CH487135A - Verfahren zur Herstellung von 19-Nor-Steroiden - Google Patents

Verfahren zur Herstellung von 19-Nor-Steroiden

Info

Publication number: CH487135A
Authority: CH; Switzerland
Prior art keywords: sep; oxo; solvent; acid; starting materials
Prior art date: 1961-07-14

Application number

CH1516961A

Other languages

German (de)

English (en)

Inventor

Wettstein Albert Dr Prof

Georg Dr Anner

Karl Dr Heusler

Jaroslav Dr Kalvoda

Peter Dr Wieland

Original Assignee

Ciba Geigy

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.)

1961-07-14

Filing date

1961-12-29

Publication date

1970-03-15

1961-07-14 Priority claimed from CH827061A external-priority patent/CH425774A/de

1961-12-29 Application filed by Ciba Geigy filed Critical Ciba Geigy

1961-12-29 Priority to CH1516961A priority Critical patent/CH487135A/de

1962-07-11 Priority to GB1091764A priority patent/GB1007758A/en

1962-07-11 Priority to GB2672162A priority patent/GB1007757A/en

1962-07-13 Priority to ES279208A priority patent/ES279208A1/es

1962-07-13 Priority to DK315162A priority patent/DK118076B/da

1962-07-13 Priority to SE788962A priority patent/SE306734B/xx

1962-07-13 Priority to AT568362A priority patent/AT249882B/de

1962-07-13 Priority to DK391963A priority patent/DK109958C/da

1962-10-12 Priority to FR912034A priority patent/FR6461M/fr

1962-10-12 Priority to FR912035A priority patent/FR6462M/fr

1966-01-07 Priority to NL6600218A priority patent/NL6600218A/xx

1966-11-01 Priority to SE14961/66A priority patent/SE323957B/xx

1967-09-13 Priority to NL676712537A priority patent/NL138942B/xx

1967-09-13 Priority to NL676712536A priority patent/NL139455B/xx

1970-03-15 Publication of CH487135A publication Critical patent/CH487135A/de

Links

238000000034 method Methods 0.000 title claims description 20
238000004519 manufacturing process Methods 0.000 title description 5
239000002253 acid Substances 0.000 claims description 20
239000002904 solvent Substances 0.000 claims description 14
239000007858 starting material Substances 0.000 claims description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
230000007935 neutral effect Effects 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
-1 norsteroid dienes Chemical class 0.000 claims description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
239000000463 material Substances 0.000 claims description 2
BZQFBWGGLXLEPQ-REOHCLBHSA-N phosphoserine Chemical compound OC(=O)[C@@H](N)COP(O)(O)=O BZQFBWGGLXLEPQ-REOHCLBHSA-N 0.000 description 537
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
150000001875 compounds Chemical class 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
LXMQZGGLHVSEBA-UHFFFAOYSA-N chromium;trihydrate Chemical compound O.O.O.[Cr] LXMQZGGLHVSEBA-UHFFFAOYSA-N 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
125000004043 oxo group Chemical group O=* 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
238000006114 decarboxylation reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000155 melt Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
YLTCTXBDDHSLCS-KOUJMVCDSA-N 19-hydroxytestosterone Chemical compound O=C1CC[C@]2(CO)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 YLTCTXBDDHSLCS-KOUJMVCDSA-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
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
PXXNTAGJWPJAGM-VCOUNFBDSA-N Decaline Chemical compound C=1([C@@H]2C3)C=C(OC)C(OC)=CC=1OC(C=C1)=CC=C1CCC(=O)O[C@H]3C[C@H]1N2CCCC1 PXXNTAGJWPJAGM-VCOUNFBDSA-N 0.000 description 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
DJPZSBANTAQNFN-UHFFFAOYSA-N Testosterone acetate Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(OC(=O)C)C1(C)CC2 DJPZSBANTAQNFN-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
230000001195 anabolic effect Effects 0.000 description 1
230000001548 androgenic effect Effects 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
230000002513 anti-ovulatory effect Effects 0.000 description 1
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
LKLAOWLOTDVVGF-UHFFFAOYSA-N chromium(6+) oxygen(2-) sulfuric acid Chemical compound [O-2].[O-2].[O-2].[Cr+6].OS(O)(=O)=O LKLAOWLOTDVVGF-UHFFFAOYSA-N 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002084 enol ethers Chemical class 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
150000005217 methyl ethers Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000000203 mixture Substances 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
125000000369 oxido group Chemical group [*]=O 0.000 description 1
DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 description 1
150000003128 pregnanes Chemical class 0.000 description 1
230000001072 progestational effect Effects 0.000 description 1
238000010992 reflux Methods 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
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

