DE2159674A1 - Neue 2-Acryloy!benzimidazole, Verfahren zu ihrer Herstellung und ihre Verwendung als Wirkstoffkomponente in Arzneimitteln - Google Patents
Neue 2-Acryloy!benzimidazole, Verfahren zu ihrer Herstellung und ihre Verwendung als Wirkstoffkomponente in ArzneimittelnInfo
- Publication number
- DE2159674A1 DE2159674A1 DE19712159674 DE2159674A DE2159674A1 DE 2159674 A1 DE2159674 A1 DE 2159674A1 DE 19712159674 DE19712159674 DE 19712159674 DE 2159674 A DE2159674 A DE 2159674A DE 2159674 A1 DE2159674 A1 DE 2159674A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- active ingredient
- benzimidazole
- new
- benzimidaz
- 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.)
- Pending
Links
- 239000004480 active ingredient Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 239000003814 drug Substances 0.000 title claims 2
- 150000001556 benzimidazoles Chemical class 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- SBKMFVRKUCKHLB-UHFFFAOYSA-N 1-(1H-benzimidazol-2-yl)prop-2-en-1-one Chemical compound C(=O)(C=C)C=1NC2=C(N1)C=CC=C2 SBKMFVRKUCKHLB-UHFFFAOYSA-N 0.000 claims description 6
- UYFMRVDIXXOWLR-UHFFFAOYSA-N 1-(1h-benzimidazol-2-yl)ethanone Chemical compound C1=CC=C2NC(C(=O)C)=NC2=C1 UYFMRVDIXXOWLR-UHFFFAOYSA-N 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 229940126601 medicinal product Drugs 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 206010030113 Oedema Diseases 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- -1 alkoxy radical Chemical class 0.000 claims 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- JYZIHLWOWKMNNX-UHFFFAOYSA-N benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000001631 hypertensive effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- QSCCDAGMEXKGHL-DHZHZOJOSA-N (e)-1-(1h-benzimidazol-2-yl)-3-(4-methoxyphenyl)prop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1\C=C\C(=O)C1=NC2=CC=CC=C2N1 QSCCDAGMEXKGHL-DHZHZOJOSA-N 0.000 description 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 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 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
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7043089A FR2116246B1 (enExample) | 1970-12-01 | 1970-12-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2159674A1 true DE2159674A1 (de) | 1972-06-22 |
Family
ID=9064992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712159674 Pending DE2159674A1 (de) | 1970-12-01 | 1971-12-01 | Neue 2-Acryloy!benzimidazole, Verfahren zu ihrer Herstellung und ihre Verwendung als Wirkstoffkomponente in Arzneimitteln |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3755314A (enExample) |
| BE (1) | BE775669A (enExample) |
| CA (1) | CA945163A (enExample) |
| CH (1) | CH525217A (enExample) |
| DE (1) | DE2159674A1 (enExample) |
| ES (1) | ES397512A1 (enExample) |
| FR (1) | FR2116246B1 (enExample) |
| GB (1) | GB1311460A (enExample) |
| IL (1) | IL38199A (enExample) |
| LU (1) | LU64365A1 (enExample) |
| NL (1) | NL7116540A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4107489A1 (de) * | 1991-03-08 | 1992-09-10 | Beiersdorf Ag | Kosmetische mittel, die 2-(3'-arylacryloyl)benzimidazol-derivate enthalten, neue 2-(3'-arylacryloyl)benzimidazol-derivate, verfahren zu ihrer herstellung und ihre verwendung |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE791908A (fr) * | 1971-11-24 | 1973-05-24 | Beecham Group Ltd | Derives du benzimidazole |
| CN104140415B (zh) * | 2014-06-03 | 2017-02-15 | 中国医学科学院医药生物技术研究所 | 含有苯并五元不饱和杂环结构的α、β不饱和酮类化合物及其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2754299A (en) * | 1954-07-02 | 1956-07-10 | Lasdon Foundation Inc | Heterocyclic chalcone compounds |
| US3577419A (en) * | 1969-10-24 | 1971-05-04 | Sandoz Ag | 2,6-disubstituted-4-(omega-aminoalkoxy) phenyl pyrimidines |
-
1970
- 1970-12-01 FR FR7043089A patent/FR2116246B1/fr not_active Expired
-
1971
- 1971-11-16 GB GB5301971A patent/GB1311460A/en not_active Expired
- 1971-11-22 CH CH1697671A patent/CH525217A/fr not_active IP Right Cessation
- 1971-11-22 IL IL38199A patent/IL38199A/en unknown
- 1971-11-22 BE BE775669A patent/BE775669A/xx unknown
- 1971-11-26 US US00202637A patent/US3755314A/en not_active Expired - Lifetime
- 1971-11-29 LU LU64365D patent/LU64365A1/xx unknown
- 1971-11-30 CA CA128,994*7A patent/CA945163A/en not_active Expired
- 1971-11-30 ES ES397512A patent/ES397512A1/es not_active Expired
- 1971-12-01 NL NL7116540A patent/NL7116540A/xx unknown
- 1971-12-01 DE DE19712159674 patent/DE2159674A1/de active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4107489A1 (de) * | 1991-03-08 | 1992-09-10 | Beiersdorf Ag | Kosmetische mittel, die 2-(3'-arylacryloyl)benzimidazol-derivate enthalten, neue 2-(3'-arylacryloyl)benzimidazol-derivate, verfahren zu ihrer herstellung und ihre verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2116246A1 (enExample) | 1972-07-13 |
| IL38199A0 (en) | 1972-01-27 |
| NL7116540A (enExample) | 1972-06-05 |
| ES397512A1 (es) | 1975-03-16 |
| IL38199A (en) | 1974-11-29 |
| FR2116246B1 (enExample) | 1974-03-22 |
| BE775669A (fr) | 1972-05-23 |
| CA945163A (en) | 1974-04-09 |
| US3755314A (en) | 1973-08-28 |
| LU64365A1 (enExample) | 1972-08-03 |
| GB1311460A (en) | 1973-03-28 |
| CH525217A (fr) | 1972-07-15 |
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