IL26799A - 16 - Methylene - 17 - Hydroxy - 19 - Norprogesterone, its sites and esters and pharmaceutical preparations containing them - Google Patents

16 - Methylene - 17 - Hydroxy - 19 - Norprogesterone, its sites and esters and pharmaceutical preparations containing them

Info

Publication number: IL26799A
Authority: IL; Israel
Prior art keywords: acid; hydroxy; compound; methylene; group
Prior art date: 1965-11-26

Application number

IL26799A

Other languages

English (en)

Hebrew (he)

Original Assignee

Merck Ag E

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1965-11-26

Filing date

1966-11-03

Publication date

1970-07-19

1966-11-03 Application filed by Merck Ag E filed Critical Merck Ag E

1970-07-19 Publication of IL26799A publication Critical patent/IL26799A/en

Links

150000002148 esters Chemical class 0.000 title description 6
150000002170 ethers Chemical class 0.000 title description 5
239000008194 pharmaceutical composition Substances 0.000 title 1
239000002253 acid Substances 0.000 claims description 51
150000001875 compounds Chemical class 0.000 claims description 48
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
239000000203 mixture Substances 0.000 claims description 17
238000000034 method Methods 0.000 claims description 16
239000003513 alkali Substances 0.000 claims description 10
125000000468 ketone group Chemical group 0.000 claims description 10
239000007800 oxidant agent Substances 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
125000004185 ester group Chemical group 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims 4
230000003301 hydrolyzing effect Effects 0.000 claims 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 55
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 35
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
-1 ester radicals Chemical class 0.000 description 26
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 19
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
150000007513 acids Chemical class 0.000 description 18
239000000047 product Substances 0.000 description 18
229960000583 acetic acid Drugs 0.000 description 16
239000007858 starting material Substances 0.000 description 16
230000003647 oxidation Effects 0.000 description 15
238000007254 oxidation reaction Methods 0.000 description 15
239000002904 solvent Substances 0.000 description 15
238000006114 decarboxylation reaction Methods 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
238000009835 boiling Methods 0.000 description 11
239000012362 glacial acetic acid Substances 0.000 description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
238000003756 stirring Methods 0.000 description 11
239000001117 sulphuric acid Substances 0.000 description 11
235000011149 sulphuric acid Nutrition 0.000 description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
238000007127 saponification reaction Methods 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000005457 ice water Substances 0.000 description 9
150000002596 lactones Chemical class 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
229940117975 chromium trioxide Drugs 0.000 description 8
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 8
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 8
238000005886 esterification reaction Methods 0.000 description 8
239000012442 inert solvent Substances 0.000 description 8
229960003387 progesterone Drugs 0.000 description 8
239000000186 progesterone Substances 0.000 description 8
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
238000010992 reflux Methods 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 5
230000032050 esterification Effects 0.000 description 5
238000006266 etherification reaction Methods 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
150000003431 steroids Chemical class 0.000 description 5
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 4
239000012043 crude product Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
230000006324 decarbonylation Effects 0.000 description 4
238000006606 decarbonylation reaction Methods 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
238000000605 extraction Methods 0.000 description 4
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
150000004702 methyl esters Chemical class 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
125000004423 acyloxy group Chemical group 0.000 description 3
239000004411 aluminium Substances 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
125000005997 bromomethyl group Chemical group 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 3
230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
150000002923 oximes Chemical class 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
239000011701 zinc Substances 0.000 description 3
FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 2
YSULOORXQBDPCU-UHFFFAOYSA-N 2-(trimethylazaniumyl)ethanehydrazonate;hydrochloride Chemical compound [Cl-].C[N+](C)(C)CC(=O)NN YSULOORXQBDPCU-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical group CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
239000004157 Nitrosyl chloride Substances 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012024 dehydrating agents‎ Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
125000001475 halogen functional group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 2
235000019392 nitrosyl chloride Nutrition 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
150000003891 oxalate salts Chemical class 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
150000003145 progesterone derivatives Chemical class 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
239000010453 quartz Substances 0.000 description 2
229910001923 silver oxide Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
150000003890 succinate salts Chemical class 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
OVTZIJOGPKGLQV-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1C=C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 OVTZIJOGPKGLQV-BYZMTCBYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Epidemiology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL26799A 1965-11-26 1966-11-03 16 - Methylene - 17 - Hydroxy - 19 - Norprogesterone, its sites and esters and pharmaceutical preparations containing them IL26799A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEM0067421		1965-11-26
DEM0070314		1966-07-21

Publications (1)

Publication Number	Publication Date
IL26799A true IL26799A (en)	1970-07-19

Family

ID=25987793

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL26799A IL26799A (en)	1965-11-26	1966-11-03	16 - Methylene - 17 - Hydroxy - 19 - Norprogesterone, its sites and esters and pharmaceutical preparations containing them

Country Status (11)

Country	Link
US (1)	US3510556A (de)
BE (1)	BE690214A (de)
CH (3)	CH481901A (de)
DE (2)	DE1543245C3 (de)
DK (1)	DK119158B (de)
ES (1)	ES333793A1 (de)
FR (1)	FR6884M (de)
GB (1)	GB1091660A (de)
IL (1)	IL26799A (de)
NL (1)	NL154218B (de)
SE (1)	SE329153B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2803660A1 (de) *	1978-01-25	1979-07-26	Schering Ag	Neue in 17-position substituierte steroide der pregnanreihe, ihre herstellung und verwendung
ES2180690T3 (es) *	1990-06-01	2003-02-16	Population Council Inc	Preparacion de composiciones que comprenden st1435 para aplicacion topica.
GB2252497B (en) *	1991-02-04	1995-01-18	Elsimar Metzker Coutinho	Pharmaceutical composition
US5710293A (en) *	1995-10-13	1998-01-20	The Population Council, Center For Biomedical Research	Method of preparation of ester derivatives of steroids

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3105840A (en) *	1958-12-12	1963-10-01	Merck & Co Inc	Alkyl ethers of 17alpha-hydroxy-19-nor progesterone
DE1277253B (de) *	1963-01-19	1968-09-12	Merck Ag E	Ungesaettigte 16-Methylen-17ª‡-alkoxy-3, 20-diketo-steroide der Pregnanreihe sowie ein Verfahren zu ihrer Herstellung
CH464194A (de) *	1963-04-10	1968-10-31	Ciba Geigy	Verfahren zur Herstellung neuer Steroide

1965
- 1965-11-26 DE DE1543245A patent/DE1543245C3/de not_active Expired
1966
- 1966-07-21 DE DE1593052A patent/DE1593052C3/de not_active Expired
- 1966-09-20 CH CH1362266A patent/CH481901A/de not_active IP Right Cessation
- 1966-09-20 CH CH1378869A patent/CH521330A/de not_active IP Right Cessation
- 1966-09-20 CH CH1378969A patent/CH480317A/de not_active IP Right Cessation
- 1966-10-31 GB GB48622/66A patent/GB1091660A/en not_active Expired
- 1966-11-03 IL IL26799A patent/IL26799A/en unknown
- 1966-11-16 NL NL666616162A patent/NL154218B/xx unknown
- 1966-11-18 FR FR84135A patent/FR6884M/fr not_active Expired
- 1966-11-23 US US596439A patent/US3510556A/en not_active Expired - Lifetime
- 1966-11-25 ES ES333793A patent/ES333793A1/es not_active Expired
- 1966-11-25 BE BE690214D patent/BE690214A/xx unknown
- 1966-11-25 DK DK612466AA patent/DK119158B/da unknown
- 1966-11-25 SE SE16122/66A patent/SE329153B/xx unknown

Also Published As

Publication number	Publication date
DE1593052B2 (de)	1974-08-15
DE1593052A1 (de)	1970-07-23
NL6616162A (de)	1967-05-29
CH521330A (de)	1972-04-15
GB1091660A (en)	1967-11-22
US3510556A (en)	1970-05-05
CH481901A (de)	1969-11-30
DE1593052C3 (de)	1975-04-17
NL154218B (nl)	1977-08-15
ES333793A1 (es)	1968-01-01
DE1543245C3 (de)	1974-07-18
CH480317A (de)	1969-10-31
DE1543245B2 (de)	1973-12-20
FR6884M (de)	1969-04-21
SE329153B (de)	1970-10-05
BE690214A (de)	1967-05-25
DE1543245A1 (de)	1969-09-11
DK119158B (da)	1970-11-23

Publication	Publication Date	Title
Marker et al.	1947	Steroidal sapogenins1a
JPS5933600B2 (ja)	1984-08-16	新規な１１，１１−アルキリデンステロイドの製造方法
US3947478A (en)	1976-03-30	Alkylated 3,20-diketo-Δ4 -steroids of the pregnane series
NO143159B (no)	1980-09-15	Fremgangsmaate for fremstilling av metylmetakrylat-alkylakrylatkopolymerer.
US2878267A (en)	1959-03-17	19-nor-steroid compounds and process for the preparation thereof
DE1468035A1 (de)	1968-12-12	Verfahren zur Herstellung von 19-Alkylsteroiden
US2874173A (en)	1959-02-17	Estrone compounds
US3510556A (en)	1970-05-05	17alpha-ethers of 16-methylene-19-nor-progesterones
US3206460A (en)	1965-09-14	6-hydroxy-and 6-keto-delta-19-norandrostene and pregnene derivatives
US2499248A (en)	1950-02-28	2,13 - dimethyl - polyhydrophenanthrene lactone derivatives and the preparation thereof
Holness et al.	1956	The identification of some adrenocortical steroids in urine
US2684376A (en)	1954-07-20	Process for the simultaneous oxidation and halogenation of steroids and compounds obtained thereby
US3409643A (en)	1968-11-05	Process for the preparation of 17alpha-alkynl-17beta-alkanoyloxy steroids of the androstane and estrane series
US2682548A (en)	1954-06-29	Delta5-androstene-3beta, 17alpha-diol-16-one ethers
US3980681A (en)	1976-09-14	Process for the preparation of 11-β-nitro-oxysteroids
Marshall et al.	1957	7-Keto steroids. I. Steroidal 3-hydroxy-3, 5-dien-7-ones
US3159643A (en)	1964-12-01	6-methylene-3-oxo-delta4 steroids and process for preparation of same
US3154569A (en)	1964-10-27	19-nitrilosteroids and process for producing 19-norsteroids
US2992217A (en)	1961-07-11	16 alpha-hydroxymethyl-progesterone and derivatives
US3053735A (en)	1962-09-11	Enol ethers of 6-chloro substituted delta-3-ketones of the androstane series
US3096353A (en)	1963-07-02	Delta9-dehydro-21-haloethisterones and the process for the production thereof
US3717627A (en)	1973-02-20	Process for the production of estrogenic steroids having a formyl group in the 1-or 4-position
US3242169A (en)	1966-03-22	6alpha-dimethylaminomethyl-3-oxo-delta4-steroids and method for producing same
US2997488A (en)	1961-08-22	2-methyl-19-nor-steroids
US3498975A (en)	1970-03-03	Haloethisterone compounds