GB1322930A - Benzimidazo 2,1-b quinazolin derivatives as immuno suppressants - Google Patents

Benzimidazo 2,1-b quinazolin derivatives as immuno suppressants

Info

Publication number
GB1322930A
GB1322930A GB5562170A GB5562170A GB1322930A GB 1322930 A GB1322930 A GB 1322930A GB 5562170 A GB5562170 A GB 5562170A GB 5562170 A GB5562170 A GB 5562170A GB 1322930 A GB1322930 A GB 1322930A
Authority
GB
United Kingdom
Prior art keywords
alkyl
carboalkoxy
compounds
carbonyl
alkoxy
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
GB5562170A
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.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
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 Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of GB1322930A publication Critical patent/GB1322930A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic 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
    • C07D487/04Ortho-condensed systems

Landscapes

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

Abstract

1322930 Benzimidazo[2,1-b]quinazolinones ELI LILLY & CO 23 Nov 1970 [24 Nov 1969] 55621/70 Heading C2C The invention comprises compounds of formula wherein R<SP>6</SP> ... R<SP>9</SP> and R<SP>11</SP> ... R<SP>14</SP> are each H, halogen, C 1-4 alkyl or alkoxy, NO 2 , NH 2 , carboalkoxy or CF 3 , or a pair of adjacent R groups may form a fused benzene ring; and R<SP>10</SP> is H, C 3-5 epoxyalkyl, -(CH 2 ) p -Z or -(CH 2 ) n CO-Y, where p is 1-4, Z is C 1-4 alkoxy, CO 2 H, carboalkoxy or di-(C 1-4 alkyl) amino, n is 0-4 and Y is carboxy-C 1-4 -alkyl, carboalkoxy-C 1-4 -alkyl, Ph or naphthyl (either of which is optionally substituted by C 1-4 alkoxy, halogen, NO 2 , NH 2 , CO 2 H or carboalkoxy), C 1-4 - alkylphenyl or trifluoromethylphenyl, with the limitations that when Y is carboxy-C 1-4 -alkyl or carboalkoxy-C 1-4 -alkyl, n is 0 or 1 and when Y is naphthyl or substituted naphthyl, n is 0; provided that when R<SP>10</SP> is H at least one of R<SP>6</SP> ... R<SP>9</SP> and R<SP>11</SP> ... R<SP>14</SP> is other than H, R<SP>7</SP>, R<SP>12</SP> and R<SP>13</SP> and one of R<SP>8</SP> and R<SP>10</SP> is Me, and any of R<SP>6</SP> ... R<SP>14</SP> is Me when any other of R<SP>6</SP> ... R<SP>14</SP> is other than H or Me. Also described are compounds wherein R<SP>10</SP> is C 1-12 alkyl, C 3-5 alkenyl, C 2-16 alkanoyl, benzyl, (C 3-10 cycloalkane) carbonyl, (C 7-12 bicycloalkane)carbonyl, or (C 7-12 bicycloalkene)carbonyl. In examples, these compounds are prepared by (1) reacting together a 2-X-benzimidazole where X is NH 2 , Cl, SH or SMe, with an anthranilic acid, ester or acid chloride, or (2) reacting a compound where R<SP>10</SP> is H (or its sodio-derivative) with an R<SP>10</SP>-halide or -sulphate. 2,4,7 - Trichloro - 5,6 - dimethylbenzimidazole is prepared by reacting 2-mercapto-5,6-dimethylbenzimidazole with Cl 2 . Immunosuppressant compositions for parenteral administration comprise compounds of the above formula as broadly described above, subject to the given limitations on Y, and to further limitations regarding the number of substituent groups in general, and the number of Me or Cl groups in particular, which may be present, but the proviso is not applicable.
GB5562170A 1969-11-24 1970-11-23 Benzimidazo 2,1-b quinazolin derivatives as immuno suppressants Expired GB1322930A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US87957969A 1969-11-24 1969-11-24

Publications (1)

Publication Number Publication Date
GB1322930A true GB1322930A (en) 1973-07-11

Family

ID=25374430

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5562170A Expired GB1322930A (en) 1969-11-24 1970-11-23 Benzimidazo 2,1-b quinazolin derivatives as immuno suppressants

Country Status (15)

Country Link
US (1) US3669969A (en)
JP (1) JPS5026560B1 (en)
AT (1) AT310758B (en)
BE (1) BE759337A (en)
CA (1) CA974992A (en)
CH (1) CH560216A5 (en)
DE (1) DE2058185A1 (en)
ES (1) ES385683A1 (en)
FR (1) FR2073408B1 (en)
GB (1) GB1322930A (en)
IE (1) IE34676B1 (en)
IL (1) IL35583A (en)
NL (1) NL7017185A (en)
SE (1) SE388617B (en)
ZA (1) ZA707509B (en)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3963720A (en) * 1972-10-27 1976-06-15 Sandoz, Inc. Tetracyclic imidazo [2,1-b] quinazolinone derivatives
ATE165T1 (en) * 1978-07-28 1981-09-15 Synthelabo FLUORENE AND FLUORANTHENE DERIVATIVES, PROCESSES FOR THEIR PRODUCTION AND THEIR THERAPEUTIC USE.
DE3220438A1 (en) * 1982-05-29 1983-12-01 Troponwerke GmbH & Co KG, 5000 Köln CHINAZOLINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE IN MEDICINAL PRODUCTS
AU623910B2 (en) * 1988-05-16 1992-05-28 United States of America, as represented by the Secretary, U.S. Department of Commerce, The Chemotherapeutic composition for aids
US6262093B1 (en) 1995-04-12 2001-07-17 The Proctor & Gamble Company Methods of treating cancer with benzimidazoles
ZA962879B (en) * 1995-04-12 1997-03-17 Procter & Gamble A pharmaceutical composition for inhibiting the growth of viruses and cancers
US6479526B1 (en) 1995-04-12 2002-11-12 The Procter & Gamble Company Pharmaceutical composition for inhibiting the growth of viruses and cancers
US6265427B1 (en) 1995-06-07 2001-07-24 The Proctor & Gamble Company Pharmaceutical composition for the method of treating leukemia
US5900429A (en) 1997-01-28 1999-05-04 The Procter & Gamble Company Method for inhibiting the growth of cancers
US6506783B1 (en) 1997-05-16 2003-01-14 The Procter & Gamble Company Cancer treatments and pharmaceutical compositions therefor
US6245789B1 (en) 1998-05-19 2001-06-12 The Procter & Gamble Company HIV and viral treatment
US6423734B1 (en) 1999-08-13 2002-07-23 The Procter & Gamble Company Method of preventing cancer
US6380232B1 (en) 2000-09-26 2002-04-30 The Procter & Gamble Company Benzimidazole urea derivatives, and pharmaceutical compositions and unit dosages thereof
US6407105B1 (en) * 2000-09-26 2002-06-18 The Procter & Gamble Company Compounds and methods for use thereof in the treatment of cancer or viral infections
US6608096B1 (en) * 2000-09-26 2003-08-19 University Of Arizona Foundation Compounds and methods for use thereof in the treatment of cancer or viral infections
US6462062B1 (en) * 2000-09-26 2002-10-08 The Procter & Gamble Company Compounds and methods for use thereof in the treatment of cancer or viral infections
US6515074B2 (en) * 2001-01-22 2003-02-04 Delphi Technologies, Inc. Thermoplastic polymer alloy compositions and process for manufacture thereof
WO2009038731A2 (en) * 2007-09-17 2009-03-26 The Trustees Of Columbia University In The City Of New York Synthesis of resveratrol-based natural products
WO2011103442A2 (en) * 2010-02-18 2011-08-25 The Trustees Of Columbia University In The City Of New York Synthesis of the potent immunosuppressant agents dalesconol a and b
DE102010024542A1 (en) * 2010-06-22 2011-12-22 Merck Patent Gmbh Materials for electronic devices
EP2897959B1 (en) * 2012-09-20 2017-12-20 UDC Ireland Limited Azadibenzofurans for electronic applications
CN112010925B (en) * 2019-05-28 2021-10-26 首都医科大学 GDE and hydroxymethyl modified benzimidazole quinazoline, synthesis, activity and application thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3244717A (en) * 1964-06-18 1966-04-05 Searle & Co 5-hydroxy-2-methyl-7-phenylimidazo [1, 2-a] pyrimidines
US3501473A (en) * 1967-11-09 1970-03-17 American Home Prod Disubstituted - 11h - quinazolino - (2,3-b) quinazoline - 11,13 (5h) - diones and the process for their preparation

Also Published As

Publication number Publication date
IE34676B1 (en) 1975-07-09
CA974992A (en) 1975-09-23
FR2073408B1 (en) 1974-05-24
IE34676L (en) 1971-05-24
ES385683A1 (en) 1973-10-01
FR2073408A1 (en) 1971-10-01
AT310758B (en) 1973-10-10
BE759337A (en) 1971-05-24
NL7017185A (en) 1971-05-26
US3669969A (en) 1972-06-13
DE2058185A1 (en) 1971-06-03
JPS5026560B1 (en) 1975-09-01
SE388617B (en) 1976-10-11
ZA707509B (en) 1971-08-25
IL35583A0 (en) 1971-01-28
CH560216A5 (en) 1975-03-27
IL35583A (en) 1975-02-10

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee