CH628907A5 - Process for the preparation of 24,25-dihydroxycholesterol derivatives - Google Patents

Process for the preparation of 24,25-dihydroxycholesterol derivatives Download PDF

Info

Publication number: CH628907A5
Authority: CH; Switzerland
Prior art keywords: hydroxy; methoxy; mixture; cyclo; acid
Prior art date: 1975-10-10

Application number

CH1224676A

Other languages

German (de)

English (en)

Inventor

John Joseph Partridge

Milan Radoje Uskokovic

Original Assignee

Hoffmann La Roche

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.)

1975-10-10

Filing date

1976-09-28

Publication date

1982-03-31

1975-10-10 Priority claimed from US05/621,319 external-priority patent/US3994878A/en

1975-10-20 Priority claimed from US05/623,859 external-priority patent/US4038272A/en

1976-09-28 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1982-03-31 Publication of CH628907A5 publication Critical patent/CH628907A5/de

Links

238000000034 method Methods 0.000 title description 14
238000002360 preparation method Methods 0.000 title description 7
OFNJCHBCBBSWHW-SUSFDCQQSA-N (6R)-6-[(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptane-2,3-diol Chemical class C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCC(O)C(C)(C)O)C)[C@@]1(C)CC2 OFNJCHBCBBSWHW-SUSFDCQQSA-N 0.000 title description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 20
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
125000004423 acyloxy group Chemical group 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 15
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
150000001875 compounds Chemical class 0.000 description 12
-1 methoxy, ethoxy, isopropyl Chemical group 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
230000008018 melting Effects 0.000 description 9
238000002844 melting Methods 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
229960001701 chloroform Drugs 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000002609 medium Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000001632 sodium acetate Substances 0.000 description 5
235000017281 sodium acetate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000008707 rearrangement Effects 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000007858 starting material Substances 0.000 description 4
150000003431 steroids Chemical group 0.000 description 4
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
OFNJCHBCBBSWHW-XVYZBDJZSA-N (24S,25)-dihydroxycholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CC[C@H](O)C(C)(C)O)C)[C@@]1(C)CC2 OFNJCHBCBBSWHW-XVYZBDJZSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000003797 solvolysis reaction Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
INBGSXNNRGWLJU-ZHHJOTBYSA-N 25-hydroxycholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCCC(C)(C)O)C)[C@@]1(C)CC2 INBGSXNNRGWLJU-ZHHJOTBYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
230000000707 stereoselective effect Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 1
FCKJYANJHNLEEP-XRWYNYHCSA-N (24R)-24,25-dihydroxycalciol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CC[C@@H](O)C(C)(C)O)C)=C\C=C1\C[C@@H](O)CCC1=C FCKJYANJHNLEEP-XRWYNYHCSA-N 0.000 description 1
239000004046 24R,25-dihydroxy-cholecalciferol Substances 0.000 description 1
125000003836 4-phenylbutoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
USURYVONRGTVIF-AMQKJUDNSA-N Dihydroxycholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C(O)O)[C@@]1(C)CC2 USURYVONRGTVIF-AMQKJUDNSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 1
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-NKMMMXOESA-N 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
150000001841 cholesterols Chemical class 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000011981 lindlar catalyst Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000002071 phenylalkoxy group Chemical group 0.000 description 1
238000006303 photolysis reaction Methods 0.000 description 1
230000015843 photosynthesis, light reaction Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
229940032091 stigmasterol Drugs 0.000 description 1
BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 description 1
235000016831 stigmasterol Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH1224676A 1975-10-10 1976-09-28 Process for the preparation of 24,25-dihydroxycholesterol derivatives CH628907A5 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/621,319 US3994878A (en)	1975-10-10	1975-10-10	Syntheses of 24R,25- and 24S,25-dihydroxycholesterol and alkanoyl derivatives thereof
US05/623,859 US4038272A (en)	1975-10-20	1975-10-20	Stereospecific syntheses of 24r,25- and 24s,25-dihydroxycholesterol and alkanoyl derivatives thereof

Publications (1)

Publication Number	Publication Date
CH628907A5 true CH628907A5 (en)	1982-03-31

Family

ID=27088923

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1224676A CH628907A5 (en)	1975-10-10	1976-09-28	Process for the preparation of 24,25-dihydroxycholesterol derivatives

Country Status (8)

Country	Link
JP (1)	JPS5246061A (2)
AT (1)	AT355236B (2)
CH (1)	CH628907A5 (2)
DE (1)	DE2645527A1 (2)
FR (2)	FR2407941A1 (2)
GB (5)	GB1564807A (2)
IT (1)	IT1068692B (2)
NL (1)	NL7611155A (2)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH644873A5 (de) *	1980-02-12	1984-08-31	Hoffmann La Roche	Verfahren zur herstellung von cholesterinderivaten.
CA2848212C (en)	2011-09-08	2022-03-29	Sage Therapeutics, Inc.	Neuroactive steroids, compositions, and uses thereof
PT2968369T (pt)	2013-03-13	2018-12-05	Sage Therapeutics Inc	Esteroides neuroativos e métodos para o seu uso
HUE071964T2 (hu)	2015-07-06	2025-10-28	Sage Therapeutics Inc	Oxiszterolok és alkalmazási eljárásaik
CA2991311C (en) *	2015-07-06	2025-05-06	Sage Therapeutics, Inc.	OXYSTEROLS AND THEIR METHODS OF USE
EP3828194B1 (en)	2015-07-06	2025-04-16	Sage Therapeutics, Inc.	Oxysterols and methods of use thereof
SMT202200300T1 (it)	2016-04-01	2022-09-14	Sage Therapeutics Inc	Ossisteroli e relativi metodi d'uso
WO2017193046A1 (en)	2016-05-06	2017-11-09	Sage Therapeutics, Inc.	Oxysterols and methods of use thereof
ES2884071T3 (es)	2016-07-07	2021-12-10	Sage Therapeutics Inc	24-hidroxiesteroles sustituidos en 11 para el tratamiento de afecciones relacionadas con NMDA
ES2935057T3 (es)	2016-09-30	2023-03-01	Sage Therapeutics Inc	C7 oxisteroles sustituidos y estos compuestos para su uso como moduladores de la NMDA
RU2019115113A (ru)	2016-10-18	2020-11-24	Сейдж Терапьютикс, Инк.	Оксистеролы и способы их применения

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL7402846A (2) *	1973-03-02	1974-09-04
US3822254A (en) *	1973-05-21	1974-07-02	Hoffmann La Roche	Synthesis of 25-hydroxycholesterol

1976
- 1976-09-28 CH CH1224676A patent/CH628907A5/de not_active IP Right Cessation
- 1976-10-08 DE DE19762645527 patent/DE2645527A1/de not_active Ceased
- 1976-10-08 GB GB2313977A patent/GB1564807A/en not_active Expired
- 1976-10-08 AT AT751376A patent/AT355236B/de not_active IP Right Cessation
- 1976-10-08 JP JP12050076A patent/JPS5246061A/ja active Pending
- 1976-10-08 NL NL7611155A patent/NL7611155A/xx not_active Application Discontinuation
- 1976-10-08 GB GB2314177A patent/GB1564809A/en not_active Expired
- 1976-10-08 IT IT2816476A patent/IT1068692B/it active
- 1976-10-08 GB GB4193876A patent/GB1564806A/en not_active Expired
- 1976-10-08 GB GB2314277A patent/GB1564810A/en not_active Expired
- 1976-10-08 GB GB2314077A patent/GB1564808A/en not_active Expired
- 1976-10-11 FR FR7630450A patent/FR2407941A1/fr active Granted
1977
- 1977-04-22 FR FR7712223A patent/FR2351998A1/fr active Granted

Also Published As

Publication number	Publication date
DE2645527A1 (de)	1977-04-21
FR2351998B1 (2)	1980-04-25
FR2407941A1 (fr)	1979-06-01
FR2351998A1 (fr)	1977-12-16
GB1564810A (en)	1980-04-16
NL7611155A (nl)	1977-04-13
GB1564809A (en)	1980-04-16
GB1564808A (en)	1980-04-16
FR2407941B1 (2)	1980-05-16
JPS5246061A (en)	1977-04-12
GB1564806A (en)	1980-04-16
GB1564807A (en)	1980-04-16
IT1068692B (it)	1985-03-21
AT355236B (de)	1980-02-25
ATA751376A (de)	1979-07-15

Legal Events

Date	Code	Title	Description
1987-05-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
Partridge et al.	1974	Vitamin D3 Metabolites I. Synthesis of 25‐hydroxycholesterol
DE2463203C2 (2)	1987-06-04
CH617442A5 (2)	1980-05-30
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EP0004621A2 (de)	1979-10-17	Verfahren zur mehrstufigen Synthese von Zeaxanthin und Alloxanthin über Cyclohexanon- und Cyclohexanolderivate; Cyclohexanon- und Cyclohexanolderivate
DE1958600A1 (de)	1970-07-09	Neue Isoxazolderivate und deren Herstellung
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CH620227A5 (2)	1980-11-14
EP0285548B1 (de)	1990-09-05	Verfahren zur Herstellung von 17alpha-Ethinyl-17beta-hydroxy-18-methyl-4,15-estradien-3-on und die neuen Zwischenprodukte für dieses Verfahren
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CH626096A5 (2)	1981-10-30
Huffman et al.	1970	Synthetic approaches to steroidal alkaloids II. Preparation and reactions of 12-oxo-dinorcholanic acids
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DE2222544C3 (de)	1976-10-07	Neue 16,17-Secoöstradi- und triene Verfahren zu ihrer Herstellung sowie diese enthaltendes Mittel
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AT276644B (de)	1969-11-25	Verfahren zur Herstellung von neuen desA-Steroiden
CH498819A (de)	1970-11-15	Verfahren zur Herstellung von Steroidketonen mit 17- oder 17a-Halogenalkinylgruppen
US3753980A (en)	1973-08-21	Process for the preparation of 14-anhydrobufaline
AT272541B (de)	1969-07-10	Verfahren zur Herstellung von Benzindenen
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AT208525B (de)	1960-04-11	Verfahren zur Herstellung von Aldosteron und seinen Derivaten
DE2710062A1 (de)	1977-09-15	Neue cholesterinderivate
AT361642B (de)	1981-03-25	Verfahren zur herstellung von neuen cholesterinderivaten
CH320945A (de)	1957-04-15	Verfahren zur Herstellung bromierter Pregnanderivate