CS196281B2 - Method of producing 2-alkoxycarbonyl-amino-5/6/-phenylsulphonyl-oxibenzimidazoles - Google Patents
Method of producing 2-alkoxycarbonyl-amino-5/6/-phenylsulphonyl-oxibenzimidazoles Download PDFInfo
- Publication number
- CS196281B2 CS196281B2 CS786322A CS632278A CS196281B2 CS 196281 B2 CS196281 B2 CS 196281B2 CS 786322 A CS786322 A CS 786322A CS 632278 A CS632278 A CS 632278A CS 196281 B2 CS196281 B2 CS 196281B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- producing
- oxibenzimidazoles
- phenylsulphonyl
- alkoxycarbonyl
- Prior art date
Links
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- -1 acyl radicals Chemical group 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
2-alkoxykarbonylaminobénzintidazolyloVé deriváty s alkylovými zbytky, acyiovýmí zbytky, fenoxyskupinami a fenylthioskupinami v poloze 5(6) jsou již jako anthelmintika známy (P. Actor a další, Nátuře 2Ϊ5, 321 .(1967); DOS 2 029 637; DOS 2 164 690; DOS 2 363 348).2-alkoxycarbonylaminobenzenesulfazolyl derivatives with alkyl radicals, acyl radicals, phenoxy and phenylthio groups in the 5-position (6) are already known as anthelmintics (P. Actor et al., Nature 2-5, 321 (1967); DOS 2 029 637; DOS 2 164 690); ; DOS 2,363,348).
Předmětem vynálezu jsou anthelminticky účinné 2-alkoxykarbonylamino-5:(-6)-fenylsulfonyloxybenzimidazoly obecného vzorce 1, The present invention provides anthelmintically active 2-alkoxycarbonylamino-5 : (-6) -phenylsulfonyloxybenzimidazoles of formula 1,
(1) v němž(1) in which:
Ri znamená alkylový zbytek s 1 až 4 atomy'uhlíku,R 1 represents an alkyl radical having 1 to 4 carbon atoms,
R2 a Rj znamenají vždy nezávisle na sobě vodík, alkoxyskupinu s 1 až 4 atomy uhlíku, halogen, trifluormethylovou skupinu, alkylo196281 vou skupinu s 1 až 4 atomy uhlíku nebo kyanoskupinu.R 2 and R 1 are each independently hydrogen, C 1 -C 4 alkoxy, halogen, trifluoromethyl, C 1 -C 4 alkyl or cyano.
Jako· alkylové zbytky v substituentech Ri, Rž a R3 přicházejí v úvahu: methyl, ethyl, propyl, isopropyl, butyl, sek.butyl, terc.butyl. Jako alkoxyskupiny v substituentech R2 a Ř3 přicházejí v úvahu: methoxyškupína, ethoxyskupina,.propoxyskupina, isopropoxyskupina a butoxyskupina. Jako atomy halogenu v substituentech R2 a R3 přicházejí v úvahu: fluor, chlor, brom a jod.Suitable alkyl radicals in the substituents R1, R2 and R3 are: methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl. Suitable alkoxy groups in substituents R 2 and R 3 are: methoxy, ethoxy, propoxy, isopropoxy and butoxy. Suitable halogen atoms in the substituents R 2 and R 3 are: fluorine, chlorine, bromine and iodine.
Zvláště výhodné jsou sloučeniny vzorce 1, v němž znamená Ri methyl, ethyl, propyl nebo butylí Rž vodík nebo chlor a R3 vodík, chlor nebo trifluormethylovou skupinu.Particularly preferred are compounds of formula 1 wherein R 1 is methyl, ethyl, propyl or butyl R 2 is hydrogen or chlorine and R 3 is hydrogen, chlorine or trifluoromethyl.
Předmětem vynálezu je způsob výroby 2-The object of the invention is a process for producing 2-
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS786322A CS196281B2 (en) | 1974-08-28 | 1978-08-29 | Method of producing 2-alkoxycarbonyl-amino-5/6/-phenylsulphonyl-oxibenzimidazoles |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2441201A DE2441201C2 (en) | 1974-08-28 | 1974-08-28 | 2-Carbalkoxyamino-5 (6) -phenyl-sulfonyloxy-benzimidazoles and process for their preparation |
| CS755619A CS196278B2 (en) | 1974-08-28 | 1975-08-15 | Method of producing 2-alkoxycarbonylamino-5/6/-phenylsulphonyl oxybenzimidazoles |
| CS786322A CS196281B2 (en) | 1974-08-28 | 1978-08-29 | Method of producing 2-alkoxycarbonyl-amino-5/6/-phenylsulphonyl-oxibenzimidazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS196281B2 true CS196281B2 (en) | 1980-03-31 |
Family
ID=25746217
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS786321A CS196280B2 (en) | 1974-08-28 | 1978-08-29 | Method of producing 2-alkoxycarbonyl-amino-5/6/-phenylsulphonyl- oxybenzimidazoles |
| CS786322A CS196281B2 (en) | 1974-08-28 | 1978-08-29 | Method of producing 2-alkoxycarbonyl-amino-5/6/-phenylsulphonyl-oxibenzimidazoles |
| CS786320A CS196279B2 (en) | 1974-08-28 | 1978-08-29 | Method of producing 2-alkoxycarbonylamino-5/6/-phenylsulphonyl oxybenzimidazoles |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS786321A CS196280B2 (en) | 1974-08-28 | 1978-08-29 | Method of producing 2-alkoxycarbonyl-amino-5/6/-phenylsulphonyl- oxybenzimidazoles |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS786320A CS196279B2 (en) | 1974-08-28 | 1978-08-29 | Method of producing 2-alkoxycarbonylamino-5/6/-phenylsulphonyl oxybenzimidazoles |
Country Status (1)
| Country | Link |
|---|---|
| CS (3) | CS196280B2 (en) |
-
1978
- 1978-08-29 CS CS786321A patent/CS196280B2/en unknown
- 1978-08-29 CS CS786322A patent/CS196281B2/en unknown
- 1978-08-29 CS CS786320A patent/CS196279B2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS196279B2 (en) | 1980-03-31 |
| CS196280B2 (en) | 1980-03-31 |
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