IL42154A - Process for the separation of stereoisomeric mixtures of 16a,17a-alkylidenedioxy-pregnane derivatives into their components and components obtained thereby - Google Patents

Process for the separation of stereoisomeric mixtures of 16a,17a-alkylidenedioxy-pregnane derivatives into their components and components obtained thereby

Info

Publication number: IL42154A
Authority: IL; Israel
Prior art keywords: stereoisomeric; hydrogen; fluorine; acid; component
Prior art date: 1972-05-19

Application number

IL42154A

Other languages

English (en)

Other versions

IL42154A0 (en

Original Assignee

Bofors Ab

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.)

1972-05-19

Filing date

1973-05-01

Publication date

1976-12-31

1973-05-01 Application filed by Bofors Ab filed Critical Bofors Ab

1973-07-30 Publication of IL42154A0 publication Critical patent/IL42154A0/xx

1976-12-31 Publication of IL42154A publication Critical patent/IL42154A/en

Links

238000000034 method Methods 0.000 title claims abstract 11
239000000203 mixture Substances 0.000 title claims abstract 7
238000000926 separation method Methods 0.000 title 1
238000002523 gelfiltration Methods 0.000 claims abstract 10
230000014759 maintenance of location Effects 0.000 claims abstract 4
150000003431 steroids Chemical class 0.000 claims abstract 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 9
229910052731 fluorine Inorganic materials 0.000 claims 9
239000011737 fluorine Substances 0.000 claims 9
229910052739 hydrogen Inorganic materials 0.000 claims 6
239000001257 hydrogen Substances 0.000 claims 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 claims 4
125000000217 alkyl group Chemical group 0.000 claims 4
125000004432 carbon atom Chemical group C* 0.000 claims 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
125000001183 hydrocarbyl group Chemical group 0.000 claims 3
229920006395 saturated elastomer Polymers 0.000 claims 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
239000003795 chemical substances by application Substances 0.000 claims 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
229960003512 nicotinic acid Drugs 0.000 claims 2
235000001968 nicotinic acid Nutrition 0.000 claims 2
239000011664 nicotinic acid Substances 0.000 claims 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 2
XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 claims 1
GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
229920005654 Sephadex Polymers 0.000 claims 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims 1
239000002253 acid Substances 0.000 claims 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 1
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims 1
GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
229920001577 copolymer Polymers 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
150000002170 ethers Chemical class 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 claims 1
150000002430 hydrocarbons Chemical class 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims 1
235000019260 propionic acid Nutrition 0.000 claims 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 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
229940005605 valeric acid Drugs 0.000 claims 1
206010061218 Inflammation Diseases 0.000 abstract 1
230000015572 biosynthetic process Effects 0.000 abstract 1
230000004054 inflammatory process Effects 0.000 abstract 1
239000008194 pharmaceutical composition Substances 0.000 abstract 1
238000003786 synthesis reaction Methods 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Rheumatology (AREA)
Chemical Kinetics & Catalysis (AREA)
Pain & Pain Management (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)

IL42154A 1972-05-19 1973-05-01 Process for the separation of stereoisomeric mixtures of 16a,17a-alkylidenedioxy-pregnane derivatives into their components and components obtained thereby IL42154A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE7206645A SE378110B (cs)	1972-05-19	1972-05-19

Publications (2)

Publication Number	Publication Date
IL42154A0 IL42154A0 (en)	1973-07-30
IL42154A true IL42154A (en)	1976-12-31

Family

ID=20269238

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL42154A IL42154A (en)	1972-05-19	1973-05-01	Process for the separation of stereoisomeric mixtures of 16a,17a-alkylidenedioxy-pregnane derivatives into their components and components obtained thereby

Country Status (17)

Country	Link
US (1)	US3928326A (cs)
JP (1)	JPS547794B2 (cs)
BE (1)	BE799728A (cs)
CA (1)	CA1003402A (cs)
CY (1)	CY1012A (cs)
DE (1)	DE2323216C3 (cs)
DK (1)	DK133249C (cs)
FI (1)	FI50711C (cs)
FR (1)	FR2185406B1 (cs)
GB (1)	GB1428416A (cs)
HK (1)	HK49079A (cs)
IL (1)	IL42154A (cs)
KE (1)	KE2969A (cs)
NL (1)	NL175917C (cs)
SE (1)	SE378110B (cs)
SU (1)	SU468408A3 (cs)
ZA (1)	ZA732956B (cs)

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IT1196142B (it) *	1984-06-11	1988-11-10	Sicor Spa	Procedimento per la preparazione di 16,17-acetali di derivati pregnanici e nuovi composti ottenuti
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SE9100341D0 (sv) *	1991-02-04	1991-02-04	Astra Ab	Novel steroids
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US3133940A (en) *	1956-04-10	1964-05-19	Glaxo Group Ltd	Process for the separation of delta-1, 4-3-keto steroid compounds from mixtures thereof with other 3-keto steroids
US3197469A (en) *	1958-08-06	1965-07-27	Pharmaceutical Res Products In	16, 17-acetals and ketals of 6-halo-16, 17-dihydroxy steroids of the pregnane seriesand intermediates therefor
US3048581A (en) *	1960-04-25	1962-08-07	Olin Mathieson	Acetals and ketals of 16, 17-dihydroxy steroids
US3128238A (en) *	1962-09-14	1964-04-07	Lilly Co Eli	delta1-dehydrogenation of steroids by fermentation with actinoplanaceae

1972
- 1972-05-19 SE SE7206645A patent/SE378110B/xx unknown
1973
- 1973-05-01 ZA ZA732956A patent/ZA732956B/xx unknown
- 1973-05-01 IL IL42154A patent/IL42154A/en unknown
- 1973-05-09 DE DE2323216A patent/DE2323216C3/de not_active Expired
- 1973-05-09 GB GB2219573A patent/GB1428416A/en not_active Expired
- 1973-05-09 CY CY1012A patent/CY1012A/xx unknown
- 1973-05-14 US US359913A patent/US3928326A/en not_active Expired - Lifetime
- 1973-05-14 FI FI731543A patent/FI50711C/fi active
- 1973-05-17 DK DK277073A patent/DK133249C/da not_active IP Right Cessation
- 1973-05-18 SU SU1918554A patent/SU468408A3/ru active
- 1973-05-18 BE BE131271A patent/BE799728A/xx not_active IP Right Cessation
- 1973-05-18 NL NLAANVRAGE7306979,A patent/NL175917C/xx not_active IP Right Cessation
- 1973-05-18 FR FR7318126A patent/FR2185406B1/fr not_active Expired
- 1973-05-18 CA CA171,781A patent/CA1003402A/en not_active Expired
- 1973-05-19 JP JP5623473A patent/JPS547794B2/ja not_active Expired
1979
- 1979-06-20 KE KE2969A patent/KE2969A/xx unknown
- 1979-07-19 HK HK490/79A patent/HK49079A/xx unknown

Also Published As

Publication number	Publication date
JPS4941379A (cs)	1974-04-18
NL175917C (nl)	1985-01-16
FI50711B (cs)	1976-03-01
NL7306979A (cs)	1973-11-21
FR2185406B1 (cs)	1976-12-31
GB1428416A (en)	1976-03-17
JPS547794B2 (cs)	1979-04-10
ZA732956B (en)	1974-04-24
CY1012A (en)	1979-11-23
BE799728A (fr)	1973-09-17
DK133249B (da)	1976-04-12
IL42154A0 (en)	1973-07-30
DE2323216B2 (de)	1977-11-03
NL175917B (nl)	1984-08-16
SU468408A3 (ru)	1975-04-25
DE2323216C3 (de)	1978-06-22
KE2969A (en)	1979-07-20
DE2323216A1 (de)	1973-11-29
AU5525273A (en)	1974-11-07
SE378110B (cs)	1975-08-18
CA1003402A (en)	1977-01-11
DK133249C (da)	1976-09-13
US3928326A (en)	1975-12-23
FI50711C (fi)	1976-06-10
FR2185406A1 (cs)	1974-01-04
HK49079A (en)	1979-07-27

Publication	Publication Date	Title
IL42154A (en)	1976-12-31	Process for the separation of stereoisomeric mixtures of 16a,17a-alkylidenedioxy-pregnane derivatives into their components and components obtained thereby
US3929768A (en)	1975-12-30	Steroids, processes for their manufacture and preparations containing same
Horst et al.	1976	Lymphatic absorption and metabolism of orally administered testosterone undecanoate in man
CA1183835A (en)	1985-03-12	4-pregnene-derivatives, a process for their preparation, composition and method for the treatment of inflammatory conditions
Eneroth et al.	1971	Extraction, purification, and chromatographic analysis of bile acids in biological materials
ES8308571A1 (es)	1983-09-16	Procedimiento para preparar complejos de inclusion de esteroides pobremente solubles en agua con -ciclodextrina.
Pasqualini et al.	1962	Identification of 3β, 21-dihydroxy-5-pregnene-20-one disulfate in human urine
HU178088B (en)	1982-03-28	Process for preparing 3,20-dioxo-4,9-dieno-21-hydroxy-steroids
EP0246654A2 (en)	1987-11-25	Use of a sulfated polysaccharide
CS195722B2 (en)	1980-02-29	Process for preparing steriod retinoste
Young et al.	1987	Triterpenoid glycosides from Rosa rugosa
D'Auria et al.	1989	Isolation and structure elucidation of seven new polyhydroxylated sulfated sterols from the ophiuroid Ophiolepis superba
O'Hare et al.	1980	Reversed-and normal-phase high-performance liquid chromatography of 18-hydroxylated steroids and their derivatives: Comparison of selectivity, efficiency and recovery from biological samples
Anderson et al.	1973	Preparation and evaluation of a hydroxycyclohexyl derivative of sephadex LH-20
HU176558B (en)	1981-03-28	Process for preparing new n-enolesters of steroids
GB1495531A (en)	1977-12-21	11beta-alkyl steroids of the estrane series
Smith et al.	1976	Trimethylsilyl group migration during electron impact and chemical ionization mass spectrometry of the trimethylsilyl ethers of 20‐hydroxy‐5α‐pregnan‐3‐ones and 20‐hydroxy‐4‐pregnen‐3‐ones
Pis et al.	2013	Analysis of ecdysteroid conjugates: chromatographic characterization of sulfates, phosphates and glucosides
Monder	1964	A new approach to the characterization of steroids containing the 17α-ketol side chain
Rao	1974	Synthesis of compounds of potential value in the radioimmunoassay of 17α-ethynylestradiol and mestranol
Benn	1963	A Reinvestigation of the Synthesis of 5, 16-Pregnadiene-3β, 20α-diol. The Nuclear Magnetic Resonance Spectra of Some Epimeric 20-Hydroxypregnane Derivatives
Lin et al.	1984	High-performance liquid chromatography of steroidal sapogenins
FANTL et al.	1973	Urinary pregn-5-ene-3α, 16α, 20α-triol in adrenal dysfunction
Heller et al.	1965	The synthesis of some 21-chloro-16α, 17α-acetonides
Heftmann	1979	Behavior of Stereoisomeric Steroids in Liquid Chromatography