GB1308370A - 1-hydroxy-3-oxo-benzimidazoles quinoxaline-di-n-oxides and benzimidazole-mono-and di-n-oxides - Google Patents
1-hydroxy-3-oxo-benzimidazoles quinoxaline-di-n-oxides and benzimidazole-mono-and di-n-oxidesInfo
- Publication number
- GB1308370A GB1308370A GB4720270A GB4720270A GB1308370A GB 1308370 A GB1308370 A GB 1308370A GB 4720270 A GB4720270 A GB 4720270A GB 4720270 A GB4720270 A GB 4720270A GB 1308370 A GB1308370 A GB 1308370A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkali metal
- alkyl
- benzimidazole
- quinoxaline
- oxides
- 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
- -1 nitro, carbonyl Chemical group 0.000 abstract 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 10
- 150000001875 compounds Chemical class 0.000 abstract 10
- 229910000102 alkali metal hydride Inorganic materials 0.000 abstract 7
- 150000008046 alkali metal hydrides Chemical class 0.000 abstract 7
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 7
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 229910021529 ammonia Inorganic materials 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 5
- 150000004703 alkoxides Chemical class 0.000 abstract 4
- 239000002585 base Substances 0.000 abstract 4
- 150000002431 hydrogen Chemical class 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 abstract 4
- 150000003512 tertiary amines Chemical class 0.000 abstract 4
- 150000004678 hydrides Chemical class 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 abstract 2
- 241001465754 Metazoa Species 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 abstract 2
- 125000006575 electron-withdrawing group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 208000015181 infectious disease Diseases 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 230000009885 systemic effect Effects 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract 1
- XQYKDQBVUBUIOU-UHFFFAOYSA-N 2,2-dimethyl-3-oxidobenzimidazol-1-ium 1-oxide Chemical compound C1=CC=CC2=[N+]([O-])C(C)(C)[N+]([O-])=C21 XQYKDQBVUBUIOU-UHFFFAOYSA-N 0.000 abstract 1
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 abstract 1
- SZJTTXODXFSAIF-UHFFFAOYSA-N 2-ethyl-2-methyl-3-oxidobenzimidazol-1-ium 1-oxide Chemical compound C1=CC=C2[N+](=O)C(CC)(C)N([O-])C2=C1 SZJTTXODXFSAIF-UHFFFAOYSA-N 0.000 abstract 1
- YCRFRHIZRKQEAG-UHFFFAOYSA-N C1=CC=C2[N+]([O-])=CNC2=C1 Chemical class C1=CC=C2[N+]([O-])=CNC2=C1 YCRFRHIZRKQEAG-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 208000014085 Chronic respiratory disease Diseases 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- UHJXDBQHKYJPEL-UHFFFAOYSA-N O=NS(=O)=O Chemical compound O=NS(=O)=O UHJXDBQHKYJPEL-UHFFFAOYSA-N 0.000 abstract 1
- 241000286209 Phasianidae Species 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 abstract 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 230000000845 anti-microbial effect Effects 0.000 abstract 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 125000005239 aroylamino group Chemical group 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000005518 carboxamido group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 229960005215 dichloroacetic acid Drugs 0.000 abstract 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- RNVIQDJIRVJYKL-UHFFFAOYSA-N ethyl 1-hydroxy-3-oxidobenzimidazol-3-ium-2-carboxylate Chemical compound C1=CC=C2[N+]([O-])=C(C(=O)OCC)N(O)C2=C1 RNVIQDJIRVJYKL-UHFFFAOYSA-N 0.000 abstract 1
- XCLBIKIQSCTANZ-UHFFFAOYSA-N ethyl 2,2-diethoxyacetate Chemical compound CCOC(OCC)C(=O)OCC XCLBIKIQSCTANZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000002458 infectious effect Effects 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- CGJMROBVSBIBKP-UHFFFAOYSA-M malonamate Chemical compound NC(=O)CC([O-])=O CGJMROBVSBIBKP-UHFFFAOYSA-M 0.000 abstract 1
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 abstract 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 150000002828 nitro derivatives Chemical group 0.000 abstract 1
- 229910052757 nitrogen Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 229940120731 pyruvaldehyde Drugs 0.000 abstract 1
- AIJULSRZWUXGPQ-UHFFFAOYSA-N pyruvic aldehyde Natural products CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 201000009890 sinusitis Diseases 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 210000001635 urinary tract Anatomy 0.000 abstract 1
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
-
- 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
- C07D235/22—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms directly attached to ring nitrogen atoms
-
- 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
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1308370 Quinoxaline-di-N-oxides and benzimidazole-N-oxides RESEARCH CORP 5 Oct 1970 [9 Dec 1969] 47202/70 Addition to 1215815 Heading C2C Novel process for preparing quinoxaline-di- N-oxides and benzimidazole mono- and di- N-oxides which comprises reacting a compound having a methylene group activated by two electron-withdrawing groups, or a compound containing a methylene group which is activated by one electron-withdrawing group selected from nitro, carbonyl of a ketone or aldehyde, with an iosbenzofuroxan in the presence of a base, the activated methylene containing compound and bases being (a) a malonic acid diester in the presence of an alkali metal hydroxide or an alkali metal hydride; (b) a malonamate in 'the presence of alkali metal hydroxide, alkali 'metal alkoxide or alkali metal hydride; (c) a malonic acid diamide in the presence of a base; (d) #-keto ester in the presence of ammonia, a primary or secondary amine or an alkali metal hydride; (e) #-diketone in the presence of ammonia, a primary or secondary amine or alkali metal hydride; (f) #-keto amide in the presence of a tertiary amine, an alkali metal hydroxide, and alkali metal alkoxide, or an alkali metal hydride; (g) a primary or secondary nitro compound in the presence of an alkali metal hydroxide, an alkali metal alkoxide or an alkali metal hydride; (h) malononitrile, cyanoacetamide or a cyano acetate with an alkali metal hydride; (i) a pyruvaldehyde acetal other than the dimethyl acetal in the presence of ammonia or a primary, secondary or tertiary amine; (j) an alicyclic ketone in the presence of alkali metal hydroxide, alkoxide or hydride; (k) a heterocyclic ketone in the presence of ammonia, primary, secondary or tertiary amine or an alkali metal hydroxide, alkoxide or hydride; (1) a ketosulphonyl compound or ketosulphonamide in the presence of a base ; or (m) a C 1-7 alkyl-γ-γ-di-(C 1-7 alkoxy)-acetoacetate other than ethyl-γ,γ-diethoxy acetoacetate in the presence of ammonia, a primary, secondary or tertiary amine or an alkali metal hydroxide, alkoxide or hydride. Novel compounds produced by the process are wherein X is fluoro, trifluoromethyl, sulphonamido, N-methyl sulphonamido or N,N-dimethylsulphonamido substituted on one or more positions of the benzene ring of the quinoxaline and each of R<SP>1</SP> and R<SP>11</SP> is hydrogen or C 1-7 alkyl; wherein R 6 is C 1-7 alkoxy, aryloxy, benzyloxy or NR 8 R 9 where R 8 and R 9 are hydrogen, C 1-7 alkyl, or phenyl; and X is hydrogen, chloro, fluoro, methyl, methoxy, trifluoromethyl, sulphonamido, N-methylsulphonamido or N, N-dimethylsulphonamido substituted on one or more positions of the benzene ring of the quinoxaline, excluding the compounds 2-carbomethoxy-3- hydroxy quinoxaline-di-N-oxide and 2-carboethoxy-3-hydroxy quinoline-di-N-oxide; where X is as in Formula XI where X and R 6 are as in Formula XII wherein X is as in Formula XII, R is C 1-7 alkyl and Y<SP>1</SP> is hydrogen, carbo-C 1-7 alkoxy, excluding 2-formyldimethyl-acetal quinoxaline di-N- oxide and 2-carboethoxy-3-formyl-diethyl acetalquinoxaline di-N-oxide; where X is as in Formula XII, R 4 is C 1-7 alkyl or phenyl and m is zero or 1; where X is as in Formula XII, Z is oxygen, sulphur imino or N-methylimino, m is zero or 1 and n is 2 or 3; where X is as in Formula XII, R 7 is C 1-7 alkyl and Z<SP>1</SP> is halogen, C 1-7 alkoxy, C 1-7 alkanoyloxy, cyano, phenoxy, amino, mercapto or C 1-7 alkylmercapto ; where X is as in Formula XII, R 11 and R 12 are each methyl or ethyl optionally substituted'with chloro, bromo, hydroxy or diethylamino or, taken with the carbon to which they are attached, are cyclohexyl, excluding 2,2-dimethyl- 2H-benzimidazole-1,3-dioxide and 2-methyl-2- ethyl-2H-benzimidazole-1,3-dioxide ; where X is as defined in XII and R 10 is hydrogen, optionally substituted alkyl or aryl, carbalkoxy, or carboxamido, excluding 1-hydroxy-2-benzimidazole propionamide-3-oxide and 1-hydroxy- 2-carbethoxy benzimidazole-3-oxide; where X is as defined in Formula XII, m is 2 to 16, R 3 is halogen, hydroxyl, alkoxy, acetoxy, alkyl, aryl, acetyl, amino, alkylamino, arylamino, acylamino, aroylamino, carboxy, carbalkoxy, nitrile or amido. Other known compounds may also be prepared by the process. Methyl γ,γ-diethoxyacetoacetate may be prepared by reaction of ethyl diethoxyacetate and methyl acetate in the presence of sodium, the former reactant being prepared by reaction of sodium ethoxide and dichloroacetic acid. Pharmaceutical compositions of the compounds of the process show antimicrobial activity when administered topically with the usual excipients and many of the compounds described show growth promotion activity in animals, control chronic respiratory disease in pultry, infectious sinusitis in turkeys, urinary-tract and systemic and non-systemic infections in animals. The compounds are also useful as industrial antimicrobials.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US04/883,577 US4343942A (en) | 1966-11-08 | 1969-12-09 | Quinoxaline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1308370A true GB1308370A (en) | 1973-02-21 |
Family
ID=25382881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4720270A Expired GB1308370A (en) | 1969-12-09 | 1970-10-05 | 1-hydroxy-3-oxo-benzimidazoles quinoxaline-di-n-oxides and benzimidazole-mono-and di-n-oxides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1308370A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2527157A1 (en) * | 1974-06-18 | 1976-02-05 | Egyt Gyogyszervegyeszeti Gyar | PROCESS FOR THE PREPARATION OF (QUINOXALINE-N HIGH 1, N HIGH 4-DIOXYDE-2-YLMETHYLENE) -CARBAZIC ACID METHYLESTER |
| US3997535A (en) * | 1973-03-16 | 1976-12-14 | Allen & Hanburys Limited | Quinoxaline-2-carboxamidotetrazoles |
| US4228151A (en) | 1976-05-03 | 1980-10-14 | L'oreal | Cosmetic composition for imparting to human skin a coloration resembling a natural tan |
| US4228283A (en) | 1978-11-24 | 1980-10-14 | Marxer S.P.A. | Process for preparing pure 2-methyl-3-(β-hydroxyethylcarbamoyl)quinoxaline 1,4-di-N-oxide, and other compounds similar thereto |
| US4264600A (en) | 1978-10-20 | 1981-04-28 | Eli Lilly And Company | Treatment of influenza with 2-estersubstituted-3,4-dihydro-3-oxoquinoxalines |
| FR2482963A1 (en) * | 1980-05-23 | 1981-11-27 | Egyt Gyogyszervegyeszeti Gyar | NOVEL QUINOXALINE-1,4-DIOXIDE DERIVATIVES, THEIR PREPARATION METHODS AND VETERINARY USE COMPOSITIONS CONTAINING SAME |
| US4333931A (en) | 1978-12-19 | 1982-06-08 | Ciba-Geigy Corporation | Method of combatting harmful microorganisms using quinoxaline compounds |
| EP0287806A1 (en) * | 1987-04-13 | 1988-10-26 | The Firestone Tire & Rubber Company | Rubber compositions modified with hydroxy-benzimidazole oxides |
-
1970
- 1970-10-05 GB GB4720270A patent/GB1308370A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3997535A (en) * | 1973-03-16 | 1976-12-14 | Allen & Hanburys Limited | Quinoxaline-2-carboxamidotetrazoles |
| DE2527157A1 (en) * | 1974-06-18 | 1976-02-05 | Egyt Gyogyszervegyeszeti Gyar | PROCESS FOR THE PREPARATION OF (QUINOXALINE-N HIGH 1, N HIGH 4-DIOXYDE-2-YLMETHYLENE) -CARBAZIC ACID METHYLESTER |
| US4228151A (en) | 1976-05-03 | 1980-10-14 | L'oreal | Cosmetic composition for imparting to human skin a coloration resembling a natural tan |
| US4264600A (en) | 1978-10-20 | 1981-04-28 | Eli Lilly And Company | Treatment of influenza with 2-estersubstituted-3,4-dihydro-3-oxoquinoxalines |
| US4228283A (en) | 1978-11-24 | 1980-10-14 | Marxer S.P.A. | Process for preparing pure 2-methyl-3-(β-hydroxyethylcarbamoyl)quinoxaline 1,4-di-N-oxide, and other compounds similar thereto |
| US4333931A (en) | 1978-12-19 | 1982-06-08 | Ciba-Geigy Corporation | Method of combatting harmful microorganisms using quinoxaline compounds |
| FR2482963A1 (en) * | 1980-05-23 | 1981-11-27 | Egyt Gyogyszervegyeszeti Gyar | NOVEL QUINOXALINE-1,4-DIOXIDE DERIVATIVES, THEIR PREPARATION METHODS AND VETERINARY USE COMPOSITIONS CONTAINING SAME |
| EP0287806A1 (en) * | 1987-04-13 | 1988-10-26 | The Firestone Tire & Rubber Company | Rubber compositions modified with hydroxy-benzimidazole oxides |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 429A | Application made for amendment of specification (sect. 29/1949) | ||
| 429H | Application (made) for amendment of specification now open to opposition (sect. 29/1949) | ||
| 429D | Case decided by the comptroller ** specification amended (sect. 29/1949) | ||
| SPA | Amended specification published | ||
| PE20 | Patent expired after termination of 20 years |