JP2003505383A5 - - Google Patents
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- Publication number
- JP2003505383A5 JP2003505383A5 JP2001511441A JP2001511441A JP2003505383A5 JP 2003505383 A5 JP2003505383 A5 JP 2003505383A5 JP 2001511441 A JP2001511441 A JP 2001511441A JP 2001511441 A JP2001511441 A JP 2001511441A JP 2003505383 A5 JP2003505383 A5 JP 2003505383A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- piperidinyl
- diphenyl
- chlorobenzyl
- pyrazol
- Prior art date
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 description 32
- 150000003839 salts Chemical class 0.000 description 16
- 239000012453 solvate Substances 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 206010039083 rhinitis Diseases 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- -1 nitro, cyano, hydroxy, methylenedioxy Chemical group 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 208000030507 AIDS Diseases 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 206010025135 lupus erythematosus Diseases 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 2
- LVVPQYPTJYMPMR-UHFFFAOYSA-N 1-[3-[(4-chlorophenyl)methyl]-5-[(4,4-diphenylpiperidin-1-yl)methyl]imidazole-4-carbonyl]pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1C(=O)C(N(C=N1)CC=2C=CC(Cl)=CC=2)=C1CN1CCC(C=2C=CC=CC=2)(C=2C=CC=CC=2)CC1 LVVPQYPTJYMPMR-UHFFFAOYSA-N 0.000 description 2
- GPFREBMIYIUEQR-UHFFFAOYSA-N 2-[5-chloro-2-[[3-[(4,4-diphenylpiperidin-1-yl)methyl]pyrazol-1-yl]methyl]phenoxy]-n,n-dimethylacetamide Chemical compound CN(C)C(=O)COC1=CC(Cl)=CC=C1CN1N=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 GPFREBMIYIUEQR-UHFFFAOYSA-N 0.000 description 2
- PARZHTAKOREGGF-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-5-[(4,4-diphenylpiperidin-1-yl)methyl]-n-(1-hydroxybutan-2-yl)imidazole-4-carboxamide Chemical compound N1=CN(CC=2C=CC(Cl)=CC=2)C(C(=O)NC(CO)CC)=C1CN(CC1)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 PARZHTAKOREGGF-UHFFFAOYSA-N 0.000 description 2
- YDWDVRASHBRSSY-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-5-[(4,4-diphenylpiperidin-1-yl)methyl]imidazole-4-carboxamide Chemical compound N1=CN(CC=2C=CC(Cl)=CC=2)C(C(=O)N)=C1CN(CC1)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 YDWDVRASHBRSSY-UHFFFAOYSA-N 0.000 description 2
- VFMNZXZBOXLJEM-UHFFFAOYSA-N 4-[3-[(4-chlorophenyl)methyl]-5-[(4,4-diphenylpiperidin-1-yl)methyl]imidazole-4-carbonyl]piperazin-2-one Chemical compound C1=CC(Cl)=CC=C1CN1C(C(=O)N2CC(=O)NCC2)=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)N=C1 VFMNZXZBOXLJEM-UHFFFAOYSA-N 0.000 description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
- 201000008283 Atrophic Rhinitis Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 206010039088 Rhinitis atrophic Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052770 Uranium Inorganic materials 0.000 description 2
