UA78745C2 - Imidazoquinoline derivatives - Google Patents
Imidazoquinoline derivatives Download PDFInfo
- Publication number
- UA78745C2 UA78745C2 UA20040706065A UA20040706065A UA78745C2 UA 78745 C2 UA78745 C2 UA 78745C2 UA 20040706065 A UA20040706065 A UA 20040706065A UA 20040706065 A UA20040706065 A UA 20040706065A UA 78745 C2 UA78745 C2 UA 78745C2
- Authority
- UA
- Ukraine
- Prior art keywords
- group
- linear
- branched chain
- alkyl group
- atom
- Prior art date
Links
- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 239000012453 solvate Substances 0.000 claims abstract description 35
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 239000005557 antagonist Substances 0.000 claims abstract description 7
- 239000003446 ligand Substances 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 85
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 54
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 45
- -1 methylenedioxy group Chemical group 0.000 claims description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 34
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 31
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 30
- 229960005305 adenosine Drugs 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
- 125000002541 furyl group Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000001544 thienyl group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000004434 sulfur atom Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 230000005764 inhibitory process Effects 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 claims description 6
- 210000004027 cell Anatomy 0.000 claims description 5
- 210000003169 central nervous system Anatomy 0.000 claims description 5
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- 206010020751 Hypersensitivity Diseases 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 210000003630 histaminocyte Anatomy 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 210000002216 heart Anatomy 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- 208000009079 Bronchial Spasm Diseases 0.000 claims description 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 102000004127 Cytokines Human genes 0.000 claims description 2
- 108090000695 Cytokines Proteins 0.000 claims description 2
- 208000000059 Dyspnea Diseases 0.000 claims description 2
- 206010013975 Dyspnoeas Diseases 0.000 claims description 2
- 206010014561 Emphysema Diseases 0.000 claims description 2
- 206010015866 Extravasation Diseases 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 206010021143 Hypoxia Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 208000005374 Poisoning Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 206010039710 Scleroderma Diseases 0.000 claims description 2
- 208000024780 Urticaria Diseases 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 230000000172 allergic effect Effects 0.000 claims description 2
- 230000003288 anthiarrhythmic effect Effects 0.000 claims description 2
- 230000001088 anti-asthma Effects 0.000 claims description 2
- 230000001430 anti-depressive effect Effects 0.000 claims description 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 2
- 230000002253 anti-ischaemic effect Effects 0.000 claims description 2
- 230000000648 anti-parkinson Effects 0.000 claims description 2
- 230000000259 anti-tumor effect Effects 0.000 claims description 2
- 239000003416 antiarrhythmic agent Substances 0.000 claims description 2
- 239000000924 antiasthmatic agent Substances 0.000 claims description 2
- 239000000935 antidepressant agent Substances 0.000 claims description 2
- 229940005513 antidepressants Drugs 0.000 claims description 2
- 239000000939 antiparkinson agent Substances 0.000 claims description 2
- 206010003119 arrhythmia Diseases 0.000 claims description 2
- 230000006793 arrhythmia Effects 0.000 claims description 2
- 206010003246 arthritis Diseases 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 206010006451 bronchitis Diseases 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 208000007451 chronic bronchitis Diseases 0.000 claims description 2
- 230000037411 cognitive enhancing Effects 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 210000003979 eosinophil Anatomy 0.000 claims description 2
- 230000036251 extravasation Effects 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 230000007954 hypoxia Effects 0.000 claims description 2
- 210000000987 immune system Anatomy 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- 230000004410 intraocular pressure Effects 0.000 claims description 2
- 208000028867 ischemia Diseases 0.000 claims description 2
- 210000003734 kidney Anatomy 0.000 claims description 2
- 208000017169 kidney disease Diseases 0.000 claims description 2
- 230000005012 migration Effects 0.000 claims description 2
- 238000013508 migration Methods 0.000 claims description 2
- 230000002107 myocardial effect Effects 0.000 claims description 2
- 230000001607 nephroprotective effect Effects 0.000 claims description 2
- 230000007658 neurological function Effects 0.000 claims description 2
- 210000000440 neutrophil Anatomy 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 231100000572 poisoning Toxicity 0.000 claims description 2
- 230000000607 poisoning effect Effects 0.000 claims description 2
- 230000010410 reperfusion Effects 0.000 claims description 2
- 206010039083 rhinitis Diseases 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 208000014181 Bronchial disease Diseases 0.000 claims 1
- 206010006482 Bronchospasm Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000005332 alkyl sulfoxy group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000002464 receptor antagonist Substances 0.000 claims 1
- 229940044551 receptor antagonist Drugs 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 208000013220 shortness of breath Diseases 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 238000000844 transformation Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 11
- 102000008161 Adenosine A3 Receptor Human genes 0.000 abstract 1
- 108010060261 Adenosine A3 Receptor Proteins 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 102000005962 receptors Human genes 0.000 description 31
- 108020003175 receptors Proteins 0.000 description 31
- 230000000694 effects Effects 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 14
- 230000027455 binding Effects 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 239000012528 membrane Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000872 buffer Substances 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- 102000009346 Adenosine receptors Human genes 0.000 description 6
- 108050000203 Adenosine receptors Proteins 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 6
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- RRHVNLMYGHTZJC-UHFFFAOYSA-N 2-amino-4-chloroquinoline-3-carbonitrile Chemical compound C1=CC=C2C(Cl)=C(C#N)C(N)=NC2=C1 RRHVNLMYGHTZJC-UHFFFAOYSA-N 0.000 description 4
- 229920002873 Polyethylenimine Polymers 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 102000030621 adenylate cyclase Human genes 0.000 description 3
- 108060000200 adenylate cyclase Proteins 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000009871 nonspecific binding Effects 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- XMNBZTMWILHWPS-UHFFFAOYSA-N 2-amino-4-(benzylamino)quinoline-3-carbonitrile Chemical compound N#CC=1C(N)=NC2=CC=CC=C2C=1NCC1=CC=CC=C1 XMNBZTMWILHWPS-UHFFFAOYSA-N 0.000 description 2
- GRNHLFULJDXJKR-UHFFFAOYSA-N 3-(2-sulfanylethyl)-1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)NC2=C1 GRNHLFULJDXJKR-UHFFFAOYSA-N 0.000 description 2
- 101710169336 5'-deoxyadenosine deaminase Proteins 0.000 description 2
- 102000055025 Adenosine deaminases Human genes 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- 241000238558 Eucarida Species 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 244000300264 Spinacia oleracea Species 0.000 description 2
- 235000009337 Spinacia oleracea Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 244000275904 brauner Senf Species 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 150000002500 ions Chemical class 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
- 230000001404 mediated effect Effects 0.000 description 2
- 108020004999 messenger RNA Proteins 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 230000035790 physiological processes and functions Effects 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 230000000946 synaptic effect Effects 0.000 description 2
- 210000001550 testis Anatomy 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 1
- RLLPVAHGXHCWKJ-IEBWSBKVSA-N (3-phenoxyphenyl)methyl (1s,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-IEBWSBKVSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical group C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
- UABIXNSHHIMZEP-UHFFFAOYSA-N 2-[2-[(dimethylamino)methyl]phenyl]sulfanyl-5-methylaniline Chemical compound CN(C)CC1=CC=CC=C1SC1=CC=C(C)C=C1N UABIXNSHHIMZEP-UHFFFAOYSA-N 0.000 description 1
- YWZLDHIVSMYVMH-UHFFFAOYSA-N 2-amino-2-[(quinolin-2-ylamino)methyl]-3H-furan-3-carbonitrile Chemical compound NC1(CNC2=NC3=CC=CC=C3C=C2)C(C=CO1)C#N YWZLDHIVSMYVMH-UHFFFAOYSA-N 0.000 description 1
- MCLFCZKVPRPRDS-UHFFFAOYSA-N 2-amino-4-(furan-2-ylmethylamino)quinoline-3-carbonitrile Chemical compound N#CC=1C(N)=NC2=CC=CC=C2C=1NCC1=CC=CO1 MCLFCZKVPRPRDS-UHFFFAOYSA-N 0.000 description 1
- DBDLIOZPGDCWQA-UHFFFAOYSA-N 2-amino-4-(quinolin-2-ylamino)thiophene-3-carbonitrile Chemical compound N#CC1=C(N)SC=C1NC1=CC=C(C=CC=C2)C2=N1 DBDLIOZPGDCWQA-UHFFFAOYSA-N 0.000 description 1
- ZZHUVUGNUROUHA-UHFFFAOYSA-N 2-amino-4-(thiophen-2-ylamino)quinoline-3-carbonitrile Chemical compound N#CC=1C(N)=NC2=CC=CC=C2C=1NC1=CC=CS1 ZZHUVUGNUROUHA-UHFFFAOYSA-N 0.000 description 1
- USKBIWBLJHCVOP-UHFFFAOYSA-N 2-amino-4-oxo-1h-quinoline-3-carbonitrile Chemical compound C1=CC=C2C(O)=C(C#N)C(N)=NC2=C1 USKBIWBLJHCVOP-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 241001519451 Abramis brama Species 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 101100310222 Caenorhabditis briggsae she-1 gene Proteins 0.000 description 1
- 101100273638 Caenorhabditis elegans cya-1 gene Proteins 0.000 description 1
- 101100123850 Caenorhabditis elegans her-1 gene Proteins 0.000 description 1
- 235000017399 Caesalpinia tinctoria Nutrition 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000132536 Cirsium Species 0.000 description 1
- 235000010205 Cola acuminata Nutrition 0.000 description 1
- 244000228088 Cola acuminata Species 0.000 description 1
- 235000015438 Cola nitida Nutrition 0.000 description 1
- FFBDFADSZUINTG-UHFFFAOYSA-N DPCPX Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1CCCC1 FFBDFADSZUINTG-UHFFFAOYSA-N 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
- 102000015554 Dopamine receptor Human genes 0.000 description 1
- 108050004812 Dopamine receptor Proteins 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
- 101150093335 KIN1 gene Proteins 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
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- LLPBSGARCAXPFM-UHFFFAOYSA-N N1CCCCC1.C=N.C=N.C=N.C=N.C=N Chemical compound N1CCCCC1.C=N.C=N.C=N.C=N.C=N LLPBSGARCAXPFM-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 241001602688 Pama Species 0.000 description 1
- 101150034459 Parpbp gene Proteins 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 240000004760 Pimpinella anisum Species 0.000 description 1
- 241000549435 Pria Species 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 235000011449 Rosa Nutrition 0.000 description 1
- 235000014548 Rubus moluccanus Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000388430 Tara Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 102000014384 Type C Phospholipases Human genes 0.000 description 1
- 108010079194 Type C Phospholipases Proteins 0.000 description 1
- 241001440806 Tyta Species 0.000 description 1
- 241001255741 Vanna Species 0.000 description 1
- 206010047141 Vasodilatation Diseases 0.000 description 1
- 241000750042 Vini Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 210000005056 cell body Anatomy 0.000 description 1
- 230000002057 chronotropic effect Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
- 229960000913 crospovidone Drugs 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000001091 dromotropic effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 210000002865 immune cell Anatomy 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 244000145841 kine Species 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 101150093826 par1 gene Proteins 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 125000003395 phenylethylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-M quinaldate Chemical compound C1=CC=CC2=NC(C(=O)[O-])=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-M 0.000 description 1
- XEORENVXIPLVSZ-UHFFFAOYSA-N quinoline-2-carboxylic acid hydrate Chemical compound O.N1=C(C=CC2=CC=CC=C12)C(=O)O XEORENVXIPLVSZ-UHFFFAOYSA-N 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000009711 regulatory function Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 150000008634 thiazolopyrimidines Chemical class 0.000 description 1
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000583 toxicological profile Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000006442 vascular tone Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0105406A HUP0105406A3 (en) | 2001-12-21 | 2001-12-21 | Imidazo[1,2-a]quinolin derivatives, process for their preparation, pharmaceutical compositions thereof and intermediates |
| PCT/HU2002/000144 WO2003053969A1 (en) | 2001-12-21 | 2002-12-17 | Imidazoquinoline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA78745C2 true UA78745C2 (en) | 2007-04-25 |
Family
ID=47711504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20040706065A UA78745C2 (en) | 2001-12-21 | 2002-12-17 | Imidazoquinoline derivatives |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7176213B2 (hu) |
| EP (1) | EP1456205A1 (hu) |
| JP (1) | JP4530663B2 (hu) |
| KR (2) | KR20070034136A (hu) |
| CN (1) | CN1307174C (hu) |
| AU (1) | AU2002353241B2 (hu) |
| BR (1) | BR0215272A (hu) |
| CA (1) | CA2470067C (hu) |
| EA (1) | EA007226B1 (hu) |
| HR (1) | HRP20040671A2 (hu) |
| HU (1) | HUP0105406A3 (hu) |
| IL (2) | IL162443A0 (hu) |
| IS (1) | IS7317A (hu) |
| MA (1) | MA27240A1 (hu) |
| MX (1) | MXPA04006115A (hu) |
| NO (1) | NO329743B1 (hu) |
| NZ (1) | NZ534015A (hu) |
| PL (1) | PL370761A1 (hu) |
| RS (1) | RS56104A (hu) |
| TN (1) | TNSN04105A1 (hu) |
| UA (1) | UA78745C2 (hu) |
| WO (1) | WO2003053969A1 (hu) |
| ZA (1) | ZA200404807B (hu) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1430032A2 (en) * | 2001-09-24 | 2004-06-23 | Elan Pharmaceuticals, Inc. | Substituted amides for the treatment of neurological disorders |
| HUP0203976A3 (en) * | 2002-11-15 | 2004-08-30 | Sanofi Aventis | Adenozine a3 receptors, process for their preparation and pharmaceutical compositions containing them |
| HUP0400812A2 (en) * | 2004-04-19 | 2006-02-28 | Sanofi Aventis | Crystalline forms of 2-amino-3-cyano-quinoline derivatives, process for their preparation and pharmaceutical compositions containing them |
| JP2008531502A (ja) * | 2005-02-22 | 2008-08-14 | ザ レジェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 胃腸の炎症を処置する方法 |
| HUP0700395A2 (en) * | 2007-06-07 | 2009-03-02 | Sanofi Aventis | Substituted [1,2,4] triazolo [1,5-a] quinolines, process for their preparation, pharmaceutical compositions thereof, and intermediates |
| US8357132B1 (en) | 2009-10-21 | 2013-01-22 | Lekweuwa Agatha N | Urine capturing assembly |
| KR20210007046A (ko) | 2013-02-01 | 2021-01-19 | 웰스태트 테러퓨틱스 코포레이션 | 항염증, 항진균, 항기생충, 및 항암 활성을 갖는 아민 화합물 |
| ES2578363B1 (es) | 2015-01-22 | 2017-01-31 | Palobiofarma, S.L. | Moduladores de los receptores A3 de adenosina |
| WO2017023905A1 (en) * | 2015-08-03 | 2017-02-09 | Bristol-Myers Squibb Company | Heterocyclic compounds useful as modulators of tnf alpha |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4075343A (en) * | 1976-09-13 | 1978-02-21 | Pfizer Inc. | Anti-allergenic 5-alkoxyimidazo[1,2-A]quinoline-2-carboxylic acids and derivatives thereof |
| GB1596652A (en) * | 1977-01-20 | 1981-08-26 | Roussel Lab Ltd | Imidazo (1,2-a) quinoline-2-carboxylic acid and derivatives |
| SE441449B (sv) | 1979-02-09 | 1985-10-07 | Roussel Uclaf | Heterocykliska derivat och farmaceutiska kompositioner innehallande dessa derivat |
| GR76063B (hu) * | 1981-04-03 | 1984-08-03 | Roussel Uclaf | |
| HUP0203976A3 (en) * | 2002-11-15 | 2004-08-30 | Sanofi Aventis | Adenozine a3 receptors, process for their preparation and pharmaceutical compositions containing them |
-
2001
- 2001-12-21 HU HU0105406A patent/HUP0105406A3/hu unknown
-
2002
- 2002-12-17 EA EA200400847A patent/EA007226B1/ru not_active IP Right Cessation
- 2002-12-17 EP EP02788261A patent/EP1456205A1/en not_active Withdrawn
- 2002-12-17 US US10/499,251 patent/US7176213B2/en not_active Expired - Fee Related
- 2002-12-17 CN CNB02825645XA patent/CN1307174C/zh not_active Expired - Fee Related
- 2002-12-17 CA CA2470067A patent/CA2470067C/en not_active Expired - Fee Related
- 2002-12-17 JP JP2003554685A patent/JP4530663B2/ja not_active Expired - Fee Related
- 2002-12-17 UA UA20040706065A patent/UA78745C2/uk unknown
- 2002-12-17 MX MXPA04006115A patent/MXPA04006115A/es active IP Right Grant
- 2002-12-17 PL PL02370761A patent/PL370761A1/xx not_active Application Discontinuation
- 2002-12-17 WO PCT/HU2002/000144 patent/WO2003053969A1/en active Application Filing
- 2002-12-17 NZ NZ534015A patent/NZ534015A/en not_active IP Right Cessation
- 2002-12-17 KR KR1020077004953A patent/KR20070034136A/ko not_active Application Discontinuation
- 2002-12-17 AU AU2002353241A patent/AU2002353241B2/en not_active Ceased
- 2002-12-17 RS YU56104A patent/RS56104A/sr unknown
- 2002-12-17 IL IL16244302A patent/IL162443A0/xx unknown
- 2002-12-17 BR BR0215272-0A patent/BR0215272A/pt not_active IP Right Cessation
- 2002-12-17 KR KR1020047009788A patent/KR100725298B1/ko not_active IP Right Cessation
-
2004
- 2004-06-07 MA MA27725A patent/MA27240A1/fr unknown
- 2004-06-08 TN TNP2004000105A patent/TNSN04105A1/en unknown
- 2004-06-10 IL IL162443A patent/IL162443A/en not_active IP Right Cessation
- 2004-06-16 IS IS7317A patent/IS7317A/is unknown
- 2004-06-17 ZA ZA200404807A patent/ZA200404807B/xx unknown
- 2004-07-20 HR HR20040671A patent/HRP20040671A2/xx not_active Application Discontinuation
- 2004-07-20 NO NO20043117A patent/NO329743B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1307174C (zh) | 2007-03-28 |
| HUP0105406A2 (hu) | 2003-10-28 |
| CA2470067C (en) | 2011-02-15 |
| ZA200404807B (en) | 2005-08-29 |
| JP4530663B2 (ja) | 2010-08-25 |
| NO329743B1 (no) | 2010-12-13 |
| PL370761A1 (en) | 2005-05-30 |
| TNSN04105A1 (en) | 2006-06-01 |
| CA2470067A1 (en) | 2003-07-03 |
| EP1456205A1 (en) | 2004-09-15 |
| IS7317A (is) | 2004-06-16 |
| KR20040072670A (ko) | 2004-08-18 |
| KR100725298B1 (ko) | 2007-06-07 |
| KR20070034136A (ko) | 2007-03-27 |
| AU2002353241B2 (en) | 2008-07-10 |
| IL162443A (en) | 2010-05-17 |
| HUP0105406A3 (en) | 2003-12-29 |
| IL162443A0 (en) | 2005-11-20 |
| NZ534015A (en) | 2005-04-29 |
| MXPA04006115A (es) | 2005-06-08 |
| HRP20040671A2 (en) | 2005-08-31 |
| CN1606555A (zh) | 2005-04-13 |
| EA200400847A1 (ru) | 2004-12-30 |
| WO2003053969A1 (en) | 2003-07-03 |
| JP2005516956A (ja) | 2005-06-09 |
| US7176213B2 (en) | 2007-02-13 |
| MA27240A1 (fr) | 2005-03-01 |
| NO20043117L (no) | 2004-07-20 |
| US20050070566A1 (en) | 2005-03-31 |
| RS56104A (en) | 2006-10-27 |
| AU2002353241A1 (en) | 2003-07-09 |
| EA007226B1 (ru) | 2006-08-25 |
| HUP0105406D0 (en) | 2002-03-28 |
| BR0215272A (pt) | 2004-12-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101229504B1 (ko) | 리버스턴 유사체의 신규 화합물 및 그의 용도(1) | |
| ES2415863T3 (es) | Heterociclos sustituidos como inhibidores de Janus Quinasas | |
| US7713992B2 (en) | Triazolo-quinolin derivatives useful as adenosine receptor ligands | |
| AU2016272057B2 (en) | Use of pteridinone derivative serving as EGFR inhibitor | |
| DE102007012645A1 (de) | Substituierte Imidazo- und Triazolopyrimidine | |
| KR20120099250A (ko) | 벤조디아제핀 브로모도메인 억제제 | |
| BR112016003247B1 (pt) | Composto substituído por quinolina, composição farmacêutica compreendendo o referido composto e seu uso | |
| US20080255110A1 (en) | Imidazoquinoline derivatives as adenosine a3 receptor ligands | |
| JP6983873B2 (ja) | 化合物（２ｓ，３ｒ）−イソプロピル２−（（（２−（１，５−ジメチル−６−オキソ−１，６−ジヒドロピリジン−３−イル）−１−（（テトラヒドロ−２ｈ−ピラン−４−イル）メチル）−１ｈ−ベンゾ［ｄ］イミダゾール−５−イル）メチル）アミノ）−３−ヒドロキシブタノエートエジシレートの水和物結晶 | |
| CN105960237A (zh) | Ccr6化合物 | |
| UA78745C2 (en) | Imidazoquinoline derivatives | |
| JP3279633B2 (ja) | ピリダジンジオン化合物 | |
| JP4409935B2 (ja) | アミノキノリンおよびアミノピリジン誘導体およびそのアデノシンａ３リガンドとしての使用 | |
| JP2017525716A (ja) | キナーゼ阻害剤としての置換マクロサイクル及びその使用方法 | |
| US20050080261A1 (en) | Purine inhibitors of cyclin dependent kinase 2 and IkappaB-alpha | |
| CN117088867A (zh) | 可吸入型芳环并噻嗪及类似物、含其的药物组合物及其在抗炎、抗肿瘤中的应用 | |
| WO2015020565A1 (ru) | Замещенные [1,2,4]триазоло[4,3-a]пиридины, проявляющие свойства антогонистов аденозиновых а2а рецепторов, и их применение | |
| CN105008346B (zh) | 作为磷酸二酯酶10（pde-10）抑制剂的嘧啶衍生物 | |
| AU2002361374A1 (en) | Pyrazolyl-substituted triazoloquinoxalines | |
| RU2797117C2 (ru) | Новое хинолин-замещенное соединение | |
| Peréz-Pérez et al. | Novel antiviral compounds |