KR20040013090A - 케모킨 수용체 활성의 조절자로서 유용한 피페리딘 유도체 - Google Patents
케모킨 수용체 활성의 조절자로서 유용한 피페리딘 유도체 Download PDFInfo
- Publication number
- KR20040013090A KR20040013090A KR10-2004-7000023A KR20047000023A KR20040013090A KR 20040013090 A KR20040013090 A KR 20040013090A KR 20047000023 A KR20047000023 A KR 20047000023A KR 20040013090 A KR20040013090 A KR 20040013090A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- formula
- compound
- dichlorophenoxy
- carbonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 230000000694 effects Effects 0.000 title abstract description 14
- 102000009410 Chemokine receptor Human genes 0.000 title description 6
- 108050000299 Chemokine receptor Proteins 0.000 title description 6
- 150000003053 piperidines Chemical class 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 282
- 150000001875 compounds Chemical class 0.000 claims abstract description 235
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 58
- 239000001257 hydrogen Substances 0.000 claims abstract description 51
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 102000019034 Chemokines Human genes 0.000 claims abstract description 9
- 108010012236 Chemokines Proteins 0.000 claims abstract description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- -1 nitro, hydroxy Chemical group 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 59
- 239000002904 solvent Substances 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical group 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 239000012453 solvate Substances 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 239000000460 chlorine Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 7
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 230000008878 coupling Effects 0.000 claims description 5
- 239000007822 coupling agent Substances 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000001266 acyl halides Chemical class 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 229960005141 piperazine Drugs 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 150000001450 anions Chemical class 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 abstract description 33
- 208000006673 asthma Diseases 0.000 abstract description 17
- 102100024167 C-C chemokine receptor type 3 Human genes 0.000 abstract description 7
- 101710149862 C-C chemokine receptor type 3 Proteins 0.000 abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 82
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 47
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 31
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000047 product Substances 0.000 description 21
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 20
- 238000001819 mass spectrum Methods 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000003643 water by type Substances 0.000 description 17
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
- 229910021529 ammonia Inorganic materials 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 208000010668 atopic eczema Diseases 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- 102100023688 Eotaxin Human genes 0.000 description 10
- 101710139422 Eotaxin Proteins 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 230000000172 allergic effect Effects 0.000 description 9
- GBOCNHMVRBRTAT-UHFFFAOYSA-N 4-(3,4-dichlorophenoxy)-1-piperidin-4-ylpiperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCNCC2)CC1 GBOCNHMVRBRTAT-UHFFFAOYSA-N 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 7
- 201000004624 Dermatitis Diseases 0.000 description 7
- 239000005557 antagonist Substances 0.000 description 7
- 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 7
- 210000003979 eosinophil Anatomy 0.000 description 7
- 125000004995 haloalkylthio group Chemical group 0.000 description 7
- 229960001340 histamine Drugs 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 125000003386 piperidinyl group Chemical group 0.000 description 7
- 210000003491 skin Anatomy 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- 125000001544 thienyl group Chemical group 0.000 description 7
- 208000030507 AIDS Diseases 0.000 description 6
- 201000008283 Atrophic Rhinitis Diseases 0.000 description 6
- 206010015150 Erythema Diseases 0.000 description 6
- 241000282412 Homo Species 0.000 description 6
- 206010024229 Leprosy Diseases 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 206010039088 Rhinitis atrophic Diseases 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 231100000321 erythema Toxicity 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 206010025135 lupus erythematosus Diseases 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- ONWSVWFUKSRUGQ-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-sulfonamide Chemical compound C1CN(S(=O)(=O)N)CCC1N1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 ONWSVWFUKSRUGQ-UHFFFAOYSA-N 0.000 description 5
- 102000004499 CCR3 Receptors Human genes 0.000 description 5
- 108010017316 CCR3 Receptors Proteins 0.000 description 5
- 206010020751 Hypersensitivity Diseases 0.000 description 5
- 230000001154 acute effect Effects 0.000 description 5
- 230000001684 chronic effect Effects 0.000 description 5
- 229960004132 diethyl ether Drugs 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- SFQQVXPYNZUIRQ-UHFFFAOYSA-N ethyl 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OCC)CCC1N1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 SFQQVXPYNZUIRQ-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 4
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- DQNSSLUVUXZLEO-UHFFFAOYSA-N 4-(3,4-dichlorophenoxy)piperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCNCC1 DQNSSLUVUXZLEO-UHFFFAOYSA-N 0.000 description 4
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 4
- 206010011224 Cough Diseases 0.000 description 4
- 229920002785 Croscarmellose sodium Polymers 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000007815 allergy Effects 0.000 description 4
- 230000001363 autoimmune Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 229960001681 croscarmellose sodium Drugs 0.000 description 4
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 4
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 210000004072 lung Anatomy 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 4
- KINKZEDQCGUBRF-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 KINKZEDQCGUBRF-UHFFFAOYSA-N 0.000 description 4
- 210000000440 neutrophil Anatomy 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- AQNGCIRCKWJYTG-UHFFFAOYSA-N tert-butyl n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylcarbamate Chemical compound C1CN(S(=O)(=O)NC(=O)OC(C)(C)C)CCC1N1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 AQNGCIRCKWJYTG-UHFFFAOYSA-N 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 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
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
- YRYUWEQXLZBDLN-UHFFFAOYSA-N 3-cyano-n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=C(C=CC=2)C#N)CC1 YRYUWEQXLZBDLN-UHFFFAOYSA-N 0.000 description 3
- QVLZVRFIGXNZMN-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 QVLZVRFIGXNZMN-UHFFFAOYSA-N 0.000 description 3
- ZDWNUSDUXVXKFB-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-propan-2-ylsulfonylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)NS(=O)(=O)C(C)C)CCC1N1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 ZDWNUSDUXVXKFB-UHFFFAOYSA-N 0.000 description 3
- RBYHGWYAMASYRV-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1CN(C(=O)N)CCC1N1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 RBYHGWYAMASYRV-UHFFFAOYSA-N 0.000 description 3
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- 201000001320 Atherosclerosis Diseases 0.000 description 3
- NVKOAYGOEXSEII-WGSAOQKQSA-N C1=CC(C)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 NVKOAYGOEXSEII-WGSAOQKQSA-N 0.000 description 3
- 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 3
- 102000009123 Fibrin Human genes 0.000 description 3
- 108010073385 Fibrin Proteins 0.000 description 3
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 241000721454 Pemphigus Species 0.000 description 3
- 206010035664 Pneumonia Diseases 0.000 description 3
- 208000002200 Respiratory Hypersensitivity Diseases 0.000 description 3
- 208000036284 Rhinitis seasonal Diseases 0.000 description 3
- 208000024780 Urticaria Diseases 0.000 description 3
- 206010047115 Vasculitis Diseases 0.000 description 3
- 230000010085 airway hyperresponsiveness Effects 0.000 description 3
- 208000026935 allergic disease Diseases 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 210000003651 basophil Anatomy 0.000 description 3
- 201000009151 chronic rhinitis Diseases 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
- 239000000284 extract Substances 0.000 description 3
- 229950003499 fibrin Drugs 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 3
- 230000001969 hypertrophic effect Effects 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000002953 phosphate buffered saline Substances 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- QGPLVRDUDYHISP-UHFFFAOYSA-M sodium;4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]cyclohexane-1-carboxylate Chemical compound [Na+].C1CC(C(=O)[O-])CCC1N1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 QGPLVRDUDYHISP-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 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 3
- 208000001319 vasomotor rhinitis Diseases 0.000 description 3
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 2
- XJVONDCVBSAKPU-UHFFFAOYSA-N 2,4-dichloro-3-fluorophenol Chemical compound OC1=CC=C(Cl)C(F)=C1Cl XJVONDCVBSAKPU-UHFFFAOYSA-N 0.000 description 2
- WKHAUPVZXUOYTL-UHFFFAOYSA-N 2-chloro-n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C(=CC=CC=2)Cl)CC1 WKHAUPVZXUOYTL-UHFFFAOYSA-N 0.000 description 2
- KXAXWOVWFPVEPH-UHFFFAOYSA-N 4-(2,4-dichloro-3-methylphenoxy)-1-piperidin-4-ylpiperidine Chemical compound CC1=C(Cl)C=CC(OC2CCN(CC2)C2CCNCC2)=C1Cl KXAXWOVWFPVEPH-UHFFFAOYSA-N 0.000 description 2
- CUINHOHYNRFZSB-UHFFFAOYSA-N 4-(3,4-dichlorophenoxy)-1-(4-methylpiperidin-4-yl)piperidine;dihydrochloride Chemical compound Cl.Cl.C1CC(OC=2C=C(Cl)C(Cl)=CC=2)CCN1C1(C)CCNCC1 CUINHOHYNRFZSB-UHFFFAOYSA-N 0.000 description 2
- REIZYHKXRGEBEI-UHFFFAOYSA-N 4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=C(C)C(Cl)=CC=2)Cl)CC1 REIZYHKXRGEBEI-UHFFFAOYSA-N 0.000 description 2
- HZUZFBPRVMJMHT-UHFFFAOYSA-N 4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]-n-(4-fluorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=C(Cl)C=CC(OC2CCN(CC2)C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC(F)=CC=2)=C1Cl HZUZFBPRVMJMHT-UHFFFAOYSA-N 0.000 description 2
- RDZRONBJZUCQAD-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(F)=CC=2)Cl)CC1 RDZRONBJZUCQAD-UHFFFAOYSA-N 0.000 description 2
- FHLJNJSZPGMALO-UHFFFAOYSA-N 4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=C(Cl)C(Cl)=CC=2)C)CC1 FHLJNJSZPGMALO-UHFFFAOYSA-N 0.000 description 2
- IUWXMHJXYHLXSR-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2,4,5-trifluorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=C(F)C(F)=CC(F)=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 IUWXMHJXYHLXSR-UHFFFAOYSA-N 0.000 description 2
- YISQPKPMJJVCCU-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2,5-dichlorothiophen-3-yl)sulfonylpiperidine-1-carboxamide Chemical compound S1C(Cl)=CC(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1Cl YISQPKPMJJVCCU-UHFFFAOYSA-N 0.000 description 2
- SWEHCFKMAYPEHK-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2,5-difluorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound FC1=CC=C(F)C(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 SWEHCFKMAYPEHK-UHFFFAOYSA-N 0.000 description 2
