IL39883A - 2-aminomethyl-6-phenyl-4h-s-triazolo(1,5-alpha)(1,4)benzodiazepine derivatives,their production and pharmaceutical compositions containing them - Google Patents
2-aminomethyl-6-phenyl-4h-s-triazolo(1,5-alpha)(1,4)benzodiazepine derivatives,their production and pharmaceutical compositions containing themInfo
- Publication number
- IL39883A IL39883A IL39883A IL3988372A IL39883A IL 39883 A IL39883 A IL 39883A IL 39883 A IL39883 A IL 39883A IL 3988372 A IL3988372 A IL 3988372A IL 39883 A IL39883 A IL 39883A
- Authority
- IL
- Israel
- Prior art keywords
- acid addition
- general formula
- triazolo
- phenyl
- chloro
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims 5
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 17
- 239000002253 acid Substances 0.000 claims 16
- 238000000034 method Methods 0.000 claims 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 239000003085 diluting agent Substances 0.000 claims 4
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims 3
- 150000001557 benzodiazepines Chemical class 0.000 claims 3
- 239000007795 chemical reaction product Substances 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- -1 sulphonic acid ester Chemical class 0.000 claims 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 229940071870 hydroiodic acid Drugs 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims 1
- 229910003446 platinum oxide Inorganic materials 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 235000011150 stannous chloride Nutrition 0.000 claims 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (34)
1. aums dlazepine derivatives having the general formula I wherein fig and R^, independently of each other, represent a hydrogen atom or an alkyl group having from 1 to 6 carbon represent atoms, or/together with the adjacent nitrogen atom 1-pyrrolidinyl, piperldino, morpholino or 4-methyl-1 -piperazinyl radical, and each of the rings A and B, independently of the other, is unsubstltuted or substituted by a chlorine or fluorine atom.
2. Compounds as claimed in Claim 1 , wherein ring A is substituted by a chlorine atom and ring B is unsubstltuted or substituted by a fluorine or chlorine atom,
3. · Compounds as claimed in any one of Claims 1 and 2, wherei the substituent of ring A is in the 8-position.
4. · Compounds as claimed in any one of Claims 1 to 3, wherein the substituent of ring B is in the ortho-position.
5. Compounds as claimed in any one of Claims 1 to 4, wherein B2 and R^, independently of each other, represent a 39883/2
6. Compounds as claimed in Claim 5# wherein B2 and R^, independently of each other, represent a hydrogen atom or methyl group.
7. The aoid addition salts of a compound as claimed in any one of Claims 1 to 6.
8. Acid addition salts as claimed i Claim 7 which are physiologically tolerable.
9. 2- TDimethylamino)~methyl7-6-phenyl-8-chloro-4H-s-triazolo7,5-a7 ,^benzodiazepine.
10. 2-(Aminomethyl)-6-phQnyl-8-ohloro-4H-s-triazolo T,5-a7 .^benzodiazepin .
11. 2- ΜΘthylamino)-methyl7-6-phenyl-8-chloro-4H-s-triazolo ΐ",5-a7β.^benzodiazepine.
12. 2^(Piperidlnomethyl)-6-phenyl-8-chloro-4H-s-triazolo ϊ".5-a7/i,^benzodiazepine.
13. 2- -iyrrolidinyl)-methyl7-6-phenyl-8-chloro-4H-.s-
14. 2-(Morpholinomethyl)-6-phenyl-8-chloro-4H-s-triazolo T,5½7 Γ,^001120^^2^**1®·
15. 2- T4-Methyl-1-piperazinyl)-methyl7-6-phenyl-8~ chloro-4H-s-triazolo f,5-a7 .^benzodiazepine.
16. 2- riyrethylamino)-methyl7-6-(o-fluorophenyl)-8-chloro-4H-s-tria olo f,5-a7^»47Denz diazspine and its hydrochloride. 39883/2
17. 2-[ (Dimethylamlno)-methyl]-6-(o-ffluorophenyl)-8-chloro-4H-s-triazolo[l,5-a][1,4]benzodiazepine.
18. · 2-[(Hethylamlno)j-methy1]-6-(o-chloropheny1)-8-chloro-4H-s-triazolo[l,5-a][l,4]benzodiazeplne and its (2:l)-fumarate.
19. · The acid addition salts of a compound as claimed in any one of Claims 9 to 18.
20. Acid addition salts as claimed In Claim 19 which are physiologically tolerable.
21. Process for the production of 2-ajninomethyl-6-phenyl-4H-s-triazolo[l,5-a][l»4]benzodiazepine derivatives having the general formula I as defined in Claim 1 and of their acid addition salts, which process comprises reacting a reactive ester of the corresponding compound having the general formula wherein the rings A and B are unsubstltuted or substituted as defined in Claim 1, with an amine having the general formula H - (III) 39883/2 wherein Rg and have the meanings given in Claim 1 or with an alkali metal derivative thereof and further, when required, converting a reaction product thus obtained into an acid addition salt thereof*
22. · Process according to Claim 21 wherein a sulphonic acid ester or hydrohalic acid ester of the compound of the general formula II is employed as reactive ester thereof.
23. · Process according to Claim 22 wherein the methane-sulphonic, o- or p-toluenesulphonic, o- or p-nitrobenzene-sulphonic, o~ or p-chlorobenzenesulphonic. hydrochloric, hydrobromlc or hydroiodic acid ester of the compound of the general formula II is employed.
24. · Process for the production of 2-aminoraethyl-6-phenyl- 4H-s-triazolo[l,5-a][l,4]benzodiazepine derivatives having the general formula I as defined in Claim 1, but wherein R2 and R^ may represent hydrogen atoms only, and of their acid addition salts, which process comprises reducing the corresponding compound havin the general formula 39883/2 wherein the rings A and B are unsubstltuted or substituted as defined in Claim 1, and further, when required, converting a reduction product thus obtained into an acid addition salt thereof.
25. Process according to Claim 24 wherein the reduction is effected b means of a palladium charcoal, platinum oxide or Raney nickel catalyst In an inert organic solvent*
26. Process according to Claim 24 wherein the reduction is effected by means of tin( II)-chloride i£ an alkaline, lower alkanolic-aqueous medium.
27. Process for the production of 2-aminomethyl-6-phenyl-4H-s-triazolo[l,5-a][l,4]benzodiazepine derivatives having the general formula I as ddlned in Claim 1, but wherein represents a hydrogen atom only, and of their acid addition salts, which comprises hydrolysing the corresponding compound having the general formula wherein R* represents an acyl radical and R2 represents hydrogen or an alkyl group having from 1 to 6 carbon atoms, and the - - - ·,«> · 39883/2 rings A and B are unsubstituted or substituted as defined in Claim 1, and further, when required, converting a reaction product thus obtained into an acid addition salt thereof or converting an acid addition salt of a reaction product thus obtained into the free base or Into another acid addition salt thereof.
28. · Process according to Claim 27 wherein R^a is an acetyl, formyl or cyano group or a methoxycarbonyl, ethoxy-carbonyl, tert.butoxycarbonyl, phenox carbon 1, benz loxycarbony1 or corresponding thiocarbonyl group, or a ehlorocarbonyl or benzoyl group.
29. · A compound having the general formula I as defined in Claim 1, or an acid addition salt thereof, whenever prepared by a process as claimedin any one of claims 21 to 28.
30. , A process for the production of compounds having the general formula I as defined in Claim 1 and their acid addition salts, substantially as hereinbefore described with reference to any one of the specifio Examples 4 to6 and 7 parts (a1) and (b').
31. A process for the production of compounds having the general formula I as defined in Claim 1 and their acid addition salts, substantially as hereinbefore described with reference to any one of the specific Examples 1 to 3 and 7 excluding parts (a*) and (V).
32. · A pharmaceutical composition comprising a compound as claimed in any one of Claims 1 to 6, together with a 39883/2 pharmaceutically acceptable diluent or carrier therefor.
33. · pharmaceutical composition comprising a compound as claimed in any one of Claims 9 to 18 together with a pharmaceutically acceptable diluent or carrier therefor.
34. Δ pharmaceutical composition comprising an sold addition salt as claimed in Claim 8, together with a pharmaceutically acceptable diluent or carrier therefor* 35· A pharmaceutical composition comprising an acid addition salt as claimed in Claim 20 together with a pharmaceutically acceptable diluent or carrier therefor. PC/rb
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1088571A CH553801A (en) | 1971-07-23 | 1971-07-23 | PROCESS FOR THE PRODUCTION OF NEW DIAZEPIN DERIVATIVES. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL39883A0 IL39883A0 (en) | 1972-09-28 |
| IL39883A true IL39883A (en) | 1976-06-30 |
Family
ID=4367854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL39883A IL39883A (en) | 1971-07-23 | 1972-07-11 | 2-aminomethyl-6-phenyl-4h-s-triazolo(1,5-alpha)(1,4)benzodiazepine derivatives,their production and pharmaceutical compositions containing them |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3878205A (en) |
| JP (1) | JPS561316B1 (en) |
| AR (2) | AR194603A1 (en) |
| AT (2) | AT318625B (en) |
