IL37331A - Process for producing 3-(morpholino-alkoxy)-1h and 2h indazoles and pharmaceutical compositions containing the same - Google Patents
Process for producing 3-(morpholino-alkoxy)-1h and 2h indazoles and pharmaceutical compositions containing the sameInfo
- Publication number
- IL37331A IL37331A IL37331A IL3733171A IL37331A IL 37331 A IL37331 A IL 37331A IL 37331 A IL37331 A IL 37331A IL 3733171 A IL3733171 A IL 3733171A IL 37331 A IL37331 A IL 37331A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compound
- morpholino
- hydrochloride
- residue
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 5
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical class C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 6
- 238000001704 evaporation Methods 0.000 claims 6
- 229910052700 potassium Inorganic materials 0.000 claims 6
- 239000011591 potassium Substances 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 3
- 230000029936 alkylation Effects 0.000 claims 3
- 238000005804 alkylation reaction Methods 0.000 claims 3
- 239000012230 colorless oil Substances 0.000 claims 3
- 239000013078 crystal Substances 0.000 claims 3
- 239000012259 ether extract Substances 0.000 claims 3
- 230000008020 evaporation Effects 0.000 claims 3
- 238000002156 mixing Methods 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000003208 petroleum Substances 0.000 claims 3
- 238000003756 stirring Methods 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims 2
- UFNPJQRQWKZJNL-UHFFFAOYSA-N 1,2,4,5,6,7-hexahydroindazol-3-one Chemical compound C1CCCC2=C1NNC2=O UFNPJQRQWKZJNL-UHFFFAOYSA-N 0.000 claims 1
- SWEICGMKXPNXNU-UHFFFAOYSA-N 1,2-dihydroindazol-3-one Chemical compound C1=CC=C2C(O)=NNC2=C1 SWEICGMKXPNXNU-UHFFFAOYSA-N 0.000 claims 1
- ZAPMTSHEXFEPSD-UHFFFAOYSA-N 4-(2-chloroethyl)morpholine Chemical compound ClCCN1CCOCC1 ZAPMTSHEXFEPSD-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000012298 atmosphere Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229960003750 ethyl chloride Drugs 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (6)
1. A process for producing a compound of the formula X - 0 - (CH - N 0 211 \ / wherein n is 2 or 3 and X is or its hydrobromide or hydrochloride, which comprises a) reacting in absolute diozane the potassium enolate of 1-H-indazo-5-lone with β-ciorpholino-ethylchlorlde to form the compound of the formula I wherein n is 2 and X is H b) reacting in absolute diozane the potassium enolate of 1-H-indazo-3-lone with jf-morpholino-propylchloride to form the compound of fomula I wherein n is 3 and X is c) reacting in absolute diozane the potassium enolate of 4»5,6,7-tetrahydro-2H-indazo-3~lone with β-morpholino-ethylchloride to form the compound of the formula I wherein n is 2 and X is where required, converting the compound of the formula I thus formed into its hydrobromide or hydrochloride.
2. A process of' claim 1 wherein 3-(β-morpholino-ethox )-1H-indazole of the formula - 18 - is prepared by suspending in absolute diozane the potassium enolate of the 1H-indazol-3-one obtained in vacuum from 1-H-indazol-5-one and an equimelar amount of KDH in methanol, after evaporation of the solvent, then adding freshly prepared p-morphollno-ethyl-chloride obtained by alkylation from the hydrochloride, stirring the mixture in a nitrogen atmosphere at a o temperature of about 100 C» removing the solvent, mixing the residue with water, extracting the residue by means of ether, evaporating the ether extract to dryness and dissolving the thus obtained colorless oil in acetone, adding petroleum ether until the solution becomes cloudy and recovering the precipitated crystals of the compound of the formula II.
3. A process of claim 1 wherein 3-(lJ-H-iorpholino-propoxy)-1H-indazole of the formula is prepared by suspending in absolute dioxane the potassium enolate of the 1H-indazolone-3-obtained in vacuum from 1-H-indazol-3-ozte and an equimolar amount of OH in methanol, after evaporation of the solvent, then adding freshly prepared ^-morpholino-propyl-chloride obtained by alkylation from the hydrochloride, stirring the mixture in a nitrogen' atmosphere at a temperature of about 100°C removing the solvent, mixing the residue with water, extracting the residue by means of ether, evaporating the ether extract to dryness and dissolving the 19 - 37331/3 thus obtained colorless oil in acetone, adding petroleum ether until the solution becomes cloudy and recovering the preeipitated crystals of the compound of the formula XXX.
4. A process of claim 1 wherein 3-0 -xaorpholino-ethoxy) -4,5,6,7-tetrabydro-2H-lndasole of the formula is prepared by suspending in absolute dioxane the potassium enolate of the 4,5,6,7-tetrahydro-2H-lndasol-3-one obtained in vacuum from 4,5,6,7-tetrahydro-2H-indazol-3-one and an equimolar amount of KOH in methanol, after evaporation of the solvent, then adding freshly prepared^ -morpholino-ethyl-chloride obtained by alkylation from the hydrochloride, stirring the mixture in a nitrogen atmosphere at a temperature of about 100 C, removing the solvent, mixing the residue with water, extracting the residue by means of ether, evaporating the ether extract to dryness and dissolving the thus obtained colorless oil in acetone, adding petroleum ether until the solution becomes cloudy and recovering the precipitated crystals of the compound of the formula IV,
5. A drug comprising an active Ingredient selected from the group consisting of 3-1 -morphollno-ethoxy)-4,5,e,7-tetrahydro-2H-indasol-hydrobromide, 3-0 -morpholino-ethoxy) -IH-indazol or the hydrobromide thereof and 3-f -raorpholino-propoxy)-lH-indazole or the hydrochloride thereof; and an inert carrier.
6. A chemical compound characterised by the formula
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702035494 DE2035494C (en) | 1970-07-17 | A new derivative of 2H indazolone 3, its hydrobromide and drugs made from these compounds | |
| DE19712134592 DE2134592C3 (en) | 1971-07-10 | 1971-07-10 | Process for the preparation of 3- (beta-morpholinoethoxy) -lH-indazole, 3- (gamma, morpholinopropoxy) -1H-indazole and 3- (beta-morpholinoethoxy) -4,5,6,7 tetrahydro-2H-indazole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL37331A0 IL37331A0 (en) | 1972-01-27 |
| IL37331A true IL37331A (en) | 1976-12-31 |
Family
ID=25759450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL37331A IL37331A (en) | 1970-07-17 | 1971-07-18 | Process for producing 3-(morpholino-alkoxy)-1h and 2h indazoles and pharmaceutical compositions containing the same |
Country Status (9)
| Country | Link |
|---|---|
| AU (1) | AU474762B2 (en) |
| CA (1) | CA957370A (en) |
| CH (1) | CH554889A (en) |
| DK (1) | DK129845B (en) |
| ES (1) | ES393379A1 (en) |
| FR (1) | FR2100928A1 (en) |
| IL (1) | IL37331A (en) |
| NL (1) | NL169469C (en) |
| SE (1) | SE379767B (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3428634A (en) * | 1965-03-13 | 1969-02-18 | Acraf | 3-tertiary amino alkoxy-1-hydrocarbon indazoles |
-
1971
- 1971-07-16 NL NLAANVRAGE7109842,A patent/NL169469C/en not_active IP Right Cessation
- 1971-07-16 SE SE7109242A patent/SE379767B/xx unknown
- 1971-07-16 DK DK352071AA patent/DK129845B/en not_active IP Right Cessation
- 1971-07-16 CH CH1050571A patent/CH554889A/en not_active IP Right Cessation
- 1971-07-17 ES ES393379A patent/ES393379A1/en not_active Expired
- 1971-07-18 IL IL37331A patent/IL37331A/en unknown
- 1971-07-19 FR FR7126341A patent/FR2100928A1/en active Granted
- 1971-07-19 AU AU31422/71A patent/AU474762B2/en not_active Expired
- 1971-07-19 CA CA118,519A patent/CA957370A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2100928B1 (en) | 1975-02-07 |
| CA957370A (en) | 1974-11-05 |
| CH554889A (en) | 1974-10-15 |
| AU3142271A (en) | 1973-01-25 |
| ES393379A1 (en) | 1974-09-16 |
| DK129845C (en) | 1975-05-12 |
| IL37331A0 (en) | 1972-01-27 |
| NL169469C (en) | 1982-07-16 |
| NL7109842A (en) | 1972-01-19 |
| FR2100928A1 (en) | 1972-03-24 |
| NL169469B (en) | 1982-02-16 |
| SE379767B (en) | 1975-10-20 |
| DK129845B (en) | 1974-11-25 |
| AU474762B2 (en) | 1976-08-05 |
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