PT1423121E - Inibidores da protease de cisteína com estrutura de 2-ciano-4-amino-pirimidina e actividade inibidora da catepsi-na k para o tratamento de inflamações e de outras doenças - Google Patents
Inibidores da protease de cisteína com estrutura de 2-ciano-4-amino-pirimidina e actividade inibidora da catepsi-na k para o tratamento de inflamações e de outras doenças Download PDFInfo
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- PT1423121E PT1423121E PT02797650T PT02797650T PT1423121E PT 1423121 E PT1423121 E PT 1423121E PT 02797650 T PT02797650 T PT 02797650T PT 02797650 T PT02797650 T PT 02797650T PT 1423121 E PT1423121 E PT 1423121E
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- Portugal
- Prior art keywords
- alkyl
- heterocyclyl
- aryl
- dimethyl
- optionally substituted
- Prior art date
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 20
- 201000010099 disease Diseases 0.000 title claims abstract description 18
- 238000011282 treatment Methods 0.000 title abstract description 11
- 206010061218 Inflammation Diseases 0.000 title abstract description 6
- 230000004054 inflammatory process Effects 0.000 title abstract description 6
- 230000002401 inhibitory effect Effects 0.000 title description 5
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- 108010084457 Cathepsins Proteins 0.000 title description 3
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- 239000002852 cysteine proteinase inhibitor Substances 0.000 title description 2
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- DRJWNQZFYUQSPR-UHFFFAOYSA-N n-[[2-cyano-4-(2,2-dimethylpropylamino)pyrimidin-5-yl]methyl]-3-(4-methylpiperazin-1-yl)benzamide Chemical compound C1CN(C)CCN1C1=CC=CC(C(=O)NCC=2C(=NC(=NC=2)C#N)NCC(C)(C)C)=C1 DRJWNQZFYUQSPR-UHFFFAOYSA-N 0.000 description 1
- QBTANFWYJLWRSN-UHFFFAOYSA-N n-[[2-cyano-4-(2,2-dimethylpropylamino)pyrimidin-5-yl]methyl]-3-[3-[4-(2-ethoxyethyl)piperazin-1-yl]phenyl]-2,2-dimethylpropanamide Chemical compound C1CN(CCOCC)CCN1C1=CC=CC(CC(C)(C)C(=O)NCC=2C(=NC(=NC=2)C#N)NCC(C)(C)C)=C1 QBTANFWYJLWRSN-UHFFFAOYSA-N 0.000 description 1
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- VOOUHCIDGIMESB-UHFFFAOYSA-N n-[[2-cyano-4-(2,2-dimethylpropylamino)pyrimidin-5-yl]methyl]-3-[4-(4-ethylpiperazin-1-yl)phenyl]-2,2-dimethylpropanamide Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1CC(C)(C)C(=O)NCC1=CN=C(C#N)N=C1NCC(C)(C)C VOOUHCIDGIMESB-UHFFFAOYSA-N 0.000 description 1
- DHPWTWPWCNIICL-UHFFFAOYSA-N n-[[2-cyano-4-(2,2-dimethylpropylamino)pyrimidin-5-yl]methyl]-4-(4-ethylpiperazin-1-yl)benzamide Chemical compound C1CN(CC)CCN1C1=CC=C(C(=O)NCC=2C(=NC(=NC=2)C#N)NCC(C)(C)C)C=C1 DHPWTWPWCNIICL-UHFFFAOYSA-N 0.000 description 1
- ZEKUOOQATCFBAQ-UHFFFAOYSA-N n-[[2-cyano-4-(2,2-dimethylpropylamino)pyrimidin-5-yl]methyl]-4-methoxy-3-(2-piperidin-1-ylethoxy)benzamide Chemical compound COC1=CC=C(C(=O)NCC=2C(=NC(=NC=2)C#N)NCC(C)(C)C)C=C1OCCN1CCCCC1 ZEKUOOQATCFBAQ-UHFFFAOYSA-N 0.000 description 1
- KSQFQUOMMQRYIE-UHFFFAOYSA-N n-[[2-cyano-4-(2-methylpropylamino)pyrimidin-5-yl]methyl]-4-(1-propylpiperidin-4-yl)benzamide Chemical compound C1CN(CCC)CCC1C1=CC=C(C(=O)NCC=2C(=NC(=NC=2)C#N)NCC(C)C)C=C1 KSQFQUOMMQRYIE-UHFFFAOYSA-N 0.000 description 1
- NVAYZSKZLOXBPN-UHFFFAOYSA-N n-[[2-cyano-4-(2-methylpropylamino)pyrimidin-5-yl]methyl]-4-(4-propan-2-ylpiperazin-1-yl)benzamide Chemical compound CC(C)CNC1=NC(C#N)=NC=C1CNC(=O)C1=CC=C(N2CCN(CC2)C(C)C)C=C1 NVAYZSKZLOXBPN-UHFFFAOYSA-N 0.000 description 1
- UUNPUWRNQPLKSA-UHFFFAOYSA-N n-[[2-cyano-4-(2-methylpropylamino)pyrimidin-5-yl]methyl]-4-(4-propylpiperazin-1-yl)benzamide Chemical compound C1CN(CCC)CCN1C1=CC=C(C(=O)NCC=2C(=NC(=NC=2)C#N)NCC(C)C)C=C1 UUNPUWRNQPLKSA-UHFFFAOYSA-N 0.000 description 1
- QZUIJMNAECHJBL-UHFFFAOYSA-N n-[[2-cyano-4-(2-methylpropylamino)pyrimidin-5-yl]methyl]-4-[4-(2-methoxyethyl)piperazin-1-yl]benzamide Chemical compound C1CN(CCOC)CCN1C1=CC=C(C(=O)NCC=2C(=NC(=NC=2)C#N)NCC(C)C)C=C1 QZUIJMNAECHJBL-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 201000001245 periodontitis Diseases 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- CYJAWBVQRMVFEO-UHFFFAOYSA-N piperazine-2,6-dione Chemical compound O=C1CNCC(=O)N1 CYJAWBVQRMVFEO-UHFFFAOYSA-N 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- IIHQNAXFIODVDU-UHFFFAOYSA-N pyrimidine-2-carbonitrile Chemical compound N#CC1=NC=CC=N1 IIHQNAXFIODVDU-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 201000004409 schistosomiasis Diseases 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- CDRDBOVXTXJGKD-UHFFFAOYSA-M sodium;4-[4-(2-methoxyethyl)piperazin-1-yl]benzoate Chemical compound [Na+].C1CN(CCOC)CCN1C1=CC=C(C([O-])=O)C=C1 CDRDBOVXTXJGKD-UHFFFAOYSA-M 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- 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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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
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- Immunology (AREA)
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- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Neurology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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| GB0121024A GB0121024D0 (en) | 2001-08-30 | 2001-08-30 | Organic compounds |
| GBGB0121026.9A GB0121026D0 (en) | 2001-08-30 | 2001-08-30 | Organic compounds |
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| PT1423121E true PT1423121E (pt) | 2007-02-28 |
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| PT02797650T PT1423121E (pt) | 2001-08-30 | 2002-08-29 | Inibidores da protease de cisteína com estrutura de 2-ciano-4-amino-pirimidina e actividade inibidora da catepsi-na k para o tratamento de inflamações e de outras doenças |
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| DE (1) | DE60216122T2 (enExample) |
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| HU (1) | HUP0401431A3 (enExample) |
| IL (1) | IL160295A0 (enExample) |
| MX (1) | MXPA04001930A (enExample) |
| NZ (1) | NZ531287A (enExample) |
| PE (1) | PE20030772A1 (enExample) |
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| PT (1) | PT1423121E (enExample) |
| RU (1) | RU2326119C2 (enExample) |
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| WO2005014006A1 (en) * | 2003-07-21 | 2005-02-17 | Novartis Ag | Combinations of a cathepsin k inhibitor and a bisphophonate in the treatment of bone metastasis, tumor growth and tumor-induced bone loss |
| WO2005011703A1 (en) * | 2003-08-04 | 2005-02-10 | Akzo Nobel N.V. | 2-cyano-1,3,5-triazine-4,6-diamine derivatives |
| EP1667983A4 (en) * | 2003-09-23 | 2010-07-21 | Merck Sharp & Dohme | PYRAZOL MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS |
| WO2005049028A1 (en) * | 2003-11-19 | 2005-06-02 | Novartis Ag | Use of cathepsin k inhibitors in severe bone loss diseases |
| US20070232586A1 (en) * | 2004-04-21 | 2007-10-04 | Kazuyuki Ohmoto | Hydrazino-Substituted Heterocyclic Nitrile Compounds and Use Thereof |
| TW200614993A (en) * | 2004-06-11 | 2006-05-16 | Akzo Nobel Nv | 4-phenyl-pyrimidine-2-carbonitrile derivatives |
| WO2006027211A1 (en) * | 2004-09-07 | 2006-03-16 | Glaxo Group Limited | 2,4-substituted pyrimidines as cysteine protease inhibitors |
| WO2006040300A1 (en) * | 2004-10-12 | 2006-04-20 | N.V. Organon | 4-cycloalkyl-pyrimidine-2-carbonitrile derivatives |
| IL164942A0 (en) * | 2004-10-31 | 2005-12-18 | Yeda Res & Dev | The use of a protease or a protease inhibitor for the manufacture of medicaments |
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| CA2617725C (en) * | 2005-08-05 | 2012-04-03 | Hybrigenics Sa | Novel cysteine protease inhibitors and their therapeutic applications |
| WO2007025776A2 (en) * | 2005-09-02 | 2007-03-08 | Glaxo Group Limited | Cysteine protease inhibitors |
| US7326715B2 (en) | 2005-09-23 | 2008-02-05 | N.V. Organon | 4-Phenyl-6-substituted-pyrimidine-2-carbonitrile derivatives |
| TW200745055A (en) * | 2005-09-23 | 2007-12-16 | Organon Nv | 4-Phenyl-6-substituted-pyrimidine-2-carbonitrile derivatives |
| US7687515B2 (en) | 2006-01-17 | 2010-03-30 | N.V. Organon | 6-phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile derivatives |
| CA2652600A1 (en) * | 2006-05-22 | 2007-11-29 | Velcura Therapeutics, Inc. | Use of cathepsin k antagonists in bone production |
| US20090227579A1 (en) * | 2006-06-23 | 2009-09-10 | Astrazeneca Ab | Pteridine Derivatives and their Use as Cathespin Inhibitors |
| EP1947091A1 (en) * | 2007-01-16 | 2008-07-23 | Glaxo Group Limited | Pyrimidyl nitrile derivatives as cysteine protease inhibitors |
| US7932251B2 (en) | 2007-07-16 | 2011-04-26 | N.V. Organon | 6-phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile derivatives |
| EP2489656A1 (en) | 2007-12-21 | 2012-08-22 | Ligand Pharmaceuticals Inc. | Selective androgen receptor modulators (sarms) and uses thereof |
| WO2009087379A2 (en) | 2008-01-09 | 2009-07-16 | Amura Therapeutics Limited | Tetrahydrofuro (3, 2 -b) pyrrol- 3 -one derivatives as inhibitors of cysteine proteinases |
| TW201035094A (en) | 2009-01-16 | 2010-10-01 | Organon Nv | 6-phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile derivatives |
| US8026236B2 (en) | 2009-01-16 | 2011-09-27 | N.V. Organon | 6-phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile derivatives |
| EP2316820A1 (en) * | 2009-10-28 | 2011-05-04 | Dompe S.p.A. | 2-aryl-propionamide derivatives useful as bradykinin receptor antagonists and pharmaceutical compositions containing them |
| US9115126B2 (en) | 2010-01-15 | 2015-08-25 | Merck Sharp & Dohme B.V. | 1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile derivatives |
| EP3091085B1 (en) | 2010-10-06 | 2019-02-27 | Institució Catalana de Recerca I Estudis Avançats | Method of designing a therapy for breast cancer metastasis |
| US8524710B2 (en) * | 2010-11-05 | 2013-09-03 | Hoffmann-La Roche Inc. | Pyrrolidine derivatives |
| EP2650682A1 (en) | 2012-04-09 | 2013-10-16 | Fundació Privada Institut de Recerca Biomèdica | Method for the prognosis and treatment of cancer metastasis |
| BR112014030750A2 (pt) | 2012-06-06 | 2017-08-22 | Inst Catalana Recerca Estudis Avancats | Método para diagnóstico, prognóstico e tratamento da metástase do câncer pulmonar |
| US10119171B2 (en) | 2012-10-12 | 2018-11-06 | Inbiomotion S.L. | Method for the diagnosis, prognosis and treatment of prostate cancer metastasis |
| US20140105918A1 (en) | 2012-10-12 | 2014-04-17 | Inbiomotion S.L. | Method for the diagnosis, prognosis and treatment of prostate cancer metastasis |
| CA2906394A1 (en) | 2013-03-15 | 2014-09-18 | Fundacio Institut De Recerca Biomedica (Irb Barcelona) | Method for the prognosis and treatment of cancer metastasis |
| US20160032399A1 (en) | 2013-03-15 | 2016-02-04 | Inbiomotion S.L. | Method for the Prognosis and Treatment of Renal Cell Carcinoma Metastasis |
| MX362041B (es) | 2013-10-09 | 2019-01-07 | Fundacio Inst De Recerca Biomedica Irb Barcelona | Método para el pronóstico y tratamiento de cáncer metastásico de los huesos originado de cáncer de mama. |
| EP3094323A4 (en) | 2014-01-17 | 2017-10-11 | Ligand Pharmaceuticals Incorporated | Methods and compositions for modulating hormone levels |
| CA2967224C (en) | 2014-12-11 | 2023-08-22 | Inbiomotion S.L. | Binding members for human c-maf |
| DK3458610T3 (da) | 2016-05-25 | 2021-06-07 | Inbiomotion Sl | Terapeutisk behandling af brystcancer baseret på c-MAF-status |
| WO2018138356A1 (en) * | 2017-01-27 | 2018-08-02 | Genfit | Rorgamma modulators and uses thereof |
| CN108586356B (zh) * | 2017-03-16 | 2021-02-19 | 杭州科巢生物科技有限公司 | 瑞博西尼新中间体及其制备瑞博西尼的合成方法 |
| AU2018372762B2 (en) | 2017-11-22 | 2025-08-21 | Inbiomotion S.L. | Therapeutic treatment of breast cancer based on c-maf status |
| CN109467536B (zh) * | 2018-12-23 | 2020-06-05 | 沧州普瑞东方科技有限公司 | 2-氯/羟基嘧啶-5-羧酸的合成方法 |
| WO2020201572A1 (en) | 2019-04-05 | 2020-10-08 | Université De Bretagne Occidentale | Protease-activated receptor-2 inhibitors for the treatment of sensory neuropathy induced by a marine neurotoxic poisoning |
| CA3133929A1 (en) | 2019-04-19 | 2020-10-22 | Lin Zhi | Crystalline forms and methods of producing crystalline forms of a compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| NL270922A (enExample) | 1960-11-02 | |||
| NL295648A (enExample) * | 1962-07-26 | |||
| BR6915234D0 (pt) | 1969-05-22 | 1973-06-07 | American Cyanamid Co | Novos derivados de melamina e processo para sua preparaca |
| CH627919A5 (de) * | 1977-04-14 | 1982-02-15 | Ciba Geigy Ag | Herbizide mittel. |
| WO1997009315A1 (en) * | 1995-09-01 | 1997-03-13 | Signal Pharmaceuticals, Inc. | Pyrimidine carboxamides and related compounds and methods for treating inflammatory conditions |
| AU1608397A (en) | 1996-02-02 | 1997-08-22 | Zeneca Limited | Heterocyclic compounds useful as pharmaceutical agents |
| DE19817459A1 (de) | 1998-04-20 | 1999-10-21 | Basf Ag | Neue heterozyklische substituierte Amide, Herstellung und Anwendung |
| HUP0302380A2 (hu) | 1999-09-13 | 2004-03-01 | Boehringer Ingelheim Pharmaceuticals, Inc. | Cisztein-proteázok reverzibilis inhibitoraiként alkalmazható új spiroheterociklusos vegyületek, eljárás az előállításukra és ezeket tartalmazó gyógyszerkészítmények |
| IL148291A0 (en) * | 1999-09-16 | 2002-09-12 | Tanabe Seiyaku Co | Aromatic nitrogen-containing 6-membered cyclic compounds |
| CN1440393A (zh) * | 2000-04-28 | 2003-09-03 | 田边制药株式会社 | 环状化合物 |
| GB0013383D0 (en) | 2000-06-01 | 2000-07-26 | Glaxo Group Ltd | Therapeutic benzamide derivatives |
| AR036375A1 (es) * | 2001-08-30 | 2004-09-01 | Novartis Ag | Compuestos pirrolo [2,3-d] pirimidina -2- carbonitrilo, un proceso para su preparacion, una composicion farmaceutica y el uso de dichos compuestos para la preparacion de medicamentos |
| SE0201980D0 (sv) | 2002-06-24 | 2002-06-24 | Astrazeneca Ab | Novel compounds |
| SE0201976D0 (sv) | 2002-06-24 | 2002-06-24 | Astrazeneca Ab | Novel compounds |
-
2002
- 2002-08-28 AR ARP020103230A patent/AR036375A1/es not_active Application Discontinuation
- 2002-08-29 PL PL367821A patent/PL208280B1/pl not_active IP Right Cessation
- 2002-08-29 US US10/487,741 patent/US7112589B2/en not_active Expired - Fee Related
- 2002-08-29 BR BR0212141-7A patent/BR0212141A/pt not_active IP Right Cessation
- 2002-08-29 AU AU2002333758A patent/AU2002333758B2/en not_active Ceased
- 2002-08-29 EP EP02797650A patent/EP1423121B1/en not_active Expired - Lifetime
- 2002-08-29 ES ES02797650T patent/ES2275946T3/es not_active Expired - Lifetime
- 2002-08-29 KR KR1020047002973A patent/KR100629834B1/ko not_active Expired - Fee Related
- 2002-08-29 IL IL16029502A patent/IL160295A0/xx unknown
- 2002-08-29 PE PE2002000834A patent/PE20030772A1/es not_active Application Discontinuation
- 2002-08-29 HU HU0401431A patent/HUP0401431A3/hu unknown
- 2002-08-29 CN CN028169638A patent/CN1549717B/zh not_active Expired - Fee Related
- 2002-08-29 RU RU2004109812/04A patent/RU2326119C2/ru not_active IP Right Cessation
- 2002-08-29 AT AT02797650T patent/ATE345136T1/de active
- 2002-08-29 MX MXPA04001930A patent/MXPA04001930A/es active IP Right Grant
- 2002-08-29 DE DE60216122T patent/DE60216122T2/de not_active Expired - Lifetime
- 2002-08-29 CA CA002456127A patent/CA2456127C/en not_active Expired - Fee Related
- 2002-08-29 NZ NZ531287A patent/NZ531287A/en unknown
- 2002-08-29 JP JP2003524585A patent/JP4131701B2/ja not_active Expired - Fee Related
- 2002-08-29 PT PT02797650T patent/PT1423121E/pt unknown
- 2002-08-29 WO PCT/EP2002/009661 patent/WO2003020278A1/en not_active Ceased
-
2004
- 2004-02-25 CO CO04016657A patent/CO5560576A2/es not_active Application Discontinuation
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2005
- 2005-11-30 US US11/291,007 patent/US20060074092A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA04001930A (es) | 2004-06-15 |
| DE60216122T2 (de) | 2007-09-06 |
| ES2275946T3 (es) | 2007-06-16 |
| KR20040029101A (ko) | 2004-04-03 |
| CO5560576A2 (es) | 2005-09-30 |
| CN1549717B (zh) | 2011-08-17 |
| CA2456127C (en) | 2009-10-20 |
| JP2005505550A (ja) | 2005-02-24 |
| WO2003020278A1 (en) | 2003-03-13 |
| DE60216122D1 (de) | 2006-12-28 |
| AR036375A1 (es) | 2004-09-01 |
| PL208280B1 (pl) | 2011-04-29 |
| BR0212141A (pt) | 2004-08-24 |
| KR100629834B1 (ko) | 2006-09-29 |
| US7112589B2 (en) | 2006-09-26 |
| NZ531287A (en) | 2005-12-23 |
| US20060074092A1 (en) | 2006-04-06 |
| AU2002333758B2 (en) | 2006-01-19 |
| PE20030772A1 (es) | 2003-10-02 |
| ATE345136T1 (de) | 2006-12-15 |
| HUP0401431A2 (hu) | 2004-10-28 |
| IL160295A0 (en) | 2004-07-25 |
| PL367821A1 (en) | 2005-03-07 |
| CA2456127A1 (en) | 2003-03-13 |
| EP1423121A1 (en) | 2004-06-02 |
| RU2326119C2 (ru) | 2008-06-10 |
| RU2004109812A (ru) | 2005-10-20 |
| JP4131701B2 (ja) | 2008-08-13 |
| US20040249153A1 (en) | 2004-12-09 |
| HUP0401431A3 (en) | 2004-11-29 |
| EP1423121B1 (en) | 2006-11-15 |
| CN1549717A (zh) | 2004-11-24 |
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