DK174183B1 - Fremgangsmåde til fremstilling af 1alfa-3beta, 24-dihydroxy-delta5-steroider - Google Patents

Fremgangsmåde til fremstilling af 1alfa-3beta, 24-dihydroxy-delta5-steroider Download PDF

Info

Publication number: DK174183B1
Authority: DK; Denmark
Prior art keywords: formula; reaction; epoxy; alpha; reaction mixture
Prior art date: 1988-07-04

Application number

DK198903166A

Other languages

Danish (da)

English (en)

Other versions

DK316689D0 (da

DK316689A (da

Inventor

Tatuo Yarino

Takao Fujii

Original Assignee

Teijin Ltd

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.)

1988-07-04

Filing date

1989-06-26

Publication date

2002-08-19

1989-06-26 Application filed by Teijin Ltd filed Critical Teijin Ltd

1989-06-26 Publication of DK316689D0 publication Critical patent/DK316689D0/da

1990-01-05 Publication of DK316689A publication Critical patent/DK316689A/da

2002-08-19 Application granted granted Critical

2002-08-19 Publication of DK174183B1 publication Critical patent/DK174183B1/da

Links

238000000034 method Methods 0.000 title claims abstract description 28
238000002360 preparation method Methods 0.000 title description 13
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 38
238000006243 chemical reaction Methods 0.000 claims abstract description 16
229910021529 ammonia Inorganic materials 0.000 claims abstract description 15
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 10
150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
150000001412 amines Chemical class 0.000 claims abstract description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
239000002904 solvent Substances 0.000 claims abstract description 5
238000004519 manufacturing process Methods 0.000 claims abstract description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 15
-1 alkali metal alkoxide Chemical class 0.000 claims description 15
150000001340 alkali metals Chemical class 0.000 claims description 12
150000003431 steroids Chemical class 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000003138 primary alcohols Chemical class 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 abstract 2
239000002184 metal Substances 0.000 abstract 2
239000013067 intermediate product Substances 0.000 abstract 1
239000011541 reaction mixture Substances 0.000 description 28
229910052744 lithium Inorganic materials 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
230000000052 comparative effect Effects 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
238000001704 evaporation Methods 0.000 description 7
239000012299 nitrogen atmosphere Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
239000000539 dimer Substances 0.000 description 5
AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 5
150000004703 alkoxides Chemical class 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000003973 alkyl amines Chemical group 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
QAXCUKPIFMXXIG-HPVZSNEMSA-N (6r)-6-[(8s,9s,10r,13r,14s,17r)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylheptane-1,1,1-triol Chemical compound C1C=C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCCC(C)C(O)(O)O)C)[C@@]1(C)CC2 QAXCUKPIFMXXIG-HPVZSNEMSA-N 0.000 description 2
ZKNAEXQLQMRALD-AEJDUDARSA-N 1α, 2α-epoxycholesta-4,6-dien-3,24- dione Chemical compound C1=CC2=CC(=O)[C@@H]3O[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCC(=O)C(C)C)[C@@]1(C)CC2 ZKNAEXQLQMRALD-AEJDUDARSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229960005084 calcitriol Drugs 0.000 description 2
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
150000002576 ketones Chemical group 0.000 description 2
LTRVAZKHJRYLRJ-UHFFFAOYSA-N lithium;butan-1-olate Chemical compound [Li+].CCCC[O-] LTRVAZKHJRYLRJ-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
241000282320 Panthera leo Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KWIWNNXEBIRRJT-UHFFFAOYSA-N [NH4+].[Cl-].[Li] Chemical compound [NH4+].[Cl-].[Li] KWIWNNXEBIRRJT-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
TZQYSYAJCZUIFL-UHFFFAOYSA-N azane;furan-2,3,4,5-tetrol Chemical compound N.OC=1OC(O)=C(O)C=1O TZQYSYAJCZUIFL-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012467 final product Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000002367 halogens Chemical group 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
239000012442 inert solvent Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
MXIRPJHGXWFUAE-UHFFFAOYSA-N lithium;propan-1-olate Chemical compound [Li+].CCC[O-] MXIRPJHGXWFUAE-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
AWDMDDKZURRKFG-UHFFFAOYSA-N potassium;propan-1-olate Chemical compound [K+].CCC[O-] AWDMDDKZURRKFG-UHFFFAOYSA-N 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005039 triarylmethyl group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
150000003704 vitamin D3 derivatives Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
- 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)

DK198903166A 1988-07-04 1989-06-26 Fremgangsmåde til fremstilling af 1alfa-3beta, 24-dihydroxy-delta5-steroider DK174183B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP16514888		1988-07-04
JP63165148A JPH0749435B2 (ja)	1988-07-04	1988-07-04	１α，３β，２４−トリヒドロキシ−△▲上５▼−ステロイド類の製造方法

Publications (3)

Publication Number	Publication Date
DK316689D0 DK316689D0 (da)	1989-06-26
DK316689A DK316689A (da)	1990-01-05
DK174183B1 true DK174183B1 (da)	2002-08-19

Family

ID=15806795

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK198903166A DK174183B1 (da)	1988-07-04	1989-06-26	Fremgangsmåde til fremstilling af 1alfa-3beta, 24-dihydroxy-delta5-steroider

Country Status (8)

Country	Link
US (1)	US5117015A (de)
EP (1)	EP0349869B1 (de)
JP (1)	JPH0749435B2 (de)
AT (1)	ATE127126T1 (de)
DE (1)	DE68924010T2 (de)
DK (1)	DK174183B1 (de)
ES (1)	ES2076175T3 (de)
PT (1)	PT91011B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2001506656A (ja)	1996-12-20	2001-05-22	ノボノルディスクアクティーゼルスカブ	減数分裂調節化合物
JP2007517877A (ja) *	2004-01-15	2007-07-05	ワーナー・チルコット・カンパニー・インコーポレーテッド	エストラジオールのジ−ステロイド型プロドラッグ
WO2005070950A1 (en) *	2004-01-15	2005-08-04	Warner Chilcott Company, Inc.	Di-steroidal prodrugs of ethinyl estradiol
CN101218245B (zh) *	2005-07-12	2011-08-17	沃纳奇尔科特有限责任公司	炔雌醇的3-酯前药
CA2610481A1 (en) *	2005-07-12	2007-01-18	Warner Chilcott Company, Inc.	3-ester prodrugs of estradiol

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1081424A (fr) *	1953-05-26	1954-12-20	Ile De Rech S Tech Soc Civ	Procédé de préparation de dérivés du cholestane et des cholestènes di-oxygénés en position 3 et 24
US4670190A (en) *	1973-01-10	1987-06-02	Hesse Robert H	1-α-hydroxy vitamin D compounds and process for preparing same
US3901928A (en) *	1973-01-10	1975-08-26	Robert Henry Hesse	1' ,3' -dihydroxy steroid-5-enes method of preparing same and their use for preparing 1' -hydroxy-25-hydrogen vitamin d compounds
DE2400189A1 (de) *	1974-01-03	1975-07-17	Basf Ag	Verfahren zur herstellung von 1 alphahydroxy-cholesterinen
US3907843A (en) *	1974-06-14	1975-09-23	Wisconsin Alumni Res Found	1{60 -Hydroxyergocalciferol and processes for preparing same
US4022891A (en) *	1974-06-18	1977-05-10	Teijin Limited	Novel 1α,24-dihydroxycholecalciferol compositions, novel precursors thereof, and processes for preparing them
IL45897A (en) *	1974-10-22	1978-12-17	Yeda Res & Dev	Process for the preparation of 1 hydroxy-provitamin d3
LU80545A1 (de) *	1978-11-17	1980-06-05	Hoffmann La Roche	Verfahren zur herstellung von 1a,3s-dihydroxy->5-steroiden
JPS5854160A (ja) *	1981-09-28	1983-03-31	旭化成株式会社	床下収納庫
JPH0681758B2 (ja) *	1988-04-28	1994-10-19	帝人株式会社	１α，３β−ジヒドロキシ−△▲上５▼−ステロイドの製造方法

1988
- 1988-07-04 JP JP63165148A patent/JPH0749435B2/ja not_active Expired - Lifetime
1989
- 1989-06-24 DE DE68924010T patent/DE68924010T2/de not_active Expired - Lifetime
- 1989-06-24 ES ES89111561T patent/ES2076175T3/es not_active Expired - Lifetime
- 1989-06-24 AT AT89111561T patent/ATE127126T1/de not_active IP Right Cessation
- 1989-06-24 EP EP89111561A patent/EP0349869B1/de not_active Expired - Lifetime
- 1989-06-26 DK DK198903166A patent/DK174183B1/da not_active IP Right Cessation
- 1989-06-29 PT PT91011A patent/PT91011B/pt not_active IP Right Cessation
1991
- 1991-04-30 US US07/696,255 patent/US5117015A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
PT91011B (pt)	1995-01-31
DE68924010T2 (de)	1996-01-25
DK316689D0 (da)	1989-06-26
JPH0215093A (ja)	1990-01-18
ES2076175T3 (es)	1995-11-01
EP0349869B1 (de)	1995-08-30
PT91011A (pt)	1990-02-08
US5117015A (en)	1992-05-26
DK316689A (da)	1990-01-05
EP0349869A2 (de)	1990-01-10
JPH0749435B2 (ja)	1995-05-31
DE68924010D1 (de)	1995-10-05
EP0349869A3 (en)	1990-04-25
ATE127126T1 (de)	1995-09-15

Legal Events

Date	Code	Title	Description
2009-07-13	PUP	Patent expired

Publication	Publication Date	Title
CA1184920A (en)	1985-04-02	Process for the preparation of 1-hydroxylated vitamin d compounds
DK174183B1 (da)	2002-08-19	Fremgangsmåde til fremstilling af 1alfa-3beta, 24-dihydroxy-delta5-steroider
COXON et al.	1961	Simplified preparation of sophorose (2-O-β-D-glucopyranosyl-D-glucose)
GB799269A (en)	1958-08-06	Production of intermediates for the synthesis of reserpine and related compounds
US4294766A (en)	1981-10-13	Preparation of pure potassium ribonate and ribonolactone
US2451740A (en)	1948-10-19	Process for the manufacture of an aldehyde
US3153077A (en)	1964-10-13	Process for preparing organic bis-thiosulfates
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