JPS5835200A - ヨ−ドステロイドの還元方法 - Google Patents

ヨ−ドステロイドの還元方法

Info

Publication number: JPS5835200A
Authority: JP; Japan
Prior art keywords: reducing; dione; general formula; iodosteroids; formula
Prior art date: 1981-08-27
Legal status (The legal status 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 status listed.): Granted

Application number

JP13476881A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0122279B2 (da

Inventor

Kazumasa Nitta

新田　一誠

Shinichiro Fujimori

信一郎藤森

Toshio Haruyama

春山　敏夫

Shinya Inoue

伸哉井上

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mitsubishi Chemical Corp

Original Assignee

Mitsubishi Chemical Industries 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.)

1981-08-27

Filing date

1981-08-27

Publication date

1983-03-01

1981-08-27 Application filed by Mitsubishi Chemical Industries Ltd filed Critical Mitsubishi Chemical Industries Ltd

1981-08-27 Priority to JP13476881A priority Critical patent/JPS5835200A/ja

1982-07-08 Priority to US06/396,447 priority patent/US4440689A/en

1982-07-21 Priority to DE8282106585T priority patent/DE3266939D1/de

1982-07-21 Priority to EP82106585A priority patent/EP0071178B1/en

1982-07-21 Priority to DD82241836A priority patent/DD202439A5/de

1983-03-01 Publication of JPS5835200A publication Critical patent/JPS5835200A/ja

1989-04-25 Publication of JPH0122279B2 publication Critical patent/JPH0122279B2/ja

Status Granted legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
150000007513 acids Chemical class 0.000 claims description 8
150000003431 steroids Chemical class 0.000 claims description 6
125000004423 acyloxy group Chemical group 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class 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 7
238000004519 manufacturing process Methods 0.000 description 5
239000000186 progesterone Substances 0.000 description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
-1 madanesium Chemical compound 0.000 description 3
229960003387 progesterone Drugs 0.000 description 3
238000003756 stirring Methods 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol 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)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
239000013078 crystal Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
150000003146 progesterones Chemical class 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 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
DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
QRDYCDIUGUAUBZ-SRWWVFQWSA-N (7r,8s,9s,10r,13s,14s,17s)-17-acetyl-7-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C([C@H]1O)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 QRDYCDIUGUAUBZ-SRWWVFQWSA-N 0.000 description 1
DBPWSSGDRRHUNT-UHFFFAOYSA-N 17alpha-hydroxy progesterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(=O)C)(O)C1(C)CC2 DBPWSSGDRRHUNT-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
229910052689 Holmium Inorganic materials 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DOMWKUIIPQCAJU-LJHIYBGHSA-N Hydroxyprogesterone caproate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)CCCCC)[C@@]1(C)CC2 DOMWKUIIPQCAJU-LJHIYBGHSA-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
229910000831 Steel Inorganic materials 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
DWCSNWXARWMZTG-UHFFFAOYSA-N Trigonegenin A Natural products CC1C(C2(CCC3C4(C)CCC(O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 DWCSNWXARWMZTG-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
229940124558 contraceptive agent Drugs 0.000 description 1
239000003433 contraceptive agent Substances 0.000 description 1
235000004879 dioscorea Nutrition 0.000 description 1
WQLVFSAGQJTQCK-VKROHFNGSA-N diosgenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 WQLVFSAGQJTQCK-VKROHFNGSA-N 0.000 description 1
WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 description 1
229960003399 estrone Drugs 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
JYGYEBCBALMPDC-UHFFFAOYSA-N heptane;propan-2-one Chemical compound CC(C)=O.CCCCCCC JYGYEBCBALMPDC-UHFFFAOYSA-N 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
229950000801 hydroxyprogesterone caproate Drugs 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
244000005700 microbiome Species 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000000583 progesterone congener Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
229960002256 spironolactone Drugs 0.000 description 1
239000010959 steel Substances 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Landscapes

Steroid Compounds (AREA)

JP13476881A 1981-07-22 1981-08-27 ヨ−ドステロイドの還元方法 Granted JPS5835200A (ja)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
JP13476881A JPS5835200A (ja)	1981-08-27	1981-08-27	ヨ−ドステロイドの還元方法
US06/396,447 US4440689A (en)	1981-07-22	1982-07-08	Acyloxysteroids and process for producing same
DE8282106585T DE3266939D1 (en)	1981-07-22	1982-07-21	Acyloxysteroids and process for producing same
EP82106585A EP0071178B1 (en)	1981-07-22	1982-07-21	Acyloxysteroids and process for producing same
DD82241836A DD202439A5 (de)	1981-07-22	1982-07-21	Verfahren zur herstellung von acyloxysteroiden

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP13476881A JPS5835200A (ja)	1981-08-27	1981-08-27	ヨ−ドステロイドの還元方法

Publications (2)

Publication Number	Publication Date
JPS5835200A true JPS5835200A (ja)	1983-03-01
JPH0122279B2 JPH0122279B2 (da)	1989-04-25

Family

ID=15136105

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP13476881A Granted JPS5835200A (ja)	1981-07-22	1981-08-27	ヨ−ドステロイドの還元方法

Country Status (1)

Country	Link
JP (1)	JPS5835200A (da)

1981
- 1981-08-27 JP JP13476881A patent/JPS5835200A/ja active Granted

Also Published As

Publication number	Publication date
JPH0122279B2 (da)	1989-04-25

Publication	Publication Date	Title
JPS5854160B2 (ja)	1983-12-02	１α，３β−ジヒドロキシステロイド−５−エンまたはその誘導体の製造方法
IL95359A (en)	1995-08-31	B-71) Cyclopropylphoxy (Androst-5-AN-B-3-ol and similar compounds, 4-transducts used as inhibitors of C71-02-Liaz
Nitta et al.	1985	The syntheses of the corticoid side chain. I. An improved method for the preparation of 17. ALPHA.-hydroxyprogesterone from androst-4-ene-3, 17-dione.
RS90504A (sr)	2006-10-27	C-17 spirolaktonizacija i 6,7-oksidacija steroida
US4383947A (en)	1983-05-17	Introduction of a fluorine atom
JP5399711B2 (ja)	2014-01-29	高純度な１７α−シアノメチル−１７β−ヒドロキシ−エストラ−４，９−ジエン−３−オン及びその合成方法
JPS5835200A (ja)	1983-03-01	ヨ−ドステロイドの還元方法
JPH04502906A (ja)	1992-05-28	１４α，１７α―エタノ―エストラトリエン
US2910486A (en)	1959-10-27	10-hydroxyestra-1, 4-diene-3, 17-dione and acetate
US2798082A (en)	1957-07-02	Delta22-11-oxygenated-steroids and process of preparing them
JPS5813600A (ja)	1983-01-26	２β，１６β−ジ−アミノ５α−アンドロスタン類の新規なモノ−及びビス第四級アンモニウム誘導体及びこれらを含有する医薬製剤
US2855413A (en)	1958-10-07	16-haloestradiol esters and ethers
US3318917A (en)	1967-05-09	17alpha-(4-alkoxy-3-buten-1-ynyl)estra-1, 3, 5(10)-triene-3, 17beta-diols and derivatives thereof
HU187843B (en)	1986-02-28	Process for producing 17-alpha-hydroxy-17-beta-bracket-hydroxy-acetyl-bracket closed-steroides
US2691029A (en)	1954-10-05	Steroid oxidation
US2623054A (en)	1952-12-23	Steroid aldehydes
US3040065A (en)	1962-06-19	Process for the production of 8(9)-dehydroprogesterone and 9alpha-hydroxyprogesterone
US3374253A (en)	1968-03-19	Process for the preparation of 17(20)-21-al pregnenes
US2932638A (en)	1960-04-12	Process for the manufacture of 3-cycloketal derivatives of pregnan-3, 11, 20-triones and reduction products thereof and compounds obtained thereby
AU684946B2 (en)	1998-01-08	SYNTHESIS OF 17B CYANO-3-ETHOXY-17a-HYDROXY-6-METHYLANDROSTA-3,5,9-(11)-TRIEN 9(11)-triene
JPS62223190A (ja)	1987-10-01	１７α−プレグネン−カルボン酸メチルエステル化合物
US2727908A (en)	1955-12-20	16-aminomethyl pregnenes
US2912444A (en)	1959-11-10	Process of preparing 17-hydroxy-20-ketosteroids
JP4361976B2 (ja)	2009-11-11	エストロゲン混合物の硫酸化
US3112306A (en)	1963-11-26	16beta-mercapto-17beta-hydroxy-2-androsten-3-one 16, 17-cyclic acetals and intermediates thereof