IE33075B1 - Benzodiazepine derivatives and a process for the manufacture thereof - Google Patents
Benzodiazepine derivatives and a process for the manufacture thereofInfo
- Publication number
- IE33075B1 IE33075B1 IE630/69A IE63069A IE33075B1 IE 33075 B1 IE33075 B1 IE 33075B1 IE 630/69 A IE630/69 A IE 630/69A IE 63069 A IE63069 A IE 63069A IE 33075 B1 IE33075 B1 IE 33075B1
- Authority
- IE
- Ireland
- Prior art keywords
- added
- evapd
- stirred
- phh
- nh4oh
- Prior art date
Links
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 title 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract 2
- 235000019439 ethyl acetate Nutrition 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- 239000012267 brine Substances 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 229910052681 coesite Inorganic materials 0.000 abstract 1
- 229910052906 cristobalite Inorganic materials 0.000 abstract 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229940125723 sedative agent Drugs 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 235000012239 silicon dioxide Nutrition 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 abstract 1
- 229910052682 stishovite Inorganic materials 0.000 abstract 1
- 229940014800 succinic anhydride Drugs 0.000 abstract 1
- 229910052905 tridymite Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
(A) Cpds. of the general formula (I) R = H or (2-7C) lower alkanoyl (B) Salts of I. Sedatives. 4.69N NaOEt/MeOH (0.9 ml) was added to III (1 g.) in DMF (15 ml), stirred 0.5 h., and ethylene oxide (0.45 g.) in DMF (5 ml) added. The mixture was stirred 2 h. at 25 deg., 1 h. at 60 deg., evapd. in vac., and succinic anhydride (1.5 g.) in PhMe (50 ml) added. After refluxing 3 h., the mixture was cooled in ice, basified (NH4OH) and sepd. The H2O phase was treated with 3N-NaOH (5 ml), stirred 30 mins., acidified (cHCl), and basified (NH4OH), extd. with CH2Cl2, washed with brine (50 ml), dried and evapd. The residue in PhH (15 ml) was filtered through SiO2 (50 g), eluted with PhH (200 ml) and EtOAc (250 ml), the EtOAc evapd., dissolved in EtOH (5 ml), and HCl-EtOH added, giving I-HCl (R=H), m.p.195-7 deg.
[FR2007969A1]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72735668A | 1968-05-07 | 1968-05-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE33075L IE33075L (en) | 1969-11-07 |
| IE33075B1 true IE33075B1 (en) | 1974-03-06 |
Family
ID=24922333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE630/69A IE33075B1 (en) | 1968-05-07 | 1969-05-05 | Benzodiazepine derivatives and a process for the manufacture thereof |
Country Status (17)
| Country | Link |
|---|---|
| BE (1) | BE732557A (en) |
| BR (1) | BR6908524D0 (en) |
| CH (1) | CH512476A (en) |
| CS (1) | CS154270B2 (en) |
| DE (1) | DE1923250C3 (en) |
| DK (1) | DK120440B (en) |
| ES (1) | ES366840A1 (en) |
| FI (1) | FI49039C (en) |
| FR (1) | FR2007969A1 (en) |
| GB (1) | GB1192729A (en) |
| IE (1) | IE33075B1 (en) |
| IL (1) | IL32059A (en) |
| MY (1) | MY7100056A (en) |
| NL (1) | NL164557C (en) |
| NO (1) | NO122654B (en) |
| SE (1) | SE351646B (en) |
| YU (1) | YU33274B (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT224121B (en) * | 1959-12-10 | 1962-11-12 | Hoffmann La Roche | Process for the preparation of new 1,4-benzodiazepine derivatives |
| AT256114B (en) * | 1964-08-13 | 1967-08-10 | Hoffmann La Roche | Process for the preparation of new benzodiazepine derivatives |
-
1969
- 1969-04-22 IL IL32059A patent/IL32059A/en unknown
- 1969-04-23 CH CH614169A patent/CH512476A/en not_active IP Right Cessation
- 1969-04-30 DK DK239669AA patent/DK120440B/en not_active IP Right Cessation
- 1969-05-05 IE IE630/69A patent/IE33075B1/en unknown
- 1969-05-05 CS CS317969A patent/CS154270B2/cs unknown
- 1969-05-05 BR BR208524/69A patent/BR6908524D0/en unknown
- 1969-05-05 GB GB22779/69A patent/GB1192729A/en not_active Expired
- 1969-05-06 NO NO1864/69A patent/NO122654B/no unknown
- 1969-05-06 ES ES366840A patent/ES366840A1/en not_active Expired
- 1969-05-06 BE BE732557D patent/BE732557A/xx not_active IP Right Cessation
- 1969-05-06 FR FR6914419A patent/FR2007969A1/en not_active Withdrawn
- 1969-05-06 YU YU1104/69A patent/YU33274B/en unknown
- 1969-05-07 FI FI691348A patent/FI49039C/en active
- 1969-05-07 NL NL6906970.A patent/NL164557C/en not_active IP Right Cessation
- 1969-05-07 DE DE1923250A patent/DE1923250C3/en not_active Expired
- 1969-05-07 SE SE06467/69A patent/SE351646B/xx unknown
-
1971
- 1971-12-31 MY MY197156A patent/MY7100056A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL32059A0 (en) | 1969-06-25 |
| DE1923250C3 (en) | 1981-04-02 |
| NO122654B (en) | 1971-07-26 |
| ES366840A1 (en) | 1971-04-01 |
| FR2007969A1 (en) | 1970-01-16 |
| YU33274B (en) | 1976-08-31 |
| NL6906970A (en) | 1969-11-11 |
| GB1192729A (en) | 1970-05-20 |
| FI49039B (en) | 1974-12-02 |
| NL164557B (en) | 1980-08-15 |
| IE33075L (en) | 1969-11-07 |
| SE351646B (en) | 1972-12-04 |
| IL32059A (en) | 1972-08-30 |
| CH512476A (en) | 1971-09-15 |
| MY7100056A (en) | 1971-12-31 |
| YU110469A (en) | 1976-03-31 |
| FI49039C (en) | 1975-03-10 |
| DE1923250A1 (en) | 1969-11-20 |
| BR6908524D0 (en) | 1973-01-04 |
| BE732557A (en) | 1969-11-06 |
| DE1923250B2 (en) | 1980-07-24 |
| DK120440B (en) | 1971-06-01 |
| CS154270B2 (en) | 1974-03-29 |
| NL164557C (en) | 1981-01-15 |
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