IL28465A - 6-halo-21-fluoro-1alpha,2alpha-methylene-17alpha-hydroxy-pregna-4,6-diene-3,20-dione 17 esters - Google Patents

6-halo-21-fluoro-1alpha,2alpha-methylene-17alpha-hydroxy-pregna-4,6-diene-3,20-dione 17 esters

Info

Publication number: IL28465A
Authority: IL; Israel
Prior art keywords: water; acid; general formula; methylene; dione
Prior art date: 1966-08-11

Application number

IL2846567A

Other languages

English (en)

Original Assignee

Schering 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.)

1966-08-11

Filing date

1967-08-07

Publication date

1972-01-27

1967-08-07 Application filed by Schering Ag filed Critical Schering Ag

1972-01-27 Publication of IL28465A publication Critical patent/IL28465A/en

Links

150000002148 esters Chemical class 0.000 title claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 8
238000000034 method Methods 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 4
239000013543 active substance Substances 0.000 claims description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
229910052782 aluminium Inorganic materials 0.000 claims description 3
239000004411 aluminium Substances 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 2
230000008030 elimination Effects 0.000 claims description 2
238000003379 elimination reaction Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
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 9
239000011734 sodium Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 4
239000000292 calcium oxide Substances 0.000 description 4
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000005457 ice water Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
206010001928 Amenorrhoea Diseases 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
239000001828 Gelatine Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
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 2
238000009835 boiling Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
230000003152 gestagenic effect Effects 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
229910052757 nitrogen Inorganic materials 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
210000002307 prostate Anatomy 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
210000001625 seminal vesicle Anatomy 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
201000010653 vesiculitis Diseases 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241001502381 Budorcas taxicolor Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 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
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
241000700159 Rattus Species 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000011790 ferrous sulphate Substances 0.000 description 1
235000003891 ferrous sulphate Nutrition 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
-1 methylene compound Chemical class 0.000 description 1
BDRTVPCFKSUHCJ-UHFFFAOYSA-N molecular hydrogen;potassium Chemical compound [K].[H][H] BDRTVPCFKSUHCJ-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000009877 rendering Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007858 starting material Substances 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
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
229960001712 testosterone propionate Drugs 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
238000005303 weighing Methods 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
- A61K31/573—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 substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone

Landscapes

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

IL2846567A 1966-08-11 1967-08-07 6-halo-21-fluoro-1alpha,2alpha-methylene-17alpha-hydroxy-pregna-4,6-diene-3,20-dione 17 esters IL28465A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DESC039385		1966-08-11
DESC040710		1967-05-13

Publications (1)

Publication Number	Publication Date
IL28465A true IL28465A (en)	1972-01-27

Family

ID=25993399

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL2846567A IL28465A (en)	1966-08-11	1967-08-07	6-halo-21-fluoro-1alpha,2alpha-methylene-17alpha-hydroxy-pregna-4,6-diene-3,20-dione 17 esters

Country Status (12)

Country	Link
BE (1)	BE702583A (de)
CH (1)	CH515227A (de)
DE (2)	DE1593515C3 (de)
DK (1)	DK117227B (de)
ES (1)	ES343859A1 (de)
FI (1)	FI45172C (de)
FR (1)	FR1561096A (de)
GB (1)	GB1196476A (de)
IL (1)	IL28465A (de)
NL (1)	NL152267B (de)
NO (1)	NO126525B (de)
SE (1)	SE320067B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19908762A1 (de) *	1999-02-18	2000-08-31	Jenapharm Gmbh	Verwendung von Dienogest in hoher Dosierung

1966
- 1966-08-11 DE DE19661593515 patent/DE1593515C3/de not_active Expired
1967
- 1967-05-13 DE DE19671643021 patent/DE1643021A1/de active Pending
- 1967-06-28 SE SE9525/67*A patent/SE320067B/xx unknown
- 1967-07-11 FI FI191467A patent/FI45172C/fi active
- 1967-08-01 GB GB3531267A patent/GB1196476A/en not_active Expired
- 1967-08-02 DK DK394967A patent/DK117227B/da unknown
- 1967-08-04 CH CH1100967A patent/CH515227A/de not_active IP Right Cessation
- 1967-08-05 ES ES343859A patent/ES343859A1/es not_active Expired
- 1967-08-07 IL IL2846567A patent/IL28465A/en unknown
- 1967-08-10 NL NL6711020A patent/NL152267B/xx unknown
- 1967-08-10 FR FR1561096D patent/FR1561096A/fr not_active Expired
- 1967-08-10 NO NO16932167A patent/NO126525B/no unknown
- 1967-08-11 BE BE702583D patent/BE702583A/xx unknown

Also Published As

Publication number	Publication date
FI45172B (de)	1971-12-31
CH515227A (de)	1971-11-15
DK117227B (da)	1970-03-31
NO126525B (de)	1973-02-19
SE320067B (de)	1970-02-02
ES343859A1 (es)	1968-10-01
FI45172C (fi)	1972-04-10
NL6711020A (de)	1968-02-12
FR1561096A (de)	1969-03-28
BE702583A (de)	1968-02-12
DE1593515C3 (de)	1975-08-14
DE1593515A1 (de)	1970-08-13
DE1643021A1 (de)	1971-03-11
GB1196476A (en)	1970-06-24
NL152267B (nl)	1977-02-15
DE1593515B2 (de)	1975-01-09

Publication	Publication Date	Title
US2183589A (en)	1939-12-19	Derivatives of compounds of the
US3318926A (en)	1967-05-09	7alpha-methyl-16alpha-hydroxy-estrones
US2656366A (en)	1953-10-20	Water-soluble esters of cortisone and related compounds
US3682983A (en)	1972-08-08	Preparation of {66 {11 {11 -17 ethinyl steroids
NO132558B (de)	1975-08-18
US3254074A (en)	1966-05-31	Spiroxenones
IL28465A (en)	1972-01-27	6-halo-21-fluoro-1alpha,2alpha-methylene-17alpha-hydroxy-pregna-4,6-diene-3,20-dione 17 esters
US3787396A (en)	1974-01-22	17-hydroxy-7-(lower alkoxy)carbonyl-3-oxo-17alpha-pregn-4-ene-21-carboxylic acid ypsilon-lactones and congeners
US2509248A (en)	1950-05-30	Process for producing delta9, 11-3(alpha)-hydroxy-17-ketoetiocholene
IE832337L (en)	1984-04-05	Pregnane compounds
US2906758A (en)	1959-09-29	3-(hydroxyalkyl)-ethers of estradiol
US3159622A (en)	1964-12-01	17 alpha-(2-carboxyethyl)-17 belta-hydroxy-6-nitroandrost-4-en-3-one gamma-lactones
US2908694A (en)	1959-10-13	7-substituted thio-4-androstenes
US3483235A (en)	1969-12-09	New oestratrienes and process for their manufacture
US3296075A (en)	1967-01-03	17alpha-acyloxy-16-methylene-pregn-4-ene-3, 20-diones, pharmaceutical preparations containing same, and intermediate thereto
US3872076A (en)	1975-03-18	16-Diazoketones of the androstane, pregnane, estrane, and 19-norpregnane series
US3103510A (en)	1963-09-10	Cx c cx o oej
US3115440A (en)	1963-12-24	3-enolethers of free and esterified 17alpha-ethynyl-19-nortestosterone
US3128291A (en)	1964-04-07	New hemiacetals and hemicaetal esters of the androstane series and a method for their production
US3641009A (en)	1972-02-08	Cardio-active oxido-bufadienolides
US3354151A (en)	1967-11-21	Method of preparing 1beta-methyl-2, 3alpha-methylene-steroids
US3012941A (en)	1961-12-12	delta 4-9alpha-halogeno-3beta, 11beta, 17beta-trihydroxy-11alpha-methyl-androstenes and esters thereof
US2235661A (en)	1941-03-18	Hydrohaodes of pseudotropine
US3504003A (en)	1970-03-31	A-nor-b-homosteroids
US3475537A (en)	1969-10-28	Steroid esters