JP2010531345A5 - - Google Patents
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- Publication number
- JP2010531345A5 JP2010531345A5 JP2010514138A JP2010514138A JP2010531345A5 JP 2010531345 A5 JP2010531345 A5 JP 2010531345A5 JP 2010514138 A JP2010514138 A JP 2010514138A JP 2010514138 A JP2010514138 A JP 2010514138A JP 2010531345 A5 JP2010531345 A5 JP 2010531345A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cyclopropyl
- amino
- alkoxy
- pharmaceutically acceptable
- 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
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 16
- -1 methoxy, ethoxy Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 26
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 238000002441 X-ray diffraction Methods 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229940124750 glucocorticoid receptor agonist Drugs 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- FBFWRFSQOQBANB-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-5-[3-[[1-[2-[2-(2-hydroxyethylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]-4-methylbenzamide Chemical compound CC1=C(F)C=C(C(=O)NC2CC2)C=C1N(C1=O)C=CN=C1NC1(C=2C(=CC=CC=2)OCCNCCO)CC1 FBFWRFSQOQBANB-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 230000003637 steroidlike Effects 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 claims 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 claims 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims 1
- IRLYGRLEBKCYPY-UHFFFAOYSA-N 2,5-dimethylbenzenesulfonic acid Chemical compound CC1=CC=C(C)C(S(O)(=O)=O)=C1 IRLYGRLEBKCYPY-UHFFFAOYSA-N 0.000 claims 1
- 229940080296 2-naphthalenesulfonate Drugs 0.000 claims 1
- ZJWQYMZURGETJD-UHFFFAOYSA-N 3-[3-[[1-[2-(2-aminoethoxy)phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]-n-cyclopropyl-5-fluoro-4-methylbenzamide Chemical compound CC1=C(F)C=C(C(=O)NC2CC2)C=C1N(C1=O)C=CN=C1NC1(C=2C(=CC=CC=2)OCCN)CC1 ZJWQYMZURGETJD-UHFFFAOYSA-N 0.000 claims 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 claims 1
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 claims 1
- JFUAWXPBHXKZGA-IBGZPJMESA-N 4-fluoro-2-[(4r)-5,5,5-trifluoro-4-hydroxy-2-methyl-4-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-yl]phenol Chemical compound C([C@@](O)(CC=1NC2=CN=CC=C2C=1)C(F)(F)F)C(C)(C)C1=CC(F)=CC=C1O JFUAWXPBHXKZGA-IBGZPJMESA-N 0.000 claims 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 102100039705 Beta-2 adrenergic receptor Human genes 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 102000009410 Chemokine receptor Human genes 0.000 claims 1
- 108050000299 Chemokine receptor Proteins 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims 1
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 229920002230 Pectic acid Polymers 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000000048 adrenergic agonist Substances 0.000 claims 1
- 229940126157 adrenergic receptor agonist Drugs 0.000 claims 1
- 229940072056 alginate Drugs 0.000 claims 1
- 235000010443 alginic acid Nutrition 0.000 claims 1
- 229920000615 alginic acid Polymers 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 claims 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 229940072107 ascorbate Drugs 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- 229940009098 aspartate Drugs 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 229940077388 benzenesulfonate Drugs 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 108010014499 beta-2 Adrenergic Receptors Proteins 0.000 claims 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 229930195712 glutamate Natural products 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims 1
- 229940070765 laurate Drugs 0.000 claims 1
- 229940049920 malate Drugs 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 claims 1
- NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 claims 1
- WABIFCXMZKETLV-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-5-[3-[2-[2-[2-(2-hydroxyethylamino)ethoxy]phenyl]propan-2-ylamino]-2-oxopyrazin-1-yl]-4-methylbenzamide Chemical compound CC1=C(F)C=C(C(=O)NC2CC2)C=C1N(C1=O)C=CN=C1NC(C)(C)C1=CC=CC=C1OCCNCCO WABIFCXMZKETLV-UHFFFAOYSA-N 0.000 claims 1
- BXNTVZZUMZOUAK-SFHVURJKSA-N n-cyclopropyl-3-fluoro-5-[3-[2-[2-[2-[[(2s)-2-hydroxypropyl]amino]ethoxy]phenyl]propan-2-ylamino]-2-oxopyrazin-1-yl]-4-methylbenzamide Chemical compound C[C@H](O)CNCCOC1=CC=CC=C1C(C)(C)NC(C1=O)=NC=CN1C1=CC(C(=O)NC2CC2)=CC(F)=C1C BXNTVZZUMZOUAK-SFHVURJKSA-N 0.000 claims 1
- HSPRNUYKOMESSJ-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-5-[3-[[1-[2-[2-[2-hydroxyethyl(methyl)amino]ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]-4-methylbenzamide Chemical compound OCCN(C)CCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 HSPRNUYKOMESSJ-UHFFFAOYSA-N 0.000 claims 1
- SAZVRXTVWZAHBI-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[3-[2-[2-[2-(methylamino)ethoxy]phenyl]propan-2-ylamino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C(C)(C)NC(C1=O)=NC=CN1C1=CC(C(=O)NC2CC2)=CC=C1C SAZVRXTVWZAHBI-UHFFFAOYSA-N 0.000 claims 1
- LFIFOOUCEUUIHK-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=CC=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 LFIFOOUCEUUIHK-UHFFFAOYSA-N 0.000 claims 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 claims 1
- 229940014662 pantothenate Drugs 0.000 claims 1
- 235000019161 pantothenic acid Nutrition 0.000 claims 1
- 239000011713 pantothenic acid Substances 0.000 claims 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 claims 1
- 229950010765 pivalate Drugs 0.000 claims 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims 1
- 229940081974 saccharin Drugs 0.000 claims 1
- 235000019204 saccharin Nutrition 0.000 claims 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims 1
- 229960001860 salicylate Drugs 0.000 claims 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 claims 1
- 229940114926 stearate Drugs 0.000 claims 1
- 229940086735 succinate Drugs 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 claims 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 claims 1
- 229950000339 xinafoate Drugs 0.000 claims 1
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Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2479580C2 (ru) | 2007-06-27 | 2013-04-20 | Астразенека Аб | Производные пиразинона и их применение для лечения легочных заболеваний |
| US20090011994A1 (en) | 2007-07-06 | 2009-01-08 | Bristol-Myers Squibb Company | Non-basic melanin concentrating hormone receptor-1 antagonists and methods |
| AR073711A1 (es) | 2008-10-01 | 2010-11-24 | Astrazeneca Ab | Derivados de isoquinolina |
| WO2010043721A1 (en) | 2008-10-17 | 2010-04-22 | Oryzon Genomics, S.A. | Oxidase inhibitors and their use |
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| US8859555B2 (en) | 2009-09-25 | 2014-10-14 | Oryzon Genomics S.A. | Lysine Specific Demethylase-1 inhibitors and their use |
| EP2486002B1 (en) | 2009-10-09 | 2019-03-27 | Oryzon Genomics, S.A. | Substituted heteroaryl- and aryl- cyclopropylamine acetamides and their use |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| US9138441B2 (en) | 2009-12-31 | 2015-09-22 | Ira Milton Trachtman | Compositions and method for treatment and prophylaxis of inflammatory bowel disease |
| WO2011106573A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with hepadnaviridae |
| US9616058B2 (en) | 2010-02-24 | 2017-04-11 | Oryzon Genomics, S.A. | Potent selective LSD1 inhibitors and dual LSD1/MAO-B inhibitors for antiviral use |
| MX2012012111A (es) | 2010-04-19 | 2013-05-30 | Oryzon Genomics Sa | Inhibidores de demetilasa-1 especifica de lisina y su uso. |
| WO2012013727A1 (en) | 2010-07-29 | 2012-02-02 | Oryzon Genomics S.A. | Cyclopropylamine derivatives useful as lsd1 inhibitors |
| SI2598482T1 (sl) | 2010-07-29 | 2018-09-28 | Oryzon Genomics, S.A. | Inhibitorji demetilaze lsd1 na osnovi arilciklopropilamina in njihova medicinska uporaba |
| TWI535712B (zh) * | 2010-08-06 | 2016-06-01 | 阿斯特捷利康公司 | 化合物 |
| GB201016912D0 (en) | 2010-10-07 | 2010-11-24 | Astrazeneca Ab | Novel combination |
| WO2012045883A1 (en) | 2010-10-08 | 2012-04-12 | Oryzon Genomics S.A. | Cyclopropylamine inhibitors of oxidases |
| WO2012072713A2 (en) | 2010-11-30 | 2012-06-07 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with flaviviridae |
| GB201021992D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | Compound |
| GB201021979D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | New compound |
| WO2012107498A1 (en) | 2011-02-08 | 2012-08-16 | Oryzon Genomics S.A. | Lysine demethylase inhibitors for myeloproliferative disorders |
| EP2741741A2 (en) * | 2011-05-19 | 2014-06-18 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for inflammatory diseases or conditions |
| CN107266345B (zh) | 2011-10-20 | 2021-08-17 | 奥瑞泽恩基因组学股份有限公司 | 作为lsd1抑制剂的(杂)芳基环丙胺化合物 |
| RS58475B1 (sr) | 2011-10-20 | 2019-04-30 | Oryzon Genomics Sa | Jedinjenja (hetero)aril ciklopropilamina kao lsd1 inhibitori |
| BR112014025201A2 (pt) | 2012-04-10 | 2017-07-11 | Sumitomo Dainippon Pharma Co Ltd | derivado de indazol 1-substituído |
| ES2716008T3 (es) | 2012-07-18 | 2019-06-07 | Sunshine Lake Pharma Co Ltd | Derivados heterocíclicos nitrogenados y su aplicación en fármacos |
| US9242969B2 (en) | 2013-03-14 | 2016-01-26 | Novartis Ag | Biaryl amide compounds as kinase inhibitors |
| US20140302819A1 (en) * | 2013-04-05 | 2014-10-09 | Microsoft Corporation | Techniques for selecting a proximity card of a mobile device for access |
| AU2014306149B2 (en) | 2013-08-06 | 2019-09-19 | Imago Biosciences Inc. | KDM1A inhibitors for the treatment of disease |
| MX376632B (es) * | 2014-06-27 | 2025-03-07 | Celgene Quanticel Res Inc | Inhibidores de demetilasa-1 especifica de lisina. |
| UY36294A (es) | 2014-09-12 | 2016-04-29 | Novartis Ag | Compuestos y composiciones como inhibidores de quinasa |
| KR102626978B1 (ko) | 2015-02-12 | 2024-01-18 | 이마고 바이오사이언시즈 인코포레이티드 | 질환 치료를 위한 kdm1a 저해제 |
| JP6691972B2 (ja) * | 2016-03-24 | 2020-05-13 | アストラゼネカ・アクチエボラーグＡｓｔｒａｚｅｎｅｃａ Ａｋｔｉｅｂｏｌａｇ | 結晶形態 |
| CN108884070B (zh) * | 2016-04-07 | 2021-07-02 | 葛兰素史克知识产权第二有限公司 | 作为溴结构域抑制剂的吡啶基衍生物 |
| US11390590B2 (en) | 2016-08-16 | 2022-07-19 | Imago Biosciences, Inc. | Methods and processes for the preparation of KDM1A inhibitors |
| EP3515446B1 (en) | 2016-09-19 | 2023-12-20 | Novartis AG | Therapeutic combinations comprising a raf inhibitor and a erk inhibitor |
| EP3529242A1 (en) * | 2016-10-19 | 2019-08-28 | Constellation Pharmaceuticals, Inc. | Synthesis of inhibitors of ezh2 |
| CN106674029B (zh) * | 2016-12-23 | 2018-08-21 | 四川久凌制药科技有限公司 | 一种他喷他多中间体的制备方法 |
| US11266653B2 (en) | 2017-05-02 | 2022-03-08 | Novartis Ag | Combination therapy |
| KR102684364B1 (ko) | 2018-05-11 | 2024-07-11 | 이마고 바이오사이언시즈 인코포레이티드 | 질환의 치료를 위한 kdm1a 저해제 |
| KR102865950B1 (ko) * | 2019-03-22 | 2025-09-30 | 사니오나 에이/에스 | 신규의 칼륨 채널 억제제 |
| ES3025633T3 (en) | 2019-05-13 | 2025-06-09 | Novartis Ag | New crystalline forms of n-(3-(2-(2-hydroxyethoxy)-6-morpholinopyridin-4-yl)-4-methvlphenyl)-2(trifluoromethyl)isonicotinamide as raf inhibitors for the treatment of cancer |
| DK4122926T3 (da) * | 2021-04-14 | 2025-06-30 | Shionogi & Co | Triazinderivater med virusreplikationsinhiberende aktivitet og farmaceutisk sammensætning, der omfatter disse |
| CN113999129B (zh) * | 2021-11-23 | 2023-09-01 | 长沙普济生物科技股份有限公司 | 一种含酚羟基氨基酸表面活性剂的合成方法 |
| WO2025122555A1 (en) * | 2023-12-05 | 2025-06-12 | Valo Health, Inc. | S1p 1 receptor agonists and uses thereof |
| CN119350255B (zh) * | 2024-10-21 | 2025-12-09 | 海南大学 | 一种酮衍生物及其合成方法和用途 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4199309B2 (ja) * | 1996-09-06 | 2008-12-17 | 日本化薬株式会社 | 新規アセトアミド誘導体およびプロテアーゼ阻害 |
| TWI328007B (en) | 2002-01-16 | 2010-08-01 | Astrazeneca Ab | Novel compounds |
| MXPA04008822A (es) | 2002-03-14 | 2004-11-26 | Bayer Healthcare Ag | Aroilpiridinonas monociclicas. |
| MXPA05000784A (es) | 2002-07-19 | 2005-06-17 | Biovitrum Ab | Derivados de piperazinil-pirazinona novedosos para el tratamiento de los trastornos relacionados con el receptor 5-ht2a. |
| MXPA06003615A (es) | 2003-09-30 | 2006-06-05 | Amgen Inc | Ligandos del receptor vanilloide y su uso en tratamientos. |
| WO2005035527A1 (en) * | 2003-10-14 | 2005-04-21 | Pharmacia Corporation | Substituted pyrazinone compounds for the treatment of inflammation |
| NZ545694A (en) * | 2003-12-03 | 2010-04-30 | Ym Bioscience Australia Pty Lt | Azole-based kinase inhibitors |
| GB0402812D0 (en) * | 2004-02-09 | 2004-03-10 | Tanabe Seiyaku Co | Novel compounds |
| CA2572119A1 (en) | 2004-06-29 | 2006-01-12 | Warner-Lambert Company Llc | Combination therapies utilizing benzamide inhibitors of the p2x7 receptor |
| JP4496092B2 (ja) | 2005-01-12 | 2010-07-07 | 信越化学工業株式会社 | 光ファイバ母材の製造方法及び装置 |
| ES2412007T3 (es) | 2005-12-21 | 2013-07-09 | Janssen Pharmaceutica, N.V. | Derivados de pirazinona sustituida novedosos para uso en enfermedades mediadas por MCH-1 |
| GB0608837D0 (en) | 2006-05-04 | 2006-06-14 | Chroma Therapeutics Ltd | Inhibitors of MAP kinase |
| NZ573348A (en) | 2006-05-04 | 2012-01-12 | Chroma Therapeutics Ltd | p38 MAP KINASE INHIBITORS |
| TW200808771A (en) * | 2006-05-08 | 2008-02-16 | Astrazeneca Ab | Novel compounds II |
| JP2009537602A (ja) * | 2006-05-22 | 2009-10-29 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 薬剤として用いるための置換ピラジノン誘導体 |
| TW200924754A (en) * | 2006-06-21 | 2009-06-16 | Du Pont | Pyrazinones as cellular proliferation inhibitors |
| EP2034993A2 (en) * | 2006-06-21 | 2009-03-18 | E.I. Du Pont De Nemours And Company | Pyrazinones as cellular proliferation inhibitors |
| RU2479580C2 (ru) * | 2007-06-27 | 2013-04-20 | Астразенека Аб | Производные пиразинона и их применение для лечения легочных заболеваний |
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