CH557336A - Verfahren zur herstellung von 3-hydroxyimino-steroiden. - Google Patents

Verfahren zur herstellung von 3-hydroxyimino-steroiden.

Info

Publication number: CH557336A
Authority: CH; Switzerland
Prior art keywords: oxime; acetoxy; androst; prepared; ethynyl
Prior art date: 1966-07-06

Application number

CH950967A

Other languages

German (de)

English (en)

Inventor

A P Shroff

Original Assignee

Ortho Pharma Corp

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.)

1966-07-06

Filing date

1967-07-05

Publication date

1974-12-31

1967-07-05 Application filed by Ortho Pharma Corp filed Critical Ortho Pharma Corp

1974-12-31 Publication of CH557336A publication Critical patent/CH557336A/de

Links

239000003433 contraceptive agent Substances 0.000 title description 3
230000002254 contraceptive effect Effects 0.000 title description 3
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 title 2
229960003604 testosterone Drugs 0.000 title 1
150000002923 oximes Chemical class 0.000 claims abstract description 21
150000002443 hydroxylamines Chemical class 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 30
238000000034 method Methods 0.000 claims description 26
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
-1 acyl radical Chemical class 0.000 claims description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000003544 oxime group Chemical group 0.000 claims description 2
239000001632 sodium acetate Substances 0.000 claims description 2
235000017281 sodium acetate Nutrition 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 9
229960004719 nandrolone Drugs 0.000 abstract description 3
125000002252 acyl group Chemical group 0.000 abstract 2
230000001113 coital effect Effects 0.000 abstract 1
NPAGDVCDWIYMMC-IZPLOLCNSA-N nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 abstract 1
150000003431 steroids Chemical class 0.000 abstract 1
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
241000700159 Rattus Species 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
230000037396 body weight Effects 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000007858 starting material Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
230000035935 pregnancy Effects 0.000 description 3
241001465754 Metazoa Species 0.000 description 2
239000003651 drinking water Substances 0.000 description 2
235000020188 drinking water Nutrition 0.000 description 2
238000002513 implantation Methods 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 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
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
RPOYGOULCHMVBB-ADDDGJNWSA-N Pipercide Chemical compound CC(C)CNC(=O)\C=C\C=C\CCCC\C=C\C1=CC=C2OCOC2=C1 RPOYGOULCHMVBB-ADDDGJNWSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
XEHVFKKSDRMODV-UHFFFAOYSA-N ethynyl Chemical compound C#[C] XEHVFKKSDRMODV-UHFFFAOYSA-N 0.000 description 1
230000004720 fertilization Effects 0.000 description 1
PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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 1
230000016087 ovulation Effects 0.000 description 1
239000003408 postcoitus contraceptive agent Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000003449 preventive 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
239000012056 semi-solid material Substances 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
210000001215 vagina Anatomy 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 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
- 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
- A61K31/568—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 positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- A61K31/569—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 positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone substituted in position 17 alpha, e.g. ethisterone
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Organic Chemistry (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)

CH950967A 1966-07-06 1967-07-05 Verfahren zur herstellung von 3-hydroxyimino-steroiden. CH557336A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US56308166A	1966-07-06	1966-07-06
US63530867A	1967-04-20	1967-04-20

Publications (1)

Publication Number	Publication Date
CH557336A true CH557336A (de)	1974-12-31

Family

ID=27073165

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH950967A CH557336A (de)	1966-07-06	1967-07-05	Verfahren zur herstellung von 3-hydroxyimino-steroiden.

Country Status (6)

Country	Link
CH (1)	CH557336A (fr)
DK (1)	DK134691B (fr)
FR (1)	FR321F (fr)
GB (1)	GB1195555A (fr)
SE (1)	SE318561B (fr)
YU (1)	YU33881B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH558346A (de) *	1971-06-17	1975-01-31	Sandoz Ag	Verfahren zur herstellung neuer 3-oximino-17(alpha)-propadienyl-substituierter steroide.

