JP2006504711A5 - - Google Patents
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- Publication number
- JP2006504711A5 JP2006504711A5 JP2004540862A JP2004540862A JP2006504711A5 JP 2006504711 A5 JP2006504711 A5 JP 2006504711A5 JP 2004540862 A JP2004540862 A JP 2004540862A JP 2004540862 A JP2004540862 A JP 2004540862A JP 2006504711 A5 JP2006504711 A5 JP 2006504711A5
- Authority
- JP
- Japan
- Prior art keywords
- indazole
- carboxamide
- nhr
- phenyl
- pyridin
- 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.)
- Granted
Links
- -1 CH 2 OH Chemical group 0.000 claims description 106
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 125000001072 heteroaryl group Chemical group 0.000 claims description 54
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 43
- 125000005843 halogen group Chemical group 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 28
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000004001 thioalkyl group Chemical group 0.000 claims description 22
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 19
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000001246 bromo group Chemical group Br* 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052786 argon Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 150000003839 salts Chemical group 0.000 claims 11
- 239000012453 solvate Substances 0.000 claims 11
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 9
- 125000006239 protecting group Chemical group 0.000 claims 8
- 239000002253 acid Substances 0.000 claims 7
- 238000002512 chemotherapy Methods 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims 4
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 2
- 201000004384 Alopecia Diseases 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 101150012716 CDK1 gene Proteins 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 229940083347 Cyclin-dependent kinase 4 inhibitor Drugs 0.000 claims 2
- 101100059559 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) nimX gene Proteins 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 206010017533 Fungal infection Diseases 0.000 claims 2
- 206010028116 Mucosal inflammation Diseases 0.000 claims 2
- 201000010927 Mucositis Diseases 0.000 claims 2
- 208000031888 Mycoses Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 208000036142 Viral infection Diseases 0.000 claims 2
- 231100000360 alopecia Toxicity 0.000 claims 2
- 230000001363 autoimmune Effects 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 101150073031 cdk2 gene Proteins 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Chemical group 0.000 claims 2
- 208000014951 hematologic disease Diseases 0.000 claims 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 201000002364 leukopenia Diseases 0.000 claims 2
- 231100001022 leukopenia Toxicity 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- 206010043554 thrombocytopenia Diseases 0.000 claims 2
- 239000003053 toxin Substances 0.000 claims 2
- 231100000765 toxin Toxicity 0.000 claims 2
- 108700012359 toxins Proteins 0.000 claims 2
- 230000003612 virological effect Effects 0.000 claims 2
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- BMJAFUGCPSXEBZ-UHFFFAOYSA-N n-[3-(2,6-dimethylphenyl)propyl]-5-nitro-1h-indazole-3-carboxamide Chemical compound CC1=CC=CC(C)=C1CCCNC(=O)C1=NNC2=CC=C([N+]([O-])=O)C=C12 BMJAFUGCPSXEBZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 235000011056 potassium acetate Nutrition 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR02/12188 | 2002-10-02 | ||
| FR0212188A FR2845382A1 (fr) | 2002-10-02 | 2002-10-02 | Derives d'indazolecarboxamides, leur preparation et leur utilisation en therapeutique |
| PCT/FR2003/002862 WO2004031158A1 (fr) | 2002-10-02 | 2003-09-30 | Derives d'indazolecarboxamides, leur preparation et leur utilisation comme inhibiteurs des cdk1, cdk2 et cdk4 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006504711A JP2006504711A (ja) | 2006-02-09 |
| JP2006504711A5 true JP2006504711A5 (https=) | 2006-11-16 |
| JP4762543B2 JP4762543B2 (ja) | 2011-08-31 |
Family
ID=32011336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004540862A Expired - Fee Related JP4762543B2 (ja) | 2002-10-02 | 2003-09-30 | インダゾールカルボキサミド誘導体、それらの製造法ならびにｃｄｋ１、ｃｄｋ２およびｃｄｋ４阻害剤としての用途 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7482342B2 (https=) |
| EP (1) | EP1549620A1 (https=) |
| JP (1) | JP4762543B2 (https=) |
| AR (1) | AR041459A1 (https=) |
| AU (1) | AU2003299125A1 (https=) |
| FR (1) | FR2845382A1 (https=) |
| TW (1) | TWI331603B (https=) |
| WO (1) | WO2004031158A1 (https=) |
Families Citing this family (100)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005014554A1 (en) * | 2003-08-08 | 2005-02-17 | Astex Therapeutics Limited | 1h-indazole-3-carboxamide compounds as mapkap kinase modulators |
| FR2867778B1 (fr) * | 2004-03-16 | 2006-06-09 | Sanofi Synthelabo | Utilisation de derives d'indazolecarboxamides pour la preparation d'un medicament destine au traitement et a la prevention du paludisme |
| US7626021B2 (en) | 2004-07-27 | 2009-12-01 | Sgx Pharmaceuticals, Inc. | Fused ring heterocycle kinase modulators |
| CA2573573A1 (en) * | 2004-07-27 | 2006-02-09 | Sgx Pharmaceuticals, Inc. | Fused ring heterocycle kinase modulators |
| CA2644910C (en) * | 2006-03-31 | 2014-01-28 | Abbott Laboratories | Indazole compounds |
| DE102006030479A1 (de) | 2006-07-01 | 2008-03-20 | Merck Patent Gmbh | Indazolderivate |
| CA2668859A1 (en) | 2006-11-07 | 2008-05-15 | Proteologics Ltd. | Pyrimidine derivatives as posh and posh-ap inhibitors |
| MX2009013213A (es) * | 2007-06-08 | 2010-03-30 | Abbott Lab | Indazoles 5-sustituidos 5-heteroarilo como inhibidores de cinasa. |
| US8648069B2 (en) | 2007-06-08 | 2014-02-11 | Abbvie Inc. | 5-substituted indazoles as kinase inhibitors |
| WO2009061345A2 (en) * | 2007-11-07 | 2009-05-14 | Cornell Research Foundation, Inc. | Targeting cdk4 and cdk6 in cancer therapy |
| WO2009106980A2 (en) * | 2008-02-29 | 2009-09-03 | Pfizer Inc. | Indazole derivatives |
| JP5370957B2 (ja) | 2008-08-20 | 2013-12-18 | 学校法人日本大学 | アポトーシス抑制剤 |
| KR101061599B1 (ko) * | 2008-12-05 | 2011-09-02 | 한국과학기술연구원 | 비정상 세포 성장 질환의 치료를 위한 단백질 키나아제 저해제인 신규 인다졸 유도체, 이의 약학적으로 허용가능한염 및 이를 유효성분으로 함유하는 약학적 조성물 |
| CN102595899A (zh) * | 2009-08-10 | 2012-07-18 | 埃皮瑟瑞克斯有限公司 | 作为wnt/b-联蛋白信号传导途径抑制剂的吲唑及其治疗用途 |
| CN105037355B (zh) | 2009-08-10 | 2017-06-06 | 萨穆梅德有限公司 | Wnt信号传导途径的吲唑抑制剂及其治疗用途 |
| LT3001903T (lt) | 2009-12-21 | 2018-01-10 | Samumed, Llc | 1h-pirazolo[3,4-b]piridinai ir jų terapinis panaudojimas |
| WO2012064744A2 (en) | 2010-11-08 | 2012-05-18 | Lycera Corporation | Tetrahydroquinoline and related bicyclic compounds for inhibition of rorϒ activity and the treatment of disease |
| IN2014CN02646A (https=) * | 2011-09-14 | 2015-08-07 | Samumed Llc | |
| WO2013113762A1 (en) | 2012-01-31 | 2013-08-08 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and kits for predicting the risk of having a cutaneous melanoma in a subject |
| PH12017500997A1 (en) | 2012-04-04 | 2018-02-19 | Samumed Llc | Indazole inhibitors of the wnt signal pathway and therapeutic uses thereof |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| NZ629282A (en) | 2012-05-04 | 2017-04-28 | Samumed Llc | 1h-pyrazolo[3,4-b]pyridines and therapeutic uses thereof |
| JP6242868B2 (ja) | 2012-05-08 | 2017-12-06 | リセラ・コーポレイションＬｙｃｅｒａ Ｃｏｒｐｏｒａｔｉｏｎ | ＲＯＲγのアゴニストとしての使用のためおよび疾患の処置のためのテトラヒドロ［１，８］ナフチリジンスルホンアミドおよび関連化合物 |
| WO2013169704A2 (en) | 2012-05-08 | 2013-11-14 | Merck Sharp & Dohme Corp. | TETRAHYDRONAPHTHYRIDINE AND RELATED BICYCLIC COMPOUNDS FOR INHIBITION OF RORgamma ACTIVITY AND THE TREATMENT OF DISEASE |
| RU2015106013A (ru) * | 2012-08-10 | 2016-10-10 | Ф. Хоффманн-Ля Рош Аг | Соединения пиразолкарбоксамида, композиции и способы применения |
| MX365640B (es) | 2012-12-21 | 2019-06-10 | Plexxikon Inc | Compuestos y metodos para la modulacion de quinasas y sus indicaciones. |
| EP2943198B1 (en) | 2013-01-08 | 2019-07-17 | Samumed, LLC | 3-(benzoimidazol-2-yl)-indazole inhibitors of the wnt signaling pathway and therapeutic uses thereof |
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2003
- 2003-09-30 AU AU2003299125A patent/AU2003299125A1/en not_active Abandoned
- 2003-09-30 JP JP2004540862A patent/JP4762543B2/ja not_active Expired - Fee Related
- 2003-09-30 WO PCT/FR2003/002862 patent/WO2004031158A1/fr not_active Ceased
- 2003-09-30 EP EP03798949A patent/EP1549620A1/fr not_active Withdrawn
- 2003-10-01 AR ARP030103581A patent/AR041459A1/es unknown
- 2003-10-01 TW TW092127213A patent/TWI331603B/zh not_active IP Right Cessation
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2005
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