DE69628019T2 - Chinolone und deren therapeutische verwendung - Google Patents
Chinolone und deren therapeutische verwendung Download PDFInfo
- Publication number
- DE69628019T2 DE69628019T2 DE69628019T DE69628019T DE69628019T2 DE 69628019 T2 DE69628019 T2 DE 69628019T2 DE 69628019 T DE69628019 T DE 69628019T DE 69628019 T DE69628019 T DE 69628019T DE 69628019 T2 DE69628019 T2 DE 69628019T2
- Authority
- DE
- Germany
- Prior art keywords
- ethyl
- dihydro
- oxo
- quinolinecarboxamide
- pyridyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 230000001225 therapeutic effect Effects 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 122
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 230000005764 inhibitory process Effects 0.000 claims abstract description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 3
- -1 alkyl amides Chemical class 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 206010017533 Fungal infection Diseases 0.000 claims description 8
- 206010040070 Septic Shock Diseases 0.000 claims description 8
- 125000005907 alkyl ester group Chemical group 0.000 claims description 8
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 241000701022 Cytomegalovirus Species 0.000 claims description 5
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 201000008937 atopic dermatitis Diseases 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 230000002490 cerebral effect Effects 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 208000031888 Mycoses Diseases 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 4
- 206010039966 Senile dementia Diseases 0.000 claims description 4
- 206010040047 Sepsis Diseases 0.000 claims description 4
- 208000036142 Viral infection Diseases 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
- 230000000172 allergic effect Effects 0.000 claims description 4
- 206010003246 arthritis Diseases 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 230000009385 viral infection Effects 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 3
- 206010006895 Cachexia Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 206010014824 Endotoxic shock Diseases 0.000 claims description 3
- 206010035664 Pneumonia Diseases 0.000 claims description 3
- 206010063837 Reperfusion injury Diseases 0.000 claims description 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 201000010105 allergic rhinitis Diseases 0.000 claims description 3
- 230000002917 arthritic effect Effects 0.000 claims description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 208000010668 atopic eczema Diseases 0.000 claims description 3
- 206010006451 bronchitis Diseases 0.000 claims description 3
- 208000007451 chronic bronchitis Diseases 0.000 claims description 3
- 201000010064 diabetes insipidus Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 201000003651 pulmonary sarcoidosis Diseases 0.000 claims description 3
- 230000004044 response Effects 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 230000036303 septic shock Effects 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 241000701161 unidentified adenovirus Species 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
- QSSPHZJBIQILKH-UHFFFAOYSA-N 1-ethyl-4-oxo-n-(2-pyridin-3-ylethyl)-6-(trifluoromethyl)quinoline-3-carboxamide;hydrochloride Chemical compound Cl.O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCCC1=CC=CN=C1 QSSPHZJBIQILKH-UHFFFAOYSA-N 0.000 claims description 2
- LGUCOZFVDDTKDQ-UHFFFAOYSA-N 1-ethyl-4-oxo-n-(2-pyridin-4-ylethyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC=C(C(F)(F)F)C=C2N(CC)C=C1C(=O)NCCC1=CC=NC=C1 LGUCOZFVDDTKDQ-UHFFFAOYSA-N 0.000 claims description 2
- QHFAMBQGQKNSIS-UHFFFAOYSA-N 1-ethyl-4-oxo-n-(pyridin-2-ylmethyl)-6-(trifluoromethyl)quinoline-3-carboxamide;hydrochloride Chemical compound Cl.O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCC1=CC=CC=N1 QHFAMBQGQKNSIS-UHFFFAOYSA-N 0.000 claims description 2
- YAVWEBULNQMGFA-UHFFFAOYSA-N 1-ethyl-6-fluoro-8-methoxy-4-oxo-n-(2-pyridin-4-ylethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(F)=CC(OC)=C2N(CC)C=C1C(=O)NCCC1=CC=NC=C1 YAVWEBULNQMGFA-UHFFFAOYSA-N 0.000 claims description 2
- MOQSGPGLZFYABG-UHFFFAOYSA-N 1-ethyl-n-(2-pyridin-4-ylethyl)-4-(sulfanylidenemethylidene)-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound S=C=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCCC1=CC=NC=C1 MOQSGPGLZFYABG-UHFFFAOYSA-N 0.000 claims description 2
- FRKZOIDQNLRYBN-UHFFFAOYSA-N 1-ethyl-n-[2-(3-methoxyphenyl)ethyl]-4-oxo-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCCC1=CC=CC(OC)=C1 FRKZOIDQNLRYBN-UHFFFAOYSA-N 0.000 claims description 2
- RDHWMVHLPCKHTK-UHFFFAOYSA-N 1-ethyl-n-[2-(4-methoxyphenyl)ethyl]-4-oxo-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCCC1=CC=C(OC)C=C1 RDHWMVHLPCKHTK-UHFFFAOYSA-N 0.000 claims description 2
