ES378917A1 - Isoindoline and benzoisothiazoline derivatives, their preparation and pharmaceutical compositions containing them - Google Patents
Isoindoline and benzoisothiazoline derivatives, their preparation and pharmaceutical compositions containing themInfo
- Publication number
- ES378917A1 ES378917A1 ES378917A ES378917A ES378917A1 ES 378917 A1 ES378917 A1 ES 378917A1 ES 378917 A ES378917 A ES 378917A ES 378917 A ES378917 A ES 378917A ES 378917 A1 ES378917 A1 ES 378917A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- reacting
- ethyl
- compounds
- alpha
- 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
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 title abstract 3
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- HWLOCGLMEHUBAQ-UHFFFAOYSA-N 2-(1,2-benzothiazol-3-yl)acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=NSC2=C1 HWLOCGLMEHUBAQ-UHFFFAOYSA-N 0.000 abstract 1
- IYNFJKUJHGHOJF-UHFFFAOYSA-N 2-(3-oxo-1H-isoindol-2-yl)acetyl chloride Chemical compound O=C1N(CC2=CC=CC=C12)CC(=O)Cl IYNFJKUJHGHOJF-UHFFFAOYSA-N 0.000 abstract 1
- ZRWICZHXYMHBDP-UHFFFAOYSA-N 2-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1S(Cl)(=O)=O ZRWICZHXYMHBDP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- YKCQHUPTHHPHGX-UHFFFAOYSA-N ethyl 2-(1,1,3-trioxo-1,2-benzothiazol-2-yl)acetate Chemical compound C1=CC=C2S(=O)(=O)N(CC(=O)OCC)C(=O)C2=C1 YKCQHUPTHHPHGX-UHFFFAOYSA-N 0.000 abstract 1
- 125000005067 haloformyl group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
-
- 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
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Novel isoindoline or benzisothiazoline derivatives of the formula wherein R1 is H, halogen, C 1-3 alkyl, C 1-3 alkoxy or NO 2 R2 is H, C 1-5 alkyl, phenyl or substituted phenyl R3 and R4, which may be the same or different each are H, or C 1-5 alkyl or together represent an alkylene group which may be interrupted by O, S or N, and together with the N atom to which they are attached form a heterocyclic ring and R5 is >CH 2 or >SO 2 are prepared by reacting the appropriate isoindolineacetic or benzisothiazolineacetic acid or reactive derivatives thereof with ammonia or amines of the formula or by reacting the appropriate isoindolines or benzisothiazolines with amides of the formula wherein A is a reactive atom or group such as a halogen atom or by hydrolysing the corresponding nitrile derivatives to give compounds of Formula I above in which R3 and R4 are both H or by cyclizing compounds of the Formula V wherein Y is halogen or OH to give compounds in which R5 is > CH 2 or by reacting compounds of the formula with compounds of the formula wherein B is COOH, alkoxy carbonyl or haloformyl, and C is halosulphonyl or by oxidizing compounds of Formula XV 1-Oxo-isoindoline-2-acetic acid chloride is obtained by reacting the corresponding acid with thionyl chloride. The triethylamine salt of [alpha]-(o-carboxybenzenesulphonamido)butyramide is obtained by reacting o-carboxybenzenesulphonic acid monochloride with [alpha]-aminobutyramide and triethylamine. Ethyl [alpha] - ethyl - 1 - oxo - 2 - isoindolineacetate is prepared by reacting the sodium salt of 1- oxoisoindoline with ethyl [alpha]-bromobutyrate. By a similar process ethyl 3-oxo- 1,2-benzisothiazoline- 2-acetate 1,1-dioxide and ethyl [alpha]-ethyl-3-oxo-1,2- benzoisothiazoline-2-acetate 1,1-dioxide are obtained. Pharmaceutical compositions, having tranquillizing and sedative activities and suitable for oral administration, contain one or more of the above novel compounds of Formula I and pharmaceutically acceptable carriers.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE05806/69A SE333734B (en) | 1969-04-23 | 1969-04-23 | |
| SE07055/69A SE361667B (en) | 1969-05-20 | 1969-05-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES378917A1 true ES378917A1 (en) | 1973-01-16 |
Family
ID=26654657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES378917A Expired ES378917A1 (en) | 1969-04-23 | 1970-04-22 | Isoindoline and benzoisothiazoline derivatives, their preparation and pharmaceutical compositions containing them |
Country Status (8)
| Country | Link |
|---|---|
| AU (1) | AU1404370A (en) |
| BE (1) | BE749416A (en) |
| DE (1) | DE2019476A1 (en) |
| DK (1) | DK124953B (en) |
| ES (1) | ES378917A1 (en) |
| FR (1) | FR2042365A1 (en) |
| GB (1) | GB1271054A (en) |
| IL (1) | IL34317A0 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7907121L (en) | 1979-08-27 | 1981-02-28 | Astra Laekemedel Ab | FTALIMIDINDERIVAT |
| JPS6169773A (en) * | 1984-09-14 | 1986-04-10 | Takeda Chem Ind Ltd | Isoindolinone derivative |
| EP2344479B1 (en) * | 2008-09-23 | 2015-04-08 | Georgetown University | 1,2-benzisothiazolinone and isoindolinone derivatives |
| WO2013025897A1 (en) | 2011-08-16 | 2013-02-21 | Georgetown University | Methods of treating bacterial infections with 1,2-benzisothiazolinone and isoindolinone derivatives |
-
1970
- 1970-04-14 IL IL34317A patent/IL34317A0/en unknown
- 1970-04-17 AU AU14043/70A patent/AU1404370A/en not_active Expired
- 1970-04-22 ES ES378917A patent/ES378917A1/en not_active Expired
- 1970-04-22 DK DK202670AA patent/DK124953B/en unknown
- 1970-04-22 GB GB09363/70A patent/GB1271054A/en not_active Expired
- 1970-04-22 DE DE19702019476 patent/DE2019476A1/en active Pending
- 1970-04-23 FR FR7014786A patent/FR2042365A1/fr not_active Withdrawn
- 1970-04-23 BE BE749416D patent/BE749416A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL34317A0 (en) | 1970-06-17 |
| DE2019476A1 (en) | 1970-12-03 |
| FR2042365A1 (en) | 1971-02-12 |
| BE749416A (en) | 1970-10-01 |
| GB1271054A (en) | 1972-04-19 |
| AU1404370A (en) | 1971-10-21 |
| DK124953B (en) | 1972-12-11 |
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