NL8103357A - Nieuwe 20-isonitril-17(20) onverzadigde steroiden, werkwijze voor het bereiden daarvan en werkwijze voor het bereiden van 17alfa-hydroxy-20-ketosteroiden daar- uit. - Google Patents

Nieuwe 20-isonitril-17(20) onverzadigde steroiden, werkwijze voor het bereiden daarvan en werkwijze voor het bereiden van 17alfa-hydroxy-20-ketosteroiden daar- uit. Download PDF

Info

Publication number: NL8103357A
Authority: NL; Netherlands
Prior art keywords: formula; compound; alk; group; carbon atoms
Prior art date: 1980-07-15

Application number

NL8103357A

Other languages

English (en)

Dutch (nl)

Original Assignee

Roussel Uclaf

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.)

1980-07-15

Filing date

1981-07-15

Publication date

1982-02-01

1981-07-15 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1982-02-01 Publication of NL8103357A publication Critical patent/NL8103357A/nl

Links

238000000034 method Methods 0.000 title claims description 20
150000003431 steroids Chemical class 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims description 70
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 14
101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
-1 diethyl 1-isocyanoethyl phosphonate Chemical compound 0.000 claims description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
JEAYUBBKDZTAGJ-VPSDZCSPSA-N (8R,9S,10R,13S,14S)-17-(1-isocyanoethylidene)-3-methoxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene Chemical compound [N+](#[C-])C(C)=C1CC[C@H]2[C@@H]3CC=C4C=C(CC[C@]4(C)[C@H]3CC[C@]12C)OC JEAYUBBKDZTAGJ-VPSDZCSPSA-N 0.000 claims description 5
238000011282 treatment Methods 0.000 claims description 5
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
238000006735 epoxidation reaction Methods 0.000 claims description 3
230000036571 hydration Effects 0.000 claims description 3
238000006703 hydration reaction Methods 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
238000007127 saponification reaction Methods 0.000 claims description 3
WSIQEGIPGPEMTC-TXTPUJOMSA-N (8r,9s,10r,13s,14s)-3-methoxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-one Chemical compound C1C[C@@H]2[C@](CCC(OC)=C3)(C)C3=CC[C@H]2[C@@H]2CCC(=O)[C@]21C WSIQEGIPGPEMTC-TXTPUJOMSA-N 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
125000006241 alcohol protecting group Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 2
150000002576 ketones Chemical group 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
101150052147 ALLC gene Proteins 0.000 claims 1
GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
235000019253 formic acid Nutrition 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-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
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
229940106681 chloroacetic acid Drugs 0.000 description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000002609 medium Substances 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
150000004965 peroxy acids Chemical class 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
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 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
KQZSMOGWYFPKCH-UJPCIWJBSA-N (8s,9s,10r,11s,13s,14s,17r)-17-acetyl-11,17-dihydroxy-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)C[C@@H]2O KQZSMOGWYFPKCH-UJPCIWJBSA-N 0.000 description 1
QSSNXCGGHSSHJJ-UHFFFAOYSA-N 1-diethoxyphosphoryl-1-isocyanoethane Chemical compound CCOP(=O)(OCC)C(C)[N+]#[C-] QSSNXCGGHSSHJJ-UHFFFAOYSA-N 0.000 description 1
SQAAQHWGIOAIST-UHFFFAOYSA-N 1-diethoxyphosphorylethanamine Chemical compound CCOP(=O)(C(C)N)OCC SQAAQHWGIOAIST-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
PUKLDDOGISCFCP-JSQCKWNTSA-N 21-Deoxycortisone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2=O PUKLDDOGISCFCP-JSQCKWNTSA-N 0.000 description 1
LCZBQMKVFQNSJR-UJPCIWJBSA-N 21-deoxycortisol Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)C[C@@H]2O LCZBQMKVFQNSJR-UJPCIWJBSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
ORNBQBCIOKFOEO-YQUGOWONSA-N Pregnenolone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC3)C[C@@H](O)CC4)CC2)CC1 ORNBQBCIOKFOEO-YQUGOWONSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
230000022244 formylation Effects 0.000 description 1
238000006170 formylation reaction Methods 0.000 description 1
125000004970 halomethyl group Chemical group 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
QGEBPTGBBRQVPC-UHFFFAOYSA-N n-(1-diethoxyphosphorylethyl)formamide Chemical compound CCOP(=O)(OCC)C(C)NC=O QGEBPTGBBRQVPC-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
ORNBQBCIOKFOEO-QGVNFLHTSA-N pregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 ORNBQBCIOKFOEO-QGVNFLHTSA-N 0.000 description 1
229960000249 pregnenolone Drugs 0.000 description 1
229960003387 progesterone Drugs 0.000 description 1
239000000186 progesterone Substances 0.000 description 1
238000001953 recrystallisation 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
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NL8103357A 1980-07-15 1981-07-15 Nieuwe 20-isonitril-17(20) onverzadigde steroiden, werkwijze voor het bereiden daarvan en werkwijze voor het bereiden van 17alfa-hydroxy-20-ketosteroiden daar- uit. NL8103357A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8015603A FR2486947A1 (fr)	1980-07-15	1980-07-15	Nouveaux derives steroides 20-isonitriles 17(20) insatures, leur procede de preparation et leur application a la preparation des steroides 17a-hydroxy 20-ceto
FR8015603		1980-07-15

Publications (1)

Publication Number	Publication Date
NL8103357A true NL8103357A (nl)	1982-02-01

Family

ID=9244163

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8103357A NL8103357A (nl)	1980-07-15	1981-07-15	Nieuwe 20-isonitril-17(20) onverzadigde steroiden, werkwijze voor het bereiden daarvan en werkwijze voor het bereiden van 17alfa-hydroxy-20-ketosteroiden daar- uit.

Country Status (14)

Country	Link
US (1)	US4501701A (sv)
JP (2)	JPS5749000A (sv)
AT (1)	AT376985B (sv)
CH (1)	CH650516A5 (sv)
DE (1)	DE3127989C2 (sv)
DK (1)	DK314581A (sv)
FI (1)	FI73223C (sv)
FR (1)	FR2486947A1 (sv)
GB (2)	GB2079756B (sv)
HU (1)	HU185639B (sv)
IT (1)	IT1171387B (sv)
NL (1)	NL8103357A (sv)
PT (1)	PT73360B (sv)
SE (1)	SE449752B (sv)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2521567A1 (fr) *	1982-02-18	1983-08-19	Roussel Uclaf	Nouveaux derives steroides 17(20)nitro, leur procede de preparation et leur application a la preparation de corticosteroides
EP0123735A1 (en) *	1983-04-29	1984-11-07	Gist-Brocades N.V.	New process for the preparation of 20-keto-delta-16-steroids and new intermediate compounds formed in this process
EP0123734A1 (en) *	1983-04-29	1984-11-07	Gist-Brocades N.V.	17-(Isocyano-sulfonylmethylene)-steroids, 17-(formamido-sulfonylmethylene)-steroids and their preparation
EP0153001B1 (en) *	1984-02-03	1992-03-11	The Upjohn Company	Steroids having an enamide or enimide group and their preparation
EP0336521B1 (en) *	1988-04-08	1992-04-01	Roussel-Uclaf	9-alpha-hydroxy-17-methylene steroids, process for their preparation and their use in the preparation of corticosteroids
FR2724174B1 (fr) *	1994-09-06	1997-01-17	Roussel Uclaf	Procede de preparation d'un derive steroide 17beta-carboxy et nouveaux intermediaires
US20140060391A1 (en) *	2012-08-28	2014-03-06	Pkl Corporation	Shrinkage-compensating concrete
EP4392036A1 (en) *	2021-08-26	2024-07-03	Brandeis University	Selective isonitrile inhibitors of cytochrome p450 subtypes

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL301670A (sv) *	1962-12-17
US3705179A (en) *	1971-03-15	1972-12-05	American Home Prod	Antiandrogenic steroids
DE2140291C3 (de) *	1971-08-06	1981-08-27	Schering Ag Berlin Und Bergkamen, 1000 Berlin	Verfahren zur Herstellung von Pregnan-Derivaten
US4041055A (en) *	1975-11-17	1977-08-09	The Upjohn Company	Process for the preparation of 17α-hydroxyprogesterones and corticoids from androstenes
US4251450A (en) *	1980-02-19	1981-02-17	Henkel Corporation	Nitrogen transhalogenation process

1980
- 1980-07-15 FR FR8015603A patent/FR2486947A1/fr active Granted
1981
- 1981-06-17 SE SE8103812A patent/SE449752B/sv not_active IP Right Cessation
- 1981-07-07 US US06/281,552 patent/US4501701A/en not_active Expired - Fee Related
- 1981-07-13 PT PT73360A patent/PT73360B/pt unknown
- 1981-07-14 CH CH4613/81A patent/CH650516A5/fr not_active IP Right Cessation
- 1981-07-14 HU HU812064A patent/HU185639B/hu not_active IP Right Cessation
- 1981-07-14 IT IT48898/81A patent/IT1171387B/it active
- 1981-07-15 NL NL8103357A patent/NL8103357A/nl not_active Application Discontinuation
- 1981-07-15 DK DK314581A patent/DK314581A/da not_active Application Discontinuation
- 1981-07-15 JP JP56109517A patent/JPS5749000A/ja active Granted
- 1981-07-15 AT AT0312881A patent/AT376985B/de active
- 1981-07-15 FI FI812234A patent/FI73223C/sv not_active IP Right Cessation
- 1981-07-15 DE DE3127989A patent/DE3127989C2/de not_active Expired - Fee Related
- 1981-07-15 GB GB8121805A patent/GB2079756B/en not_active Expired
1983
- 1983-07-18 GB GB08319389A patent/GB2132619B/en not_active Expired
1989
- 1989-01-19 JP JP1008743A patent/JPH01238593A/ja active Granted

Also Published As

Publication number	Publication date
GB2079756A (en)	1982-01-27
JPH01238593A (ja)	1989-09-22
ATA312881A (de)	1984-06-15
DK314581A (da)	1982-01-16
PT73360A (fr)	1981-08-01
GB8319389D0 (en)	1983-08-17
IT1171387B (it)	1987-06-10
JPH0262558B2 (sv)	1990-12-26
GB2132619B (en)	1985-01-09
PT73360B (fr)	1983-06-20
DE3127989A1 (de)	1982-03-18
AT376985B (de)	1985-01-25
FI812234L (fi)	1982-01-16
FI73223B (fi)	1987-05-29
FR2486947B1 (sv)	1982-10-15
SE449752B (sv)	1987-05-18
FR2486947A1 (fr)	1982-01-22
HU185639B (en)	1985-03-28
JPS5749000A (en)	1982-03-20
SE8103812L (sv)	1982-01-16
DE3127989C2 (de)	1995-05-18
JPH0323559B2 (sv)	1991-03-29
GB2132619A (en)	1984-07-11
IT8148898A0 (it)	1981-07-14
GB2079756B (en)	1984-01-11
FI73223C (sv)	1987-09-10
CH650516A5 (fr)	1985-07-31
US4501701A (en)	1985-02-26

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EP0103233B1 (en)	1987-11-25	A method to trap the enolate ion of the malonic acid or its derivatives
JP2007506805A (ja)	2007-03-22	７α−アルキル化された１９−ノルステロイドの調製方法
NL8103357A (nl)	1982-02-01	Nieuwe 20-isonitril-17(20) onverzadigde steroiden, werkwijze voor het bereiden daarvan en werkwijze voor het bereiden van 17alfa-hydroxy-20-ketosteroiden daar- uit.
EP0050325A2 (de)	1982-04-28	Verfahren zur Herstellung von Zwischenprodukten in der Synthese von Vitamin D3-Metaboliten und neue Zwischenprodukte
JPH026359B2 (sv)	1990-02-08
JPH0320399B2 (sv)	1991-03-19
RU2099346C1 (ru)	1997-12-20	Стероиды, способ получения стероидов, способ получения 16-метиленстероидов, соединения
CA1156646A (en)	1983-11-08	5.beta.-HYDROXY-.DELTA..SUP.6-STEROIDS
WO1986000907A1 (en)	1986-02-13	Process for the manufacture of 6alpha-methyl steroids
EP0532562A1 (de)	1993-03-24	VERFAHREN ZUR HERSTELLUNG VON 10-g(b)-H-STEROIDEN.
US4451404A (en)	1984-05-29	16β-Methyl steroid process
JPH0776231B2 (ja)	1995-08-16	１７α―エチニル―１７β―ヒドロキシ―１８―メチル―４，１５―エストラジエン―３―オンの製法
JPH0480889B2 (sv)	1992-12-21
US5003063A (en)	1991-03-26	Conversion of steroidal 17-cyanohydrins to corticoids
EP0322819B1 (en)	1994-07-27	Method for the preparation of beta-substituted allylsilane
JPH11279104A (ja)	1999-10-12	芳香族アルデヒドの製造法
GB2088354A (en)	1982-06-09	Preparation of a-pivaloyl acetic esters
US4329294A (en)	1982-05-11	Process for preparing 17α-hydroxy-20-ketosteroids
Barton et al.	1985	20-Isocyano-Δ 17 (20)-steroids
ES2668461T3 (es)	2018-05-18	Un procedimiento para la producción de 19-norpregn-4-en-3,20-diona-17?-ol (gestonorona) y productos intermedios correspondientes
SU450405A3 (ru)	1974-11-15	Способ получени 17 -этинилэстриолов
HU187382B (en)	1985-12-28	Process for producing 17-beta-ethnyl-steroides
JPH0348909B2 (sv)	1991-07-25
JPH0761979A (ja)	1995-03-07	ビスフェノール誘導体及びその製造方法
JP2714392B2 (ja)	1998-02-16	ステロイド誘導体の製造法

Legal Events

Date	Code	Title
1985-01-01	A85	Still pending on 85-01-01
1988-06-01	BA	A request for search or an international-type search has been filed
1988-07-01	BB	A search report has been drawn up
1988-08-01	BC	A request for examination has been filed
1998-04-01	BV	The patent application has lapsed