GB1356763A - Substituted benzimidazole derivatives - Google Patents
Substituted benzimidazole derivativesInfo
- Publication number
- GB1356763A GB1356763A GB1791772A GB1791772A GB1356763A GB 1356763 A GB1356763 A GB 1356763A GB 1791772 A GB1791772 A GB 1791772A GB 1791772 A GB1791772 A GB 1791772A GB 1356763 A GB1356763 A GB 1356763A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- methoxy
- substituted
- benzothiazolyl
- reacting
- 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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1356763 2 - Benzo(heterocyclic)ethyl benzimidazoles and derivatives thereof MERCK & CO Inc 18 April 1972 [21 April 1971] 17917/72 Heading C2C [Also in Division C4] Novel compounds of the Formula I wherein m is 0, 1 or 2, n is 0 or 1, each R is C 1-5 alkyl, alkoxy, haloalkoxy or alkylthio, C 3-6 cycloalkoxy, C 2-6 alkenyl, or halogen or when m is 2 the R groups together form a methylene dioxy group; R 1 is hydrogen or C 1-5 alkyl; each R 2 is hydrogen or hydroxyl; X is carbonyl; A is oxygen, sulphur, nitrogen, imino, methylene or methine; the dotted lines indicate that a double bond is located at one of the two positions available between A and N with a hydrogen atom attached to N if valency considerations require it; with the provisos that when n is 0, A is not hydrogen or imino, and that when n is 0 and A is oxygen or sulphur at least one m is not 0; and acid addition salts thereof are prepared (a) by reacting the compounds and wherein R, R<SP>1</SP>, R 2 and m are as defined above Z is a carboxylic acid group, an aldehyde or Schiff base derivative thereof, or a nitrile, carboxylic ester, carboximidic ester or carboxylic amide group, and Z 1 is a group of the type defined for Z or is a group of the Formula IV wherein R, X, A, m and n and the dotted lines are as defined above and when Z 1 is a group of the type defined for Z reacting the intermediate of the formula wherein A* is oxygen or sulphur, and then closing the ring; and (b) reacting the above compound of Formula IV when Z is cyano with or when Z is other than cyano with to produce Various [2R,3R] - 2,3 - dihydroxy - 3 - (6- substituted - 2 - benzothiazolyl) - propion - [2- amino-4(5)-methoxy]anilides may be prepared by acetylation of the sodium salt of [2R,3R]-2, 3 - dihydroxy - 3 - (6 - substituted - 2 - benzothiazolyl propionic acid to yield the sodium salt of [2R,3R] - 2,3 - diacetoxy - 3 - (6 - substituted- 2-benzothiazolyl propionic acid which on treatment with 4-methoxy-o-phenylene diamine in the presence of acid and a dehydrating agent yields [2R,3R] - 2,3 - diacetoxy - 3 - (6 - substituted - 2 - benzothiazolyl) - propion - [2 - amino- 4(5)-methoxy]-anilide which on treatment with sodium methoxide yields the required compound. The sodium salt of [2R,3R]-2,3-dihydroxy-3- (6 - methoxy - 2 - benzothiazolyl)propionic acid may be prepared by reacting 2-amino-5-methoxythiophenol with L-diacetyl tartaric anhydride to yield [2R,3R]-2,3-diacetoxy-3-(6-methoxy-2-benzothiazolyl) propionic acid which was converted to its ammonium salt and hydrolsyed with sodium methoxide to the required compound. Various substituted 2-(#-cyanoethyl)benzimidazoles may be prepared by reacting the appropriate o-phenylenediamine with methyl-3-cyanopropyl carboximidate hydrochloride. Various ethyl - 3 - benzimidazolyl - (2) - propionimidate dihydrochlorides substituted in the benzimidazole ring may be prepared by reacting the appropriate 2-(#-cyanoethyl)benzimidazole with ethanol and hydrogen chloride in anhydrous conditions. [2R,3R] - 2,3 - Dihydroxy - 3 - [2 - 4(3H)- quinazolinonyl] - propion - [2 - amino - 4(5). methoxy]-anilide and various derivatives substituted in the 7-position of the quinazoline ring may be prepared by reaction of 4-methoxy-ophenylene diamine with the appropriate [2R, 3R] - 2,3 - dihydroxy - 3 - [2 - 4(3H) - quinazolinonyl]propionic acid which in turn is prepared by treatment of a [αR,#R]-diacetyltartar-2-carbamoyl anilide with sodium hydroxide, which anilide is prepared by treatment of an anthranilamide with L-diacetyl tartaric anhydride. Pharmaceutical compositions of the compounds I show antiviral activity when administered orally, parenterally, topically or as an oral or nasal spray with the usual excipients.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13618671A | 1971-04-21 | 1971-04-21 | |
US13818671A | 1971-04-21 | 1971-04-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1356763A true GB1356763A (en) | 1974-06-12 |
Family
ID=26834087
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1791772A Expired GB1356763A (en) | 1971-04-21 | 1972-04-18 | Substituted benzimidazole derivatives |
Country Status (4)
Country | Link |
---|---|
DE (1) | DE2219408A1 (en) |
FR (1) | FR2133979B1 (en) |
GB (1) | GB1356763A (en) |
NL (1) | NL7204972A (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003035075A1 (en) * | 2001-10-19 | 2003-05-01 | Icos Corporation | Inhibitors of human phosphatidyl-inositol 3-kinase delta |
US7932260B2 (en) | 2004-05-13 | 2011-04-26 | Icos Corporation | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
US8440677B2 (en) | 2009-03-24 | 2013-05-14 | Gilead Calistoga Llc | Atropisomers of 2-purinyl-3-tolyl-quinazolinone derivatives and methods of use |
US8546409B2 (en) | 2009-04-20 | 2013-10-01 | Gilead Calistoga Llc | Methods of treatment for solid tumors |
EP2663565A2 (en) * | 2011-01-11 | 2013-11-20 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
US8691829B2 (en) | 2009-07-21 | 2014-04-08 | Gilead Calistoga Llc | Treatment of liver disorders with PI3K inhibitors |
US8865730B2 (en) | 2012-03-05 | 2014-10-21 | Gilead Calistoga Llc | Polymorphic forms of (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one |
US9238070B2 (en) | 2008-11-13 | 2016-01-19 | Gilead Calistoga Llc | Therapies for hematologic malignancies |
US9492449B2 (en) | 2008-11-13 | 2016-11-15 | Gilead Calistoga Llc | Therapies for hematologic malignancies |
US9567337B2 (en) | 2013-12-20 | 2017-02-14 | Gilead Calistoga Llc | Process methods for phosphatidylinositol 3-kinase inhibitors |
US9708327B2 (en) | 2013-12-20 | 2017-07-18 | Gilead Calistoga Llc | Polymorphic forms of a hydrochloride salt of (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one |
US9834564B2 (en) | 2010-05-26 | 2017-12-05 | Sunovion Pharmaceuticals Inc. | Substituted quinolines as PDE-10 inhibitors |
US11021467B2 (en) | 2014-06-13 | 2021-06-01 | Gilead Sciences, Inc. | Phosphatidylinositol 3-kinase inhibitors |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111944340B (en) * | 2020-08-21 | 2022-08-05 | 无锡市乐卡新材料有限公司 | Salt-fog-resistant antirust coating |
-
1972
- 1972-04-13 NL NL7204972A patent/NL7204972A/xx unknown
- 1972-04-18 GB GB1791772A patent/GB1356763A/en not_active Expired
- 1972-04-20 FR FR7214052A patent/FR2133979B1/fr not_active Expired
- 1972-04-20 DE DE19722219408 patent/DE2219408A1/en active Pending
Cited By (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8623881B2 (en) | 2000-04-25 | 2014-01-07 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
