DE2159919A1 - Verfahren zur Herstellung von Derivaten des 5-Phenyl-3H-l,4-benzodiazepins - Google Patents
Verfahren zur Herstellung von Derivaten des 5-Phenyl-3H-l,4-benzodiazepinsInfo
- Publication number
- DE2159919A1 DE2159919A1 DE19712159919 DE2159919A DE2159919A1 DE 2159919 A1 DE2159919 A1 DE 2159919A1 DE 19712159919 DE19712159919 DE 19712159919 DE 2159919 A DE2159919 A DE 2159919A DE 2159919 A1 DE2159919 A1 DE 2159919A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- compound
- primary amino
- reaction
- amino group
- 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.)
- Pending
Links
- 229940049706 benzodiazepine Drugs 0.000 title abstract 2
- 239000012965 benzophenone Substances 0.000 title description 3
- 150000004985 diamines Chemical class 0.000 title description 2
- 150000001557 benzodiazepines Chemical class 0.000 title 1
- 150000008366 benzophenones Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003310 benzodiazepinyl group Chemical group N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims description 4
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- -1 ethylenediamino compound Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000000873 masking effect Effects 0.000 claims description 3
- DBFLXAXACNTBEP-UHFFFAOYSA-N 5-phenyl-3h-1,4-benzodiazepine Chemical class N=1CC=NC2=CC=CC=C2C=1C1=CC=CC=C1 DBFLXAXACNTBEP-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- FIQIEWYXLLEXNR-UHFFFAOYSA-N [O-][N+](=O)S(=O)(=O)[N+]([O-])=O Chemical compound [O-][N+](=O)S(=O)(=O)[N+]([O-])=O FIQIEWYXLLEXNR-UHFFFAOYSA-N 0.000 claims 1
- 239000000370 acceptor Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 abstract 1
- 229910006074 SO2NH2 Inorganic materials 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- FAVKIHMGRWRACA-UHFFFAOYSA-N (2,5-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC=C(Cl)C(C(=O)C=2C=CC=CC=2)=C1 FAVKIHMGRWRACA-UHFFFAOYSA-N 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 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- VMHYWKBKHMYRNF-UHFFFAOYSA-N (2-chlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC=C1C(=O)C1=CC=CC=C1 VMHYWKBKHMYRNF-UHFFFAOYSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid group Chemical group C(C=1C(C(=O)O)=CC=CC1)(=O)O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AR23457971 | 1971-03-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2159919A1 true DE2159919A1 (de) | 1972-09-28 |
Family
ID=3461927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712159919 Pending DE2159919A1 (de) | 1971-03-19 | 1971-12-02 | Verfahren zur Herstellung von Derivaten des 5-Phenyl-3H-l,4-benzodiazepins |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE772935A (https=) |
| CH (1) | CH580088A5 (https=) |
| DE (1) | DE2159919A1 (https=) |
| ES (1) | ES393999A1 (https=) |
-
1971
- 1971-08-07 ES ES393999A patent/ES393999A1/es not_active Expired
- 1971-09-22 BE BE772935A patent/BE772935A/xx unknown
- 1971-12-02 DE DE19712159919 patent/DE2159919A1/de active Pending
- 1971-12-09 CH CH1793871A patent/CH580088A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES393999A1 (es) | 1974-06-01 |
| CH580088A5 (https=) | 1976-09-30 |
| BE772935A (fr) | 1972-01-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1620501A1 (de) | Neue Sydnonimin-Derivate und Verfahren zu ihrer Herstellung | |
| DE1129153B (de) | Verfahren zur Herstellung von ª-Cyan-ª-Alkyl-ª-phenylacrylsaeureestern | |
| DE2455887C2 (de) | Verfahren zur Herstellung von chlorierten Phenylhydroxylaminen | |
| EP0012983B1 (de) | Diaminophenylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Aminobenzimidazolonen-(2) | |
| DE2159919A1 (de) | Verfahren zur Herstellung von Derivaten des 5-Phenyl-3H-l,4-benzodiazepins | |
| DE2715785C2 (de) | Verfahren zur Herstellung von aromatischen oder heterocyclischen Hydroxylamino- oder Aminoverbindungen | |
| DE1795741A1 (de) | Verfahren zur herstellung eines fuer die gewinnung von 3-formylrifamycin svderivaten geeigneten zwischenproduktes | |
| DE1795344B2 (de) | Verfahren zur herstellung von 3-aminoisothiazolen | |
| DE959460C (de) | Verfahren zur Herstellung von Lactamen | |
| DE1695653A1 (de) | Verfahren zur Herstellung von Chinoxalin-di-N-oxiden und verwandten Verbindungen | |
| DE1206879B (de) | Verfahren zur Herstellung von p-Aminoarylaldehyden | |
| DE1077222B (de) | Verfahren zur Herstellung von Benzimidazolylidenverbindungen | |
| DE2617967C3 (de) | Verfahren zur Herstellung von 2,4-Diamino-5-benzylpyrimidinen | |
| DE959097C (de) | Verfahren zur Herstellung von basisch substituierten Diarylacetonitrilen | |
| DE2159920A1 (de) | Verfahren zur Herstellung von substituierten 5-Phenyl-3-H-l,4-benzodiazepinen | |
| DE3514384A1 (de) | Substituierte furane und deren vorprodukte | |
| AT310175B (de) | Verfahren zur Herstellung neuer 2(1H)-Chinazolinone | |
| DE1045393B (de) | Verfahren zur Herstellung von Derivaten der 1, 1-Dimethyloctahydronaphthalinreihe | |
| EP0110202A2 (de) | Verfahren zur Herstellung von Phenylethanolaminen | |
| DE1271713B (de) | Verfahren zur Herstellung von organischen Carbonylverbindungen | |
| AT305973B (de) | Verfahren zur Herstellung von neuen Aminoalkyladamantanen | |
| CH581634A5 (en) | 7-Chloro-1,2-dihydro-5-phenyl-1,4-benzodiazepin-2-ones - new method of preparation | |
| DE838747C (de) | Verfahren zur Herstellung von Thiosemicarbazonen | |
| AT293362B (de) | Verfahren zur Herstellung von N-substituierten β-Aminopropiophenonen | |
| DE1173082B (de) | Verfahren zur Herstellung von N-mono-substituierten ª‡-Hydroxycarbonsaeureamiden |