TW200823204A - Biphenyl sulfonyl and phenyl-heteroaryl sulfonyl modulators of the histamine H3-receptor useful for the treatment of disorders related thereto - Google Patents

Info

Publication number

TW200823204A

TW200823204A TW096136478A TW96136478A TW200823204A TW 200823204 A TW200823204 A TW 200823204A TW 096136478 A TW096136478 A TW 096136478A TW 96136478 A TW96136478 A TW 96136478A TW 200823204 A TW200823204 A TW 200823204A

Authority

TW

Taiwan

Prior art keywords

group

ethyl

compound

methyl

biphenyl

Prior art date

2006-10-17

Links

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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 34
• 238000011282 treatment Methods 0.000 title claims abstract description 30
• 102000004384 Histamine H3 receptors Human genes 0.000 title claims abstract description 21
• 108090000981 Histamine H3 receptors Proteins 0.000 title claims abstract description 21
• 208000035475 disorder Diseases 0.000 title claims abstract description 11
• 239000004305 biphenyl Substances 0.000 title claims description 60
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title claims description 42
• 235000010290 biphenyl Nutrition 0.000 title claims description 21
• 150000001875 compounds Chemical class 0.000 claims abstract description 306
• 238000000034 method Methods 0.000 claims abstract description 57
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims abstract description 52
• 239000003814 drug Substances 0.000 claims abstract description 43
• 230000007958 sleep Effects 0.000 claims abstract description 35
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 28
• 229960001340 histamine Drugs 0.000 claims abstract description 26
• 206010041349 Somnolence Diseases 0.000 claims abstract description 17
• 201000003631 narcolepsy Diseases 0.000 claims abstract description 16
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims abstract description 12
• 201000000980 schizophrenia Diseases 0.000 claims abstract description 12
• 206010020751 Hypersensitivity Diseases 0.000 claims abstract description 11
• 206010015037 epilepsy Diseases 0.000 claims abstract description 11
• 208000010877 cognitive disease Diseases 0.000 claims abstract description 10
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 9
• 208000008589 Obesity Diseases 0.000 claims abstract description 8
• 206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 8
• 201000010105 allergic rhinitis Diseases 0.000 claims abstract description 8
• 235000020824 obesity Nutrition 0.000 claims abstract description 8
• 206010012289 Dementia Diseases 0.000 claims abstract description 7
• 206010028735 Nasal congestion Diseases 0.000 claims abstract description 6
• 208000032140 Sleepiness Diseases 0.000 claims abstract description 5
• 208000030886 Traumatic Brain injury Diseases 0.000 claims abstract description 5
• 208000001573 Cataplexy Diseases 0.000 claims abstract description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 200
• -1 nitro, phenyl Chemical group 0.000 claims description 158
• 239000000203 mixture Substances 0.000 claims description 96
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 92
• 125000000217 alkyl group Chemical group 0.000 claims description 91
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 69
• 229910052757 nitrogen Inorganic materials 0.000 claims description 65
• 125000000623 heterocyclic group Chemical group 0.000 claims description 64
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 61
• 125000003545 alkoxy group Chemical group 0.000 claims description 57
• 150000003839 salts Chemical class 0.000 claims description 51
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 48
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 46
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 43
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 38
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
• 125000006413 ring segment Chemical group 0.000 claims description 35
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 34
• 125000001424 substituent group Chemical group 0.000 claims description 34
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 30
• 239000012453 solvate Substances 0.000 claims description 30
• 150000001412 amines Chemical class 0.000 claims description 27
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
• 229910052736 halogen Inorganic materials 0.000 claims description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims description 25
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 23
• 150000002367 halogens Chemical class 0.000 claims description 23
• 229940124530 sulfonamide Drugs 0.000 claims description 22
• 125000003282 alkyl amino group Chemical group 0.000 claims description 19
• 125000000468 ketone group Chemical group 0.000 claims description 19
• 229910052717 sulfur Inorganic materials 0.000 claims description 19
• 125000003342 alkenyl group Chemical group 0.000 claims description 18
• 125000000304 alkynyl group Chemical group 0.000 claims description 18
• 150000003456 sulfonamides Chemical class 0.000 claims description 18
• 150000003857 carboxamides Chemical class 0.000 claims description 17
• 125000001188 haloalkyl group Chemical group 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 16
• 125000004414 alkyl thio group Chemical group 0.000 claims description 15
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• 125000005363 dialkylsulfonamide group Chemical group 0.000 claims description 14
• 239000007789 gas Substances 0.000 claims description 14
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 14
• 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 13
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
• 125000006612 decyloxy group Chemical group 0.000 claims description 13
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 12
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
• 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 12
• 125000003277 amino group Chemical group 0.000 claims description 12
• 150000004677 hydrates Chemical class 0.000 claims description 12
• 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 11
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 11
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
• 229910052707 ruthenium Inorganic materials 0.000 claims description 11
• 239000011593 sulfur Substances 0.000 claims description 11
• 229910021653 sulphate ion Inorganic materials 0.000 claims description 11
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 9
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 9
• 239000004575 stone Substances 0.000 claims description 9
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• 150000002923 oximes Chemical class 0.000 claims description 8
• RGHPCLZJAFCTIK-UHFFFAOYSA-N 2-methylpyrrolidine Chemical group CC1CCCN1 RGHPCLZJAFCTIK-UHFFFAOYSA-N 0.000 claims description 7
• 206010003497 Asphyxia Diseases 0.000 claims description 7
• 208000030961 allergic reaction Diseases 0.000 claims description 7
• 239000004202 carbamide Substances 0.000 claims description 7
• 235000013877 carbamide Nutrition 0.000 claims description 7
• 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 7
• 208000019116 sleep disease Diseases 0.000 claims description 7
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 6
• 208000002193 Pain Diseases 0.000 claims description 6
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
• 125000005281 alkyl ureido group Chemical group 0.000 claims description 6
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 230000036407 pain Effects 0.000 claims description 6
• 125000005102 carbonylalkoxy group Chemical group 0.000 claims description 5
• 125000005265 dialkylamine group Chemical group 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 claims description 5
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 5
• 102000000543 Histamine Receptors Human genes 0.000 claims description 4
• 108010002059 Histamine Receptors Proteins 0.000 claims description 4
• 125000002947 alkylene group Chemical group 0.000 claims description 4
• 230000037321 sleepiness Effects 0.000 claims description 4
• RGHPCLZJAFCTIK-RXMQYKEDSA-N (R)-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1 RGHPCLZJAFCTIK-RXMQYKEDSA-N 0.000 claims description 3
• 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 3
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 3
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 3
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
• CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims description 3
• 229960005286 carbaryl Drugs 0.000 claims description 3
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• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 3
• FRUWMYWEARDNTC-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-indole Chemical compound C1C=CC=C2NCCC21 FRUWMYWEARDNTC-UHFFFAOYSA-N 0.000 claims description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
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• PTLMIIUMLITBQT-NCOIDOBVSA-N CpC Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2CO)N2C(N=C(N)C=C2)=O)O)O1 PTLMIIUMLITBQT-NCOIDOBVSA-N 0.000 claims description 2
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
• 239000006071 cream Substances 0.000 claims description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
• 238000002156 mixing Methods 0.000 claims description 2
• 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 229910052727 yttrium Inorganic materials 0.000 claims description 2
• LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims 6
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• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 2
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