DE2642150A1 - Benzodiazepine und verfahren zu ihrer herstellung sowie diese enthaltende arzneimittel - Google Patents
Benzodiazepine und verfahren zu ihrer herstellung sowie diese enthaltende arzneimittelInfo
- Publication number
- DE2642150A1 DE2642150A1 DE19762642150 DE2642150A DE2642150A1 DE 2642150 A1 DE2642150 A1 DE 2642150A1 DE 19762642150 DE19762642150 DE 19762642150 DE 2642150 A DE2642150 A DE 2642150A DE 2642150 A1 DE2642150 A1 DE 2642150A1
- Authority
- DE
- Germany
- Prior art keywords
- deep
- benzodiazepine
- formula
- imidazo
- ethyl
- 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.)
- Ceased
Links
- 229940049706 benzodiazepine Drugs 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 23
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 title claims 13
- 238000004519 manufacturing process Methods 0.000 title description 6
- 229940126601 medicinal product Drugs 0.000 title 1
- -1 8-chloro-1- [2- (dimethylamino) ethyl] -6-phenyl-4H-imidazo [1,2-a] [1,4] benzodiazepine Chemical compound 0.000 claims description 210
- 150000001875 compounds Chemical class 0.000 claims description 75
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 47
- 229910052801 chlorine Inorganic materials 0.000 claims description 41
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 229910052731 fluorine Inorganic materials 0.000 claims description 34
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 34
- 239000000460 chlorine Substances 0.000 claims description 30
- 125000001153 fluoro group Chemical group F* 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 22
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 20
- 150000001557 benzodiazepines Chemical class 0.000 claims description 18
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 18
- 239000012279 sodium borohydride Substances 0.000 claims description 17
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 17
- CETGYTZOZAIXBU-UHFFFAOYSA-N 4-aminobut-2-yn-1-ol Chemical compound NCC#CCO CETGYTZOZAIXBU-UHFFFAOYSA-N 0.000 claims description 16
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 16
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 15
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 9
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000005604 azodicarboxylate group Chemical group 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical class [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 claims description 5
- IFAHLJKLSJBYHX-UHFFFAOYSA-N 2-[6-(2-chlorophenyl)-4H-imidazo[1,2-a][1,4]benzodiazepin-1-yl]ethanamine Chemical compound NCCC1=CN=C2N1C1=C(C(=NC2)C2=C(C=CC=C2)Cl)C=CC=C1 IFAHLJKLSJBYHX-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 125000005265 dialkylamine group Chemical group 0.000 claims description 4
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 4
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims description 3
- HFJYVPKIKWZKPW-UHFFFAOYSA-N 2-(8-fluoro-6-phenyl-4H-imidazo[1,2-a][1,4]benzodiazepin-1-yl)-N,N-dimethylethanamine Chemical compound FC=1C=CC2=C(C(=NCC=3N2C(=CN3)CCN(C)C)C3=CC=CC=C3)C1 HFJYVPKIKWZKPW-UHFFFAOYSA-N 0.000 claims description 3
- NCNGLPPDHCACDW-UHFFFAOYSA-N 2-[8-chloro-6-(2-chlorophenyl)-4H-imidazo[1,2-a][1,4]benzodiazepin-1-yl]-N,N-dimethylethanamine Chemical compound ClC=1C=CC2=C(C(=NCC=3N2C(=CN=3)CCN(C)C)C2=C(C=CC=C2)Cl)C=1 NCNGLPPDHCACDW-UHFFFAOYSA-N 0.000 claims description 3
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000010792 warming Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- 241000699670 Mus sp. Species 0.000 description 16
- 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 13
- DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 13
- 229910000372 mercury(II) sulfate Inorganic materials 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- ZVIJZRNLKXUVGP-UHFFFAOYSA-N 2-[2-(8-chloro-6-phenyl-4H-imidazo[1,2-a][1,4]benzodiazepin-1-yl)ethyl]isoindole-1,3-dione Chemical compound ClC=1C=CC2=C(C(=NCC=3N2C(=CN3)CCN3C(C=2C(C3=O)=CC=CC2)=O)C2=CC=CC=C2)C1 ZVIJZRNLKXUVGP-UHFFFAOYSA-N 0.000 description 6
- XRVPRXZYYZWWBV-UHFFFAOYSA-N 2-[2-[2-(azidomethyl)-1,3-dioxolan-2-yl]ethyl]isoindole-1,3-dione Chemical compound N(=[N+]=[N-])CC1(OCCO1)CCN1C(C=2C(C1=O)=CC=CC2)=O XRVPRXZYYZWWBV-UHFFFAOYSA-N 0.000 description 6
