IL25744A - Gonane derivatives - Google Patents
Gonane derivativesInfo
- Publication number
- IL25744A IL25744A IL25744A IL2574466A IL25744A IL 25744 A IL25744 A IL 25744A IL 25744 A IL25744 A IL 25744A IL 2574466 A IL2574466 A IL 2574466A IL 25744 A IL25744 A IL 25744A
- Authority
- IL
- Israel
- Prior art keywords
- carbon
- group
- hydrogen
- compound
- carbon atoms
- Prior art date
Links
- 150000003803 gonane derivatives Chemical class 0.000 title 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 150000003431 steroids Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- -1 carbon steroid Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 230000001548 androgenic effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000001076 estrogenic effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000001195 anabolic effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000871 hypocholesterolemic effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000002345 steroid group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07J41/0072—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the A ring of the steroid being aromatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0059—Estrane derivatives substituted in position 17 by a keto group
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR17103A FR4941M (en:Method) | 1965-05-14 | 1965-05-14 | |
| FR28020A FR1453966A (fr) | 1965-05-14 | 1965-08-11 | Dérivés du gonane et procédé de préparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL25744A true IL25744A (en) | 1970-08-19 |
Family
ID=26163858
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL25744A IL25744A (en) | 1965-05-14 | 1966-05-10 | Gonane derivatives |
| IL34076A IL34076A (en) | 1965-05-14 | 1966-05-10 | 13beta-ethyl-3-hydroxy-16-hydroxy-methylene-gona-1,3,5(10)-trien-17-one and process for preparing it |
| IL25743A IL25743A (en) | 1965-05-14 | 1966-05-10 | 16-oximidomethylene-gonanes |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL34076A IL34076A (en) | 1965-05-14 | 1966-05-10 | 13beta-ethyl-3-hydroxy-16-hydroxy-methylene-gona-1,3,5(10)-trien-17-one and process for preparing it |
| IL25743A IL25743A (en) | 1965-05-14 | 1966-05-10 | 16-oximidomethylene-gonanes |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3409722A (en:Method) |
| AT (2) | AT259774B (en:Method) |
| BE (2) | BE680857A (en:Method) |
| BR (1) | BR6679469D0 (en:Method) |
| CH (2) | CH467768A (en:Method) |
| DE (2) | DE1593301A1 (en:Method) |
| DK (2) | DK116998B (en:Method) |
| FR (2) | FR4941M (en:Method) |
| GB (3) | GB1096765A (en:Method) |
| IL (3) | IL25744A (en:Method) |
| NL (3) | NL6606579A (en:Method) |
| SE (2) | SE327398B (en:Method) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3030357A (en) * | 1960-01-29 | 1962-04-17 | Sterling Drug Inc | 16-aminomethylene-17-oxo steroids and preparation thereof |
-
0
- NL NL126186D patent/NL126186C/xx active
-
1965
- 1965-05-14 FR FR17103A patent/FR4941M/fr not_active Expired
- 1965-08-11 FR FR28020A patent/FR1453966A/fr not_active Expired
-
1966
- 1966-05-04 DE DE19661593301 patent/DE1593301A1/de active Pending
- 1966-05-04 DE DE1966R0043191 patent/DE1593300A1/de active Pending
- 1966-05-09 US US548414A patent/US3409722A/en not_active Expired - Lifetime
- 1966-05-10 IL IL25744A patent/IL25744A/en unknown
- 1966-05-10 IL IL34076A patent/IL34076A/xx unknown
- 1966-05-10 IL IL25743A patent/IL25743A/xx unknown
- 1966-05-11 BE BE680857A patent/BE680857A/xx unknown
- 1966-05-11 BE BE680856A patent/BE680856A/xx unknown
- 1966-05-12 CH CH688966A patent/CH467768A/fr unknown
- 1966-05-12 CH CH689066A patent/CH468367A/fr unknown
- 1966-05-12 DK DK243066AA patent/DK116998B/da unknown
- 1966-05-12 BR BR179469/66A patent/BR6679469D0/pt unknown
- 1966-05-12 DK DK243166AA patent/DK113777B/da unknown
- 1966-05-13 AT AT456766A patent/AT259774B/de active
- 1966-05-13 AT AT456866A patent/AT261819B/de active
- 1966-05-13 GB GB21291/66A patent/GB1096765A/en not_active Expired
- 1966-05-13 SE SE06664/66A patent/SE327398B/xx unknown
- 1966-05-13 SE SE6665/66A patent/SE314063B/xx unknown
- 1966-05-13 GB GB11282/67A patent/GB1096770A/en not_active Expired
- 1966-05-13 GB GB21290/66A patent/GB1096764A/en not_active Expired
- 1966-05-13 NL NL6606579A patent/NL6606579A/xx unknown
- 1966-05-13 NL NL6606578A patent/NL6606578A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK116998B (da) | 1970-03-09 |
| IL34076A (en) | 1970-11-30 |
| AT259774B (de) | 1968-02-12 |
| GB1096764A (en) | 1967-12-29 |
| GB1096765A (en) | 1967-12-29 |
| AT261819B (de) | 1968-05-10 |
| CH468367A (fr) | 1969-02-15 |
| SE327398B (en:Method) | 1970-08-24 |
| DE1593300A1 (de) | 1970-10-22 |
| BR6679469D0 (pt) | 1973-10-23 |
| DE1593301A1 (de) | 1970-07-16 |
| CH467768A (fr) | 1969-01-31 |
| FR1453966A (fr) | 1966-07-22 |
| BE680857A (en:Method) | 1966-11-14 |
| GB1096770A (en) | 1967-12-29 |
| NL6606579A (en:Method) | 1966-11-15 |
| BE680856A (en:Method) | 1966-11-14 |
| IL25743A (en) | 1970-06-17 |
| NL126186C (en:Method) | |
| US3409722A (en) | 1968-11-05 |
| DK113777B (da) | 1969-04-28 |
| NL6606578A (en:Method) | 1966-11-15 |
| FR4941M (en:Method) | 1967-03-28 |
| SE314063B (en:Method) | 1969-09-01 |
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