CS230343B1 - Amides derived from 2-aminobenzimidazole - Google Patents
Amides derived from 2-aminobenzimidazole Download PDFInfo
- Publication number
- CS230343B1 CS230343B1 CS112583A CS112583A CS230343B1 CS 230343 B1 CS230343 B1 CS 230343B1 CS 112583 A CS112583 A CS 112583A CS 112583 A CS112583 A CS 112583A CS 230343 B1 CS230343 B1 CS 230343B1
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- CS
- Czechoslovakia
- Prior art keywords
- propanol
- formula
- aminobenzimidazole
- methylcellosolv
- amides
- Prior art date
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- 150000001408 amides Chemical class 0.000 title claims description 7
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 title claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 2
- -1 2-chlorophenoxy Chemical group 0.000 claims 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- YBADLXQNJCMBKR-UHFFFAOYSA-N (4-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C([N+]([O-])=O)C=C1 YBADLXQNJCMBKR-UHFFFAOYSA-N 0.000 description 1
- AZTFYJYLDIQSAG-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(propan-2-ylamino)propan-1-one Chemical compound CC(C)NC(C)C(=O)C1=CC=C(Cl)C=C1 AZTFYJYLDIQSAG-UHFFFAOYSA-N 0.000 description 1
- MEDUMEPHJCDDHQ-UHFFFAOYSA-N 2-amino-2H-phenazin-1-one 4-(dimethylamino)-1,5-dimethyl-2-phenylpyrazol-3-one Chemical compound C1=CC=C2N=C(C(C(N)C=C3)=O)C3=NC2=C1.O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 MEDUMEPHJCDDHQ-UHFFFAOYSA-N 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Vynález se týká amidů, odvozených od 2-aminobenzimidazolu obecného vzorce IThe invention relates to amides derived from 2-aminobenzimidazole of the general formula I
ve kterém skupina RCO— značí zbytek kyseliny 1- (p-chlorbenzoyl) -5-methoxy-2-methyl-3-indolylcctové, benzylové, difenyloctové, 4-chlorfenyloctové, 4-methoxyfenyloctové, 4-fluorfenyloctové, 4-nitrofenyloctové, 3,4-dimethoxyfenyloctové, fenoxyoctové, 2-chlorfenoxyoctové, 4-chlorfenoxyoctové, 2,4-dichlorfenoxyoctové, fenoxyisomáselné, 4-chlorfenoxyisomáselné, 4-chlorbenzoové, nikotinové a isonikotinové.wherein the RCO group is 1- (p-chlorobenzoyl) -5-methoxy-2-methyl-3-indolyl acetic acid, benzyl, diphenylacetic, 4-chlorophenylacetic, 4-methoxyphenylacetic, 4-fluorophenylacetic, 4-nitrophenylacetic acid, 3, 4-dimethoxyphenylacetic, phenoxyacetic, 2-chlorophenoxyacetic, 4-chlorophenoxyacetic, 2,4-dichlorophenoxyacetic, phenoxyisobutyric, 4-chlorophenoxyisobutyric, 4-chlorobenzoic, nicotinic and isonicotinic.
Látky obecného vzorce I, které jsou nové, byly testovány na analgetickou účinnost ve srovnávacích testech s aminofenazonem (l-fenyl-2,3-dimelhyl-4-dimethylamino-5-pyrazolon. Z připravených látek byla jako nejzajímavější vyhodnocena látka 1 (viz příklad lj, která vykázala v uvedených testech významnou analgetickou aktivitu při podstatně nižší toxicitě oproti standardu.Compounds of formula I that are novel have been tested for analgesic activity in comparative tests with aminophenazone (1-phenyl-2,3-dimethyl-4-dimethylamino-5-pyrazolone). 1j, which showed significant analgesic activity in the above assays with substantially lower toxicity than the standard.
Vynález se týká také způsobu výroby látek obecného vzorce I. Podle vynálezu se látky obecného vzorce I připravují například tak, že se nejprve kyselina obecného vzorce IIThe invention also relates to a process for the preparation of the compounds of the formula I. According to the invention, the compounds of the formula I are prepared, for example, by first preparing an acid of the formula II
RCOOH (II).RCOOH (II).
ve kterém skupina RCO— značí totéž co ve vzorci I, převádí reakcí s Ι,Γ-karbonyldiimidazolem na příslušný imidazolid, který reaguje in šitu s 2-aminobenzimidazolem vzorce IIIin which the RCO-group denotes the same as in formula I, by reaction with Ι, Γ-carbonyldiimidazole, the corresponding imidazolide, which reacts in situ with the 2-aminobenzimidazole of formula III
Reakce se výhodně provádí v prostředí dichlormethanu při teplotě místnosti a během 24 h je skončena.The reaction is preferably carried out in dichloromethane at room temperature and is complete in 24 h.
Všechny použité meziprodukty jsou známé a lze je připravit známými postupy.All intermediates used are known and can be prepared by known methods.
Podrobnosti způsobu provedení jsou uvedeny v následujících příkladech provedení.Details of the embodiment are given in the following examples.
PřikladlHe did
K roztoku 0,02 mol Ι,Γ-karbonyldiimidazolu v 50 ml dichlormethanu se přidá při teplotě místnosti 0,02 mol kyseliny l-(p-chlorbenzoyl) -5-methoxy-2-methyl-3-indolyloctové, směs se míchá 5 minut a k takto připravenému imidazolidu se přidá 0,02 mol 2-aminobenzimidazolu. V míchání při teplotž místnosti se pokračuje 6 h, směs se ponechá do příštího dne, vyloučené krystaly se odsají, promyjí dichlormethanem a překrystalují z 2-propanolu. Získá se 4,2 g žádaného amidu, t. t. 216 až 217 °C. (Látka 1]To a solution of 0.02 mol of Ι, Γ-carbonyldiimidazole in 50 ml of dichloromethane was added at room temperature 0.02 mol of 1- (p-chlorobenzoyl) -5-methoxy-2-methyl-3-indolylacetic acid, stirred for 5 minutes and to the thus prepared imidazolide is added 0.02 mol of 2-aminobenzimidazole. Stirring at room temperature is continued for 6 h, the mixture is left until the next day, the precipitated crystals are filtered off with suction, washed with dichloromethane and recrystallized from 2-propanol. 4.2 g of the desired amide is obtained, m.p. 216-217 ° C. (Fabric 1)
Tabulka 1 (látky 2 až 17)Table 1 (substances 2 to 17)
Látka RFabric R
Příklad 2Example 2
Stejným způsobem jak bylo popsáno v příkladu 1 se připraví amidy 2 až 17. Způsob izolace amidů 3, 9, 10, 13 a 14 se liší od popsaného tím, že produkt nekrystaluje z reakční směsi, ale získá se ve formě odparku po několikanásobném promytí dichlormeíhanového roztoku vodou a oddestilování rozpouštědla za sníženého tlaku k suchu. Krystalizace odparku z vhodného rozpouštědla poskytne čistou látku.In the same manner as described in Example 1, amides 2 to 17 are prepared. The process for isolating amides 3, 9, 10, 13 and 14 differs from that described in that the product does not crystallize from the reaction mixture but is obtained as a residue after washing several times with dichloromethane. of water and distilling off the solvent to dryness under reduced pressure. Crystallization of the residue from a suitable solvent gives the pure material.
T. t. °C Rozpouštědlo (C6H5)2C(OH) (C6H5)2CHMp. ° C Solvent (C6 H5) 2 C (OH) (C 6 H 5) 2 CH
4-C1C6H4CI-I24-ClC6H4Cl-I2
4 CH3OC6IT4CH24 CH3OC6IT4CH2
4-FC6H4CH24-FC6H4CH2
4-NO2C8H4CH24-NO2C8H4CH2
3,4-(CH3O)aC8H3CH23,4- (CH 3 O) and C 8 H 3 CH 2
C6H5OCH2C6H5OCH2
2-CIC6H4OCH22-CIC 6 H 4 OCH 2
4-CIC6H4OCH24-CIC 6 H 4 OCH 2
2,4-Cl2C6H3OCH22,4-Cl 2 C 6 H 3 OCH 2
CsH5OC(CH3)2CsH5OC (CH3) 2
4-ClC6H4OC(CH3)24-ClC6H4OC (CH3) 2
4-C1C6H44-C1C6H4
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS112583A CS230343B1 (en) | 1983-02-18 | 1983-02-18 | Amides derived from 2-aminobenzimidazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS112583A CS230343B1 (en) | 1983-02-18 | 1983-02-18 | Amides derived from 2-aminobenzimidazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS230343B1 true CS230343B1 (en) | 1984-08-13 |
Family
ID=5344819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS112583A CS230343B1 (en) | 1983-02-18 | 1983-02-18 | Amides derived from 2-aminobenzimidazole |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS230343B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118221668A (en) * | 2024-03-19 | 2024-06-21 | 华南农业大学 | An indomethacin derivative containing 2-amino-1,3,4-thiadiazole and its preparation method and application |
-
1983
- 1983-02-18 CS CS112583A patent/CS230343B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118221668A (en) * | 2024-03-19 | 2024-06-21 | 华南农业大学 | An indomethacin derivative containing 2-amino-1,3,4-thiadiazole and its preparation method and application |
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