GB1307306A - Alkyl esters of n-5 -6- acyl-2-benzimidazolyl carbamic acid and a process for the preparation thereof - Google Patents

Alkyl esters of n-5 -6- acyl-2-benzimidazolyl carbamic acid and a process for the preparation thereof

Info

Publication number
GB1307306A
GB1307306A GB2604470A GB2604470A GB1307306A GB 1307306 A GB1307306 A GB 1307306A GB 2604470 A GB2604470 A GB 2604470A GB 2604470 A GB2604470 A GB 2604470A GB 1307306 A GB1307306 A GB 1307306A
Authority
GB
United Kingdom
Prior art keywords
formula
benzimidazole derivatives
ketones
acyl
preparation
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
GB2604470A
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.)
Janssen Pharmaceutica NV
Original Assignee
Janssen Pharmaceutica NV
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 Janssen Pharmaceutica NV filed Critical Janssen Pharmaceutica NV
Publication of GB1307306A publication Critical patent/GB1307306A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
    • 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
    • C07D235/30—Nitrogen atoms not forming part of a nitro radical
    • C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Fodder In General (AREA)

Abstract

1307306 Benzimidazole derivatives JANSSEN PHARMACEUTICA NV 29 May 1970 [20 June 1969] 26044/70 Heading C2C Novel benzimidazole derivatives of the formula wherein R is C 1-6 alkyl, C 3-6 cycloalkyl , phenyl, halophenyl, C 1-6 alkylphenyl,. C 1-6 alkoxyphenyl or 2-thienyl, and R 1 is CH 3 or CH 3 CH 2 , and RCO is located at the 5(6)-position, are prepared by reacting compounds of the formula with aminoketones of the Formula V: in the presence of protonic acids. Aminoketones of Formula V above are obtained by hydrogenating the corresponding 4-amino-3-nitropheoyl ketones obtained by ammonolysis of the corresponding 4-halo-3-nitrophenyl ketones resulting from the Friedel- Crafts reaction between the appropriate 3-halo - 4-nitrobenzoyl chloride and compounds of the formula RH, or by nitrating the-corresponding 4-halophenyl ketones resulting from the Friedel- Crafts reaction between the appropriate halobenzene and carbonyl chlorides of the formula RCOCl. Antihelmintic compositions, suitable for the usual routes of administration, contain the above novel benzimidazole derivatives in admixture with suitable carriers.
GB2604470A 1969-06-20 1970-05-29 Alkyl esters of n-5 -6- acyl-2-benzimidazolyl carbamic acid and a process for the preparation thereof Expired GB1307306A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US83524669A 1969-06-20 1969-06-20

Publications (1)

Publication Number Publication Date
GB1307306A true GB1307306A (en) 1973-02-21

Family

ID=25269027

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2604470A Expired GB1307306A (en) 1969-06-20 1970-05-29 Alkyl esters of n-5 -6- acyl-2-benzimidazolyl carbamic acid and a process for the preparation thereof

Country Status (20)

Country Link
US (1) US3657267A (en)
JP (1) JPS501272B1 (en)
AT (2) AT307798B (en)
BE (1) BE752089A (en)
CH (1) CH520684A (en)
CS (1) CS201522B2 (en)
DK (2) DK134602B (en)
ES (1) ES380579A1 (en)
FI (1) FI52719C (en)
FR (1) FR2052988B1 (en)
GB (1) GB1307306A (en)
HK (1) HK77976A (en)
IL (1) IL34746A (en)
IT (1) IT1035027B (en)
MY (1) MY7300477A (en)
NL (1) NL147139B (en)
PL (1) PL72724B1 (en)
SE (1) SE366045B (en)
YU (1) YU34195B (en)
ZA (1) ZA704191B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109467512A (en) * 2018-12-18 2019-03-15 苏州开元民生科技股份有限公司 A kind of synthetic method of 3,4- diamino-benzophenone

