CA2486495A1 - 9-alpha-substituted estratrienes as selectively active estrogens - Google Patents
9-alpha-substituted estratrienes as selectively active estrogens Download PDFInfo
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- C07J1/0051—Estrane derivatives
- C07J1/0055—Estrane derivatives not substituted in position 17
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- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
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- A—HUMAN NECESSITIES
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- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- 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
- A61P5/30—Oestrogens
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- 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
- C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
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- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
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- 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
- C07J41/0072—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the A ring of the steroid being aromatic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
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Abstract
The invention relates to novel 9.alpha.-substituted estratrienes of general formula (I) - wherein R3, R7, R7', R13, R16, R17 and R17' have the designations cited in the description, and R9 represents a linear-chain or branched-chain, optionally partially or fully halogenated alkenyl radical comprising between 2 and 6 carbon atoms, or an ethinyl radical or a prop-1- inyl radical - as pharmaceutical active ingredients which have, in vitro, a higher affinity to estrogen receptor preparations of the rat prostate than t o estrogen receptor preparation of the rat uterus, and, in vivo, preferably a preferential action on the ovary compared to the uterus. The invention also relates to the production of said estratrienes, to the therapeutic applicati on thereof and to pharmaceutical forms of administration containing the novel compounds. The invention further relates to the use of said compounds for treating illnesses and states related to estrogen deficiency.
Claims (23)
1. 9.alpha.-Substituted estra-1,3,5(10)-triene derivatives of general formula I
in which radicals R3, R7, R7', R9, R13, R16 as well as R17 and R17', independently of one another, have the following meaning:
R3 means a hydrogen atom or a group R18, in which R18 means a straight-chain or branched-chain, saturated or unsaturated hydrocarbon radical with up to 6 carbon atoms, a trifluoromethyl group, an aryl, heteroaryl or aralkyl radical, a substituted aryl, heteroaryl radical with a methyl, ethyl, trifluoromethyl, pentafluoroethyl, trifluoromethylthio, methoxy, ethoxy, nitro, cyano, halo- (fluorine, chlorine, bromine, iodine), hydroxy, amino, mono(C1-6-alkyl) or di(C1-6-alkyl)amino, whereby both alkyl groups are identical or different, di(aralkyl)amino, whereby both aralkyl groups are identical or different, carboxyl, carboxyalkoxy, C1-C20-acyl or C1-C20-acyloxy groups as substituents, an acyl radical COR19, in which R19 is a straight-chain or branched-chain hydrocarbon radical with up to 10 carbon atoms that is saturated or unsaturated in up to three places and is partially or completely halogenated, or R18 ~means a group R20SO2, in which R20 ~is an R21R22N group, whereby R21 and R22, independently of one another, mean a hydrogen atom, a C1-C5-alkyl radical, a group C(O)R23, in which R23 [represents] a straight-chain or branched-chain hydrocarbon radical with up to 10 carbon atoms that is saturated or unsaturated in up to three places and is partially or completely halogenated, a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group, a C4-C15-cycloalkylalkyl radical with 3 to 7 carbon atoms in the cycloalkyl portion and with an alkyl portion of up to 8 carbon atoms or an aryl, heteroaryl or aralkyl radical, or a substituted aryl, or heteroaryl radical, with a methyl, ethyl, trifluoromethyl, pentafluroethyl, trifluoromethylthio, methoxy, ethoxy, nitro, cyano, halo- (fluorine, chlorine, bromine, iodine), hydroxy, amino, mono(C1-4-alkyl) or di(C1-6-alkyl) amino, whereby both alkyl groups are identical or different, di (aralkyl)amino, whereby both aralkyl groups are identical or different, carboxyl, carboxyalkoxy, C1-C20-acyl or C1-C20-acyloxy groups as substituents, or, together with the N atom, a 43a polymethylenimino radical with 4 to 6 C atoms or a morpholino radical, R7 and R7', in each case independently of one another, are a hydrogen atom or a halogen atom, R9 ~is a straight-chain or branched-chain alkenyl or alkinyl radical with 2 to 6 carbon atoms, which can be partially or completely fluorinated, or an ethinyl- or prop-1-prop-1-inyl radical, R13 ~is a methyl group or an ethyl group, R16 ~is a hydroxy group or a group R18O-, R20SO2- or OC(O)R23 with R18, R20 and R23 in each case in the meaning that is indicated under R3, R17 and R17', in each case independently of one another, are a hydrogen atom or a halogen atom.
in which radicals R3, R7, R7', R9, R13, R16 as well as R17 and R17', independently of one another, have the following meaning:
R3 means a hydrogen atom or a group R18, in which R18 means a straight-chain or branched-chain, saturated or unsaturated hydrocarbon radical with up to 6 carbon atoms, a trifluoromethyl group, an aryl, heteroaryl or aralkyl radical, a substituted aryl, heteroaryl radical with a methyl, ethyl, trifluoromethyl, pentafluoroethyl, trifluoromethylthio, methoxy, ethoxy, nitro, cyano, halo- (fluorine, chlorine, bromine, iodine), hydroxy, amino, mono(C1-6-alkyl) or di(C1-6-alkyl)amino, whereby both alkyl groups are identical or different, di(aralkyl)amino, whereby both aralkyl groups are identical or different, carboxyl, carboxyalkoxy, C1-C20-acyl or C1-C20-acyloxy groups as substituents, an acyl radical COR19, in which R19 is a straight-chain or branched-chain hydrocarbon radical with up to 10 carbon atoms that is saturated or unsaturated in up to three places and is partially or completely halogenated, or R18 ~means a group R20SO2, in which R20 ~is an R21R22N group, whereby R21 and R22, independently of one another, mean a hydrogen atom, a C1-C5-alkyl radical, a group C(O)R23, in which R23 [represents] a straight-chain or branched-chain hydrocarbon radical with up to 10 carbon atoms that is saturated or unsaturated in up to three places and is partially or completely halogenated, a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group, a C4-C15-cycloalkylalkyl radical with 3 to 7 carbon atoms in the cycloalkyl portion and with an alkyl portion of up to 8 carbon atoms or an aryl, heteroaryl or aralkyl radical, or a substituted aryl, or heteroaryl radical, with a methyl, ethyl, trifluoromethyl, pentafluroethyl, trifluoromethylthio, methoxy, ethoxy, nitro, cyano, halo- (fluorine, chlorine, bromine, iodine), hydroxy, amino, mono(C1-4-alkyl) or di(C1-6-alkyl) amino, whereby both alkyl groups are identical or different, di (aralkyl)amino, whereby both aralkyl groups are identical or different, carboxyl, carboxyalkoxy, C1-C20-acyl or C1-C20-acyloxy groups as substituents, or, together with the N atom, a 43a polymethylenimino radical with 4 to 6 C atoms or a morpholino radical, R7 and R7', in each case independently of one another, are a hydrogen atom or a halogen atom, R9 ~is a straight-chain or branched-chain alkenyl or alkinyl radical with 2 to 6 carbon atoms, which can be partially or completely fluorinated, or an ethinyl- or prop-1-prop-1-inyl radical, R13 ~is a methyl group or an ethyl group, R16 ~is a hydroxy group or a group R18O-, R20SO2- or OC(O)R23 with R18, R20 and R23 in each case in the meaning that is indicated under R3, R17 and R17', in each case independently of one another, are a hydrogen atom or a halogen atom.
2. Compounds of general formula I according to claim 1, in which R3 is a hydrogen atom.
3. Compounds of general formula I according to claim 1 or 2, in which R7 is a hydrogen atom or an .alpha.-position fluorine atom, R9 is a vinyl, ethinyl or prop-1-inyl group, R16 is a hydroxy group, and R17 is a hydrogen atom or an .alpha.-position fluorine atom.
4. Compounds of general formula I according to claim 1 or 2, in which R16 stands for a group R18-O- or R19SO2-O- with R18 and R19 in each case in the meaning that is indicated under R3.
5. Estratrienes of general formula I according to claim 1 or 2, namely:
9.alpha.-Vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 9.alpha.-Allyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 18a-Homo-9.alpha.-vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 18a-Homo-9.alpha.-allyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 3-Methoxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-16.alpha.-ol 9.alpha.-Allyl-3-methoxy-estra-1,3,5(10)-trien-16.alpha.-ol 18a-Homo-3-methoxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-16.alpha.-ol 18a-Homo-9.alpha.-allyl-3-methoxy-estra-1,3,5(10)-trien-16.alpha.-ol 9.alpha.-(2',2'-Difluorovinyl)-estra-1,3,5(10)-triene-3,16.alpha.-diol 9.alpha.-(2',2'-Difluorovinyl)-3-methoxy-estra-1,3,5(10)-trien-16.alpha.-ol 16.alpha.-Hydroxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-3yl-sulfamate 9.alpha.-Allyl-16.alpha.-hydroxy-estra-1,3,5(10)-trien-3yl-sulfamate 18a-Homo-16.alpha.-hydroxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-3yl-sulfamate 18a-Homo-9.alpha.-allyl-16.alpha.-hydroxy-estra-1,3,5(10)-trien-3yl-sulfamate 9.alpha.-Vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diyl-disulfamate 9.alpha.-Allyl-estra-1,3,5(10)-triene-3,16.alpha.-diyl-disulfamate 18.alpha.-Homo-9.alpha.-vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diyl-disulfamate 18a-Homo-9.alpha.-allyl-estra-1,3,5(10)-triene-3,16.alpha.-diyl-disulfamate 16.alpha.-Hydroxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-3yl-(N-acetyl)-sulfamate 9a-Allyl-16.alpha.-hydroxy-estra-1,3,5(10)-trien-3yl-(N-acetyl)-sulfamate 18a-Homo-16.alpha.-hydroxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-3yl-(N-acetyl)-sulfamate 18a-Homo-9.alpha.-allyl-16.alpha.-hydroxy-estra-1,3,5(10)-trien-3yl-(N-acetyl)-sulfamate 9.alpha.-(Prop-(Z)-enyl)-estra-1,3,5(10)-triene-3,16.alpha.-diol 9.alpha.-(n-Propyl)-estra-1,3,5(10)-triene-3,16.alpha.-diol 9.alpha.-Ethinyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 9.alpha.-Vinyl-estra-1,3,5(10)-triene-3,16a-diol-diacetate 18a-Homo-9.alpha.-vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diol-diacetate 16.alpha.-Valeroyloxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-3-ol 16.alpha.-Acetoxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-3-ol 18a-Homo-16.alpha.-acetoxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-3-ol 7.alpha.-Fluoro-9.alpha.-vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 7.alpha.-Fluoro-9.alpha.-allyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 17.beta.3-Fluoro-9.alpha.-vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 17.beta.3-Fluoro-9.alpha.-allyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 18a-Homo-7.alpha.-fluoro-9.alpha.-vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 18a-Homo-7.alpha.-fluoro-9.alpha.-allyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 18a-Homo-17.beta.-fluoro-9.alpha.-vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 18a-Homo-17.beta.-fluoro-9.alpha.-allyl-estra-1,3,5(10)-triene-3,16.alpha.-diol
9.alpha.-Vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 9.alpha.-Allyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 18a-Homo-9.alpha.-vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 18a-Homo-9.alpha.-allyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 3-Methoxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-16.alpha.-ol 9.alpha.-Allyl-3-methoxy-estra-1,3,5(10)-trien-16.alpha.-ol 18a-Homo-3-methoxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-16.alpha.-ol 18a-Homo-9.alpha.-allyl-3-methoxy-estra-1,3,5(10)-trien-16.alpha.-ol 9.alpha.-(2',2'-Difluorovinyl)-estra-1,3,5(10)-triene-3,16.alpha.-diol 9.alpha.-(2',2'-Difluorovinyl)-3-methoxy-estra-1,3,5(10)-trien-16.alpha.-ol 16.alpha.-Hydroxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-3yl-sulfamate 9.alpha.-Allyl-16.alpha.-hydroxy-estra-1,3,5(10)-trien-3yl-sulfamate 18a-Homo-16.alpha.-hydroxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-3yl-sulfamate 18a-Homo-9.alpha.-allyl-16.alpha.-hydroxy-estra-1,3,5(10)-trien-3yl-sulfamate 9.alpha.-Vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diyl-disulfamate 9.alpha.-Allyl-estra-1,3,5(10)-triene-3,16.alpha.-diyl-disulfamate 18.alpha.-Homo-9.alpha.-vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diyl-disulfamate 18a-Homo-9.alpha.-allyl-estra-1,3,5(10)-triene-3,16.alpha.-diyl-disulfamate 16.alpha.-Hydroxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-3yl-(N-acetyl)-sulfamate 9a-Allyl-16.alpha.-hydroxy-estra-1,3,5(10)-trien-3yl-(N-acetyl)-sulfamate 18a-Homo-16.alpha.-hydroxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-3yl-(N-acetyl)-sulfamate 18a-Homo-9.alpha.-allyl-16.alpha.-hydroxy-estra-1,3,5(10)-trien-3yl-(N-acetyl)-sulfamate 9.alpha.-(Prop-(Z)-enyl)-estra-1,3,5(10)-triene-3,16.alpha.-diol 9.alpha.-(n-Propyl)-estra-1,3,5(10)-triene-3,16.alpha.-diol 9.alpha.-Ethinyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 9.alpha.-Vinyl-estra-1,3,5(10)-triene-3,16a-diol-diacetate 18a-Homo-9.alpha.-vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diol-diacetate 16.alpha.-Valeroyloxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-3-ol 16.alpha.-Acetoxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-3-ol 18a-Homo-16.alpha.-acetoxy-9.alpha.-vinyl-estra-1,3,5(10)-trien-3-ol 7.alpha.-Fluoro-9.alpha.-vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 7.alpha.-Fluoro-9.alpha.-allyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 17.beta.3-Fluoro-9.alpha.-vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 17.beta.3-Fluoro-9.alpha.-allyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 18a-Homo-7.alpha.-fluoro-9.alpha.-vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 18a-Homo-7.alpha.-fluoro-9.alpha.-allyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 18a-Homo-17.beta.-fluoro-9.alpha.-vinyl-estra-1,3,5(10)-triene-3,16.alpha.-diol 18a-Homo-17.beta.-fluoro-9.alpha.-allyl-estra-1,3,5(10)-triene-3,16.alpha.-diol
6. Pharmaceutical compositions that contain at least one compound according to one of claims 1 to 5 as well as a pharmaceutically compatible vehicle.
7. ~Use of the compounds of general formula I according to claims 1-5 above for production of pharmaceutical agents.
8. ~Use according to claim 7 for treatment of estrogen-deficiency-induced diseases and conditions in women and in men.
9. ~Use according to claim 7 for treatment of peri- and postmenopausal symptoms.
10. ~Use according to claim 7 for the in-vitro treatment of female infertility.
11. ~Use according to claim 7 for the in-vivo treatment of female infertility.
12. ~Use according to claim 7 for the therapy of hormone-deficiency-induced symptoms in ovarian dysfunction that is caused by surgery, medication, etc.
13. ~Use according to claim 7 for hormone replacement therapy (HRT).
14. ~Use according to claim 13 in combination with selective estrogen receptor modulators (SERM), for example raloxifene.
15. ~Use according to claim 7 for prophylaxis and therapy of a hormone-deficiency-induced bone mass loss.
16. ~Use according to claim 7 for prophylaxis and therapy of osteoporosis.
17. ~Use according to claim 7 for prophylaxis and therapy of cardiovascular diseases.
18. ~Use according to claim 7 for prevention and treatment of prostate hyperplasia.
19. ~Use according to claim 18 in combination with antiestrogens and selective estrogen receptor modulators (SERM) for prophylaxis and therapy of prostate hyperplasia.
20. ~Use according to claim 7 for treatment of diseases of the immune system.
21. ~Use according to claim 20 for treatment of autoimmune diseases.
22. ~Use according to claim 21 for treatment of rheumatoid arthritis.
