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 therebyInfo
- Publication number
- IL42154A IL42154A IL42154A IL4215473A IL42154A IL 42154 A IL42154 A IL 42154A IL 42154 A IL42154 A IL 42154A IL 4215473 A IL4215473 A IL 4215473A IL 42154 A IL42154 A IL 42154A
- Authority
- IL
- Israel
- Prior art keywords
- stereoisomeric
- hydrogen
- fluorine
- acid
- component
- Prior art date
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)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE7206645A SE378110B (forum.php) | 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 (forum.php) |
JP (1) | JPS547794B2 (forum.php) |
BE (1) | BE799728A (forum.php) |
CA (1) | CA1003402A (forum.php) |
CY (1) | CY1012A (forum.php) |
DE (1) | DE2323216C3 (forum.php) |
DK (1) | DK133249C (forum.php) |
FI (1) | FI50711C (forum.php) |
FR (1) | FR2185406B1 (forum.php) |
GB (1) | GB1428416A (forum.php) |
HK (1) | HK49079A (forum.php) |
IL (1) | IL42154A (forum.php) |
KE (1) | KE2969A (forum.php) |
NL (1) | NL175917C (forum.php) |
SE (1) | SE378110B (forum.php) |
SU (1) | SU468408A3 (forum.php) |
ZA (1) | ZA732956B (forum.php) |
Families Citing this family (71)
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NL188581C (nl) * | 1974-07-15 | 1992-08-03 | Akzo Nv | Werkwijze voor het bereiden van 11beta-hydroxy-18-alkylestraanverbindingen. |
ZA763131B (en) * | 1975-05-27 | 1978-01-25 | Syntex Inc | Use of flunisolide to treat respiratory diseases |
SE8008524L (sv) * | 1980-12-04 | 1982-06-05 | Draco Ab | 4-pregnen-derivat, ett forfarande for deras framstellning, beredning och metod for behandling av inflammatoriska tillstand |
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 |
SE8604059D0 (sv) * | 1986-09-25 | 1986-09-25 | Astra Pharma Prod | A method of controlling the epimeric distribution in the preparation of 16,17-acetals of pregnane derivatives |
GR1001529B (el) * | 1990-09-07 | 1994-03-31 | Elmuquimica Farm Sl | Μέ?οδος για την λήψη νέων 21-εστέρων της 16-17-ακετάλης της πρ να-1,4-διενο-3,20-διόνης. |
SE9100341D0 (sv) * | 1991-02-04 | 1991-02-04 | Astra Ab | Novel steroids |
DK0678097T3 (da) * | 1993-01-08 | 2000-02-07 | Astra Ab | Hidtil ukendte colon- eller ileumspecifikke steroidderivater |
DE19635498A1 (de) * | 1996-09-03 | 1998-03-26 | Byk Gulden Lomberg Chem Fab | Verfahren zur Epimerenanreicherung |
IT1291288B1 (it) | 1997-04-30 | 1999-01-07 | Farmabios Srl | Processo per la preparazione di 16,17 acetali di derivati pregnanici con controllo della distribuzione epimerica al c-22. |
US6266556B1 (en) | 1998-04-27 | 2001-07-24 | Beth Israel Deaconess Medical Center, Inc. | Method and apparatus for recording an electroencephalogram during transcranial magnetic stimulation |
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WO2008035316A2 (en) * | 2006-09-22 | 2008-03-27 | Ranbaxy Laboratories Limited | Phosphodiesterase inhibitors |
US20110218176A1 (en) | 2006-11-01 | 2011-09-08 | Barbara Brooke Jennings-Spring | Compounds, methods, and treatments for abnormal signaling pathways for prenatal and postnatal development |
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US8071623B2 (en) | 2007-01-10 | 2011-12-06 | Instituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa | Amide substituted indazoles as poly(ADP-ribose)polymerase(PARP) inhibitors |
EP1958947A1 (en) | 2007-02-15 | 2008-08-20 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type 4 |
EP2124943A1 (en) * | 2007-03-14 | 2009-12-02 | Ranbaxy Laboratories Limited | Pyrazolo [3, 4-b]pyridine derivatives as phosphodiesterase inhibitors |
CN103497185A (zh) | 2007-03-14 | 2014-01-08 | 兰贝克赛实验室有限公司 | 用作磷酸二酯酶抑制剂的吡唑并(3,4-b)吡啶衍生物 |
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ITMI20080645A1 (it) | 2008-04-11 | 2009-10-12 | Ind Chimica Srl | Procedimento per la preparazione di budesonide |
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US8603521B2 (en) | 2009-04-17 | 2013-12-10 | Pharmacyclics, Inc. | Formulations of histone deacetylase inhibitor and uses thereof |
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JP2013518909A (ja) | 2010-02-08 | 2013-05-23 | キナゲン,インク. | アロステリックキナーゼ阻害が関係する治療方法および組成物 |
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WO2012143874A1 (en) | 2011-04-21 | 2012-10-26 | Piramal Healthcare Limited | A process for the preparation of morpholino sulfonyl indole derivatives |
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WO2013063214A1 (en) | 2011-10-27 | 2013-05-02 | Merck Sharp & Dohme Corp. | Novel compounds that are erk inhibitors |
EP3919620A1 (en) | 2012-05-02 | 2021-12-08 | Sirna Therapeutics, Inc. | Short interfering nucleic acid (sina) compositions |
NZ704799A (en) | 2012-08-24 | 2018-06-29 | Univ Texas | Heterocyclic modulators of hif activity for treatment of disease |
US9155747B2 (en) * | 2012-09-13 | 2015-10-13 | Chiesi Farmaceutici S.P.A. | Isoxazolidine derivatives |
WO2014052563A2 (en) | 2012-09-28 | 2014-04-03 | Merck Sharp & Dohme Corp. | Novel compounds that are erk inhibitors |
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Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 GB GB2219573A patent/GB1428416A/en not_active Expired
- 1973-05-09 CY CY1012A patent/CY1012A/xx unknown
- 1973-05-09 DE DE2323216A patent/DE2323216C3/de not_active Expired
- 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 NL NLAANVRAGE7306979,A patent/NL175917C/xx 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 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 |
---|---|
DE2323216A1 (de) | 1973-11-29 |
JPS547794B2 (forum.php) | 1979-04-10 |
IL42154A0 (en) | 1973-07-30 |
BE799728A (fr) | 1973-09-17 |
NL175917B (nl) | 1984-08-16 |
SU468408A3 (ru) | 1975-04-25 |
SE378110B (forum.php) | 1975-08-18 |
HK49079A (en) | 1979-07-27 |
DE2323216C3 (de) | 1978-06-22 |
AU5525273A (en) | 1974-11-07 |
NL175917C (nl) | 1985-01-16 |
FR2185406A1 (forum.php) | 1974-01-04 |
GB1428416A (en) | 1976-03-17 |
CY1012A (en) | 1979-11-23 |
US3928326A (en) | 1975-12-23 |
FI50711B (forum.php) | 1976-03-01 |
DK133249C (da) | 1976-09-13 |
DK133249B (da) | 1976-04-12 |
CA1003402A (en) | 1977-01-11 |
NL7306979A (forum.php) | 1973-11-21 |
JPS4941379A (forum.php) | 1974-04-18 |
KE2969A (en) | 1979-07-20 |
FR2185406B1 (forum.php) | 1976-12-31 |
FI50711C (fi) | 1976-06-10 |
DE2323216B2 (de) | 1977-11-03 |
ZA732956B (en) | 1974-04-24 |
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