GB920412A - Pyrimidine derivatives and the manufacture thereof - Google Patents

Pyrimidine derivatives and the manufacture thereof

Info

Publication number
GB920412A
GB920412A GB12355/58A GB1235558A GB920412A GB 920412 A GB920412 A GB 920412A GB 12355/58 A GB12355/58 A GB 12355/58A GB 1235558 A GB1235558 A GB 1235558A GB 920412 A GB920412 A GB 920412A
Authority
GB
United Kingdom
Prior art keywords
methoxy
hydrogen
compounds
formula
carbon atoms
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
GB12355/58A
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation 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
Application filed by Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB12355/58A priority Critical patent/GB920412A/en
Priority to CH7217059A priority patent/CH451944A/en
Priority to CH121368A priority patent/CH457451A/en
Priority to BE577871A priority patent/BE577871A/en
Priority to FR837267A priority patent/FR495M/fr
Publication of GB920412A publication Critical patent/GB920412A/en
Expired legal-status Critical Current

Links

Classifications

    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
    • F16C—SHAFTS; FLEXIBLE SHAFTS; ELEMENTS OR CRANKSHAFT MECHANISMS; ROTARY BODIES OTHER THAN GEARING ELEMENTS; BEARINGS
    • F16C3/00—Shafts; Axles; Cranks; Eccentrics
    • F16C3/04—Crankshafts, eccentric-shafts; Cranks, eccentrics
    • F16C3/06—Crankshafts
    • F16C3/14—Features relating to lubrication
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide

Landscapes

  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Mechanical Engineering (AREA)
  • Ocean & Marine Engineering (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0920412/IV(a)/1> wherein R1 is an alkyl group of 1-4 carbon atoms, R2 is hydrogen, isopropyl, an alkyl group of 4-6 carbon atoms or benzyl and R3, R4 and R5 are hydrogen or halogen e.g. bromine; when at least one of R3, R4 and R5 is halogen R2 may also be n-propyl. The compounds are prepared by formylating a compound of the formula <FORM:0920412/IV(a)/2> wherein R6 has the values of R2 other than hydrogen and R7 is an alkyl group of 1-4 carbon atoms, condensing the product with guanidine to give a 2-amino-4-hydroxy-5benzyl-pyrimidine derivative, chlorinating e.g. with POCl3 and aminating. Compounds wherein R2 is hydrogen are made by hydrogenolysis of a compound wherein R2 is a benzyl group. Compounds wherein one or more of R3, R4 and R5 are halogen atoms may be prepared by halogenating, e.g. brominating, the corresponding unsubstituted compound. Hydrocinnamic esters of the formula II used as starting materials namely 3-methoxy-4isopropoxy-, 3-methoxy-4-butoxy-, 3-methoxy4-isoamyloxy-, 3-methoxy-4-propoxy-5-bromoand 3 - methoxy - 4 - butoxy-5-bromo-, hydrocinnamic acid ethyl esters are made by alkylating vanillin, or the appropriately substituted vanillin, in the 4-position, condensing the 3methoxy-4-alkoxy-benzaldehyde (or bromobenzaldehyde) obtained with malonic acid, esterifying the resulting corresponding substituted cinnamic acid to give the ethyl ester and reducing catalytically. Specifications 598,514, 671,926, 671,927 and 734,801 are referred to.
GB12355/58A 1958-04-18 1958-04-18 Pyrimidine derivatives and the manufacture thereof Expired GB920412A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
GB12355/58A GB920412A (en) 1958-04-18 1958-04-18 Pyrimidine derivatives and the manufacture thereof
CH7217059A CH451944A (en) 1958-04-18 1959-04-17 Process for the preparation of pyrimidine derivatives
CH121368A CH457451A (en) 1958-04-18 1959-04-17 Process for the preparation of pyrimidine derivatives
BE577871A BE577871A (en) 1958-04-18 1959-04-18 Pyrimidine derivatives and their preparation
FR837267A FR495M (en) 1958-04-18 1960-08-30

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB12355/58A GB920412A (en) 1958-04-18 1958-04-18 Pyrimidine derivatives and the manufacture thereof

Publications (1)

Publication Number Publication Date
GB920412A true GB920412A (en) 1963-03-06

Family

ID=10002999

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12355/58A Expired GB920412A (en) 1958-04-18 1958-04-18 Pyrimidine derivatives and the manufacture thereof

Country Status (4)

Country Link
BE (1) BE577871A (en)
CH (2) CH457451A (en)
FR (1) FR495M (en)
GB (1) GB920412A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2249532A1 (en) * 1971-10-12 1973-04-26 Wellcome Found PROCESS FOR THE PREPARATION OF 2,4-DIAMINO-5-BENZYLPYRIMIDINES

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3603577A1 (en) * 1986-02-06 1987-08-13 Joachim K Prof Dr Seydel NEW SUBSTITUTED 2,4-DIAMINO-5-BENZYLPYRIMIDINE, THEIR PRODUCTION AND USE THEREOF AS A MEDICINE WITH ANTIBACTERIAL EFFECTIVENESS

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2249532A1 (en) * 1971-10-12 1973-04-26 Wellcome Found PROCESS FOR THE PREPARATION OF 2,4-DIAMINO-5-BENZYLPYRIMIDINES

Also Published As

Publication number Publication date
CH451944A (en) 1968-05-15
FR495M (en) 1961-05-08
BE577871A (en) 1959-08-17
CH457451A (en) 1968-06-15

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