- CPGNWUXPMNXYJX-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(3,5-dichlorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound ClC1=CC(Cl)=CC(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 CPGNWUXPMNXYJX-UHFFFAOYSA-N 0.000 description 2
- FJXUEXJXAXDKTR-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(4,5-dichlorothiophen-2-yl)sulfonylpiperidine-1-carboxamide Chemical compound S1C(Cl)=C(Cl)C=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 FJXUEXJXAXDKTR-UHFFFAOYSA-N 0.000 description 2
- FRYRCDHNALIZSR-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-[2-(trifluoromethoxy)phenyl]sulfonylpiperidine-1-carboxamide Chemical compound FC(F)(F)OC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 FRYRCDHNALIZSR-UHFFFAOYSA-N 0.000 description 2
- NMSKJGUEGMOBLP-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-[4-(trifluoromethoxy)phenyl]sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 NMSKJGUEGMOBLP-UHFFFAOYSA-N 0.000 description 2
- LPHIWCBAJGQIIF-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-methyl-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N(C)C(=O)N(CC1)CCC1N(CC1)CCC1OC1=CC=C(Cl)C(Cl)=C1 LPHIWCBAJGQIIF-UHFFFAOYSA-N 0.000 description 2
- OYPBUCVUQHHURD-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1N1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 OYPBUCVUQHHURD-UHFFFAOYSA-N 0.000 description 2
- HHYBIQJOLMHLOC-UHFFFAOYSA-N 4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]-n-(2-chlorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)CC1 HHYBIQJOLMHLOC-UHFFFAOYSA-N 0.000 description 2
- IGCXNQLEJAPTMB-UHFFFAOYSA-N 4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)CC1 IGCXNQLEJAPTMB-UHFFFAOYSA-N 0.000 description 2
- OFFJHZRFEDVMAQ-UHFFFAOYSA-N 4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]-n-(4-chlorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC(Cl)=CC=2)CC1 OFFJHZRFEDVMAQ-UHFFFAOYSA-N 0.000 description 2
- QMOXERAIWSSOEG-UHFFFAOYSA-N 4-chloro-n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 QMOXERAIWSSOEG-UHFFFAOYSA-N 0.000 description 2
- VHUHQRQHGZKQJL-UHFFFAOYSA-N 4-chloro-n-[4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=CC(Cl)=CC=2)CC1 VHUHQRQHGZKQJL-UHFFFAOYSA-N 0.000 description 2
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 208000035939 Alveolitis allergic Diseases 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 2
- 102100022718 Atypical chemokine receptor 2 Human genes 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- PQHXPPICWGPBON-IYARVYRRSA-N C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C=CC=CC=2)CC1 Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C=CC=CC=2)CC1 PQHXPPICWGPBON-IYARVYRRSA-N 0.000 description 2
- DCPZHBDTBOMBAJ-SAABIXHNSA-N C1=CC(Cl)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 DCPZHBDTBOMBAJ-SAABIXHNSA-N 0.000 description 2
- PAEZTKREROBBNB-WGSAOQKQSA-N CC1=CC=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 PAEZTKREROBBNB-WGSAOQKQSA-N 0.000 description 2
- 208000015943 Coeliac disease Diseases 0.000 description 2
- 206010009900 Colitis ulcerative Diseases 0.000 description 2
- 206010010741 Conjunctivitis Diseases 0.000 description 2
- 208000011231 Crohn disease Diseases 0.000 description 2
- 206010012438 Dermatitis atopic Diseases 0.000 description 2
- 206010012442 Dermatitis contact Diseases 0.000 description 2
- 206010014950 Eosinophilia Diseases 0.000 description 2
- 206010065563 Eosinophilic bronchitis Diseases 0.000 description 2
- 206010014954 Eosinophilic fasciitis Diseases 0.000 description 2
- 208000027445 Farmer Lung Diseases 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 2
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 2
- 208000001204 Hashimoto Disease Diseases 0.000 description 2
- 208000030836 Hashimoto thyroiditis Diseases 0.000 description 2
- 101000678892 Homo sapiens Atypical chemokine receptor 2 Proteins 0.000 description 2
- 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 description 2
- 102000004890 Interleukin-8 Human genes 0.000 description 2
- 108090001007 Interleukin-8 Proteins 0.000 description 2
- 208000009388 Job Syndrome Diseases 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- 206010029164 Nephrotic syndrome Diseases 0.000 description 2
- 206010036774 Proctitis Diseases 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 description 2
- 208000021386 Sjogren Syndrome Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000006045 Spondylarthropathies Diseases 0.000 description 2
- 201000009594 Systemic Scleroderma Diseases 0.000 description 2
- 206010042953 Systemic sclerosis Diseases 0.000 description 2
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 description 2
- 206010046851 Uveitis Diseases 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 208000004631 alopecia areata Diseases 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000005219 aminonitrile group Chemical group 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000000954 anitussive effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 201000008937 atopic dermatitis Diseases 0.000 description 2
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 210000001185 bone marrow Anatomy 0.000 description 2
- 239000012267 brine Substances 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
- 206010006451 bronchitis Diseases 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000000451 chemical ionisation Methods 0.000 description 2
- 239000002975 chemoattractant Substances 0.000 description 2
- 230000003399 chemotactic effect Effects 0.000 description 2
- 230000035605 chemotaxis Effects 0.000 description 2
- 208000013116 chronic cough Diseases 0.000 description 2
- 208000017760 chronic graft versus host disease Diseases 0.000 description 2
- 208000010247 contact dermatitis Diseases 0.000 description 2
- 210000004087 cornea Anatomy 0.000 description 2
- ZOGHDTBRWUEJDP-UHFFFAOYSA-N diethylalumanylium;cyanide Chemical compound N#[C-].CC[Al+]CC ZOGHDTBRWUEJDP-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000013764 eosinophil chemotaxis Effects 0.000 description 2
- 201000001564 eosinophilic gastroenteritis Diseases 0.000 description 2
- 230000001037 epileptic effect Effects 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
- 208000022195 farmer lung disease Diseases 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 210000002216 heart Anatomy 0.000 description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 description 2
- 210000003630 histaminocyte Anatomy 0.000 description 2
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 2
- 206010051040 hyper-IgE syndrome Diseases 0.000 description 2
- 208000036260 idiopathic disease Diseases 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 230000002458 infectious effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 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
- 210000000936 intestine Anatomy 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 201000011486 lichen planus Diseases 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
- 208000008585 mastocytosis Diseases 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- 206010028417 myasthenia gravis Diseases 0.000 description 2
- SMIYSQCMVAZNCD-UHFFFAOYSA-N n-(2-bromophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Br)CC1 SMIYSQCMVAZNCD-UHFFFAOYSA-N 0.000 description 2
- INFQIOWPORYTNN-UHFFFAOYSA-N n-(2-chlorophenyl)sulfonyl-4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound CC1=C(Cl)C=CC(OC2CCN(CC2)C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=C1Cl INFQIOWPORYTNN-UHFFFAOYSA-N 0.000 description 2
- OQGRVNBEJUFCBU-UHFFFAOYSA-N n-(2-chlorophenyl)sulfonyl-4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=CC(Cl)=C(Cl)C(C)=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)CC1 OQGRVNBEJUFCBU-UHFFFAOYSA-N 0.000 description 2
- XMLJPFPDQATYIF-UHFFFAOYSA-N n-(4-bromophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC(Br)=CC=2)CC1 XMLJPFPDQATYIF-UHFFFAOYSA-N 0.000 description 2
- CXBGWBYHXGZMTD-UHFFFAOYSA-N n-(4-bromothiophen-2-yl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2SC=C(Br)C=2)CC1 CXBGWBYHXGZMTD-UHFFFAOYSA-N 0.000 description 2
- BGBZPKPXJHATBP-UHFFFAOYSA-N n-(4-chloro-2,5-difluorophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(F)=CC(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1F BGBZPKPXJHATBP-UHFFFAOYSA-N 0.000 description 2
- HBRSFVOYUOMDPA-UHFFFAOYSA-N n-(4-chloro-2,5-dimethylphenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(C)=CC(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1C HBRSFVOYUOMDPA-UHFFFAOYSA-N 0.000 description 2
- ZFLFDJDKLXKKDY-UHFFFAOYSA-N n-(5-chloro-2,4-difluorophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(F)=CC(F)=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 ZFLFDJDKLXKKDY-UHFFFAOYSA-N 0.000 description 2
- RYOAZTXPWXIRGP-UHFFFAOYSA-N n-(5-chlorothiophen-2-yl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound S1C(Cl)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 RYOAZTXPWXIRGP-UHFFFAOYSA-N 0.000 description 2
- BVFZDVXLSAKDGN-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-1-oxo-2h-isoquinoline-4-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C3=CC=CC=C3C(=O)NC=2)CC1 BVFZDVXLSAKDGN-UHFFFAOYSA-N 0.000 description 2
- YRQBSYRJUNLWLK-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 YRQBSYRJUNLWLK-UHFFFAOYSA-N 0.000 description 2
- PPPFEIVSKMCULR-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-2-methylpropanamide Chemical compound C1CN(S(=O)(=O)NC(=O)C(C)C)CCC1N1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 PPPFEIVSKMCULR-UHFFFAOYSA-N 0.000 description 2
- IVQUMPVXWDQUTI-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-2-phenylacetamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)CC=2C=CC=CC=2)CC1 IVQUMPVXWDQUTI-UHFFFAOYSA-N 0.000 description 2
- PFONVERWXQYUJF-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-3-methylsulfonylbenzamide Chemical compound CS(=O)(=O)C1=CC=CC(C(=O)NS(=O)(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 PFONVERWXQYUJF-UHFFFAOYSA-N 0.000 description 2
- OTHSFIWXSYZYEU-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-fluorobenzamide Chemical compound C1=CC(F)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 OTHSFIWXSYZYEU-UHFFFAOYSA-N 0.000 description 2
- FMRWQXJQGRYCHJ-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 FMRWQXJQGRYCHJ-UHFFFAOYSA-N 0.000 description 2
- TYJQOZIXCKQDQW-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylcyclohexanecarboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C2CCCCC2)CC1 TYJQOZIXCKQDQW-UHFFFAOYSA-N 0.000 description 2
- VSDZDXBYHPHYLG-UHFFFAOYSA-N n-[4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-3-methylsulfonylbenzamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=C(C=CC=2)S(C)(=O)=O)CC1 VSDZDXBYHPHYLG-UHFFFAOYSA-N 0.000 description 2
- HWWDVFCLZIAAPG-UHFFFAOYSA-N n-benzoyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NC(=O)C=2C=CC=CC=2)CC1 HWWDVFCLZIAAPG-UHFFFAOYSA-N 0.000 description 2
- ZVCZLEUNRRXCAW-UHFFFAOYSA-N n-benzoylsulfamoyl chloride Chemical compound ClS(=O)(=O)NC(=O)C1=CC=CC=C1 ZVCZLEUNRRXCAW-UHFFFAOYSA-N 0.000 description 2
- SHRVEEBUQYOBLS-UHFFFAOYSA-N n-benzylsulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)CC=2C=CC=CC=2)CC1 SHRVEEBUQYOBLS-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000000414 obstructive effect Effects 0.000 description 2
- 230000027758 ovulation cycle Effects 0.000 description 2
- 210000005259 peripheral blood Anatomy 0.000 description 2
- 239000011886 peripheral blood Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 208000015768 polyposis Diseases 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 208000005069 pulmonary fibrosis Diseases 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 230000000241 respiratory effect Effects 0.000 description 2
- 238000004007 reversed phase HPLC Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 201000000306 sarcoidosis Diseases 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 208000008742 seborrheic dermatitis Diseases 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 201000005671 spondyloarthropathy Diseases 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- LRCPIOSOSCTABO-UHFFFAOYSA-N tert-butyl 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-4-methylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(C)N1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 LRCPIOSOSCTABO-UHFFFAOYSA-N 0.000 description 2
- BYOLVJYCTOABMK-UHFFFAOYSA-N tert-butyl 4-cyano-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(C#N)N1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 BYOLVJYCTOABMK-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
- 238000002054 transplantation Methods 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
- JAYFJCQVACHCGU-UHFFFAOYSA-N (3-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=CC(OC(Cl)=O)=C1 JAYFJCQVACHCGU-UHFFFAOYSA-N 0.000 description 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- BUKMJNTWBSQMNS-UHFFFAOYSA-N 1-(3,4-dichlorophenoxy)piperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1ON1CCCCC1 BUKMJNTWBSQMNS-UHFFFAOYSA-N 0.000 description 1
- XAODVHPYSGIONI-UHFFFAOYSA-N 1-(3-methyl-4-piperidin-4-yloxyphenyl)ethanone Chemical compound CC1=CC(C(=O)C)=CC=C1OC1CCNCC1 XAODVHPYSGIONI-UHFFFAOYSA-N 0.000 description 1
- DFPYXQYWILNVAU-UHFFFAOYSA-N 1-hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1.C1=CC=C2N(O)N=NC2=C1 DFPYXQYWILNVAU-UHFFFAOYSA-N 0.000 description 1
- ZUZJLYZREKXIEV-UHFFFAOYSA-N 1-oxo-2h-isoquinoline-4-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CNC(=O)C2=C1 ZUZJLYZREKXIEV-UHFFFAOYSA-N 0.000 description 1
- LPCZFCQMWDLPAV-UHFFFAOYSA-N 1-piperidin-4-ylpiperidin-4-ol Chemical compound C1CC(O)CCN1C1CCNCC1 LPCZFCQMWDLPAV-UHFFFAOYSA-N 0.000 description 1
- GVLRTOYGRNLSDW-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine Chemical compound C1=CC=C2C=NNC2=N1 GVLRTOYGRNLSDW-UHFFFAOYSA-N 0.000 description 1
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 description 1
- AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-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
- ZEBMBNNVUIWRIC-UHFFFAOYSA-N 2,6-dimethylbenzenesulfonamide Chemical compound CC1=CC=CC(C)=C1S(N)(=O)=O ZEBMBNNVUIWRIC-UHFFFAOYSA-N 0.000 description 1
- QCLJODDRBGKIRW-UHFFFAOYSA-N 2,6-dimethylbenzenethiol Chemical compound CC1=CC=CC(C)=C1S QCLJODDRBGKIRW-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
- AUWBHBTZPIFESB-UHFFFAOYSA-N 2-chloro-n-[4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound CC1=C(Cl)C=CC(OC2CCN(CC2)C2CCN(CC2)S(=O)(=O)NC(=O)C=2C(=CC=CC=2)Cl)=C1Cl AUWBHBTZPIFESB-UHFFFAOYSA-N 0.000 description 1
- TYQGISWUUNEUJW-UHFFFAOYSA-N 2-chloro-n-[4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound C1=CC(Cl)=C(Cl)C(C)=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C(=CC=CC=2)Cl)CC1 TYQGISWUUNEUJW-UHFFFAOYSA-N 0.000 description 1
- IELATJVSFXDBOL-UHFFFAOYSA-N 2-chloro-n-[4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C(=CC=CC=2)Cl)CC1 IELATJVSFXDBOL-UHFFFAOYSA-N 0.000 description 1
- JCCBZCMSYUSCFM-UHFFFAOYSA-N 2-chlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1Cl JCCBZCMSYUSCFM-UHFFFAOYSA-N 0.000 description 1
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 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
- GUPZJUWYMNFAAY-UHFFFAOYSA-N 3,4-dichloro-n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=C(Cl)C(Cl)=CC=2)CC1 GUPZJUWYMNFAAY-UHFFFAOYSA-N 0.000 description 1
- VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- ZQXLIXHVJVAPLW-UHFFFAOYSA-N 3-chloro-4-fluorophenol Chemical compound OC1=CC=C(F)C(Cl)=C1 ZQXLIXHVJVAPLW-UHFFFAOYSA-N 0.000 description 1
- XVEPKNMWBQMARY-UHFFFAOYSA-N 3-cyano-n-[4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound CC1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=C(C=CC=2)C#N)CC1 XVEPKNMWBQMARY-UHFFFAOYSA-N 0.000 description 1
- CVRNRWQZRAGHLC-UHFFFAOYSA-N 4-(2,3-dihydro-1h-inden-5-yloxy)piperidine Chemical compound C1=C2CCCC2=CC=C1OC1CCNCC1 CVRNRWQZRAGHLC-UHFFFAOYSA-N 0.000 description 1
- MGDQYPPGUOXAJQ-UHFFFAOYSA-N 4-(2,4-dichloro-3-methylphenoxy)piperidine Chemical compound CC1=C(Cl)C=CC(OC2CCNCC2)=C1Cl MGDQYPPGUOXAJQ-UHFFFAOYSA-N 0.000 description 1
- YNWKRZPBAFSZSC-UHFFFAOYSA-N 4-(2,4-dichloro-6-methylphenoxy)piperidine Chemical compound CC1=CC(Cl)=CC(Cl)=C1OC1CCNCC1 YNWKRZPBAFSZSC-UHFFFAOYSA-N 0.000 description 1
- YANGNDLVJNSLBN-UHFFFAOYSA-N 4-(2,4-dichlorophenoxy)-1-piperidin-4-ylpiperidine Chemical compound ClC1=CC(Cl)=CC=C1OC1CCN(C2CCNCC2)CC1 YANGNDLVJNSLBN-UHFFFAOYSA-N 0.000 description 1
- XINVQNFMLVRDTP-UHFFFAOYSA-N 4-(2,4-dichlorophenoxy)piperidine Chemical compound ClC1=CC(Cl)=CC=C1OC1CCNCC1 XINVQNFMLVRDTP-UHFFFAOYSA-N 0.000 description 1
- LJTKODIQFDAGSL-UHFFFAOYSA-N 4-(2,4-difluorophenoxy)piperidine Chemical compound FC1=CC(F)=CC=C1OC1CCNCC1 LJTKODIQFDAGSL-UHFFFAOYSA-N 0.000 description 1
- NNKFUNWCEKSGND-UHFFFAOYSA-N 4-(2,5-dichlorophenoxy)piperidine Chemical compound ClC1=CC=C(Cl)C(OC2CCNCC2)=C1 NNKFUNWCEKSGND-UHFFFAOYSA-N 0.000 description 1
- XHJCECGMJQUEFX-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenoxy)-1-piperidin-4-ylpiperidine Chemical compound ClC1=CC(F)=CC=C1OC1CCN(C2CCNCC2)CC1 XHJCECGMJQUEFX-UHFFFAOYSA-N 0.000 description 1
- LZIIPYMGXICIBO-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenoxy)piperidine Chemical compound ClC1=CC(F)=CC=C1OC1CCNCC1 LZIIPYMGXICIBO-UHFFFAOYSA-N 0.000 description 1
- PTNWYRFHTGYWCU-UHFFFAOYSA-N 4-(2-chloro-4-methylphenoxy)piperidine Chemical compound ClC1=CC(C)=CC=C1OC1CCNCC1 PTNWYRFHTGYWCU-UHFFFAOYSA-N 0.000 description 1
- MTMIZXIWQUAWTF-UHFFFAOYSA-N 4-(2-chloro-5-methylphenoxy)piperidine Chemical compound CC1=CC=C(Cl)C(OC2CCNCC2)=C1 MTMIZXIWQUAWTF-UHFFFAOYSA-N 0.000 description 1
- PCFCSONHOHKCLP-UHFFFAOYSA-N 4-(2-chloro-6-methylphenoxy)piperidine Chemical compound CC1=CC=CC(Cl)=C1OC1CCNCC1 PCFCSONHOHKCLP-UHFFFAOYSA-N 0.000 description 1
- DZPPMPHWYRTPBR-UHFFFAOYSA-N 4-(2-ethyl-4-fluorophenoxy)piperidine Chemical compound CCC1=CC(F)=CC=C1OC1CCNCC1 DZPPMPHWYRTPBR-UHFFFAOYSA-N 0.000 description 1
- JRVLGEHIWSKAQM-UHFFFAOYSA-N 4-(2-tert-butylphenoxy)piperidine Chemical compound CC(C)(C)C1=CC=CC=C1OC1CCNCC1 JRVLGEHIWSKAQM-UHFFFAOYSA-N 0.000 description 1
- JTTTUWCNTDEICS-UHFFFAOYSA-N 4-(3,4-dichloro-2-methylphenoxy)-1-piperidin-4-ylpiperidine Chemical compound C1=CC(Cl)=C(Cl)C(C)=C1OC1CCN(C2CCNCC2)CC1 JTTTUWCNTDEICS-UHFFFAOYSA-N 0.000 description 1
- VQPPZPNATYRMNX-UHFFFAOYSA-N 4-(3,4-dichloro-2-methylphenoxy)piperidine Chemical compound CC1=C(Cl)C(Cl)=CC=C1OC1CCNCC1 VQPPZPNATYRMNX-UHFFFAOYSA-N 0.000 description 1
- VQTHFSCSZWMXOU-UHFFFAOYSA-N 4-(3,4-difluorophenoxy)-1-piperidin-4-ylpiperidine Chemical compound C1=C(F)C(F)=CC=C1OC1CCN(C2CCNCC2)CC1 VQTHFSCSZWMXOU-UHFFFAOYSA-N 0.000 description 1
- LZUGMPVNADMJOU-UHFFFAOYSA-N 4-(3-chloro-4-fluorophenoxy)piperidine Chemical compound C1=C(Cl)C(F)=CC=C1OC1CCNCC1 LZUGMPVNADMJOU-UHFFFAOYSA-N 0.000 description 1
- PRNWCAGRLWIJFZ-UHFFFAOYSA-N 4-(4-chloro-2,6-dimethylphenoxy)piperidine Chemical compound CC1=CC(Cl)=CC(C)=C1OC1CCNCC1 PRNWCAGRLWIJFZ-UHFFFAOYSA-N 0.000 description 1
- CWZIEDACJJQIBJ-UHFFFAOYSA-N 4-(4-chloro-2-cyclohexylphenoxy)piperidine Chemical compound C1CCCCC1C1=CC(Cl)=CC=C1OC1CCNCC1 CWZIEDACJJQIBJ-UHFFFAOYSA-N 0.000 description 1
- ACBAMBGSIWNLTL-UHFFFAOYSA-N 4-(4-chloro-2-ethylphenoxy)piperidine Chemical compound CCC1=CC(Cl)=CC=C1OC1CCNCC1 ACBAMBGSIWNLTL-UHFFFAOYSA-N 0.000 description 1
- MIRJXYNRRGFRQS-UHFFFAOYSA-N 4-(4-chloro-2-fluorophenoxy)piperidine Chemical compound FC1=CC(Cl)=CC=C1OC1CCNCC1 MIRJXYNRRGFRQS-UHFFFAOYSA-N 0.000 description 1
- QGORDVCWTACESA-UHFFFAOYSA-N 4-(4-chloro-2-methoxyphenoxy)piperidine Chemical compound COC1=CC(Cl)=CC=C1OC1CCNCC1 QGORDVCWTACESA-UHFFFAOYSA-N 0.000 description 1
- FJKAGGOQQGZLCB-UHFFFAOYSA-N 4-(4-chloro-2-methylphenoxy)-1-piperidin-4-ylpiperidine Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCNCC2)CC1 FJKAGGOQQGZLCB-UHFFFAOYSA-N 0.000 description 1
- MTVAZFCWBDHYEZ-UHFFFAOYSA-N 4-(4-chloro-2-methylphenoxy)piperidine Chemical compound CC1=CC(Cl)=CC=C1OC1CCNCC1 MTVAZFCWBDHYEZ-UHFFFAOYSA-N 0.000 description 1
- FKKIMHRWJDGOEQ-UHFFFAOYSA-N 4-(4-chloro-3-fluorophenoxy)piperidine Chemical compound C1=C(Cl)C(F)=CC(OC2CCNCC2)=C1 FKKIMHRWJDGOEQ-UHFFFAOYSA-N 0.000 description 1
- XGUPBEQGBNKGGU-UHFFFAOYSA-N 4-(4-chloro-3-methylphenoxy)piperidine Chemical compound C1=C(Cl)C(C)=CC(OC2CCNCC2)=C1 XGUPBEQGBNKGGU-UHFFFAOYSA-N 0.000 description 1
- VOQMPZXAFLPTMM-UHFFFAOYSA-N 4-(4-chlorophenoxy)piperidine Chemical compound C1=CC(Cl)=CC=C1OC1CCNCC1 VOQMPZXAFLPTMM-UHFFFAOYSA-N 0.000 description 1
- YAKQXRNHKUKGDR-UHFFFAOYSA-N 4-(4-fluoro-2-methoxyphenoxy)piperidine Chemical compound COC1=CC(F)=CC=C1OC1CCNCC1 YAKQXRNHKUKGDR-UHFFFAOYSA-N 0.000 description 1
- VUTZZQWPOVITLA-UHFFFAOYSA-N 4-(4-fluoro-2-methylphenoxy)piperidine Chemical compound CC1=CC(F)=CC=C1OC1CCNCC1 VUTZZQWPOVITLA-UHFFFAOYSA-N 0.000 description 1
- QUPXFCLFBNUVGX-UHFFFAOYSA-N 4-(4-fluorophenoxy)piperidine Chemical compound C1=CC(F)=CC=C1OC1CCNCC1 QUPXFCLFBNUVGX-UHFFFAOYSA-N 0.000 description 1
- HRMYEAQYLDCUGG-UHFFFAOYSA-N 4-(4-methoxyphenoxy)piperidine Chemical compound C1=CC(OC)=CC=C1OC1CCNCC1 HRMYEAQYLDCUGG-UHFFFAOYSA-N 0.000 description 1
- FFFNUHGMXGAUFY-UHFFFAOYSA-N 4-(4-methylphenoxy)piperidine Chemical compound C1=CC(C)=CC=C1OC1CCNCC1 FFFNUHGMXGAUFY-UHFFFAOYSA-N 0.000 description 1
- SHNVGFLRGUBNLI-UHFFFAOYSA-N 4-(4-methylsulfonylphenoxy)piperidine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC1CCNCC1 SHNVGFLRGUBNLI-UHFFFAOYSA-N 0.000 description 1
- QKUIPKBWUGLOQX-UHFFFAOYSA-N 4-(5-chloro-2-methylphenoxy)piperidine Chemical compound CC1=CC=C(Cl)C=C1OC1CCNCC1 QKUIPKBWUGLOQX-UHFFFAOYSA-N 0.000 description 1
- XFFZHNBYTRGXGQ-UHFFFAOYSA-N 4-[(3,4-dichlorophenyl)methyl]-1-piperidin-4-ylpiperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1CC1CCN(C2CCNCC2)CC1 XFFZHNBYTRGXGQ-UHFFFAOYSA-N 0.000 description 1
- YMACOJXOWHVFPA-UHFFFAOYSA-N 4-[4-(2,4-dichloro-3-fluorophenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=C(F)C(Cl)=CC=2)Cl)CC1 YMACOJXOWHVFPA-UHFFFAOYSA-N 0.000 description 1
- HZSIJCWSKQVTBQ-UHFFFAOYSA-N 4-[4-(2,4-dichloro-3-fluorophenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=C(F)C(Cl)=CC=2)Cl)CC1 HZSIJCWSKQVTBQ-UHFFFAOYSA-N 0.000 description 1
- HFWLILWGBZWYRI-UHFFFAOYSA-N 4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=C(C)C(Cl)=CC=2)Cl)CC1 HFWLILWGBZWYRI-UHFFFAOYSA-N 0.000 description 1
- PHVOHKKANUOFGH-UHFFFAOYSA-N 4-[4-(2,4-dichlorophenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(Cl)=CC=2)Cl)CC1 PHVOHKKANUOFGH-UHFFFAOYSA-N 0.000 description 1
- STXMJDYUJFBELE-UHFFFAOYSA-N 4-[4-(2,4-dichlorophenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(Cl)=CC=2)Cl)CC1 STXMJDYUJFBELE-UHFFFAOYSA-N 0.000 description 1
- SULNOZZZTPIFLF-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenoxy)piperidin-1-yl]-n-(2-chlorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound ClC1=CC(F)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)CC1 SULNOZZZTPIFLF-UHFFFAOYSA-N 0.000 description 1
- BRGLVRDQJXVXIU-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenoxy)piperidin-1-yl]-n-(4-chlorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound ClC1=CC(F)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC(Cl)=CC=2)CC1 BRGLVRDQJXVXIU-UHFFFAOYSA-N 0.000 description 1
- JOQJAHXOGPPLHV-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenoxy)piperidin-1-yl]-n-(4-fluorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(F)=CC=2)Cl)CC1 JOQJAHXOGPPLHV-UHFFFAOYSA-N 0.000 description 1
- RSUJBLZGGJXMPA-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(F)=CC=2)Cl)CC1 RSUJBLZGGJXMPA-UHFFFAOYSA-N 0.000 description 1
