ES2289143T3 - Metodos para aumentar los niveles de testosterona endogena. - Google Patents
Metodos para aumentar los niveles de testosterona endogena. Download PDFInfo
- Publication number
- ES2289143T3 ES2289143T3 ES02766382T ES02766382T ES2289143T3 ES 2289143 T3 ES2289143 T3 ES 2289143T3 ES 02766382 T ES02766382 T ES 02766382T ES 02766382 T ES02766382 T ES 02766382T ES 2289143 T3 ES2289143 T3 ES 2289143T3
- Authority
- ES
- Spain
- Prior art keywords
- pyrazol
- tert
- pyridin
- butylphenyl
- tyrosinamide
- 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 - Lifetime
Links
- 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 title abstract description 90
- 229960003604 testosterone Drugs 0.000 title abstract description 45
- 238000000034 method Methods 0.000 title description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 32
- 208000035475 disorder Diseases 0.000 claims abstract description 20
- 201000010099 disease Diseases 0.000 claims abstract description 11
- -1 pyrazole compound Chemical class 0.000 claims description 209
- PQFMNVGMJJMLAE-QMMMGPOBSA-N L-tyrosinamide Chemical compound NC(=O)[C@@H](N)CC1=CC=C(O)C=C1 PQFMNVGMJJMLAE-QMMMGPOBSA-N 0.000 claims description 98
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 48
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 26
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
- 150000001413 amino acids Chemical class 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000003352 4-tert-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 16
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 206010002261 Androgen deficiency Diseases 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 150000003973 alkyl amines Chemical class 0.000 claims description 9
- 125000002837 carbocyclic group Chemical group 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 125000004419 alkynylene group Chemical group 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- PQFMNVGMJJMLAE-UHFFFAOYSA-N tyrosinamide Chemical compound NC(=O)C(N)CC1=CC=C(O)C=C1 PQFMNVGMJJMLAE-UHFFFAOYSA-N 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 230000021595 spermatogenesis Effects 0.000 claims description 5
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 150000003862 amino acid derivatives Chemical class 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- MGOGKPMIZGEGOZ-REOHCLBHSA-N (2s)-2-amino-3-hydroxypropanamide Chemical compound OC[C@H](N)C(N)=O MGOGKPMIZGEGOZ-REOHCLBHSA-N 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- WGKITHRCAVTOMZ-UHFFFAOYSA-N 4-[2-[4-[[2-(4-tert-butylphenyl)-5-pyridin-3-ylpyrazol-3-yl]amino]butylamino]ethyl]phenol Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(NCCCCNCCC=2C=CC(O)=CC=2)=CC(C=2C=NC=CC=2)=N1 WGKITHRCAVTOMZ-UHFFFAOYSA-N 0.000 claims description 3
- FMMHXFMDUAUIIT-UHFFFAOYSA-N 5-[2-(4-tert-butylphenyl)-5-pyridin-3-ylpyrazol-3-yl]pentanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(CCCCC(O)=O)=CC(C=2C=NC=CC=2)=N1 FMMHXFMDUAUIIT-UHFFFAOYSA-N 0.000 claims description 3
- LZSJMMLWYRJDOA-UHFFFAOYSA-N 5-[2-(4-tert-butylphenyl)-5-pyridin-4-ylpyrazol-3-yl]pentanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(CCCCC(O)=O)=CC(C=2C=CN=CC=2)=N1 LZSJMMLWYRJDOA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
- 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 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- MABSPILDWJKHFT-NDEPHWFRSA-N n-[(2s)-2-amino-3-(3-hydroxyphenyl)propanoyl]-6-[2-(4-tert-butylphenyl)-5-pyridin-2-ylpyrazol-3-yl]hexanamide Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(CCCCCC(=O)NC(=O)[C@@H](N)CC=2C=C(O)C=CC=2)=CC(C=2N=CC=CC=2)=N1 MABSPILDWJKHFT-NDEPHWFRSA-N 0.000 claims description 3
- PMRGBQGHMSTEFL-QFIPXVFZSA-N n-[(2s)-2-amino-3-hydroxypropanoyl]-6-[2-(4-propan-2-ylphenyl)-5-pyridin-2-ylpyrazol-3-yl]hexanamide Chemical compound C1=CC(C(C)C)=CC=C1N1C(CCCCCC(=O)NC(=O)[C@@H](N)CO)=CC(C=2N=CC=CC=2)=N1 PMRGBQGHMSTEFL-QFIPXVFZSA-N 0.000 claims description 3
- DZFSKNAODBHZEK-QFIPXVFZSA-N n-[(2s)-2-amino-3-hydroxypropanoyl]-6-[2-(4-tert-butylphenyl)-5-pyridin-2-ylpyrazol-3-yl]hexanamide Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(CCCCCC(=O)NC(=O)[C@@H](N)CO)=CC(C=2N=CC=CC=2)=N1 DZFSKNAODBHZEK-QFIPXVFZSA-N 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000005556 thienylene group Chemical group 0.000 claims description 3
- TUEXMSFXLWQHFG-UHFFFAOYSA-N 4-[2-[3-[2-(4-tert-butylphenyl)-5-pyridin-4-ylpyrazol-3-yl]propylamino]ethyl]phenol Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(CCCNCCC=2C=CC(O)=CC=2)=CC(C=2C=CN=CC=2)=N1 TUEXMSFXLWQHFG-UHFFFAOYSA-N 0.000 claims description 2
- 208000030507 AIDS Diseases 0.000 claims description 2
- 206010006895 Cachexia Diseases 0.000 claims description 2
- 201000006938 muscular dystrophy Diseases 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 230000000750 progressive effect Effects 0.000 claims description 2
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical class C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 230000008901 benefit Effects 0.000 abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 100
- 125000004429 atom Chemical group 0.000 description 52
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
- 125000005842 heteroatom Chemical group 0.000 description 28
- 150000003217 pyrazoles Chemical class 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- 229910052740 iodine Inorganic materials 0.000 description 24
- 229910052760 oxygen Inorganic materials 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- 239000011347 resin Substances 0.000 description 21
- 229920005989 resin Polymers 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 18
- 229910052717 sulfur Inorganic materials 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 16
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 10
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
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- 125000004122 cyclic group Chemical group 0.000 description 8
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 125000005647 linker group Chemical group 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
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- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 5
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- 125000003545 alkoxy group Chemical group 0.000 description 5
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32547001P | 2001-09-27 | 2001-09-27 | |
| US325470P | 2001-09-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2289143T3 true ES2289143T3 (es) | 2008-02-01 |
Family
ID=23268011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02766382T Expired - Lifetime ES2289143T3 (es) | 2001-09-27 | 2002-09-27 | Metodos para aumentar los niveles de testosterona endogena. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20040198799A1 (enExample) |
| EP (1) | EP1441724B8 (enExample) |
| JP (1) | JP2005504093A (enExample) |
| AT (1) | ATE372114T1 (enExample) |
| AU (1) | AU2002330120B2 (enExample) |
| CA (1) | CA2458661A1 (enExample) |
| DE (1) | DE60222286T2 (enExample) |
| DK (1) | DK1441724T3 (enExample) |
| ES (1) | ES2289143T3 (enExample) |
| IL (1) | IL161047A0 (enExample) |
| PT (1) | PT1441724E (enExample) |
| WO (1) | WO2003026649A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60112742T2 (de) * | 2000-05-19 | 2006-02-02 | Applied Research Systems Ars Holding N.V. | Verwendung von pyrazolderivaten zur behandlung von unfruchtbarkeit |
| AU2003265395A1 (en) * | 2002-08-14 | 2004-03-03 | Ppd Discovery, Inc. | Prenylation inhibitors and methods of their synthesis and use |
| US8492369B2 (en) | 2010-04-12 | 2013-07-23 | Clarus Therapeutics Inc | Oral testosterone ester formulations and methods of treating testosterone deficiency comprising same |
| WO2006113505A2 (en) | 2005-04-15 | 2006-10-26 | Clarus Therapeutics, Inc. | Pharmaceutical delivery systems for hydrophobic drugs and compositions comprising same |
| WO2007002563A1 (en) | 2005-06-27 | 2007-01-04 | Exelixis, Inc. | Imidazole based lxr modulators |
| KR20090023562A (ko) | 2006-06-23 | 2009-03-05 | 제이-오일 밀스, 인코포레이티드 | 테스토스테론 증가제 |
| UY30892A1 (es) * | 2007-02-07 | 2008-09-02 | Smithkline Beckman Corp | Inhibidores de la actividad akt |
| CA2750565C (en) * | 2009-01-30 | 2015-10-20 | Glaxosmithkline Llc | Crystalline n-{(1s)-2-amino-1-[(3-fluorophenyl)methyl]ethyl}-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)-2-thiophenecarboxamide hydrochloride |
| WO2011161615A1 (en) | 2010-06-24 | 2011-12-29 | Ranbaxy Laboratories Limited | 5-lipoxygenase inhibitors |
| WO2011161645A1 (en) | 2010-06-25 | 2011-12-29 | Ranbaxy Laboratories Limited | 5-lipoxygenase inhibitors |
| WO2012003405A1 (en) | 2010-06-30 | 2012-01-05 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
| NZ609955A (en) | 2010-11-09 | 2015-05-29 | Ironwood Pharmaceuticals Inc | Sgc stimulators |
| CN104066731B (zh) | 2011-12-27 | 2016-06-15 | 铁木医药有限公司 | 可用作sgc刺激剂的2-苄基、3-(嘧啶-2-基)取代的吡唑类 |
| US11564933B2 (en) | 2019-04-12 | 2023-01-31 | Tolmar, Inc. | Methods of treating testosterone deficiency |
| US20250171429A1 (en) * | 2022-02-23 | 2025-05-29 | Biohaven Therapeutics Ltd. | Pyrazolyl compounds as kv7 channel activators |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2665898B1 (fr) * | 1990-08-20 | 1994-03-11 | Sanofi | Derives d'amido-3 pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| DE4039733A1 (de) * | 1990-12-13 | 1992-06-17 | Basf Ag | Substituierte 5-aminopyrazole |
| CA2150703C (en) * | 1992-12-17 | 2002-01-08 | Pfizer Limited | Substituted pyrazoles |
| CN1174504A (zh) * | 1993-11-09 | 1998-02-25 | 麦克公司 | 促进生长激素释放的哌啶、吡咯烷和六氢－1h－吖庚因 |
| US5869688A (en) * | 1994-07-20 | 1999-02-09 | Monsanto Company | Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity |
| JP2002502380A (ja) * | 1997-05-22 | 2002-01-22 | ジー．ディー．サール アンド カンパニー | ｐ３８キナーゼ阻害剤としてのピラゾール誘導体 |
| US6080763A (en) * | 1997-11-03 | 2000-06-27 | Boehringer Ingelheim Pharmaceuticals, Inc. | Aromatic heterocyclic compounds and their use as anti-inflammatory agents |
| CZ20013912A3 (cs) * | 1999-05-04 | 2002-05-15 | Strakan Limited | Androgen glykosid, sloučenina, testosteron-ß-D-glukosid, 5 alfa-Dihydrotestosteron- 17ß-D-glukosid, farmaceutický prostředek a pouľití sloučeniny |
| DE60112742T2 (de) * | 2000-05-19 | 2006-02-02 | Applied Research Systems Ars Holding N.V. | Verwendung von pyrazolderivaten zur behandlung von unfruchtbarkeit |
| NZ523656A (en) * | 2000-08-31 | 2004-11-26 | Pfizer Prod Inc | Pyrazole derivatives and their use as protein kinase inhibitors |
-
2002
- 2002-09-27 IL IL16104702A patent/IL161047A0/xx unknown
- 2002-09-27 WO PCT/US2002/030801 patent/WO2003026649A1/en not_active Ceased
- 2002-09-27 JP JP2003530286A patent/JP2005504093A/ja active Pending
- 2002-09-27 CA CA002458661A patent/CA2458661A1/en not_active Abandoned
- 2002-09-27 AT AT02766382T patent/ATE372114T1/de not_active IP Right Cessation
- 2002-09-27 AU AU2002330120A patent/AU2002330120B2/en not_active Ceased
- 2002-09-27 ES ES02766382T patent/ES2289143T3/es not_active Expired - Lifetime
- 2002-09-27 DK DK02766382T patent/DK1441724T3/da active
- 2002-09-27 EP EP02766382A patent/EP1441724B8/en not_active Expired - Lifetime
- 2002-09-27 US US10/489,863 patent/US20040198799A1/en not_active Abandoned
- 2002-09-27 DE DE60222286T patent/DE60222286T2/de not_active Expired - Fee Related
- 2002-09-27 PT PT02766382T patent/PT1441724E/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003026649A1 (en) | 2003-04-03 |
| PT1441724E (pt) | 2007-10-15 |
| AU2002330120B2 (en) | 2007-10-11 |
| EP1441724B8 (en) | 2007-10-17 |
| DK1441724T3 (da) | 2007-12-03 |
| ATE372114T1 (de) | 2007-09-15 |
| JP2005504093A (ja) | 2005-02-10 |
| US20040198799A1 (en) | 2004-10-07 |
| IL161047A0 (en) | 2004-08-31 |
| EP1441724B1 (en) | 2007-09-05 |
| DE60222286D1 (de) | 2007-10-18 |
| CA2458661A1 (en) | 2003-04-03 |
| EP1441724A1 (en) | 2004-08-04 |
| DE60222286T2 (de) | 2008-06-19 |
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