- HHKCINDBCMHWJM-UHFFFAOYSA-N [2-[(4-chlorophenyl)methyl]-1h-imidazol-5-yl]-(4,4-diphenylpiperidin-1-yl)methanone Chemical compound C1=CC(Cl)=CC=C1CC1=NC=C(C(=O)N2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)N1 HHKCINDBCMHWJM-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OXYAHFWRYGADFR-UHFFFAOYSA-N 1-[(1-benzylpyrazol-3-yl)methyl]-4,4-diphenylpiperidine Chemical compound C1=CN(CC=2C=CC=CC=2)N=C1CN(CC1)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 OXYAHFWRYGADFR-UHFFFAOYSA-N 0.000 description 1
- RGGLTAAJBMKRPE-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-3-[(4,4-diphenylpiperidin-1-yl)methyl]pyrazole-4-carbaldehyde Chemical compound C1=CC(Cl)=CC=C1CN1N=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C(C=O)=C1 RGGLTAAJBMKRPE-UHFFFAOYSA-N 0.000 description 1
- OCKGZYMKGRRCIR-UHFFFAOYSA-N 1-[2-[5-chloro-2-[[3-[(4,4-diphenylpiperidin-1-yl)methyl]pyrazol-1-yl]methyl]phenoxy]acetyl]pyrazolidin-3-one Chemical compound C1CC(=O)NN1C(=O)COC1=CC(Cl)=CC=C1CN(N=1)C=CC=1CN(CC1)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 OCKGZYMKGRRCIR-UHFFFAOYSA-N 0.000 description 1
- ZNOXDLNGKDWJRL-UHFFFAOYSA-N 1-[4-[3-[(4-chlorophenyl)methyl]-5-[(4,4-diphenylpiperidin-1-yl)methyl]imidazole-4-carbonyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(=O)C(N(C=N1)CC=2C=CC(Cl)=CC=2)=C1CN1CCC(C=2C=CC=CC=2)(C=2C=CC=CC=2)CC1 ZNOXDLNGKDWJRL-UHFFFAOYSA-N 0.000 description 1
- CCDRRRNNFZCYFU-UHFFFAOYSA-N 1-[4-[[1-[(4-chlorophenyl)methyl]-3-[(4,4-diphenylpiperidin-1-yl)methyl]pyrazol-4-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC(C(=N1)CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=CN1CC1=CC=C(Cl)C=C1 CCDRRRNNFZCYFU-UHFFFAOYSA-N 0.000 description 1
- VLJRJYNFOLSIKP-UHFFFAOYSA-N 1-[[1-[(2,4-dichlorophenyl)methyl]pyrazol-3-yl]methyl]-4,4-diphenylpiperidine Chemical compound ClC1=CC(Cl)=CC=C1CN1N=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 VLJRJYNFOLSIKP-UHFFFAOYSA-N 0.000 description 1
- YKJMPZWWKKHDMV-UHFFFAOYSA-N 1-[[1-[(3,4-dichlorophenyl)methyl]pyrazol-3-yl]methyl]-4,4-diphenylpiperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1N=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 YKJMPZWWKKHDMV-UHFFFAOYSA-N 0.000 description 1
- HJSJVHAPTLMEPB-UHFFFAOYSA-N 1-[[1-[(3,4-difluorophenyl)methyl]pyrazol-3-yl]methyl]-4,4-diphenylpiperidine Chemical compound C1=C(F)C(F)=CC=C1CN1N=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 HJSJVHAPTLMEPB-UHFFFAOYSA-N 0.000 description 1
- AVMJQHSFKBFJSI-UHFFFAOYSA-N 1-[[1-[(3,4-dimethylphenyl)methyl]pyrazol-3-yl]methyl]-4,4-diphenylpiperidine Chemical compound C1=C(C)C(C)=CC=C1CN1N=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 AVMJQHSFKBFJSI-UHFFFAOYSA-N 0.000 description 1
- XVHYCITYUZYQNI-UHFFFAOYSA-N 1-[[1-[(3-chlorophenyl)methyl]pyrazol-3-yl]methyl]-4,4-diphenylpiperidine Chemical compound ClC1=CC=CC(CN2N=C(CN3CCC(CC3)(C=3C=CC=CC=3)C=3C=CC=CC=3)C=C2)=C1 XVHYCITYUZYQNI-UHFFFAOYSA-N 0.000 description 1
- IFMLUHGYBPEENF-UHFFFAOYSA-N 1-[[1-[(4-chloro-2-methoxyphenyl)methyl]pyrazol-3-yl]methyl]-4,4-diphenylpiperidine Chemical compound COC1=CC(Cl)=CC=C1CN1N=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 IFMLUHGYBPEENF-UHFFFAOYSA-N 0.000 description 1
