HRP20041218A2 - Novel benzimidazole derivatives - Google Patents
Novel benzimidazole derivatives Download PDFInfo
- Publication number
- HRP20041218A2 HRP20041218A2 HR20041218A HRP20041218A HRP20041218A2 HR P20041218 A2 HRP20041218 A2 HR P20041218A2 HR 20041218 A HR20041218 A HR 20041218A HR P20041218 A HRP20041218 A HR P20041218A HR P20041218 A2 HRP20041218 A2 HR P20041218A2
- Authority
- HR
- Croatia
- Prior art keywords
- halogen
- lower alkyl
- hydroxy
- methine
- group
- Prior art date
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- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 359
- 150000001875 compounds Chemical class 0.000 claims description 296
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 274
- 125000003545 alkoxy group Chemical group 0.000 claims description 200
- -1 nitro, hydroxy Chemical group 0.000 claims description 182
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 171
- 125000001424 substituent group Chemical group 0.000 claims description 138
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 131
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 114
- 229910052736 halogen Inorganic materials 0.000 claims description 111
- 125000003118 aryl group Chemical group 0.000 claims description 105
- 229910052757 nitrogen Inorganic materials 0.000 claims description 87
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 239000001257 hydrogen Substances 0.000 claims description 74
- 238000000034 method Methods 0.000 claims description 73
- 208000008589 Obesity Diseases 0.000 claims description 68
- 235000020824 obesity Nutrition 0.000 claims description 68
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 57
- 238000011282 treatment Methods 0.000 claims description 56
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 55
- 238000006243 chemical reaction Methods 0.000 claims description 52
- 125000001589 carboacyl group Chemical group 0.000 claims description 50
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 48
- 125000003282 alkyl amino group Chemical group 0.000 claims description 46
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 45
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 45
- 150000002367 halogens Chemical class 0.000 claims description 45
- 229910052760 oxygen Inorganic materials 0.000 claims description 45
- 239000001301 oxygen Substances 0.000 claims description 45
- 229910052720 vanadium Inorganic materials 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 40
- 206010012601 diabetes mellitus Diseases 0.000 claims description 38
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 29
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
- 125000004414 alkyl thio group Chemical group 0.000 claims description 27
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 26
- 239000003814 drug Substances 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 24
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 24
- 125000006239 protecting group Chemical group 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 239000011593 sulfur Chemical group 0.000 claims description 24
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 20
- 150000001204 N-oxides Chemical class 0.000 claims description 16
- 229940079593 drug Drugs 0.000 claims description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 claims description 13
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 208000032841 Bulimia Diseases 0.000 claims description 8
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- LCIUZPZUSKOTTG-UHFFFAOYSA-N 1'-(5,6-dichloro-1h-benzimidazol-2-yl)-1-methylsulfonylspiro[2h-indole-3,4'-piperidine] Chemical compound C12=CC=CC=C2N(S(=O)(=O)C)CC11CCN(C=2NC3=CC(Cl)=C(Cl)C=C3N=2)CC1 LCIUZPZUSKOTTG-UHFFFAOYSA-N 0.000 claims description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 4
- ZBWVKSIGXFSIPR-UHFFFAOYSA-N 1'-(6-chloro-1h-benzimidazol-2-yl)-1-methylsulfonylspiro[2h-indole-3,4'-piperidine] Chemical compound C12=CC=CC=C2N(S(=O)(=O)C)CC11CCN(C=2NC3=CC(Cl)=CC=C3N=2)CC1 ZBWVKSIGXFSIPR-UHFFFAOYSA-N 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- KUXZGRCCXVZOJT-UHFFFAOYSA-N imidazo[4,5-c]pyridine Chemical compound C1=N[CH]C2=NC=NC2=C1 KUXZGRCCXVZOJT-UHFFFAOYSA-N 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- IMPIFTUKLVAMKX-UHFFFAOYSA-N 1'-(6-chloro-1h-benzimidazol-2-yl)-1-ethylsulfonylspiro[2h-indole-3,4'-piperidine] Chemical compound C12=CC=CC=C2N(S(=O)(=O)CC)CC11CCN(C=2NC3=CC(Cl)=CC=C3N=2)CC1 IMPIFTUKLVAMKX-UHFFFAOYSA-N 0.000 claims description 2
- NVOITFNSLADCKT-UHFFFAOYSA-N imidazo[4,5-b]pyrazine Chemical compound C1=C[N]C2=NC=NC2=N1 NVOITFNSLADCKT-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002660 neuropeptide Y receptor antagonist Substances 0.000 claims description 2
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 67
- JYZIHLWOWKMNNX-UHFFFAOYSA-N benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 claims 4
- 229940119154 Neuropeptide Y receptor antagonist Drugs 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
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- C07D473/30—Oxygen atom attached in position 6, e.g. hypoxanthine
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
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- 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
- C07D471/10—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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