NO329743B1 - Imidazokinolinderivater, fremgangsmate for fremstilling derav, mellomprodukter i fremgangsmaten for fremstilling av forbindelsene, farmasoytiske preparater inneholdende forbindelsene og anvendelse av forbindelsene til fremstilling av farmasoytiske preparater - Google Patents
Imidazokinolinderivater, fremgangsmate for fremstilling derav, mellomprodukter i fremgangsmaten for fremstilling av forbindelsene, farmasoytiske preparater inneholdende forbindelsene og anvendelse av forbindelsene til fremstilling av farmasoytiske preparater Download PDFInfo
- Publication number
- NO329743B1 NO329743B1 NO20043117A NO20043117A NO329743B1 NO 329743 B1 NO329743 B1 NO 329743B1 NO 20043117 A NO20043117 A NO 20043117A NO 20043117 A NO20043117 A NO 20043117A NO 329743 B1 NO329743 B1 NO 329743B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- branched
- straight
- compounds
- stands
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 88
- 238000000034 method Methods 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 21
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 15
- 230000008569 process Effects 0.000 title claims description 6
- 239000000543 intermediate Substances 0.000 title description 4
- 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
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 30
- -1 methylenedioxy group Chemical group 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- 239000012453 solvate Substances 0.000 claims description 27
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 27
- 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 26
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 21
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 14
- 229960005305 adenosine Drugs 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 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 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 210000004027 cell Anatomy 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 230000005764 inhibitory process Effects 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 6
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 238000005917 acylation reaction Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 210000003169 central nervous system Anatomy 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 210000003630 histaminocyte Anatomy 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 238000011161 development Methods 0.000 claims description 3
- 210000002216 heart Anatomy 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 208000026872 Addison Disease Diseases 0.000 claims description 2
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 2
- 206010006482 Bronchospasm Diseases 0.000 claims description 2
- 208000011231 Crohn disease 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
- 206010020751 Hypersensitivity 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
- 208000007201 Myocardial reperfusion injury Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 206010039710 Scleroderma Diseases 0.000 claims description 2
- 241000159243 Toxicodendron radicans Species 0.000 claims description 2
- 208000024780 Urticaria Diseases 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 208000026935 allergic disease Diseases 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
- 206010006451 bronchitis Diseases 0.000 claims description 2
- 230000007885 bronchoconstriction Effects 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 208000007451 chronic bronchitis Diseases 0.000 claims description 2
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 claims description 2
- 230000037411 cognitive enhancing Effects 0.000 claims description 2
- 230000016396 cytokine production 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
- 150000004820 halides Chemical class 0.000 claims description 2
- 230000007954 hypoxia Effects 0.000 claims description 2
- 210000002865 immune cell 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
- 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
- 230000002265 prevention Effects 0.000 claims description 2
- 230000004044 response Effects 0.000 claims description 2
- 206010039083 rhinitis Diseases 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000002464 receptor antagonist Substances 0.000 claims 2
- 229940044551 receptor antagonist Drugs 0.000 claims 2
- 230000009466 transformation Effects 0.000 claims 2
- 125000005332 alkyl sulfoxy group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 230000012292 cell migration Effects 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 230000009251 neurologic dysfunction Effects 0.000 claims 1
- 208000015015 neurological dysfunction Diseases 0.000 claims 1
- 230000009467 reduction Effects 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 28
- 230000000694 effects Effects 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 102000005962 receptors Human genes 0.000 description 16
- 108020003175 receptors Proteins 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 230000027455 binding Effects 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000012528 membrane Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 239000000872 buffer Substances 0.000 description 8
- 239000002178 crystalline material Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 7
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 7
- 101150051188 Adora2a gene Proteins 0.000 description 6
- 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 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 229910001629 magnesium chloride Inorganic materials 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
- 102000009346 Adenosine receptors Human genes 0.000 description 5
- 108050000203 Adenosine receptors Proteins 0.000 description 5
- 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 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 101710169336 5'-deoxyadenosine deaminase Proteins 0.000 description 4
- 102000055025 Adenosine deaminases Human genes 0.000 description 4
- 101150078577 Adora2b gene Proteins 0.000 description 4
- 229920002873 Polyethylenimine Polymers 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 230000014155 detection of activity Effects 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000009871 nonspecific binding Effects 0.000 description 4
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 101000783645 Homo sapiens Adenosine receptor A3 Proteins 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
- 108060000200 adenylate cyclase Proteins 0.000 description 3
- 102000030621 adenylate cyclase Human genes 0.000 description 3
- 239000003795 chemical substances by application Substances 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
- 102000046278 human ADORA3 Human genes 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 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 2
- 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
- 101150046889 ADORA3 gene Proteins 0.000 description 2
- 108010060261 Adenosine A3 Receptor Proteins 0.000 description 2
- 102000008161 Adenosine A3 Receptor Human genes 0.000 description 2
- FFBDFADSZUINTG-UHFFFAOYSA-N DPCPX Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1CCCC1 FFBDFADSZUINTG-UHFFFAOYSA-N 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
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 108020004999 messenger RNA Proteins 0.000 description 2
- 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 2
- 230000003287 optical effect 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
- 239000007787 solid Substances 0.000 description 2
- 210000001550 testis Anatomy 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- LOGOEBMHHXYBID-WBKNRDRNSA-N (2s,3s,4r,5r)-5-[6-[(4-amino-3-iodanylphenyl)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=NC(NCC=3C=C([125I])C(N)=CC=3)=C2N=C1 LOGOEBMHHXYBID-WBKNRDRNSA-N 0.000 description 1
- LDYMCRRFCMRFKB-MOROJQBDSA-N (2s,3s,4r,5r)-5-[6-[(4-aminophenyl)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=NC(NCC=3C=CC(N)=CC=3)=C2N=C1 LDYMCRRFCMRFKB-MOROJQBDSA-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
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-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
- LELCQSVSHYQGMI-UHFFFAOYSA-N 2-amino-4-(thiophen-2-ylmethylamino)quinoline-3-carbonitrile Chemical compound N#CC=1C(N)=NC2=CC=CC=C2C=1NCC1=CC=CS1 LELCQSVSHYQGMI-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
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 101150007969 ADORA1 gene Proteins 0.000 description 1
- 108010060263 Adenosine A1 Receptor Proteins 0.000 description 1
- 102000007471 Adenosine A2A receptor Human genes 0.000 description 1
- 108010085277 Adenosine A2A receptor Proteins 0.000 description 1
- 229940123786 Adenosine A3 receptor antagonist Drugs 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 208000000059 Dyspnea Diseases 0.000 description 1
- 101000783751 Homo sapiens Adenosine receptor A2a Proteins 0.000 description 1
- 102000018697 Membrane Proteins Human genes 0.000 description 1
- 108010052285 Membrane Proteins Proteins 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 102000011420 Phospholipase D Human genes 0.000 description 1
- 108090000553 Phospholipase D Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 1
- 102000014384 Type C Phospholipases Human genes 0.000 description 1
- 108010079194 Type C Phospholipases Proteins 0.000 description 1
- 206010045240 Type I hypersensitivity Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000002580 adenosine A3 receptor antagonist Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 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
- 230000009286 beneficial effect Effects 0.000 description 1
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 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
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 230000002057 chronotropic effect Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 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
- 230000001419 dependent effect Effects 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
- 238000001035 drying Methods 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 150000002148 esters Chemical class 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
- 230000002349 favourable effect Effects 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
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 102000055905 human ADORA2A Human genes 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 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
- 239000008188 pellet Substances 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
- 238000011321 prophylaxis Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 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
- LOAUVZALPPNFOQ-UHFFFAOYSA-M quinaldate Chemical compound C1=CC=CC2=NC(C(=O)[O-])=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-M 0.000 description 1
- ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 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
- 238000013391 scatchard analysis Methods 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 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
- 230000000946 synaptic effect Effects 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 231100000048 toxicity data 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Hematology (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Psychology (AREA)
- Child & Adolescent Psychology (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 (2)
Publication Number | Publication Date |
---|---|
NO20043117L NO20043117L (no) | 2004-07-20 |
NO329743B1 true NO329743B1 (no) | 2010-12-13 |
Family
ID=47711504
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20043117A NO329743B1 (no) | 2001-12-21 | 2004-07-20 | Imidazokinolinderivater, fremgangsmate for fremstilling derav, mellomprodukter i fremgangsmaten for fremstilling av forbindelsene, farmasoytiske preparater inneholdende forbindelsene og anvendelse av forbindelsene til fremstilling av farmasoytiske preparater |
Country Status (23)
Country | Link |
---|---|
US (1) | US7176213B2 (zh) |
EP (1) | EP1456205A1 (zh) |
JP (1) | JP4530663B2 (zh) |
KR (2) | KR20070034136A (zh) |
CN (1) | CN1307174C (zh) |
AU (1) | AU2002353241B2 (zh) |
BR (1) | BR0215272A (zh) |
CA (1) | CA2470067C (zh) |
EA (1) | EA007226B1 (zh) |
HR (1) | HRP20040671A2 (zh) |
HU (1) | HUP0105406A3 (zh) |
IL (2) | IL162443A0 (zh) |
IS (1) | IS7317A (zh) |
MA (1) | MA27240A1 (zh) |
MX (1) | MXPA04006115A (zh) |
NO (1) | NO329743B1 (zh) |
NZ (1) | NZ534015A (zh) |
PL (1) | PL370761A1 (zh) |
RS (1) | RS56104A (zh) |
TN (1) | TNSN04105A1 (zh) |
UA (1) | UA78745C2 (zh) |
WO (1) | WO2003053969A1 (zh) |
ZA (1) | ZA200404807B (zh) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MXPA04002785A (es) * | 2001-09-24 | 2004-07-29 | Elan Pharm Inc | Aminas sustituidas para tratamiento de enfermedad de alzheimer. |
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 |
EP1858326A4 (en) * | 2005-02-22 | 2008-10-15 | Univ California | METHODS OF TREATING GASTROINTESTINAL INFLAMMATION |
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 |
BR112015018282B1 (pt) | 2013-02-01 | 2021-08-24 | Wellstat Therapeutics Corporation | Compostos de amina, composição compreendendo os referidos compostos e usos dos mesmos |
ES2578363B1 (es) | 2015-01-22 | 2017-01-31 | Palobiofarma, S.L. | Moduladores de los receptores A3 de adenosina |
AU2016302144B2 (en) * | 2015-08-03 | 2020-10-08 | 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 (zh) | 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 KR KR1020077004953A patent/KR20070034136A/ko not_active Application Discontinuation
- 2002-12-17 MX MXPA04006115A patent/MXPA04006115A/es active IP Right Grant
- 2002-12-17 EA EA200400847A patent/EA007226B1/ru not_active IP Right Cessation
- 2002-12-17 AU AU2002353241A patent/AU2002353241B2/en not_active Ceased
- 2002-12-17 NZ NZ534015A patent/NZ534015A/en not_active IP Right Cessation
- 2002-12-17 UA UA20040706065A patent/UA78745C2/uk unknown
- 2002-12-17 RS YU56104A patent/RS56104A/sr unknown
- 2002-12-17 JP JP2003554685A patent/JP4530663B2/ja not_active Expired - Fee Related
- 2002-12-17 KR KR1020047009788A patent/KR100725298B1/ko not_active IP Right Cessation
- 2002-12-17 IL IL16244302A patent/IL162443A0/xx unknown
- 2002-12-17 WO PCT/HU2002/000144 patent/WO2003053969A1/en active Application Filing
- 2002-12-17 BR BR0215272-0A patent/BR0215272A/pt not_active IP Right Cessation
- 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 EP EP02788261A patent/EP1456205A1/en not_active Withdrawn
- 2002-12-17 PL PL02370761A patent/PL370761A1/xx not_active Application Discontinuation
- 2002-12-17 CA CA2470067A patent/CA2470067C/en not_active Expired - Fee Related
-
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 NO NO20043117A patent/NO329743B1/no not_active IP Right Cessation
- 2004-07-20 HR HR20040671A patent/HRP20040671A2/xx not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
EP1456205A1 (en) | 2004-09-15 |
HUP0105406A3 (en) | 2003-12-29 |
HUP0105406D0 (en) | 2002-03-28 |
IL162443A (en) | 2010-05-17 |
KR100725298B1 (ko) | 2007-06-07 |
MA27240A1 (fr) | 2005-03-01 |
AU2002353241A1 (en) | 2003-07-09 |
BR0215272A (pt) | 2004-12-14 |
JP4530663B2 (ja) | 2010-08-25 |
CN1606555A (zh) | 2005-04-13 |
PL370761A1 (en) | 2005-05-30 |
CA2470067C (en) | 2011-02-15 |
EA007226B1 (ru) | 2006-08-25 |
RS56104A (en) | 2006-10-27 |
AU2002353241B2 (en) | 2008-07-10 |
NZ534015A (en) | 2005-04-29 |
UA78745C2 (en) | 2007-04-25 |
IL162443A0 (en) | 2005-11-20 |
KR20040072670A (ko) | 2004-08-18 |
JP2005516956A (ja) | 2005-06-09 |
NO20043117L (no) | 2004-07-20 |
MXPA04006115A (es) | 2005-06-08 |
ZA200404807B (en) | 2005-08-29 |
CA2470067A1 (en) | 2003-07-03 |
TNSN04105A1 (en) | 2006-06-01 |
CN1307174C (zh) | 2007-03-28 |
EA200400847A1 (ru) | 2004-12-30 |
WO2003053969A1 (en) | 2003-07-03 |
US20050070566A1 (en) | 2005-03-31 |
HUP0105406A2 (hu) | 2003-10-28 |
HRP20040671A2 (en) | 2005-08-31 |
US7176213B2 (en) | 2007-02-13 |
IS7317A (is) | 2004-06-16 |
KR20070034136A (ko) | 2007-03-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7709489B2 (en) | Imidazoquinoline derivatives as adenosine A3 receptor ligands | |
JP2011042653A (ja) | アデノシン受容体リガンドとして有用なトリアゾロ−キノリン誘導体 | |
AU2002304358B2 (en) | Aminoquinoline and aminopyridine derivatives and their use as adenosine A3 ligands | |
AU2002304358A1 (en) | Aminoquinoline and aminopyridine derivatives and their use as adenosine A3 ligands | |
NO329743B1 (no) | Imidazokinolinderivater, fremgangsmate for fremstilling derav, mellomprodukter i fremgangsmaten for fremstilling av forbindelsene, farmasoytiske preparater inneholdende forbindelsene og anvendelse av forbindelsene til fremstilling av farmasoytiske preparater | |
KR20070020335A (ko) | 아미노퀴놀린 유도체 및 아데노신 a3 리간드로서의 이의용도 | |
ZA200308865B (en) | Aminoquinoline derivatives and their use as adenosine A3 ligands. |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM1K | Lapsed by not paying the annual fees |