IL42947A - Process for the preparation of 1,3-dihydro-2h-1,4-benzodiazepin-2-ones - Google Patents
Process for the preparation of 1,3-dihydro-2h-1,4-benzodiazepin-2-onesInfo
- Publication number
- IL42947A IL42947A IL42947A IL4294773A IL42947A IL 42947 A IL42947 A IL 42947A IL 42947 A IL42947 A IL 42947A IL 4294773 A IL4294773 A IL 4294773A IL 42947 A IL42947 A IL 42947A
- Authority
- IL
- Israel
- Prior art keywords
- ammonia
- process according
- phenyl
- nitro
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 51
- 238000002360 preparation method Methods 0.000 title description 5
- UDLAUVFRZXIQJS-UHFFFAOYSA-N 1,3-dihydro-1,4-benzodiazepin-2-one Chemical class N1C(=O)CN=CC2=CC=CC=C21 UDLAUVFRZXIQJS-UHFFFAOYSA-N 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 201
- 229910021529 ammonia Inorganic materials 0.000 claims description 99
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 84
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 42
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 40
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 239000003960 organic solvent Substances 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 238000002955 isolation Methods 0.000 claims description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 11
- 239000000543 intermediate Substances 0.000 claims 5
- 238000011065 in-situ storage Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 90
- 238000010992 reflux Methods 0.000 description 55
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 229960004011 methenamine Drugs 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000012429 reaction media Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- 230000005587 bubbling Effects 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 239000007858 starting material Substances 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- HDXLZRWEZZFDKA-UHFFFAOYSA-N n-(2-benzoyl-4-chlorophenyl)-2-chloroacetamide Chemical compound ClCC(=O)NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 HDXLZRWEZZFDKA-UHFFFAOYSA-N 0.000 description 6
- 239000002002 slurry Substances 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- 238000001914 filtration Methods 0.000 description 3
- HIMNRRQRDQNAEN-UHFFFAOYSA-N n-(2-benzoylphenyl)-2-chloroacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1C(=O)C1=CC=CC=C1 HIMNRRQRDQNAEN-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011369 resultant mixture Substances 0.000 description 2
- XSTMFEOLMKEEMU-UHFFFAOYSA-N 2-bromo-n-[2-(2-chlorobenzoyl)-4-nitrophenyl]acetamide Chemical compound [O-][N+](=O)C1=CC=C(NC(=O)CBr)C(C(=O)C=2C(=CC=CC=2)Cl)=C1 XSTMFEOLMKEEMU-UHFFFAOYSA-N 0.000 description 1
- DGIHQJAKOHGCOQ-UHFFFAOYSA-N 2-bromo-n-[2-(2-fluorobenzoyl)-4-nitrophenyl]acetamide Chemical compound [O-][N+](=O)C1=CC=C(NC(=O)CBr)C(C(=O)C=2C(=CC=CC=2)F)=C1 DGIHQJAKOHGCOQ-UHFFFAOYSA-N 0.000 description 1
- JQMAWYRGSOSWNJ-UHFFFAOYSA-N 2-bromo-n-[4-chloro-2-(2-chlorobenzoyl)phenyl]acetamide Chemical compound ClC1=CC=C(NC(=O)CBr)C(C(=O)C=2C(=CC=CC=2)Cl)=C1 JQMAWYRGSOSWNJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- DSAWUUVGNZAARH-UHFFFAOYSA-N n-(2-benzoyl-4-chlorophenyl)-2-chloro-n-methylacetamide Chemical compound ClCC(=O)N(C)C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 DSAWUUVGNZAARH-UHFFFAOYSA-N 0.000 description 1
- ZHJLHAOWFYEIOC-UHFFFAOYSA-N n-(2-benzoyl-4-nitrophenyl)-2-chloroacetamide Chemical compound [O-][N+](=O)C1=CC=C(NC(=O)CCl)C(C(=O)C=2C=CC=CC=2)=C1 ZHJLHAOWFYEIOC-UHFFFAOYSA-N 0.000 description 1
- LYISZEZBKBGONS-UHFFFAOYSA-N n-[4-bromo-2-(pyridine-2-carbonyl)phenyl]-2-chloroacetamide Chemical compound ClCC(=O)NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=N1 LYISZEZBKBGONS-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 238000005406 washing 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
- 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
- C07D243/24—Oxygen atoms
-
- 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
- C07D243/24—Oxygen atoms
- C07D243/28—Preparation including building-up the benzodiazepine skeleton from compounds containing no hetero rings
-
- 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
- C07D243/24—Oxygen atoms
- C07D243/30—Preparation including building-up the benzodiazepine skeleton from compounds already containing hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28221772A | 1972-08-21 | 1972-08-21 | |
| US35981473A | 1973-05-14 | 1973-05-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42947A0 IL42947A0 (en) | 1973-11-28 |
| IL42947A true IL42947A (en) | 1977-01-31 |
Family
ID=26961312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42947A IL42947A (en) | 1972-08-21 | 1973-08-10 | Process for the preparation of 1,3-dihydro-2h-1,4-benzodiazepin-2-ones |
Country Status (24)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5334792A (en) * | 1976-09-13 | 1978-03-31 | Scherico Ltd | Production of 1*44 benzodiazepines and 1*44 benzodiazepinee22ones |
| RU2120441C1 (ru) * | 1996-10-18 | 1998-10-20 | Олег Иванович Лукашов | Способ получения 7-бром-1,3-дигидро-5-/2-хлорфенил/-2н-1,4-бензидиазепин-2-она, промежуточное соединение 5-бром-2-/2-хлорацетамидо/-2'-хлорбензофенон |
| RU2150467C1 (ru) * | 1998-01-06 | 2000-06-10 | Петрунин Александр Иванович | Способ получения 1,3-дигидро-7-нитро-5-фенил-2h-1,4-бензодиазепин-2-она (нитразепама) (варианты) |
| CN113149915B (zh) * | 2021-03-01 | 2024-03-15 | 中国科学院成都有机化学有限公司 | 一种合成氯硝西泮化合物的方法 |
| CN116023342B (zh) * | 2021-10-26 | 2024-06-25 | 江苏昱林生物科技有限公司 | 一种高纯度氯硝西泮的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1136709B (de) * | 1959-12-10 | 1962-09-20 | Hoffmann La Roche | Verfahren zur Herstellung von 2-Oxo-1, 2-dihydro-1, 4-benzodiazepinen |
| CH537393A (de) * | 1969-10-16 | 1973-05-31 | Hoffmann La Roche | Verfahren zur Herstellung von 1,4-Benzodiazepin-derivaten |
| BE785962A (fr) * | 1971-07-08 | 1973-01-08 | Hoffmann La Roche | Procede pour la preparation de derives de benzodiazepine |
-
1973
- 1973-08-02 CH CH1121873A patent/CH578544A5/xx not_active IP Right Cessation
- 1973-08-08 DE DE19732340159 patent/DE2340159A1/de active Granted
- 1973-08-10 IL IL42947A patent/IL42947A/en unknown
- 1973-08-13 AU AU59180/73A patent/AU472777B2/en not_active Expired
- 1973-08-14 YU YU02198/73A patent/YU219873A/xx unknown
- 1973-08-15 IE IE1409/73A patent/IE38091B1/xx unknown
- 1973-08-15 PH PH14926A patent/PH13640A/en unknown
- 1973-08-16 HU HUHO1604A patent/HU170153B/hu not_active IP Right Cessation
- 1973-08-16 AR AR249597A patent/AR198108A1/es active
- 1973-08-17 AT AT720773A patent/AT341527B/de not_active IP Right Cessation
- 1973-08-20 SE SE7311319A patent/SE408302B/xx unknown
- 1973-08-20 CA CA179,143A patent/CA1012535A/en not_active Expired
- 1973-08-20 PL PL1973164759A patent/PL99162B1/pl unknown
- 1973-08-20 JP JP48093220A patent/JPS5911589B2/ja not_active Expired
- 1973-08-20 LU LU68269A patent/LU68269A1/xx unknown
- 1973-08-20 NO NO3285/73A patent/NO139481C/no unknown
- 1973-08-20 ES ES418014A patent/ES418014A1/es not_active Expired
- 1973-08-20 GB GB3921873A patent/GB1392681A/en not_active Expired
- 1973-08-20 SU SU1959095A patent/SU550980A3/ru active
- 1973-08-20 DD DD172980A patent/DD107040A5/xx unknown
- 1973-08-20 DK DK457773A patent/DK155326C/da not_active IP Right Cessation
- 1973-08-21 NL NLAANVRAGE7311507,A patent/NL179582C/xx not_active IP Right Cessation
- 1973-08-21 FI FI2613/73A patent/FI57939C/fi active
- 1973-08-21 FR FR7330353A patent/FR2197003B1/fr not_active Expired
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