CH376100A - Verfahren zur Herstellung neuer Steroidverbindungen - Google Patents

Verfahren zur Herstellung neuer Steroidverbindungen

Info

Publication number: CH376100A
Authority: CH; Switzerland
Prior art keywords: sep; methyl; solution; oxytestosterone; oxy
Prior art date: 1958-06-06

Application number

CH7411159A

Other languages

German (de)

English (en)

Inventor

Campbell J Allan

Claude Babcock John

Original Assignee

Upjohn Co

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.)

1958-06-06

Filing date

1959-06-06

Publication date

1964-03-31

1959-06-06 Application filed by Upjohn Co filed Critical Upjohn Co

1964-03-31 Publication of CH376100A publication Critical patent/CH376100A/de

Links

-1 steroid compounds Chemical class 0.000 title claims description 23
238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 claims description 14
HZWZHWTZLZZBFF-OLGCGSEZSA-N (8r,9s,10r,13s,14s,17s)-17-hydroxy-7,10,13-trimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical class C1C[C@]2(C)[C@@H](O)CC[C@H]2[C@@H]2C(C)CC3=CC(=O)CC[C@]3(C)[C@H]21 HZWZHWTZLZZBFF-OLGCGSEZSA-N 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 10
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical group Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 7
239000007818 Grignard reagent Substances 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical group [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 3
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 3
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 claims description 3
150000004795 grignard reagents Chemical class 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
230000003647 oxidation Effects 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
230000001737 promoting effect Effects 0.000 claims description 3
150000008064 anhydrides Chemical class 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 46
239000000243 solution Substances 0.000 description 46
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 41
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
239000000203 mixture Substances 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000004458 analytical method Methods 0.000 description 9
239000000047 product Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 7
239000000391 magnesium silicate Substances 0.000 description 7
229910052919 magnesium silicate Inorganic materials 0.000 description 7
235000019792 magnesium silicate Nutrition 0.000 description 7
150000003431 steroids Chemical class 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 6
229930195733 hydrocarbon Natural products 0.000 description 6
239000007787 solid Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 5
UMDCOKNNLDEKJB-DYKIIFRCSA-N 6-dehydrotestosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3C=CC2=C1 UMDCOKNNLDEKJB-DYKIIFRCSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
BRQAXEKVGOTNJM-HLXURNFRSA-N 17alpha-Methyl-17beta-hydroxyandrosta-4,6-dien-3-one Chemical compound C1=CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 BRQAXEKVGOTNJM-HLXURNFRSA-N 0.000 description 3
230000001195 anabolic effect Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 3
229960003604 testosterone Drugs 0.000 description 3
IVFYLRMMHVYGJH-AKDLPHLISA-N (8r,9s,10r,13s,14s,17s)-17-hydroxy-7,10,13,17-tetramethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1C[C@]2(C)[C@](O)(C)CC[C@H]2[C@@H]2C(C)CC3=CC(=O)CC[C@]3(C)[C@H]21 IVFYLRMMHVYGJH-AKDLPHLISA-N 0.000 description 2
BFMZZSBHQOCQFQ-HTDHLNIYSA-N 17beta-Hydroxy-17-methylandrosta-4,9(11)-dien-3-one Chemical compound O=C1CC[C@]2(C)C3=CC[C@]4(C)[C@@](C)(O)CC[C@H]4[C@@H]3CCC2=C1 BFMZZSBHQOCQFQ-HTDHLNIYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
239000003513 alkali Substances 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
229960005235 piperonyl butoxide Drugs 0.000 description 2
229920006395 saturated elastomer Polymers 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
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WTPMRQZHJLJSBO-XQALERBDSA-N 11-oxotestosterone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 WTPMRQZHJLJSBO-XQALERBDSA-N 0.000 description 1
GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 description 1
KYLCHXHHSBPYCB-GECNCUIPSA-N 17beta-Hydroxy-17-methylandrost-4-ene-3,11-dione Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2=O KYLCHXHHSBPYCB-GECNCUIPSA-N 0.000 description 1
IUFOPOQNYKRRML-FQQAFBJJSA-N 17beta-Hydroxyandrosta-4,9(11)-dien-3-one Chemical compound O=C1CC[C@]2(C)C3=CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 IUFOPOQNYKRRML-FQQAFBJJSA-N 0.000 description 1
208000026310 Breast neoplasm Diseases 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
239000004280 Sodium formate Substances 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
230000001548 androgenic effect Effects 0.000 description 1
230000001833 anti-estrogenic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
SDCJMBBHNJPYGW-UHFFFAOYSA-L disodium;hydrogen carbonate;chloride Chemical compound [Na+].[Na+].Cl.[O-]C([O-])=O SDCJMBBHNJPYGW-UHFFFAOYSA-L 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000000328 estrogen antagonist Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011344 liquid material Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
239000006201 parenteral dosage form Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Substances [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001072 progestational effect Effects 0.000 description 1
239000012264 purified product Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration 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
- C07J75/00—Processes for the preparation of steroids in general

Landscapes

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

CH7411159A 1958-06-06 1959-06-06 Verfahren zur Herstellung neuer Steroidverbindungen CH376100A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US74019458A	1958-06-06	1958-06-06

Publications (1)

Publication Number	Publication Date
CH376100A true CH376100A (de)	1964-03-31

Family

ID=24975440

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH7411159A CH376100A (de)	1958-06-06	1959-06-06	Verfahren zur Herstellung neuer Steroidverbindungen

Country Status (2)

Country	Link
BE (1)	BE598469A (fr)
CH (1)	CH376100A (fr)

1959
- 1959-06-06 CH CH7411159A patent/CH376100A/de unknown
1960
- 1960-12-22 BE BE598469A patent/BE598469A/fr unknown

Also Published As

Publication number	Publication date
BE598469A (fr)	1961-06-22

Publication	Publication Date	Title
DE2400931A1 (de)	1974-07-25	Derivate des vitamin d und verfahren zu ihrer herstellung
CH561739A5 (en)	1975-05-15	4-Hydroxy-2-butenoic acid lactone steroid derivs - cardiotonic, anti-inflammatory, hypocholesterolaemic, mineralocorticoid agents
CH376100A (de)	1964-03-31	Verfahren zur Herstellung neuer Steroidverbindungen
DE1618871C3 (de)	1974-02-21	Verfahren zur Herstellung eines Steroidketonderivates. Ausscheidung aus: 1468988
DE2409971C3 (de)	1978-03-23	5-Cholestenderivate und Verfahren zu ihrer Herstellung
DE2119708C3 (de)	1981-10-08	4,14-Östradiene, Verfahren zu ihrer Herstellung und diese enthaltende Arzneipräparate
DE1543992C3 (de)	1975-06-05	Verfahren zur Herstellung von Equilin
CH561230A5 (en)	1975-04-30	6,8-Pentaenes - has oestrogenic activity
DE2441647A1 (de)	1975-03-06	17beta-aethinyl-3,17alpha-oestradiolverbindungen, verfahren zu ihrer herstellung, arzneimittel und 17beta-aethinyl-16alpha, 17alpha-epoxyoestran-3-olverbindungen
DE1264441B (de)	1968-03-28	Verfahren zur Herstellung von 17alpha-AEthinyl-delta 5(10-19-nor-androsten-17beta-ol-3-on und 17alpha-AEthynil-19-nor-testosteron sowie dessen Estern
DE843411C (de)	1952-07-07	Verfahren zur Gewinnung in 21-Stellung substituierter Pregnanderivate
DE1468561C (de)	1971-04-15	Verfahren zur Herstellung von 13 Alkyl gona l,3,5(10),8,14 pentaenen
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