IL32494A - 1-oxa-a-nor-androstanes - Google Patents

1-oxa-a-nor-androstanes

Info

Publication number: IL32494A
Authority: IL; Israel
Prior art keywords: formula; action; obtains; agent; residue
Prior art date: 1968-07-09

Application number

IL32494A

Other languages

English (en)

Other versions

IL32494A0 (en

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.)

1968-07-09

Filing date

1969-06-27

Publication date

1973-06-29

1969-06-27 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1969-08-27 Publication of IL32494A0 publication Critical patent/IL32494A0/xx

1973-06-29 Publication of IL32494A publication Critical patent/IL32494A/en

Links

239000003795 chemical substances by application Substances 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 9
238000000034 method Methods 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
239000004593 Epoxy Substances 0.000 claims description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
239000000460 chlorine 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
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
238000007127 saponification reaction Methods 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000001548 androgenic effect Effects 0.000 description 3
-1 heterocyclic steroids Chemical class 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000006071 cream Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
208000002874 Acne Vulgaris Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-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
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
206010000496 acne Diseases 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
230000001195 anabolic effect Effects 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Chemical group 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
229940005991 chloric acid Drugs 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical class CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229940099990 ogen Drugs 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
- C07J73/001—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom
- C07J73/003—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom by oxygen as hetero atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL32494A 1968-07-09 1969-06-27 1-oxa-a-nor-androstanes IL32494A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR158476A FR7498M (fr)	1968-07-09	1968-07-09

Publications (2)

Publication Number	Publication Date
IL32494A0 IL32494A0 (en)	1969-08-27
IL32494A true IL32494A (en)	1973-06-29

Family

ID=8652292

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL32494A IL32494A (en)	1968-07-09	1969-06-27	1-oxa-a-nor-androstanes

Country Status (8)

Country	Link
US (1)	US3714203A (fr)
BE (1)	BE652722A (fr)
CH (1)	CH513209A (fr)
DE (1)	DE1934057A1 (fr)
FR (1)	FR7498M (fr)
GB (2)	GB1274031A (fr)
IL (1)	IL32494A (fr)
NL (1)	NL6910353A (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3483223A (en) *	1966-10-26	1969-12-09	Squibb & Sons Inc	Synthesis of a-norandrostane steroids

0
- BE BE652722D patent/BE652722A/xx unknown
1968
- 1968-07-09 FR FR158476A patent/FR7498M/fr not_active Expired
1969
- 1969-06-27 IL IL32494A patent/IL32494A/en unknown
- 1969-06-30 CH CH998169A patent/CH513209A/fr not_active IP Right Cessation
- 1969-07-04 NL NL6910353A patent/NL6910353A/xx unknown
- 1969-07-04 DE DE19691934057 patent/DE1934057A1/de active Pending
- 1969-07-07 US US00839659A patent/US3714203A/en not_active Expired - Lifetime
- 1969-07-09 GB GB34477/69A patent/GB1274031A/en not_active Expired
- 1969-07-09 GB GB30116/71A patent/GB1274034A/en not_active Expired

Also Published As

Publication number	Publication date
FR7498M (fr)	1969-12-08
BE652722A (fr)	1900-01-01
CH513209A (fr)	1971-09-30
GB1274034A (en)	1972-05-10
US3714203A (en)	1973-01-30
IL32494A0 (en)	1969-08-27
GB1274031A (en)	1972-05-10
DE1934057A1 (de)	1970-01-15
NL6910353A (fr)	1970-01-13

Publication	Publication Date	Title
US2232438A (en)	1941-02-18	Unsaturated pregnanolones and pregnandiones and a method of producing the same
US2686181A (en)	1954-08-10	16, 17-oxido-5-pregnenes and method of preparing
US2945852A (en)	1960-07-19	17-oxygenated 9alpha-substituted androstano [3, 2-c] pyrazoles and derivatives
Allen et al.	1954	Steroidal Cyclic Ketals. XI. 1 The Conversion of 11-epi-Hydrocortisone into Hydrocortisone
US2656349A (en)	1953-10-20	14,15-oxides of the cyclopentanopolyhydrophenanthrene and polyhydrochrysene series
IL32494A (en)	1973-06-29	1-oxa-a-nor-androstanes
Marker et al.	1940	Sterols. LXXXIV. Progesterone from Hyodesoxycholic Acid
US2918463A (en)	1959-12-22	17-carboxyalkylated 17-hydroxy-19-norandrosten-3-ones
US2366204A (en)	1945-01-02	Keto-steroids and method of obtaining same
US3346602A (en)	1967-10-10	13beta-alkyl-11-alkylgona-1, 3, 5 (10)-trien-17-ones, ethers and esters thereof
US3478062A (en)	1969-11-11	Certain tetrahydroindane derivatives
Hoehn et al.	1946	3-Keto-6 (β)-hydroxycholanic Acid and 3 (α)-Hydroxy-6-ketocholanic Acid
IL26986A (en)	1971-04-28	7alpha-methyl-delta4,9-steroids of the estrane and gonane series
US2875215A (en)	1959-02-24	1-acylthio substitution products of 3, 17-dioxygenated androstane derivatives
US3080360A (en)	1963-03-05	17alpha-alkyl-17beta-hydroxy-18-norandrost-4-en-3-ones
US2773885A (en)	1956-12-11	Steroids of the ergosta series
US2868784A (en)	1959-01-13	Process for the manufacture of steroids
US2686790A (en)	1954-08-17	Tritylated hydroxyetiocholanic acids
US3890304A (en)	1975-06-17	7{60 -carbam oyl-17-hydroxy-3-oxo-17{60 -pregn-4-ene-21-carboxylic acid {65 -lactone and related compounds
US3313703A (en)	1967-04-11	19-nor-deta4, 9, 11-pregnatriene-3, 20-dione, process and intermediates
US3766248A (en)	1973-10-16	Substituted tricyclic compounds and process for their preparation
US2976284A (en)	1961-03-21	19-hydroxypregnene-3, 11, 20-triones, derivatives and intermediate 1, 19-isopropylidenedioxy steroids used in their preparation
US3257428A (en)	1966-06-21	1, 17-dioxygenated 5alpha-androstanes and delta analogs
US3080381A (en)	1963-03-05	Optionally 6-methylated and optionally 17-alkanoyloxygenated 2-oxapregnane-3, 20-diones, a-homo compounds corresponding, and 4, 5-dehydro and 4, 5; 6, 7-bisdehydro derivatives thereof
US4213912A (en)	1980-07-22	Process for preparing steroidal [16α,17-d]cyclohexene-21-carboxylic acid esters