DE2227487C3 - Derivate von 3-Äthoxycarbonyl-S-hydroxy-2-methyl-4-piperazinomethyl-indol, Verfahren zu ihrer Herstellung und Arzneimittel - Google Patents
Derivate von 3-Äthoxycarbonyl-S-hydroxy-2-methyl-4-piperazinomethyl-indol, Verfahren zu ihrer Herstellung und ArzneimittelInfo
- Publication number
- DE2227487C3 DE2227487C3 DE19722227487 DE2227487A DE2227487C3 DE 2227487 C3 DE2227487 C3 DE 2227487C3 DE 19722227487 DE19722227487 DE 19722227487 DE 2227487 A DE2227487 A DE 2227487A DE 2227487 C3 DE2227487 C3 DE 2227487C3
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- compounds
- ethoxycarbonyl
- hydroxy
- indole
- 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
- 239000003814 drug Substances 0.000 title description 5
- 238000000034 method Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 230000001624 sedative effect Effects 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- -1 morpholine radical Chemical class 0.000 description 4
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229960001789 papaverine Drugs 0.000 description 3
- 239000000932 sedative agent Substances 0.000 description 3
- 230000002048 spasmolytic effect Effects 0.000 description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- 150000003254 radicals Chemical group 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- OVDSBRUMFDTCKF-UHFFFAOYSA-N 2-(piperazin-1-ylmethyl)-1h-indole Chemical compound C=1C2=CC=CC=C2NC=1CN1CCNCC1 OVDSBRUMFDTCKF-UHFFFAOYSA-N 0.000 description 1
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical class C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 1
- 208000018672 Dilatation Diseases 0.000 description 1
- 206010017999 Gastrointestinal pain Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010029216 Nervousness Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- ALDDGIVIDJHNDZ-UHFFFAOYSA-N [CH2]C(=O)OCC Chemical group [CH2]C(=O)OCC ALDDGIVIDJHNDZ-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- BSNHKSUAAMJXBB-UHFFFAOYSA-N ethyl 5-hydroxy-2-methyl-1h-indole-3-carboxylate Chemical compound C1=C(O)C=C2C(C(=O)OCC)=C(C)NC2=C1 BSNHKSUAAMJXBB-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229940126904 hypoglycaemic agent Drugs 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7120476A FR2140260B1 (https=) | 1971-06-07 | 1971-06-07 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2227487A1 DE2227487A1 (de) | 1972-12-21 |
| DE2227487B2 DE2227487B2 (de) | 1977-06-30 |
| DE2227487C3 true DE2227487C3 (de) | 1978-03-16 |
Family
ID=9078186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722227487 Expired DE2227487C3 (de) | 1971-06-07 | 1972-06-06 | Derivate von 3-Äthoxycarbonyl-S-hydroxy-2-methyl-4-piperazinomethyl-indol, Verfahren zu ihrer Herstellung und Arzneimittel |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5132632B1 (https=) |
| BE (1) | BE784196A (https=) |
| CA (1) | CA954862A (https=) |
| CH (1) | CH540918A (https=) |
| DE (1) | DE2227487C3 (https=) |
| ES (1) | ES403546A1 (https=) |
| FR (1) | FR2140260B1 (https=) |
| GB (1) | GB1333359A (https=) |
| IT (1) | IT1051252B (https=) |
| LU (1) | LU65463A1 (https=) |
| NL (1) | NL7207639A (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2421900A1 (fr) * | 1977-03-17 | 1979-11-02 | Sauba Lab | Piperazino-3-indoles, leur procede de preparation et leurs applications therapeutiques |
-
1971
- 1971-06-07 FR FR7120476A patent/FR2140260B1/fr not_active Expired
-
1972
- 1972-05-31 BE BE784196A patent/BE784196A/xx unknown
- 1972-05-31 GB GB2537272A patent/GB1333359A/en not_active Expired
- 1972-06-02 CH CH821272A patent/CH540918A/fr not_active IP Right Cessation
- 1972-06-05 LU LU65463D patent/LU65463A1/xx unknown
- 1972-06-06 CA CA144,052*7A patent/CA954862A/en not_active Expired
- 1972-06-06 DE DE19722227487 patent/DE2227487C3/de not_active Expired
- 1972-06-06 ES ES403546A patent/ES403546A1/es not_active Expired
- 1972-06-06 JP JP5568472A patent/JPS5132632B1/ja active Pending
- 1972-06-06 NL NL7207639A patent/NL7207639A/xx not_active Application Discontinuation
- 1972-06-07 IT IT6880272A patent/IT1051252B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| CA954862A (en) | 1974-09-17 |
| IT1051252B (it) | 1981-04-21 |
| GB1333359A (en) | 1973-10-10 |
| NL7207639A (https=) | 1972-12-11 |
| CH540918A (fr) | 1973-08-31 |
| FR2140260B1 (https=) | 1974-08-30 |
| DE2227487B2 (de) | 1977-06-30 |
| DE2227487A1 (de) | 1972-12-21 |
| FR2140260A1 (https=) | 1973-01-19 |
| LU65463A1 (https=) | 1973-01-22 |
| JPS5132632B1 (https=) | 1976-09-14 |
| BE784196A (fr) | 1972-11-30 |
| ES403546A1 (es) | 1975-05-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |