NZ585697A - 2-propynyl adenosine analogs with modified 5'-ribose groups having A2A agonist activity - Google Patents

Info

Publication number

NZ585697A

NZ585697A NZ585697A NZ58569705A NZ585697A NZ 585697 A NZ585697 A NZ 585697A NZ 585697 A NZ585697 A NZ 585697A NZ 58569705 A NZ58569705 A NZ 58569705A NZ 585697 A NZ585697 A NZ 585697A

Authority

NZ

New Zealand

Prior art keywords

compound

alkylene

alkyl

aryl

methyl

Prior art date

2004-08-02

Links

• Espacenet
• Global Dossier
• Discuss

• 230000000694 effects Effects 0.000 title claims description 29
• 239000000556 agonist Substances 0.000 title abstract description 30
• UBWAYMVIDZVHHG-ZRFIDHNTSA-N (2r,3r,4s,5r)-2-(6-amino-2-prop-1-ynylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical class C12=NC(C#CC)=NC(N)=C2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O UBWAYMVIDZVHHG-ZRFIDHNTSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 160
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 70
• 239000000203 mixture Substances 0.000 claims abstract description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 22
• 230000028709 inflammatory response Effects 0.000 claims abstract description 18
• 239000003814 drug Substances 0.000 claims abstract description 16
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 13
• 201000010099 disease Diseases 0.000 claims abstract description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
• 238000004519 manufacturing process Methods 0.000 claims abstract description 11
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 9
• 125000001424 substituent group Chemical group 0.000 claims abstract description 7
• 230000005764 inhibitory process Effects 0.000 claims abstract description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 169
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 136
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 124
• 125000002947 alkylene group Chemical group 0.000 claims description 111
• 125000003118 aryl group Chemical group 0.000 claims description 102
• -1 pyrrolidino, piperidino, morpholino Chemical group 0.000 claims description 98
• 125000000217 alkyl group Chemical group 0.000 claims description 95
• 125000001072 heteroaryl group Chemical group 0.000 claims description 86
• 229910052739 hydrogen Inorganic materials 0.000 claims description 76
• 239000001257 hydrogen Substances 0.000 claims description 74
• 238000002360 preparation method Methods 0.000 claims description 45
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
• 125000005843 halogen group Chemical group 0.000 claims description 29
• 125000004429 atom Chemical group 0.000 claims description 27
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
• 101150051188 Adora2a gene Proteins 0.000 claims description 22
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 18
• 229910003827 NRaRb Inorganic materials 0.000 claims description 17
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 229910052705 radium Inorganic materials 0.000 claims description 15
• 229910052701 rubidium Inorganic materials 0.000 claims description 15
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 125000006413 ring segment Chemical group 0.000 claims description 13
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 claims description 12
• UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 12
• 241000124008 Mammalia Species 0.000 claims description 11
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
• 229960005141 piperazine Drugs 0.000 claims description 11
• HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical group COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 claims description 11
• 229950005741 rolipram Drugs 0.000 claims description 11
• 229940099471 Phosphodiesterase inhibitor Drugs 0.000 claims description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims description 10
• 150000001412 amines Chemical class 0.000 claims description 10
• QEGNUYASOUJEHD-UHFFFAOYSA-N gem-dimethylcyclohexane Natural products CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 claims description 10
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 10
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 10
• 150000002978 peroxides Chemical class 0.000 claims description 10
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
• 150000001413 amino acids Chemical class 0.000 claims description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 8
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 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 8
• 239000002571 phosphodiesterase inhibitor Substances 0.000 claims description 8
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 8
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
• 125000005505 thiomorpholino group Chemical group 0.000 claims description 8
• XJLSEXAGTJCILF-YFKPBYRVSA-N (S)-nipecotic acid Chemical compound OC(=O)[C@H]1CCCNC1 XJLSEXAGTJCILF-YFKPBYRVSA-N 0.000 claims description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
• QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 6
• LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexyl-acetic acid Natural products OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 claims description 6
• IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 claims description 6
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 229920006395 saturated elastomer Polymers 0.000 claims description 6
• FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims description 6
• XTVMZZBLCLWBPM-UHFFFAOYSA-N tert-butylcyclohexane Chemical compound CC(C)(C)C1CCCCC1 XTVMZZBLCLWBPM-UHFFFAOYSA-N 0.000 claims description 6
• 125000001589 carboacyl group Chemical group 0.000 claims description 5
• 125000002837 carbocyclic group Chemical group 0.000 claims description 5
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims description 4
• RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 4
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
• 230000001575 pathological effect Effects 0.000 claims description 4
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 4
• 230000001225 therapeutic effect Effects 0.000 claims description 4
• AULUDJRRNHDTJI-UHFFFAOYSA-N 1,1,3,3-tetramethylcyclohexane Chemical compound CC1(C)CCCC(C)(C)C1 AULUDJRRNHDTJI-UHFFFAOYSA-N 0.000 claims description 3
• XAZKFISIRYLAEE-UHFFFAOYSA-N 1,3-dimethylcyclopentane Chemical compound CC1CCC(C)C1 XAZKFISIRYLAEE-UHFFFAOYSA-N 0.000 claims description 3
• FUFZNHHSSMCXCZ-UHFFFAOYSA-N 5-piperidin-4-yl-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical group FC(F)(F)C1=CC=CC(C=2N=C(ON=2)C2CCNCC2)=C1 FUFZNHHSSMCXCZ-UHFFFAOYSA-N 0.000 claims description 3
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• HJZLEGIHUQOJBA-UHFFFAOYSA-N cyclohexane propionic acid Chemical compound OC(=O)CCC1CCCCC1 HJZLEGIHUQOJBA-UHFFFAOYSA-N 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 3
• 208000024891 symptom Diseases 0.000 claims description 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
• OQJVXNHMUWQQEW-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrazine Chemical compound C1CNC=CN1 OQJVXNHMUWQQEW-UHFFFAOYSA-N 0.000 claims description 2
• QYMGRIFMUQCAJW-UHFFFAOYSA-N 1,2-dihydropyrazine Chemical compound C1NC=CN=C1 QYMGRIFMUQCAJW-UHFFFAOYSA-N 0.000 claims description 2
• WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 claims description 2
• DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 claims description 2
• YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 2
• LWTIGYSPAXKMDG-UHFFFAOYSA-N 2,3-dihydro-1h-imidazole Chemical compound C1NC=CN1 LWTIGYSPAXKMDG-UHFFFAOYSA-N 0.000 claims description 2
• KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical compound C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 claims description 2
• VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 2
• PXXNTAGJWPJAGM-VCOUNFBDSA-N Decaline Chemical compound C=1([C@@H]2C3)C=C(OC)C(OC)=CC=1OC(C=C1)=CC=C1CCC(=O)O[C@H]3C[C@H]1N2CCCC1 PXXNTAGJWPJAGM-VCOUNFBDSA-N 0.000 claims description 2
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 2
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
• 230000008484 agonism Effects 0.000 claims description 2
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
• 229950001653 cilomilast Drugs 0.000 claims description 2
• 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 claims description 2
• 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 claims description 2
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 2
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
• YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 2
• 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 claims description 2
• PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 claims description 2
• NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 2
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
• 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 claims 2
• 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims 2
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
• OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims 1
• 239000003937 drug carrier Substances 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
• 239000000243 solution Substances 0.000 description 61
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 34
• ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 34
• 238000003756 stirring Methods 0.000 description 34
• 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 description 32
• 238000000034 method Methods 0.000 description 31
• 210000000440 neutrophil Anatomy 0.000 description 27
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
• 150000002431 hydrogen Chemical group 0.000 description 26
• 238000011282 treatment Methods 0.000 description 25
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 24
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
• 239000000047 product Substances 0.000 description 22
• 238000006243 chemical reaction Methods 0.000 description 21
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
• 238000007429 general method Methods 0.000 description 20
• 210000004027 cell Anatomy 0.000 description 19
• 239000003795 chemical substances by application Substances 0.000 description 19
• 239000003921 oil Substances 0.000 description 19
• 235000019198 oils Nutrition 0.000 description 19
• 239000007787 solid Substances 0.000 description 19
• 210000001519 tissue Anatomy 0.000 description 19
• 229910001868 water Inorganic materials 0.000 description 19
• 206010061218 Inflammation Diseases 0.000 description 18
• 238000005481 NMR spectroscopy Methods 0.000 description 18
• 230000004054 inflammatory process Effects 0.000 description 18
• 239000002126 C01EB10 - Adenosine Substances 0.000 description 17
• 229960005305 adenosine Drugs 0.000 description 17
• 239000002904 solvent Substances 0.000 description 16
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 238000003384 imaging method Methods 0.000 description 15
• 230000002757 inflammatory effect Effects 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• 150000001345 alkine derivatives Chemical class 0.000 description 13
• 239000003379 purinergic P1 receptor agonist Substances 0.000 description 13
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 12
• 206010040047 Sepsis Diseases 0.000 description 12
• 206010040070 Septic Shock Diseases 0.000 description 12
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 12
• 235000019439 ethyl acetate Nutrition 0.000 description 12
• 235000019253 formic acid Nutrition 0.000 description 12
• 208000015181 infectious disease Diseases 0.000 description 12
• 239000007788 liquid Substances 0.000 description 12
• 230000001590 oxidative effect Effects 0.000 description 12
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 11
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 11
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 11
• 239000003112 inhibitor Substances 0.000 description 11
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
• 239000003242 anti bacterial agent Substances 0.000 description 10
• 239000002552 dosage form Substances 0.000 description 10
• 238000004809 thin layer chromatography Methods 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
• 230000036772 blood pressure Effects 0.000 description 9
• 230000010412 perfusion Effects 0.000 description 9
• 230000000144 pharmacologic effect Effects 0.000 description 9
• 230000036303 septic shock Effects 0.000 description 9
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
• 241000894006 Bacteria Species 0.000 description 8
• 150000001204 N-oxides Chemical class 0.000 description 8
• 101150024701 PPH3 gene Proteins 0.000 description 8
• 241000700605 Viruses Species 0.000 description 8
• 239000005557 antagonist Substances 0.000 description 8
• 238000003818 flash chromatography Methods 0.000 description 8
• 208000014674 injury Diseases 0.000 description 8
• 208000028867 ischemia Diseases 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 238000000746 purification Methods 0.000 description 8
• 150000003254 radicals Chemical class 0.000 description 8
• 239000007858 starting material Substances 0.000 description 8
• 241000193738 Bacillus anthracis Species 0.000 description 7
• 101150041968 CDC13 gene Proteins 0.000 description 7
• 108091006905 Human Serum Albumin Proteins 0.000 description 7
• 102000008100 Human Serum Albumin Human genes 0.000 description 7
• 108010008211 N-Formylmethionine Leucyl-Phenylalanine Proteins 0.000 description 7
• 206010035148 Plague Diseases 0.000 description 7
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
• 208000034784 Tularaemia Diseases 0.000 description 7
• 241000607479 Yersinia pestis Species 0.000 description 7
• 239000002253 acid Substances 0.000 description 7
• 239000004480 active ingredient Substances 0.000 description 7
• 230000002411 adverse Effects 0.000 description 7
• 230000001580 bacterial effect Effects 0.000 description 7
• PRQROPMIIGLWRP-BZSNNMDCSA-N chemotactic peptide Chemical compound CSCC[C@H](NC=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 PRQROPMIIGLWRP-BZSNNMDCSA-N 0.000 description 7
• 210000004351 coronary vessel Anatomy 0.000 description 7
• 238000004128 high performance liquid chromatography Methods 0.000 description 7
• 238000001802 infusion Methods 0.000 description 7
• 230000002107 myocardial effect Effects 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• 102000005962 receptors Human genes 0.000 description 7
• 108020003175 receptors Proteins 0.000 description 7
• 239000000377 silicon dioxide Substances 0.000 description 7
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• 108050000203 Adenosine receptors Proteins 0.000 description 6
• 102000009346 Adenosine receptors Human genes 0.000 description 6
• 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 6
• 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 6
• JADDQZYHOWSFJD-FLNNQWSLSA-N N-ethyl-5'-carboxamidoadenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 JADDQZYHOWSFJD-FLNNQWSLSA-N 0.000 description 6
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
• OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 6
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 6
• 239000003443 antiviral agent Substances 0.000 description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
• 230000027455 binding Effects 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 6
• 210000000265 leukocyte Anatomy 0.000 description 6
• 210000000056 organ Anatomy 0.000 description 6
• 239000001301 oxygen Substances 0.000 description 6
• 230000002829 reductive effect Effects 0.000 description 6
• 230000035939 shock Effects 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• 239000011780 sodium chloride Substances 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• 238000002560 therapeutic procedure Methods 0.000 description 6
• 230000008733 trauma Effects 0.000 description 6
• 229940122614 Adenosine receptor agonist Drugs 0.000 description 5
• 102000004127 Cytokines Human genes 0.000 description 5
• 108090000695 Cytokines Proteins 0.000 description 5
• 241000282412 Homo Species 0.000 description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
• 201000003176 Severe Acute Respiratory Syndrome Diseases 0.000 description 5
• 208000036142 Viral infection Diseases 0.000 description 5
• 238000002399 angioplasty Methods 0.000 description 5
• 229940088710 antibiotic agent Drugs 0.000 description 5
• 239000003429 antifungal agent Substances 0.000 description 5
• 229940121375 antifungal agent Drugs 0.000 description 5
• 230000017531 blood circulation Effects 0.000 description 5
• 238000010511 deprotection reaction Methods 0.000 description 5
• 238000002474 experimental method Methods 0.000 description 5
• 238000001990 intravenous administration Methods 0.000 description 5
• 239000010410 layer Substances 0.000 description 5
• HWYHZTIRURJOHG-UHFFFAOYSA-N luminol Chemical compound O=C1NNC(=O)C2=C1C(N)=CC=C2 HWYHZTIRURJOHG-UHFFFAOYSA-N 0.000 description 5
• 210000002540 macrophage Anatomy 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 210000001616 monocyte Anatomy 0.000 description 5
• 239000003208 petroleum Substances 0.000 description 5
• 239000008194 pharmaceutical composition Substances 0.000 description 5
• 230000003389 potentiating effect Effects 0.000 description 5
• 239000002287 radioligand Substances 0.000 description 5
• 239000011541 reaction mixture Substances 0.000 description 5
• 230000009885 systemic effect Effects 0.000 description 5
• 238000002054 transplantation Methods 0.000 description 5
• 230000009385 viral infection Effects 0.000 description 5
• MGEBVSZZNFOIRB-UUOKFMHZSA-N (2r,3r,4s,5r)-2-(6-amino-2-iodopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC(I)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O MGEBVSZZNFOIRB-UUOKFMHZSA-N 0.000 description 4
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
• HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 4
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 4
• 201000000057 Coronary Stenosis Diseases 0.000 description 4
• 241000588722 Escherichia Species 0.000 description 4
• 241000725303 Human immunodeficiency virus Species 0.000 description 4
• 108010003541 Platelet Activating Factor Proteins 0.000 description 4
• 206010063837 Reperfusion injury Diseases 0.000 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
• 230000009471 action Effects 0.000 description 4
• 230000004913 activation Effects 0.000 description 4
• 229910021529 ammonia Inorganic materials 0.000 description 4
• 239000002775 capsule Substances 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• 208000029078 coronary artery disease Diseases 0.000 description 4
• 230000006378 damage Effects 0.000 description 4
• 230000034994 death Effects 0.000 description 4
• 231100000517 death Toxicity 0.000 description 4
• 230000007423 decrease Effects 0.000 description 4
• 239000006185 dispersion Substances 0.000 description 4
• 229940079593 drug Drugs 0.000 description 4
• 238000002592 echocardiography Methods 0.000 description 4
• 230000006870 function Effects 0.000 description 4
• 210000002216 heart Anatomy 0.000 description 4
• 238000004896 high resolution mass spectrometry Methods 0.000 description 4
• 238000001727 in vivo Methods 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
• AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
• 239000012528 membrane Substances 0.000 description 4
• 231100000252 nontoxic Toxicity 0.000 description 4
• 230000003000 nontoxic effect Effects 0.000 description 4
• AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 4
• 230000001717 pathogenic effect Effects 0.000 description 4
• YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 4
• 239000012217 radiopharmaceutical Substances 0.000 description 4
• 229940121896 radiopharmaceutical Drugs 0.000 description 4
• 230000002799 radiopharmaceutical effect Effects 0.000 description 4
• 238000010992 reflux Methods 0.000 description 4
• 238000004007 reversed phase HPLC Methods 0.000 description 4
• 210000003491 skin Anatomy 0.000 description 4
• 230000035882 stress Effects 0.000 description 4
• 239000011593 sulfur Substances 0.000 description 4
• 239000003826 tablet Substances 0.000 description 4
• 238000012360 testing method Methods 0.000 description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• 239000003053 toxin Substances 0.000 description 4
• 231100000765 toxin Toxicity 0.000 description 4
• 108700012359 toxins Proteins 0.000 description 4
• MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 4
• FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 4
• 235000012141 vanillin Nutrition 0.000 description 4
• 239000003071 vasodilator agent Substances 0.000 description 4
• RIRGCFBBHQEQQH-SSFGXONLSA-N (-)-n6-(2-phenylisopropyl)adenosine Chemical compound C([C@@H](C)NC=1C=2N=CN(C=2N=CN=1)[C@H]1[C@@H]([C@H](O)[C@@H](CO)O1)O)C1=CC=CC=C1 RIRGCFBBHQEQQH-SSFGXONLSA-N 0.000 description 3
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
• 101710169336 5'-deoxyadenosine deaminase Proteins 0.000 description 3
• 208000030507 AIDS Diseases 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• 102000055025 Adenosine deaminases Human genes 0.000 description 3
• 201000001320 Atherosclerosis Diseases 0.000 description 3
• 208000035143 Bacterial infection Diseases 0.000 description 3
• 201000011001 Ebola Hemorrhagic Fever Diseases 0.000 description 3
• 206010017533 Fungal infection Diseases 0.000 description 3
• 108010010803 Gelatin Proteins 0.000 description 3
• 239000007995 HEPES buffer Substances 0.000 description 3
• 239000012981 Hank's balanced salt solution Substances 0.000 description 3
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
• 241001465754 Metazoa Species 0.000 description 3
• 102000003896 Myeloperoxidases Human genes 0.000 description 3
• 108090000235 Myeloperoxidases Proteins 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• 241000700159 Rattus Species 0.000 description 3
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 description 3
• 208000009982 Ventricular Dysfunction Diseases 0.000 description 3
• 238000002583 angiography Methods 0.000 description 3
• 230000003110 anti-inflammatory effect Effects 0.000 description 3
• 206010003246 arthritis Diseases 0.000 description 3
• 208000006673 asthma Diseases 0.000 description 3
• 208000022362 bacterial infectious disease Diseases 0.000 description 3
• 125000002619 bicyclic group Chemical group 0.000 description 3
• 239000000872 buffer Substances 0.000 description 3
• 125000004112 carboxyamino group Chemical group [H]OC(=O)N([H])[*] 0.000 description 3
• 239000000969 carrier Substances 0.000 description 3
• 238000002591 computed tomography Methods 0.000 description 3
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
• 206010012601 diabetes mellitus Diseases 0.000 description 3
• 239000003085 diluting agent Substances 0.000 description 3
• 239000002158 endotoxin Substances 0.000 description 3
• 210000003979 eosinophil Anatomy 0.000 description 3
• 239000000499 gel Substances 0.000 description 3
• 229920000159 gelatin Polymers 0.000 description 3
• 239000008273 gelatin Substances 0.000 description 3
• 235000019322 gelatine Nutrition 0.000 description 3
• 235000011852 gelatine desserts Nutrition 0.000 description 3
• 208000027866 inflammatory disease Diseases 0.000 description 3
• 238000002955 isolation Methods 0.000 description 3
• 150000002576 ketones Chemical class 0.000 description 3
• 229910052744 lithium Inorganic materials 0.000 description 3
• 210000004698 lymphocyte Anatomy 0.000 description 3
• 238000004949 mass spectrometry Methods 0.000 description 3
• 210000003622 mature neutrocyte Anatomy 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
• 230000008018 melting Effects 0.000 description 3
• 244000005700 microbiome Species 0.000 description 3
• 125000002950 monocyclic group Chemical group 0.000 description 3
• 229920001223 polyethylene glycol Polymers 0.000 description 3
• 230000010410 reperfusion Effects 0.000 description 3
• 230000010076 replication Effects 0.000 description 3
• 230000004044 response Effects 0.000 description 3
• 150000008223 ribosides Chemical group 0.000 description 3
• 239000004576 sand Substances 0.000 description 3
• 238000003860 storage Methods 0.000 description 3
• 239000004094 surface-active agent Substances 0.000 description 3
• 238000003786 synthesis reaction Methods 0.000 description 3
• 239000006188 syrup Substances 0.000 description 3
• 235000020357 syrup Nutrition 0.000 description 3
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
• 229940124549 vasodilator Drugs 0.000 description 3
• 239000003981 vehicle Substances 0.000 description 3
• 230000006815 ventricular dysfunction Effects 0.000 description 3
• 239000003643 water by type Substances 0.000 description 3
• BIXYYZIIJIXVFW-UUOKFMHZSA-N (2R,3R,4S,5R)-2-(6-amino-2-chloro-9-purinyl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O BIXYYZIIJIXVFW-UUOKFMHZSA-N 0.000 description 2
• GCYUJISWSVALJD-UHFFFAOYSA-N 1,1-diethylcyclohexane Chemical group CCC1(CC)CCCCC1 GCYUJISWSVALJD-UHFFFAOYSA-N 0.000 description 2
• LOZWAPSEEHRYPG-UHFFFAOYSA-N 1,4-dithiane Chemical compound C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 2
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
• 102000004023 5-Lipoxygenase-Activating Proteins Human genes 0.000 description 2
• 108090000411 5-Lipoxygenase-Activating Proteins Proteins 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
• APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 description 2
• 108010039627 Aprotinin Proteins 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• 208000023275 Autoimmune disease Diseases 0.000 description 2
• 241000167854 Bourreria succulenta Species 0.000 description 2
• PAOANWZGLPPROA-RQXXJAGISA-N CGS-21680 Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(NCCC=3C=CC(CCC(O)=O)=CC=3)=NC(N)=C2N=C1 PAOANWZGLPPROA-RQXXJAGISA-N 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• 229920002261 Corn starch Polymers 0.000 description 2
• PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 2
• 108010036949 Cyclosporine Proteins 0.000 description 2
• 206010014824 Endotoxic shock Diseases 0.000 description 2
• 241000588724 Escherichia coli Species 0.000 description 2
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
• 229930091371 Fructose Natural products 0.000 description 2
• RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
• 239000005715 Fructose Substances 0.000 description 2
• 241000233866 Fungi Species 0.000 description 2
• 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 2
• 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
• 208000001953 Hypotension Diseases 0.000 description 2
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• 238000011050 LAL assay Methods 0.000 description 2
• GDBQQVLCIARPGH-UHFFFAOYSA-N Leupeptin Natural products CC(C)CC(NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(C=O)CCCN=C(N)N GDBQQVLCIARPGH-UHFFFAOYSA-N 0.000 description 2
• 208000016604 Lyme disease Diseases 0.000 description 2
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
• 208000031888 Mycoses Diseases 0.000 description 2
• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
• NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
• 206010053879 Sepsis syndrome Diseases 0.000 description 2
• 208000006011 Stroke Diseases 0.000 description 2
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
• 229930006000 Sucrose Natural products 0.000 description 2
• 210000001744 T-lymphocyte Anatomy 0.000 description 2
• 206010052779 Transplant rejections Diseases 0.000 description 2
• GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 2
• 206010047163 Vasospasm Diseases 0.000 description 2
• 208000027418 Wounds and injury Diseases 0.000 description 2
• 238000010521 absorption reaction Methods 0.000 description 2
• 229960000583 acetic acid Drugs 0.000 description 2
• 239000002597 adenosine A2 receptor agonist Substances 0.000 description 2
• 150000003835 adenosine derivatives Chemical class 0.000 description 2
• 238000011360 adjunctive therapy Methods 0.000 description 2
• PYMYPHUHKUWMLA-LMVFSUKVSA-N aldehydo-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 2
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
• 208000026935 allergic disease Diseases 0.000 description 2
• APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 2
• 229960003942 amphotericin b Drugs 0.000 description 2
• 238000004458 analytical method Methods 0.000 description 2
• 150000001450 anions Chemical class 0.000 description 2
• 230000000844 anti-bacterial effect Effects 0.000 description 2
• 239000002220 antihypertensive agent Substances 0.000 description 2
• 229940030600 antihypertensive agent Drugs 0.000 description 2
• 208000007474 aortic aneurysm Diseases 0.000 description 2
• 229960004405 aprotinin Drugs 0.000 description 2
• 230000001363 autoimmune Effects 0.000 description 2
• 230000003115 biocidal effect Effects 0.000 description 2
• 210000004369 blood Anatomy 0.000 description 2
• 239000008280 blood Substances 0.000 description 2
• 230000037396 body weight Effects 0.000 description 2
• 230000005587 bubbling Effects 0.000 description 2
• 150000001721 carbon Chemical group 0.000 description 2
• 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 235000019693 cherries Nutrition 0.000 description 2
• OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
• 229960001265 ciclosporin Drugs 0.000 description 2
• 230000000295 complement effect Effects 0.000 description 2
• 239000008120 corn starch Substances 0.000 description 2
• 239000012043 crude product Substances 0.000 description 2
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
• 229930182912 cyclosporin Natural products 0.000 description 2
• 210000004443 dendritic cell Anatomy 0.000 description 2
• 230000001419 dependent effect Effects 0.000 description 2
• 238000011161 development Methods 0.000 description 2
• 238000002405 diagnostic procedure Methods 0.000 description 2
• 238000000502 dialysis Methods 0.000 description 2
• 235000014113 dietary fatty acids Nutrition 0.000 description 2
• 230000002526 effect on cardiovascular system Effects 0.000 description 2
• 238000001378 electrochemiluminescence detection Methods 0.000 description 2
• 239000000194 fatty acid Substances 0.000 description 2
• 229930195729 fatty acid Natural products 0.000 description 2
• 239000012530 fluid Substances 0.000 description 2
• 235000003599 food sweetener Nutrition 0.000 description 2
• 125000002541 furyl group Chemical group 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• 210000003630 histaminocyte Anatomy 0.000 description 2
• 150000002430 hydrocarbons Chemical group 0.000 description 2
• 125000002883 imidazolyl group Chemical group 0.000 description 2
• 210000000987 immune system Anatomy 0.000 description 2
• 230000001965 increasing effect Effects 0.000 description 2
• 125000001041 indolyl group Chemical group 0.000 description 2
• 230000001939 inductive effect Effects 0.000 description 2
• 230000002458 infectious effect Effects 0.000 description 2
• 230000004968 inflammatory condition Effects 0.000 description 2
• 239000004615 ingredient Substances 0.000 description 2
• ZPNFWUPYTFPOJU-LPYSRVMUSA-N iniprol Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC=4C=CC=CC=4)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC2=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]2N(CCC2)C(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N2[C@@H](CCC2)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N2[C@@H](CCC2)C(=O)N3)C(=O)NCC(=O)NCC(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](C(=O)N1)C(C)C)[C@@H](C)O)[C@@H](C)CC)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 ZPNFWUPYTFPOJU-LPYSRVMUSA-N 0.000 description 2
• 125000006303 iodophenyl group Chemical group 0.000 description 2
• 230000000302 ischemic effect Effects 0.000 description 2
• 210000004153 islets of langerhan Anatomy 0.000 description 2
• 125000005956 isoquinolyl group Chemical group 0.000 description 2
• 210000003734 kidney Anatomy 0.000 description 2
• CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 2
• 231100000518 lethal Toxicity 0.000 description 2
• 230000001665 lethal effect Effects 0.000 description 2
• 150000002617 leukotrienes Chemical class 0.000 description 2
• GDBQQVLCIARPGH-ULQDDVLXSA-N leupeptin Chemical compound CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCN=C(N)N GDBQQVLCIARPGH-ULQDDVLXSA-N 0.000 description 2
• 108010052968 leupeptin Proteins 0.000 description 2
• 239000003446 ligand Substances 0.000 description 2
• 230000000670 limiting effect Effects 0.000 description 2
• 239000002502 liposome Substances 0.000 description 2
• 210000004185 liver Anatomy 0.000 description 2
• 208000012866 low blood pressure Diseases 0.000 description 2
• 239000012139 lysis buffer Substances 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• LROBJRRFCPYLIT-UHFFFAOYSA-M magnesium;ethyne;bromide Chemical compound [Mg+2].[Br-].[C-]#C LROBJRRFCPYLIT-UHFFFAOYSA-M 0.000 description 2
• 230000001404 mediated effect Effects 0.000 description 2
• 238000013160 medical therapy Methods 0.000 description 2
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
• FLEVIENZILQUKB-DMJMAAGCSA-N methyl 4-[3-[6-amino-9-[(2r,3r,4s,5s)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]purin-2-yl]prop-2-ynyl]cyclohexane-1-carboxylate Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(C#CCC3CCC(CC3)C(=O)OC)=NC(N)=C2N=C1 FLEVIENZILQUKB-DMJMAAGCSA-N 0.000 description 2
• 150000004702 methyl esters Chemical class 0.000 description 2
• 238000012544 monitoring process Methods 0.000 description 2
• 201000006417 multiple sclerosis Diseases 0.000 description 2
• 208000031225 myocardial ischemia Diseases 0.000 description 2
• 239000012299 nitrogen atmosphere Substances 0.000 description 2
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 2
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 2
• 244000052769 pathogen Species 0.000 description 2
• 230000007170 pathology Effects 0.000 description 2
• 108010091212 pepstatin Proteins 0.000 description 2
• FAXGPCHRFPCXOO-LXTPJMTPSA-N pepstatin A Chemical compound OC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)CC(C)C FAXGPCHRFPCXOO-LXTPJMTPSA-N 0.000 description 2
• 208000008494 pericarditis Diseases 0.000 description 2
• 239000000546 pharmaceutical excipient Substances 0.000 description 2
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 2
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
• 239000006187 pill Substances 0.000 description 2
• 150000004885 piperazines Chemical class 0.000 description 2
• 238000002600 positron emission tomography Methods 0.000 description 2
• 239000003755 preservative agent Substances 0.000 description 2
• 230000008569 process Effects 0.000 description 2
• 230000004224 protection Effects 0.000 description 2
• 125000003373 pyrazinyl group Chemical group 0.000 description 2
• 125000004076 pyridyl group Chemical group 0.000 description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 description 2
• 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
• 125000000168 pyrrolyl group Chemical group 0.000 description 2
• 125000005493 quinolyl group Chemical group 0.000 description 2
• 238000003653 radioligand binding assay Methods 0.000 description 2
• 239000003642 reactive oxygen metabolite Substances 0.000 description 2
• 230000009467 reduction Effects 0.000 description 2
• 238000011160 research Methods 0.000 description 2
• 208000037803 restenosis Diseases 0.000 description 2
• 229910052702 rhenium Inorganic materials 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• 230000002966 stenotic effect Effects 0.000 description 2
• 230000000638 stimulation Effects 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• 235000000346 sugar Nutrition 0.000 description 2
• 239000000725 suspension Substances 0.000 description 2
• 239000003765 sweetening agent Substances 0.000 description 2
• CTEDVGRUGMPBHE-UHFFFAOYSA-N tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CO)CC1 CTEDVGRUGMPBHE-UHFFFAOYSA-N 0.000 description 2
• OAXARSVKYJPDPA-UHFFFAOYSA-N tert-butyl 4-prop-2-ynylpiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(CC#C)CC1 OAXARSVKYJPDPA-UHFFFAOYSA-N 0.000 description 2
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
• 125000003831 tetrazolyl group Chemical group 0.000 description 2
• BKVIYDNLLOSFOA-OIOBTWANSA-N thallium-201 Chemical compound [201Tl] BKVIYDNLLOSFOA-OIOBTWANSA-N 0.000 description 2
• ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
• 125000000335 thiazolyl group Chemical group 0.000 description 2
• URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
• 125000004306 triazinyl group Chemical group 0.000 description 2
• 125000001425 triazolyl group Chemical group 0.000 description 2
• SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 2
• 238000000825 ultraviolet detection Methods 0.000 description 2
• 235000015112 vegetable and seed oil Nutrition 0.000 description 2
• 239000008158 vegetable oil Substances 0.000 description 2
• 238000010626 work up procedure Methods 0.000 description 2
• IYTOEVMGMNJZEV-TVKKRMFBSA-N (1r)-3-tert-butyl-1-ethynylcyclohexan-1-ol Chemical compound CC(C)(C)C1CCC[C@](O)(C#C)C1 IYTOEVMGMNJZEV-TVKKRMFBSA-N 0.000 description 1
• YXHKSLYHWCBOIN-RKDXNWHRSA-N (1r,3r)-1-ethynyl-3-methylcyclohexan-1-ol Chemical compound C[C@@H]1CCC[C@](O)(C#C)C1 YXHKSLYHWCBOIN-RKDXNWHRSA-N 0.000 description 1
• YXHKSLYHWCBOIN-DTWKUNHWSA-N (1r,3s)-1-ethynyl-3-methylcyclohexan-1-ol Chemical compound C[C@H]1CCC[C@](O)(C#C)C1 YXHKSLYHWCBOIN-DTWKUNHWSA-N 0.000 description 1
• GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
• YIXUMADNPZDKRU-MCPWVCTESA-N (2r,3r,4r,5r)-3-amino-2-(6-aminopurin-9-yl)-2-benzyl-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@]1(CC=2C=CC=CC=2)O[C@H](CO)[C@@H](O)[C@@]1(N)O YIXUMADNPZDKRU-MCPWVCTESA-N 0.000 description 1
• SRWUHMQKNPGXOP-SCFUHWHPSA-N (2r,3r,4s,5r)-2-[6-amino-2-[2-(4-methylphenyl)ethoxy]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=CC(C)=CC=C1CCOC1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=N1 SRWUHMQKNPGXOP-SCFUHWHPSA-N 0.000 description 1
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
• IPSYPUKKXMNCNQ-PFHKOEEOSA-N (2s,3s,4r,5r)-5-[2-chloro-6-[(3-iodophenyl)methylamino]purin-9-yl]-3,4-dihydroxy-n-methyloxolane-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NC)O[C@H]1N1C2=NC(Cl)=NC(NCC=3C=C(I)C=CC=3)=C2N=C1 IPSYPUKKXMNCNQ-PFHKOEEOSA-N 0.000 description 1
• UJBOOUHRTQVGRU-ZCFIWIBFSA-N (3r)-3-methylcyclohexan-1-one Chemical compound C[C@@H]1CCCC(=O)C1 UJBOOUHRTQVGRU-ZCFIWIBFSA-N 0.000 description 1
• AUOSNWRMEZTDNZ-UHFFFAOYSA-N (4-prop-2-ynylcyclohexyl)methanol Chemical compound OCC1CCC(CC#C)CC1 AUOSNWRMEZTDNZ-UHFFFAOYSA-N 0.000 description 1
• MZQFKSOFJMUQEK-UHFFFAOYSA-N (4-prop-2-ynylcyclohexyl)methyl acetate Chemical compound CC(=O)OCC1CCC(CC#C)CC1 MZQFKSOFJMUQEK-UHFFFAOYSA-N 0.000 description 1
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
• CDBKXBLTORGAHK-UHFFFAOYSA-N 1,1-dicyclohexylprop-2-yn-1-ol Chemical compound C1CCCCC1C(C#C)(O)C1CCCCC1 CDBKXBLTORGAHK-UHFFFAOYSA-N 0.000 description 1
• JPBLHOJFMBOCAF-UHFFFAOYSA-N 1,3-benzoxazol-2-amine Chemical compound C1=CC=C2OC(N)=NC2=C1 JPBLHOJFMBOCAF-UHFFFAOYSA-N 0.000 description 1
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• DMLRCHPNMVUSCM-UHFFFAOYSA-N 1-(4-prop-2-ynylpiperidin-1-yl)ethanone Chemical compound CC(=O)N1CCC(CC#C)CC1 DMLRCHPNMVUSCM-UHFFFAOYSA-N 0.000 description 1
• OLZHFFKRBCZHHT-SNVBAGLBSA-N 1-[(2r)-4-[5-(4-fluorophenoxy)furan-2-yl]but-3-yn-2-yl]-1-hydroxyurea Chemical compound O1C(C#C[C@@H](C)N(O)C(N)=O)=CC=C1OC1=CC=C(F)C=C1 OLZHFFKRBCZHHT-SNVBAGLBSA-N 0.000 description 1
• MMSNEKOTSJRTRI-LLVKDONJSA-N 1-[(2r)-4-[5-[(4-fluorophenyl)methyl]thiophen-2-yl]but-3-yn-2-yl]-1-hydroxyurea Chemical compound S1C(C#C[C@@H](C)N(O)C(N)=O)=CC=C1CC1=CC=C(F)C=C1 MMSNEKOTSJRTRI-LLVKDONJSA-N 0.000 description 1
• MWXPQCKCKPYBDR-UHFFFAOYSA-N 1-[4-[3-(4-fluorophenoxy)phenyl]but-3-yn-2-yl]-1-hydroxyurea Chemical compound NC(=O)N(O)C(C)C#CC1=CC=CC(OC=2C=CC(F)=CC=2)=C1 MWXPQCKCKPYBDR-UHFFFAOYSA-N 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
• XPDSXKIDJNKIQY-UHFFFAOYSA-N 1-cyclohexylpiperazine Chemical compound C1CCCCC1N1CCNCC1 XPDSXKIDJNKIQY-UHFFFAOYSA-N 0.000 description 1
• CMJHRFATHWISFN-UHFFFAOYSA-N 1-cyclohexylprop-2-yn-1-ol Chemical compound C#CC(O)C1CCCCC1 CMJHRFATHWISFN-UHFFFAOYSA-N 0.000 description 1
• WGMHMVLZFAJNOT-UHFFFAOYSA-N 1-ethoxyethylideneazanium;chloride Chemical compound [Cl-].CCOC(C)=[NH2+] WGMHMVLZFAJNOT-UHFFFAOYSA-N 0.000 description 1
• ASALCNATAHHPAH-UHFFFAOYSA-N 1-ethyl-4-prop-2-ynylcyclohexane Chemical compound CCC1CCC(CC#C)CC1 ASALCNATAHHPAH-UHFFFAOYSA-N 0.000 description 1
• HCPOYBYENQYVTB-UHFFFAOYSA-N 1-ethynyl-3,3,5,5-tetramethylcyclohexan-1-ol Chemical compound CC1(C)CC(C)(C)CC(O)(C#C)C1 HCPOYBYENQYVTB-UHFFFAOYSA-N 0.000 description 1
• HIHHHOINJQWJTO-UHFFFAOYSA-N 1-ethynyl-3,3-dimethylcyclohexan-1-ol Chemical compound CC1(C)CCCC(O)(C#C)C1 HIHHHOINJQWJTO-UHFFFAOYSA-N 0.000 description 1
• 125000006039 1-hexenyl group Chemical group 0.000 description 1
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
• 125000006023 1-pentenyl group Chemical group 0.000 description 1
• 125000006017 1-propenyl group Chemical group 0.000 description 1
• 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
• YAONEUNUMVOKNQ-NHTLRXQVSA-N 15-(4-iodanylphenyl)pentadecanoic acid Chemical compound OC(=O)CCCCCCCCCCCCCCC1=CC=C([123I])C=C1 YAONEUNUMVOKNQ-NHTLRXQVSA-N 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• FIMVGLUURUZSMJ-UHFFFAOYSA-N 2,2-dimethyl-1-(4-prop-2-ynylpiperidin-1-yl)propan-1-one Chemical compound CC(C)(C)C(=O)N1CCC(CC#C)CC1 FIMVGLUURUZSMJ-UHFFFAOYSA-N 0.000 description 1
• FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
• MUTPFTWCSRAELY-UHFFFAOYSA-N 2-(4-prop-2-ynylpiperazin-1-yl)pyrimidine Chemical compound C1CN(CC#C)CCN1C1=NC=CC=N1 MUTPFTWCSRAELY-UHFFFAOYSA-N 0.000 description 1
• FDSYTWVNUJTPMA-UHFFFAOYSA-N 2-[3,9-bis(carboxymethyl)-3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-6-yl]acetic acid Chemical compound C1N(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC2=CC=CC1=N2 FDSYTWVNUJTPMA-UHFFFAOYSA-N 0.000 description 1
• JELDFLOBXROBFH-UHFFFAOYSA-N 2-[[4-[[2-(2h-tetrazol-5-ylmethyl)phenyl]methoxy]phenoxy]methyl]quinoline Chemical compound C=1C=C2C=CC=CC2=NC=1COC(C=C1)=CC=C1OCC1=CC=CC=C1CC=1N=NNN=1 JELDFLOBXROBFH-UHFFFAOYSA-N 0.000 description 1
• QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
• 125000006040 2-hexenyl group Chemical group 0.000 description 1
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
• HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
• IYXZAFAKQKJEJN-UHFFFAOYSA-N 2-methylpropyl 4-prop-2-ynylpiperazine-1-carboxylate Chemical compound CC(C)COC(=O)N1CCN(CC#C)CC1 IYXZAFAKQKJEJN-UHFFFAOYSA-N 0.000 description 1
• YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
• 125000006024 2-pentenyl group Chemical group 0.000 description 1
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
• CFAYSSJLDFROOT-UHFFFAOYSA-N 3,3-dimethyl-1-(4-prop-2-ynylpiperidin-1-yl)butan-1-one Chemical compound CC(C)(C)CC(=O)N1CCC(CC#C)CC1 CFAYSSJLDFROOT-UHFFFAOYSA-N 0.000 description 1
• DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 1
• AXUZQJFHDNNPFG-LHAVAQOQSA-N 3-[(r)-[3-[(e)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-[3-(dimethylamino)-3-oxopropyl]sulfanylmethyl]sulfanylpropanoic acid Chemical compound CN(C)C(=O)CCS[C@H](SCCC(O)=O)C1=CC=CC(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)=C1 AXUZQJFHDNNPFG-LHAVAQOQSA-N 0.000 description 1
• WDJUZGPOPHTGOT-UHFFFAOYSA-N 3-[3-[5-[5-(4,5-dihydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2h-furan-5-one Chemical compound C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O WDJUZGPOPHTGOT-UHFFFAOYSA-N 0.000 description 1
• 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
• 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
• 125000006041 3-hexenyl group Chemical group 0.000 description 1
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
• HUJXGQILHAUCCV-MOROJQBDSA-N 3-iodobenzyl-5'-N-methylcarboxamidoadenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NC)O[C@H]1N1C2=NC=NC(NCC=3C=C(I)C=CC=3)=C2N=C1 HUJXGQILHAUCCV-MOROJQBDSA-N 0.000 description 1
• MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 1
• MBLJFKQACMILLC-UHFFFAOYSA-N 4-[[3-[[4-[2-(4-hydroxyphenyl)propan-2-yl]phenoxy]methyl]phenyl]methoxy]benzenecarboximidamide Chemical compound C=1C=C(OCC=2C=C(COC=3C=CC(=CC=3)C(N)=N)C=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 MBLJFKQACMILLC-UHFFFAOYSA-N 0.000 description 1
• DQOKLANLGFDDEB-UHFFFAOYSA-N 4-ethyl-1-ethynylcyclohexan-1-ol Chemical compound CCC1CCC(O)(C#C)CC1 DQOKLANLGFDDEB-UHFFFAOYSA-N 0.000 description 1
• 125000006042 4-hexenyl group Chemical group 0.000 description 1
• SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
• ZYJXERACFBLAME-UHFFFAOYSA-N 4-prop-2-ynylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(CC#C)CC1 ZYJXERACFBLAME-UHFFFAOYSA-N 0.000 description 1
• BPCZRRZEJCLZEW-UHFFFAOYSA-N 4-tert-butyl-1-ethynylcyclohexan-1-ol Chemical compound CC(C)(C)C1CCC(O)(C#C)CC1 BPCZRRZEJCLZEW-UHFFFAOYSA-N 0.000 description 1
• MRUWJENAYHTDQG-UHFFFAOYSA-N 4H-pyran Chemical compound C1C=COC=C1 MRUWJENAYHTDQG-UHFFFAOYSA-N 0.000 description 1
• 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
• GYYYCXNTQMDLMC-UHFFFAOYSA-N 5-(6-amino-2-iodopurin-9-yl)-n-cyclopropyl-3,4-dihydroxyoxolane-2-carboxamide Chemical compound C1=NC=2C(N)=NC(I)=NC=2N1C(C(C1O)O)OC1C(=O)NC1CC1 GYYYCXNTQMDLMC-UHFFFAOYSA-N 0.000 description 1
• YEBHQRSEUJCFMN-UHFFFAOYSA-N 5-(6-amino-2-iodopurin-9-yl)-n-ethyl-3,4-dihydroxyoxolane-2-carboxamide Chemical compound OC1C(O)C(C(=O)NCC)OC1N1C2=NC(I)=NC(N)=C2N=C1 YEBHQRSEUJCFMN-UHFFFAOYSA-N 0.000 description 1
• FCDBTWBTNXSZLF-UHFFFAOYSA-N 5-[6-amino-2-[2-(1-hydroxy-3-methylcyclohexyl)ethynyl]purin-9-yl]-n-cyclopropyl-3,4-dihydroxyoxolane-2-carboxamide Chemical compound C1C(C)CCCC1(O)C#CC1=NC(N)=C(N=CN2C3C(C(O)C(O3)C(=O)NC3CC3)O)C2=N1 FCDBTWBTNXSZLF-UHFFFAOYSA-N 0.000 description 1
• JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 1
• 125000006043 5-hexenyl group Chemical group 0.000 description 1
• 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
• USQCUKQZXOWUDF-YWZLYKJASA-N 6-chloro-n-[(3s)-1-[(2s)-1-(4-methyl-5-oxo-1,4-diazepan-1-yl)-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]naphthalene-2-sulfonamide Chemical compound O=C([C@@H](N1C([C@@H](NS(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1)=O)C)N1CCN(C)C(=O)CC1 USQCUKQZXOWUDF-YWZLYKJASA-N 0.000 description 1
• IXJCHVMUTFCRBH-SDUHDBOFSA-N 7-[(1r,2s,3e,5z)-10-(4-acetyl-3-hydroxy-2-propylphenoxy)-1-hydroxy-1-[3-(trifluoromethyl)phenyl]deca-3,5-dien-2-yl]sulfanyl-4-oxochromene-2-carboxylic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCC\C=C/C=C/[C@@H]([C@H](O)C=1C=C(C=CC=1)C(F)(F)F)SC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1 IXJCHVMUTFCRBH-SDUHDBOFSA-N 0.000 description 1
• 101150046889 ADORA3 gene Proteins 0.000 description 1
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
• 102000007471 Adenosine A2A receptor Human genes 0.000 description 1
• 108010085277 Adenosine A2A receptor Proteins 0.000 description 1
• 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• 108010011485 Aspartame Proteins 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 206010003671 Atrioventricular Block Diseases 0.000 description 1
• 208000037157 Azotemia Diseases 0.000 description 1
• KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone 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)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 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 description 1
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
• 206010006895 Cachexia Diseases 0.000 description 1
• 239000004215 Carbon black (E152) Substances 0.000 description 1
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
• 206010007559 Cardiac failure congestive Diseases 0.000 description 1
• 206010007882 Cellulitis Diseases 0.000 description 1
• 206010063094 Cerebral malaria Diseases 0.000 description 1
• 206010008190 Cerebrovascular accident Diseases 0.000 description 1
• RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• 206010009900 Colitis ulcerative Diseases 0.000 description 1
• 208000035473 Communicable disease Diseases 0.000 description 1
• 206010010744 Conjunctivitis allergic Diseases 0.000 description 1
• 208000011231 Crohn disease Diseases 0.000 description 1
• 102000018832 Cytochromes Human genes 0.000 description 1
• 108010052832 Cytochromes Proteins 0.000 description 1
• 125000000824 D-ribofuranosyl group Chemical group [H]OC([H])([H])[C@@]1([H])OC([H])(*)[C@]([H])(O[H])[C@]1([H])O[H] 0.000 description 1
• 201000004624 Dermatitis Diseases 0.000 description 1
• 206010012442 Dermatitis contact Diseases 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
• 201000009273 Endometriosis Diseases 0.000 description 1
• 102000004190 Enzymes Human genes 0.000 description 1
• 108090000790 Enzymes Proteins 0.000 description 1
• 108010008165 Etanercept Proteins 0.000 description 1
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
• 239000005977 Ethylene Substances 0.000 description 1
• 240000002989 Euphorbia neriifolia Species 0.000 description 1
• 108010049003 Fibrinogen Proteins 0.000 description 1
• 102000008946 Fibrinogen Human genes 0.000 description 1
• 230000005526 G1 to G0 transition Effects 0.000 description 1
• CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
• 229930182566 Gentamicin Natural products 0.000 description 1
• 201000005569 Gout Diseases 0.000 description 1
• 208000009329 Graft vs Host Disease Diseases 0.000 description 1
• 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 1
• 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 1
• 208000031886 HIV Infections Diseases 0.000 description 1
• 208000037357 HIV infectious disease Diseases 0.000 description 1
• 208000010271 Heart Block Diseases 0.000 description 1
• 206010019280 Heart failures Diseases 0.000 description 1
• 208000032759 Hemolytic-Uremic Syndrome Diseases 0.000 description 1
• 208000032456 Hemorrhagic Shock Diseases 0.000 description 1
• 208000007514 Herpes zoster Diseases 0.000 description 1
• 241000238631 Hexapoda Species 0.000 description 1
• 108010093488 His-His-His-His-His-His Proteins 0.000 description 1
• 206010020751 Hypersensitivity Diseases 0.000 description 1
• 206010020772 Hypertension Diseases 0.000 description 1
• 206010021143 Hypoxia Diseases 0.000 description 1
• NPCIWINHUDIWAV-NSYCNWAXSA-N I-123 BMIPP Chemical compound OC(=O)CC(C)CCCCCCCCCCCCC1=CC=C([123I])C=C1 NPCIWINHUDIWAV-NSYCNWAXSA-N 0.000 description 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
• 206010062016 Immunosuppression Diseases 0.000 description 1
• 208000004575 Infectious Arthritis Diseases 0.000 description 1
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
• 108010008212 Integrin alpha4beta1 Proteins 0.000 description 1
• 102000000588 Interleukin-2 Human genes 0.000 description 1
• 108010002350 Interleukin-2 Proteins 0.000 description 1
• ZCYVEMRRCGMTRW-AHCXROLUSA-N Iodine-123 Chemical compound [123I] ZCYVEMRRCGMTRW-AHCXROLUSA-N 0.000 description 1
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 208000005230 Leg Ulcer Diseases 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
• 102000018697 Membrane Proteins Human genes 0.000 description 1
• 108010052285 Membrane Proteins Proteins 0.000 description 1
• 201000009906 Meningitis Diseases 0.000 description 1
• 206010027202 Meningitis bacterial Diseases 0.000 description 1
• 244000246386 Mentha pulegium Species 0.000 description 1
• 235000016257 Mentha pulegium Nutrition 0.000 description 1
• 235000004357 Mentha x piperita Nutrition 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• XNCNNDVCAUWAIT-UHFFFAOYSA-N Methyl heptanoate Chemical compound CCCCCCC(=O)OC XNCNNDVCAUWAIT-UHFFFAOYSA-N 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 description 1
• 206010028116 Mucosal inflammation Diseases 0.000 description 1
• 201000010927 Mucositis Diseases 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• 241000238367 Mya arenaria Species 0.000 description 1
• TWWFAXQOKNBUCR-UHFFFAOYSA-N N-[9-chloro-2-(2-furanyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-yl]-2-phenylacetamide Chemical compound N12N=C(C=3OC=CC=3)N=C2C2=CC(Cl)=CC=C2N=C1NC(=O)CC1=CC=CC=C1 TWWFAXQOKNBUCR-UHFFFAOYSA-N 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• 206010028980 Neoplasm Diseases 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• QJGQUHMNIGDVPM-BJUDXGSMSA-N Nitrogen-13 Chemical compound [13N] QJGQUHMNIGDVPM-BJUDXGSMSA-N 0.000 description 1
• 208000001132 Osteoporosis Diseases 0.000 description 1
• 229910019213 POCl3 Inorganic materials 0.000 description 1
• 241001494479 Pecora Species 0.000 description 1
• 102000035195 Peptidases Human genes 0.000 description 1
• 108091005804 Peptidases Proteins 0.000 description 1
• 208000018262 Peripheral vascular disease Diseases 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 239000004365 Protease Substances 0.000 description 1
• 201000004681 Psoriasis Diseases 0.000 description 1
• IGLNJRXAVVLDKE-OIOBTWANSA-N Rubidium-82 Chemical compound [82Rb] IGLNJRXAVVLDKE-OIOBTWANSA-N 0.000 description 1
• 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
• 101100545004 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YSP2 gene Proteins 0.000 description 1
• 229920001800 Shellac Polymers 0.000 description 1
• 206010049771 Shock haemorrhagic Diseases 0.000 description 1
• 206010040943 Skin Ulcer Diseases 0.000 description 1
• 208000032851 Subarachnoid Hemorrhage Diseases 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
• 102000019197 Superoxide Dismutase Human genes 0.000 description 1
• 108010012715 Superoxide dismutase Proteins 0.000 description 1
• 230000006044 T cell activation Effects 0.000 description 1
• GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 description 1
• 240000007313 Tilia cordata Species 0.000 description 1
• 240000007591 Tilia tomentosa Species 0.000 description 1
• 206010044016 Tooth abscess Diseases 0.000 description 1
• 206010044248 Toxic shock syndrome Diseases 0.000 description 1
• 231100000650 Toxic shock syndrome Toxicity 0.000 description 1
• 241000159243 Toxicodendron radicans Species 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 102100040247 Tumor necrosis factor Human genes 0.000 description 1
• 206010054094 Tumour necrosis Diseases 0.000 description 1
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
• 201000006704 Ulcerative Colitis Diseases 0.000 description 1
• 208000024248 Vascular System injury Diseases 0.000 description 1
• 208000012339 Vascular injury Diseases 0.000 description 1
• 206010047115 Vasculitis Diseases 0.000 description 1
• 208000010399 Wasting Syndrome Diseases 0.000 description 1
• 206010052428 Wound Diseases 0.000 description 1
• YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 description 1
• YPFLFUJKZDAXRA-UHFFFAOYSA-N [3-(carbamoylamino)-2-(2,4-dichlorobenzoyl)-1-benzofuran-6-yl] methanesulfonate Chemical compound O1C2=CC(OS(=O)(=O)C)=CC=C2C(NC(N)=O)=C1C(=O)C1=CC=C(Cl)C=C1Cl YPFLFUJKZDAXRA-UHFFFAOYSA-N 0.000 description 1
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
• FGGYJWZYDAROFF-UHFFFAOYSA-N ablukast Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCCCOC(C(=C1)C(C)=O)=CC2=C1CCC(C(O)=O)O2 FGGYJWZYDAROFF-UHFFFAOYSA-N 0.000 description 1
• 229950006882 ablukast Drugs 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• 230000005856 abnormality Effects 0.000 description 1
• 239000002250 absorbent Substances 0.000 description 1
• 230000002745 absorbent Effects 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 239000012190 activator Substances 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• 150000003838 adenosines Chemical class 0.000 description 1
• 230000001464 adherent effect Effects 0.000 description 1
• 239000002671 adjuvant Substances 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• OQIQSTLJSLGHID-WNWIJWBNSA-N aflatoxin B1 Chemical compound C=1([C@@H]2C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O OQIQSTLJSLGHID-WNWIJWBNSA-N 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 239000000783 alginic acid Substances 0.000 description 1
• 235000010443 alginic acid Nutrition 0.000 description 1
• 229920000615 alginic acid Polymers 0.000 description 1
• 229960001126 alginic acid Drugs 0.000 description 1
• 150000004781 alginic acids Chemical class 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 150000001340 alkali metals Chemical class 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• 125000002877 alkyl aryl group Chemical group 0.000 description 1
• 150000001350 alkyl halides Chemical class 0.000 description 1
• 125000000304 alkynyl group Chemical group 0.000 description 1
• 239000013566 allergen Substances 0.000 description 1
• 208000002205 allergic conjunctivitis Diseases 0.000 description 1
• 230000007815 allergy Effects 0.000 description 1
• 230000000735 allogeneic effect Effects 0.000 description 1
• VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 229940126575 aminoglycoside Drugs 0.000 description 1
• PECIYKGSSMCNHN-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=NC=N[C]21.O=C1N(C)C(=O)N(C)C2=NC=N[C]21 PECIYKGSSMCNHN-UHFFFAOYSA-N 0.000 description 1
• 229960003556 aminophylline Drugs 0.000 description 1
• 238000010171 animal model Methods 0.000 description 1
• 230000000879 anti-atherosclerotic effect Effects 0.000 description 1
• 230000003466 anti-cipated effect Effects 0.000 description 1
• 230000002253 anti-ischaemic effect Effects 0.000 description 1
• 230000001775 anti-pathogenic effect Effects 0.000 description 1
• 230000000259 anti-tumor effect Effects 0.000 description 1
• 230000000840 anti-viral effect Effects 0.000 description 1
• 230000000656 anti-yeast Effects 0.000 description 1
• 239000000427 antigen Substances 0.000 description 1
• 108091007433 antigens Proteins 0.000 description 1
• 102000036639 antigens Human genes 0.000 description 1
• 229960002708 antigout preparations Drugs 0.000 description 1
• 239000004599 antimicrobial Substances 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
• 125000003710 aryl alkyl group Chemical group 0.000 description 1
• 229940072107 ascorbate Drugs 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
• 239000000605 aspartame Substances 0.000 description 1
• 229960003438 aspartame Drugs 0.000 description 1
• 235000010357 aspartame Nutrition 0.000 description 1
• 238000003556 assay Methods 0.000 description 1
• 239000012298 atmosphere Substances 0.000 description 1
• 238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 1
• 208000010668 atopic eczema Diseases 0.000 description 1
• LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 1
• 229960002170 azathioprine Drugs 0.000 description 1
• 201000009904 bacterial meningitis Diseases 0.000 description 1
• 244000052616 bacterial pathogen Species 0.000 description 1
• 201000005008 bacterial sepsis Diseases 0.000 description 1
• 239000003855 balanced salt solution Substances 0.000 description 1
• 150000007514 bases Chemical class 0.000 description 1
• 210000003651 basophil Anatomy 0.000 description 1
• 229950000210 beclometasone dipropionate Drugs 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
• 229940050390 benzoate Drugs 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
• 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 230000000975 bioactive effect Effects 0.000 description 1
• 229960000074 biopharmaceutical Drugs 0.000 description 1
• 230000036765 blood level Effects 0.000 description 1
• 210000004204 blood vessel Anatomy 0.000 description 1
• 210000000746 body region Anatomy 0.000 description 1
• 210000001185 bone marrow Anatomy 0.000 description 1
• 210000004556 brain Anatomy 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• 125000005997 bromomethyl group Chemical group 0.000 description 1
• 239000006189 buccal tablet Substances 0.000 description 1
• 229960004436 budesonide Drugs 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 230000001593 cAMP accumulation Effects 0.000 description 1
• 150000001669 calcium Chemical class 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
• 229960004424 carbon dioxide Drugs 0.000 description 1
• 235000011089 carbon dioxide Nutrition 0.000 description 1
• 150000005323 carbonate salts Chemical class 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 230000000747 cardiac effect Effects 0.000 description 1
• 238000004113 cell culture Methods 0.000 description 1
• 210000000170 cell membrane Anatomy 0.000 description 1
• 230000036755 cellular response Effects 0.000 description 1
• 235000010980 cellulose Nutrition 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 238000005119 centrifugation Methods 0.000 description 1
• 208000026106 cerebrovascular disease Diseases 0.000 description 1
• 230000008859 change Effects 0.000 description 1
• 238000012512 characterization method Methods 0.000 description 1
• 239000003610 charcoal Substances 0.000 description 1
• 239000002975 chemoattractant Substances 0.000 description 1
• 239000007958 cherry flavor Substances 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 229960004926 chlorobutanol Drugs 0.000 description 1
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
• 238000013375 chromatographic separation Methods 0.000 description 1
• 238000011097 chromatography purification Methods 0.000 description 1
• 229940117975 chromium trioxide Drugs 0.000 description 1
• WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
• GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
• BZMKNPGKXJAIDV-VAWYXSNFSA-N cinalukast Chemical compound CCC(CC)(C(O)=O)CC(=O)NC1=CC=CC(\C=C\C=2SC=C(N=2)C2CCC2)=C1 BZMKNPGKXJAIDV-VAWYXSNFSA-N 0.000 description 1
• 239000004927 clay Substances 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 238000004440 column chromatography Methods 0.000 description 1
• 229940125758 compound 15 Drugs 0.000 description 1
• 208000010247 contact dermatitis Diseases 0.000 description 1
• 230000009091 contractile dysfunction Effects 0.000 description 1
• 239000000994 contrast dye Substances 0.000 description 1
• GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
• 210000004087 cornea Anatomy 0.000 description 1
• 238000012937 correction Methods 0.000 description 1
• 229940111134 coxibs Drugs 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 239000003260 cyclooxygenase 1 inhibitor Substances 0.000 description 1
• 231100000433 cytotoxic Toxicity 0.000 description 1
• 230000001472 cytotoxic effect Effects 0.000 description 1
• 239000003405 delayed action preparation Substances 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• 230000035487 diastolic blood pressure Effects 0.000 description 1
• PIZLBWGMERQCOC-UHFFFAOYSA-N dibenzyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OCC1=CC=CC=C1 PIZLBWGMERQCOC-UHFFFAOYSA-N 0.000 description 1
• JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
• NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
• 229940038472 dicalcium phosphate Drugs 0.000 description 1
• 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
• 235000005911 diet Nutrition 0.000 description 1
• 230000037213 diet Effects 0.000 description 1
• UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
• 230000010339 dilation Effects 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• 239000002612 dispersion medium Substances 0.000 description 1
• 238000006073 displacement reaction Methods 0.000 description 1
• 238000010494 dissociation reaction Methods 0.000 description 1
• 230000005593 dissociations Effects 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 238000009826 distribution Methods 0.000 description 1
• 238000002651 drug therapy Methods 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 230000009977 dual effect Effects 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 230000004064 dysfunction Effects 0.000 description 1
• 239000012039 electrophile Substances 0.000 description 1
• 206010014599 encephalitis Diseases 0.000 description 1
• 210000002889 endothelial cell Anatomy 0.000 description 1
• 210000003989 endothelium vascular Anatomy 0.000 description 1
• 230000002255 enzymatic effect Effects 0.000 description 1
• 229960000403 etanercept Drugs 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• 239000012259 ether extract Substances 0.000 description 1
• FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
• SGUWICZLPJPOSU-UHFFFAOYSA-N ethyl 4-(cyanomethyl)piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCN(CC#N)CC1 SGUWICZLPJPOSU-UHFFFAOYSA-N 0.000 description 1
• AETZFVZYFDHOLG-UHFFFAOYSA-N ethyl 4-prop-2-ynylpiperazine-1-carboxylate Chemical compound CCOC(=O)N1CCN(CC#C)CC1 AETZFVZYFDHOLG-UHFFFAOYSA-N 0.000 description 1
• UXOZIKXHTYNEFJ-UHFFFAOYSA-N ethyl 4-prop-2-ynylpiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(CC#C)CC1 UXOZIKXHTYNEFJ-UHFFFAOYSA-N 0.000 description 1
• SBVYURPQULDJTI-UHFFFAOYSA-N ethyl n-[amino-[4-[[3-[[4-[2-(4-hydroxyphenyl)propan-2-yl]phenoxy]methyl]phenyl]methoxy]phenyl]methylidene]carbamate Chemical compound C1=CC(C(=N)NC(=O)OCC)=CC=C1OCC1=CC=CC(COC=2C=CC(=CC=2)C(C)(C)C=2C=CC(O)=CC=2)=C1 SBVYURPQULDJTI-UHFFFAOYSA-N 0.000 description 1
• LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 1
• RUJPPJYDHHAEEK-UHFFFAOYSA-N ethyl piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCNCC1 RUJPPJYDHHAEEK-UHFFFAOYSA-N 0.000 description 1
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
• 230000007717 exclusion Effects 0.000 description 1
• 239000000284 extract Substances 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 238000013213 extrapolation Methods 0.000 description 1
• 150000004665 fatty acids Chemical class 0.000 description 1
• 150000002191 fatty alcohols Chemical class 0.000 description 1
• 230000002349 favourable effect Effects 0.000 description 1
• 229950002170 fenleuton Drugs 0.000 description 1
• 239000012091 fetal bovine serum Substances 0.000 description 1
• 229940012952 fibrinogen Drugs 0.000 description 1
• 210000002950 fibroblast Anatomy 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 229960000676 flunisolide Drugs 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
• 229960000289 fluticasone propionate Drugs 0.000 description 1
• WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate 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)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 description 1
• 235000013305 food Nutrition 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 238000009472 formulation Methods 0.000 description 1
• 239000003205 fragrance Substances 0.000 description 1
• 238000004108 freeze drying Methods 0.000 description 1
• 230000002538 fungal effect Effects 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 239000003862 glucocorticoid Substances 0.000 description 1
• 125000005908 glyceryl ester group Chemical group 0.000 description 1
• 239000001087 glyceryl triacetate Substances 0.000 description 1
• 235000013773 glyceryl triacetate Nutrition 0.000 description 1
• 150000002334 glycols Chemical class 0.000 description 1
• 208000024908 graft versus host disease Diseases 0.000 description 1
• 239000003102 growth factor Substances 0.000 description 1
• 230000035876 healing Effects 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 238000000703 high-speed centrifugation Methods 0.000 description 1
• 235000001050 hortel pimenta Nutrition 0.000 description 1
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 230000002209 hydrophobic effect Effects 0.000 description 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
• 230000000544 hyperemic effect Effects 0.000 description 1
• QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
• 230000007954 hypoxia Effects 0.000 description 1
• 125000002632 imidazolidinyl group Chemical group 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 230000028993 immune response Effects 0.000 description 1
• 230000001506 immunosuppresive effect Effects 0.000 description 1
• 239000003018 immunosuppressive agent Substances 0.000 description 1
• 229940125721 immunosuppressive agent Drugs 0.000 description 1
• 238000002650 immunosuppressive therapy Methods 0.000 description 1
• 230000001976 improved effect Effects 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 239000003701 inert diluent Substances 0.000 description 1
• 208000000509 infertility Diseases 0.000 description 1
• 230000036512 infertility Effects 0.000 description 1
• 231100000535 infertility Toxicity 0.000 description 1
• 230000003960 inflammatory cascade Effects 0.000 description 1
• 210000004969 inflammatory cell Anatomy 0.000 description 1
• 229960000598 infliximab Drugs 0.000 description 1
• 206010022000 influenza Diseases 0.000 description 1
• 208000023372 inhalational anthrax Diseases 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 239000007972 injectable composition Substances 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000010253 intravenous injection Methods 0.000 description 1
• 230000009545 invasion Effects 0.000 description 1
• 125000002346 iodo group Chemical group I* 0.000 description 1
• 229950000831 iralukast Drugs 0.000 description 1
• 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 description 1
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
• 239000007951 isotonicity adjuster Substances 0.000 description 1
• 230000002147 killing effect Effects 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 210000005240 left ventricle Anatomy 0.000 description 1
• VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 1
• GWNVDXQDILPJIG-NXOLIXFESA-N leukotriene C4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-NXOLIXFESA-N 0.000 description 1
• 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 description 1
• OTZRAYGBFWZKMX-JUDRUQEKSA-N leukotriene E4 Chemical compound CCCCCC=CCC=C\C=C\C=C\[C@@H](SC[C@H](N)C(O)=O)[C@@H](O)CCCC(O)=O OTZRAYGBFWZKMX-JUDRUQEKSA-N 0.000 description 1
• XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
• 150000002632 lipids Chemical class 0.000 description 1
• 229920006008 lipopolysaccharide Polymers 0.000 description 1
• 238000004811 liquid chromatography Methods 0.000 description 1
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
• 230000033001 locomotion Effects 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• 206010025135 lupus erythematosus Diseases 0.000 description 1
• 230000002132 lysosomal effect Effects 0.000 description 1
• UJBOOUHRTQVGRU-UHFFFAOYSA-N m-methylcyclohexanone Natural products CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 1
• 229910001629 magnesium chloride Inorganic materials 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
• 235000019341 magnesium sulphate Nutrition 0.000 description 1
• 238000012423 maintenance Methods 0.000 description 1
• 229940049920 malate Drugs 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 238000001819 mass spectrum Methods 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
• 229960000485 methotrexate Drugs 0.000 description 1
• SQJXTUJMBYVDBB-RQXXJAGISA-N methyl 4-[3-[6-amino-9-[(2r,3r,4s,5s)-5-(cyclopropylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]purin-2-yl]prop-2-ynyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCC1CC#CC1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@H](O3)C(=O)NC3CC3)O)C2=N1 SQJXTUJMBYVDBB-RQXXJAGISA-N 0.000 description 1
• GOBXIGSMYAMLAM-UHFFFAOYSA-N methyl 4-[3-[6-amino-9-[5-(cyclopropylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]purin-2-yl]prop-2-ynyl]cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OC)CCC1CC#CC1=NC(N)=C(N=CN2C3C(C(O)C(O3)C(=O)NC3CC3)O)C2=N1 GOBXIGSMYAMLAM-UHFFFAOYSA-N 0.000 description 1
• VFOQETNBTUILTQ-UHFFFAOYSA-N methyl 4-prop-2-ynylcyclohexane-1-carboxylate Chemical compound COC(=O)C1CCC(CC#C)CC1 VFOQETNBTUILTQ-UHFFFAOYSA-N 0.000 description 1
• CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
• XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
• 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
• APCHKWZTSCBBJX-UHFFFAOYSA-N methyl piperidine-2-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1CCCCN1 APCHKWZTSCBBJX-UHFFFAOYSA-N 0.000 description 1
• RZVWBASHHLFBJF-UHFFFAOYSA-N methyl piperidine-4-carboxylate Chemical compound COC(=O)C1CCNCC1 RZVWBASHHLFBJF-UHFFFAOYSA-N 0.000 description 1
• OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 230000003278 mimic effect Effects 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000010369 molecular cloning Methods 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• 229960002744 mometasone furoate Drugs 0.000 description 1
• WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 description 1
• 229960005127 montelukast Drugs 0.000 description 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
• 210000003205 muscle Anatomy 0.000 description 1
• 210000000107 myocyte Anatomy 0.000 description 1
• GINQYTLDMNFGQP-UHFFFAOYSA-N n,n-dimethylformamide;methylsulfinylmethane Chemical compound CS(C)=O.CN(C)C=O GINQYTLDMNFGQP-UHFFFAOYSA-N 0.000 description 1
• RVXKHAITGKBBAC-SFHVURJKSA-N n-[(1s)-2-cyclohexyl-1-pyridin-2-ylethyl]-5-methyl-1,3-benzoxazol-2-amine Chemical compound C([C@H](NC=1OC2=CC=C(C=C2N=1)C)C=1N=CC=CC=1)C1CCCCC1 RVXKHAITGKBBAC-SFHVURJKSA-N 0.000 description 1
• SQMWSBKSHWARHU-SDBHATRESA-N n6-cyclopentyladenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(NC3CCCC3)=C2N=C1 SQMWSBKSHWARHU-SDBHATRESA-N 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
• 230000009871 nonspecific binding Effects 0.000 description 1
• 230000001473 noxious effect Effects 0.000 description 1
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 229950010666 ontazolast Drugs 0.000 description 1
• 239000007968 orange flavor Substances 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 239000012044 organic layer Substances 0.000 description 1
• 150000004866 oxadiazoles Chemical class 0.000 description 1
• 125000004043 oxo group Chemical group O=* 0.000 description 1
• LVSJDHGRKAEGLX-UHFFFAOYSA-N oxolane;2,2,2-trifluoroacetic acid Chemical compound C1CCOC1.OC(=O)C(F)(F)F LVSJDHGRKAEGLX-UHFFFAOYSA-N 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 239000006072 paste Substances 0.000 description 1
• 230000008506 pathogenesis Effects 0.000 description 1
• 231100000255 pathogenic effect Toxicity 0.000 description 1
• 239000008188 pellet Substances 0.000 description 1
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 206010034674 peritonitis Diseases 0.000 description 1
• 229960003742 phenol Drugs 0.000 description 1
• YKGCCFHSXQHWIG-UHFFFAOYSA-N phenothiazin-3-one Chemical compound C1=CC=C2SC3=CC(=O)C=CC3=NC2=C1 YKGCCFHSXQHWIG-UHFFFAOYSA-N 0.000 description 1
• 230000006461 physiological response Effects 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000005936 piperidyl group Chemical group 0.000 description 1
• 230000036470 plasma concentration Effects 0.000 description 1
• 208000008423 pleurisy Diseases 0.000 description 1
• 229920005862 polyol Polymers 0.000 description 1
• 150000003077 polyols Chemical class 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229920001592 potato starch Polymers 0.000 description 1
• 229940124606 potential therapeutic agent Drugs 0.000 description 1
• UAJUXJSXCLUTNU-UHFFFAOYSA-N pranlukast Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 UAJUXJSXCLUTNU-UHFFFAOYSA-N 0.000 description 1
• 229960004583 pranlukast Drugs 0.000 description 1
• 239000002243 precursor Substances 0.000 description 1
• 229960005205 prednisolone Drugs 0.000 description 1
• OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
• 229960004618 prednisone Drugs 0.000 description 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 description 1
• 238000002953 preparative HPLC Methods 0.000 description 1
• 238000012746 preparative thin layer chromatography Methods 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 108090000765 processed proteins & peptides Proteins 0.000 description 1
• 238000012545 processing Methods 0.000 description 1
• 230000000750 progressive effect Effects 0.000 description 1
• 230000000770 proinflammatory effect Effects 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• 230000001737 promoting effect Effects 0.000 description 1
• 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
• 238000000159 protein binding assay Methods 0.000 description 1
• 238000001742 protein purification Methods 0.000 description 1
• 230000005180 public health Effects 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000002755 pyrazolinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
• ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 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 description 1
• 150000003248 quinolines Chemical class 0.000 description 1
• 229940044551 receptor antagonist Drugs 0.000 description 1
• 239000002464 receptor antagonist Substances 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 230000019254 respiratory burst Effects 0.000 description 1
• 206010039073 rheumatoid arthritis Diseases 0.000 description 1
• 206010039083 rhinitis Diseases 0.000 description 1
• 210000005241 right ventricle Anatomy 0.000 description 1
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 1
• 229960000371 rofecoxib Drugs 0.000 description 1
• RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 1
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
• 201000001223 septic arthritis Diseases 0.000 description 1
• 208000013223 septicemia Diseases 0.000 description 1
• 238000013207 serial dilution Methods 0.000 description 1
• ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
• 239000004208 shellac Substances 0.000 description 1
• 229940113147 shellac Drugs 0.000 description 1
• 235000013874 shellac Nutrition 0.000 description 1
• 238000002603 single-photon emission computed tomography Methods 0.000 description 1
• 208000017520 skin disease Diseases 0.000 description 1
• 231100000019 skin ulcer Toxicity 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
• 239000000344 soap Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• YPURUCMVRRNPHJ-UHFFFAOYSA-M sodium;3-[3-tert-butylsulfanyl-1-[(4-chlorophenyl)methyl]-5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate Chemical compound [Na+].C12=CC=C(OCC=3N=C4C=CC=CC4=CC=3)C=C2C(SC(C)(C)C)=C(CC(C)(C)C([O-])=O)N1CC1=CC=C(Cl)C=C1 YPURUCMVRRNPHJ-UHFFFAOYSA-M 0.000 description 1
• 239000007892 solid unit dosage form Substances 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 230000009870 specific binding Effects 0.000 description 1
• 208000020431 spinal cord injury Diseases 0.000 description 1
• 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
• 238000012453 sprague-dawley rat model Methods 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 230000001954 sterilising effect Effects 0.000 description 1
• 238000004659 sterilization and disinfection Methods 0.000 description 1
• 239000011550 stock solution Substances 0.000 description 1
• 208000003265 stomatitis Diseases 0.000 description 1
• 238000007920 subcutaneous administration Methods 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
• 150000008163 sugars Chemical class 0.000 description 1
• 235000011149 sulphuric acid Nutrition 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 230000002195 synergetic effect Effects 0.000 description 1
• 229920001059 synthetic polymer Polymers 0.000 description 1
• 229940037128 systemic glucocorticoids Drugs 0.000 description 1
• 230000035488 systolic blood pressure Effects 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• 229940056501 technetium 99m Drugs 0.000 description 1
• XYKWNRUXCOIMFZ-UHFFFAOYSA-N tepoxalin Chemical compound C1=CC(OC)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(CCC(=O)N(C)O)=N1 XYKWNRUXCOIMFZ-UHFFFAOYSA-N 0.000 description 1
• 229950009638 tepoxalin Drugs 0.000 description 1
• CHTFWVDBUXUMCE-UHFFFAOYSA-N tert-butyl 4-prop-2-ynylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC#C)CC1 CHTFWVDBUXUMCE-UHFFFAOYSA-N 0.000 description 1
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
• 229960000278 theophylline Drugs 0.000 description 1
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
• 239000002562 thickening agent Substances 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
• 229940033663 thimerosal Drugs 0.000 description 1
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
• 230000000451 tissue damage Effects 0.000 description 1
• 231100000827 tissue damage Toxicity 0.000 description 1
• 238000011200 topical administration Methods 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 238000012546 transfer Methods 0.000 description 1
• 230000000472 traumatic effect Effects 0.000 description 1
• 229960002622 triacetin Drugs 0.000 description 1
• 229960002117 triamcinolone acetonide Drugs 0.000 description 1
• YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
• 150000003852 triazoles Chemical class 0.000 description 1
• 125000006168 tricyclic group Chemical group 0.000 description 1
• ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 1
• 238000001665 trituration Methods 0.000 description 1
• 241001430294 unidentified retrovirus Species 0.000 description 1
• 238000001291 vacuum drying Methods 0.000 description 1
• 208000019553 vascular disease Diseases 0.000 description 1
• 210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
• 230000000304 vasodilatating effect Effects 0.000 description 1
• 230000002861 ventricular Effects 0.000 description 1
• 229950003905 verlukast Drugs 0.000 description 1
• 201000005539 vernal conjunctivitis Diseases 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 230000003612 virological effect Effects 0.000 description 1
• 235000012431 wafers Nutrition 0.000 description 1
• 239000001993 wax Substances 0.000 description 1
• 239000009637 wintergreen oil Substances 0.000 description 1
• 229960004764 zafirlukast Drugs 0.000 description 1
• MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
• 229960005332 zileuton Drugs 0.000 description 1
• DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1