DE2539114A1 - 7-substituierte 3-(aminomethyl)- 3,5-dihydro-as-triazino eckige klammer auf 4,3-a eckige klammer zu eckige klammer auf 1,4 eckige klammer zu benzodiazepin-2-(1h)-one und ein verfahren zu deren herstellung - Google Patents
7-substituierte 3-(aminomethyl)- 3,5-dihydro-as-triazino eckige klammer auf 4,3-a eckige klammer zu eckige klammer auf 1,4 eckige klammer zu benzodiazepin-2-(1h)-one und ein verfahren zu deren herstellungInfo
- Publication number
- DE2539114A1 DE2539114A1 DE19752539114 DE2539114A DE2539114A1 DE 2539114 A1 DE2539114 A1 DE 2539114A1 DE 19752539114 DE19752539114 DE 19752539114 DE 2539114 A DE2539114 A DE 2539114A DE 2539114 A1 DE2539114 A1 DE 2539114A1
- Authority
- DE
- Germany
- Prior art keywords
- dihydro
- triazino
- atom
- chlorine
- benzodiazepine
- 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
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- 229910052757 nitrogen Inorganic materials 0.000 description 11
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- 230000036461 convulsion Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- CHIFCDOIPRCHCF-UHFFFAOYSA-N delorazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl CHIFCDOIPRCHCF-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- HALUWNYEYARWGC-UHFFFAOYSA-N ethyl 2-(2-oxo-5-phenyl-3h-1,4-benzodiazepin-1-yl)acetate Chemical compound N=1CC(=O)N(CC(=O)OCC)C2=CC=CC=C2C=1C1=CC=CC=C1 HALUWNYEYARWGC-UHFFFAOYSA-N 0.000 description 1
- YPSJZQPXDXXFBJ-UHFFFAOYSA-N ethyl 2-(7-chloro-2-oxo-5-phenyl-3h-1,4-benzodiazepin-1-yl)acetate Chemical compound N=1CC(=O)N(CC(=O)OCC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 YPSJZQPXDXXFBJ-UHFFFAOYSA-N 0.000 description 1
- GMKWTYPHEBBAGK-UHFFFAOYSA-N ethyl 2-(7-nitro-5-phenyl-2-sulfanylidene-3h-1,4-benzodiazepin-1-yl)acetate Chemical compound N=1CC(=S)N(CC(=O)OCC)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 GMKWTYPHEBBAGK-UHFFFAOYSA-N 0.000 description 1
- URLHDOJKVOMNBW-UHFFFAOYSA-N ethyl 2-(diazepin-1-yl)acetate Chemical compound C(C)OC(CN1N=CC=CC=C1)=O URLHDOJKVOMNBW-UHFFFAOYSA-N 0.000 description 1
- OLOQWEMEEAMPOJ-UHFFFAOYSA-N ethyl 2-[5-phenyl-2-sulfanylidene-7-(trifluoromethyl)-3h-1,4-benzodiazepin-1-yl]acetate Chemical compound N=1CC(=S)N(CC(=O)OCC)C2=CC=C(C(F)(F)F)C=C2C=1C1=CC=CC=C1 OLOQWEMEEAMPOJ-UHFFFAOYSA-N 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- KAUMQWXRWJBSDZ-UHFFFAOYSA-N heptan-4-ylideneazanium;chloride Chemical compound [Cl-].CCCC(=[NH2+])CCC KAUMQWXRWJBSDZ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- QGXVVZXXVJDOEM-UHFFFAOYSA-N methanimine;hydrochloride Chemical compound [Cl-].[NH2+]=C QGXVVZXXVJDOEM-UHFFFAOYSA-N 0.000 description 1
- DXXHWOFFFFGVGH-UHFFFAOYSA-N methyl 2-(1,2-benzodiazepin-1-yl)acetate Chemical compound COC(CN1N=CC=CC2=C1C=CC=C2)=O DXXHWOFFFFGVGH-UHFFFAOYSA-N 0.000 description 1
- DVXCSQWIOWVZDO-UHFFFAOYSA-N methyl 2-(1,4-benzodiazepin-1-yl)acetate Chemical compound COC(CN1C=CN=CC2=C1C=CC=C2)=O DVXCSQWIOWVZDO-UHFFFAOYSA-N 0.000 description 1
- YTGSGKZPSIVQHL-UHFFFAOYSA-N methyl 2-(7-bromo-2-oxo-5-pyridin-2-yl-3h-1,4-benzodiazepin-1-yl)acetate Chemical compound N=1CC(=O)N(CC(=O)OC)C2=CC=C(Br)C=C2C=1C1=CC=CC=N1 YTGSGKZPSIVQHL-UHFFFAOYSA-N 0.000 description 1
- GYSSDYYRRUNCGK-UHFFFAOYSA-N methyl 2-(7-bromo-5-phenyl-2-sulfanylidene-3h-1,4-benzodiazepin-1-yl)acetate Chemical compound N=1CC(=S)N(CC(=O)OC)C2=CC=C(Br)C=C2C=1C1=CC=CC=C1 GYSSDYYRRUNCGK-UHFFFAOYSA-N 0.000 description 1
- UZSXYEFRDOKGKJ-UHFFFAOYSA-N methyl 2-(7-chloro-2-oxo-5-phenyl-3h-1,4-benzodiazepin-1-yl)acetate Chemical compound N=1CC(=O)N(CC(=O)OC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 UZSXYEFRDOKGKJ-UHFFFAOYSA-N 0.000 description 1
- USDOUOQWADRQAV-UHFFFAOYSA-N methyl 2-(7-chloro-5-phenyl-2-sulfanylidene-3h-1,4-benzodiazepin-1-yl)acetate Chemical compound N=1CC(=S)N(CC(=O)OC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 USDOUOQWADRQAV-UHFFFAOYSA-N 0.000 description 1
- YFFXQMWXIUZFNF-UHFFFAOYSA-N methyl 2-[5-(2-chlorophenyl)-2-oxo-3h-1,4-benzodiazepin-1-yl]acetate Chemical compound N=1CC(=O)N(CC(=O)OC)C2=CC=CC=C2C=1C1=CC=CC=C1Cl YFFXQMWXIUZFNF-UHFFFAOYSA-N 0.000 description 1
- FXUBWEKABXTQCY-UHFFFAOYSA-N methyl 2-[5-(2-chlorophenyl)-2-sulfanylidene-3h-1,4-benzodiazepin-1-yl]acetate Chemical compound N=1CC(=S)N(CC(=O)OC)C2=CC=CC=C2C=1C1=CC=CC=C1Cl FXUBWEKABXTQCY-UHFFFAOYSA-N 0.000 description 1
- DGSFTMJPCFGVOR-UHFFFAOYSA-N methyl 2-[7-bromo-5-(2-fluorophenyl)-2-oxo-3h-1,4-benzodiazepin-1-yl]acetate Chemical compound N=1CC(=O)N(CC(=O)OC)C2=CC=C(Br)C=C2C=1C1=CC=CC=C1F DGSFTMJPCFGVOR-UHFFFAOYSA-N 0.000 description 1
- LDQYGERMFMNKRY-UHFFFAOYSA-N methyl 2-[7-chloro-5-(2,6-difluorophenyl)-2-oxo-3h-1,4-benzodiazepin-1-yl]acetate Chemical compound N=1CC(=O)N(CC(=O)OC)C2=CC=C(Cl)C=C2C=1C1=C(F)C=CC=C1F LDQYGERMFMNKRY-UHFFFAOYSA-N 0.000 description 1
- PWPIKWMTYLLJRE-UHFFFAOYSA-N methyl 2-[7-chloro-5-(2,6-difluorophenyl)-2-sulfanylidene-3h-1,4-benzodiazepin-1-yl]acetate Chemical compound N=1CC(=S)N(CC(=O)OC)C2=CC=C(Cl)C=C2C=1C1=C(F)C=CC=C1F PWPIKWMTYLLJRE-UHFFFAOYSA-N 0.000 description 1
- YNBUTFIJSYMHGQ-UHFFFAOYSA-N methyl 2-[7-chloro-5-(2-fluorophenyl)-2-sulfanylidene-3h-1,4-benzodiazepin-1-yl]acetate Chemical compound N=1CC(=S)N(CC(=O)OC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F YNBUTFIJSYMHGQ-UHFFFAOYSA-N 0.000 description 1
- YAWDKHMOYXWWRS-UHFFFAOYSA-N methyl 2-[7-fluoro-5-(2-fluorophenyl)-2-sulfanylidene-3h-1,4-benzodiazepin-1-yl]acetate Chemical compound N=1CC(=S)N(CC(=O)OC)C2=CC=C(F)C=C2C=1C1=CC=CC=C1F YAWDKHMOYXWWRS-UHFFFAOYSA-N 0.000 description 1
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 1
- OBLFAWFQIVEBOV-UHFFFAOYSA-N methyl(propylidene)azanium;chloride Chemical compound [Cl-].CCC=[NH+]C OBLFAWFQIVEBOV-UHFFFAOYSA-N 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- ISYUCUGTDNJIHV-UHFFFAOYSA-N propyl 2-bromoacetate Chemical compound CCCOC(=O)CBr ISYUCUGTDNJIHV-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- UUBMOUNXQFMBQF-UHFFFAOYSA-N ro5-2904 Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 UUBMOUNXQFMBQF-UHFFFAOYSA-N 0.000 description 1
- 239000004248 saffron Substances 0.000 description 1
