PL101952B1 - A method of producing new derivatives of benzodiazepine - Google Patents
A method of producing new derivatives of benzodiazepine Download PDFInfo
- Publication number
- PL101952B1 PL101952B1 PL1975181497A PL18149775A PL101952B1 PL 101952 B1 PL101952 B1 PL 101952B1 PL 1975181497 A PL1975181497 A PL 1975181497A PL 18149775 A PL18149775 A PL 18149775A PL 101952 B1 PL101952 B1 PL 101952B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- compound
- defined above
- acid
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 37
- 150000001557 benzodiazepines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 5
- 229910052783 alkali metal Inorganic materials 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- -1 nitroso, amino Chemical group 0.000 claims 4
- 230000029936 alkylation Effects 0.000 claims 3
- 238000005804 alkylation reaction Methods 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 239000011230 binding agent Substances 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 229960000583 acetic acid Drugs 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical group [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- ROXAFEIDZVHGFX-UHFFFAOYSA-N 1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Chemical class N1C(=O)CNCC2=CC=CC=C21 ROXAFEIDZVHGFX-UHFFFAOYSA-N 0.000 claims 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 150000001351 alkyl iodides Chemical class 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- 239000012267 brine Substances 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 150000008050 dialkyl sulfates Chemical class 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- 150000007529 inorganic bases Chemical group 0.000 claims 1
- 239000000395 magnesium oxide Substances 0.000 claims 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical group [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 230000009935 nitrosation Effects 0.000 claims 1
- 238000007034 nitrosation reaction Methods 0.000 claims 1
- 150000007530 organic bases Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000009467 reduction Effects 0.000 claims 1
- 235000010288 sodium nitrite Nutrition 0.000 claims 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims 1
- 238000003797 solvolysis reaction Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 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 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 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
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- 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
- C07D243/26—Preparation from compounds already containing the benzodiazepine skeleton
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Toxicology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Anesthesiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HURI540A HU170623B (forum.php) | 1974-06-25 | 1974-06-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL101952B1 true PL101952B1 (pl) | 1979-02-28 |
Family
ID=11000952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1975181497A PL101952B1 (pl) | 1974-06-25 | 1975-06-24 | A method of producing new derivatives of benzodiazepine |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4021421A (forum.php) |
| JP (2) | JPS541716B2 (forum.php) |
| AT (1) | AT344698B (forum.php) |
| AU (1) | AU499054B2 (forum.php) |
| BE (1) | BE830582A (forum.php) |
| BG (2) | BG32570A3 (forum.php) |
| CA (1) | CA1047493A (forum.php) |
| CH (2) | CH632254A5 (forum.php) |
| CS (1) | CS195707B2 (forum.php) |
| DD (1) | DD123887A5 (forum.php) |
| DE (1) | DE2527901A1 (forum.php) |
| DK (1) | DK284675A (forum.php) |
| FR (1) | FR2276054A1 (forum.php) |
| GB (1) | GB1509445A (forum.php) |
| HU (1) | HU170623B (forum.php) |
| IL (1) | IL47495A (forum.php) |
| NL (1) | NL7507556A (forum.php) |
| PL (1) | PL101952B1 (forum.php) |
| SE (1) | SE423711B (forum.php) |
| SU (1) | SU1080744A3 (forum.php) |
| YU (1) | YU161075A (forum.php) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU187262B (en) * | 1979-08-16 | 1985-12-28 | Richter Gedeon Vegyeszet | Process for preparing new tetrahydro-1,4-benzodiazepin-2-ones |
| WO2000073284A2 (en) | 1999-05-26 | 2000-12-07 | Du Pont Pharmaceuticals Company | 1,4-benzodiazepin-2-ones useful as hiv reverse transcriptase inhibitors |
| CN105716725B (zh) * | 2016-03-10 | 2019-02-12 | 中国科学院光电技术研究所 | 一种基于叠层扫描的相位差波前探测和图像复原方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3236838A (en) * | 1964-06-09 | 1966-02-22 | Hoffmann La Roche | Certain 1-substituted-benzodiazepin-2-one compounds |
-
1974
- 1974-06-25 HU HURI540A patent/HU170623B/hu not_active IP Right Cessation
-
1975
- 1975-06-17 IL IL47495A patent/IL47495A/xx unknown
- 1975-06-18 SE SE7507039A patent/SE423711B/xx not_active IP Right Cessation
- 1975-06-19 AU AU82238/75A patent/AU499054B2/en not_active Expired
- 1975-06-19 FR FR7519196A patent/FR2276054A1/fr active Granted
- 1975-06-23 CS CS754443A patent/CS195707B2/cs unknown
- 1975-06-23 DE DE19752527901 patent/DE2527901A1/de not_active Withdrawn
- 1975-06-23 US US05/589,079 patent/US4021421A/en not_active Expired - Lifetime
- 1975-06-23 CH CH811075A patent/CH632254A5/de not_active IP Right Cessation
- 1975-06-24 JP JP7854575A patent/JPS541716B2/ja not_active Expired
- 1975-06-24 DD DD186853A patent/DD123887A5/xx unknown
- 1975-06-24 BG BG032384A patent/BG32570A3/xx unknown
- 1975-06-24 YU YU01610/75A patent/YU161075A/xx unknown
- 1975-06-24 DK DK284675A patent/DK284675A/da not_active Application Discontinuation
- 1975-06-24 SU SU752149105A patent/SU1080744A3/ru active
- 1975-06-24 AT AT481975A patent/AT344698B/de not_active IP Right Cessation
- 1975-06-24 BG BG030386A patent/BG32569A3/xx unknown
- 1975-06-24 BE BE157631A patent/BE830582A/xx not_active IP Right Cessation
- 1975-06-24 PL PL1975181497A patent/PL101952B1/pl unknown
- 1975-06-24 CA CA230,062A patent/CA1047493A/en not_active Expired
- 1975-06-25 NL NL7507556A patent/NL7507556A/xx unknown
- 1975-06-25 GB GB26920/75A patent/GB1509445A/en not_active Expired
-
1977
- 1977-11-25 JP JP52140842A patent/JPS6026113B2/ja not_active Expired
-
1979
- 1979-04-11 CH CH342479A patent/CH634835A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1047493A (en) | 1979-01-30 |
| JPS5119783A (forum.php) | 1976-02-17 |
| JPS5377079A (en) | 1978-07-08 |
| ATA481975A (de) | 1977-12-15 |
| FR2276054B1 (forum.php) | 1979-08-10 |
| AU499054B2 (en) | 1979-04-05 |
| AT344698B (de) | 1978-08-10 |
| CS195707B2 (en) | 1980-02-29 |
| IL47495A0 (en) | 1975-08-31 |
| BG32569A3 (en) | 1982-08-16 |
| CH632254A5 (de) | 1982-09-30 |
| BE830582A (fr) | 1975-10-16 |
| IL47495A (en) | 1979-03-12 |
| GB1509445A (en) | 1978-05-04 |
| DK284675A (da) | 1975-12-26 |
| DE2527901A1 (de) | 1976-01-15 |
| US4021421A (en) | 1977-05-03 |
| JPS541716B2 (forum.php) | 1979-01-27 |
| BG32570A3 (en) | 1982-08-16 |
| FR2276054A1 (fr) | 1976-01-23 |
| SE7507039L (sv) | 1975-12-29 |
| HU170623B (forum.php) | 1977-07-28 |
| JPS6026113B2 (ja) | 1985-06-21 |
| DD123887A5 (forum.php) | 1977-01-19 |
| NL7507556A (nl) | 1975-12-30 |
| AU8223875A (en) | 1976-12-23 |
| SE423711B (sv) | 1982-05-24 |
| CH634835A5 (de) | 1983-02-28 |
| YU161075A (en) | 1983-01-21 |
| SU1080744A3 (ru) | 1984-03-15 |
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