- WXZJUKWTUSSTBH-UHFFFAOYSA-N 1-[[1-[(4-chlorophenyl)methyl]-3-[(4,4-diphenylpiperidin-1-yl)methyl]pyrazol-4-yl]methyl]-4-methyl-1,4-diazepane Chemical compound C1CN(C)CCCN1CC(C(=N1)CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=CN1CC1=CC=C(Cl)C=C1 WXZJUKWTUSSTBH-UHFFFAOYSA-N 0.000 description 1
- AOFUBLCRNKYMCK-UHFFFAOYSA-N 1-[[1-[(4-chlorophenyl)methyl]imidazol-4-yl]methyl]-4,4-diphenylpiperidine Chemical compound C1=CC(Cl)=CC=C1CN1C=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)N=C1 AOFUBLCRNKYMCK-UHFFFAOYSA-N 0.000 description 1
- UDFOHCDIQUCBOH-UHFFFAOYSA-N 1-[[1-[(4-chlorophenyl)methyl]pyrazol-3-yl]methyl]-4,4-diphenylpiperidine Chemical compound C1=CC(Cl)=CC=C1CN1N=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 UDFOHCDIQUCBOH-UHFFFAOYSA-N 0.000 description 1
- ZBFMXEPJGDYRBO-UHFFFAOYSA-N 1-[[1-[(4-chlorophenyl)methyl]triazol-4-yl]methyl]-4,4-diphenylpiperidine Chemical compound C1=CC(Cl)=CC=C1CN1N=NC(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 ZBFMXEPJGDYRBO-UHFFFAOYSA-N 0.000 description 1
- VSLKXQVAPSRPFQ-UHFFFAOYSA-N 1-[[1-[(4-fluorophenyl)methyl]pyrazol-3-yl]methyl]-4,4-diphenylpiperidine Chemical compound C1=CC(F)=CC=C1CN1N=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 VSLKXQVAPSRPFQ-UHFFFAOYSA-N 0.000 description 1
- IZCCOWLSOXUOOD-UHFFFAOYSA-N 1-[[1-[(4-methylphenyl)methyl]pyrazol-3-yl]methyl]-4,4-diphenylpiperidine Chemical compound C1=CC(C)=CC=C1CN1N=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 IZCCOWLSOXUOOD-UHFFFAOYSA-N 0.000 description 1
- KFBVQVBKBKTSBP-UHFFFAOYSA-N 1-[[1-[[4-chloro-2-(2-methoxy-1-methylimidazol-4-yl)phenyl]methyl]pyrazol-3-yl]methyl]-4,4-diphenylpiperidine Chemical compound COC=1N(C=C(N1)C1=C(C=CC(=C1)Cl)CN1N=C(C=C1)CN1CCC(CC1)(C1=CC=CC=C1)C1=CC=CC=C1)C KFBVQVBKBKTSBP-UHFFFAOYSA-N 0.000 description 1
- RRNRBZAXYCPLPN-UHFFFAOYSA-N 1-[[2-[(4-chlorophenyl)methyl]-1-methylimidazol-4-yl]methyl]-4,4-diphenylpiperidine Chemical compound N1=C(CC=2C=CC(Cl)=CC=2)N(C)C=C1CN(CC1)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 RRNRBZAXYCPLPN-UHFFFAOYSA-N 0.000 description 1
- XNFOCQUXTDUVLX-UHFFFAOYSA-N 1-[[2-[(4-chlorophenyl)methyl]-1h-imidazol-5-yl]methyl]-4,4-diphenylpiperidine Chemical compound C1=CC(Cl)=CC=C1CC(N1)=NC=C1CN1CCC(C=2C=CC=CC=2)(C=2C=CC=CC=2)CC1 XNFOCQUXTDUVLX-UHFFFAOYSA-N 0.000 description 1
- RAIRIKPNGFSDRL-UHFFFAOYSA-N 1-[[2-[(4-chlorophenyl)methyl]-3-methylimidazol-4-yl]methyl]-4,4-diphenylpiperidine Chemical compound C=1N=C(CC=2C=CC(Cl)=CC=2)N(C)C=1CN(CC1)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 RAIRIKPNGFSDRL-UHFFFAOYSA-N 0.000 description 1
- FFMJFCBKDHXHIZ-UHFFFAOYSA-N 1-[[3-[(4-chlorophenyl)methyl]triazol-4-yl]methyl]-4,4-diphenylpiperidine Chemical compound C1=CC(Cl)=CC=C1CN1C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=CN=N1 FFMJFCBKDHXHIZ-UHFFFAOYSA-N 0.000 description 1
- KZQXMISNAJFMMG-UHFFFAOYSA-N 1-[[4-(azetidin-1-ylmethyl)-1-[(4-chlorophenyl)methyl]pyrazol-3-yl]methyl]-4,4-diphenylpiperidine Chemical compound C1=CC(Cl)=CC=C1CN1N=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C(CN2CCC2)=C1 KZQXMISNAJFMMG-UHFFFAOYSA-N 0.000 description 1
- HQLCFLVWKYMRBG-UHFFFAOYSA-N 2-[1-[[1-[(4-chlorophenyl)methyl]-3-[(4,4-diphenylpiperidin-1-yl)methyl]pyrazol-4-yl]methyl]piperidin-4-yl]ethanol Chemical compound C1CC(CCO)CCN1CC(C(=N1)CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=CN1CC1=CC=C(Cl)C=C1 HQLCFLVWKYMRBG-UHFFFAOYSA-N 0.000 description 1
- OVVLMMXGUPCGCP-UHFFFAOYSA-N 2-[4-[[1-[(4-chlorophenyl)methyl]-3-[(4,4-diphenylpiperidin-1-yl)methyl]pyrazol-4-yl]methyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1CC(C(=N1)CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=CN1CC1=CC=C(Cl)C=C1 OVVLMMXGUPCGCP-UHFFFAOYSA-N 0.000 description 1
- JANRXQVQIMXLAA-UHFFFAOYSA-N 2-[5-chloro-2-[[3-[(4,4-diphenylpiperidin-1-yl)methyl]pyrazol-1-yl]methyl]phenoxy]-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)COC1=CC(Cl)=CC=C1CN1N=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 JANRXQVQIMXLAA-UHFFFAOYSA-N 0.000 description 1
- ICOMYXLANMBOJR-UHFFFAOYSA-N 2-[5-chloro-2-[[3-[(4,4-diphenylpiperidin-1-yl)methyl]pyrazol-1-yl]methyl]phenoxy]-n-methylacetamide Chemical compound CNC(=O)COC1=CC(Cl)=CC=C1CN1N=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 ICOMYXLANMBOJR-UHFFFAOYSA-N 0.000 description 1
- GEZPZYVFBPZVJM-UHFFFAOYSA-N 2-[5-chloro-2-[[3-[(4,4-diphenylpiperidin-1-yl)methyl]pyrazol-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC(Cl)=CC=C1CN1N=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 GEZPZYVFBPZVJM-UHFFFAOYSA-N 0.000 description 1
- YCRMNFXIYAPXEH-UHFFFAOYSA-N 2-[[1-[(4-chlorophenyl)methyl]-3-[(4,4-diphenylpiperidin-1-yl)methyl]pyrazol-4-yl]methylamino]acetic acid Chemical compound N1=C(CN2CCC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C(CNCC(=O)O)=CN1CC1=CC=C(Cl)C=C1 YCRMNFXIYAPXEH-UHFFFAOYSA-N 0.000 description 1
- IDLHTECVNDEOIY-UHFFFAOYSA-N 2-pyridin-4-ylethanamine Chemical compound NCCC1=CC=NC=C1 IDLHTECVNDEOIY-UHFFFAOYSA-N 0.000 description 1
- GCFXSYCQLVOFDF-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-5-[(4,4-diphenylpiperidin-1-yl)methyl]-n,n-dimethylimidazole-4-carboxamide Chemical compound N1=CN(CC=2C=CC(Cl)=CC=2)C(C(=O)N(C)C)=C1CN(CC1)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 GCFXSYCQLVOFDF-UHFFFAOYSA-N 0.000 description 1
- FNZCCNDTMHRBHW-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-5-[(4,4-diphenylpiperidin-1-yl)methyl]-n-(1-hydroxy-2-methylpropan-2-yl)imidazole-4-carboxamide Chemical compound N1=CN(CC=2C=CC(Cl)=CC=2)C(C(=O)NC(C)(CO)C)=C1CN(CC1)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 FNZCCNDTMHRBHW-UHFFFAOYSA-N 0.000 description 1
- RITZGHOXWNMDOU-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-5-[(4,4-diphenylpiperidin-1-yl)methyl]-n-(1-hydroxypropan-2-yl)imidazole-4-carboxamide Chemical compound N1=CN(CC=2C=CC(Cl)=CC=2)C(C(=O)NC(CO)C)=C1CN(CC1)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 RITZGHOXWNMDOU-UHFFFAOYSA-N 0.000 description 1
