JP2008509177A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008509177A5 JP2008509177A5 JP2007525227A JP2007525227A JP2008509177A5 JP 2008509177 A5 JP2008509177 A5 JP 2008509177A5 JP 2007525227 A JP2007525227 A JP 2007525227A JP 2007525227 A JP2007525227 A JP 2007525227A JP 2008509177 A5 JP2008509177 A5 JP 2008509177A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- phenyl
- group
- partially
- 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.)
- Pending
Links
- 125000000217 alkyl group Chemical group 0.000 claims 348
- -1 3-fluoro-benzyloxy Chemical group 0.000 claims 223
- 125000003545 alkoxy group Chemical group 0.000 claims 87
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 86
- 125000000623 heterocyclic group Chemical group 0.000 claims 75
- 229910052736 halogen Inorganic materials 0.000 claims 68
- 150000002367 halogens Chemical class 0.000 claims 68
- 125000003118 aryl group Chemical group 0.000 claims 57
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 55
- 239000008194 pharmaceutical composition Substances 0.000 claims 54
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 52
- 229910052717 sulfur Inorganic materials 0.000 claims 52
- 125000004432 carbon atom Chemical group C* 0.000 claims 51
- 150000002825 nitriles Chemical class 0.000 claims 48
- 125000001624 naphthyl group Chemical group 0.000 claims 46
- 125000004076 pyridyl group Chemical group 0.000 claims 41
- 125000001072 heteroaryl group Chemical group 0.000 claims 40
- 229910052760 oxygen Inorganic materials 0.000 claims 40
- 125000002883 imidazolyl group Chemical group 0.000 claims 35
- 239000001257 hydrogen Substances 0.000 claims 34
- 229910052739 hydrogen Inorganic materials 0.000 claims 34
- 229910052757 nitrogen Inorganic materials 0.000 claims 31
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 28
- 125000003373 pyrazinyl group Chemical group 0.000 claims 27
- 125000002098 pyridazinyl group Chemical group 0.000 claims 27
- 125000000168 pyrrolyl group Chemical group 0.000 claims 27
- 125000002541 furyl group Chemical group 0.000 claims 26
- 125000003226 pyrazolyl group Chemical group 0.000 claims 26
- 125000001544 thienyl group Chemical group 0.000 claims 26
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 24
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims 22
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 21
- 125000004043 oxo group Chemical group O=* 0.000 claims 21
- 125000001786 isothiazolyl group Chemical group 0.000 claims 20
- 125000000842 isoxazolyl group Chemical group 0.000 claims 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 19
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 18
- 239000004480 active ingredient Substances 0.000 claims 17
- 229940122696 MAP kinase inhibitor Drugs 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 16
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 claims 16
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims 16
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims 16
- 125000003435 aroyl group Chemical group 0.000 claims 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 14
- 125000005842 heteroatom Chemical group 0.000 claims 14
- 125000004193 piperazinyl group Chemical group 0.000 claims 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 13
- 125000003342 alkenyl group Chemical group 0.000 claims 13
- 125000003831 tetrazolyl group Chemical group 0.000 claims 13
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 12
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims 12
- 125000003282 alkyl amino group Chemical group 0.000 claims 11
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims 10
- VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 claims 10
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 10
- 125000002252 acyl group Chemical group 0.000 claims 10
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims 10
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims 10
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 10
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 10
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 10
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 10
- 150000003431 steroids Chemical class 0.000 claims 10
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 9
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 9
- 239000011593 sulfur Chemical class 0.000 claims 9
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 229940121647 egfr inhibitor Drugs 0.000 claims 8
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 8
- 125000001041 indolyl group Chemical group 0.000 claims 8
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 8
- 239000002742 neurokinin 1 receptor antagonist Substances 0.000 claims 8
- 239000001301 oxygen Substances 0.000 claims 8
- 125000003386 piperidinyl group Chemical group 0.000 claims 8
- 239000003380 propellant Substances 0.000 claims 8
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 8
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 7
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 7
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims 7
- QBACGOWRJDBXSG-ONEGZZNKSA-N (e)-n-[4-(3-bromo-4-chloroanilino)pyrido[3,4-d]pyrimidin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N1=CN=C2C=NC(NC(=O)/C=C/CN(C)C)=CC2=C1NC1=CC=C(Cl)C(Br)=C1 QBACGOWRJDBXSG-ONEGZZNKSA-N 0.000 claims 6
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 6
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 6
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 6
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000003107 substituted aryl group Chemical group 0.000 claims 6
- 229930192474 thiophene Natural products 0.000 claims 6
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 5
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 5
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 5
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims 5
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 claims 5
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 claims 5
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims 5
- 239000003937 drug carrier Substances 0.000 claims 5
- 239000002308 endothelin receptor antagonist Substances 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 5
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 5
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 5
- 125000001425 triazolyl group Chemical group 0.000 claims 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 206010009137 Chronic sinusitis Diseases 0.000 claims 4
- 229910004013 NO 2 Inorganic materials 0.000 claims 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 239000000443 aerosol Substances 0.000 claims 4
- 125000002837 carbocyclic group Chemical group 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 4
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 4
- 125000005241 heteroarylamino group Chemical group 0.000 claims 4
- 150000004677 hydrates Chemical class 0.000 claims 4
- 208000027866 inflammatory disease Diseases 0.000 claims 4
- 230000002757 inflammatory effect Effects 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 230000000414 obstructive effect Effects 0.000 claims 4
- 239000000843 powder Substances 0.000 claims 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims 3
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 3
- ATALOFNDEOCMKK-OITMNORJSA-N aprepitant Chemical compound O([C@@H]([C@@H]1C=2C=CC(F)=CC=2)O[C@H](C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CCN1CC1=NNC(=O)N1 ATALOFNDEOCMKK-OITMNORJSA-N 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims 3
- 125000005879 dioxolanyl group Chemical group 0.000 claims 3
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 3
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 3
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 3
- 150000003335 secondary amines Chemical class 0.000 claims 3
- 150000003512 tertiary amines Chemical class 0.000 claims 3
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims 3
- 150000003536 tetrazoles Chemical class 0.000 claims 3
- XPNMCDYOYIKVGB-CONSDPRKSA-N (2s,3s)-2-benzhydryl-n-[(2-methoxy-5-propan-2-ylphenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine Chemical compound COC1=CC=C(C(C)C)C=C1CN[C@@H]1[C@H](C(C=2C=CC=CC=2)C=2C=CC=CC=2)N2CCC1CC2 XPNMCDYOYIKVGB-CONSDPRKSA-N 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 206010001076 Acute sinusitis Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 208000004882 Intestinal Polyposis Diseases 0.000 claims 2
- 208000019693 Lung disease Diseases 0.000 claims 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 2
- 208000037062 Polyps Diseases 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
- DHCOPPHTVOXDKU-UHFFFAOYSA-N Tofimilast Chemical compound C1CN2C(C=3SC=CC=3)=NN=C2C2=C1C(CC)=NN2C1CCCC1 DHCOPPHTVOXDKU-UHFFFAOYSA-N 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 208000024716 acute asthma Diseases 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 2
- 230000004075 alteration Effects 0.000 claims 2
- 229960001372 aprepitant Drugs 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 claims 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 2
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 2
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims 2
- 125000005647 linker group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 2
- 210000003097 mucus Anatomy 0.000 claims 2
- DPHDSIQHVGSITN-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-2-[1-[(4-fluorophenyl)methyl]-5-hydroxyindol-3-yl]-2-oxoacetamide Chemical compound C1=C(C(=O)C(=O)NC=2C(=CN=CC=2Cl)Cl)C2=CC(O)=CC=C2N1CC1=CC=C(F)C=C1 DPHDSIQHVGSITN-UHFFFAOYSA-N 0.000 claims 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 2
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims 2
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 2
- 208000015768 polyposis Diseases 0.000 claims 2
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 2
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 claims 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims 2
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 claims 2
- NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000004001 thioalkyl group Chemical group 0.000 claims 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 2
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims 1
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims 1
- HUTHJVYJUPXHDF-DEOSSOPVSA-N (2s)-n-[2-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-[4-(cyclopropylmethyl)piperazin-1-yl]-n-methyl-2-phenylacetamide Chemical compound O=C([C@@H](N1CCN(CC2CC2)CC1)C=1C=CC=CC=1)N(C)CCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HUTHJVYJUPXHDF-DEOSSOPVSA-N 0.000 claims 1
- XILNRORTJVDYRH-HKUYNNGSSA-N (2s,3s)-n-[[2-methoxy-5-[5-(trifluoromethyl)tetrazol-1-yl]phenyl]methyl]-2-phenylpiperidin-3-amine Chemical compound C1([C@@H]2NCCC[C@@H]2NCC2=CC(=CC=C2OC)N2C(=NN=N2)C(F)(F)F)=CC=CC=C1 XILNRORTJVDYRH-HKUYNNGSSA-N 0.000 claims 1
- XTNYQMSCYWBFJX-KRWDZBQOSA-N (4r)-1-[(4-bromophenyl)methyl]-4-(2-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one Chemical compound C([C@H](CC1=O)C2=CC=C(C=C2OC2CCCC2)OC)N1CC1=CC=C(Br)C=C1 XTNYQMSCYWBFJX-KRWDZBQOSA-N 0.000 claims 1
- YTKFKKLZSIVJMX-ZDUSSCGKSA-N (6s)-4-[2-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxyethyl]-6-methylmorpholin-2-one Chemical compound C=12C=C(OCCN3CC(=O)O[C@@H](C)C3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 YTKFKKLZSIVJMX-ZDUSSCGKSA-N 0.000 claims 1
- LDXQLWNPGRANTO-GOSISDBHSA-N (9r)-7-[[3,5-bis(trifluoromethyl)phenyl]methyl]-9-methyl-5-(4-methylphenyl)-8,9,10,11-tetrahydro-[1,4]diazocino[2,1-g][1,7]naphthyridine-6,13-dione Chemical compound C([C@H](CN(CC=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)C1=O)C)CN(C(C2=NC=CC=C22)=O)C1=C2C1=CC=C(C)C=C1 LDXQLWNPGRANTO-GOSISDBHSA-N 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- NDAUXUAQIAJITI-LBPRGKRZSA-N (R)-salbutamol Chemical compound CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-LBPRGKRZSA-N 0.000 claims 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 1
- NQHFSECYQAQZBN-LSYPWIJNSA-M 1-[(3s)-3-(3,4-dichlorophenyl)-3-[2-(4-phenyl-1-azoniabicyclo[2.2.2]octan-1-yl)ethyl]piperidin-1-yl]-2-(3-propan-2-yloxyphenyl)ethanone;chloride Chemical compound [Cl-].CC(C)OC1=CC=CC(CC(=O)N2C[C@](CC[N+]34CCC(CC3)(CC4)C=3C=CC=CC=3)(CCC2)C=2C=C(Cl)C(Cl)=CC=2)=C1 NQHFSECYQAQZBN-LSYPWIJNSA-M 0.000 claims 1
- KKAZLOJEJTXUKC-UHFFFAOYSA-N 1-[2-[4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]ethyl]-1,3-diazinan-2-one Chemical compound C=12C=C(OC3CCN(CCN4C(NCCC4)=O)CC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 KKAZLOJEJTXUKC-UHFFFAOYSA-N 0.000 claims 1
- JOVBQIOLZWIOBT-UHFFFAOYSA-N 1-[2-[4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]ethyl]-3-methylimidazolidin-2-one Chemical compound C=12C=C(OC3CCN(CCN4C(N(C)CC4)=O)CC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 JOVBQIOLZWIOBT-UHFFFAOYSA-N 0.000 claims 1
- BAAGBGCDSAOQJY-UHFFFAOYSA-N 1-[2-[4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]ethyl]pyrrolidin-2-one Chemical compound C=12C=C(OC3CCN(CCN4C(CCC4)=O)CC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 BAAGBGCDSAOQJY-UHFFFAOYSA-N 0.000 claims 1
- IPJVSNMIMHDDHQ-UHFFFAOYSA-N 1-[4-[4-(3-chloro-4-fluoroanilino)-7-(2-methoxyethoxy)quinazolin-6-yl]oxypiperidin-1-yl]-2-methoxyethanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)COC)C(OCCOC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 IPJVSNMIMHDDHQ-UHFFFAOYSA-N 0.000 claims 1
- KCXAZEJYKXXQIS-UHFFFAOYSA-N 1-[4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-2-methoxyethanone Chemical compound C1CN(C(=O)COC)CCC1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=C(F)C(Cl)=C1 KCXAZEJYKXXQIS-UHFFFAOYSA-N 0.000 claims 1
- SDBIIHIBMQQOFY-UHFFFAOYSA-N 1-[4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-3-methoxypropan-1-one Chemical compound C1CN(C(=O)CCOC)CCC1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=C(F)C(Cl)=C1 SDBIIHIBMQQOFY-UHFFFAOYSA-N 0.000 claims 1
- ZKDJZZJMEPYFDP-UHFFFAOYSA-N 1-[4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(C)=O)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 ZKDJZZJMEPYFDP-UHFFFAOYSA-N 0.000 claims 1
- JLXUOMMQRMSKFX-UHFFFAOYSA-N 1-[4-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-2-methoxyethanone Chemical compound C1CN(C(=O)COC)CCC1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 JLXUOMMQRMSKFX-UHFFFAOYSA-N 0.000 claims 1
- AKIFEYGFKPNSFG-UHFFFAOYSA-N 1-[4-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]ethanone Chemical compound C=12C=C(OC3CCN(CC3)C(C)=O)C(OC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AKIFEYGFKPNSFG-UHFFFAOYSA-N 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- DWKBIQXIOVLREL-UHFFFAOYSA-N 2-[4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-n,n-dimethylacetamide Chemical compound C=12C=C(OC3CCN(CC(=O)N(C)C)CC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 DWKBIQXIOVLREL-UHFFFAOYSA-N 0.000 claims 1
- YWIZTPKVSNXXRX-UHFFFAOYSA-N 2-[4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]acetamide Chemical compound C=12C=C(OC3CCN(CC(N)=O)CC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 YWIZTPKVSNXXRX-UHFFFAOYSA-N 0.000 claims 1
- 125000005975 2-phenylethyloxy group Chemical group 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- DDYUBCCTNHWSQM-UHFFFAOYSA-N 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-(1,3-dioxoisoindol-2-yl)propanamide Chemical compound COC1=CC=C(C(CC(N)=O)N2C(C3=CC=CC=C3C2=O)=O)C=C1OC1CCCC1 DDYUBCCTNHWSQM-UHFFFAOYSA-N 0.000 claims 1
- KHXXMSARUQULRI-UHFFFAOYSA-N 3-(cyclopropylmethoxy)-n-(3,5-dichloro-1-hydroxypyridin-4-ylidene)-4-(difluoromethoxy)benzamide Chemical compound ClC1=CN(O)C=C(Cl)C1=NC(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1 KHXXMSARUQULRI-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- ZAQVAMIBXWWRPQ-NSHDSACASA-N 4-(3-chloro-4-fluoroanilino)-6-[(3S)-oxolan-3-yl]oxyquinazolin-7-ol Chemical compound C=12C=C(O[C@@H]3COCC3)C(O)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 ZAQVAMIBXWWRPQ-NSHDSACASA-N 0.000 claims 1
- UTUUPXBCDMQYRR-HSZRJFAPSA-N 4-[(2r)-2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethyl]pyridine Chemical compound COC1=CC=C([C@H](CC=2C=CN=CC=2)C=2C=CC=CC=2)C=C1OC1CCCC1 UTUUPXBCDMQYRR-HSZRJFAPSA-N 0.000 claims 1
- RUFRPXDLUOPBBC-UHFFFAOYSA-N 4-[1-[2-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxyethyl]piperidin-4-yl]morpholin-2-one Chemical compound C=12C=C(OCCN3CCC(CC3)N3CC(=O)OCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 RUFRPXDLUOPBBC-UHFFFAOYSA-N 0.000 claims 1
- RTLJQOLVPIGICL-UHFFFAOYSA-N 4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(methylsulfonylmethyl)phenol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CS(C)(=O)=O)=C1 RTLJQOLVPIGICL-UHFFFAOYSA-N 0.000 claims 1
- LIXBJWRFCNRAPA-UHFFFAOYSA-N 4-[2-(tert-butylamino)-1-hydroxyethyl]-3-chlorophenol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C=C1Cl LIXBJWRFCNRAPA-UHFFFAOYSA-N 0.000 claims 1
- UEYNRDAAZHSJHD-SFHVURJKSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-6-[[(2s)-oxolan-2-yl]methoxy]quinazolin-7-yl]oxyethyl]-6,6-dimethylmorpholin-2-one Chemical compound C1C(=O)OC(C)(C)CN1CCOC1=CC2=NC=NC(NC=3C=C(Cl)C(F)=CC=3)=C2C=C1OC[C@H]1OCCC1 UEYNRDAAZHSJHD-SFHVURJKSA-N 0.000 claims 1
- ALPHJXMCUQHURK-SFHVURJKSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-7-[[(2s)-oxolan-2-yl]methoxy]quinazolin-6-yl]oxyethyl]-6,6-dimethylmorpholin-2-one Chemical compound C1C(=O)OC(C)(C)CN1CCOC(C(=CC1=NC=N2)OC[C@H]3OCCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 ALPHJXMCUQHURK-SFHVURJKSA-N 0.000 claims 1
- DAIBLUSVAFXMJJ-UHFFFAOYSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxyethyl]-6,6-dimethylmorpholin-2-one Chemical compound C=12C=C(OCCN3CC(C)(C)OC(=O)C3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 DAIBLUSVAFXMJJ-UHFFFAOYSA-N 0.000 claims 1
- DYJUTMKGOQMFFN-UHFFFAOYSA-N 4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxy-n-(2-methoxyethyl)-n-methylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)N(C)CCOC)CCC1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=C(F)C(Cl)=C1 DYJUTMKGOQMFFN-UHFFFAOYSA-N 0.000 claims 1
- KJGKVANCDSTYDH-UHFFFAOYSA-N 4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxy-n-(3-methoxypropyl)piperidine-1-carboxamide Chemical compound C1CN(C(=O)NCCCOC)CCC1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=C(F)C(Cl)=C1 KJGKVANCDSTYDH-UHFFFAOYSA-N 0.000 claims 1
- JAFDYPYUQHLWBH-UHFFFAOYSA-N 4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carbonitrile Chemical compound C=12C=C(OC3CCN(CC3)C#N)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 JAFDYPYUQHLWBH-UHFFFAOYSA-N 0.000 claims 1
- XRYJULCDUUATMC-CYBMUJFWSA-N 4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenol Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=C(O)C=C1 XRYJULCDUUATMC-CYBMUJFWSA-N 0.000 claims 1
- KPIAZBMUYPPOHQ-UHFFFAOYSA-N 4-[bis(2-methoxyethyl)amino]-n-[4-(3-chloro-4-fluoroanilino)-7-(oxolan-2-ylmethoxy)quinazolin-6-yl]but-2-enamide Chemical compound N1=CN=C2C=C(OCC3OCCC3)C(NC(=O)C=CCN(CCOC)CCOC)=CC2=C1NC1=CC=C(F)C(Cl)=C1 KPIAZBMUYPPOHQ-UHFFFAOYSA-N 0.000 claims 1
- AZHVHFBKXHCSIL-JOCHJYFZSA-N 4-[bis(2-methoxyethyl)amino]-n-[7-(cyclopropylmethoxy)-4-[[(1r)-1-phenylethyl]amino]quinazolin-6-yl]but-2-enamide Chemical compound C1([C@@H](C)NC2=C3C=C(C(=CC3=NC=N2)OCC2CC2)NC(=O)C=CCN(CCOC)CCOC)=CC=CC=C1 AZHVHFBKXHCSIL-JOCHJYFZSA-N 0.000 claims 1
- LSLYOANBFKQKPT-DIFFPNOSSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]benzene-1,3-diol Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(O)C=C(O)C=1)C1=CC=C(O)C=C1 LSLYOANBFKQKPT-DIFFPNOSSA-N 0.000 claims 1
- IHOXNOQMRZISPV-YJYMSZOUSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-methoxyphenyl)propan-2-yl]azaniumyl]ethyl]-2-oxo-1h-quinolin-8-olate Chemical compound C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 IHOXNOQMRZISPV-YJYMSZOUSA-N 0.000 claims 1
- VHRSUDSXCMQTMA-PJHHCJLFSA-N 6alpha-methylprednisolone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)CO)CC[C@H]21 VHRSUDSXCMQTMA-PJHHCJLFSA-N 0.000 claims 1
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims 1
- QGBIFMJAQARMNQ-QISPFCDLSA-N C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3O[C@@H](CCC)O[C@@]3(SC)[C@@]2(C)C[C@@H]1O Chemical compound C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3O[C@@H](CCC)O[C@@]3(SC)[C@@]2(C)C[C@@H]1O QGBIFMJAQARMNQ-QISPFCDLSA-N 0.000 claims 1
- CPYZOSMOOHLXBK-CTYIDZIISA-N C1C[C@@H](NC)CC[C@@H]1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=C(F)C(Cl)=C1 Chemical compound C1C[C@@H](NC)CC[C@@H]1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=C(F)C(Cl)=C1 CPYZOSMOOHLXBK-CTYIDZIISA-N 0.000 claims 1
- CPYZOSMOOHLXBK-OTVXOJSOSA-N C1C[C@@H](NC)CC[C@H]1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=C(F)C(Cl)=C1 Chemical compound C1C[C@@H](NC)CC[C@H]1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=C(F)C(Cl)=C1 CPYZOSMOOHLXBK-OTVXOJSOSA-N 0.000 claims 1
- SMDWTNSXNDYDPS-KOMQPUFPSA-N C1C[C@@H](NS(=O)(=O)CC)CC[C@@H]1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=C(F)C(Cl)=C1 Chemical compound C1C[C@@H](NS(=O)(=O)CC)CC[C@@H]1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=C(F)C(Cl)=C1 SMDWTNSXNDYDPS-KOMQPUFPSA-N 0.000 claims 1
- KGEDETVMWLCPSA-CALCHBBNSA-N C1C[C@H](N(C)C(=O)COC)CC[C@@H]1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=C(F)C(Cl)=C1 Chemical compound C1C[C@H](N(C)C(=O)COC)CC[C@@H]1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=C(F)C(Cl)=C1 KGEDETVMWLCPSA-CALCHBBNSA-N 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- LCVXWZSYIUNUJR-BGYRXZFFSA-N C=12C=C(O[C@@H]3CC[C@@H](CC3)N(C)C(=O)C3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@@H]3CC[C@@H](CC3)N(C)C(=O)C3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 LCVXWZSYIUNUJR-BGYRXZFFSA-N 0.000 claims 1
- JFTQPPRTBFOLRM-BGYRXZFFSA-N C=12C=C(O[C@@H]3CC[C@@H](CC3)N(C)C(=O)N3CCCCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@@H]3CC[C@@H](CC3)N(C)C(=O)N3CCCCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 JFTQPPRTBFOLRM-BGYRXZFFSA-N 0.000 claims 1
- PDOSWZJDBOBQAN-BGYRXZFFSA-N C=12C=C(O[C@@H]3CC[C@@H](CC3)N(C)C(=O)N3CCN(C)CC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@@H]3CC[C@@H](CC3)N(C)C(=O)N3CCN(C)CC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 PDOSWZJDBOBQAN-BGYRXZFFSA-N 0.000 claims 1
- JEFIMDCWCOALTI-KDURUIRLSA-N C=12C=C(O[C@@H]3CC[C@@H](CC3)N(C)C(=O)N3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@@H]3CC[C@@H](CC3)N(C)C(=O)N3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 JEFIMDCWCOALTI-KDURUIRLSA-N 0.000 claims 1
- FPTTXLPPNCBKID-CALCHBBNSA-N C=12C=C(O[C@@H]3CC[C@@H](CC3)N(C)C(C)=O)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@@H]3CC[C@@H](CC3)N(C)C(C)=O)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 FPTTXLPPNCBKID-CALCHBBNSA-N 0.000 claims 1
- JPDAWFGHLHITNT-KDURUIRLSA-N C=12C=C(O[C@@H]3CC[C@@H](CC3)N(C)S(=O)(=O)N3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@@H]3CC[C@@H](CC3)N(C)S(=O)(=O)N3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 JPDAWFGHLHITNT-KDURUIRLSA-N 0.000 claims 1
- PEHNBYTXRHCHKF-IYBDPMFKSA-N C=12C=C(O[C@@H]3CC[C@@H](CC3)N(C)S(C)(=O)=O)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@@H]3CC[C@@H](CC3)N(C)S(C)(=O)=O)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 PEHNBYTXRHCHKF-IYBDPMFKSA-N 0.000 claims 1
- CYBRSHQMQMRQGS-MQMHXKEQSA-N C=12C=C(O[C@@H]3CC[C@@H](N)CC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@@H]3CC[C@@H](N)CC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 CYBRSHQMQMRQGS-MQMHXKEQSA-N 0.000 claims 1
- JEFIMDCWCOALTI-WGSAOQKQSA-N C=12C=C(O[C@@H]3CC[C@H](CC3)N(C)C(=O)N3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@@H]3CC[C@H](CC3)N(C)C(=O)N3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 JEFIMDCWCOALTI-WGSAOQKQSA-N 0.000 claims 1
- FOMMTKFJEREKRS-WKILWMFISA-N C=12C=C(O[C@@H]3CC[C@H](CC3)N(C)C)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@@H]3CC[C@H](CC3)N(C)C)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 FOMMTKFJEREKRS-WKILWMFISA-N 0.000 claims 1
- PEHNBYTXRHCHKF-WKILWMFISA-N C=12C=C(O[C@@H]3CC[C@H](CC3)N(C)S(C)(=O)=O)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@@H]3CC[C@H](CC3)N(C)S(C)(=O)=O)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 PEHNBYTXRHCHKF-WKILWMFISA-N 0.000 claims 1
- LACBJYAZTCFDGP-SAABIXHNSA-N C=12C=C(O[C@@H]3CC[C@H](CC3)NC(=O)N3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@@H]3CC[C@H](CC3)NC(=O)N3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 LACBJYAZTCFDGP-SAABIXHNSA-N 0.000 claims 1
- CUELDVKCEKJXBE-KOMQPUFPSA-N C=12C=C(O[C@@H]3CC[C@H](CC3)NS(=O)(=O)N(C)C)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@@H]3CC[C@H](CC3)NS(=O)(=O)N(C)C)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 CUELDVKCEKJXBE-KOMQPUFPSA-N 0.000 claims 1
- OTLJXOJEXWTEBW-SAABIXHNSA-N C=12C=C(O[C@@H]3CC[C@H](CC3)NS(=O)(=O)N3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@@H]3CC[C@H](CC3)NS(=O)(=O)N3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 OTLJXOJEXWTEBW-SAABIXHNSA-N 0.000 claims 1
- FJNIWTSYKPLARM-CTYIDZIISA-N C=12C=C(O[C@@H]3CC[C@H](CC3)NS(C)(=O)=O)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@@H]3CC[C@H](CC3)NS(C)(=O)=O)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 FJNIWTSYKPLARM-CTYIDZIISA-N 0.000 claims 1
- LACBJYAZTCFDGP-MAEOIBBWSA-N C=12C=C(O[C@H]3CC[C@H](CC3)NC(=O)N3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@H]3CC[C@H](CC3)NC(=O)N3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 LACBJYAZTCFDGP-MAEOIBBWSA-N 0.000 claims 1
- KUYBTTXROYFBAT-FZNQNYSPSA-N C=12C=C(O[C@H]3CC[C@H](CC3)NC(C)=O)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 Chemical compound C=12C=C(O[C@H]3CC[C@H](CC3)NC(C)=O)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 KUYBTTXROYFBAT-FZNQNYSPSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- LUKZNWIVRBCLON-GXOBDPJESA-N Ciclesonide Chemical compound C1([C@H]2O[C@@]3([C@H](O2)C[C@@H]2[C@@]3(C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]32)C)C(=O)COC(=O)C(C)C)CCCCC1 LUKZNWIVRBCLON-GXOBDPJESA-N 0.000 claims 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical class C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical class C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
- 102000002045 Endothelin Human genes 0.000 claims 1
- 108050009340 Endothelin Proteins 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- HUYWAWARQUIQLE-UHFFFAOYSA-N Isoetharine Chemical compound CC(C)NC(CC)C(O)C1=CC=C(O)C(O)=C1 HUYWAWARQUIQLE-UHFFFAOYSA-N 0.000 claims 1
- 108010092101 MEN 11420 Proteins 0.000 claims 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 1
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical group S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims 1
- ULXXDDBFHOBEHA-INIZCTEOSA-N N-[4-(3-chloro-4-fluoroanilino)-7-[[(3S)-3-oxolanyl]oxy]-6-quinazolinyl]-4-(dimethylamino)-2-butenamide Chemical compound N1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)C=CCN(C)C)=CC2=C1NC1=CC=C(F)C(Cl)=C1 ULXXDDBFHOBEHA-INIZCTEOSA-N 0.000 claims 1
- JWNPDZNEKVCWMY-UHFFFAOYSA-N N-[4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino)-2-butenamide Chemical compound C=12C=C(NC(=O)C=CCN(C)C)C(OCC)=CC2=NC=C(C#N)C=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 JWNPDZNEKVCWMY-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- RUOGJYKOQBFJIG-UHFFFAOYSA-N SCH-351591 Chemical compound C12=CC=C(C(F)(F)F)N=C2C(OC)=CC=C1C(=O)NC1=C(Cl)C=[N+]([O-])C=C1Cl RUOGJYKOQBFJIG-UHFFFAOYSA-N 0.000 claims 1
- VPMWDFRZSIMDKW-YJYMSZOUSA-N Salmefamol Chemical compound C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C(CO)=C1 VPMWDFRZSIMDKW-YJYMSZOUSA-N 0.000 claims 1
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 claims 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims 1
- CDKNUFNIFGPFSF-AYVLZSQQSA-N [(8s,9s,10r,11s,13s,14s,17r)-11-hydroxy-10,13-dimethyl-3-oxo-17-(2-propanoylsulfanylacetyl)-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] butanoate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)CSC(=O)CC)(OC(=O)CCC)[C@@]1(C)C[C@@H]2O CDKNUFNIFGPFSF-AYVLZSQQSA-N 0.000 claims 1
- WKHOPHIMYDJVSA-UHFFFAOYSA-N [3-[2-(tert-butylamino)-1-hydroxyethyl]-5-(2-methylpropanoyloxy)phenyl] 2-methylpropanoate Chemical compound CC(C)C(=O)OC1=CC(OC(=O)C(C)C)=CC(C(O)CNC(C)(C)C)=C1 WKHOPHIMYDJVSA-UHFFFAOYSA-N 0.000 claims 1
- HGQSWGUVSJUFJD-UHFFFAOYSA-N [4-[4-(3-chloro-4-fluoroanilino)-7-(2-methoxyethoxy)quinazolin-6-yl]oxypiperidin-1-yl]-morpholin-4-ylmethanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)N3CCOCC3)C(OCCOC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 HGQSWGUVSJUFJD-UHFFFAOYSA-N 0.000 claims 1
- GDZDVSVAWGOPPB-CALCHBBNSA-N [4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-[(2r,6s)-2,6-dimethylmorpholin-4-yl]methanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)N3C[C@@H](C)O[C@@H](C)C3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 GDZDVSVAWGOPPB-CALCHBBNSA-N 0.000 claims 1
- SGPQZLAIXLGTBH-UHFFFAOYSA-N [4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-morpholin-4-ylmethanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)N3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 SGPQZLAIXLGTBH-UHFFFAOYSA-N 0.000 claims 1
- COUMVWRRFZOSEJ-UHFFFAOYSA-N [4-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]-morpholin-4-ylmethanone Chemical compound C=12C=C(OC3CCN(CC3)C(=O)N3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 COUMVWRRFZOSEJ-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- YLFIGGHWWPSIEG-UHFFFAOYSA-N aminoxyl Chemical class [O]N YLFIGGHWWPSIEG-UHFFFAOYSA-N 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 229960003060 bambuterol Drugs 0.000 claims 1
- ANZXOIAKUNOVQU-UHFFFAOYSA-N bambuterol Chemical compound CN(C)C(=O)OC1=CC(OC(=O)N(C)C)=CC(C(O)CNC(C)(C)C)=C1 ANZXOIAKUNOVQU-UHFFFAOYSA-N 0.000 claims 1
- NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 claims 1
- 229940092705 beclomethasone Drugs 0.000 claims 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 229960003065 bosentan Drugs 0.000 claims 1
- SXTRWVVIEPWAKM-UHFFFAOYSA-N bosentan hydrate Chemical compound O.COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 SXTRWVVIEPWAKM-UHFFFAOYSA-N 0.000 claims 1
- 229950008847 broxaterol Drugs 0.000 claims 1
- JBRBWHCVRGURBA-UHFFFAOYSA-N broxaterol Chemical compound CC(C)(C)NCC(O)C1=CC(Br)=NO1 JBRBWHCVRGURBA-UHFFFAOYSA-N 0.000 claims 1
- 229960004436 budesonide Drugs 0.000 claims 1
- 239000001273 butane Chemical class 0.000 claims 1
- OMZCMEYTWSXEPZ-UHFFFAOYSA-N canertinib Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC=NC2=CC(OCCCN3CCOCC3)=C(NC(=O)C=C)C=C12 OMZCMEYTWSXEPZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 229960001386 carbuterol Drugs 0.000 claims 1
- KEMXXQOFIRIICG-UHFFFAOYSA-N carbuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(NC(N)=O)=C1 KEMXXQOFIRIICG-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 229960005395 cetuximab Drugs 0.000 claims 1
- PHIVEUQACADDGU-UHFFFAOYSA-N chembl218103 Chemical compound C1CN(C(=NN=2)C(C)(C)C)C=2C2=C1C(CC)=NN2C1CCCC1 PHIVEUQACADDGU-UHFFFAOYSA-N 0.000 claims 1
- CFBUZOUXXHZCFB-OYOVHJISSA-N chembl511115 Chemical compound COC1=CC=C([C@@]2(CC[C@H](CC2)C(O)=O)C#N)C=C1OC1CCCC1 CFBUZOUXXHZCFB-OYOVHJISSA-N 0.000 claims 1
- 229960003728 ciclesonide Drugs 0.000 claims 1
- 229960001117 clenbuterol Drugs 0.000 claims 1
- STJMRWALKKWQGH-UHFFFAOYSA-N clenbuterol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1 STJMRWALKKWQGH-UHFFFAOYSA-N 0.000 claims 1
- 239000008139 complexing agent Substances 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 239000006184 cosolvent Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 229960003957 dexamethasone Drugs 0.000 claims 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 1
- 150000002016 disaccharides Chemical class 0.000 claims 1
- ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 claims 1
- QVDKSPUZWYTNQA-UHFFFAOYSA-N enprofylline Chemical compound O=C1NC(=O)N(CCC)C2=NC=N[C]21 QVDKSPUZWYTNQA-UHFFFAOYSA-N 0.000 claims 1
- 229950000579 enprofylline Drugs 0.000 claims 1
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims 1
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims 1
- AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- DHZKMLSTTZFTMK-UHFFFAOYSA-N ethyl 3-[3-[[4-[[(3-hydroxybenzoyl)amino]methyl]phenyl]methylcarbamoyl]pyridin-2-yl]oxybenzoate Chemical compound CCOC(=O)C1=CC=CC(OC=2C(=CC=CN=2)C(=O)NCC=2C=CC(CNC(=O)C=3C=C(O)C=CC=3)=CC=2)=C1 DHZKMLSTTZFTMK-UHFFFAOYSA-N 0.000 claims 1
- FIFVQZLUEWHMSV-UHFFFAOYSA-N ethyl n-[4-[2-(tert-butylamino)-1-hydroxyethyl]-2-cyano-6-fluorophenyl]carbamate Chemical compound CCOC(=O)NC1=C(F)C=C(C(O)CNC(C)(C)C)C=C1C#N FIFVQZLUEWHMSV-UHFFFAOYSA-N 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 229960001022 fenoterol Drugs 0.000 claims 1
- 229960000676 flunisolide Drugs 0.000 claims 1
- 229960002714 fluticasone Drugs 0.000 claims 1
- MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 claims 1
- 235000013355 food flavoring agent Nutrition 0.000 claims 1
- 229960002848 formoterol Drugs 0.000 claims 1
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 claims 1
- 150000004676 glycans Chemical class 0.000 claims 1
- 150000002334 glycols Chemical class 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- OXLZNBCNGJWPRV-UHFFFAOYSA-N hexoprenaline Chemical compound C=1C=C(O)C(O)=CC=1C(O)CNCCCCCCNCC(O)C1=CC=C(O)C(O)=C1 OXLZNBCNGJWPRV-UHFFFAOYSA-N 0.000 claims 1
- TWTMQRXNAZGSCE-UHFFFAOYSA-N hydron;[6-(methylamino)-1-(2-methylpropanoyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl] 2-methylpropanoate;chloride Chemical compound Cl.C1=CC(OC(=O)C(C)C)=C(OC(=O)C(C)C)C2=C1CC(NC)CC2 TWTMQRXNAZGSCE-UHFFFAOYSA-N 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 229950002451 ibuterol Drugs 0.000 claims 1
- QZZUEBNBZAPZLX-QFIPXVFZSA-N indacaterol Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 QZZUEBNBZAPZLX-QFIPXVFZSA-N 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 238000007918 intramuscular administration Methods 0.000 claims 1
- 238000007912 intraperitoneal administration Methods 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 239000001282 iso-butane Substances 0.000 claims 1
- 229960001268 isoetarine Drugs 0.000 claims 1
- 229960001317 isoprenaline Drugs 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- 229950005286 lanepitant Drugs 0.000 claims 1
- 229950008204 levosalbutamol Drugs 0.000 claims 1
- 229950004407 mabuterol Drugs 0.000 claims 1
- JSJCTEKTBOKRST-UHFFFAOYSA-N mabuterol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(C(F)(F)F)=C1 JSJCTEKTBOKRST-UHFFFAOYSA-N 0.000 claims 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 229960004584 methylprednisolone Drugs 0.000 claims 1
- 229960001664 mometasone Drugs 0.000 claims 1
- QLIIKPVHVRXHRI-CXSFZGCWSA-N mometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O QLIIKPVHVRXHRI-CXSFZGCWSA-N 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 150000002772 monosaccharides Chemical class 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- LJGUZUROJOJEMI-UHFFFAOYSA-N n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-[4-(1,3-oxazol-2-yl)phenyl]benzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)C=2C=CC(=CC=2)C=2OC=CN=2)=C1C LJGUZUROJOJEMI-UHFFFAOYSA-N 0.000 claims 1
- NNAIRLNUMRYQDU-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-(1-ethylpiperidin-4-yl)oxy-7-methoxyquinazolin-4-amine Chemical compound C1CN(CC)CCC1OC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=C(F)C(Cl)=C1 NNAIRLNUMRYQDU-UHFFFAOYSA-N 0.000 claims 1
- ILHNRRSUBPVKAI-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound C1CN(S(=O)(=O)C)CCC1OC1=CC=C(N=CN=C2NC=3C=C(Cl)C(F)=CC=3)C2=C1 ILHNRRSUBPVKAI-UHFFFAOYSA-N 0.000 claims 1
- FMGCFCDPXYSVBU-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-7-(2-methoxyethoxy)-6-(1-methylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound C=12C=C(OC3CCN(C)CC3)C(OCCOC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 FMGCFCDPXYSVBU-UHFFFAOYSA-N 0.000 claims 1
- GUJVPVDEFQJUQY-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-7-(2-methoxyethoxy)-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound C=12C=C(OC3CCN(CC3)S(C)(=O)=O)C(OCCOC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 GUJVPVDEFQJUQY-UHFFFAOYSA-N 0.000 claims 1
- YAHVBINRULXWJV-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-7-(2-methoxyethoxy)-6-(oxan-4-yloxy)quinazolin-4-amine Chemical compound C=12C=C(OC3CCOCC3)C(OCCOC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 YAHVBINRULXWJV-UHFFFAOYSA-N 0.000 claims 1
- BNEJWYNZRHVGGU-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-7-ethoxy-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound C=12C=C(OC3CCN(CC3)S(C)(=O)=O)C(OCC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 BNEJWYNZRHVGGU-UHFFFAOYSA-N 0.000 claims 1
- HPSUJEVGXIZVDC-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-7-ethoxy-6-(oxan-4-yloxy)quinazolin-4-amine Chemical compound C=12C=C(OC3CCOCC3)C(OCC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 HPSUJEVGXIZVDC-UHFFFAOYSA-N 0.000 claims 1
- AHPPMJNZFROCCT-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-7-methoxy-6-(1-methylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound C=12C=C(OC3CCN(C)CC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 AHPPMJNZFROCCT-UHFFFAOYSA-N 0.000 claims 1
- XFENZNCAYAJOQE-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-7-methoxy-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound C=12C=C(OC3CCN(CC3)S(C)(=O)=O)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XFENZNCAYAJOQE-UHFFFAOYSA-N 0.000 claims 1
- WZBWYRUTRBGTAL-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-7-methoxy-6-(oxan-3-yloxy)quinazolin-4-amine Chemical compound C=12C=C(OC3COCCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 WZBWYRUTRBGTAL-UHFFFAOYSA-N 0.000 claims 1
- XNHQKLXMYJHGPA-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-7-methoxy-6-(oxan-4-yloxy)quinazolin-4-amine Chemical compound C=12C=C(OC3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XNHQKLXMYJHGPA-UHFFFAOYSA-N 0.000 claims 1
- RZYANQUZIRWZBS-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-7-methoxy-6-piperidin-3-yloxyquinazolin-4-amine Chemical compound C=12C=C(OC3CNCCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 RZYANQUZIRWZBS-UHFFFAOYSA-N 0.000 claims 1
- YOBLCEDHQQYBEJ-UHFFFAOYSA-N n-(3-ethynylphenyl)-7-methoxy-6-(1-methylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound C=12C=C(OC3CCN(C)CC3)C(OC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 YOBLCEDHQQYBEJ-UHFFFAOYSA-N 0.000 claims 1
- AXUKMHZUBSEERL-UHFFFAOYSA-N n-(3-ethynylphenyl)-7-methoxy-6-(1-methylsulfonylpiperidin-4-yl)oxyquinazolin-4-amine Chemical compound C=12C=C(OC3CCN(CC3)S(C)(=O)=O)C(OC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AXUKMHZUBSEERL-UHFFFAOYSA-N 0.000 claims 1
- QROHAWMNESUZHZ-UHFFFAOYSA-N n-(3-ethynylphenyl)-7-methoxy-6-(oxan-4-yloxy)quinazolin-4-amine Chemical compound C=12C=C(OC3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 QROHAWMNESUZHZ-UHFFFAOYSA-N 0.000 claims 1
- FAKQAHQFVKSUIO-UHFFFAOYSA-N n-(3-ethynylphenyl)-7-methoxy-6-piperidin-4-yloxyquinazolin-4-amine Chemical compound C=12C=C(OC3CCNCC3)C(OC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 FAKQAHQFVKSUIO-UHFFFAOYSA-N 0.000 claims 1
- JXDKAWGCUBTYFX-BMPTZRATSA-N n-[(1s,2r)-2-[[(2r)-2-[methyl-[2-(4-methylphenyl)acetyl]amino]-3-naphthalen-2-ylpropanoyl]amino]cyclohexyl]-1h-indole-3-carboxamide Chemical compound CN([C@H](CC=1C=C2C=CC=CC2=CC=1)C(=O)N[C@H]1[C@H](CCCC1)NC(=O)C=1C2=CC=CC=C2NC=1)C(=O)CC1=CC=C(C)C=C1 JXDKAWGCUBTYFX-BMPTZRATSA-N 0.000 claims 1
- CVXJAPZTZWLRBP-MUUNZHRXSA-N n-[(2r)-1-[acetyl-[(2-methoxyphenyl)methyl]amino]-3-(1h-indol-3-yl)propan-2-yl]-2-(4-piperidin-1-ylpiperidin-1-yl)acetamide Chemical compound COC1=CC=CC=C1CN(C(C)=O)C[C@H](NC(=O)CN1CCC(CC1)N1CCCCC1)CC1=CNC2=CC=CC=C12 CVXJAPZTZWLRBP-MUUNZHRXSA-N 0.000 claims 1
- NGCNKEZHGRXHNL-WVWQGFTISA-N n-[(2r,3r,4r,5s,6r)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-[(1s,4s,7s,10s,13s,16s)-13-benzyl-16-(1h-indol-3-ylmethyl)-7-(2-methylpropyl)-3,6,9,12,15,18,20-heptaoxo-2,5,8,11,14,17,21-heptazabicyclo[8.8.4]docosan-4-yl]acetamide Chemical compound C([C@H]1C(=O)N[C@H]2CC(=O)NC[C@H](NC(=O)[C@H](CC=3C=CC=CC=3)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC2=O)C(=O)N[C@H](C(N1)=O)CC(C)C)C(=O)N[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1NC(C)=O NGCNKEZHGRXHNL-WVWQGFTISA-N 0.000 claims 1
- IGAXDMFXJYIUIV-XIFFEERXSA-N n-[1-[[(2s)-1-[benzyl(methyl)amino]-3-naphthalen-2-yl-1-oxopropan-2-yl]carbamoyl]cyclohexyl]-1h-indole-3-carboxamide Chemical compound O=C([C@H](CC=1C=C2C=CC=CC2=CC=1)NC(=O)C1(CCCCC1)NC(=O)C=1C2=CC=CC=C2NC=1)N(C)CC1=CC=CC=C1 IGAXDMFXJYIUIV-XIFFEERXSA-N 0.000 claims 1
- HUTHJVYJUPXHDF-UHFFFAOYSA-N n-[2-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-[4-(cyclopropylmethyl)piperazin-1-yl]-n-methyl-2-phenylacetamide Chemical compound C1CN(CC2CC2)CCN1C(C=1C=CC=CC=1)C(=O)N(C)CCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HUTHJVYJUPXHDF-UHFFFAOYSA-N 0.000 claims 1
- QDYICOKSXMTYPO-UHFFFAOYSA-N n-[2-[4-(3-chloro-4-fluoroanilino)-6-(oxan-4-yloxy)quinazolin-7-yl]oxyethyl]acetamide Chemical compound C=12C=C(OC3CCOCC3)C(OCCNC(=O)C)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 QDYICOKSXMTYPO-UHFFFAOYSA-N 0.000 claims 1
- MWHCFCZAROGOAF-UHFFFAOYSA-N n-[2-[4-(3-chloro-4-fluoroanilino)-6-(oxan-4-yloxy)quinazolin-7-yl]oxyethyl]methanesulfonamide Chemical compound C=12C=C(OC3CCOCC3)C(OCCNS(=O)(=O)C)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 MWHCFCZAROGOAF-UHFFFAOYSA-N 0.000 claims 1
- YBTWSPCOMHYEKP-UHFFFAOYSA-N n-[2-[4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]ethyl]acetamide Chemical compound C=12C=C(OC3CCN(CCNC(C)=O)CC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 YBTWSPCOMHYEKP-UHFFFAOYSA-N 0.000 claims 1
- HHRNQOGXBRYCHF-UHFFFAOYSA-N n-[2-hydroxy-5-[1-hydroxy-2-(propan-2-ylamino)ethyl]phenyl]methanesulfonamide Chemical compound CC(C)NCC(O)C1=CC=C(O)C(NS(C)(=O)=O)=C1 HHRNQOGXBRYCHF-UHFFFAOYSA-N 0.000 claims 1
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims 1
- ARFWPHOPKFABNZ-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-(diethylamino)but-2-enamide Chemical compound N1=CN=C2C=C(OCC3CC3)C(NC(=O)C=CCN(CC)CC)=CC2=C1NC1=CC=C(F)C(Cl)=C1 ARFWPHOPKFABNZ-UHFFFAOYSA-N 0.000 claims 1
- BHEXDWNZKZGCJR-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N1=CN=C2C=C(OCC3CC3)C(NC(=O)C=CCN(C)C)=CC2=C1NC1=CC=C(F)C(Cl)=C1 BHEXDWNZKZGCJR-UHFFFAOYSA-N 0.000 claims 1
- RZWHMWFZGYRQSS-LJQANCHMSA-N n-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-[(2r)-2-(methoxymethyl)-6-oxomorpholin-4-yl]but-2-enamide Chemical compound C1C(=O)O[C@@H](COC)CN1CC=CC(=O)NC(C(=CC1=NC=N2)OCC3CC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 RZWHMWFZGYRQSS-LJQANCHMSA-N 0.000 claims 1
- CCOKBACMAWRBJZ-MRXNPFEDSA-N n-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-[(2r)-2-methyl-6-oxomorpholin-4-yl]but-2-enamide Chemical compound C1C(=O)O[C@H](C)CN1CC=CC(=O)NC(C(=CC1=NC=N2)OCC3CC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 CCOKBACMAWRBJZ-MRXNPFEDSA-N 0.000 claims 1
- KMAPIHHPUBUULD-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-[2-methoxyethyl(methyl)amino]but-2-enamide Chemical compound N1=CN=C2C=C(OCC3CC3)C(NC(=O)C=CCN(C)CCOC)=CC2=C1NC1=CC=C(F)C(Cl)=C1 KMAPIHHPUBUULD-UHFFFAOYSA-N 0.000 claims 1
- PQTDSJWQNYBZMA-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]-4-morpholin-4-ylbut-2-enamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=NC=NC1=CC(OCC1CC1)=C2NC(=O)C=CCN1CCOCC1 PQTDSJWQNYBZMA-UHFFFAOYSA-N 0.000 claims 1
- ZDYRBVHJJSUYCX-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-(oxolan-2-ylmethoxy)quinazolin-6-yl]-4-morpholin-4-ylbut-2-enamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=NC=NC1=CC(OCC1OCCC1)=C2NC(=O)C=CCN1CCOCC1 ZDYRBVHJJSUYCX-UHFFFAOYSA-N 0.000 claims 1
- ULXXDDBFHOBEHA-MRXNPFEDSA-N n-[4-(3-chloro-4-fluoroanilino)-7-[(3r)-oxolan-3-yl]oxyquinazolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N1=CN=C2C=C(O[C@H]3COCC3)C(NC(=O)C=CCN(C)C)=CC2=C1NC1=CC=C(F)C(Cl)=C1 ULXXDDBFHOBEHA-MRXNPFEDSA-N 0.000 claims 1
- YHDXPFVJAIHRAS-AEFFLSMTSA-N n-[4-(3-chloro-4-fluoroanilino)-7-[(3s)-oxolan-3-yl]oxyquinazolin-6-yl]-4-[(2r)-2-methyl-6-oxomorpholin-4-yl]but-2-enamide Chemical compound C1C(=O)O[C@H](C)CN1CC=CC(=O)NC(C(=CC1=NC=N2)O[C@@H]3COCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 YHDXPFVJAIHRAS-AEFFLSMTSA-N 0.000 claims 1
- UIJGHCUIUFFXJL-QGZVFWFLSA-N n-[4-(3-chloro-4-fluoroanilino)-7-[[(2r)-oxolan-2-yl]methoxy]quinazolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N1=CN=C2C=C(OC[C@@H]3OCCC3)C(NC(=O)C=CCN(C)C)=CC2=C1NC1=CC=C(F)C(Cl)=C1 UIJGHCUIUFFXJL-QGZVFWFLSA-N 0.000 claims 1
- UIJGHCUIUFFXJL-KRWDZBQOSA-N n-[4-(3-chloro-4-fluoroanilino)-7-[[(2s)-oxolan-2-yl]methoxy]quinazolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N1=CN=C2C=C(OC[C@H]3OCCC3)C(NC(=O)C=CCN(C)C)=CC2=C1NC1=CC=C(F)C(Cl)=C1 UIJGHCUIUFFXJL-KRWDZBQOSA-N 0.000 claims 1
- GWFMAFOGZMQEDM-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-cyclopentyloxyquinazolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N1=CN=C2C=C(OC3CCCC3)C(NC(=O)C=CCN(C)C)=CC2=C1NC1=CC=C(F)C(Cl)=C1 GWFMAFOGZMQEDM-UHFFFAOYSA-N 0.000 claims 1
- IMBFFWDWIAWOLR-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-cyclopentyloxyquinazolin-6-yl]-4-[2-methoxyethyl(methyl)amino]but-2-enamide Chemical compound N1=CN=C2C=C(OC3CCCC3)C(NC(=O)C=CCN(C)CCOC)=CC2=C1NC1=CC=C(F)C(Cl)=C1 IMBFFWDWIAWOLR-UHFFFAOYSA-N 0.000 claims 1
- UBUIJVSWEKUFRP-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-7-cyclopentyloxyquinazolin-6-yl]-4-[cyclopropyl(methyl)amino]but-2-enamide Chemical compound C1CC1N(C)CC=CC(=O)NC(C(=CC1=NC=N2)OC3CCCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 UBUIJVSWEKUFRP-UHFFFAOYSA-N 0.000 claims 1
- TUYWTLTWNJOZNY-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]-5-propan-2-ylpyridine-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C2=NNN=N2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)C)C=N1 TUYWTLTWNJOZNY-UHFFFAOYSA-N 0.000 claims 1
- FATKBDRSEQUQER-HXUWFJFHSA-N n-[7-(cyclopropylmethoxy)-4-[[(1r)-1-phenylethyl]amino]quinazolin-6-yl]-4-[2-methoxyethyl(methyl)amino]but-2-enamide Chemical compound C1([C@@H](C)NC2=C3C=C(C(=CC3=NC=N2)OCC2CC2)NC(=O)C=CCN(C)CCOC)=CC=CC=C1 FATKBDRSEQUQER-HXUWFJFHSA-N 0.000 claims 1
- RHTFXIJREGOKBI-OAQYLSRUSA-N n-[7-(cyclopropylmethoxy)-4-[[(1r)-1-phenylethyl]amino]quinazolin-6-yl]-4-[ethyl(2-methoxyethyl)amino]but-2-enamide Chemical compound C1([C@@H](C)NC2=C3C=C(C(=CC3=NC=N2)OCC2CC2)NC(=O)C=CCN(CCOC)CC)=CC=CC=C1 RHTFXIJREGOKBI-OAQYLSRUSA-N 0.000 claims 1
- BTSVDJBLKHJYMN-OAQYLSRUSA-N n-[7-(cyclopropylmethoxy)-4-[[(1r)-1-phenylethyl]amino]quinazolin-6-yl]-4-[methyl(oxan-4-yl)amino]but-2-enamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C1=CC=2NC(=O)C=CCN(C)C3CCOCC3)=NC=NC1=CC=2OCC1CC1 BTSVDJBLKHJYMN-OAQYLSRUSA-N 0.000 claims 1
- ADOYXBQVLRRQGX-OAQYLSRUSA-N n-[7-cyclopentyloxy-4-[[(1r)-1-phenylethyl]amino]quinazolin-6-yl]-4-morpholin-4-ylbut-2-enamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C1=CC=2NC(=O)C=CCN3CCOCC3)=NC=NC1=CC=2OC1CCCC1 ADOYXBQVLRRQGX-OAQYLSRUSA-N 0.000 claims 1
- WOWRAEPIBQSHBM-QZTJIDSGSA-N n-[7-methoxy-4-[[(1r)-1-phenylethyl]amino]quinazolin-6-yl]-4-[(2r)-2-methyl-6-oxomorpholin-4-yl]but-2-enamide Chemical compound C1([C@@H](C)NC=2N=CN=C3C=C(C(=CC3=2)NC(=O)C=CCN2CC(=O)O[C@H](C)C2)OC)=CC=CC=C1 WOWRAEPIBQSHBM-QZTJIDSGSA-N 0.000 claims 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 1
- 229920001542 oligosaccharide Polymers 0.000 claims 1
- 150000002482 oligosaccharides Chemical class 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 229960001972 panitumumab Drugs 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- WVUNYSQLFKLYNI-AATRIKPKSA-N pelitinib Chemical compound C=12C=C(NC(=O)\C=C\CN(C)C)C(OCC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 WVUNYSQLFKLYNI-AATRIKPKSA-N 0.000 claims 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
- 229920001282 polysaccharide Polymers 0.000 claims 1
- 239000005017 polysaccharide Substances 0.000 claims 1
- 229960004618 prednisone Drugs 0.000 claims 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims 1
- 239000003755 preservative agent Substances 0.000 claims 1
- 230000002335 preservative effect Effects 0.000 claims 1
- 229960002288 procaterol Drugs 0.000 claims 1
- FKNXQNWAXFXVNW-BLLLJJGKSA-N procaterol Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)[C@@H](NC(C)C)CC FKNXQNWAXFXVNW-BLLLJJGKSA-N 0.000 claims 1
- DQORBCOTYYJLTB-UHFFFAOYSA-N propan-2-yl 4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical compound C=12C=C(OC3CCN(CC3)C(=O)OC(C)C)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 DQORBCOTYYJLTB-UHFFFAOYSA-N 0.000 claims 1
- 239000001294 propane Chemical class 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 claims 1
- 125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 229940044601 receptor agonist Drugs 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
- 229960002720 reproterol Drugs 0.000 claims 1
- WVLAAKXASPCBGT-UHFFFAOYSA-N reproterol Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CCCNCC(O)C1=CC(O)=CC(O)=C1 WVLAAKXASPCBGT-UHFFFAOYSA-N 0.000 claims 1
- 229960001634 ritodrine Drugs 0.000 claims 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 claims 1
- IXTCZMJQGGONPY-XJAYAHQCSA-N rofleponide Chemical compound C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3O[C@@H](CCC)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O IXTCZMJQGGONPY-XJAYAHQCSA-N 0.000 claims 1
- 229950004432 rofleponide Drugs 0.000 claims 1
- MNDBXUUTURYVHR-UHFFFAOYSA-N roflumilast Chemical compound FC(F)OC1=CC=C(C(=O)NC=2C(=CN=CC=2Cl)Cl)C=C1OCC1CC1 MNDBXUUTURYVHR-UHFFFAOYSA-N 0.000 claims 1
- 229960002586 roflumilast Drugs 0.000 claims 1
- 229960002052 salbutamol Drugs 0.000 claims 1
- 229950001879 salmefamol Drugs 0.000 claims 1
- 229960004017 salmeterol Drugs 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 229950010289 soterenol Drugs 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 239000000021 stimulant Substances 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 150000005846 sugar alcohols Polymers 0.000 claims 1
- 229950007862 sulfonterol Drugs 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 229960000195 terbutaline Drugs 0.000 claims 1
- LLTCDTSMNWDXIP-UHFFFAOYSA-N tert-butyl 4-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical compound C=12C=C(OC3CCN(CC3)C(=O)OC(C)(C)C)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 LLTCDTSMNWDXIP-UHFFFAOYSA-N 0.000 claims 1
- QJQCSXAKSADYBA-UHFFFAOYSA-N tert-butyl 4-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]oxypiperidine-1-carboxylate Chemical compound C=12C=C(OC3CCN(CC3)C(=O)OC(C)(C)C)C(OC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 QJQCSXAKSADYBA-UHFFFAOYSA-N 0.000 claims 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 1
- 229950000584 tezosentan Drugs 0.000 claims 1
- 229960000278 theophylline Drugs 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 229960000575 trastuzumab Drugs 0.000 claims 1
- 229960005294 triamcinolone Drugs 0.000 claims 1
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 claims 1
- 229940088594 vitamin Drugs 0.000 claims 1
- 229930003231 vitamin Natural products 0.000 claims 1
- 235000013343 vitamin Nutrition 0.000 claims 1
- 239000011782 vitamin Substances 0.000 claims 1
- 0 Cc1ccc2N=NC(*)c2c1* Chemical compound Cc1ccc2N=NC(*)c2c1* 0.000 description 5
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04018808 | 2004-08-07 | ||
| PCT/EP2005/008385 WO2006015775A2 (en) | 2004-08-07 | 2005-08-03 | Egfr kinase inhibitor combinations for treating respiratory and gastrointestinal disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008509177A JP2008509177A (ja) | 2008-03-27 |
| JP2008509177A5 true JP2008509177A5 (enExample) | 2008-09-18 |
Family
ID=35149668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007525227A Pending JP2008509177A (ja) | 2004-08-07 | 2005-08-03 | 呼吸器系及び消化器系疾患治療用の新規な医薬組成物 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US20060035893A1 (enExample) |
| EP (2) | EP1784224A2 (enExample) |
| JP (1) | JP2008509177A (enExample) |
| CA (1) | CA2575541A1 (enExample) |
| WO (1) | WO2006015775A2 (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050096332A1 (en) * | 2003-10-30 | 2005-05-05 | Boehringer Ingelheim International Gmbh | Use of tyrosine kinase inhibitors for the treatment of inflammatory processes |
| CA2643130A1 (en) * | 2006-02-22 | 2007-08-30 | Valorisation Recherche Hscm, Limited Partnership | Compounds and methods of treating disorders associated with activation of metachromatic cells |
| CA2667543A1 (en) * | 2006-10-26 | 2008-05-02 | Boehringer Ingelheim International Gmbh | New pharmaceutical combinations for treatment of respiratory and gastrointestinal disorders |
| CA2735875A1 (en) * | 2008-09-03 | 2010-03-11 | Boehringer Ingelheim International Gmbh | Use of quinazoline derivatives for the treatment of viral diseases |
| GB0818033D0 (en) | 2008-10-02 | 2008-11-05 | Respivert Ltd | Novel compound |
| BRPI0920707A2 (pt) | 2008-10-02 | 2015-12-29 | Respivert Ltd | compostos |
| MX353900B (es) | 2008-11-07 | 2018-02-01 | Massachusetts Inst Technology | Lipidoides de aminoalcohol y usos de los mismos. |
| US8507502B2 (en) | 2008-11-10 | 2013-08-13 | National Health Research Institutes | Fused bicyclic and tricyclic pyrimidine compounds as tyrosine kinase inhibitors |
| EP2370428B1 (en) | 2008-12-11 | 2016-08-10 | Respivert Limited | P38 map kinase inhibitors |
| GB0905955D0 (en) | 2009-04-06 | 2009-05-20 | Respivert Ltd | Novel compounds |
| US9238716B2 (en) | 2011-03-28 | 2016-01-19 | Massachusetts Institute Of Technology | Conjugated lipomers and uses thereof |
| US8809372B2 (en) | 2011-09-30 | 2014-08-19 | Asana Biosciences, Llc | Pyridine derivatives |
| US9199975B2 (en) | 2011-09-30 | 2015-12-01 | Asana Biosciences, Llc | Biaryl imidazole derivatives for regulating CYP17 |
| PE20181541A1 (es) * | 2011-10-27 | 2018-09-26 | Massachusetts Inst Technology | Derivados de aminoacidos funcionalizados en la terminal n capaces de formar microesferas encapsuladoras de farmaco |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| US9394285B2 (en) | 2013-03-15 | 2016-07-19 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| EP2981535B8 (en) | 2013-04-02 | 2021-03-10 | Oxular Acquisitions Limited | Urea derivatives useful as kinase inhibitors |
| EP3083604A1 (en) | 2013-12-20 | 2016-10-26 | Respivert Limited | Urea derivatives useful as kinase inhibitors |
| CA2956022A1 (en) * | 2014-07-24 | 2016-01-28 | Plus Vitech,S.L | Neurokinin-1 receptor antagonist composition for treatment of diseases and conditions of the respiratory tract |
| BR112017003745A2 (pt) | 2014-08-29 | 2017-12-05 | Tes Pharma S R L | inibidores de semialdeído descarboxilase de ácido alfa-amino-beta-carboximucônico |
| MA40774A (fr) | 2014-10-01 | 2017-08-08 | Respivert Ltd | Dérivés de diaryle-urée en tant qu'inhibiteurs de kinase p38 |
| BR112018067552A2 (pt) | 2016-04-06 | 2019-01-08 | Topivert Pharma Ltd | inibidores de cinase |
| PT3691620T (pt) | 2017-10-05 | 2022-10-06 | Fulcrum Therapeutics Inc | Os inibidores da quinase p38 reduzem a expressão de dux4 e genes a jusante para o tratamento de fshd |
| US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
| US11407771B2 (en) | 2018-05-30 | 2022-08-09 | Washington University | Mitogen-activated protein kinase inhibitors, methods of making, and methods of use thereof |
| WO2022067063A1 (en) * | 2020-09-25 | 2022-03-31 | Dana-Farber Cancer Institute, Inc. | Mutant selective egfr inhibitors and methods of use thereof |
| CN114652826B (zh) * | 2022-01-24 | 2022-10-14 | 景泽生物医药(合肥)有限公司 | 抗egfr抗体的用途 |
| CN118252832A (zh) * | 2022-12-27 | 2024-06-28 | 上海数因信科智能科技有限公司 | Vofopitant用于治疗硬皮病的用途 |
| CN118252833A (zh) * | 2022-12-27 | 2024-06-28 | 上海数因信科智能科技有限公司 | Vofopitant用于治疗肺纤维化的用途 |
Family Cites Families (167)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4570630A (en) | 1983-08-03 | 1986-02-18 | Miles Laboratories, Inc. | Medicament inhalation device |
| AT396872B (de) | 1985-07-30 | 1993-12-27 | Glaxo Group Ltd | Gerät zur verabreichung von medikamenten in pulverform |
| SE453566B (sv) | 1986-03-07 | 1988-02-15 | Draco Ab | Anordning vid pulverinhalatorer |
| SG45171A1 (en) | 1990-03-21 | 1998-01-16 | Boehringer Ingelheim Int | Atomising devices and methods |
| JPH06502178A (ja) | 1990-12-31 | 1994-03-10 | 藤沢薬品工業株式会社 | イミダゾトリアジン誘導体 |
| GB9816837D0 (en) | 1998-08-04 | 1998-09-30 | Zeneca Ltd | Amide derivatives |
| US5716972A (en) | 1993-01-13 | 1998-02-10 | Smithkline Beecham Corporation | Pyridyl substituted imidazoles |
| US5656644A (en) | 1994-07-20 | 1997-08-12 | Smithkline Beecham Corporation | Pyridyl imidazoles |
| IL104369A0 (en) | 1992-01-13 | 1993-05-13 | Smithkline Beecham Corp | Novel compounds and compositions |
| IL107120A (en) | 1992-09-29 | 1997-09-30 | Boehringer Ingelheim Int | Atomising nozzle and filter and spray generating device |
| GB9303993D0 (en) | 1993-02-26 | 1993-04-14 | Fujisawa Pharmaceutical Co | New heterocyclic derivatives |
| DE4318455A1 (de) | 1993-06-03 | 1994-12-08 | Boehringer Ingelheim Kg | Kapselhalterung |
| US5670527A (en) | 1993-07-16 | 1997-09-23 | Smithkline Beecham Corporation | Pyridyl imidazole compounds and compositions |
| US5593992A (en) | 1993-07-16 | 1997-01-14 | Smithkline Beecham Corporation | Compounds |
| US5593991A (en) | 1993-07-16 | 1997-01-14 | Adams; Jerry L. | Imidazole compounds, use and process of making |
| ATE325113T1 (de) | 1993-10-01 | 2006-06-15 | Novartis Pharma Gmbh | Pharmacologisch wirksame pyrimidinderivate und verfahren zu deren herstellung |
| DK0672041T3 (da) | 1993-10-01 | 2002-02-25 | Novartis Ag | Farmakologisk aktive pyridinderivater og fremgangsmåder til fremstilling deraf |
| WO1995009847A1 (en) | 1993-10-01 | 1995-04-13 | Ciba-Geigy Ag | Pyrimidineamine derivatives and processes for the preparation thereof |
| US5543520A (en) | 1993-10-01 | 1996-08-06 | Ciba-Geigy Corporation | Pyrimidine derivatives |
| GB9401182D0 (en) | 1994-01-21 | 1994-03-16 | Inst Of Cancer The Research | Antibodies to EGF receptor and their antitumour effect |
| US5559137A (en) | 1994-05-16 | 1996-09-24 | Smithkline Beecham Corp. | Compounds |
| WO2000023072A1 (en) | 1998-10-20 | 2000-04-27 | Omeros Medical Systems, Inc. | Irrigation solution containing mapk inhibitors and their use for treating pain and inflammation |
| DE69536015D1 (de) | 1995-03-30 | 2009-12-10 | Pfizer Prod Inc | Chinazolinone Derivate |
| TW449590B (en) | 1995-04-14 | 2001-08-11 | Boehringer Ingelheim Kg | New arylglycinamide derivatives, processes for the manufacture thereof and pharmaceutical compositions containing these compounds |
| US5739143A (en) | 1995-06-07 | 1998-04-14 | Smithkline Beecham Corporation | Imidazole compounds and compositions |
| US5658903A (en) | 1995-06-07 | 1997-08-19 | Smithkline Beecham Corporation | Imidazole compounds, compositions and use |
| DK0836605T3 (da) | 1995-07-06 | 2002-05-13 | Novartis Ag | Pyrrolopyrimidiner og fremgangsmåder til deres fremstilling |
| DE19536903C2 (de) | 1995-10-04 | 1998-09-10 | Boehringer Ingelheim Int | Vorrichtung zum Haltern eines fluidischen Bauteils |
| DE19536902A1 (de) | 1995-10-04 | 1997-04-10 | Boehringer Ingelheim Int | Vorrichtung zur Hochdruckerzeugung in einem Fluid in Miniaturausführung |
| EE03681B1 (et) | 1995-10-06 | 2002-04-15 | Merck & Co., Inc. | Asendatud imidasoolid, millel on vähivastane ja tsütokiine inhibeeriv toime |
| WO1997016441A1 (en) | 1995-10-31 | 1997-05-09 | Merck & Co., Inc. | Substituted aryl pyrroles, compositions containing such compounds and methods of use |
| WO1997016442A1 (en) | 1995-10-31 | 1997-05-09 | Merck & Co., Inc. | Substituted pyridyl pyrroles, compositions containing such compounds and methods of use |
| DE19545226C1 (de) | 1995-12-05 | 1997-06-19 | Boehringer Ingelheim Int | Sperrspannwerk für einen federbetätigten Abtrieb |
| US5977103A (en) | 1996-01-11 | 1999-11-02 | Smithkline Beecham Corporation | Substituted imidazole compounds |
| ZA97175B (en) | 1996-01-11 | 1997-11-04 | Smithkline Beecham Corp | Novel substituted imidazole compounds. |
| EP0883402A4 (en) | 1996-01-11 | 1999-08-11 | Smithkline Beecham Corp | NEW CYCLOALKYL-SUBSTITUTED IMIDAZOLES |
| AP9700912A0 (en) | 1996-01-11 | 1997-01-31 | Smithkline Beecham Corp | Novel cycloalkyl substituted imidazoles |
| DE19608665A1 (de) | 1996-03-06 | 1997-09-11 | Boehringer Ingelheim Kg | Neue Arylglycinamidderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
| JP2000506532A (ja) | 1996-03-13 | 2000-05-30 | スミスクライン・ビーチャム・コーポレイション | サイトカイン介在疾患の治療にて有用な新規ピリミジン化合物 |
| JP2000507558A (ja) | 1996-03-25 | 2000-06-20 | スミスクライン・ビーチャム・コーポレイション | Ｃｎｓ損傷についての新規な治療 |
| JP2000507545A (ja) | 1996-03-25 | 2000-06-20 | スミスクライン・ビーチャム・コーポレイション | Ｃｎｓ損傷についての新規な治療 |
| CA2250232A1 (en) | 1996-04-03 | 1997-10-09 | Allen I. Oliff | A method of treating cancer |
| ES2239357T3 (es) | 1996-06-10 | 2005-09-16 | MERCK & CO., INC. | Imidazoles sustituidos que tienen actividad inhibidora de citoquinas. |
| JP2001506230A (ja) | 1996-08-09 | 2001-05-15 | スミスクライン・ビーチャム・コーポレイション | 新規ピペラジン含有化合物 |
| EP0956018A4 (en) | 1996-08-21 | 2000-01-12 | Smithkline Beecham Corp | IMIDAZOLE COMPOUNDS, COMPOSITIONS CONTAINING THEM AND THEIR USE |
| DE19633640C2 (de) | 1996-08-21 | 1999-05-06 | Ford Global Tech Inc | Vorrichtung zur Winkelverstellung einer Welle gegenüber einem Antriebsrad |
| DK0948495T3 (da) | 1996-11-19 | 2004-06-01 | Amgen Inc | Aryl- og heteroarylsubstitueret, kondenseret pyrrol som antiinflammatoriske midler |
| AU730295B2 (en) | 1996-11-20 | 2001-03-01 | Merck & Co., Inc. | Triaryl substituted imidazoles as glucagon antagonists |
| JP2002514195A (ja) | 1996-12-05 | 2002-05-14 | アムジエン・インコーポレーテツド | 置換ピリミジン化合物およびそれの使用 |
| CN1328277C (zh) | 1996-12-05 | 2007-07-25 | 安姆根有限公司 | 取代的嘧啶酮和吡啶酮化合物和它们的应用 |
| ZA9711092B (en) | 1996-12-11 | 1999-07-22 | Smithkline Beecham Corp | Novel compounds. |
| US6147080A (en) | 1996-12-18 | 2000-11-14 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
| AU723895B2 (en) | 1997-01-29 | 2000-09-07 | Pfizer Inc. | Sulfonyl urea derivatives and their use in the control of interleukin-1 activity |
| PL191111B1 (pl) | 1997-04-24 | 2006-03-31 | Ortho Mcneil Pharm Inc | Podstawione imidazole, sposób ich wytwarzania, kompozycje zawierające podstawione imidazole oraz ich zastosowanie |
| WO1998047899A1 (en) | 1997-04-24 | 1998-10-29 | Ortho-Mcneil Corporation, Inc. | Substituted pyrrolopyridines useful in the treatment of inflammatory diseases |
| US6235883B1 (en) | 1997-05-05 | 2001-05-22 | Abgenix, Inc. | Human monoclonal antibodies to epidermal growth factor receptor |
| WO1998050356A1 (en) | 1997-05-07 | 1998-11-12 | Sugen, Inc. | 2-indolinone derivatives as modulators of protein kinase activity |
| RU2249591C2 (ru) | 1997-05-22 | 2005-04-10 | Дж.Д. Серл Энд Ко. | 3(5)-гетероарилзамещенные пиразолы в качестве ингибиторов киназы p38 |
| CA2288787A1 (en) | 1997-05-22 | 1998-11-26 | G.D. Searle And Co. | Pyrazole derivatives as p38 kinase inhibitors |
| TR200000235T2 (tr) | 1997-05-22 | 2000-05-22 | G.D. Searle &Co. | p38 kinaz inhibitörleri olarak ikame edilmiş pirazoller. |
| US6514977B1 (en) | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
| DE1019040T1 (de) | 1997-05-23 | 2001-02-08 | Bayer Corp., West Haven | Hemmung von p38 kinase aktivität durch arylharnstoff |
| EP0986382B1 (en) | 1997-05-23 | 2008-06-25 | Bayer Pharmaceuticals Corporation | Raf kinase inhibitors |
| SK286940B6 (sk) | 1997-06-12 | 2009-07-06 | Aventis Pharma Limited | Spôsob prípravy imidazolového derivátu |
| AU7966198A (en) | 1997-06-13 | 1998-12-30 | Smithkline Beecham Corporation | Novel pyrazole and pyrazoline substituted compounds |
| US6093742A (en) | 1997-06-27 | 2000-07-25 | Vertex Pharmaceuticals, Inc. | Inhibitors of p38 |
| EP0994858A1 (en) | 1997-06-30 | 2000-04-26 | Ortho-McNeil Pharmaceutical, Inc. | 2-substituted imidazoles useful in the treatment of inflammatory diseases |
| GB9713726D0 (en) | 1997-06-30 | 1997-09-03 | Ciba Geigy Ag | Organic compounds |
| US5939421A (en) | 1997-07-01 | 1999-08-17 | Signal Pharmaceuticals, Inc. | Quinazoline analogs and related compounds and methods for treating inflammatory conditions |
| US6251914B1 (en) | 1997-07-02 | 2001-06-26 | Smithkline Beecham Corporation | Cycloalkyl substituted imidazoles |
| TW517055B (en) | 1997-07-02 | 2003-01-11 | Smithkline Beecham Corp | Novel substituted imidazole compounds |
| AR016294A1 (es) | 1997-07-02 | 2001-07-04 | Smithkline Beecham Corp | Compuesto de imidazol sustituido, composicion farmaceutica que la contiene, su uso en la fabricacion de un medicamento y procedimiento para supreparacion |
| US5981710A (en) | 1997-07-21 | 1999-11-09 | Baxter International, Inc. | Therapeutic hemoglobin composition having isotropically increased size |
| KR20010024175A (ko) | 1997-09-23 | 2001-03-26 | 돈 리사 로얄 | 시토킨에 의해 매개되는 질환 치료용 아미드 유도체 |
| US5975738A (en) | 1997-09-30 | 1999-11-02 | Lsi Logic Corporation | Method for detecting failure in redundant controllers using a private LUN |
| WO1999017776A1 (en) | 1997-10-08 | 1999-04-15 | Smithkline Beecham Corporation | Novel cycloalkenyl substituted compounds |
| BR9814961A (pt) | 1997-11-14 | 2000-10-03 | Sankyo Co | Composto ou um sal ou derivado deste farmacologicamente aceitáveis, e, medicamentos antiinflamatório, para prevenção ou tratamento de reumatismo crÈnico, e para prevenção ou tratamento de osteoartrite |
| JP2002515891A (ja) | 1997-12-19 | 2002-05-28 | スミスクライン・ビーチャム・コーポレイション | 新規なピペリジン含有化合物 |
| US6335340B1 (en) | 1997-12-19 | 2002-01-01 | Smithkline Beecham Corporation | compounds of heteroaryl substituted imidazole, their pharmaceutical compositons and uses |
| DE69836563T2 (de) | 1997-12-22 | 2007-05-16 | Bayer Pharmaceuticals Corp., West Haven | INHIBIERUNG DER p38 KINASE-AKTIVITÄT DURCH DIE VERWENDUNG VON ARYL- UND HETEROARYL-SUBSTITUIERTEN HARNSTOFFEN |
| ATE529109T1 (de) | 1997-12-22 | 2011-11-15 | Bayer Healthcare Llc | Hemmung der p38 kinase aktivität durch substituierte heterocyclische harnstoffe |
| AU1939999A (en) | 1997-12-22 | 1999-07-12 | Bayer Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
| GB9800569D0 (en) | 1998-01-12 | 1998-03-11 | Glaxo Group Ltd | Heterocyclic compounds |
| CA2321559A1 (en) | 1998-02-26 | 1999-09-02 | Ortho-Mcneil Pharmaceutical, Inc. | Substituted pyrrolobenzimidazoles for treating inflammatory diseases |
| WO1999050238A1 (en) | 1998-03-26 | 1999-10-07 | Santen Pharmaceutical Co., Ltd. | Novel urea derivatives |
| US6316466B1 (en) | 1998-05-05 | 2001-11-13 | Syntex (U.S.A.) Llc | Pyrazole derivatives P-38 MAP kinase inhibitors |
| IL139169A0 (en) | 1998-05-05 | 2001-11-25 | Hoffmann La Roche | Pyrazole derivatives as p-38 map kinase inhibitors |
| MY132496A (en) | 1998-05-11 | 2007-10-31 | Vertex Pharma | Inhibitors of p38 |
| CA2331878A1 (en) | 1998-05-14 | 1999-11-18 | G.D. Searle & Co. | 1,5-diaryl substituted pyrazoles as p38 kinase inhibitors |
| PL195600B1 (pl) | 1998-05-15 | 2007-10-31 | Astrazeneca Ab | Pochodne benzamidowe, sposób ich wytwarzania, zawierające je kompozycje farmaceutyczne oraz ich zastosowanie do wytwarzania leku do leczenia stanów medycznych powstających za pośrednictwem cytokin |
| WO1999059960A1 (en) | 1998-05-15 | 1999-11-25 | Astrazeneca Ab | Benzamide derivatives for the treatment of diseases mediated by cytokines |
| US6589954B1 (en) | 1998-05-22 | 2003-07-08 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
| KR20010025087A (ko) | 1998-05-22 | 2001-03-26 | 스튜어트 알. 수터 | 신규한 2-알킬 치환된 이미다졸 화합물 |
| US6340685B1 (en) | 1998-05-22 | 2002-01-22 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
| ES2258331T3 (es) | 1998-05-22 | 2006-08-16 | Scios Inc. | Compuestos heterociclicos y procedimientos de tratamiento de insuficiencia cardiaca y otros trastornos. |
| JP2002516325A (ja) | 1998-05-26 | 2002-06-04 | スミスクライン・ビーチャム・コーポレイション | 新規な置換イミダゾール化合物 |
| AU4429799A (en) | 1998-06-12 | 1999-12-30 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
| AU4395399A (en) | 1998-07-02 | 2000-01-24 | Sankyo Company Limited | Five-membered heteroaryl compounds |
| US6207687B1 (en) | 1998-07-31 | 2001-03-27 | Merck & Co., Inc. | Substituted imidazoles having cytokine inhibitory activity |
| BR9912729A (pt) | 1998-08-04 | 2001-05-02 | Astrazeneca Ab | Derivado de amida, processo para prepará-lo, e, uso do mesmo |
| EP1103543A4 (en) | 1998-08-05 | 2005-06-22 | Santen Pharmaceutical Co Ltd | NOVEL UREA DERIVATIVES CONTAINING NITROGENIC AROMATIC HETEROCYCLES |
| US6599910B1 (en) | 1998-08-20 | 2003-07-29 | Smithkline Beecham Corporation | Substituted triazole compounds |
| US6184226B1 (en) | 1998-08-28 | 2001-02-06 | Scios Inc. | Quinazoline derivatives as inhibitors of P-38 α |
| BR9913654A (pt) | 1998-08-28 | 2001-11-27 | Scios Inc | Inibidores de p-38alfa quinase |
| JP4191825B2 (ja) | 1998-09-10 | 2008-12-03 | あすか製薬株式会社 | ５−アミノイソキサゾール誘導体 |
| AR023659A1 (es) | 1998-09-18 | 2002-09-04 | Vertex Pharma | Un compuesto inhibidor de p38, una composicion farmaceutica que lo comprende y el uso de dicha composicion en el tratamiento y prevencion de estados patologicos |
| CA2337755C (en) | 1998-09-18 | 2008-07-29 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
| DE19842833B4 (de) | 1998-09-18 | 2005-04-14 | Merckle Gmbh | 2-Arylalkylthio-imidazole, 2-Arylalkenylthio-imidazole und 2-Arylalkinylthio-imidazole als Entzündungs-Hemmstoffe und Hemmstoffe der Cytokin-Freisetzung |
| AU761361B2 (en) | 1998-09-25 | 2003-06-05 | Astrazeneca Ab | Benzamide derivatives and their use as cytokine inhibitors |
| BR9914162A (pt) | 1998-10-01 | 2001-06-26 | Astrazeneca Ab | Derivado de amida, processo para preparar um derivado de amida, ou um sal farmaceuticamente aceitável ou éster clivável in vivo do mesmo, composição farmacêutica e uso de um derivado de amida, ou um sal farmaceuticamente aceitável ou éster clivável in vivo do mesmo |
| DE19847968A1 (de) | 1998-10-17 | 2000-04-20 | Boehringer Ingelheim Pharma | Verschlußkappe und Behälter als Zweikammer-Kartusche für Vernebler zur Erzeugung von Aerosolen |
| AU6476599A (en) | 1998-11-03 | 2000-05-22 | Novartis Ag | Anti-inflammatory 4-phenyl-5-pyrimidinyl-imidazoles |
| JP2002528506A (ja) | 1998-11-04 | 2002-09-03 | スミスクライン・ビーチャム・コーポレイション | ピリジン−４−イルまたはピリミジン−４−イル置換ピラジン |
| WO2000031048A1 (en) | 1998-11-19 | 2000-06-02 | Warner-Lambert Company | N-[4-(3-chloro-4-fluoro-phenylamino)-7-(3-morpholin-4-yl-propoxy)-quinazolin-6-yl]-acrylamide, an irreversible inhibitor of tyrosine kinases |
| US6350744B1 (en) | 1998-11-20 | 2002-02-26 | Merck & Co., Inc. | Compounds having cytokine inhibitory activity |
| CA2350081A1 (en) | 1998-11-20 | 2000-06-02 | G.D. Searle & Co. | Process for making 5-substituted pyrazoles using dithietanes |
| WO2000036096A1 (en) | 1998-12-16 | 2000-06-22 | Vertex Pharmaceuticals Incorporated | Crystallized p38 complexes |
| DE69903976T2 (de) | 1998-12-16 | 2003-07-24 | Aventis Pharma Ltd | Heteroaryl-zyklische acetale |
| CA2356263C (en) | 1998-12-25 | 2009-04-21 | Teikoku Hormone Mfg. Co., Ltd. | Aminopyrazole derivatives |
| ATE538794T1 (de) | 1999-01-13 | 2012-01-15 | Bayer Healthcare Llc | Gamma carboxyarylsubstituierte diphenylharnstoffverbindungen als p38 kinasehemmer |
| UA73492C2 (en) | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| ATE309237T1 (de) | 1999-03-12 | 2005-11-15 | Boehringer Ingelheim Pharma | Aromatische heterozyklische verbindungen als antientzündungwirkstoffe |
| IL144897A0 (en) | 1999-03-12 | 2002-06-30 | Boehringer Ingelheim Pharma | Compounds useful as anti-inflammatory agents |
| ATE266023T1 (de) | 1999-03-17 | 2004-05-15 | Astrazeneca Ab | Amid-derivate |
| CN100352804C (zh) | 1999-03-17 | 2007-12-05 | 阿斯特拉曾尼卡有限公司 | 酰胺衍生物 |
| GB9906566D0 (en) | 1999-03-23 | 1999-05-19 | Zeneca Ltd | Chemical compounds |
| CO5170501A1 (es) | 1999-04-14 | 2002-06-27 | Novartis Ag | AZOLES SUSTITUIDOS UTILES PARA EL TRATAMIENTO DE ENFERMEDADES MEDIADAS POR TNFa eIL-1 Y ENFERMEDADES DEL METABOLISMO OSEO |
| US6492516B1 (en) | 1999-05-14 | 2002-12-10 | Merck & Co., Inc. | Compounds having cytokine inhibitory activity |
| AU772295B2 (en) | 1999-05-21 | 2004-04-22 | Scios Inc. | Indole-type derivatives as inhibitors of p38 kinase |
| WO2000078735A1 (de) | 1999-06-21 | 2000-12-28 | Boehringer Ingelheim Pharma Kg | Bicyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| US6403596B1 (en) | 1999-06-28 | 2002-06-11 | Merck & Co., Inc. | Substituted pyridones having cytokine inhibitory activity |
| PL352944A1 (en) | 1999-07-16 | 2003-09-22 | Leo Pharma | Aminobenzophenones as inhibitors of il-1beta and tnf-alpha |
| DK1202954T3 (da) | 1999-07-16 | 2004-02-09 | Leo Pharma As | Nye aminobenzophenoner |
| RU2247719C2 (ru) | 1999-07-16 | 2005-03-10 | Лео Фармасьютикал Продактс Лтд.А/С (Левенс Кемиске Фабрик Продукционсактиесельскаб) | Аминобензофеноны как ингибиторы il-1 бета и tnf-альфа, фармацевтическая композиция и способ лечения и/или профилактики воспалительных заболеваний |
| NZ516825A (en) | 1999-07-16 | 2004-05-28 | Leo Pharm Prod Ltd | Aminobenzophenones as inhibitors of IL-1beta and TNF-alpha |
| PT1202957E (pt) | 1999-07-16 | 2005-01-31 | Leo Pharma As | Aminobenzofenonas como inibidoras de il-1beta e tnf-alpha |
| JP2003511055A (ja) | 1999-10-13 | 2003-03-25 | レオ・ファーマ・アクティーゼルスカブ | Ｍｓｋ１に作用する物質をスクリーニングする方法 |
| GB9924092D0 (en) | 1999-10-13 | 1999-12-15 | Zeneca Ltd | Pyrimidine derivatives |
| CZ20021743A3 (cs) | 1999-10-21 | 2002-08-14 | F. Hoffmann-La Roche Ag | Bicyklické dusíkové heterocykly substituované alkylaminoskupinou jako inhibitory P38 proteinkinázy |
| CA2388142C (en) | 1999-10-21 | 2008-12-09 | F. Hoffmann-La Roche Ag | Heteroalkylamino-substituted bicyclic nitrogen heterocycles as inhibitors of p38 protein kinase |
| KR20010089805A (ko) | 1999-11-10 | 2001-10-08 | 오르토-맥네일 파마슈티칼, 인코퍼레이티드 | 치환된 2-아릴-3-(헤테로아릴)-이미다조[1,2-ａ]피리미딘,및 관련 약제학적 조성물 및 방법 |
| UA74803C2 (uk) | 1999-11-11 | 2006-02-15 | Осі Фармасьютікалз, Інк. | Стійкий поліморф гідрохлориду n-(3-етинілфеніл)-6,7-біс(2-метоксіетокси)-4-хіназолінаміну, спосіб його одержання (варіанти) та фармацевтичне застосування |
| WO2001036403A1 (en) | 1999-11-16 | 2001-05-25 | Boehringer Ingelheim Pharmaceuticals, Inc. | Urea derivatives as anti-inflammatory agents |
| EP1248624A4 (en) | 1999-11-23 | 2003-01-22 | Smithkline Beecham Corp | 3,4-DIHYDRO- (1H) -CHIRAZOLINE-2-ONES AND THE USE THEREOF AS CSBP / P38 KINASE INHIBITORS |
| JP2003514899A (ja) | 1999-11-23 | 2003-04-22 | スミスクライン・ビーチャム・コーポレイション | ＣＳＢＰ／ｐ３８キナーゼ阻害剤としての３，４‐ジヒドロ−（１Ｈ）−キナゾリン−２−オン化合物 |
| DE60023025T2 (de) | 1999-11-23 | 2006-07-13 | Smithkline Beecham Corp. | 3,4-dihydro-(1h)chinazolin-2-on-verbindungen als csbp/p39-kinase-inhibitoren |
| AU1783201A (en) | 1999-11-23 | 2001-06-04 | Smithkline Beecham Corporation | 3,4-dihydro-(1h)quinazolin-2-one compounds as csbp/p38 kinase inhibitors |
| HUP0203813A3 (en) | 1999-12-06 | 2008-03-28 | Leo Pharma As | Aminobenzophenones as inhibitors of il-1betha and tnf-alpha, pharmaceutical compositions containing them and their use |
| US6602872B1 (en) | 1999-12-13 | 2003-08-05 | Merck & Co., Inc. | Substituted pyridazines having cytokine inhibitory activity |
| DE60043397D1 (de) | 1999-12-28 | 2010-01-07 | Pharmacopeia Inc | Cytokine, insbesondere tnf-alpha, hemmer |
| DE20002820U1 (de) | 2000-02-16 | 2000-05-25 | Igus Spritzgußteile für die Industrie GmbH, 51147 Köln | Energieführungskette |
| AU2001238651A1 (en) | 2000-02-23 | 2001-09-03 | Iconix Pharmaceuticals, Inc. | Pyridine-amidines as modulators of p38 map kinase |
| AU2001241927A1 (en) | 2000-02-28 | 2001-09-12 | Scios Inc. | Inhibitors of p38-alpha kinase |
| ATE350378T1 (de) | 2000-04-08 | 2007-01-15 | Boehringer Ingelheim Pharma | Bicyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| US6653305B2 (en) * | 2000-08-26 | 2003-11-25 | Boehringer Ingelheim Pharma Kg | Bicyclic heterocycles, pharmaceutical compositions containing them, their use, and processes for preparing them |
| DE10042062A1 (de) | 2000-08-26 | 2002-03-07 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Hertellung |
| DE10042060A1 (de) | 2000-08-26 | 2002-03-07 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| DE10042058A1 (de) | 2000-08-26 | 2002-03-07 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| DE10042059A1 (de) | 2000-08-26 | 2002-03-07 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| DE10051320A1 (de) | 2000-10-17 | 2002-04-25 | Boehringer Ingelheim Pharma | Neue Neurokininantagonisten, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
| DE10206505A1 (de) * | 2002-02-16 | 2003-08-28 | Boehringer Ingelheim Pharma | Neue Arzneimittelkompositionen auf der Basis von Anticholinergika und EGFR-Kinase-Hemmern |
| DE10063435A1 (de) | 2000-12-20 | 2002-07-04 | Boehringer Ingelheim Pharma | Chinazolinderviate,diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| AU2003226705B2 (en) | 2002-03-30 | 2008-11-06 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 4-(N-phenylamino)-quinazolines / quinolines as tyrosine kinase inhibitors |
| US6924285B2 (en) * | 2002-03-30 | 2005-08-02 | Boehringer Ingelheim Pharma Gmbh & Co. | Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them |
| US7244728B2 (en) * | 2004-03-17 | 2007-07-17 | Boehringer Ingelheim International Gmbh | Long acting betamimetics for the treatment of respiratory diseases |
| US20050239778A1 (en) * | 2004-04-22 | 2005-10-27 | Boehringer Ingelheim International Gmbh | Novel medicament combinations for the treatment of respiratory diseases |
| DE102005030733A1 (de) * | 2005-07-01 | 2007-01-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Arzneimittelkombinationen zur Behandlung von Atemwegserkrankungen enthaltend langwirksame Beta-2-Agonisten und wenigstens einen weiteren Wirkstoff |
-
2005
- 2005-07-26 US US11/189,643 patent/US20060035893A1/en not_active Abandoned
- 2005-08-03 CA CA002575541A patent/CA2575541A1/en not_active Abandoned
- 2005-08-03 EP EP05773706A patent/EP1784224A2/en not_active Withdrawn
- 2005-08-03 EP EP09167644A patent/EP2116245A3/en not_active Withdrawn
- 2005-08-03 WO PCT/EP2005/008385 patent/WO2006015775A2/en not_active Ceased
- 2005-08-03 JP JP2007525227A patent/JP2008509177A/ja active Pending
-
2008
- 2008-09-02 US US12/202,784 patent/US20090017036A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2008509177A5 (enExample) | ||
| JP2008509177A (ja) | 呼吸器系及び消化器系疾患治療用の新規な医薬組成物 | |
| JP4966192B2 (ja) | 抗ムスカリン剤およびβ−アドレナリンアゴニストを含む組合せ剤 | |
| ES2666098T3 (es) | Combinación de fármacos | |
| ES2828070T3 (es) | Métodos para tratar trastornos autoinmunitarios, respiratorios e inflamatorios mediante la inhalación de n-oxido de roflumilast | |
| CA2764867C (en) | Treatment of chronic obstructive pulmonary disease with nebulized beta 2-agonist or combined nebulized beta 2-agonist and anticholinergic administration | |
| JP2009503014A (ja) | 呼吸器系疾患の治療におけるジヒドロプテリジノン | |
| KR20050006149A (ko) | 항콜린제 및 ｐ38 키나아제 억제제를 기본으로 하는신규한 약제학적 조성물 | |
| ZA200600411B (en) | Methods of treating COPD and Pulmonary Hypertension | |
| Malerba et al. | Single Inhaler LABA/LAMA for COPD | |
| MXPA01011400A (es) | Nuevas composiciones de medicamentos a base de compuestos anitolinergicmanete activos y beta-mimeticos. | |
| TW200800294A (en) | Pharmaceutical composition for aerosols with two or more active substances and at least one surfactant | |
| CN105407890B (zh) | 包含maba化合物和皮质类固醇的结合物 | |
| HUE028008T2 (en) | sGC STIMULATORS OR sGC ACTIVATORS ALONE AND IN COMBINATION WITH PDE5 INHBITORS FOR THE TREATMENT OF CYSTIC FIBROSIS | |
| BR112018013903B1 (pt) | Usos de orvepitante ou de uma composição que compreende o mesmo para tratar tosse crônica | |
| Prakash et al. | Profile of inhaled glycopyrronium bromide as monotherapy and in fixed-dose combination with indacaterol maleate for the treatment of COPD | |
| JP6346618B2 (ja) | アクリジニウムの新規用途 | |
| JP2005517039A5 (enExample) | ||
| JP2005538066A5 (enExample) | ||
| JP2005538066A (ja) | 新規な抗コリン作用薬及びｐ３８キナーゼ阻害剤を用いた新規な医薬組成物 | |
| RU2422144C2 (ru) | Применение солей тиотропия для лечения тяжелых форм персистирующей астмы | |
| Kelly | Umeclidinium bromide and vilanterol in combination for the treatment of chronic obstructive pulmonary disease | |
| JP2007500146A5 (enExample) | ||
| JP6527305B2 (ja) | 禁煙のためのβ−アドレナリン作動性インバースアゴニストの使用 | |
| Rabe | GFF MDI for the improvement of lung function in COPD–a look at the PINNACLE-1 and PINNACLE-2 data and beyond |