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2201208A1 (en) * 1972-01-12 1973-08-02 Basf Ag PROCESS FOR MANUFACTURING AROMATIC KETONES
US3929821A (en) * 1972-12-29 1975-12-30 Syntex Inc 5 (6)-Benzene ring substituted benzimidazole-2-carbamate derivatives
US4258198A (en) * 1973-05-29 1981-03-24 Smithkline Corporation 5-Cycloalkyl thio- and oxy-2-carbalkoxyaminobenzimidazoles
US3969526A (en) * 1973-05-29 1976-07-13 Smithkline Corporation Anthelmintic 5-heterocycliothio and oxy-2-carbalkoxyaminobenzimidazles
DE2443297A1 (en) * 1974-09-10 1976-03-18 Hoechst Ag ANTHELMINTHICALLY ACTIVE BASIC SUBSTITUTED 2-CARBALKOXY-AMINO-BENZIMIDAZOLYL-5 (6) -PHENYL ETHERS AND KETONES AND THE PROCESS FOR THEIR PRODUCTION
US4026936A (en) * 1975-08-07 1977-05-31 Hoffmann-La Roche Inc. Anthelmintic pyridine and thiazole substituted benzimidazole carbamates
US4031234A (en) * 1975-08-18 1977-06-21 Syntex (U.S.A.) Inc. 1,5(6)-Disubstituted benzimidazole-2-carbamate derivatives having anthelmintic activity
US4032536A (en) * 1976-07-22 1977-06-28 Janssen Pharmaceutica N.V. (1h-benzimidazol-2-yl)carbamates
IT1076022B (en) * 1977-04-20 1985-04-22 Montedison Spa ANTIELMINTIC BENZIMIDAZOLCARBAMMATES
JPS5535611A (en) * 1978-08-31 1980-03-12 Matsushita Electric Works Ltd Instrument with mouth washing instrument
US4299837A (en) 1979-12-05 1981-11-10 Montedison S.P.A. Anthelmintic benzimidazole-carbamates
US4435418A (en) 1982-12-13 1984-03-06 Smithkline Beckman Corporation 5-Phenylethenylbenzimidazoles
US4438135A (en) 1983-01-07 1984-03-20 Smithkline Beckman Corporation 1-(3,4-Bis-(3-(lower alkoxycarbonyl)-2-thioureido)-phenyl-1-phenylthylenes
US5256681A (en) * 1989-03-15 1993-10-26 Janssen Pharmaceutica N.V. [5(6)-(benzisoxa-,benzisothia-or indazol-3-yl)-1H-benzimidazol-2-yl]carbamates
WO1990010630A1 (en) * 1989-03-15 1990-09-20 Janssen Pharmaceutica N.V. [5(6)-(benzisoxa-, benzisothia- or indazol-3-yl)-1h-benzimidazol-2-yl] carbamates
NZ232785A (en) * 1989-03-15 1991-03-26 Janssen Pharmaceutica Nv 5-(1,2 benzisoxazol-, benzimidazol and benzisothiazol-3- yl)-1h-benzimadazol-2-yl carbamic acid ester derivatives preparatory processes, intermediates and anthelmintic compositions
US5278181A (en) * 1992-05-12 1994-01-11 Board Of Regents Acting On Behalf Of The University Of Michigan Soluble alkyl[5-[amino (phenyl)methyl]-1H-benzimidazol-2-yl] carbamate anthelmintics
US7893271B2 (en) * 2005-07-28 2011-02-22 Intervet International B.V. Benzimidazole carbamates and (thio) carbamates, and the synthesis and use thereof
EP2032046B1 (en) * 2006-06-12 2015-11-04 Smith & Nephew, Inc. Systems and devices for tibial resection
CA2660647C (en) 2006-06-14 2015-07-28 Intervet International B.V. A suspension comprising benzimidazole carbamate and a polysorbate
WO2013110975A1 (en) 2012-01-27 2013-08-01 Siegfried Rhein S.A. De C.V. Improved nitazoxanide composition and preparation method thereof
WO2014049397A1 (en) 2012-09-27 2014-04-03 Siegfried Rhein S.A. De C.V. Synergic composition of nitazoxanide and mebendazole, methods for the preparation thereof, and use of said composition for the treatment of human parasitosis
CN108884054B (en) 2015-11-30 2022-08-02 儿童医学中心公司 Compounds for the treatment of proliferative diseases
ES2962526T3 (en) 2017-06-22 2024-03-19 Cipla Ltd PAR-4 secretagogues for cancer treatment
CN113979949A (en) * 2021-12-17 2022-01-28 山东国邦药业有限公司 Preparation method of fluorobenzene imidazole

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1111957A (en) * 1966-05-20 1968-05-01 Smith Kline French Lab Improvements in or relating to anthelmintic compositions

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109467512A (en) * 2018-12-18 2019-03-15 苏州开元民生科技股份有限公司 A kind of synthetic method of 3,4- diamino-benzophenone
CN109467512B (en) * 2018-12-18 2021-06-08 苏州开元民生科技股份有限公司 Synthetic method of 3, 4-diamino-benzophenone

Also Published As

Publication number Publication date
DK134602B (en) 1976-12-06
DK134602C (en) 1977-06-27
JPS501272B1 (en) 1975-01-16
SE366045B (en) 1974-04-08
AT302358B (en) 1972-10-10
DE2029637A1 (en) 1971-02-18
DK580275A (en) 1975-12-19
YU34195B (en) 1979-02-28
NL147139B (en) 1975-09-15
CS201522B2 (en) 1980-11-28
IL34746A (en) 1973-01-30
FI52719B (en) 1977-08-01
FI52719C (en) 1977-11-10
US3657267A (en) 1972-04-18
YU154470A (en) 1978-09-18
IT1035027B (en) 1979-10-20
HK77976A (en) 1976-12-17
FR2052988A1 (en) 1971-04-16
FR2052988B1 (en) 1973-08-10
ZA704191B (en) 1972-02-23
AT307798B (en) 1973-06-12
MY7300477A (en) 1973-12-31
PL72724B1 (en) 1974-08-30
NL7009024A (en) 1970-12-22
BE752089A (en) 1970-12-17
DE2029637B2 (en) 1976-09-23
ES380579A1 (en) 1973-04-01
IL34746A0 (en) 1970-08-19
CH520684A (en) 1972-03-31

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
746B Proceeding under section 46(3) patents act 1977
PE20 Patent expired after termination of 20 years