CA2564963A1 - Steroid prodrugs with androgenic effect - Google Patents
Steroid prodrugs with androgenic effect Download PDFInfo
- Publication number
- CA2564963A1 CA2564963A1 CA002564963A CA2564963A CA2564963A1 CA 2564963 A1 CA2564963 A1 CA 2564963A1 CA 002564963 A CA002564963 A CA 002564963A CA 2564963 A CA2564963 A CA 2564963A CA 2564963 A1 CA2564963 A1 CA 2564963A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- beta
- sulfamoyl benzoate
- oxo
- sulfamoyl
- 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.)
- Abandoned
Links
- 150000003431 steroids Chemical class 0.000 title claims abstract description 22
- 239000000651 prodrug Substances 0.000 title claims abstract description 8
- 229940002612 prodrug Drugs 0.000 title claims abstract description 8
- 230000001548 androgenic effect Effects 0.000 title abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Chemical group 0.000 claims abstract description 7
- 239000003098 androgen Substances 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- -1 perhydropyran-2-yl Chemical group 0.000 claims description 31
- 229940030486 androgens Drugs 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 238000002560 therapeutic procedure Methods 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 15
- 238000006467 substitution reaction Methods 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- JOMQIRBLMOXBAZ-UHFFFAOYSA-N sulfamoyl benzoate Chemical compound NS(=O)(=O)OC(=O)C1=CC=CC=C1 JOMQIRBLMOXBAZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000008177 pharmaceutical agent Substances 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite group Chemical group N(=O)[O-] IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 230000003637 steroidlike Effects 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 239000003862 glucocorticoid Substances 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 4
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 3
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- 230000008569 process Effects 0.000 claims description 3
- 239000000583 progesterone congener Substances 0.000 claims description 3
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 claims description 3
- KDNIOKSLVIGAAN-UHFFFAOYSA-N 2-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC=CC=C1C(O)=O KDNIOKSLVIGAAN-UHFFFAOYSA-N 0.000 claims description 2
- NMJREATYWWNIKX-UHFFFAOYSA-N GnRH Chemical class C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CC(C)C)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 NMJREATYWWNIKX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 238000002657 hormone replacement therapy Methods 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- FOKNEOPXGZGGBW-UHFFFAOYSA-N sulfamoyl isocyanate Chemical compound NS(=O)(=O)N=C=O FOKNEOPXGZGGBW-UHFFFAOYSA-N 0.000 claims description 2
- 229910006074 SO2NH2 Inorganic materials 0.000 claims 7
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 101100240526 Caenorhabditis elegans nhr-20 gene Proteins 0.000 claims 3
- 125000002560 nitrile group Chemical group 0.000 claims 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000002345 steroid group Chemical group 0.000 abstract 1
- 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 80
- 238000012360 testing method Methods 0.000 description 51
- 239000000126 substance Substances 0.000 description 49
- 229960003604 testosterone Drugs 0.000 description 40
- 239000000243 solution Substances 0.000 description 35
- 238000005160 1H NMR spectroscopy Methods 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 210000003743 erythrocyte Anatomy 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
- 230000000875 corresponding effect Effects 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- YSGQGNQWBLYHPE-CFUSNLFHSA-N (7r,8r,9s,10r,13s,14s,17s)-17-hydroxy-7,13-dimethyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1C[C@]2(C)[C@@H](O)CC[C@H]2[C@@H]2[C@H](C)CC3=CC(=O)CC[C@@H]3[C@H]21 YSGQGNQWBLYHPE-CFUSNLFHSA-N 0.000 description 19
- 101000954831 Homo sapiens Protein MENT Proteins 0.000 description 19
- 102100037056 Protein MENT Human genes 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 238000001704 evaporation Methods 0.000 description 17
- 230000008020 evaporation Effects 0.000 description 17
- 230000009471 action Effects 0.000 description 16
- 241000700159 Rattus Species 0.000 description 13
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- 210000004185 liver Anatomy 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 230000028327 secretion Effects 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000006870 function Effects 0.000 description 9
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- 229940088597 hormone Drugs 0.000 description 9
- 239000005556 hormone Substances 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- XWEBTVZIZWEJOO-UHFFFAOYSA-N 3-chlorosulfonylbenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 XWEBTVZIZWEJOO-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 108010010234 HDL Lipoproteins Proteins 0.000 description 8
- 102000015779 HDL Lipoproteins Human genes 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
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- 230000012010 growth Effects 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
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- 239000000047 product Substances 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
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- JFEPJTGMGDGPHJ-PNKHAZJDSA-N (8r,9s,10r,13s,14s)-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 JFEPJTGMGDGPHJ-PNKHAZJDSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
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- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 210000004999 sex organ Anatomy 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 210000000106 sweat gland Anatomy 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0038—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an androstane skeleton, including 18- or 19-substituted derivatives, 18-nor derivatives and also derivatives where position 17-beta is substituted by a carbon atom not directly bonded to a further carbon atom and not being part of an amide group
-
- 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
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0044—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an estrane or gonane skeleton, including 18-substituted derivatives and derivatives where position 17-beta is substituted by a carbon atom not directly bonded to another carbon atom and not being part of an amide group
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004025986.0 | 2004-05-21 | ||
DE102004025986A DE102004025986A1 (de) | 2004-05-21 | 2004-05-21 | Steroid-Prodrugs mit androgener Wirkung |
PCT/EP2005/005256 WO2005113575A1 (de) | 2004-05-21 | 2005-05-10 | Steroid-prodrugs mit androgener wirkung |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2564963A1 true CA2564963A1 (en) | 2005-12-01 |
Family
ID=34968657
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002564963A Abandoned CA2564963A1 (en) | 2004-05-21 | 2005-05-10 | Steroid prodrugs with androgenic effect |
Country Status (22)
Country | Link |
---|---|
EP (1) | EP1747229A1 (es) |
JP (1) | JP2007538026A (es) |
CN (1) | CN1993375A (es) |
AR (1) | AR049547A1 (es) |
AU (1) | AU2005245568A1 (es) |
BR (1) | BRPI0510136A (es) |
CA (1) | CA2564963A1 (es) |
CR (1) | CR8785A (es) |
DE (1) | DE102004025986A1 (es) |
EA (1) | EA200602049A1 (es) |
EC (1) | ECSP067028A (es) |
GT (1) | GT200500122A (es) |
IL (1) | IL179293A0 (es) |
MX (1) | MXPA06013469A (es) |
NO (1) | NO20065885L (es) |
PA (1) | PA8633601A1 (es) |
PE (1) | PE20060271A1 (es) |
SV (1) | SV2006002123A (es) |
TW (1) | TW200613317A (es) |
UY (1) | UY28911A1 (es) |
WO (1) | WO2005113575A1 (es) |
ZA (1) | ZA200610769B (es) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10027887A1 (de) | 2000-05-31 | 2001-12-13 | Jenapharm Gmbh | Verbindungen mit einer Sulfonamidgruppe und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
US7534780B2 (en) | 2004-05-21 | 2009-05-19 | Bayer Schering Pharma Aktiengesellschaft | Estradiol prodrugs |
DE102005057224A1 (de) * | 2005-11-29 | 2007-05-31 | Bayer Schering Pharma Ag | Prodrugs ERß-selektiver Substanzen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
DE102005057408A1 (de) * | 2005-11-30 | 2007-05-31 | Bayer Schering Pharma Ag | Sulfamoylsulfonat-Prodrugs |
CN101708338B (zh) * | 2008-12-26 | 2014-06-04 | 中国人民解放军军事医学科学院放射与辐射医学研究所 | 含甾体结构的前药及其高度分散制剂 |
CN102964417A (zh) * | 2012-11-30 | 2013-03-13 | 华中药业股份有限公司 | 17-羟基四氢吡喃醚甾族化合物的合成方法 |
CN107556258B (zh) * | 2017-08-22 | 2021-06-04 | 湖北江田精密化学有限公司 | 一种4-氨基-2-氯-5(1h-四唑基-5)苯磺酰胺的制备方法 |
EP3533619A1 (en) * | 2018-03-02 | 2019-09-04 | Basf Se | Heat sensitive recording material and color developer |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH545316A (de) * | 1970-07-17 | 1973-12-15 | Hoffmann La Roche | Verfahren zur Herstellung von Acylderivaten |
US5001234A (en) * | 1987-04-16 | 1991-03-19 | The Upjohn Company | Cyclic hydrocarbons with an aminoalkyl sidechain |
US5571933A (en) * | 1994-11-17 | 1996-11-05 | Duquesne University Of The Holy Ghost | Derivatives of estra 1,3,5(10)triene-17-one, 3-amino compounds and their use |
DE19712488A1 (de) * | 1997-03-25 | 1998-10-01 | Knoell Hans Forschung Ev | Steroidsulfamate, Verfahren zu ihrer Herstellung und Anwendung derselben |
DE10027887A1 (de) * | 2000-05-31 | 2001-12-13 | Jenapharm Gmbh | Verbindungen mit einer Sulfonamidgruppe und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
-
2004
- 2004-05-21 DE DE102004025986A patent/DE102004025986A1/de not_active Ceased
-
2005
- 2005-05-10 CN CNA200580016339XA patent/CN1993375A/zh active Pending
- 2005-05-10 EA EA200602049A patent/EA200602049A1/ru unknown
- 2005-05-10 WO PCT/EP2005/005256 patent/WO2005113575A1/de active Application Filing
- 2005-05-10 BR BRPI0510136-0A patent/BRPI0510136A/pt not_active Application Discontinuation
- 2005-05-10 CA CA002564963A patent/CA2564963A1/en not_active Abandoned
- 2005-05-10 JP JP2007517047A patent/JP2007538026A/ja active Pending
- 2005-05-10 MX MXPA06013469A patent/MXPA06013469A/es not_active Application Discontinuation
- 2005-05-10 AU AU2005245568A patent/AU2005245568A1/en not_active Abandoned
- 2005-05-10 EP EP05742657A patent/EP1747229A1/de not_active Withdrawn
- 2005-05-20 PE PE2005000556A patent/PE20060271A1/es not_active Application Discontinuation
- 2005-05-20 PA PA20058633601A patent/PA8633601A1/es unknown
- 2005-05-20 AR ARP050102084A patent/AR049547A1/es not_active Application Discontinuation
- 2005-05-20 GT GT200500122A patent/GT200500122A/es unknown
- 2005-05-20 TW TW094116504A patent/TW200613317A/zh unknown
- 2005-05-20 UY UY28911A patent/UY28911A1/es not_active Application Discontinuation
- 2005-05-23 SV SV2005002123A patent/SV2006002123A/es not_active Application Discontinuation
-
2006
- 2006-11-15 IL IL179293A patent/IL179293A0/en unknown
- 2006-11-27 EC EC2006007028A patent/ECSP067028A/es unknown
- 2006-12-05 CR CR8785A patent/CR8785A/es not_active Application Discontinuation
- 2006-12-19 NO NO20065885A patent/NO20065885L/no unknown
- 2006-12-20 ZA ZA200610769A patent/ZA200610769B/xx unknown
Also Published As
Publication number | Publication date |
---|---|
PA8633601A1 (es) | 2006-07-03 |
DE102004025986A1 (de) | 2005-12-15 |
BRPI0510136A (pt) | 2007-10-02 |
EP1747229A1 (de) | 2007-01-31 |
GT200500122A (es) | 2006-01-24 |
WO2005113575A1 (de) | 2005-12-01 |
NO20065885L (no) | 2006-12-19 |
TW200613317A (en) | 2006-05-01 |
AR049547A1 (es) | 2006-08-16 |
MXPA06013469A (es) | 2007-01-23 |
IL179293A0 (en) | 2007-03-08 |
ECSP067028A (es) | 2006-12-29 |
UY28911A1 (es) | 2005-12-30 |
SV2006002123A (es) | 2006-02-15 |
PE20060271A1 (es) | 2006-05-25 |
JP2007538026A (ja) | 2007-12-27 |
ZA200610769B (en) | 2008-08-27 |
CN1993375A (zh) | 2007-07-04 |
CR8785A (es) | 2007-02-05 |
AU2005245568A1 (en) | 2005-12-01 |
EA200602049A1 (ru) | 2007-06-29 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FZDE | Discontinued |