IE38091B1 - Process for the manufacture of benzodiazepine derivatives - Google Patents
Process for the manufacture of benzodiazepine derivativesInfo
- Publication number
- IE38091B1 IE38091B1 IE1409/73A IE140973A IE38091B1 IE 38091 B1 IE38091 B1 IE 38091B1 IE 1409/73 A IE1409/73 A IE 1409/73A IE 140973 A IE140973 A IE 140973A IE 38091 B1 IE38091 B1 IE 38091B1
- Authority
- IE
- Ireland
- Prior art keywords
- ammonia
- benzodiazepine derivatives
- general formula
- hexamethylenetetramine
- aug
- Prior art date
Links
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 title abstract 3
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 6
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 229910021529 ammonia Inorganic materials 0.000 abstract 3
- 239000004312 hexamethylene tetramine Substances 0.000 abstract 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 abstract 2
- 238000011065 in-situ storage Methods 0.000 abstract 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 abstract 1
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 235000012501 ammonium carbonate Nutrition 0.000 abstract 1
- 239000001099 ammonium carbonate Substances 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 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 |
|---|---|
| IE38091L IE38091L (en) | 1974-02-21 |
| IE38091B1 true IE38091B1 (en) | 1977-12-21 |
Family
ID=26961312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1409/73A IE38091B1 (en) | 1972-08-21 | 1973-08-15 | Process for the manufacture of benzodiazepine derivatives |
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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