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| SE9902765-8 | 1999-07-21 | ||
| PCT/GB2000/002756 WO2001005782A1 (en) | 1999-07-21 | 2000-07-18 | Novel diphenyl-piperidine derivate |
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| EP (1) | EP1202984B1 (https=) |
| JP (1) | JP2003505383A (https=) |
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| AU (1) | AU771344B2 (https=) |
| BR (1) | BR0012610A (https=) |
| CA (1) | CA2378084A1 (https=) |
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| IL (1) | IL147149A0 (https=) |
| MX (1) | MXPA02000671A (https=) |
| NO (1) | NO20020282L (https=) |
| NZ (1) | NZ516606A (https=) |
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| WO (1) | WO2001005782A1 (https=) |
| ZA (1) | ZA200110540B (https=) |
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| TW200303304A (en) * | 2002-02-18 | 2003-09-01 | Astrazeneca Ab | Chemical compounds |
| SE0400208D0 (sv) | 2004-02-02 | 2004-02-02 | Astrazeneca Ab | Chemical compounds |
| EP1962605A2 (en) * | 2005-12-12 | 2008-09-03 | Merck & Co., Inc. | 2-arylthiazole derivatives as cxcr3 receptor modulators |
| US10344095B2 (en) * | 2006-02-16 | 2019-07-09 | University Of Kentucky Research Foundation | CCR3 inhibition for ocular angiogenesis and macular degeneration |
| TW200812582A (en) * | 2006-04-06 | 2008-03-16 | Astrazeneca Ab | Medicaments |
| CN101687844B (zh) * | 2007-07-02 | 2013-11-13 | 弗·哈夫曼-拉罗切有限公司 | 用作ccr2受体拮抗剂的咪唑衍生物 |
| WO2010129351A1 (en) | 2009-04-28 | 2010-11-11 | Schepens Eye Research Institute | Method to identify and treat age-related macular degeneration |
| WO2010138591A1 (en) | 2009-05-26 | 2010-12-02 | University Of Kentucky Research Foundation | Ccr3 and its ligands are therapeutic and diagnostic targets for neovascular age-related macular degeneration |
| US9045455B2 (en) | 2013-03-14 | 2015-06-02 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| EP2970136A1 (en) | 2013-03-14 | 2016-01-20 | Epizyme, Inc. | Arginine methyl transferase inhibtors and uses thereof |
| US9120757B2 (en) | 2013-03-14 | 2015-09-01 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| WO2014153172A1 (en) | 2013-03-14 | 2014-09-25 | Epizyme, Inc. | Pyrazole derivatives as prmt1 inhibitors and uses thereof |
| PL2970132T3 (pl) | 2013-03-14 | 2021-04-06 | Epizyme, Inc. | Inhibitory metylotransferazy argininy i ich zastosowania |
| CA2903264A1 (en) | 2013-03-14 | 2014-11-06 | Epizyme, Inc. | Pyrazole derivatives as arginine methyltransferase inhibitors and uses thereof |
| EP3363434A1 (en) | 2013-03-14 | 2018-08-22 | Epizyme Inc | Arginine methyltransferase inhibitors and uses thereof |
| US9023883B2 (en) | 2013-03-14 | 2015-05-05 | Epizyme, Inc. | PRMT1 inhibitors and uses thereof |
| US9765035B2 (en) | 2013-03-14 | 2017-09-19 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| EP2970134B1 (en) | 2013-03-14 | 2018-02-28 | Epizyme, Inc. | Pyrazole derivatives as prmt1 inhibitors and uses thereof |
