NO123180B - - Google Patents
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- Publication number
- NO123180B NO123180B NO169616A NO16961667A NO123180B NO 123180 B NO123180 B NO 123180B NO 169616 A NO169616 A NO 169616A NO 16961667 A NO16961667 A NO 16961667A NO 123180 B NO123180 B NO 123180B
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- phenyl
- compound
- denotes
- methyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- DEBLVPJOLMXEAW-UHFFFAOYSA-N 7-chloro-1,4-benzodiazepin-2-one Chemical compound O=C1C=NC=C2C=C(Cl)C=CC2=N1 DEBLVPJOLMXEAW-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000002936 tranquilizing 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Det er kjent at 1,4-benzodiazepiner med formelIt is known that 1,4-benzodiazepines with formula
hvor X har ovennevnte betydning, kan oksyderes ved hjelp av alminnelige oksydasjonsmidier, f.eks. CrO-^, til dannelse av en dobbeltbinding i 4-5-stilling. where X has the above-mentioned meaning, can be oxidized with the help of ordinary oxidation media, e.g. CrO-^, to form a double bond in the 4-5 position.
Hvis imidlertid nitrogenatomet i 1-stillingen erIf, however, the nitrogen atom in the 1-position is
substituert med en alkylgruppe, f.eks. en metylgruppe, har det ikke hittil lykkedes ved hjelp av vanlige oksydasjonsmidier å substituted with an alkyl group, e.g. a methyl group, it has not been possible to date with the help of ordinary oxidation media
gjennomføre denne oksydasjon for innførelse av nevnte dobbeltbinding,carry out this oxidation to introduce said double bond,
idet oksydasjonen i slike tilfelle går videre, hvorved det hoved-as the oxidation proceeds in such cases, whereby the main
sakelig fremkommer 2,3~diokso-forbindelsen (J. Org. Chem.,matter-of-factly, the 2,3~dioxo compound appears (J. Org. Chem.,
30, 1308, 1965). 30, 1308, 1965).
Det har nå overraskende vist seg at man kan fremstilleIt has now surprisingly turned out that it is possible to produce
forbindelser med den ovenfor angitte generelle formel I, hvis man ifølge oppfinnelsen behandler en forbindelse med den generelle formel compounds with the above-mentioned general formula I, if according to the invention one treats a compound with the general formula
med azodikarboksylsyredietylester, idet det inntrer følgende reaksjon: with azodicarboxylic acid diethyl ester, the following reaction occurring:
Denne reaksjon forløper glatt på kort tid og full-stendig kvantitativt, hvilket er en stor fordel, fordi man derved unngår de rensningsproblemer som ellers er karakteristiske for de foran omtalte oksydasjonsmetoder med vanlige oksydasjonsmidier. This reaction proceeds smoothly in a short time and completely quantitatively, which is a great advantage, because the purification problems which are otherwise characteristic of the above-mentioned oxidation methods with ordinary oxidation media are thereby avoided.
Ifølge en hensiktsmessig utførelsesform for oppfinnelsen oksyderes l-metyl-1,2,4,5-tetrahydro-5~fenyl-3H~7-klor-l,4-benzo-diazepin-2-on til l-metyl-l,2-dihydro-5-fenyl-3H-7-klor-l,4-benzodiazepin-2-on. According to an appropriate embodiment of the invention, 1-methyl-1,2,4,5-tetrahydro-5~phenyl-3H~7-chloro-1,4-benzo-diazepin-2-one is oxidized to 1-methyl-1,2 -dihydro-5-phenyl-3H-7-chloro-1,4-benzodiazepine-2-one.
De ved fremgangsmåten fremstilte forbindelser, og spesielt den ovenfor nevnte, utmerker seg som det er kjent ved kraftig sedativ og tranquilliserende virkning. The compounds produced by the process, and especially the one mentioned above, are known to have a strong sedative and tranquilizing effect.
Fremgangsmåten ifølge oppfinnelsen skal forklares nærmere ved hjelp av et utførelseseksempel. The method according to the invention will be explained in more detail with the help of an example.
Eksempel.Example.
Til 1,4 g l-metyl-1,2,4,5-tetrahydro-5~fenyl-3H-7-klor-l,4-benzodiazepin-2-on oppløst i 20 ml tørr benzol settes 0,87 g azodikarboksylsyre-dietylester. Blandingen kokes under tilbakeløp i 1 time og hensettes natten over ved værelsetemperatur. De utskilte krystaller av hydrazodikarboksylsyre-dietylester suges fra (0,7 g, smp. 130-133°C). Benzoloppløsningen inndampes i vakuum til tørrhet. Residuet oppløses i 10 ml kokende isopropanol. Ved avkjøling ut-skilles 1,1 g l-metyl-l,2-dihydro-5-fenyl-3H-7-klor-l,4-benzo-diazepin-2-on med smp. 128-130°C. To 1.4 g of 1-methyl-1,2,4,5-tetrahydro-5~phenyl-3H-7-chloro-1,4-benzodiazepine-2-one dissolved in 20 ml of dry benzene is added 0.87 g of azodicarboxylic acid -diethyl ester. The mixture is boiled under reflux for 1 hour and left overnight at room temperature. The separated crystals of hydrazodicarboxylic acid diethyl ester are sucked off (0.7 g, m.p. 130-133°C). The benzene solution is evaporated in vacuo to dryness. The residue is dissolved in 10 ml of boiling isopropanol. On cooling, 1.1 g of 1-methyl-1,2-dihydro-5-phenyl-3H-7-chloro-1,4-benzo-diazepin-2-one with m.p. 128-130°C.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK466266AA DK124260B (en) | 1966-09-09 | 1966-09-09 | Process for the preparation of 1-alkyl-1,2-dihydro-3H-2-oxo-5-phenyl-1,4-benzodiazepine compounds. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123180B true NO123180B (en) | 1971-10-11 |
Family
ID=8135555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO169616A NO123180B (en) | 1966-09-09 | 1967-09-05 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3513159A (en) |
| CH (1) | CH487907A (en) |
| DE (1) | DE1645992A1 (en) |
| DK (1) | DK124260B (en) |
| ES (1) | ES344822A1 (en) |
| FI (1) | FI47772C (en) |
| NL (1) | NL6712101A (en) |
| NO (1) | NO123180B (en) |
| SE (1) | SE335988B (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3371085A (en) * | 1959-12-10 | 1968-02-27 | Hoffmann La Roche | 5-aryl-3h-1,4-benzodiazepin-2(1h)-ones |
-
1966
- 1966-09-09 DK DK466266AA patent/DK124260B/en unknown
-
1967
- 1967-08-28 US US663499A patent/US3513159A/en not_active Expired - Lifetime
- 1967-08-30 FI FI672330A patent/FI47772C/en active
- 1967-09-01 DE DE19671645992 patent/DE1645992A1/en active Pending
- 1967-09-04 NL NL6712101A patent/NL6712101A/xx unknown
- 1967-09-04 CH CH1235667A patent/CH487907A/en not_active IP Right Cessation
- 1967-09-05 NO NO169616A patent/NO123180B/no unknown
- 1967-09-06 SE SE12298/67A patent/SE335988B/xx unknown
- 1967-09-07 ES ES344822A patent/ES344822A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES344822A1 (en) | 1968-11-01 |
| SE335988B (en) | 1971-06-21 |
| FI47772C (en) | 1974-03-11 |
| FI47772B (en) | 1973-11-30 |
| US3513159A (en) | 1970-05-19 |
| NL6712101A (en) | 1968-03-11 |
| CH487907A (en) | 1970-03-31 |
| DK124260B (en) | 1972-10-02 |
| DE1645992A1 (en) | 1970-07-16 |
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