IT1235489B - Angiotensin converting enzyme inhibiting cpds. - Google Patents

Angiotensin converting enzyme inhibiting cpds.

Info

Publication number
IT1235489B
IT1235489B IT8621546A IT2154686A IT1235489B IT 1235489 B IT1235489 B IT 1235489B IT 8621546 A IT8621546 A IT 8621546A IT 2154686 A IT2154686 A IT 2154686A IT 1235489 B IT1235489 B IT 1235489B
Authority
IT
Italy
Prior art keywords
soln
stirred
ch2cl2
prod
cpds
Prior art date
Application number
IT8621546A
Other languages
Italian (it)
Other versions
IT8621546A0 (en
Inventor
Roger Charles Brown
David Hulme Robinson
John Dixon
Original Assignee
Fisons Plc
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 GB858521697A external-priority patent/GB8521697D0/en
Priority claimed from GB858524932A external-priority patent/GB8524932D0/en
Priority claimed from GB858530143A external-priority patent/GB8530143D0/en
Priority claimed from GB868609793A external-priority patent/GB8609793D0/en
Priority claimed from GB868612060A external-priority patent/GB8612060D0/en
Application filed by Fisons Plc filed Critical Fisons Plc
Publication of IT8621546A0 publication Critical patent/IT8621546A0/en
Priority claimed from SU874202059A external-priority patent/RU1804458C/en
Application granted granted Critical
Publication of IT1235489B publication Critical patent/IT1235489B/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/15—Six-membered rings
    • C07D285/16—Thiadiazines; Hydrogenated thiadiazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
    • C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
    • 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
    • C07K5/06086—Dipeptides with the first amino acid being basic
    • 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)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Peptides Or Proteins (AREA)
  • Pyrrole Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

With glyoxylic acid, e.g. in an alkanol. (II) in which n = 1 may be prepd. by reacting (IV) with CH2=(X)COOH. In an example, a soln. of benzenecarbothioic acid hydrazide (2g) and benzyl glyoxylate (2.6g) in EtOH was stirred for 18 hrs. under N2. A stirred mixt. of N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanine (3.1g) and 1-hydroxybenzotriazole (1.7g) in CH2Cl2 (100 ml) was treated with a soln. of the prod. (6.85g) in CH2Cl2. A soln. of dicyclohexylcarbodiimide (2.26g) in CH2Cl2 (20 ml) was added over 20 mins. and the mixt. stirred for 2 days under N2. A soln. of the prod. obtd. (0.16g), pyrrolidine (0.16 ml) and 3A molecular sieves (0.2g) in acetonitrile (3.2 ml) was stirred for 3.5 hrs. A soln. of the prod. obtd. (0.26g) in EtOH was treated with 10% Pd/charcoal (0.1g) and stirred in a pressure vessel under hydrogen at 3 atmospheres for 3 days. The catalyst was filtered off and the filtrate evapd. The residue was triturated with ether to give (Ia), m.pt. 180.5-182 deg.C.
IT8621546A 1985-08-31 1986-08-28 Angiotensin converting enzyme inhibiting cpds. IT1235489B (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
GB858521697A GB8521697D0 (en) 1985-08-31 1985-08-31 Nitrogen & sulphur heterocycles
GB858524932A GB8524932D0 (en) 1985-10-09 1985-10-09 Nitrogen & sulphur heterocycles
GB858530143A GB8530143D0 (en) 1985-12-06 1985-12-06 Nitrogen
GB868609793A GB8609793D0 (en) 1986-04-22 1986-04-22 Nitrogen containing heterocycles
GB868612060A GB8612060D0 (en) 1986-05-17 1986-05-17 Nitrogen containing heterocycles
GB8619943A GB2179655B (en) 1985-08-31 1986-08-15 Angiotensin converting enzyme inhibiting compounds
SU874202059A RU1804458C (en) 1985-08-31 1987-02-09 Method of 1,3,4 -thiadiazole -2- carboxylic acid derivatives or theirs pharmaceutically acceptable salts, esters or amides synthesis

Publications (2)

Publication Number Publication Date
IT8621546A0 IT8621546A0 (en) 1986-08-28
IT1235489B true IT1235489B (en) 1992-09-04

Family

ID=27562736

Family Applications (1)

Application Number Title Priority Date Filing Date
IT8621546A IT1235489B (en) 1985-08-31 1986-08-28 Angiotensin converting enzyme inhibiting cpds.

Country Status (2)

Country Link
GB (1) GB2179655B (en)
IT (1) IT1235489B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NO178294C (en) * 1989-07-24 1996-02-28 Wiggins Teape Group Ltd Process for producing an air-permeable sheet of fiberglass-reinforced thermoplastic material

Also Published As

Publication number Publication date
IT8621546A0 (en) 1986-08-28
GB8619943D0 (en) 1986-09-24
GB2179655B (en) 1989-08-09
GB2179655A (en) 1987-03-11

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Legal Events

Date Code Title Description
TA Fee payment date (situation as of event date), data collected since 19931001

Effective date: 19960830