CA2458035C - Quaternary ammonium salts of omega-aminoalkylamides of r-2-aryl-propionic acids and pharmaceutical compositions containing them - Google Patents
Quaternary ammonium salts of omega-aminoalkylamides of r-2-aryl-propionic acids and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- CA2458035C CA2458035C CA2458035A CA2458035A CA2458035C CA 2458035 C CA2458035 C CA 2458035C CA 2458035 A CA2458035 A CA 2458035A CA 2458035 A CA2458035 A CA 2458035A CA 2458035 C CA2458035 C CA 2458035C
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- group
- propionylamino
- iodide
- methyl
- 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
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 238000000034 method Methods 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 210000001616 monocyte Anatomy 0.000 claims abstract description 6
- 230000007170 pathology Effects 0.000 claims abstract description 5
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims abstract description 4
- 206010009900 Colitis ulcerative Diseases 0.000 claims abstract description 4
- 206010016654 Fibrosis Diseases 0.000 claims abstract description 4
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims abstract description 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims abstract description 4
- 208000027418 Wounds and injury Diseases 0.000 claims abstract description 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims abstract description 4
- 230000006378 damage Effects 0.000 claims abstract description 4
- 230000004761 fibrosis Effects 0.000 claims abstract description 4
- 208000014674 injury Diseases 0.000 claims abstract description 4
- 208000028867 ischemia Diseases 0.000 claims abstract description 4
- 210000000440 neutrophil Anatomy 0.000 claims abstract description 4
- 230000002265 prevention Effects 0.000 claims abstract description 4
- 230000010410 reperfusion Effects 0.000 claims abstract description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 3
- 201000003883 Cystic fibrosis Diseases 0.000 claims abstract description 3
- 206010034277 Pemphigoid Diseases 0.000 claims abstract description 3
- 230000001684 chronic effect Effects 0.000 claims abstract description 3
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 3
- 230000000968 intestinal effect Effects 0.000 claims abstract description 3
- 206010018367 Glomerulonephritis chronic Diseases 0.000 claims abstract 2
- 241000721454 Pemphigus Species 0.000 claims abstract 2
- -1 C3-C6-alkynyl Chemical group 0.000 claims description 68
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 230000035605 chemotaxis Effects 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- DTYCLCKCZXMPME-UHFFFAOYSA-N propanamide hydroiodide Chemical compound CCC(N)=O.I DTYCLCKCZXMPME-UHFFFAOYSA-N 0.000 claims description 7
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 5
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- MITFXPHMIHQXPI-UHFFFAOYSA-N Oraflex Chemical compound N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- HBPSMMXRESDUSG-UHFFFAOYSA-N piperidine;hydroiodide Chemical compound I.C1CCNCC1 HBPSMMXRESDUSG-UHFFFAOYSA-N 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- YEVPPETYWLJSBU-VEIFNGETSA-N (2r)-2-(3-benzoylphenyl)-n-[3-(1-methylpiperidin-1-ium-1-yl)propyl]propanamide;iodide Chemical compound [I-].O=C([C@H](C)C=1C=C(C=CC=1)C(=O)C=1C=CC=CC=1)NCCC[N+]1(C)CCCCC1 YEVPPETYWLJSBU-VEIFNGETSA-N 0.000 claims description 2
