GB1582528A - Amino pyrimidone derivatives - Google Patents

Amino pyrimidone derivatives Download PDF

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Publication number
GB1582528A
GB1582528A GB4330779A GB4330779A GB1582528A GB 1582528 A GB1582528 A GB 1582528A GB 4330779 A GB4330779 A GB 4330779A GB 4330779 A GB4330779 A GB 4330779A GB 1582528 A GB1582528 A GB 1582528A
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United Kingdom
Prior art keywords
compound
pyridyl
het
formula
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
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GB4330779A
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Smith Kline and French Laboratories Ltd
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Smith Kline and French Laboratories 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 Smith Kline and French Laboratories Ltd filed Critical Smith Kline and French Laboratories Ltd
Priority to GB4330779A priority Critical patent/GB1582528A/en
Publication of GB1582528A publication Critical patent/GB1582528A/en
Expired legal-status Critical Current

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Classifications

    • 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
    • C07D417/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

(54) AMINO PYRIMIDONE DERIVATIVES (71) We, SMITH KLINE & FRENCH LABORATORIES LIMITED, of Mundells, Welwyn Garden City, Hert fordshire, a British Company, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: This invention relates to amino pyrimidone derivatives which are useful as intermediates in the synthesis of certain biologically active pyrinaidones.
Our co-pending cognate British Patent Application No. 53001/75 and 48605/76 (Serial No. 1582527) disclose and claim compounds of formula (I):-
and salts thereof where Het is a 2- or 4imidazolyl group optionally substituted with lower alkyl, halogen, trifluoromethyl or hydroxyl methyl; a 2-pyridyl group optionally substituted with lower alkyl, lower alkoxy, halogen, amino or hydroxy; a 2thiazolyl group, a 3-isothiazolyl group optionally substituted with chlorine or bromine; a 3-( 1,2,5)-thiadiazolyl group optionally substituted with chlorine or bromine; or 2 (5-amino-1,3,4-thiadiazolyl) group; Y is sulphur or a methylene group; Z is hydrogen or lower alkyl; X is oxygen or sulphur; W is methylene, oxygen or sulphur; p and q are such that their sum is from 1 to 4 when W is oxygen or sulphur, or from 0 to 4 when W is methylene; Het' is a 5 or 6-membered heteroaryl group optionally substituted with lower alkyl or lower alkoxy, or it may have a phenyl group or substituted phenyl group fused to it.
Herein lower alkyl and lower alkoxy mean such groups containing up to 4 carbon atoms.
The amino pyrimidone-derivatives of this invention are useful in the preparation of compounds of formula (I) above where W is methylene.
Accordingly the present invention provides a compound of formula (II)
where Z and Het' are as defined with reference to formula (I) above and a is 0 or 1 to 4.
By way of example Het' is a pyridyl, furyl, thienyl, thiazolyl, oxazolyl, isothiazolyl, imidazolyl, pyrimidyl, pyrazinyl or pyridazyl group optionally substituted with lower alkyl, lower alkoxy, or may have a phenyl group or substituted phenyl group fused to it.
Preferably Het' is a 2-furyl, 2-thienyl, 2pyridyl, 3-pyridyl, 4-pyridyl, 2-thiazolyl, 2imidazoyl, 2-pyrimidyl, 2-pyrazinyl or 4pyridazyl group, each of which are optionally substituted with lower alkyl or lower alkoxy.
More preferably Het' is a 2-thienyl, 2pyridyl, 3-pyridyl, 4-pyridyl or 2-thiazolyl.
Most preferably Het' is a 3-pyridyl.
Preferably a is 0.
Preferably Z is hydrogen.
Compounds of formula (11) above can be prepared by reacting the sodium salt of a compound of formula (III):-
where Z, a and Het' are as defined with reference to formula (II) and Et is ethyl, with guanidine.
This reaction can be carried out in a manner analogous to known reactions.
Compounds of formula (III) can be prepared by methods described in co-pending cognate Applications Nos. 53001/75 and.
48605/76 (Serial No. 1582527) and the compounds of formula (II) can be converted into the corresponding compounds of formula (.1) as described in co-pending cognate Applications No. 53001/75 and 48605/76 (Serial No. 1582527).
WHAT WE CLAIM IS:- 1. A compound of formula (II):--
where Z is hydrogen or lower alkyl, a is 0 or 1 to 4 and Het' is a 5 or 6-membered heteroaryl group optionally substituted with lower alkyl or lower alkoxy or may have a phenyl group or substituted phenyl group fused to it.
2. A compound as claimed in claim 1 where Het' is a pyridyl, furyl, thienyl, thiazolyl, oxazolyl, isothiazolyl, imidazolyl, pyrimidyl, pyrazinyl or pyridazyl group, each of which are optionally substituted with lower alkyl, lower alkoxy, or may have a phenyl group or substituted phenyl group fused to it.
3. A compound as claimed in claim 2 where Het' is a 2-furyl, 2-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thiazolyl, 2-imidazoyl, 2-pyrimidyl, 2-pyrazinyl or 4-pyridazyl group optionally substituted with lower alkyl or lower alkoxy.
4. A compound as claimed in claim 3 where Het' is a 2 thienyl, 2-pyridyl, 3pyridyl, 4-pyridyl or 2-thiazolyl group.
5. A compound as claimed in claim 4 where Het' is a 3-pyridyl group.
6. A compound as claimed in any one of claims 1 to 5 where Z is hydrogen.
7. A compound as claimed in any one of claims 1 to 6 where a is 0.
8. A process for preparing a compound as claimed in claim 1 which comprises reacting the sodium salt of a compound of formula (III):-
where Z, a and Het' are as defined with reference to formula (II) and Et is ethyl, with guanidine.
9. A compound as claimed in any one of claims 1 to 7 whenever prepared by a process as claimed in claim 8.
**WARNING** end of DESC field may overlap start of CLMS **.

Claims (9)

  1. **WARNING** start of CLMS field may overlap end of DESC **.
    where Z, a and Het' are as defined with reference to formula (II) and Et is ethyl, with guanidine.
    This reaction can be carried out in a manner analogous to known reactions.
    Compounds of formula (III) can be prepared by methods described in co-pending cognate Applications Nos. 53001/75 and.
    48605/76 (Serial No. 1582527) and the compounds of formula (II) can be converted into the corresponding compounds of formula (.1) as described in co-pending cognate Applications No. 53001/75 and 48605/76 (Serial No. 1582527).
    WHAT WE CLAIM IS:- 1. A compound of formula (II):--
    where Z is hydrogen or lower alkyl, a is 0 or 1 to 4 and Het' is a 5 or 6-membered heteroaryl group optionally substituted with lower alkyl or lower alkoxy or may have a phenyl group or substituted phenyl group fused to it.
  2. 2. A compound as claimed in claim 1 where Het' is a pyridyl, furyl, thienyl, thiazolyl, oxazolyl, isothiazolyl, imidazolyl, pyrimidyl, pyrazinyl or pyridazyl group, each of which are optionally substituted with lower alkyl, lower alkoxy, or may have a phenyl group or substituted phenyl group fused to it.
  3. 3. A compound as claimed in claim 2 where Het' is a 2-furyl, 2-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thiazolyl, 2-imidazoyl, 2-pyrimidyl, 2-pyrazinyl or 4-pyridazyl group optionally substituted with lower alkyl or lower alkoxy.
  4. 4. A compound as claimed in claim 3 where Het' is a 2 thienyl, 2-pyridyl, 3pyridyl, 4-pyridyl or 2-thiazolyl group.
  5. 5. A compound as claimed in claim 4 where Het' is a 3-pyridyl group.
  6. 6. A compound as claimed in any one of claims 1 to 5 where Z is hydrogen.
  7. 7. A compound as claimed in any one of claims 1 to 6 where a is 0.
  8. 8. A process for preparing a compound as claimed in claim 1 which comprises reacting the sodium salt of a compound of formula (III):-
    where Z, a and Het' are as defined with reference to formula (II) and Et is ethyl, with guanidine.
  9. 9. A compound as claimed in any one of claims 1 to 7 whenever prepared by a process as claimed in claim 8.
GB4330779A 1977-03-25 1977-03-25 Amino pyrimidone derivatives Expired GB1582528A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB4330779A GB1582528A (en) 1977-03-25 1977-03-25 Amino pyrimidone derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4330779A GB1582528A (en) 1977-03-25 1977-03-25 Amino pyrimidone derivatives

Publications (1)

Publication Number Publication Date
GB1582528A true GB1582528A (en) 1981-01-07

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Family Applications (1)

Application Number Title Priority Date Filing Date
GB4330779A Expired GB1582528A (en) 1977-03-25 1977-03-25 Amino pyrimidone derivatives

Country Status (1)

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GB (1) GB1582528A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4352933A (en) * 1981-02-06 1982-10-05 Smithkline Beckman Corporation Chemical methods and intermediates for preparing substituted pyrimidinones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4352933A (en) * 1981-02-06 1982-10-05 Smithkline Beckman Corporation Chemical methods and intermediates for preparing substituted pyrimidinones

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