CZ20013451A3 - Nové sloučeniny - Google Patents
Nové sloučeniny Download PDFInfo
- Publication number
- CZ20013451A3 CZ20013451A3 CZ20013451A CZ20013451A CZ20013451A3 CZ 20013451 A3 CZ20013451 A3 CZ 20013451A3 CZ 20013451 A CZ20013451 A CZ 20013451A CZ 20013451 A CZ20013451 A CZ 20013451A CZ 20013451 A3 CZ20013451 A3 CZ 20013451A3
- Authority
- CZ
- Czechia
- Prior art keywords
- piperidyl
- ethyl
- dichlorophenoxy
- amino
- methyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 104
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 6
- 239000001301 oxygen Chemical group 0.000 claims abstract description 6
- 229910052717 sulfur Chemical group 0.000 claims abstract description 6
- 239000011593 sulfur Chemical group 0.000 claims abstract description 6
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 3
- -1 -NR 5 R ® Chemical group 0.000 claims description 323
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 231
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 27
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000012453 solvate Substances 0.000 claims description 19
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 17
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229940124530 sulfonamide Drugs 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- 150000003456 sulfonamides Chemical class 0.000 claims description 7
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
- MHIFSXJQGYPPDB-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4-fluorobenzamide Chemical compound C1=CC(F)=CC=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 MHIFSXJQGYPPDB-UHFFFAOYSA-N 0.000 claims description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- BPPZIPHINXIUFJ-UHFFFAOYSA-N [1-[2-[(5-chloro-1,3-dimethylpyrazol-4-yl)methylamino]ethyl]piperidin-4-yl]-(4-chlorophenyl)methanone Chemical compound CC1=NN(C)C(Cl)=C1CNCCN1CCC(C(=O)C=2C=CC(Cl)=CC=2)CC1 BPPZIPHINXIUFJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- NVFNOMAXNHPMEV-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorobenzoyl)piperazin-1-yl]ethyl]-3-methoxybenzamide;hydrochloride Chemical compound Cl.COC1=CC=CC(C(=O)NCCN2CCN(CC2)C(=O)C=2C=C(Cl)C(Cl)=CC=2)=C1 NVFNOMAXNHPMEV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 claims description 4
- QWDIDFWRSBMBFV-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-(3-methylsulfanylbutylamino)ethyl]piperidin-4-yl]methanone Chemical compound C1CN(CCNCCC(C)SC)CCC1C(=O)C1=CC=C(Cl)C=C1 QWDIDFWRSBMBFV-UHFFFAOYSA-N 0.000 claims description 3
- DPZYXLJALIJPHJ-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-(quinolin-3-ylmethylamino)ethyl]piperidin-4-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNCC=2C=C3C=CC=CC3=NC=2)CC1 DPZYXLJALIJPHJ-UHFFFAOYSA-N 0.000 claims description 3
- CAMLOMWWSRNMDR-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(1-methylbenzimidazol-2-yl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound N=1C2=CC=CC=C2N(C)C=1CNCCN(CC1)CCC1C(=O)C1=CC=C(Cl)C=C1 CAMLOMWWSRNMDR-UHFFFAOYSA-N 0.000 claims description 3
- BZZQZDAWAXXDRW-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(2,5-difluorophenyl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound FC1=CC=C(F)C(CNCCN2CCC(CC2)C(=O)C=2C=CC(Cl)=CC=2)=C1 BZZQZDAWAXXDRW-UHFFFAOYSA-N 0.000 claims description 3
- QNHDEZAQQYUODX-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(2,6-dichlorophenyl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNCC=2C(=CC=CC=2Cl)Cl)CC1 QNHDEZAQQYUODX-UHFFFAOYSA-N 0.000 claims description 3
- PLIWJSGXSUYJCZ-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(2,6-dichloropyridin-4-yl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNCC=2C=C(Cl)N=C(Cl)C=2)CC1 PLIWJSGXSUYJCZ-UHFFFAOYSA-N 0.000 claims description 3
- FIHOVKRJUWICRZ-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(2-chloroquinolin-3-yl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNCC=2C(=NC3=CC=CC=C3C=2)Cl)CC1 FIHOVKRJUWICRZ-UHFFFAOYSA-N 0.000 claims description 3
- FBZOJNNRWXMQGT-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(2-phenyl-1h-imidazol-5-yl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNCC=2N=C(NC=2)C=2C=CC=CC=2)CC1 FBZOJNNRWXMQGT-UHFFFAOYSA-N 0.000 claims description 3
- CRHYLKKTXOMRKU-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(2-phenylpyrazol-3-yl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNCC=2N(N=CC=2)C=2C=CC=CC=2)CC1 CRHYLKKTXOMRKU-UHFFFAOYSA-N 0.000 claims description 3
- NIRSYNGGTPBPRP-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(3,4,5-trimethoxyphenyl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound COC1=C(OC)C(OC)=CC(CNCCN2CCC(CC2)C(=O)C=2C=CC(Cl)=CC=2)=C1 NIRSYNGGTPBPRP-UHFFFAOYSA-N 0.000 claims description 3
- BQSJOJBQVLBVLW-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(3,5-difluorophenyl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound FC1=CC(F)=CC(CNCCN2CCC(CC2)C(=O)C=2C=CC(Cl)=CC=2)=C1 BQSJOJBQVLBVLW-UHFFFAOYSA-N 0.000 claims description 3
- ZGEADYISVFOZKM-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(3-nitrophenyl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound [O-][N+](=O)C1=CC=CC(CNCCN2CCC(CC2)C(=O)C=2C=CC(Cl)=CC=2)=C1 ZGEADYISVFOZKM-UHFFFAOYSA-N 0.000 claims description 3
- SNSLWGMYHQXIKB-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(4-nitrophenyl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1CNCCN1CCC(C(=O)C=2C=CC(Cl)=CC=2)CC1 SNSLWGMYHQXIKB-UHFFFAOYSA-N 0.000 claims description 3
- OVNYNSHJGJUENX-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(5-nitro-2-pyridin-2-ylsulfanylphenyl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound C1CC(C(=O)C=2C=CC(Cl)=CC=2)CCN1CCNCC1=CC([N+](=O)[O-])=CC=C1SC1=CC=CC=N1 OVNYNSHJGJUENX-UHFFFAOYSA-N 0.000 claims description 3
- LQNLIYRHRPZSPL-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(6-nitro-1,3-benzodioxol-5-yl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound [O-][N+](=O)C1=CC=2OCOC=2C=C1CNCCN(CC1)CCC1C(=O)C1=CC=C(Cl)C=C1 LQNLIYRHRPZSPL-UHFFFAOYSA-N 0.000 claims description 3
- PFYFSSBSMWQHOT-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(7-hydroxy-3,7-dimethyloctyl)amino]ethyl]piperidin-4-yl]methanone Chemical compound C1CN(CCNCCC(CCCC(C)(C)O)C)CCC1C(=O)C1=CC=C(Cl)C=C1 PFYFSSBSMWQHOT-UHFFFAOYSA-N 0.000 claims description 3
- USCYTAXQSSZRJK-OWOJBTEDSA-N (4-chlorophenyl)-[1-[2-[[(e)-3-(4-nitrophenyl)prop-2-enyl]amino]ethyl]piperidin-4-yl]methanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1\C=C\CNCCN1CCC(C(=O)C=2C=CC(Cl)=CC=2)CC1 USCYTAXQSSZRJK-OWOJBTEDSA-N 0.000 claims description 3
- ZWXDDWDWMCESKH-RMKNXTFCSA-N (e)-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3-phenylprop-2-enamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)\C=C\C=2C=CC=CC=2)CC1 ZWXDDWDWMCESKH-RMKNXTFCSA-N 0.000 claims description 3
- GNTLPZAHICFRRC-XCVCLJGOSA-N (e)-n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]-3-(4-nitrophenyl)prop-2-enamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1\C=C\C(=O)NCCN1CCC(C(=O)C=2C=CC(Cl)=CC=2)CC1 GNTLPZAHICFRRC-XCVCLJGOSA-N 0.000 claims description 3
- OLFUWQFGAVROEA-UHFFFAOYSA-N 2-[[2-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propylamino]pyrimidin-4-yl]amino]ethanol Chemical compound OCCNC1=CC=NC(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 OLFUWQFGAVROEA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- ZJWLHFWEFOMZAL-UHFFFAOYSA-N 3-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-6-methoxy-1h-quinazoline-2,4-dione Chemical compound O=C1C2=CC(OC)=CC=C2NC(=O)N1CCN(CC1)CCC1OC1=CC=C(Cl)C(Cl)=C1 ZJWLHFWEFOMZAL-UHFFFAOYSA-N 0.000 claims description 3
- QWSWUJUPZKKMCB-UHFFFAOYSA-N 3-[[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethylamino]methyl]-6,7-dimethylchromen-4-one Chemical compound O=C1C=2C=C(C)C(C)=CC=2OC=C1CNCCN(CC1)CCC1C(=O)C1=CC=C(Cl)C=C1 QWSWUJUPZKKMCB-UHFFFAOYSA-N 0.000 claims description 3
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- APSKKFUPDZBWNV-UHFFFAOYSA-N 4-[[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethylamino]methyl]-1,5-dimethyl-2-phenylpyrazol-3-one Chemical compound O=C1N(C=2C=CC=CC=2)N(C)C(C)=C1CNCCN(CC1)CCC1C(=O)C1=CC=C(Cl)C=C1 APSKKFUPDZBWNV-UHFFFAOYSA-N 0.000 claims description 3
- ATAPQCXFQQJJQF-UHFFFAOYSA-N 6-chloro-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]pyrazin-2-amine Chemical compound ClC1=CN=CC(NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 ATAPQCXFQQJJQF-UHFFFAOYSA-N 0.000 claims description 3
- GDPQAWMLYMBYKE-UHFFFAOYSA-N 6-chloro-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]pyridazin-3-amine Chemical compound N1=NC(Cl)=CC=C1NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 GDPQAWMLYMBYKE-UHFFFAOYSA-N 0.000 claims description 3
- WWRGONNHZFUSAT-UHFFFAOYSA-N 6-chloro-n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]pyrazin-2-amine Chemical compound ClC1=CN=CC(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 WWRGONNHZFUSAT-UHFFFAOYSA-N 0.000 claims description 3
- YLGDPKLRWDOCHX-UHFFFAOYSA-N [1-[2-[(2-chloro-6-fluorophenyl)methylamino]ethyl]piperidin-4-yl]-(4-chlorophenyl)methanone Chemical compound FC1=CC=CC(Cl)=C1CNCCN1CCC(C(=O)C=2C=CC(Cl)=CC=2)CC1 YLGDPKLRWDOCHX-UHFFFAOYSA-N 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- KETMPDYDKCWDQW-UHFFFAOYSA-N n-[2-[4-(3,4-dichloroanilino)piperidin-1-yl]ethyl]-3-methoxybenzamide;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC(C(=O)NCCN2CCC(CC2)NC=2C=C(Cl)C(Cl)=CC=2)=C1 KETMPDYDKCWDQW-UHFFFAOYSA-N 0.000 claims description 3
- KWXJUNDUJSJTBH-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-1,3-benzothiazol-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC=2SC3=CC=CC=C3N=2)CC1 KWXJUNDUJSJTBH-UHFFFAOYSA-N 0.000 claims description 3
- SJDLHXHEAZDEPB-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-1-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2N(C)N=CC2=C1NCCN(CC1)CCC1OC1=CC=C(Cl)C(Cl)=C1 SJDLHXHEAZDEPB-UHFFFAOYSA-N 0.000 claims description 3
- PCKWFEMVMVVWBW-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(C)=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 PCKWFEMVMVVWBW-UHFFFAOYSA-N 0.000 claims description 3
- VNNOZQFEDPIYTO-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-2,5-dimethyl-1,3-oxazole-4-carboxamide Chemical compound O1C(C)=NC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1C VNNOZQFEDPIYTO-UHFFFAOYSA-N 0.000 claims description 3
- LHCHQRNVSKTWFV-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-2-(methylsulfanylmethyl)pyrimidin-4-amine Chemical compound CSCC1=NC=CC(NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 LHCHQRNVSKTWFV-UHFFFAOYSA-N 0.000 claims description 3
- OABROTVIJSOZCG-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-2-methoxyacetamide Chemical compound C1CN(CCNC(=O)COC)CCC1OC1=CC=C(Cl)C(Cl)=C1 OABROTVIJSOZCG-UHFFFAOYSA-N 0.000 claims description 3
- VOEFLKXNTZWMOY-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-2-methylsulfanylpyrimidin-4-amine Chemical compound CSC1=NC=CC(NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 VOEFLKXNTZWMOY-UHFFFAOYSA-N 0.000 claims description 3
- CUCPXUJTZQFAEV-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-2-phenoxyacetamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)COC=2C=CC=CC=2)CC1 CUCPXUJTZQFAEV-UHFFFAOYSA-N 0.000 claims description 3
- FBTMKTZWRAXPLD-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-2-phenylacetamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)CC=2C=CC=CC=2)CC1 FBTMKTZWRAXPLD-UHFFFAOYSA-N 0.000 claims description 3
- WUBLBLSCBTYXAY-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-2-pyridin-4-yl-1,3-thiazole-4-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C=2N=C(SC=2)C=2C=CN=CC=2)CC1 WUBLBLSCBTYXAY-UHFFFAOYSA-N 0.000 claims description 3
- HCZDPNORRYKRTB-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3,5-difluorobenzamide Chemical compound FC1=CC(F)=CC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 HCZDPNORRYKRTB-UHFFFAOYSA-N 0.000 claims description 3
- KBKXFOOUOMDXLU-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3-fluorobenzamide Chemical compound FC1=CC=CC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 KBKXFOOUOMDXLU-UHFFFAOYSA-N 0.000 claims description 3
- LBJLDURINCUAHI-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3-methoxy-4-methylbenzamide Chemical compound C1=C(C)C(OC)=CC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 LBJLDURINCUAHI-UHFFFAOYSA-N 0.000 claims description 3
- DZAFQLBGKORWFO-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3-phenylpropanamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)CCC=2C=CC=CC=2)CC1 DZAFQLBGKORWFO-UHFFFAOYSA-N 0.000 claims description 3
- REXMJLJELCTNFZ-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4-phenylbutanamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)CCCC=2C=CC=CC=2)CC1 REXMJLJELCTNFZ-UHFFFAOYSA-N 0.000 claims description 3
- AHSSAFRUOLFUBM-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-5-methylthieno[2,3-d]pyrimidin-4-amine Chemical compound C=12C(C)=CSC2=NC=NC=1NCCN(CC1)CCC1OC1=CC=C(Cl)C(Cl)=C1 AHSSAFRUOLFUBM-UHFFFAOYSA-N 0.000 claims description 3
- BNSSXUYAHFYQHZ-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-6-methyl-2-methylsulfanylpyrimidin-4-amine Chemical compound CSC1=NC(C)=CC(NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 BNSSXUYAHFYQHZ-UHFFFAOYSA-N 0.000 claims description 3
- YRFKXMUBFJVPGU-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-7h-purin-6-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC2=C3N=CN=C3N=CN2)CC1 YRFKXMUBFJVPGU-UHFFFAOYSA-N 0.000 claims description 3
- KWRJZKYBEXODFN-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]cyclobutanecarboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C2CCC2)CC1 KWRJZKYBEXODFN-UHFFFAOYSA-N 0.000 claims description 3
- PZAASYQJPDVLGT-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]cyclopentanecarboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C2CCCC2)CC1 PZAASYQJPDVLGT-UHFFFAOYSA-N 0.000 claims description 3
- YZTPNTWVGMYLQS-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]naphthalene-2-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C=2C=C3C=CC=CC3=CC=2)CC1 YZTPNTWVGMYLQS-UHFFFAOYSA-N 0.000 claims description 3
- GCVCTXVBOIRBAE-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]-2-(2,3-dihydro-1,4-benzodioxin-3-yl)-1,3-thiazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNC(=O)C=2N=C(SC=2)C2OC3=CC=CC=C3OC2)CC1 GCVCTXVBOIRBAE-UHFFFAOYSA-N 0.000 claims description 3
- UGTFRXYQCXLGLY-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]-3-cyanobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNC(=O)C=2C=C(C=CC=2)C#N)CC1 UGTFRXYQCXLGLY-UHFFFAOYSA-N 0.000 claims description 3
- DPCKMLABADQZQK-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)NCCN2CCC(CC2)C(=O)C=2C=CC(Cl)=CC=2)=C1 DPCKMLABADQZQK-UHFFFAOYSA-N 0.000 claims description 3
- BCXZRGJIBCYTLQ-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]-3-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NCCN2CCC(CC2)C(=O)C=2C=CC(Cl)=CC=2)=C1 BCXZRGJIBCYTLQ-UHFFFAOYSA-N 0.000 claims description 3
- SRSUXJTVUYNDTA-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]-4-methyl-3-nitrobenzamide Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1C(=O)NCCN1CCC(C(=O)C=2C=CC(Cl)=CC=2)CC1 SRSUXJTVUYNDTA-UHFFFAOYSA-N 0.000 claims description 3
- VVAOLFLNBAIMMQ-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NCCN1CCC(C(=O)C=2C=CC(Cl)=CC=2)CC1 VVAOLFLNBAIMMQ-UHFFFAOYSA-N 0.000 claims description 3
- SGGCUGPPYADYEG-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]-4-nitrobenzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NCCN1CCC(C(=O)C=2C=CC(Cl)=CC=2)CC1 SGGCUGPPYADYEG-UHFFFAOYSA-N 0.000 claims description 3
- NNTVHXHZODJAQQ-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]bicyclo[2.2.1]hept-2-ene-5-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNC(=O)C2C3CC(C=C3)C2)CC1 NNTVHXHZODJAQQ-UHFFFAOYSA-N 0.000 claims description 3
- AZAIECPMCVIVON-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]cyclohexanecarboxamide Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNC(=O)C2CCCCC2)CC1 AZAIECPMCVIVON-UHFFFAOYSA-N 0.000 claims description 3
- XOWPNWWZNRGDRP-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]furan-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNC(=O)C=2OC=CC=2)CC1 XOWPNWWZNRGDRP-UHFFFAOYSA-N 0.000 claims description 3
- GWUDMKBOTHPMTO-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]naphthalene-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNC(=O)C=2C=C3C=CC=CC3=CC=2)CC1 GWUDMKBOTHPMTO-UHFFFAOYSA-N 0.000 claims description 3
- UJKHZNIBYNNKDX-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]quinoxaline-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNC(=O)C=2N=C3C=CC=CC3=NC=2)CC1 UJKHZNIBYNNKDX-UHFFFAOYSA-N 0.000 claims description 3
- HNMNYNMOFINIKE-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]thiophene-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNC(=O)C=2SC=CC=2)CC1 HNMNYNMOFINIKE-UHFFFAOYSA-N 0.000 claims description 3
- PNAHIPAYIBRUFT-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-1,3-benzothiazol-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCCNC=2SC3=CC=CC=C3N=2)CC1 PNAHIPAYIBRUFT-UHFFFAOYSA-N 0.000 claims description 3
- GTMVVEHZVVCYQH-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-1,3-benzoxazol-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCCNC=2OC3=CC=CC=C3N=2)CC1 GTMVVEHZVVCYQH-UHFFFAOYSA-N 0.000 claims description 3
- JORCUBGWXPAPNG-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-1,8-naphthyridin-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCCNC=2N=C3N=CC=CC3=CC=2)CC1 JORCUBGWXPAPNG-UHFFFAOYSA-N 0.000 claims description 3
- YSHXZDCGHBLWIB-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-4,6-dimethoxypyrimidin-2-amine Chemical compound COC1=CC(OC)=NC(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 YSHXZDCGHBLWIB-UHFFFAOYSA-N 0.000 claims description 3
- WVOAEJYFEHFEIU-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-4-(furan-3-yl)pyrimidin-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCCNC=2N=C(C=CN=2)C2=COC=C2)CC1 WVOAEJYFEHFEIU-UHFFFAOYSA-N 0.000 claims description 3
- WPYKSZLRMQEQSG-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-4-phenylpyrimidin-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCCNC=2N=C(C=CN=2)C=2C=CC=CC=2)CC1 WPYKSZLRMQEQSG-UHFFFAOYSA-N 0.000 claims description 3
- NQSGHKUNRWAANG-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-4-pyridin-3-ylpyrimidin-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCCNC=2N=C(C=CN=2)C=2C=NC=CC=2)CC1 NQSGHKUNRWAANG-UHFFFAOYSA-N 0.000 claims description 3
- LULOKMHNHCLNTA-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-4-thiophen-2-ylpyrimidin-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCCNC=2N=C(C=CN=2)C=2SC=CC=2)CC1 LULOKMHNHCLNTA-UHFFFAOYSA-N 0.000 claims description 3
- YRGRRKBIZLQZEY-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-4-thiophen-3-ylpyrimidin-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCCNC=2N=C(C=CN=2)C2=CSC=C2)CC1 YRGRRKBIZLQZEY-UHFFFAOYSA-N 0.000 claims description 3
- YBPQRVURRORWIE-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-7h-purin-6-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCCNC2=C3N=CN=C3N=CN2)CC1 YBPQRVURRORWIE-UHFFFAOYSA-N 0.000 claims description 3
- AXGODTPMEJUMJX-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]pyrimidin-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCCNC=2N=CC=CN=2)CC1 AXGODTPMEJUMJX-UHFFFAOYSA-N 0.000 claims description 3
- RUHMSOCBISJCEB-UHFFFAOYSA-N n-[4-[[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethylamino]methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CNCCN1CCC(C(=O)C=2C=CC(Cl)=CC=2)CC1 RUHMSOCBISJCEB-UHFFFAOYSA-N 0.000 claims description 3
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- IRHNODZMYZXIQC-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(3-nitro-4-pyridin-2-ylsulfanylphenyl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound C=1C=C(SC=2N=CC=CC=2)C([N+](=O)[O-])=CC=1CNCCN(CC1)CCC1C(=O)C1=CC=C(Cl)C=C1 IRHNODZMYZXIQC-UHFFFAOYSA-N 0.000 claims description 2
- XNGVLISOMZWKAQ-UHFFFAOYSA-N 2-[[2-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propylamino]pyrimidin-4-yl]-methylamino]ethanol Chemical compound OCCN(C)C1=CC=NC(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 XNGVLISOMZWKAQ-UHFFFAOYSA-N 0.000 claims description 2
- VVWOJGLYFQOSHE-UHFFFAOYSA-N 2-[[4-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propylamino]pyrimidin-2-yl]amino]ethanol Chemical compound OCCNC1=NC=CC(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 VVWOJGLYFQOSHE-UHFFFAOYSA-N 0.000 claims description 2
- LXRQUFJGFDAHOE-UHFFFAOYSA-N 4-chloro-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3-methoxybenzamide Chemical compound C1=C(Cl)C(OC)=CC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 LXRQUFJGFDAHOE-UHFFFAOYSA-N 0.000 claims description 2
- MNMGURNXXQQXDV-UHFFFAOYSA-N 6-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethylamino]-1,3-dimethylpyrimidine-2,4-dione Chemical compound O=C1N(C)C(=O)N(C)C(NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 MNMGURNXXQQXDV-UHFFFAOYSA-N 0.000 claims description 2
- 102000009410 Chemokine receptor Human genes 0.000 claims description 2
- 108050000299 Chemokine receptor Proteins 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
- SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 2
- 150000004820 halides Chemical group 0.000 claims description 2
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- BLRWPDDIYQWCLQ-UHFFFAOYSA-N n-[1-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-3-methylbutan-2-yl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC(CN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)C(C)C)=C1 BLRWPDDIYQWCLQ-UHFFFAOYSA-N 0.000 claims description 2
- GKLCGRWCVOIQRH-UHFFFAOYSA-N n-[1-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-3-methylbutan-2-yl]-4-methylbenzamide Chemical compound C=1C=C(C)C=CC=1C(=O)NC(C(C)C)CN(CC1)CCC1OC1=CC=C(Cl)C(Cl)=C1 GKLCGRWCVOIQRH-UHFFFAOYSA-N 0.000 claims description 2
- QLDSETCYASKHSM-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-1,3-benzoxazol-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC=2OC3=CC=CC=C3N=2)CC1 QLDSETCYASKHSM-UHFFFAOYSA-N 0.000 claims description 2
- VEEOQIODRFAASP-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4-phenylpyrimidin-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC=2N=C(C=CN=2)C=2C=CC=CC=2)CC1 VEEOQIODRFAASP-UHFFFAOYSA-N 0.000 claims description 2
- XHZUGNRUYREDGZ-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-5-methoxy-2-methylpyrimidin-4-amine Chemical compound COC1=CN=C(C)N=C1NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 XHZUGNRUYREDGZ-UHFFFAOYSA-N 0.000 claims description 2
- DJOYNOJKWBOLTJ-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-5-methoxy-2-methylsulfanylpyrimidin-4-amine Chemical compound COC1=CN=C(SC)N=C1NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 DJOYNOJKWBOLTJ-UHFFFAOYSA-N 0.000 claims description 2
- OJZLSZAYGQCTEK-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-7-methylthieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=CSC2=C1NCCN(CC1)CCC1OC1=CC=C(Cl)C(Cl)=C1 OJZLSZAYGQCTEK-UHFFFAOYSA-N 0.000 claims description 2
- BLPURSJNUZZDBX-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]cyclohexanecarboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C2CCCCC2)CC1 BLPURSJNUZZDBX-UHFFFAOYSA-N 0.000 claims description 2
- KQDWDIXMRXFLKT-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]-2-phenoxyacetamide Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNC(=O)COC=2C=CC=CC=2)CC1 KQDWDIXMRXFLKT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- LALDGZAOEXVHEY-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(4-phenylpiperidin-4-yl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNCC2(CCNCC2)C=2C=CC=CC=2)CC1 LALDGZAOEXVHEY-UHFFFAOYSA-N 0.000 claims 1
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 1
- KFFDPUVRJFFJRV-UHFFFAOYSA-N 3-[[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethylamino]methyl]chromen-4-one Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNCC=2C(C3=CC=CC=C3OC=2)=O)CC1 KFFDPUVRJFFJRV-UHFFFAOYSA-N 0.000 claims 1
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- ZTUUVDYQBLRAAC-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxamide Chemical compound C1C2C(C(=O)N)CC1C=C2 ZTUUVDYQBLRAAC-UHFFFAOYSA-N 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 238000004949 mass spectrometry Methods 0.000 description 271
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 120
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 112
- 239000000047 product Substances 0.000 description 83
- 102000052567 Anaphase-Promoting Complex-Cyclosome Apc1 Subunit Human genes 0.000 description 75
- 108091006463 SLC25A24 Proteins 0.000 description 75
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 42
- 239000007787 solid Substances 0.000 description 39
- 238000005481 NMR spectroscopy Methods 0.000 description 30
- 239000012074 organic phase Substances 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 21
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 21
- 239000003921 oil Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000004587 chromatography analysis Methods 0.000 description 14
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 206010039083 rhinitis Diseases 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 210000000222 eosinocyte Anatomy 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 238000011097 chromatography purification Methods 0.000 description 7
- RUQIUASLAXJZIE-UHFFFAOYSA-N 3-methoxybenzoyl chloride Chemical compound COC1=CC=CC(C(Cl)=O)=C1 RUQIUASLAXJZIE-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 5
- 102100023688 Eotaxin Human genes 0.000 description 5
- 101710139422 Eotaxin Proteins 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 208000006673 asthma Diseases 0.000 description 5
- 230000035605 chemotaxis Effects 0.000 description 5
- 210000001616 monocyte Anatomy 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- 208000030507 AIDS Diseases 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- OZLGRUXZXMRXGP-UHFFFAOYSA-N Fluo-3 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=C(C=2)C2=C3C=C(Cl)C(=O)C=C3OC3=CC(O)=C(Cl)C=C32)N(CC(O)=O)CC(O)=O)=C1 OZLGRUXZXMRXGP-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 102000019034 Chemokines Human genes 0.000 description 3
- 108010012236 Chemokines Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 239000003146 anticoagulant agent Substances 0.000 description 3
- 229940127219 anticoagulant drug Drugs 0.000 description 3
- 208000010668 atopic eczema Diseases 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 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 description 3
- 238000003384 imaging method Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- FTAFETTVRQXSRZ-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 FTAFETTVRQXSRZ-UHFFFAOYSA-N 0.000 description 3
- 210000004493 neutrocyte Anatomy 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002953 phosphate buffered saline Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 210000003491 skin Anatomy 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- TZRQZPMQUXEZMC-UHFFFAOYSA-N tert-butyl n-(2-bromoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCBr TZRQZPMQUXEZMC-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- CCKAMSOSAWJYBF-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(2-fluoro-4,5-dimethoxyphenyl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound C1=C(OC)C(OC)=CC(F)=C1CNCCN1CCC(C(=O)C=2C=CC(Cl)=CC=2)CC1 CCKAMSOSAWJYBF-UHFFFAOYSA-N 0.000 description 2
- GQWDJTMFSZHGMX-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(3-hydroxy-4-methoxyphenyl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound C1=C(O)C(OC)=CC=C1CNCCN1CCC(C(=O)C=2C=CC(Cl)=CC=2)CC1 GQWDJTMFSZHGMX-UHFFFAOYSA-N 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- ZOPXEBJEWRETPJ-IZZDOVSWSA-N (e)-n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]-3-phenylprop-2-enamide Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNC(=O)\C=C\C=2C=CC=CC=2)CC1 ZOPXEBJEWRETPJ-IZZDOVSWSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- QPIPEHZSHGDUEL-UHFFFAOYSA-N 2-acetamido-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-1,3-thiazole-4-carboxamide Chemical compound S1C(NC(=O)C)=NC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 QPIPEHZSHGDUEL-UHFFFAOYSA-N 0.000 description 2
- PFODAJFKGNHIKF-UHFFFAOYSA-N 2-amino-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-1,3-thiazole-4-carboxamide Chemical compound S1C(N)=NC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 PFODAJFKGNHIKF-UHFFFAOYSA-N 0.000 description 2
- XBPPLECAZBTMMK-UHFFFAOYSA-N 2-chloro-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CCl XBPPLECAZBTMMK-UHFFFAOYSA-N 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
- JXLSUJLHSUIKHP-UHFFFAOYSA-N 3-amino-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4-methoxybenzamide Chemical compound C1=C(N)C(OC)=CC=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 JXLSUJLHSUIKHP-UHFFFAOYSA-N 0.000 description 2
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
- JHZCXLDNXHWXJA-UHFFFAOYSA-N 4-chloro-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3-nitrobenzamide Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 JHZCXLDNXHWXJA-UHFFFAOYSA-N 0.000 description 2
- SHSGDXCJYVZFTP-UHFFFAOYSA-N 4-ethoxybenzoic acid Chemical compound CCOC1=CC=C(C(O)=O)C=C1 SHSGDXCJYVZFTP-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 2
- MMXKXXGRZUAQGP-UHFFFAOYSA-N 6-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propylamino]-1,3-dimethylpyrimidine-2,4-dione Chemical compound O=C1N(C)C(=O)N(C)C(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 MMXKXXGRZUAQGP-UHFFFAOYSA-N 0.000 description 2
- DYXDOWBDPGAJHK-UHFFFAOYSA-N 6-chloro-n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]pyridazin-3-amine Chemical compound N1=NC(Cl)=CC=C1NCCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 DYXDOWBDPGAJHK-UHFFFAOYSA-N 0.000 description 2
- OVGRJQQHTOESDL-UHFFFAOYSA-N 6-chloro-n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]pyridin-2-amine Chemical compound ClC1=CC=CC(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 OVGRJQQHTOESDL-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 102100022718 Atypical chemokine receptor 2 Human genes 0.000 description 2
- 102100031172 C-C chemokine receptor type 1 Human genes 0.000 description 2
- 101710149814 C-C chemokine receptor type 1 Proteins 0.000 description 2
- 102100024167 C-C chemokine receptor type 3 Human genes 0.000 description 2
- 101710149862 C-C chemokine receptor type 3 Proteins 0.000 description 2
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
- OABOXRPGTFRBFZ-IMJSIDKUSA-N Cys-Cys Chemical compound SC[C@H](N)C(=O)N[C@@H](CS)C(O)=O OABOXRPGTFRBFZ-IMJSIDKUSA-N 0.000 description 2
- 101000678892 Homo sapiens Atypical chemokine receptor 2 Proteins 0.000 description 2
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 description 2
- 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 2
- 102100026236 Interleukin-8 Human genes 0.000 description 2
- 108090001007 Interleukin-8 Proteins 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- RATAYRRRZOWEPY-UHFFFAOYSA-N N-[1-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-3-methylbutan-2-yl]-4-methylbenzamide hydrochloride Chemical compound Cl.CC(C)C(CN1CCC(CC1)Oc1ccc(Cl)c(Cl)c1)NC(=O)c1ccc(C)cc1 RATAYRRRZOWEPY-UHFFFAOYSA-N 0.000 description 2
- 241000721454 Pemphigus Species 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229910006074 SO2NH2 Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002975 chemoattractant Substances 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 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 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 210000003979 eosinophil Anatomy 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 2
- 229940096397 interleukin-8 Drugs 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- 206010025135 lupus erythematosus Diseases 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- NSKZINWLPRKWDC-UHFFFAOYSA-N methyl 4-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethylamino]-4-oxobutanoate Chemical compound C1CN(CCNC(=O)CCC(=O)OC)CCC1OC1=CC=C(Cl)C(Cl)=C1 NSKZINWLPRKWDC-UHFFFAOYSA-N 0.000 description 2
- QIIHHUHGQJPRND-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-1,3-benzodioxole-5-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C=2C=C3OCOC3=CC=2)CC1 QIIHHUHGQJPRND-UHFFFAOYSA-N 0.000 description 2
- KQSSUXAOULQXIV-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-1,8-naphthyridin-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC=2N=C3N=CC=CC3=CC=2)CC1 KQSSUXAOULQXIV-UHFFFAOYSA-N 0.000 description 2
- ZISSECHEDKXQAI-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-1h-imidazole-5-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C=2N=CNC=2)CC1 ZISSECHEDKXQAI-UHFFFAOYSA-N 0.000 description 2
- LGAZSGRGURZRHR-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-2,4-difluorobenzamide Chemical compound FC1=CC(F)=CC=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 LGAZSGRGURZRHR-UHFFFAOYSA-N 0.000 description 2
- JVSQVHSJEFXFRT-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-2-iodobenzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C=2C(=CC=CC=2)I)CC1 JVSQVHSJEFXFRT-UHFFFAOYSA-N 0.000 description 2
- MQERTRHDLBTFFH-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 MQERTRHDLBTFFH-UHFFFAOYSA-N 0.000 description 2
- DYGZKAWWMOSVJK-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-2-methylbenzamide Chemical compound CC1=CC=CC=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 DYGZKAWWMOSVJK-UHFFFAOYSA-N 0.000 description 2
- JCZWLPKVMPQFQD-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-2-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 JCZWLPKVMPQFQD-UHFFFAOYSA-N 0.000 description 2
- MRTWXQBKCWYQLW-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-2-phenylacetamide;hydrochloride Chemical compound Cl.C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)CC=2C=CC=CC=2)CC1 MRTWXQBKCWYQLW-UHFFFAOYSA-N 0.000 description 2
- ZZJXRWKPAZSRJC-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3,5-dinitrobenzamide Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 ZZJXRWKPAZSRJC-UHFFFAOYSA-N 0.000 description 2
- SBCGODLUNFOCIX-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3-fluoro-4-methoxybenzamide Chemical compound C1=C(F)C(OC)=CC=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 SBCGODLUNFOCIX-UHFFFAOYSA-N 0.000 description 2
- SETIHLUZSWNKTG-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3-hydroxybenzamide;hydrochloride Chemical compound Cl.OC1=CC=CC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 SETIHLUZSWNKTG-UHFFFAOYSA-N 0.000 description 2
- WOCAUAGFAOCBHT-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 WOCAUAGFAOCBHT-UHFFFAOYSA-N 0.000 description 2
- HTVQOZOZAIYPRA-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3-methoxybenzamide;hydrochloride Chemical compound Cl.COC1=CC=CC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 HTVQOZOZAIYPRA-UHFFFAOYSA-N 0.000 description 2
- YSRLFWOFKGYOFR-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 YSRLFWOFKGYOFR-UHFFFAOYSA-N 0.000 description 2
- YTUKBSHEPUURCK-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3-methylfuran-2-carboxamide Chemical compound C1=COC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1C YTUKBSHEPUURCK-UHFFFAOYSA-N 0.000 description 2
- MZVLWYDCCWHQFH-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4,5-dimethylfuran-2-carboxamide Chemical compound O1C(C)=C(C)C=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 MZVLWYDCCWHQFH-UHFFFAOYSA-N 0.000 description 2
- QOYIEWYJWVPSNB-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4,6-dimethoxypyrimidin-2-amine Chemical compound COC1=CC(OC)=NC(NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 QOYIEWYJWVPSNB-UHFFFAOYSA-N 0.000 description 2
- OJMHDQHNQCORBV-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4-(furan-3-yl)pyrimidin-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC=2N=C(C=CN=2)C2=COC=C2)CC1 OJMHDQHNQCORBV-UHFFFAOYSA-N 0.000 description 2
- FVYCULJCSOBDLR-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4-(trifluoromethyl)pyrimidin-2-amine Chemical compound FC(F)(F)C1=CC=NC(NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 FVYCULJCSOBDLR-UHFFFAOYSA-N 0.000 description 2
- ZYHXWIHFKNVOSJ-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4-ethoxybenzamide Chemical compound C1=CC(OCC)=CC=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 ZYHXWIHFKNVOSJ-UHFFFAOYSA-N 0.000 description 2
- MMRUIYLXLJUSGC-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4-iodobenzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C=2C=CC(I)=CC=2)CC1 MMRUIYLXLJUSGC-UHFFFAOYSA-N 0.000 description 2
- LSECCOKTVBGCPQ-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4-methyl-3-nitrobenzamide Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 LSECCOKTVBGCPQ-UHFFFAOYSA-N 0.000 description 2
- VZWJVDVJJFOVHX-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 VZWJVDVJJFOVHX-UHFFFAOYSA-N 0.000 description 2
- NMOPBBNBMLLCEV-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4-nitrobenzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 NMOPBBNBMLLCEV-UHFFFAOYSA-N 0.000 description 2
- RZTSRZKJOOOKMA-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4-propan-2-yloxybenzamide Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 RZTSRZKJOOOKMA-UHFFFAOYSA-N 0.000 description 2
- ISOOYEFAGWGFOV-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4-propylsulfanylpyrimidin-2-amine Chemical compound CCCSC1=CC=NC(NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 ISOOYEFAGWGFOV-UHFFFAOYSA-N 0.000 description 2
- ZGHGGEVGIQQCMZ-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-4-pyridin-3-ylpyrimidin-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC=2N=C(C=CN=2)C=2C=NC=CC=2)CC1 ZGHGGEVGIQQCMZ-UHFFFAOYSA-N 0.000 description 2
- VNGXYAQDIVSFEJ-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-5-methoxy-1-benzofuran-2-carboxamide Chemical compound C=1C2=CC(OC)=CC=C2OC=1C(=O)NCCN(CC1)CCC1OC1=CC=C(Cl)C(Cl)=C1 VNGXYAQDIVSFEJ-UHFFFAOYSA-N 0.000 description 2
- LIMGNCBIBIFOEN-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-7-ethoxy-1-benzofuran-2-carboxamide Chemical compound O1C=2C(OCC)=CC=CC=2C=C1C(=O)NCCN(CC1)CCC1OC1=CC=C(Cl)C(Cl)=C1 LIMGNCBIBIFOEN-UHFFFAOYSA-N 0.000 description 2
- CNUGRMNAHHHHRM-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-7-methoxy-1-benzofuran-2-carboxamide Chemical compound O1C=2C(OC)=CC=CC=2C=C1C(=O)NCCN(CC1)CCC1OC1=CC=C(Cl)C(Cl)=C1 CNUGRMNAHHHHRM-UHFFFAOYSA-N 0.000 description 2
- OHVFGEMUTFGUOR-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]bicyclo[2.2.1]hept-2-ene-5-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C2C3CC(C=C3)C2)CC1 OHVFGEMUTFGUOR-UHFFFAOYSA-N 0.000 description 2
- ZOFJDGSINAIGAX-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C=2OC=CC=2)CC1 ZOFJDGSINAIGAX-UHFFFAOYSA-N 0.000 description 2
- LPMFADILUGHIAD-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]furan-2-carboxamide;hydrochloride Chemical compound Cl.C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C=2OC=CC=2)CC1 LPMFADILUGHIAD-UHFFFAOYSA-N 0.000 description 2
- ANTCGVOAMRTSJJ-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]pyrimidin-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC=2N=CC=CN=2)CC1 ANTCGVOAMRTSJJ-UHFFFAOYSA-N 0.000 description 2
- ONYTZTZSTPRUHS-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]quinoxaline-2-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C=2N=C3C=CC=CC3=NC=2)CC1 ONYTZTZSTPRUHS-UHFFFAOYSA-N 0.000 description 2
- FSZPXCGKPJLDGK-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]thiophene-2-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C=2SC=CC=2)CC1 FSZPXCGKPJLDGK-UHFFFAOYSA-N 0.000 description 2
- UIHNEYBTKXCMPS-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNC(=O)C=2C=CC=CC=2)CC1 UIHNEYBTKXCMPS-UHFFFAOYSA-N 0.000 description 2
- QGUVTCMYSOSXFE-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-1-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2N(C)N=CC2=C1NCCCN(CC1)CCC1OC1=CC=C(Cl)C(Cl)=C1 QGUVTCMYSOSXFE-UHFFFAOYSA-N 0.000 description 2
- NOWGGYMOFSIVHA-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-2,6-dimethoxypyrimidin-4-amine Chemical compound COC1=NC(OC)=CC(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 NOWGGYMOFSIVHA-UHFFFAOYSA-N 0.000 description 2
- YLZWVBYTKXBFFI-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-2-(methylsulfanylmethyl)pyrimidin-4-amine Chemical compound CSCC1=NC=CC(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 YLZWVBYTKXBFFI-UHFFFAOYSA-N 0.000 description 2
- YWBQKEHSNGDHKJ-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-2-methylsulfanyl-6-(trifluoromethyl)pyrimidin-4-amine Chemical compound FC(F)(F)C1=NC(SC)=NC(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 YWBQKEHSNGDHKJ-UHFFFAOYSA-N 0.000 description 2
- KKEHZASRXRMVEW-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-2-methylsulfanylpyrimidin-4-amine Chemical compound CSC1=NC=CC(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 KKEHZASRXRMVEW-UHFFFAOYSA-N 0.000 description 2
- IUKWUWOTBICNEV-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-4-(trifluoromethyl)pyrimidin-2-amine Chemical compound FC(F)(F)C1=CC=NC(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 IUKWUWOTBICNEV-UHFFFAOYSA-N 0.000 description 2
- WWOINECOLZVMKL-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-4-propylsulfanylpyrimidin-2-amine Chemical compound CCCSC1=CC=NC(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 WWOINECOLZVMKL-UHFFFAOYSA-N 0.000 description 2
- OGGFUYHLQSDNBL-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-5-methoxy-2-methylpyrimidin-4-amine Chemical compound COC1=CN=C(C)N=C1NCCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 OGGFUYHLQSDNBL-UHFFFAOYSA-N 0.000 description 2
- KYRIOZQSGUKCBI-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-5-methoxy-2-methylsulfanylpyrimidin-4-amine Chemical compound COC1=CN=C(SC)N=C1NCCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 KYRIOZQSGUKCBI-UHFFFAOYSA-N 0.000 description 2
- QKBVECZBMTUOCW-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-5-methylthieno[2,3-d]pyrimidin-4-amine Chemical compound C=12C(C)=CSC2=NC=NC=1NCCCN(CC1)CCC1OC1=CC=C(Cl)C(Cl)=C1 QKBVECZBMTUOCW-UHFFFAOYSA-N 0.000 description 2
- NTTHUHDBOMNZQH-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-6-methylpyridin-2-amine Chemical compound CC1=CC=CC(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 NTTHUHDBOMNZQH-UHFFFAOYSA-N 0.000 description 2
- MPDOZIITBQYNNJ-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-7-methylthieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=CSC2=C1NCCCN(CC1)CCC1OC1=CC=C(Cl)C(Cl)=C1 MPDOZIITBQYNNJ-UHFFFAOYSA-N 0.000 description 2
- NCDKWNZTPAKVCQ-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-9-methylpurin-6-amine Chemical compound N1=CN=C2N(C)C=NC2=C1NCCCN(CC1)CCC1OC1=CC=C(Cl)C(Cl)=C1 NCDKWNZTPAKVCQ-UHFFFAOYSA-N 0.000 description 2
- VODYKEUGXCHTEC-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]pyridin-2-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCCNC=2N=CC=CC=2)CC1 VODYKEUGXCHTEC-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 210000005259 peripheral blood Anatomy 0.000 description 2
- 239000011886 peripheral blood Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 125000005936 piperidyl group Chemical group 0.000 description 2
- 229920001992 poloxamer 407 Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 230000001052 transient effect Effects 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- SZXBQTSZISFIAO-ZETCQYMHSA-N (2s)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)OC(C)(C)C SZXBQTSZISFIAO-ZETCQYMHSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- HIRXHSWOYNEDIE-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-(pyridin-4-ylmethylamino)ethyl]piperidin-4-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNCC=2C=CN=CC=2)CC1 HIRXHSWOYNEDIE-UHFFFAOYSA-N 0.000 description 1
- RMTAXKXHFKSHPJ-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(2,4-dimethoxypyrimidin-5-yl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound COC1=NC(OC)=NC=C1CNCCN1CCC(C(=O)C=2C=CC(Cl)=CC=2)CC1 RMTAXKXHFKSHPJ-UHFFFAOYSA-N 0.000 description 1
- NTICZMKTSNVWMT-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(3-hydroxy-4-nitrophenyl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound C1=C([N+]([O-])=O)C(O)=CC(CNCCN2CCC(CC2)C(=O)C=2C=CC(Cl)=CC=2)=C1 NTICZMKTSNVWMT-UHFFFAOYSA-N 0.000 description 1
- LRKHJDIAAFTZID-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(3-methylthiophen-2-yl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound C1=CSC(CNCCN2CCC(CC2)C(=O)C=2C=CC(Cl)=CC=2)=C1C LRKHJDIAAFTZID-UHFFFAOYSA-N 0.000 description 1
- QQZVTJZQPKPZAV-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(5-ethylthiophen-2-yl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound S1C(CC)=CC=C1CNCCN1CCC(C(=O)C=2C=CC(Cl)=CC=2)CC1 QQZVTJZQPKPZAV-UHFFFAOYSA-N 0.000 description 1
- PSTVENQTOPIJHX-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[(6-methylpyridin-2-yl)methylamino]ethyl]piperidin-4-yl]methanone Chemical compound CC1=CC=CC(CNCCN2CCC(CC2)C(=O)C=2C=CC(Cl)=CC=2)=N1 PSTVENQTOPIJHX-UHFFFAOYSA-N 0.000 description 1
- NTMOXDJIDPKQKQ-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-[[5-(3-nitrophenyl)furan-2-yl]methylamino]ethyl]piperidin-4-yl]methanone Chemical compound [O-][N+](=O)C1=CC=CC(C=2OC(CNCCN3CCC(CC3)C(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 NTMOXDJIDPKQKQ-UHFFFAOYSA-N 0.000 description 1
- LZUYKOBTHSPKED-UHFFFAOYSA-N (4-chlorophenyl)-piperidin-4-ylmethanone;hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1C(=O)C1CCNCC1 LZUYKOBTHSPKED-UHFFFAOYSA-N 0.000 description 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 1
- UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
- LICYXSOFOZSZRD-UHFFFAOYSA-N 1-(2-aminoethyl)-N-(3,4-dichlorophenyl)piperidin-4-amine 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(CCN)CCC1NC1=CC=C(Cl)C(Cl)=C1 LICYXSOFOZSZRD-UHFFFAOYSA-N 0.000 description 1
- DGMOTMRIAMJQOR-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-3-methylbutan-2-amine Chemical compound C1CN(CC(N)C(C)C)CCC1OC1=CC=C(Cl)C(Cl)=C1 DGMOTMRIAMJQOR-UHFFFAOYSA-N 0.000 description 1
- JBMTUXVKTGBMLE-UHFFFAOYSA-N 1-methylpyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2N(C)N=CC2=C1N JBMTUXVKTGBMLE-UHFFFAOYSA-N 0.000 description 1
- RZHVGRFYLWCTRZ-UHFFFAOYSA-N 2,4-dichloro-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]benzamide Chemical compound ClC1=CC(Cl)=CC=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 RZHVGRFYLWCTRZ-UHFFFAOYSA-N 0.000 description 1
- WEEMDRWIKYCTQM-UHFFFAOYSA-N 2,6-dimethoxybenzenecarbothioamide Chemical compound COC1=CC=CC(OC)=C1C(N)=S WEEMDRWIKYCTQM-UHFFFAOYSA-N 0.000 description 1
- VKJCJJYNVIYVQR-UHFFFAOYSA-N 2-(3-bromopropyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCBr)C(=O)C2=C1 VKJCJJYNVIYVQR-UHFFFAOYSA-N 0.000 description 1
- UMKSAURFQFUULT-UHFFFAOYSA-N 2-Amino-5-methoxybenzoic acid Chemical compound COC1=CC=C(N)C(C(O)=O)=C1 UMKSAURFQFUULT-UHFFFAOYSA-N 0.000 description 1
- HNLXNOZHXNSSPN-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCOCCOCCOCCO)C=C1 HNLXNOZHXNSSPN-UHFFFAOYSA-N 0.000 description 1
- GUXFOLSWRZODOX-UHFFFAOYSA-N 2-[3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-2,4-dioxoquinazolin-1-yl]-n,n-dimethylacetamide;hydrochloride Chemical compound Cl.O=C1N(CC(=O)N(C)C)C2=CC=CC=C2C(=O)N1CCN(CC1)CCC1C(=O)C1=CC=C(F)C=C1 GUXFOLSWRZODOX-UHFFFAOYSA-N 0.000 description 1
- DYNHVEHBIMYLRY-UHFFFAOYSA-N 2-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]isoindole-1,3-dione Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCCN2C(C3=CC=CC=C3C2=O)=O)CC1 DYNHVEHBIMYLRY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SKHPRKKQGKNLMB-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethanamine Chemical compound C1CN(CCN)CCC1OC1=CC=C(Cl)C(Cl)=C1 SKHPRKKQGKNLMB-UHFFFAOYSA-N 0.000 description 1
- JVWAQHJVSLHDTG-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethanamine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(CCN)CCC1OC1=CC=C(Cl)C(Cl)=C1 JVWAQHJVSLHDTG-UHFFFAOYSA-N 0.000 description 1
- PVPXVESRTMPRRZ-UHFFFAOYSA-N 2-[[4-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethylamino]pyrimidin-2-yl]-methylamino]ethanol Chemical compound OCCN(C)C1=NC=CC(NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 PVPXVESRTMPRRZ-UHFFFAOYSA-N 0.000 description 1
- SSDVFNNGIZCJGU-UHFFFAOYSA-N 2-[[4-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propylamino]pyrimidin-2-yl]-methylamino]ethanol Chemical compound OCCN(C)C1=NC=CC(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 SSDVFNNGIZCJGU-UHFFFAOYSA-N 0.000 description 1
- CHBIQFITKYJGFF-UHFFFAOYSA-N 2-amino-1-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-3-methylbutan-1-one Chemical compound C1CN(C(=O)C(N)C(C)C)CCC1OC1=CC=C(Cl)C(Cl)=C1 CHBIQFITKYJGFF-UHFFFAOYSA-N 0.000 description 1
- BKBSYZAFDNAPCD-UHFFFAOYSA-N 2-amino-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-5-methoxybenzamide Chemical compound COC1=CC=C(N)C(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 BKBSYZAFDNAPCD-UHFFFAOYSA-N 0.000 description 1
- WFTYOJFJHQSUGC-UHFFFAOYSA-N 2-bromo-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-5-methoxybenzamide Chemical compound COC1=CC=C(Br)C(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 WFTYOJFJHQSUGC-UHFFFAOYSA-N 0.000 description 1
- RUDMXUVERBPUIU-UHFFFAOYSA-N 2-chloro-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C=2C(=CC=CC=2)Cl)CC1 RUDMXUVERBPUIU-UHFFFAOYSA-N 0.000 description 1
- HOZLOOPIXHWKCI-UHFFFAOYSA-N 2-chloro-n-methylacetamide Chemical compound CNC(=O)CCl HOZLOOPIXHWKCI-UHFFFAOYSA-N 0.000 description 1
- WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-UHFFFAOYSA-N 0.000 description 1
- HCHICBXDFQPKED-UHFFFAOYSA-N 3,4-dichloro-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C=2C=C(Cl)C(Cl)=CC=2)CC1 HCHICBXDFQPKED-UHFFFAOYSA-N 0.000 description 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 1
- VMDAAZKIKNFBNL-UHFFFAOYSA-N 3,5-dichloro-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]benzamide Chemical compound ClC1=CC(Cl)=CC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 VMDAAZKIKNFBNL-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- OKPFIWIMBJNFSE-UHFFFAOYSA-N 3-(trifluoromethoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC(OC(F)(F)F)=C1 OKPFIWIMBJNFSE-UHFFFAOYSA-N 0.000 description 1
- YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
- SUTPYJMEFYTZQV-UHFFFAOYSA-N 3-bromo-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C=2C=C(Br)C=CC=2)CC1 SUTPYJMEFYTZQV-UHFFFAOYSA-N 0.000 description 1
- ZEARWRCUZVYMGQ-UHFFFAOYSA-N 3-chloro-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]benzamide Chemical compound ClC1=CC=CC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 ZEARWRCUZVYMGQ-UHFFFAOYSA-N 0.000 description 1
- WHIHIKVIWVIIER-UHFFFAOYSA-N 3-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1 WHIHIKVIWVIIER-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- DTFQMPQJMDEWKJ-UHFFFAOYSA-N 3-ethoxybenzoic acid Chemical compound CCOC1=CC=CC(C(O)=O)=C1 DTFQMPQJMDEWKJ-UHFFFAOYSA-N 0.000 description 1
- SYVNVEGIRVXRQH-UHFFFAOYSA-N 3-fluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1 SYVNVEGIRVXRQH-UHFFFAOYSA-N 0.000 description 1
- DQNSSLUVUXZLEO-UHFFFAOYSA-N 4-(3,4-dichlorophenoxy)piperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCNCC1 DQNSSLUVUXZLEO-UHFFFAOYSA-N 0.000 description 1
- RATSANVPHHXDCT-UHFFFAOYSA-N 4-(trifluoromethoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OC(F)(F)F)C=C1 RATSANVPHHXDCT-UHFFFAOYSA-N 0.000 description 1
- VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
- YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
- XYWIPYBIIRTJMM-IBGZPJMESA-N 4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1-yl]butanoyl]amino]-2-fluorobenzamide Chemical compound CC[C@H](N1C=C(OC)C(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(N=N1)C(F)(F)F)C(=O)NC1=CC(F)=C(C=C1)C(N)=O XYWIPYBIIRTJMM-IBGZPJMESA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- BAXBAKNPTIKXDR-UHFFFAOYSA-N 4-amino-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3-methoxybenzamide Chemical compound C1=C(N)C(OC)=CC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 BAXBAKNPTIKXDR-UHFFFAOYSA-N 0.000 description 1
- GNMSBVLIQKMYJS-UHFFFAOYSA-N 4-bromo-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C=2C=CC(Br)=CC=2)CC1 GNMSBVLIQKMYJS-UHFFFAOYSA-N 0.000 description 1
- AVFLNALVPBLGEV-UHFFFAOYSA-N 4-chloro-1-methylpyrazolo[3,4-d]pyrimidine Chemical compound N1=CN=C2N(C)N=CC2=C1Cl AVFLNALVPBLGEV-UHFFFAOYSA-N 0.000 description 1
- POBRWJKFEQDGKH-UHFFFAOYSA-N 4-chloro-2-[2-(dimethylamino)-2-oxoethoxy]benzoic acid Chemical compound CN(C)C(=O)COC1=CC(Cl)=CC=C1C(O)=O POBRWJKFEQDGKH-UHFFFAOYSA-N 0.000 description 1
- LWXFCZXRFBUOOR-UHFFFAOYSA-N 4-chloro-2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1O LWXFCZXRFBUOOR-UHFFFAOYSA-N 0.000 description 1
- HGTBPXAJTIBUGT-UHFFFAOYSA-N 4-chloro-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 HGTBPXAJTIBUGT-UHFFFAOYSA-N 0.000 description 1
- NPKBHANCRFKYRT-UHFFFAOYSA-N 4-cyano-n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C=2C=CC(=CC=2)C#N)CC1 NPKBHANCRFKYRT-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
- ZVERWTXKKWSSHH-UHFFFAOYSA-N 4-propan-2-yloxybenzoic acid Chemical compound CC(C)OC1=CC=C(C(O)=O)C=C1 ZVERWTXKKWSSHH-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- NPMFBHDRRWILOH-UHFFFAOYSA-N 5-chloro-n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]pyridin-2-amine Chemical compound N1=CC(Cl)=CC=C1NCCCN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 NPMFBHDRRWILOH-UHFFFAOYSA-N 0.000 description 1
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
- JNYLMODTPLSLIF-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine-3-carboxylic acid Chemical group OC(=O)C1=CC=C(C(F)(F)F)N=C1 JNYLMODTPLSLIF-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 208000035939 Alveolitis allergic Diseases 0.000 description 1
- 201000008283 Atrophic Rhinitis Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 208000009137 Behcet syndrome Diseases 0.000 description 1
- 102100031151 C-C chemokine receptor type 2 Human genes 0.000 description 1
- 101710149815 C-C chemokine receptor type 2 Proteins 0.000 description 1
- 102100037853 C-C chemokine receptor type 4 Human genes 0.000 description 1
- 101710149863 C-C chemokine receptor type 4 Proteins 0.000 description 1
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 description 1
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 description 1
- 102100036301 C-C chemokine receptor type 7 Human genes 0.000 description 1
- 102100036305 C-C chemokine receptor type 8 Human genes 0.000 description 1
- 102100025074 C-C chemokine receptor-like 2 Human genes 0.000 description 1
- 102100021943 C-C motif chemokine 2 Human genes 0.000 description 1
- 101710155857 C-C motif chemokine 2 Proteins 0.000 description 1
- 102100032366 C-C motif chemokine 7 Human genes 0.000 description 1
- 101710155834 C-C motif chemokine 7 Proteins 0.000 description 1
- 102100034871 C-C motif chemokine 8 Human genes 0.000 description 1
- 101710155833 C-C motif chemokine 8 Proteins 0.000 description 1
- 102100036166 C-X-C chemokine receptor type 1 Human genes 0.000 description 1
- VQBPHBSKCQGAMI-UHFFFAOYSA-N C1CN(C(=O)C(NC(C)=O)C(C)C)CCC1OC1=CC=C(Cl)C(Cl)=C1 Chemical compound C1CN(C(=O)C(NC(C)=O)C(C)C)CCC1OC1=CC=C(Cl)C(Cl)=C1 VQBPHBSKCQGAMI-UHFFFAOYSA-N 0.000 description 1
- 102000001902 CC Chemokines Human genes 0.000 description 1
- 108010040471 CC Chemokines Proteins 0.000 description 1
- 108050006947 CXC Chemokine Proteins 0.000 description 1
- 102000019388 CXC chemokine Human genes 0.000 description 1
- 101710178035 Chorismate synthase 2 Proteins 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 208000015943 Coeliac disease Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 101710152694 Cysteine synthase 2 Proteins 0.000 description 1
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 108010092408 Eosinophil Peroxidase Proteins 0.000 description 1
- 102100028471 Eosinophil peroxidase Human genes 0.000 description 1
- 206010053177 Epidermolysis Diseases 0.000 description 1
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- 208000027445 Farmer Lung Diseases 0.000 description 1
- 102100037362 Fibronectin Human genes 0.000 description 1
- 108010067306 Fibronectins Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 108091006027 G proteins Proteins 0.000 description 1
- 102000030782 GTP binding Human genes 0.000 description 1
- 108091000058 GTP-Binding Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 description 1
- 101000777558 Homo sapiens C-C chemokine receptor type 10 Proteins 0.000 description 1
- 101000716068 Homo sapiens C-C chemokine receptor type 6 Proteins 0.000 description 1
- 101000716065 Homo sapiens C-C chemokine receptor type 7 Proteins 0.000 description 1
- 101000716063 Homo sapiens C-C chemokine receptor type 8 Proteins 0.000 description 1
- 101000716070 Homo sapiens C-C chemokine receptor type 9 Proteins 0.000 description 1
- 101000947174 Homo sapiens C-X-C chemokine receptor type 1 Proteins 0.000 description 1
- 101000973997 Homo sapiens Nucleosome assembly protein 1-like 4 Proteins 0.000 description 1
- 101000947178 Homo sapiens Platelet basic protein Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 201000003838 Idiopathic interstitial pneumonia Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 206010065764 Mucosal infection Diseases 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 102100036154 Platelet basic protein Human genes 0.000 description 1
- 206010036774 Proctitis Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 1
- 208000033464 Reiter syndrome Diseases 0.000 description 1
- 206010039088 Rhinitis atrophic Diseases 0.000 description 1
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 description 1
- 208000021386 Sjogren Syndrome Diseases 0.000 description 1
- 208000026062 Tissue disease Diseases 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 206010047115 Vasculitis Diseases 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- GCXMRXDGZLNADK-UHFFFAOYSA-N [1-(2-aminoethyl)piperidin-4-yl]-(4-chlorophenyl)methanone Chemical compound C1CN(CCN)CCC1C(=O)C1=CC=C(Cl)C=C1 GCXMRXDGZLNADK-UHFFFAOYSA-N 0.000 description 1
- XRJGJSBHSFQMHU-UHFFFAOYSA-N [1-[2-[(4-bromo-1h-pyrazol-5-yl)methylamino]ethyl]piperidin-4-yl]-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(CCNCC=2C(=CNN=2)Br)CC1 XRJGJSBHSFQMHU-UHFFFAOYSA-N 0.000 description 1
- XCKQLBGYDBLQCS-UHFFFAOYSA-N [1-[2-[[5-chloro-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylamino]ethyl]piperidin-4-yl]-(4-chlorophenyl)methanone Chemical compound CN1N=C(C(F)(F)F)C(CNCCN2CCC(CC2)C(=O)C=2C=CC(Cl)=CC=2)=C1Cl XCKQLBGYDBLQCS-UHFFFAOYSA-N 0.000 description 1
- QGMUEVREFCMCGY-UHFFFAOYSA-N [4-(2-aminoethyl)piperazin-1-yl]-(3,4-dichlorophenyl)methanone;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(CCN)CCN1C(=O)C1=CC=C(Cl)C(Cl)=C1 QGMUEVREFCMCGY-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
- 125000004422 alkyl sulphonamide group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 230000003185 calcium uptake Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 239000013592 cell lysate Substances 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000003399 chemotactic effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 0.000 description 1
- 201000009151 chronic rhinitis Diseases 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 108010004073 cysteinylcysteine Proteins 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000005363 dialkylsulfonamide group Chemical group 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000002327 eosinophilic effect Effects 0.000 description 1
- 201000001564 eosinophilic gastroenteritis Diseases 0.000 description 1
- 230000010437 erythropoiesis Effects 0.000 description 1
- ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 description 1
- PWDGLIWNOMOQHM-UHFFFAOYSA-N ethanol;hydrazine;hydrate Chemical compound O.NN.CCO PWDGLIWNOMOQHM-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 208000022195 farmer lung disease Diseases 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003463 hyperproliferative effect Effects 0.000 description 1
- 230000001969 hypertrophic effect Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000008105 immune reaction Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- FPCCSQOGAWCVBH-UHFFFAOYSA-N ketanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1 FPCCSQOGAWCVBH-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 201000010260 leiomyoma Diseases 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 208000008585 mastocytosis Diseases 0.000 description 1
- AEUKDPKXTPNBNY-XEYRWQBLSA-N mcp 2 Chemical compound C([C@@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)C1=CC=CC=C1 AEUKDPKXTPNBNY-XEYRWQBLSA-N 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- VQBMLPAOWGPBON-UHFFFAOYSA-N n-(3,4-dichlorophenyl)piperidin-4-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C(Cl)=CC=C1NC1CCNCC1 VQBMLPAOWGPBON-UHFFFAOYSA-N 0.000 description 1
- FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
- ISWAUFMGBSNAHJ-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-2,6-dimethoxypyrimidin-4-amine Chemical compound COC1=NC(OC)=CC(NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 ISWAUFMGBSNAHJ-UHFFFAOYSA-N 0.000 description 1
- BIWQWPKNOLOQCG-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3-ethoxybenzamide;hydrochloride Chemical compound Cl.CCOC1=CC=CC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 BIWQWPKNOLOQCG-UHFFFAOYSA-N 0.000 description 1
- CBWVUHWMSNTREN-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-3-fluorobenzamide;hydrochloride Chemical compound Cl.FC1=CC=CC(C(=O)NCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 CBWVUHWMSNTREN-UHFFFAOYSA-N 0.000 description 1
- OTUMJJOKQMKNJO-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]-9-methylpurin-6-amine Chemical compound N1=CN=C2N(C)C=NC2=C1NCCN(CC1)CCC1OC1=CC=C(Cl)C(Cl)=C1 OTUMJJOKQMKNJO-UHFFFAOYSA-N 0.000 description 1
- DWHOBDRNYCOIBB-UHFFFAOYSA-N n-[2-[4-(3,4-dichlorophenoxy)piperidin-1-yl]ethyl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(CCNC(=O)C=2C=CC=CC=2)CC1 DWHOBDRNYCOIBB-UHFFFAOYSA-N 0.000 description 1
- QHMOPGAWYKLAAQ-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]-3-hydroxybenzamide;hydrochloride Chemical compound Cl.OC1=CC=CC(C(=O)NCCN2CCC(CC2)C(=O)C=2C=CC(Cl)=CC=2)=C1 QHMOPGAWYKLAAQ-UHFFFAOYSA-N 0.000 description 1
- VYDYGKPUNOMESB-UHFFFAOYSA-N n-[2-[4-(4-chlorobenzoyl)piperidin-1-yl]ethyl]-3-methoxybenzamide;hydrochloride Chemical compound Cl.COC1=CC=CC(C(=O)NCCN2CCC(CC2)C(=O)C=2C=CC(Cl)=CC=2)=C1 VYDYGKPUNOMESB-UHFFFAOYSA-N 0.000 description 1
- CPXQTHVKAINDHE-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-2-ethylsulfanyl-6-methylpyrimidin-4-amine Chemical compound CCSC1=NC(C)=CC(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 CPXQTHVKAINDHE-UHFFFAOYSA-N 0.000 description 1
- CENUZHTZTUCONP-UHFFFAOYSA-N n-[3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propyl]-6-methyl-2-methylsulfanylpyrimidin-4-amine Chemical compound CSC1=NC(C)=CC(NCCCN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=N1 CENUZHTZTUCONP-UHFFFAOYSA-N 0.000 description 1
- NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
- LKFYDKLTDCPTTJ-UHFFFAOYSA-N n-hexylcyclopentanamine Chemical group CCCCCCNC1CCCC1 LKFYDKLTDCPTTJ-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- 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 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 238000004634 pharmacological analysis method Methods 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- MYIGUVWXDJBPEV-UHFFFAOYSA-N piperazin-2-amine Chemical compound NC1CNCCN1 MYIGUVWXDJBPEV-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- MTURGQJJIULABB-UHFFFAOYSA-N propan-1-amine;dihydrochloride Chemical compound Cl.Cl.CCCN MTURGQJJIULABB-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 208000002574 reactive arthritis Diseases 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 201000005671 spondyloarthropathy Diseases 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229960002385 streptomycin sulfate Drugs 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- HZSDDUWKKKTJSZ-UHFFFAOYSA-N tert-butyl 4-(3,4-dichloroanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC=C(Cl)C(Cl)=C1 HZSDDUWKKKTJSZ-UHFFFAOYSA-N 0.000 description 1
- FKRKGPPELQBYCJ-UHFFFAOYSA-N tert-butyl 4-(3,4-dichlorophenoxy)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=C(Cl)C(Cl)=C1 FKRKGPPELQBYCJ-UHFFFAOYSA-N 0.000 description 1
- PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 1
- ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
- VPOIPCJBJNWHSJ-UHFFFAOYSA-N tert-butyl n-(2-piperazin-1-ylethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCN1CCNCC1 VPOIPCJBJNWHSJ-UHFFFAOYSA-N 0.000 description 1
- VQOVZEJDCVLCOI-UHFFFAOYSA-N tert-butyl n-[2-[4-(3,4-dichlorobenzoyl)piperazin-1-yl]ethyl]carbamate Chemical compound C1CN(CCNC(=O)OC(C)(C)C)CCN1C(=O)C1=CC=C(Cl)C(Cl)=C1 VQOVZEJDCVLCOI-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 208000001319 vasomotor rhinitis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Virology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Communicable Diseases (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9901117A SE9901117D0 (sv) | 1999-03-26 | 1999-03-26 | Novel compounds |
| SE9902194A SE9902194D0 (sv) | 1999-06-10 | 1999-06-10 | Novel compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ20013451A3 true CZ20013451A3 (cs) | 2002-04-17 |
Family
ID=26663543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20013451A CZ20013451A3 (cs) | 1999-03-26 | 2000-03-22 | Nové sloučeniny |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US6518286B1 (enExample) |
| EP (1) | EP1165545A1 (enExample) |
| JP (1) | JP2002540204A (enExample) |
| KR (1) | KR20010108394A (enExample) |
| CN (1) | CN1344266A (enExample) |
| AU (1) | AU4157500A (enExample) |
| BR (1) | BR0009338A (enExample) |
| CA (1) | CA2361366A1 (enExample) |
| CZ (1) | CZ20013451A3 (enExample) |
| EE (1) | EE200100502A (enExample) |
| HU (1) | HUP0202017A3 (enExample) |
| IL (1) | IL144353A0 (enExample) |
| IS (1) | IS6024A (enExample) |
| NO (1) | NO20014518D0 (enExample) |
| PL (1) | PL350904A1 (enExample) |
| SK (1) | SK11822001A3 (enExample) |
| TR (1) | TR200102800T2 (enExample) |
| WO (1) | WO2000058305A1 (enExample) |
Families Citing this family (71)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EE200100502A (et) | 1999-03-26 | 2002-12-16 | Astrazeneca Ab | Ühendid |
| SE9902987D0 (sv) | 1999-08-24 | 1999-08-24 | Astra Pharma Prod | Novel compounds |
| DE19952147A1 (de) * | 1999-10-29 | 2001-05-03 | Boehringer Ingelheim Pharma | Neue Cyclopropane, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| GB0004151D0 (en) | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel use |
| GB0004152D0 (en) | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel compounds |
| GB0004153D0 (en) | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel use |
| CO5300399A1 (es) | 2000-02-25 | 2003-07-31 | Astrazeneca Ab | Heterocicliocs que contienen nitrogeno, proceso para su preparacion y composiciones farmaceuticas que los contienen |
| GB0013060D0 (en) | 2000-05-31 | 2000-07-19 | Astrazeneca Ab | Chemical compounds |
| AR028948A1 (es) | 2000-06-20 | 2003-05-28 | Astrazeneca Ab | Compuestos novedosos |
| US7005439B2 (en) | 2000-06-20 | 2006-02-28 | Astrazeneca Ab | Compounds |
| TWI227231B (en) * | 2000-07-12 | 2005-02-01 | Novartis Ag | 4-benzoyl-piperidine derivatives for treating conditions mediated by CCR-3 |
| GB0021670D0 (en) * | 2000-09-04 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| AU2002215928A1 (en) * | 2000-10-09 | 2002-04-22 | Novartis Pharma Gmbh | N-(4-aryloxypiperidin-1-ylalkyl) cinnamic amides as ccr3 receptor antagonists |
| US7034042B2 (en) | 2000-10-09 | 2006-04-25 | Novartis Ag | N-(4-aryloxypiperidin-1-ylalkyl) cinnamic amides as CCR33 receptor antagonists |
| UY27003A1 (es) | 2000-11-06 | 2002-07-31 | Schering Ag | Productos radiofarmacéuticos para el diagnóstico de la enfermedad de alzheimer |
| GB0104050D0 (en) | 2001-02-19 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| AR035230A1 (es) | 2001-03-19 | 2004-05-05 | Astrazeneca Ab | Compuestos de bencimidazol, proceso para su preparacion, composicion farmaceutica, proceso para la preparacion de dicha composicion farmaceutica, y usos de estos compuestos para la elaboracion de medicamentos |
| GB0107228D0 (en) | 2001-03-22 | 2001-05-16 | Astrazeneca Ab | Chemical compounds |
| SE0101038D0 (sv) | 2001-03-23 | 2001-03-23 | Astrazeneca Ab | Novel compounds |
| US7115635B2 (en) | 2001-04-27 | 2006-10-03 | Mitsubishi Pharma Corporation | Benzylpiperidine compound |
| GB0114699D0 (en) * | 2001-06-15 | 2001-08-08 | Novartis Ag | Organic compounds |
| GB0117387D0 (en) * | 2001-07-17 | 2001-09-05 | Novartis Ag | Organic compounds |
| GB0117899D0 (en) | 2001-07-23 | 2001-09-12 | Astrazeneca Ab | Chemical compounds |
| SE0102640D0 (sv) | 2001-07-31 | 2001-07-31 | Astrazeneca Ab | Novel compounds |
| SE0102809D0 (sv) * | 2001-08-22 | 2001-08-22 | Astrazeneca Ab | Novel compounds |
| SE0103818D0 (sv) | 2001-11-15 | 2001-11-15 | Astrazeneca Ab | Chemical compounds |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| TW200303304A (en) | 2002-02-18 | 2003-09-01 | Astrazeneca Ab | Chemical compounds |
| CN103169708B (zh) | 2002-07-29 | 2018-02-02 | 里格尔药品股份有限公司 | 用2,4‑嘧啶二胺化合物治疗或者预防自体免疫性疾病的方法 |
| KR101297924B1 (ko) * | 2002-07-29 | 2013-08-20 | 리겔 파마슈티칼스, 인크. | 2,4-피리미딘디아민 화합물을 이용한 자가면역질환의 치료및 예방 방법 |
| EP2130541A3 (en) * | 2002-07-29 | 2013-12-18 | Rigel Pharmaceuticals, Inc. | Methods of treating or preventing autoimmune diseases with 2,4-pyrimidinediamine compounds |
| WO2004048343A1 (en) * | 2002-11-28 | 2004-06-10 | Schering Aktiengesellschaft | Chk-, pdk- and akt-inhibitory pyrimidines, their production and use as pharmaceutical agents |
| CN1744899A (zh) * | 2002-12-13 | 2006-03-08 | 史密丝克莱恩比彻姆公司 | 作为ccr5拮抗剂的哌啶衍生物 |
| EP2385040A1 (en) | 2003-03-14 | 2011-11-09 | ONO Pharmaceutical Co., Ltd. | Nitrogen-containing heterocyclic derivatives and drugs containing the same as the active ingredient |
| US7498323B2 (en) | 2003-04-18 | 2009-03-03 | Ono Pharmaceuticals Co., Ltd. | Spiro-piperidine compounds and medicinal use thereof |
| SE0301369D0 (sv) | 2003-05-09 | 2003-05-09 | Astrazeneca Ab | Chemical compounds |
| US7122542B2 (en) | 2003-07-30 | 2006-10-17 | Rigel Pharmaceuticals, Inc. | Methods of treating or preventing autoimmune diseases with 2,4-pyrimidinediamine compounds |
| WO2005040129A2 (en) * | 2003-10-24 | 2005-05-06 | F. Hoffmann-La Roche Ag | Ccr3 receptor antagonists |
| SE0400208D0 (sv) | 2004-02-02 | 2004-02-02 | Astrazeneca Ab | Chemical compounds |
| GB0412468D0 (en) * | 2004-06-04 | 2004-07-07 | Astrazeneca Ab | Chemical compounds |
| BRPI0512535A (pt) | 2004-06-24 | 2008-03-25 | Incyte Corp | compostos de piperidinas n-substituìdas, suas composições e métodos de modulações |
| KR101011848B1 (ko) | 2004-09-08 | 2011-02-01 | 미쓰비시 타나베 파마 코퍼레이션 | 모르폴린 화합물 |
| WO2006030925A1 (ja) | 2004-09-13 | 2006-03-23 | Ono Pharmaceutical Co., Ltd. | 含窒素複素環誘導体およびそれらを有効成分とする薬剤 |
| ATE540035T1 (de) | 2004-11-24 | 2012-01-15 | Rigel Pharmaceuticals Inc | Spiro-2,4-pyrimidindiamin-verbindungen und ihre verwendungen |
| US7576080B2 (en) * | 2004-12-23 | 2009-08-18 | Memory Pharmaceuticals Corporation | Certain thienopyrimidine derivatives as phosphodiesterase 10 inhibitors |
| EP1889622A4 (en) | 2005-05-31 | 2009-12-23 | Ono Pharmaceutical Co | SPIROPIPERIDINE COMPOUND AND MEDICINAL USE THEREOF |
| CA2612325A1 (en) * | 2005-06-15 | 2006-12-28 | Anormed Inc. | Chemokine receptor binding compounds |
| TW200738634A (en) | 2005-08-02 | 2007-10-16 | Astrazeneca Ab | New salt |
| JP5251127B2 (ja) | 2005-10-28 | 2013-07-31 | 小野薬品工業株式会社 | 塩基性基を含有する化合物およびその用途 |
| TW200800895A (en) * | 2005-11-02 | 2008-01-01 | Astrazeneca Ab | Novel compounds |
| PL1961744T3 (pl) | 2005-11-18 | 2013-09-30 | Ono Pharmaceutical Co | Związek zawierający grupę zasadową oraz jego zastosowanie |
| RU2396265C2 (ru) | 2006-02-17 | 2010-08-10 | Ф. Хоффманн-Ля Рош Аг | Производные бензоилпиперидина в качестве модуляторов рецепторов 5ht2 и d3 |
| EP1994003A4 (en) * | 2006-03-07 | 2009-12-02 | Astrazeneca Ab | PIPERIDINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, THEIR USE AS THERAPEUTIC AGENTS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEY |
| EP1994002A1 (en) * | 2006-03-07 | 2008-11-26 | AstraZeneca AB | Piperidine derivatives, their process for preparation, their use as therapeutic agents and pharmaceutical compositions containing them |
| US8003642B2 (en) | 2006-03-10 | 2011-08-23 | Ono Pharmaceutical Co., Ltd. | Nitrogenated heterocyclic derivative, and pharmaceutical agent comprising the derivative as active ingredient |
| EP2042503B1 (en) | 2006-05-16 | 2013-01-30 | Ono Pharmaceutical Co., Ltd. | Compound having acidic group which may be protected, and use thereof |
| WO2007146981A2 (en) * | 2006-06-15 | 2007-12-21 | Boehringer Ingelheim International Gmbh | 2-anilino-4-(heterocyclic)amino-pyrimidines as inhibitors of protein kinase c-alpha |
| CN101506176A (zh) | 2006-06-15 | 2009-08-12 | 贝林格尔.英格海姆国际有限公司 | 2-苯胺基-4-氨基亚烷基氨基嘧啶 |
| EP2055705A4 (en) | 2006-07-31 | 2014-08-20 | Ono Pharmaceutical Co | COMPOUND WITH A CYCLIC GROUP BOUND BY A SPIRO BINDING THEREOF AND APPLY THEREOF |
| EP2079693B1 (en) | 2006-10-31 | 2013-02-27 | F. Hoffmann-La Roche AG | Ether derivatives dual modulators of the 5-ht2a and d3 receptors |
| WO2008097976A1 (en) * | 2007-02-09 | 2008-08-14 | Kalypsys, Inc. | Heterocyclic modulators of tgr5 for treatment of disease |
| KR20090115953A (ko) * | 2007-03-06 | 2009-11-10 | 노파르티스 아게 | 염증성 또는 알레르기성 상태의 치료에 적합한 바이시클릭 유기 화합물 |
| JP5539190B2 (ja) * | 2007-06-12 | 2014-07-02 | エフ.ホフマン−ラ ロシュ アーゲー | チアゾロピリミジン類及びホスファチジルイノシトール−3キナーゼのインヒビターとしてのそれらの使用 |
| ES2399774T3 (es) * | 2007-09-24 | 2013-04-03 | Genentech, Inc. | Compuestos de tiazolopirimidina inhibidores de PI3K y métodos de uso |
| ES2842289T3 (es) | 2008-02-29 | 2021-07-13 | Vm Therapeutics Llc | Compuestos para tratar el síndrome del dolor y otros trastornos |
| WO2010129351A1 (en) | 2009-04-28 | 2010-11-11 | Schepens Eye Research Institute | Method to identify and treat age-related macular degeneration |
| CN104918940B (zh) * | 2012-11-16 | 2017-03-08 | 默沙东公司 | 人磷脂酰肌醇3‑激酶δ的嘌呤抑制剂 |
| CN111004218B (zh) * | 2018-10-08 | 2023-10-13 | 沈阳中化农药化工研发有限公司 | 含哌啶的嘧啶类化合物及用途 |
| US10702525B1 (en) * | 2019-09-04 | 2020-07-07 | United Arab Emirates University | Pyrimidine derivatives as anti-diabetic agents |
| WO2021217143A1 (en) * | 2020-04-24 | 2021-10-28 | Emory University | Aminopiperidine amides, derivatives, compositions, and uses related to cxcr4 modulation |
| JP2023528546A (ja) * | 2020-05-29 | 2023-07-04 | テグ-キョンプク メディカル イノベーション ファウンデーション | カルボキサミド誘導体およびそれを有効成分とする精神病の予防または治療に使用するための医薬組成物 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4335127A (en) * | 1979-01-08 | 1982-06-15 | Janssen Pharmaceutica, N.V. | Piperidinylalkyl quinazoline compounds, composition and method of use |
| DK159420C (da) | 1983-03-09 | 1991-03-11 | Ciba Geigy Ag | N-(piperidinyl-alkyl)-carboxamider og salte deraf, farmaceutiske praeparater indeholdende disse forbindelser samt anvendelsen af forbindelserne til fremstilling af antipsykotiske farmaceutiske praeparater |
| IL76366A (en) | 1984-09-14 | 1989-07-31 | Ciba Geigy Ag | 2,6-dialkyl-4-aryl-3,5-diacyl-1,4-dihydropyridine derivatives,processes for their manufacture and pharmaceutical preparations containing them |
| CA1246074A (en) * | 1984-12-05 | 1988-12-06 | Albertus H.M.T. Van Heertum | Derivatives of hydroxy- or amino-substituted (piperidinylalkyl)quinazolines |
| KR910006138B1 (ko) | 1986-09-30 | 1991-08-16 | 에자이 가부시끼가이샤 | 환상아민 유도체 |
| JP2860689B2 (ja) * | 1990-03-14 | 1999-02-24 | 第一製薬株式会社 | ピリミジン誘導体 |
| FR2667317B1 (fr) | 1990-10-02 | 1992-12-04 | Synthelabo | Derives de 2-aminopyrimidine-4-carboxamide, leur preparation et leur application en therapeutique. |
| US5143923B1 (en) * | 1991-04-29 | 1993-11-02 | Hoechst-Roussel Pharmaceuticals Incorporated | Benzoisothiazole-and benzisoxazole-3-carboxamides |
| FR2724382B1 (fr) | 1994-09-13 | 1996-10-18 | Synthelabo | Derives de 2-aminopyrimidine-4-carboxamide, leur preparation et leur application en therapeutique |
| EP0816362A4 (en) * | 1995-03-22 | 1998-07-08 | Taisho Pharmaceutical Co Ltd | THIAZOLE DERIVATIVES |
| JPH0940646A (ja) | 1995-07-27 | 1997-02-10 | Yamanouchi Pharmaceut Co Ltd | ベンゼン縮合環誘導体又はその塩 |
| JPH0977742A (ja) | 1995-09-12 | 1997-03-25 | Kyorin Pharmaceut Co Ltd | 新規なベンズアミド誘導体 |
| JP2000506904A (ja) | 1996-05-16 | 2000-06-06 | シナプティック・ファーマスーティカル・コーポレーション | ジヒドロピリミジン類およびその使用 |
| IL125658A0 (en) * | 1997-08-18 | 1999-04-11 | Hoffmann La Roche | Ccr-3 receptor antagonists |
| EP1047675A1 (en) * | 1998-01-21 | 2000-11-02 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| US6613905B1 (en) * | 1998-01-21 | 2003-09-02 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| JP3475177B2 (ja) * | 1998-11-17 | 2003-12-08 | エフ.ホフマン−ラ ロシュ アーゲー | 4−アロイルピペリジンccr−3受容体拮抗剤iii |
| EE200100502A (et) | 1999-03-26 | 2002-12-16 | Astrazeneca Ab | Ühendid |
-
2000
- 2000-03-22 EE EEP200100502A patent/EE200100502A/xx unknown
- 2000-03-22 CN CN00805451A patent/CN1344266A/zh active Pending
- 2000-03-22 PL PL00350904A patent/PL350904A1/xx not_active Application Discontinuation
- 2000-03-22 EP EP00921237A patent/EP1165545A1/en not_active Withdrawn
- 2000-03-22 TR TR2001/02800T patent/TR200102800T2/xx unknown
- 2000-03-22 SK SK1182-2001A patent/SK11822001A3/sk unknown
- 2000-03-22 KR KR1020017012174A patent/KR20010108394A/ko not_active Withdrawn
- 2000-03-22 JP JP2000608007A patent/JP2002540204A/ja active Pending
- 2000-03-22 HU HU0202017A patent/HUP0202017A3/hu unknown
- 2000-03-22 IL IL14435300A patent/IL144353A0/xx unknown
- 2000-03-22 AU AU41575/00A patent/AU4157500A/en not_active Abandoned
- 2000-03-22 CZ CZ20013451A patent/CZ20013451A3/cs unknown
- 2000-03-22 BR BR0009338-6A patent/BR0009338A/pt not_active IP Right Cessation
- 2000-03-22 CA CA002361366A patent/CA2361366A1/en not_active Abandoned
- 2000-03-22 US US09/555,565 patent/US6518286B1/en not_active Expired - Fee Related
- 2000-03-22 WO PCT/SE2000/000563 patent/WO2000058305A1/en not_active Ceased
-
2001
- 2001-07-26 IS IS6024A patent/IS6024A/is unknown
- 2001-09-17 NO NO20014518A patent/NO20014518D0/no unknown
-
2003
- 2003-01-09 US US10/339,261 patent/US6946478B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US6946478B2 (en) | 2005-09-20 |
| US20030134840A1 (en) | 2003-07-17 |
| JP2002540204A (ja) | 2002-11-26 |
| IL144353A0 (en) | 2002-05-23 |
| US6518286B1 (en) | 2003-02-11 |
| CN1344266A (zh) | 2002-04-10 |
| EP1165545A1 (en) | 2002-01-02 |
| PL350904A1 (en) | 2003-02-10 |
| HUP0202017A3 (en) | 2003-03-28 |
| SK11822001A3 (sk) | 2002-09-10 |
| TR200102800T2 (tr) | 2002-01-21 |
| KR20010108394A (ko) | 2001-12-07 |
| HUP0202017A2 (hu) | 2002-11-28 |
| WO2000058305A1 (en) | 2000-10-05 |
| AU4157500A (en) | 2000-10-16 |
| NO20014518L (no) | 2001-09-17 |
| NO20014518D0 (no) | 2001-09-17 |
| IS6024A (is) | 2001-07-26 |
| EE200100502A (et) | 2002-12-16 |
| CA2361366A1 (en) | 2000-10-05 |
| BR0009338A (pt) | 2001-12-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CZ20013451A3 (cs) | Nové sloučeniny | |
| US7304077B2 (en) | Chemical compounds | |
| US7348341B2 (en) | Chemical compounds | |
| US6525070B2 (en) | Bipiperidine derivatives as modulators of CCR3 activity and as H1 antagonists | |
| US7265227B2 (en) | Piperidine derivatives useful as modulators of chemokine receptor activity | |
| US6960602B2 (en) | Piperidine derivatives as modulators of chemokine receptors | |
| JP3857270B2 (ja) | ケモカイン受容体活性のモジュレーターとして有用なピペリジン誘導体 | |
| US20070161646A1 (en) | Piperidine Derivatives and Their Use as Modulators of Chemokine Receptor Activity (Especially CCR5) | |
| KR20050052511A (ko) | 케모킨 매개된 질병 상태의 치료에서 사용하기 위한 신규피페리딘 유도체 | |
| SK16152002A3 (sk) | Farmacueticky účinné piperidínové deriváty, najmä ako modulátory aktivity chemokínového receptora | |
| ES2269806T3 (es) | Derivados de piperidina y su uso como moduladores de la actividad de quimioquinas (especialmente de la ccr3). | |
| US6566376B1 (en) | Diphenyl-piperidine derivative | |
| US20040266823A1 (en) | Novel piperidine derivatives as modulators of chemokine receptors | |
| EP1363902B1 (en) | Chemical compounds | |
| US20040110952A1 (en) | N-4-piperidinyl compounds as ccr5 modulators | |
| US6562825B1 (en) | Piperazine derivatives as modulators of chemokine receptor activity | |
| JP2005526089A (ja) | ケモカイン受容体活性のモジュレーターとして有用なピペリジン誘導体 | |
| JP4380508B2 (ja) | 医薬組成物 | |
| SK17942002A3 (sk) | Deriváty fenylu, spôsoby ich prípravy, farmaceutické kompozície, ktoré ich obsahujú, a ich použitie v terapii | |
| MXPA01009665A (en) | Novel compounds | |
| ZA200106858B (en) | Novel compounds. |