ES2251995T3 - Compuestos farmaceuticos que contienen derivados de piridina o pirimidina para la inhibicion de produccion y secrecin de citoquinas. - Google Patents
Compuestos farmaceuticos que contienen derivados de piridina o pirimidina para la inhibicion de produccion y secrecin de citoquinas.Info
- Publication number
- ES2251995T3 ES2251995T3 ES00926142T ES00926142T ES2251995T3 ES 2251995 T3 ES2251995 T3 ES 2251995T3 ES 00926142 T ES00926142 T ES 00926142T ES 00926142 T ES00926142 T ES 00926142T ES 2251995 T3 ES2251995 T3 ES 2251995T3
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- amine
- pyridyl
- pentene
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 209
- 102000004127 Cytokines Human genes 0.000 title description 31
- 108090000695 Cytokines Proteins 0.000 title description 31
- 238000004519 manufacturing process Methods 0.000 title description 19
- 230000005764 inhibitory process Effects 0.000 title description 12
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 241000894007 species Species 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 208000030507 AIDS Diseases 0.000 claims description 4
- 206010006895 Cachexia Diseases 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 206010040047 Sepsis Diseases 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 208000002399 aphthous stomatitis Diseases 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 208000014674 injury Diseases 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 230000008733 trauma Effects 0.000 claims description 3
- 230000003612 virological effect Effects 0.000 claims description 3
- OKONKJZCUFNZOF-IWQZZHSRSA-N (z)-1,1,1-trifluoro-5-pyridin-3-ylpent-4-en-2-amine Chemical compound FC(F)(F)C(N)C\C=C/C1=CC=CN=C1 OKONKJZCUFNZOF-IWQZZHSRSA-N 0.000 claims description 2
- LRJBNZMEHQPINH-HYXAFXHYSA-N (z)-2-methyl-5-pyridin-3-ylpent-4-en-2-amine Chemical compound CC(C)(N)C\C=C/C1=CC=CN=C1 LRJBNZMEHQPINH-HYXAFXHYSA-N 0.000 claims description 2
- SMRNAYABIZGXAA-WAYWQWQTSA-N (z)-3-methyl-5-pyridin-3-ylpent-4-en-2-amine Chemical compound CC(N)C(C)\C=C/C1=CC=CN=C1 SMRNAYABIZGXAA-WAYWQWQTSA-N 0.000 claims description 2
- NWQWDVKTTVXDAK-NTMALXAHSA-N (z)-4-methyl-5-pyridin-3-ylpent-4-en-1-amine Chemical compound NCCCC(/C)=C\C1=CC=CN=C1 NWQWDVKTTVXDAK-NTMALXAHSA-N 0.000 claims description 2
- CHDSWCRTHLGIKG-CLFYSBASSA-N (z)-4-methyl-5-pyridin-3-ylpent-4-en-2-amine Chemical compound CC(N)C\C(C)=C/C1=CC=CN=C1 CHDSWCRTHLGIKG-CLFYSBASSA-N 0.000 claims description 2
- XSQFFUBHSNBOOI-NTMALXAHSA-N (z)-5-methyl-6-pyridin-3-ylhex-5-en-2-amine Chemical compound CC(N)CC\C(C)=C/C1=CC=CN=C1 XSQFFUBHSNBOOI-NTMALXAHSA-N 0.000 claims description 2
- DMKFUPLBEUFWTG-YFHOEESVSA-N (z)-5-methyl-6-pyridin-3-ylhex-5-en-3-amine Chemical compound CCC(N)C\C(C)=C/C1=CC=CN=C1 DMKFUPLBEUFWTG-YFHOEESVSA-N 0.000 claims description 2
- UWEZIEFFXYXCTQ-DJWKRKHSSA-N (z)-5-pyridin-3-ylpent-4-en-2-amine Chemical compound CC(N)C\C=C/C1=CC=CN=C1 UWEZIEFFXYXCTQ-DJWKRKHSSA-N 0.000 claims description 2
- DVKLSFIDWUOOLI-UTCJRWHESA-N (z)-6-pyridin-3-ylhex-5-en-2-amine Chemical compound CC(N)CC\C=C/C1=CC=CN=C1 DVKLSFIDWUOOLI-UTCJRWHESA-N 0.000 claims description 2
- UBQUHVNXMNZXMC-HYXAFXHYSA-N (z)-6-pyridin-3-ylhex-5-en-3-amine Chemical compound CCC(N)C\C=C/C1=CC=CN=C1 UBQUHVNXMNZXMC-HYXAFXHYSA-N 0.000 claims description 2
- CHTJZZLVNQDJDX-XQRVVYSFSA-N (z)-n,2-dimethyl-5-pyridin-3-ylpent-4-en-2-amine Chemical compound CNC(C)(C)C\C=C/C1=CC=CN=C1 CHTJZZLVNQDJDX-XQRVVYSFSA-N 0.000 claims description 2
- BJOOOCRHDUOKGE-SREVYHEPSA-N (z)-n,3-dimethyl-5-pyridin-3-ylpent-4-en-2-amine Chemical compound CNC(C)C(C)\C=C/C1=CC=CN=C1 BJOOOCRHDUOKGE-SREVYHEPSA-N 0.000 claims description 2
- YHQKIXRDSWTUJK-LUAWRHEFSA-N (z)-n,4-dimethyl-5-pyridin-3-ylpent-4-en-1-amine Chemical compound CNCCC\C(C)=C/C1=CC=CN=C1 YHQKIXRDSWTUJK-LUAWRHEFSA-N 0.000 claims description 2
- HUGUNCUQATWKMX-LUAWRHEFSA-N (z)-n,5-dimethyl-6-pyridin-3-ylhex-5-en-2-amine Chemical compound CNC(C)CC\C(C)=C/C1=CC=CN=C1 HUGUNCUQATWKMX-LUAWRHEFSA-N 0.000 claims description 2
- TUDIQGZXIAJHPV-FLIBITNWSA-N (z)-n,5-dimethyl-6-pyridin-3-ylhex-5-en-3-amine Chemical compound CCC(NC)C\C(C)=C/C1=CC=CN=C1 TUDIQGZXIAJHPV-FLIBITNWSA-N 0.000 claims description 2
- IEVJOUFGBRDCNE-UTCJRWHESA-N (z)-n-methyl-5-pyridin-3-ylpent-4-en-2-amine Chemical compound CNC(C)C\C=C/C1=CC=CN=C1 IEVJOUFGBRDCNE-UTCJRWHESA-N 0.000 claims description 2
- RUUGQRVCWASUJC-DAXSKMNVSA-N (z)-n-methyl-6-pyridin-3-ylhex-5-en-2-amine Chemical compound CNC(C)CC\C=C/C1=CC=CN=C1 RUUGQRVCWASUJC-DAXSKMNVSA-N 0.000 claims description 2
- DOWXVOMJGXCXRP-XQRVVYSFSA-N (z)-n-methyl-6-pyridin-3-ylhex-5-en-3-amine Chemical compound CCC(NC)C\C=C/C1=CC=CN=C1 DOWXVOMJGXCXRP-XQRVVYSFSA-N 0.000 claims description 2
- 206010037660 Pyrexia Diseases 0.000 claims description 2
- 201000010312 acute cholangitis Diseases 0.000 claims description 2
- 208000022531 anorexia Diseases 0.000 claims description 2
- 206010003246 arthritis Diseases 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 206010061428 decreased appetite Diseases 0.000 claims description 2
- 230000002538 fungal effect Effects 0.000 claims description 2
- 206010025135 lupus erythematosus Diseases 0.000 claims description 2
- 201000004792 malaria Diseases 0.000 claims description 2
- DBYGQAGUKUTJAX-NTMALXAHSA-N (z)-n,4-dimethyl-5-pyridin-3-ylpent-4-en-2-amine Chemical compound CNC(C)C\C(C)=C/C1=CC=CN=C1 DBYGQAGUKUTJAX-NTMALXAHSA-N 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- -1 amine compounds Chemical class 0.000 description 188
- 238000000034 method Methods 0.000 description 103
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 100
- 238000006243 chemical reaction Methods 0.000 description 58
- 239000000126 substance Substances 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 39
- 125000003107 substituted aryl group Chemical group 0.000 description 37
- 150000001412 amines Chemical group 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 32
- 230000000694 effects Effects 0.000 description 28
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 27
- 150000001336 alkenes Chemical group 0.000 description 27
- 239000003054 catalyst Substances 0.000 description 27
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 26
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- 229910052763 palladium Inorganic materials 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 23
- 230000028327 secretion Effects 0.000 description 23
- 239000000543 intermediate Substances 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 22
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 22
- 238000013459 approach Methods 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 19
- 239000008194 pharmaceutical composition Substances 0.000 description 19
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 17
- 210000004027 cell Anatomy 0.000 description 17
- 150000003839 salts Chemical class 0.000 description 17
- 239000012312 sodium hydride Substances 0.000 description 17
- 229910000104 sodium hydride Inorganic materials 0.000 description 17
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 16
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 16
- 230000016396 cytokine production Effects 0.000 description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 125000000623 heterocyclic group Chemical group 0.000 description 14
- 229910052744 lithium Inorganic materials 0.000 description 14
- OJZQOQNSUZLSMV-UHFFFAOYSA-N (3-aminophenyl)methanol Chemical compound NC1=CC=CC(CO)=C1 OJZQOQNSUZLSMV-UHFFFAOYSA-N 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 13
- 230000029936 alkylation Effects 0.000 description 13
- 238000005804 alkylation reaction Methods 0.000 description 13
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 13
- 230000002829 reductive effect Effects 0.000 description 13
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 12
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 11
- 238000007341 Heck reaction Methods 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 11
- 238000006073 displacement reaction Methods 0.000 description 11
- 229960002715 nicotine Drugs 0.000 description 11
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 11
- 208000024891 symptom Diseases 0.000 description 11
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 230000002265 prevention Effects 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- 239000000306 component Substances 0.000 description 9
- 208000037765 diseases and disorders Diseases 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- 150000003335 secondary amines Chemical class 0.000 description 9
- MGFRWLSGAABYES-UHFFFAOYSA-N tert-butyl n-methyl-n-pent-4-en-2-ylcarbamate Chemical compound C=CCC(C)N(C)C(=O)OC(C)(C)C MGFRWLSGAABYES-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 230000004913 activation Effects 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 208000035475 disorder Diseases 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- QURLPTIXXSGZQG-UHFFFAOYSA-N n-methyl-3-pyridin-3-yloxypropan-1-amine Chemical compound CNCCCOC1=CC=CN=C1 QURLPTIXXSGZQG-UHFFFAOYSA-N 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- ZHZCYWWNFQUZOR-RXMQYKEDSA-N (2r)-pent-4-en-2-ol Chemical compound C[C@@H](O)CC=C ZHZCYWWNFQUZOR-RXMQYKEDSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 230000004064 dysfunction Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- ZHZCYWWNFQUZOR-UHFFFAOYSA-N pent-4-en-2-ol Chemical compound CC(O)CC=C ZHZCYWWNFQUZOR-UHFFFAOYSA-N 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 7
- FHUSNGUPJXGLPL-UHFFFAOYSA-N 3-bromo-5-methoxyaniline Chemical compound COC1=CC(N)=CC(Br)=C1 FHUSNGUPJXGLPL-UHFFFAOYSA-N 0.000 description 6
- ASEHPOZWQJRWAD-UHFFFAOYSA-N 3-bromo-5-propan-2-yloxypyridine Chemical compound CC(C)OC1=CN=CC(Br)=C1 ASEHPOZWQJRWAD-UHFFFAOYSA-N 0.000 description 6
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 6
- BVUBIWPMRYHPBW-UHFFFAOYSA-N 3-iodo-5-methoxyaniline Chemical compound COC1=CC(N)=CC(I)=C1 BVUBIWPMRYHPBW-UHFFFAOYSA-N 0.000 description 6
- FFCSRWGYGMRBGD-UHFFFAOYSA-N 3-iodoaniline Chemical compound NC1=CC=CC(I)=C1 FFCSRWGYGMRBGD-UHFFFAOYSA-N 0.000 description 6
- 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 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 150000001448 anilines Chemical class 0.000 description 6
- 150000001502 aryl halides Chemical class 0.000 description 6
- 235000019445 benzyl alcohol Nutrition 0.000 description 6
- 230000008030 elimination Effects 0.000 description 6
- 238000003379 elimination reaction Methods 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 150000003141 primary amines Chemical group 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- SFOYQZYQTQDRIY-UHFFFAOYSA-N 1-chloro-3-iodopropane Chemical compound ClCCCI SFOYQZYQTQDRIY-UHFFFAOYSA-N 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 5
- FZWUIWQMJFAWJW-UHFFFAOYSA-N 3-bromo-5-methoxypyridine Chemical class COC1=CN=CC(Br)=C1 FZWUIWQMJFAWJW-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 5
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
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- QCETXLFSWJGTAZ-UHFFFAOYSA-N tert-butyl 2-(iodomethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1CI QCETXLFSWJGTAZ-UHFFFAOYSA-N 0.000 description 1
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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- 108700012359 toxins Proteins 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
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Classifications
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- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
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- 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
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| US6979695B2 (en) * | 1996-04-23 | 2005-12-27 | Targacept, Inc. | Compounds capable of activating cholinergic receptors |
| US20020052497A1 (en) * | 2000-03-09 | 2002-05-02 | Targacept, Inc. | Compounds capable of activating cholinergic receptors |
| CA2317572A1 (en) | 1998-04-02 | 1999-10-14 | Jared Miller Wagner | Pharmaceutical compositions and methods for use |
| US7790757B2 (en) * | 1998-06-16 | 2010-09-07 | Targacept, Inc. | Compounds capable of activating cholinergic receptors |
| US20010031771A1 (en) | 1999-05-24 | 2001-10-18 | Gary Maurice Dull | Pharmaceutical compositions and methods for use |
| WO2000071520A2 (en) * | 1999-05-24 | 2000-11-30 | Targacept, Inc. | Aryl substituted alkylamines capable of activating nicotinic cholinergic receptors |
| DE19956786A1 (de) * | 1999-11-25 | 2001-05-31 | Basf Ag | Verfahren zur Herstellung optisch aktiver Amine |
| US6656958B2 (en) | 2000-02-02 | 2003-12-02 | Abbott Laboratories | Substituted pyridine compounds useful for controlling chemical synaptic transmission |
| US20010034357A1 (en) * | 2000-02-02 | 2001-10-25 | Nan-Horng Lin | Substituted pyridine compounds useful for controlling chemical synaptic transmission |
| US8914114B2 (en) | 2000-05-23 | 2014-12-16 | The Feinstein Institute For Medical Research | Inhibition of inflammatory cytokine production by cholinergic agonists and vagus nerve stimulation |
| US6610713B2 (en) | 2000-05-23 | 2003-08-26 | North Shore - Long Island Jewish Research Institute | Inhibition of inflammatory cytokine production by cholinergic agonists and vagus nerve stimulation |
| GB2381750A (en) * | 2001-10-10 | 2003-05-14 | Inspire Pharmaceuticals Inc | Treatment for enhancing joint lubrication |
| US7442546B2 (en) * | 2002-03-15 | 2008-10-28 | The Regents Of The University Of Michigan | Method of modulating inflammatory response |
| AU2003304297A1 (en) * | 2002-08-23 | 2005-01-21 | Sungho Jin | Article comprising gated field emission structures with centralized nanowires and method for making the same |
| US6987027B2 (en) | 2002-08-23 | 2006-01-17 | The Regents Of The University Of California | Microscale vacuum tube device and method for making same |
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| US5212188A (en) * | 1992-03-02 | 1993-05-18 | R. J. Reynolds Tabacco Company | Method for treatment of neurodegenerative diseases |
| US5852041A (en) * | 1993-04-07 | 1998-12-22 | Sibia Neurosciences, Inc. | Substituted pyridines useful as modulators of acethylcholine receptors |
| WO1995029892A1 (en) * | 1994-04-28 | 1995-11-09 | The Du Pont Merck Pharmaceutical Company | Hydroxamic acid and amino acid derivatives and their use as anti-arthritic agents |
| US5597919A (en) * | 1995-01-06 | 1997-01-28 | Dull; Gary M. | Pyrimidinyl or Pyridinyl alkenyl amine compounds |
| US5604231A (en) * | 1995-01-06 | 1997-02-18 | Smith; Carr J. | Pharmaceutical compositions for prevention and treatment of ulcerative colitis |
| US5616707A (en) * | 1995-01-06 | 1997-04-01 | Crooks; Peter A. | Compounds which are useful for prevention and treatment of central nervous system disorders |
| US5583140A (en) * | 1995-05-17 | 1996-12-10 | Bencherif; Merouane | Pharmaceutical compositions for the treatment of central nervous system disorders |
| US5616716A (en) * | 1996-01-06 | 1997-04-01 | Dull; Gary M. | (3-(5-ethoxypyridin)yl)-alkenyl 1 amine compounds |
| ATE416164T1 (de) * | 1996-04-23 | 2008-12-15 | Targacept Inc | Pharmazeutische zusammenstellungen zur prävention und behandlung von zns-erkrankungen |
| US5663356A (en) * | 1996-04-23 | 1997-09-02 | Ruecroft; Graham | Method for preparation of aryl substituted alefinic secondary amino compounds |
| ZA9711092B (en) * | 1996-12-11 | 1999-07-22 | Smithkline Beecham Corp | Novel compounds. |
| US5861423A (en) * | 1997-02-21 | 1999-01-19 | Caldwell; William Scott | Pharmaceutical compositions incorporating aryl substituted olefinic amine compounds |
| US5811442A (en) * | 1997-02-21 | 1998-09-22 | Bencherif; Merouane | Pharmaceutical compositions for the treatment of conditions associated with decreased blood flow |
| WO1998047899A1 (en) * | 1997-04-24 | 1998-10-29 | Ortho-Mcneil Corporation, Inc. | Substituted pyrrolopyridines useful in the treatment of inflammatory diseases |
-
1999
- 1999-04-20 US US09/295,181 patent/US6166048A/en not_active Expired - Fee Related
-
2000
- 2000-04-20 DK DK00926142T patent/DK1171127T3/da active
- 2000-04-20 WO PCT/US2000/010551 patent/WO2000062767A2/en not_active Ceased
- 2000-04-20 DE DE60022637T patent/DE60022637T2/de not_active Expired - Lifetime
- 2000-04-20 KR KR1020017013390A patent/KR100816898B1/ko not_active Expired - Fee Related
- 2000-04-20 BR BR0009869-8A patent/BR0009869A/pt not_active IP Right Cessation
- 2000-04-20 JP JP2000611904A patent/JP2002542188A/ja active Pending
- 2000-04-20 MX MXPA01010635A patent/MXPA01010635A/es active IP Right Grant
- 2000-04-20 AU AU44719/00A patent/AU4471900A/en not_active Abandoned
- 2000-04-20 AT AT00926142T patent/ATE304355T1/de active
- 2000-04-20 EP EP00926142A patent/EP1171127B1/en not_active Expired - Lifetime
- 2000-04-20 CA CA2370206A patent/CA2370206C/en not_active Expired - Fee Related
- 2000-04-20 ES ES00926142T patent/ES2251995T3/es not_active Expired - Lifetime
- 2000-09-06 US US09/656,284 patent/US6489349B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE60022637T2 (de) | 2006-06-29 |
| US6489349B1 (en) | 2002-12-03 |
| MXPA01010635A (es) | 2002-03-14 |
| EP1171127A2 (en) | 2002-01-16 |
| CA2370206A1 (en) | 2000-10-26 |
| KR100816898B1 (ko) | 2008-03-26 |
| JP2002542188A (ja) | 2002-12-10 |
| EP1171127B1 (en) | 2005-09-14 |
| ATE304355T1 (de) | 2005-09-15 |
| DE60022637D1 (de) | 2005-10-20 |
| WO2000062767A3 (en) | 2001-03-08 |
| CA2370206C (en) | 2011-09-27 |
| KR20020002434A (ko) | 2002-01-09 |
| BR0009869A (pt) | 2002-03-26 |
| DK1171127T3 (da) | 2005-10-03 |
| US6166048A (en) | 2000-12-26 |
| WO2000062767A2 (en) | 2000-10-26 |
| AU4471900A (en) | 2000-11-02 |
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