GB1360312A - N-substituted derivatives of bleomycins - Google Patents

N-substituted derivatives of bleomycins

Info

Publication number
GB1360312A
GB1360312A GB1958572A GB1958572A GB1360312A GB 1360312 A GB1360312 A GB 1360312A GB 1958572 A GB1958572 A GB 1958572A GB 1958572 A GB1958572 A GB 1958572A GB 1360312 A GB1360312 A GB 1360312A
Authority
GB
United Kingdom
Prior art keywords
bleomycins
hydrogen
amino
alkyl
group
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
GB1958572A
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.)
Nippon Kayaku Co Ltd
Original Assignee
Nippon Kayaku Co 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 JP2755371A external-priority patent/JPS5010841B1/ja
Priority claimed from JP7543071A external-priority patent/JPS5031122B2/ja
Application filed by Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd
Publication of GB1360312A publication Critical patent/GB1360312A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D333/40—Thiophene-2-carboxylic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
    • C07G11/00—Antibiotics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
    • C07K9/001—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure
    • C07K9/003—Peptides being substituted by heterocyclic radicals, e.g. bleomycin, phleomycin

Abstract

1360312 N-substituted bleomycin derivatives NIPPON KAYAKU KK 27 April 1972 [28 April 1971 29 Sept 1971] 19585/72 Heading C2A The invention comprises bleomycins showing no definite melting, decomposition or boiling points and inhibiting gram-positive and gramnegative bacteria and having anti-tumour activity, the bleomycins being soluble in water and aqueous methanol; forming salts with acids and chelating with copper, giving positive reactions in Pauly, Ehrlich, Dragendorff and permanganate tests but negative Molisch, Biuret, Elson-Morgan, Maltol, Fehling, Tollens, Anthrone and ferric chloride reactions, having infra-red absorption bands at the following wave numbers (cm.<SP>-1</SP>) 1040-1075, 1710-1735, 1625-1680, 2910-2940 and being further characterized in that they give L-threonine; # - amino - # - (4 - amino - 6 - carboxy - 5- methyl - pyrimidine - 2 - yl) - propionic acid; 4 - amino - 3 - hydroxy - 2 - methyl - n - valeric acid; # - hydroxyhistidine ; L - # - aminoalanine; L - gulose; 3 - 0 - carbamoyl - D - maunose; 2<SP>1 </SP>- (2 - aminoethyl) - 2,4<SP>1</SP> - bithiazole - 4- carboxylic acid and each amino component compound corresponding to the side chain portion upon acid hydrolysis, and said bleomycins having a partial hydrolysate structure represented by the Formula I wherein P is -NH-(CH 2 ) 3 -NH-, wherein R is hydrogen except where Q represents R or -SO 2 R, a saturated or unsaturated, straight or branched chain alkyl group, or a cycloalkyl, phenyl, naphthyl, aralkyl or heterocyclic group, these groups being optionally substituted, R<SP>2</SP> is an alkyl group, R<SP>3</SP> is hydrogen, a C 1 -C 3 alkyl group or a methyne group, R<SP>4</SP> is hydrogen, a C 1 -C 3 alkyl or nitro group and n is an integer of from 1 to 7. A process for producing N-substituted derivatives of bleomycins comprises reacting 3-aminopropylaminobleomycin, 3 - (N - 4 - aminobutyl)aminopropylaminobleomycin or 3 - (N - methyl - N - 3- aminopropyl)aminopropylaminobleomycin with a compound of formula R-Y wherein R is hydrogen (except when R represents -X or -SO 2 X), a saturated or unsaturated, straight chain or branched chain alkyl, cycloalkyl, phenyl, naphthyl, aralkyl or heterocyclic group, these groups being optionally substituted and Y is carboxyl or a reactive derivative thereof, -X wherein X is halogen, -SO 2 X, NCO- or wherein R<SP>2</SP> is alkyl. The reaction may be carried out in a solvent consisting of water, methanol, ethanol, acetone or a mixture thereof. The reaction may be carried out at a temperature of 10 to 25‹ C. in the presence of pyridine, sodium bicarbonate and triethylamine. The bleomycins are believed to have the formula wherein P and Q are as defined above.
GB1958572A 1971-04-28 1972-04-27 N-substituted derivatives of bleomycins Expired GB1360312A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2755371A JPS5010841B1 (en) 1971-04-28 1971-04-28
JP7543071A JPS5031122B2 (en) 1971-09-29 1971-09-29

Publications (1)

Publication Number Publication Date
GB1360312A true GB1360312A (en) 1974-07-17

Family

ID=26365487

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1958572A Expired GB1360312A (en) 1971-04-28 1972-04-27 N-substituted derivatives of bleomycins

Country Status (7)

Country Link
CA (1) CA982122A (en)
CH (2) CH577465A5 (en)
CS (1) CS167982B2 (en)
DE (1) DE2220766C3 (en)
FR (1) FR2134653B1 (en)
GB (1) GB1360312A (en)
NL (1) NL150802B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4057618A (en) * 1976-04-30 1977-11-08 University Patents, Inc. Radioiodinated bleomycin
JPS58116497A (en) * 1981-12-29 1983-07-11 Microbial Chem Res Found Aminopropylaminobleomycin derivative and its preparation

Also Published As

Publication number Publication date
CA982122A (en) 1976-01-20
DE2220766A1 (en) 1972-11-16
DE2220766C3 (en) 1978-08-24
NL150802B (en) 1976-09-15
CS167982B2 (en) 1976-05-28
CH575912A5 (en) 1976-05-31
CH577465A5 (en) 1976-07-15
NL7205753A (en) 1972-10-31
AU4153072A (en) 1973-06-14
FR2134653B1 (en) 1975-12-26
DE2220766B2 (en) 1978-01-12
FR2134653A1 (en) 1972-12-08

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Legal Events

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