23. ~Use according to claim 21 for treatment of multiple sclerosis.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10226326A DE10226326A1 (en) | 2002-06-11 | 2002-06-11 | 9-alpha-substituted estratrienes as selective estrogens |
| DE10226326.4 | 2002-06-11 | ||
| PCT/EP2003/006172 WO2003104253A2 (en) | 2002-06-11 | 2003-06-11 | 9-alpha-substituted estratrienes as selectively active estrogen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2486495A1 true CA2486495A1 (en) | 2003-12-18 |
| CA2486495C CA2486495C (en) | 2011-04-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2486495A Expired - Fee Related CA2486495C (en) | 2002-06-11 | 2003-06-11 | 9-alpha-substituted estratrienes as selectively active estrogens |
Country Status (28)
| Country | Link |
|---|---|
| EP (1) | EP1517914B1 (en) |
| JP (1) | JP4615998B2 (en) |
| KR (1) | KR101006612B1 (en) |
| CN (1) | CN1293090C (en) |
| AR (1) | AR040188A1 (en) |
| AT (1) | ATE303397T1 (en) |
| AU (1) | AU2003242683B9 (en) |
| BR (1) | BR0312140A (en) |
| CA (1) | CA2486495C (en) |
| CR (1) | CR10289A (en) |
| CU (1) | CU23414B7 (en) |
| DE (2) | DE10226326A1 (en) |
| DK (1) | DK1517914T3 (en) |
| EA (1) | EA008442B1 (en) |
| EC (1) | ECSP055530A (en) |
| ES (1) | ES2248770T3 (en) |
| HR (1) | HRP20050009B1 (en) |
| IL (1) | IL165321A (en) |
| MX (1) | MXPA04012491A (en) |
| NO (1) | NO329563B1 (en) |
| PE (1) | PE20040613A1 (en) |
| PL (1) | PL209910B1 (en) |
| RS (1) | RS50878B (en) |
| TW (1) | TWI286140B (en) |
| UA (1) | UA78062C2 (en) |
| UY (1) | UY27844A1 (en) |
| WO (1) | WO2003104253A2 (en) |
| ZA (1) | ZA200500217B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110052699A1 (en) * | 2008-02-13 | 2011-03-03 | Adrian Funke | Drug delivery system with stabilising effect |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10027887A1 (en) | 2000-05-31 | 2001-12-13 | Jenapharm Gmbh | Compounds with a sulfonamide group and pharmaceutical compositions containing these compounds |
| DE602004014020D1 (en) * | 2003-11-26 | 2008-07-03 | Bayer Schering Pharma Ag | PREVENTION AND TREATMENT OF HYPERTONE DISEASES WITH THE SELECTIVE ESTROGENIC 8BETA-VINYL-ESTRA-1,3,5 (10) -TRIEN-3,17BETA-DIOL AND 17BETA-FLUOR-9ALPHA-VINYL-ESTRA-1,3,5 (10 ) -triene-3,16ALPHA-dIOL |
| US7534780B2 (en) | 2004-05-21 | 2009-05-19 | Bayer Schering Pharma Aktiengesellschaft | Estradiol prodrugs |
| DE102005057224A1 (en) | 2005-11-29 | 2007-05-31 | Bayer Schering Pharma Ag | New 9-alpha substituted estratriene derivatives esterified with a sulfamoylphenyl-substituted acid residue, are prodrugs useful as carboanhydrase inhibitors for treating estrogen deficiency disorders |
| EP2143432A1 (en) | 2008-07-11 | 2010-01-13 | Bayer Schering Pharma AG | 9-alpha estratriene derivatives as ER-beta selective ligands for the prevention and treatment of intestinal cancer |
| EP2358351A1 (en) * | 2008-11-21 | 2011-08-24 | Bayer Pharma Aktiengesellschaft | Drug delivery system |
| EP3185881B1 (en) | 2014-08-26 | 2022-03-09 | Betanien Hospital | Methods, agents and compositions for treatment of inflammatory conditions |