| AU (1) | AU472145B2 (en) |
| BE (1) | BE786530A (en) |
| CA (1) | CA967956A (en) |
| CH (1) | CH553801A (en) |
| CS (2) | CS178450B2 (en) |
| DD (1) | DD99578A5 (en) |
| DE (1) | DE2234652A1 (en) |
| FI (1) | FI52729C (en) |
| FR (1) | FR2147092B1 (en) |
| GB (1) | GB1395416A (en) |
| HU (1) | HU165319B (en) |
| IE (1) | IE36563B1 (en) |
| IL (1) | IL39883A (en) |
| NL (1) | NL7209809A (en) |
| NO (1) | NO134868C (en) |
| PL (1) | PL85681B1 (en) |
| SE (1) | SE380804B (en) |
| SU (2) | SU472505A3 (en) |
| ZA (1) | ZA724839B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4209516A (en) * | 1974-01-14 | 1980-06-24 | Ciba-Geigy Corporation | Triazole derivatives |
| JPS5747915B2 (en) * | 1974-04-17 | 1982-10-13 | ||
| US4209515A (en) * | 1974-06-14 | 1980-06-24 | Ciba-Geigy Corporation | Triazole derivatives |
| US3996230A (en) * | 1975-03-28 | 1976-12-07 | The Upjohn Company | 1-Piperazino-6-(2-pyridyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepines |
| US4510141A (en) * | 1982-09-13 | 1985-04-09 | Ciba-Geigy Corporation | Tricyclic polyazaheterocycles for treating depression or anxiety |
| AR127157A1 (en) | 2021-09-29 | 2023-12-27 | Hoffmann La Roche | NEW BENZODIAZEPINE DERIVATIVES AS POSITIVE ALLESTERIC MODULATORS OF GABAA g1 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE758921A (en) * | 1969-11-15 | 1971-04-16 | Takeda Chemical Industries Ltd | BENZODIAZEPINE DERIVATIVES |
-
0
- BE BE786530D patent/BE786530A/en unknown
-
1971
- 1971-07-23 CH CH1088571A patent/CH553801A/en not_active IP Right Cessation
-
1972
- 1972-06-28 FI FI721828A patent/FI52729C/en active
- 1972-07-11 IL IL39883A patent/IL39883A/en unknown
- 1972-07-12 IE IE982/72A patent/IE36563B1/en unknown
- 1972-07-13 SE SE7209242A patent/SE380804B/en unknown
- 1972-07-13 ZA ZA724839A patent/ZA724839B/en unknown
- 1972-07-14 DE DE2234652A patent/DE2234652A1/en active Pending
- 1972-07-14 US US272088A patent/US3878205A/en not_active Expired - Lifetime
- 1972-07-14 NL NL7209809A patent/NL7209809A/xx not_active Application Discontinuation
- 1972-07-17 CA CA147,245A patent/CA967956A/en not_active Expired
- 1972-07-19 NO NO2588/72A patent/NO134868C/no unknown
- 1972-07-20 CS CS489A patent/CS178450B2/cs unknown
- 1972-07-20 CS CS5172A patent/CS178411B2/cs unknown
- 1972-07-21 DD DD164605A patent/DD99578A5/xx unknown
- 1972-07-21 SU SU1813891A patent/SU472505A3/en active
- 1972-07-21 AT AT631372A patent/AT318625B/en not_active IP Right Cessation
- 1972-07-21 FR FR7226331A patent/FR2147092B1/fr not_active Expired
- 1972-07-21 AT AT1013073A patent/AT319956B/en not_active IP Right Cessation
- 1972-07-21 HU HUCI1256A patent/HU165319B/hu unknown
- 1972-07-21 AU AU44837/72A patent/AU472145B2/en not_active Expired
- 1972-07-21 GB GB3421672A patent/GB1395416A/en not_active Expired
- 1972-07-21 PL PL1972156882A patent/PL85681B1/pl unknown
- 1972-07-22 JP JP7305972A patent/JPS561316B1/ja active Pending
- 1972-07-24 AR AR243233A patent/AR194603A1/en active
-
1973
- 1973-05-29 AR AR248269A patent/AR197989A1/en active
-
1974
- 1974-01-30 SU SU1993157A patent/SU497776A3/en active
Also Published As
| Publication number | Publication date |
|---|---|
| FI52729C (en) | 1977-11-10 |
| FR2147092A1 (en) | 1973-03-09 |
| AT318625B (en) | 1974-11-11 |
| AR194603A1 (en) | 1973-07-31 |
| IL39883A0 (en) | 1972-09-28 |
| CS178450B2 (en) | 1977-09-15 |
| NL7209809A (en) | 1973-01-25 |
| ZA724839B (en) | 1973-04-25 |
| HU165319B (en) | 1974-08-28 |
| IE36563L (en) | 1973-01-23 |
| SU472505A3 (en) | 1975-05-30 |
| NO134868B (en) | 1976-09-20 |
| AR197989A1 (en) | 1974-05-24 |
| NO134868C (en) | 1976-12-29 |
| US3878205A (en) | 1975-04-15 |
| SU497776A3 (en) | 1975-12-30 |
| PL85681B1 (en) | 1976-04-30 |
| CS178411B2 (en) | 1977-09-15 |
| AU472145B2 (en) | 1976-05-20 |
| CH553801A (en) | 1974-09-13 |
| IE36563B1 (en) | 1976-12-08 |
| CA967956A (en) | 1975-05-20 |
| BE786530A (en) | 1973-01-22 |
| SE380804B (en) | 1975-11-17 |
| FI52729B (en) | 1977-08-01 |
| AT319956B (en) | 1975-01-27 |
| DD99578A5 (en) | 1973-08-12 |
| JPS561316B1 (en) | 1981-01-13 |
| FR2147092B1 (en) | 1975-08-08 |
| AU4483772A (en) | 1974-01-24 |
| DE2234652A1 (en) | 1973-02-01 |
| GB1395416A (en) | 1975-05-29 |
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