SK11202002A3 - Deriváty 1H-imidazopyridínu - Google Patents

Deriváty 1H-imidazopyridínu Download PDF

Info

Publication number: SK11202002A3
Authority: SK; Slovakia
Prior art keywords: group; substituted; ethyl; imidazo; trifluoromethyl
Prior art date: 2000-02-09

Application number

SK1120-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Hideo Kato

Jun Sakaguchi

Tomoyuki Izumi

Ken-Ichi Kato

Original Assignee

Hokuriku Seiyaku Co., Ltd.

Priority date (The priority date 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 date listed.)

2000-02-09

Filing date

2001-02-06

Publication date

2003-03-04

2001-02-06 Application filed by Hokuriku Seiyaku Co., Ltd. filed Critical Hokuriku Seiyaku Co., Ltd.

2003-03-04 Publication of SK11202002A3 publication Critical patent/SK11202002A3/sk

Links

GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 title claims abstract description 13
150000001875 compounds Chemical class 0.000 claims abstract description 114
150000003839 salts Chemical class 0.000 claims abstract description 31
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 28
125000000217 alkyl group Chemical group 0.000 claims abstract description 20
125000003277 amino group Chemical group 0.000 claims abstract description 15
125000003118 aryl group Chemical group 0.000 claims abstract description 14
102000004127 Cytokines Human genes 0.000 claims abstract description 13
108090000695 Cytokines Proteins 0.000 claims abstract description 13
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 13
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 4
-1 thiocarbamoyl group Chemical group 0.000 claims description 240
238000000034 method Methods 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 18
239000003814 drug Substances 0.000 claims description 14
108010002352 Interleukin-1 Proteins 0.000 claims description 10
125000002252 acyl group Chemical group 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
201000010099 disease Diseases 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
239000004480 active ingredient Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
230000016396 cytokine production Effects 0.000 claims description 5
239000003112 inhibitor Substances 0.000 claims description 5
230000001225 therapeutic effect Effects 0.000 claims description 5
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
230000003449 preventive effect Effects 0.000 claims description 4
241000124008 Mammalia Species 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000000320 amidine group Chemical group 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 abstract description 10
238000004519 manufacturing process Methods 0.000 abstract description 8
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
239000013078 crystal Substances 0.000 description 156
238000000921 elemental analysis Methods 0.000 description 151
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 143
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
239000002904 solvent Substances 0.000 description 100
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 88
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 71
229910052799 carbon Inorganic materials 0.000 description 61
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
238000001953 recrystallisation Methods 0.000 description 54
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 51
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 46
239000000203 mixture Substances 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
230000000704 physical effect Effects 0.000 description 29
239000000243 solution Substances 0.000 description 29
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 26
238000000354 decomposition reaction Methods 0.000 description 26
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 20
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
108060008682 Tumor Necrosis Factor Proteins 0.000 description 16
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 16
229910052739 hydrogen Inorganic materials 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
239000002585 base Substances 0.000 description 14
125000004433 nitrogen atom Chemical group N* 0.000 description 14
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
229910000027 potassium carbonate Inorganic materials 0.000 description 13
125000001424 substituent group Chemical group 0.000 description 13
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 12
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
238000010992 reflux Methods 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
238000010189 synthetic method Methods 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
102000000589 Interleukin-1 Human genes 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
229960001760 dimethyl sulfoxide Drugs 0.000 description 9
239000007788 liquid Substances 0.000 description 9
101100441092 Danio rerio crlf3 gene Proteins 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
238000001914 filtration Methods 0.000 description 7
125000000524 functional group Chemical group 0.000 description 7
238000002329 infrared spectrum Methods 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 6
PQXZBJMOJWEJQA-UHFFFAOYSA-N C1=CC=C2C(=C1)C3=C(C(=N2)C(F)(F)F)NC=N3 Chemical compound C1=CC=C2C(=C1)C3=C(C(=N2)C(F)(F)F)NC=N3 PQXZBJMOJWEJQA-UHFFFAOYSA-N 0.000 description 6
230000001363 autoimmune Effects 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
239000008279 sol Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 5
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 5
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108010001336 Horseradish Peroxidase Proteins 0.000 description 5
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210000004027 cell Anatomy 0.000 description 5
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ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 description 4
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BEQYJCXRZALRJN-UHFFFAOYSA-N 2-[2-[7-fluoro-2-thiophen-2-yl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCC1CNCCO1 BEQYJCXRZALRJN-UHFFFAOYSA-N 0.000 description 4
HKXLCKHMOVSPFA-UHFFFAOYSA-N 2-[2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethanamine Chemical compound N=1C2=C(C(F)(F)F)N=C3C=CC=CC3=C2N(CCN)C=1C1=CC=CC=C1 HKXLCKHMOVSPFA-UHFFFAOYSA-N 0.000 description 4
ABZGJBAMTLQZAW-UHFFFAOYSA-N 2-phenyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 ABZGJBAMTLQZAW-UHFFFAOYSA-N 0.000 description 4
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101000611183 Homo sapiens Tumor necrosis factor Proteins 0.000 description 4
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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102000057041 human TNF Human genes 0.000 description 4
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238000003756 stirring Methods 0.000 description 4
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 4
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BDHMYEXCAFRKAM-UHFFFAOYSA-N 2-(4-iodophenyl)-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=C(I)C=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 BDHMYEXCAFRKAM-UHFFFAOYSA-N 0.000 description 3
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AQTUZBFJCBKQBI-UHFFFAOYSA-N n-[2-(2-nitroacetyl)phenyl]benzamide Chemical compound [O-][N+](=O)CC(=O)C1=CC=CC=C1NC(=O)C1=CC=CC=C1 AQTUZBFJCBKQBI-UHFFFAOYSA-N 0.000 description 1
KRIGCHTYSRHJNQ-UHFFFAOYSA-N n-[2-[2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]acetamide Chemical compound N=1C2=C(C(F)(F)F)N=C3C=CC=CC3=C2N(CCNC(=O)C)C=1C1=CC=CC=C1 KRIGCHTYSRHJNQ-UHFFFAOYSA-N 0.000 description 1
LJHWDTJTJRGFGS-UHFFFAOYSA-N n-[2-[2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]methanesulfonamide Chemical compound N=1C2=C(C(F)(F)F)N=C3C=CC=CC3=C2N(CCNS(=O)(=O)C)C=1C1=CC=CC=C1 LJHWDTJTJRGFGS-UHFFFAOYSA-N 0.000 description 1
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239000007923 nasal drop Substances 0.000 description 1
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LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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239000002674 ointment Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000003002 pH adjusting agent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
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239000002245 particle Substances 0.000 description 1
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UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
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125000003386 piperidinyl group Chemical group 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
208000005069 pulmonary fibrosis Diseases 0.000 description 1
UCQFSGCWHRTMGG-UHFFFAOYSA-N pyrazole-1-carboximidamide Chemical compound NC(=N)N1C=CC=N1 UCQFSGCWHRTMGG-UHFFFAOYSA-N 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
125000005554 pyridyloxy group Chemical group 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical compound OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229960004029 silicic acid Drugs 0.000 description 1
229960001866 silicon dioxide Drugs 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
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208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
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239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
LBQDLHPFISVBRU-UHFFFAOYSA-N tert-butyl 4-(2-aminoethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CCN)CC1 LBQDLHPFISVBRU-UHFFFAOYSA-N 0.000 description 1
FSROTDSLIAOVEJ-UHFFFAOYSA-N tert-butyl 4-[2-(2-phenylimidazo[4,5-c]quinolin-1-yl)ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCN1C2=C3C=CC=CC3=NC=C2N=C1C1=CC=CC=C1 FSROTDSLIAOVEJ-UHFFFAOYSA-N 0.000 description 1
KXZVDQAMYGQXBP-UHFFFAOYSA-N tert-butyl 4-[2-(4-chloro-2-phenylimidazo[4,5-c]quinolin-1-yl)ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCN1C2=C3C=CC=CC3=NC(Cl)=C2N=C1C1=CC=CC=C1 KXZVDQAMYGQXBP-UHFFFAOYSA-N 0.000 description 1
CKZFJESKIMEODW-UHFFFAOYSA-N tert-butyl 4-[2-(4-cyano-2-phenylimidazo[4,5-c]quinolin-1-yl)ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCN1C2=C3C=CC=CC3=NC(C#N)=C2N=C1C1=CC=CC=C1 CKZFJESKIMEODW-UHFFFAOYSA-N 0.000 description 1
OAOYTKFLHIOBAU-UHFFFAOYSA-N tert-butyl 4-[2-[2-(4-iodophenyl)-8-methyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCN1C=2C3=CC(C)=CC=C3N=C(C(F)(F)F)C=2N=C1C1=CC=C(I)C=C1 OAOYTKFLHIOBAU-UHFFFAOYSA-N 0.000 description 1
LCLPKKKLIPFUGL-UHFFFAOYSA-N tert-butyl 4-[2-[[3-amino-6-methyl-2-(trifluoromethyl)quinolin-4-yl]amino]ethyl]piperidine-1-carboxylate Chemical compound C12=CC(C)=CC=C2N=C(C(F)(F)F)C(N)=C1NCCC1CCN(C(=O)OC(C)(C)C)CC1 LCLPKKKLIPFUGL-UHFFFAOYSA-N 0.000 description 1
VTVAUYPEELMWPX-UHFFFAOYSA-N tert-butyl 4-[2-[[3-nitro-2-(trifluoromethyl)quinolin-4-yl]amino]ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCNC1=C([N+]([O-])=O)C(C(F)(F)F)=NC2=CC=CC=C12 VTVAUYPEELMWPX-UHFFFAOYSA-N 0.000 description 1
TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
239000001069 triethyl citrate Substances 0.000 description 1
VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
235000013769 triethyl citrate Nutrition 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
230000006433 tumor necrosis factor production Effects 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
208000018464 vernal keratoconjunctivitis Diseases 0.000 description 1
239000001993 wax Substances 0.000 description 1
DYWSVUBJGFTOQC-UHFFFAOYSA-N xi-2-Ethylheptanoic acid Chemical compound CCCCCC(CC)C(O)=O DYWSVUBJGFTOQC-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D471/04—Ortho-condensed systems
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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]
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Pulmonology (AREA)
Epidemiology (AREA)
Diabetes (AREA)
Pain & Pain Management (AREA)
Hematology (AREA)
Neurology (AREA)
Rheumatology (AREA)
Biomedical Technology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Neurosurgery (AREA)
Obesity (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Dermatology (AREA)
Transplantation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK1120-2002A 2000-02-09 2001-02-06 Deriváty 1H-imidazopyridínu SK11202002A3 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP2000031270		2000-02-09
JP2000277507		2000-09-13
PCT/JP2001/000816 WO2001058900A1 (en)	2000-02-09	2001-02-06	1h-imidazopyridine derivatives

Publications (1)

Publication Number	Publication Date
SK11202002A3 true SK11202002A3 (sk)	2003-03-04

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ID=26585077

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1120-2002A SK11202002A3 (sk)	2000-02-09	2001-02-06	Deriváty 1H-imidazopyridínu

Country Status (16)

Country	Link
US (1)	US20040054182A1 (cs)
EP (1)	EP1256582A1 (cs)
KR (1)	KR20020073211A (cs)
CN (1)	CN1422269A (cs)
AU (1)	AU2001230584A1 (cs)
BG (1)	BG107067A (cs)
BR (1)	BR0108303A (cs)
CA (1)	CA2399136A1 (cs)
CZ (1)	CZ20022626A3 (cs)
HU (1)	HUP0204474A3 (cs)
IL (1)	IL150841A0 (cs)
MX (1)	MXPA02007525A (cs)
NO (1)	NO20023750L (cs)
PL (1)	PL355866A1 (cs)
SK (1)	SK11202002A3 (cs)
WO (1)	WO2001058900A1 (cs)

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DK1474425T3 (da)	2002-01-07	2006-09-25	Eisai Co Ltd	Deazapuriner og anvendelser deraf
GB0211649D0 (en) *	2002-05-21	2002-07-03	Novartis Ag	Organic compounds
PT1539752E (pt)	2002-07-26	2007-05-31	Teva Gyogyszergyar Zartkoeruen	Preparação de 1h-imidazo [4,5-c] quinolina-4-aminas via novos intermediários imidazo [4,5-c] quinolina-4-ciano e 1h-imidazo [4,5-c] quinolina-4-carboxamida
MXPA05007485A (es)	2003-01-14	2006-01-30	Arena Pharm Inc	Derivados de arilo y heteroarilo 1,2,3-trisubstituidos como moduladores del metabolismo y la profilaxis y tratamiento de trastornos relacionados con ello tales como diabetes e hiperglicemia.
BRPI0407519A (pt)	2003-03-07	2006-02-14	Kowa Co	derivados de benzofurano
JP2006519877A (ja) *	2003-03-07	2006-08-31	スリーエムイノベイティブプロパティズカンパニー	１−アミノ１ｈ−イミダゾキノリン
US7163947B2 (en)	2003-03-07	2007-01-16	3M Innovative Properties Company	1-Amino 1H-imidazoquinolines
AR045047A1 (es)	2003-07-11	2005-10-12	Arena Pharm Inc	Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos
BRPI0413558A (pt)	2003-08-12	2006-10-17	3M Innovative Properties Co	compostos contendo imidazo substituìdo por hidroxilamina
AU2004268625B2 (en)	2003-08-27	2011-03-31	3M Innovative Properties Company	Aryloxy and arylalkyleneoxy substituted imidazoquinolines
AU2004270201A1 (en)	2003-09-05	2005-03-17	3M Innovative Properties Company	Treatment for CD5+ B cell lymphoma
AR046046A1 (es)	2003-10-03	2005-11-23	3M Innovative Properties Co	Imidazoquinolinas alcoxi sustituidas. composiciones farmaceuticas.
US7544697B2 (en)	2003-10-03	2009-06-09	Coley Pharmaceutical Group, Inc.	Pyrazolopyridines and analogs thereof
EP1685129A4 (en)	2003-11-14	2008-10-22	3M Innovative Properties Co	OXIMSUBSTITUTED IMIDAZORING CONNECTIONS
CA2545825A1 (en)	2003-11-14	2005-06-02	3M Innovative Properties Company	Hydroxylamine substituted imidazo ring compounds
PT1687305E (pt) *	2003-11-21	2008-10-17	Novartis Ag	Derivados de 1h-imidazoquinolina como inibidores de proteína quinase
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2001
- 2001-02-06 CA CA002399136A patent/CA2399136A1/en not_active Abandoned
- 2001-02-06 CZ CZ20022626A patent/CZ20022626A3/cs unknown
- 2001-02-06 EP EP01902774A patent/EP1256582A1/en not_active Withdrawn
- 2001-02-06 HU HU0204474A patent/HUP0204474A3/hu unknown
- 2001-02-06 CN CN01807727A patent/CN1422269A/zh active Pending
- 2001-02-06 KR KR1020027010326A patent/KR20020073211A/ko not_active Withdrawn
- 2001-02-06 WO PCT/JP2001/000816 patent/WO2001058900A1/ja not_active Ceased
- 2001-02-06 MX MXPA02007525A patent/MXPA02007525A/es not_active Application Discontinuation
- 2001-02-06 PL PL01355866A patent/PL355866A1/xx unknown
- 2001-02-06 US US10/181,407 patent/US20040054182A1/en not_active Abandoned
- 2001-02-06 SK SK1120-2002A patent/SK11202002A3/sk unknown
- 2001-02-06 BR BR0108303-1A patent/BR0108303A/pt not_active Application Discontinuation
- 2001-02-06 AU AU2001230584A patent/AU2001230584A1/en not_active Abandoned
- 2001-02-06 IL IL15084101A patent/IL150841A0/xx unknown
2002
- 2002-08-08 NO NO20023750A patent/NO20023750L/no not_active Application Discontinuation
- 2002-09-05 BG BG107067A patent/BG107067A/bg unknown

Also Published As

Publication number	Publication date
US20040054182A1 (en)	2004-03-18
HUP0204474A2 (hu)	2003-04-28
CN1422269A (zh)	2003-06-04
BG107067A (bg)	2003-09-30
CZ20022626A3 (cs)	2003-02-12
PL355866A1 (en)	2004-05-31
HUP0204474A3 (en)	2004-07-28
KR20020073211A (ko)	2002-09-19
WO2001058900A1 (en)	2001-08-16
EP1256582A1 (en)	2002-11-13
NO20023750L (no)	2002-10-07
IL150841A0 (en)	2003-02-12
MXPA02007525A (es)	2002-12-13
BR0108303A (pt)	2003-03-05
NO20023750D0 (no)	2002-08-08
AU2001230584A1 (en)	2001-08-20
CA2399136A1 (en)	2001-08-16

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