CA2772194A1

CA2772194A1 - Benzimidazole derivatives

Benzimidazole derivatives Download PDF

Info

Publication number: CA2772194A1
Authority: CA; Canada
Prior art keywords: cr13r14; methyl; nmr; alkyl; pyridin
Prior art date: 2009-09-01
Legal status : Abandoned

Application number

CA2772194A

Other languages

English (en)

French (fr)

Inventor

Sajiv Krishnan Nair

Simon Paul Planken

Michael Bruno Plewe

William Francois Vernier

Yi Yang

Huichun Zhu

Current Assignee

Pfizer Corp SRL

Original Assignee

Pfizer Corp SRL

Priority date

2009-09-01

Filing date

2010-08-11

Publication date

2011-03-10

2010-08-11 Application filed by Pfizer Corp SRL filed Critical Pfizer Corp SRL

2011-03-10 Publication of CA2772194A1 publication Critical patent/CA2772194A1/en

Status Abandoned legal-status Critical Current

Links

229940058303 antinematodal benzimidazole derivative Drugs 0.000 title abstract description 4
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 299
150000003839 salts Chemical class 0.000 claims abstract description 111
230000002159 abnormal effect Effects 0.000 claims abstract description 42
230000010261 cell growth Effects 0.000 claims abstract description 42
241000124008 Mammalia Species 0.000 claims abstract description 32
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 86
125000005843 halogen group Chemical group 0.000 claims description 82
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 50
239000003112 inhibitor Substances 0.000 claims description 40
125000000623 heterocyclic group Chemical group 0.000 claims description 39
239000003795 chemical substances by application Substances 0.000 claims description 28
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 25
125000001072 heteroaryl group Chemical group 0.000 claims description 22
125000003118 aryl group Chemical group 0.000 claims description 18
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 15
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 12
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 10
230000001028 anti-proliverative effect Effects 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
239000004037 angiogenesis inhibitor Substances 0.000 claims description 5
230000019491 signal transduction Effects 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims 4
101150020251 NR13 gene Proteins 0.000 claims 3
206010028980 Neoplasm Diseases 0.000 abstract description 68
238000000034 method Methods 0.000 abstract description 39
201000011510 cancer Diseases 0.000 abstract description 35
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 17
201000010099 disease Diseases 0.000 abstract description 9
230000001404 mediated effect Effects 0.000 abstract description 7
238000002560 therapeutic procedure Methods 0.000 abstract description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 403
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 298
238000005481 NMR spectroscopy Methods 0.000 description 193
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 171
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 95
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 89
238000005160 1H NMR spectroscopy Methods 0.000 description 87
239000000203 mixture Substances 0.000 description 73
229910052739 hydrogen Inorganic materials 0.000 description 71
238000002360 preparation method Methods 0.000 description 66
-1 hydrocarbon radicals Chemical class 0.000 description 59
239000000243 solution Substances 0.000 description 57
239000007787 solid Substances 0.000 description 47
235000019439 ethyl acetate Nutrition 0.000 description 46
238000006243 chemical reaction Methods 0.000 description 42
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 41
125000000217 alkyl group Chemical group 0.000 description 41
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
229910001868 water Inorganic materials 0.000 description 40
239000000543 intermediate Substances 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
210000004027 cell Anatomy 0.000 description 32
239000000047 product Substances 0.000 description 32
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 31
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 31
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 26
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
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239000011541 reaction mixture Substances 0.000 description 26
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239000002253 acid Substances 0.000 description 22
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150000001412 amines Chemical class 0.000 description 20
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 19
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239000011734 sodium Substances 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 16
239000012043 crude product Substances 0.000 description 15
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 15
229910052717 sulfur Inorganic materials 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
239000002585 base Substances 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
229940124530 sulfonamide Drugs 0.000 description 14
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 13
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239000012044 organic layer Substances 0.000 description 13
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 11
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229940100197 antimetabolite Drugs 0.000 description 11
239000002256 antimetabolite Substances 0.000 description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
239000012453 solvate Substances 0.000 description 11
238000006467 substitution reaction Methods 0.000 description 11
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206010046766 uterine cancer Diseases 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
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210000003169 central nervous system Anatomy 0.000 description 10
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208000014829 head and neck neoplasm Diseases 0.000 description 10
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
239000000725 suspension Substances 0.000 description 10
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229960004276 zoledronic acid Drugs 0.000 description 1
XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1