PL81437B1 - - Google Patents
Download PDFInfo
- Publication number
- PL81437B1 PL81437B1 PL1971151697A PL15169771A PL81437B1 PL 81437 B1 PL81437 B1 PL 81437B1 PL 1971151697 A PL1971151697 A PL 1971151697A PL 15169771 A PL15169771 A PL 15169771A PL 81437 B1 PL81437 B1 PL 81437B1
- Authority
- PL
- Poland
- Prior art keywords
- chloro
- dihydro
- fluorophenyl
- monohydrochloride
- dihydrochloride
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 14
- -1 2-diethylaminoethyl Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 208000019116 sleep disease Diseases 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002618 waking effect Effects 0.000 description 2
- RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical compound O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 description 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-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
- 208000017667 Chronic Disease Diseases 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960004977 anhydrous lactose Drugs 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 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 description 1
- 229910052733 gallium Inorganic materials 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
- 230000035876 healing Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 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
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic 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 (1)
| Publication Number | Publication Date |
|---|---|
| PL81437B1 true PL81437B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-08-30 |
Family
ID=4338591
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1971151697A PL81437B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-06-08 | 1971-11-22 |
Country Status (31)
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 HU HUHO1433A patent/HU170152B/hu unknown
- 1971-11-17 DE DE2157112A patent/DE2157112C3/de not_active Expired
- 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 ZA ZA717880A patent/ZA717880B/xx unknown
- 1971-11-23 CA CA128,336A patent/CA945989A/en not_active Expired
- 1971-11-23 GB GB5436871A patent/GB1331823A/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 IL IL38252A patent/IL38252A/xx unknown
- 1971-11-29 NL NL7116376A patent/NL7116376A/xx unknown
- 1971-11-29 SU SU1721027A patent/SU444369A3/ru active
- 1971-11-29 SU SU1959119A patent/SU475776A3/ru active
- 1971-12-02 RO RO68930A patent/RO59000A/ro unknown
- 1971-12-02 JP JP46096838A patent/JPS5230568B1/ja active Pending
- 1971-12-02 RO RO75458A patent/RO58965A/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 FR FR7200802A patent/FR2140371B1/fr not_active Expired
- 1972-01-11 BE BE777897A patent/BE777897A/xx not_active IP Right Cessation
- 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
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3642775A (en) | 10-oxo-10 11-dihydro-dibenzazepine derivative | |
| US3109843A (en) | Process for preparing | |
| IL23999A (en) | History of benzodiazepines and the process for their production | |
| US3131178A (en) | Process for producing s-phenyl-l | |
| US3422091A (en) | 5-phenyl-3h-1,4-benzodiazepine-2(ih)-thione and derivatives thereof | |
| US3546212A (en) | Oxidation of benzodiazepines with ruthenium tetroxide | |
| PL81437B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| US3340253A (en) | Preparation of certain benzodiazepine compounds | |
| US3442946A (en) | 2-aminomercapto- and 2-aminoalkylcaptobenzophenone oximes | |
| US3903103A (en) | 4-Amino-s-triazolo-{8 4,3-a{9 {8 1,4{9 benzodiazepine | |
| US3757008A (en) | Sses for preparing same 1 - (carboxyl-heteroalkyl) - 1,4-benzodiazepine derivatives and proce | |
| US3644334A (en) | 7-azido-benzodiazepines | |
| US3686308A (en) | 5-lower alkanoyl-2-glycylamino-benzophenones | |
| US3336296A (en) | Preparation of 5-substituted-2h-1, 4-benzodiazepin-2-one-4-oxides | |
| US3678043A (en) | 2,3-dihydro-2-oxo-1h-1,4-benzodiazepine-3-carboxylic acid esters and related compounds | |
| US3177201A (en) | Substituted 5-phenyl-3h-1, 4-benzodiazepines and hydrogenation products thereof | |
| US3338886A (en) | 5-cycloalkyl-3h-1, 4-benzodiazepin-2(1h)-ones | |
| DE2244573A1 (de) | Triazolo-benzodiazepine und verfahren zu ihrer herstellung | |
| US3215694A (en) | Quinazoline-z-carboxaldehydes, acids, intermediates and process | |
| EP0008045B1 (de) | (1,2)-Anellierte 7-Phenyl-1,4-benzodiazepinderivate und deren Salze; Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| US3897446A (en) | 6-Phenylthiazolo{8 3,2-a{9 {8 1,4{9 benzodiazepin-1-(2H)-ones, and processes | |
| US3773768A (en) | 7-amino-2-chloro-11-(4-methyl-1-piperazinyl)dibenz(b,f)(1,4)oxazepine and salts thereof | |
| US3294782A (en) | 3, 4-dihydro-6-phenyl-1, 5-benzodiazocin-2-ones | |
| US3499027A (en) | Intermediates for preparing certain 1,4-benzodiazepin-2-(1h)-ones | |
| US3845039A (en) | 1-polyfluoroalkyl-1,4-benzodiazepin-2-thiones |