JP2003511450A - ｔ−ブチル−（７−メチル−イミダゾ［１，２−ａ］ピリジン−３−イル）−アミン誘導体 - Google Patents
ｔ−ブチル−（７−メチル−イミダゾ［１，２−ａ］ピリジン−３−イル）−アミン誘導体Info
- Publication number
- JP2003511450A JP2003511450A JP2001530327A JP2001530327A JP2003511450A JP 2003511450 A JP2003511450 A JP 2003511450A JP 2001530327 A JP2001530327 A JP 2001530327A JP 2001530327 A JP2001530327 A JP 2001530327A JP 2003511450 A JP2003511450 A JP 2003511450A
- Authority
- JP
- Japan
- Prior art keywords
- unsubstituted
- substituted
- alkyl
- unsaturated
- saturated
- 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
- YZGFPSZQJDPTGW-UHFFFAOYSA-N n-tert-butyl-7-methylimidazo[1,2-a]pyridin-3-amine Chemical class C1=C(C)C=CN2C(NC(C)(C)C)=CN=C21 YZGFPSZQJDPTGW-UHFFFAOYSA-N 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 238000000034 method Methods 0.000 claims abstract description 36
- 239000003814 drug Substances 0.000 claims abstract description 17
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims abstract description 14
- 108010021487 Nitric Oxide Synthase Proteins 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 6
- 206010027599 migraine Diseases 0.000 claims abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 118
- 125000000217 alkyl group Chemical class 0.000 claims description 63
- -1 7-methyl-2-pyridin-3-yl-imidazo [1,2-a] pyridin-3-yl Chemical group 0.000 claims description 56
- 150000003839 salts Chemical class 0.000 claims description 44
- 125000000623 heterocyclic group Chemical group 0.000 claims description 43
- 125000001072 heteroaryl group Chemical class 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 238000006467 substitution reaction Methods 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 11
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 8
- 150000003927 aminopyridines Chemical class 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- GAOXLBQDTVDEJH-UHFFFAOYSA-N n-tert-butyl-2-(furan-2-yl)-7-methylimidazo[1,2-a]pyridin-3-amine Chemical compound N1=C2C=C(C)C=CN2C(NC(C)(C)C)=C1C1=CC=CO1 GAOXLBQDTVDEJH-UHFFFAOYSA-N 0.000 claims description 8
- FAGLEPBREOXSAC-UHFFFAOYSA-N tert-butyl isocyanide Chemical compound CC(C)(C)[N+]#[C-] FAGLEPBREOXSAC-UHFFFAOYSA-N 0.000 claims description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- RCQFFBBGAATMLI-UHFFFAOYSA-N 5-[3-(tert-butylamino)-7-methylimidazo[1,2-a]pyridin-2-yl]thiophene-2-carboxylic acid Chemical compound N1=C2C=C(C)C=CN2C(NC(C)(C)C)=C1C1=CC=C(C(O)=O)S1 RCQFFBBGAATMLI-UHFFFAOYSA-N 0.000 claims description 7
- XBIJCAKRLAMAPN-UHFFFAOYSA-N [5-[3-(tert-butylamino)-7-methylimidazo[1,2-a]pyridin-2-yl]furan-2-yl]methanol Chemical compound N1=C2C=C(C)C=CN2C(NC(C)(C)C)=C1C1=CC=C(CO)O1 XBIJCAKRLAMAPN-UHFFFAOYSA-N 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 7
- PILXZSKVZNJVJB-UHFFFAOYSA-N n-tert-butyl-2,7-dimethylimidazo[1,2-a]pyridin-3-amine Chemical compound C1=C(C)C=CN2C(NC(C)(C)C)=C(C)N=C21 PILXZSKVZNJVJB-UHFFFAOYSA-N 0.000 claims description 7
- LYCYZJPXXHLUGQ-UHFFFAOYSA-N n-tert-butyl-2-[5-(1,3-dioxolan-2-yl)furan-2-yl]-7-methylimidazo[1,2-a]pyridin-3-amine Chemical compound N1=C2C=C(C)C=CN2C(NC(C)(C)C)=C1C(O1)=CC=C1C1OCCO1 LYCYZJPXXHLUGQ-UHFFFAOYSA-N 0.000 claims description 7
- AVUXSWKQTDMSKC-UHFFFAOYSA-N n-tert-butyl-2-cyclohexyl-7-methylimidazo[1,2-a]pyridin-3-amine Chemical compound N1=C2C=C(C)C=CN2C(NC(C)(C)C)=C1C1CCCCC1 AVUXSWKQTDMSKC-UHFFFAOYSA-N 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 6
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 5
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 206010040070 Septic Shock Diseases 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 230000036303 septic shock Effects 0.000 claims description 5
- 230000029663 wound healing Effects 0.000 claims description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 201000006474 Brain Ischemia Diseases 0.000 claims description 4
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 4
- 206010049119 Emotional distress Diseases 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 4
- 206010008118 cerebral infarction Diseases 0.000 claims description 4
- 230000009429 distress Effects 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 230000002757 inflammatory effect Effects 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 239000012528 membrane Substances 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical class 0.000 claims description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 2
- 238000005580 one pot reaction Methods 0.000 claims description 2
- NNGDTFNYWWYMKI-UHFFFAOYSA-N 3-[3-(tert-butylamino)-5,7-dimethylimidazo[1,2-a]pyridin-2-yl]phenol Chemical compound N1=C2C=C(C)C=C(C)N2C(NC(C)(C)C)=C1C1=CC=CC(O)=C1 NNGDTFNYWWYMKI-UHFFFAOYSA-N 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 206010052428 Wound Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 230000035876 healing Effects 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 239000005051 trimethylchlorosilane Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 10
- 239000003112 inhibitor Substances 0.000 abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 235000002639 sodium chloride Nutrition 0.000 description 30
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 15
- 238000003556 assay Methods 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- 239000004475 Arginine Substances 0.000 description 12
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 12
- 235000009697 arginine Nutrition 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 10
- 108090000790 Enzymes Proteins 0.000 description 10
- 229940079593 drug Drugs 0.000 description 9
- 150000002527 isonitriles Chemical class 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 229960002173 citrulline Drugs 0.000 description 7
- 238000011534 incubation Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 6
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 235000013477 citrulline Nutrition 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 125000005213 alkyl heteroaryl group Chemical group 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 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 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 235000015165 citric acid Nutrition 0.000 description 4
- 229960004106 citric acid Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- XKXCEJQFBQELLH-UHFFFAOYSA-N n-tert-butyl-7-methyl-2-phenylimidazo[1,2-a]pyridin-3-amine Chemical compound N1=C2C=C(C)C=CN2C(NC(C)(C)C)=C1C1=CC=CC=C1 XKXCEJQFBQELLH-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 3
- PQCAUHUKTBHUSA-UHFFFAOYSA-N 7-nitro-1h-indazole Chemical compound [O-][N+](=O)C1=CC=CC2=C1NN=C2 PQCAUHUKTBHUSA-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000001506 calcium phosphate Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000004220 glutamic acid Substances 0.000 description 3
- 235000013922 glutamic acid Nutrition 0.000 description 3
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 241001655883 Adeno-associated virus - 1 Species 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- 229920001800 Shellac Polymers 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- C—CHEMISTRY; METALLURGY
- C40—COMBINATORIAL TECHNOLOGY
- C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
- C40B40/00—Libraries per se, e.g. arrays, mixtures
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- Engineering & Computer Science (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Molecular Biology (AREA)
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- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19948434A DE19948434A1 (de) | 1999-10-08 | 1999-10-08 | Substanzbibliothek enthaltend bicyclische Imidazo-5-amine und/oder bicyclische Imidazo-3-amine |
| DE19948434.1 | 1999-10-08 | ||
| PCT/EP2000/009791 WO2001027109A2 (de) | 1999-10-08 | 2000-10-06 | Tert.-butyl-(7-methyl-imidazo[1,2-a]pyridin-3-yl)-amin-derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003511450A true JP2003511450A (ja) | 2003-03-25 |
| JP2003511450A5 JP2003511450A5 (https=) | 2007-09-27 |
Family
ID=7924888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2001530327A Pending JP2003511450A (ja) | 1999-10-08 | 2000-10-06 | ｔ−ブチル−（７−メチル−イミダゾ［１，２−ａ］ピリジン−３−イル）−アミン誘導体 |
Country Status (28)
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| US (1) | US6703404B2 (https=) |
| EP (1) | EP1218378B1 (https=) |
| JP (1) | JP2003511450A (https=) |
| KR (1) | KR100793619B1 (https=) |
| CN (1) | CN1208336C (https=) |
| AR (2) | AR025960A1 (https=) |
| AT (1) | ATE238304T1 (https=) |
| AU (2) | AU7419900A (https=) |
| BR (1) | BR0014827A (https=) |
| CA (1) | CA2386804A1 (https=) |
| CO (2) | CO5210861A1 (https=) |
| CZ (1) | CZ20021241A3 (https=) |
| DE (2) | DE19948434A1 (https=) |
| DK (1) | DK1218378T3 (https=) |
| ES (1) | ES2198355T3 (https=) |
| HK (1) | HK1047749B (https=) |
| HU (1) | HUP0203545A3 (https=) |
| IL (3) | IL148997A0 (https=) |
| MX (1) | MXPA02003546A (https=) |
| NO (1) | NO20021564L (https=) |
| NZ (1) | NZ518438A (https=) |
| PE (2) | PE20010632A1 (https=) |
| PL (1) | PL355109A1 (https=) |
| PT (1) | PT1218378E (https=) |
| RU (1) | RU2002110281A (https=) |
| SK (1) | SK4622002A3 (https=) |
| WO (2) | WO2001027119A2 (https=) |
| ZA (2) | ZA200203581B (https=) |
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1999
- 1999-10-08 DE DE19948434A patent/DE19948434A1/de not_active Withdrawn
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- 2000-09-18 AU AU74199/00A patent/AU7419900A/en not_active Abandoned
- 2000-10-02 CO CO00074640A patent/CO5210861A1/es not_active Application Discontinuation
- 2000-10-05 AR ARP000105251A patent/AR025960A1/es not_active Application Discontinuation
- 2000-10-05 AR ARP000105250A patent/AR025959A1/es not_active Application Discontinuation
- 2000-10-06 BR BR0014827-0A patent/BR0014827A/pt not_active IP Right Cessation
- 2000-10-06 EP EP00969439A patent/EP1218378B1/de not_active Expired - Lifetime
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- 2000-10-06 CN CNB008167079A patent/CN1208336C/zh not_active Expired - Fee Related
- 2000-10-06 MX MXPA02003546A patent/MXPA02003546A/es active IP Right Grant
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- 2000-10-06 WO PCT/EP2000/009791 patent/WO2001027109A2/de not_active Ceased
- 2000-10-06 JP JP2001530327A patent/JP2003511450A/ja active Pending
- 2000-10-06 PT PT00969439T patent/PT1218378E/pt unknown
- 2000-10-06 PE PE2000001063A patent/PE20010632A1/es not_active Application Discontinuation
- 2000-10-06 CZ CZ20021241A patent/CZ20021241A3/cs unknown
- 2000-10-06 PE PE2000001062A patent/PE20010706A1/es not_active Application Discontinuation
- 2000-10-06 HU HU0203545A patent/HUP0203545A3/hu unknown
- 2000-10-06 ES ES00969439T patent/ES2198355T3/es not_active Expired - Lifetime
- 2000-10-06 SK SK462-2002A patent/SK4622002A3/sk unknown
- 2000-10-06 HK HK02109385.2A patent/HK1047749B/zh not_active IP Right Cessation
- 2000-10-06 RU RU2002110281/04A patent/RU2002110281A/ru not_active Application Discontinuation
- 2000-10-06 DE DE50001911T patent/DE50001911D1/de not_active Expired - Lifetime
- 2000-10-06 KR KR1020027004518A patent/KR100793619B1/ko not_active Expired - Fee Related
- 2000-10-06 CO CO00076179A patent/CO5251429A1/es not_active Application Discontinuation
- 2000-10-06 IL IL14899900A patent/IL148999A0/xx active IP Right Grant
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2002
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- 2002-04-04 IL IL148999A patent/IL148999A/en not_active IP Right Cessation
- 2002-04-08 US US10/117,339 patent/US6703404B2/en not_active Expired - Fee Related
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08333258A (ja) * | 1994-12-14 | 1996-12-17 | Japan Tobacco Inc | チアジン又はチアゼピン誘導体及びそれら化合物を含有してなる一酸化窒素合成酵素阻害剤 |
| JPH11503121A (ja) * | 1995-03-27 | 1999-03-23 | 藤沢薬品工業株式会社 | アミジン誘導体 |
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| JPN6010065641, ＢＩＥＮＡＹＭＥ，Ｈ． ｅｔ ａｌ．, "Ａ ｎｅｗ ｈｅｔｅｒｏｃｙｃｌｉｃ ｍｕｌｔｉｃｏｍｐｏｎｅｎｔ ｒｅａｃｔｉｏｎ ｆｏｒ ｔｈｅ ｃｏｍｂｉｎａｔｏｒｉａｌ ｓｙｎｔｈｅｓｉｓ ｏｆ ｆｕｓｅｄ ３−ａｍｉｎｏｉｍｉｄａｚｏｌｅ", Ａｎｇｅｗａｎｄｔｅ Ｃｈｅｍｉｅ， Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｅｄｉｔｉｏｎ, 1998, Ｖｏｌ．３７， Ｎｏ．１６, ｐ．２２３４−２２３７ * |
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