- AXQYNOIRKUMBLX-UHFFFAOYSA-N 4-oxo-1-propyl-n-(2-pyridin-4-ylethyl)-6-(trifluoromethyl)quinoline-3-carboxamide;hydrochloride Chemical compound Cl.O=C1C2=CC(C(F)(F)F)=CC=C2N(CCC)C=C1C(=O)NCCC1=CC=NC=C1 AXQYNOIRKUMBLX-UHFFFAOYSA-N 0.000 claims description 2
- YQDGQEKUTLYWJU-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinoline Chemical compound C1=CC=C2CCCCC2=N1 YQDGQEKUTLYWJU-UHFFFAOYSA-N 0.000 claims description 2
- SUAHRYPPIUNSPS-UHFFFAOYSA-N 5-ethyl-n-[(4-methoxyphenyl)methyl]-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxamide Chemical compound O=C1C2=CC=3OCOC=3C=C2N(CC)C=C1C(=O)NCC1=CC=C(OC)C=C1 SUAHRYPPIUNSPS-UHFFFAOYSA-N 0.000 claims description 2
- GLFLNVCELMQGGU-UHFFFAOYSA-N 6-fluoro-4-oxo-n-(2-pyridin-4-ylethyl)-1-(pyridin-4-ylmethyl)quinoline-3-carboxamide Chemical compound C1=C(C(=O)NCCC=2C=CN=CC=2)C(=O)C2=CC(F)=CC=C2N1CC1=CC=NC=C1 GLFLNVCELMQGGU-UHFFFAOYSA-N 0.000 claims description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 claims description 2
- 206010063094 Cerebral malaria Diseases 0.000 claims description 2
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 206010018367 Glomerulonephritis chronic Diseases 0.000 claims description 2
- 201000005569 Gout Diseases 0.000 claims description 2
- 206010018634 Gouty Arthritis Diseases 0.000 claims description 2
- 208000010496 Heart Arrest Diseases 0.000 claims description 2
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 206010069698 Langerhans' cell histiocytosis Diseases 0.000 claims description 2
- 208000026139 Memory disease Diseases 0.000 claims description 2
- 208000005314 Multi-Infarct Dementia Diseases 0.000 claims description 2
- 208000000112 Myalgia Diseases 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 206010044248 Toxic shock syndrome Diseases 0.000 claims description 2
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims description 2
- 206010052779 Transplant rejections Diseases 0.000 claims description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
- 201000004810 Vascular dementia Diseases 0.000 claims description 2
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 2
- 208000003455 anaphylaxis Diseases 0.000 claims description 2
- 208000024998 atopic conjunctivitis Diseases 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 208000019664 bone resorption disease Diseases 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 208000003401 eosinophilic granuloma Diseases 0.000 claims description 2
- 230000002496 gastric effect Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 206010022000 influenza Diseases 0.000 claims description 2
- 208000018937 joint inflammation Diseases 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000004060 metabolic process Effects 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 201000008383 nephritis Diseases 0.000 claims description 2
- 230000000926 neurological effect Effects 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 230000036647 reaction Effects 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 2
- 208000018464 vernal keratoconjunctivitis Diseases 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- VJQGLSHWTOZIKP-UHFFFAOYSA-N 5-ethyl-8-oxo-N-(2-pyridin-2-ylethyl)-[1,3]dioxolo[4,5-g]quinoline-7-carboxamide 5-ethyl-8-oxo-N-(2-pyridin-4-ylethyl)-[1,3]dioxolo[4,5-g]quinoline-7-carboxamide Chemical compound C(C)N1C=C(C(C=2C=C3C(=CC12)OCO3)=O)C(=O)NCCC3=CC=NC=C3.C(C)N3C=C(C(C=1C=C2C(=CC31)OCO2)=O)C(=O)NCCC2=NC=CC=C2 VJQGLSHWTOZIKP-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 208000010370 Adenoviridae Infections Diseases 0.000 claims 1
- 206010060931 Adenovirus infection Diseases 0.000 claims 1
- 206010011831 Cytomegalovirus infection Diseases 0.000 claims 1
- 208000001860 Eye Infections Diseases 0.000 claims 1
- 208000029433 Herpesviridae infectious disease Diseases 0.000 claims 1
- 206010020649 Hyperkeratosis Diseases 0.000 claims 1
- 208000001126 Keratosis Diseases 0.000 claims 1
- 208000024780 Urticaria Diseases 0.000 claims 1
- 208000011589 adenoviridae infectious disease Diseases 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 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 claims 1
- 208000011323 eye infectious disease Diseases 0.000 claims 1
- 230000002538 fungal effect Effects 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 208000028774 intestinal disease Diseases 0.000 claims 1
- 210000001503 joint Anatomy 0.000 claims 1
- 208000021601 lentivirus infection Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000004792 malaria Diseases 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 7
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 abstract description 6
- 102000018594 Tumour necrosis factor Human genes 0.000 abstract 1
- 108050007852 Tumour necrosis factor Proteins 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 94
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 42
- 239000000543 intermediate Substances 0.000 description 42
- 239000000460 chlorine Substances 0.000 description 34
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 32
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 32
- 238000000034 method Methods 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 210000001744 T-lymphocyte Anatomy 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 241000725303 Human immunodeficiency virus Species 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- KYGZCKSPAKDVKC-UHFFFAOYSA-N Oxolinic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 KYGZCKSPAKDVKC-UHFFFAOYSA-N 0.000 description 11
- 229960000321 oxolinic acid Drugs 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 241000700605 Viruses Species 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 8
- 208000031886 HIV Infections Diseases 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- 230000001404 mediated effect Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000004913 activation Effects 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 230000000699 topical effect Effects 0.000 description 5
- 102000004127 Cytokines Human genes 0.000 description 4
- 108090000695 Cytokines Proteins 0.000 description 4
- 208000037357 HIV infectious disease Diseases 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 4
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 3
- 241000713340 Human immunodeficiency virus 2 Species 0.000 description 3
- 108090000542 Lymphotoxin-alpha Proteins 0.000 description 3
- 102000004083 Lymphotoxin-alpha Human genes 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 239000002158 endotoxin Substances 0.000 description 3
- 210000003979 eosinophil Anatomy 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000014509 gene expression Effects 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 210000001616 monocyte Anatomy 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 230000010076 replication Effects 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 230000029812 viral genome replication Effects 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 2
- 206010001513 AIDS related complex Diseases 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 208000035473 Communicable disease Diseases 0.000 description 2
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000713800 Feline immunodeficiency virus Species 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 206010020164 HIV infection CDC Group III Diseases 0.000 description 2
- 108010002352 Interleukin-1 Proteins 0.000 description 2
- 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 2
- 241001465754 Metazoa Species 0.000 description 2
- 102000013967 Monokines Human genes 0.000 description 2
- 108010050619 Monokines Proteins 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229940124630 bronchodilator Drugs 0.000 description 2
- 239000000168 bronchodilator agent Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 229940095074 cyclic amp Drugs 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000036039 immunity Effects 0.000 description 2
- 230000002458 infectious effect Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229920006008 lipopolysaccharide Polymers 0.000 description 2
- 210000002540 macrophage Anatomy 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
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 201000008482 osteoarthritis Diseases 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000007660 quinolones Chemical class 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 241000712461 unidentified influenza virus Species 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- PAMKMOPNUVVQAE-UHFFFAOYSA-N 1-ethyl-2-oxoquinoline-3-carboxamide Chemical compound C1=CC=C2C=C(C(N)=O)C(=O)N(CC)C2=C1 PAMKMOPNUVVQAE-UHFFFAOYSA-N 0.000 description 1
- PMPAFROTYMTHFU-UHFFFAOYSA-N 1-ethyl-4-(sulfanylidenemethylidene)-6-(trifluoromethyl)quinoline-3-carboxylic acid Chemical compound FC(F)(F)C1=CC=C2N(CC)C=C(C(O)=O)C(=C=S)C2=C1 PMPAFROTYMTHFU-UHFFFAOYSA-N 0.000 description 1
- FUUBNHWVURTHHX-UHFFFAOYSA-N 1-ethyl-4-oxo-n-(2-phenylethyl)-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCCC1=CC=CC=C1 FUUBNHWVURTHHX-UHFFFAOYSA-N 0.000 description 1
- RQYQPDZVXWOILI-UHFFFAOYSA-N 1-ethyl-4-oxo-n-(2-pyridin-2-ylethyl)-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCCC1=CC=CC=N1 RQYQPDZVXWOILI-UHFFFAOYSA-N 0.000 description 1
- FQXDXUPRYMEQJF-UHFFFAOYSA-N 1-ethyl-4-oxo-n-(2-pyridin-3-ylethyl)-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCCC1=CC=CN=C1 FQXDXUPRYMEQJF-UHFFFAOYSA-N 0.000 description 1
