KR20080050475A - Ａ2ｂ 아데노신 수용체 안타고니스트로서의 이미다조피리딘유도체 - Google Patents

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Publication number

KR20080050475A

KR20080050475A KR1020087008297A KR20087008297A KR20080050475A KR 20080050475 A KR20080050475 A KR 20080050475A KR 1020087008297 A KR1020087008297 A KR 1020087008297A KR 20087008297 A KR20087008297 A KR 20087008297A KR 20080050475 A KR20080050475 A KR 20080050475A

Authority

KR

South Korea

Prior art keywords

pyridin

imidazo

fluoropyridin

pyridine

mmol

Prior art date

2005-10-06

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.)

Withdrawn

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• 229940121359 adenosine receptor antagonist Drugs 0.000 title description 4
• 239000000296 purinergic P1 receptor antagonist Substances 0.000 title description 4
• 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title 1
• 239000005557 antagonist Substances 0.000 claims abstract description 13
• 108050000203 Adenosine receptors Proteins 0.000 claims abstract description 11
• 102000009346 Adenosine receptors Human genes 0.000 claims abstract description 11
• 150000001875 compounds Chemical class 0.000 claims description 200
• 238000000034 method Methods 0.000 claims description 89
• -1 piperidinylamino Chemical group 0.000 claims description 60
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 36
• 125000001424 substituent group Chemical group 0.000 claims description 22
• 125000005843 halogen group Chemical group 0.000 claims description 20
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 19
• 238000011282 treatment Methods 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 201000010099 disease Diseases 0.000 claims description 13
• 150000003839 salts Chemical class 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 125000003282 alkyl amino group Chemical group 0.000 claims description 9
• 125000000623 heterocyclic group Chemical group 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 229940043355 kinase inhibitor Drugs 0.000 claims description 9
• 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 9
• GTAJJJFAEJTSKM-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-2-methylsulfanyl-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound C=1C=CN=CC=1C=1N=C2NC(SC)=NC2=CC=1C1=CC=NC=C1F GTAJJJFAEJTSKM-UHFFFAOYSA-N 0.000 claims description 8
• OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 8
• 125000001072 heteroaryl group Chemical group 0.000 claims description 8
• 230000001575 pathological effect Effects 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
• 230000008485 antagonism Effects 0.000 claims description 6
• 208000006673 asthma Diseases 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 125000002950 monocyclic group Chemical group 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 201000001320 Atherosclerosis Diseases 0.000 claims description 5
• 208000018522 Gastrointestinal disease Diseases 0.000 claims description 5
• 206010020772 Hypertension Diseases 0.000 claims description 5
• 206010061218 Inflammation Diseases 0.000 claims description 5
• 206010063837 Reperfusion injury Diseases 0.000 claims description 5
• 208000017442 Retinal disease Diseases 0.000 claims description 5
• 206010038923 Retinopathy Diseases 0.000 claims description 5
• 208000026935 allergic disease Diseases 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 230000004054 inflammatory process Effects 0.000 claims description 5
• 208000031225 myocardial ischemia Diseases 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• HAODEOLEIIJMMV-UHFFFAOYSA-N (3,5-difluorophenyl)-[6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridin-2-yl]methanone Chemical compound FC1=CC(F)=CC(C(=O)C=2NC3=NC(=C(C=4C(=CN=CC=4)F)C=C3N=2)C=2C=NC=CC=2)=C1 HAODEOLEIIJMMV-UHFFFAOYSA-N 0.000 claims description 4
• NEKLJQZEHUUVND-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl]-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(F)=CC=C1CC1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 NEKLJQZEHUUVND-UHFFFAOYSA-N 0.000 claims description 4
• ZBWYPXKJPAXPEP-UHFFFAOYSA-N 4-[6-(3,5-difluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridin-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC2=CC(C=3C(=CN=CC=3F)F)=C(C=3C=NC=CC=3)N=C2N1 ZBWYPXKJPAXPEP-UHFFFAOYSA-N 0.000 claims description 4
• LGHGHJRAFKVZEZ-UHFFFAOYSA-N 4-[6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridin-2-yl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 LGHGHJRAFKVZEZ-UHFFFAOYSA-N 0.000 claims description 4
• QNRWWMIRCJNAGS-UHFFFAOYSA-N 4-[[6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridin-2-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 QNRWWMIRCJNAGS-UHFFFAOYSA-N 0.000 claims description 4
• GCETZIHCDDRCER-UHFFFAOYSA-N 6-(3,5-difluoropyridin-4-yl)-2-(4-fluorophenyl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(F)=CC=C1C1=NC2=CC(C=3C(=CN=CC=3F)F)=C(C=3C=NC=CC=3)N=C2N1 GCETZIHCDDRCER-UHFFFAOYSA-N 0.000 claims description 4
• NMMRGCUIBJKKIO-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-2-(3-methylimidazol-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound CN1C=NC=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 NMMRGCUIBJKKIO-UHFFFAOYSA-N 0.000 claims description 4
• MMAZBBTVGGVGIM-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-2-(4-methoxyphenyl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 MMAZBBTVGGVGIM-UHFFFAOYSA-N 0.000 claims description 4
• DOKIWYXXGULGJJ-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-2-(1H-1,2,4-triazol-5-yl)-1H-imidazo[4,5-b]pyridine Chemical compound FC1=CN=CC=C1C(C(=N1)C=2C=NC=CC=2)=CC2=C1NC(C=1NC=NN=1)=N2 DOKIWYXXGULGJJ-UHFFFAOYSA-N 0.000 claims description 4
• QCAGPDXBMNNMBH-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-2-pyridin-4-yl-1h-imidazo[4,5-b]pyridine Chemical compound FC1=CN=CC=C1C(C(=N1)C=2C=NC=CC=2)=CC2=C1NC(C=1C=CN=CC=1)=N2 QCAGPDXBMNNMBH-UHFFFAOYSA-N 0.000 claims description 4
• 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 4
• 229960005305 adenosine Drugs 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000005647 linker group Chemical group 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• ZQYYXKXTXVOABI-UHFFFAOYSA-N methyl 4-[6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 ZQYYXKXTXVOABI-UHFFFAOYSA-N 0.000 claims description 4
• CVKYNSKSNYSKPL-UHFFFAOYSA-N n-(4-fluorophenyl)-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridin-2-amine Chemical compound C1=CC(F)=CC=C1NC1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 CVKYNSKSNYSKPL-UHFFFAOYSA-N 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 102000005962 receptors Human genes 0.000 claims description 4
• 108020003175 receptors Proteins 0.000 claims description 4
• CNOMOQJYMHEVNH-UHFFFAOYSA-N 1-[6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 CNOMOQJYMHEVNH-UHFFFAOYSA-N 0.000 claims description 3
• CMGXDPCRFRFEQJ-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound FC1=CN=CC=C1C(C(=N1)C=2C=NC=CC=2)=CC2=C1NC(C=1C=C3OCCOC3=CC=1)=N2 CMGXDPCRFRFEQJ-UHFFFAOYSA-N 0.000 claims description 3
• LOUMZSUMBGYUSB-UHFFFAOYSA-N 2-(2,4-dichloro-5-fluorophenyl)-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound C1=C(Cl)C(F)=CC(C=2NC3=NC(=C(C=4C(=CN=CC=4)F)C=C3N=2)C=2C=NC=CC=2)=C1Cl LOUMZSUMBGYUSB-UHFFFAOYSA-N 0.000 claims description 3
• BORHYOMEYOQQOE-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound N1=C(C)C=C(C)N1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 BORHYOMEYOQQOE-UHFFFAOYSA-N 0.000 claims description 3
• UQDQYSLQDYYJQJ-UHFFFAOYSA-N 2-(3-chloropyridin-4-yl)-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound FC1=CN=CC=C1C(C(=N1)C=2C=NC=CC=2)=CC2=C1NC(C=1C(=CN=CC=1)Cl)=N2 UQDQYSLQDYYJQJ-UHFFFAOYSA-N 0.000 claims description 3
• KAZUSWOHYPVEKM-UHFFFAOYSA-N 2-(4-fluorophenyl)-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(F)=CC=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 KAZUSWOHYPVEKM-UHFFFAOYSA-N 0.000 claims description 3
• WELTYXZXXJRVNV-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 WELTYXZXXJRVNV-UHFFFAOYSA-N 0.000 claims description 3
• CEEBIXJLOBIHFK-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)ethyl]-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound C=1C=C(Cl)C=CC=1C(C)C(NC1=NC=2C=3C=NC=CC=3)=NC1=CC=2C1=CC=NC=C1F CEEBIXJLOBIHFK-UHFFFAOYSA-N 0.000 claims description 3
• JMNOPWJKGOGKSU-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)propan-2-yl]-6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound C=1C=C(Cl)C=CC=1C(C)(C)C(NC1=NC=2C=3C=NC=CC=3)=NC1=CC=2C1=CC=NC=C1F JMNOPWJKGOGKSU-UHFFFAOYSA-N 0.000 claims description 3
• SIBXJJSFYUSKKF-UHFFFAOYSA-N 3-[6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridin-2-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2NC3=NC(=C(C=4C(=CN=CC=4)F)C=C3N=2)C=2C=NC=CC=2)=C1 SIBXJJSFYUSKKF-UHFFFAOYSA-N 0.000 claims description 3
• CREHNQNSIKXYDP-UHFFFAOYSA-N 4-[2-[6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridin-2-yl]ethyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CCC1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 CREHNQNSIKXYDP-UHFFFAOYSA-N 0.000 claims description 3
• VENIDIZFNHVWLJ-UHFFFAOYSA-N 5,6-bis(3-chloropyridin-4-yl)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound ClC1=CN=CC=C1C(C(=N1)C=2C(=CN=CC=2)Cl)=CC2=C1NC(=O)N2 VENIDIZFNHVWLJ-UHFFFAOYSA-N 0.000 claims description 3
• MUUGCFKLOVKSDN-UHFFFAOYSA-N 5-(3-chloropyridin-4-yl)-2-(4-fluorophenyl)-6-(3-fluoropyridin-4-yl)-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(F)=CC=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C(=CN=CC=3)Cl)N=C2N1 MUUGCFKLOVKSDN-UHFFFAOYSA-N 0.000 claims description 3
• AUHKQACTCSTFNA-UHFFFAOYSA-N 6-(3-chloropyridin-4-yl)-2-(4-fluorophenyl)-5-pyridin-4-yl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(F)=CC=C1C1=NC2=CC(C=3C(=CN=CC=3)Cl)=C(C=3C=CN=CC=3)N=C2N1 AUHKQACTCSTFNA-UHFFFAOYSA-N 0.000 claims description 3
• QEFGTGPZSGHXNT-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-2-(2-methylpyrazol-3-yl)-5-pyridin-3-yl-1H-imidazo[4,5-b]pyridine Chemical compound CN1N=CC=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 QEFGTGPZSGHXNT-UHFFFAOYSA-N 0.000 claims description 3
• JSSLEBFKIMPAHU-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-2-(2-phenylethyl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound FC1=CN=CC=C1C(C(=N1)C=2C=NC=CC=2)=CC2=C1NC(CCC=1C=CC=CC=1)=N2 JSSLEBFKIMPAHU-UHFFFAOYSA-N 0.000 claims description 3
• YJJBVCAWJOZRLC-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-2-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]-5-pyridin-3-yl-1H-imidazo[4,5-b]pyridine Chemical compound CN1N=C(C(F)(F)F)C=C1C1=NC2=CC(C=3C(=CN=CC=3)F)=C(C=3C=NC=CC=3)N=C2N1 YJJBVCAWJOZRLC-UHFFFAOYSA-N 0.000 claims description 3
• JVJZXCPOFNLDOW-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-2-[3-fluoro-4-(trifluoromethyl)phenyl]-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound FC1=CN=CC=C1C(C(=N1)C=2C=NC=CC=2)=CC2=C1NC(C=1C=C(F)C(=CC=1)C(F)(F)F)=N2 JVJZXCPOFNLDOW-UHFFFAOYSA-N 0.000 claims description 3
• HLKCDGMRIKFNNR-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-2-(2-pyridin-3-ylethyl)-1h-imidazo[4,5-b]pyridine Chemical compound FC1=CN=CC=C1C(C(=N1)C=2C=NC=CC=2)=CC2=C1NC(CCC=1C=NC=CC=1)=N2 HLKCDGMRIKFNNR-UHFFFAOYSA-N 0.000 claims description 3
• CSPSBRHWRRLXMI-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-2-[4-(trifluoromethyl)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound FC1=CN=CC=C1C(C(=N1)C=2C=NC=CC=2)=CC2=C1NC(C=1C=CC(=CC=1)C(F)(F)F)=N2 CSPSBRHWRRLXMI-UHFFFAOYSA-N 0.000 claims description 3
• JEBZHYRMRJAPRX-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-2-[[3-(trifluoromethyl)phenyl]methyl]-1h-imidazo[4,5-b]pyridine Chemical compound FC1=CN=CC=C1C(C(=N1)C=2C=NC=CC=2)=CC2=C1NC(CC=1C=C(C=CC=1)C(F)(F)F)=N2 JEBZHYRMRJAPRX-UHFFFAOYSA-N 0.000 claims description 3
• JNJZPKODYHXOKE-UHFFFAOYSA-N 6-(3-fluoropyridin-4-yl)-n,5-dipyridin-3-yl-1h-imidazo[4,5-b]pyridin-2-amine Chemical compound FC1=CN=CC=C1C(C(=N1)C=2C=NC=CC=2)=CC2=C1NC(NC=1C=NC=CC=1)=N2 JNJZPKODYHXOKE-UHFFFAOYSA-N 0.000 claims description 3
• 239000005711 Benzoic acid Substances 0.000 claims description 3
• 102100024167 C-C chemokine receptor type 3 Human genes 0.000 claims description 3
• 101710149862 C-C chemokine receptor type 3 Proteins 0.000 claims description 3
• 108010008212 Integrin alpha4beta1 Proteins 0.000 claims description 3
• 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 3
• 150000001204 N-oxides Chemical class 0.000 claims description 3
• 108010040718 Neurokinin-1 Receptors Proteins 0.000 claims description 3
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 3
• 102100037346 Substance-P receptor Human genes 0.000 claims description 3
• 102000000551 Syk Kinase Human genes 0.000 claims description 3
• 108010016672 Syk Kinase Proteins 0.000 claims description 3
• 235000010233 benzoic acid Nutrition 0.000 claims description 3
• 229940124748 beta 2 agonist Drugs 0.000 claims description 3
• 230000008602 contraction Effects 0.000 claims description 3
• 239000003246 corticosteroid Substances 0.000 claims description 3
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• 208000035475 disorder Diseases 0.000 claims description 3
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• YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims description 3
• 125000002971 oxazolyl group Chemical group 0.000 claims description 3
• 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 3
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 3
• 230000002062 proliferating effect Effects 0.000 claims description 3
• 150000003222 pyridines Chemical class 0.000 claims description 3
• 229940044601 receptor agonist Drugs 0.000 claims description 3
• 239000000018 receptor agonist Substances 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• 241001465754 Metazoa Species 0.000 claims description 2
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 230000003042 antagnostic effect Effects 0.000 claims description 2
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 2
• 235000012054 meals Nutrition 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• 150000004885 piperazines Chemical class 0.000 claims description 2
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000003386 piperidinyl group Chemical group 0.000 claims description 2
• 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 2
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