NO784094L - 3-di-n-propyl-acetoxy-benzodiazepin-2-oner og fremgangsmaate til deres fremstilling - Google Patents
3-di-n-propyl-acetoxy-benzodiazepin-2-oner og fremgangsmaate til deres fremstillingInfo
- Publication number
- NO784094L NO784094L NO784094A NO784094A NO784094L NO 784094 L NO784094 L NO 784094L NO 784094 A NO784094 A NO 784094A NO 784094 A NO784094 A NO 784094A NO 784094 L NO784094 L NO 784094L
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- radical
- solvent
- halogen
- analogous method
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 3
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000011877 solvent mixture Substances 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 5
- GYIUDLLQLVWKPP-UHFFFAOYSA-N 2-propylpentanoyl 2-propylpentanoate Chemical compound CCCC(CCC)C(=O)OC(=O)C(CCC)CCC GYIUDLLQLVWKPP-UHFFFAOYSA-N 0.000 description 4
- PITHYUDHKJKJNQ-UHFFFAOYSA-N 2-propylpentanoyl chloride Chemical compound CCCC(C(Cl)=O)CCC PITHYUDHKJKJNQ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229960000604 valproic acid Drugs 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000001773 anti-convulsant effect Effects 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- -1 oxazepam ester Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FERBACJQVQVCKH-UHFFFAOYSA-N 3-Hydroxy-N-desalkyl-2-Oxoquazepam Natural products C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1F FERBACJQVQVCKH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000006972 Polonovski rearrangement reaction Methods 0.000 description 2
- QRUFWTOCUCFKLZ-UHFFFAOYSA-N [7-chloro-5-(2-fluorophenyl)-2-oxo-1,3-dihydro-1,4-benzodiazepin-3-yl] 2-propylpentanoate Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(OC(=O)C(CCC)CCC)N=C1C1=CC=CC=C1F QRUFWTOCUCFKLZ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229960004535 oxazepam Drugs 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- DIWRORZWFLOCLC-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N([C@H](C(NC1=CC=C(Cl)C=C11)=O)O)=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-HNNXBMFYSA-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
- CQQUWTMMFMJEFE-UHFFFAOYSA-N 2-chloro-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CCl CQQUWTMMFMJEFE-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- SEQDDYPDSLOBDC-UHFFFAOYSA-N Temazepam Chemical compound N=1C(O)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 SEQDDYPDSLOBDC-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000004423 acyloxy group Chemical group 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
- YEJAJYAHJQIWNU-UHFFFAOYSA-N azelastine hydrochloride Chemical compound Cl.C1CN(C)CCCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 YEJAJYAHJQIWNU-UHFFFAOYSA-N 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229960004391 lorazepam Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000005547 pivalate group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229960003188 temazepam Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 230000009466 transformation 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT893877A AT359509B (de) | 1977-12-14 | 1977-12-14 | Verfahren zur herstellung von neuen 3-di-n- -propylacetoxybenzodiazepin-2-onen |
| AT831278A AT358051B (de) | 1978-11-21 | 1978-11-21 | Verfahren zur herstellung von neuen 3-di-n- -propyl-acetoxy-benzodiazepin-2-onen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO784094L true NO784094L (no) | 1979-06-15 |
Family
ID=25604664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO784094A NO784094L (no) | 1977-12-14 | 1978-12-06 | 3-di-n-propyl-acetoxy-benzodiazepin-2-oner og fremgangsmaate til deres fremstilling |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4261987A (pl) |
| JP (1) | JPS54138589A (pl) |
| AU (1) | AU4255778A (pl) |
| BG (2) | BG29284A3 (pl) |
| DD (1) | DD139851A5 (pl) |
| DE (1) | DE2852606A1 (pl) |
| DK (1) | DK562478A (pl) |
| ES (1) | ES475960A1 (pl) |
| FI (1) | FI783743A (pl) |
| FR (1) | FR2411836A1 (pl) |
| GB (1) | GB2010267A (pl) |
| GR (1) | GR65190B (pl) |
| IT (1) | IT1104583B (pl) |
| LU (1) | LU80632A1 (pl) |
| NL (1) | NL7812144A (pl) |
| NO (1) | NO784094L (pl) |
| PL (1) | PL114759B1 (pl) |
| RO (1) | RO79702A (pl) |
| SE (1) | SE7812649L (pl) |
| YU (1) | YU294378A (pl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190133B (it) * | 1986-06-19 | 1988-02-10 | Chiesi Farma Spa | Derivati di acido valproico e di acido (e)-2-valproenoico,procedimento per la loro preparazione e relative composizioni farmaceutiche |
| US5211954A (en) * | 1986-09-23 | 1993-05-18 | Sandoz Ltd. | Low dose temazepam |
| US5629310A (en) * | 1986-09-23 | 1997-05-13 | Sterling; William R. | Low dose temazepam |
| US5030632A (en) * | 1986-09-23 | 1991-07-09 | Sandoz Pharm. Corp. | Low dose temazepam |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3176009A (en) * | 1965-03-30 | Hydrolysis of l-acylated-j-acyloxy benzodiazepines | ||
| BE621819A (pl) * | 1961-08-29 | |||
| AT242706B (de) * | 1962-11-28 | 1965-10-11 | Hoffmann La Roche | Verfahren zur Herstellung von neuen Benzodiazepin-Derivaten |
| GB1051795A (pl) * | 1964-02-11 | |||
| US3236838A (en) * | 1964-06-09 | 1966-02-22 | Hoffmann La Roche | Certain 1-substituted-benzodiazepin-2-one compounds |
| FR135F (pl) * | 1964-08-13 | |||
| US3801568A (en) * | 1972-02-07 | 1974-04-02 | American Home Prod | Optically active 1,3-dihydro-3-substituted 5-phenyl-2h-1,4-benzodiazepin-2-ones and process for their separation |
| FR2269349B1 (pl) * | 1974-04-30 | 1979-03-16 | Ferrer Labor |
-
1978
- 1978-12-05 DE DE19782852606 patent/DE2852606A1/de not_active Withdrawn
- 1978-12-05 FI FI783743A patent/FI783743A/fi unknown
- 1978-12-06 GR GR57804A patent/GR65190B/el unknown
- 1978-12-06 NO NO784094A patent/NO784094L/no unknown
- 1978-12-08 SE SE7812649A patent/SE7812649L/xx unknown
- 1978-12-08 LU LU80632A patent/LU80632A1/de unknown
- 1978-12-12 PL PL1978211668A patent/PL114759B1/pl unknown
- 1978-12-12 BG BG041705A patent/BG29284A3/xx unknown
- 1978-12-12 BG BG044352A patent/BG29285A3/xx unknown
- 1978-12-12 FR FR7834868A patent/FR2411836A1/fr not_active Withdrawn
- 1978-12-12 GB GB7848060A patent/GB2010267A/en not_active Withdrawn
- 1978-12-13 NL NL7812144A patent/NL7812144A/xx not_active Application Discontinuation
- 1978-12-13 IT IT7830778A patent/IT1104583B/it active
- 1978-12-13 DD DD78209726A patent/DD139851A5/de unknown
- 1978-12-13 ES ES475960A patent/ES475960A1/es not_active Expired
- 1978-12-14 DK DK562478A patent/DK562478A/da unknown
- 1978-12-14 AU AU42557/78A patent/AU4255778A/en active Pending
- 1978-12-14 JP JP15565978A patent/JPS54138589A/ja active Pending
- 1978-12-14 YU YU02943/78A patent/YU294378A/xx unknown
- 1978-12-14 RO RO78101144A patent/RO79702A/ro unknown
- 1978-12-14 US US05/970,057 patent/US4261987A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2411836A1 (fr) | 1979-07-13 |
| NL7812144A (nl) | 1979-06-18 |
| GB2010267B (pl) | |
| FI783743A (fi) | 1979-06-15 |
| RO79702A (ro) | 1982-08-17 |
| PL211668A1 (pl) | 1979-07-30 |
| ES475960A1 (es) | 1979-05-01 |
| AU4255778A (en) | 1979-06-21 |
| BG29285A3 (en) | 1980-10-15 |
| GR65190B (en) | 1980-07-29 |
| BG29284A3 (en) | 1980-10-15 |
| DD139851A5 (de) | 1980-01-23 |
| IT1104583B (it) | 1985-10-21 |
| YU294378A (en) | 1983-06-30 |
| SE7812649L (sv) | 1979-06-15 |
| PL114759B1 (en) | 1981-02-28 |
| LU80632A1 (de) | 1979-04-09 |
| IT7830778A0 (it) | 1978-12-13 |
| DE2852606A1 (de) | 1979-06-21 |
| DK562478A (da) | 1979-06-15 |
| JPS54138589A (en) | 1979-10-27 |
| GB2010267A (en) | 1979-06-27 |
| US4261987A (en) | 1981-04-14 |
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