CS215073B2 - Method of making the derivatives of the 5-phenylselenobenzimidazole - Google Patents

Method of making the derivatives of the 5-phenylselenobenzimidazole Download PDF

Info

Publication number: CS215073B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; derivatives; carbon atoms; alkyl; methyl
Prior art date: 1979-10-12

Application number

CS806831A

Other languages

Czech (cs)

English (en)

Inventor

Anthony P Flynn

Original Assignee

Ici Ltd

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.)

1979-10-12

Filing date

1980-10-09

Publication date

1982-07-30

1980-10-09 Application filed by Ici Ltd filed Critical Ici Ltd

1982-07-30 Publication of CS215073B2 publication Critical patent/CS215073B2/cs

Links

238000004519 manufacturing process Methods 0.000 title abstract 2
KMJKJNISPZTEMO-UHFFFAOYSA-N 6-phenylselanyl-1h-benzimidazole Chemical compound C=1C=C2N=CNC2=CC=1[Se]C1=CC=CC=C1 KMJKJNISPZTEMO-UHFFFAOYSA-N 0.000 title description 5
238000000034 method Methods 0.000 claims abstract description 11
150000001875 compounds Chemical class 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
150000004985 diamines Chemical class 0.000 claims description 5
-1 alkyl chloroformate Chemical compound 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
230000003647 oxidation Effects 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
229910052799 carbon Inorganic materials 0.000 claims 2
229910052749 magnesium Inorganic materials 0.000 claims 2
239000011777 magnesium Substances 0.000 claims 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
125000005529 alkyleneoxy group Chemical group 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 11
OSTZICHUZHXZEY-UHFFFAOYSA-N methyl n-(6-phenylselanyl-1h-benzimidazol-2-yl)carbamate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1[Se]C1=CC=CC=C1 OSTZICHUZHXZEY-UHFFFAOYSA-N 0.000 abstract description 5
230000000507 anthelmentic effect Effects 0.000 abstract description 4
230000003549 fasciolicidal effect Effects 0.000 abstract description 2
JEDAHMZLUROSDB-UHFFFAOYSA-N (6-phenylselanyl-1H-benzimidazol-2-yl)carbamic acid Chemical class C1=C2NC(NC(=O)O)=NC2=CC=C1[Se]C1=CC=CC=C1 JEDAHMZLUROSDB-UHFFFAOYSA-N 0.000 abstract 1
238000009472 formulation Methods 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 4
150000001556 benzimidazoles Chemical class 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
235000013361 beverage Nutrition 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000012265 solid product Substances 0.000 description 3
LLJFYYUNCNXLQR-UHFFFAOYSA-N 4-phenylselanylbenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1[Se]C1=CC=CC=C1 LLJFYYUNCNXLQR-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241001494479 Pecora Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
KHBXLYPOXVQKJG-UHFFFAOYSA-N methyl n-[(methoxycarbonylamino)-methylsulfanylmethylidene]carbamate Chemical compound COC(=O)NC(SC)=NC(=O)OC KHBXLYPOXVQKJG-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
TVNWWWMLLUZALK-UHFFFAOYSA-N 2-nitro-5-phenylselanylaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC([Se]C=2C=CC=CC=2)=C1 TVNWWWMLLUZALK-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
ZCWXYZBQDNFULS-UHFFFAOYSA-N 5-chloro-2-nitroaniline Chemical compound NC1=CC(Cl)=CC=C1[N+]([O-])=O ZCWXYZBQDNFULS-UHFFFAOYSA-N 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
241000283707 Capra Species 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
208000025011 Distomatosis Diseases 0.000 description 1
241000283086 Equidae Species 0.000 description 1
208000006968 Helminthiasis Diseases 0.000 description 1
SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 1
PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
239000003674 animal food additive Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
238000011109 contamination Methods 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
YWWZCHLUQSHMCL-UHFFFAOYSA-N diphenyl diselenide Chemical compound C=1C=CC=CC=1[Se][Se]C1=CC=CC=C1 YWWZCHLUQSHMCL-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
244000000013 helminth Species 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
230000000366 juvenile effect Effects 0.000 description 1
230000001418 larval effect Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
WCOYXXNAWMTBEV-UHFFFAOYSA-N methyl n-(6-phenylseleninyl-1h-benzimidazol-2-yl)carbamate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1[Se](=O)C1=CC=CC=C1 WCOYXXNAWMTBEV-UHFFFAOYSA-N 0.000 description 1
MKOPKYLNCJEXRS-UHFFFAOYSA-N methyl n-[6-(4-methoxyphenyl)selanyl-1h-benzimidazol-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1[Se]C1=CC=C(OC)C=C1 MKOPKYLNCJEXRS-UHFFFAOYSA-N 0.000 description 1
208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C391/00—Compounds containing selenium
- C07C391/02—Compounds containing selenium having selenium atoms bound to carbon atoms of six-membered aromatic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
- 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

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Tropical Medicine & Parasitology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CS806831A 1979-10-12 1980-10-09 Method of making the derivatives of the 5-phenylselenobenzimidazole CS215073B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7935502		1979-10-12

Publications (1)

Publication Number	Publication Date
CS215073B2 true CS215073B2 (en)	1982-07-30

Family

ID=10508467

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS806831A CS215073B2 (en)	1979-10-12	1980-10-09	Method of making the derivatives of the 5-phenylselenobenzimidazole

Country Status (11)

Country	Link
US (1)	US4303666A (da)
EP (1)	EP0028455A1 (da)
JP (1)	JPS5661363A (da)
AU (1)	AU6293380A (da)
CA (1)	CA1153381A (da)
CS (1)	CS215073B2 (da)
DK (1)	DK422980A (da)
ES (1)	ES8201141A1 (da)
NZ (1)	NZ195096A (da)
YU (1)	YU259380A (da)
ZA (1)	ZA806020B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN103601684B (zh) *	2013-11-29	2016-01-20	沈阳药科大学	5-芳硒基苯并咪唑类化合物及其用途

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE793358A (fr) *	1971-12-27	1973-06-27	Hoechst Ag	Nouveaux derives de 2-carbalcoxy-amino-benzimidazole presentantune activite anthelmintique et leur procede de preparation
US3929824A (en) *	1972-12-29	1975-12-30	Syntex Inc	5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity
US3929821A (en) *	1972-12-29	1975-12-30	Syntex Inc	5 (6)-Benzene ring substituted benzimidazole-2-carbamate derivatives
US3965113A (en) *	1972-12-29	1976-06-22	Syntex (U.S.A.) Inc.	5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity
DE2365362A1 (de) *	1973-06-25	1975-01-23	Hoechst Ag	2,1,4-benzothiadiazinderivate und ihre herstellung
DE2332398A1 (de) *	1973-06-26	1975-01-23	Hoechst Ag	2-carbalkoxy-amino-benzimidazol-5(6)phenylaether, ihre herstellung und verwendung in mitteln gegen helminthen
DE2332343A1 (de) *	1973-06-26	1975-01-16	Hoechst Ag	2-carbalkoxy-amino-benzimidazol-5(6)phenylaether, ihre herstellung und verwendung in mitteln gegen helminthen
DE2432631A1 (de) *	1974-07-06	1976-01-22	Hoechst Ag	5-phenylsulfinyl-2-benzimidazol-carbaminsaeureester und verfahren zu ihrer herstellung
DE2438120A1 (de) *	1974-08-08	1976-02-19	Bayer Ag	Substituierte benzimidazolylcarbamidsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
YU40704B (en) *	1977-05-10	1986-04-30	Chinoin Gyogyszer Es Vegyeszet	Process for obtaininga 5(6)-thiobenzamidazole derivatives

1980
- 1980-09-26 EP EP80303401A patent/EP0028455A1/en not_active Ceased
- 1980-09-29 ZA ZA00806020A patent/ZA806020B/xx unknown
- 1980-09-30 NZ NZ195096A patent/NZ195096A/xx unknown
- 1980-10-03 AU AU62933/80A patent/AU6293380A/en not_active Abandoned
- 1980-10-07 DK DK422980A patent/DK422980A/da not_active Application Discontinuation
- 1980-10-07 US US06/194,932 patent/US4303666A/en not_active Expired - Lifetime
- 1980-10-09 CS CS806831A patent/CS215073B2/cs unknown
- 1980-10-09 YU YU02593/80A patent/YU259380A/xx unknown
- 1980-10-10 ES ES495828A patent/ES8201141A1/es not_active Expired
- 1980-10-10 CA CA000362239A patent/CA1153381A/en not_active Expired
- 1980-10-13 JP JP14215380A patent/JPS5661363A/ja active Pending

Also Published As

Publication number	Publication date
AU6293380A (en)	1981-04-16
JPS5661363A (en)	1981-05-26
YU259380A (en)	1983-02-28
CA1153381A (en)	1983-09-06
ES495828A0 (es)	1981-12-01
NZ195096A (en)	1982-12-21
DK422980A (da)	1981-04-13
US4303666A (en)	1981-12-01
EP0028455A1 (en)	1981-05-13
ES8201141A1 (es)	1982-01-16
ZA806020B (en)	1981-11-25

Publication	Publication Date	Title
US3929823A (en)	1975-12-30	5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity
US3956262A (en)	1976-05-11	Triazenoimidazoles
HU192972B (en)	1987-08-28	Process for producing substituted phenyl-/sulfonyl-oxy/-benzimidazole-carbamate derivatives and pharmaceutical compositions containing them
US3401171A (en)	1968-09-10	2-amidobenzimidazoles
EP1913009B1 (en)	2010-05-12	Novel benzimidazole (thio) carbamates with antiparasitic activity and the synthesis thereof
US4086336A (en)	1978-04-25	Phosphonothioureide anthelmintics
CS215073B2 (en)	1982-07-30	Method of making the derivatives of the 5-phenylselenobenzimidazole
US3868418A (en)	1975-02-25	Novel N-(ortho- and para-nitrobenzoyl)-sulfoximine intermediates and process for their production
PL101396B1 (pl)	1978-12-30	Sposob wytwarzania estrow fenylowych kwasu 2-karboalkoksyaminobenzimidazolilo-5 /6/-sulfonowego
US3880871A (en)	1975-04-29	Isothiocyanophenyl substituted imidazoles
US3661966A (en)	1972-05-09	Bisammonium compounds and process for preparing them
US3993769A (en)	1976-11-23	1,5(6)-Disubstituted benzimidazole-2-carbamate derivatives having anthelmintic activity
US4031234A (en)	1977-06-21	1,5(6)-Disubstituted benzimidazole-2-carbamate derivatives having anthelmintic activity
US4217358A (en)	1980-08-12	Substituted phenylguanidines and method
US4136174A (en)	1979-01-23	Benzimidazolecarbamates and method
US4328241A (en)	1982-05-04	Substituted phenylguanidines and method
US3993768A (en)	1976-11-23	5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity
US3326753A (en)	1967-06-20	Benzimidazole anthelmintic compositions and method of use
US4062952A (en)	1977-12-13	Substituted benzenedisulfonamides as anthelmintics
US4156006A (en)	1979-05-22	Vinyl sulfide derivatives of benzimidazoles
US4006242A (en)	1977-02-01	Certain benzothiazoles used in the treatment of helminthiasis
IL45189A (en)	1977-03-31	5-phenylsulfinyl-2-benzimidazolyl-carbamic acid esters and process for their manufacture
US4093731A (en)	1978-06-06	Methyl-6-n-propoxybenzothiazole-2-carbamate and anthelmintic pharmaceutical compositions thereof
US3962437A (en)	1976-06-08	5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity
US4154846A (en)	1979-05-15	Substituted thio-, sulfinyl-, and sulfonyl-alkyl benzimidazole carbamates