- HJNPTYXKCYNFHI-UHFFFAOYSA-N 4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=C(Cl)C(Cl)=CC=2)C)CC1 HJNPTYXKCYNFHI-UHFFFAOYSA-N 0.000 description 1
- JZWQTITXFPEKEB-UHFFFAOYSA-N 4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]-n-(4-fluorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC(F)=CC=2)CC1 JZWQTITXFPEKEB-UHFFFAOYSA-N 0.000 description 1
- RFSWRLDFDGCIKQ-UHFFFAOYSA-N 4-[4-(3,4-dichloroanilino)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)NC=2C=C(Cl)C(Cl)=CC=2)CC1 RFSWRLDFDGCIKQ-UHFFFAOYSA-N 0.000 description 1
- CLHMIPRHBVGJLN-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-4-methyl-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(C)(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 CLHMIPRHBVGJLN-UHFFFAOYSA-N 0.000 description 1
- TUUDOWGNTAVHGG-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-4-methyl-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(C)(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 TUUDOWGNTAVHGG-UHFFFAOYSA-N 0.000 description 1
- YCMJYSJIIXJFAN-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-4-methyl-n-[3-(trifluoromethyl)phenyl]sulfonylpiperidine-1-carboxamide Chemical compound C1CC(C)(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CCN1C(=O)NS(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 YCMJYSJIIXJFAN-UHFFFAOYSA-N 0.000 description 1
- UUSKKXQELGBNOG-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(1-methylimidazol-4-yl)sulfonylpiperidine-1-carboxamide Chemical compound CN1C=NC(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 UUSKKXQELGBNOG-UHFFFAOYSA-N 0.000 description 1
- STBLJTMWOFWZNU-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2,5-dimethoxyphenyl)sulfonylpiperidine-1-carboxamide Chemical compound COC1=CC=C(OC)C(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 STBLJTMWOFWZNU-UHFFFAOYSA-N 0.000 description 1
- NYWULHVCPFACAK-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2,6-dimethylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC(C)=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 NYWULHVCPFACAK-UHFFFAOYSA-N 0.000 description 1
- UOWPMQNCLJZBEA-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2-methoxyphenyl)sulfonylpiperidine-1-carboxamide Chemical compound COC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 UOWPMQNCLJZBEA-UHFFFAOYSA-N 0.000 description 1
- QACKNSQCZAMGSU-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2-methylbenzoyl)piperidine-1-carboxamide Chemical compound CC1=CC=CC=C1C(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 QACKNSQCZAMGSU-UHFFFAOYSA-N 0.000 description 1
- IGLADUDHPDHSRD-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 IGLADUDHPDHSRD-UHFFFAOYSA-N 0.000 description 1
- ZNIHOYUYQMMJSD-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2-morpholin-4-ylpyridin-3-yl)sulfonylpiperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=NC=CC=2)N2CCOCC2)CC1 ZNIHOYUYQMMJSD-UHFFFAOYSA-N 0.000 description 1
- RYFIOOFJCDQMTQ-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(2-piperidin-1-ylpyridin-3-yl)sulfonylpiperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=NC=CC=2)N2CCCCC2)CC1 RYFIOOFJCDQMTQ-UHFFFAOYSA-N 0.000 description 1
- QASDPIRCOYWLRS-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(3,4-dimethoxyphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 QASDPIRCOYWLRS-UHFFFAOYSA-N 0.000 description 1
- MPZGRQNIZNSJFU-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(4-fluorophenyl)sulfonyl-4-methylpiperidine-1-carboxamide Chemical compound C1CC(C)(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CCN1C(=O)NS(=O)(=O)C1=CC=C(F)C=C1 MPZGRQNIZNSJFU-UHFFFAOYSA-N 0.000 description 1
- FGWSLMPEBIIYTF-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(4-fluorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 FGWSLMPEBIIYTF-UHFFFAOYSA-N 0.000 description 1
- KGIUUTHNCGIMIN-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(4-hydroxyphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(O)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 KGIUUTHNCGIMIN-UHFFFAOYSA-N 0.000 description 1
- ZLPRNWIDJZJYMH-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(4-methoxyphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 ZLPRNWIDJZJYMH-UHFFFAOYSA-N 0.000 description 1
- RGNXGXQEPIZBHK-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(4-methylbenzoyl)piperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 RGNXGXQEPIZBHK-UHFFFAOYSA-N 0.000 description 1
- LKTJWMWPPOBGRZ-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-sulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 LKTJWMWPPOBGRZ-UHFFFAOYSA-N 0.000 description 1
- SXHFGQYBSOOBMO-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-sulfonamide;sodium Chemical compound [Na].C1=CC(C)=CC=C1S(=O)(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 SXHFGQYBSOOBMO-UHFFFAOYSA-N 0.000 description 1
- ROYPZYCKZGQLHO-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(5-methylpyridin-2-yl)sulfonylpiperidine-1-carboxamide Chemical compound N1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 ROYPZYCKZGQLHO-UHFFFAOYSA-N 0.000 description 1
- GEDDJESUGMPCOM-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-(thiolan-3-ylsulfonyl)piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C2CSCC2)CC1 GEDDJESUGMPCOM-UHFFFAOYSA-N 0.000 description 1
- KHTRUHWLPBNEHC-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-[(2,4-dimethyl-1,3-thiazol-5-yl)sulfonyl]piperidine-1-carboxamide Chemical compound S1C(C)=NC(C)=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 KHTRUHWLPBNEHC-UHFFFAOYSA-N 0.000 description 1
- GZPFSRZSBWRGKZ-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-[3-(3-methyl-5-oxo-4h-pyrazol-1-yl)phenyl]sulfonylpiperidine-1-carboxamide Chemical compound O=C1CC(C)=NN1C1=CC=CC(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 GZPFSRZSBWRGKZ-UHFFFAOYSA-N 0.000 description 1
- AQIZHUDMGJRAMJ-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-[3-(trifluoromethyl)phenyl]sulfonylpiperidine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 AQIZHUDMGJRAMJ-UHFFFAOYSA-N 0.000 description 1
- LPACELNJGFYJCV-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-[4-(3,3-dimethyl-2-oxoazetidin-1-yl)phenyl]sulfonylpiperidine-1-carboxamide Chemical compound O=C1C(C)(C)CN1C1=CC=C(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)C=C1 LPACELNJGFYJCV-UHFFFAOYSA-N 0.000 description 1
- LXPNXDXYMIAXRD-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-[4-(3-methyl-5-oxo-4h-pyrazol-1-yl)phenyl]sulfonylpiperidine-1-carboxamide Chemical compound O=C1CC(C)=NN1C1=CC=C(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)C=C1 LXPNXDXYMIAXRD-UHFFFAOYSA-N 0.000 description 1
- GDRRHBZSXZXDLL-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-[4-(dimethylamino)phenyl]sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 GDRRHBZSXZXDLL-UHFFFAOYSA-N 0.000 description 1
- LEMWHRJBHFWFAS-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-[5-(dimethylamino)naphthalen-1-yl]sulfonylpiperidine-1-carboxamide Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NC(=O)N(CC1)CCC1N(CC1)CCC1OC1=CC=C(Cl)C(Cl)=C1 LEMWHRJBHFWFAS-UHFFFAOYSA-N 0.000 description 1
- RPDZLVJWWJIDIP-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-methylsulfonylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)NS(=O)(=O)C)CCC1N1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 RPDZLVJWWJIDIP-UHFFFAOYSA-N 0.000 description 1
- VSWARJJGFQHZIH-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-n-naphthalen-2-ylsulfonylpiperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)CC1 VSWARJJGFQHZIH-UHFFFAOYSA-N 0.000 description 1
- BOAPKJOUZMUEJW-UHFFFAOYSA-N 4-[4-(3,4-difluorophenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(F)C(F)=CC=2)CC1 BOAPKJOUZMUEJW-UHFFFAOYSA-N 0.000 description 1
- GKKYKABOCZBQRA-UHFFFAOYSA-N 4-[4-(3,4-difluorophenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(F)C(F)=CC=2)CC1 GKKYKABOCZBQRA-UHFFFAOYSA-N 0.000 description 1
- WZOCHMRWFYCLIS-UHFFFAOYSA-N 4-[4-(3-chloro-2-methylphenoxy)piperidin-1-yl]-n-(2-chlorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=C(Cl)C=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)CC1 WZOCHMRWFYCLIS-UHFFFAOYSA-N 0.000 description 1
- ZEGIBJWDMGVXPO-UHFFFAOYSA-N 4-[4-(3-chloro-2-methylphenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=C(Cl)C=CC=2)C)CC1 ZEGIBJWDMGVXPO-UHFFFAOYSA-N 0.000 description 1
- XCWHZUWYSIWDFY-UHFFFAOYSA-N 4-[4-(3-chlorophenoxy)piperidin-1-yl]-n-(2-chlorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound ClC1=CC=CC(OC2CCN(CC2)C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=C1 XCWHZUWYSIWDFY-UHFFFAOYSA-N 0.000 description 1
- UPGBABSPENZSEO-UHFFFAOYSA-N 4-[4-(3-chlorophenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C=CC=2)CC1 UPGBABSPENZSEO-UHFFFAOYSA-N 0.000 description 1
- VBBGBUPKVZSEAE-UHFFFAOYSA-N 4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]-n-(4-fluorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC(F)=CC=2)CC1 VBBGBUPKVZSEAE-UHFFFAOYSA-N 0.000 description 1
- IGXXJZSHANKJAD-UHFFFAOYSA-N 4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(Cl)=CC=2)C)CC1 IGXXJZSHANKJAD-UHFFFAOYSA-N 0.000 description 1
- WCUOOPGSUYRJOM-UHFFFAOYSA-N 4-[4-(4-chloro-3-methylphenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=C(Cl)C(C)=CC(OC2CCN(CC2)C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=C1 WCUOOPGSUYRJOM-UHFFFAOYSA-N 0.000 description 1
- BAZIVMILAZYNFK-UHFFFAOYSA-N 4-[4-(4-chloro-3-methylphenoxy)piperidin-1-yl]-n-(4-chlorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=C(Cl)C(C)=CC(OC2CCN(CC2)C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 BAZIVMILAZYNFK-UHFFFAOYSA-N 0.000 description 1
- OIGSSOYBTOKCJR-UHFFFAOYSA-N 4-[4-(4-chloro-3-methylphenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(C)C(Cl)=CC=2)CC1 OIGSSOYBTOKCJR-UHFFFAOYSA-N 0.000 description 1
- FCQFSOXWEAOCAK-UHFFFAOYSA-N 4-[4-(4-chlorophenoxy)piperidin-1-yl]-n-(2-chlorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)CC1 FCQFSOXWEAOCAK-UHFFFAOYSA-N 0.000 description 1
- YMUKRGFOXCVQDE-UHFFFAOYSA-N 4-[4-(4-chlorophenoxy)piperidin-1-yl]-n-(2-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=CC(Cl)=CC=2)CC1 YMUKRGFOXCVQDE-UHFFFAOYSA-N 0.000 description 1
- FGBHFNCOQMRPHY-UHFFFAOYSA-N 4-[4-(4-chlorophenoxy)piperidin-1-yl]-n-(4-chlorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC(Cl)=CC=2)CC1 FGBHFNCOQMRPHY-UHFFFAOYSA-N 0.000 description 1
- RUMOWLXMMCFECC-UHFFFAOYSA-N 4-[4-(4-chlorophenoxy)piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=CC(Cl)=CC=2)CC1 RUMOWLXMMCFECC-UHFFFAOYSA-N 0.000 description 1
- QKVUWCHUFJQKBQ-UHFFFAOYSA-N 4-[4-[(3,4-dichlorophenyl)methyl]piperidin-1-yl]-n-(4-methylphenyl)sulfonylpiperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC=3C=C(Cl)C(Cl)=CC=3)CC2)CC1 QKVUWCHUFJQKBQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- SQGJZRXIBWFFTO-UHFFFAOYSA-N 4-[[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carbonyl]sulfamoyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 SQGJZRXIBWFFTO-UHFFFAOYSA-N 0.000 description 1
- XLHYAEBESNFTCA-UHFFFAOYSA-N 4-chloro-3-fluorophenol Chemical compound OC1=CC=C(Cl)C(F)=C1 XLHYAEBESNFTCA-UHFFFAOYSA-N 0.000 description 1
- ZCICCHRWMSJDOB-UHFFFAOYSA-N 4-chloro-n-[4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound CC1=C(Cl)C=CC(OC2CCN(CC2)C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=CC(Cl)=CC=2)=C1Cl ZCICCHRWMSJDOB-UHFFFAOYSA-N 0.000 description 1
- QBBXXYIFANZUIE-UHFFFAOYSA-N 4-chloro-n-[4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound C1=CC(Cl)=C(Cl)C(C)=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=CC(Cl)=CC=2)CC1 QBBXXYIFANZUIE-UHFFFAOYSA-N 0.000 description 1
- FHMRJRSOWRCSKA-UHFFFAOYSA-N 4-fluoro-n-(oxomethylidene)benzenesulfonamide Chemical compound FC1=CC=C(S(=O)(=O)N=C=O)C=C1 FHMRJRSOWRCSKA-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
