GB1133406A - Substituted 1-amino phthalazines - Google Patents

Substituted 1-amino phthalazines

Info

Publication number
GB1133406A
GB1133406A GB2938367A GB2938367A GB1133406A GB 1133406 A GB1133406 A GB 1133406A GB 2938367 A GB2938367 A GB 2938367A GB 2938367 A GB2938367 A GB 2938367A GB 1133406 A GB1133406 A GB 1133406A
Authority
GB
United Kingdom
Prior art keywords
group
lower alkyl
amino
substituted
hydrogen
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
GB2938367A
Inventor
David Gordon Parsons
Alan Frederick Turner
Brian George Murray
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.)
Vantorex Ltd
Original Assignee
Vantorex 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
Priority to DE19671695994 priority Critical patent/DE1695994A1/en
Application filed by Vantorex Ltd filed Critical Vantorex Ltd
Priority to GB2938367A priority patent/GB1133406A/en
Publication of GB1133406A publication Critical patent/GB1133406A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • C07D237/30—Phthalazines
    • C07D237/34—Phthalazines with nitrogen atoms directly attached to carbon atoms of the nitrogen-containing ring, e.g. hydrazine radicals
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond

Abstract

1,133,406. Phthalazine derivatives. VANTOREX Ltd. 26 June, 1967, No. 29383/67. Addition to 1,094,044. Heading C2C. Novel compounds of the general formula and quaternary ammonium and acid addition salts thereof, wherein R is a lower alkoxy-lower alkyl group, a phenoxy group, a hydroxy-lower alkoxy group, a lower alkoxy-lower alkoxy group, a di-lower alkyl amino-lower alkyl group, a cyclic saturated organic base-lower alkyl group, a cyclic saturated organic base-lower alkoxy group, a cyclic saturated organic base group, or a di-lower alkyl amino group; wherein R 1 is hydrogen, a lower alkyl group, a phenyl group or a phenyl-lower alkyl group; wherein R 2 is hydrogen, a lower alkyl group or an alkanoyl group; wherein the benzenoid portion of the phthalazine nucleus and/or the phenyl group(s) of the R and/or R 1 substituents when present may be unsubstituted or substituted with one or more halogen atoms or lower alkyl, lower alkoxy, nitro, amino, di-lower alkyl amino, or carboxy groups; and wherein the cyclic saturated organic base when present may be substituted with one or more lower alkyl groups, are prepared by one of the following methods, (a) a hydroxy amine of the formula R 1 -NH-OR 2 is reacted with the compound of the general formula wherein X is a halogen atom, (b) a suitably substituted 1-aminophthalazine wherein R 2 is hydrogen is reacted with a lower alkyl carboxylic anhydride to produce a compound above wherein R 2 is an alkanoyl group, (c) the compounds falling within the general formula wherein the group-OR 3 is a phenoxy group, a hydroxy-lower alkoxy group, a lower alkoxylower alkoxy group, or a cyclic saturated organic base-lower alkoxy group said group being linked to the phthalazine nucleus by the oxygen atom, O; wherein R 1 is hydrogen, a lower alkyl group, a phenyl group or a phenyllower alkyl group; wherein R 2 is hydrogen, a lower alkyl group or an alkanoyl group; wherein the benzenoid portion of the phthalazine nucleus and/or the phenyl group(s) of the R and/or R 1 substituents when present may be unsubstituted or substituted with one or more halogen atoms or lower alkyl, lower alkoxy, nitro, amino, di-lower alkyl amino, or carboxy groups; and wherein the cyclic saturated organic base group when present may be substituted with one or more lower alkyl groups, which process comprises reacting a compound of the formula R 1 -NH-OR 2 with a compound of the formula which may be prepared by reacting a 1,4-dihalophthalazine with a sodium alcoholate or sodium phenolate of formula Na-OR 3 , (d) those compounds falling within the general formula wherein the group R 4 is a cyclic saturated organic base group linked to the phthalazine nucleus by the nitrogen atom, or a di-lower alkyl amino group; wherein R 1 is hydrogen, a lower alkyl group, a phenyl group or a phenyl-lower alkyl group; wherein R 2 is hydrogen, a lower alkyl group or an alkanyl group; wherein the benzenoid portion of the phthalazine nucleus and/or the phenyl group of the R 1 substituent when present may be unsubstituted or substituted but with one or more halogen atoms or lower alkyl, lower alkoxy, nitro, amino, di-lower alkyl amino, or carboxy groups; and wherein the cyclic saturated organic base group may be substituted with one or more lower alkyl groups, are prepared by reacting a substituted hydroxylamine of the formula R 1 -NH-OR 2 with a compound of the formula which may optionally be prepared by reacting a 1,4-diphenoxy-phthalazine with a di-lower alkyl amine or a saturated organic base. The di-phenoxy compound may be prepared by reacting the corresponding di-halo compound with a sodium alcoholate or sodium phenate. Method (c) above is also used to prepare compounds falling within the scope of Patent No. 1,094,044 and having the formula wherein the group -OR 3 is a lower alkoxy group or a di-lower alkyl amino-lower alkoxy group linked to the phthalazine nucleus by the oxygen atom, O, wherein R 1 is hydrogen, a lower alkyl group, a phenyl group or a phenyllower alkyl group; wherein R 2 is hydrogen, a lower alkyl group or an alkanoyl group; and wherein the benzenoid portion of the phthalazine nucleus and/or the phenyl group(s) of the R and/or R 1 substituents when present may be unsubstituted or substituted with one or more halogen atoms or lower alkyl, lower alkoxy nitro, amino, di-lower alkyl-amino. The term lower used above indicates groups containing up to 6 carbon atoms. Pharmaceutical compositions in conventional forms for oral, rectal or parenteral administration and having use as antipyretic, antiinflammatory, hypotensive, bronchodilator, and respiratory stimulant agents comprise an above novel compound and a diluent or carrier therefor. A method of treatment of animals excluding man which comprises administering the above novel compounds is also claimed.
GB2938367A 1967-05-05 1967-06-26 Substituted 1-amino phthalazines Expired GB1133406A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE19671695994 DE1695994A1 (en) 1967-05-05 1967-05-05 Process for the production of phthalazines
GB2938367A GB1133406A (en) 1967-05-05 1967-06-26 Substituted 1-amino phthalazines

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEV0033605 1967-05-05
GB2938367A GB1133406A (en) 1967-05-05 1967-06-26 Substituted 1-amino phthalazines

Publications (1)

Publication Number Publication Date
GB1133406A true GB1133406A (en) 1968-11-13

Family

ID=26002053

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2938367A Expired GB1133406A (en) 1967-05-05 1967-06-26 Substituted 1-amino phthalazines

Country Status (2)

Country Link
DE (1) DE1695994A1 (en)
GB (1) GB1133406A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4370328A (en) 1977-11-03 1983-01-25 Pfizer Inc. Cardiac stimulant 1-(3- or 4-substituted piperidino)phthalazines
US6258812B1 (en) 1997-02-13 2001-07-10 Novartis Ag Phthalazines with angiogenesis inhibiting activity

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4370328A (en) 1977-11-03 1983-01-25 Pfizer Inc. Cardiac stimulant 1-(3- or 4-substituted piperidino)phthalazines
US6258812B1 (en) 1997-02-13 2001-07-10 Novartis Ag Phthalazines with angiogenesis inhibiting activity
US6514974B2 (en) 1997-02-13 2003-02-04 Novartis Ag Pyrido-, pyrimido-, pyridazo- and pyrazo- pyridazines having angiogenesis inhibiting activity

Also Published As

Publication number Publication date
DE1695994A1 (en) 1971-05-19

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