IL31732A - 6,6-difluoro-17alpha-ethynyl-estr-4-ene-3beta,17beta-diol diacetate - Google Patents

6,6-difluoro-17alpha-ethynyl-estr-4-ene-3beta,17beta-diol diacetate

Info

Publication number: IL31732A
Authority: IL; Israel
Prior art keywords: solution; ethynyl; 17alpha; estr; 17beta
Prior art date: 1968-04-11

Application number

IL31732A

Other languages

English (en)

Other versions

IL31732A0 (en

Original Assignee

Du Pont

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.)

1968-04-11

Filing date

1969-03-04

Publication date

1973-06-29

1969-03-04 Application filed by Du Pont filed Critical Du Pont

1969-05-28 Publication of IL31732A0 publication Critical patent/IL31732A0/xx

1973-06-29 Publication of IL31732A publication Critical patent/IL31732A/en

Links

UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
150000001875 compounds Chemical class 0.000 description 9
239000000047 product Substances 0.000 description 9
239000000203 mixture Substances 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
230000001072 progestational effect Effects 0.000 description 6
238000003756 stirring Methods 0.000 description 6
230000007935 neutral effect Effects 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000010828 elution Methods 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
229940053934 norethindrone Drugs 0.000 description 4
VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000000538 analytical sample Substances 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000011369 resultant mixture Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
GNLJBJNONOOOQC-UHFFFAOYSA-N $l^{3}-carbane;magnesium Chemical compound [Mg]C GNLJBJNONOOOQC-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 description 1
BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
UYIFTLBWAOGQBI-BZDYCCQFSA-N Benzhormovarine Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1CC[C@@H]4O)C)CC2=CC=3OC(=O)C1=CC=CC=C1 UYIFTLBWAOGQBI-BZDYCCQFSA-N 0.000 description 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229960001701 chloroform Drugs 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229950002007 estradiol benzoate Drugs 0.000 description 1
GRXPVLPQNMUNNX-MHJRRCNVSA-N estrane Chemical compound C1CC2CCCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 GRXPVLPQNMUNNX-MHJRRCNVSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
230000035558 fertility Effects 0.000 description 1
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 description 1
238000003304 gavage Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
-1 lithium aluminum butoxy hydride Chemical compound 0.000 description 1
LROBJRRFCPYLIT-UHFFFAOYSA-M magnesium;ethyne;bromide Chemical compound [Mg+2].[Br-].[C-]#C LROBJRRFCPYLIT-UHFFFAOYSA-M 0.000 description 1
238000000034 method Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 description 1
ZEIYBPGWHWECHV-UHFFFAOYSA-N nitrosyl fluoride Chemical compound FN=O ZEIYBPGWHWECHV-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001817 pituitary effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
229960003387 progesterone Drugs 0.000 description 1
239000000186 progesterone Substances 0.000 description 1
239000000583 progesterone congener Substances 0.000 description 1
239000000523 sample Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical class [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000010902 straw Substances 0.000 description 1
QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 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
- A61K31/565—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
- A61K31/567—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 substituted in position 17 alpha, e.g. mestranol, norethandrolone
- 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
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- 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)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Epidemiology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL31732A 1968-04-11 1969-03-04 6,6-difluoro-17alpha-ethynyl-estr-4-ene-3beta,17beta-diol diacetate IL31732A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US72049368A	1968-04-11	1968-04-11

Publications (2)

Publication Number	Publication Date
IL31732A0 IL31732A0 (en)	1969-05-28
IL31732A true IL31732A (en)	1973-06-29

Family

ID=24894202

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL31732A IL31732A (en)	1968-04-11	1969-03-04	6,6-difluoro-17alpha-ethynyl-estr-4-ene-3beta,17beta-diol diacetate

Country Status (12)

Country	Link
US (1)	US3511861A (de)
AT (2)	AT305501B (de)
BE (1)	BE731318A (de)
DE (1)	DE1918182A1 (de)
DK (1)	DK130834B (de)
ES (1)	ES365895A1 (de)
FI (1)	FI46620C (de)
FR (1)	FR2007436A1 (de)
GB (1)	GB1269241A (de)
IL (1)	IL31732A (de)
NL (1)	NL6905530A (de)
SE (1)	SE361473B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE758013A (fr) *	1969-11-17	1971-04-01	Du Pont	Esters superieurs de 6,6-difluoro steroides servant d'agents progestinogenes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3219673A (en) *	1963-07-25	1965-11-23	Du Pont	6,6-difluoro-3-keto-delta4 steroids and their preparation

1968
- 1968-04-11 US US720493A patent/US3511861A/en not_active Expired - Lifetime
1969
- 1969-03-04 IL IL31732A patent/IL31732A/en unknown
- 1969-04-01 FI FI690955A patent/FI46620C/fi active
- 1969-04-08 SE SE04911/69A patent/SE361473B/xx unknown
- 1969-04-10 DE DE19691918182 patent/DE1918182A1/de active Pending
- 1969-04-10 FR FR6911039A patent/FR2007436A1/fr not_active Withdrawn
- 1969-04-10 ES ES365895A patent/ES365895A1/es not_active Expired
- 1969-04-10 DK DK199169AA patent/DK130834B/da unknown
- 1969-04-10 NL NL6905530A patent/NL6905530A/xx unknown
- 1969-04-10 GB GB08583/69A patent/GB1269241A/en not_active Expired
- 1969-04-10 BE BE731318D patent/BE731318A/xx unknown
- 1969-04-11 AT AT578770A patent/AT305501B/de not_active IP Right Cessation
- 1969-04-11 AT AT356269A patent/AT298688B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
ES365895A1 (es)	1971-03-16
DE1918182A1 (de)	1969-10-23
FR2007436A1 (de)	1970-01-09
IL31732A0 (en)	1969-05-28
DK130834B (da)	1975-04-21
NL6905530A (de)	1969-10-14
SE361473B (de)	1973-11-05
DK130834C (de)	1975-09-22
FI46620B (de)	1973-01-31
FI46620C (fi)	1973-05-08
BE731318A (de)	1969-10-10
AT298688B (de)	1972-05-25
AT305501B (de)	1973-02-26
GB1269241A (en)	1972-04-06
US3511861A (en)	1970-05-12

Publication	Publication Date	Title
Baran	1967	The synthesis, stereochemistry, and biology of 16-hetero and 17-oxa-D-homo steroids
IL31732A (en)	1973-06-29	6,6-difluoro-17alpha-ethynyl-estr-4-ene-3beta,17beta-diol diacetate
Starnes	1964	Concurrent Carbon-to-Oxygen Rearrangement, Cyclization, and Decarboxylation in the Reaction of 3, 3, 3-Triarylpropionic Acids with Lead Tetraacetate
Sakakibara et al.	1976	Phase transfer catalyzed reactions. II. Reactions of methyl 3-deoxy-3-nitro-. beta.-D-hexopyranosides with active methylene compounds
US2760966A (en)	1956-08-28	Compounds for synthesizing steroids
Huffman et al.	1970	Synthetic approaches to steroidal alkaloids II. Preparation and reactions of 12-oxo-dinorcholanic acids
US2704768A (en)	1955-03-22	17-(beta-hydroxyethylidene)-13-methyl-1, 2, 3, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17-tetradecahydro-15h-cyclopenta [a] phenanthren-3-one and esters thereof
US3291814A (en)	1966-12-13	Novel synthesis of 19-norsteroids and novel 19-norsteroid intermediates
US3450720A (en)	1969-06-17	3-difluoromethylene steroids
US3248392A (en)	1966-04-26	Steroid lactones and process
US2125772A (en)	1938-08-02	Sexual hormone compositions and process of producing same
Mitsuhashi et al.	1960	Studies on the Constituents of Asclepiadaceae Plants. II. On the Struture of Cynanchogenin from Cynanchum caudatum Max.
US3598811A (en)	1971-08-10	Derivatives of 4alpha,8,14-trimethyl-18-nor-5alpha,8alpha,9beta,13alpha,14beta,17alpha-pregnane
US3975412A (en)	1976-08-17	Mono-acylation of 17-hydroxy-3-alkoxygona-2,5-(10)dienes
DE917971C (de)	1954-09-16	Verfahren zur Herstellung von Steroidlactamen
DE903333C (de)	1954-02-04	Verfahren zur Herstellung von Steroid-20, 21-enolacetaten
US3192266A (en)	1965-06-29	17alpha-ethynyl-17beta-hydroxy-a-nor-b-homoestranes and their process of preparation
US3686226A (en)	1972-08-22	17-oxygenated-2-oxaestra-1(10),4-dien-3-ones and compounds corresponding
DE2154649C3 (de)	1974-03-14	Verfahren zur Herstellung von 19-Acetoxy-Delta hoch 4 /Delta hoch 5 -Dehydrocardenoliden
US3381004A (en)	1968-04-30	Nitrogen-containing pregnenes and method of preparing the same
DE1443123C (de)	1971-08-26	Verfahren zur Herstellung von 13 Alkyl gona 1,3,5(10) tnenen
US3180865A (en)	1965-04-27	18-20 lactone of 20beta-hydroxy-5beta-pregnane-3, 11-dione-18-oic acid
US4108851A (en)	1978-08-22	3β,17-Dihydroxy-5α,17α-pregn-20-ene-21-carboxylic acid γ-lactone and esters thereof
PL71511B1 (de)	1974-06-29
US3384646A (en)	1968-05-21	16-hydroxy-17-oxy-16-xoymethylandrost-4-en-3-ones