IE40329B1 - Alkyl 6,7-dialkoyz-2-methyl-4-oxo-1-carboxylates - Google Patents
Alkyl 6,7-dialkoyz-2-methyl-4-oxo-1-carboxylatesInfo
- Publication number
- IE40329B1 IE40329B1 IE2561/74A IE256174A IE40329B1 IE 40329 B1 IE40329 B1 IE 40329B1 IE 2561/74 A IE2561/74 A IE 2561/74A IE 256174 A IE256174 A IE 256174A IE 40329 B1 IE40329 B1 IE 40329B1
- Authority
- IE
- Ireland
- Prior art keywords
- dimethoxyanilino
- formula
- carboxylates
- methyl
- oxotetrahydroquinoline
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- MALUFRPCQWHCJQ-UHFFFAOYSA-N 3-(3,4-dimethoxyanilino)butanoic acid Chemical compound COC1=CC=C(NC(C)CC(O)=O)C=C1OC MALUFRPCQWHCJQ-UHFFFAOYSA-N 0.000 abstract 1
- QRIUARMGAKHYFL-UHFFFAOYSA-N 4-oxo-2,3,4a,5-tetrahydroquinoline-1-carboxylic acid Chemical class C1CN(C2=CC=CCC2C1=O)C(=O)O QRIUARMGAKHYFL-UHFFFAOYSA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- MBHFIOOFCDTZMD-UHFFFAOYSA-N ethyl 3-(3,4-dimethoxyanilino)but-2-enoate Chemical compound CCOC(=O)C=C(C)NC1=CC=C(OC)C(OC)=C1 MBHFIOOFCDTZMD-UHFFFAOYSA-N 0.000 abstract 1
- PVELCDFGBLEXRI-UHFFFAOYSA-N ethyl 3-(3,4-dimethoxyanilino)butanoate Chemical compound CCOC(=O)CC(C)NC1=CC=C(OC)C(OC)=C1 PVELCDFGBLEXRI-UHFFFAOYSA-N 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 229940093858 ethyl acetoacetate Drugs 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
Abstract
1454039 Substituted 4-oxotetrahydroquinoline 1-carboxylates PFIZER Inc 13 Sept 1974 [26 Dec 1973] 40126/74 Heading C2C The invention comprises compounds of Formula I wherein R, R 1 and R 2 are the same or different and are C 1-4 alkyl groups which may be prepared by acylation of a compound of Formula II with an appropriate agent, e.g. alkylchloroformate. Ethyl - 3 - [3,4 - dimethoxyanilino] - 2 - butenoate is prepared by reaction of 4-animoveratrole with ethylacetoacetate and is hydrogenated to obtain ethyl - 3 - [3,4 - dimethoxyanilino]- butanoate which on treatment under reflux with methanolic aqueous sodium hydroxide is hydrolysed to 3-[3,4-dimethoxyanilino]butanoic acid which is cyclized by heating with polyphosphoric acid to obtain 6,7-dimethyoxy-2-methyl- 4-oxotetrahydroquinoline. Pharmaceutical compositions having analgesic and tranquillizing activity for oral or parenteral application comprise a compound of Formula I together with a pharmaceutically acceptable carrier.
