SU433673A3 - СПОСОБ ПОЛУЧЕНИЯ ОКСИМОВ 3-КЕТО-17а ПРОИАДИЕНИЛ СТЕРОИДОВ - Google Patents
СПОСОБ ПОЛУЧЕНИЯ ОКСИМОВ 3-КЕТО-17а ПРОИАДИЕНИЛ СТЕРОИДОВInfo
- Publication number
- SU433673A3 SU433673A3 SU1707216A SU1707216A SU433673A3 SU 433673 A3 SU433673 A3 SU 433673A3 SU 1707216 A SU1707216 A SU 1707216A SU 1707216 A SU1707216 A SU 1707216A SU 433673 A3 SU433673 A3 SU 433673A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- oxime
- propadienyl
- estra
- keto
- prodienyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 10
- 150000003431 steroids Chemical class 0.000 title 1
- 150000002923 oximes Chemical class 0.000 description 18
- 239000000203 mixture Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HMNQNULAYXDEEQ-UHFFFAOYSA-N acetic acid;hydroxylamine Chemical compound ON.CC(O)=O HMNQNULAYXDEEQ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000002443 hydroxylamines Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-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
- -1 Propadienyl residue Chemical group 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical group C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15419071A | 1971-06-17 | 1971-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU433673A3 true SU433673A3 (ru) | 1974-06-25 |
Family
ID=22550367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1707216A SU433673A3 (ru) | 1971-06-17 | 1971-10-20 | СПОСОБ ПОЛУЧЕНИЯ ОКСИМОВ 3-КЕТО-17а ПРОИАДИЕНИЛ СТЕРОИДОВ |
Country Status (14)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2522328B1 (fr) * | 1982-03-01 | 1986-02-14 | Roussel Uclaf | Nouveaux produits derives de la structure 3-ceto 4,9 19-nor steroides, leur procede de preparation et leur application comme medicaments |
| DE3723788A1 (de) * | 1987-07-16 | 1989-01-26 | Schering Ag | 11(beta)-phenyl-4,9,15-estratriene, deren herstellung und diese enthaltende pharmazeutische praeparate |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU33881B (en) * | 1966-07-06 | 1978-06-30 | Ortho Pharma Corp | Process for preparing azasteroids |
| SU402209A3 (enrdf_load_stackoverflow) * | 1968-11-25 | 1973-10-12 |
-
1971
- 1971-10-15 CH CH1480571A patent/CH558346A/xx not_active IP Right Cessation
- 1971-10-18 NL NL7114314A patent/NL7114314A/xx unknown
- 1971-10-19 BE BE774168A patent/BE774168A/xx unknown
- 1971-10-19 CA CA125,511A patent/CA952515A/en not_active Expired
- 1971-10-19 ZA ZA716984A patent/ZA716984B/xx unknown
- 1971-10-19 FR FR7137417A patent/FR2141647B1/fr not_active Expired
- 1971-10-19 GB GB4856171A patent/GB1363150A/en not_active Expired
- 1971-10-20 AU AU34835/71A patent/AU3483571A/en not_active Expired
- 1971-10-20 PL PL1971151125A patent/PL81417B1/pl unknown
- 1971-10-20 HU HUSA2259A patent/HU163033B/hu unknown
- 1971-10-20 SU SU1707216A patent/SU433673A3/ru active
- 1971-10-20 AT AT906971A patent/ATA906971A/de not_active Application Discontinuation
- 1971-10-21 ES ES396243A patent/ES396243A1/es not_active Expired
- 1971-10-21 DE DE19712152378 patent/DE2152378A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE774168A (fr) | 1972-04-19 |
| HU163033B (enrdf_load_stackoverflow) | 1973-05-28 |
| ZA716984B (en) | 1973-06-27 |
| NL7114314A (enrdf_load_stackoverflow) | 1972-12-19 |
| AU3483571A (en) | 1973-05-03 |
| CH558346A (de) | 1975-01-31 |
| DE2152378A1 (de) | 1972-12-21 |
| ATA906971A (de) | 1976-02-15 |
| PL81417B1 (enrdf_load_stackoverflow) | 1975-08-30 |
| FR2141647A1 (enrdf_load_stackoverflow) | 1973-01-26 |
| FR2141647B1 (enrdf_load_stackoverflow) | 1975-08-01 |
| GB1363150A (en) | 1974-08-14 |
| ES396243A1 (es) | 1975-01-01 |
| CA952515A (en) | 1974-08-06 |
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