NO125314B - - Google Patents
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- Publication number
- NO125314B NO125314B NO0968/70A NO96870A NO125314B NO 125314 B NO125314 B NO 125314B NO 0968/70 A NO0968/70 A NO 0968/70A NO 96870 A NO96870 A NO 96870A NO 125314 B NO125314 B NO 125314B
- Authority
- NO
- Norway
- Prior art keywords
- benzodiazepine
- tetrahydro
- chloro
- methyl
- phenyl
- Prior art date
Links
- 239000002904 solvent Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 92
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 4
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 3
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910017053 inorganic salt Inorganic materials 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011833 salt mixture Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- NFCPRRWCTNLGSN-UHFFFAOYSA-N 2-n-phenylbenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NC1=CC=CC=C1 NFCPRRWCTNLGSN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- DVLRNCUAXRYSPF-UHFFFAOYSA-N 1,3,4,5,5a,6-hexahydro-1,5-benzodiazepin-2-one Chemical compound N1C(CCNC2C1=CC=CC2)=O DVLRNCUAXRYSPF-UHFFFAOYSA-N 0.000 description 1
- PXMPUBOXRURGJG-UHFFFAOYSA-N 1-(2-anilinophenyl)-3,3-diethylazetidin-2-one Chemical compound O=C1C(CC)(CC)CN1C1=CC=CC=C1NC1=CC=CC=C1 PXMPUBOXRURGJG-UHFFFAOYSA-N 0.000 description 1
- ZVDKTPOXSAEUQU-UHFFFAOYSA-N 3-bromo-2-methylpropanoyl chloride Chemical compound BrCC(C)C(Cl)=O ZVDKTPOXSAEUQU-UHFFFAOYSA-N 0.000 description 1
- MCXNAPPGXLEHEH-UHFFFAOYSA-N 3-bromobutanoyl chloride Chemical compound CC(Br)CC(Cl)=O MCXNAPPGXLEHEH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 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
- C07D243/12—1,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691913536 DE1913536C2 (de) | 1969-03-18 | 1969-03-18 | 1-Phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one und Verfahren zu deren Herstellung |
| DE19691953647 DE1953647A1 (de) | 1969-10-24 | 1969-10-24 | 1-Aryl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one und Verfahren zu deren Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO125314B true NO125314B (cs) | 1972-08-21 |
Family
ID=25757147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO0968/70A NO125314B (cs) | 1969-03-18 | 1970-03-17 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4239684A (cs) |
| AT (1) | AT296994B (cs) |
| BE (1) | BE747400A (cs) |
| BG (1) | BG17601A3 (cs) |
| CH (1) | CH533629A (cs) |
| CS (1) | CS161871B2 (cs) |
| DK (1) | DK127784B (cs) |
| ES (1) | ES377621A1 (cs) |
| FI (1) | FI49964C (cs) |
| FR (1) | FR2038904A5 (cs) |
| GB (1) | GB1279915A (cs) |
| IE (1) | IE33750B1 (cs) |
| IL (1) | IL34044A (cs) |
| NL (1) | NL166935C (cs) |
| NO (1) | NO125314B (cs) |
| PH (1) | PH10103A (cs) |
| SE (1) | SE357366B (cs) |
| YU (1) | YU33790B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3635768C2 (de) * | 1985-10-24 | 1988-05-26 | Sharp K.K., Osaka, Jp | Lesevorrichtung fuer kodierte information |
| FR2610899B1 (fr) * | 1987-02-16 | 1989-10-20 | Pigny Adrien | Caisse-palette a compartiments superposes |
| US5855610A (en) * | 1995-05-19 | 1999-01-05 | Children's Medical Center Corporation | Engineering of strong, pliable tissues |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3321486A (en) * | 1965-02-24 | 1967-05-23 | American Cyanamid Co | Substituted 4-oxo-4, 5, 6, 7-tetra-hydroindoles |
| US3321468A (en) * | 1965-03-09 | 1967-05-23 | Squibb & Sons Inc | Novel 2h-1, 5-benzodiazepin-2-ones |
| US3816409A (en) * | 1970-06-08 | 1974-06-11 | Boehringer Sohn Ingelheim | 5-(pyridyl or phenyl)-1h-2,3,4,5-tetra-hydro-1,5-benzodiazepin-4-ones and salts thereof |
-
1970
- 1970-03-09 GB GB01080/70A patent/GB1279915A/en not_active Expired
- 1970-03-10 IL IL34044A patent/IL34044A/xx unknown
- 1970-03-12 CS CS1650A patent/CS161871B2/cs unknown
- 1970-03-13 FR FR7009086A patent/FR2038904A5/fr not_active Expired
- 1970-03-13 IE IE335/70A patent/IE33750B1/xx unknown
- 1970-03-16 BE BE747400D patent/BE747400A/xx not_active IP Right Cessation
- 1970-03-16 CH CH387470A patent/CH533629A/de not_active IP Right Cessation
- 1970-03-16 AT AT243970A patent/AT296994B/de not_active IP Right Cessation
- 1970-03-17 NO NO0968/70A patent/NO125314B/no unknown
- 1970-03-17 DK DK132070AA patent/DK127784B/da unknown
- 1970-03-17 BG BG014206A patent/BG17601A3/xx unknown
- 1970-03-17 YU YU662/70A patent/YU33790B/xx unknown
- 1970-03-17 FI FI700738A patent/FI49964C/fi active
- 1970-03-17 ES ES377621A patent/ES377621A1/es not_active Expired
- 1970-03-18 PH PH11246A patent/PH10103A/en unknown
- 1970-03-18 NL NL7003883.A patent/NL166935C/xx not_active IP Right Cessation
- 1970-03-18 SE SE03653/70A patent/SE357366B/xx unknown
-
1978
- 1978-06-02 US US05/911,831 patent/US4239684A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SU400100A3 (cs) | 1973-10-03 |
| BE747400A (fr) | 1970-09-16 |
| FR2038904A5 (cs) | 1971-01-08 |
| YU66270A (en) | 1977-10-31 |
| FI49964C (fi) | 1975-11-10 |
| ES377621A1 (es) | 1973-01-01 |
| SE357366B (cs) | 1973-06-25 |
| PH10103A (en) | 1976-08-25 |
| DK127784B (da) | 1974-01-07 |
| AT296994B (de) | 1972-03-10 |
| BG17601A3 (bg) | 1973-11-10 |
| CS161871B2 (cs) | 1975-06-10 |
| IL34044A (en) | 1974-12-31 |
| NL7003883A (cs) | 1970-09-22 |
| IE33750B1 (en) | 1974-10-16 |
| IE33750L (en) | 1970-09-18 |
| NL166935B (nl) | 1981-05-15 |
| YU33790B (en) | 1978-05-15 |
| NL166935C (nl) | 1981-10-15 |
| GB1279915A (en) | 1972-06-28 |
| US4239684A (en) | 1980-12-16 |
| CH533629A (de) | 1973-02-15 |
| FI49964B (cs) | 1975-07-31 |
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