CH551959A - Verfahren zur herstellung neuer oestrogen hochwirksamer steroide. - Google Patents

Verfahren zur herstellung neuer oestrogen hochwirksamer steroide.

Info

Publication number: CH551959A
Authority: CH; Switzerland
Prior art keywords: methyl; oestratriene; dihydroxy; hydroxyl group; cyclopentanol
Prior art date: 1970-04-24

Application number

CH621970A

Other languages

German (de)

English (en)

Original Assignee

Ciba Geigy Ag

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.)

1970-04-24

Filing date

1970-04-24

Publication date

1974-07-31

1970-04-24 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1970-04-24 Priority to CH1870372A priority Critical patent/CH536295A/de

1970-04-24 Priority to CH1870272A priority patent/CH536290A/de

1970-04-24 Priority to CH621970A priority patent/CH551959A/de

1971-04-19 Priority to IL36654A priority patent/IL36654A/xx

1971-04-19 Priority to CA110656A priority patent/CA931944A/en

1971-04-20 Priority to DE19712118995 priority patent/DE2118995A1/de

1971-04-20 Priority to ZA712525A priority patent/ZA712525B/xx

1971-04-20 Priority to IE491/71A priority patent/IE35147B1/xx

1971-04-21 Priority to US00136170A priority patent/US3804866A/en

1971-04-22 Priority to FR7114322A priority patent/FR2092082B1/fr

1971-04-22 Priority to PL1971147684A priority patent/PL81612B1/pl

1971-04-22 Priority to HUCI1106A priority patent/HU162762B/hu

1971-04-23 Priority to CS298671A priority patent/CS157118B2/cs

1971-04-23 Priority to AT351171A priority patent/AT311567B/de

1971-04-23 Priority to CS173873*1A priority patent/CS157119B2/cs

1971-04-23 Priority to AT273172A priority patent/AT312826B/de

1971-04-23 Priority to AT273072A priority patent/AT312825B/de

1971-04-23 Priority to NL7105578A priority patent/NL7105578A/xx

1971-04-23 Priority to SE7105303A priority patent/SE373577B/xx

1971-04-23 Priority to SU1649123A priority patent/SU450404A3/ru

1971-04-23 Priority to SU1815023A priority patent/SU434651A3/ru

1971-04-23 Priority to FI711131A priority patent/FI48729C/fi

1971-04-23 Priority to CS173973*1A priority patent/CS157120B2/cs

1971-04-23 Priority to SU1816332A priority patent/SU447884A3/ru

1971-04-23 Priority to BE766184A priority patent/BE766184A/xx

1971-12-27 Priority to AR239826A priority patent/AR192730A1/es

1971-12-27 Priority to AR239837A priority patent/AR192731A1/es

1971-12-27 Priority to AR239825A priority patent/AR192605A1/es

1972-08-18 Priority to DK412172AA priority patent/DK128533B/da

1974-07-31 Publication of CH551959A publication Critical patent/CH551959A/de

Links

XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims abstract description 5
230000001076 estrogenic effect Effects 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 22
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
238000000034 method Methods 0.000 claims description 8
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 5
150000003254 radicals Chemical class 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 3
BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
238000006266 etherification reaction Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
150000003431 steroids Chemical class 0.000 claims 1
230000001836 utereotrophic effect Effects 0.000 abstract description 4
238000002513 implantation Methods 0.000 abstract description 3
230000002401 inhibitory effect Effects 0.000 abstract description 3
210000001109 blastomere Anatomy 0.000 abstract description 2
230000035558 fertility Effects 0.000 abstract description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 abstract 1
238000003776 cleavage reaction Methods 0.000 abstract 1
229910000489 osmium tetroxide Inorganic materials 0.000 abstract 1
230000007017 scission Effects 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
-1 acyloxy radicals Chemical class 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 5
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
241000700159 Rattus Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
HLCRYAZDZCJZFG-BDXSIMOUSA-N (8s,9s,13s,14s)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene Chemical compound C1CC2=CC=CC=C2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 HLCRYAZDZCJZFG-BDXSIMOUSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229940092714 benzenesulfonic acid Drugs 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-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
239000012043 crude product Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000007788 liquid Substances 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
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 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
238000002211 ultraviolet spectrum Methods 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
230000027326 copulation Effects 0.000 description 1
BOTLEXFFFSMRLQ-UHFFFAOYSA-N cyclopentyloxycyclopentane Chemical compound C1CCCC1OC1CCCC1 BOTLEXFFFSMRLQ-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000000262 estrogen Substances 0.000 description 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000003780 keratinization Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
230000000624 ovulatory effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229920001515 polyalkylene glycol Polymers 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
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000002966 varnish Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent 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
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/168—Steroids
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/184—Hormones
- 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
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Husbandry (AREA)
Zoology (AREA)
Engineering & Computer Science (AREA)
Food Science & Technology (AREA)
Endocrinology (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Steroid Compounds (AREA)