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
- 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
- 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
- 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)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)

CH1516961A 1961-07-14 1961-12-29 Verfahren zur Herstellung von 19-Nor-Steroiden CH487135A (de)

Priority Applications (14)

Application Number	Priority Date	Filing Date	Title
CH1516961A CH487135A (de)	1961-07-14	1961-12-29	Verfahren zur Herstellung von 19-Nor-Steroiden
GB1091764A GB1007758A (en)	1961-07-14	1962-07-11	í¸-3:19-dioxo-steroids and í¸-3-oxo-steroid-19-acids
GB2672162A GB1007757A (en)	1961-07-14	1962-07-11	19-nor-steroids and process for their manufacture
DK391963A DK109958C (da)	1961-07-14	1962-07-13	Fremgangsmåde til fremstilling af Δ<4,6>-3,20-dioxo-4-chlor- eller -4-brom-19-nor-pregnadiener.
AT568362A AT249882B (de)	1961-07-14	1962-07-13	Verfahren zur Herstellung von 19-Nor-steroiden
DK315162A DK118076B (da)	1961-07-14	1962-07-13	Fremgangsmåde til fremstilling af Δ<4,6>-eller Δ<5(10),6>-3-oxo-19-norsteroider.
SE788962A SE306734B (da)	1961-07-14	1962-07-13
ES279208A ES279208A1 (es)	1961-07-14	1962-07-13	Procedimiento para la obtención de 19-nor-esteroides
FR912034A FR6461M (da)	1961-07-14	1962-10-12
FR912035A FR6462M (da)	1961-07-14	1962-10-12
NL6600218A NL6600218A (da)	1961-07-14	1966-01-07
SE14961/66A SE323957B (da)	1961-07-14	1966-11-01
NL676712537A NL138942B (nl)	1961-07-14	1967-09-13	Werkwijze ter bereiding van 19-nor-steroiden.
NL676712536A NL139455B (nl)	1961-07-14	1967-09-13	Werkwijze ter bereiding van farmaceutische preparaten met gestagene en de vruchtbaarheid regelende eigenschappen, aldus verkregen gevormde preparaten en werkwijze ter bereiding van steroiden.

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH827061A CH425774A (de)	1961-07-14	1961-07-14	Verfahren zur Herstellung von 19-Nor-steroiden
CH1516961A CH487135A (de)	1961-07-14	1961-12-29	Verfahren zur Herstellung von 19-Nor-Steroiden

Publications (1)

Publication Number	Publication Date
CH487135A true CH487135A (de)	1970-03-15

Family

ID=25703092

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1516961A CH487135A (de)	1961-07-14	1961-12-29	Verfahren zur Herstellung von 19-Nor-Steroiden

Country Status (6)

Country	Link
AT (1)	AT249882B (da)
CH (1)	CH487135A (da)
DK (2)	DK118076B (da)
ES (1)	ES279208A1 (da)
NL (1)	NL6600218A (da)
SE (2)	SE306734B (da)

1961
- 1961-12-29 CH CH1516961A patent/CH487135A/de not_active IP Right Cessation
1962
- 1962-07-13 ES ES279208A patent/ES279208A1/es not_active Expired
- 1962-07-13 DK DK315162A patent/DK118076B/da unknown
- 1962-07-13 SE SE788962A patent/SE306734B/xx unknown
- 1962-07-13 AT AT568362A patent/AT249882B/de active
- 1962-07-13 DK DK391963A patent/DK109958C/da active
1966
- 1966-01-07 NL NL6600218A patent/NL6600218A/xx unknown
- 1966-11-01 SE SE14961/66A patent/SE323957B/xx unknown