1967
- 1967-06-28 YU YU129067A patent/YU33881B/xx unknown
- 1967-06-29 SE SE974867A patent/SE318561B/xx unknown
- 1967-07-03 FR FR321D patent/FR321F/fr not_active Expired
- 1967-07-05 CH CH950967A patent/CH557336A/de not_active IP Right Cessation
- 1967-07-05 GB GB3094867A patent/GB1195555A/en not_active Expired
- 1967-07-06 DK DK347467A patent/DK134691B/da unknown

Also Published As

Publication number	Publication date
DK134691B (da)	1976-12-27
SE318561B (fr)	1969-12-15
GB1195555A (en)	1970-06-17
YU129067A (en)	1977-12-31
DK134691C (fr)	1977-07-11
YU33881B (en)	1978-06-30
FR321F (fr)	1970-07-27

Legal Events

Date	Code	Title	Description
1986-12-31	PL	Patent ceased

Publication	Publication Date	Title
DE2661002C2 (fr)	1988-03-17
DE1543273C3 (de)	1974-02-21	7 alpha-Methyl-Delta hoch 5(16) -steroide der Oestranreihe und Verfahren zu deren Herstellung
DE2818164A1 (de)	1979-10-31	1,3-dibenzoesaeureester des 17alpha- ethinyl-7 alpha -methyl-1,3,5(10)-oestratrien- 1,3,17 beta -triols, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzungen
DE3741801A1 (de)	1989-06-15	17-methylen-estratriene
DE1290141B (de)	1969-03-06	Verfahren zur Herstellung von in 3-Stellung Sauerstoff enthaltenden 20ª‡-(ª‰-N, N-Dimethylaminoaethyl)-amino-19-nor-delta 1, 3, 5(10)-pregnatrienen bzw. Salzen derselben
US3532689A (en)	1970-10-06	3-oxime and 3-oxime esters of 19-nortestosterone
US3780073A (en)	1973-12-18	3-oximes of 19-nortestosterone esters
DE1298993B (de)	1969-07-10	3-Oxo-8ª‡-17ª‰-hydroxy-17ª‡-aethinyl-oestr-5(10)-en in seiner racemischen und linksdrehenden Form und Verfahren zur Herstellung dieser Verbindungen
DE1468902B1 (de)	1970-04-23	25-Aza-19-nor-1,3,5(10)-cholestatriene und deren therapeutisch vertraegliche Saeureadditionssalze sowie ein Verfahren zur Herstellung dieser Verbindungen
DE1618752C3 (de)	1977-04-07	Oral verabreichbares Mittel mit konzeptionsverhütender Wirksamkeit
DE1618752A1 (de)	1971-02-25	Azasteroide
US3629415A (en)	1971-12-21	Suppression of reproduction with 3-oxime and 3-oxime esters of 19-nortestosterone
DE2348197C3 (de)	1979-08-30	Norethisteron-O-alkyloxime, Verfahren zu ihrer Herstellung sowie ihre Verwendung
DE2059190A1 (de)	1971-08-12	Aryloxime von Ketosteroiden und Verfahren zu ihrer Herstellung
DE2037155A1 (fr)	1971-02-11
DE1620102C3 (de)	1976-08-26	3-Oxime der Androsten- und Gonenreihe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel
CH494218A (de)	1970-07-31	Verfahren zur Herstellung von 3-Hydroxyimino-steroiden
DE60026608T2 (de)	2006-12-28	3-methylen steroid derivate zur behandlung von autoimmunerkrankungen
DE1904586C3 (fr)	1978-07-06
AT224277B (de)	1962-11-12	Verfahren zur Herstellung von neuen 16-Methylen-17α-acetoxy-progesteron-derivaten
DE1618977C (de)	1973-03-01	Nitroostratnene und Verfahren zu deren Herstellung
DE1493032C (de)		Verfahren zur Herstellung von 2 alpha. 3 alpha-Epithiosteroiden
CH493506A (de)	1970-07-15	Verfahren zur Herstellung von neuen Nitroöstratrienen
EP0707593B1 (fr)	1997-12-29	Esters du 14 alpha,15 alpha-methylene- stradiol a action strogene administrables par voie orale
DE1593465C (de)	1971-10-28	3-(2Chloräthoxy> 17alpha-äthinyl-17 beta-hydroxy-Delta hoch 1,3,5(10)-östratrien und Verfahren zu dessen Herstellung