- RJMIEHBSYVWVIN-LLVKDONJSA-N (2r)-2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]propanoic acid Chemical compound C1=CC([C@H](C(O)=O)C)=CC=C1N1C(=O)C2=CC=CC=C2C1 RJMIEHBSYVWVIN-LLVKDONJSA-N 0.000 claims description 2
- CQECGMFUMPDYPA-FSRHSHDFSA-N (2r)-n-[3-(1-methylpiperidin-1-ium-1-yl)propyl]-2-[4-(2-methylpropyl)phenyl]propanamide;iodide Chemical compound [I-].C1=CC(CC(C)C)=CC=C1[C@@H](C)C(=O)NCCC[N+]1(C)CCCCC1 CQECGMFUMPDYPA-FSRHSHDFSA-N 0.000 claims description 2
- IUISTMZCVYVSRL-GMUIIQOCSA-N (2r)-n-[3-(4-methylmorpholin-4-ium-4-yl)propyl]-2-[4-(2-methylpropyl)phenyl]propanamide;iodide Chemical compound [I-].C1=CC(CC(C)C)=CC=C1[C@@H](C)C(=O)NCCC[N+]1(C)CCOCC1 IUISTMZCVYVSRL-GMUIIQOCSA-N 0.000 claims description 2
- RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 claims description 2
- GUHPRPJDBZHYCJ-SECBINFHSA-N (2s)-2-(5-benzoylthiophen-2-yl)propanoic acid Chemical compound S1C([C@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CC=C1 GUHPRPJDBZHYCJ-SECBINFHSA-N 0.000 claims description 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 2
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 2
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 2
- MNKFLCYZIHOFRQ-UHFFFAOYSA-N 1-cyclohexyl-n,n-dimethylmethanamine Chemical compound CN(C)CC1CCCCC1 MNKFLCYZIHOFRQ-UHFFFAOYSA-N 0.000 claims description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- IQBGCARFBIPTJJ-FSRHSHDFSA-N 3-[[(2r)-2-(3-benzoylphenyl)propanoyl]amino]propyl-dimethyl-propan-2-ylazanium;iodide Chemical compound [I-].CC(C)[N+](C)(C)CCCNC(=O)[C@H](C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 IQBGCARFBIPTJJ-FSRHSHDFSA-N 0.000 claims description 2
- SNTRLALYUNHMAK-UNTBIKODSA-N 3-[[(2r)-2-(3-benzoylphenyl)propanoyl]amino]propyl-trimethylazanium;iodide Chemical compound [I-].C[N+](C)(C)CCCNC(=O)[C@H](C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 SNTRLALYUNHMAK-UNTBIKODSA-N 0.000 claims description 2
- DCHZLHDQGXJAAP-XFULWGLBSA-N 3-[[(2r)-2-[2-(2,6-dichloroanilino)phenyl]propanoyl]amino]propyl-trimethylazanium;methanesulfonate Chemical compound CS([O-])(=O)=O.C[N+](C)(C)CCCNC(=O)[C@H](C)C1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCHZLHDQGXJAAP-XFULWGLBSA-N 0.000 claims description 2
- ZVBRKKUDZPQBRZ-UNTBIKODSA-N 3-[[(2r)-2-[4-(cyclopentylmethyl)phenyl]propanoyl]amino]propyl-trimethylazanium;iodide Chemical compound [I-].C1=CC([C@H](C(=O)NCCC[N+](C)(C)C)C)=CC=C1CC1CCCC1 ZVBRKKUDZPQBRZ-UNTBIKODSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- KDTVWEHAAISPNW-UHFFFAOYSA-N 4-methylthiomorpholine Chemical compound CN1CCSCC1 KDTVWEHAAISPNW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 2
- SOWBFZRMHSNYGE-UHFFFAOYSA-N Monoamide-Oxalic acid Natural products NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims description 2
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 2
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 claims description 2
- TVQZAMVBTVNYLA-UHFFFAOYSA-N Pranoprofen Chemical compound C1=CC=C2CC3=CC(C(C(O)=O)C)=CC=C3OC2=N1 TVQZAMVBTVNYLA-UHFFFAOYSA-N 0.000 claims description 2
- MUXFZBHBYYYLTH-UHFFFAOYSA-N Zaltoprofen Chemical compound O=C1CC2=CC(C(C(O)=O)C)=CC=C2SC2=CC=CC=C21 MUXFZBHBYYYLTH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 229960004663 alminoprofen Drugs 0.000 claims description 2
- FPHLBGOJWPEVME-UHFFFAOYSA-N alminoprofen Chemical compound OC(=O)C(C)C1=CC=C(NCC(C)=C)C=C1 FPHLBGOJWPEVME-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229960005430 benoxaprofen Drugs 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- XWBIZYHDVFHTID-UHFFFAOYSA-M butyl(trimethyl)azanium;iodide Chemical compound [I-].CCCC[N+](C)(C)C XWBIZYHDVFHTID-UHFFFAOYSA-M 0.000 claims description 2
- 229960003184 carprofen Drugs 0.000 claims description 2
- IVUMCTKHWDRRMH-UHFFFAOYSA-N carprofen Chemical compound C1=CC(Cl)=C[C]2C3=CC=C(C(C(O)=O)C)C=C3N=C21 IVUMCTKHWDRRMH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- ITKDGNDHTCDLFN-ZMBIFBSDSA-N cyclohexylmethyl-dimethyl-[3-[[(2r)-2-[4-(2-methylpropyl)phenyl]propanoyl]amino]propyl]azanium;iodide Chemical compound [I-].C1=CC(CC(C)C)=CC=C1[C@@H](C)C(=O)NCCC[N+](C)(C)CC1CCCCC1 ITKDGNDHTCDLFN-ZMBIFBSDSA-N 0.000 claims description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 2
- UMSGVWVBUHUHEH-UHFFFAOYSA-M ethyl(trimethyl)azanium;bromide Chemical compound [Br-].CC[N+](C)(C)C UMSGVWVBUHUHEH-UHFFFAOYSA-M 0.000 claims description 2
- XMXGJNCYISPPDR-UNTBIKODSA-N ethyl-dimethyl-[3-[[(2r)-2-[4-(2-methylpropyl)phenyl]propanoyl]amino]propyl]azanium;iodide Chemical compound [I-].CC[N+](C)(C)CCCNC(=O)[C@H](C)C1=CC=C(CC(C)C)C=C1 XMXGJNCYISPPDR-UNTBIKODSA-N 0.000 claims description 2
- 229960001395 fenbufen Drugs 0.000 claims description 2
- ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 claims description 2
- 229960001419 fenoprofen Drugs 0.000 claims description 2
- 229960002390 flurbiprofen Drugs 0.000 claims description 2
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 claims description 2
- 229960001680 ibuprofen Drugs 0.000 claims description 2
- 229960004187 indoprofen Drugs 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims description 2
- 229960000991 ketoprofen Drugs 0.000 claims description 2
- 229960002373 loxoprofen Drugs 0.000 claims description 2
- YMBXTVYHTMGZDW-UHFFFAOYSA-N loxoprofen Chemical compound C1=CC(C(C(O)=O)C)=CC=C1CC1C(=O)CCC1 YMBXTVYHTMGZDW-UHFFFAOYSA-N 0.000 claims description 2
- CBATUQSECWXTQY-UHFFFAOYSA-N methanesulfonic acid propanamide Chemical compound CCC(N)=O.CS(O)(=O)=O CBATUQSECWXTQY-UHFFFAOYSA-N 0.000 claims description 2
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 claims description 2
- ISRXMEYARGEVIU-UHFFFAOYSA-N n-methyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C)C(C)C ISRXMEYARGEVIU-UHFFFAOYSA-N 0.000 claims description 2
- 229960002009 naproxen Drugs 0.000 claims description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229960000851 pirprofen Drugs 0.000 claims description 2
- PIDSZXPFGCURGN-UHFFFAOYSA-N pirprofen Chemical compound ClC1=CC(C(C(O)=O)C)=CC=C1N1CC=CC1 PIDSZXPFGCURGN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 229960003101 pranoprofen Drugs 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 2
- 229960001312 tiaprofenic acid Drugs 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 2
- UHRTUOQJNRWDMI-PKLMIRHRSA-N trimethyl-[3-[[(2r)-2-[4-(2-methylpropyl)phenyl]propanoyl]amino]propyl]azanium;iodide Chemical compound [I-].CC(C)CC1=CC=C([C@@H](C)C(=O)NCCC[N+](C)(C)C)C=C1 UHRTUOQJNRWDMI-PKLMIRHRSA-N 0.000 claims description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 2
- 229950004227 zaltoprofen Drugs 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- GHCVDAJWXCXGEN-UHFFFAOYSA-N CN(C)NC1CCCC1 Chemical compound CN(C)NC1CCCC1 GHCVDAJWXCXGEN-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene 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
- 150000004820 halides Chemical class 0.000 claims 1
- YZHIFLREQAZKAB-UNTBIKODSA-N methanesulfonate;(2r)-n-[3-(4-methylthiomorpholin-4-ium-4-yl)propyl]-2-(3-propan-2-ylphenyl)propanamide Chemical compound CS([O-])(=O)=O.CC(C)C1=CC=CC([C@@H](C)C(=O)NCCC[N+]2(C)CCSCC2)=C1 YZHIFLREQAZKAB-UNTBIKODSA-N 0.000 claims 1
- 230000000295 complement effect Effects 0.000 abstract description 3
- 230000030505 negative regulation of chemotaxis Effects 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 30
- 238000005160 1H NMR spectroscopy Methods 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229940080818 propionamide Drugs 0.000 description 9
- 101150041968 CDC13 gene Proteins 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 230000003399 chemotactic effect Effects 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 4
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000012981 Hank's balanced salt solution Substances 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
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- 239000000047 product Substances 0.000 description 1
- 150000004672 propanoic acids Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- 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]
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/40—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/44—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/51—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/76—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C235/78—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2001MI002025A ITMI20012025A1 (it) | 2001-09-28 | 2001-09-28 | Sali di ammonio quaternari di omega-amminoalchilammidi di acidi r 2-aril-propionici e composizioni farmaceutiche che li contengono |
| ITMI2001A002025 | 2001-09-28 | ||
| PCT/EP2002/010746 WO2003029187A1 (en) | 2001-09-28 | 2002-09-25 | Quaternary ammonium salts of omega-aminoalkylamides of r-2-aryl-propionic acids and pharmaceutical compositions containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2458035A1 CA2458035A1 (en) | 2003-04-10 |
| CA2458035C true CA2458035C (en) | 2011-04-12 |
Family
ID=11448449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2458035A Expired - Fee Related CA2458035C (en) | 2001-09-28 | 2002-09-25 | Quaternary ammonium salts of omega-aminoalkylamides of r-2-aryl-propionic acids and pharmaceutical compositions containing them |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7026510B2 (enExample) |
| EP (1) | EP1430020B1 (enExample) |
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| EP1457485A1 (en) * | 2003-03-14 | 2004-09-15 | Dompé S.P.A. | Sulfonic acids, their derivatives and pharmaceutical compositions containing them |
| WO2004091597A2 (en) * | 2003-04-15 | 2004-10-28 | Pharmacia & Upjohn Company Llc | Method of treating irritable bowel syndrome (ibs) |
| SI1776336T1 (sl) * | 2004-03-23 | 2010-01-29 | Dompe Spa | Derivati 2-fenilpropionske kisline in farmacevtski sestavki, ki jih vsebujejo |
| AU2005315591B2 (en) * | 2004-12-15 | 2011-03-17 | Dompe' Farmaceutici S.P.A. | 2-arylpropionic acid derivatives and pharmaceutical compositions containing them |
| EP1739078A1 (de) | 2005-05-30 | 2007-01-03 | Jerini AG | C5a-Rezeptor-Antagonisten |
| WO2008012605A1 (en) * | 2006-07-27 | 2008-01-31 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of ketoprofen and related compounds with very fast skin penetration rate |
| US20090238763A1 (en) | 2006-07-09 | 2009-09-24 | Chongxi Yu | High penetration compositions and uses thereof |
| WO2008010025A1 (en) * | 2006-07-18 | 2008-01-24 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of ibuprofen with very fast skin penetration rate |
| US20090221703A1 (en) | 2006-07-09 | 2009-09-03 | Chongxi Yu | High penetration composition and uses thereof |
| WO2008020270A1 (en) * | 2006-08-15 | 2008-02-21 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin penetration rate |
| CN104610077B (zh) * | 2006-07-27 | 2020-04-14 | 于崇曦 | 具有快速皮肤穿透速度的带正电荷的水溶性酮洛芬及相关化合物的前药 |
| CN103772258B (zh) * | 2006-08-08 | 2016-09-28 | 于崇曦 | 具有快速皮肤穿透速度的带正电荷的芳基和杂芳基乙酸类前药 |
| EP2990402A1 (en) * | 2006-08-08 | 2016-03-02 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of aryl- and heteroarylacetic acids with very fast skin penetration rate |
| CN103772259B (zh) * | 2006-08-08 | 2016-08-31 | 于崇曦 | 具有快速皮肤穿透速度的带正电荷的芳基和杂芳基乙酸类前药 |
| AU2013206218B2 (en) * | 2006-08-15 | 2016-06-30 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin penetration rate |
| KR20190091378A (ko) | 2007-06-04 | 2019-08-05 | 테크필즈 인크 | 매우 높은 피부 및 막 침투율을 가지는 비스테로이드성 소염제(ｎｓａｉａ) 약물전구체 및 이들의 새로운 의약적 용도 |
| DE602008005488D1 (de) * | 2007-10-18 | 2011-04-21 | Dompe Spa | (r)-4-(heteroaryl)phenylethylderivate und pharmazeutische zusammensetzungen damit |
| KR20210123406A (ko) | 2008-12-04 | 2021-10-13 | 충시 위 | 고투과력을 가진 조성물 및 이의 적용 |
| EP3508477B1 (en) | 2008-12-22 | 2021-11-10 | ChemoCentryx, Inc. | C5ar antagonists |
| EP3485881B1 (en) | 2009-07-10 | 2024-03-13 | President and Fellows of Harvard College | Permanently charged sodium and calcium channel blockers as anti-inflammatory agents |
| KR20130073822A (ko) * | 2011-12-23 | 2013-07-03 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 이온 액체, 비수 전해질 및 축전 장치 |
| JP5940036B2 (ja) * | 2013-10-08 | 2016-06-29 | テックフィールズ バイオケム カンパニー リミテッド | 非常に速い皮膚透過率を有するアリール−及びヘテロアリールプロピオン酸の正荷電水溶性プロドラッグ |
| US10100012B2 (en) * | 2014-05-30 | 2018-10-16 | Sphaera Pharma Pvt. Ltd. | Compounds as anti-tubercular agents |
| EP3200791B1 (en) | 2014-09-29 | 2020-04-22 | ChemoCentryx, Inc. | Processes and intermediates in the preparation of c5ar antagonists |
| CA2994545A1 (en) * | 2015-08-03 | 2017-02-09 | President And Fellows Of Harvard College | Charged ion channel blockers and methods for use |
| MA43872A (fr) | 2016-01-14 | 2021-05-19 | Chemocentryx Inc | Procédé de traitement d'une glomérulopathie à c3 |
| WO2017176620A2 (en) | 2016-04-04 | 2017-10-12 | Chemocentryx, Inc. | SOLUBLE C5aR ANTAGONISTS |
| CN111032658B (zh) | 2017-05-31 | 2022-12-20 | 凯莫森特里克斯股份有限公司 | 作为C5a抑制剂的5-5稠合环类 |
| JP7141130B2 (ja) | 2017-05-31 | 2022-09-22 | ケモセントリックス，インコーポレイティド | Ｃ５ａ阻害剤としての６－５融合環 |
| KR20200109298A (ko) | 2017-10-30 | 2020-09-22 | 케모센트릭스, 인크. | 면역조절제로서의 중수소화된 화합물 |
| SG11202005799XA (en) | 2017-12-22 | 2020-07-29 | Chemocentryx Inc | DIARYL SUBSTITUTED 5,5-FUSED RING COMPOUNDS AS C5aR INHIBITORS |
| MA51331A (fr) | 2017-12-22 | 2020-10-28 | Chemocentryx Inc | COMPOSÉS CYCLIQUES CONDENSÉS 6,5 À SUBSTITUTION DIARYLE, UTILISÉS EN TANT QU'INHIBITEURS DU C5aR |
| BR112020019822A2 (pt) | 2018-04-02 | 2021-03-16 | Chemocentryx, Inc. | Profármacos de antagonistas bicíclicos fundidos de c5ar |
| WO2020142657A1 (en) * | 2019-01-03 | 2020-07-09 | President And Fellows Of Harvard College | Charged ion channel blockers and methods for use thereof |
| US10828287B2 (en) | 2019-03-11 | 2020-11-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10780083B1 (en) | 2019-03-11 | 2020-09-22 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| WO2020185915A1 (en) | 2019-03-11 | 2020-09-17 | Nocion Therapeutics, Inc. | Ester substituted ion channel blockers and methods for use |
| AU2020237474C1 (en) | 2019-03-11 | 2025-09-18 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| CA3129111A1 (en) | 2019-03-11 | 2020-09-17 | Bridget M. Cole | Charged ion channel blockers and methods for use |
| KR102890953B1 (ko) | 2019-11-06 | 2025-11-24 | 녹시온 테라퓨틱스 인코포레이티드 | 하전된 이온 채널 차단제 및 사용 방법 |
| US10933055B1 (en) | 2019-11-06 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| WO2021183639A1 (en) | 2020-03-11 | 2021-09-16 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US12162851B2 (en) | 2020-03-11 | 2024-12-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
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| FR1593024A (enExample) * | 1968-09-18 | 1970-05-25 | ||
| IT1090782B (it) * | 1977-11-30 | 1985-06-26 | Menarini Sas | 2 4 bifenilil 2 dietilamino alchil propionamide suoi sali e procedimenti di fabbricazione relativi |
| RU2105554C1 (ru) * | 1997-06-24 | 1998-02-27 | Всероссийский научный центр по безопасности биологически активных веществ | N-(2,4,6-триметилфенилкарбамоилметил)-n-аллилморфолиний бромид, проявляющий противоишемическое и антиаритмическое действие при ишемической болезни сердца и способ его получения |
| IT1317826B1 (it) | 2000-02-11 | 2003-07-15 | Dompe Spa | Ammidi, utili nell'inibizione della chemiotassi dei neutrofiliindotta da il-8. |
| US20020160988A1 (en) * | 2001-02-20 | 2002-10-31 | Israel Institute For Biological Research | Compounds co-inducing cholinergic up-regulation and inflammation down-regulation and uses thereof |
| ITMI20010395A1 (it) * | 2001-02-27 | 2002-08-27 | Dompe Spa | Omega-amminoalchilammidi di acidi r-2-aril-propionici come inibitori della chemiotassi di cellule polimorfonucleate e mononucleate |
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2001
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- 2002-09-25 JP JP2003532442A patent/JP4405801B2/ja not_active Expired - Fee Related
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- 2002-09-25 RU RU2004113099/04A patent/RU2291857C2/ru not_active IP Right Cessation
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Also Published As
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| ES2573531T3 (es) | 2016-06-08 |
| PL214275B1 (pl) | 2013-07-31 |
| NO328879B1 (no) | 2010-06-07 |
| US20040266870A1 (en) | 2004-12-30 |
| EP1430020A1 (en) | 2004-06-23 |
| HU230541B1 (hu) | 2016-11-28 |
| NO20041609L (no) | 2004-04-20 |
| WO2003029187A1 (en) | 2003-04-10 |
| RU2291857C2 (ru) | 2007-01-20 |
| ITMI20012025A0 (it) | 2001-09-28 |
| CA2458035A1 (en) | 2003-04-10 |
| RU2004113099A (ru) | 2005-09-10 |
| CY1117657T1 (el) | 2017-05-17 |
| HUP0401763A3 (en) | 2006-01-30 |
| JP2005504121A (ja) | 2005-02-10 |
| EP1430020B1 (en) | 2016-03-02 |
| HUP0401763A2 (hu) | 2004-12-28 |
| PT1430020E (pt) | 2016-06-08 |
| US7026510B2 (en) | 2006-04-11 |
| AU2002338784B2 (en) | 2008-08-14 |
| ITMI20012025A1 (it) | 2003-03-28 |
| DK1430020T3 (en) | 2016-05-30 |
| SI1430020T1 (sl) | 2016-06-30 |
| PL369511A1 (en) | 2005-04-18 |
| JP4405801B2 (ja) | 2010-01-27 |
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