Also Published As

Publication number	Publication date
SE323957B (da)	1970-05-19
NL6600218A (da)	1966-03-25
ES279208A1 (es)	1963-04-16
AT249882B (de)	1966-10-10
DK109958C (da)	1968-08-12
DK118076B (da)	1970-07-06
SE306734B (da)	1968-12-09

Legal Events

Date	Code	Title	Description
1978-08-31	PL	Patent ceased

Publication	Publication Date	Title
CH487135A (de)	1970-03-15	Verfahren zur Herstellung von 19-Nor-Steroiden
DE1793633B2 (de)	1973-03-08	Verfahren zur herstellung von gona4(5),9(10)-dien-3-onen
DE1012299B (de)	1957-07-18	Verfahren zur Herstellung eines Pregnan-3-ol-20-on-3-aethers oder -esters
DE1131213B (de)	1962-06-14	Verfahren zur Herstellung neuer Pregnanverbindungen
DE2433178A1 (de)	1975-01-30	In 21-stellung alkylierte steroide der pregnanreihe
AT238381B (de)	1965-02-10	Verfahren zur Herstellung 18-oxygenierter Steroide
DE957661C (de)	1957-01-17	Verfahren zur Herstellung von 17-Oxy-20-keto-21acyl-oxypregnanen
AT241703B (de)	1965-08-10	Verfahren zur Herstellung von 4-Methyl-3-oxo-5α-steroiden
DE1493344B1 (de)	1970-07-09	Verfahren zur Herstellung von 16 alpha-Chlor- oder -Fluor-17(20)-pregnen-21-saeureestern und daraus erhaeltlichen 16 alpha-Chlor- oder -Fluor-17 alpha-hydroxy-20-keto-21-acyloxyverbindungen der Pregnanreihe
DE2148631B2 (de)	1973-03-22	Verfahren zur herstellung von in der 9(11)- und/oder 16-stellung ungesaettigten steroiden
AT233184B (de)	1964-04-25	Verfahren zur Herstellung von 3-Oxo-Δ<1,4>-steroiden
AT208525B (de)	1960-04-11	Verfahren zur Herstellung von Aldosteron und seinen Derivaten
AT239967B (de)	1965-05-10	Verfahren zur Herstellung von 18,20-Oxidosteroiden
DE1468642C (de)	1971-10-28	Gona-4(5), 9(10>dien-3-one
CH364254A (de)	1962-09-15	Verfahren zur Herstellung von Steroiden
CH380116A (de)	1964-07-31	Verfahren zur Herstellung neuer Cyclosteroide
DE1300941B (de)	1969-08-14	Verfahren zur Herstellung von delta 4-3-Ketonandrosten- oder -pregnenverbindungen
DE1166775B (de)	1964-04-02	Verfahren zur Herstellung von 19-nor-í¸-3-Ketosteroiden
DE1543992A1 (de)	1970-02-05	Verfahren zur Herstellung von Equilin
DE1147942B (de)	1963-05-02	Verfahren zur Herstellung von 16ª‡, 17ª‡-(1-Alkoxy)-alkylidendioxysteroiden
CH376909A (de)	1964-04-30	Verfahren zur Herstellung von 6a,6a-Dichlor-6,7-methylen- und 6a,6a-Dibrom-6,7-methylenverbindungen von 4-3-Ketosteroiden
CH561229A5 (en)	1975-04-30	Substd. tetra-enes and trienes - oestrogenic and antilipaemic
DE1081888B (de)	1960-05-19	Verfahren zur Herstellung von ?-3-Keto-9 ª‡-halogensteroiden
DE1145170B (de)	1963-03-14	Verfahren zur Herstellung von 9,11-Oxidosteroiden der Androstan- und Pregnanreihe
CH424769A (de)	1966-11-30	Verfahren zur Herstellung von 11-Oxo-19-hydroxy-steroiden