- KBYPITRKIJKGMD-UHFFFAOYSA-N 4-phenoxypiperidine Chemical compound C1CNCCC1OC1=CC=CC=C1 KBYPITRKIJKGMD-UHFFFAOYSA-N 0.000 description 1
- BYTCXMYONXXBCH-UHFFFAOYSA-N 5-(5-chloro-2-piperidin-4-yloxyphenyl)-1,2-oxazole Chemical compound C=1C=NOC=1C1=CC(Cl)=CC=C1OC1CCNCC1 BYTCXMYONXXBCH-UHFFFAOYSA-N 0.000 description 1
- DCFQSCNJHJRVEO-UHFFFAOYSA-N 5-chloro-2-(1-piperidin-4-ylpiperidin-4-yl)oxypyridine Chemical compound N1=CC(Cl)=CC=C1OC1CCN(C2CCNCC2)CC1 DCFQSCNJHJRVEO-UHFFFAOYSA-N 0.000 description 1
- GHJZALSLZWKKAA-UHFFFAOYSA-N 5-chloro-2-piperidin-4-yloxybenzamide Chemical compound NC(=O)C1=CC(Cl)=CC=C1OC1CCNCC1 GHJZALSLZWKKAA-UHFFFAOYSA-N 0.000 description 1
- QWRYSXWYAHOJPR-UHFFFAOYSA-N 5-chloro-2-piperidin-4-yloxybenzonitrile Chemical compound N#CC1=CC(Cl)=CC=C1OC1CCNCC1 QWRYSXWYAHOJPR-UHFFFAOYSA-N 0.000 description 1
- WWPAQYCRZMQXEM-UHFFFAOYSA-N 7-piperidin-4-yloxyquinoline Chemical compound C1CNCCC1OC1=CC=C(C=CC=N2)C2=C1 WWPAQYCRZMQXEM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 206010003645 Atopy Diseases 0.000 description 1
- 102100031172 C-C chemokine receptor type 1 Human genes 0.000 description 1
- 101710149814 C-C chemokine receptor type 1 Proteins 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
- 102100028989 C-X-C chemokine receptor type 2 Human genes 0.000 description 1
- 102100028990 C-X-C chemokine receptor type 3 Human genes 0.000 description 1
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 description 1
- IKEIUCASBAOJLM-WGSAOQKQSA-N C1=C(Cl)C(C)=CC(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1C Chemical compound C1=C(Cl)C(C)=CC(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1C IKEIUCASBAOJLM-WGSAOQKQSA-N 0.000 description 1
- QZZLGNLWUMZMGQ-WGSAOQKQSA-N C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NC(=O)C=2C=CC=CC=2)CC1 Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NC(=O)C=2C=CC=CC=2)CC1 QZZLGNLWUMZMGQ-WGSAOQKQSA-N 0.000 description 1
- FGAGRINEPRVSGP-DBTMUERSSA-N C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C2CSCC2)CC1 Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C2CSCC2)CC1 FGAGRINEPRVSGP-DBTMUERSSA-N 0.000 description 1
- IOOQBHHFBXUJFW-QAQDUYKDSA-N C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Br)CC1 Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Br)CC1 IOOQBHHFBXUJFW-QAQDUYKDSA-N 0.000 description 1
- IPZATHRUSPHDSY-MEMLXQNLSA-N C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C(=NC=CC=2)N2CCCCC2)CC1 Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C(=NC=CC=2)N2CCCCC2)CC1 IPZATHRUSPHDSY-MEMLXQNLSA-N 0.000 description 1
- HCBIGIUEJJIXKK-MXVIHJGJSA-N C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C(=NC=CC=2)N2CCOCC2)CC1 Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C(=NC=CC=2)N2CCOCC2)CC1 HCBIGIUEJJIXKK-MXVIHJGJSA-N 0.000 description 1
- WQXUGWCJEBGWEM-SAABIXHNSA-N C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C=C(Br)C=CC=2)CC1 Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C=C(Br)C=CC=2)CC1 WQXUGWCJEBGWEM-SAABIXHNSA-N 0.000 description 1
- PODCQKNTGSRCKN-WGSAOQKQSA-N C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C=C(C=CC=2)C#N)CC1 Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C=C(C=CC=2)C#N)CC1 PODCQKNTGSRCKN-WGSAOQKQSA-N 0.000 description 1
- SERMZJPEAAELFZ-AQYVVDRMSA-N C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)CC1 Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C=C3C=CC=CC3=CC=2)CC1 SERMZJPEAAELFZ-AQYVVDRMSA-N 0.000 description 1
- IEHMJPDUJWDCMH-SAABIXHNSA-N C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C=CC(Br)=CC=2)CC1 Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C=CC(Br)=CC=2)CC1 IEHMJPDUJWDCMH-SAABIXHNSA-N 0.000 description 1
- LVFYPTLSLCCWPB-WKILWMFISA-N C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C=NC(Br)=CC=2)CC1 Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2C=NC(Br)=CC=2)CC1 LVFYPTLSLCCWPB-WKILWMFISA-N 0.000 description 1
- CYATYWZILUZMBW-KOMQPUFPSA-N C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2SC=C(Br)C=2)CC1 Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)C(=O)NS(=O)(=O)C=2SC=C(Br)C=2)CC1 CYATYWZILUZMBW-KOMQPUFPSA-N 0.000 description 1
- RSUCUFPHNJNDGI-XGAFWQRZSA-N C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)S(=O)(=O)NC(=O)C=2C=CC=CC=2)CC1 Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)S(=O)(=O)NC(=O)C=2C=CC=CC=2)CC1 RSUCUFPHNJNDGI-XGAFWQRZSA-N 0.000 description 1
- ZOZNPRQFDBFILY-CYWCHRQTSA-N C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)S(=O)(=O)NS(=O)(=O)C=2C=CC=CC=2)CC1 Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN([C@@H]2CC[C@H](CC2)S(=O)(=O)NS(=O)(=O)C=2C=CC=CC=2)CC1 ZOZNPRQFDBFILY-CYWCHRQTSA-N 0.000 description 1
- YGNMNKWXIRWXLB-SHTZXODSSA-N C1=C(Cl)C(F)=CC(F)=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound C1=C(Cl)C(F)=CC(F)=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 YGNMNKWXIRWXLB-SHTZXODSSA-N 0.000 description 1
- CNDMNKWEBPQHNH-SHTZXODSSA-N C1=C(Cl)C(F)=CC(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1F Chemical compound C1=C(Cl)C(F)=CC(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1F CNDMNKWEBPQHNH-SHTZXODSSA-N 0.000 description 1
- AJGIWFHSYLTQAQ-SHTZXODSSA-N C1=C(F)C(F)=CC(F)=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound C1=C(F)C(F)=CC(F)=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 AJGIWFHSYLTQAQ-SHTZXODSSA-N 0.000 description 1
- JASZRZYJBQVSIJ-IYARVYRRSA-N C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 JASZRZYJBQVSIJ-IYARVYRRSA-N 0.000 description 1
- BEJKOOCOYDBICL-XUTJKUGGSA-N C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 BEJKOOCOYDBICL-XUTJKUGGSA-N 0.000 description 1
- RQJVPCNWPSIKAX-HZCBDIJESA-N C1=CC(CCCC)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound C1=CC(CCCC)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 RQJVPCNWPSIKAX-HZCBDIJESA-N 0.000 description 1
- BKZYWTQDRKECNU-KESTWPANSA-N C1=CC(N(C)C)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound C1=CC(N(C)C)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 BKZYWTQDRKECNU-KESTWPANSA-N 0.000 description 1
- FRSSQVUZMUQNFT-QAQDUYKDSA-N C1=CC(O)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound C1=CC(O)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 FRSSQVUZMUQNFT-QAQDUYKDSA-N 0.000 description 1
- NZGJMBNFCPWUME-QAQDUYKDSA-N C1=CC(OC(F)(F)F)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound C1=CC(OC(F)(F)F)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 NZGJMBNFCPWUME-QAQDUYKDSA-N 0.000 description 1
- CKSFTJNXAQTEAL-MEMLXQNLSA-N C1=CC(OCCCC)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 CKSFTJNXAQTEAL-MEMLXQNLSA-N 0.000 description 1
- VKJLNBNLBYFHJJ-MXVIHJGJSA-N C1CN([C@H]2CC[C@@H](CC2)C(=O)N(C)S(=O)(=O)C=2C=CC(C)=CC=2)CCC1OC1=CC=C(Cl)C(Cl)=C1 Chemical compound C1CN([C@H]2CC[C@@H](CC2)C(=O)N(C)S(=O)(=O)C=2C=CC(C)=CC=2)CCC1OC1=CC=C(Cl)C(Cl)=C1 VKJLNBNLBYFHJJ-MXVIHJGJSA-N 0.000 description 1
- QDVICFRRCYVLQH-MEMLXQNLSA-N C1CN([C@H]2CC[C@@H](CC2)C(=O)NS(=O)(=O)C2=C3C=CC=C(C3=CC=C2)N(C)C)CCC1OC1=CC=C(Cl)C(Cl)=C1 Chemical compound C1CN([C@H]2CC[C@@H](CC2)C(=O)NS(=O)(=O)C2=C3C=CC=C(C3=CC=C2)N(C)C)CCC1OC1=CC=C(Cl)C(Cl)=C1 QDVICFRRCYVLQH-MEMLXQNLSA-N 0.000 description 1
- 102000001902 CC Chemokines Human genes 0.000 description 1
- 108010040471 CC Chemokines Proteins 0.000 description 1
- KEMOVJWTVVHJTA-SAABIXHNSA-N CC1=C(Cl)C=C(F)C=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound CC1=C(Cl)C=C(F)C=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 KEMOVJWTVVHJTA-SAABIXHNSA-N 0.000 description 1
- DBCRHRSXVGDVII-MXVIHJGJSA-N CC1=CC=CC(C)=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound CC1=CC=CC(C)=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 DBCRHRSXVGDVII-MXVIHJGJSA-N 0.000 description 1
- 108700012434 CCL3 Proteins 0.000 description 1
- OTXZFSVSTPEMNV-WKILWMFISA-N CN1C=NC(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 Chemical compound CN1C=NC(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 OTXZFSVSTPEMNV-WKILWMFISA-N 0.000 description 1
- ZJHGYTSUEZVVNL-IYARVYRRSA-N COC1=CC=C(OC)C(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 Chemical compound COC1=CC=C(OC)C(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 ZJHGYTSUEZVVNL-IYARVYRRSA-N 0.000 description 1
- VUSUKCUJOGPNDI-IYARVYRRSA-N COC1=CC=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound COC1=CC=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 VUSUKCUJOGPNDI-IYARVYRRSA-N 0.000 description 1
- 108050006947 CXC Chemokine Proteins 0.000 description 1
- 102000019388 CXC chemokine Human genes 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- 102000000013 Chemokine CCL3 Human genes 0.000 description 1
- 102000001326 Chemokine CCL4 Human genes 0.000 description 1
- 108010055165 Chemokine CCL4 Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 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
- TYUOEFYCGCBMLU-RZDIXWSQSA-N ClC1=CC(Cl)=CC(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 Chemical compound ClC1=CC(Cl)=CC(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 TYUOEFYCGCBMLU-RZDIXWSQSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 1
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 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
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 108010092408 Eosinophil Peroxidase Proteins 0.000 description 1
- 102100028471 Eosinophil peroxidase Human genes 0.000 description 1
- RYGSUSBLXKZSQP-SAABIXHNSA-N FC(F)(F)C1=CC=CC(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 RYGSUSBLXKZSQP-SAABIXHNSA-N 0.000 description 1
- ZUNDJAHDADQYHH-QAQDUYKDSA-N FC(F)(F)OC1=CC=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound FC(F)(F)OC1=CC=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 ZUNDJAHDADQYHH-QAQDUYKDSA-N 0.000 description 1
- CTIXOCBOPSQQPF-JCNLHEQBSA-N FC1=CC=C(F)C(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 Chemical compound FC1=CC=C(F)C(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 CTIXOCBOPSQQPF-JCNLHEQBSA-N 0.000 description 1
- 102100037362 Fibronectin Human genes 0.000 description 1
- 108010067306 Fibronectins Proteins 0.000 description 1
- 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 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 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
- 238000003747 Grignard reaction Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 102000003834 Histamine H1 Receptors Human genes 0.000 description 1
- 108090000110 Histamine H1 Receptors Proteins 0.000 description 1
- 108010014095 Histidine decarboxylase Proteins 0.000 description 1
- 102100037095 Histidine decarboxylase Human genes 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
- 101000916050 Homo sapiens C-X-C chemokine receptor type 3 Proteins 0.000 description 1
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 108010018951 Interleukin-8B Receptors Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 102000009571 Macrophage Inflammatory Proteins Human genes 0.000 description 1
- 108010009474 Macrophage Inflammatory Proteins Proteins 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 102000014962 Monocyte Chemoattractant Proteins Human genes 0.000 description 1
- 108010064136 Monocyte Chemoattractant Proteins Proteins 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- UURPNYFUFRQNPD-IYARVYRRSA-N N1=CC(C)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound N1=CC(C)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 UURPNYFUFRQNPD-IYARVYRRSA-N 0.000 description 1
- RTAZLJFWQBSMCZ-MXVIHJGJSA-N O=C1CC(C)=NN1C1=CC=C(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)C=C1 Chemical compound O=C1CC(C)=NN1C1=CC=C(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)C=C1 RTAZLJFWQBSMCZ-MXVIHJGJSA-N 0.000 description 1
- UILFELMZHPVIEP-MXVIHJGJSA-N O=C1CC(C)=NN1C1=CC=CC(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 Chemical compound O=C1CC(C)=NN1C1=CC=CC(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 UILFELMZHPVIEP-MXVIHJGJSA-N 0.000 description 1
- CUJJKYQCILEWAI-QAQDUYKDSA-N OC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound OC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 CUJJKYQCILEWAI-QAQDUYKDSA-N 0.000 description 1
- 206010030113 Oedema Diseases 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 206010062106 Respiratory tract infection viral Diseases 0.000 description 1
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
- 241000698291 Rugosa Species 0.000 description 1
- WRRDFOUPXWMVHX-QAQDUYKDSA-N S1C(C)=NC(C)=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound S1C(C)=NC(C)=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 WRRDFOUPXWMVHX-QAQDUYKDSA-N 0.000 description 1
- HIKFNVMNJKASSW-HDJSIYSDSA-N S1C(Cl)=C(Cl)C=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound S1C(Cl)=C(Cl)C=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 HIKFNVMNJKASSW-HDJSIYSDSA-N 0.000 description 1
- MMRQNVQPLCOLIP-HDJSIYSDSA-N S1C(Cl)=CC(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1Cl Chemical compound S1C(Cl)=CC(S(=O)(=O)NC(=O)[C@@H]2CC[C@H](CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1Cl MMRQNVQPLCOLIP-HDJSIYSDSA-N 0.000 description 1
- PSGARVIKOGVANZ-SHTZXODSSA-N S1C(Cl)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound S1C(Cl)=CC=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 PSGARVIKOGVANZ-SHTZXODSSA-N 0.000 description 1
- MTVJULOFSIRQJT-SHTZXODSSA-N S1C(NC(=O)C)=NN=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 Chemical compound S1C(NC(=O)C)=NN=C1S(=O)(=O)NC(=O)[C@@H]1CC[C@@H](N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 MTVJULOFSIRQJT-SHTZXODSSA-N 0.000 description 1
- 208000009359 Sezary Syndrome Diseases 0.000 description 1
- 208000021388 Sezary disease Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 210000001552 airway epithelial cell Anatomy 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 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
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 208000002352 blister Diseases 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 230000003185 calcium uptake Effects 0.000 description 1
- 239000013592 cell lysate Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
- 125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 1
- 108010004073 cysteinylcysteine Proteins 0.000 description 1
- LEVWYRKDKASIDU-IMJSIDKUSA-N cystine group Chemical group C([C@@H](C(=O)O)N)SSC[C@@H](C(=O)O)N LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 1
- DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- JMRYOSQOYJBDOI-UHFFFAOYSA-N dilithium;di(propan-2-yl)azanide Chemical compound [Li+].CC(C)[N-]C(C)C.CC(C)N([Li])C(C)C JMRYOSQOYJBDOI-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 1
- ZXYAWONOWHSQRU-UHFFFAOYSA-N ethyl 4-oxocyclohexanecarboxylate Chemical compound CCOC(=O)C1CCC(=O)CC1 ZXYAWONOWHSQRU-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000010265 fast atom bombardment Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
- 239000000938 histamine H1 antagonist Substances 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000003463 hyperproliferative effect Effects 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 210000004698 lymphocyte 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
- 230000035800 maturation Effects 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
- 230000007246 mechanism Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- JQNQLGMNSVSFOW-UHFFFAOYSA-N methyl 2-[[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carbonyl]sulfamoyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 JQNQLGMNSVSFOW-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 210000002464 muscle smooth vascular Anatomy 0.000 description 1
- 201000005962 mycosis fungoides Diseases 0.000 description 1
- FGNGTWFJQFTFGN-UHFFFAOYSA-N n,n,n',n'-tetramethylethane-1,2-diamine Chemical compound CN(C)CCN(C)C.CN(C)CCN(C)C FGNGTWFJQFTFGN-UHFFFAOYSA-N 0.000 description 1
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
- FMGFDEORYNNBHE-UHFFFAOYSA-N n-(2-chlorophenyl)sulfonyl-4-[4-(2,4-dichloro-3-fluorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound FC1=C(Cl)C=CC(OC2CCN(CC2)C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=C1Cl FMGFDEORYNNBHE-UHFFFAOYSA-N 0.000 description 1
- IEALZODAKCCZSO-UHFFFAOYSA-N n-(2-chlorophenyl)sulfonyl-4-[4-(2,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)CC1 IEALZODAKCCZSO-UHFFFAOYSA-N 0.000 description 1
- ZPQUVLUFFZOLSX-UHFFFAOYSA-N n-(2-chlorophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-4-methylpiperidine-1-carboxamide Chemical compound C1CC(C)(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CCN1C(=O)NS(=O)(=O)C1=CC=CC=C1Cl ZPQUVLUFFZOLSX-UHFFFAOYSA-N 0.000 description 1
- XMHWLUWBBIZHDL-UHFFFAOYSA-N n-(2-chlorophenyl)sulfonyl-4-[4-(3,4-difluorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(F)C(F)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)CC1 XMHWLUWBBIZHDL-UHFFFAOYSA-N 0.000 description 1
- QKXNPEDTSYCUEM-UHFFFAOYSA-N n-(3-bromophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=C(Br)C=CC=2)CC1 QKXNPEDTSYCUEM-UHFFFAOYSA-N 0.000 description 1
- ZFVQRQOPWCBDOI-UHFFFAOYSA-N n-(3-chlorophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound ClC1=CC=CC(S(=O)(=O)NC(=O)N2CCC(CC2)N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 ZFVQRQOPWCBDOI-UHFFFAOYSA-N 0.000 description 1
- TUSJFJSSKRVWIG-UHFFFAOYSA-N n-(3-cyanophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-4-methylpiperidine-1-carboxamide Chemical compound C1CC(C)(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CCN1C(=O)NS(=O)(=O)C1=CC=CC(C#N)=C1 TUSJFJSSKRVWIG-UHFFFAOYSA-N 0.000 description 1
- NWUBEEIEKUQVJL-UHFFFAOYSA-N n-(3-cyanophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=C(C=CC=2)C#N)CC1 NWUBEEIEKUQVJL-UHFFFAOYSA-N 0.000 description 1
- GKMPVSSEQDCTQR-UHFFFAOYSA-N n-(4-butoxyphenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 GKMPVSSEQDCTQR-UHFFFAOYSA-N 0.000 description 1
- STMZOGBDSBMUTA-UHFFFAOYSA-N n-(4-butylphenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=CC(CCCC)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 STMZOGBDSBMUTA-UHFFFAOYSA-N 0.000 description 1
- VTPLZHNAWPCUOJ-UHFFFAOYSA-N n-(4-chlorobenzoyl)-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 VTPLZHNAWPCUOJ-UHFFFAOYSA-N 0.000 description 1
- NYVXQSCVPJZOAZ-UHFFFAOYSA-N n-(4-chlorophenyl)sulfonyl-4-[4-(2,4-dichloro-3-fluorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound FC1=C(Cl)C=CC(OC2CCN(CC2)C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1Cl NYVXQSCVPJZOAZ-UHFFFAOYSA-N 0.000 description 1
- HLXYWALFMSUJDV-UHFFFAOYSA-N n-(4-chlorophenyl)sulfonyl-4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound CC1=C(Cl)C=CC(OC2CCN(CC2)C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC(Cl)=CC=2)=C1Cl HLXYWALFMSUJDV-UHFFFAOYSA-N 0.000 description 1
- KZGHMOVDCUXART-UHFFFAOYSA-N n-(4-chlorophenyl)sulfonyl-4-[4-(2,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(Cl)=CC=2)Cl)CC1 KZGHMOVDCUXART-UHFFFAOYSA-N 0.000 description 1
- KOXGMRYLXURNPV-UHFFFAOYSA-N n-(4-chlorophenyl)sulfonyl-4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=CC(Cl)=C(Cl)C(C)=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC(Cl)=CC=2)CC1 KOXGMRYLXURNPV-UHFFFAOYSA-N 0.000 description 1
- YYKWMEDZZXIYBI-UHFFFAOYSA-N n-(4-chlorophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-4-methylpiperidine-1-carboxamide Chemical compound C1CC(C)(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CCN1C(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 YYKWMEDZZXIYBI-UHFFFAOYSA-N 0.000 description 1
- LKFICSFQSQYFJF-UHFFFAOYSA-N n-(4-chlorophenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 LKFICSFQSQYFJF-UHFFFAOYSA-N 0.000 description 1
- DQSIUMYRQVJMJS-UHFFFAOYSA-N n-(4-chlorophenyl)sulfonyl-4-[4-[(3,4-dichlorophenyl)methyl]piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC=3C=C(Cl)C(Cl)=CC=3)CC2)CC1 DQSIUMYRQVJMJS-UHFFFAOYSA-N 0.000 description 1
- PMSMBBRVHXHLDX-UHFFFAOYSA-N n-(4-tert-butylphenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 PMSMBBRVHXHLDX-UHFFFAOYSA-N 0.000 description 1
- DIDSWSVCYQLAFM-UHFFFAOYSA-N n-(4-tert-butylphenyl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-sulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 DIDSWSVCYQLAFM-UHFFFAOYSA-N 0.000 description 1
- SHSADLHNRFJEOQ-UHFFFAOYSA-N n-(5-bromothiophen-2-yl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2SC(Br)=CC=2)CC1 SHSADLHNRFJEOQ-UHFFFAOYSA-N 0.000 description 1
- IHBIVTZODAJMEF-UHFFFAOYSA-N n-(6-bromopyridin-3-yl)sulfonyl-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=NC(Br)=CC=2)CC1 IHBIVTZODAJMEF-UHFFFAOYSA-N 0.000 description 1
- RBELTHMUNIMIOR-UHFFFAOYSA-N n-(benzenesulfonyl)-4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound CC1=C(Cl)C=CC(OC2CCN(CC2)C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC=CC=2)=C1Cl RBELTHMUNIMIOR-UHFFFAOYSA-N 0.000 description 1
- NVMPGECBPYRNOD-UHFFFAOYSA-N n-(benzenesulfonyl)-4-[4-(2-chloro-4-fluorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound ClC1=CC(F)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC=CC=2)CC1 NVMPGECBPYRNOD-UHFFFAOYSA-N 0.000 description 1
- MNMFLFGIEQJGDX-UHFFFAOYSA-N n-(benzenesulfonyl)-4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=CC(Cl)=C(Cl)C(C)=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC=CC=2)CC1 MNMFLFGIEQJGDX-UHFFFAOYSA-N 0.000 description 1
- MFJWXRIWIGLCGD-UHFFFAOYSA-N n-(benzenesulfonyl)-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC=CC=2)CC1 MFJWXRIWIGLCGD-UHFFFAOYSA-N 0.000 description 1
- YGDDALUUSRVNRI-UHFFFAOYSA-N n-(benzenesulfonyl)-4-[4-(3-chloro-2-methylphenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound CC1=C(Cl)C=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC=CC=2)CC1 YGDDALUUSRVNRI-UHFFFAOYSA-N 0.000 description 1
- RLCLYMFXZZTRJW-UHFFFAOYSA-N n-(benzenesulfonyl)-4-[4-(3-chlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound ClC1=CC=CC(OC2CCN(CC2)C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC=CC=2)=C1 RLCLYMFXZZTRJW-UHFFFAOYSA-N 0.000 description 1
- ITDYJENTYQYMNL-UHFFFAOYSA-N n-(benzenesulfonyl)-4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)C(=O)NS(=O)(=O)C=2C=CC=CC=2)CC1 ITDYJENTYQYMNL-UHFFFAOYSA-N 0.000 description 1
- KXSAZCOXROGCGW-UHFFFAOYSA-N n-[(5-acetamido-1,3,4-thiadiazol-2-yl)sulfonyl]-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical compound S1C(NC(=O)C)=NN=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 KXSAZCOXROGCGW-UHFFFAOYSA-N 0.000 description 1
- YRHORXSZBMLYAF-UHFFFAOYSA-N n-[(5-amino-1,3,4-thiadiazol-2-yl)sulfonyl]-4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxamide Chemical class S1C(N)=NN=C1S(=O)(=O)NC(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 YRHORXSZBMLYAF-UHFFFAOYSA-N 0.000 description 1
- DPZBGMCGKGMCTQ-UHFFFAOYSA-N n-[4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C(=C(C)C(Cl)=CC=2)Cl)CC1 DPZBGMCGKGMCTQ-UHFFFAOYSA-N 0.000 description 1
- QIVQQOSKKRQCMQ-UHFFFAOYSA-N n-[4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-3-methylsulfonylbenzamide Chemical compound CC1=C(Cl)C=CC(OC2CCN(CC2)C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=C(C=CC=2)S(C)(=O)=O)=C1Cl QIVQQOSKKRQCMQ-UHFFFAOYSA-N 0.000 description 1
- UQYDBZNBJJSRRU-UHFFFAOYSA-N n-[4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-(dimethylamino)benzamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C(=C(C)C(Cl)=CC=2)Cl)CC1 UQYDBZNBJJSRRU-UHFFFAOYSA-N 0.000 description 1
- LLIZCEZFOHDTTH-UHFFFAOYSA-N n-[4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-ethylbenzamide Chemical compound C1=CC(CC)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C(=C(C)C(Cl)=CC=2)Cl)CC1 LLIZCEZFOHDTTH-UHFFFAOYSA-N 0.000 description 1
- CMFABGJDPXNAEF-UHFFFAOYSA-N n-[4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-fluorobenzamide Chemical compound CC1=C(Cl)C=CC(OC2CCN(CC2)C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=CC(F)=CC=2)=C1Cl CMFABGJDPXNAEF-UHFFFAOYSA-N 0.000 description 1
- JOXWPTVIULXBIK-UHFFFAOYSA-N n-[4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C(=C(C)C(Cl)=CC=2)Cl)CC1 JOXWPTVIULXBIK-UHFFFAOYSA-N 0.000 description 1
- BQPGQDZMUKXJKT-UHFFFAOYSA-N n-[4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C(=C(C)C(Cl)=CC=2)Cl)CC1 BQPGQDZMUKXJKT-UHFFFAOYSA-N 0.000 description 1
- DJGWTFPDOGEBKS-UHFFFAOYSA-N n-[4-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound CC1=C(Cl)C=CC(OC2CCN(CC2)C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=CC=CC=2)=C1Cl DJGWTFPDOGEBKS-UHFFFAOYSA-N 0.000 description 1
- DVGHIKBFVGZSDP-UHFFFAOYSA-N n-[4-[4-(2,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound ClC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=CC=CC=2)CC1 DVGHIKBFVGZSDP-UHFFFAOYSA-N 0.000 description 1
- TWRZBZSMUVLHJK-UHFFFAOYSA-N n-[4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C(=C(Cl)C(Cl)=CC=2)C)CC1 TWRZBZSMUVLHJK-UHFFFAOYSA-N 0.000 description 1
- NUKYCFGZZOINJE-UHFFFAOYSA-N n-[4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-3-methylsulfonylbenzamide Chemical compound C1=CC(Cl)=C(Cl)C(C)=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=C(C=CC=2)S(C)(=O)=O)CC1 NUKYCFGZZOINJE-UHFFFAOYSA-N 0.000 description 1
- ZOHYBESHYVCLGM-UHFFFAOYSA-N n-[4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-(dimethylamino)benzamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C(=C(Cl)C(Cl)=CC=2)C)CC1 ZOHYBESHYVCLGM-UHFFFAOYSA-N 0.000 description 1
- WHBLCUAVTHFDHC-UHFFFAOYSA-N n-[4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-ethylbenzamide Chemical compound C1=CC(CC)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C(=C(Cl)C(Cl)=CC=2)C)CC1 WHBLCUAVTHFDHC-UHFFFAOYSA-N 0.000 description 1
- RMTKNZPLPFOBCU-UHFFFAOYSA-N n-[4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-fluorobenzamide Chemical compound CC1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=CC(F)=CC=2)CC1 RMTKNZPLPFOBCU-UHFFFAOYSA-N 0.000 description 1
- QVLMAOZFJKQXOH-UHFFFAOYSA-N n-[4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C(=C(Cl)C(Cl)=CC=2)C)CC1 QVLMAOZFJKQXOH-UHFFFAOYSA-N 0.000 description 1
- AHZQIOMFBBVGPA-UHFFFAOYSA-N n-[4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C(=C(Cl)C(Cl)=CC=2)C)CC1 AHZQIOMFBBVGPA-UHFFFAOYSA-N 0.000 description 1
- LWWKBWCIXTWDPG-UHFFFAOYSA-N n-[4-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound C1=CC(Cl)=C(Cl)C(C)=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=CC=CC=2)CC1 LWWKBWCIXTWDPG-UHFFFAOYSA-N 0.000 description 1
- DNHMUVZXPLXLIA-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-(dimethylamino)benzamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 DNHMUVZXPLXLIA-UHFFFAOYSA-N 0.000 description 1
- XDGWAONOYFLXFG-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-ethylbenzamide Chemical compound C1=CC(CC)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)CC1 XDGWAONOYFLXFG-UHFFFAOYSA-N 0.000 description 1
- SDPQHMHFTWVGGO-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidin-1-yl]sulfonylbenzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=CC=CC=2)CC1 SDPQHMHFTWVGGO-UHFFFAOYSA-N 0.000 description 1
- XJCDHGNEONSCGI-UHFFFAOYSA-N n-[4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(Cl)=CC=2)C)CC1 XJCDHGNEONSCGI-UHFFFAOYSA-N 0.000 description 1
- TXUZGLXMOOGEFH-UHFFFAOYSA-N n-[4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-3-cyanobenzamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=C(C=CC=2)C#N)CC1 TXUZGLXMOOGEFH-UHFFFAOYSA-N 0.000 description 1
- JBYTUBCCYDKMIT-UHFFFAOYSA-N n-[4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-(dimethylamino)benzamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(Cl)=CC=2)C)CC1 JBYTUBCCYDKMIT-UHFFFAOYSA-N 0.000 description 1
- XHGKLXLKSWDTAO-UHFFFAOYSA-N n-[4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-ethylbenzamide Chemical compound C1=CC(CC)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(Cl)=CC=2)C)CC1 XHGKLXLKSWDTAO-UHFFFAOYSA-N 0.000 description 1
- SUEIIQUMTHHMJG-UHFFFAOYSA-N n-[4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-fluorobenzamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C2CCN(CC2)S(=O)(=O)NC(=O)C=2C=CC(F)=CC=2)CC1 SUEIIQUMTHHMJG-UHFFFAOYSA-N 0.000 description 1
- UWKSOWVPQJIHIB-UHFFFAOYSA-N n-[4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(Cl)=CC=2)C)CC1 UWKSOWVPQJIHIB-UHFFFAOYSA-N 0.000 description 1
- ASXONCVDUDKIFC-UHFFFAOYSA-N n-[4-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]piperidin-1-yl]sulfonyl-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NS(=O)(=O)N1CCC(N2CCC(CC2)OC=2C(=CC(Cl)=CC=2)C)CC1 ASXONCVDUDKIFC-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
- 210000004126 nerve fiber Anatomy 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- VWBWQOUWDOULQN-UHFFFAOYSA-N nmp n-methylpyrrolidone Chemical compound CN1CCCC1=O.CN1CCCC1=O VWBWQOUWDOULQN-UHFFFAOYSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 238000004634 pharmacological analysis method Methods 0.000 description 1
- ABOYDMHGKWRPFD-UHFFFAOYSA-N phenylmethanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC=C1 ABOYDMHGKWRPFD-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 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
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 229920001992 poloxamer 407 Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- DRINJBFRTLBHNF-UHFFFAOYSA-N propane-2-sulfonyl chloride Chemical compound CC(C)S(Cl)(=O)=O DRINJBFRTLBHNF-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 206010041232 sneezing Diseases 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 229960002385 streptomycin sulfate Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 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
- FEZOKVOFDDONLX-UHFFFAOYSA-N tert-butyl 4-[4-(3,4-dichlorophenoxy)piperidin-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 FEZOKVOFDDONLX-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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 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
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- BQFPCTXLBRVFJL-UHFFFAOYSA-N triethoxymethylbenzene Chemical compound CCOC(OCC)(OCC)C1=CC=CC=C1 BQFPCTXLBRVFJL-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 230000008728 vascular permeability Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000003039 volatile agent Substances 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
-
- 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
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- 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
- A61P11/06—Antiasthmatics
-
- 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
- A61P11/14—Antitussive agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- 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
- A61P17/04—Antipruritics
-
- 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
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P31/04—Antibacterial agents
- A61P31/08—Antibacterial agents for leprosy
-
- 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
-
- 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
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- 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
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Obesity (AREA)
- Ophthalmology & Optometry (AREA)
- AIDS & HIV (AREA)
- Child & Adolescent Psychology (AREA)
- Otolaryngology (AREA)
- Psychiatry (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0116179.3 | 2001-07-02 | ||
| GB0116179A GB0116179D0 (en) | 2001-07-02 | 2001-07-02 | Chemical compounds |
| GB0123037.4 | 2001-09-25 | ||
| GB0123037A GB0123037D0 (en) | 2001-09-25 | 2001-09-25 | Chemical compounds |
| PCT/SE2002/001311 WO2003004487A1 (en) | 2001-07-02 | 2002-07-01 | Piperidine derivatives useful as modulators of chemokine receptor activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20040013090A true KR20040013090A (ko) | 2004-02-11 |
Family
ID=26246268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2004-7000023A Ceased KR20040013090A (ko) | 2001-07-02 | 2002-07-01 | 케모킨 수용체 활성의 조절자로서 유용한 피페리딘 유도체 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7307090B2 (enExample) |
| EP (2) | EP1604982A1 (enExample) |
| JP (1) | JP3857270B2 (enExample) |
| KR (1) | KR20040013090A (enExample) |
| CN (1) | CN1545509A (enExample) |
| AR (1) | AR042401A1 (enExample) |
| AT (1) | ATE319703T1 (enExample) |
| BR (1) | BR0210733A (enExample) |
| CA (1) | CA2452597A1 (enExample) |
| CO (1) | CO5540307A2 (enExample) |
| CY (1) | CY1106095T1 (enExample) |
| DE (1) | DE60209736T2 (enExample) |
| DK (1) | DK1404667T3 (enExample) |
| ES (1) | ES2258642T3 (enExample) |
| HU (1) | HUP0401886A2 (enExample) |
| IL (1) | IL159256A0 (enExample) |
| IS (1) | IS7094A (enExample) |
| MX (1) | MXPA03011722A (enExample) |
| NO (1) | NO20035729L (enExample) |
| NZ (1) | NZ530202A (enExample) |
| PL (1) | PL368041A1 (enExample) |
| PT (1) | PT1404667E (enExample) |
| RU (1) | RU2004100839A (enExample) |
| SA (1) | SA02230184B1 (enExample) |
| WO (1) | WO2003004487A1 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR033517A1 (es) * | 2000-04-08 | 2003-12-26 | Astrazeneca Ab | Derivados de piperidina, proceso para su preparacion y uso de estos derivados en la fabricacion de medicamentos |
| GB0120461D0 (en) | 2001-08-22 | 2001-10-17 | Astrazeneca Ab | Novel compounds |
| GB0122503D0 (en) | 2001-09-18 | 2001-11-07 | Astrazeneca Ab | Chemical compounds |
| US6949590B2 (en) * | 2002-01-10 | 2005-09-27 | University Of Washington | Hydrogels formed by non-covalent linkages |
| AU2003209388A1 (en) * | 2002-01-29 | 2003-09-02 | Merck And Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
| SE0200843D0 (sv) * | 2002-03-19 | 2002-03-19 | Astrazeneca Ab | Chemical compounds |
| SE0200844D0 (sv) * | 2002-03-19 | 2002-03-19 | Astrazeneca Ab | Chemical compounds |
| US7030115B2 (en) * | 2002-03-21 | 2006-04-18 | Abbott Laboratories | N-sulfonylurea apoptosis promoters |
| MXPA04009141A (es) * | 2002-03-21 | 2004-11-26 | Abbott Lab | Promotores de apoptosis, de n-sulfonilurea. |
| PE20040167A1 (es) | 2002-03-28 | 2004-05-26 | Novartis Ag | Amidas del acido sulfamico |
| SE0202838D0 (sv) * | 2002-09-24 | 2002-09-24 | Astrazeneca Ab | Chemical compounds |
| US20040192738A1 (en) * | 2003-03-18 | 2004-09-30 | Aventis Pharma Deutschland Gmbh | 2-(Butyl-1-sulfonylamino)-N-[1(R)-(6-methoxypyridin-3-yl)propyl] benzamide, its use as a medicament, and pharmaceutical preparations comprising it |
| SE0300957D0 (sv) * | 2003-04-01 | 2003-04-01 | Astrazeneca Ab | Chemical compounds |
| SE0302956D0 (sv) * | 2003-11-07 | 2003-11-07 | Astrazeneca Ab | Chemical compounds |
| SE0400925D0 (sv) * | 2004-04-06 | 2004-04-06 | Astrazeneca Ab | Chemical compounds |
| SE0403003D0 (sv) * | 2004-12-09 | 2004-12-09 | Astrazeneca Ab | Chemical compound 1 |
| WO2006071875A1 (en) * | 2004-12-29 | 2006-07-06 | Millennium Pharmaceuticals, Inc. | Compounds useful as chemokine receptor antagonists |
| US7635698B2 (en) | 2004-12-29 | 2009-12-22 | Millennium Pharmaceuticals, Inc. | Compounds useful as chemokine receptor antagonists |
| EP1888527A1 (en) * | 2005-05-27 | 2008-02-20 | AstraZeneca AB | Piperidines for the treatment of chemokine mediated diseases |
| TW200722419A (en) * | 2005-05-27 | 2007-06-16 | Astrazeneca Ab | Chemical compounds |
| JP2009501793A (ja) | 2005-07-21 | 2009-01-22 | アストラゼネカ・アクチエボラーグ | 新規ピペリジン誘導体 |
| EP1957076A2 (en) * | 2005-11-29 | 2008-08-20 | Merck & Co., Inc. | Thiazole derivatives as cxcr3 receptor modulators |
| CN101378756A (zh) * | 2006-02-10 | 2009-03-04 | 詹森药业有限公司 | 作为cxcr3受体拮抗剂的哌啶衍生物 |
| AU2007213734A1 (en) * | 2006-02-10 | 2007-08-16 | Janssen Pharmaceutica N.V. | Piperidine derivatives as CXCR3 receptor antagonists |
| CN101801954B (zh) * | 2007-09-20 | 2013-10-09 | Irm责任有限公司 | 作为gpr119活性调节剂的化合物和组合物 |
| EP4585589A3 (en) | 2008-12-03 | 2025-11-19 | The Scripps Research Institute | Stem cell cultures |
| CN108135168B (zh) | 2015-05-21 | 2021-07-20 | 凯莫森特里克斯股份有限公司 | Ccr2调节剂 |
| AR112831A1 (es) | 2017-09-25 | 2019-12-18 | Chemocentryx Inc | Terapia de combinación usando un antagonista del receptor 2 de quimiocina (ccr2) y un inhibidor de pd-1 / pd-l1 |
| US20190269664A1 (en) | 2018-01-08 | 2019-09-05 | Chemocentryx, Inc. | Methods of treating solid tumors with ccr2 antagonists |
| CN112105353B (zh) | 2018-01-08 | 2024-04-19 | 凯莫森特里克斯股份有限公司 | Ccr2拮抗剂治疗实体瘤的方法 |
| TWI730297B (zh) * | 2018-02-27 | 2021-06-11 | 日商組合化學工業股份有限公司 | 巰基酚化合物的製造方法及巰基酚化合物的中間體 |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1250719A (enExample) | 1969-03-19 | 1971-10-20 | ||
| US4556660A (en) | 1982-07-12 | 1985-12-03 | Janssen Pharmaceutica N.V. | N-(Bicyclic heterocyclyl)-4-piperidinamines |
| DK139684A (da) | 1983-04-11 | 1984-10-12 | Janssen Pharmaceutica Nv | N-aryl-alpha-amino-carboxamider |
| US4634704A (en) | 1983-10-06 | 1987-01-06 | Janssen Pharmaceutica, N.V. | Anti-allergic five membered heterocyclic ring containing N-(bicyclic heterocycyl)-4-piperidinamines |
| US4695575A (en) * | 1984-11-13 | 1987-09-22 | Janssen Pharmaceutica, N.V. | 4-[(bicycle heterocyclyl)-methyl and -hetero]-piperidines |
| PH23995A (en) | 1984-01-09 | 1990-02-09 | Janssen Pharmaceutica Nv | 4((bicycle heterocyclyl)-methyl and hetero)piperidines |
| US4588722A (en) | 1984-01-09 | 1986-05-13 | Janssen Pharmaceutica N.V. | N-(4-piperidinyl) bicyclic condensed 2-imidazolamine derivatives |
| EP0612313A1 (en) | 1991-11-14 | 1994-08-31 | Glaxo Group Limited | Piperidine acetic acid derivatives as inhibitors of fibrinogen-dependent blood platelet aggregation |
| GB9319534D0 (en) | 1993-09-22 | 1993-11-10 | Boots Co Plc | Therapeutic agents |
| IL117149A0 (en) | 1995-02-23 | 1996-06-18 | Schering Corp | Muscarinic antagonists |
| US5889006A (en) * | 1995-02-23 | 1999-03-30 | Schering Corporation | Muscarinic antagonists |
| US5696267A (en) | 1995-05-02 | 1997-12-09 | Schering Corporation | Substituted oximes, hydrazones and olefins as neurokinin antagonists |
| WO1996041631A1 (en) | 1995-06-09 | 1996-12-27 | Eli Lilly And Company | Methods of treating cold and allergic rhinitis |
| TW531537B (en) | 1995-12-27 | 2003-05-11 | Janssen Pharmaceutica Nv | 1-(1,2-disubstituted piperidinyl)-4-substituted piperidine derivatives |
| EP0912515B1 (en) | 1996-07-10 | 2002-11-13 | Schering Corporation | 1,4-di-substituted piperidines as muscarinic antagonists |
| US5952349A (en) * | 1996-07-10 | 1999-09-14 | Schering Corporation | Muscarinic antagonists for treating memory loss |
| EP0821954A1 (en) | 1996-08-01 | 1998-02-04 | Eli Lilly And Company | Method for treating mental retardation |
| NZ334017A (en) | 1996-08-15 | 2000-04-28 | Schering Corp | 1,4-di-substituted piperidines and use in combination with acetylcholinesterase inhibitors for treating cognitive disorders |
| US5977138A (en) * | 1996-08-15 | 1999-11-02 | Schering Corporation | Ether muscarinic antagonists |
| JP3483893B2 (ja) | 1996-09-10 | 2004-01-06 | ドクトル カルル トーマエ ゲゼルシャフト ミット ベシュレンクテル ハフツング | 修飾アミノ酸、これらの化合物を含む薬物及びそれらの調製方法 |
| JP2002510327A (ja) | 1997-07-25 | 2002-04-02 | メルク エンド カンパニー インコーポレーテッド | 環状アミンケモカイン受容体活性調節剤 |
| UA59433C2 (uk) | 1998-01-27 | 2003-09-15 | Авентіс Фармасьютікалс Продактс Інк. | ЗАМІЩЕНІ ОКСОАЗАГЕТЕРОЦИКЛІЧНІ ІНГІБІТОРИ ФАКТОРА Хa ТА ПРОМІЖНІ СПОЛУКИ ДЛЯ ЇХ ОТРИМАННЯ |
| CA2319781A1 (en) | 1998-02-02 | 1999-08-05 | Liping Wang | Cyclic amine modulators of chemokine receptor activity |
| TWI245763B (en) | 1998-04-02 | 2005-12-21 | Janssen Pharmaceutica Nv | Biocidal benzylbiphenyl derivatives |
| EP1076055B1 (en) | 1998-04-28 | 2004-11-24 | Dainippon Pharmaceutical Co., Ltd. | 1- (1-substituted-4-piperidinyl)methyl]-4-piperidine derivatives, process for producing the same, medicinal compositions containing the same and intermediates of these compounds |
| US6066636A (en) * | 1998-06-30 | 2000-05-23 | Schering Corporation | Muscarinic antagonists |
| CA2336000C (en) | 1998-06-30 | 2006-10-10 | Schering Corporation | N-substituted piperazines and 1,4-disubstituted piperidines |
| GB9919776D0 (en) | 1998-08-31 | 1999-10-27 | Zeneca Ltd | Compoujnds |
| WO2000032590A1 (en) | 1998-11-25 | 2000-06-08 | Aventis Pharmaceuticals Products Inc. | SUBSTITUTED OXOAZAHETEROCYCLYL FACTOR Xa INHIBITORS |
| AU2056800A (en) * | 1998-12-18 | 2000-07-03 | Du Pont Pharmaceuticals Company | Heterocyclic piperidines as modulators of chemokine receptor activity |
| HK1039330B (en) * | 1999-05-04 | 2005-12-09 | Schering Corporation | Piperidine derivatives useful as ccr5 antagonists |
| US6387930B1 (en) * | 1999-05-04 | 2002-05-14 | Schering Corporation | Piperidine derivatives useful as CCR5 antagonists |
| SE9902551D0 (sv) | 1999-07-02 | 1999-07-02 | Astra Pharma Prod | Novel compounds |
| EP1208097B1 (en) | 1999-07-28 | 2009-02-18 | Aventis Pharmaceuticals Inc. | Substituted oxoazaheterocyclyl compounds |
| IT1307809B1 (it) | 1999-10-21 | 2001-11-19 | Menarini Ricerche Spa | Composti monociclici basici ad azione nk-2 antagonista, processi difabbricazione e formulazioni che li contengono. |
| AR033517A1 (es) * | 2000-04-08 | 2003-12-26 | Astrazeneca Ab | Derivados de piperidina, proceso para su preparacion y uso de estos derivados en la fabricacion de medicamentos |
| GB0013060D0 (en) * | 2000-05-31 | 2000-07-19 | Astrazeneca Ab | Chemical compounds |
| WO2002018335A1 (en) | 2000-08-28 | 2002-03-07 | Yamanouchi Pharmaceutical Co., Ltd. | Cyclic amine derivatives |
| GB0021670D0 (en) | 2000-09-04 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| GB0107907D0 (en) | 2001-03-29 | 2001-05-23 | Smithkline Beecham Plc | Novel compounds |
| KR100613528B1 (ko) | 2001-03-29 | 2006-08-16 | 쉐링 코포레이션 | Ｃｃｒ5 길항제, 및 이를 포함하는 약제학적 조성물 및 키트 |
| GB0108876D0 (en) | 2001-04-09 | 2001-05-30 | Novartis Ag | Organic Compounds |
| GB0120461D0 (en) | 2001-08-22 | 2001-10-17 | Astrazeneca Ab | Novel compounds |
| AR036366A1 (es) | 2001-08-29 | 2004-09-01 | Schering Corp | Derivados de piperidina utiles como antagonistas de ccr5, composiciones farmaceuticas, el uso de dichos derivados para la fabricación de un medicamento y un kit |
| GB0122503D0 (en) | 2001-09-18 | 2001-11-07 | Astrazeneca Ab | Chemical compounds |
| SE0200844D0 (sv) | 2002-03-19 | 2002-03-19 | Astrazeneca Ab | Chemical compounds |
| SE0200843D0 (sv) | 2002-03-19 | 2002-03-19 | Astrazeneca Ab | Chemical compounds |
| SE0202838D0 (sv) | 2002-09-24 | 2002-09-24 | Astrazeneca Ab | Chemical compounds |
| SE0300850D0 (sv) | 2003-03-25 | 2003-03-25 | Astrazeneca Ab | Chemical compounds |
| SE0300957D0 (sv) | 2003-04-01 | 2003-04-01 | Astrazeneca Ab | Chemical compounds |
| SE0301368D0 (sv) | 2003-05-09 | 2003-05-09 | Astrazeneca Ab | Chemical compounds |
| CA2529161A1 (en) | 2003-06-13 | 2004-12-29 | Schering Aktiengesellschaft | Quinolyl amide derivatives as ccr-5 antagonists |
-
2002
- 2002-07-01 EP EP05018449A patent/EP1604982A1/en not_active Withdrawn
- 2002-07-01 WO PCT/SE2002/001311 patent/WO2003004487A1/en not_active Ceased
- 2002-07-01 BR BR0210733-3A patent/BR0210733A/pt not_active IP Right Cessation
- 2002-07-01 DK DK02747793T patent/DK1404667T3/da active
- 2002-07-01 AT AT02747793T patent/ATE319703T1/de not_active IP Right Cessation
- 2002-07-01 ES ES02747793T patent/ES2258642T3/es not_active Expired - Lifetime
- 2002-07-01 KR KR10-2004-7000023A patent/KR20040013090A/ko not_active Ceased
- 2002-07-01 HU HU0401886A patent/HUP0401886A2/hu unknown
- 2002-07-01 PL PL02368041A patent/PL368041A1/xx not_active Application Discontinuation
- 2002-07-01 CN CNA028162714A patent/CN1545509A/zh active Pending
- 2002-07-01 JP JP2003510654A patent/JP3857270B2/ja not_active Expired - Fee Related
- 2002-07-01 IL IL15925602A patent/IL159256A0/xx unknown
- 2002-07-01 CA CA002452597A patent/CA2452597A1/en not_active Abandoned
- 2002-07-01 RU RU2004100839/04A patent/RU2004100839A/ru not_active Application Discontinuation
- 2002-07-01 NZ NZ530202A patent/NZ530202A/en unknown
- 2002-07-01 EP EP02747793A patent/EP1404667B1/en not_active Expired - Lifetime
- 2002-07-01 DE DE60209736T patent/DE60209736T2/de not_active Expired - Lifetime
- 2002-07-01 MX MXPA03011722A patent/MXPA03011722A/es active IP Right Grant
- 2002-07-01 PT PT02747793T patent/PT1404667E/pt unknown
- 2002-07-01 US US10/480,625 patent/US7307090B2/en not_active Expired - Fee Related
- 2002-07-02 AR ARP020102488A patent/AR042401A1/es not_active Application Discontinuation
- 2002-07-02 SA SA02230184A patent/SA02230184B1/ar unknown
-
2003
- 2003-12-19 NO NO20035729A patent/NO20035729L/no not_active Application Discontinuation
- 2003-12-29 CO CO03112957A patent/CO5540307A2/es not_active Application Discontinuation
- 2003-12-30 IS IS7094A patent/IS7094A/is unknown
-
2006
- 2006-06-07 CY CY20061100755T patent/CY1106095T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SA02230184B1 (ar) | 2007-03-25 |
| BR0210733A (pt) | 2004-07-20 |
| WO2003004487A1 (en) | 2003-01-16 |
| ATE319703T1 (de) | 2006-03-15 |
| JP3857270B2 (ja) | 2006-12-13 |
| DE60209736D1 (de) | 2006-05-04 |
| HUP0401886A2 (hu) | 2004-12-28 |
| HK1062559A1 (en) | 2004-11-12 |
| NO20035729D0 (no) | 2003-12-19 |
| PT1404667E (pt) | 2006-07-31 |
| CO5540307A2 (es) | 2005-07-29 |
| PL368041A1 (en) | 2005-03-21 |
| CA2452597A1 (en) | 2003-01-16 |
| DK1404667T3 (da) | 2006-07-10 |
| CY1106095T1 (el) | 2011-06-08 |
| DE60209736T2 (de) | 2006-11-02 |
| IS7094A (is) | 2003-12-30 |
| NZ530202A (en) | 2005-06-24 |
| EP1604982A1 (en) | 2005-12-14 |
| EP1404667A1 (en) | 2004-04-07 |
| CN1545509A (zh) | 2004-11-10 |
| IL159256A0 (en) | 2004-06-01 |
| RU2004100839A (ru) | 2005-06-20 |
| JP2004536112A (ja) | 2004-12-02 |
| AR042401A1 (es) | 2005-06-22 |
| US20040235894A1 (en) | 2004-11-25 |
| MXPA03011722A (es) | 2004-03-19 |
| NO20035729L (no) | 2004-02-23 |
| EP1404667B1 (en) | 2006-03-08 |
| US7307090B2 (en) | 2007-12-11 |
| ES2258642T3 (es) | 2006-09-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20040013090A (ko) | 케모킨 수용체 활성의 조절자로서 유용한 피페리딘 유도체 | |
| US7265227B2 (en) | Piperidine derivatives useful as modulators of chemokine receptor activity | |
| US7348341B2 (en) | Chemical compounds | |
| US6903115B2 (en) | Bipiperidine compounds | |
| US7304077B2 (en) | Chemical compounds | |
| AU2003206554B2 (en) | Chemical compounds | |
| US20040110794A1 (en) | Novel piperidine derivatives as modulators of chemokine receptors | |
| KR20050052511A (ko) | 케모킨 매개된 질병 상태의 치료에서 사용하기 위한 신규피페리딘 유도체 | |
| KR20010108394A (ko) | 신규 화합물 | |
| US20040266823A1 (en) | Novel piperidine derivatives as modulators of chemokine receptors | |
| US7482363B2 (en) | Piperidine derivatives useful as modulators of chemokine receptor activity | |
| KR20050013526A (ko) | 피페리딘 유도체 및 그의 케모킨 수용체 활성의조절제로서의 용도 (특히 ｃｃｒ5) | |
| JP2005526087A (ja) | ケモカインレセプター活性モジュレーターとして有用なピペリジン誘導体 | |
| HK1062559B (en) | Piperidine derivatives useful as modulators of chemokine receptor activity | |
| AU2002318097A1 (en) | Piperidine derivatives useful as modulators of chemokine receptor activity | |
| ZA200309922B (en) | Piperidine derivatives useful as modulators of chemokine receptor activity. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20040102 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20070702 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20080624 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20080908 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20080624 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |