HU230541B1 - R-2-aril-propionsavak omega-aminoalkilamidjai kvaterner ammóniumsói és e vegyületeket tartalmazó gyógyszerészeti készítmények - Google Patents
R-2-aril-propionsavak omega-aminoalkilamidjai kvaterner ammóniumsói és e vegyületeket tartalmazó gyógyszerészeti készítmények Download PDFInfo
- Publication number
- HU230541B1 HU230541B1 HU0401763A HUP0401763A HU230541B1 HU 230541 B1 HU230541 B1 HU 230541B1 HU 0401763 A HU0401763 A HU 0401763A HU P0401763 A HUP0401763 A HU P0401763A HU 230541 B1 HU230541 B1 HU 230541B1
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- phenyl
- iodide
- group
- pro
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- -1 3-benzoylphenyl Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 16
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 150000004694 iodide salts Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 6
- 206010016654 Fibrosis Diseases 0.000 claims description 5
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 5
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 230000004761 fibrosis Effects 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 208000028867 ischemia Diseases 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 208000027418 Wounds and injury Diseases 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000006378 damage Effects 0.000 claims description 3
- 208000014674 injury Diseases 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 206010029897 Obsessive thoughts Diseases 0.000 claims description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 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
- 230000001684 chronic effect Effects 0.000 claims description 2
- 235000005911 diet Nutrition 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 230000010410 reperfusion Effects 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 241000721454 Pemphigus Species 0.000 claims 2
- OUCCVXVYGFBXSV-UHFFFAOYSA-N (4-chlorophenyl)sulfanylmethylsulfanyl-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCSC1=CC=C(Cl)C=C1 OUCCVXVYGFBXSV-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 1
- 241000009298 Trigla lyra Species 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
- 230000037213 diet Effects 0.000 claims 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-O dimethylaminium Chemical compound C[NH2+]C ROSDSFDQCJNGOL-UHFFFAOYSA-O 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 238000001665 trituration Methods 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 23
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000035605 chemotaxis Effects 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 210000003622 mature neutrocyte Anatomy 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 230000000295 complement effect Effects 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 230000003399 chemotactic effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229940080818 propionamide Drugs 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000012981 Hank's balanced salt solution Substances 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 229940098773 bovine serum albumin Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- AQOSPGCCTHGZFL-UHFFFAOYSA-N 1-(3a-hydroxy-7-methoxy-1,2,4,8b-tetrahydropyrrolo[2,3-b]indol-3-yl)ethanone Chemical compound COC1=CC=C2NC3(O)N(C(C)=O)CCC3C2=C1 AQOSPGCCTHGZFL-UHFFFAOYSA-N 0.000 description 1
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- 102000005590 Anaphylatoxin C5a Receptor Human genes 0.000 description 1
- 108010059426 Anaphylatoxin C5a Receptor Proteins 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000019034 Chemokines Human genes 0.000 description 1
- 108010012236 Chemokines Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 101000985278 Escherichia coli 5-carboxymethyl-2-hydroxymuconate Delta-isomerase Proteins 0.000 description 1
