DE57631T1 - ((indol-3-yl)-3-amino-2-propionyloxy)-2-essigsaeurederivate, verfahren zu ihrer herstellung und heilmittel, die sie enthalten. - Google Patents
((indol-3-yl)-3-amino-2-propionyloxy)-2-essigsaeurederivate, verfahren zu ihrer herstellung und heilmittel, die sie enthalten.Info
- Publication number
- DE57631T1 DE57631T1 DE198282400126T DE82400126T DE57631T1 DE 57631 T1 DE57631 T1 DE 57631T1 DE 198282400126 T DE198282400126 T DE 198282400126T DE 82400126 T DE82400126 T DE 82400126T DE 57631 T1 DE57631 T1 DE 57631T1
- Authority
- DE
- Germany
- Prior art keywords
- acetic acid
- indol
- hydroxy
- propionyloxy
- ester
- 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
- -1 INDOL-3-YL Chemical class 0.000 title claims 8
- 238000000034 method Methods 0.000 title claims 6
- 229940126601 medicinal product Drugs 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
- 239000003814 drug Substances 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 150000001412 amines Chemical group 0.000 claims 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 2
- JHFAEUICJHBVHB-UHFFFAOYSA-N 1h-indol-2-ol Chemical compound C1=CC=C2NC(O)=CC2=C1 JHFAEUICJHBVHB-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- ZCZSIDMEHXZRLG-UHFFFAOYSA-N acetic acid heptyl ester Natural products CCCCCCCOC(C)=O ZCZSIDMEHXZRLG-UHFFFAOYSA-N 0.000 claims 1
- 238000010306 acid treatment Methods 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000002981 blocking agent Substances 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- JPXGPRBLTIYFQG-UHFFFAOYSA-N heptan-4-yl acetate Chemical compound CCCC(CCC)OC(C)=O JPXGPRBLTIYFQG-UHFFFAOYSA-N 0.000 claims 1
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000007812 deficiency Effects 0.000 abstract 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 abstract 1
- 230000002295 serotoninergic effect Effects 0.000 abstract 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8101931A FR2499076A1 (fr) | 1981-02-02 | 1981-02-02 | Nouveaux derives de l'acide ((indol-3 yl)-3 amino-2 propionyloxy)-2 acetique, procedes pour leur preparation et medicaments les contenant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE57631T1 true DE57631T1 (de) | 1983-04-28 |
Family
ID=9254719
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE198282400126T Pending DE57631T1 (de) | 1981-02-02 | 1982-01-22 | ((indol-3-yl)-3-amino-2-propionyloxy)-2-essigsaeurederivate, verfahren zu ihrer herstellung und heilmittel, die sie enthalten. |
| DE8282400126T Expired DE3262357D1 (en) | 1981-02-02 | 1982-01-22 | ((indol-3-yl)-3-amino-2 propionyloxy)-2-acetic-acid derivatives, process for their preparation and pharmaceutical preparations containing them |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8282400126T Expired DE3262357D1 (en) | 1981-02-02 | 1982-01-22 | ((indol-3-yl)-3-amino-2 propionyloxy)-2-acetic-acid derivatives, process for their preparation and pharmaceutical preparations containing them |
Country Status (6)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2499076A1 (fr) * | 1981-02-02 | 1982-08-06 | Panmedica Laboratoires | Nouveaux derives de l'acide ((indol-3 yl)-3 amino-2 propionyloxy)-2 acetique, procedes pour leur preparation et medicaments les contenant |
| FR2531713A2 (fr) * | 1981-09-16 | 1984-02-17 | Panmedica Sa | Nouvelles compositions a base de 5-hydroxytryptophane, leur procede de preparation et medicaments les contenant |
| FR2546517B1 (fr) * | 1983-05-24 | 1987-04-24 | Panmedica | Nouveaux dipeptides du -l-5-hydroxy-tryptophane, procedes pour leur preparation et medicaments les contenant |
| US4888427A (en) * | 1987-04-07 | 1989-12-19 | University Of Florida | Amino acids containing dihydropyridine ring systems for site-specific delivery of peptides to the brain |
| US5079366A (en) * | 1987-04-07 | 1992-01-07 | University Of Florida | Quarternary pyridinium salts |
| US4822812A (en) * | 1987-05-21 | 1989-04-18 | Merrell Dow Pharmaceuticals Inc. | β-(Fluoromethylene)-5-hydroxytryptophan and derivatives and their use as prodrugs for MAO inhibition |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB873777A (en) * | 1959-01-26 | 1961-07-26 | Upjohn Co | 5-hydroxy-ª--alkyltryptophans |
| GB895034A (en) * | 1959-10-15 | 1962-04-26 | Caterpillar Tractor Co | Improvements in or relating to pipe-laying tractors |
| GB1080470A (en) * | 1963-12-31 | 1967-08-23 | Merck & Co Inc | Indole derivatives |
| US4000297A (en) * | 1971-05-18 | 1976-12-28 | Rotta Research Laboratorium S.P.A. | N-p-chlorobenzoyl tryptophane, salts and compositions thereof |
| IT1055518B (it) * | 1971-05-18 | 1982-01-11 | Rotta Research Lab | Derivatives del triptofano |
| DE2234651C3 (de) * | 1972-07-14 | 1978-11-09 | Troponwerke Gmbh & Co Kg, 5000 Koeln | Eckige Klammer auf l-(p-Chlorbenzoyl)-5-methoxy-2-methyl-3-indol] -acetoxj essigsaure, ihre Salze mit Basen, Verfahren zu ihrer Herstellung sowie pharmakologische Zubereitungen |
| US3988341A (en) * | 1974-06-25 | 1976-10-26 | Merck & Co., Inc. | Esterification process |
| DE2940373A1 (de) * | 1979-10-05 | 1981-04-23 | Troponwerke GmbH & Co KG, 5000 Köln | Lysin-(1-(p-chlorbenzoyl)-5-methoxy-2-methyl-3-indol) -acetoxy-acetate, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| FR2499076A1 (fr) * | 1981-02-02 | 1982-08-06 | Panmedica Laboratoires | Nouveaux derives de l'acide ((indol-3 yl)-3 amino-2 propionyloxy)-2 acetique, procedes pour leur preparation et medicaments les contenant |
-
1981
- 1981-02-02 FR FR8101931A patent/FR2499076A1/fr active Granted
-
1982
- 1982-01-22 AT AT82400126T patent/ATE11912T1/de not_active IP Right Cessation
- 1982-01-22 EP EP82400126A patent/EP0057631B1/fr not_active Expired
- 1982-01-22 DE DE198282400126T patent/DE57631T1/de active Pending
- 1982-01-22 DE DE8282400126T patent/DE3262357D1/de not_active Expired
- 1982-01-26 US US06/342,929 patent/US4456611A/en not_active Expired - Fee Related
- 1982-02-02 JP JP57016176A patent/JPS57188566A/ja active Granted
-
1984
- 1984-03-07 US US06/587,043 patent/US4568754A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0057631A1 (fr) | 1982-08-11 |
| FR2499076A1 (fr) | 1982-08-06 |
| US4568754A (en) | 1986-02-04 |
| DE3262357D1 (en) | 1985-03-28 |
| FR2499076B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-04-01 |
| JPS57188566A (en) | 1982-11-19 |
| JPS6136830B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-08-20 |
| US4456611A (en) | 1984-06-26 |
| EP0057631B1 (fr) | 1985-02-20 |
| ATE11912T1 (de) | 1985-03-15 |
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