- FBHOZQQLUQDXLO-UHFFFAOYSA-N 1-ethyl-4-oxo-n-(2-pyridin-4-ylethyl)-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCCC1=CC=NC=C1 FBHOZQQLUQDXLO-UHFFFAOYSA-N 0.000 description 1
- JGWXWCHGVSWBOP-UHFFFAOYSA-N 1-ethyl-4-oxo-n-(2-pyridin-4-ylethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC=CC=C2N(CC)C=C1C(=O)NCCC1=CC=NC=C1 JGWXWCHGVSWBOP-UHFFFAOYSA-N 0.000 description 1
- DGWYVSDXSNFQQR-UHFFFAOYSA-N 1-ethyl-4-oxo-n-(3-phenylpropyl)-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCCCC1=CC=CC=C1 DGWYVSDXSNFQQR-UHFFFAOYSA-N 0.000 description 1
- KAFKXSZHWOCIRW-UHFFFAOYSA-N 1-ethyl-4-oxo-n-(pyridin-2-ylmethyl)-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCC1=CC=CC=N1 KAFKXSZHWOCIRW-UHFFFAOYSA-N 0.000 description 1
- FXZBYIPLMJMOHH-UHFFFAOYSA-N 1-ethyl-4-oxo-n-(pyridin-3-ylmethyl)-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCC1=CC=CN=C1 FXZBYIPLMJMOHH-UHFFFAOYSA-N 0.000 description 1
- YZAJDDUPLPASSI-UHFFFAOYSA-N 1-ethyl-4-oxo-n-(pyridin-4-ylmethyl)-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCC1=CC=NC=C1 YZAJDDUPLPASSI-UHFFFAOYSA-N 0.000 description 1
- ZSEJADLCFCHIGX-UHFFFAOYSA-N 1-ethyl-4-oxoquinoline-3-carboxylic acid Chemical compound C1=CC=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 ZSEJADLCFCHIGX-UHFFFAOYSA-N 0.000 description 1
- OORSJSGSBGVYJN-UHFFFAOYSA-N 1-ethyl-6,7-dimethoxy-4-oxo-n-(2-pyridin-4-ylethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(OC)=C(OC)C=C2N(CC)C=C1C(=O)NCCC1=CC=NC=C1 OORSJSGSBGVYJN-UHFFFAOYSA-N 0.000 description 1
- VVEQWCWCKFNYTL-UHFFFAOYSA-N 1-ethyl-6-fluoro-8-methyl-4-oxo-n-(2-pyridin-4-ylethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(F)=CC(C)=C2N(CC)C=C1C(=O)NCCC1=CC=NC=C1 VVEQWCWCKFNYTL-UHFFFAOYSA-N 0.000 description 1
- QNPOUBIFUAYGBH-UHFFFAOYSA-N 1-ethyl-6-fluoro-8-methyl-4-oxo-n-(2-pyridin-4-ylethyl)quinoline-3-carboxamide;hydrochloride Chemical compound Cl.O=C1C2=CC(F)=CC(C)=C2N(CC)C=C1C(=O)NCCC1=CC=NC=C1 QNPOUBIFUAYGBH-UHFFFAOYSA-N 0.000 description 1
- ZTSJBXSCYNOMGQ-UHFFFAOYSA-N 1-ethyl-6-methyl-4-oxo-n-(2-pyridin-4-ylethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C)=CC=C2N(CC)C=C1C(=O)NCCC1=CC=NC=C1 ZTSJBXSCYNOMGQ-UHFFFAOYSA-N 0.000 description 1
- KJEQZZRCQSKUNM-UHFFFAOYSA-N 1-ethyl-6-methyl-4-oxo-n-(2-pyridin-4-ylethyl)quinoline-3-carboxamide;hydrochloride Chemical compound Cl.O=C1C2=CC(C)=CC=C2N(CC)C=C1C(=O)NCCC1=CC=NC=C1 KJEQZZRCQSKUNM-UHFFFAOYSA-N 0.000 description 1
- BXCLYVRHLWNJSJ-UHFFFAOYSA-N 1-ethyl-6-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound CC1=CC=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 BXCLYVRHLWNJSJ-UHFFFAOYSA-N 0.000 description 1
- QEGQFXBQYBNDSO-UHFFFAOYSA-N 1-ethyl-n-[2-(2-methoxyphenyl)ethyl]-4-oxo-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCCC1=CC=CC=C1OC QEGQFXBQYBNDSO-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical class OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
- IDLHTECVNDEOIY-UHFFFAOYSA-N 2-pyridin-4-ylethanamine Chemical compound NCCC1=CC=NC=C1 IDLHTECVNDEOIY-UHFFFAOYSA-N 0.000 description 1
- KFKSGGUYYZSXEA-UHFFFAOYSA-N 4-oxo-1-propyl-n-(2-pyridin-4-ylethyl)-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CCC)C=C1C(=O)NCCC1=CC=NC=C1 KFKSGGUYYZSXEA-UHFFFAOYSA-N 0.000 description 1
- JNBHCKOEIOIRBZ-UHFFFAOYSA-N 5-ethyl-8-oxo-n-(1,2,3,4-tetrahydronaphthalen-1-yl)-[1,3]dioxolo[4,5-g]quinoline-7-carboxamide Chemical compound O=C1C2=CC=3OCOC=3C=C2N(CC)C=C1C(=O)NC1C2=CC=CC=C2CCC1 JNBHCKOEIOIRBZ-UHFFFAOYSA-N 0.000 description 1
- NUROVTWUYFNHMB-UHFFFAOYSA-N 5-ethyl-8-oxo-n-(1,2,3,4-tetrahydronaphthalen-2-yl)-[1,3]dioxolo[4,5-g]quinoline-7-carboxamide Chemical compound O=C1C2=CC=3OCOC=3C=C2N(CC)C=C1C(=O)NC1CC2=CC=CC=C2CC1 NUROVTWUYFNHMB-UHFFFAOYSA-N 0.000 description 1
- IOOKYMVMUFSNON-UHFFFAOYSA-N 5-ethyl-8-oxo-n-(2-phenylethyl)-[1,3]dioxolo[4,5-g]quinoline-7-carboxamide Chemical compound O=C1C2=CC=3OCOC=3C=C2N(CC)C=C1C(=O)NCCC1=CC=CC=C1 IOOKYMVMUFSNON-UHFFFAOYSA-N 0.000 description 1
- WARXYOJEFWSMAH-UHFFFAOYSA-N 5-ethyl-8-oxo-n-(2-pyridin-2-ylethyl)-[1,3]dioxolo[4,5-g]quinoline-7-carboxamide Chemical compound O=C1C2=CC=3OCOC=3C=C2N(CC)C=C1C(=O)NCCC1=CC=CC=N1 WARXYOJEFWSMAH-UHFFFAOYSA-N 0.000 description 1
- RWQUYEFZTSWDNB-UHFFFAOYSA-N 5-ethyl-8-oxo-n-(2-pyridin-4-ylethyl)-[1,3]dioxolo[4,5-g]quinoline-7-carboxamide Chemical compound O=C1C2=CC=3OCOC=3C=C2N(CC)C=C1C(=O)NCCC1=CC=NC=C1 RWQUYEFZTSWDNB-UHFFFAOYSA-N 0.000 description 1
- COECVXZYLDBRNU-UHFFFAOYSA-N 5-ethyl-8-oxo-n-(2-pyridin-4-ylethyl)-[1,3]dioxolo[4,5-g]quinoline-7-carboxamide;hydrochloride Chemical compound Cl.O=C1C2=CC=3OCOC=3C=C2N(CC)C=C1C(=O)NCCC1=CC=NC=C1 COECVXZYLDBRNU-UHFFFAOYSA-N 0.000 description 1
- IHRYKRWCMHAEQT-UHFFFAOYSA-N 6-fluoro-4-oxo-1-(pyridin-4-ylmethyl)quinoline-3-carboxylic acid Chemical compound C12=CC=C(F)C=C2C(=O)C(C(=O)O)=CN1CC1=CC=NC=C1 IHRYKRWCMHAEQT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- 208000031295 Animal disease Diseases 0.000 description 1
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 1
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 0 C*(NC(C1=CN(C2C3C2C3)c2c(*)c(*)c(*)c(*)c2C1=*)O)=C Chemical compound C*(NC(C1=CN(C2C3C2C3)c2c(*)c(*)c(*)c(*)c2C1=*)O)=C 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000283073 Equus caballus Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 206010017577 Gait disturbance Diseases 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- 208000007514 Herpes zoster Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 206010020751 Hypersensitivity Diseases 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
- 108090001005 Interleukin-6 Proteins 0.000 description 1
- 150000000994 L-ascorbates Chemical class 0.000 description 1
- 241000713666 Lentivirus Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010027236 Meningitis fungal Diseases 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000001388 Opportunistic Infections Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
- 206010037549 Purpura Diseases 0.000 description 1
- 241001672981 Purpura Species 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 201000010001 Silicosis Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000000150 Sympathomimetic Substances 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 108010067390 Viral Proteins Proteins 0.000 description 1
- 241000713325 Visna/maedi virus Species 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000000924 antiasthmatic agent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000496 cardiotonic agent Substances 0.000 description 1
- 230000003177 cardiotonic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 1
- 229960000258 corticotropin Drugs 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 230000005574 cross-species transmission Effects 0.000 description 1
- ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- HJODSEHATBSZGJ-UHFFFAOYSA-N ethyl 1-ethyl-4-(sulfanylidenemethylidene)-6-(trifluoromethyl)quinoline-3-carboxylate Chemical compound C1=C(C(F)(F)F)C=C2C(=C=S)C(C(=O)OCC)=CN(CC)C2=C1 HJODSEHATBSZGJ-UHFFFAOYSA-N 0.000 description 1
- OUIIOINZTCLLEE-UHFFFAOYSA-N ethyl 1-ethyl-4-oxoquinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)=CN(CC)C2=C1 OUIIOINZTCLLEE-UHFFFAOYSA-N 0.000 description 1
- WPOJSOSMSXFTKF-UHFFFAOYSA-N ethyl 1-ethyl-6,7-dimethoxy-4-oxoquinoline-3-carboxylate Chemical compound COC1=C(OC)C=C2C(=O)C(C(=O)OCC)=CN(CC)C2=C1 WPOJSOSMSXFTKF-UHFFFAOYSA-N 0.000 description 1
- ZQSXVXUZVAFZCO-UHFFFAOYSA-N ethyl 6-fluoro-4-oxo-1-(pyridin-4-ylmethyl)quinoline-3-carboxylate Chemical compound C12=CC=C(F)C=C2C(=O)C(C(=O)OCC)=CN1CC1=CC=NC=C1 ZQSXVXUZVAFZCO-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 201000010056 fungal meningitis Diseases 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000033065 inborn errors of immunity Diseases 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 208000011379 keloid formation Diseases 0.000 description 1
- 210000001865 kupffer cell Anatomy 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 230000002969 morbid Effects 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- UBCDMAUJCRQKAB-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-1-yl)-5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxamide Chemical compound O=C1C2=CC=3OCOC=3C=C2N(CC)C=C1C(=O)NC1C2=CC=CC=C2CC1 UBCDMAUJCRQKAB-UHFFFAOYSA-N 0.000 description 1
- BVWLJGGHEABACS-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxamide Chemical compound O=C1C2=CC=3OCOC=3C=C2N(CC)C=C1C(=O)NC1CC2=CC=CC=C2C1 BVWLJGGHEABACS-UHFFFAOYSA-N 0.000 description 1
- LEZLNQZVFWYAPQ-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-1-ethyl-4-oxo-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCC1=CC=CC=C1Cl LEZLNQZVFWYAPQ-UHFFFAOYSA-N 0.000 description 1
- SSVXQOJVYZBQAL-UHFFFAOYSA-N n-[2-(2,3-dimethoxyphenyl)ethyl]-5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxamide Chemical compound O=C1C2=CC=3OCOC=3C=C2N(CC)C=C1C(=O)NCCC1=CC=CC(OC)=C1OC SSVXQOJVYZBQAL-UHFFFAOYSA-N 0.000 description 1
- GDNXKLLWPYQZSX-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]-1-ethyl-4-oxo-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCCC1=CC=CC=C1Cl GDNXKLLWPYQZSX-UHFFFAOYSA-N 0.000 description 1
- OHWZTLGIBTYGJB-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-1-ethyl-4-oxo-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCCC1=CC=C(OC)C(OC)=C1 OHWZTLGIBTYGJB-UHFFFAOYSA-N 0.000 description 1
- OWOIFZSKQWPQLM-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxamide Chemical compound O=C1C2=CC=3OCOC=3C=C2N(CC)C=C1C(=O)NCCC1=CC=C(OC)C(OC)=C1 OWOIFZSKQWPQLM-UHFFFAOYSA-N 0.000 description 1
- ZYMUJYPMULTQRY-UHFFFAOYSA-N n-benzyl-1-ethyl-4-oxo-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCC1=CC=CC=C1 ZYMUJYPMULTQRY-UHFFFAOYSA-N 0.000 description 1
- 210000000822 natural killer cell Anatomy 0.000 description 1
- 210000004498 neuroglial cell Anatomy 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229960001802 phenylephrine Drugs 0.000 description 1
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 208000028529 primary immunodeficiency disease Diseases 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- AMMGCGVWJMRTQI-UHFFFAOYSA-N prop-1-en-2-yl carbonochloridate Chemical compound CC(=C)OC(Cl)=O AMMGCGVWJMRTQI-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- MMCIXNVRVDTQSG-UHFFFAOYSA-N quinoline-7-carboxamide Chemical compound C1=CC=NC2=CC(C(=O)N)=CC=C21 MMCIXNVRVDTQSG-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 210000003019 respiratory muscle Anatomy 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000007391 self-medication Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 238000005486 sulfidation Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 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
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009772 tissue formation Effects 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 description 1
- 239000002451 tumor necrosis factor inhibitor Substances 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- 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
-
- 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
- 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
- A61P19/00—Drugs for skeletal disorders
-
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- 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
- A61P25/28—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
-
- 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
- A61P27/16—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
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Ophthalmology & Optometry (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Virology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Cardiology (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9515811.9A GB9515811D0 (en) | 1995-08-02 | 1995-08-02 | Novel compounds |
| GB9515811 | 1995-08-02 | ||
| GB9526377 | 1995-12-22 | ||
| GBGB9526377.8A GB9526377D0 (en) | 1995-12-22 | 1995-12-22 | Novel compounds |
| GBGB9605868.0A GB9605868D0 (en) | 1996-03-20 | 1996-03-20 | Novel compounds |
| GB9605868 | 1996-03-20 | ||
| GB9611898 | 1996-06-07 | ||
| GBGB9611898.9A GB9611898D0 (en) | 1996-06-07 | 1996-06-07 | Quinolones and their therapeutic use |
| PCT/GB1996/001862 WO1997004779A1 (en) | 1995-08-02 | 1996-08-02 | Quinolones and their therapeutic use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69628019D1 DE69628019D1 (de) | 2003-06-12 |
| DE69628019T2 true DE69628019T2 (de) | 2004-01-22 |
Family
ID=27451319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69628019T Expired - Fee Related DE69628019T2 (de) | 1995-08-02 | 1996-08-02 | Chinolone und deren therapeutische verwendung |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5891878A (enExample) |
| EP (1) | EP0841929B1 (enExample) |
| JP (1) | JPH11513021A (enExample) |
| AT (1) | ATE239477T1 (enExample) |
| AU (1) | AU696390B2 (enExample) |
| CA (1) | CA2225552A1 (enExample) |
| DE (1) | DE69628019T2 (enExample) |
| DK (1) | DK0841929T3 (enExample) |
| ES (1) | ES2193252T3 (enExample) |
| MX (1) | MX9800922A (enExample) |
| PT (1) | PT841929E (enExample) |
| WO (1) | WO1997004779A1 (enExample) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6077850A (en) * | 1997-04-21 | 2000-06-20 | G.D. Searle & Co. | Substituted benzopyran analogs for the treatment of inflammation |
| IT1296985B1 (it) | 1997-12-19 | 1999-08-03 | Zambon Spa | Derivati benzazinici inibitori della fosfodiesterasi 4 |
| ATE303993T1 (de) * | 1997-12-22 | 2005-09-15 | Pharmacia & Upjohn Co Llc | 4-hydroxychinolin-3-carboxamide und hydrazide als antivirale wirkstoffe |
| IT1302677B1 (it) | 1998-10-15 | 2000-09-29 | Zambon Spa | Derivati benzazinici inibitori della fosfodiesterasi 4 |
| US6248736B1 (en) * | 1999-01-08 | 2001-06-19 | Pharmacia & Upjohn Company | 4-oxo-1,4-dihydro-3-quinolinecarboxamides as antiviral agents |
| US6248739B1 (en) * | 1999-01-08 | 2001-06-19 | Pharmacia & Upjohn Company | Quinolinecarboxamides as antiviral agents |
| HRP20020158B1 (en) | 1999-08-21 | 2007-08-31 | Altana Pharma Ag | Action of synergistic combination |
| US6436971B2 (en) * | 2000-02-09 | 2002-08-20 | Smithkline Beecham Corporation | Use of PDE 4-specific inhibitors to reduce the severity of a bacterial infection after a respiratory viral infection |
| SI1265873T1 (en) | 2000-03-21 | 2004-02-29 | Pharmacia & Upjohn Company | 4-oxo-1,4-dihydro-3-cinnolinecarboxamides as antiviral agents |
| AU2001243240A1 (en) | 2000-03-21 | 2001-10-15 | Pharmacia And Upjohn Company Llc | 4-oxo-1,4-dihydro(1,8)naphthyridine-3-carboxamides as antiviral agents |
| CN1398258A (zh) | 2000-03-21 | 2003-02-19 | 法玛西雅厄普约翰美国公司 | 用作抗病毒剂的4－羟基噌啉－3－甲酰胺化合物 |
| HK1054037A1 (zh) | 2000-03-21 | 2003-11-14 | 法玛西雅厄普约翰美国公司 | 作为抗病毒剂的4-羟基-1，8-二氮杂萘-3-羧酰胺 |
| PE20011349A1 (es) * | 2000-06-16 | 2002-01-19 | Upjohn Co | 1-aril-4-oxo-1,4-dihidro-3-quinolincarboxamidas como agentes antivirales |
| US6730682B2 (en) * | 2000-07-12 | 2004-05-04 | Pharmacia & Upjohn Company | Heterocycle carboxamides as antiviral agents |
| US6559145B2 (en) | 2000-07-12 | 2003-05-06 | Pharmacia & Upjohn Company | Heterocycle carboxamides as antiviral agents |
| US6562822B2 (en) | 2000-07-12 | 2003-05-13 | Pharmacia & Upjohn Company | Heterocyle carboxamides as antiviral agents |
| PE20020856A1 (es) | 2001-02-13 | 2002-11-11 | Aventis Pharma Gmbh | 1,2,3,4-tetrahidronaftil aminas aciladas |
| TWI243164B (en) | 2001-02-13 | 2005-11-11 | Aventis Pharma Gmbh | Acylated indanyl amines and their use as pharmaceuticals |
| CA2433467A1 (en) | 2001-03-01 | 2002-09-12 | Joseph W. Strohbach | Substituted quinolinecarboxamides as antiviral agents |
| BR0212829A (pt) * | 2001-09-26 | 2004-08-03 | Bayer Pharmaceuticals Corp | Derivados de 1,8-naftiridina e seu uso para tratar diabetes e distúrbios relacionados |
| US7186707B2 (en) * | 2002-04-01 | 2007-03-06 | University Of Florida | Prodrugs for use as ophthalmic agents |
| WO2003084978A1 (en) * | 2002-04-01 | 2003-10-16 | University Of Florida | Steroidal quinols as prodrugs of antioxidants |
| US7300926B2 (en) * | 2002-04-01 | 2007-11-27 | University Of Florida Research Foundation, Inc. | Steroidal quinols and their use for estrogen replacement therapy |
| US20070213310A1 (en) * | 2002-04-01 | 2007-09-13 | Laszlo Prokai | Prodrugs for Use as Ophthalmic Agents |
| EP1569648A4 (en) * | 2002-12-09 | 2006-10-04 | Univ Florida | PRODRUGS FOR OPHTHALMIKA |
| EP1624893A2 (en) | 2003-04-01 | 2006-02-15 | Applied Research Systems ARS Holding N.V. | Inhibitors of phosphodiesterases in infertility |
| KR20060041254A (ko) | 2003-07-24 | 2006-05-11 | 아스텔라스세이야쿠 가부시키가이샤 | 퀴놀론 유도체 또는 그의 염 |
| DE102004004971B3 (de) * | 2004-01-31 | 2005-09-15 | Aventis Pharma Deutschland Gmbh | Cycloalkyl substituierte 7-Amino-4-chinolon-3-carbonsäure-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arnzeimittel |
| US7470706B2 (en) * | 2004-01-31 | 2008-12-30 | Sanofi-Aventis Deutschland Gmbh | Cycloalkyl-substituted 7-amino-4-quinolone-3-carboxylic acid derivatives, process for their preparation and their use as medicaments |
| JP4775259B2 (ja) | 2004-03-31 | 2011-09-21 | 味の素株式会社 | アニリン誘導体 |
| RU2525115C2 (ru) * | 2004-06-24 | 2014-08-10 | Вертекс Фармасьютикалз Инкорпорейтед | Способ модуляции транспортеров атф-связывающей кассеты |
| US8354427B2 (en) | 2004-06-24 | 2013-01-15 | Vertex Pharmaceutical Incorporated | Modulators of ATP-binding cassette transporters |
| PT1773816E (pt) * | 2004-06-24 | 2015-04-29 | Vertex Pharma | Moduladores de transportadores de cassete de ligação de atp |
| EP3216787B1 (en) * | 2004-06-24 | 2020-02-19 | Vertex Pharmaceuticals Incorporated | Intermediates for the preparation of modulators of atp-binding cassette transporters |
| DE102004035203A1 (de) | 2004-07-21 | 2006-02-16 | Bayer Healthcare Ag | Substituierte Chinolone |
| DE102005030524A1 (de) | 2005-06-30 | 2007-01-18 | Aicuris Gmbh & Co. Kg | Substituierte Chinolone II |
| EP1979367A2 (en) * | 2005-12-24 | 2008-10-15 | Vertex Pharmaceuticals Incorporated | Quinolin-4-one derivatives as modulators of abc transporters |
| AU2006331565A1 (en) * | 2005-12-27 | 2007-07-05 | Vertex Pharmaceuticals Incorporated | Compounds useful in CFTR assays and methods therewith |
| RS55940B1 (sr) | 2005-12-28 | 2017-09-29 | Vertex Pharma | Čvrsti oblici n-[2,4-bis(1,1-dimetiletil)-5-hidroksifenil]-1,4-dihidro-4-oksohinolin-3-karboksamida |
| DE102006005861A1 (de) | 2006-02-09 | 2007-08-23 | Aicuris Gmbh & Co. Kg | Substituierte Chinolone III |
| JP5424480B2 (ja) * | 2006-03-13 | 2014-02-26 | 杏林製薬株式会社 | Ｇｓｋ−３インヒビターとしてのアミノキノロン |
| US12458635B2 (en) | 2008-08-13 | 2025-11-04 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| US20100074949A1 (en) | 2008-08-13 | 2010-03-25 | William Rowe | Pharmaceutical composition and administration thereof |
| PL2349263T3 (pl) | 2008-10-23 | 2014-11-28 | Vertex Pharma | Modulatory mukowiscydozowego regulatora przewodnictwa przezbłonowego |
| EP2821400B1 (en) | 2009-03-20 | 2017-09-27 | Vertex Pharmaceuticals Incorporated | Process for making modulators of cystic fibrosis transmembrane conductance regulator |
| US8802700B2 (en) | 2010-12-10 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| MX2014010253A (es) | 2012-02-27 | 2014-11-12 | Vertex Pharma | Composicion farmaceutica y administraciones de la misma. |