[GB1454039A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42844173A | 1973-12-26 | 1973-12-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE40329L IE40329L (en) | 1975-06-26 |
| IE40329B1 true IE40329B1 (en) | 1979-05-09 |
Family
ID=23698907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2561/74A IE40329B1 (en) | 1973-12-26 | 1974-12-12 | Alkyl 6,7-dialkoyz-2-methyl-4-oxo-1-carboxylates |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS582937B2 (en) |
| AR (1) | AR205807A1 (en) |
| BE (1) | BE823811A (en) |
| CA (1) | CA1035360A (en) |
| DD (1) | DD117454A5 (en) |
| DE (1) | DE2461050C2 (en) |
| DK (1) | DK138889B (en) |
| ES (1) | ES433305A1 (en) |
| FI (1) | FI368374A7 (en) |
| FR (1) | FR2255906B1 (en) |
| GB (1) | GB1454039A (en) |
| HU (1) | HU169380B (en) |
| IE (1) | IE40329B1 (en) |
| IL (1) | IL46232A0 (en) |
| LU (1) | LU71558A1 (en) |
| NL (1) | NL7416666A (en) |
| NO (1) | NO744670L (en) |
| RO (1) | RO64270A (en) |
| SE (1) | SE421417B (en) |
| SU (1) | SU538663A3 (en) |
| ZA (1) | ZA748171B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3978064A (en) * | 1975-11-04 | 1976-08-31 | Pfizer Inc. | 3-Aminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid esters and intermediates leading thereto |
-
1974
- 1974-01-01 AR AR257070A patent/AR205807A1/en active
- 1974-09-13 GB GB4012674A patent/GB1454039A/en not_active Expired
- 1974-12-10 SE SE7415497A patent/SE421417B/en unknown
- 1974-12-12 IE IE2561/74A patent/IE40329B1/en unknown
- 1974-12-12 IL IL46232A patent/IL46232A0/en unknown
- 1974-12-16 DK DK653874AA patent/DK138889B/en unknown
- 1974-12-19 FI FI3683/74A patent/FI368374A7/fi unknown
- 1974-12-20 DE DE2461050A patent/DE2461050C2/en not_active Expired
- 1974-12-20 HU HUPI440A patent/HU169380B/hu unknown
- 1974-12-20 NL NL7416666A patent/NL7416666A/en not_active Application Discontinuation
- 1974-12-23 ZA ZA00748171A patent/ZA748171B/en unknown
- 1974-12-23 NO NO744670A patent/NO744670L/no unknown
- 1974-12-24 BE BE1006357A patent/BE823811A/en unknown
- 1974-12-24 ES ES433305A patent/ES433305A1/en not_active Expired
- 1974-12-24 LU LU71558A patent/LU71558A1/xx unknown
- 1974-12-24 DD DD183378A patent/DD117454A5/xx unknown
- 1974-12-24 CA CA216,781A patent/CA1035360A/en not_active Expired
- 1974-12-25 SU SU2098256A patent/SU538663A3/en active
- 1974-12-26 JP JP752045A patent/JPS582937B2/en not_active Expired
- 1974-12-26 FR FR7442911A patent/FR2255906B1/fr not_active Expired
- 1974-12-26 RO RO7480945A patent/RO64270A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD117454A5 (en) | 1976-01-12 |
| FR2255906B1 (en) | 1978-06-30 |
| GB1454039A (en) | 1976-10-27 |
| DK653874A (en) | 1975-08-25 |
| IL46232A0 (en) | 1975-03-13 |
| DK138889B (en) | 1978-11-13 |
| HU169380B (en) | 1976-11-28 |
| DE2461050C2 (en) | 1983-12-29 |
| ZA748171B (en) | 1976-01-28 |
| JPS50105672A (en) | 1975-08-20 |
| SE421417B (en) | 1981-12-21 |
| SE7415497L (en) | 1975-06-27 |
| DE2461050A1 (en) | 1975-07-17 |
| NO744670L (en) | 1975-07-21 |
| AU7658174A (en) | 1976-06-24 |
| SU538663A3 (en) | 1976-12-05 |
| JPS582937B2 (en) | 1983-01-19 |
| AR205807A1 (en) | 1976-06-07 |
| RO64270A (en) | 1979-05-15 |
| IE40329L (en) | 1975-06-26 |
| FR2255906A1 (en) | 1975-07-25 |
| NL7416666A (en) | 1975-06-30 |
| CA1035360A (en) | 1978-07-25 |
| FI368374A7 (en) | 1975-06-27 |
| LU71558A1 (en) | 1975-08-20 |
| DK138889C (en) | 1979-04-30 |
| BE823811A (en) | 1975-06-24 |
| ES433305A1 (en) | 1977-03-01 |
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