IL36101A - 5 or 6-substituted amino-2-(4'-thiazolyl)-benzimidazoles and their preparation - Google Patents
5 or 6-substituted amino-2-(4'-thiazolyl)-benzimidazoles and their preparationInfo
- Publication number
- IL36101A IL36101A IL36101A IL3610171A IL36101A IL 36101 A IL36101 A IL 36101A IL 36101 A IL36101 A IL 36101A IL 3610171 A IL3610171 A IL 3610171A IL 36101 A IL36101 A IL 36101A
- Authority
- IL
- Israel
- Prior art keywords
- loweralkyl
- compound
- derivatives
- formula
- alkoxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims 23
- 239000002253 acid Substances 0.000 claims 9
- 150000002148 esters Chemical class 0.000 claims 9
- 150000004820 halides Chemical class 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 3
- -1 amine salts Chemical class 0.000 claims 2
- 125000003051 glycosyloxy group Chemical group 0.000 claims 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 2
- 150000003462 sulfoxides Chemical class 0.000 claims 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims 1
- IRSPCJLMPFDMGD-UHFFFAOYSA-N 1-hydroxybenzimidazole Chemical compound C1=CC=C2N(O)C=NC2=C1 IRSPCJLMPFDMGD-UHFFFAOYSA-N 0.000 claims 1
- IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002431 aminoalkoxy group Chemical group 0.000 claims 1
- 230000000507 anthelmentic effect Effects 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000010531 catalytic reduction reaction Methods 0.000 claims 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims 1
- 229910001385 heavy metal Inorganic materials 0.000 claims 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Claims (14)
1. Compounds having the formula: significations: -X represents oxygen or sulfur; ie in the 5-posltion, R2 represents (lower carbalkox )(lower alkoxy), aminoloweralkpxy containing from 2 to 6 oaron atoms in the ■•4* - - - -- _ alkoxy moiety and the E-loweraikyl, Ν,Η-diloweralkyl and triloweralkylaminoniuni halide derivatives thereof, phosphonolower-alkoxy and loweralkyl esters thereof, phoephatoloweralkoxy and loweralkyl esters thereof, loweralkylthioloweralkoxy and the sulfoxide and eulfone derivatives thereof, sulf loweralkoxy, C-amidinoloweralkoxy and M^ and - loweralkyl derivatives thereof, B-amidinoloweralkoxy vherein oe anld no moiety is derived from a lotieralfeanoic acid and the H-loweralkyl derivatives thereof, biguanidoloweralkoxy, guanldinoloweralkoxy and the fig, and 3SL loweralkyl derivatives 36101/3 thereof, aminoguanidinoloweralkoxy and the N* , N^, N2, and lower alkyl derivatives thereof, iraidazolinylaminolower-alkoxy and the 1-loweralkyl derivatives thereof, 1,4,5(6-tetrahydropyriraidinylaminoloweralkoxy and the 1-loweralkyl derivatives thereof, thiazolinylarainoloweralkoxy, imidaaolinoloweralkoxy and the 1-loweralkyl derivatives thereof, l,4,5,6-tetrahydropyrimidinoloweralk6xy and the 1-loweralkyl derivatives thereof, lowerelkanoyloxy, glycoayloxy, j-loweralkylphenacyloxy and j -loweralkoxyphenacyloxy; and non-toxio alkali metal, alkaline earth meatal and pharmaceutically acceptable amine salts and heavy metal oomplexes ^ , _ (lower csrbalkpxy) (lower alkoxy), thereof when Rg is ee ¾o.tyloworal¾
2. A compound of Claim 1 wherein X is oxygen and R2 is loweralkyl, loweralkanoyl, loweralkanoyloxy, loweralkox carbonyl or carbamoyl.
3. A compound of Claim 1 wherein X is oxygen and R2 is hydroxy, loweralkoxy, carboxylower-alkoxy, and loweralkyl esters thereof, aminoloweralkoxy containing from 2 to 6 carbon atoms in the alkoxy moiety and the N-loweralk l , Ν,Ν-diloweralkyl, and triloweralkyl-ammonium halide derivatives thereof, phosphonoloweralkox , and loweralkyl esters thereof, loweralkylthioloweralkoxy, and the sulfoxide, and sulfone derivatives thereof, sulfo-loweralkoxy, C-amidinoloweralkoxy and N^- and Hj-loweralkyl derivatives thereof, N-amidinoloweralkoxy wherein the amidino moiety is derived from a loweralkanoic acid and the N-loweralkyl derivatives thereof, biguanidolower- alkoxy, guanidinoloweralkoxy, and the N^, N2, and N3 loweralkyl derivatives thereof, aminoguanidinoloweralkoxy and the Ν' , N2, and N3 loweralkyl derivatives thereof, imidazolylaminoloweralkoxy and the l-loweralkyl derivatives thereof, 1,4, 5, 6-tetrahydropyrimidinylaminoloweralkoxy and the l-loweralkyl derivatives thereof, thiazolinylamino- loweralkoxy, imidazolinolower- -66- 36101/3 alkoxy and the 1-loweralkyl derivatives thereof, 1,4, 5*6" tetrahydropyrimidinoloweraikoxy and the l-loweralkyl derivatives thereof, lo eralkanoyloxy, glycosyloxy, £-loweralkylphenacyloxy and £-loweralkoxyphenacyloxy; and pharmaceutically acceptable salts thereof where the R2 group contains a, free hydrogen.
4. A compound of Claim 1 wherein X is oxygen and ¾2 is phosphonoloweralkoxy, phosphatoloweralkoxy, sulfoloweralkoxy, C-amidinolowe alkoxy, N-amidinolower- alkoxy (wherein the amidino moiety is derived from a loweralkanoic acid) biguanidoloweralkox , guanidinolowerr alkoxy, aminoguanidinoloweralkoxy, imidazolylaminolower- alkoxy; 1,4, 5,6-tetrahydropyrimidinylaminoloweralkoxy, 1,4,5 »6-tetrehydropyrimidinoloweralkoxy, and glycosyloxy, end the loweralkyl esters thereof. ,
5. Λ compound of Claim 1 wherein is oxygen and R2 is carboxyalkoxy, aminoalkoxy, N-alkylaminoalkoxy, Ν,Ν-dialkylaminoalkoxy, diaminoalkoxy, phosphonoloweralkoxy, eulfoloweralkoxy, C-amid noalkoxy, N-amidinoalkoxy, or guanidinoloweralkox .
6. ". A compound of Claim 1- wherein : is hydrogen, and is selected from loweralkoxy and phenyl.
7. A compound of Claim 6 which is 5- or 6- loweralkoxycarbonylamino-l-R2-2-(4'-thiazolyl)-benzimidazole.
8. The compo nd of Claim 7 which is 5- or 6- iaopropoxycarDonylamino-l-{2,-sulfoethoxy)-2-(4'.-thiazolyl)- benzimidazole. 56101/5
9. An anthelmintic compoeiton ha comprises a carrier vehicle having intimately dispersed therein an anthelmintically effective amount of a compound according to anyone of the preceding claims . (
10. The composition of Claim .9: wherein the carrier vehicle is in the form of a drench. 11· A process for preparing a compound of the formulaj wherein R^, R^, ^, and X are as defined in Claim 1, and R2 is loweralkoxy, carboxyloweralkoxy and · , loweralkyl esters thereof, phosphonoloweralkoxy and lower* alkyl esters thereof, loweralkylthioloweralkoxy, sulfo- loweralkoxy, guanidinoloweralkoxy, imidazolinoloweralkoxy and the 1-loweralkyl derivatives thereof, 1,4,5,6- tetrahydropyrimidinoloweralkoxy and the 1-loweralkyl derivatives thereof, loweralkanoyloxy, glycoeyloxy, jj-loweralkylphenacyloxy and jj- 13615 36101/2 loweralkoxyphenacylox , which comprises reacting a 1-hydroxy benzimidazole of the formula: wherein ^, R^, R^, and X are as defined in Claim 1, in the presence of a base with a 'member selected from the group consisting of a loweralkyl halide, a haloloweralkanoic acid, a loweralkyl ester of a halolower-. alkanoic acid, a haloloweralkylphosphonic acid, a halo-loweralkylsulfonic acid, a loweralkylthioloweralkyl halide, an imidazolinoloweralkyl halide, a 1-loweralkylimidazolino-loweralkyl halide, a 1, 4, 5, 6-tetrahydropyrimidinoloweralkyl halide, a loweralkanoic acid halide, an a-aminocarboxy- loweralkyl halide, a glycosyl halide, an a-halo-g- loweralkoxy acetophenone and an a-halo-£-loweralkyl acetophenone.
11. 1. Ί2.
12. A process for preparing a compound of the formula: wherein ^, R^, ^, and X are as defined in Claim 1, and R- is aminoloweralkoxy, which comprises reacting a compound of the formula: wherein R^, R^, R^, and X are as defined in Claim 1, and Rg is loweralkyl, with hydrazine hydrate. .1/6.
13. A process for preparing a compound of the formula : wherein 1 R3, 4 and X are as defined in Claim 1, and R2 is imidazolylaminoloweralkoxy and the 1-loweralkyl derivatives thereof, 1,4,5,6-tetrahydropyrimidinylamino-loweralkoxy and the 1-loweralkyl derivatives thereof, thiazolinylaminoloweralkoxy, thiaainylaminoloweiralkoxy , and guanidinoloweralkoxy, which comprises reacting a compound of the formula: wherein R^, R^, 4, and X are as defined in Claim 1 and Rg is loweralkyl with a compound of the formula: CH3 - S - R? wherein R? is a member selected from the group consisting of 2-imidazolino, l-loweralkyl-2-imidazolino, 2- (1,4, 5,6-tetrahydropyrimidino) , l-loweralkyl-2-(l,4,5,6-tetrahydro pyrimidino) , 2-thiazolino, | and amidino.
14. i A process for preparing a compound of the formula: wherein R^, ^, R4, and X are as defined in Claim 1, and R2 is biguanidoloweralkoxy, which comprises reacting a compound of the formula: wherein R^, R^, ^, and X are as defined in Claim 1, and Rg is loweralkyl, in an aqueous solvent with dicyandiamide . 15 · ί A process for preparing a compound of the formula: wherein ^, R^, R^, and X are as defined in Claim 1 and R2 is aminoguanidinoloweralkoxy, which comprises reacting a compound of the formula: wherein R^, R^/ and X are as defined in Claim 1 and Rg is loweralkyl, with nitroguanidine to produce the corresponding 1-nitroguanidinoloweralkoxy benzimidazole and reduc.ing the nitro group by catalytic reduction. ib i§-. The method for preparing an N-amidine compound of the formula: wherein R^, R^, R4, and X are as defined in Claim 1, Rg is loweralkyl; and Rg, Rg, and ^Q are members selected from the group consisting of hydrogen and loweralkyl, which comprises reacting an imino ether of the formula: ♦ 136 wherein R^, R^, R^, and X are as defined in Claim 1 and ^ is loweralkyl, in the presence of a catalytic quantity of hydrochloric acid with a compound of the formula : H - N - R10 wherein Rg and R1Q are defined above, n The method of preparing a N-amidino compound of the formula: wherein R^, R3, R4, and X are as defined in Claim lr Rg is loweralkyl, and R^2 and R^3 are members selected from the group consisting of hydrogen and loweralkyl, which comprises reacting a compound of the formula: wherein R. , R, , R. , and X are as defined in Claim 1, with a loweralkyl imino ester hydrochloride of the formula: wherein R1 is as defined above and R, A is loweralkyl. The method of preparing a C-amidino compound of the formula: wherein R^, R^, R^, and X are as defined in Claim 1, Rg is loweralkyl, and R^ and R^g are members selected from the group consisting of hydrogen and loweralkyl, which comprises reacting an imino ester hydrochloride of the formula: wherein ^, R^, R4, and X are as defined in Claim 1, with a compound of the formula: wherein R^,. and R^g are as described above. -2-2. The method of preparing a compound of the formula: wherein R^, R3, R4, and X are as defined in Claim 1, and R-. is phosphatoloweralkoxy which comprises reacting a compound of the formula: wherein ^, R^, ^, and X are as defined in Claim 1, Rg is loweralkyl, with orthophosphonic acid in the presence of phosphoric acid anhydride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1695770A | 1970-03-05 | 1970-03-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL36101A0 IL36101A0 (en) | 1971-04-28 |
| IL36101A true IL36101A (en) | 1976-02-29 |
Family
ID=21779932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL36101A IL36101A (en) | 1970-03-05 | 1971-02-01 | 5 or 6-substituted amino-2-(4'-thiazolyl)-benzimidazoles and their preparation |
Country Status (10)
| Country | Link |
|---|---|
| AR (3) | AR199179A1 (en) |
| CS (1) | CS180571B2 (en) |
| ES (5) | ES388211A1 (en) |
| IE (2) | IE34938B1 (en) |
| IL (1) | IL36101A (en) |
| NO (1) | NO131932C (en) |
| SU (1) | SU472504A3 (en) |
| YU (1) | YU34895B (en) |
| ZA (1) | ZA7164B (en) |
| ZM (1) | ZM2571A1 (en) |
-
1971
- 1971-01-06 ZA ZA710064A patent/ZA7164B/en unknown
- 1971-02-01 IL IL36101A patent/IL36101A/en unknown
- 1971-02-09 IE IE14871A patent/IE34938B1/en unknown
- 1971-02-09 IE IE14971A patent/IE34939B1/en unknown
- 1971-02-10 NO NO48771A patent/NO131932C/no unknown
- 1971-02-12 ES ES388211A patent/ES388211A1/en not_active Expired
- 1971-03-01 CS CS152171A patent/CS180571B2/en unknown
- 1971-03-02 YU YU51571A patent/YU34895B/en unknown
- 1971-03-04 ZM ZM2571A patent/ZM2571A1/en unknown
- 1971-03-04 SU SU1629945A patent/SU472504A3/en active
- 1971-12-01 AR AR23935671A patent/AR199179A1/en active
- 1971-12-01 AR AR23935471A patent/AR199177A1/en active
- 1971-12-01 AR AR23935571A patent/AR199178A1/en active
-
1973
- 1973-06-02 ES ES415483A patent/ES415483A1/en not_active Expired
- 1973-06-02 ES ES415482A patent/ES415482A1/en not_active Expired
- 1973-06-02 ES ES415481A patent/ES415481A1/en not_active Expired
- 1973-06-02 ES ES415480A patent/ES415480A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE34938L (en) | 1971-09-05 |
| ES415483A1 (en) | 1976-02-16 |
| AR199177A1 (en) | 1974-08-14 |
| SU472504A3 (en) | 1975-05-30 |
| AR199178A1 (en) | 1974-08-14 |
| IE34939B1 (en) | 1975-10-01 |
| YU51571A (en) | 1979-10-31 |
| ZA7164B (en) | 1972-08-30 |
| CS180571B2 (en) | 1978-01-31 |
| IE34939L (en) | 1971-09-05 |
| AR199179A1 (en) | 1974-08-14 |
| ES415482A1 (en) | 1976-11-16 |
| YU34895B (en) | 1980-04-30 |
| IL36101A0 (en) | 1971-04-28 |
| NO131932C (en) | 1975-08-27 |
| ZM2571A1 (en) | 1972-10-23 |
| ES415481A1 (en) | 1976-02-16 |
| ES388211A1 (en) | 1974-02-16 |
| ES415480A1 (en) | 1976-02-16 |
| NO131932B (en) | 1975-05-20 |
| IE34938B1 (en) | 1975-10-01 |
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