NO129570B - - Google Patents
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- Publication number
- NO129570B NO129570B NO04896/68A NO489668A NO129570B NO 129570 B NO129570 B NO 129570B NO 04896/68 A NO04896/68 A NO 04896/68A NO 489668 A NO489668 A NO 489668A NO 129570 B NO129570 B NO 129570B
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- ene
- norpregn
- dione
- acetoxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- -1 oxy compound Chemical class 0.000 claims description 5
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012346 acetyl chloride Substances 0.000 claims description 4
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims description 4
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 11
- 230000010933 acylation Effects 0.000 description 9
- 238000005917 acylation reaction Methods 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 8
- 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
- 230000000694 effects Effects 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229960003387 progesterone Drugs 0.000 description 4
- 239000000186 progesterone Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229960003399 estrone Drugs 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
- 230000001072 progestational effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 210000004291 uterus Anatomy 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000006027 Birch reduction reaction Methods 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000001833 anti-estrogenic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 2
- 239000012285 osmium tetroxide Substances 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 241000551547 Dione <red algae> Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000328 estrogen antagonist Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- 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
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J61/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by contraction of only one ring by one or two atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO60273A NO130645C (ru) | 1967-12-08 | 1973-02-14 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68898867A | 1967-12-08 | 1967-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO129570B true NO129570B (ru) | 1974-04-29 |
Family
ID=24766615
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO04896/68A NO129570B (ru) | 1967-12-08 | 1968-12-06 |
Country Status (17)
| Country | Link |
|---|---|
| AT (4) | AT297954B (ru) |
| BE (1) | BE725078A (ru) |
| CH (3) | CH503004A (ru) |
| CY (1) | CY756A (ru) |
| DE (1) | DE1813083B2 (ru) |
| DK (1) | DK124882B (ru) |
| ES (5) | ES361100A1 (ru) |
| FI (1) | FI45552C (ru) |
| FR (1) | FR8324M (ru) |
| GB (1) | GB1235742A (ru) |
| IE (1) | IE32820B1 (ru) |
| IL (1) | IL31232A (ru) |
| MY (1) | MY7400268A (ru) |
| NL (1) | NL155556B (ru) |
| NO (1) | NO129570B (ru) |
| SE (3) | SE345263B (ru) |
| YU (2) | YU33974B (ru) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH606088A5 (ru) * | 1970-07-29 | 1978-10-13 | Richter Gedeon Vegyeszet | |
| HU230397B1 (hu) * | 2013-11-25 | 2016-04-28 | Richter Gedeon Nyrt. | Eljárás (11b,17a)-17-acetoxi-11-metil-19-norpregn-4-én-3,20-dion előállítására |
| CN109575098B (zh) * | 2019-01-18 | 2021-01-01 | 湖南成大生物科技有限公司 | 诺孕美特的合成方法 |
-
1968
- 1968-12-05 ES ES361100A patent/ES361100A1/es not_active Expired
- 1968-12-05 FI FI683505A patent/FI45552C/fi active
- 1968-12-06 SE SE16706/68A patent/SE345263B/xx unknown
- 1968-12-06 GB GB58044/68A patent/GB1235742A/en not_active Expired
- 1968-12-06 CH CH1830968A patent/CH503004A/de not_active IP Right Cessation
- 1968-12-06 DE DE1813083A patent/DE1813083B2/de active Granted
- 1968-12-06 AT AT684670A patent/AT297954B/de not_active IP Right Cessation
- 1968-12-06 AT AT684570A patent/AT301055B/de not_active IP Right Cessation
- 1968-12-06 AT AT1192368A patent/AT293634B/de not_active IP Right Cessation
- 1968-12-06 BE BE725078D patent/BE725078A/xx unknown
- 1968-12-06 YU YU2873/68A patent/YU33974B/xx unknown
- 1968-12-06 IL IL31232A patent/IL31232A/xx unknown
- 1968-12-06 NO NO04896/68A patent/NO129570B/no unknown
- 1968-12-06 AT AT684770A patent/AT297955B/de not_active IP Right Cessation
- 1968-12-06 CH CH3371A patent/CH503008A/de not_active IP Right Cessation
- 1968-12-06 FR FR177069A patent/FR8324M/fr not_active Expired
- 1968-12-06 SE SE11170/71A patent/SE365210B/xx unknown
- 1968-12-06 SE SE11171/71A patent/SE365211B/xx unknown
- 1968-12-06 CH CH3471A patent/CH503009A/de not_active IP Right Cessation
- 1968-12-06 DK DK599568AA patent/DK124882B/da unknown
- 1968-12-09 IE IE1496/68A patent/IE32820B1/xx unknown
- 1968-12-09 NL NL6817626.A patent/NL155556B/xx unknown
-
1970
- 1970-04-30 ES ES70379194A patent/ES379194A1/es not_active Expired
- 1970-04-30 ES ES379193A patent/ES379193A1/es not_active Expired
- 1970-04-30 ES ES379196A patent/ES379196A1/es not_active Expired
- 1970-04-30 ES ES379195A patent/ES379195A1/es not_active Expired
-
1974
- 1974-09-18 CY CY75674A patent/CY756A/xx unknown
- 1974-12-30 MY MY268/74A patent/MY7400268A/xx unknown
-
1975
- 1975-03-17 YU YU652/75A patent/YU34301B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES361100A1 (es) | 1970-10-16 |
| ES379194A1 (es) | 1972-09-01 |
| ES379195A1 (es) | 1972-09-01 |
| AT301055B (de) | 1972-08-25 |
| SE345263B (ru) | 1972-05-23 |
| YU65275A (en) | 1978-10-31 |
| FI45552B (ru) | 1972-04-04 |
| SE365210B (ru) | 1974-03-18 |
| DE1813083C3 (ru) | 1974-09-19 |
| CY756A (en) | 1974-09-18 |
| YU34301B (en) | 1979-04-30 |
| IL31232A0 (en) | 1969-02-27 |
| MY7400268A (en) | 1974-12-31 |
| CH503008A (de) | 1971-02-15 |
| FR8324M (ru) | 1970-12-07 |
| YU33974B (en) | 1978-09-08 |
| NL155556B (nl) | 1978-01-16 |
| CH503009A (de) | 1971-02-15 |
| AT297955B (de) | 1972-04-25 |
| DK124882B (da) | 1972-12-04 |
| CH503004A (de) | 1971-02-15 |
| DE1813083A1 (de) | 1969-10-02 |
| IE32820L (en) | 1969-06-08 |
| IL31232A (en) | 1972-12-29 |
| YU287368A (en) | 1978-02-28 |
| BE725078A (ru) | 1969-06-06 |
| AT293634B (de) | 1971-10-25 |
| NL6817626A (ru) | 1969-06-10 |
| GB1235742A (en) | 1971-06-16 |
| ES379196A1 (es) | 1972-09-01 |
| IE32820B1 (en) | 1973-12-12 |
| ES379193A1 (es) | 1972-09-01 |
| DE1813083B2 (de) | 1974-02-07 |
| SE365211B (ru) | 1974-03-18 |
| FI45552C (fi) | 1972-07-10 |
| AT297954B (de) | 1972-04-25 |
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