DD297651A5 - Verfahren zur herstellung von progesteron-derivaten - Google Patents

Verfahren zur herstellung von progesteron-derivaten Download PDF

Info

Publication number: DD297651A5
Authority: DD; German Democratic Republic
Prior art keywords: group; general formula; reaction; progesterone derivatives; grignard reagent
Prior art date: 1989-09-14

Application number

DD90343978A

Other languages

German (de)

English (en)

Inventor

Helmut Haeuser

Hans D Berndt

Original Assignee

��@��k��

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.)

1989-09-14

Filing date

1990-09-12

Publication date

1992-01-16

1990-09-12 Application filed by ��@��k�� filed Critical ��@��k��

1992-01-16 Publication of DD297651A5 publication Critical patent/DD297651A5/de

Links

150000003145 progesterone derivatives Chemical class 0.000 title claims abstract description 11
238000004519 manufacturing process Methods 0.000 title abstract description 3
238000000034 method Methods 0.000 claims abstract description 13
150000004795 grignard reagents Chemical class 0.000 claims abstract description 11
239000007818 Grignard reagent Substances 0.000 claims abstract description 10
150000002825 nitriles Chemical class 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims abstract description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
239000000543 intermediate Substances 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
-1 1,2-ethylenedioxy group Chemical group 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
238000001256 steam distillation Methods 0.000 description 2
150000003431 steroids Chemical class 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
102100027324 2-hydroxyacyl-CoA lyase 1 Human genes 0.000 description 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
101001009252 Homo sapiens 2-hydroxyacyl-CoA lyase 1 Proteins 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
238000007605 air drying Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
244000309464 bull Species 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000001816 cooling 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
238000002474 experimental method Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
GNWXVOQHLPBSSR-UHFFFAOYSA-N oxolane;toluene Chemical compound C1CCOC1.CC1=CC=CC=C1 GNWXVOQHLPBSSR-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 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
238000003786 synthesis reaction Methods 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
- 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
- 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
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
- C07J7/0045—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa not substituted in position 16

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Toxicology (AREA)
Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD90343978A 1989-09-14 1990-09-12 Verfahren zur herstellung von progesteron-derivaten DD297651A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3931064A DE3931064A1 (de)	1989-09-14	1989-09-14	Verfahren zur herstellung von progesteron-derivaten

Publications (1)

Publication Number	Publication Date
DD297651A5 true DD297651A5 (de)	1992-01-16

Family

ID=6389636

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90343978A DD297651A5 (de)	1989-09-14	1990-09-12	Verfahren zur herstellung von progesteron-derivaten

Country Status (10)

Country	Link
US (1)	US5132440A (fr)
EP (1)	EP0443000B1 (fr)
JP (1)	JP2837271B2 (fr)
AT (1)	ATE117695T1 (fr)
CA (1)	CA2041644A1 (fr)
DD (1)	DD297651A5 (fr)
DE (2)	DE3931064A1 (fr)
ES (1)	ES2070334T3 (fr)
MX (1)	MX172229B (fr)
WO (1)	WO1991004265A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN103467555A (zh) *	2013-03-29	2013-12-25	山东新华制药股份有限公司	17α-羟基黄体酮的合成方法
CN104072565B (zh) *	2014-07-11	2017-03-01	山东众诚药业股份有限公司	一种高收率的17α‑羟基黄体酮的简捷制备方法
CN104119415B (zh) *	2014-08-06	2017-01-25	湖南科瑞生物制药股份有限公司	一种17a‑羟基黄体酮的制备方法
CN107286215A (zh) *	2016-03-31	2017-10-24	天津金耀集团有限公司	一种多个烯烃基团的甾体化合物制备方法
CN105801651B (zh) *	2016-04-19	2018-03-06	浙江仙居君业药业有限公司	一种17α‑羟基黄体酮的合成方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2082129A5 (fr) *	1970-03-04	1971-12-10	Roussel Uclaf
US4585590A (en) *	1984-02-03	1986-04-29	The Upjohn Company	Cyanohydrin process
DE3585547D1 (de) *	1984-02-03	1992-04-16	Upjohn Co	Steroide mit einer enamid- oder enimidgruppe sowie ihre herstellung.
US4831131A (en) *	1984-02-03	1989-05-16	The Upjohn Company	11β,17α-Dihydroxy-17β-cyano-androstanes
DE3427486A1 (de) *	1984-07-23	1986-01-30	Schering AG, Berlin und Bergkamen, 1000 Berlin	Verfahren zur herstellung von 6(alpha)-methylsteroiden

1989
- 1989-09-14 DE DE3931064A patent/DE3931064A1/de not_active Withdrawn
1990
- 1990-09-06 EP EP90913165A patent/EP0443000B1/fr not_active Expired - Lifetime
- 1990-09-06 US US07/720,822 patent/US5132440A/en not_active Expired - Lifetime
- 1990-09-06 CA CA002041644A patent/CA2041644A1/fr not_active Abandoned
- 1990-09-06 WO PCT/DE1990/000688 patent/WO1991004265A1/fr not_active Ceased
- 1990-09-06 ES ES90913165T patent/ES2070334T3/es not_active Expired - Lifetime
- 1990-09-06 AT AT90913165T patent/ATE117695T1/de not_active IP Right Cessation
- 1990-09-06 DE DE59008362T patent/DE59008362D1/de not_active Expired - Fee Related
- 1990-09-06 JP JP2512107A patent/JP2837271B2/ja not_active Expired - Lifetime
- 1990-09-12 DD DD90343978A patent/DD297651A5/de not_active IP Right Cessation
- 1990-09-13 MX MX022367A patent/MX172229B/es unknown

Also Published As

Publication number	Publication date
DE59008362D1 (de)	1995-03-09
EP0443000A1 (fr)	1991-08-28
WO1991004265A1 (fr)	1991-04-04
ES2070334T3 (es)	1995-06-01
CA2041644A1 (fr)	1991-03-15
JP2837271B2 (ja)	1998-12-14
DE3931064A1 (de)	1991-03-28
EP0443000B1 (fr)	1995-01-25
US5132440A (en)	1992-07-21
MX172229B (es)	1993-12-08
JPH04501861A (ja)	1992-04-02
ATE117695T1 (de)	1995-02-15

Legal Events

Date	Code	Title	Description
1997-06-19	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
CH629222A5 (de)	1982-04-15	Verfahren zur herstellung von androstan-derivaten.
DE69709655T2 (de)	2002-09-12	Verfahren zur herstellung von 17-estern von 9alpha,21-dihalopregan-11beta,17alpha-diol-20-onen
DD297651A5 (de)	1992-01-16	Verfahren zur herstellung von progesteron-derivaten
DE3427486A1 (de)	1986-01-30	Verfahren zur herstellung von 6(alpha)-methylsteroiden
CH624684A5 (fr)	1981-08-14
DE2729501A1 (de)	1978-01-05	Verfahren zur herstellung von 17beta-hydroxy-3-oxo-17alpha-pregn-4- en-21-carbonsaeure-gamma-lacton
DE2237202A1 (de)	1973-02-22	Verfahren zur herstellung von 17(2-haloaethyliden)-steroiden
WO2001096277A1 (fr)	2001-12-20	Procede de production d'acide 2,3,4,6-tetramethylmandelique et d'acetate d'acide 2,3,4,6-tetramethylmandelique
AT203474B (de)	1959-05-25	Verfahren zur Herstellung von α,β-ungesättigten Aldehyden
DE960819C (de)	1957-03-28	Verfahren zur Herstellung von 11ª‰ -Oxyprogesteron
DE4319998A1 (de)	1994-12-15	Verfahren zur Herstellung von Derivaten des Estra-1,3,5(10),14-tetraen-3,17alpha-diols
DE602004009544T2 (de)	2008-08-07	Neue 3,3-Dimethyl-5-Cyano-Benzoxepinderivate verwendbar zur Herstellung von 5-Formyl-Benzoxepinderivaten
CH632263A5 (de)	1982-09-30	Verfahren zur herstellung cyclischer 2-methyl-2,4-dialkoxy-3-buten-1-al-acetale und deren verwendung.
DE4301461A1 (de)	1994-09-29	Verfahren zur Herstellung von Derivaten des Estra-1,3,5(10),14-tetraen-3,17alpha-diols
DE1643008C3 (de)	1976-06-24	Verfahren zur Herstellung von 17Äthinyl-Delta hoch 16 -steroiden
EP0290378A1 (fr)	1988-11-09	Procédé de préparation de 1-méthyl-androsta-1,4-diène-3,17-dione et intermédiaires nécéssaires pour ce procédé
DE2222544C3 (de)	1976-10-07	Neue 16,17-Secoöstradi- und triene Verfahren zu ihrer Herstellung sowie diese enthaltendes Mittel
AT273387B (de)	1969-08-11	Verfahren zur Herstellung von neuen Cholesterinderivaten sowie von deren Säureadditionssalzen
DE69502438T2 (de)	1998-10-15	Verbessertes Verfahren zur Herstellung von 3-beta, 14-beta-Dihydroxyethialnaldehyde
DE2204366A1 (de)	1973-08-02	Steroid-abkoemmlinge
DD281394A5 (de)	1990-08-08	Verfahren zur herstellung von steroid-c-17 alpha-carbonitrilen
DE2222544B2 (de)	1976-02-19	Neue 16,17-secooestradi- und triene verfahren zu ihrer herstellung sowie diese enthaltendes mittel
WO2000056758A1 (fr)	2000-09-28	PROCEDE PERMETTANT DE PRODUIRE DES ESTERS DE L'ACIDE 4,4-DIMETHYL-3β-HYDROXYPREGNA-8,14-DIENE-21-CARBOXYLIQUE ET PRODUITS INTERMEDIAIRES OBTENUS PAR LEDIT PROCEDE
DE3627154A1 (de)	1988-02-25	Verfahren zur herstellung von (z)-17(alpha)-halogenvinyl-steroiden und (z)-17(alpha)-chlorvinyl-steroide
DD298408A5 (de)	1992-02-20	Verfahren zur herstellung von 17 alpha-allyl-17 beta-hydroxysteroidderivaten