FR2417M - - Google Patents
Download PDFInfo
- Publication number
- FR2417M FR2417M FR923183A FR923183A FR2417M FR 2417 M FR2417 M FR 2417M FR 923183 A FR923183 A FR 923183A FR 923183 A FR923183 A FR 923183A FR 2417 M FR2417 M FR 2417M
- Authority
- FR
- France
- Prior art keywords
- methyl
- androstene
- hydroxy
- anabolic
- ani
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- NXQOQNROJJFYCJ-UGCZWRCOSA-N 5alpha-androst-16-ene Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3CC[C@H]21 NXQOQNROJJFYCJ-UGCZWRCOSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 230000001195 anabolic effect Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 230000001548 androgenic effect Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000007943 implant Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
- 229960004719 nandrolone Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- 210000002307 prostate Anatomy 0.000 description 2
- 210000001625 seminal vesicle Anatomy 0.000 description 2
- 201000010653 vesiculitis Diseases 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- -1 M.p. 140 ° C Chemical compound 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- ZXSWTMLNIIZPET-ZOFHRBRSSA-N Normethandrolone Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 ZXSWTMLNIIZPET-ZOFHRBRSSA-N 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000037063 Thinness Diseases 0.000 description 1
- 150000001345 alkine derivatives Chemical class 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
- NXQOQNROJJFYCJ-FZFXZXLVSA-N androst-16-ene Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3CCC21 NXQOQNROJJFYCJ-FZFXZXLVSA-N 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 206010003549 asthenia Diseases 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000007596 consolidation process Methods 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009758 senescence Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 238000005303 weighing Methods 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
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR916520A FR1426068A (fr) | 1962-11-24 | 1962-11-24 | Nouveaux stéroïdes alcoyles, alcoylènes ou alcynes et procédé de préparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2417M true FR2417M (enrdf_load_stackoverflow) | 1964-04-24 |
Family
ID=8791520
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR916520A Expired FR1426068A (fr) | 1962-11-24 | 1962-11-24 | Nouveaux stéroïdes alcoyles, alcoylènes ou alcynes et procédé de préparation |
| FR923183A Expired FR2417M (enrdf_load_stackoverflow) | 1962-11-24 | 1963-01-30 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR916520A Expired FR1426068A (fr) | 1962-11-24 | 1962-11-24 | Nouveaux stéroïdes alcoyles, alcoylènes ou alcynes et procédé de préparation |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT253697B (enrdf_load_stackoverflow) |
| BE (1) | BE640319A (enrdf_load_stackoverflow) |
| BR (1) | BR6354775D0 (enrdf_load_stackoverflow) |
| CH (1) | CH426796A (enrdf_load_stackoverflow) |
| DK (1) | DK106670C (enrdf_load_stackoverflow) |
| ES (1) | ES293710A1 (enrdf_load_stackoverflow) |
| FR (2) | FR1426068A (enrdf_load_stackoverflow) |
| GB (1) | GB993588A (enrdf_load_stackoverflow) |
-
1962
- 1962-11-24 FR FR916520A patent/FR1426068A/fr not_active Expired
-
1963
- 1963-01-30 FR FR923183A patent/FR2417M/fr not_active Expired
- 1963-11-14 CH CH1400363A patent/CH426796A/fr unknown
- 1963-11-20 DK DK543163AA patent/DK106670C/da active
- 1963-11-21 ES ES0293710A patent/ES293710A1/es not_active Expired
- 1963-11-22 BR BR154775/63A patent/BR6354775D0/pt unknown
- 1963-11-22 GB GB46226/63A patent/GB993588A/en not_active Expired
- 1963-11-22 BE BE640319A patent/BE640319A/fr unknown
- 1963-11-22 AT AT939963A patent/AT253697B/de active
Also Published As
| Publication number | Publication date |
|---|---|
| DK106670C (da) | 1967-03-06 |
| AT253697B (de) | 1967-04-25 |
| BE640319A (fr) | 1964-05-22 |
| GB993588A (en) | 1965-05-26 |
| ES293710A1 (es) | 1964-01-16 |
| CH426796A (fr) | 1966-12-31 |
| FR1426068A (fr) | 1966-01-28 |
| BR6354775D0 (pt) | 1973-07-03 |
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