CH621970A 1970-04-24 1970-04-24 Verfahren zur herstellung neuer oestrogen hochwirksamer steroide. CH551959A (de)

Priority Applications (29)

Application Number	Priority Date	Filing Date	Title
CH1870372A CH536295A (de)	1970-04-24	1970-04-24	Verfahren zur Herstellung eines neuen östrogen hochwirksamen Steroids
CH1870272A CH536290A (de)	1970-04-24	1970-04-24	Verfahren zur Herstellung eines neuen östrogen hochwirksamen Steroids
CH621970A CH551959A (de)	1970-04-24	1970-04-24	Verfahren zur herstellung neuer oestrogen hochwirksamer steroide.
IL36654A IL36654A (en)	1970-04-24	1971-04-19	3-cyclopentyl ethers of 7alpha-methyl-3,16alpha,17(alpha and beta)-trihydroxy-delta 1,3,5(10)-estratriene,their manufacture and estrogenic pharmaceutical compositions containing them
CA110656A CA931944A (en)	1970-04-24	1971-04-19	Oestrogenically highly active steroids and process for their manufacture
DE19712118995 DE2118995A1 (de)	1970-04-24	1971-04-20	Neue oestrogen hochwirksame Steroide und ein Verfahren zu deren Herstellung
ZA712525A ZA712525B (en)	1970-04-24	1971-04-20	New oestrogenically highly active steroids and a process for their manufacture
IE491/71A IE35147B1 (en)	1970-04-24	1971-04-20	New trihydroxy-oestratriene derivatives and a process for their manufacture
US00136170A US3804866A (en)	1970-04-24	1971-04-21	Oestrogenically highly active steroids and a process for their manufacture
FR7114322A FR2092082B1 (cs)	1970-04-24	1971-04-22
PL1971147684A PL81612B1 (cs)	1970-04-24	1971-04-22
HUCI1106A HU162762B (cs)	1970-04-24	1971-04-22
CS298671A CS157118B2 (cs)	1970-04-24	1971-04-23
AT351171A AT311567B (de)	1970-04-24	1971-04-23	Verfahren zur Herstellung von neuen Steroiden
CS173873*1A CS157119B2 (cs)	1970-04-24	1971-04-23
AT273172A AT312826B (de)	1970-04-24	1971-04-23	Verfahren zur Herstellung von neuen Steroiden
AT273072A AT312825B (de)	1970-04-24	1971-04-23	Verfahren zur Herstellung von neuen Steroiden
NL7105578A NL7105578A (cs)	1970-04-24	1971-04-23
SE7105303A SE373577B (sv)	1970-04-24	1971-04-23	Forfarande for framstellning av 3-cyklopentyleter av 7 -metyl- 3, 16 17-trihydroxi-1,3,5(10)-ostratrien samt 16, 17-diacetat derav
SU1649123A SU450404A3 (ru)	1970-04-24	1971-04-23	СПОСОБ ПОЛУЧЕНИЯ 3-ЦИКЛОПЕНТИЛОВОГО ЭФИРА7а-МЕТИЛ-3,16а, П-ТРИОКСИ-А^з.^сю) ЭСТРАТРИЕПА ИЛИ ЕГО 16,17-ДИАЦЕТАТОВ
SU1815023A SU434651A3 (ru)	1970-04-24	1971-04-23	СПОСОБ ПОЛУЧЕНИЯ3-ЦИКЛОПЕНТИЛОКСИ-7а-МЕТИЛ-3, 16а, 17сс--ТРИОКСИЭСТРАТРИЕНА
FI711131A FI48729C (fi)	1970-04-24	1971-04-23	Menetelmä estrogeenisesti korkeatehoisen 3-syklopetyylioksi-7alfa-mety yli16alfa,17-dihydroksi- 1,3,5(10)-estratrieenin valmistamiseksi.
CS173973*1A CS157120B2 (cs)	1970-04-24	1971-04-23
SU1816332A SU447884A3 (ru)	1970-04-24	1971-04-23	Способ получения 3-циклопентилокси-7 -метил-3,16 ,17-триоксиэстратриенов
BE766184A BE766184A (fr)	1970-04-24	1971-04-23	Nouveaux steroides a haute activite oestrogene et procede pour leur preparation
AR239826A AR192730A1 (es)	1970-04-24	1971-12-27	Procedimiento para la preparacion de 3-ciclopentileter de 7a-metil-3,16a,17-trihidroxi-delta1,3,5(10)-estratrienos
AR239837A AR192731A1 (es)	1970-04-24	1971-12-27	Procedimiento para la preparacion de 3-ciclopentileper de 7a-metil-3,16a,17-trihidroxi-delta1,3,5(10)-estratrienos
AR239825A AR192605A1 (es)	1970-04-24	1971-12-27	Procedimiento para la preparacion de 3-ciclopentil-eter de 7alpha-metil-3,16alpha,17-trihidroxi-delta-estratrienos
DK412172AA DK128533B (da)	1970-04-24	1972-08-18	Analogifremgangsmåde til fremstilling af 3-cyclopentylether af 7α-methyl-3, 16α,17-trihydroxy-Δ<1,3,5(10)>-estratriener.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH621970A CH551959A (de)	1970-04-24	1970-04-24	Verfahren zur herstellung neuer oestrogen hochwirksamer steroide.

Publications (1)

Publication Number	Publication Date
CH551959A true CH551959A (de)	1974-07-31

Family

ID=4306158

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH621970A CH551959A (de)	1970-04-24	1970-04-24	Verfahren zur herstellung neuer oestrogen hochwirksamer steroide.
CH1870372A CH536295A (de)	1970-04-24	1970-04-24	Verfahren zur Herstellung eines neuen östrogen hochwirksamen Steroids
CH1870272A CH536290A (de)	1970-04-24	1970-04-24	Verfahren zur Herstellung eines neuen östrogen hochwirksamen Steroids

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH1870372A CH536295A (de)	1970-04-24	1970-04-24	Verfahren zur Herstellung eines neuen östrogen hochwirksamen Steroids
CH1870272A CH536290A (de)	1970-04-24	1970-04-24	Verfahren zur Herstellung eines neuen östrogen hochwirksamen Steroids

Country Status (5)

Country	Link
AT (1)	AT312826B (cs)
CH (3)	CH551959A (cs)
CS (1)	CS157120B2 (cs)
SU (1)	SU434651A3 (cs)
ZA (1)	ZA712525B (cs)

1970
- 1970-04-24 CH CH621970A patent/CH551959A/de not_active IP Right Cessation
- 1970-04-24 CH CH1870372A patent/CH536295A/de not_active IP Right Cessation
- 1970-04-24 CH CH1870272A patent/CH536290A/de not_active IP Right Cessation
1971
- 1971-04-20 ZA ZA712525A patent/ZA712525B/xx unknown
- 1971-04-23 CS CS173973*1A patent/CS157120B2/cs unknown
- 1971-04-23 SU SU1815023A patent/SU434651A3/ru active
- 1971-04-23 AT AT273172A patent/AT312826B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
CH536290A (de)	1973-04-30
AT312826B (de)	1974-01-25
CH536295A (de)	1973-04-30
CS157120B2 (cs)	1974-08-23
SU434651A3 (ru)	1974-06-30
ZA712525B (en)	1972-01-26