- 235000013974 saffron Nutrition 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- C07D243/22—Sulfur 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| US05/505,507 US3933816A (en) | 1974-09-12 | 1974-09-12 | 3-(Substituted aminomethyl)-7-substituted-3,5-dihydro-as-triazino[4,3-a][1,5]benzodiazepines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2539114A1 true DE2539114A1 (de) | 1976-03-25 |
Family
ID=24010587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752539114 Pending DE2539114A1 (de) | 1974-09-12 | 1975-09-03 | 7-substituierte 3-(aminomethyl)- 3,5-dihydro-as-triazino eckige klammer auf 4,3-a eckige klammer zu eckige klammer auf 1,4 eckige klammer zu benzodiazepin-2-(1h)-one und ein verfahren zu deren herstellung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3933816A (enExample) |
| JP (1) | JPS5156496A (enExample) |
| CH (1) | CH602736A5 (enExample) |
| DE (1) | DE2539114A1 (enExample) |
| FR (1) | FR2342069A1 (enExample) |
| GB (1) | GB1468114A (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4028356A (en) * | 1976-02-09 | 1977-06-07 | The Upjohn Company | Triazinobenzodiazepines |
| US4016165A (en) * | 1976-02-09 | 1977-04-05 | The Upjohn Company | Triazino benzodiazepines |
| US4017492A (en) * | 1976-04-02 | 1977-04-12 | The Upjohn Company | As-triazinobenzodiazepin-1-ones |
| US4086230A (en) * | 1977-03-09 | 1978-04-25 | The Upjohn Company | 1,5-Dihydro-7-aryl-as-triazine[4,3,-α][1,4]benzodiazepin-1-ols |
| US4073784A (en) * | 1977-03-09 | 1978-02-14 | The Upjohn Company | Certain as-triazino 4,3-a! 1,4!benzodiazepine-1,2-dione compounds |
| US4073785A (en) * | 1977-03-09 | 1978-02-14 | The Upjohn Company | Certain as-triazino 4,3-a! 1,4!benzodiazepine derivatives |
| JPS5572177A (en) * | 1978-11-27 | 1980-05-30 | Shionogi & Co Ltd | 4,1-benzoxazepine or 4,1-benzothiazepine |
| HU179158B (en) * | 1979-04-11 | 1982-08-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing triasolo-benzo-asimetrical-triasine derivatives |
| DE3151597A1 (de) * | 1981-12-28 | 1983-07-07 | Kali-Chemie Pharma Gmbh, 3000 Hannover | (1,2)-anellierte 1,4-benzodiazepin-verbindungen sowie verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US5177071A (en) * | 1991-06-17 | 1993-01-05 | Merck & Co., Inc. | 1,4-benzodiazepines with 6-membered heterocyclic rings to treat panic and anxiety disorder |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE793629A (fr) * | 1972-01-03 | 1973-07-03 | Upjohn Co | Nouveaux derives de benzodiazepines et leur preparation |
-
1974
- 1974-09-12 US US05/505,507 patent/US3933816A/en not_active Expired - Lifetime
-
1975
- 1975-08-27 CH CH1111975A patent/CH602736A5/xx not_active IP Right Cessation
- 1975-09-03 DE DE19752539114 patent/DE2539114A1/de active Pending
- 1975-09-03 GB GB3625675A patent/GB1468114A/en not_active Expired
- 1975-09-11 FR FR7527960A patent/FR2342069A1/fr active Granted
- 1975-09-12 JP JP50110852A patent/JPS5156496A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2342069A1 (fr) | 1977-09-23 |
| FR2342069B1 (enExample) | 1978-09-08 |
| JPS5156496A (en) | 1976-05-18 |
| US3933816A (en) | 1976-01-20 |
| CH602736A5 (enExample) | 1978-07-31 |
| GB1468114A (en) | 1977-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |