JP2002542188A - サイトカインの産生および分泌を阻害する製薬学的組成物 - Google Patents
サイトカインの産生および分泌を阻害する製薬学的組成物Info
- Publication number
- JP2002542188A JP2002542188A JP2000611904A JP2000611904A JP2002542188A JP 2002542188 A JP2002542188 A JP 2002542188A JP 2000611904 A JP2000611904 A JP 2000611904A JP 2000611904 A JP2000611904 A JP 2000611904A JP 2002542188 A JP2002542188 A JP 2002542188A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- amine
- pyridyl
- methylamine
- penten
- 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.)
- Pending
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 50
- 230000028327 secretion Effects 0.000 title claims abstract description 28
- 230000016396 cytokine production Effects 0.000 title abstract description 23
- -1 amine compounds Chemical class 0.000 claims abstract description 212
- 150000001875 compounds Chemical class 0.000 claims abstract description 182
- 102000004127 Cytokines Human genes 0.000 claims abstract description 28
- 108090000695 Cytokines Proteins 0.000 claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 claims abstract description 17
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 133
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 110
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 45
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
- 150000001412 amines Chemical class 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 230000002401 inhibitory effect Effects 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- IAOMYGPUHHWELN-UHFFFAOYSA-N n-methyl-4-pyridin-3-yloxybutan-2-amine Chemical compound CNC(C)CCOC1=CC=CN=C1 IAOMYGPUHHWELN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- QURLPTIXXSGZQG-UHFFFAOYSA-N n-methyl-3-pyridin-3-yloxypropan-1-amine Chemical compound CNCCCOC1=CC=CN=C1 QURLPTIXXSGZQG-UHFFFAOYSA-N 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- SBOUHGZVYFYWMK-UHFFFAOYSA-N n-methyl-3-phenoxypropan-1-amine Chemical compound CNCCCOC1=CC=CC=C1 SBOUHGZVYFYWMK-UHFFFAOYSA-N 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 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 5
- LYIVXPJPEPNDIO-UHFFFAOYSA-N 3-(4-methoxyphenoxy)-n-methylpropan-1-amine Chemical compound CNCCCOC1=CC=C(OC)C=C1 LYIVXPJPEPNDIO-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- SLZXWWUDMJWZMP-RQOWECAXSA-N (z)-1,1,1-trifluoro-n-methyl-5-pyridin-3-ylpent-4-en-2-amine Chemical compound CNC(C(F)(F)F)C\C=C/C1=CC=CN=C1 SLZXWWUDMJWZMP-RQOWECAXSA-N 0.000 claims description 3
- KRDMBTGZQZKPMM-XQRVVYSFSA-N (z)-1-pyridin-3-yloct-1-en-4-amine Chemical compound CCCCC(N)C\C=C/C1=CC=CN=C1 KRDMBTGZQZKPMM-XQRVVYSFSA-N 0.000 claims description 3
- DKYGQOACSMJSAU-PLNGDYQASA-N (z)-2-methyl-4-pyridin-3-ylbut-3-en-1-amine Chemical compound NCC(C)\C=C/C1=CC=CN=C1 DKYGQOACSMJSAU-PLNGDYQASA-N 0.000 claims description 3
- MRIJAYUZKYDWER-CLFYSBASSA-N (z)-3-methyl-4-pyridin-3-ylbut-3-en-1-amine Chemical compound NCCC(/C)=C\C1=CC=CN=C1 MRIJAYUZKYDWER-CLFYSBASSA-N 0.000 claims description 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- HHXVWPMGEAPFLJ-WAYWQWQTSA-N (z)-n,2-dimethyl-4-pyridin-3-ylbut-3-en-1-amine Chemical compound CNCC(C)\C=C/C1=CC=CN=C1 HHXVWPMGEAPFLJ-WAYWQWQTSA-N 0.000 claims description 3
- 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 3
- 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 description 3
- IERLPSICESFRNB-ALCCZGGFSA-N (z)-n,5-dimethyl-1-pyridin-3-ylhept-1-en-4-amine Chemical compound CCC(C)C(NC)C\C=C/C1=CC=CN=C1 IERLPSICESFRNB-ALCCZGGFSA-N 0.000 claims description 3
- 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 3
- 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 3
- JGGVBSFRKVZGAC-ALCCZGGFSA-N (z)-n-methyl-1-pyridin-3-yloct-1-en-4-amine Chemical compound CCCCC(NC)C\C=C/C1=CC=CN=C1 JGGVBSFRKVZGAC-ALCCZGGFSA-N 0.000 claims description 3
- 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 3
- 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 3
- NKGVBMWSNYPWCY-NTMALXAHSA-N (z)-n,3-dimethyl-4-pyridin-3-ylbut-3-en-1-amine Chemical compound CNCC\C(C)=C/C1=CC=CN=C1 NKGVBMWSNYPWCY-NTMALXAHSA-N 0.000 claims 2
- 230000000694 effects Effects 0.000 abstract description 22
- 208000037765 diseases and disorders Diseases 0.000 abstract description 12
- 208000022559 Inflammatory bowel disease Diseases 0.000 abstract description 5
- 206010006895 Cachexia Diseases 0.000 abstract description 4
- 206010028980 Neoplasm Diseases 0.000 abstract description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical class NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 abstract description 3
- 206010061218 Inflammation Diseases 0.000 abstract description 3
- 230000004054 inflammatory process Effects 0.000 abstract description 3
- 208000030507 AIDS Diseases 0.000 abstract description 2
- 206010003246 arthritis Diseases 0.000 abstract description 2
- 201000011510 cancer Diseases 0.000 abstract description 2
- 230000004064 dysfunction Effects 0.000 abstract 1
- 230000036210 malignancy Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 50
- 239000000126 substance Substances 0.000 description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 238000005859 coupling reaction Methods 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 238000010168 coupling process Methods 0.000 description 34
- 230000008878 coupling Effects 0.000 description 33
- 150000001336 alkenes Chemical class 0.000 description 31
- 125000006239 protecting group Chemical group 0.000 description 29
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 29
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 28
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 28
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 27
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 19
- 229910000104 sodium hydride Inorganic materials 0.000 description 19
- 239000012312 sodium hydride Substances 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- 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 18
- 229960002715 nicotine Drugs 0.000 description 17
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 16
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
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- 230000015572 biosynthetic process Effects 0.000 description 16
- 125000000623 heterocyclic group Chemical group 0.000 description 16
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 15
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 14
- 125000003277 amino group Chemical group 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 238000010189 synthetic method Methods 0.000 description 13
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 12
- OJZQOQNSUZLSMV-UHFFFAOYSA-N (3-aminophenyl)methanol Chemical class NC1=CC=CC(CO)=C1 OJZQOQNSUZLSMV-UHFFFAOYSA-N 0.000 description 12
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 12
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- 241000894007 species Species 0.000 description 12
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- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
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- 239000002253 acid Substances 0.000 description 10
- 125000003710 aryl alkyl group Chemical group 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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- 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
- 239000007864 aqueous solution Substances 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 9
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- 150000003335 secondary amines Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
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- 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 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
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 5
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- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000037323 metabolic rate Effects 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-KHWXYDKHSA-N methanesulfonyl chloride Chemical group C[35S](Cl)(=O)=O QARBMVPHQWIHKH-KHWXYDKHSA-N 0.000 description 1
- LDLDJEAVRNAEBW-SCSAIBSYSA-N methyl (3r)-3-hydroxybutanoate Chemical compound COC(=O)C[C@@H](C)O LDLDJEAVRNAEBW-SCSAIBSYSA-N 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 210000005087 mononuclear cell Anatomy 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- DMQSHEKGGUOYJS-UHFFFAOYSA-N n,n,n',n'-tetramethylpropane-1,3-diamine Chemical compound CN(C)CCCN(C)C DMQSHEKGGUOYJS-UHFFFAOYSA-N 0.000 description 1
- BHRXIBGMHFBVKX-UHFFFAOYSA-N n-[3-(1-hydroxycyclohexyl)phenyl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC=CC(C2(O)CCCCC2)=C1 BHRXIBGMHFBVKX-UHFFFAOYSA-N 0.000 description 1
- FYRUBQBOBNOGMJ-UHFFFAOYSA-N n-[3-[(3-aminophenyl)methoxy]propyl]-1,3-thiazol-2-amine Chemical compound NC1=CC=CC(COCCCNC=2SC=CN=2)=C1 FYRUBQBOBNOGMJ-UHFFFAOYSA-N 0.000 description 1
- CWZXGLMWQHYQGQ-UHFFFAOYSA-N n-[3-[(3-nitrophenyl)methoxy]propyl]-1,3-thiazol-2-amine Chemical compound [O-][N+](=O)C1=CC=CC(COCCCNC=2SC=CN=2)=C1 CWZXGLMWQHYQGQ-UHFFFAOYSA-N 0.000 description 1
- ABPVOVVFNFRBRZ-UHFFFAOYSA-N n-bromo-3-methoxyaniline Chemical compound COC1=CC=CC(NBr)=C1 ABPVOVVFNFRBRZ-UHFFFAOYSA-N 0.000 description 1
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
- NIYOROJNMQRKOE-UHFFFAOYSA-N n-methyl-2-[(3-nitrophenyl)methoxy]ethanamine Chemical compound CNCCOCC1=CC=CC([N+]([O-])=O)=C1 NIYOROJNMQRKOE-UHFFFAOYSA-N 0.000 description 1
- ILUNFMUCNQMEJJ-UHFFFAOYSA-N n-methyl-2-[(4-methyl-3-nitrophenyl)methoxy]ethanamine Chemical compound CNCCOCC1=CC=C(C)C([N+]([O-])=O)=C1 ILUNFMUCNQMEJJ-UHFFFAOYSA-N 0.000 description 1
- WBAIXNUCEGCLDC-UHFFFAOYSA-N n-methyl-4-pyridin-3-ylbut-3-yn-1-amine Chemical class CNCCC#CC1=CC=CN=C1 WBAIXNUCEGCLDC-UHFFFAOYSA-N 0.000 description 1
- QHJKYFYKNOSLTL-UHFFFAOYSA-N n-methyl-4-pyridin-3-yloxybutan-1-amine Chemical compound CNCCCCOC1=CC=CN=C1 QHJKYFYKNOSLTL-UHFFFAOYSA-N 0.000 description 1
- 230000007302 negative regulation of cytokine production Effects 0.000 description 1
- 230000019079 negative regulation of cytokine secretion Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 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 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- NYYDZOSYLUOKEM-UHFFFAOYSA-N oxaldehyde;hydrate Chemical compound O.O=CC=O NYYDZOSYLUOKEM-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- FSEKYSAWZRQAPN-UHFFFAOYSA-N pent-1-en-1-amine Chemical compound CCCC=CN FSEKYSAWZRQAPN-UHFFFAOYSA-N 0.000 description 1
- FPKGXWLAUMDRRC-UHFFFAOYSA-N pent-1-en-2-amine Chemical compound CCCC(N)=C FPKGXWLAUMDRRC-UHFFFAOYSA-N 0.000 description 1
- ALJBLKAIECRRNL-UHFFFAOYSA-N pent-3-yn-2-yl 4-methylbenzenesulfonate Chemical compound CC#CC(C)OS(=O)(=O)c1ccc(C)cc1 ALJBLKAIECRRNL-UHFFFAOYSA-N 0.000 description 1
- LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 description 1
- BPIDLOWRIYHHBQ-UHFFFAOYSA-N pent-4-en-2-amine Chemical compound CC(N)CC=C BPIDLOWRIYHHBQ-UHFFFAOYSA-N 0.000 description 1
- WIWURRFVCSTIAY-UHFFFAOYSA-N pent-4-en-2-yl 4-methylbenzenesulfonate Chemical compound C=CCC(C)OS(=O)(=O)C1=CC=C(C)C=C1 WIWURRFVCSTIAY-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 229960002429 proline Drugs 0.000 description 1
- POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical compound C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000024833 regulation of cytokine production Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- JUOSGGQXEBBCJB-GORDUTHDSA-N rivanicline Chemical compound CNCC\C=C\C1=CC=CN=C1 JUOSGGQXEBBCJB-GORDUTHDSA-N 0.000 description 1
- 229940063148 rowasa Drugs 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- BFFLLBPMZCIGRM-MRVPVSSYSA-N tert-butyl (2r)-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@@H]1CO BFFLLBPMZCIGRM-MRVPVSSYSA-N 0.000 description 1
- XIRUXUKRGUFEKC-ZETCQYMHSA-N tert-butyl (2s)-2-(hydroxymethyl)azetidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@H]1CO XIRUXUKRGUFEKC-ZETCQYMHSA-N 0.000 description 1
- 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YTMUZPNFZCUDLK-UHFFFAOYSA-N tert-butyl n-(4-oxohexyl)carbamate Chemical compound CCC(=O)CCCNC(=O)OC(C)(C)C YTMUZPNFZCUDLK-UHFFFAOYSA-N 0.000 description 1
- LDPZRDDGSNDUNX-UHFFFAOYSA-N tert-butyl n-ethyl-n-methylcarbamate Chemical compound CCN(C)C(=O)OC(C)(C)C LDPZRDDGSNDUNX-UHFFFAOYSA-N 0.000 description 1
- RFHBVZLFGHWDMM-CSKARUKUSA-N tert-butyl n-methyl-n-[(e)-5-(5-propan-2-yloxypyridin-3-yl)pent-4-en-2-yl]carbamate Chemical compound CC(C)OC1=CN=CC(\C=C\CC(C)N(C)C(=O)OC(C)(C)C)=C1 RFHBVZLFGHWDMM-CSKARUKUSA-N 0.000 description 1
- FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D213/24—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
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Rheumatology (AREA)
- Virology (AREA)
- Diabetes (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Nutrition Science (AREA)
- Dermatology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/295,181 US6166048A (en) | 1999-04-20 | 1999-04-20 | Pharmaceutical compositions for inhibition of cytokine production and secretion |
| US09/295,181 | 1999-04-20 | ||
| PCT/US2000/010551 WO2000062767A2 (en) | 1999-04-20 | 2000-04-20 | Pharmaceutical compositions containing pyridine or pyrimidine derivates for inhibition of cytokine production and secretion |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002542188A true JP2002542188A (ja) | 2002-12-10 |
| JP2002542188A5 JP2002542188A5 (enExample) | 2007-06-14 |
Family
ID=23136585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000611904A Pending JP2002542188A (ja) | 1999-04-20 | 2000-04-20 | サイトカインの産生および分泌を阻害する製薬学的組成物 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6166048A (enExample) |
| EP (1) | EP1171127B1 (enExample) |
| JP (1) | JP2002542188A (enExample) |
| KR (1) | KR100816898B1 (enExample) |
| AT (1) | ATE304355T1 (enExample) |
| AU (1) | AU4471900A (enExample) |
| BR (1) | BR0009869A (enExample) |
| CA (1) | CA2370206C (enExample) |
| DE (1) | DE60022637T2 (enExample) |
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- 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
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- 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
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| JP2003514888A (ja) * | 1999-11-25 | 2003-04-22 | ビーエーエスエフ アクチェンゲゼルシャフト | 光学活性アミンの製造方法 |
| JP4776846B2 (ja) * | 1999-11-25 | 2011-09-21 | ビーエーエスエフ ソシエタス・ヨーロピア | 光学活性アミンの製造方法 |
Also Published As
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| 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 |
| 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 |
| ES2251995T3 (es) | 2006-05-16 |
| US6166048A (en) | 2000-12-26 |
| WO2000062767A2 (en) | 2000-10-26 |
| AU4471900A (en) | 2000-11-02 |
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