BG107067A - Прозводни на 1н-имидазопиридин - Google Patents

Прозводни на 1н-имидазопиридин Download PDF

Info

Publication number: BG107067A
Authority: BG; Bulgaria
Prior art keywords: group; substituted; ethyl; calculated; found
Prior art date: 2000-02-09

Application number

BG107067A

Other languages

Bulgarian (bg)

English (en)

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

2002-09-05

Publication date

2003-09-30

2002-09-05 Application filed by Hokuriku Seiyaku Co., Ltd filed Critical Hokuriku Seiyaku Co., Ltd

2003-09-30 Publication of BG107067A publication Critical patent/BG107067A/bg

Links

GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 title claims abstract description 11
-1 cyano, mercapto, carboxy Chemical group 0.000 claims abstract description 255
150000003839 salts Chemical class 0.000 claims abstract description 40
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 25
125000000217 alkyl group Chemical group 0.000 claims abstract description 17
125000003118 aryl group Chemical group 0.000 claims abstract description 14
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
150000001875 compounds Chemical class 0.000 claims description 115
UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 claims description 19
239000004062 cytokinin Substances 0.000 claims description 19
108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 17
238000004519 manufacturing process Methods 0.000 claims description 17
125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
229910052757 nitrogen Inorganic materials 0.000 claims description 15
125000003277 amino group Chemical group 0.000 claims description 14
239000003814 drug Substances 0.000 claims description 14
102000003390 tumor necrosis factor Human genes 0.000 claims description 13
102000000589 Interleukin-1 Human genes 0.000 claims description 12
108010002352 Interleukin-1 Proteins 0.000 claims description 12
201000010099 disease Diseases 0.000 claims description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
125000002252 acyl group Chemical group 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 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
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
230000003449 preventive effect Effects 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
230000001225 therapeutic effect Effects 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
125000000547 substituted alkyl group Chemical group 0.000 claims description 4
125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
239000003112 inhibitor Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 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
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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
239000011593 sulfur Substances 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 abstract description 12
230000000694 effects Effects 0.000 abstract description 4
239000001257 hydrogen Substances 0.000 abstract description 3
229910052739 hydrogen Inorganic materials 0.000 abstract description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 3
230000016396 cytokine production Effects 0.000 abstract 1
229910052799 carbon Inorganic materials 0.000 description 372
238000000921 elemental analysis Methods 0.000 description 186
239000013078 crystal Substances 0.000 description 158
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 135
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 124
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 113
239000002904 solvent Substances 0.000 description 102
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 91
238000001953 recrystallisation Methods 0.000 description 55
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 53
238000000354 decomposition reaction Methods 0.000 description 53
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 45
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 44
238000002844 melting Methods 0.000 description 43
230000008018 melting Effects 0.000 description 43
239000000203 mixture Substances 0.000 description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 32
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 31
238000000034 method Methods 0.000 description 31
230000000704 physical effect Effects 0.000 description 31
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
MBEOKCONJLQHKT-UHFFFAOYSA-N 1-methylimidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(C)C=NC3=CN=C21 MBEOKCONJLQHKT-UHFFFAOYSA-N 0.000 description 29
125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 28
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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 19
238000006243 chemical reaction Methods 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 18
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
239000002585 base Substances 0.000 description 18
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
238000002360 preparation method Methods 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 14
125000001424 substituent group Chemical group 0.000 description 14
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 13
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 13
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 13
229910000027 potassium carbonate Inorganic materials 0.000 description 13
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000002253 acid Substances 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
102000003777 Interleukin-1 beta Human genes 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
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 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
DLKYQYMXPSONJP-UHFFFAOYSA-N cyclopenta[b]pyridine Chemical compound C1=C[N]C2=CC=CC2=C1 DLKYQYMXPSONJP-UHFFFAOYSA-N 0.000 description 9
239000007788 liquid Substances 0.000 description 9
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
108090000193 Interleukin-1 beta 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
238000009835 boiling Methods 0.000 description 8
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
238000012360 testing method Methods 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
MEOYIJFTDKUQMA-UHFFFAOYSA-N 1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 MEOYIJFTDKUQMA-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
239000012156 elution solvent Substances 0.000 description 6
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
229960001866 silicon dioxide Drugs 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
KRNSYSYRLQDHDK-UHFFFAOYSA-N 2,3-Cyclopentenopyridine Natural products C1=CN=C2CCCC2=C1 KRNSYSYRLQDHDK-UHFFFAOYSA-N 0.000 description 5
LXDQAYVVBNBFNK-UHFFFAOYSA-N 8-methyl-2-phenyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CNCCC1CCN1C=2C3=CC(C)=CC=C3N=C(C(F)(F)F)C=2N=C1C1=CC=CC=C1 LXDQAYVVBNBFNK-UHFFFAOYSA-N 0.000 description 5
108010001336 Horseradish Peroxidase Proteins 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
238000001816 cooling Methods 0.000 description 5
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 5
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 5
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 5
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 5
125000005936 piperidyl group Chemical group 0.000 description 5
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 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
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
102000014150 Interferons Human genes 0.000 description 4
108010050904 Interferons Proteins 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 4
235000011054 acetic acid Nutrition 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
230000001363 autoimmune Effects 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 4
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 4
235000011087 fumaric acid Nutrition 0.000 description 4
229940079322 interferon Drugs 0.000 description 4
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000011591 potassium Substances 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
238000001228 spectrum Methods 0.000 description 4
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
FYSYVVFOPRAZJC-UHFFFAOYSA-N 1-(2-piperidin-4-ylethyl)-2,4-bis(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound FC(F)(F)C1=NC2=C(C(F)(F)F)N=C3C=CC=CC3=C2N1CCC1CCNCC1 FYSYVVFOPRAZJC-UHFFFAOYSA-N 0.000 description 3
GROOAWILZDAAFL-UHFFFAOYSA-N 2-(methylamino)-n-[2-[2-(1h-pyrrol-2-yl)-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)CNC)C=1C1=CC=CN1 GROOAWILZDAAFL-UHFFFAOYSA-N 0.000 description 3
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 3
FTZWNHXSZYXEJO-UHFFFAOYSA-N 2-cyclohexyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCCC1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 FTZWNHXSZYXEJO-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
PPAKZWZXDSHBFO-UHFFFAOYSA-N n-[2-(4-methyl-2-phenylimidazo[4,5-c]quinolin-1-yl)ethyl]butan-1-amine Chemical compound N=1C2=C(C)N=C3C=CC=CC3=C2N(CCNCCCC)C=1C1=CC=CC=C1 PPAKZWZXDSHBFO-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
125000006606 n-butoxy group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
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239000007923 nasal drop Substances 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
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
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical group CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
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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
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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
235000005985 organic acids Nutrition 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
239000003002 pH adjusting agent Substances 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
238000007911 parenteral administration Methods 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
108040007629 peroxidase activity proteins Proteins 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 1
229960005235 piperonyl butoxide Drugs 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
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000006308 propyl amino group Chemical group 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 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
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
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000011002 quantification Methods 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
238000000926 separation method Methods 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
229960004029 silicic acid Drugs 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
235000002316 solid fats Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
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
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
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
PFUNHNGQUCDGDX-UHFFFAOYSA-N tert-butyl 4-[2-[2-phenyl-4-(trifluoromethyl)imidazo[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(F)(F)F)=C2N=C1C1=CC=CC=C1 PFUNHNGQUCDGDX-UHFFFAOYSA-N 0.000 description 1
BOEDFAOCQPHVGX-UHFFFAOYSA-N tert-butyl 4-[2-[[3-amino-2-(trifluoromethyl)quinolin-4-yl]amino]ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCNC1=C(N)C(C(F)(F)F)=NC2=CC=CC=C12 BOEDFAOCQPHVGX-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
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
208000014754 thrombocytosis disease Diseases 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
150000003673 urethanes Chemical class 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003871 white petrolatum 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)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (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)
Diabetes (AREA)
Epidemiology (AREA)
Pulmonology (AREA)
Rheumatology (AREA)
Biomedical Technology (AREA)
Pain & Pain Management (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Hematology (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)

BG107067A 2000-02-09 2002-09-05 Прозводни на 1н-имидазопиридин BG107067A (bg)

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
BG107067A true BG107067A (bg)	2003-09-30

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

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GB0211649D0 (en)	2002-05-21	2002-07-03	Novartis Ag	Organic compounds
IL166307A0 (en)	2002-07-26	2006-01-15		Preparation of 1h-imidazoÄ4,5-cÜquinolin-4-amines via novel 1h-imidazoÄ4,5-cÜquinolin-4-cyano and 1h-imidazo Ä4,5-cÜquinolin-4-cyano and 1h-imidazoÄ4,5-cÜquinolin-4-carboxamide intermediates
AU2004205642C1 (en)	2003-01-14	2012-01-12	Arena Pharmaceuticals, Inc.	1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia
US7163947B2 (en)	2003-03-07	2007-01-16	3M Innovative Properties Company	1-Amino 1H-imidazoquinolines
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
US7314877B2 (en)	2003-03-07	2008-01-01	Kowa Co., Ltd.	Benzofuran derivative
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
TW200510412A (en)	2003-08-12	2005-03-16	3M Innovative Properties Co	Oxime substituted imidazo-containing compounds
AR045529A1 (es)	2003-08-27	2005-11-02	3M Innovative Properties Co	Imidazoquinolinas sustituidas con grupos ariloxi o arilalquilenoxi
CA2537763A1 (en)	2003-09-05	2005-03-17	3M Innovative Properties Company	Treatment for cd5+ b cell lymphoma
WO2005032484A2 (en)	2003-10-03	2005-04-14	3M Innovative Properties Company	Alkoxy substituted imidazoquinolines
US7544697B2 (en)	2003-10-03	2009-06-09	Coley Pharmaceutical Group, Inc.	Pyrazolopyridines and analogs thereof
EP1682544A4 (en)	2003-11-14	2009-05-06	3M Innovative Properties Co	HYDROXYLAMINE SUBSTITUTED IMIDAZO RING COMPOUNDS
JP2007511527A (ja)	2003-11-14	2007-05-10	スリーエムイノベイティブプロパティズカンパニー	オキシム置換イミダゾ環化合物
AR046845A1 (es) *	2003-11-21	2005-12-28	Novartis Ag	Derivados de 1h-imidazo[4,5-c]quinolina para tratamiento de enfermedades dependientes de las proteino-quinasas
AU2004295061B2 (en) *	2003-11-21	2008-11-20	Novartis Ag	1H-imidazoquinoline derivatives as protein kinase inhibitors
AU2004293078B2 (en)	2003-11-25	2012-01-19	3M Innovative Properties Company	Substituted imidazo ring systems and methods
US8802853B2 (en)	2003-12-29	2014-08-12	3M Innovative Properties Company	Arylalkenyl and arylalkynyl substituted imidazoquinolines
EP1699788A2 (en)	2003-12-30	2006-09-13	3M Innovative Properties Company	Imidazoquinolinyl, imidazopyridinyl and imidazonaphthyridinyl sulfonamides
EP1730143A2 (en)	2004-03-24	2006-12-13	3M Innovative Properties Company	Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines
EP3001990A1 (en)	2004-05-28	2016-04-06	Oryxe	A mixture for transdermal delivery of low& and high molecular weight compounds
US8017779B2 (en)	2004-06-15	2011-09-13	3M Innovative Properties Company	Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines
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2001
- 2001-02-06 HU HU0204474A patent/HUP0204474A3/hu unknown
- 2001-02-06 BR BR0108303-1A patent/BR0108303A/pt not_active Application Discontinuation
- 2001-02-06 CZ CZ20022626A patent/CZ20022626A3/cs unknown
- 2001-02-06 MX MXPA02007525A patent/MXPA02007525A/es not_active Application Discontinuation
- 2001-02-06 PL PL01355866A patent/PL355866A1/xx unknown
- 2001-02-06 CA CA002399136A patent/CA2399136A1/en not_active Abandoned
- 2001-02-06 AU AU2001230584A patent/AU2001230584A1/en not_active Abandoned
- 2001-02-06 SK SK1120-2002A patent/SK11202002A3/sk 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 US US10/181,407 patent/US20040054182A1/en not_active Abandoned
- 2001-02-06 WO PCT/JP2001/000816 patent/WO2001058900A1/ja not_active Ceased
- 2001-02-06 EP EP01902774A patent/EP1256582A1/en not_active Withdrawn
- 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
WO2001058900A1 (en)	2001-08-16
NO20023750D0 (no)	2002-08-08
IL150841A0 (en)	2003-02-12
AU2001230584A1 (en)	2001-08-20
NO20023750L (no)	2002-10-07
KR20020073211A (ko)	2002-09-19
US20040054182A1 (en)	2004-03-18
CZ20022626A3 (cs)	2003-02-12
HUP0204474A2 (hu)	2003-04-28
MXPA02007525A (es)	2002-12-13
PL355866A1 (en)	2004-05-31
CA2399136A1 (en)	2001-08-16
SK11202002A3 (sk)	2003-03-04
EP1256582A1 (en)	2002-11-13
CN1422269A (zh)	2003-06-04
HUP0204474A3 (en)	2004-07-28
BR0108303A (pt)	2003-03-05

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