OA13010A - 4-tetrazolyl-4phenylpiperidine derivatives for treating pain. - Google Patents

Info

Publication number

OA13010A

OA13010A OA1200500145A OA1200500145A OA13010A OA 13010 A OA13010 A OA 13010A OA 1200500145 A OA1200500145 A OA 1200500145A OA 1200500145 A OA1200500145 A OA 1200500145A OA 13010 A OA13010 A OA 13010A

Authority

OA

OAPI

Prior art keywords

compound

alkyl

tetrazolyl

pharmaceutically acceptable

acceptable sait

Prior art date

2002-11-18

Links

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• 208000002193 Pain Diseases 0.000 title claims abstract description 53
• OGPKTRWLBLRODW-UHFFFAOYSA-N 4-phenyl-4-(2h-tetrazol-5-yl)piperidine Chemical class C1CNCCC1(C=1C=CC=CC=1)C1=NNN=N1 OGPKTRWLBLRODW-UHFFFAOYSA-N 0.000 title abstract description 417
• -1 4-Tetrazolyl-4-phenylpiperidine Compound Chemical class 0.000 claims abstract description 118
• 239000000203 mixture Substances 0.000 claims abstract description 88
• 238000000034 method Methods 0.000 claims abstract description 76
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• 206010012735 Diarrhoea Diseases 0.000 claims abstract description 33
• 102000003840 Opioid Receptors Human genes 0.000 claims abstract description 22
• 108090000137 Opioid Receptors Proteins 0.000 claims abstract description 22
• 230000004936 stimulating effect Effects 0.000 claims abstract description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 192
• 150000001875 compounds Chemical class 0.000 claims description 188
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
• 125000001072 heteroaryl group Chemical group 0.000 claims description 28
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 27
• 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 26
• 125000005561 phenanthryl group Chemical group 0.000 claims description 26
• 125000001624 naphthyl group Chemical group 0.000 claims description 25
• 108010020615 nociceptin receptor Proteins 0.000 claims description 24
• 239000003795 chemical substances by application Substances 0.000 claims description 19
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• 229940125683 antiemetic agent Drugs 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 239000003937 drug carrier Substances 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 108020001612 μ-opioid receptors Proteins 0.000 claims description 9
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• 101100244562 Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) oprD gene Proteins 0.000 claims description 3
• 125000002947 alkylene group Chemical group 0.000 claims description 3
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• 108700023159 delta Opioid Receptors Proteins 0.000 claims description 3
• 102000048124 delta Opioid Receptors Human genes 0.000 claims description 3
• 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims description 2
• 102000048260 kappa Opioid Receptors Human genes 0.000 claims description 2
• 108020001588 κ-opioid receptors Proteins 0.000 claims description 2
• SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 14
• 125000005843 halogen group Chemical group 0.000 claims 3
• GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
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• JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 170
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 156
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
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• 150000001721 carbon Chemical group 0.000 description 26
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
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• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
• 108010050904 Interferons Proteins 0.000 description 6
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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 6
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• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 6
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• 229910052708 sodium Inorganic materials 0.000 description 6
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• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
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• LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical class C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 description 4
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• 229940100198 alkylating agent Drugs 0.000 description 4
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• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
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