JP2013543512A - アリールスルホンアミドｃｃｒ３アンタゴニストの塩 - Google Patents
アリールスルホンアミドｃｃｒ３アンタゴニストの塩 Download PDFInfo
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- JP2013543512A JP2013543512A JP2013533904A JP2013533904A JP2013543512A JP 2013543512 A JP2013543512 A JP 2013543512A JP 2013533904 A JP2013533904 A JP 2013533904A JP 2013533904 A JP2013533904 A JP 2013533904A JP 2013543512 A JP2013543512 A JP 2013543512A
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- Prior art keywords
- certain embodiments
- salt
- alkyl
- ylsulfonyl
- acid
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- -1 Arylsulfonamide CCR3 antagonist salts Chemical class 0.000 title claims description 131
- 150000003839 salts Chemical class 0.000 claims abstract description 116
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims abstract description 109
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 87
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 83
- 201000010099 disease Diseases 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 44
- 208000035475 disorder Diseases 0.000 claims abstract description 37
- 208000024891 symptom Diseases 0.000 claims abstract description 23
- 230000000694 effects Effects 0.000 claims abstract description 14
- 230000001404 mediated effect Effects 0.000 claims abstract description 11
- 102100024167 C-C chemokine receptor type 3 Human genes 0.000 claims abstract 4
- 101710149862 C-C chemokine receptor type 3 Proteins 0.000 claims abstract 4
- 125000001424 substituent group Chemical group 0.000 claims description 192
- 239000000203 mixture Substances 0.000 claims description 171
- 125000000217 alkyl group Chemical group 0.000 claims description 166
- 239000001257 hydrogen Substances 0.000 claims description 101
- 229910052739 hydrogen Inorganic materials 0.000 claims description 101
- 125000000623 heterocyclic group Chemical group 0.000 claims description 76
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 125000001072 heteroaryl group Chemical group 0.000 claims description 61
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 59
- 125000005843 halogen group Chemical group 0.000 claims description 59
- 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 claims description 57
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 54
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 53
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 51
- 230000000155 isotopic effect Effects 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 46
- 239000012453 solvate Substances 0.000 claims description 45
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 44
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 44
- 150000002431 hydrogen Chemical class 0.000 claims description 40
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 39
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 27
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
- 208000006673 asthma Diseases 0.000 claims description 19
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 19
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 18
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 15
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
- 239000003937 drug carrier Substances 0.000 claims description 14
- 102000004499 CCR3 Receptors Human genes 0.000 claims description 13
- 108010017316 CCR3 Receptors Proteins 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 125000004043 oxo group Chemical group O=* 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 201000010105 allergic rhinitis Diseases 0.000 claims description 11
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 10
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 10
- 150000004677 hydrates Chemical class 0.000 claims description 10
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims description 9
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 9
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 9
- 201000008937 atopic dermatitis Diseases 0.000 claims description 9
- 239000002775 capsule Substances 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 210000003979 eosinophil Anatomy 0.000 claims description 9
- 239000011975 tartaric acid Substances 0.000 claims description 9
- 235000002906 tartaric acid Nutrition 0.000 claims description 9
- KKIWICIYPDOJJA-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-4-ethylpiperazine Chemical compound C1CN(CC)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 KKIWICIYPDOJJA-UHFFFAOYSA-N 0.000 claims description 8
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 8
- GLLAHPRABJRRPF-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)sulfanyl-3-(4-propan-2-ylpiperazin-1-yl)sulfonylbenzonitrile Chemical compound C1CN(C(C)C)CCN1S(=O)(=O)C1=CC(C#N)=CC=C1SC1=CC(Cl)=CC(Cl)=C1 GLLAHPRABJRRPF-UHFFFAOYSA-N 0.000 claims description 8
- XSJLCFHDVJVLJX-UHFFFAOYSA-N 1-[1-[5-cyano-2-(3,5-dichlorophenoxy)phenyl]sulfonylpiperidin-4-yl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C1CN(C)CCN1CCNC(=O)NC1CCN(S(=O)(=O)C=2C(=CC=C(C=2)C#N)OC=2C=C(Cl)C=C(Cl)C=2)CC1 XSJLCFHDVJVLJX-UHFFFAOYSA-N 0.000 claims description 7
- ASKFSGUALHUIFB-UHFFFAOYSA-N 4-(3,5-dimethylphenoxy)-3-(4-ethylpiperazin-1-yl)sulfonylbenzonitrile Chemical compound C1CN(CC)CCN1S(=O)(=O)C1=CC(C#N)=CC=C1OC1=CC(C)=CC(C)=C1 ASKFSGUALHUIFB-UHFFFAOYSA-N 0.000 claims description 7
- 201000004624 Dermatitis Diseases 0.000 claims description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 7
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 208000010668 atopic eczema Diseases 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 235000006408 oxalic acid Nutrition 0.000 claims description 6
- ATUWDAWZVQFESZ-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)sulfanyl-3-(4-methylpiperazin-1-yl)sulfonylbenzonitrile Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC(C#N)=CC=C1SC1=CC(Cl)=CC(Cl)=C1 ATUWDAWZVQFESZ-UHFFFAOYSA-N 0.000 claims description 5
- 206010003557 Asthma exercise induced Diseases 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 5
- 208000004657 Exercise-Induced Asthma Diseases 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 5
- 208000024998 atopic conjunctivitis Diseases 0.000 claims description 5
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 5
- 208000024695 exercise-induced bronchoconstriction Diseases 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- NOJGUESAGOUKOD-UHFFFAOYSA-N 1-[1-[5-cyano-2-(3,5-dichlorophenoxy)phenyl]sulfonylpiperidin-4-yl]-3-(2-morpholin-4-ylethyl)urea Chemical compound ClC1=CC(Cl)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCC(CC2)NC(=O)NCCN2CCOCC2)=C1 NOJGUESAGOUKOD-UHFFFAOYSA-N 0.000 claims description 4
- OSBOHMHEAXMJAN-UHFFFAOYSA-N 3-(4-cyclopentylpiperazin-1-yl)sulfonyl-4-(3,5-dichlorophenyl)sulfanylbenzonitrile Chemical compound ClC1=CC(Cl)=CC(SC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCN(CC2)C2CCCC2)=C1 OSBOHMHEAXMJAN-UHFFFAOYSA-N 0.000 claims description 4
- WBQKRUYPISYLCP-UHFFFAOYSA-N 4-(3,5-dichlorophenoxy)-3-(4-ethylpiperazin-1-yl)sulfonylbenzonitrile Chemical compound C1CN(CC)CCN1S(=O)(=O)C1=CC(C#N)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 WBQKRUYPISYLCP-UHFFFAOYSA-N 0.000 claims description 4
- 201000009961 allergic asthma Diseases 0.000 claims description 4
- 208000010247 contact dermatitis Diseases 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 4
- GRJYPFDWVKLDAF-UHFFFAOYSA-N 1-[1-[5-cyano-2-(3,5-dichlorophenoxy)phenyl]sulfonylpiperidin-4-yl]-3-(2-morpholin-4-ylethyl)urea;hydrochloride Chemical compound Cl.ClC1=CC(Cl)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCC(CC2)NC(=O)NCCN2CCOCC2)=C1 GRJYPFDWVKLDAF-UHFFFAOYSA-N 0.000 claims description 3
- GRMOEBACDZAOGV-UHFFFAOYSA-N 1-[1-[5-cyano-2-(3,5-dichlorophenoxy)phenyl]sulfonylpiperidin-4-yl]-3-(2-morpholin-4-ylethyl)urea;methanesulfonic acid Chemical compound CS(O)(=O)=O.ClC1=CC(Cl)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCC(CC2)NC(=O)NCCN2CCOCC2)=C1 GRMOEBACDZAOGV-UHFFFAOYSA-N 0.000 claims description 3
- GVOFWMOXQVCDBS-UHFFFAOYSA-N 1-[1-[5-cyano-2-(3,5-dichlorophenoxy)phenyl]sulfonylpiperidin-4-yl]-3-(2-morpholin-4-ylethyl)urea;phosphoric acid Chemical compound OP(O)(O)=O.ClC1=CC(Cl)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCC(CC2)NC(=O)NCCN2CCOCC2)=C1 GVOFWMOXQVCDBS-UHFFFAOYSA-N 0.000 claims description 3
- FUJAHCGFCBMWSI-UHFFFAOYSA-N 1-[1-[5-cyano-2-(3,5-dichlorophenoxy)phenyl]sulfonylpiperidin-4-yl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea;hydrochloride Chemical compound Cl.C1CN(C)CCN1CCNC(=O)NC1CCN(S(=O)(=O)C=2C(=CC=C(C=2)C#N)OC=2C=C(Cl)C=C(Cl)C=2)CC1 FUJAHCGFCBMWSI-UHFFFAOYSA-N 0.000 claims description 3
- UOLQDMVOEZRHTO-UHFFFAOYSA-N 1-[1-[5-cyano-2-(3,5-dichlorophenoxy)phenyl]sulfonylpiperidin-4-yl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea;phosphoric acid Chemical compound OP(O)(O)=O.C1CN(C)CCN1CCNC(=O)NC1CCN(S(=O)(=O)C=2C(=CC=C(C=2)C#N)OC=2C=C(Cl)C=C(Cl)C=2)CC1 UOLQDMVOEZRHTO-UHFFFAOYSA-N 0.000 claims description 3
- ZHDOHUGWRDDJBS-UHFFFAOYSA-N 1-[1-[5-cyano-2-(3,5-dichlorophenoxy)phenyl]sulfonylpiperidin-4-yl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea;sulfuric acid Chemical compound OS(O)(=O)=O.C1CN(C)CCN1CCNC(=O)NC1CCN(S(=O)(=O)C=2C(=CC=C(C=2)C#N)OC=2C=C(Cl)C=C(Cl)C=2)CC1 ZHDOHUGWRDDJBS-UHFFFAOYSA-N 0.000 claims description 3
- KGVNBJVYRDXAIN-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-4-ethylpiperazine;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.C1CN(CC)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 KGVNBJVYRDXAIN-UHFFFAOYSA-N 0.000 claims description 3
- HVILSSVCMQPUAD-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-4-ethylpiperazine;hydrobromide Chemical compound Br.C1CN(CC)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 HVILSSVCMQPUAD-UHFFFAOYSA-N 0.000 claims description 3
- JMZBWXFSEWHWDW-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-4-ethylpiperazine;hydrochloride Chemical compound Cl.C1CN(CC)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 JMZBWXFSEWHWDW-UHFFFAOYSA-N 0.000 claims description 3
- ZTVAXZYCSWTTDA-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-4-ethylpiperazine;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1CN(CC)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 ZTVAXZYCSWTTDA-UHFFFAOYSA-N 0.000 claims description 3
- MJLAVXWHAANLIC-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-4-ethylpiperazine;phosphoric acid Chemical compound OP(O)(O)=O.C1CN(CC)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 MJLAVXWHAANLIC-UHFFFAOYSA-N 0.000 claims description 3
- ZGSHOKXPRNWAJY-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-4-ethylpiperazine;sulfuric acid Chemical compound OS(O)(=O)=O.C1CN(CC)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 ZGSHOKXPRNWAJY-UHFFFAOYSA-N 0.000 claims description 3
- CTHZJVQHSOYHDU-UHFFFAOYSA-N 3-(4-cyclopentylpiperazin-1-yl)sulfonyl-4-(3,5-dichlorophenyl)sulfanylbenzonitrile;hydrochloride Chemical compound Cl.ClC1=CC(Cl)=CC(SC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCN(CC2)C2CCCC2)=C1 CTHZJVQHSOYHDU-UHFFFAOYSA-N 0.000 claims description 3
- ASWXDFQTOHQFSQ-UHFFFAOYSA-N 3-(4-cyclopentylpiperazin-1-yl)sulfonyl-4-(3,5-dichlorophenyl)sulfanylbenzonitrile;methanesulfonic acid Chemical compound CS(O)(=O)=O.ClC1=CC(Cl)=CC(SC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCN(CC2)C2CCCC2)=C1 ASWXDFQTOHQFSQ-UHFFFAOYSA-N 0.000 claims description 3
- OBEMBFORCLYJDH-UHFFFAOYSA-N 3-(4-cyclopentylpiperazin-1-yl)sulfonyl-4-(3,5-dichlorophenyl)sulfanylbenzonitrile;phosphoric acid Chemical compound OP(O)(O)=O.ClC1=CC(Cl)=CC(SC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCN(CC2)C2CCCC2)=C1 OBEMBFORCLYJDH-UHFFFAOYSA-N 0.000 claims description 3
- LTJAGSXSBNWHCP-UHFFFAOYSA-N 3-(4-cyclopentylpiperazin-1-yl)sulfonyl-4-(3,5-dichlorophenyl)sulfanylbenzonitrile;sulfuric acid Chemical compound OS(O)(=O)=O.ClC1=CC(Cl)=CC(SC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCN(CC2)C2CCCC2)=C1 LTJAGSXSBNWHCP-UHFFFAOYSA-N 0.000 claims description 3
- CPBINKGAXXOYQF-UHFFFAOYSA-N 4-(3,5-dichlorophenoxy)-3-(4-ethylpiperazin-1-yl)sulfonylbenzonitrile;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1CN(CC)CCN1S(=O)(=O)C1=CC(C#N)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 CPBINKGAXXOYQF-UHFFFAOYSA-N 0.000 claims description 3
- RVXFSWHPWWXUBL-UHFFFAOYSA-N 4-(3,5-dichlorophenoxy)-3-(4-ethylpiperazin-1-yl)sulfonylbenzonitrile;phosphoric acid Chemical compound OP(O)(O)=O.C1CN(CC)CCN1S(=O)(=O)C1=CC(C#N)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 RVXFSWHPWWXUBL-UHFFFAOYSA-N 0.000 claims description 3
- ZOGXHAKYDFSYRN-UHFFFAOYSA-N 4-(3,5-dichlorophenoxy)-3-(4-ethylpiperazin-1-yl)sulfonylbenzonitrile;sulfuric acid Chemical compound OS(O)(=O)=O.C1CN(CC)CCN1S(=O)(=O)C1=CC(C#N)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 ZOGXHAKYDFSYRN-UHFFFAOYSA-N 0.000 claims description 3
- WWXZUHJSPVSOPB-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)sulfanyl-3-(4-methylpiperazin-1-yl)sulfonylbenzonitrile;2,3-dihydroxybutanedioic acid Chemical compound OC(=O)C(O)C(O)C(O)=O.C1CN(C)CCN1S(=O)(=O)C1=CC(C#N)=CC=C1SC1=CC(Cl)=CC(Cl)=C1 WWXZUHJSPVSOPB-UHFFFAOYSA-N 0.000 claims description 3
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- HFKHLWDAYLPLQX-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)sulfanyl-3-(4-methylpiperazin-1-yl)sulfonylbenzonitrile;hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC(C#N)=CC=C1SC1=CC(Cl)=CC(Cl)=C1 HFKHLWDAYLPLQX-UHFFFAOYSA-N 0.000 claims description 3
- ABUNNHTUSPXNCC-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)sulfanyl-3-(4-methylpiperazin-1-yl)sulfonylbenzonitrile;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1CN(C)CCN1S(=O)(=O)C1=CC(C#N)=CC=C1SC1=CC(Cl)=CC(Cl)=C1 ABUNNHTUSPXNCC-UHFFFAOYSA-N 0.000 claims description 3
- QTMGROAHQHWVFI-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)sulfanyl-3-(4-methylpiperazin-1-yl)sulfonylbenzonitrile;phosphoric acid Chemical compound OP(O)(O)=O.C1CN(C)CCN1S(=O)(=O)C1=CC(C#N)=CC=C1SC1=CC(Cl)=CC(Cl)=C1 QTMGROAHQHWVFI-UHFFFAOYSA-N 0.000 claims description 3
- JRZCZFXLDXYJLW-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)sulfanyl-3-(4-methylpiperazin-1-yl)sulfonylbenzonitrile;sulfuric acid Chemical compound OS(O)(=O)=O.C1CN(C)CCN1S(=O)(=O)C1=CC(C#N)=CC=C1SC1=CC(Cl)=CC(Cl)=C1 JRZCZFXLDXYJLW-UHFFFAOYSA-N 0.000 claims description 3
- OKICKDZRWLSQFW-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)sulfanyl-3-(4-propan-2-ylpiperazin-1-yl)sulfonylbenzonitrile;hydrobromide Chemical compound Br.C1CN(C(C)C)CCN1S(=O)(=O)C1=CC(C#N)=CC=C1SC1=CC(Cl)=CC(Cl)=C1 OKICKDZRWLSQFW-UHFFFAOYSA-N 0.000 claims description 3
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US39192610P | 2010-10-11 | 2010-10-11 | |
| US61/391,926 | 2010-10-11 | ||
| PCT/US2011/055550 WO2012051090A1 (en) | 2010-10-11 | 2011-10-10 | Salts of arylsulfonamide ccr3 antagonists |
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| JP2013543512A true JP2013543512A (ja) | 2013-12-05 |
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| JP2013533904A Pending JP2013543512A (ja) | 2010-10-11 | 2011-10-10 | アリールスルホンアミドｃｃｒ３アンタゴニストの塩 |
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| US (1) | US20120088769A1 (enExample) |
| EP (1) | EP2627635A1 (enExample) |
| JP (1) | JP2013543512A (enExample) |
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| TW (1) | TW201226400A (enExample) |
| WO (1) | WO2012051090A1 (enExample) |
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| US8410098B2 (en) * | 2007-12-28 | 2013-04-02 | Topharman Shanghai Co., Ltd. | N-{1-[3-(2-ethoxy-5-(4-ethylpiperazinyl)sulfonylphenyl)-4,5-dihydro-5-OXO-1,2,4-triazin-6-yl]ethyl}butyramide, the preparation method and use thereof |
| NZ595823A (en) | 2009-04-22 | 2014-03-28 | Axikin Pharmaceuticals Inc | 2,5-disubstituted arylsulfonamide ccr3 antagonists |
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|---|---|
| US20120088769A1 (en) | 2012-04-12 |
| AR083383A1 (es) | 2013-02-21 |
| AU2011313906B2 (en) | 2015-08-13 |
| TW201226400A (en) | 2012-07-01 |
| CN103298786A (zh) | 2013-09-11 |
| AU2011313906A1 (en) | 2013-05-02 |
| CN103298786B (zh) | 2016-01-20 |
| MX2013003954A (es) | 2013-08-01 |
| EP2627635A1 (en) | 2013-08-21 |
| WO2012051090A1 (en) | 2012-04-19 |
| IL225717A0 (en) | 2013-06-27 |
| CA2814011A1 (en) | 2012-04-19 |
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