GB1178329A - N-[delta-(6-Purinylthio) Valeryl] Amino Acids and derivatives thereof, and a method of producing the same - Google Patents

N-[delta-(6-Purinylthio) Valeryl] Amino Acids and derivatives thereof, and a method of producing the same

Info

Publication number
GB1178329A
GB1178329A GB27367/67A GB2736767A GB1178329A GB 1178329 A GB1178329 A GB 1178329A GB 27367/67 A GB27367/67 A GB 27367/67A GB 2736767 A GB2736767 A GB 2736767A GB 1178329 A GB1178329 A GB 1178329A
Authority
GB
United Kingdom
Prior art keywords
amino acid
purinylthio
valeryl
general formula
ester
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
GB27367/67A
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.)
Spofa Vereinigte Pharma Werke
Original Assignee
Spofa Vereinigte Pharma Werke
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 Spofa Vereinigte Pharma Werke filed Critical Spofa Vereinigte Pharma Werke
Publication of GB1178329A publication Critical patent/GB1178329A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/36—Sulfur atom
    • C07D473/38—Sulfur atom attached in position 6

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,178,329. N - [# - (6 - Purinylthio) - valeryl]- amino acid derivatives. SPOFA, UNITED PHARMACEUTICAL WORKS. 14 June, 1967 [1 July, 1966], No. 27367/67. Heading C2C. Novel N - [8 - (6 - purinylthio) - valeryl]- amino acid derivatives of the general formula wherein n is 0 or an integer from 1 to 5; R is a C 1-8 straight or branch chain alkoxy or hydroxy group or a residue of a peptidically bound amino acid or dipeptide having the carboxyl group(s) either free or esterified with an alcohol containing a straight or branched carbon chain with 1-7 carbon atoms, wherein said residues, so far as they contain an asymmetric carbon atom, can be optically active or racemic; Y is hydrogen, or a C 1-5 alkyl, phenyl, benzyl, α-hydroxybenzyl, 3-indolyl, 3-indolylmethyl, -CH 2 OH, -CH 2 SH, -(CH 2 ) m SCH 3 , -(CH 2 ) m COR 1 , or group, wherein m is an integer from 1 to 3 and R 1 is an alkoxy group with a straight or branched carbon chain having 1-8 carbon atoms, are prepared, when R is a C 1-8 alkoxy group, by condensation of a 6-(4-carboxybutyl)-thiopurine derivative and an amino acid ester of the respective general formulµ wherein X is chlorine or -N 3 and R 2 is an alkoxy group containing a straight or branched carbon chain with 1-8 carbon atoms; or, when R is a hydroxy group, by saponification with alkali of the resulting N-[#-(6-purinylthio)-valeryl]- amino acid derivative of the first general formula above wherein R is a C 1-8 alkoxy group; or, when R 1 is a residue of a peptidically bound amino acid or dipeptide, by reaction of said resulting amino acid derivative with hydrazine hydrate to form the corresponding N-[#-(6- purinylthio)-valeryl]-amino acid hydrazide, reaction of said hydrazide with nitrous acid to form the corresponding N-[#-(6-purinylthio)- valeryl]-amino acid azide and subsequent condensation with an amino acid ester of the third general formula above to give an ester of a dipeptide of the first general formula above, which can be alkali-saponified to the corresponding free acid and the latter optionally converted to a tripeptide ester of the first general formula above by reaction with an amino acid ester of the third general formula above in the presence of N,N<SP>1</SP>-dicyclohexyl carbodiimide, which ester can in turn be alkali-saponified to the corresponding free acid.
GB27367/67A 1966-07-01 1967-06-14 N-[delta-(6-Purinylthio) Valeryl] Amino Acids and derivatives thereof, and a method of producing the same Expired GB1178329A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CS443666 1966-07-01

Publications (1)

Publication Number Publication Date
GB1178329A true GB1178329A (en) 1970-01-21

Family

ID=5387083

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27367/67A Expired GB1178329A (en) 1966-07-01 1967-06-14 N-[delta-(6-Purinylthio) Valeryl] Amino Acids and derivatives thereof, and a method of producing the same

Country Status (12)

Country Link
US (1) US3567705A (en)
JP (1) JPS4832119B1 (en)
AT (1) AT274000B (en)
BE (1) BE700727A (en)
CH (1) CH501652A (en)
DE (1) DE1695744C3 (en)
DK (1) DK118136B (en)
FI (1) FI48737C (en)
GB (1) GB1178329A (en)
NL (1) NL144615B (en)
SE (3) SE353715B (en)
YU (1) YU33829B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4011221A (en) * 1974-08-22 1977-03-08 Funai Pharmaceutical Industries, Ltd. S-inosylcysteine and a process for producing the same

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4180576A (en) * 1975-09-16 1979-12-25 Commonwealth Scientific Industrial Research Organization Purines useful for the potentiation of antibiotics
CS249576B1 (en) * 1984-12-22 1987-04-16 Antonin Cerny 6-purinyl n-(2-chlorethyl)carbamate and thiocarbamate and method of their production
US5120740A (en) * 1989-11-03 1992-06-09 Wisconsin Alumni Research Foundation Prodrugs of 6-mercaptopurine and 6-thioguanine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4011221A (en) * 1974-08-22 1977-03-08 Funai Pharmaceutical Industries, Ltd. S-inosylcysteine and a process for producing the same

Also Published As

Publication number Publication date
US3567705A (en) 1971-03-02
SE339473B (en) 1971-10-11
JPS4832119B1 (en) 1973-10-04
DK118136B (en) 1970-07-13
BE700727A (en) 1967-12-01
DE1695744A1 (en) 1972-04-20
FI48737C (en) 1974-12-10
NL6709151A (en) 1968-01-02
FI48737B (en) 1974-09-02
NL144615B (en) 1975-01-15
SE353715B (en) 1973-02-12
YU33829B (en) 1978-06-30
DE1695744C3 (en) 1981-09-24
CH501652A (en) 1971-01-15
YU130167A (en) 1977-12-31
SE353716B (en) 1973-02-12
AT274000B (en) 1969-09-10
DE1695744B2 (en) 1980-09-11

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