GB1395416A - Diazepine derivatives and processes for their production - Google Patents
Diazepine derivatives and processes for their productionInfo
- Publication number
- GB1395416A GB1395416A GB3421672A GB3421672A GB1395416A GB 1395416 A GB1395416 A GB 1395416A GB 3421672 A GB3421672 A GB 3421672A GB 3421672 A GB3421672 A GB 3421672A GB 1395416 A GB1395416 A GB 1395416A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- compounds
- methyl
- hydrogen
- imino
- 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
- 125000002576 diazepinyl group Chemical class N1N=C(C=CC=C1)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 239000000460 chlorine Substances 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 229910052731 fluorine Inorganic materials 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000005277 alkyl imino group Chemical group 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000004494 ethyl ester group Chemical group 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 abstract 2
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 2
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 abstract 1
- QSZGTNZUJRNSEM-UHFFFAOYSA-N 1H-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine Chemical class N1C=NC=2N1C1=C(C=NC2)C=CC=C1 QSZGTNZUJRNSEM-UHFFFAOYSA-N 0.000 abstract 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- -1 CF 3 Inorganic materials 0.000 abstract 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000005189 alkyl hydroxy group Chemical group 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
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- GLELQNLTICCTEG-UHFFFAOYSA-N diethyl 2-[(2-benzoylphenyl)diazenyl]-2-[(2-chloroacetyl)amino]propanedioate Chemical compound C(C)OC(C(C(=O)OCC)(N=NC1=C(C=CC=C1)C(C1=CC=CC=C1)=O)NC(CCl)=O)=O GLELQNLTICCTEG-UHFFFAOYSA-N 0.000 abstract 1
- FIRXYFZXNJPHDX-UHFFFAOYSA-N diethyl 2-[(2-chloroacetyl)amino]propanedioate Chemical compound CCOC(=O)C(NC(=O)CCl)C(=O)OCC FIRXYFZXNJPHDX-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 abstract 1
- 239000004312 hexamethylene tetramine Substances 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229960004011 methenamine Drugs 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methyl alcohol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 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
Abstract
1395416 S - triazolo[1,5-a][1,4]benzodiazepines CIBA-GEIGY AG 21 July 1972 [23 July 1971] 34216/72 Heading C2C Novel compounds I in which R 1 is hydrogen or C 1-3 alkyl, R 2 and R 3 are hydrogen, C 1-6 alkyl, hydroxy C 1-6 alkyl or C 7-9 aralkyl or R 2 and R 3 are both C 2-6 alkyl joined together at the # or γ positions either directly or via oxygen, imino, C 1-4 alkyl-imino or hydroxy-C 1-4 alkyl-imino and rings A and B are optionally substituted by one or more radicals selected from Cl, Br, F, CF 3 , NO 2 , C 1-6 alkyl and C 1-6 alkoxy and their 5-oxides and acid addition salts are prepared by (1) reacting the corresponding reactive ester of the 2-methyl alcohol with an amine HNR 2 R 3 or with an alkali metal derivative thereof (2) reducing a corresponding 2-methyl azido compound to form a compound (I) in which R 2 and R 3 are hydrogen or (3) hydrolysing a compound V or a 5-oxide thereof in which R 3 <SP>a</SP> is an acyl radical or R 2 and R 3 <SP>a</SP> are C 2-6 alkyl bound together in the # or γ position via an acylimino group, to form compounds I in which R 3 is hydrogen or R 2 and R 3 are C 2-6 alkyl bound to each other in the # or γ position via an imino group. Preferred compounds I are those in which ring A has a single substituent in the 8- position chosen from fluorine, chlorine, bromine, nitro, trifluoromethyl and ring B has no substituent or is substituted in the ortho position by fluorine, chlorine or trifluoro methyl. Compounds II are prepared by reduction of the ethyl ester of the corresponding 2-carboxylic acid which is formed by ring closure of a compound VII with ammonia or hexamethylene tetramine. Compounds VII and their ethyl esters are prepared from a 2-amino-benzophenone by diazotization and reaction with 2-chloroacetamidomalonic acid diethyl ester followed by ring closure in the presence of NaOH of the 2- chloroacetamido - (2 - benzoyl - phenylazo) malonic acid diethyl ester formed. Reactive esters of compounds II are the methyl sulphonates which are also converted into the 2-azido methyl compounds by reaction with sodium azide. Compounds I their 5-oxides and acid addition salts are tranquillizers and anticonvulsants and form with a carrier or diluent a pharmaceutical composition which may be administered orally.
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 (1)
| Publication Number | Publication Date |
|---|---|
| GB1395416A true GB1395416A (en) | 1975-05-29 |
Family
ID=4367854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3421672A Expired GB1395416A (en) | 1971-07-23 | 1972-07-21 | Diazepine derivatives and processes for their production |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3878205A (en) |
| JP (1) | JPS561316B1 (en) |
| AR (2) | AR194603A1 (en) |
| AT (2) | AT319956B (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 US US272088A patent/US3878205A/en not_active Expired - Lifetime
- 1972-07-14 NL NL7209809A patent/NL7209809A/xx not_active Application Discontinuation
- 1972-07-14 DE DE2234652A patent/DE2234652A1/en active Pending
- 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 AT AT1013073A patent/AT319956B/en not_active IP Right Cessation
- 1972-07-21 SU SU1813891A patent/SU472505A3/en active
- 1972-07-21 PL PL1972156882A patent/PL85681B1/pl unknown
- 1972-07-21 HU HUCI1256A patent/HU165319B/hu unknown
- 1972-07-21 AT AT631372A patent/AT318625B/en not_active IP Right Cessation
- 1972-07-21 GB GB3421672A patent/GB1395416A/en not_active Expired
- 1972-07-21 AU AU44837/72A patent/AU472145B2/en not_active Expired
- 1972-07-21 FR FR7226331A patent/FR2147092B1/fr not_active Expired
- 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 |
|---|---|
| IL39883A0 (en) | 1972-09-28 |
| IE36563B1 (en) | 1976-12-08 |
| FR2147092B1 (en) | 1975-08-08 |
| CS178450B2 (en) | 1977-09-15 |
| AT318625B (en) | 1974-11-11 |
| CS178411B2 (en) | 1977-09-15 |
| ZA724839B (en) | 1973-04-25 |
| AU4483772A (en) | 1974-01-24 |
| SE380804B (en) | 1975-11-17 |
| IE36563L (en) | 1973-01-23 |
| AT319956B (en) | 1975-01-27 |
| DE2234652A1 (en) | 1973-02-01 |
| DD99578A5 (en) | 1973-08-12 |
| CA967956A (en) | 1975-05-20 |
| NO134868C (en) | 1976-12-29 |
| US3878205A (en) | 1975-04-15 |
| FR2147092A1 (en) | 1973-03-09 |
| JPS561316B1 (en) | 1981-01-13 |
| NL7209809A (en) | 1973-01-25 |
| CH553801A (en) | 1974-09-13 |
| BE786530A (en) | 1973-01-22 |
| SU472505A3 (en) | 1975-05-30 |
| AR197989A1 (en) | 1974-05-24 |
| IL39883A (en) | 1976-06-30 |
| AR194603A1 (en) | 1973-07-31 |
| HU165319B (en) | 1974-08-28 |
| AU472145B2 (en) | 1976-05-20 |
| FI52729B (en) | 1977-08-01 |
| SU497776A3 (en) | 1975-12-30 |
| FI52729C (en) | 1977-11-10 |
| NO134868B (en) | 1976-09-20 |
| PL85681B1 (en) | 1976-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |