IE45427L - PYRROLO [3,2-f] QUINAZOLINE-1, 3-DIAMINE AND RELATED¹COMPOUNDS - Google Patents

PYRROLO [3,2-f] QUINAZOLINE-1, 3-DIAMINE AND RELATED¹COMPOUNDS

Info

Publication number
IE45427L
IE45427L IE771345A IE134577A IE45427L IE 45427 L IE45427 L IE 45427L IE 771345 A IE771345 A IE 771345A IE 134577 A IE134577 A IE 134577A IE 45427 L IE45427 L IE 45427L
Authority
IE
Ireland
Prior art keywords
methyl
phenyl
quinolinyl
pyridinyl
trifluoromethyl
Prior art date
Application number
IE771345A
Other versions
IE45427B1 (en
Original Assignee
American Home Prod
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 American Home Prod filed Critical American Home Prod
Publication of IE45427L publication Critical patent/IE45427L/en
Publication of IE45427B1 publication Critical patent/IE45427B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
    • C07D209/34—Oxygen atoms in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Nutrition Science (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The present invention provides a compound if the general formula: or a non-toxic acid addition salt thereof, wherein: (a) X is hydrogen and Y is -CH2R or -R1 wherein: R is hydrogen; methyl; ethyl; n-propyl; i-propyl; n-butyl; i-butyl; n-pentyl; n-hexyl; 2-methyl-1-propenyl; cyclobutyl; cyclopentyl; cyclohexyl; 2-phenylethyl; 2-phenylvinyl; phenyl; phenyl monosubstituted in the 2-, 3-, or 4-position by chlorine, bromine, iodine, fluorine, trifluoromethyl, methyl, ethyl, n-propyl, i-prophyl, n-butyl, i-butyl, t-butyl, methoxy, ethoxy, n-propoxy, trifluoromethoxy, cyano, methylsulfonyl, acetyl, propionyl, methlthio, ethylthio, carbethoxy, carbonyl, sodium carboxy, or potassium carboxy; phenyl monsubstituted in the 3-position by amino or nitro; phenyl disubstituted in the 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, or 3,5-positions by methyl, ethyl, n-propyl, methoxy, ethoxy, n-propoxy, chlorine, bromine, iodine, or fluorine; phenyl trisubstituted in the 2,4,6- or 3,4,5-positions by methyl, ethyl, methoxy, or ethoxy; 2,3,5,6tetramethylphenyl; 3,4-(methylene dioxy)phenyl; 1-naphthalenyl; 2-naphthalenyl; 2-methyl-1-naphthalenyl; 1-bromo-2-naphthalenyl; 2-pyridinyl; 3-pyridinyl; 4-pyridinyl; 2-quinolinyl; 8-quinolinyl; 2-thienyl; 3-thienyl; 4-thiazolyl; 3,5-dimethyl-4-isoxazolyl; tetrahydro-2-furanyl; or benzo(B)thein-3-yl; and R1 is hydrogen; phenyl monosubstituted in the 2- or 4position by amino, nitro, cyano, acetyl, propionyl, methylsulfonyl, trifluoromethyl or carbethoxy: 2,4-dinitrophenyl; 2,4-diamino-phenyl; 2-cyano-4-nitrophenyl; 2-cyano-4-aminophenyl; 3-methyl-4-nitrophenyl; 3-methyl-4-aminophenyl; 2-trifluoromethyl-4-nitro-phenyl; 2-trifluoromethyl-4-aminophenyl; 2-thiazolyl; 2-pyridinyl; 5-nitro-2-pyridinyl; 2-pyrimidinyl; 2-pyrazinyl; 2-quinolinyl; 4-quinolinyl, 4-methyl-2-quinolinyl; 7-chloro-4-quinolinyl; 7-trifluoromethyl-4-quinolinyl; 2-methyl-4-quinolinyl; 3methyl-2-quinoxalinyl; 2-phenyl-4-quinolinyl; or 2-benzothiazolyl; and (b) X is methyl, phenyl, or chlorine: and Y is hydrogen, methyl, benzyl, 3-cyanobenzyl, 4-cyanobenzyl, or 2,5-dimethylbenzyl; provided that when X is phenyl, Y may only be hydrogen or methyl, and when X is chlorine, Y may only be benzyl. The compounds inhibit the growth of bacteria in vitro as demonstrated in a standard tube dilution test employing seed agar or Wellcotest Sensitivity. In addition the compounds exhibit in vitro antifolic acid activity, as demonstrated by the inhibition of Streptoccus faecalis ATCC 8043 grown in a folic acid medium. [CA1093555A]
IE1345/77A 1976-07-09 1977-06-29 Pyrrold 3,2if quinazoline-1,3-diamine and related compounds IE45427B1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US70400276A 1976-07-09 1976-07-09
US70400176A 1976-07-09 1976-07-09
GB5382176 1976-12-23
US78498777A 1977-04-06 1977-04-06

Publications (2)

Publication Number Publication Date
IE45427L true IE45427L (en) 1978-10-06
IE45427B1 IE45427B1 (en) 1982-08-25

Family

ID=27449036

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1345/77A IE45427B1 (en) 1976-07-09 1977-06-29 Pyrrold 3,2if quinazoline-1,3-diamine and related compounds

Country Status (13)

Country Link
JP (1) JPS539796A (en)
AU (1) AU507828B2 (en)
BE (1) BE856647A (en)
CA (1) CA1093555A (en)
CH (1) CH634069A5 (en)
DE (1) DE2731039A1 (en)
DK (1) DK309977A (en)
FR (1) FR2357563A1 (en)
IE (1) IE45427B1 (en)
IN (1) IN147488B (en)
MX (1) MX5133E (en)
NL (1) NL7707658A (en)
PH (1) PH13539A (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PT99514B (en) * 1990-11-14 1999-04-30 Chiron Corp PROCESS OF PREPARATION OF COMPOUNDS FOR THE TREATMENT OF FUNGIC INFECTIONS
KR100810468B1 (en) * 2001-10-10 2008-03-07 씨제이제일제당 (주) 1H-indole derivatives as a highly selective cyclooxygenase-2 inhibitor
US7262297B2 (en) * 2003-05-15 2007-08-28 Hoffmann-La Roche Inc. Diaminopyrroloquinazolines compounds as protein tyrosine phosphatase inhibitors
US11077109B2 (en) * 2017-08-01 2021-08-03 The Trustees Of Princeton University Compounds having antibacterial activity and methods of use

Also Published As

Publication number Publication date
IN147488B (en) 1980-03-15
IE45427B1 (en) 1982-08-25
NL7707658A (en) 1978-01-11
AU507828B2 (en) 1980-02-28
JPS6254111B2 (en) 1987-11-13
JPS539796A (en) 1978-01-28
MX5133E (en) 1983-03-28
CA1093555A (en) 1981-01-13
CH634069A5 (en) 1983-01-14
FR2357563B1 (en) 1983-03-11
PH13539A (en) 1980-06-26
DK309977A (en) 1978-01-10
BE856647A (en) 1978-01-09
DE2731039A1 (en) 1978-01-19
FR2357563A1 (en) 1978-02-03
AU2668777A (en) 1979-01-04

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