GB1030030A - Derivatives of phthalimide - Google Patents
Derivatives of phthalimideInfo
- Publication number
- GB1030030A GB1030030A GB5253464A GB5253464A GB1030030A GB 1030030 A GB1030030 A GB 1030030A GB 5253464 A GB5253464 A GB 5253464A GB 5253464 A GB5253464 A GB 5253464A GB 1030030 A GB1030030 A GB 1030030A
- Authority
- GB
- United Kingdom
- Prior art keywords
- optically active
- reacting
- ethyl
- hydrogen
- acetyl
- 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
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical class CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 125000003047 N-acetyl group Chemical group 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 229940125681 anticonvulsant agent Drugs 0.000 abstract 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 229910052736 halogen Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000005544 phthalimido group Chemical group 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 239000003204 tranquilizing agent Substances 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
- 235000012431 wafers Nutrition 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
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
Novel a - monosubstituted - a - phthalimidoacetamides of formula <FORM:1030030/C2/1> where R is ethyl, propyl or isopropyl, R1 is hydrogen, methyl, ethyl or acetyl, R2 is methyl or ethyl, and X is hydrogen or halogen, as racemates and optically active isomers, are prepared by reacting the corresponding phthalimido acid, either in optically active or inactive form, with an agent suitable for converting carboxyl groups to carboxylic acyl chloride groups, and reacting the phthalimidoacid chloride formed with ammonia or an amine HNR1R2, R1 and R2 being as defined in Claim 1 except that R1 is not acetyl, and treating, if desired, the resulting phthalimidoacetamide when R1 is hydrogen with acetic anhydride to obtain the N-acetyl derivative. The optically active phthalimidiacids can be obtained by optical resolution of the corresponding racemic acid, e.g. by fractional crystallization of its ephedrine salts, or by reacting the appropriate phthalic anhydride with an optically active a -amino-acid of formula RCH(NH2)COOH. Therapeutic compositions which are useful as tranquilizers and anticonvulsants and which may be administered orally, e.g. as tablets, pills, wafers, or cachets, contain as active ingredient the compounds described above.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5253464A GB1030030A (en) | 1964-12-28 | 1964-12-28 | Derivatives of phthalimide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5253464A GB1030030A (en) | 1964-12-28 | 1964-12-28 | Derivatives of phthalimide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1030030A true GB1030030A (en) | 1966-05-18 |
Family
ID=10464276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5253464A Expired GB1030030A (en) | 1964-12-28 | 1964-12-28 | Derivatives of phthalimide |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1030030A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995001348A3 (en) * | 1993-07-02 | 1995-03-09 | Celgene Corp | Imides as inhibitors of tnp alpha |
-
1964
- 1964-12-28 GB GB5253464A patent/GB1030030A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995001348A3 (en) * | 1993-07-02 | 1995-03-09 | Celgene Corp | Imides as inhibitors of tnp alpha |
| EP1477486A3 (en) * | 1993-07-02 | 2004-12-15 | Celgene Corporation | Imides as inhibitors of TNF alpha |
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