- 206010018498 Goitre Diseases 0.000 description 1
- 102100040448 Leukocyte cell-derived chemotaxin 1 Human genes 0.000 description 1
- 241000195908 Mnium Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241001597330 Septoria sii Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 208000000594 bullous pemphigoid Diseases 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 238000007705 chemical test Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- IABZFPLSDXDLRS-UHFFFAOYSA-N cyclohexylmethyl methanesulfonate Chemical compound CS(=O)(=O)OCC1CCCCC1 IABZFPLSDXDLRS-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 230000001434 glomerular Effects 0.000 description 1
- 201000003872 goiter Diseases 0.000 description 1
- 210000000224 granular leucocyte Anatomy 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 239000000815 hypotonic solution Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HEFNNWSXXWATRW-SNVBAGLBSA-N levibuprofen Chemical compound CC(C)CC1=CC=C([C@@H](C)C(O)=O)C=C1 HEFNNWSXXWATRW-SNVBAGLBSA-N 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 210000004088 microvessel Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002815 nickel Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000003362 replicative effect Effects 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
- 239000012137 tryptone Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
-
- 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pulmonology (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 (3)
| Publication Number | Publication Date |
|---|---|
| HUP0401763A2 HUP0401763A2 (hu) | 2004-12-28 |
| HUP0401763A3 HUP0401763A3 (en) | 2006-01-30 |
| HU230541B1 true HU230541B1 (hu) | 2016-11-28 |
Family
ID=11448449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0401763A HU230541B1 (hu) | 2001-09-28 | 2002-09-25 | R-2-aril-propionsavak omega-aminoalkilamidjai kvaterner ammóniumsói és e vegyületeket tartalmazó gyógyszerészeti készítmények |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7026510B2 (enExample) |
| EP (1) | EP1430020B1 (enExample) |
| JP (1) | JP4405801B2 (enExample) |
| AU (1) | AU2002338784B2 (enExample) |
| CA (1) | CA2458035C (enExample) |
| CY (1) | CY1117657T1 (enExample) |
| DK (1) | DK1430020T3 (enExample) |
| ES (1) | ES2573531T3 (enExample) |
| HU (1) | HU230541B1 (enExample) |
| IT (1) | ITMI20012025A1 (enExample) |
| NO (1) | NO328879B1 (enExample) |
| PL (1) | PL214275B1 (enExample) |
| PT (1) | PT1430020E (enExample) |
| RU (1) | RU2291857C2 (enExample) |
| SI (1) | SI1430020T1 (enExample) |
| WO (1) | WO2003029187A1 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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) |
| HRP20090681T1 (hr) * | 2004-03-23 | 2010-02-28 | Dompe' S.P.A. | Derivati 2-fenilpropionske kiseline i farmaceutski pripravci koji ih sadrže |
| KR101291483B1 (ko) * | 2004-12-15 | 2013-07-30 | 돔페 파르마 에스.피.에이. | 2-아릴프로피온산 유도체 및 이들을 함유하는 제약학적조성물 |
| EP1739078A1 (de) | 2005-05-30 | 2007-01-03 | Jerini AG | C5a-Rezeptor-Antagonisten |
| US20090238763A1 (en) | 2006-07-09 | 2009-09-24 | Chongxi Yu | High penetration compositions and uses thereof |
| US20090221703A1 (en) | 2006-07-09 | 2009-09-03 | Chongxi Yu | High penetration composition and uses thereof |
| HUE033687T2 (en) * | 2006-07-18 | 2017-12-28 | Techfields Biochem Co Ltd | Ibuprofen positively charged water soluble prodrugs with very fast skin penetration rates |
| 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 |
| CN101500984A (zh) * | 2006-07-27 | 2009-08-05 | 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 |
| 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 |
| 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 |
| PT2049482E (pt) * | 2006-08-08 | 2016-02-24 | Techfields Biochem Co Ltd | Profármacos solúveis em água carregados positivamente de ácidos aril- e heteroarilacéticos com velocidade de penetração na pele muito rápida |
| EP2054384A4 (en) * | 2006-08-15 | 2010-11-03 | Techfields Biochem Co Ltd | POSITIVELY LOADED WATER-SOLUBLE PRODRUGS OF ARYL AND HETEROARYLPROPIONIC ACIDS WITH A VERY FAST SKIN PUNCHING RATE |
| 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 |
| JP2010529101A (ja) | 2007-06-04 | 2010-08-26 | テックフィールズ インコーポレイテッド | 非常に速い皮膚及び膜浸透速度を有するｎｓａｉａプロドラッグ及びその新規医薬使用 |
| ES2361233T3 (es) * | 2007-10-18 | 2011-06-15 | Dompé S.p.A. | Derivados (r)-4-(heteroaril)feniletilo y composiciones farmacéuticas que los contienen. |
| CN108191846B (zh) | 2008-12-04 | 2021-08-20 | 于崇曦 | 高穿透性组合物及其应用 |
| JP5819730B2 (ja) | 2008-12-22 | 2015-11-24 | ケモセントリックス，インコーポレイティド | Ｃ５ａＲアンタゴニスト |
| WO2011006073A1 (en) | 2009-07-10 | 2011-01-13 | 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 |
| CN106659697B (zh) * | 2014-05-30 | 2022-03-29 | 斯菲叶尔制药私有公司 | 作为抗结核剂的化合物 |
| JP6898229B6 (ja) | 2014-09-29 | 2021-07-28 | ケモセントリックス，インコーポレイティド | Ｃ５ａＲアンタゴニスト製造における方法及び中間体 |
| US11021443B2 (en) * | 2015-08-03 | 2021-06-01 | President And Fellows Of Harvard College | Charged ion channel blockers and methods for use |
| SG11201805828YA (en) | 2016-01-14 | 2018-08-30 | Chemocentryx Inc | Method of treating c3 glomerulopathy |
| SG11201808625QA (en) | 2016-04-04 | 2018-10-30 | Chemocentryx Inc | SOLUBLE C5aR ANTAGONISTS |
| JP7141129B2 (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５－５融合環 |
| KR102638253B1 (ko) | 2017-05-31 | 2024-02-16 | 케모센트릭스, 인크. | C5a 억제제로서의 6-5 융합 고리 |
| CN111741754A (zh) | 2017-10-30 | 2020-10-02 | 凯莫森特里克斯股份有限公司 | 作为免疫调节剂的氘代化合物 |
| MX2020006459A (es) | 2017-12-22 | 2020-11-06 | Chemocentryx Inc | Compuestos de anillos fusionados 6,5 diaril sustituidos como inhibidores de c5ar. |
| MA51327A (fr) | 2017-12-22 | 2021-05-26 | Chemocentryx Inc | Composés cycliques fusionnés en 5,5 à substitution diaryle, utilisés en tant qu'inhibiteurs du c5ar |
| ES2993034T3 (en) | 2018-04-02 | 2024-12-20 | Chemocentryx Inc | Prodrugs of fused-bicyclic c5ar antagonists |
| WO2020142657A1 (en) * | 2019-01-03 | 2020-07-09 | President And Fellows Of Harvard College | Charged ion channel blockers and methods for use thereof |
| US10780083B1 (en) | 2019-03-11 | 2020-09-22 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US11377422B2 (en) | 2019-03-11 | 2022-07-05 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| CA3129089A1 (en) | 2019-03-11 | 2020-09-17 | Bridget Mccarthy Cole | Ester substituted ion channel blockers and methods for use |
| US10828287B2 (en) | 2019-03-11 | 2020-11-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| CN113811305A (zh) | 2019-03-11 | 2021-12-17 | 诺西恩医疗公司 | 带电的离子通道阻滞剂及其使用方法 |
| CA3155568A1 (en) | 2019-11-06 | 2021-05-14 | Bridget Mccarthy Cole | Charged ion channel blockers and methods for use |
| AU2020380118B2 (en) | 2019-11-06 | 2026-06-11 | 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 |
| US11332446B2 (en) | 2020-03-11 | 2022-05-17 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
2001
- 2001-09-28 IT IT2001MI002025A patent/ITMI20012025A1/it unknown
-
2002
- 2002-09-25 RU RU2004113099/04A patent/RU2291857C2/ru not_active IP Right Cessation
- 2002-09-25 DK DK02777207.8T patent/DK1430020T3/en active
- 2002-09-25 ES ES02777207.8T patent/ES2573531T3/es not_active Expired - Lifetime
- 2002-09-25 JP JP2003532442A patent/JP4405801B2/ja not_active Expired - Fee Related
- 2002-09-25 SI SI200231073A patent/SI1430020T1/sl unknown
- 2002-09-25 EP EP02777207.8A patent/EP1430020B1/en not_active Expired - Lifetime
- 2002-09-25 PL PL369511A patent/PL214275B1/pl unknown
- 2002-09-25 HU HU0401763A patent/HU230541B1/hu unknown
- 2002-09-25 US US10/487,679 patent/US7026510B2/en not_active Expired - Lifetime
- 2002-09-25 PT PT02777207T patent/PT1430020E/pt unknown
- 2002-09-25 AU AU2002338784A patent/AU2002338784B2/en not_active Ceased
- 2002-09-25 CA CA2458035A patent/CA2458035C/en not_active Expired - Fee Related
- 2002-09-25 WO PCT/EP2002/010746 patent/WO2003029187A1/en not_active Ceased
-
2004
- 2004-04-20 NO NO20041609A patent/NO328879B1/no not_active IP Right Cessation
-
2016
- 2016-05-27 CY CY20161100463T patent/CY1117657T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK1430020T3 (en) | 2016-05-30 |
| PL214275B1 (pl) | 2013-07-31 |
| RU2291857C2 (ru) | 2007-01-20 |
| SI1430020T1 (sl) | 2016-06-30 |
| US7026510B2 (en) | 2006-04-11 |
| NO20041609L (no) | 2004-04-20 |
| WO2003029187A1 (en) | 2003-04-10 |
| ITMI20012025A1 (it) | 2003-03-28 |
| CA2458035C (en) | 2011-04-12 |
| PL369511A1 (en) | 2005-04-18 |
| JP2005504121A (ja) | 2005-02-10 |
| EP1430020B1 (en) | 2016-03-02 |
| PT1430020E (pt) | 2016-06-08 |
| ES2573531T3 (es) | 2016-06-08 |
| CY1117657T1 (el) | 2017-05-17 |
| JP4405801B2 (ja) | 2010-01-27 |
| HUP0401763A2 (hu) | 2004-12-28 |
| US20040266870A1 (en) | 2004-12-30 |
| HUP0401763A3 (en) | 2006-01-30 |
| AU2002338784B2 (en) | 2008-08-14 |
| NO328879B1 (no) | 2010-06-07 |
| ITMI20012025A0 (it) | 2001-09-28 |
| CA2458035A1 (en) | 2003-04-10 |
| RU2004113099A (ru) | 2005-09-10 |
| EP1430020A1 (en) | 2004-06-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7026510B2 (en) | Quaternary ammonium salts of omega-aminoalkylamides of r-2-aryl-propionic acids and pharmaceutical compositions containing them | |
| ES2594614T3 (es) | Omega-aminoalquilamidas de ácidos R-2-arilpropiónicos como inhibidores del quimiotactismo de células polimorfonucleares y mononucleares | |
| JP5868948B2 (ja) | リジン特異的脱メチル化酵素１阻害薬およびその使用 | |
| DK2297120T3 (en) | Aminodihydrothiazine derivatives as bace inhibitors for the treatment of Alzheimer's disease | |
| AU2002338784A1 (en) | Quaternary ammonium salts of omega-aminoalkylamides of R-2-aryl-propionic acids and pharmaceutical compositions containing them | |
| CZ26297A3 (cs) | Arylthiolové sloučeniny jako antibakteriální a antivirová činidla | |
| KR100654328B1 (ko) | 피페라지닐알킬피라졸계 ｔ-타입 칼슘 채널 억제 화합물 및이의 제조방법 | |
| CN112805270B (zh) | 1-甲基-4-[(4-苯基苯基)磺酰甲基]环己醇和1-甲基-4-[[4-(2-吡啶基)苯基]磺酰甲基]环己醇化合物以及它们的治疗用途 | |
| JP2003528825A (ja) | ８ａ位で置換された８，８ａ−ジヒドロ−インデノ［１，２−ｄ］チアゾール誘導体、その製造方法及び医薬、例えば食欲抑制薬としてのその使用 | |
| JP5179190B2 (ja) | 神経変性疾病の治療において１，４−ビス（３−アミノアルキル）ピペラジン誘導体を使用する方法 | |
| EP0229370B1 (en) | Guanidinobenzoic ester derivative, a process for preparing same and pharmaceutical compositions containing same | |
| US20110065919A1 (en) | 5-Substituted Indol-3-Carboxylic Acid Derivatives Exhibiting Antiviral Activity a Method for the Production and Use Thereof | |
| HUP0104202A2 (hu) | Tiazol-származékok, eljárás az előállításukra és ezeket tartalmazó gyógyászati készítmények | |
| US7217707B2 (en) | Amide of R-2-(aminoaryl)-propionic acid for use in the prevention of leucocyte activation | |
| SK16222002A3 (sk) | Amidy (R)-enantiomérov 2-arylpropiónových kyselín, spôsob ich výroby, farmaceutický prostriedok s ich obsahom a ich použitie | |
| EP1663960A2 (en) | Amidines and derivatives thereof and pharmaceutical compositions containing them | |
| HK1069815B (en) | Omega-aminoalkylamides of r-2-aryl-propionic acids as inhibitors of the chemotaxis of polymorphonucleate and mononucleate cells | |
| HK1051035B (en) | Amides of r-2-(aminoaryl)-propionic acids for use in theprevention of leucocyte activation | |
| EP0265806A1 (en) | 2-(Substituted sulfamyl)-6-nitrobenzoic acids, amides and esters thereof useful as adjuncts to radiation therapy |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| GB9A | Succession in title |
Owner name: DOMPE PHA.R.MA S.P.A., IT Free format text: FORMER OWNER(S): DOMPE S.P.A., IT |
|
| GB9A | Succession in title |
Owner name: DOMPE FARMACEUTICI S.P.A., IT Free format text: FORMER OWNER(S): DOMPE S.P.A., IT; DOMPE PHA.R.MA S.P.A., IT |