Legal Events

Date	Code	Title	Description
1978-12-15	PL	Patent ceased

Publication	Publication Date	Title
CH628641A5 (de)	1982-03-15	Verfahren zur herstellung neuer androstadien-17beta-carbonsaeuren, ihrer ester und salze.
DE1568308B2 (de)	1976-09-09	Verfahren zur herstellung von delta hoch 4,9,11-trienen der 19-nor- androstanreihe, 17-oxygenierte 3-oxo- 7 alpha-methyl-delta hoch 4,9,11-19 nor- androstatriene und diese enthaltende pharmazeutische praeparate sowie 3-oxo-7 alpha -methyl-delta hoch 5 (10), 9 (11) -19-nor- androstadiene
CH551959A (de)	1974-07-31	Verfahren zur herstellung neuer oestrogen hochwirksamer steroide.
US2332486A (en)	1943-10-19	Acyl compounds of polycyclic alcohols with germinal gland hormone characteristics and a method for producing the same
DE2118995A1 (de)	1971-11-04	Neue oestrogen hochwirksame Steroide und ein Verfahren zu deren Herstellung
CH522622A (de)	1972-06-30	Verfahren zur Herstellung eines neuen 6a-Methyl-19-nor-progesterons
DE2100319C3 (de)	1974-10-31	Neue Östranverbindungen, ihre Herstellung und sie enthaltende Arzneimittel
US3818075A (en)	1974-06-18	3{13 oxo{13 a{13 nor{13 b{13 homo{13 oestra{13 5(10),6{13 dienes
AT263226B (de)	1968-07-10	Verfahren zur Herstellung des neuen 7α-Methyl-17α-äthinyl-östradiols oder seines 3-Methyläthers
DE1768416C3 (de)	1977-09-01	4-ChIor-7 a-methyl-4-androstenolone, Verfahren zu deren Herstellung sowie diese enthaltende Arzneimittel
DE1468302C3 (de)	1977-02-10	6-Chk>r-4,6-pregnadlen-3 beta, 17 alpha-dlol-20-on-diacetat sowie Verfahren zu dessen Herstellung und dieses enthaltende pharmazeutische Zubereitungen
DE2651364A1 (de)	1977-05-12	Neue d-homosteroide
DE1957473A1 (de)	1971-05-27	16-Methylsteroide und Verfahren zu ihrer Herstellung
DE765847C (de)	1956-03-15	Verfahren zur Darstellung von Cyclopentanopolyhydrophenanthrenketolen und deren Ester
CH536296A (de)	1973-04-30	Verfahren zur Herstellung eines neuen östrogen hochwirksamen Steroids
DE2007464A1 (de)	1970-09-10	Ein neues Oestratriol und ein Verfahren zu dessen Herstellung
CH505809A (de)	1971-04-15	Verfahren zur Herstellung 1(10)-5-oxo-5,10-Seco-steroiden
CH531496A (de)	1972-12-15	Verfahren zur Herstellung von 18-Methylensteroiden
DE2118996A1 (de)	1971-11-11	Ein neues, oestrogen hochwirksames Steroid und ein Verfahren zu dessen Herstellung
DE1668444A1 (de)	1971-07-01	AEther der Pregnanreihe und Verfahren zu ihrer Herstellung
CH563411A5 (en)	1975-06-30	2 3-epithiosteroids androgenic anti-oestrogenic
DE1618960A1 (de)	1971-04-29	Neue Steroide und Verfahren zu ihrer Herstellung
CH534139A (de)	1973-02-28	Verfahren zur Herstellung von neuen 2-Halogen-18-methyl-1-androstenen
DE2204147A1 (de)	1972-08-17	Verfahren zur Herstellung neuer Steroidepoxide der 19-Nor-pregnanreihe
DE2118997A1 (de)	1971-11-11	Ein neues, oestrogen hochwirksames Steroid und ein Verfahren zu dessen Herstellung