IL32496A - 1-oxa-a-nor-androstanes - Google Patents

1-oxa-a-nor-androstanes

Info

Publication number: IL32496A
Authority: IL; Israel
Prior art keywords: formula; carbon; compound; action; methyl
Prior art date: 1968-07-24

Application number

IL32496A

Other languages

English (en)

Other versions

IL32496A0 (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.)

1968-07-24

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 IL32496A0 publication Critical patent/IL32496A0/xx

1973-06-29 Publication of IL32496A publication Critical patent/IL32496A/en

Links

150000001875 compounds Chemical class 0.000 claims description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
-1 ethyl methyl Chemical group 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
238000000034 method Methods 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
239000004593 Epoxy Substances 0.000 claims description 2
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
150000007530 organic bases Chemical group 0.000 claims description 2
DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 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 claims 1
150000008065 acid anhydrides Chemical class 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
229960003399 estrone Drugs 0.000 claims 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
239000000284 extract Substances 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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 3
239000007864 aqueous solution Substances 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
GRXPVLPQNMUNNX-MHJRRCNVSA-N estrane Chemical compound C1CC2CCCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 GRXPVLPQNMUNNX-MHJRRCNVSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000001476 alcoholic effect Effects 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
230000001195 anabolic effect Effects 0.000 description 1
230000001548 androgenic effect Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000003385 bacteriostatic effect Effects 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
238000009826 distribution Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229940102213 injectable suspension Drugs 0.000 description 1
ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Classifications

- 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
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes

Landscapes

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

IL32496A 1968-07-24 1969-06-27 1-oxa-a-nor-androstanes IL32496A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR160425		1968-07-24

Publications (2)

Publication Number	Publication Date
IL32496A0 IL32496A0 (en)	1969-08-27
IL32496A true IL32496A (en)	1973-06-29

Family

ID=8652984

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL32496A IL32496A (en)	1968-07-24	1969-06-27	1-oxa-a-nor-androstanes

Country Status (6)

Country	Link
US (1)	US3676461A (fr)
CH (1)	CH515277A (fr)
DE (1)	DE1934105A1 (fr)
GB (2)	GB1274033A (fr)
IL (1)	IL32496A (fr)
NL (1)	NL6910354A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5206415A (en) *	1991-12-20	1993-04-27	Washington University	Tricyclic steroid analogs
US5434274A (en) *	1991-12-20	1995-07-18	Washington University	Benz(epsilon)indene compounds

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

1969
- 1969-06-27 IL IL32496A patent/IL32496A/en unknown
- 1969-06-30 CH CH998269A patent/CH515277A/fr not_active IP Right Cessation
- 1969-07-04 NL NL6910354A patent/NL6910354A/xx unknown
- 1969-07-04 DE DE19691934105 patent/DE1934105A1/de active Pending
- 1969-07-07 US US839706A patent/US3676461A/en not_active Expired - Lifetime
- 1969-07-09 GB GB30115/71A patent/GB1274033A/en not_active Expired
- 1969-07-09 GB GB34478/69A patent/GB1274032A/en not_active Expired

Also Published As

Publication number	Publication date
IL32496A0 (en)	1969-08-27
US3676461A (en)	1972-07-11
DE1934105A1 (de)	1970-01-29
GB1274033A (en)	1972-05-10
GB1274032A (en)	1972-05-10
NL6910354A (fr)	1970-01-27
CH515277A (fr)	1971-11-15

Publication	Publication Date	Title
Wallis et al.	1937	Molecular Rearrangements in the Sterols. I. The Action of Anhydrous Potassium Acetate on Cholesteryl p-Toluenesulfonate in Acetic Anhydride Solution
VALENTINE Jr et al.	1941	Contributions to the study of marine products. VIII. The sterol of sponges: Clionasterol and poriferasterol
Pearlman	1947	The preparation of C-27 steroids from bile acids. I. Coprostanetetrol-3 (α), 7 (α), 12 (α), 25
McGuckin et al.	1952	Steroids Derived from Bile Acids. XVIII. Introduction of the 4, 5-Double Bond of Cortisone1, 2
US2918463A (en)	1959-12-22	17-carboxyalkylated 17-hydroxy-19-norandrosten-3-ones
IL32496A (en)	1973-06-29	1-oxa-a-nor-androstanes
Salce et al.	1970	Preparation of 16-unsaturated steroids by elimination of 17. alpha.-acyloxyl
Mueller et al.	1953	The conversion of hecogenin and manogenin into derivatives of allopregnane-12, 20-dione
US2694080A (en)	1954-11-09	11-hydroxy-13-methyl-17-(beta-hydroxyethylidene)-1, 2, 3, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17-tetradecahydro-15h-cyclopenta[a]-phenanthren-3-one
DE1298993B (de)	1969-07-10	3-Oxo-8ª‡-17ª‰-hydroxy-17ª‡-aethinyl-oestr-5(10)-en in seiner racemischen und linksdrehenden Form und Verfahren zur Herstellung dieser Verbindungen
EHRENSTEIN et al.	1951	INVESTIGATIONS ON STEROIDS. XIII. TRANSFORMATION OF STROPHANTHIDIN INTO COMPOUNDS STRUCTURALLY RELATED TO STEROID HORMONES1
US2900383A (en)	1959-08-18	Dehydro-17alpha-carboxyethyl-17beta-hydroxyandrost-4-en-3-one lactones
Ungnade et al.	1948	The hydrogenation of phenolic acids
US2547949A (en)	1951-04-10	Lower alkoxyalkanoates of hydroxylated hormones and process of producing same
Adackaparayil et al.	1977	Preparation and reactivity of a new spin label reagent
JPS5850240B2 (ja)	1983-11-09	アンドロスタン系の新規なジエン誘導体の製造法
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
US3053861A (en)	1962-09-11	3alpha-amino-pregnane compounds
KR100413753B1 (ko)	2004-03-31	에퀼린의이성질체화방법
US3238197A (en)	1966-03-01	19-nor-20-spiroxa-4, 9(10)-dien-3-one, the corresponding 3, 21-dione and intermediates therefor
US2917507A (en)	1959-12-15	Synthesis of steroids
US2140480A (en)	1938-12-13	3-keto-d-pentonic acid lactone and process for the manufacture of same
Murr et al.	1955	2, 2, 4, 4-Tetramethyl-3-oxetanone
US2661357A (en)	1953-12-01	Production of 16-keto-17-hydroxy steroids
US2601168A (en)	1952-06-17	delta 4-17alpha-methyl-3, 20-dioxo-pregnene compounds