JPH01131193A - １４α−ヒドロキシ−アンドロスト−４−エン−３，６，１７−トリオンのエステル誘導体 - Google Patents
１４α−ヒドロキシ−アンドロスト−４−エン−３，６，１７−トリオンのエステル誘導体Info
- Publication number
- JPH01131193A JPH01131193A JP62270417A JP27041787A JPH01131193A JP H01131193 A JPH01131193 A JP H01131193A JP 62270417 A JP62270417 A JP 62270417A JP 27041787 A JP27041787 A JP 27041787A JP H01131193 A JPH01131193 A JP H01131193A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- androst
- trione
- ethyl acetate
- androstene
- 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.)
- Granted
Links
- -1 Ester derivative of 14alpha-hydroxy-androst-4-ene-3,6,17-trione Chemical class 0.000 title description 2
- 239000000126 substance Substances 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 34
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 6
- 210000002826 placenta Anatomy 0.000 abstract description 6
- 102000014654 Aromatase Human genes 0.000 abstract description 5
- 108010078554 Aromatase Proteins 0.000 abstract description 5
- 230000002401 inhibitory effect Effects 0.000 abstract description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 4
- UKVVNEHFNYKGMX-KIVPVIKRSA-N (8r,9s,10r,13s,14r)-14-hydroxy-10,13-dimethyl-2,7,8,9,11,12,15,16-octahydro-1h-cyclopenta[a]phenanthrene-3,6,17-trione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@]4(O)[C@@H]3CC(=O)C2=C1 UKVVNEHFNYKGMX-KIVPVIKRSA-N 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 208000005156 Dehydration Diseases 0.000 abstract 1
- 230000003327 cancerostatic effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 238000004811 liquid chromatography Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001443 androstenes Chemical class 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 230000004071 biological effect Effects 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 239000012156 elution solvent Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 3
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 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
- 238000000862 absorption spectrum Methods 0.000 description 2
- 229960005471 androstenedione Drugs 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- DJPCGJZXEONFLB-MEYPQBBUSA-N (8r,9s,10r,13s,14s)-13-(hydroxymethyl)-10-methyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,6,17-trione Chemical compound C([C@]1(CO)C(=O)CC[C@H]1[C@@H]1CC2=O)C[C@@H]1[C@]1(C)C2=CC(=O)CC1 DJPCGJZXEONFLB-MEYPQBBUSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000228417 Sarocladium strictum Species 0.000 description 1
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 description 1
- AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000003560 cancer drug Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000003028 enzyme activity measurement method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62270417A JPH01131193A (ja) | 1987-08-07 | 1987-10-28 | １４α−ヒドロキシ−アンドロスト−４−エン−３，６，１７−トリオンのエステル誘導体 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62-197590 | 1987-08-07 | ||
| JP19759087 | 1987-08-07 | ||
| JP62270417A JPH01131193A (ja) | 1987-08-07 | 1987-10-28 | １４α−ヒドロキシ−アンドロスト−４−エン−３，６，１７−トリオンのエステル誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01131193A true JPH01131193A (ja) | 1989-05-24 |
| JPH0369357B2 JPH0369357B2 (cs) | 1991-10-31 |
Family
ID=26510452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62270417A Granted JPH01131193A (ja) | 1987-08-07 | 1987-10-28 | １４α−ヒドロキシ−アンドロスト−４−エン−３，６，１７−トリオンのエステル誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01131193A (cs) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03294230A (ja) * | 1990-04-12 | 1991-12-25 | Snow Brand Milk Prod Co Ltd | 子宮内膜症治療剤 |
| JPH04112898A (ja) * | 1990-08-31 | 1992-04-14 | Snow Brand Milk Prod Co Ltd | 新規なアンドロステン誘導体及びそれを用いる６‐アルキルカルボニルオキシ‐１４α‐ヒドロキシ‐アンドロスト‐４，６‐ジエン‐３，１７‐ジオンの製造法 |
-
1987
- 1987-10-28 JP JP62270417A patent/JPH01131193A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03294230A (ja) * | 1990-04-12 | 1991-12-25 | Snow Brand Milk Prod Co Ltd | 子宮内膜症治療剤 |
| JPH04112898A (ja) * | 1990-08-31 | 1992-04-14 | Snow Brand Milk Prod Co Ltd | 新規なアンドロステン誘導体及びそれを用いる６‐アルキルカルボニルオキシ‐１４α‐ヒドロキシ‐アンドロスト‐４，６‐ジエン‐３，１７‐ジオンの製造法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0369357B2 (cs) | 1991-10-31 |
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