IL40485A - '2 - )4 - פירידיל( - a ,616 - דימתיל - 02 - אוקסו - בa ,7111, 12 - טריהידרוקסי - פרגנא - 4, 6 - דיאנו ]c ,3 - 2[ פיראזול ותהליך להכנתו - Google Patents
'2 - )4 - פירידיל( - a ,616 - דימתיל - 02 - אוקסו - בa ,7111, 12 - טריהידרוקסי - פרגנא - 4, 6 - דיאנו ]c ,3 - 2[ פיראזול ותהליך להכנתוInfo
- Publication number
- IL40485A IL40485A IL40485A IL4048572A IL40485A IL 40485 A IL40485 A IL 40485A IL 40485 A IL40485 A IL 40485A IL 4048572 A IL4048572 A IL 4048572A IL 40485 A IL40485 A IL 40485A
- Authority
- IL
- Israel
- Prior art keywords
- dimethyl
- pregna
- pyridyl
- pyrazole
- dieno
- Prior art date
Links
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 230000000699 topical effect Effects 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000009885 systemic effect Effects 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- -1 methylenedioxy Chemical group 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 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
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013058 crude material Substances 0.000 description 3
- FDNPVQXLGFNHGX-UHFFFAOYSA-N ethoxycyclododecane Chemical compound CCOC1CCCCCCCCCCC1 FDNPVQXLGFNHGX-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WOKDGCSTFUDXQF-UHFFFAOYSA-N N-pyridin-4-ylbenzohydrazide Chemical compound N1=CC=C(C=C1)N(N)C(C1=CC=CC=C1)=O WOKDGCSTFUDXQF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- MBNYHKLFPUHDNO-GVWFROBISA-N (8S,9S,10R,13S,14S,17S)-17-(1,3-dioxolan-4-yl)-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1OCC([C@H]2CC[C@H]3[C@@H]4C=CC5=CC(CC[C@]5(C)[C@H]4CC[C@]23C)=O)O1 MBNYHKLFPUHDNO-GVWFROBISA-N 0.000 description 1
- PVMNPAUTCMBOMO-UHFFFAOYSA-N 4-chloropyridine Chemical compound ClC1=CC=NC=C1 PVMNPAUTCMBOMO-UHFFFAOYSA-N 0.000 description 1
- RJWLQXJFXPZHJR-KFEAHILISA-N C1OC2(COCO2)[C@]2(CC[C@H]3[C@@H]4C=CC5=CC(CC[C@]5(C)[C@H]4CC[C@]23C)=O)O1 Chemical compound C1OC2(COCO2)[C@]2(CC[C@H]3[C@@H]4C=CC5=CC(CC[C@]5(C)[C@H]4CC[C@]23C)=O)O1 RJWLQXJFXPZHJR-KFEAHILISA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- KRTLKPFLTASKCG-UHFFFAOYSA-N pyridin-4-ylhydrazine Chemical compound NNC1=CC=NC=C1 KRTLKPFLTASKCG-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL40485A IL40485A (he) | 1972-10-03 | 1972-10-03 | '2 - )4 - פירידיל( - a ,616 - דימתיל - 02 - אוקסו - בa ,7111, 12 - טריהידרוקסי - פרגנא - 4, 6 - דיאנו ]c ,3 - 2[ פיראזול ותהליך להכנתו |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL40485A IL40485A (he) | 1972-10-03 | 1972-10-03 | '2 - )4 - פירידיל( - a ,616 - דימתיל - 02 - אוקסו - בa ,7111, 12 - טריהידרוקסי - פרגנא - 4, 6 - דיאנו ]c ,3 - 2[ פיראזול ותהליך להכנתו |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL40485A0 IL40485A0 (en) | 1972-12-29 |
| IL40485A true IL40485A (he) | 1977-02-28 |
Family
ID=11046721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40485A IL40485A (he) | 1972-10-03 | 1972-10-03 | '2 - )4 - פירידיל( - a ,616 - דימתיל - 02 - אוקסו - בa ,7111, 12 - טריהידרוקסי - פרגנא - 4, 6 - דיאנו ]c ,3 - 2[ פיראזול ותהליך להכנתו |
Country Status (1)
| Country | Link |
|---|---|
| IL (1) | IL40485A (he) |
-
1972
- 1972-10-03 IL IL40485A patent/IL40485A/he unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL40485A0 (en) | 1972-12-29 |
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