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 6
- ADCKEOMMOFWLON-UHFFFAOYSA-N 2-[6-(2-chlorophenyl)-8-fluoro-4H-imidazo[1,2-a][1,4]benzodiazepin-1-yl]ethanamine Chemical compound FC=1C=CC2=C(C(=NCC=3N2C(=CN3)CCN)C3=C(C=CC=C3)Cl)C1 ADCKEOMMOFWLON-UHFFFAOYSA-N 0.000 description 5
- ZBSQVLQPJQPNCH-UHFFFAOYSA-N 2-[6-(2-chlorophenyl)-8-nitro-4H-imidazo[1,2-a][1,4]benzodiazepin-1-yl]ethanamine Chemical compound [N+](=O)([O-])C=1C=CC2=C(C(=NCC=3N2C(=CN3)CCN)C3=C(C=CC=C3)Cl)C1 ZBSQVLQPJQPNCH-UHFFFAOYSA-N 0.000 description 5
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- FFHNKDNVNWTFLU-UHFFFAOYSA-N 2-(8-chloro-6-phenyl-4H-imidazo[1,2-a][1,4]benzodiazepin-1-yl)ethanamine Chemical compound ClC=1C=CC2=C(C(=NCC=3N2C(=CN3)CCN)C3=CC=CC=C3)C1 FFHNKDNVNWTFLU-UHFFFAOYSA-N 0.000 description 4
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- WEBYMXPETNSTKH-UHFFFAOYSA-N 2-[2-[6-(2-chlorophenyl)-8-(trifluoromethyl)-4H-imidazo[1,2-a][1,4]benzodiazepin-1-yl]ethyl]isoindole-1,3-dione Chemical compound FC(C=1C=CC2=C(C(=NCC=3N2C(=CN3)CCN3C(C=2C(C3=O)=CC=CC2)=O)C2=C(C=CC=C2)Cl)C1)(F)F WEBYMXPETNSTKH-UHFFFAOYSA-N 0.000 description 3
- FDZVRKFEAYLMLB-UHFFFAOYSA-N 2-[2-[8-bromo-6-(2-chlorophenyl)-4H-imidazo[1,2-a][1,4]benzodiazepin-1-yl]ethyl]isoindole-1,3-dione Chemical compound BrC=1C=CC2=C(C(=NCC=3N2C(=CN3)CCN3C(C=2C(C3=O)=CC=CC2)=O)C2=C(C=CC=C2)Cl)C1 FDZVRKFEAYLMLB-UHFFFAOYSA-N 0.000 description 3
- JWSMHZFLMDSHEV-UHFFFAOYSA-N 2-[6-(2-chlorophenyl)-8-fluoro-4H-imidazo[1,2-a][1,4]benzodiazepin-1-yl]-N,N-dimethylethanamine Chemical compound FC=1C=CC2=C(C(=NCC=3N2C(=CN3)CCN(C)C)C3=C(C=CC=C3)Cl)C1 JWSMHZFLMDSHEV-UHFFFAOYSA-N 0.000 description 3
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- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical class OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61785175A | 1975-09-29 | 1975-09-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2642150A1 true DE2642150A1 (de) | 1977-04-07 |
Family
ID=24475310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762642150 Ceased DE2642150A1 (de) | 1975-09-29 | 1976-09-20 | Benzodiazepine und verfahren zu ihrer herstellung sowie diese enthaltende arzneimittel |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5242898A (enExample) |
| CH (2) | CH623588A5 (enExample) |
| DE (1) | DE2642150A1 (enExample) |
| FR (1) | FR2325382A1 (enExample) |
| GB (2) | GB1492159A (enExample) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3422091A (en) | 1962-07-10 | 1969-01-14 | Hoffmann La Roche | 5-phenyl-3h-1,4-benzodiazepine-2(ih)-thione and derivatives thereof |
-
1976
- 1976-08-17 GB GB21967/77A patent/GB1492159A/en not_active Expired
- 1976-08-17 GB GB34126/76A patent/GB1492158A/en not_active Expired
- 1976-09-20 DE DE19762642150 patent/DE2642150A1/de not_active Ceased
- 1976-09-24 CH CH1215476A patent/CH623588A5/de not_active IP Right Cessation
- 1976-09-28 JP JP51116478A patent/JPS5242898A/ja active Pending
- 1976-09-28 FR FR7629127A patent/FR2325382A1/fr active Granted
-
1980
- 1980-08-05 CH CH593380A patent/CH623821A5/de not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3422091A (en) | 1962-07-10 | 1969-01-14 | Hoffmann La Roche | 5-phenyl-3h-1,4-benzodiazepine-2(ih)-thione and derivatives thereof |
Non-Patent Citations (8)
| Title |
|---|
| Archer und Mitarbeiter in "J. Org. Chem.", Band 29, Seite 231 (1964) und |
| Eaton und Mitarbeiter in "J. Org. Chem.", Band 38, Seite 1014 (1973) |
| Juenge und Mitarbeitern in "J. Org. Chem.", Band 29, Seite 226 (1964) |
| Kamintext "Med. Exp.", Band 4, Seite 145-1961 |
| R.A. Crochet und Mitarbeitern in "Synthesis" (1974), Seite 55 |
| R.G. Jones und Mitarbeiter in "J. Am. Chem. Soc.", Band 72, Seite 4526-1950 |
| The Benzodiazepines", Monograph, Raven Press, New York 1973, Seite 285 |
| W. J. Baily und Mitarbeiter in "J. Am. Chem. Soc.", Band 77, Seite 165 - 1955 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2325382B1 (enExample) | 1978-11-17 |
| CH623821A5 (en) | 1981-06-30 |
| CH623588A5 (en) | 1981-06-15 |
| GB1492158A (en) | 1977-11-16 |
| GB1492159A (en) | 1977-11-16 |
| JPS5242898A (en) | 1977-04-04 |
| FR2325382A1 (fr) | 1977-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: HENKEL, G., DR.PHIL. FEILER, L., DR.RER.NAT. HAENZ |
|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |