TWI221154B - 17alpha-hydroxy-14beta-steroids with hormonal effect - Google Patents
17alpha-hydroxy-14beta-steroids with hormonal effect Download PDFInfo
- Publication number
- TWI221154B TWI221154B TW091116164A TW91116164A TWI221154B TW I221154 B TWI221154 B TW I221154B TW 091116164 A TW091116164 A TW 091116164A TW 91116164 A TW91116164 A TW 91116164A TW I221154 B TWI221154 B TW I221154B
- Authority
- TW
- Taiwan
- Prior art keywords
- scope
- patent application
- compound
- androgen
- steroid
- Prior art date
Links
- 230000003054 hormonal effect Effects 0.000 title description 5
- 231100000508 hormonal effect Toxicity 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 239000003098 androgen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 238000011282 treatment Methods 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000011049 filling Methods 0.000 claims description 14
- -1 steroid compound Chemical class 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000001548 androgenic effect Effects 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 150000003431 steroids Chemical class 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- 239000005556 hormone Substances 0.000 claims description 4
- 229940088597 hormone Drugs 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 claims 1
- 229960003399 estrone Drugs 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 230000003637 steroidlike Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000002503 metabolic effect Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 241000282414 Homo sapiens Species 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 206010002261 Androgen deficiency Diseases 0.000 description 4
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000002079 cooperative effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000003433 contraceptive agent Substances 0.000 description 3
- 210000003494 hepatocyte Anatomy 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001311 chemical methods and process Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000002254 contraceptive effect Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane Chemical compound CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 239000004575 stone Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229960003604 testosterone Drugs 0.000 description 2
- GHPPUCVMSSFORU-GVHMLJDKSA-N (8R,9S,13S,14S)-13,15-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol Chemical compound CC1[C@@H]2[C@](C(C1)O)(C)CC[C@@H]1C3=C(CC[C@@H]21)C=C(O)C=C3 GHPPUCVMSSFORU-GVHMLJDKSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000006027 Birch reduction reaction Methods 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 101000775732 Homo sapiens Androgen receptor Proteins 0.000 description 1
- 101000928259 Homo sapiens NADPH:adrenodoxin oxidoreductase, mitochondrial Proteins 0.000 description 1
- 206010058359 Hypogonadism Diseases 0.000 description 1
- 101710186630 Insulin-1 Proteins 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 108060001084 Luciferase Proteins 0.000 description 1
- 241000699729 Muridae Species 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- DJSISFGPUUYILV-UHFFFAOYSA-N UNPD161792 Natural products O1C(C(O)=O)C(O)C(O)C(O)C1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC(O)=CC=1)O2 DJSISFGPUUYILV-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 229940030486 androgens Drugs 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 238000001574 biopsy Methods 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- NPLTVGMLNDMOQE-UHFFFAOYSA-N carthamidin Natural products C1=CC(O)=CC=C1C1OC2=CC(O)=C(O)C(O)=C2C(=O)C1 NPLTVGMLNDMOQE-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 108010050792 glutenin Proteins 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000010224 hepatic metabolism Effects 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