| CA3109978A1 (en) * | 2018-09-07 | 2020-03-12 | Trustees Of Dartmouth College | C19 scaffolds and steroids and methods of use and manufacture thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2336432A1 (en) * | 1973-07-13 | 1975-01-30 | Schering Ag | 3.17.18-TRIHYDROXY-1.3.5 (10) -OESTRATRIENE |
| US6154158A (en) * | 1998-06-30 | 2000-11-28 | Qualcomm Incorporated | Digital-to-analog converter D.C. offset correction comparing converter input and output signals |
| DE19906159A1 (en) * | 1999-02-09 | 2000-08-10 | Schering Ag | 16-hydroxyestratrienes as selectively active estrogens |
| JP2003513102A (en) * | 1999-11-02 | 2003-04-08 | シエーリング アクチエンゲゼルシャフト | 18-nor-steroids as estrogen with selective action |
| US7378404B2 (en) * | 2000-04-12 | 2008-05-27 | Schering Aktiengesellschaft | 8β-hydrocarbyl-substituted estratrienes for use as selective estrogens |
-
2002
- 2002-06-11 DE DE10226326A patent/DE10226326A1/en not_active Ceased
-
2003
- 2003-06-10 PE PE2003000575A patent/PE20040613A1/en not_active Application Discontinuation
- 2003-06-11 EA EA200401544A patent/EA008442B1/en not_active IP Right Cessation
- 2003-06-11 JP JP2004511321A patent/JP4615998B2/en not_active Expired - Fee Related
- 2003-06-11 AT AT03757065T patent/ATE303397T1/en active
- 2003-06-11 PL PL373090A patent/PL209910B1/en not_active IP Right Cessation
- 2003-06-11 RS YUP-1070/04A patent/RS50878B/en unknown
- 2003-06-11 DE DE50301116T patent/DE50301116D1/en not_active Expired - Lifetime
- 2003-06-11 MX MXPA04012491A patent/MXPA04012491A/en active IP Right Grant
- 2003-06-11 AU AU2003242683A patent/AU2003242683B9/en not_active Ceased
- 2003-06-11 BR BR0312140-2A patent/BR0312140A/en not_active IP Right Cessation
- 2003-06-11 DK DK03757065T patent/DK1517914T3/en active
- 2003-06-11 UY UY27844A patent/UY27844A1/en not_active Application Discontinuation
- 2003-06-11 HR HRP20050009AA patent/HRP20050009B1/en not_active IP Right Cessation
- 2003-06-11 AR ARP030102079A patent/AR040188A1/en active IP Right Grant
- 2003-06-11 ES ES03757065T patent/ES2248770T3/en not_active Expired - Lifetime
- 2003-06-11 CN CNB038135027A patent/CN1293090C/en not_active Expired - Fee Related
- 2003-06-11 KR KR1020047020133A patent/KR101006612B1/en not_active Expired - Fee Related
- 2003-06-11 CA CA2486495A patent/CA2486495C/en not_active Expired - Fee Related
- 2003-06-11 WO PCT/EP2003/006172 patent/WO2003104253A2/en not_active Ceased
- 2003-06-11 TW TW092115863A patent/TWI286140B/en not_active IP Right Cessation
- 2003-06-11 EP EP03757065A patent/EP1517914B1/en not_active Expired - Lifetime
- 2003-11-06 UA UAA200500212A patent/UA78062C2/en unknown
-
2004
- 2004-11-22 IL IL165321A patent/IL165321A/en not_active IP Right Cessation
- 2004-12-10 CU CU20040282A patent/CU23414B7/en not_active IP Right Cessation
-
2005
- 2005-01-10 NO NO20050127A patent/NO329563B1/en not_active IP Right Cessation
- 2005-01-10 EC EC2005005530A patent/ECSP055530A/en unknown
-
2006
- 2006-01-10 ZA ZA200500217A patent/ZA200500217B/en unknown
-
2008
- 2008-09-16 CR CR10289A patent/CR10289A/en not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110052699A1 (en) * | 2008-02-13 | 2011-03-03 | Adrian Funke | Drug delivery system with stabilising effect |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20160613 |