CA2682231A1 - Imidazo[1,2-a]pyridine compounds as receptor tyrosine kinase inhibitors - Google Patents

Imidazo[1,2-a]pyridine compounds as receptor tyrosine kinase inhibitors Download PDF

Info

Publication number: CA2682231A1
Authority: CA; Canada
Prior art keywords: alkyl; mmol; compound; formula; reaction
Prior art date: 2007-03-28
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002682231A

Other languages

English (en)

French (fr)

Inventor

Fredrik P. Marmsaeter

Mark C. Munson

James P. Rizzi

John E. Robinson

Stephen T. Schlachter

George T. Topalov

Qian Zhao

Joseph P. Lyssikatos

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Array Biopharma Inc

Original Assignee

Individual

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.)

2007-03-28

Filing date

2008-03-27

Publication date

2008-10-09

2008-03-27 Application filed by Individual filed Critical Individual

2008-10-09 Publication of CA2682231A1 publication Critical patent/CA2682231A1/en

Status Abandoned legal-status Critical Current

Links

229940127361 Receptor Tyrosine Kinase Inhibitors Drugs 0.000 title description 3
150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 177
238000011282 treatment Methods 0.000 claims abstract description 19
108091008598 receptor tyrosine kinases Proteins 0.000 claims abstract description 16
102000027426 receptor tyrosine kinases Human genes 0.000 claims abstract description 16
230000001404 mediated effect Effects 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims description 237
238000002360 preparation method Methods 0.000 claims description 184
238000000034 method Methods 0.000 claims description 74
-1 C(O)NHMe Chemical compound 0.000 claims description 55
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 48
229910052739 hydrogen Inorganic materials 0.000 claims description 46
150000003839 salts Chemical class 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
125000000753 cycloalkyl group Chemical group 0.000 claims description 27
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 25
229910052731 fluorine Inorganic materials 0.000 claims description 23
229910052801 chlorine Inorganic materials 0.000 claims description 17
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
206010028980 Neoplasm Diseases 0.000 claims description 16
229910052757 nitrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 15
125000004429 atom Chemical group 0.000 claims description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 13
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 12
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
125000004076 pyridyl group Chemical group 0.000 claims description 10
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
241000124008 Mammalia Species 0.000 claims description 9
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
229910052763 palladium Inorganic materials 0.000 claims description 9
XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 8
206010016654 Fibrosis Diseases 0.000 claims description 8
125000003386 piperidinyl group Chemical group 0.000 claims description 8
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 7
230000008878 coupling Effects 0.000 claims description 7
238000010168 coupling process Methods 0.000 claims description 7
238000005859 coupling reaction Methods 0.000 claims description 7
230000004761 fibrosis Effects 0.000 claims description 7
239000003446 ligand Substances 0.000 claims description 7
125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 6
239000003153 chemical reaction reagent Substances 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
125000002971 oxazolyl group Chemical group 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 5
239000003638 chemical reducing agent Substances 0.000 claims description 5
VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 5
201000011510 cancer Diseases 0.000 claims description 4
125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
230000001335 demethylating effect Effects 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 18
239000003112 inhibitor Substances 0.000 abstract description 16
101001001642 Xenopus laevis Serine/threonine-protein kinase pim-3 Proteins 0.000 abstract description 11
201000010099 disease Diseases 0.000 abstract description 10
102000005962 receptors Human genes 0.000 abstract description 3
108020003175 receptors Proteins 0.000 abstract description 3
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 abstract 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 322
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 275
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 267
238000006243 chemical reaction Methods 0.000 description 235
239000000203 mixture Substances 0.000 description 133
239000007787 solid Substances 0.000 description 128
201000006417 multiple sclerosis Diseases 0.000 description 124
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 106
235000019439 ethyl acetate Nutrition 0.000 description 104
239000000243 solution Substances 0.000 description 103
239000000047 product Substances 0.000 description 102
238000007792 addition Methods 0.000 description 90
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 77
239000011541 reaction mixture Substances 0.000 description 76
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
229910001868 water Inorganic materials 0.000 description 59
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 54
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 53
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 48
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 44
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 44
239000010410 layer Substances 0.000 description 43
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 43
229910052938 sodium sulfate Inorganic materials 0.000 description 41
235000011152 sodium sulphate Nutrition 0.000 description 41
238000010992 reflux Methods 0.000 description 40
239000007832 Na2SO4 Substances 0.000 description 39
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
239000012044 organic layer Substances 0.000 description 39
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 36
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 35
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
238000003818 flash chromatography Methods 0.000 description 32
BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 description 32
238000003756 stirring Methods 0.000 description 32
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
239000003921 oil Substances 0.000 description 29
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 28
229920006395 saturated elastomer Polymers 0.000 description 28
239000012074 organic phase Substances 0.000 description 24
CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 23
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
229910052786 argon Inorganic materials 0.000 description 22
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 22
229910000041 hydrogen chloride Inorganic materials 0.000 description 22
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
235000011114 ammonium hydroxide Nutrition 0.000 description 21
229910052943 magnesium sulfate Inorganic materials 0.000 description 18
229910000024 caesium carbonate Inorganic materials 0.000 description 17
210000004027 cell Anatomy 0.000 description 17
235000019341 magnesium sulphate Nutrition 0.000 description 17
238000010898 silica gel chromatography Methods 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 16
239000000706 filtrate Substances 0.000 description 15
HBBYDTFNQNAFJA-UHFFFAOYSA-N 4-(2-methoxyethoxy)pyridin-2-amine Chemical compound COCCOC1=CC=NC(N)=C1 HBBYDTFNQNAFJA-UHFFFAOYSA-N 0.000 description 14
239000000741 silica gel Substances 0.000 description 14
229910002027 silica gel Inorganic materials 0.000 description 14
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 14
CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 0.000 description 14
CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 14
101150041968 CDC13 gene Proteins 0.000 description 13
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical group C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 13
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102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 description 10
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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 10
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KDBADDXDBJFAAO-UHFFFAOYSA-N 7-(2-methoxyethoxy)imidazo[1,2-a]pyridine Chemical compound C1=C(OCCOC)C=CN2C=CN=C21 KDBADDXDBJFAAO-UHFFFAOYSA-N 0.000 description 8
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VBGAGHHSRWJFCP-UHFFFAOYSA-N [2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinolin-8-yl] trifluoromethanesulfonate Chemical compound C1=CC=C(OS(=O)(=O)C(F)(F)F)C2=NC(C=3N4C=CC(=CC4=NC=3)OCCOC)=CC=C21 VBGAGHHSRWJFCP-UHFFFAOYSA-N 0.000 description 8
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SRJOCJYGOFTFLH-UHFFFAOYSA-M piperidine-4-carboxylate Chemical compound [O-]C(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-M 0.000 description 7
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239000002904 solvent Substances 0.000 description 7
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238000003556 assay Methods 0.000 description 6
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JXBLMDWEOQDVAC-CABCVRRESA-N tert-butyl (3r,4s)-4-(benzylamino)-3-fluoropiperidine-1-carboxylate Chemical compound F[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]1NCC1=CC=CC=C1 JXBLMDWEOQDVAC-CABCVRRESA-N 0.000 description 1
ZQRYPCAUVKVMLZ-SFYZADRCSA-N tert-butyl (3r,4s)-4-amino-3-fluoropiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@H](N)[C@H](F)C1 ZQRYPCAUVKVMLZ-SFYZADRCSA-N 0.000 description 1
DHHKPEUQJIEKOA-UHFFFAOYSA-N tert-butyl 2-[6-(nitromethyl)-6-bicyclo[3.2.0]hept-3-enyl]acetate Chemical class C1C=CC2C(CC(=O)OC(C)(C)C)(C[N+]([O-])=O)CC21 DHHKPEUQJIEKOA-UHFFFAOYSA-N 0.000 description 1
WQBMVRTXKYXMKT-UHFFFAOYSA-N tert-butyl 3,3-difluoro-4,4-dihydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)(O)C(F)(F)C1 WQBMVRTXKYXMKT-UHFFFAOYSA-N 0.000 description 1
ZTMJHPULXULBFM-UHFFFAOYSA-N tert-butyl 4-(benzylamino)-3,3-difluoropiperidine-1-carboxylate Chemical compound FC1(F)CN(C(=O)OC(C)(C)C)CCC1NCC1=CC=CC=C1 ZTMJHPULXULBFM-UHFFFAOYSA-N 0.000 description 1
USCZMHLECBLPPD-UHFFFAOYSA-N tert-butyl 4-[2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinolin-8-yl]-2,2-dimethylpiperazine-1-carboxylate Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2N1CCN(C(=O)OC(C)(C)C)C(C)(C)C1 USCZMHLECBLPPD-UHFFFAOYSA-N 0.000 description 1
XEZSCKXSAIFPAD-UHFFFAOYSA-N tert-butyl 4-[2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinolin-8-yl]piperazine-1-carboxylate Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2N1CCN(C(=O)OC(C)(C)C)CC1 XEZSCKXSAIFPAD-UHFFFAOYSA-N 0.000 description 1
SSVAIVLVDFIXMM-UHFFFAOYSA-N tert-butyl 4-[5-fluoro-2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinolin-8-yl]-2,2-dimethylpiperazine-1-carboxylate Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C(F)=CC=C2N1CCN(C(=O)OC(C)(C)C)C(C)(C)C1 SSVAIVLVDFIXMM-UHFFFAOYSA-N 0.000 description 1
SAOQAHPRZCCSTJ-UHFFFAOYSA-N tert-butyl 4-[6-fluoro-2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinolin-8-yl]-2,2-dimethylpiperazine-1-carboxylate Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=C(F)C=C2N1CCN(C(=O)OC(C)(C)C)C(C)(C)C1 SAOQAHPRZCCSTJ-UHFFFAOYSA-N 0.000 description 1
QZVYQNHTMJZPLS-UHFFFAOYSA-N tert-butyl n-(2-iodo-6-methoxyphenyl)carbamate Chemical compound COC1=CC=CC(I)=C1NC(=O)OC(C)(C)C QZVYQNHTMJZPLS-UHFFFAOYSA-N 0.000 description 1
DHSWMVURURVRDB-UHFFFAOYSA-N tert-butyl n-(2-methoxyphenyl)carbamate Chemical compound COC1=CC=CC=C1NC(=O)OC(C)(C)C DHSWMVURURVRDB-UHFFFAOYSA-N 0.000 description 1
VDQMWAAIGRWIGJ-HZPDHXFCSA-N tert-butyl n-[(3r,4r)-3-fluoro-1-(5-fluoro-2-methylquinolin-8-yl)piperidin-4-yl]carbamate Chemical compound C12=NC(C)=CC=C2C(F)=CC=C1N1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](F)C1 VDQMWAAIGRWIGJ-HZPDHXFCSA-N 0.000 description 1
OAJHHZOPBGGGSM-UHFFFAOYSA-N tert-butyl n-[1-[2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-6-(trifluoromethyl)quinolin-8-yl]piperidin-4-yl]carbamate Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=C(C(F)(F)F)C=C2N1CCC(NC(=O)OC(C)(C)C)CC1 OAJHHZOPBGGGSM-UHFFFAOYSA-N 0.000 description 1
IYJNYSQLKKOOBC-UHFFFAOYSA-N tert-butyl n-[2-methoxy-6-(2-trimethylsilylethynyl)phenyl]carbamate Chemical compound COC1=CC=CC(C#C[Si](C)(C)C)=C1NC(=O)OC(C)(C)C IYJNYSQLKKOOBC-UHFFFAOYSA-N 0.000 description 1
RWPNJSUSYUZBDY-UHFFFAOYSA-N tert-butyl n-[2-methoxy-6-[3-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-3-oxoprop-1-ynyl]phenyl]carbamate Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(=O)C#CC1=CC=CC(OC)=C1NC(=O)OC(C)(C)C RWPNJSUSYUZBDY-UHFFFAOYSA-N 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
239000012085 test solution Substances 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical compound C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
210000005166 vasculature Anatomy 0.000 description 1
230000035899 viability Effects 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
239000003039 volatile agent 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
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
- 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
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics

Landscapes

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

CA002682231A 2007-03-28 2008-03-27 Imidazo[1,2-a]pyridine compounds as receptor tyrosine kinase inhibitors Abandoned CA2682231A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US90855607P	2007-03-28	2007-03-28
US60/908,556		2007-03-28
PCT/US2008/058385 WO2008121687A2 (en)	2007-03-28	2008-03-27	Imidazo[1,2-a]pyridine compounds as receptor tyrosine kinase inhibitors

Publications (1)

Publication Number	Publication Date
CA2682231A1 true CA2682231A1 (en)	2008-10-09

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ID=39731287

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002682231A Abandoned CA2682231A1 (en)	2007-03-28	2008-03-27	Imidazo[1,2-a]pyridine compounds as receptor tyrosine kinase inhibitors

Country Status (7)

Country	Link
US (1)	US20100144751A1 (2)
EP (1)	EP2139888A2 (2)
JP (1)	JP2010522765A (2)
CN (1)	CN101679422A (2)
CA (1)	CA2682231A1 (2)
TW (1)	TW200843757A (2)
WO (1)	WO2008121687A2 (2)

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US20050256309A1 (en) *	2004-05-12	2005-11-17	Altenbach Robert J	Tri-and bi-cyclic heteroaryl histamine-3 receptor ligands

2008
- 2008-03-27 JP JP2010501214A patent/JP2010522765A/ja active Pending
- 2008-03-27 US US12/593,041 patent/US20100144751A1/en not_active Abandoned
- 2008-03-27 CN CN200880017972A patent/CN101679422A/zh active Pending
- 2008-03-27 EP EP08732914A patent/EP2139888A2/en not_active Withdrawn
- 2008-03-27 WO PCT/US2008/058385 patent/WO2008121687A2/en not_active Ceased
- 2008-03-27 CA CA002682231A patent/CA2682231A1/en not_active Abandoned
- 2008-03-28 TW TW097111546A patent/TW200843757A/zh unknown

Also Published As

Publication number	Publication date
EP2139888A2 (en)	2010-01-06
CN101679422A (zh)	2010-03-24
JP2010522765A (ja)	2010-07-08
US20100144751A1 (en)	2010-06-10
TW200843757A (en)	2008-11-16
WO2008121687A2 (en)	2008-10-09
WO2008121687A3 (en)	2008-11-20

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Date	Code	Title	Description
2014-05-22	FZDE	Discontinued	Effective date: 20140327

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