DE2158801C3 - - Google Patents
Info
- Publication number
- DE2158801C3 DE2158801C3 DE19712158801 DE2158801A DE2158801C3 DE 2158801 C3 DE2158801 C3 DE 2158801C3 DE 19712158801 DE19712158801 DE 19712158801 DE 2158801 A DE2158801 A DE 2158801A DE 2158801 C3 DE2158801 C3 DE 2158801C3
- Authority
- DE
- Germany
- Prior art keywords
- respiratory
- compounds according
- formula
- compounds
- substituted
- 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
- 150000001875 compounds Chemical class 0.000 claims description 18
- -1 dipropylaminomethyl Chemical group 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- HRTNGSCQAGSUOB-UHFFFAOYSA-N 1-(3-phenylprop-2-enyl)benzimidazole Chemical group C1=NC2=CC=CC=C2N1CC=CC1=CC=CC=C1 HRTNGSCQAGSUOB-UHFFFAOYSA-N 0.000 claims description 2
- 150000001556 benzimidazoles Chemical class 0.000 claims description 2
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 2
- 230000000241 respiratory Effects 0.000 description 8
- BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Chemical compound [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 description 6
- 230000002048 spasmolytic Effects 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 230000000202 analgesic Effects 0.000 description 4
- 230000004936 stimulating Effects 0.000 description 4
- ZDHWSRRZUPRQBD-UHFFFAOYSA-N 2-[but-2-enoyl(ethyl)amino]-N,N-dimethylbutanamide;2-[but-2-enoyl(propyl)amino]-N,N-dimethylbutanamide Chemical compound CN(C)C(=O)C(CC)N(CC)C(=O)C=CC.CN(C)C(=O)C(CC)N(CCC)C(=O)C=CC ZDHWSRRZUPRQBD-UHFFFAOYSA-N 0.000 description 3
- IWTYTFSSTWXZFU-QPJJXVBHSA-N [(E)-3-chloroprop-1-enyl]benzene Chemical compound ClC\C=C\C1=CC=CC=C1 IWTYTFSSTWXZFU-QPJJXVBHSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000003555 analeptic Effects 0.000 description 3
- 230000001077 hypotensive Effects 0.000 description 3
- 229940042542 prethcamide Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N Papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000002269 analeptic agent Substances 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drugs Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 229960001789 papaverine Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000000304 vasodilatating Effects 0.000 description 2
- 230000000261 vasodilator Effects 0.000 description 2
- 239000003071 vasodilator agent Substances 0.000 description 2
- WBDCCRNAPCOHAV-UHFFFAOYSA-N 4-(1H-benzimidazol-2-ylmethyl)morpholine Chemical compound N=1C2=CC=CC=C2NC=1CN1CCOCC1 WBDCCRNAPCOHAV-UHFFFAOYSA-N 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L Barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 210000004351 Coronary Vessels Anatomy 0.000 description 1
- 210000001198 Duodenum Anatomy 0.000 description 1
- 206010058061 Gastrointestinal oedema Diseases 0.000 description 1
- 206010017999 Gastrointestinal pain Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229960005195 Morphine hydrochloride Drugs 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive Effects 0.000 description 1
- 230000001396 anti-anti-diuretic Effects 0.000 description 1
- 230000003276 anti-hypertensive Effects 0.000 description 1
- 230000003110 anti-inflammatory Effects 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000001882 diuretic Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- XCKKIKBIPZJUET-VYKNHSEDSA-N morphine hydrochloride Chemical compound Cl.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O XCKKIKBIPZJUET-VYKNHSEDSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 210000000056 organs Anatomy 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000035812 respiration Effects 0.000 description 1
- 230000036391 respiratory frequency Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000036387 respiratory rate Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7042636A FR2115067B1 (ja) | 1970-11-27 | 1970-11-27 | |
| FR7042636 | 1970-11-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2158801A1 DE2158801A1 (de) | 1972-06-22 |
| DE2158801B2 DE2158801B2 (de) | 1977-01-27 |
| DE2158801C3 true DE2158801C3 (ja) | 1977-09-15 |
Family
ID=9064819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712158801 Granted DE2158801B2 (de) | 1970-11-27 | 1971-11-26 | In 2-stellung substituierte 1-cinnamylbenzimidazolderivate, verfahren zu ihrer herstellung und arzneimittel |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3758459A (ja) |
| AU (1) | AU457142B2 (ja) |
| BE (1) | BE775040A (ja) |
| CA (1) | CA955253A (ja) |
| CH (1) | CH523889A (ja) |
| CS (1) | CS174851B2 (ja) |
| DE (1) | DE2158801B2 (ja) |
| ES (1) | ES397205A1 (ja) |
| FR (1) | FR2115067B1 (ja) |
| GB (1) | GB1311419A (ja) |
| IL (1) | IL38149A (ja) |
| LU (1) | LU64306A1 (ja) |
| NL (1) | NL7116314A (ja) |
| SE (1) | SE378245B (ja) |
| SU (1) | SU432718A3 (ja) |
| ZA (1) | ZA717617B (ja) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2244500B1 (ja) * | 1973-07-03 | 1977-07-01 | Delalande Sa | |
| EP0000574B1 (de) * | 1977-08-01 | 1982-08-04 | Ciba-Geigy Ag | Benzimidazol-2-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Arzneimitteln |
| JPH07137179A (ja) * | 1993-07-19 | 1995-05-30 | Xerox Corp | ２つの部材を移動可能に連結した組立体を製造する方法 |
-
1970
- 1970-11-27 FR FR7042636A patent/FR2115067B1/fr not_active Expired
-
1971
- 1971-11-04 CH CH1614071A patent/CH523889A/fr not_active IP Right Cessation
- 1971-11-08 BE BE775040A patent/BE775040A/xx unknown
- 1971-11-12 ZA ZA717617A patent/ZA717617B/xx unknown
- 1971-11-15 IL IL38149A patent/IL38149A/en unknown
- 1971-11-16 GB GB5302071A patent/GB1311419A/en not_active Expired
- 1971-11-18 AU AU35877/71A patent/AU457142B2/en not_active Expired
- 1971-11-19 CS CS8113A patent/CS174851B2/cs unknown
- 1971-11-20 ES ES397205A patent/ES397205A1/es not_active Expired
- 1971-11-22 LU LU64306D patent/LU64306A1/xx unknown
- 1971-11-26 CA CA128,736*7A patent/CA955253A/en not_active Expired
- 1971-11-26 US US00202596A patent/US3758459A/en not_active Expired - Lifetime
- 1971-11-26 DE DE19712158801 patent/DE2158801B2/de active Granted
- 1971-11-26 SU SU1718586A patent/SU432718A3/ru active
- 1971-11-26 SE SE7115183A patent/SE378245B/xx unknown
- 1971-11-26 NL NL7116314A patent/NL7116314A/xx unknown
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