GB1322930A - Benzimidazo 2,1-b quinazolin derivatives as immuno suppressants - Google Patents
Benzimidazo 2,1-b quinazolin derivatives as immuno suppressantsInfo
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; 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
-
- 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)
- 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.
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)
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)
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 |
-
0
- BE BE759337D patent/BE759337A/en unknown
-
1969
- 1969-11-24 US US879579A patent/US3669969A/en not_active Expired - Lifetime
-
1970
- 1970-11-02 IE IE1392/70A patent/IE34676B1/en unknown
- 1970-11-04 IL IL35583A patent/IL35583A/en unknown
- 1970-11-05 ZA ZA707509A patent/ZA707509B/en unknown
- 1970-11-17 CA CA098,317A patent/CA974992A/en not_active Expired
- 1970-11-18 ES ES385683A patent/ES385683A1/en not_active Expired
- 1970-11-23 SE SE7015860A patent/SE388617B/en unknown
- 1970-11-23 DE DE19702058185 patent/DE2058185A1/en active Pending
- 1970-11-23 GB GB5562170A patent/GB1322930A/en not_active Expired
- 1970-11-24 FR FR7042071A patent/FR2073408B1/fr not_active Expired
- 1970-11-24 AT AT1058970A patent/AT310758B/en not_active IP Right Cessation
- 1970-11-24 CH CH1737470A patent/CH560216A5/xx not_active IP Right Cessation
- 1970-11-24 JP JP45103606A patent/JPS5026560B1/ja active Pending
- 1970-11-24 NL NL7017185A patent/NL7017185A/xx not_active Application Discontinuation
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 |