IE38091L - Manufacture of benzodiazepine derivatives. - Google Patents
Manufacture of benzodiazepine derivatives.Info
- Publication number
- IE38091L IE38091L IE731409A IE140973A IE38091L IE 38091 L IE38091 L IE 38091L IE 731409 A IE731409 A IE 731409A IE 140973 A IE140973 A IE 140973A IE 38091 L IE38091 L IE 38091L
- 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
- 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1392681 Benzodiazepine derivatives F HOFFMANN-LA ROCHE & CO AG 20 Aug 1973 [21 Aug 1972 14 May 1973] 39218/73 Heading C2C Benzodiazepine derivatives of general formula where R 1 is a hydrogen or halogen atom or a nitro or trifluoromethyl group, R 2 is a hydrogen atom or a C 1 -C 5 alkyl group, and R 3 is a phenyl, o-halophenyl or 2-pyridyl group are prepared by reacting a compound of general formula where X is Cl, Br or I, with hexamethylenetetramine in an inert organic solvent and in the presence of ammonia, with the possible isolation of an intermediate of general formula The ammonia may be formed in situ from an ammonia-generating agent, e.g. ammonium carbonate, and the hexamethylenetetramine may also be formed in situ from formaldehyde and ammonia.
[GB1392681A]
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 true IE38091L (en) | 1974-02-21 |
| IE38091B1 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)
| Country | Link |
|---|---|
| JP (1) | JPS5911589B2 (en) |
| AR (1) | AR198108A1 (en) |
| AT (1) | AT341527B (en) |
| AU (1) | AU472777B2 (en) |
| CA (1) | CA1012535A (en) |
| CH (1) | CH578544A5 (en) |
| DD (1) | DD107040A5 (en) |
| DE (1) | DE2340159A1 (en) |
| DK (1) | DK155326C (en) |
| ES (1) | ES418014A1 (en) |
| FI (1) | FI57939C (en) |
| FR (1) | FR2197003B1 (en) |
| GB (1) | GB1392681A (en) |
| HU (1) | HU170153B (en) |
| IE (1) | IE38091B1 (en) |
| IL (1) | IL42947A (en) |
| LU (1) | LU68269A1 (en) |
| NL (1) | NL179582C (en) |
| NO (1) | NO139481C (en) |
| PH (1) | PH13640A (en) |
| PL (1) | PL99162B1 (en) |
| SE (1) | SE408302B (en) |
| SU (1) | SU550980A3 (en) |
| YU (1) | YU219873A (en) |
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 (en) * | 1996-10-18 | 1998-10-20 | Олег Иванович Лукашов | Method of preparing 7-bromo-1,3-dihydro-5-[2- chlorophenyl]-2h-1,4-benzdiazepin-2-one, 5-bromo-2-[2- chloroacetamido]-2′-clorobenzophenone |
| RU2150467C1 (en) * | 1998-01-06 | 2000-06-10 | Петрунин Александр Иванович | Method of synthesis of 1,3-dihydro-7-nitro-5-phenyl-2h-1,4- -benzodiazepine-2-one (nitrazepam) (variants) |
| CN113149915B (en) * | 2021-03-01 | 2024-03-15 | 中国科学院成都有机化学有限公司 | A kind of method for synthesizing clonazepam compound |
| CN116023342B (en) * | 2021-10-26 | 2024-06-25 | 江苏昱林生物科技有限公司 | Preparation method of high-purity clonazepam |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1136709B (en) * | 1959-12-10 | 1962-09-20 | Hoffmann La Roche | Process for the preparation of 2-oxo-1, 2-dihydro-1, 4-benzodiazepines |
| CH537393A (en) * | 1969-10-16 | 1973-05-31 | Hoffmann La Roche | Process for the preparation of 1,4-benzodiazepine derivatives |
| BE785962A (en) * | 1971-07-08 | 1973-01-08 | Hoffmann La Roche | PROCESS FOR THE PREPARATION OF BENZODIAZEPINE DERIVATIVES |
-
1973
- 1973-08-02 CH CH1121873A patent/CH578544A5/xx not_active IP Right Cessation
- 1973-08-08 DE DE19732340159 patent/DE2340159A1/en 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/en unknown
- 1973-08-15 IE IE1409/73A patent/IE38091B1/en unknown
- 1973-08-15 PH PH14926A patent/PH13640A/en unknown
- 1973-08-16 AR AR249597A patent/AR198108A1/en active
- 1973-08-16 HU HUHO1604A patent/HU170153B/hu not_active IP Right Cessation
- 1973-08-17 AT AT720773A patent/AT341527B/en not_active IP Right Cessation
- 1973-08-20 DK DK457773A patent/DK155326C/en not_active IP Right Cessation
- 1973-08-20 DD DD172980A patent/DD107040A5/xx unknown
- 1973-08-20 ES ES418014A patent/ES418014A1/en not_active Expired
- 1973-08-20 PL PL1973164759A patent/PL99162B1/en unknown
- 1973-08-20 JP JP48093220A patent/JPS5911589B2/en not_active Expired
- 1973-08-20 GB GB3921873A patent/GB1392681A/en not_active Expired
- 1973-08-20 LU LU68269A patent/LU68269A1/xx unknown
- 1973-08-20 NO NO3285/73A patent/NO139481C/en unknown
- 1973-08-20 SU SU1959095A patent/SU550980A3/en active
- 1973-08-20 CA CA179,143A patent/CA1012535A/en not_active Expired
- 1973-08-20 SE SE7311319A patent/SE408302B/en unknown
- 1973-08-21 FI FI2613/73A patent/FI57939C/en active
- 1973-08-21 NL NLAANVRAGE7311507,A patent/NL179582C/en not_active IP Right Cessation
- 1973-08-21 FR FR7330353A patent/FR2197003B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2197003A1 (en) | 1974-03-22 |
| AT341527B (en) | 1978-02-10 |
| NL179582C (en) | 1986-10-01 |
| ES418014A1 (en) | 1976-03-16 |
| NL7311507A (en) | 1974-02-25 |
| AR198108A1 (en) | 1974-05-31 |
| NL179582B (en) | 1986-05-01 |
| ATA720773A (en) | 1977-06-15 |
| NO139481B (en) | 1978-12-11 |
| JPS5911589B2 (en) | 1984-03-16 |
| LU68269A1 (en) | 1975-05-21 |
| AU472777B2 (en) | 1976-06-03 |
| IL42947A0 (en) | 1973-11-28 |
| DD107040A5 (en) | 1974-07-12 |
| AU5918073A (en) | 1975-02-13 |
| FI57939B (en) | 1980-07-31 |
| CA1012535A (en) | 1977-06-21 |
| SU550980A3 (en) | 1977-03-15 |
| DK155326B (en) | 1989-03-28 |
| PH13640A (en) | 1980-08-18 |
| FR2197003B1 (en) | 1978-01-13 |
| YU219873A (en) | 1982-06-30 |
| IE38091B1 (en) | 1977-12-21 |
| JPS4956992A (en) | 1974-06-03 |
| GB1392681A (en) | 1975-04-30 |
| DE2340159A1 (en) | 1974-03-07 |
| PL99162B1 (en) | 1978-06-30 |
| NO139481C (en) | 1979-03-21 |
| FI57939C (en) | 1980-11-10 |
| CH578544A5 (en) | 1976-08-13 |
| DK155326C (en) | 1989-08-14 |
| IL42947A (en) | 1977-01-31 |
| DE2340159C2 (en) | 1989-01-19 |
| HU170153B (en) | 1977-04-28 |
| SE408302B (en) | 1979-06-05 |
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