- 102000046818 human AR Human genes 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 208000000509 infertility Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 231100000535 infertility Toxicity 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 239000002583 male contraceptive agent Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940126701 oral medication Drugs 0.000 description 1
- 229940100688 oral solution Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229930006728 pinane Natural products 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical class O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 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
- DJSISFGPUUYILV-ZFORQUDYSA-N scutellarin Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC(O)=CC=1)O2 DJSISFGPUUYILV-ZFORQUDYSA-N 0.000 description 1
- 229930190376 scutellarin Natural products 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008700 sympathetic activation Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0062—Estrane derivatives substituted in position 17 alfa not substituted in position 17 beta
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/16—Masculine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/26—Androgens
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Endocrinology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Reproductive Health (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01203455 | 2001-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI221154B true TWI221154B (en) | 2004-09-21 |
Family
ID=8180920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091116164A TWI221154B (en) | 2001-09-12 | 2002-07-19 | 17alpha-hydroxy-14beta-steroids with hormonal effect |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US7169769B2 (enExample) |
| EP (1) | EP1427748B1 (enExample) |
| JP (1) | JP4471653B2 (enExample) |
| KR (1) | KR100940054B1 (enExample) |
| CN (1) | CN1257913C (enExample) |
| AR (1) | AR036462A1 (enExample) |
| AT (1) | ATE395352T1 (enExample) |
| AU (1) | AU2002339536B2 (enExample) |
| BR (1) | BR0212409A (enExample) |
| CA (1) | CA2505575C (enExample) |
| CY (1) | CY1108152T1 (enExample) |
| DE (1) | DE60226623D1 (enExample) |
| DK (1) | DK1427748T3 (enExample) |
| EC (1) | ECSP045012A (enExample) |
| ES (1) | ES2305306T3 (enExample) |
| HR (1) | HRP20040193A2 (enExample) |
| HU (1) | HUP0402139A3 (enExample) |
| IL (2) | IL160451A0 (enExample) |
| IS (1) | IS2555B (enExample) |
| MX (1) | MXPA04002418A (enExample) |
| NO (1) | NO326624B1 (enExample) |
| NZ (1) | NZ531487A (enExample) |
| PL (1) | PL207493B1 (enExample) |
| PT (1) | PT1427748E (enExample) |
| RU (1) | RU2294332C2 (enExample) |
| TW (1) | TWI221154B (enExample) |
| WO (1) | WO2003022864A1 (enExample) |
| ZA (1) | ZA200401992B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI221154B (en) | 2001-09-12 | 2004-09-21 | Akzo Nobel Nv | 17alpha-hydroxy-14beta-steroids with hormonal effect |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3338925A (en) * | 1965-10-25 | 1967-08-29 | Syntex Corp | 17-substituted 14beta-estr-4-enes |
| WO2000053619A1 (en) * | 1999-03-08 | 2000-09-14 | Akzo Nobel N.V. | 14.beta., 17-alpha-hydroxymethylandrostane derivatives as androgens |
| AU4299301A (en) * | 2000-02-29 | 2001-09-12 | National University Of Singapore, The | A method for modulating steroidogenic activity |
| US6391868B2 (en) * | 2000-05-10 | 2002-05-21 | Lpt Research, Inc. | Use of 5-alpha-androst-1-en-3,17-dione to increase the level of the anabolic/androgenic hormone 17-beta-hydroxy-5-alpha-androst-1-en-3-one in humans |
| TWI221154B (en) | 2001-09-12 | 2004-09-21 | Akzo Nobel Nv | 17alpha-hydroxy-14beta-steroids with hormonal effect |
-
2002
- 2002-07-19 TW TW091116164A patent/TWI221154B/zh not_active IP Right Cessation
- 2002-09-06 HR HR20040193A patent/HRP20040193A2/hr not_active Application Discontinuation
- 2002-09-06 JP JP2003526937A patent/JP4471653B2/ja not_active Expired - Fee Related
- 2002-09-06 CN CNB02817853XA patent/CN1257913C/zh not_active Expired - Lifetime
- 2002-09-06 NZ NZ531487A patent/NZ531487A/en not_active IP Right Cessation
- 2002-09-06 AT AT02777036T patent/ATE395352T1/de active
- 2002-09-06 EP EP02777036A patent/EP1427748B1/en not_active Expired - Lifetime
- 2002-09-06 IL IL16045102A patent/IL160451A0/xx unknown
- 2002-09-06 US US10/489,456 patent/US7169769B2/en not_active Expired - Lifetime
- 2002-09-06 PT PT02777036T patent/PT1427748E/pt unknown
- 2002-09-06 HU HU0402139A patent/HUP0402139A3/hu unknown
- 2002-09-06 DK DK02777036T patent/DK1427748T3/da active
- 2002-09-06 ES ES02777036T patent/ES2305306T3/es not_active Expired - Lifetime
- 2002-09-06 MX MXPA04002418A patent/MXPA04002418A/es active IP Right Grant
- 2002-09-06 PL PL368727A patent/PL207493B1/pl not_active IP Right Cessation
- 2002-09-06 RU RU2004110934/04A patent/RU2294332C2/ru not_active IP Right Cessation
- 2002-09-06 BR BR0212409-2A patent/BR0212409A/pt not_active IP Right Cessation
- 2002-09-06 AU AU2002339536A patent/AU2002339536B2/en not_active Expired
- 2002-09-06 KR KR1020047003609A patent/KR100940054B1/ko not_active Expired - Fee Related
- 2002-09-06 CA CA2505575A patent/CA2505575C/en not_active Expired - Lifetime
- 2002-09-06 DE DE60226623T patent/DE60226623D1/de not_active Expired - Lifetime
- 2002-09-06 WO PCT/EP2002/010041 patent/WO2003022864A1/en not_active Ceased
- 2002-09-10 AR ARP020103415A patent/AR036462A1/es unknown
-
2004
- 2004-02-18 IL IL160451A patent/IL160451A/en not_active IP Right Cessation
- 2004-02-26 IS IS7165A patent/IS2555B/is unknown
- 2004-03-10 EC EC2004005012A patent/ECSP045012A/es unknown
- 2004-03-10 NO NO20041010A patent/NO326624B1/no not_active IP Right Cessation
- 2004-03-11 ZA ZA200401992A patent/ZA200401992B/en unknown
-
2008
- 2008-06-19 CY CY20081100653T patent/CY1108152T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Bhavnani | Pharmacokinetics and pharmacodynamics of conjugated equine estrogens: chemistry and metabolism | |
| US8076316B2 (en) | Steroid compounds and formulations | |
| JP3814292B2 (ja) | エストラ−１，３，５（１０）−トリエン誘導体、これらの製造方法及びこれら化合物を含有する製薬組成物 | |
| CN1172949C (zh) | 睾酮衍生物 | |
| JP2002517405A (ja) | アゴニストまたはアンタゴニストホルモン特性を有する１７β−ニトロ−１１β−アリルステロイドとその誘導体 | |
| CN1200126A (zh) | 1,3,5(10)－雌三烯的氨基磺酸酯衍生物、其制备方法和含有这些化合物的药物 | |
| JP3026997B2 (ja) | １９―ノルステロイドから導かれる基が芳香族核上に置換している新規なω―フェニルアミノアルカン酸及びそれらの塩類、これらの製造法、この製造法の新規な中間体、これらの薬剤としての使用並びにこれらを含有する組成物 | |
| US10351587B2 (en) | Method of making and using 7α, 11β-dimethyl-17β-hydroxyestr-4-en-3-one 17-undecanoate | |
| JPH01197438A (ja) | 更年期障害およびホルモン依存性腫瘍の治療用ならびに避妊薬として使用するための医薬調剤およびその製法 | |
| TWI221154B (en) | 17alpha-hydroxy-14beta-steroids with hormonal effect | |
| CN101218245B (zh) | 炔雌醇的3-酯前药 | |
| AU2002339536A1 (en) | 17alpha-hydroxy-14beta-steroids with hormonal effect | |
| HK1063637B (en) | 17alpha-hydroxy-14beta-steroids with hormonal effect | |
| CN1481388A (zh) | 具有雄激素-孕激素混合活性的14(15)-不饱和的15-和/或16-取代的雄激素类 | |
| CN1226304C (zh) | 作为雄激素的亚甲基类固醇 | |
| JP2009517426A (ja) | ＥＲβ−選択物質のプロドラッグ類、それらの製造方法、及びそれらの化合物を含む医薬組成物 | |
| WO2003053993A1 (en) | Androgenic 14.alpha, 17.alpha-ethenosteroids |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |