CH420143A - Verfahren zur Herstellung von Pregnan-3B,5a,6B,16B,20a-pentol und dessen Estern - Google Patents

Verfahren zur Herstellung von Pregnan-3B,5a,6B,16B,20a-pentol und dessen Estern

Info

Publication number: CH420143A
Authority: CH; Switzerland
Prior art keywords: acid; pentol; pregnan; produced; oxidizing agent
Prior art date: 1959-02-24

Application number

CH307465A

Other languages

German (de)

English (en)

Inventor

Nawa Hayao

Nishikawa Masamoto

Original Assignee

Takeda Pharmaceutical

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.)

1959-02-24

Filing date

1960-02-23

Publication date

1966-09-15

1960-02-23 Application filed by Takeda Pharmaceutical filed Critical Takeda Pharmaceutical

1966-09-15 Publication of CH420143A publication Critical patent/CH420143A/de

Links

238000000034 method Methods 0.000 title claims description 12
150000002148 esters Chemical class 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 12
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
239000007800 oxidant agent Substances 0.000 claims description 7
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
150000004653 carbonic acids Chemical class 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 2
-1 steroid compounds Chemical class 0.000 claims description 2
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 claims 1
150000004968 peroxymonosulfuric acids Chemical class 0.000 claims 1
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 8
239000005556 hormone Substances 0.000 description 8
229940088597 hormone Drugs 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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 5
238000006243 chemical reaction Methods 0.000 description 5
235000019253 formic acid Nutrition 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
150000003431 steroids Chemical class 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000013543 active substance Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000002934 diuretic Substances 0.000 description 3
239000003862 glucocorticoid Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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 2
235000011054 acetic acid Nutrition 0.000 description 2
210000004100 adrenal gland Anatomy 0.000 description 2
230000001327 anti-mineralocorticoid effect Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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 2
WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 description 2
230000001882 diuretic effect Effects 0.000 description 2
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
239000002395 mineralocorticoid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
LRJOMUJRLNCICJ-JZYPGELDSA-N Prednisolone acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O LRJOMUJRLNCICJ-JZYPGELDSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000000397 acetylating effect Effects 0.000 description 1
239000003470 adrenal cortex hormone Substances 0.000 description 1
229940083712 aldosterone antagonist Drugs 0.000 description 1
239000003513 alkali Substances 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
235000010233 benzoic acid Nutrition 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
230000036772 blood pressure Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229960004544 cortisone Drugs 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229960000890 hydrocortisone Drugs 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
CXHHBNMLPJOKQD-UHFFFAOYSA-N methyl hydrogen carbonate Chemical compound COC(O)=O CXHHBNMLPJOKQD-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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 1
238000001953 recrystallisation Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000037067 skin hydration Effects 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
INLFWQCRAJUDCR-LYLBMTSKSA-N spirostan group Chemical group [C@@H]12C[C@@H]3O[C@]4(CC[C@@H](C)CO4)[C@@H](C)[C@@H]3[C@@]1(C)CC[C@H]1[C@H]2CCC2CCCC[C@]12C INLFWQCRAJUDCR-LYLBMTSKSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229940037128 systemic glucocorticoids Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)

CH307465A 1959-02-24 1960-02-23 Verfahren zur Herstellung von Pregnan-3B,5a,6B,16B,20a-pentol und dessen Estern CH420143A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP588959		1959-02-24
JP588859		1959-02-24

Publications (1)

Publication Number	Publication Date
CH420143A true CH420143A (de)	1966-09-15

Family

ID=26339913

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH307465A CH420143A (de)	1959-02-24	1960-02-23	Verfahren zur Herstellung von Pregnan-3B,5a,6B,16B,20a-pentol und dessen Estern
CH202160A CH419115A (de)	1959-02-24	1960-02-23	Verfahren zur Herstellung von Pregnan-3B, 5a, 6B, 16B, 20a-pentol und dessen Estern

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH202160A CH419115A (de)	1959-02-24	1960-02-23	Verfahren zur Herstellung von Pregnan-3B, 5a, 6B, 16B, 20a-pentol und dessen Estern

Country Status (2)

Country	Link
BE (1)	BE587941A (fr)
CH (2)	CH420143A (fr)

1960
- 1960-02-23 BE BE587941A patent/BE587941A/fr unknown
- 1960-02-23 CH CH307465A patent/CH420143A/de unknown
- 1960-02-23 CH CH202160A patent/CH419115A/de unknown

Also Published As

Publication number	Publication date
CH419115A (de)	1966-08-31
BE587941A (fr)	1960-06-16

Publication	Publication Date	Title
CH420143A (de)	1966-09-15	Verfahren zur Herstellung von Pregnan-3B,5a,6B,16B,20a-pentol und dessen Estern
DE2852055C2 (fr)	1988-06-09
DE1807585C3 (de)	1974-11-07	14,15beta-Epoxycardenolide, Verfahren zu deren Herstellung und diese enthaltende Mittel
DE1939164A1 (de)	1971-02-11	14beta-Hydroxy-15alpha-acyloxy-cardenolide
CH526526A (de)	1972-08-15	Verfahren zur Herstellung eines neuen 6a-Methyl-19-nor-progesterons
DE2150270C3 (de)	1980-12-04	Pregnansäure-Derivate und Verfahren zu ihrer Herstellung
DE1165594B (de)	1964-03-19	Verfahren zur Herstellung von Pregnan-3ª‰, 5ª‡, 6ª‰, 16ª‰, 20ª‡-pentol und dessen Estern
DE1618747C3 (de)	1976-06-16	Verfahren zur Herstellung von Delta hoch 5(10) 3-Keto-19-nor-steroiden
DE1158507B (de)	1963-12-05	Verfahren zur Herstellung von 6a-Methyl-16-methylen-steroiden
DE1199262C2 (de)	1973-10-31	Verfahren zur Herstellung von 5alpha-Brom-6beta-hydroxysteroiden
DE1518915C (de)	1972-06-08	17 alpha Alkanoyloxy 9 alpha fluor 11 oxy bzw 11 beta hydroxy 16 beta methyl pregna 1,4 dien 3,20 dione und Verfahren zu deren Herstellung
AT257060B (de)	1967-09-25	Verfahren zur Herstellung von neuen 3-Enoläthern der 6-Methyl-3-oxo-Δ<4>-steroide der Androstan-, 19-Norandrostan-, Pregnan- und 19-Norpregnanreihe
DE1418945C3 (de)	1973-09-13	Verfahren zur Herstellung von 16 alpha Methyl 17alpha hydroxy 20 oxo pregnandenvaten
DE2247390A1 (de)	1974-03-28	Neue 1-alkylthio-androstan-derivate
CH583749A5 (en)	1977-01-14	6-oxo-delta-1,3,5 (10) steroids prepn - by treatment of 3-oxo -delta-4-steroids with base and oxygen
DE1668687A1 (de)	1971-09-02	Neue 18-Methyl-5alpha-H-androstane
DE1904586A1 (de)	1969-08-28	16alpha-Alkylsteroide
DE1101415B (de)	1961-03-09	Verfahren zur Herstellung von 6ª‡-Methyl-17ª‡-acetoxy-4-pregnen-3, 20-dion
DE1768673B1 (de)	1971-10-14	6alpha,9alpha-Difluorprednisolon-17,21-diester
DE1193041B (de)	1965-05-20	Verfahren zur Herstellung von delta 7-, delta 7,9,(11)-, delta 7,9,(11),16-, delta 7, delta 8- oder delta 8,16-Steroiden
CH390910A (de)	1965-04-30	Verfahren zur Herstellung von 19-Nor- 5-androsten-3B,17B-diolen
DE1618747B2 (de)	1975-11-06	Verfahren zur Herstellung von Delta hoch 5(10) 3-Keto-19-nor-steroiden
CH497405A (de)	1970-10-15	Verfahren zur Herstellung von 17a,21-Diestern von 9a,11B-Dihalogen-16a-alkyl-1,4-pregnadien-17a,21-diol-3,20-dionen
DE1802962B2 (de)	1975-12-04	Neue 6alpha, 6beta-Olfluorsteroide, Verfahren zu Ihrer Herstellung, sowie diese enthaltende Mittel
DE1195749B (de)	1965-07-01	Verfahren zur Herstellung von neuen Nicotinsaeureestern von Steroiden