BE844350A - 3-oximes d'esters de d-17a-ethynyl-19-nortestosterone et procede pour les preparer - Google Patents

3-oximes d'esters de d-17a-ethynyl-19-nortestosterone et procede pour les preparer

Info

Publication number: BE844350A
Authority: BE; Belgium
Prior art keywords: emi; formula; radical; compound; fertility
Prior art date: 1975-07-24

Application number

BE169095A

Other languages

English (en)

French (fr)

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.)

1975-07-24

Filing date

1976-07-20

Publication date

1977-01-20

1976-07-20 Application filed filed Critical

1977-01-20 Publication of BE844350A publication Critical patent/BE844350A/fr

Links

238000000034 method Methods 0.000 title claims description 9
229960004719 nandrolone Drugs 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 29
230000035558 fertility Effects 0.000 claims description 13
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 8
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 8
229940011871 estrogen Drugs 0.000 claims description 7
239000000262 estrogen Substances 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
-1 caproyl radical Chemical group 0.000 claims description 6
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
241000124008 Mammalia Species 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
229940088597 hormone Drugs 0.000 claims description 3
239000005556 hormone Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical group OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 claims description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
239000001632 sodium acetate Substances 0.000 claims description 2
235000017281 sodium acetate Nutrition 0.000 claims description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 1
241001465754 Metazoa Species 0.000 description 10
230000000694 effects Effects 0.000 description 8
241000700159 Rattus Species 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
235000013601 eggs Nutrition 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
230000013011 mating Effects 0.000 description 5
230000035935 pregnancy Effects 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000000583 progesterone congener Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
230000002513 anti-ovulatory effect Effects 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000002513 implantation Methods 0.000 description 3
238000001802 infusion Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
150000003431 steroids Chemical class 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
239000012267 brine Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
230000002380 cytological effect Effects 0.000 description 2
230000016087 ovulation Effects 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
239000008159 sesame oil Substances 0.000 description 2
235000011803 sesame oil Nutrition 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
238000012360 testing method Methods 0.000 description 2
208000032843 Hemorrhage Diseases 0.000 description 1
MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical compound C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
208000034158 bleeding Diseases 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940035811 conjugated estrogen Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
230000027046 diestrus Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
QTTMOCOWZLSYSV-QWAPEVOJSA-M equilin sodium sulfate Chemical compound [Na+].[O-]S(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4C3=CCC2=C1 QTTMOCOWZLSYSV-QWAPEVOJSA-M 0.000 description 1
229960005309 estradiol Drugs 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
208000007106 menorrhagia Diseases 0.000 description 1
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
RAFYDKXYXRZODZ-UHFFFAOYSA-N octanoyl octanoate Chemical compound CCCCCCCC(=O)OC(=O)CCCCCCC RAFYDKXYXRZODZ-UHFFFAOYSA-N 0.000 description 1
210000003101 oviduct Anatomy 0.000 description 1
230000027758 ovulation cycle Effects 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
210000004994 reproductive system Anatomy 0.000 description 1
210000000582 semen Anatomy 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000001665 trituration Methods 0.000 description 1
210000001215 vagina Anatomy 0.000 description 1
238000011121 vaginal smear Methods 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
- C07J41/0016—Oximes

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Chemistry (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

BE169095A 1975-07-24 1976-07-20 3-oximes d'esters de d-17a-ethynyl-19-nortestosterone et procede pour les preparer BE844350A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US59896675A	1975-07-24	1975-07-24

Publications (1)

Publication Number	Publication Date
BE844350A true BE844350A (fr)	1977-01-20

Family

ID=24397652

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE169095A BE844350A (fr)	1975-07-24	1976-07-20	3-oximes d'esters de d-17a-ethynyl-19-nortestosterone et procede pour les preparer

Country Status (6)

Country	Link
BE (1)	BE844350A (cs)
CS (1)	CS189781B2 (cs)
HU (1)	HU175021B (cs)
PL (1)	PL101800B1 (cs)
SU (1)	SU608481A3 (cs)
ZA (1)	ZA764448B (cs)

1976
- 1976-07-08 PL PL1976191020A patent/PL101800B1/pl unknown
- 1976-07-20 BE BE169095A patent/BE844350A/fr not_active IP Right Cessation
- 1976-07-22 HU HU76OO233A patent/HU175021B/hu unknown
- 1976-07-23 CS CS764880A patent/CS189781B2/cs unknown
- 1976-07-23 ZA ZA00764448A patent/ZA764448B/xx unknown
- 1976-07-23 SU SU762385902A patent/SU608481A3/ru active

Also Published As

Publication number	Publication date
SU608481A3 (ru)	1978-05-25
HU175021B (hu)	1980-04-28
CS189781B2 (en)	1979-04-30
ZA764448B (en)	1978-03-29
PL101800B1 (pl)	1979-02-28

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Legal Events

Date

Code

Title

Description

1993-06-25

CCPA

Application for a supplementary protection certificate

Free format text: 093C0109

1993-12-28

CCPV

Grant of a supplementary protection certificate

Free format text: 093C0109, EXPIRES 20010720

1996-01-01

RE20

Patent expired

Owner name: ORTHO PHARMACEUTICAL CORP.

Effective date: 19960720