RO94455B - Process for preparing 2-oxindol-1-carboxamide derivatives - Google Patents
Process for preparing 2-oxindol-1-carboxamide derivativesInfo
- Publication number
- RO94455B RO94455B RO123678A RO12367885A RO94455B RO 94455 B RO94455 B RO 94455B RO 123678 A RO123678 A RO 123678A RO 12367885 A RO12367885 A RO 12367885A RO 94455 B RO94455 B RO 94455B
- Authority
- RO
- Romania
- Prior art keywords
- chlorine
- phenyl
- formula
- trifluoromethyl
- fluorine
- Prior art date
Links
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000460 chlorine Chemical group 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
- 229910052731 fluorine Inorganic materials 0.000 abstract 3
- 239000011737 fluorine Chemical group 0.000 abstract 3
- 125000001153 fluoro group Chemical group F* 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- -1 chloro, phenylethyl Chemical group 0.000 abstract 2
- 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 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical group C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- WVKPYYLOFMTDHB-UHFFFAOYSA-N 2-norbornyl radical Chemical group C1CC2[CH]CC1C2 WVKPYYLOFMTDHB-UHFFFAOYSA-N 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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 pag.1 a descrierii) în care X este hidrogen, clor, trifluormetil, fluor, acetil, benzoil, nitro, Y este hidrogen, fluor, clor sau X si Y împreuna formeaza o catena cu formula: 4-CH2-CH2-CH2-5,5-CH2-CH2-CH2-6,6-CH2-CH2-CH2-CH2-7,5-CH=CH-CH=CH-6,5-O-CH2-CH2-6,5-CH2-CH2-O-6,5-S-CH2-CH2-6,5-O-CH=CH-6,5-S-CH=CH-6,5-CH=CH-S-6, numerele laterale indicînd pozitiile de legatura la nucleul de 2-oxindol, R1 reprezinta furil, tienil, tienilmetil, benzil, benzil substituit cu clor sau fluor, fenoximetil, piridil, metil, biciclo [2,2,1] heptan-2-il, ciclohexil, trifluormetil, fenil, ciclopropil, izopropil, ciclobutil, ciclopentil, fenil substituit cu fluor sau clor, feniletil, R2 reprezinta n-butil, t-butil, etil, izopropil, ciclohexil, benzil, fenil sau fenil mono sau disubstituit cu fluor, clor, trifluormetil si metil, care consta în aceea ca un 2-oxindol cu formula generala II (vezi formula în pag.1 a descrierii) reactioneaza cu un compus de forma R1COOH.The invention relates to a process for the preparation of 2-oxindole-1-carboxamide derivatives of the general formula I (see formula on page 1 of the description) wherein X is hydrogen, chlorine, trifluoromethyl, fluoro, acetyl, benzoyl, Y is hydrogen, fluorine, chlorine or X and Y together form a chain of the formula: 4-CH 2 -CH 2 -CH 2 -5,5 -CH 2 -CH 2 -CH 2 -6,6 -CH 2 -CH 2 -CH 2 -CH 2 -7, 5-CH = CH-CH = CH-6,5-O-CH2-CH2-CH2-CH2-6,5-6,5-O-CH2-6,5-S-CH2-O-CH = CH- 6-CH-CH = CH-6,5-CH = CH-S-6, the side numbers indicating the linkage positions of the 2-oxindole ring, R 1 represents furyl, thienyl, thienylmethyl, benzyl, benzyl substituted with chlorine or fluorine, phenoxymethyl, pyridyl, methyl, bicyclo [2.2.1] heptan-2-yl, cyclohexyl, trifluoromethyl, phenyl, cyclopropyl, isopropyl, cyclobutyl, cyclopentyl, phenyl substituted with fluoro or chloro, phenylethyl, R2 represents n- , t-butyl, ethyl, isopropyl, cyclohexyl, benzyl, phenyl or phenyl which is mono- or disubstituted by fluorine, chlorine, trifluoromethyl and methyl, which comprises reacting a 2-oxindole General Formula II (see formula on page 1 of the description) is reacted with a compound of the formula R 1 COOH.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60735684A | 1984-05-04 | 1984-05-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RO94455A RO94455A (en) | 1988-06-30 |
| RO94455B true RO94455B (en) | 1988-07-01 |
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 Before (1)
| 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 |
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 YU YU730/85A patent/YU44998B/en unknown
- 1985-04-30 PT PT80375A patent/PT80375B/en unknown
- 1985-05-02 DD DD85275898A patent/DD232916A5/en not_active IP Right Cessation
- 1985-05-02 AR AR300259A patent/AR241159A1/en active
- 1985-05-02 EG EG275/85A patent/EG17193A/en active
- 1985-05-02 IE IE851103A patent/IE851103L/en unknown
- 1985-05-02 JP JP60095275A patent/JPS60243068A/en active Granted
- 1985-05-03 PL PL1985253203A patent/PL145416B1/en unknown
- 1985-05-03 RO RO118604A patent/RO91141B/en unknown
- 1985-05-03 RO RO123678A patent/RO94455B/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 ES ES542813A patent/ES8609248A1/en not_active Expired
- 1985-05-03 ZW ZW78/85A patent/ZW7885A1/en unknown
- 1985-05-03 BG BG070071A patent/BG60208B2/en unknown
- 1985-05-03 NO NO851774A patent/NO163132C/en not_active IP Right Cessation
- 1985-05-03 MA MA20648A patent/MA20424A1/en unknown
- 1985-05-03 OA OA58583A patent/OA08098A/en unknown
- 1985-05-03 MW MW16/85A patent/MW1685A1/en unknown
- 1985-05-03 KR KR1019850003013A patent/KR870000497B1/en not_active Expired
- 1985-05-03 PL PL1985257892A patent/PL147508B1/en unknown
- 1985-05-03 ZA ZA853324A patent/ZA853324B/en unknown
- 1985-05-04 CS CS853202A patent/CS252828B2/en not_active IP Right Cessation
- 1985-05-04 RU SU853891002A patent/RU2017729C1/en active
- 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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