RO91141B - Process for the preparation of 2-oxindol-1-carboxamide derivatives - Google Patents
Process for the preparation of 2-oxindol-1-carboxamide derivativesInfo
- Publication number
- RO91141B RO91141B RO118604A RO11860485A RO91141B RO 91141 B RO91141 B RO 91141B RO 118604 A RO118604 A RO 118604A RO 11860485 A RO11860485 A RO 11860485A RO 91141 B RO91141 B RO 91141B
- Authority
- RO
- Romania
- Prior art keywords
- phenyl
- preparation
- carboxamide derivatives
- trifluoromethyl
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- UYINJAQCJCYCGO-UHFFFAOYSA-N 2-oxo-3h-indole-1-carboxamide Chemical class C1=CC=C2N(C(=O)N)C(=O)CC2=C1 UYINJAQCJCYCGO-UHFFFAOYSA-N 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 5
- -1 di-substituted phenyl Chemical group 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Inventia se refera la un procedeu pentru prepararea unor derivati de 2-oxindol-1-carboxamida cu formula generala I: ( vezi formula) în care R1 este metil, furil, tienil, trifluormetil, benzil, piridil, tienilmetil, ciclohexil, fenoximetil, feniletil, fenil, fenil substituit cu fluor, R2 este fenil, fenil mono sau disubstituit cu fluor, clor, trifluormetil, metoxi, metil sau etil, constînd din aceea ca un 2-oxindol cu formula generala II: (vezi formula) în care R1 are semnificatiile de mai sus, se trateaza cu un izocianat cu formula generala III: (vezi formula) în care R2 are semnificatiile de mai sus, în prezenta unui solvent, la o temperatura cuprinsa între temperatura camerei si cea de reflux, eventual în prezenta unui agent bazic, dupa care daca se doreste compusul cu formula I obtinut se transforma într-o sare acceptibila farmaceutic, prin metode în sine cunoscute.The invention relates to a process for the preparation of 2-oxindole-1-carboxamide derivatives of the general formula I wherein R 1 is methyl, furyl, thienyl, trifluoromethyl, benzyl, pyridyl, thienylmethyl, cyclohexyl, phenoxymethyl, phenylethyl , phenyl, phenyl substituted with fluorine, R 2 is phenyl, phenyl, mono- or di-substituted phenyl, phenyl, trifluoromethyl, methoxy, methyl or ethyl, the above-mentioned meaning is treated with an isocyanate of general formula III wherein R2 is as defined above in the presence of a solvent at a temperature between room temperature and reflux, optionally in the presence of an agent base, after which if desired, the compound of formula I obtained is converted into a pharmaceutically acceptable salt, by methods known per se.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60735684A | 1984-05-04 | 1984-05-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RO91141A RO91141A (en) | 1987-06-30 |
| RO91141B true RO91141B (en) | 1987-07-03 |
Family
ID=24431933
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RO118604A RO91141B (en) | 1984-05-04 | 1985-05-03 | Process for the preparation of 2-oxindol-1-carboxamide derivatives |
| RO123678A RO94455B (en) | 1984-05-04 | 1985-05-03 | Process for preparing 2-oxindol-1-carboxamide derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RO123678A RO94455B (en) | 1984-05-04 | 1985-05-03 | Process for preparing 2-oxindol-1-carboxamide derivatives |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS60243068A (en) |
| KR (1) | KR870000497B1 (en) |
| AR (1) | AR241159A1 (en) |
| BG (2) | BG60208B2 (en) |
| CS (1) | CS252828B2 (en) |
| DD (1) | DD232916A5 (en) |
| EG (1) | EG17193A (en) |
| ES (2) | ES8609248A1 (en) |
| FI (1) | FI80016C (en) |
| HU (1) | HU196057B (en) |
| IE (1) | IE851103L (en) |
| IN (1) | IN161509B (en) |
| MA (1) | MA20424A1 (en) |
| MW (1) | MW1685A1 (en) |
| MX (1) | MX5839A (en) |
| NO (1) | NO163132C (en) |
| OA (1) | OA08098A (en) |
| PL (2) | PL145416B1 (en) |
| PT (1) | PT80375B (en) |
| RO (2) | RO91141B (en) |
| RU (1) | RU2017729C1 (en) |
| SU (1) | SU1468413A3 (en) |
| YU (1) | YU44998B (en) |
| ZA (1) | ZA853324B (en) |
| ZW (1) | ZW7885A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5047554A (en) * | 1989-04-18 | 1991-09-10 | Pfizer Inc. | 3-substituted-2-oxindole derivatives |
| IL95880A (en) * | 1989-10-13 | 1995-12-31 | Pfizer | Use of 3-substituted-2-oxindole derivatives for the preparation of a pharmaceutical preparation for inhibiting interleukin-1 biosynthesis |
-
1985
- 1985-04-08 IN IN288/DEL/85A patent/IN161509B/en unknown
- 1985-04-30 PT PT80375A patent/PT80375B/en unknown
- 1985-04-30 YU YU730/85A patent/YU44998B/en unknown
- 1985-05-02 IE IE851103A patent/IE851103L/en unknown
- 1985-05-02 EG EG275/85A patent/EG17193A/en active
- 1985-05-02 JP JP60095275A patent/JPS60243068A/en active Granted
- 1985-05-02 DD DD85275898A patent/DD232916A5/en not_active IP Right Cessation
- 1985-05-02 AR AR300259A patent/AR241159A1/en active
- 1985-05-03 ES ES542813A patent/ES8609248A1/en not_active Expired
- 1985-05-03 MA MA20648A patent/MA20424A1/en unknown
- 1985-05-03 PL PL1985253203A patent/PL145416B1/en unknown
- 1985-05-03 MW MW16/85A patent/MW1685A1/en unknown
- 1985-05-03 RO RO118604A patent/RO91141B/en unknown
- 1985-05-03 OA OA58583A patent/OA08098A/en unknown
- 1985-05-03 NO NO851774A patent/NO163132C/en not_active IP Right Cessation
- 1985-05-03 ZA ZA853324A patent/ZA853324B/en unknown
- 1985-05-03 PL PL1985257892A patent/PL147508B1/en unknown
- 1985-05-03 BG BG070071A patent/BG60208B2/en unknown
- 1985-05-03 FI FI851756A patent/FI80016C/en not_active IP Right Cessation
- 1985-05-03 MX MX583985A patent/MX5839A/en unknown
- 1985-05-03 ZW ZW78/85A patent/ZW7885A1/en unknown
- 1985-05-03 RO RO123678A patent/RO94455B/en unknown
- 1985-05-03 KR KR1019850003013A patent/KR870000497B1/en not_active Expired
- 1985-05-04 RU SU853891002A patent/RU2017729C1/en active
- 1985-05-04 CS CS853202A patent/CS252828B2/en not_active IP Right Cessation
- 1985-05-31 HU HU851693A patent/HU196057B/en unknown
-
1986
- 1986-01-27 ES ES551275A patent/ES8707182A1/en not_active Expired
- 1986-05-12 SU SU864027453A patent/SU1468413A3/en active
-
1992
- 1992-07-08 BG BG096583A patent/BG60207B2/en unknown
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