FR2417506A1 - 2,4-Di:substd.-pyrimidine-5-carboxamide derivs. - useful as neuroleptics for treating psychic disorders (BE 20.8.79) - Google Patents

2,4-Di:substd.-pyrimidine-5-carboxamide derivs. - useful as neuroleptics for treating psychic disorders (BE 20.8.79)

Info

Publication number
FR2417506A1
FR2417506A1 FR7804921A FR7804921A FR2417506A1 FR 2417506 A1 FR2417506 A1 FR 2417506A1 FR 7804921 A FR7804921 A FR 7804921A FR 7804921 A FR7804921 A FR 7804921A FR 2417506 A1 FR2417506 A1 FR 2417506A1
Authority
FR
France
Prior art keywords
och3
oet
neuroleptics
useful
pyrimidine
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.)
Granted
Application number
FR7804921A
Other languages
French (fr)
Other versions
FR2417506B1 (en
Inventor
Jean-Francois Ancher
Bernard Bucher
Thierry Imbert
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.)
Synthelabo SA
Original Assignee
Delalande SA
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 Delalande SA filed Critical Delalande SA
Priority to FR7804921A priority Critical patent/FR2417506A1/en
Priority to GR58323A priority patent/GR66581B/el
Priority to US06/011,752 priority patent/US4250178A/en
Priority to ZA79631A priority patent/ZA79631B/en
Priority to IT20206/79A priority patent/IT1113438B/en
Priority to BE0/193541A priority patent/BE874266A/en
Priority to ES477852A priority patent/ES477852A1/en
Priority to CA321,796A priority patent/CA1096868A/en
Priority to CH159879A priority patent/CH639078A5/en
Priority to LU80937A priority patent/LU80937A1/en
Priority to SE7901493A priority patent/SE446450B/en
Priority to DE19792906461 priority patent/DE2906461A1/en
Priority to AU44392/79A priority patent/AU526298B2/en
Priority to JP1896279A priority patent/JPS54130585A/en
Priority to GB7905890A priority patent/GB2014984B/en
Priority to NL7901333A priority patent/NL7901333A/en
Priority to MX10105779U priority patent/MX6332E/en
Publication of FR2417506A1 publication Critical patent/FR2417506A1/en
Application granted granted Critical
Publication of FR2417506B1 publication Critical patent/FR2417506B1/fr
Granted legal-status Critical Current

Links

Classifications

    • 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
    • C07D239/30—Halogen atoms or nitro radicals
    • 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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • 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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
    • 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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom
    • 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

Landscapes

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

Abstract

Pyrimidine derivs. of formula (I) are new. In (I) NR2R3 is (a) azcridimyl and R, R1=NH2, OCH3, (b) NH (CH2)2NR4R5, (c) U-Q'-pyrrolidin-3-yl)amino, Q' is cyclohexyl and R, R1 as in (a), or Q' is benzyl or 4-fluorobenzyl and R R1 are CH3OCH3 or NH2, OCH3, (d) 1-benzyl-piperidin-4-yl and R, R1 are Z, OCH3, or NH2, OCH7-iso (Z is NH2, CH3, H, CH3O, (CH3)2N or CH3NH), (e) racemic (1-R10-pyrrolidin-2-yl) amino, R10 is CH3 and R, R1 are NH2. OCH3, CH3, OCH3, CH3, EOt, or Et, OEt, or R10 is Et and R, R1 are Z, OCH3, NH2, Z1 (Z1 is ErO, n - or iso-C3H7O), CH3, Z1, Et, OEt, n- or is o-C3H7, OCH3, CH3S, OCH3, or R10 is n-propyl, n-butyl, benzyl or p-fluorobenzyl and R, R1 are NH2, OCH3 or CH3, OCH3, or CH3, OCH3, or R10 is cyclohexylmethyl or allyl and R, R1 are CH3, OCH3. In (I), NR2R3 is (f) the gp. R, R1 are CH3, OCH3 CH3, OEt, (CH3)2N, OCH3 or (CH3)2N, OEt, (g) (1-methylpyrrol-2-yl)methylamino and R1R1 are CH3, OCH3. In (b) NR4R5 is (d) 1,2,3,4-tetrahydroquinoline gp. or anilino and R, R1 are R, R1 =NH2, OCH3, NH2, OEt, CH3, OCH3, CH3S, OCH3 or (CH3)2N, OCH3, (iii)-N(R6) R6, R7 are CH3, H and R, R1=NH2, OCH3, R6, R7 Et, H and R, R1 are NH2, OCH3, CH3, OCH3 or CH3, OEt, or R6R7 are Et, F and R, R1 are CH3, OCH3 or CH3, OEt, (iv) 4-Q-piperazino, Q is phenyl or 4-fluorophenyl and R, R1 are CH3, OCH3, or Q is 2-methoxyphenyl and R, R1 are CH3, OCH3 or NH2, OCH3. (I) are neuroleptics useful for treating psychic disorders. The cpd. with R, R1 = NH2, OCHo and NR2R3-2-(diethylamino) ethylamine has intraperitoneal LD50 in mice 650 mg/kg.
FR7804921A 1978-02-21 1978-02-21 2,4-Di:substd.-pyrimidine-5-carboxamide derivs. - useful as neuroleptics for treating psychic disorders (BE 20.8.79) Granted FR2417506A1 (en)

Priority Applications (17)

Application Number Priority Date Filing Date Title
FR7804921A FR2417506A1 (en) 1978-02-21 1978-02-21 2,4-Di:substd.-pyrimidine-5-carboxamide derivs. - useful as neuroleptics for treating psychic disorders (BE 20.8.79)
GR58323A GR66581B (en) 1978-02-21 1979-02-09
US06/011,752 US4250178A (en) 1978-02-21 1979-02-12 Amides derived from carboxyl-5 pyrimidines
ZA79631A ZA79631B (en) 1978-02-21 1979-02-13 Novel amides derived from carboxyl-5-pyrimidines,the preparation and the therapeutical application thereof
IT20206/79A IT1113438B (en) 1978-02-21 1979-02-15 NEW STARCHES DERIVED FROM PYRIMIDIN-5-CARBOXYLIC ACIDS, THEIR PREPARATION AND THEIR APPLICATION IN THERAPY
LU80937A LU80937A1 (en) 1978-02-21 1979-02-19 NEW AMIDES DERIVED FROM CARBOXYLIC-5-PYRIMIDINIC ACIDS, THEIR PREPARATION AND THEIR APPLICATION IN THERAPEUTICS
CA321,796A CA1096868A (en) 1978-02-21 1979-02-19 Amides derived from carboxyl-5 pyrimidine, the preparation and the therapeutical application thereof
CH159879A CH639078A5 (en) 1978-02-21 1979-02-19 AMIDES DERIVED FROM 5-PYRIMIDINIC CARBOXYLIC ACIDS, THEIR PREPARATION AND MEDICAMENTS CONTAINING THEM.
BE0/193541A BE874266A (en) 1978-02-21 1979-02-19 NEW AMIDES DERIVED FROM CARBOXYLIC-5-PYRIMIDINIC ACIDS, THEIR PREPARATION AND THEIR APPLICATION IN THERAPEUTICS
ES477852A ES477852A1 (en) 1978-02-21 1979-02-19 Amides derived from carboxyl-5 pyrimidines
DE19792906461 DE2906461A1 (en) 1978-02-21 1979-02-20 PYRIMIDINE-5-CARBONIC ACID AMIDE DERIVATIVES, THE PROCESS FOR THEIR MANUFACTURING AND MEDICINAL PRODUCTS CONTAINING SUCH DERIVATIVES
AU44392/79A AU526298B2 (en) 1978-02-21 1979-02-20 Amides derived from carboxyl-5 pyrimidines
JP1896279A JPS54130585A (en) 1978-02-21 1979-02-20 Novel amide derived from carboxyy55pyrimidine and its manufacture
GB7905890A GB2014984B (en) 1978-02-21 1979-02-20 Pyrimidine-5-carboxamides the preparation and the therapeutical application thereof
SE7901493A SE446450B (en) 1978-02-21 1979-02-20 AMID DERIVATIVES OF 5-PYRIMIDINE CARBON ACIDS FOR USE IN PSYCHOLOGICAL DISEASES, AND SET FOR THEIR PREPARATION
NL7901333A NL7901333A (en) 1978-02-21 1979-02-20 NEW 5-PYRIMIDINE CARBONIC ACID AMIDES, THEIR PREPARATION AND THERAPEUTIC USE.
MX10105779U MX6332E (en) 1978-02-21 1979-02-20 PROCEDURE FOR THE OBTAINING OF AMIDES DERIVED FROM CARBOXYLIC-5-PIRIMIDINIC ACIDS

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7804921A FR2417506A1 (en) 1978-02-21 1978-02-21 2,4-Di:substd.-pyrimidine-5-carboxamide derivs. - useful as neuroleptics for treating psychic disorders (BE 20.8.79)

Publications (2)

Publication Number Publication Date
FR2417506A1 true FR2417506A1 (en) 1979-09-14
FR2417506B1 FR2417506B1 (en) 1981-03-06

Family

ID=9204843

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7804921A Granted FR2417506A1 (en) 1978-02-21 1978-02-21 2,4-Di:substd.-pyrimidine-5-carboxamide derivs. - useful as neuroleptics for treating psychic disorders (BE 20.8.79)

Country Status (3)

Country Link
BE (1) BE874266A (en)
FR (1) FR2417506A1 (en)
ZA (1) ZA79631B (en)

Also Published As

Publication number Publication date
FR2417506B1 (en) 1981-03-06
ZA79631B (en) 1980-05-28
BE874266A (en) 1979-08-20

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