| GB201409044D0 (en) | 2014-05-21 | 2014-07-02 | Ucl Business Plc | New compounds |
| RU2749213C2 (ru) | 2014-10-07 | 2021-06-07 | Вертекс Фармасьютикалз Инкорпорейтед | Сокристаллы модуляторов регулятора трансмембранной проводимости при кистозном фиброзе |
| CN107998131B (zh) * | 2017-12-27 | 2019-09-24 | 湖北工业大学 | 芳香酯类化合物用于制备抗adv-7病毒药物 |
| CN111646941A (zh) * | 2020-07-17 | 2020-09-11 | 天津科技大学 | 一种磺酰胺类衍生物及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3524558A (en) * | 1967-03-30 | 1970-08-18 | American Mach & Foundry | Cargo loading means and method |
| US3524858A (en) * | 1967-05-18 | 1970-08-18 | Warner Lambert Pharmaceutical | 1,4 - dihydro-1-substituted alkyl-6,7-methylenedioxy - 4 - oxoquinoline-3-carboxylic acid |
| FR2564832B1 (fr) * | 1984-05-23 | 1987-05-15 | Panmedica Sa | Nouveaux n-acyl derives d'amino-acides et leurs esters, leur procede de preparation et medicaments les contenant |
| US4786644A (en) * | 1987-11-27 | 1988-11-22 | Hoechst-Roussel Pharmaceuticals Inc. | 1-aryl-3-quinolinecarboxamide |
| JPH02124871A (ja) * | 1988-07-27 | 1990-05-14 | Dainippon Pharmaceut Co Ltd | １位が置換された複素環式カルボン酸アミド誘導体 |
-
1996
- 1996-08-02 MX MX9800922A patent/MX9800922A/es not_active IP Right Cessation
- 1996-08-02 PT PT96925905T patent/PT841929E/pt unknown
- 1996-08-02 DE DE69628019T patent/DE69628019T2/de not_active Expired - Fee Related
- 1996-08-02 EP EP96925905A patent/EP0841929B1/en not_active Expired - Lifetime
- 1996-08-02 CA CA002225552A patent/CA2225552A1/en not_active Abandoned
- 1996-08-02 JP JP9507373A patent/JPH11513021A/ja not_active Ceased
- 1996-08-02 DK DK96925905T patent/DK0841929T3/da active
- 1996-08-02 AU AU66263/96A patent/AU696390B2/en not_active Ceased
- 1996-08-02 ES ES96925905T patent/ES2193252T3/es not_active Expired - Lifetime
- 1996-08-02 US US08/691,338 patent/US5891878A/en not_active Expired - Fee Related
- 1996-08-02 AT AT96925905T patent/ATE239477T1/de not_active IP Right Cessation
- 1996-08-02 WO PCT/GB1996/001862 patent/WO1997004779A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU696390B2 (en) | 1998-09-10 |
| ATE239477T1 (de) | 2003-05-15 |
| PT841929E (pt) | 2003-09-30 |
| ES2193252T3 (es) | 2003-11-01 |
| CA2225552A1 (en) | 1997-02-13 |
| US5891878A (en) | 1999-04-06 |
| AU6626396A (en) | 1997-02-26 |
| DK0841929T3 (da) | 2003-09-01 |
| JPH11513021A (ja) | 1999-11-09 |
| WO1997004779A1 (en) | 1997-02-13 |
| EP0841929A1 (en) | 1998-05-20 |
| DE69628019D1 (de) | 2003-06-12 |
| EP0841929B1 (en) | 2003-05-07 |
| MX9800922A (es) | 1998-05-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69628019T2 (de) | Chinolone und deren therapeutische verwendung | |
| DE69631423T2 (de) | Chinolone und deren therapeutische verwendung | |
| DE69721526T2 (de) | Benzofuran carboxamide und ihre therapeutische anwendung | |
| DE69723863T2 (de) | Chinoline und deren therapeutische verwendung | |
| DE60006823T2 (de) | Quinolin-derivate und deren verwendung als antibakterielle wirkstoffe | |
| DE60111498T2 (de) | Kondensierte imidazolderivate | |
| DE69118388T2 (de) | Substituierte bizyklische arylderivate mit selektiver leukotrien b4 antagonistischer wirkung | |
| DE69722656T2 (de) | Bicyclische arylcarboxamide und ihre therapeutische verwendung | |
| AU710876B2 (en) | Quinolones and their therapeutic use | |
| CZ296163B6 (cs) | Karboxyamidy chinolinu jako inhibitory TNF a inhibitory PDE-IV | |
| DE69722858T2 (de) | Intimale verdickungsinhibitoren | |
| DE69620458T2 (de) | Benzofuran-carboxamide und -sulfonamide | |
| DE69714265T2 (de) | Tetrahydrochinolinderivate als eaa antagonisten | |
| EP0129128A2 (de) | 2-Pyrimidinyl-l-piperazin-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE60016039T2 (de) | Verfahren und verbindungen für die hemmung von mrp1 | |
| DE69816290T2 (de) | Chinolin-4-carboxamidderivate als nk-2 und nk-3 rezeptor antagonisten | |
| EP0882046A1 (en) | Quinolones and their therapeutic use | |
| DE69622731T2 (de) | Tetrahydrochinoline als nmda antagonisten | |
| DE60107056T2 (de) | Benzoxazolderivate als tnf und pde iv inhibitoren | |
| US5792774A (en) | Quinolones and their therapeutic use | |
| DE69910568T2 (de) | Furopyridinderivate und ihre therapeutische verwendung | |
| DE69926776T2 (de) | Quinalozinon-derivate | |
| DE3542002A1 (de) | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7- (1-piperazinyl)-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel | |
| EP0717043B1 (de) | Verwendung von 1,2-überbrückten 1,4-Dihydropyridinen als selektive Kaliumkanalmodulatoren | |
| DE69128845T2 (de) | 4-[3-(4-Oxothiazoldinyl)]butynylamine, Verfahren zu deren Herstellung und ihre Verwendung als Medikament |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |