HRP980468A2 - Use of inhibitors of the sodium hydrogen exchange in the manufacture of a medicament for treating diseases cused by protozoa - Google Patents
Use of inhibitors of the sodium hydrogen exchange in the manufacture of a medicament for treating diseases cused by protozoaInfo
- Publication number
- HRP980468A2 HRP980468A2 HR19737463.8A HRP980468A HRP980468A2 HR P980468 A2 HRP980468 A2 HR P980468A2 HR P980468 A HRP980468 A HR P980468A HR P980468 A2 HRP980468 A2 HR P980468A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- substituted
- group
- zero
- atoms
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims description 33
- 239000003814 drug Substances 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 8
- 201000010099 disease Diseases 0.000 title claims description 7
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical group [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 title 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 548
- 229910052739 hydrogen Inorganic materials 0.000 claims description 536
- 239000001257 hydrogen Substances 0.000 claims description 507
- 239000000460 chlorine Substances 0.000 claims description 465
- 229910052731 fluorine Inorganic materials 0.000 claims description 462
- 229910052801 chlorine Inorganic materials 0.000 claims description 456
- 125000001424 substituent group Chemical group 0.000 claims description 439
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 394
- 125000004432 carbon atom Chemical group C* 0.000 claims description 389
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 355
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 323
- 229910052760 oxygen Inorganic materials 0.000 claims description 293
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 291
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 247
- 125000000217 alkyl group Chemical group 0.000 claims description 242
- -1 C5-C7-cycloalkyl Chemical group 0.000 claims description 239
- 239000001301 oxygen Substances 0.000 claims description 238
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 235
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 179
- 229910052717 sulfur Inorganic materials 0.000 claims description 179
- 150000002431 hydrogen Chemical class 0.000 claims description 151
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 144
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 135
- 229910052794 bromium Inorganic materials 0.000 claims description 132
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 92
- 150000003839 salts Chemical class 0.000 claims description 90
- 125000001624 naphthyl group Chemical group 0.000 claims description 79
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 70
- 229910052799 carbon Inorganic materials 0.000 claims description 68
- 229910052757 nitrogen Inorganic materials 0.000 claims description 66
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 63
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 61
- AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical compound NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 claims description 58
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 56
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 40
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 36
- 239000011593 sulfur Substances 0.000 claims description 35
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical group 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 239000011737 fluorine Substances 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 18
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 201000004792 malaria Diseases 0.000 claims description 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 14
- 108091006672 Sodium–hydrogen antiporter Proteins 0.000 claims description 13
- 150000001721 carbon Chemical group 0.000 claims description 13
- 229940079593 drug Drugs 0.000 claims description 13
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 12
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 12
- 150000001409 amidines Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000002883 imidazolyl group Chemical group 0.000 claims description 12
- 238000011321 prophylaxis Methods 0.000 claims description 12
- 125000005493 quinolyl group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 229910020587 CmF2m+1 Inorganic materials 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 230000001717 pathogenic effect Effects 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 206010023076 Isosporiasis Diseases 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 4
- 150000002357 guanidines Chemical class 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 230000000968 intestinal effect Effects 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 3
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
- 208000003495 Coccidiosis Diseases 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000006664 (C1-C3) perfluoroalkyl group Chemical group 0.000 claims description 2
- 125000006313 (C5-C8) alkyl group Chemical group 0.000 claims description 2
- ABSNGNUGFQIDDO-UHFFFAOYSA-N 2-benzylguanidine Chemical group NC(N)=NCC1=CC=CC=C1 ABSNGNUGFQIDDO-UHFFFAOYSA-N 0.000 claims description 2
- 206010001935 American trypanosomiasis Diseases 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 2
- 208000024699 Chagas disease Diseases 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- 206010035501 Plasmodium malariae infection Diseases 0.000 claims description 2
- 206010035503 Plasmodium vivax infection Diseases 0.000 claims description 2
- 201000005485 Toxoplasmosis Diseases 0.000 claims description 2
- 125000005872 benzooxazolyl group Chemical group 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical group COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000005413 thiopyridyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 19
- 102000050381 Na+/H+ exchanger Human genes 0.000 claims 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 6
- 150000007513 acids Chemical group 0.000 claims 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 5
- 125000003107 substituted aryl group Chemical group 0.000 claims 5
- 229910006069 SO3H Inorganic materials 0.000 claims 4
- 125000003435 aroyl group Chemical group 0.000 claims 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 3
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 229930016911 cinnamic acid Natural products 0.000 claims 2
- 235000013985 cinnamic acid Nutrition 0.000 claims 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims 2
- 125000004957 naphthylene group Chemical group 0.000 claims 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- DGUJKRSJPZVBKP-UHFFFAOYSA-N 2-[2-(4-hydroxyphenyl)-1H-benzimidazol-4-yl]guanidine Chemical compound N1C=2C(NC(=N)N)=CC=CC=2N=C1C1=CC=C(O)C=C1 DGUJKRSJPZVBKP-UHFFFAOYSA-N 0.000 claims 1
- YJSAWOJMCDFJFF-UHFFFAOYSA-N 3-chloro-n-(diaminomethylidene)-5-(trifluoromethyl)benzamide Chemical compound NC(=N)NC(=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 YJSAWOJMCDFJFF-UHFFFAOYSA-N 0.000 claims 1
- GZLSKGUQNOPNDT-UHFFFAOYSA-N 3-chloro-n-(diaminomethylidene)-5-pyrrol-1-ylbenzamide Chemical compound NC(=N)NC(=O)C1=CC(Cl)=CC(N2C=CC=C2)=C1 GZLSKGUQNOPNDT-UHFFFAOYSA-N 0.000 claims 1
- SAXWXAXJJZJOJR-UHFFFAOYSA-N 4-(3-chloroanilino)-n-(diaminomethylidene)-3-methylsulfonylbenzamide Chemical compound CS(=O)(=O)C1=CC(C(=O)NC(N)=N)=CC=C1NC1=CC=CC(Cl)=C1 SAXWXAXJJZJOJR-UHFFFAOYSA-N 0.000 claims 1
- CCQORBUUNVVMQX-UHFFFAOYSA-N 4-[4-(2-aminoethyl)phenoxy]-n-(diaminomethylidene)-3-methylsulfonylbenzamide Chemical compound CS(=O)(=O)C1=CC(C(=O)NC(N)=N)=CC=C1OC1=CC=C(CCN)C=C1 CCQORBUUNVVMQX-UHFFFAOYSA-N 0.000 claims 1
- CHAYMWGCXRGJIE-UHFFFAOYSA-N 4-[4-(2-aminoethyl)thiophen-2-yl]oxy-N-(diaminomethylidene)-3-(trifluoromethyl)benzamide Chemical compound NCCC=1C=C(SC1)OC1=C(C=C(C(=O)NC(=N)N)C=C1)C(F)(F)F CHAYMWGCXRGJIE-UHFFFAOYSA-N 0.000 claims 1
- AWYZLWBWZJMSRO-UHFFFAOYSA-N 4-[4-(2-aminoethylsulfonylmethyl)phenoxy]-n-(diaminomethylidene)-3-(trifluoromethyl)benzamide Chemical compound C1=CC(CS(=O)(=O)CCN)=CC=C1OC1=CC=C(C(=O)NC(N)=N)C=C1C(F)(F)F AWYZLWBWZJMSRO-UHFFFAOYSA-N 0.000 claims 1
- JPJZOXQIWWCTNG-UHFFFAOYSA-N 5-chloro-n-(diaminomethylidene)-1h-indole-2-carboxamide Chemical compound ClC1=CC=C2NC(C(=O)N=C(N)N)=CC2=C1 JPJZOXQIWWCTNG-UHFFFAOYSA-N 0.000 claims 1
- IBCABPCADXCOLB-UHFFFAOYSA-N 5-chloro-n-[(e)-n'-chlorocarbamimidoyl]-1h-indole-2-carboxamide Chemical compound ClC1=CC=C2NC(C(=O)N=C(NCl)N)=CC2=C1 IBCABPCADXCOLB-UHFFFAOYSA-N 0.000 claims 1
- HJVKYZZPKJMIRF-UHFFFAOYSA-N 5-chloro-n-[n'-(pyridin-4-ylmethyl)carbamimidoyl]-1h-indole-2-carboxamide Chemical compound C=1C2=CC(Cl)=CC=C2NC=1C(=O)N=C(N)NCC1=CC=NC=C1 HJVKYZZPKJMIRF-UHFFFAOYSA-N 0.000 claims 1
- XJHFSGPUVTXELK-UHFFFAOYSA-N 5-methoxy-n-(n'-propan-2-ylcarbamimidoyl)-1h-indole-2-carboxamide Chemical compound COC1=CC=C2NC(C(=O)N=C(N)NC(C)C)=CC2=C1 XJHFSGPUVTXELK-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 1
- 208000004554 Leishmaniasis Diseases 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000005024 alkenyl aryl group Chemical group 0.000 claims 1
- 125000005025 alkynylaryl group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- FZOCFRPFPKJHHP-UHFFFAOYSA-N benzyl n-(diaminomethylidene)carbamate Chemical class NC(N)=NC(=O)OCC1=CC=CC=C1 FZOCFRPFPKJHHP-UHFFFAOYSA-N 0.000 claims 1
- 244000309464 bull Species 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims 1
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
- XEHVFKKSDRMODV-UHFFFAOYSA-N ethynyl Chemical group C#[C] XEHVFKKSDRMODV-UHFFFAOYSA-N 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- WBCXYMNAMCHKSU-UHFFFAOYSA-N n-(diaminomethylidene)-1h-indene-1-carboxamide Chemical class C1=CC=C2C(C(=O)NC(=N)N)C=CC2=C1 WBCXYMNAMCHKSU-UHFFFAOYSA-N 0.000 claims 1
- XYVGHFKBGKPRSY-UHFFFAOYSA-N n-(diaminomethylidene)-3-(dimethylamino)-5-(trifluoromethyl)benzamide Chemical compound CN(C)C1=CC(C(=O)NC(N)=N)=CC(C(F)(F)F)=C1 XYVGHFKBGKPRSY-UHFFFAOYSA-N 0.000 claims 1
- GHMNMXQORGMTMD-UHFFFAOYSA-N n-(diaminomethylidene)-3-(dimethylamino)-5-pyrrol-1-ylbenzamide Chemical compound CN(C)C1=CC(C(=O)NC(N)=N)=CC(N2C=CC=C2)=C1 GHMNMXQORGMTMD-UHFFFAOYSA-N 0.000 claims 1
- GNWHPBNSCPRHHH-UHFFFAOYSA-N n-(diaminomethylidene)-3-[3-[3-(diaminomethylideneamino)-2-methyl-3-oxoprop-1-enyl]phenyl]-2-methylprop-2-enamide Chemical compound NC(N)=NC(=O)C(C)=CC1=CC=CC(C=C(C)C(=O)N=C(N)N)=C1 GNWHPBNSCPRHHH-UHFFFAOYSA-N 0.000 claims 1
- GJKVCAVODCYVDF-UHFFFAOYSA-N n-(diaminomethylidene)-3-phenyl-5-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC(C(=O)NC(=N)N)=CC(C=2C=CC=CC=2)=C1 GJKVCAVODCYVDF-UHFFFAOYSA-N 0.000 claims 1
- QIOROPMQLXMBLV-UHFFFAOYSA-N n-(diaminomethylidene)-4-fluoro-3-propan-2-yl-5-(trifluoromethyl)benzamide Chemical compound CC(C)C1=CC(C(=O)NC(N)=N)=CC(C(F)(F)F)=C1F QIOROPMQLXMBLV-UHFFFAOYSA-N 0.000 claims 1
- DXEMZMJZHWLWID-UHFFFAOYSA-N n-(diaminomethylidene)-4-phenylmethoxy-1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N=C(N)N)=CC2=C1OCC1=CC=CC=C1 DXEMZMJZHWLWID-UHFFFAOYSA-N 0.000 claims 1
- APOPAXUENTVHHC-UHFFFAOYSA-N n-(diaminomethylidene)naphthalene-1-carboxamide Chemical class C1=CC=C2C(C(=O)NC(=N)N)=CC=CC2=C1 APOPAXUENTVHHC-UHFFFAOYSA-N 0.000 claims 1
- OECMIBNCPUMKFU-UHFFFAOYSA-N n-(diaminomethylidene)naphthalene-2-carboxamide Chemical class C1=CC=CC2=CC(C(=O)N=C(N)N)=CC=C21 OECMIBNCPUMKFU-UHFFFAOYSA-N 0.000 claims 1
- RIMHNNQOMAYNHT-UHFFFAOYSA-N n-[amino-(phenylsulfanylamino)methylidene]-5-chloro-1h-indole-2-carboxamide Chemical compound C=1C2=CC(Cl)=CC=C2NC=1C(=O)N=C(N)NSC1=CC=CC=C1 RIMHNNQOMAYNHT-UHFFFAOYSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 231100000676 disease causative agent Toxicity 0.000 description 10
- 241000283690 Bos taurus Species 0.000 description 5
- 241000223960 Plasmodium falciparum Species 0.000 description 5
- 244000045947 parasite Species 0.000 description 5
- 201000008680 babesiosis Diseases 0.000 description 4
- 210000003743 erythrocyte Anatomy 0.000 description 4
- 210000005003 heart tissue Anatomy 0.000 description 4
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 241001494479 Pecora Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 229960003677 chloroquine Drugs 0.000 description 3
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 3
- 241000223836 Babesia Species 0.000 description 2
- 241000224483 Coccidia Species 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
- 241000222722 Leishmania <genus> Species 0.000 description 2
- 241000223929 Sarcocystidae Species 0.000 description 2
- 102000052126 Sodium-Hydrogen Exchangers Human genes 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- 241000223109 Trypanosoma cruzi Species 0.000 description 2
- 230000036770 blood supply Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910001415 sodium ion Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- 241000224482 Apicomplexa Species 0.000 description 1
- 241000223838 Babesia bovis Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241001490774 Cryptosporidiidae Species 0.000 description 1
- 241000205707 Cystoisospora belli Species 0.000 description 1
- 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 1
- 208000002476 Falciparum Malaria Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
- 229930182566 Gentamicin Natural products 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 208000013875 Heart injury Diseases 0.000 description 1
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 208000009182 Parasitemia Diseases 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- 241000224016 Plasmodium Species 0.000 description 1
- 201000011336 Plasmodium falciparum malaria Diseases 0.000 description 1
- 241000223821 Plasmodium malariae Species 0.000 description 1
- 241001505293 Plasmodium ovale Species 0.000 description 1
- 241000223810 Plasmodium vivax Species 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 208000006257 Rinderpest Diseases 0.000 description 1
- 241001473628 Sarcocystis suihominis Species 0.000 description 1
- 208000006775 Sarcocystosis Diseases 0.000 description 1
- 241000223777 Theileria Species 0.000 description 1
- 241000223779 Theileria parva Species 0.000 description 1
- 241000223997 Toxoplasma gondii Species 0.000 description 1
- 241001502500 Trichomonadida Species 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229960002518 gentamicin Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 229940118768 plasmodium malariae Drugs 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Tropical Medicine & Parasitology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19737463A DE19737463A1 (de) | 1997-08-28 | 1997-08-28 | Verwendung von Inhibitoren des Natrium-Wasserstoff-Austauschers zur Herstellung eines Arzneimittels zur Behandlung von Erkrankungen, die durch Protozoen verursacht werden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP980468A2 true HRP980468A2 (en) | 1999-06-30 |
Family
ID=7840411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR19737463.8A HRP980468A2 (en) | 1997-08-28 | 1998-08-27 | Use of inhibitors of the sodium hydrogen exchange in the manufacture of a medicament for treating diseases cused by protozoa |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6114393A (pl) |
| EP (1) | EP0901788A3 (pl) |
| JP (1) | JPH11171792A (pl) |
| KR (1) | KR100567144B1 (pl) |
| CN (1) | CN1244322C (pl) |
| AR (1) | AR013949A1 (pl) |
| AU (1) | AU738599B2 (pl) |
| BR (1) | BR9803243A (pl) |
| CA (1) | CA2246407A1 (pl) |
| CZ (1) | CZ296815B6 (pl) |
| DE (1) | DE19737463A1 (pl) |
| HK (1) | HK1018589A1 (pl) |
| HR (1) | HRP980468A2 (pl) |
| HU (1) | HU225583B1 (pl) |
| ID (1) | ID20794A (pl) |
| IL (1) | IL125946A0 (pl) |
| MY (1) | MY137406A (pl) |
| NO (1) | NO320368B1 (pl) |
| NZ (1) | NZ331566A (pl) |
| PL (1) | PL191267B1 (pl) |
| RU (1) | RU2225726C2 (pl) |
| SG (1) | SG74074A1 (pl) |
| SK (1) | SK285457B6 (pl) |
| TR (1) | TR199801669A2 (pl) |
| TW (1) | TW592690B (pl) |
| ZA (1) | ZA987781B (pl) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9224739D0 (en) * | 1992-11-26 | 1993-01-13 | Wellcome Found | Medicaments |
| CN1402632A (zh) * | 1999-12-23 | 2003-03-12 | 辉瑞产品公司 | 水凝胶驱动的药物剂型 |
| US7375138B2 (en) * | 2002-05-18 | 2008-05-20 | Sanofi-Aventis Deutschland Gmbh | Pentafluorosulfanylbenzoylguanidines, processes for their preparation, their use as medicaments or diagnostic aids, and medicaments comprising them |
| FR2840302B1 (fr) * | 2002-06-03 | 2004-07-16 | Aventis Pharma Sa | Derives d'isoindolones, procede de preparation et intermediaire de ce procede a titre de medicaments et compositions pharmaceutiques les renfermant |
| US6878748B2 (en) | 2002-06-13 | 2005-04-12 | Aventis Pharma Deutschland Gmbh | Fluorinated cycloalkyl-derivatized benzoylguanidines, process for their preparation, their uses as medicament, and medicament containing them |
| CA3069046A1 (en) * | 2017-07-04 | 2019-01-10 | Sanofi | Ethynyl compounds, their preparation and their therapeutic use for the treatment of malaria |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1336871A (en) * | 1970-01-02 | 1973-11-14 | Wellcome Found | Method for preparing biologically active substituted amidines |
| US4032655A (en) * | 1974-05-15 | 1977-06-28 | Bayer Aktiengesellschaft | Phenylguanidines useful as anthelmintic agents |
| US4088780A (en) * | 1974-05-15 | 1978-05-09 | Bayer Aktiengesellschaft | Substituted phenylguanidines and processes for their preparation and use |
| US4544670A (en) * | 1982-08-24 | 1985-10-01 | William H. Rorer, Inc. | Method of treating coccidiosis with acyl guanidines |
| DE3929582A1 (de) * | 1989-09-06 | 1991-03-07 | Hoechst Ag | Benzoylguanidine, verfahren zu ihrer herstellung, ihre verwendung als medikament sowie sie enthaltendes medikament |
| IN172842B (pl) * | 1990-05-17 | 1993-12-11 | Boots Pharmaceuticals Limited | |
| EP0617705B1 (en) * | 1991-11-22 | 1997-09-24 | Yeda Research And Development Company, Ltd. | Non-peptidic surrogates of the arg-gly-asp sequence and pharmaceutical compositions comprising them |
| CZ284456B6 (cs) * | 1992-02-15 | 1998-12-16 | Hoechst Aktiengesellschaft | Aminosubstituované benzoylguanidiny, způsob jejich přípravy, jejich použití jako léčiv a léčivo, které je obsahuje |
| GB9224739D0 (en) * | 1992-11-26 | 1993-01-13 | Wellcome Found | Medicaments |
| DE4318658A1 (de) * | 1993-06-04 | 1994-12-08 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4318756A1 (de) * | 1993-06-05 | 1994-12-08 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19502644A1 (de) * | 1995-01-28 | 1996-08-01 | Merck Patent Gmbh | 4-Amino-benzoylguanidin-Derivate |
| FR2734263B1 (fr) * | 1995-05-17 | 1997-06-20 | Fournier Ind & Sante | Analogues de la 15-deoxyspergualine, leur procede de preparation et leur utilisation en therapeutique |
| DE69631527T2 (de) * | 1995-06-07 | 2004-09-23 | Genaera Corp. | Aminosterinverbindungen als inhibitoren der natrium/proton-pump, pharmazeutische methoden und präparaten davon |
| DE19542306A1 (de) * | 1995-11-14 | 1997-05-15 | Hoechst Ag | Sulfonylamino-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
-
1997
- 1997-08-28 DE DE19737463A patent/DE19737463A1/de not_active Withdrawn
-
1998
- 1998-08-24 EP EP98115902A patent/EP0901788A3/de not_active Withdrawn
- 1998-08-26 TR TR1998/01669A patent/TR199801669A2/xx unknown
- 1998-08-26 NZ NZ331566A patent/NZ331566A/en unknown
- 1998-08-26 IL IL12594698A patent/IL125946A0/xx not_active IP Right Cessation
- 1998-08-26 CZ CZ0272998A patent/CZ296815B6/cs not_active IP Right Cessation
- 1998-08-26 SK SK1174-98A patent/SK285457B6/sk unknown
- 1998-08-26 ID IDP981166A patent/ID20794A/id unknown
- 1998-08-26 US US09/140,544 patent/US6114393A/en not_active Expired - Fee Related
- 1998-08-26 CA CA002246407A patent/CA2246407A1/en not_active Abandoned
- 1998-08-26 HU HU9801925A patent/HU225583B1/hu not_active IP Right Cessation
- 1998-08-26 AR ARP980104256A patent/AR013949A1/es unknown
- 1998-08-27 MY MYPI98003946A patent/MY137406A/en unknown
- 1998-08-27 KR KR1019980034759A patent/KR100567144B1/ko not_active IP Right Cessation
- 1998-08-27 BR BR9803243A patent/BR9803243A/pt not_active Application Discontinuation
- 1998-08-27 CN CNB981184928A patent/CN1244322C/zh not_active Expired - Fee Related
- 1998-08-27 HR HR19737463.8A patent/HRP980468A2/hr not_active Application Discontinuation
- 1998-08-27 AU AU81894/98A patent/AU738599B2/en not_active Ceased
- 1998-08-27 ZA ZA987781A patent/ZA987781B/xx unknown
- 1998-08-27 NO NO19983943A patent/NO320368B1/no unknown
- 1998-08-27 RU RU98116380/15A patent/RU2225726C2/ru not_active IP Right Cessation
- 1998-08-27 SG SG1998003335A patent/SG74074A1/en unknown
- 1998-08-27 JP JP10241376A patent/JPH11171792A/ja not_active Abandoned
- 1998-08-28 PL PL328265A patent/PL191267B1/pl not_active IP Right Cessation
- 1998-09-23 TW TW087114024A patent/TW592690B/zh not_active IP Right Cessation
-
1999
- 1999-07-28 HK HK99103255A patent/HK1018589A1/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU685742B2 (en) | N,N'-disubstituted guanidines and their use as excitatory amino acid antagonists | |
| US5093525A (en) | N,N'-disubstituted guanidines and their use as excitatory amino acid antagonists | |
| HRP980464A2 (en) | Combined pharmaceutical preparation containing a sodium-hydrogen exchanger inhibitor and a medicament for heart circulation diseases treatment | |
| KR20000016240A (ko) | 혈청 지질 정상화용 약제를 제조하기 위한 세포질 나트륨이온/수소 이온 교환체 억제제의 용도 | |
| HRP980468A2 (en) | Use of inhibitors of the sodium hydrogen exchange in the manufacture of a medicament for treating diseases cused by protozoa | |
| KR19990076802A (ko) | 호흡 자극용 약제를 제조하기 위한 세포성 na+/h+ 교환기(nhe) 억제제의 용도 | |
| CZ20012309A3 (cs) | Léčivo k potlačení orgánových dysfunkcí podmíněných stářím | |
| HRP980488A2 (en) | The use of a sodium-hydrogen exchanger inhibitor in the production of a medicine for the prevention of undesirable effects of substances to a heart | |
| HRP980521A2 (en) | THE USE OF Na+/H+ EXCHANGER INHIBITOR IN THE PRODUCTION OF A MEDICAMENT FOR TREATMENT OR PROPHYLAXIS OF DISEASES OF THE CENTRAL NERVOUS SYSTEM | |
| SK281559B6 (sk) | Kombinácia atovakvonu s proguanilom, jej použitie a farmaceutický prostriedok | |
| US7211696B2 (en) | Antileishmanial dinitroaniline sulfanomides with activity against parasite tubulin | |
| Maxwell et al. | A nonadrenergic musculotropic effect of 2-(cyclohexylamino)-ethylguanidine sulfate (SU-9707) in rabbit aortic strips | |
| JP2000500774A (ja) | 呼吸刺激のための医薬製造での細胞内Ｎａ▲上＋▼／Ｈ▲上＋▼交換物質（ＮＨＥ）の抑制剤の使用 | |
| DE19750498A1 (de) | Die Verwendung eines Inhibitors des Na+/H+-Austauschers zur Herstellung eines Medikaments zur Behandlung oder Prophylaxe von Erkrankungen des Zentralnervensystems |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| AIPI | Request for the grant of a patent on the basis of a substantive examination of a patent application | ||
| PNAN | Change of the applicant name, address/residence |
Owner name: AVENTIS PHARMA DEUTSCHLAND GMBH, DE |
|
| PNAN | Change of the applicant name, address/residence |
Owner name: SANOFI-AVENTIS DEUTSCHLAND GMBH, DE |
|
| ODBI | Application refused |