NO133714B - - Google Patents
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- Publication number
- NO133714B NO133714B NO4214/71A NO421471A NO133714B NO 133714 B NO133714 B NO 133714B NO 4214/71 A NO4214/71 A NO 4214/71A NO 421471 A NO421471 A NO 421471A NO 133714 B NO133714 B NO 133714B
- Authority
- NO
- Norway
- Prior art keywords
- benzodiazepine
- chloro
- diethylaminoethyl
- fluorophenyl
- dihydro
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- SAADBVWGJQAEFS-UHFFFAOYSA-N flurazepam Chemical compound N=1CC(=O)N(CCN(CC)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F SAADBVWGJQAEFS-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 150000001557 benzodiazepines Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 4
- ZIIJJOPLRSCQNX-UHFFFAOYSA-N Flurazepam hydrochloride Chemical compound Cl.Cl.N=1CC(=O)N(CCN(CC)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F ZIIJJOPLRSCQNX-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 235000019759 Maize starch Nutrition 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 208000019116 sleep disease Diseases 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- PUGVROXLRUQCAF-UHFFFAOYSA-N Flurazepam monohydrochloride Chemical compound Cl.N=1CC(=O)N(CCN(CC)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F PUGVROXLRUQCAF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229960004977 anhydrous lactose Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 210000004913 chyme Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 208000022925 sleep disturbance Diseases 0.000 description 1
- 230000008454 sleep-wake cycle Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 230000002618 waking effect Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH832571A CH553792A (de) | 1971-06-08 | 1971-06-08 | Verfahren zur herstellung von 7-chlor-1-(2-diaethyl-aminoaethyl)-5-(2-fluorphenyl)-1,3-dihydro-2h-1,4-benzodiazepin-2-on-monohydrochlorid. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133714B true NO133714B (cs) | 1976-03-08 |
| NO133714C NO133714C (cs) | 1976-06-16 |
Family
ID=4338591
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4214/71A NO133714C (cs) | 1971-06-08 | 1971-11-15 |
Country Status (31)
| Country | Link |
|---|---|
| JP (1) | JPS5230568B1 (cs) |
| AT (1) | AT313281B (cs) |
| BE (1) | BE777897A (cs) |
| BG (1) | BG19173A3 (cs) |
| BR (1) | BR7108123D0 (cs) |
| CA (1) | CA945989A (cs) |
| CH (1) | CH553792A (cs) |
| CS (2) | CS155106B2 (cs) |
| CY (1) | CY868A (cs) |
| DD (1) | DD98679A5 (cs) |
| DE (1) | DE2157112C3 (cs) |
| DK (1) | DK127506B (cs) |
| ES (1) | ES397552A1 (cs) |
| FI (1) | FI51352C (cs) |
| FR (1) | FR2140371B1 (cs) |
| GB (1) | GB1331823A (cs) |
| HU (1) | HU170152B (cs) |
| IE (1) | IE35846B1 (cs) |
| IL (1) | IL38252A (cs) |
| KE (1) | KE2652A (cs) |
| LU (1) | LU65469A1 (cs) |
| MX (1) | MX149567A (cs) |
| MY (1) | MY7400115A (cs) |
| NL (1) | NL7116376A (cs) |
| NO (1) | NO133714C (cs) |
| PH (1) | PH13530A (cs) |
| PL (1) | PL81437B1 (cs) |
| RO (2) | RO58965A (cs) |
| SE (2) | SE388856B (cs) |
| SU (1) | SU475776A3 (cs) |
| ZA (1) | ZA717880B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1199304A1 (en) * | 1997-03-05 | 2002-04-24 | Takeda Chemical Industries, Ltd. | Bicyclic compounds and pharmaceutical composition containing tricyclic compound for treating or preventing sleep disorders |
-
1971
- 1971-02-01 ES ES397552A patent/ES397552A1/es not_active Expired
- 1971-06-08 CH CH832571A patent/CH553792A/xx not_active IP Right Cessation
- 1971-11-15 FI FI713268A patent/FI51352C/fi active
- 1971-11-15 NO NO4214/71A patent/NO133714C/no unknown
- 1971-11-16 SE SE7114654A patent/SE388856B/xx unknown
- 1971-11-16 DK DK561771AA patent/DK127506B/da not_active IP Right Cessation
- 1971-11-17 DE DE2157112A patent/DE2157112C3/de not_active Expired
- 1971-11-17 HU HUHO1433A patent/HU170152B/hu unknown
- 1971-11-18 AT AT996671A patent/AT313281B/de not_active IP Right Cessation
- 1971-11-22 PL PL1971151697A patent/PL81437B1/pl unknown
- 1971-11-23 GB GB5436871A patent/GB1331823A/en not_active Expired
- 1971-11-23 ZA ZA717880A patent/ZA717880B/xx unknown
- 1971-11-23 CA CA128,336A patent/CA945989A/en not_active Expired
- 1971-11-23 CY CY868A patent/CY868A/xx unknown
- 1971-11-24 IE IE1489/71A patent/IE35846B1/xx unknown
- 1971-11-25 BG BG019094A patent/BG19173A3/xx unknown
- 1971-11-29 NL NL7116376A patent/NL7116376A/xx unknown
- 1971-11-29 SU SU1959119A patent/SU475776A3/ru active
- 1971-11-29 IL IL38252A patent/IL38252A/xx unknown
- 1971-12-02 JP JP46096838A patent/JPS5230568B1/ja active Pending
- 1971-12-02 RO RO75458A patent/RO58965A/ro unknown
- 1971-12-02 RO RO68930A patent/RO59000A/ro unknown
- 1971-12-04 MX MX131834A patent/MX149567A/es unknown
- 1971-12-08 BR BR8123/71A patent/BR7108123D0/pt unknown
- 1971-12-09 PH PH13088A patent/PH13530A/en unknown
- 1971-12-29 DD DD159994A patent/DD98679A5/xx unknown
- 1971-12-30 CS CS752472A patent/CS155106B2/cs unknown
- 1971-12-30 CS CS913171A patent/CS155105B2/cs unknown
-
1972
- 1972-01-11 BE BE777897A patent/BE777897A/xx not_active IP Right Cessation
- 1972-01-11 FR FR7200802A patent/FR2140371B1/fr not_active Expired
- 1972-06-06 LU LU65469A patent/LU65469A1/xx unknown
-
1974
- 1974-12-30 MY MY115/74A patent/MY7400115A/xx unknown
-
1975
- 1975-11-20 SE SE7513088A patent/SE7513088L/xx unknown
-
1976
- 1976-07-21 KE KE2652*UA patent/KE2652A/xx unknown
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