DE1670190A1 - Verfahren zur Herstellung von 1,5-Dihydro-5-phenyl-3H-1,5-benzodiazepin-2,4-dionen - Google Patents
Verfahren zur Herstellung von 1,5-Dihydro-5-phenyl-3H-1,5-benzodiazepin-2,4-dionenInfo
- Publication number
- DE1670190A1 DE1670190A1 DE19671670190 DE1670190A DE1670190A1 DE 1670190 A1 DE1670190 A1 DE 1670190A1 DE 19671670190 DE19671670190 DE 19671670190 DE 1670190 A DE1670190 A DE 1670190A DE 1670190 A1 DE1670190 A1 DE 1670190A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- benzodiazepine
- dihydro
- dione
- hydrogen
- 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
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 5
- CBRLXMKQJJHXPL-UHFFFAOYSA-N 5-phenyl-1h-1,5-benzodiazepine-2,4-dione Chemical class C12=CC=CC=C2NC(=O)CC(=O)N1C1=CC=CC=C1 CBRLXMKQJJHXPL-UHFFFAOYSA-N 0.000 title claims description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 206010003840 Autonomic nervous system imbalance Diseases 0.000 claims 1
- 208000001431 Psychomotor Agitation Diseases 0.000 claims 1
- 206010038743 Restlessness Diseases 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229940035676 analgesics Drugs 0.000 claims 1
- 239000000730 antalgic agent Substances 0.000 claims 1
- 229940125681 anticonvulsant agent Drugs 0.000 claims 1
- 239000001961 anticonvulsive agent Substances 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 239000012876 carrier material Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 25
- -1 1,5-dihydro-5- (2-ethylphenyl) -7-chloro-3H-1,5-benzodiazepine- Chemical compound 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 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 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 239000007868 Raney catalyst Substances 0.000 description 7
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 7
- 229910000564 Raney nickel Inorganic materials 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 229940049706 benzodiazepine Drugs 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- RUKISNQKOIKZGT-UHFFFAOYSA-N 2-nitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=CC=C1 RUKISNQKOIKZGT-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- SNXMIMURQMSZTO-UHFFFAOYSA-N 7-chloro-1,5-benzodiazepine-2,4-dione Chemical compound O=C1CC(=O)N=C2C=C(Cl)C=CC2=N1 SNXMIMURQMSZTO-UHFFFAOYSA-N 0.000 description 1
- GWVJSTVUWPHUTL-UHFFFAOYSA-N 7-chloro-1-ethyl-5-phenyl-1,5-benzodiazepine-2,4-dione Chemical compound O=C1CC(=O)N(CC)C2=CC=C(Cl)C=C2N1C1=CC=CC=C1 GWVJSTVUWPHUTL-UHFFFAOYSA-N 0.000 description 1
- VMWAMPTULNZGNW-UHFFFAOYSA-N 7-methoxy-5-phenyl-1H-1,5-benzodiazepine-2,4-dione Chemical compound COC1=CC2=C(NC(CC(N2C2=CC=CC=C2)=O)=O)C=C1 VMWAMPTULNZGNW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- PZMSAMSXJWOSMO-UHFFFAOYSA-N CC1=CC2=C(C=C1)N(C1=CC=CC=C1)C(=O)CC(=O)N2 Chemical compound CC1=CC2=C(C=C1)N(C1=CC=CC=C1)C(=O)CC(=O)N2 PZMSAMSXJWOSMO-UHFFFAOYSA-N 0.000 description 1
- HOKIWUWUMMTFHP-UHFFFAOYSA-N COC1=CC=C(C=C1)N1C2=C(NC(=O)CC1=O)C=CC=C2 Chemical compound COC1=CC=C(C=C1)N1C2=C(NC(=O)CC1=O)C=CC=C2 HOKIWUWUMMTFHP-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C07D243/12—1,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0091071 | 1967-02-07 | ||
| DEB0096282 | 1968-01-18 | ||
| DEB0096281 | 1968-01-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1670190A1 true DE1670190A1 (de) | 1970-12-03 |
Family
ID=27209412
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671670190 Pending DE1670190A1 (de) | 1967-02-07 | 1967-02-07 | Verfahren zur Herstellung von 1,5-Dihydro-5-phenyl-3H-1,5-benzodiazepin-2,4-dionen |
| DE19681670306 Pending DE1670306A1 (de) | 1967-02-07 | 1968-01-18 | Verfahren zur Herstellung von 5-Phenyl-1H-1,5-benzodiazepin-2,4-dionen |
| DE1670305A Expired DE1670305C3 (de) | 1967-02-07 | 1968-01-18 | 5-Phenyl-2,4-dioxo-1,2,3,4-tetrahydro-3H-1,5-benzodiazepine und Verfahren zu ihrer Herstellung |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681670306 Pending DE1670306A1 (de) | 1967-02-07 | 1968-01-18 | Verfahren zur Herstellung von 5-Phenyl-1H-1,5-benzodiazepin-2,4-dionen |
| DE1670305A Expired DE1670305C3 (de) | 1967-02-07 | 1968-01-18 | 5-Phenyl-2,4-dioxo-1,2,3,4-tetrahydro-3H-1,5-benzodiazepine und Verfahren zu ihrer Herstellung |
Country Status (15)
| Country | Link |
|---|---|
| US (8) | US3707539A (en, 2012) |
| AT (2) | AT281037B (en, 2012) |
| BE (1) | BE710475A (en, 2012) |
| CA (4) | CA970776A (en, 2012) |
| CH (2) | CH509330A (en, 2012) |
| DE (3) | DE1670190A1 (en, 2012) |
| DK (3) | DK127065B (en, 2012) |
| ES (2) | ES350203A1 (en, 2012) |
| FI (2) | FI56003C (en, 2012) |
| FR (2) | FR1574710A (en, 2012) |
| GB (1) | GB1214662A (en, 2012) |
| IL (1) | IL29425A (en, 2012) |
| NL (1) | NL158386B (en, 2012) |
| SE (4) | SE367416B (en, 2012) |
| YU (1) | YU39921B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001408A (en) * | 1966-12-14 | 1977-01-04 | Roussel-Uclaf | Substituted heterocyclic compounds, processes and composition including those |
| AT283372B (de) * | 1968-04-29 | 1970-08-10 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung neuer 1-Acyl-5-phenyl-1H-1,5-benzodiazepin-2,4-[3H,5H]-dione |
| DE1934607A1 (de) * | 1968-07-12 | 1970-01-22 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung neuer 5-Aryl-1H-1,5-benzodiazepin-2,4-dione |
| DE1913536C2 (de) * | 1969-03-18 | 1983-05-11 | Knoll Ag, 6700 Ludwigshafen | 1-Phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one und Verfahren zu deren Herstellung |
| DE2062237C2 (de) * | 1970-03-04 | 1983-08-04 | Knoll Ag, 6700 Ludwigshafen | 1-Phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one, ihre Herstellung und Verwendung |
| DE2052840C2 (de) * | 1970-10-28 | 1983-09-08 | Knoll Ag, 6700 Ludwigshafen | 8-Chlor-1-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-on-Derivate |
| US4442138A (en) * | 1982-02-22 | 1984-04-10 | Westinghouse Electric Corp. | Substrate pretreatment with a metal-beta keto ester complex in the method of curing an anaerobic resin |
| WO1991015464A1 (en) * | 1990-04-11 | 1991-10-17 | Warner-Lambert Company | Amide ester acat inhibitors |
| EP1127054A4 (en) * | 1998-10-29 | 2006-11-02 | Bristol Myers Squibb Co | INHIBITORS OF IMPDH ENZYME |
| WO2016151464A1 (en) * | 2015-03-24 | 2016-09-29 | Piramal Enterprises Limited | An improved process for the preparation of clobazam and its intermediate |
-
1967
- 1967-02-07 DE DE19671670190 patent/DE1670190A1/de active Pending
-
1968
- 1968-01-18 DE DE19681670306 patent/DE1670306A1/de active Pending
- 1968-01-18 DE DE1670305A patent/DE1670305C3/de not_active Expired
- 1968-02-02 CH CH157868A patent/CH509330A/de not_active IP Right Cessation
- 1968-02-02 CH CH1382070A patent/CH523894A/de not_active IP Right Cessation
- 1968-02-05 AT AT109168A patent/AT281037B/de not_active IP Right Cessation
- 1968-02-05 AT AT05454/69A patent/AT281045B/de active
- 1968-02-06 DK DK46268AA patent/DK127065B/da unknown
- 1968-02-06 IL IL6829425A patent/IL29425A/xx unknown
- 1968-02-06 ES ES350203A patent/ES350203A1/es not_active Expired
- 1968-02-07 NL NL6801696.A patent/NL158386B/xx unknown
- 1968-02-07 SE SE02850/71A patent/SE367416B/xx unknown
- 1968-02-07 SE SE02851/71A patent/SE367417B/xx unknown
- 1968-02-07 SE SE1593/68A patent/SE342628B/xx unknown
- 1968-02-07 CA CA011,826A patent/CA970776A/en not_active Expired
- 1968-02-07 FI FI325/68A patent/FI56003C/fi active
- 1968-02-07 GB GB6068/68A patent/GB1214662A/en not_active Expired
- 1968-02-07 BE BE710475D patent/BE710475A/xx unknown
- 1968-02-07 FR FR1574710D patent/FR1574710A/fr not_active Expired
- 1968-02-07 SE SE02852/71A patent/SE367418B/xx unknown
- 1968-05-07 FR FR150867A patent/FR8141M/fr not_active Expired
-
1969
- 1969-02-14 ES ES363654A patent/ES363654A1/es not_active Expired
-
1971
- 1971-02-01 US US111713A patent/US3707539A/en not_active Expired - Lifetime
- 1971-02-01 US US00111715A patent/US3711509A/en not_active Expired - Lifetime
- 1971-02-01 US US00111714A patent/US3711470A/en not_active Expired - Lifetime
- 1971-02-01 US US111716A patent/US3684798A/en not_active Expired - Lifetime
- 1971-08-27 DK DK421571AA patent/DK126330B/da unknown
- 1971-08-27 DK DK421671A patent/DK131936C/da active
-
1972
- 1972-09-27 US US00292749A patent/US3836652A/en not_active Expired - Lifetime
- 1972-09-27 US US00292748A patent/US3760074A/en not_active Expired - Lifetime
- 1972-10-30 US US00301896A patent/US3836653A/en not_active Expired - Lifetime
-
1974
- 1974-05-21 YU YU1408/74A patent/YU39921B/xx unknown
-
1975
- 1975-06-11 CA CA229,104A patent/CA997758A/en not_active Expired
- 1975-06-11 CA CA229,103A patent/CA997757A/en not_active Expired
- 1975-06-11 CA CA229,102A patent/CA1006513A/en not_active Expired
- 1975-06-17 US US05/587,591 patent/USRE28935E/en not_active Expired - Lifetime
-
1979
- 1979-03-29 FI FI791055A patent/FI61309C/fi not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| OHN | Withdrawal |