DE2010884C2 - In 4-Stellung durch einen sauerstoffhaltigen Rest substituierte 8-Chlor-6-phenyl-4H-s-triazolo-[4,3-a] [1,4]-benzodiazepine und Verfahren zu ihrer Herstellung sowie sie enthaltende Arzneimittel - Google Patents
In 4-Stellung durch einen sauerstoffhaltigen Rest substituierte 8-Chlor-6-phenyl-4H-s-triazolo-[4,3-a] [1,4]-benzodiazepine und Verfahren zu ihrer Herstellung sowie sie enthaltende ArzneimittelInfo
- Publication number
- DE2010884C2 DE2010884C2 DE2010884A DE2010884A DE2010884C2 DE 2010884 C2 DE2010884 C2 DE 2010884C2 DE 2010884 A DE2010884 A DE 2010884A DE 2010884 A DE2010884 A DE 2010884A DE 2010884 C2 DE2010884 C2 DE 2010884C2
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- benzodiazepine
- parts
- chloro
- triazolo
- 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
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims 2
- 239000003814 drug Substances 0.000 title claims 2
- 229910052760 oxygen Inorganic materials 0.000 title claims 2
- 239000001301 oxygen Substances 0.000 title claims 2
- CDCHDCWJMGXXRH-UHFFFAOYSA-N estazolam Chemical group C=1C(Cl)=CC=C(N2C=NN=C2CN=2)C=1C=2C1=CC=CC=C1 CDCHDCWJMGXXRH-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 14
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 5
- -1 alkyl radical Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000001557 benzodiazepines Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000012876 carrier material Substances 0.000 claims 1
- 238000006140 methanolysis reaction Methods 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
- 239000002904 solvent Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 17
- 229940049706 benzodiazepine Drugs 0.000 description 13
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 12
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- YWKRLOSRDGPEJR-KIUKIJHYSA-N (3z)-3-(2-chlorothioxanthen-9-ylidene)-n,n-dimethylpropan-1-amine;hydron;chloride Chemical compound Cl.C1=C(Cl)C=C2C(=C/CCN(C)C)\C3=CC=CC=C3SC2=C1 YWKRLOSRDGPEJR-KIUKIJHYSA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229960000322 chlorprothixene hydrochloride Drugs 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006136 alcoholysis reaction Methods 0.000 description 3
- 238000006266 etherification reaction Methods 0.000 description 3
- 230000000147 hypnotic effect Effects 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229940125723 sedative agent Drugs 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000028527 righting reflex Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 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
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/20—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP44017663A JPS4837280B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-03-08 | 1969-03-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2010884A1 DE2010884A1 (de) | 1970-12-10 |
| DE2010884C2 true DE2010884C2 (de) | 1982-12-09 |
Family
ID=11950078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2010884A Expired DE2010884C2 (de) | 1969-03-08 | 1970-03-07 | In 4-Stellung durch einen sauerstoffhaltigen Rest substituierte 8-Chlor-6-phenyl-4H-s-triazolo-[4,3-a] [1,4]-benzodiazepine und Verfahren zu ihrer Herstellung sowie sie enthaltende Arzneimittel |
Country Status (15)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3681343A (en) * | 1971-05-11 | 1972-08-01 | Upjohn Co | 6-phenyl-s-triazolo{8 4,3-a{9 {8 1,4{9 {0 benzodiazepines |
| US3879406A (en) * | 1972-07-13 | 1975-04-22 | Hoffmann La Roche | Preparation of triazolobenzodiazepines |
| JPS5747914B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-04-12 | 1982-10-13 | ||
| US4588721A (en) * | 1983-09-12 | 1986-05-13 | The Upjohn Company | Treatment of negative symptoms of schizophrenia |
| JPS6193487U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1984-11-22 | 1986-06-17 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3464978A (en) * | 1967-04-21 | 1969-09-02 | Hoffmann La Roche | 1-substituted urea alkyl 1,2-dihydro-1,4-benzodiazepines and benzodiazepin - 2-ones |
| US3498973A (en) * | 1967-06-19 | 1970-03-03 | Hoffmann La Roche | 2,3-dihydro-5-phenyl-1h-1,4-benzodiazepin-3-ol derivatives |
| US3523939A (en) * | 1967-07-03 | 1970-08-11 | Hoffmann La Roche | 5-(2,6-disubstituted phenyl)-1,4-benzodiazepines and methods for their preparation |
-
1969
- 1969-03-08 JP JP44017663A patent/JPS4837280B1/ja active Pending
-
1970
- 1970-02-12 SE SE01824/70A patent/SE367201B/xx unknown
- 1970-02-27 NL NL7002884.A patent/NL166023C/xx not_active IP Right Cessation
- 1970-03-02 DK DK101170AA patent/DK139973B/da unknown
- 1970-03-02 BE BE746735D patent/BE746735A/xx not_active IP Right Cessation
- 1970-03-03 ES ES377099A patent/ES377099A1/es not_active Expired
- 1970-03-05 US US016970A patent/US3907820A/en not_active Expired - Lifetime
- 1970-03-06 NO NO00796/70*[A patent/NO126326B/no unknown
- 1970-03-06 FR FR7008051A patent/FR2034750B1/fr not_active Expired
- 1970-03-06 CH CH1842972A patent/CH546778A/xx not_active IP Right Cessation
- 1970-03-06 CH CH336470A patent/CH550812A/xx not_active IP Right Cessation
- 1970-03-06 CH CH1842872A patent/CH542865A/de not_active IP Right Cessation
- 1970-03-06 AT AT212870A patent/AT297707B/de not_active IP Right Cessation
- 1970-03-06 AT AT426771A patent/AT297718B/de not_active IP Right Cessation
- 1970-03-07 DE DE2010884A patent/DE2010884C2/de not_active Expired
- 1970-03-09 GB GB01124/70A patent/GB1248727A/en not_active Expired
-
1972
- 1972-10-02 SE SE7212703A patent/SE397832B/xx unknown
-
1974
- 1974-01-03 PH PH15375*A patent/PH10048A/en unknown
- 1974-10-31 PH PH16169A patent/PH11202A/en unknown
-
1975
- 1975-12-30 MY MY10/75A patent/MY7500010A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES377099A1 (es) | 1972-06-01 |
| FR2034750A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-11 |
| US3907820A (en) | 1975-09-23 |
| SE367201B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-05-20 |
| AT297718B (de) | 1972-04-10 |
| MY7500010A (en) | 1975-12-31 |
| PH10048A (en) | 1976-07-27 |
| GB1248727A (en) | 1971-10-06 |
| FR2034750B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-04-12 |
| AT297707B (de) | 1972-04-10 |
| DE2010884A1 (de) | 1970-12-10 |
| CH542865A (de) | 1973-11-30 |
| DK139973B (da) | 1979-05-28 |
| JPS4837280B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-11-09 |
| PH11202A (en) | 1977-10-28 |
| NL166023B (nl) | 1981-01-15 |
| DK139973C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-10-29 |
| NL166023C (nl) | 1981-06-15 |
| BE746735A (fr) | 1970-08-17 |
| NL7002884A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-09-10 |
| SE397832B (sv) | 1977-11-21 |
| CH550812A (de) | 1974-06-28 |
| CH546778A (de) | 1974-03-15 |
| NO126326B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-01-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |