CA2575541A1

CA2575541A1 - New pharmaceutical compositions for treatment of respiratory and gastrointestinal disorders

New pharmaceutical compositions for treatment of respiratory and gastrointestinal disorders Download PDF

Info

Publication number: CA2575541A1
Authority: CA; Canada
Prior art keywords: alkyl; amino; phenyl; optionally; optionally substituted
Prior art date: 2004-08-07
Legal status : Abandoned

Application number

CA002575541A

Other languages

English (en)

French (fr)

Inventor

Birgit Jung

Frank Himmelsbach

Current Assignee

Boehringer Ingelheim International GmbH

Original Assignee

Individual

Priority date

2004-08-07

Filing date

2005-08-03

Publication date

2006-02-16

2005-08-03 Application filed by Individual filed Critical Individual

2006-02-16 Publication of CA2575541A1 publication Critical patent/CA2575541A1/en

Status Abandoned legal-status Critical Current

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 120
238000011282 treatment Methods 0.000 title claims abstract description 9
230000000241 respiratory effect Effects 0.000 title abstract description 5
208000018522 Gastrointestinal disease Diseases 0.000 title description 2
208000023504 respiratory system disease Diseases 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 115
102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims abstract description 62
108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims abstract description 62
229940121647 egfr inhibitor Drugs 0.000 claims abstract description 34
150000003431 steroids Chemical class 0.000 claims abstract description 29
239000000203 mixture Substances 0.000 claims abstract description 28
239000002829 mitogen activated protein kinase inhibitor Substances 0.000 claims abstract description 19
239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims abstract description 19
239000005557 antagonist Substances 0.000 claims abstract description 15
208000027866 inflammatory disease Diseases 0.000 claims abstract description 9
238000000034 method Methods 0.000 claims abstract description 9
239000003814 drug Substances 0.000 claims abstract description 6
-1 4-[(R)-(1-phenyl-ethyl)]-6-{[4-(N,N-bis-(2-methoxy-ethyl)-amino)-1-oxo- 2-buten-1-yl]amino}-7-cyclopropylmethoxy-quinazoline Chemical compound 0.000 claims description 552
125000000217 alkyl group Chemical group 0.000 claims description 426
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 252
125000000623 heterocyclic group Chemical group 0.000 claims description 170
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 168
229910052736 halogen Inorganic materials 0.000 claims description 156
150000002367 halogens Chemical class 0.000 claims description 156
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 description 145
229910020008 S(O) Inorganic materials 0.000 claims description 143
125000003545 alkoxy group Chemical group 0.000 claims description 122
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 120
125000004076 pyridyl group Chemical group 0.000 claims description 106
150000002825 nitriles Chemical class 0.000 claims description 100
125000001624 naphthyl group Chemical group 0.000 claims description 98
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 86
125000003118 aryl group Chemical group 0.000 claims description 83
125000001072 heteroaryl group Chemical group 0.000 claims description 72
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 70
125000000714 pyrimidinyl group Chemical group 0.000 claims description 69
125000002883 imidazolyl group Chemical group 0.000 claims description 68
229940043355 kinase inhibitor Drugs 0.000 claims description 63
239000003757 phosphotransferase inhibitor Substances 0.000 claims description 63
150000003839 salts Chemical class 0.000 claims description 63
125000003373 pyrazinyl group Chemical group 0.000 claims description 61
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 59
125000003226 pyrazolyl group Chemical group 0.000 claims description 58
125000002541 furyl group Chemical group 0.000 claims description 56
125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 55
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 55
125000002098 pyridazinyl group Chemical group 0.000 claims description 55
125000004043 oxo group Chemical group O=* 0.000 claims description 53
125000001544 thienyl group Chemical group 0.000 claims description 53
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 51
125000000168 pyrrolyl group Chemical group 0.000 claims description 50
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 49
229910052760 oxygen Inorganic materials 0.000 claims description 49
229910052717 sulfur Inorganic materials 0.000 claims description 49
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 47
125000005843 halogen group Chemical group 0.000 claims description 46
125000000753 cycloalkyl group Chemical group 0.000 claims description 44
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 43
125000000392 cycloalkenyl group Chemical group 0.000 claims description 42
239000002253 acid Substances 0.000 claims description 41
239000001257 hydrogen Substances 0.000 claims description 41
229910052739 hydrogen Inorganic materials 0.000 claims description 41
125000001786 isothiazolyl group Chemical group 0.000 claims description 38
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 37
229910052757 nitrogen Inorganic materials 0.000 claims description 37
125000000842 isoxazolyl group Chemical group 0.000 claims description 36
125000004193 piperazinyl group Chemical group 0.000 claims description 36
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 34
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 34
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 33
125000003435 aroyl group Chemical group 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 28
125000003282 alkyl amino group Chemical group 0.000 claims description 28
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 28
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 27
125000005842 heteroatom Chemical group 0.000 claims description 27
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 25
206010006451 bronchitis Diseases 0.000 claims description 25
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 25
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 24
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 24
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 description 23
239000013543 active substance Substances 0.000 claims description 23
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 23
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 22
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 22
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 22
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 description 21
125000003342 alkenyl group Chemical group 0.000 claims description 21
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 21
125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 20
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 20
102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims description 20
108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims description 20
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 description 20
150000004677 hydrates Chemical class 0.000 claims description 20
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 description 20
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 20
239000000546 pharmaceutical excipient Substances 0.000 claims description 20
125000003386 piperidinyl group Chemical group 0.000 claims description 20
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 20
125000003831 tetrazolyl group Chemical group 0.000 claims description 20
201000010099 disease Diseases 0.000 claims description 19
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
229960002848 formoterol Drugs 0.000 claims description 19
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 description 19
QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims description 18
VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 claims description 18
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 18
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 18
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 17
125000001041 indolyl group Chemical group 0.000 claims description 17
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 17
229930192474 thiophene Natural products 0.000 claims description 17
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 16
125000000304 alkynyl group Chemical group 0.000 claims description 16
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 16
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 description 16
150000002431 hydrogen Chemical group 0.000 claims description 16
229960004017 salmeterol Drugs 0.000 claims description 16
208000029523 Interstitial Lung disease Diseases 0.000 claims description 15
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 description 15
239000003937 drug carrier Substances 0.000 claims description 15
210000001035 gastrointestinal tract Anatomy 0.000 claims description 15
125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
229920006395 saturated elastomer Polymers 0.000 claims description 15
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 14
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 14
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 14
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 13
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 13
208000027157 chronic rhinosinusitis Diseases 0.000 claims description 13
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 description 13
230000002757 inflammatory effect Effects 0.000 claims description 13
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 13
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 13
125000003107 substituted aryl group Chemical group 0.000 claims description 13
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 12
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 12
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 12
229940122696 MAP kinase inhibitor Drugs 0.000 claims description 12
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 12
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 12
125000002757 morpholinyl group Chemical group 0.000 claims description 12
208000015768 polyposis Diseases 0.000 claims description 12
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 11
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 11
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 11
ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 11
WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 claims description 11
MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 claims description 11
229960002714 fluticasone Drugs 0.000 claims description 11
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 description 11
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 11
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 11
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 11
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
239000000808 adrenergic beta-agonist Substances 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
125000004599 benzpyrazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 10
230000003454 betamimetic effect Effects 0.000 claims description 10
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 description 10
230000001684 chronic effect Effects 0.000 claims description 10
229940125782 compound 2 Drugs 0.000 claims description 10
239000001301 oxygen Substances 0.000 claims description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
239000011593 sulfur Chemical group 0.000 claims description 10
125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 9
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 description 9
125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 claims description 9
206010035664 Pneumonia Diseases 0.000 claims description 9
206010035742 Pneumonitis Diseases 0.000 claims description 9
208000037062 Polyps Diseases 0.000 claims description 9
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 9
229960004436 budesonide Drugs 0.000 claims description 9
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 9
125000005046 dihydronaphthyl group Chemical group 0.000 claims description 9
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 9
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 9
208000005069 pulmonary fibrosis Diseases 0.000 claims description 9
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 9
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 9
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 8
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
230000000414 obstructive effect Effects 0.000 claims description 8
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 8
239000012453 solvate Substances 0.000 claims description 8
125000000547 substituted alkyl group Chemical group 0.000 claims description 8
125000001425 triazolyl group Chemical group 0.000 claims description 8
GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 7
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 7
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 7
125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 7
125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
125000005844 heterocyclyloxy group Chemical group 0.000 claims description 7
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 7
229960001664 mometasone Drugs 0.000 claims description 7
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 description 7
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 description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 7
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 description 7
229960002586 roflumilast Drugs 0.000 claims description 7
150000003335 secondary amines Chemical class 0.000 claims description 7
150000003512 tertiary amines Chemical class 0.000 claims description 7
150000003536 tetrazoles Chemical class 0.000 claims description 7
125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 6
206010009137 Chronic sinusitis Diseases 0.000 claims description 6
206010009900 Colitis ulcerative Diseases 0.000 claims description 6
208000011231 Crohn disease Diseases 0.000 claims description 6
201000003883 Cystic fibrosis Diseases 0.000 claims description 6
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 6
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
201000006704 Ulcerative Colitis Diseases 0.000 claims description 6
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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 description 1
TVBZKMHBLROHSN-UHFFFAOYSA-N n-[5-[4-[[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC=C1C(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)N=C1 TVBZKMHBLROHSN-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
125000005968 oxazolinyl group Chemical group 0.000 description 1
125000003566 oxetanyl group Chemical group 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NBFNGRDFKUJVIN-VAWYXSNFSA-N phenyl (e)-3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1/C=C/C(=O)OC1=CC=CC=C1 NBFNGRDFKUJVIN-VAWYXSNFSA-N 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
125000005545 phthalimidyl group Chemical group 0.000 description 1
125000005547 pivalate group Chemical group 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 description 1
125000006513 pyridinyl methyl group Chemical group 0.000 description 1
DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Natural products OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 1
VONGYFFEWFJHNP-UHFFFAOYSA-N pyrrolecarboxylic acid methyl ester Natural products COC(=O)C1=CC=CN1 VONGYFFEWFJHNP-UHFFFAOYSA-N 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
229940086735 succinate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
230000001975 sympathomimetic effect Effects 0.000 description 1
229940064707 sympathomimetics Drugs 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000002769 thiazolinyl group Chemical group 0.000 description 1
125000005503 thioxanyl group Chemical group 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1