US6667300B2 (en) | 2000-04-25 | 2003-12-23 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
US6949535B2 (en) | 2000-04-25 | 2005-09-27 | Icos Corporation | Inhibitors of human phosphatidyl-inositol 3-kinase delta |
US8138195B2 (en) | 2000-04-25 | 2012-03-20 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
US9487772B2 (en) | 2000-04-25 | 2016-11-08 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
US10010550B2 (en) | 2000-04-25 | 2018-07-03 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
US8492389B2 (en) | 2000-04-25 | 2013-07-23 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
US10695349B2 (en) | 2000-04-25 | 2020-06-30 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
US8653077B2 (en) | 2000-04-25 | 2014-02-18 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
US8637533B2 (en) | 2000-04-25 | 2014-01-28 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
US10398695B2 (en) | 2000-04-25 | 2019-09-03 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
WO2003035075A1 (en) * | 2001-10-19 | 2003-05-01 | Icos Corporation | Inhibitors of human phosphatidyl-inositol 3-kinase delta |
US8207153B2 (en) | 2004-05-13 | 2012-06-26 | Icos Corporation | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
USRE44638E1 (en) | 2004-05-13 | 2013-12-10 | Icos Corporation | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
US8586597B2 (en) | 2004-05-13 | 2013-11-19 | Icos Corporation | 6-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)ethyl]-3H-quinazolin-4-one as an inhibitor of human phosphatidylinositol 3-kinase delta |
USRE44599E1 (en) | 2004-05-13 | 2013-11-12 | Icos Corporation | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
US10336756B2 (en) | 2004-05-13 | 2019-07-02 | Icos Corporation | (S)-2-(1-aminopropyl)-5-fluoro-3-phenylquinazolin-4(3H)-one precursor of a quinazolinone as inhibitor of human phosphatidylinositol 3-kinase delta |
US10906907B2 (en) | 2004-05-13 | 2021-02-02 | Icos Corporation | Tert-butyl (s)-(1-(5-fluoro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)propyl)carbamate precursor of a quinazolinone inhibitor of human phosphatidylinositol 3-kinase delta and a process for preparing thereof |
US9149477B2 (en) | 2004-05-13 | 2015-10-06 | Icos Corporation | 5-fluoro-3-phenyl-2-[1-(9h-purin-6-ylamino)propyl]-3h-quinazolin-4-one as an inhibitor of human phosphatidylinositol 3-kinase delta |
US8779131B2 (en) | 2004-05-13 | 2014-07-15 | Icos Corporation | 6-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)-ethyl]-3H-quinazolin-4-one as an inhibitor of human phosphatidylinositol 3-kinase delta |
US7932260B2 (en) | 2004-05-13 | 2011-04-26 | Icos Corporation | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
US8980901B2 (en) | 2004-05-13 | 2015-03-17 | Icos Corporation | 5-fluoro-3-phenyl-2[1-(9H-purin-6-ylamino)propyl]-3H-quinazolin-4-one and 6-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)ethyl]-3H-quinazolin-4-one as inhibitors of human phosphatidylinositol 3-kinase delta |
US8993583B2 (en) | 2004-05-13 | 2015-03-31 | Icos Corporation | 5-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)propyl]-3H-quinazolin-4-one and 6-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)ethyl]-3H-quinazolin-4-one as inhibitors of human phosphatidylinositol 3-kinase delta |
US9238070B2 (en) | 2008-11-13 | 2016-01-19 | Gilead Calistoga Llc | Therapies for hematologic malignancies |
US10154998B2 (en) | 2008-11-13 | 2018-12-18 | Gilead Calistoga Llc | Therapies for hematologic malignancies |
US9492449B2 (en) | 2008-11-13 | 2016-11-15 | Gilead Calistoga Llc | Therapies for hematologic malignancies |
US8440677B2 (en) | 2009-03-24 | 2013-05-14 | Gilead Calistoga Llc | Atropisomers of 2-purinyl-3-tolyl-quinazolinone derivatives and methods of use |
US8546409B2 (en) | 2009-04-20 | 2013-10-01 | Gilead Calistoga Llc | Methods of treatment for solid tumors |
US8691829B2 (en) | 2009-07-21 | 2014-04-08 | Gilead Calistoga Llc | Treatment of liver disorders with PI3K inhibitors |
US10562916B2 (en) | 2010-05-26 | 2020-02-18 | Sunovion Pharmaceuticals, Inc. | Substituted quinoxalines as PDE-10 inhibitors |
US9834564B2 (en) | 2010-05-26 | 2017-12-05 | Sunovion Pharmaceuticals Inc. | Substituted quinolines as PDE-10 inhibitors |
EP3210984A1 (en) * | 2011-01-11 | 2017-08-30 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
CN103619841B (en) * | 2011-01-11 | 2017-03-29 | 桑诺维恩药品公司 | Heteroaryl compound and its using method |
US9856274B2 (en) | 2011-01-11 | 2018-01-02 | Sunovion Pharmaceuticals Inc. | Substituted pyrazolo[1,5-a]pyridines as PDE-10 inhibitors |
AU2012205687B2 (en) * | 2011-01-11 | 2017-03-16 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
EP2663565A4 (en) * | 2011-01-11 | 2014-07-02 | Sunovion Pharmaceuticals Inc | Heteroaryl compounds and methods of use thereof |
AU2017204007B2 (en) * | 2011-01-11 | 2018-11-08 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
CN103619841A (en) * | 2011-01-11 | 2014-03-05 | 桑诺维恩药品公司 | Heteroaryl compounds and methods of use thereof |
EP2663565A2 (en) * | 2011-01-11 | 2013-11-20 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
US10570156B2 (en) | 2011-01-11 | 2020-02-25 | Sunovion Pharmaceuticals Inc. | Substituted imidazo[1,2-a]pyridines as PDE-10 inhibitors |
US10730879B2 (en) | 2012-03-05 | 2020-08-04 | Gilead Calistoga Llc | Polymorphic forms of (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one |
US8865730B2 (en) | 2012-03-05 | 2014-10-21 | Gilead Calistoga Llc | Polymorphic forms of (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one |
US9469643B2 (en) | 2012-03-05 | 2016-10-18 | Gilead Calistoga, LLC. | Polymorphic forms of (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one |
US10047060B2 (en) | 2013-12-20 | 2018-08-14 | Gilead Calistoga Llc | Process methods for phosphatidylinositol 3-kinase inhibitors |
US10442805B2 (en) | 2013-12-20 | 2019-10-15 | Gilead Calistoga Llc | Polymorphic forms of a hydrochloride salt of (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one |
US10414737B2 (en) | 2013-12-20 | 2019-09-17 | Gilead Sciences, Inc. | Process methods for phosphatidylinositol 3-kinase inhibitors |
US10059677B2 (en) | 2013-12-20 | 2018-08-28 | Gilead Calistoga Llc | Process for preparing phosphatidylinositol 3-kinase inhibitors and intermediates thereof |
US9708327B2 (en) | 2013-12-20 | 2017-07-18 | Gilead Calistoga Llc | Polymorphic forms of a hydrochloride salt of (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one |
US9567337B2 (en) | 2013-12-20 | 2017-02-14 | Gilead Calistoga Llc | Process methods for phosphatidylinositol 3-kinase inhibitors |
US10954199B2 (en) | 2013-12-20 | 2021-03-23 | Gilead Sciences, Inc. | Process methods for phosphatidylinositol 3-kinase inhibitors |
US11021467B2 (en) | 2014-06-13 | 2021-06-01 | Gilead Sciences, Inc. | Phosphatidylinositol 3-kinase inhibitors |
Also Published As
Publication number | Publication date |
---|---|
FR2133979B1 (en) | 1975-10-31 |
DE2219408A1 (en) | 1972-10-26 |
NL7204972A (en) | 1972-10-24 |
FR2133979A1 (en) | 1972-12-01 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PLNP | Patent lapsed through nonpayment of renewal fees |