MXPA06007940A - Derivados de piridinio y quinolinio. - Google Patents
Derivados de piridinio y quinolinio.Info
- Publication number
- MXPA06007940A MXPA06007940A MXPA06007940A MXPA06007940A MXPA06007940A MX PA06007940 A MXPA06007940 A MX PA06007940A MX PA06007940 A MXPA06007940 A MX PA06007940A MX PA06007940 A MXPA06007940 A MX PA06007940A MX PA06007940 A MXPA06007940 A MX PA06007940A
- Authority
- MX
- Mexico
- Prior art keywords
- trifluoromethyl
- hydroxyl
- halogen
- optionally substituted
- alkoxy
- Prior art date
Links
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title claims description 16
- 150000003222 pyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 83
- 238000000034 method Methods 0.000 claims abstract description 21
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 13
- 150000003254 radicals Chemical class 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 13
- 150000002367 halogens Chemical group 0.000 claims description 13
- -1 hexafluorophosphate Chemical compound 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000006850 spacer group Chemical group 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 210000004072 lung Anatomy 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 230000002141 anti-parasite Effects 0.000 claims description 5
- 239000003096 antiparasitic agent Substances 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 230000000843 anti-fungal effect Effects 0.000 claims description 4
- 229940121375 antifungal agent Drugs 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 210000000481 breast Anatomy 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 230000000840 anti-viral effect Effects 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 210000004027 cell Anatomy 0.000 abstract description 17
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 102000002745 Choline Kinase Human genes 0.000 abstract description 6
- 108010018888 Choline kinase Proteins 0.000 abstract description 6
- 208000030852 Parasitic disease Diseases 0.000 abstract description 6
- 230000000903 blocking effect Effects 0.000 abstract description 4
- 201000010099 disease Diseases 0.000 abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
- 229950004354 phosphorylcholine Drugs 0.000 abstract description 4
- 210000004881 tumor cell Anatomy 0.000 abstract description 4
- 241000233866 Fungi Species 0.000 abstract description 3
- 241000700605 Viruses Species 0.000 abstract description 3
- 241001465754 Metazoa Species 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract 1
- YHHSONZFOIEMCP-UHFFFAOYSA-O phosphocholine Chemical compound C[N+](C)(C)CCOP(O)(O)=O YHHSONZFOIEMCP-UHFFFAOYSA-O 0.000 abstract 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 11
- 238000005406 washing Methods 0.000 description 11
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 8
- 231100000419 toxicity Toxicity 0.000 description 8
- 230000001988 toxicity Effects 0.000 description 8
- 108700020796 Oncogene Proteins 0.000 description 7
- 125000005997 bromomethyl group Chemical group 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- RAFYFUWHDWAUKS-UHFFFAOYSA-N 1-(bromomethyl)-3-[3-(bromomethyl)phenyl]benzene Chemical group BrCC1=CC=CC(C=2C=C(CBr)C=CC=2)=C1 RAFYFUWHDWAUKS-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 102000043276 Oncogene Human genes 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 4
- 230000003612 virological effect Effects 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 208000035143 Bacterial infection Diseases 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 208000031888 Mycoses Diseases 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 3
- 229960001231 choline Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- PYJNAPOPMIJKJZ-UHFFFAOYSA-N phosphorylcholine chloride Chemical compound [Cl-].C[N+](C)(C)CCOP(O)(O)=O PYJNAPOPMIJKJZ-UHFFFAOYSA-N 0.000 description 3
- PFZCOWLKXHIVII-UHFFFAOYSA-N pyridin-1-ium-1-amine Chemical group N[N+]1=CC=CC=C1 PFZCOWLKXHIVII-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 241000701161 unidentified adenovirus Species 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- 206010017533 Fungal infection Diseases 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 241000224016 Plasmodium Species 0.000 description 2
- 241000194017 Streptococcus Species 0.000 description 2
- 241000223104 Trypanosoma Species 0.000 description 2
- 208000036142 Viral infection Diseases 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- JQSWZKCFWIEBJL-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-n-methylpyridin-4-amine Chemical compound C=1C(Cl)=CC(Cl)=CC=1N(C)C1=CC=NC=C1 JQSWZKCFWIEBJL-UHFFFAOYSA-N 0.000 description 2
- PWQDNSSRMPSKAR-UHFFFAOYSA-N n-(4-chlorophenyl)-n-methylpyridin-4-amine Chemical compound C=1C=C(Cl)C=CC=1N(C)C1=CC=NC=C1 PWQDNSSRMPSKAR-UHFFFAOYSA-N 0.000 description 2
- PQJHOQWLZABWDM-UHFFFAOYSA-N n-(4-chlorophenyl)-n-methylquinolin-4-amine Chemical compound C=1C=NC2=CC=CC=C2C=1N(C)C1=CC=C(Cl)C=C1 PQJHOQWLZABWDM-UHFFFAOYSA-N 0.000 description 2
- 230000003071 parasitic effect Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- HMUGRILXVBKBID-UHFFFAOYSA-N 1-(bromomethyl)-4-[4-(bromomethyl)phenyl]benzene Chemical group C1=CC(CBr)=CC=C1C1=CC=C(CBr)C=C1 HMUGRILXVBKBID-UHFFFAOYSA-N 0.000 description 1
- ZFCCRPWNWOHZEN-UHFFFAOYSA-L 1-[[3-[3-[[4-(4-chloro-n-methylanilino)pyridin-1-ium-1-yl]methyl]phenyl]phenyl]methyl]-n-(4-chlorophenyl)-n-methylpyridin-1-ium-4-amine;dibromide Chemical compound [Br-].[Br-].C=1C=[N+](CC=2C=C(C=CC=2)C=2C=C(C[N+]=3C=CC(=CC=3)N(C)C=3C=CC(Cl)=CC=3)C=CC=2)C=CC=1N(C)C1=CC=C(Cl)C=C1 ZFCCRPWNWOHZEN-UHFFFAOYSA-L 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- XGAFCCUNHIMIRV-UHFFFAOYSA-N 4-chloropyridine;hydron;chloride Chemical compound Cl.ClC1=CC=NC=C1 XGAFCCUNHIMIRV-UHFFFAOYSA-N 0.000 description 1
- KNDOFJFSHZCKGT-UHFFFAOYSA-N 4-chloroquinoline Chemical compound C1=CC=C2C(Cl)=CC=NC2=C1 KNDOFJFSHZCKGT-UHFFFAOYSA-N 0.000 description 1
- RGHFOMWKDRGKOO-UHFFFAOYSA-N 7-chloro-n-(4-chlorophenyl)-n-methylquinolin-4-amine Chemical compound C=1C=NC2=CC(Cl)=CC=C2C=1N(C)C1=CC=C(Cl)C=C1 RGHFOMWKDRGKOO-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 208000005623 Carcinogenesis Diseases 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000699660 Mus musculus Species 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- 241000223960 Plasmodium falciparum Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000011712 cell development Effects 0.000 description 1
- 210000003855 cell nucleus Anatomy 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000001524 infective effect Effects 0.000 description 1
- 230000037041 intracellular level Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 208000037841 lung tumor Diseases 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- NOXDPLVCKHQSFW-UHFFFAOYSA-L n-methyl-1-[[3-[3-[[4-(n-methylanilino)pyridin-1-ium-1-yl]methyl]phenyl]phenyl]methyl]-n-phenylpyridin-1-ium-4-amine;dibromide Chemical compound [Br-].[Br-].C=1C=[N+](CC=2C=C(C=CC=2)C=2C=C(C[N+]=3C=CC(=CC=3)N(C)C=3C=CC=CC=3)C=CC=2)C=CC=1N(C)C1=CC=CC=C1 NOXDPLVCKHQSFW-UHFFFAOYSA-L 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 238000011580 nude mouse model Methods 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 208000023958 prostate neoplasm Diseases 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 108700042226 ras Genes Proteins 0.000 description 1