| MX368059B (es) | 2013-07-18 | 2019-09-18 | Novartis Ag | Inhibidores de autotaxina que comprenden un núcleo de anillo heteroaromático de bencil-amida cíclica. |
| CN108299411B (zh) * | 2017-01-13 | 2021-02-05 | 中国人民解放军军事医学科学院毒物药物研究所 | 4,4-二苯基哌啶类化合物或其可药用盐、药物组合物及用途 |
| US12221463B2 (en) | 2020-08-07 | 2025-02-11 | The Board Of Regents Of The University Of Oklahoma | Method of promoting wound healing by inhibiting CCR3 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2139084C3 (de) * | 1971-08-04 | 1979-03-01 | Byk Gulden Lomberg Chemische Fabrik Gmbh, 7750 Konstanz | Verfahren zur Herstellung von 4,4-Diphenyl-piperidinen |
| IL90858A (en) | 1988-07-07 | 1994-08-26 | Rhone Poulenc Sante | Derivatives of (AZA) naphthalensultam, their preparation and compositions containing them |
| US5352684A (en) | 1990-04-10 | 1994-10-04 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Pyridines as medicaments |
| DE4140542A1 (de) * | 1991-12-09 | 1993-06-17 | Bayer Ag | Piperdylmethyl substituierte chormanderivate |
| US6339087B1 (en) | 1997-08-18 | 2002-01-15 | Syntex (U.S.A.) Llc | Cyclic amine derivatives-CCR-3 receptor antagonists |
| IL125658A0 (en) | 1997-08-18 | 1999-04-11 | Hoffmann La Roche | Ccr-3 receptor antagonists |
| DE19756235A1 (de) | 1997-12-17 | 1999-07-01 | Klinge Co Chem Pharm Fab | Neue piperidinylsubstituierte Pyridylalkan- alken- und -alkincarbonsäureamide |
| HN1999000149A (es) * | 1998-09-09 | 2000-01-12 | Pfizer Prod Inc | Derivados de 4,4-biarilpiperidina |
| US6046331A (en) * | 1998-12-17 | 2000-04-04 | Synaptic Pharmaceutical Corporation | Imidazolones and their use in treating benign prostatic hyperplasia and other disorders |
-
1999
- 1999-07-21 SE SE9902765A patent/SE9902765D0/xx unknown
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2000
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- 2000-07-18 EP EP00946134A patent/EP1202984B1/en not_active Expired - Lifetime
- 2000-07-18 MX MXPA02000671A patent/MXPA02000671A/es active IP Right Grant
- 2000-07-18 JP JP2001511441A patent/JP2003505383A/ja not_active Withdrawn
- 2000-07-18 AU AU60016/00A patent/AU771344B2/en not_active Ceased
- 2000-07-18 IL IL14714900A patent/IL147149A0/xx unknown
- 2000-07-18 AT AT00946134T patent/ATE233754T1/de not_active IP Right Cessation
- 2000-07-18 NZ NZ516606A patent/NZ516606A/en unknown
- 2000-07-18 CN CNB008106703A patent/CN1152873C/zh not_active Expired - Fee Related
- 2000-07-18 BR BR0012610-1A patent/BR0012610A/pt not_active IP Right Cessation
- 2000-07-18 CA CA002378084A patent/CA2378084A1/en not_active Abandoned
- 2000-07-18 WO PCT/GB2000/002756 patent/WO2001005782A1/en not_active Ceased
- 2000-07-18 DE DE60001586T patent/DE60001586T2/de not_active Expired - Fee Related
- 2000-07-18 KR KR1020027000797A patent/KR20020027498A/ko not_active Ceased
-
2001
- 2001-12-21 ZA ZA200110540A patent/ZA200110540B/xx unknown
-
2002
- 2002-01-18 NO NO20020282A patent/NO20020282L/no unknown
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