lieu is isoleucine, the amino acids having the L configuration unless otherwise stated, are prepared by hydrolysing a polymyxin of Formula III wherein K is an n-octanoyl, L-6-methyloctanoyl or 6-methylheptanoyl radical, G and Dab are as above, and either (1) Y-Z is D-Leu-Thr and X is D-Dab or D-Serine, or (2) Y-Z is D-Phe- Leu or D-Leu-Leu and X is Dab, or when K is L-6-methyloctanoyl or 6-methylheptanoyl then Y-Z may be D-Leu-Ileu and X is Dab, and when X is Dab it optionally has a group G on the γ-amino group, by an enzyme which is a protease from B. subtilis A.T.C.C. 9524 or an exocellular protease from any appropriate strain of B. subtilis. The preferred enzymes are subtilisin, nagarse, pronase, colistinase or Alcalase (Registered Trade Mark). The compounds of Formula I are useful as intermediates for synthesizing polymyxin analogues having a modified side chain by reacylating the α-amino group on the Dab with an appropriate acid radical, and subsequently removing the protective groups G from the other amino groups e.g. by hydrogenolysis. The starting materials of Formula III are prepared by reacting a polymyxin e.g. colistin, polymyxin B, with a mixed carbonate of Formula V below suitably in an organic solvent such as dimethyl-formamide at 15‹ to 60‹ C. If desired the pyridyl group may be oxidized to the N-oxide before or after the reaction e.g. with p-nitroperbenzoic acid. Compounds having the general Formula V wherein Py is as hereinbefore defined and T is phenyl, substituted phenyl (e.g. p-nitrophenyl; 2,4,5-trichlorophenyl) or a heterocyclic radical (e.g. 8-quinolinyl or 2,5-dioxopyrrolidin-1-yl) are prepared by reacting an alcohol of formula Py-CH 2 -OH with a chloroformate of formula Cl-CO-O-T, and if required oxidizing the pyridyl radical to pyridyl-N-oxide, e.g. with p-nitroperbenzoic acid.
GB3763270A 1969-08-05 1970-08-04 Cyclopeptides derived from polymyxins and their preparation Expired GB1323362A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR6926912A FR2055903A5 (en) 1969-08-05 1969-08-05

Publications (1)

Publication Number Publication Date
GB1323362A true GB1323362A (en) 1973-07-11

Family

ID=9038672

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3763270A Expired GB1323362A (en) 1969-08-05 1970-08-04 Cyclopeptides derived from polymyxins and their preparation

Country Status (12)

Country Link
JP (1) JPS4829149B1 (en)
AT (2) AT299977B (en)
BE (1) BE754411A (en)
CA (1) CA950391A (en)
CH (1) CH513817A (en)
CS (1) CS152369B2 (en)
DE (1) DE2038997A1 (en)
FR (1) FR2055903A5 (en)
GB (1) GB1323362A (en)
NL (1) NL164900C (en)
SE (1) SE369713B (en)
ZA (2) ZA705377B (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2128617A (en) * 1982-10-06 1984-05-02 Martti Vaara Polypeptides for use in antibacterial therapy
WO2008017734A1 (en) 2006-08-11 2008-02-14 Northern Antibiotics Oy Polymyxin derivatives and uses thereof
US7807637B2 (en) 2006-08-11 2010-10-05 Northern Antibiotics Oy Polymyxin derivatives and uses thereof
US8193148B2 (en) 2008-02-08 2012-06-05 Northern Antibiotics Ltd. Short fatty acid tail polymyxin derivatives and uses thereof
US8329645B2 (en) 2008-02-08 2012-12-11 Northern Antibiotics Ltd. Polymyxin derivatives and uses thereof
US9096649B2 (en) 2008-02-08 2015-08-04 Northern Antibiotics Ltd. Polymyxin derivatives and uses thereof
RU2675819C1 (en) * 2015-01-15 2018-12-25 Нозерн Антибиотикс Ой Polymyxin derivatives and their use

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2128617A (en) * 1982-10-06 1984-05-02 Martti Vaara Polypeptides for use in antibacterial therapy
WO2008017734A1 (en) 2006-08-11 2008-02-14 Northern Antibiotics Oy Polymyxin derivatives and uses thereof
US7807637B2 (en) 2006-08-11 2010-10-05 Northern Antibiotics Oy Polymyxin derivatives and uses thereof
US8680234B2 (en) 2006-08-11 2014-03-25 Northern Antibiotics Oy Polymyxin derivatives and uses thereof
US9067974B2 (en) 2006-08-11 2015-06-30 Northern Antibiotics Oy Polymyxin derivatives and uses thereof
US8193148B2 (en) 2008-02-08 2012-06-05 Northern Antibiotics Ltd. Short fatty acid tail polymyxin derivatives and uses thereof
US8329645B2 (en) 2008-02-08 2012-12-11 Northern Antibiotics Ltd. Polymyxin derivatives and uses thereof
US8642535B2 (en) 2008-02-08 2014-02-04 Northern Antibiotics Ltd. Short fatty acid tail polymyxin derivatives and uses thereof
US9090669B2 (en) 2008-02-08 2015-07-28 Northern Antibiotics Ltd. Short fatty acid tail polymyxin derivatives and uses thereof
US9096649B2 (en) 2008-02-08 2015-08-04 Northern Antibiotics Ltd. Polymyxin derivatives and uses thereof
RU2675819C1 (en) * 2015-01-15 2018-12-25 Нозерн Антибиотикс Ой Polymyxin derivatives and their use

Also Published As

Publication number Publication date
CH513817A (en) 1971-10-15
FR2055903A5 (en) 1971-05-14
SE369713B (en) 1974-09-16
JPS4829149B1 (en) 1973-09-07
CA950391A (en) 1974-07-02
NL7011150A (en) 1971-02-09
BE754411A (en) 1971-02-04
ZA705377B (en) 1971-04-28
ZA705378B (en) 1971-04-28
NL164900B (en) 1980-09-15
AT299977B (en) 1972-07-10
DE2038997A1 (en) 1971-02-18
CS152369B2 (en) 1973-12-19
AT295746B (en) 1972-01-10
NL164900C (en) 1981-02-16

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Legal Events

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