- 230000025053 regulation of cell proliferation Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000009758 senescence Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200400072A ES2237332B1 (es) | 2004-01-14 | 2004-01-14 | Derivados de piridinio y quinolinio. |
| PCT/ES2005/070002 WO2005068429A1 (es) | 2004-01-14 | 2005-01-11 | Derivados de piridinio y quinolinio |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06007940A true MXPA06007940A (es) | 2007-01-23 |
Family
ID=34778265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA06007940A MXPA06007940A (es) | 2004-01-14 | 2005-01-11 | Derivados de piridinio y quinolinio. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7781458B2 (enExample) |
| EP (2) | EP1710236B1 (enExample) |
| JP (2) | JP5047627B2 (enExample) |
| KR (1) | KR101157206B1 (enExample) |
| CN (1) | CN1910153B (enExample) |
| AT (1) | ATE461918T1 (enExample) |
| BR (1) | BRPI0506486A (enExample) |
| CA (1) | CA2553328C (enExample) |
| DE (1) | DE602005020112D1 (enExample) |
| DK (1) | DK1710236T3 (enExample) |
| ES (2) | ES2237332B1 (enExample) |
| MX (1) | MXPA06007940A (enExample) |
| PL (1) | PL1710236T3 (enExample) |
| PT (1) | PT1710236E (enExample) |
| WO (1) | WO2005068429A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8586613B2 (en) * | 2004-01-14 | 2013-11-19 | Universidad De Granada | Pyridinium and quinolinium derivatives |
| CA2729857A1 (en) | 2008-07-04 | 2010-01-07 | Traslational Cancer Drugs Pharma, S.L. | Methods for the treatment and diagnosis of cancer |
| US20100068302A1 (en) * | 2008-09-17 | 2010-03-18 | Traslational Cancer Drugs Pharma, S.L. | Methods and compositions for the treatment of cancer |
| US20110212994A1 (en) * | 2009-06-26 | 2011-09-01 | Brian Clem | Small Molecule Choline Kinase Inhibitors, Screening Assays, and Methods for Safe and Effective Treatment of Neoplastic Disorders |
| WO2012041493A1 (en) * | 2010-09-28 | 2012-04-05 | Julius-Maximilians-Universität Würzburg | Aminoquinolinium salts, methods of their production and their use as active agents for biotechnological and medical applications against binary toxins |
| EP2468259A1 (en) * | 2010-12-23 | 2012-06-27 | Traslational Cancer Drugs Pharma, S.L. | Pharmaceutical compositions of pyridinium and quinolinium derivatives |
| BR112013032857A2 (pt) | 2011-06-20 | 2017-01-24 | Traslational Cancer Drugs Pharma S L | método para prever a resposta clínica à quimioterapia em um indivíduo com câncer |
| EP2758395A1 (en) * | 2011-09-22 | 2014-07-30 | Vertex Pharmaceuticals Inc. | Compounds useful as inhibitors of choline kinase |
| ES2472367B1 (es) * | 2012-12-28 | 2015-06-02 | Universidad De Granada | Inhibidores no simétricos de colina quinasa con actividad antitumoral y antimalárica |
| WO2015028662A1 (en) | 2013-08-30 | 2015-03-05 | Consejo Superior De Investigaciones Cientificas (Csic) | Compositions and methods for characterization and amelioration of rheumatoid arthritis |
| ES2482290B1 (es) * | 2014-06-05 | 2015-05-19 | Universidad De Granada | Inhibidores polares simétricos de colina cinasa con actividad antitumoral |
| JP6920411B2 (ja) | 2016-07-25 | 2021-08-18 | ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ | コリンキナーゼ阻害剤としてのプリン及び３−デアザプリンアナログ |
| CN110997678B (zh) | 2017-07-11 | 2023-02-21 | 内尔维亚诺医疗科学公司 | 作为胆碱激酶抑制剂的吡唑并喹唑啉衍生物 |
| WO2025196502A1 (en) * | 2024-03-20 | 2025-09-25 | North Carolina Agricultural & Technical State University | Choline kinase inhibitors as a therapeutic treatment for obesity |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4206215A (en) * | 1976-02-25 | 1980-06-03 | Sterling Drug Inc. | Antimicrobial bis-[4-(substituted-amino)-1-pyridinium]alkanes |
| GB1533952A (en) * | 1976-02-25 | 1978-11-29 | Sterling Drug Inc | Anti-microbial bis-pyridinium compounds |
| FR2498187A1 (fr) * | 1981-01-16 | 1982-07-23 | Rhone Poulenc Sante | Procede de preparation d'amino-4 chloro-7 quinoleines |
| IL89026A (en) * | 1988-01-29 | 1993-02-21 | Lilly Co Eli | Substituted quinolines and cinnolines, process for their preparation and fungicidal, insecticidal and miticidal compositions containing them |
| ES2117950B1 (es) | 1996-08-02 | 1999-09-16 | Univ Granada | Nuevos compuestos que bloquean la biosintesis de fosforilcolina y su uso como segundo mensajero en proliferacion celular. |
-
2004
- 2004-01-14 ES ES200400072A patent/ES2237332B1/es not_active Expired - Fee Related
-
2005
- 2005-01-11 CN CN2005800024289A patent/CN1910153B/zh not_active Expired - Fee Related
- 2005-01-11 ES ES05708100T patent/ES2343418T3/es not_active Expired - Lifetime
- 2005-01-11 PL PL05708100T patent/PL1710236T3/pl unknown
- 2005-01-11 WO PCT/ES2005/070002 patent/WO2005068429A1/es not_active Ceased
- 2005-01-11 CA CA2553328A patent/CA2553328C/en not_active Expired - Fee Related
- 2005-01-11 PT PT05708100T patent/PT1710236E/pt unknown
- 2005-01-11 MX MXPA06007940A patent/MXPA06007940A/es active IP Right Grant
- 2005-01-11 DK DK05708100.2T patent/DK1710236T3/da active
- 2005-01-11 EP EP05708100A patent/EP1710236B1/en not_active Expired - Lifetime
- 2005-01-11 BR BRPI0506486-4A patent/BRPI0506486A/pt not_active IP Right Cessation
- 2005-01-11 US US10/597,095 patent/US7781458B2/en not_active Expired - Fee Related
- 2005-01-11 JP JP2006548321A patent/JP5047627B2/ja not_active Expired - Fee Related
- 2005-01-11 KR KR1020067016298A patent/KR101157206B1/ko not_active Expired - Fee Related
- 2005-01-11 DE DE602005020112T patent/DE602005020112D1/de not_active Expired - Lifetime
- 2005-01-11 EP EP09157208A patent/EP2085386A3/en not_active Withdrawn
- 2005-01-11 AT AT05708100T patent/ATE461918T1/de active
-
2012
- 2012-03-19 JP JP2012062569A patent/JP5619805B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1910153B (zh) | 2010-05-26 |
| BRPI0506486A (pt) | 2007-02-13 |
| DK1710236T3 (da) | 2010-07-12 |
| JP2012149077A (ja) | 2012-08-09 |
| ATE461918T1 (de) | 2010-04-15 |
| PT1710236E (pt) | 2010-06-18 |
| ES2343418T3 (es) | 2010-07-30 |
| CA2553328C (en) | 2012-05-15 |
| JP5047627B2 (ja) | 2012-10-10 |
| US20070185170A1 (en) | 2007-08-09 |
| EP1710236A1 (en) | 2006-10-11 |
| WO2005068429A1 (es) | 2005-07-28 |
| ES2237332B1 (es) | 2006-11-01 |
| EP2085386A2 (en) | 2009-08-05 |
| KR101157206B1 (ko) | 2012-07-06 |
| PL1710236T3 (pl) | 2010-08-31 |
| HK1100441A1 (en) | 2007-09-21 |
| ES2237332A1 (es) | 2005-07-16 |
| EP1710236B1 (en) | 2010-03-24 |
| KR20060110364A (ko) | 2006-10-24 |
| US7781458B2 (en) | 2010-08-24 |
| DE602005020112D1 (de) | 2010-05-06 |
| CA2553328A1 (en) | 2005-07-28 |
| JP5619805B2 (ja) | 2014-11-05 |
| EP2085386A3 (en) | 2009-10-28 |
| CN1910153A (zh) | 2007-02-07 |
| JP2007517837A (ja) | 2007-07-05 |
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