JP4364513B2 - ノシセプチン類似体 - Google Patents

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Publication number

JP4364513B2

JP4364513B2 JP2002582930A JP2002582930A JP4364513B2 JP 4364513 B2 JP4364513 B2 JP 4364513B2 JP 2002582930 A JP2002582930 A JP 2002582930A JP 2002582930 A JP2002582930 A JP 2002582930A JP 4364513 B2 JP4364513 B2 JP 4364513B2

Authority

JP

Japan

Prior art keywords

alkyl

dihydro

piperidinyl

group

cycloalkyl

Prior art date

2001-04-18

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.)

Expired - Fee Related

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• PULGYDLMFSFVBL-SMFNREODSA-N nociceptin Chemical class C([C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(O)=O)[C@@H](C)O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 PULGYDLMFSFVBL-SMFNREODSA-N 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 101
• -1 —CH 2 OH Chemical group 0.000 claims description 260
• 125000000217 alkyl group Chemical group 0.000 claims description 221
• 229910052736 halogen Inorganic materials 0.000 claims description 77
• 125000003545 alkoxy group Chemical group 0.000 claims description 73
• 150000002367 halogens Chemical class 0.000 claims description 71
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 68
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 62
• 229910052739 hydrogen Inorganic materials 0.000 claims description 60
• 239000001257 hydrogen Substances 0.000 claims description 52
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
• 125000003118 aryl group Chemical group 0.000 claims description 49
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 46
• 125000001424 substituent group Chemical group 0.000 claims description 39
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 38
• 125000003282 alkyl amino group Chemical group 0.000 claims description 35
• 150000003839 salts Chemical class 0.000 claims description 32
• 125000002619 bicyclic group Chemical group 0.000 claims description 30
• 229910052799 carbon Inorganic materials 0.000 claims description 29
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 27
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 21
• 125000002950 monocyclic group Chemical group 0.000 claims description 21
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 20
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
• 125000004043 oxo group Chemical group O=* 0.000 claims description 19
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
• 125000003342 alkenyl group Chemical group 0.000 claims description 17
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
• 230000000202 analgesic effect Effects 0.000 claims description 15
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 15
• 125000001624 naphthyl group Chemical group 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 10
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 10
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
• 239000012453 solvate Substances 0.000 claims description 10
• 230000036592 analgesia Effects 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 9
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 9
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 9
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 6
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• 125000004442 acylamino group Chemical group 0.000 claims description 5
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
• 125000001475 halogen functional group Chemical group 0.000 claims description 5
• SNIKLTMOXOVPMO-UHFFFAOYSA-N n-[2-cyanoimino-3-(1-cyclooctylpiperidin-4-yl)benzimidazol-1-yl]acetamide Chemical compound N#CN=C1N(NC(=O)C)C2=CC=CC=C2N1C(CC1)CCN1C1CCCCCCC1 SNIKLTMOXOVPMO-UHFFFAOYSA-N 0.000 claims description 5
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 5
• 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 4
• 150000001408 amides Chemical class 0.000 claims description 4
• WWYKXCOJAKLOMJ-UHFFFAOYSA-N 2-[2-cyanoimino-3-(1-cyclooctylpiperidin-4-yl)benzimidazol-1-yl]acetic acid Chemical compound N#CN=C1N(CC(=O)O)C2=CC=CC=C2N1C(CC1)CCN1C1CCCCCCC1 WWYKXCOJAKLOMJ-UHFFFAOYSA-N 0.000 claims description 3
• UFTPXJJRJBLFCG-UHFFFAOYSA-N [1-(1-cyclooctylpiperidin-4-yl)-3-ethylbenzimidazol-2-ylidene]cyanamide Chemical compound N#CN=C1N(CC)C2=CC=CC=C2N1C(CC1)CCN1C1CCCCCCC1 UFTPXJJRJBLFCG-UHFFFAOYSA-N 0.000 claims description 3
• HETIMDAKSSHQRP-UHFFFAOYSA-N [1-(cyanomethyl)-3-(1-cyclooctylpiperidin-4-yl)benzimidazol-2-ylidene]cyanamide Chemical compound N#CN=C1N(CC#N)C2=CC=CC=C2N1C(CC1)CCN1C1CCCCCCC1 HETIMDAKSSHQRP-UHFFFAOYSA-N 0.000 claims description 3
• QDSHPSKNSQVGSP-UHFFFAOYSA-N [1-[1-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)piperidin-4-yl]-3-ethylbenzimidazol-2-ylidene]cyanamide Chemical compound C1CC2CCCCC2CC1N(CC1)CCC1N1C2=CC=CC=C2N(CC)C1=NC#N QDSHPSKNSQVGSP-UHFFFAOYSA-N 0.000 claims description 3
• OZXJDXIDGYLMAQ-UHFFFAOYSA-N [1-[1-(2,3-dihydro-1h-inden-2-yl)piperidin-4-yl]-3-ethylbenzimidazol-2-ylidene]cyanamide Chemical compound C1C2=CC=CC=C2CC1N(CC1)CCC1N1C2=CC=CC=C2N(CC)C1=NC#N OZXJDXIDGYLMAQ-UHFFFAOYSA-N 0.000 claims description 3
• DIKUWWGRUGWTMI-UHFFFAOYSA-N [1-[1-(3,3-diphenylpropyl)piperidin-4-yl]-3-ethylbenzimidazol-2-ylidene]cyanamide Chemical compound N#CN=C1N(CC)C2=CC=CC=C2N1C(CC1)CCN1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 DIKUWWGRUGWTMI-UHFFFAOYSA-N 0.000 claims description 3
• HRIFGNAVLJTORA-UHFFFAOYSA-N [1-[1-(cyclooctylmethyl)piperidin-4-yl]-3-ethylbenzimidazol-2-ylidene]cyanamide Chemical compound N#CN=C1N(CC)C2=CC=CC=C2N1C(CC1)CCN1CC1CCCCCCC1 HRIFGNAVLJTORA-UHFFFAOYSA-N 0.000 claims description 3
• VVWPFLHAYPZBLT-UHFFFAOYSA-N [1-butyl-3-(1-cyclooctylpiperidin-4-yl)benzimidazol-2-ylidene]cyanamide Chemical compound N#CN=C1N(CCCC)C2=CC=CC=C2N1C(CC1)CCN1C1CCCCCCC1 VVWPFLHAYPZBLT-UHFFFAOYSA-N 0.000 claims description 3
• KAVBGGWRLCYURZ-UHFFFAOYSA-N [1-ethyl-3-[1-(1,2,3,4-tetrahydronaphthalen-1-yl)piperidin-4-yl]benzimidazol-2-ylidene]cyanamide Chemical compound C1CCC2=CC=CC=C2C1N(CC1)CCC1N1C2=CC=CC=C2N(CC)C1=NC#N KAVBGGWRLCYURZ-UHFFFAOYSA-N 0.000 claims description 3
• LWVCESSZRIXQMC-UHFFFAOYSA-N [1-ethyl-3-[1-(4-propan-2-ylcyclohexyl)piperidin-4-yl]benzimidazol-2-ylidene]cyanamide Chemical compound N#CN=C1N(CC)C2=CC=CC=C2N1C(CC1)CCN1C1CCC(C(C)C)CC1 LWVCESSZRIXQMC-UHFFFAOYSA-N 0.000 claims description 3
• IOQCZCNHPOSBGQ-UHFFFAOYSA-N [1-ethyl-3-[1-(4-propylcyclohexyl)piperidin-4-yl]benzimidazol-2-ylidene]cyanamide Chemical compound C1CC(CCC)CCC1N1CCC(N2C(N(CC)C3=CC=CC=C32)=NC#N)CC1 IOQCZCNHPOSBGQ-UHFFFAOYSA-N 0.000 claims description 3
• SEWUWQFLOJZNSI-UHFFFAOYSA-N [1-ethyl-3-[1-(5-methylhexan-2-yl)piperidin-4-yl]benzimidazol-2-ylidene]cyanamide Chemical compound N#CN=C1N(CC)C2=CC=CC=C2N1C1CCN(C(C)CCC(C)C)CC1 SEWUWQFLOJZNSI-UHFFFAOYSA-N 0.000 claims description 3
• NSMWMUZETOGXDP-UHFFFAOYSA-N [1-ethyl-3-[1-(naphthalen-2-ylmethyl)piperidin-4-yl]benzimidazol-2-ylidene]cyanamide Chemical compound C1=CC=CC2=CC(CN3CCC(CC3)N3C4=CC=CC=C4N(C3=NC#N)CC)=CC=C21 NSMWMUZETOGXDP-UHFFFAOYSA-N 0.000 claims description 3
• ZJQPHRUAPTVORW-UHFFFAOYSA-N [1-ethyl-3-[1-[(4-phenylmethoxyphenyl)methyl]piperidin-4-yl]benzimidazol-2-ylidene]cyanamide Chemical compound N#CN=C1N(CC)C2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1OCC1=CC=CC=C1 ZJQPHRUAPTVORW-UHFFFAOYSA-N 0.000 claims description 3
• AEQCVDYYGKQXRD-UHFFFAOYSA-N [1-ethyl-3-[1-[(4-phenylphenyl)methyl]piperidin-4-yl]benzimidazol-2-ylidene]cyanamide Chemical compound N#CN=C1N(CC)C2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=CC=CC=C1 AEQCVDYYGKQXRD-UHFFFAOYSA-N 0.000 claims description 3
• PGFBITPNTAGGTE-UHFFFAOYSA-N methyl 2-[2-cyanoimino-3-(1-cyclooctylpiperidin-4-yl)benzimidazol-1-yl]acetate Chemical compound N#CN=C1N(CC(=O)OC)C2=CC=CC=C2N1C(CC1)CCN1C1CCCCCCC1 PGFBITPNTAGGTE-UHFFFAOYSA-N 0.000 claims description 3
• BJBJYUKLOPSINX-UHFFFAOYSA-N [1-[1-(3-bicyclo[2.2.1]heptanyl)piperidin-4-yl]-3-ethylbenzimidazol-2-ylidene]cyanamide Chemical compound N#CN=C1N(CC)C2=CC=CC=C2N1C(CC1)CCN1C1C(C2)CCC2C1 BJBJYUKLOPSINX-UHFFFAOYSA-N 0.000 claims description 2
• OVFUEINJAMEZHB-UHFFFAOYSA-N [1-[1-(6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)piperidin-4-yl]-3-ethylbenzimidazol-2-ylidene]cyanamide Chemical compound C12=CC=CC=C2CCC2=CC=CC=C2C1N(CC1)CCC1N1C2=CC=CC=C2N(CC)C1=NC#N OVFUEINJAMEZHB-UHFFFAOYSA-N 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims 21
• 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 3
• 241000023320 Luma <angiosperm> Species 0.000 claims 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
• 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
• OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims 1
• 208000002193 Pain Diseases 0.000 abstract description 12
• 230000036407 pain Effects 0.000 abstract description 4
• 101001122499 Homo sapiens Nociceptin receptor Proteins 0.000 abstract 1
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 67
• 238000005481 NMR spectroscopy Methods 0.000 description 63
• 125000001072 heteroaryl group Chemical group 0.000 description 47
• 238000005160 1H NMR spectroscopy Methods 0.000 description 46
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 42
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
• 239000000243 solution Substances 0.000 description 38
• 238000006243 chemical reaction Methods 0.000 description 36
• 238000000034 method Methods 0.000 description 36
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
• 239000002904 solvent Substances 0.000 description 36
• 150000002431 hydrogen Chemical class 0.000 description 34
• 235000019439 ethyl acetate Nutrition 0.000 description 32
• 239000007787 solid Substances 0.000 description 32
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
• 125000000623 heterocyclic group Chemical group 0.000 description 25
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• 238000004587 chromatography analysis Methods 0.000 description 14
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
• 239000000284 extract Substances 0.000 description 13
• 229910000027 potassium carbonate Inorganic materials 0.000 description 13
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
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• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 9
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