CA2238298A1 - Quinoline derivatives - Google Patents
Quinoline derivatives Download PDFInfo
- Publication number
- CA2238298A1 CA2238298A1 CA002238298A CA2238298A CA2238298A1 CA 2238298 A1 CA2238298 A1 CA 2238298A1 CA 002238298 A CA002238298 A CA 002238298A CA 2238298 A CA2238298 A CA 2238298A CA 2238298 A1 CA2238298 A1 CA 2238298A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- formula
- group
- compound
- amino
- 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.)
- Abandoned
Links
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 239000012453 solvate Substances 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 19
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract 3
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 3
- 239000003814 drug Substances 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- -1 cyano, carboxy Chemical group 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000000217 alkyl group Chemical group 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 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 230000027455 binding Effects 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000006413 ring segment Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 108010040716 Neurokinin-3 Receptors Proteins 0.000 claims description 2
- 102000002003 Neurokinin-3 Receptors Human genes 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 5
- 238000011282 treatment Methods 0.000 claims 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 239000005557 antagonist Substances 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 239000002746 neurokinin 2 receptor antagonist Substances 0.000 claims 2
- 239000002740 neurokinin 3 receptor antagonist Substances 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 108010040722 Neurokinin-2 Receptors Proteins 0.000 claims 1
- 102100037342 Substance-K receptor Human genes 0.000 claims 1
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical group ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 150
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 66
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 50
- 238000006243 chemical reaction Methods 0.000 description 48
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 42
- 238000005481 NMR spectroscopy Methods 0.000 description 32
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 32
- 239000008279 sol Substances 0.000 description 32
- 235000019439 ethyl acetate Nutrition 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
- 239000012043 crude product Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- 229910001868 water Inorganic materials 0.000 description 17
- 239000003480 eluent Substances 0.000 description 16
- 150000002500 ions Chemical class 0.000 description 16
- 239000012044 organic layer Substances 0.000 description 16
- 239000011780 sodium chloride Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 239000002253 acid Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- 241000282320 Panthera leo Species 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 229910017974 NH40H Inorganic materials 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 3
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 3
- 206010011224 Cough Diseases 0.000 description 3
- 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- RGVPOXRFEPSFGH-UHFFFAOYSA-N 1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol Chemical compound COC1=C(OC)C(OC)=CC(CC2C3=CC(O)=C(O)C=C3CCN2)=C1 RGVPOXRFEPSFGH-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 101000654298 Homo sapiens N-terminal kinase-like protein Proteins 0.000 description 2
- 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 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 102100031703 N-terminal kinase-like protein Human genes 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 102220079670 rs759826252 Human genes 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
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- QQXLDOJGLXJCSE-KNVOCYPGSA-N tropinone Chemical compound C1C(=O)C[C@H]2CC[C@@H]1N2C QQXLDOJGLXJCSE-KNVOCYPGSA-N 0.000 description 2
- HMHYXLVEFVGOPM-QKUYTOGTSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[2-[[(2s)-1-[[(2s)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1-oxo-3-phenylpropan-2-yl]-methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(3-carboxypropanoylamino)-4-oxobutan Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)N(C)C(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)CCC(O)=O)C1=CC=CC=C1 HMHYXLVEFVGOPM-QKUYTOGTSA-N 0.000 description 1
- KGLPWQKSKUVKMJ-UHFFFAOYSA-N 2,3-dihydrophthalazine-1,4-dione Chemical compound C1=CC=C2C(=O)NNC(=O)C2=C1 KGLPWQKSKUVKMJ-UHFFFAOYSA-N 0.000 description 1
- PAEXAIBDCHBNDC-UHFFFAOYSA-N 2-pyridin-4-ylacetic acid Chemical compound OC(=O)CC1=CC=NC=C1 PAEXAIBDCHBNDC-UHFFFAOYSA-N 0.000 description 1
- BPSNETAIJADFTO-UHFFFAOYSA-N 2-pyridinylacetic acid Chemical compound OC(=O)CC1=CC=CC=N1 BPSNETAIJADFTO-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- TYXBHWAYFSJVLY-UHFFFAOYSA-N 5-(cyclopropanecarbonyl)-6-(1h-indol-3-yl)-9-phenyl-8,9,10,11-tetrahydro-6h-benzo[b][1,4]benzodiazepin-7-one Chemical compound C=1NC2=CC=CC=C2C=1C1C(C(CC(C2)C=3C=CC=CC=3)=O)=C2NC2=CC=CC=C2N1C(=O)C1CC1 TYXBHWAYFSJVLY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- 206010003645 Atopy Diseases 0.000 description 1
- 241000003910 Baronia <angiosperm> Species 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 241000699802 Cricetulus griseus Species 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Pulmonology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT95MI002461 IT1276170B1 (it) | 1995-11-24 | 1995-11-24 | Derivati chinolinici |
| ITMI95A002461 | 1995-11-24 | ||
| IT96MI001689 IT1307331B1 (it) | 1996-08-02 | 1996-08-02 | Derivati chinolinici |
| ITMI96A001689 | 1996-08-02 |
Publications (1)
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|---|---|
| CA2238298A1 true CA2238298A1 (en) | 1997-06-19 |
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|---|---|---|---|
| CA002238298A Abandoned CA2238298A1 (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives |
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| NZ (1) | NZ323387A (enExample) |
| OA (1) | OA11010A (enExample) |
| PL (1) | PL326967A1 (enExample) |
| SK (1) | SK66798A3 (enExample) |
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| CA2119155C (en) * | 1991-10-18 | 1999-06-15 | Dennis Paul Phillion | Fungicides for the control of take-all disease of plants |
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| US7037922B1 (en) | 2000-03-10 | 2006-05-02 | Neurogen Corporation | Aryl fused 2,4-disubstituted pyridines: NK3 receptor ligands |
| ATE247652T1 (de) | 1999-03-29 | 2003-09-15 | Neurogen Corp | 4-substituierte chinolinderivate als nk-3 und/oder gaba(a) rezeptor liganden |
| AU4802500A (en) * | 1999-04-26 | 2000-11-10 | Neurogen Corporation | 2-aminoquinolinecarboxamides: neurokinin receptor ligands |
| WO2002083663A1 (en) * | 2001-04-11 | 2002-10-24 | Glaxosmithkline S.P.A. | Quinoline-4-carboxamide derivatives as nk-3 and nk-2 receptor antagonists |
| WO2002089802A2 (en) * | 2001-05-08 | 2002-11-14 | Schering Corporation | Use of neurokinin receptor antagonists to treat androgen-dependent diseases |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| BRPI0407071B8 (pt) | 2003-01-28 | 2021-05-25 | Ironwood Pharmaceuticals Inc | peptídeo purificado, seu método de produção e composição farmacêutica para o tratamento de distúrbios gastrointestinais |
| GB0303086D0 (en) * | 2003-02-11 | 2003-03-19 | Merck Sharp & Dohme | New compounds |
| GB0419192D0 (en) | 2004-08-27 | 2004-09-29 | Merck Sharp & Dohme | Therapeutic agents |
| SG155229A1 (en) * | 2004-11-09 | 2009-09-30 | Smithkline Beecham Corp | Glycogen phosphorylase inhibitor compounds and pharmaceutical compositions thereof |
| GB0425077D0 (en) * | 2004-11-12 | 2004-12-15 | Smithkline Beecham Corp | Novel compounds |
| GB0515580D0 (en) | 2005-07-29 | 2005-09-07 | Merck Sharp & Dohme | Therapeutic compounds |
| CN101282961A (zh) * | 2005-08-11 | 2008-10-08 | 阿斯利康(瑞典)有限公司 | 作为nk3受体调节剂的烷基吡啶基喹啉 |
| AR057130A1 (es) | 2005-09-21 | 2007-11-14 | Astrazeneca Ab | Quinolinas de alquilsulfoxido y una composicion farmaceutica |
| TW200804288A (en) | 2005-12-12 | 2008-01-16 | Astrazeneca Ab | Alkylsulphonamide quinolines |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| DK2170930T3 (da) | 2007-06-04 | 2012-11-05 | Synergy Pharmaceuticals Inc | Agonister af guanylatcyclase, anvendelige til behandlingen af gastrointestinale sygdomme, inflammation, cancer og andre sygdomme |
| JP2010540553A (ja) * | 2007-09-28 | 2010-12-24 | グラクソスミスクライン エルエルシー | グリコーゲンホスホリラーゼ阻害剤化合物及びその医薬組成物 |
| JP2010540552A (ja) * | 2007-09-28 | 2010-12-24 | グラクソスミスクライン エルエルシー | グリコーゲンホスホリラーゼ阻害剤化合物及びその医薬組成物 |
| EP2328910B1 (en) | 2008-06-04 | 2014-08-06 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| ES2624828T3 (es) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros |
| WO2018129556A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| ES2657938T3 (es) | 2008-12-31 | 2018-03-07 | Ardelyx, Inc. | Compuestos y métodos para inhibir el antipuerto mediado por NHE en el tratamiento de trastornos asociados a la retención de líquidos o a la sobrecarga de sales y trastornos del tracto gastrointestinal |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| EP2887964B1 (en) | 2012-08-21 | 2019-07-03 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| US10376481B2 (en) | 2012-08-21 | 2019-08-13 | Ardelyx, Inc. | Compounds and methods for inhibiting NHE-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| CA2905438A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| US9486494B2 (en) | 2013-03-15 | 2016-11-08 | Synergy Pharmaceuticals, Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| WO2014169094A2 (en) | 2013-04-12 | 2014-10-16 | Ardelyx, Inc | Nhe3-binding compounds and methods for inhibiting phosphate transport |
| WO2014170648A1 (en) | 2013-04-19 | 2014-10-23 | Astrazeneca Ab | A nk3 receptor antagonist compound (nk3ra) for use in a method for the treatment of polycystic ovary syndrome (pcos) |
| JP6606491B2 (ja) | 2013-06-05 | 2019-11-13 | シナジー ファーマシューティカルズ インコーポレイテッド | グアニル酸シクラーゼｃの超高純度アゴニスト、その作成および使用方法 |
| WO2017072629A1 (en) | 2015-10-29 | 2017-05-04 | Cadila Healthcare Limited | Pharmaceutical combination of nk3 receptor antagonist and biguanides |
| KR20240090875A (ko) | 2017-01-09 | 2024-06-21 | 알데릭스, 인코포레이티드 | 위장관 장애를 치료하는 데 유용한 화합물 |
| WO2018129557A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Inhibitors of nhe-mediated antiport |
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| FR2538388B1 (fr) * | 1982-12-24 | 1985-06-21 | Pharmuka Lab | Nouveaux derives de naphtalene- ou azanaphtalenecarboxamide, leurs procedes de preparation et leur utilisation comme medicaments |
| JPS6399057A (ja) * | 1986-06-27 | 1988-04-30 | Nippon Shinyaku Co Ltd | グリシン誘導体 |
| PL186665B1 (pl) * | 1994-05-27 | 2004-02-27 | Smithkline Beecham Spa | Pochodne chinoliny jako antagoniści receptorów NKtachykininy, sposób ich wytwarzania, kompozycja farmaceutyczna zawierająca pochodne chinoliny oraz ich zastosowanie |
| IT1270615B (it) * | 1994-07-14 | 1997-05-07 | Smithkline Beecham Farma | Uso di derivati di chinolina |
-
1996
- 1996-11-22 EP EP96941023A patent/EP0876347B1/en not_active Expired - Lifetime
- 1996-11-22 EA EA199800477A patent/EA002124B1/ru not_active IP Right Cessation
- 1996-11-22 AT AT96941023T patent/ATE289994T1/de not_active IP Right Cessation
- 1996-11-22 SK SK667-98A patent/SK66798A3/sk unknown
- 1996-11-22 AP APAP/P/1998/001237A patent/AP9801237A0/en unknown
- 1996-11-22 PL PL96326967A patent/PL326967A1/xx unknown
- 1996-11-22 JP JP9521658A patent/JP2000501104A/ja active Pending
- 1996-11-22 US US09/077,151 patent/US6277862B1/en not_active Expired - Fee Related
- 1996-11-22 TR TR1998/00924T patent/TR199800924T2/xx unknown
- 1996-11-22 CN CN96199753A patent/CN1207730A/zh active Pending
- 1996-11-22 WO PCT/EP1996/005203 patent/WO1997021680A1/en not_active Ceased
- 1996-11-22 NZ NZ323387A patent/NZ323387A/en unknown
- 1996-11-22 CZ CZ981579A patent/CZ157998A3/cs unknown
- 1996-11-22 BR BR9611820A patent/BR9611820A/pt not_active Application Discontinuation
- 1996-11-22 KR KR1019980703873A patent/KR19990071597A/ko not_active Withdrawn
- 1996-11-22 ES ES96941023T patent/ES2236757T3/es not_active Expired - Lifetime
- 1996-11-22 IL IL12452296A patent/IL124522A0/xx unknown
- 1996-11-22 DE DE69634416T patent/DE69634416T2/de not_active Expired - Fee Related
- 1996-11-22 CA CA002238298A patent/CA2238298A1/en not_active Abandoned
- 1996-11-23 TW TW085114500A patent/TW353066B/zh active
- 1996-11-25 AR ARP960105317A patent/AR004972A1/es not_active Application Discontinuation
-
1997
- 1997-09-30 UY UY24733A patent/UY24733A1/es not_active Application Discontinuation
-
1998
- 1998-05-22 NO NO19982331A patent/NO311212B1/no unknown
- 1998-05-22 OA OA9800061A patent/OA11010A/en unknown
- 1998-05-22 MX MX9804107A patent/MX9804107A/es unknown
- 1998-06-18 BG BG102558A patent/BG102558A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EA002124B1 (ru) | 2001-12-24 |
| PL326967A1 (en) | 1998-11-09 |
| DE69634416T2 (de) | 2005-12-29 |
| UY24733A1 (es) | 2001-08-27 |
| EA199800477A1 (ru) | 1998-12-24 |
| KR19990071597A (ko) | 1999-09-27 |
| IL124522A0 (en) | 1998-12-06 |
| NO982331D0 (no) | 1998-05-22 |
| DE69634416D1 (de) | 2005-04-07 |
| NO311212B1 (no) | 2001-10-29 |
| WO1997021680A1 (en) | 1997-06-19 |
| OA11010A (en) | 2003-03-06 |
| ES2236757T3 (es) | 2005-07-16 |
| US6277862B1 (en) | 2001-08-21 |
| CN1207730A (zh) | 1999-02-10 |
| ATE289994T1 (de) | 2005-03-15 |
| JP2000501104A (ja) | 2000-02-02 |
| EP0876347A1 (en) | 1998-11-11 |
| AP9801237A0 (en) | 1998-06-30 |
| MX9804107A (es) | 1998-09-30 |
| BG102558A (bg) | 1999-03-31 |
| BR9611820A (pt) | 1999-07-13 |
| NZ323387A (en) | 2000-02-28 |
| SK66798A3 (en) | 1999-01-11 |
| AR004972A1 (es) | 1999-04-07 |
| EP0876347B1 (en) | 2005-03-02 |
| TR199800924T2 (xx) | 1998-08-21 |
| CZ157998A3 (cs) | 1998-12-16 |
| NO982331L (no) | 1998-07-22 |
| TW353066B (en) | 1999-02-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |