IL38112A - 3alpha-hydroxy-pregn-4-en-20-one and esters thereof their preparation and anesthetic com positions comprising them - Google Patents

3alpha-hydroxy-pregn-4-en-20-one and esters thereof their preparation and anesthetic com positions comprising them

Info

Publication number: IL38112A
Authority: IL; Israel
Prior art keywords: steroid; hydroxy; group; composition; ester
Prior art date: 1970-11-06

Application number

IL38112A

Other languages

English (en)

Other versions

IL38112A0 (en

Original Assignee

Glaxo Lab Ltd

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.)

1970-11-06

Filing date

1971-11-09

Publication date

1977-06-30

1971-11-09 Application filed by Glaxo Lab Ltd filed Critical Glaxo Lab Ltd

1972-03-28 Publication of IL38112A0 publication Critical patent/IL38112A0/xx

1977-06-30 Publication of IL38112A publication Critical patent/IL38112A/en

Links

230000003444 anaesthetic effect Effects 0.000 title claims description 35
238000002360 preparation method Methods 0.000 title claims description 23
150000002148 esters Chemical class 0.000 title claims description 10
QWVWXRKHAXWWSV-QYYVTAPASA-N 1-[(3r,8s,9s,10r,13s,14s,17s)-3-hydroxy-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1CC2=C[C@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 QWVWXRKHAXWWSV-QYYVTAPASA-N 0.000 title claims description 6
239000000243 solution Substances 0.000 claims description 58
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 56
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 54
239000000203 mixture Substances 0.000 claims description 49
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
150000003431 steroids Chemical class 0.000 claims description 44
150000001875 compounds Chemical class 0.000 claims description 41
238000000034 method Methods 0.000 claims description 33
-1 alkanoyl ester Chemical class 0.000 claims description 23
239000004094 surface-active agent Substances 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 17
239000002904 solvent Substances 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 11
206010002091 Anaesthesia Diseases 0.000 claims description 10
230000037005 anaesthesia Effects 0.000 claims description 10
238000001949 anaesthesia Methods 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
230000010933 acylation Effects 0.000 claims description 9
238000005917 acylation reaction Methods 0.000 claims description 9
239000007864 aqueous solution Substances 0.000 claims description 8
238000006073 displacement reaction Methods 0.000 claims description 8
239000003921 oil Substances 0.000 claims description 8
238000006460 hydrolysis reaction Methods 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000004043 oxo group Chemical group O=* 0.000 claims description 6
230000007062 hydrolysis Effects 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
125000006353 oxyethylene group Chemical group 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
238000007911 parenteral administration Methods 0.000 claims description 4
150000003128 pregnanes Chemical class 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
229910001413 alkali metal ion Inorganic materials 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
235000014113 dietary fatty acids Nutrition 0.000 claims description 3
239000000194 fatty acid Substances 0.000 claims description 3
229930195729 fatty acid Natural products 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
230000000269 nucleophilic effect Effects 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
150000004665 fatty acids Chemical class 0.000 claims description 2
239000010685 fatty oil Substances 0.000 claims description 2
125000005456 glyceride group Chemical group 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
230000001939 inductive effect Effects 0.000 claims description 2
150000007530 organic bases Chemical group 0.000 claims description 2
239000003495 polar organic solvent Substances 0.000 claims description 2
239000003981 vehicle Substances 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims 3
150000002440 hydroxy compounds Chemical class 0.000 claims 2
241000124008 Mammalia Species 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
150000001735 carboxylic acids Chemical class 0.000 claims 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000003700 epoxy group Chemical group 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
229940124326 anaesthetic agent Drugs 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000007787 solid Substances 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
239000003208 petroleum Substances 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
238000002425 crystallisation Methods 0.000 description 8
239000000463 material Substances 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
150000007513 acids Chemical class 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
125000002252 acyl group Chemical class 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
239000000284 extract Substances 0.000 description 6
238000000926 separation method Methods 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
229940120124 dichloroacetate Drugs 0.000 description 5
239000012259 ether extract Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
238000012746 preparative thin layer chromatography Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
VSOUOXNALBTHGS-JHGMSEHPSA-N (3R,8S,9S,10R,13S,14S,17S)-17-acetyl-3-hydroxy-10,13-dimethyl-1,2,3,6,7,8,9,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-11-one Chemical compound O[C@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](C(C)=O)[C@]4(CC([C@@H]3[C@]2(CC1)C)=O)C VSOUOXNALBTHGS-JHGMSEHPSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
QRLVDLBMBULFAL-UHFFFAOYSA-N Digitonin Natural products CC1CCC2(OC1)OC3C(O)C4C5CCC6CC(OC7OC(CO)C(OC8OC(CO)C(O)C(OC9OCC(O)C(O)C9OC%10OC(CO)C(O)C(OC%11OC(CO)C(O)C(O)C%11O)C%10O)C8O)C(O)C7O)C(O)CC6(C)C5CCC4(C)C3C2C QRLVDLBMBULFAL-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000008351 acetate buffer Substances 0.000 description 4
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 4
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 4
UVYVLBIGDKGWPX-KUAJCENISA-N digitonin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)C[C@@H](O)[C@H](O[C@H]5[C@@H]([C@@H](O)[C@@H](O[C@H]6[C@@H]([C@@H](O[C@H]7[C@@H]([C@@H](O)[C@H](O)CO7)O)[C@H](O)[C@@H](CO)O6)O[C@H]6[C@@H]([C@@H](O[C@H]7[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O7)O)[C@@H](O)[C@@H](CO)O6)O)[C@@H](CO)O5)O)C[C@@H]4CC[C@H]3[C@@H]2[C@@H]1O)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 UVYVLBIGDKGWPX-KUAJCENISA-N 0.000 description 4
UVYVLBIGDKGWPX-UHFFFAOYSA-N digitonine Natural products CC1C(C2(CCC3C4(C)CC(O)C(OC5C(C(O)C(OC6C(C(OC7C(C(O)C(O)CO7)O)C(O)C(CO)O6)OC6C(C(OC7C(C(O)C(O)C(CO)O7)O)C(O)C(CO)O6)O)C(CO)O5)O)CC4CCC3C2C2O)C)C2OC11CCC(C)CO1 UVYVLBIGDKGWPX-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
230000006698 induction Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
229920002685 Polyoxyl 35CastorOil Polymers 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
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WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001914 filtration Methods 0.000 description 3
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
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 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
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238000009835 boiling Methods 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000000872 buffer Substances 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000012043 crude product Substances 0.000 description 2
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
229940113088 dimethylacetamide Drugs 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
150000002081 enamines Chemical class 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 2
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
229940117927 ethylene oxide Drugs 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000003326 hypnotic agent Substances 0.000 description 2
230000000147 hypnotic effect Effects 0.000 description 2
238000010253 intravenous injection Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 2
FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 2
229920000056 polyoxyethylene ether Polymers 0.000 description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
229920000053 polysorbate 80 Polymers 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
235000011181 potassium carbonates Nutrition 0.000 description 2
230000002285 radioactive effect Effects 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000012552 review Methods 0.000 description 2
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229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
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238000003756 stirring Methods 0.000 description 2
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JNYAEWCLZODPBN-KVTDHHQDSA-N (2r,3r,4r)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@@H](O)[C@H]1O JNYAEWCLZODPBN-KVTDHHQDSA-N 0.000 description 1
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BXXMZDAZGQYNGT-OSBZKKERSA-N (3R,8S,9S,10R,13R,14S,17S)-17-ethyl-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol Chemical class O[C@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](CC)[C@]4(CC[C@@H]3[C@]2(CC1)C)C BXXMZDAZGQYNGT-OSBZKKERSA-N 0.000 description 1
LDAVQTPZUVZVKG-DADBAOPHSA-N (8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,7,8,9,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-11-one Chemical compound O=C1[C@@H]2[C@]3(CCC=CC3=CC[C@H]2[C@@H]2CC[C@H](C(C)=O)[C@]2(C1)C)C LDAVQTPZUVZVKG-DADBAOPHSA-N 0.000 description 1
BXXMZDAZGQYNGT-CDXRDQLVSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-ol Chemical class C1CC2=CC(O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 BXXMZDAZGQYNGT-CDXRDQLVSA-N 0.000 description 1
DJVDBKCOQPFYBH-BMHRSWJNSA-N (8s,9s,10r,13s,14s,17s)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-2,6,7,8,9,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene-3,11-dione Chemical compound CC1([C@@H]2[C@]3(CC(=O)[C@@H]4[C@@]5(C)CCC(=O)C=C5CC[C@H]4[C@@H]3CC2)C)OCCO1 DJVDBKCOQPFYBH-BMHRSWJNSA-N 0.000 description 1
AYFVZTVXUPIKOP-YFWFAHHUSA-N 1-[(8s,9s,10r,13s,14s,17s)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethanone Chemical compound C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 AYFVZTVXUPIKOP-YFWFAHHUSA-N 0.000 description 1
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BWSQKOKULIALEW-UHFFFAOYSA-N 2-[2-[4-fluoro-3-(trifluoromethyl)phenyl]-3-[2-(piperidin-3-ylamino)pyrimidin-4-yl]imidazol-4-yl]acetonitrile Chemical compound FC1=C(C=C(C=C1)C=1N(C(=CN=1)CC#N)C1=NC(=NC=C1)NC1CNCCC1)C(F)(F)F BWSQKOKULIALEW-UHFFFAOYSA-N 0.000 description 1
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 1
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-pregnane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-NUNROCCHSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical class CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
244000166102 Eucalyptus leucoxylon Species 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
241000906446 Theraps Species 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
FESLGEDALGYOHR-MFXMNTOZSA-N [(3R,8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-11-oxo-1,2,3,6,7,8,9,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C(C)(=O)O[C@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](C(C)=O)[C@]4(CC([C@@H]3[C@]2(CC1)C)=O)C FESLGEDALGYOHR-MFXMNTOZSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
150000001243 acetic acids Chemical class 0.000 description 1
238000007605 air drying Methods 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000036592 analgesia Effects 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
CASOXAYOCHCWQU-UHFFFAOYSA-N butan-2-one;ethanol Chemical compound CCO.CCC(C)=O CASOXAYOCHCWQU-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003874 central nervous system depressant Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940093499 ethyl acetate Drugs 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 1
229960003132 halothane Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000000155 isotopic effect Effects 0.000 description 1
125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
150000004668 long chain fatty acids Chemical class 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
239000000693 micelle Substances 0.000 description 1
239000001272 nitrous oxide Substances 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
150000002924 oxiranes Chemical group 0.000 description 1
208000035824 paresthesia Diseases 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 1
239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
150000003126 pregnane derivatives Chemical class 0.000 description 1
JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane group Chemical group [C@@H]12CC[C@H](CC)[C@@]1(C)CC[C@H]1[C@H]2CCC2CCCC[C@]12C JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
238000011160 research Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
241000894007 species Species 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000012360 testing method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
AWLILQARPMWUHA-UHFFFAOYSA-M thiopental sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC([S-])=NC1=O AWLILQARPMWUHA-UHFFFAOYSA-M 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
125000005457 triglyceride group Chemical group 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000011179 visual inspection Methods 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
- 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
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)

IL38112A 1970-11-06 1971-11-09 3alpha-hydroxy-pregn-4-en-20-one and esters thereof their preparation and anesthetic com positions comprising them IL38112A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB5303870A GB1372175A (en)	1970-11-06	1970-11-06	3alpha-hydroxy-pregn-4-enes

Publications (2)

Publication Number	Publication Date
IL38112A0 IL38112A0 (en)	1972-03-28
IL38112A true IL38112A (en)	1977-06-30

Family

ID=10466377

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL38112A IL38112A (en)	1970-11-06	1971-11-09	3alpha-hydroxy-pregn-4-en-20-one and esters thereof their preparation and anesthetic com positions comprising them

Country Status (10)

Country	Link
AU (1)	AU470121B2 (fr)
BE (1)	BE774988A (fr)
CA (1)	CA981251A (fr)
DE (1)	DE2155137A1 (fr)
DK (1)	DK128898B (fr)
FR (1)	FR2112503B1 (fr)
GB (1)	GB1372175A (fr)
IL (1)	IL38112A (fr)
NL (1)	NL7115297A (fr)
ZA (1)	ZA717449B (fr)

1970
- 1970-11-06 GB GB5303870A patent/GB1372175A/en not_active Expired
1971
- 1971-11-05 CA CA126,960A patent/CA981251A/en not_active Expired
- 1971-11-05 AU AU35398/71A patent/AU470121B2/en not_active Expired
- 1971-11-05 BE BE774988A patent/BE774988A/fr unknown
- 1971-11-05 ZA ZA717449A patent/ZA717449B/xx unknown
- 1971-11-05 FR FR7139810A patent/FR2112503B1/fr not_active Expired
- 1971-11-05 NL NL7115297A patent/NL7115297A/xx not_active Application Discontinuation
- 1971-11-05 DK DK542071AA patent/DK128898B/da unknown
- 1971-11-05 DE DE19712155137 patent/DE2155137A1/de active Pending
- 1971-11-09 IL IL38112A patent/IL38112A/en unknown

Also Published As

Publication number	Publication date
GB1372175A (en)	1974-10-30
IL38112A0 (en)	1972-03-28
CA981251A (en)	1976-01-06
AU470121B2 (en)	1976-03-04
DK128898B (da)	1974-07-22
ZA717449B (en)	1973-06-27
NL7115297A (fr)	1972-05-09
FR2112503A1 (fr)	1972-06-16
BE774988A (fr)	1972-05-05
FR2112503B1 (fr)	1975-11-28
AU3539871A (en)	1973-05-10
DE2155137A1 (de)	1972-05-10

Publication	Publication Date	Title
US2183589A (en)	1939-12-19	Derivatives of compounds of the
US3580937A (en)	1971-05-25	7alpha- and 7beta-methyl-3alpha,5alpha-cycloandrostanes,6-methyl derivatives thereof and the 19-nor analogues of the foregoing
DE69023947T2 (de)	1996-05-30	Fluorierte Gallensäure-Derivate, Verfahren zu deren Herstellung und pharmazeutische Zusammensetzungen daraus.
Hershberg et al.	1951	Catalytic hydrogenation of cholesterol
US3781435A (en)	1973-12-25	Steroid anaesthetics
US3318926A (en)	1967-05-09	7alpha-methyl-16alpha-hydroxy-estrones
US3953429A (en)	1976-04-27	Anaesthetic steroids of the androstance and pregnane series
Ringold et al.	1956	Steroids. LXXV. Dehydrogenation of testosterone to Δ1, 4-androstadien-17β-ol-3-one with selenium dioxide
US3380886A (en)	1968-04-30	7alpha-methyl-3beta-hydroxy-5-androstenes
US4427671A (en)	1984-01-24	Steroids esterified in position 17 and thioesterified in position 21, a process for preparing them and their use as medicaments
US3825565A (en)	1974-07-23	3alpha-hydroxy-delta4-steroids of the pregnane series and esters thereof
Salce et al.	1970	Preparation of 16-unsaturated steroids by elimination of 17. alpha.-acyloxyl
IL38112A (en)	1977-06-30	3alpha-hydroxy-pregn-4-en-20-one and esters thereof their preparation and anesthetic com positions comprising them
US3883569A (en)	1975-05-13	Novel 3{60 -hydroxysteroids of the 5{60 -pregnane series
US3377366A (en)	1968-04-09	17alpha-alkynyl/alkenyl-11, 13beta-dialkylgon-5(10)-en-3-ones and esters thereof
IL28867A (en)	1972-04-27	1-adamantyl and 1-adamantylmethyl carbonates of testosterone and derivatives thereof
US3347880A (en)	1967-10-17	17alpha-halogenoethinylestranes
US4390530A (en)	1983-06-28	3-Deoxy-Δ15 -steroids
US3525757A (en)	1970-08-25	Methods of preparing 15,16beta-methylene-testosterone and esters thereof
US3189625A (en)	1965-06-15	Novel 17-ketals of equilenin and method for preparing
IE49235B1 (en)	1985-09-04	New derivatives of 2-substituted-19-nor steroids,processes for their preparation and pharmaceutical compositions containing them
JP2834721B2 (ja)	1998-12-14	１７α−シアノメチルエストラ−４，９−ジエン誘導体、その製造方法および該化合物を含有する医薬品
US3488346A (en)	1970-01-06	17-alpha-substituted-6-alpha-methyl-pregn-4-en compounds
US3475419A (en)	1969-10-28	17 - hydroxy - 3 - oxyestra - 1,3,5(10) - triene-17alpha-carboxaldehydes and derivatives
US3522281A (en)	1970-07-28	Delta**3,5-7alpha-methyloestradienes