GB1232758A - - Google Patents

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Publication number
GB1232758A
GB1232758A GB1232758DA GB1232758A GB 1232758 A GB1232758 A GB 1232758A GB 1232758D A GB1232758D A GB 1232758DA GB 1232758 A GB1232758 A GB 1232758A
Authority
GB
United Kingdom
Prior art keywords
general formula
amino
diamino
alkyl
alkyl 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
Application number
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 filed Critical
Publication of GB1232758A publication Critical patent/GB1232758A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

1,232,758. 5 - Amino - 6 - chloro - 1H - imidazo[4,5-b]pyrazin-2-ones. MERCK & CO. Inc. 25 Aug., 1969 [31 Aug., 1968], No. 42184/69. Heading C2C. 5 - Amino - 6 - chloro - 1H- imidazo[4,5 - b]- pyrazin-2-ones of the general formula wherein R and X 1 are each a hydrogen atom or a C 1-5 alkyl group, X 2 is a hydrogen atom or a C 1-5 alkyl, C 1-5 alkoxy-C 1-5 alkyl, monocyclic aryl (optionally halo-substituted), pyridyl or R 4 R 5 N-C 1-5 alkyl group, in which R 4 and R 5 are each a C 1-5 alkyl group or R 4 R 5 N is a saturated 5- or 6-membered heterocyclic ring optionally containing an NH or N-C 1-5 alkyl group or an oxygen atom, are prepared by refluxing a solution of a 2,5-diamino-3- (alkoxycarbonylamino or ureido)-6-chloropyrazine of the general formula wherein Y is an amino, C 1-5 alkylamino, di- (C 1-5 alkyl)-amino or C 1-5 alkoxy group. 2,5 - Diamino - 3 - [alkoxycarbonylamino or ureido)-6-chloropyrazines of the second general formula above are prepared by reaction of methyl 3 - amino - 5,6 - dichloropyrazinoate with an amine of the general formula X 1 X 2 CHNHR, alkaline hydrolysis of the resulting methyl 3,5-diamino- 6-chloropyrazinoate of the general formula concomitant decarboxylation and nitration of the 3,5-diamino-6-chloropyrazinoic acid of the general formula so formed, reaction of the resulting 2-nitro-3,5- diamino-6-chloropyrazine of the general formula with (a) a urea of the general formula H 2 NCON(R1) 2 , wherein R<SP>1</SP> is a hydrogen atom or a C 1-5 alkyl group, (b) a chlorocarbonyl compound of the general formula ClCOY, (c) a di- (C 1-5 alkyl)carbonate or (d) an alkali metal cyanate and hydrogenation of the 2-nitro-3- (alkoxycarbonylamino or ureido) - 5 - amino - 6- chloropyrazine of the general formula thus produced in the presence of a catalyst.
GB1232758D 1968-08-31 1969-08-25 Expired GB1232758A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA28996 1968-08-31

Publications (1)

Publication Number Publication Date
GB1232758A true GB1232758A (en) 1971-05-19

Family

ID=4084474

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1232758D Expired GB1232758A (en) 1968-08-31 1969-08-25

Country Status (6)

Country Link
AT (1) AT289813B (en)
BR (1) BR6911906D0 (en)
CH (1) CH517763A (en)
ES (1) ES370874A1 (en)
GB (1) GB1232758A (en)
NL (1) NL6911867A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4414215A (en) * 1981-08-24 1983-11-08 Merck & Co., Inc. N-Acyl derivatives of 6-alkylamino 5-chloro-3-nitropyrazinamines for radiation therapy
US4418062A (en) * 1981-08-24 1983-11-29 Merck & Co., Inc. Amino derivatives of chloro nitro amino pyrazines useful as adjuncts to radiation therapy
EP0096125A1 (en) * 1982-06-09 1983-12-21 Merck & Co. Inc. Amino and amido derivatives of chloro nitro amino and alkylamino pyrazines useful as adjuncts to radiation therapy
US4609659A (en) * 1985-01-16 1986-09-02 Merck & Co., Inc. 2,6-disubstituted derivatives of 3-nitropyrazines useful as adjuncts to radiation therapy
US4709035A (en) * 1982-11-12 1987-11-24 Merck & Co., Inc. 2,6-disubstituted derivatives of 3-nitropyrazines useful as adjuncts to radiation therapy

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4414215A (en) * 1981-08-24 1983-11-08 Merck & Co., Inc. N-Acyl derivatives of 6-alkylamino 5-chloro-3-nitropyrazinamines for radiation therapy
US4418062A (en) * 1981-08-24 1983-11-29 Merck & Co., Inc. Amino derivatives of chloro nitro amino pyrazines useful as adjuncts to radiation therapy
EP0096125A1 (en) * 1982-06-09 1983-12-21 Merck & Co. Inc. Amino and amido derivatives of chloro nitro amino and alkylamino pyrazines useful as adjuncts to radiation therapy
US4709035A (en) * 1982-11-12 1987-11-24 Merck & Co., Inc. 2,6-disubstituted derivatives of 3-nitropyrazines useful as adjuncts to radiation therapy
US4609659A (en) * 1985-01-16 1986-09-02 Merck & Co., Inc. 2,6-disubstituted derivatives of 3-nitropyrazines useful as adjuncts to radiation therapy

Also Published As

Publication number Publication date
AT289813B (en) 1971-05-10
BR6911906D0 (en) 1973-01-18
CH517763A (en) 1972-01-15
NL6911867A (en) 1970-03-03
ES370874A1 (en) 1971-10-16

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees