IL28936A - 11beta-nitro-9alpha-hydroxy-1,3,5(10)-estratrienes and process for preparing them - Google Patents
11beta-nitro-9alpha-hydroxy-1,3,5(10)-estratrienes and process for preparing themInfo
- Publication number
- IL28936A IL28936A IL28936A IL2893667A IL28936A IL 28936 A IL28936 A IL 28936A IL 28936 A IL28936 A IL 28936A IL 2893667 A IL2893667 A IL 2893667A IL 28936 A IL28936 A IL 28936A
- Authority
- IL
- Israel
- Prior art keywords
- carbon
- radical containing
- formula
- preparing
- process according
- Prior art date
Links
- -1 11beta-nitro-9alpha-hydroxy-1,3,5(10)-estratrienes Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 6
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 230000000802 nitrating effect Effects 0.000 claims description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 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 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000001076 estrogenic effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 229960003399 estrone Drugs 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000012044 organic layer 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 230000002513 anti-ovulatory effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 230000027046 diestrus Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002167 estrones Chemical class 0.000 description 1
- 230000001158 estrous effect Effects 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 210000003101 oviduct Anatomy 0.000 description 1
- 230000016087 ovulation Effects 0.000 description 1
- 230000000624 ovulatory effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/567—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in position 17 alpha, e.g. mestranol, norethandrolone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/566—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol having an oxo group in position 17, e.g. estrone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Steroid Compounds (AREA)
- Manufacture And Refinement Of Metals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3007766 | 1966-11-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL28936A true IL28936A (en) | 1972-07-26 |
Family
ID=11228982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL28936A IL28936A (en) | 1966-11-18 | 1967-11-13 | 11beta-nitro-9alpha-hydroxy-1,3,5(10)-estratrienes and process for preparing them |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3520909A (de) |
| AT (1) | AT271757B (de) |
| BE (1) | BE706686A (de) |
| CH (1) | CH493506A (de) |
| DE (1) | DE1618977B1 (de) |
| DK (1) | DK116659B (de) |
| ES (1) | ES347318A1 (de) |
| FR (1) | FR7064M (de) |
| GB (1) | GB1145437A (de) |
| GR (1) | GR38947B (de) |
| IL (1) | IL28936A (de) |
| NL (2) | NL6715106A (de) |
| NO (1) | NO128023B (de) |
| SE (1) | SE335527B (de) |
| YU (1) | YU31806B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5554603A (en) * | 1993-09-17 | 1996-09-10 | The United States Of America As Represented By The Department Of Health And Human Services | Orally active derivatives of 1,3,5(10)-estratriene |
-
0
- NL NL135316D patent/NL135316C/xx active
-
1967
- 1967-11-07 NL NL6715106A patent/NL6715106A/xx unknown
- 1967-11-13 DE DE1967S0112800 patent/DE1618977B1/de not_active Withdrawn
- 1967-11-13 IL IL28936A patent/IL28936A/en unknown
- 1967-11-14 FR FR128076A patent/FR7064M/fr not_active Expired
- 1967-11-14 GB GB51714/67A patent/GB1145437A/en not_active Expired
- 1967-11-14 AT AT1024767A patent/AT271757B/de active
- 1967-11-15 YU YU2225/67A patent/YU31806B/xx unknown
- 1967-11-15 DK DK569867AA patent/DK116659B/da unknown
- 1967-11-17 CH CH1615667A patent/CH493506A/de not_active IP Right Cessation
- 1967-11-17 SE SE15811/67A patent/SE335527B/xx unknown
- 1967-11-17 ES ES347318A patent/ES347318A1/es not_active Expired
- 1967-11-17 GR GR670138947A patent/GR38947B/el unknown
- 1967-11-17 BE BE706686D patent/BE706686A/xx unknown
- 1967-11-17 NO NO00170574A patent/NO128023B/no unknown
-
1969
- 1969-02-28 US US803415*A patent/US3520909A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NO128023B (de) | 1973-09-17 |
| DK116659B (da) | 1970-02-02 |
| US3520909A (en) | 1970-07-21 |
| DE1618977B1 (de) | 1972-07-20 |
| YU31806B (en) | 1973-12-31 |
| FR7064M (de) | 1969-06-23 |
| AT271757B (de) | 1969-06-10 |
| SE335527B (de) | 1971-06-01 |
| ES347318A1 (es) | 1969-02-01 |
| YU222567A (en) | 1973-06-30 |
| GB1145437A (en) | 1969-03-12 |
| NL135316C (de) | |
| CH493506A (de) | 1970-07-15 |
| BE706686A (de) | 1968-05-17 |
| GR38947B (el) | 1970-01-20 |
| NL6715106A (de) | 1968-05-20 |
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