SK1942001A3 - 1h-imidazopyridine derivatives - Google Patents

1h-imidazopyridine derivatives Download PDF

Info

Publication number: SK1942001A3
Authority: SK; Slovakia
Prior art keywords: found; calculated; elemental analysis; group; optionally substituted
Prior art date: 1998-08-12

Application number

SK194-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Hideo Kato

Jun Sakaguchi

Makoto Aoyama

Tomoyuki Izumi

Ken-Ichi Kato

Original Assignee

Hokuriku Pharmaceutical

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.)

1998-08-12

Filing date

1999-08-12

Publication date

2001-12-03

1999-08-12 Application filed by Hokuriku Pharmaceutical filed Critical Hokuriku Pharmaceutical

2001-12-03 Publication of SK1942001A3 publication Critical patent/SK1942001A3/sk

Links

GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 title claims abstract description 12
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 26
150000003839 salts Chemical class 0.000 claims abstract description 23
125000000217 alkyl group Chemical group 0.000 claims abstract description 21
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 19
125000002887 hydroxy group Chemical group [H]O* 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
239000003814 drug Substances 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
125000003277 amino group Chemical group 0.000 claims abstract description 9
125000003118 aryl group Chemical group 0.000 claims abstract description 9
125000005843 halogen group Chemical group 0.000 claims abstract description 8
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 8
201000010099 disease Diseases 0.000 claims abstract description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
125000004122 cyclic group Chemical group 0.000 claims abstract description 6
230000001404 mediated effect Effects 0.000 claims abstract description 6
230000003449 preventive effect Effects 0.000 claims abstract description 6
125000005504 styryl group Chemical group 0.000 claims abstract description 4
-1 hydroxy, amino Chemical group 0.000 claims description 154
150000001875 compounds Chemical class 0.000 claims description 125
125000001424 substituent group Chemical group 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
230000001225 therapeutic effect Effects 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
125000001589 carboacyl group Chemical group 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
229910052717 sulfur Inorganic materials 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
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
108010002352 Interleukin-1 Proteins 0.000 abstract description 11
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125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
229940124597 therapeutic agent Drugs 0.000 abstract description 2
239000013078 crystal Substances 0.000 description 276
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238000000921 elemental analysis Methods 0.000 description 221
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239000002904 solvent Substances 0.000 description 136
238000001953 recrystallisation Methods 0.000 description 106
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 70
230000000704 physical effect Effects 0.000 description 70
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238000002360 preparation method Methods 0.000 description 31
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 30
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239000011541 reaction mixture Substances 0.000 description 27
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238000002329 infrared spectrum Methods 0.000 description 25
238000001819 mass spectrum Methods 0.000 description 25
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238000000354 decomposition reaction Methods 0.000 description 24
239000007787 solid Substances 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 20
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
238000010992 reflux Methods 0.000 description 19
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
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102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 18
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 17
239000002253 acid Substances 0.000 description 16
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239000000725 suspension Substances 0.000 description 16
239000002585 base Substances 0.000 description 15
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 13
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
235000017557 sodium bicarbonate Nutrition 0.000 description 12
229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
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229920006395 saturated elastomer Polymers 0.000 description 11
102000000589 Interleukin-1 Human genes 0.000 description 10
238000004458 analytical method Methods 0.000 description 10
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239000000706 filtrate Substances 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
235000011181 potassium carbonates Nutrition 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 9
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
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DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 8
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229910000041 hydrogen chloride Inorganic materials 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
125000001309 chloro group Chemical group Cl* 0.000 description 7
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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
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QMVWLIJVQMAPNJ-UHFFFAOYSA-N 4-chloro-2-phenyl-1-(2-piperidin-4-ylethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CC=CC=1C1=NC=2C(Cl)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 QMVWLIJVQMAPNJ-UHFFFAOYSA-N 0.000 description 4
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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
239000011664 nicotinic acid Substances 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
230000000802 nitrating effect Effects 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
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235000006408 oxalic acid Nutrition 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
229940049954 penicillin Drugs 0.000 description 1
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125000004193 piperazinyl group Chemical group 0.000 description 1
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239000011698 potassium fluoride Substances 0.000 description 1
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230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
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235000019260 propionic acid Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
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125000003373 pyrazinyl group Chemical group 0.000 description 1
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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
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125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
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125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 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
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239000011775 sodium fluoride Substances 0.000 description 1
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239000012312 sodium hydride Substances 0.000 description 1
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235000009518 sodium iodide Nutrition 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
235000002316 solid fats Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
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239000011593 sulfur Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
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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
QLEBCEWTHGUFFL-UHFFFAOYSA-N tert-butyl 2-(2-aminoethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CCN QLEBCEWTHGUFFL-UHFFFAOYSA-N 0.000 description 1
LTVQOFUGXMVESU-UHFFFAOYSA-N tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CCO LTVQOFUGXMVESU-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
BMVYEMPFWRVJDI-UHFFFAOYSA-N tert-butyl 4-[2-(4-chloro-2-phenylimidazo[4,5-c]quinolin-1-yl)ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CCN1C2=C3C=CC=CC3=NC(Cl)=C2N=C1C1=CC=CC=C1 BMVYEMPFWRVJDI-UHFFFAOYSA-N 0.000 description 1
TZDSMIRVTHMPJX-UHFFFAOYSA-N tert-butyl 4-[2-(4-chloroimidazo[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=C1 TZDSMIRVTHMPJX-UHFFFAOYSA-N 0.000 description 1
VFLQQXGRWRNPDV-UHFFFAOYSA-N tert-butyl 4-[2-(4-methyl-2-phenylimidazo[4,5-c]quinolin-1-yl)ethyl]piperidine-1-carboxylate Chemical compound C=1C=CC=CC=1C1=NC=2C(C)=NC3=CC=CC=C3C=2N1CCC1CCN(C(=O)OC(C)(C)C)CC1 VFLQQXGRWRNPDV-UHFFFAOYSA-N 0.000 description 1
FBRKJQSDUVTTSS-UHFFFAOYSA-N tert-butyl 4-[2-(4-phenoxyimidazo[4,5-c]quinolin-1-yl)ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCN1C2=C3C=CC=CC3=NC(OC=3C=CC=CC=3)=C2N=C1 FBRKJQSDUVTTSS-UHFFFAOYSA-N 0.000 description 1
XUXPCJCADQDFMU-UHFFFAOYSA-N tert-butyl 4-[2-[(3-amino-2-chloroquinolin-4-yl)amino]ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCNC1=C(N)C(Cl)=NC2=CC=CC=C12 XUXPCJCADQDFMU-UHFFFAOYSA-N 0.000 description 1
YIXXKCRXDCSEHP-UHFFFAOYSA-N tert-butyl 4-[2-[(3-amino-2-methylquinolin-4-yl)amino]ethyl]piperidine-1-carboxylate Chemical compound NC=1C(C)=NC2=CC=CC=C2C=1NCCC1CCN(C(=O)OC(C)(C)C)CC1 YIXXKCRXDCSEHP-UHFFFAOYSA-N 0.000 description 1
VMXWCDCVPIBFHA-UHFFFAOYSA-N tert-butyl 4-[2-[4-(4-methylpiperazin-1-yl)-2-phenylimidazo[4,5-c]quinolin-1-yl]ethyl]piperidine-1-carboxylate Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2C2=C1N=C(C=1C=CC=CC=1)N2CCC1CCN(C(=O)OC(C)(C)C)CC1 VMXWCDCVPIBFHA-UHFFFAOYSA-N 0.000 description 1
UZGZHCCVZAZESA-UHFFFAOYSA-N tert-butyl 4-[2-[4-(dimethylamino)-2-phenylimidazo[4,5-c]quinolin-1-yl]ethyl]piperidine-1-carboxylate Chemical compound C=1C=CC=CC=1C1=NC=2C(N(C)C)=NC3=CC=CC=C3C=2N1CCC1CCN(C(=O)OC(C)(C)C)CC1 UZGZHCCVZAZESA-UHFFFAOYSA-N 0.000 description 1
HXUDZPPHWGODFI-UHFFFAOYSA-N tert-butyl 4-[2-[4-chloro-2-(4-methylsulfanylphenyl)imidazo[4,5-c]quinolin-1-yl]ethyl]piperidine-1-carboxylate Chemical compound C1=CC(SC)=CC=C1C1=NC2=C(Cl)N=C(C=CC=C3)C3=C2N1CCC1CCN(C(=O)OC(C)(C)C)CC1 HXUDZPPHWGODFI-UHFFFAOYSA-N 0.000 description 1
ZFIRSVJOUWWRQK-UHFFFAOYSA-N tert-butyl 4-[2-[4-chloro-2-(4-methylsulfinylphenyl)imidazo[4,5-c]quinolin-1-yl]ethyl]piperidine-1-carboxylate Chemical compound C1=CC(S(=O)C)=CC=C1C1=NC2=C(Cl)N=C(C=CC=C3)C3=C2N1CCC1CCN(C(=O)OC(C)(C)C)CC1 ZFIRSVJOUWWRQK-UHFFFAOYSA-N 0.000 description 1
YCLQBDDMASWAJG-UHFFFAOYSA-N tert-butyl 4-[2-[4-chloro-2-(4-methylsulfonylphenyl)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(Cl)=C2N=C1C1=CC=C(S(C)(=O)=O)C=C1 YCLQBDDMASWAJG-UHFFFAOYSA-N 0.000 description 1
JUVKPFCLAYXDPB-UHFFFAOYSA-N tert-butyl n-[1-(cyanomethyl)piperidin-4-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1CCN(CC#N)CC1 JUVKPFCLAYXDPB-UHFFFAOYSA-N 0.000 description 1
DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
208000018464 vernal keratoconjunctivitis Diseases 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
239000008096 xylene Substances 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
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- A61P35/00—Antineoplastic 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
- 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
- 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)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Pulmonology (AREA)
Rheumatology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

SK194-2001A 1998-08-12 1999-08-12 1h-imidazopyridine derivatives SK1942001A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP24106298		1998-08-12
JP11216125A JP2000119271A (ja)	1998-08-12	1999-07-30	１ｈ―イミダゾピリジン誘導体
PCT/JP1999/004381 WO2000009506A1 (en)	1998-08-12	1999-08-12	1h-imidazopyridine derivatives

Publications (1)

Publication Number	Publication Date
SK1942001A3 true SK1942001A3 (en)	2001-12-03

Family

ID=26521247

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK194-2001A SK1942001A3 (en)	1998-08-12	1999-08-12	1h-imidazopyridine derivatives

Country Status (21)

Country	Link
US (1)	US6518265B1 (pt)
EP (1)	EP1104764A4 (pt)
JP (1)	JP2000119271A (pt)
CN (1)	CN1323307A (pt)
AU (1)	AU744388B2 (pt)
BG (1)	BG105271A (pt)
BR (1)	BR9914306A (pt)
CA (1)	CA2339562A1 (pt)
CZ (1)	CZ292544B6 (pt)
EA (1)	EA200100230A1 (pt)
HK (1)	HK1042295A1 (pt)
HR (1)	HRP20010144A2 (pt)
HU (1)	HUP0103406A3 (pt)
IL (1)	IL141226A0 (pt)
NO (1)	NO20010676L (pt)
NZ (1)	NZ509939A (pt)
PL (1)	PL346155A1 (pt)
SK (1)	SK1942001A3 (pt)
TR (1)	TR200100439T2 (pt)
TW (1)	TW533209B (pt)
WO (1)	WO2000009506A1 (pt)

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JP3436512B2 (ja) *	1999-12-28	2003-08-11	株式会社デンソー	アクセル装置
CA2399136A1 (en) *	2000-02-09	2001-08-16	Hideo Kato	1h-imidazopyridine derivatives
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AU2001278790A1 (en) *	2000-08-22	2002-03-04	Hokuriku Seiyaku Co. Ltd	1h-imidazopyridine derivatives
US6576644B2 (en)	2000-09-06	2003-06-10	Bristol-Myers Squibb Co.	Quinoline inhibitors of cGMP phosphodiesterase
WO2002024684A1 (en) *	2000-09-21	2002-03-28	Smithkline Beecham P.L.C.	Quinoline derivatives as antibacterials
US7087224B2 (en) *	2000-10-31	2006-08-08	Amgen Inc.	Method of treating anemia by administering IL-1ra
US6660735B2 (en) *	2000-12-08	2003-12-09	3M Innovative Properties Company	Urea substituted imidazoquinoline ethers
UA74852C2 (en)	2000-12-08	2006-02-15	3M Innovative Properties Co	Urea-substituted imidazoquinoline ethers
US6660747B2 (en) *	2000-12-08	2003-12-09	3M Innovative Properties Company	Amido ether substituted imidazoquinolines
US6664260B2 (en)	2000-12-08	2003-12-16	3M Innovative Properties Company	Heterocyclic ether substituted imidazoquinolines
US6545016B1 (en)	2000-12-08	2003-04-08	3M Innovative Properties Company	Amide substituted imidazopyridines
EP1850850A4 (en) *	2000-12-08	2011-06-15	3M Innovative Properties Co	COMPOSITIONS AND METHOD FOR TARGETED ADMINISTRATION OF IMMUNE RESPONSE MODIFICATORS
US6677347B2 (en) *	2000-12-08	2004-01-13	3M Innovative Properties Company	Sulfonamido ether substituted imidazoquinolines
US6525064B1 (en)	2000-12-08	2003-02-25	3M Innovative Properties Company	Sulfonamido substituted imidazopyridines
US6664265B2 (en)	2000-12-08	2003-12-16	3M Innovative Properties Company	Amido ether substituted imidazoquinolines
US6664264B2 (en) *	2000-12-08	2003-12-16	3M Innovative Properties Company	Thioether substituted imidazoquinolines
US6677348B2 (en)	2000-12-08	2004-01-13	3M Innovative Properties Company	Aryl ether substituted imidazoquinolines
US6545017B1 (en)	2000-12-08	2003-04-08	3M Innovative Properties Company	Urea substituted imidazopyridines
US6667312B2 (en)	2000-12-08	2003-12-23	3M Innovative Properties Company	Thioether substituted imidazoquinolines
US7226928B2 (en)	2001-06-15	2007-06-05	3M Innovative Properties Company	Methods for the treatment of periodontal disease
ES2312659T3 (es)	2001-11-29	2009-03-01	3M Innovative Properties Company	Formulaciones farmaceuticas que comprenden un modificador de la respuesta inmune.
CA2365732A1 (en)	2001-12-20	2003-06-20	Ibm Canada Limited-Ibm Canada Limitee	Testing measurements
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- 1999-08-12 NZ NZ509939A patent/NZ509939A/xx unknown
- 1999-08-12 EA EA200100230A patent/EA200100230A1/ru unknown
- 1999-08-12 BR BR9914306-2A patent/BR9914306A/pt not_active IP Right Cessation
- 1999-08-12 AU AU51974/99A patent/AU744388B2/en not_active Ceased
- 1999-08-12 PL PL99346155A patent/PL346155A1/xx unknown
- 1999-08-12 HR HR20010144A patent/HRP20010144A2/hr not_active Application Discontinuation
- 1999-08-12 IL IL14122699A patent/IL141226A0/xx unknown
- 1999-08-12 CA CA002339562A patent/CA2339562A1/en not_active Abandoned
- 1999-08-12 WO PCT/JP1999/004381 patent/WO2000009506A1/ja not_active Ceased
- 1999-08-12 HK HK02103246.4A patent/HK1042295A1/zh unknown
- 1999-08-12 US US09/744,959 patent/US6518265B1/en not_active Expired - Fee Related
- 1999-08-12 CZ CZ2001503A patent/CZ292544B6/cs not_active IP Right Cessation
- 1999-08-12 TR TR2001/00439T patent/TR200100439T2/xx unknown
- 1999-08-12 EP EP99937053A patent/EP1104764A4/en not_active Withdrawn
- 1999-08-12 HU HU0103406A patent/HUP0103406A3/hu unknown
- 1999-08-12 CN CN99812056A patent/CN1323307A/zh active Pending
- 1999-08-12 SK SK194-2001A patent/SK1942001A3/sk unknown
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Also Published As

Publication number	Publication date
BR9914306A (pt)	2002-05-21
CN1323307A (zh)	2001-11-21
HUP0103406A2 (hu)	2002-02-28
EA200100230A1 (ru)	2001-10-22
CZ2001503A3 (cs)	2001-11-14
NO20010676D0 (no)	2001-02-09
US6518265B1 (en)	2003-02-11
HK1042295A1 (zh)	2002-08-09
JP2000119271A (ja)	2000-04-25
CZ292544B6 (cs)	2003-10-15
IL141226A0 (en)	2002-03-10
NO20010676L (no)	2001-04-10
NZ509939A (en)	2002-08-28
AU5197499A (en)	2000-03-06
AU744388B2 (en)	2002-02-21
EP1104764A4 (en)	2003-01-15
PL346155A1 (en)	2002-01-28
CA2339562A1 (en)	2000-02-24
BG105271A (bg)	2001-11-30
TW533209B (en)	2003-05-21
TR200100439T2 (tr)	2001-05-21
HRP20010144A2 (en)	2002-04-30
WO2000009506A1 (en)	2000-02-24
EP1104764A1 (en)	2001-06-06
HUP0103406A3 (en)	2002-11-28

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