CA2459432C - Arylsulfonamide derivatives for use as ccr3 antagonists in the treatment of inflammatory and immunological disorders - Google Patents
Arylsulfonamide derivatives for use as ccr3 antagonists in the treatment of inflammatory and immunological disorders Download PDFInfo
- Publication number
- CA2459432C CA2459432C CA002459432A CA2459432A CA2459432C CA 2459432 C CA2459432 C CA 2459432C CA 002459432 A CA002459432 A CA 002459432A CA 2459432 A CA2459432 A CA 2459432A CA 2459432 C CA2459432 C CA 2459432C
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- CA
- Canada
- Prior art keywords
- hydrogen
- branched
- straight
- piperazine
- nitrophenylsulfonyl
- 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.)
- Expired - Fee Related
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- 230000002757 inflammatory effect Effects 0.000 title claims abstract description 9
- 238000011282 treatment Methods 0.000 title abstract description 12
- 208000026278 immune system disease Diseases 0.000 title abstract description 4
- 208000027866 inflammatory disease Diseases 0.000 title description 2
- 239000005557 antagonist Substances 0.000 title 1
- 125000004421 aryl sulphonamide group Chemical group 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 39
- 201000010099 disease Diseases 0.000 claims abstract description 23
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 claims abstract description 22
- 208000006673 asthma Diseases 0.000 claims abstract description 11
- 206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 4
- 201000010105 allergic rhinitis Diseases 0.000 claims abstract description 4
- 206010012438 Dermatitis atopic Diseases 0.000 claims abstract description 3
- 201000008937 atopic dermatitis Diseases 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 235
- 239000001257 hydrogen Substances 0.000 claims description 229
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 221
- 239000000203 mixture Substances 0.000 claims description 198
- -1 cyano, carboxy Chemical group 0.000 claims description 130
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 124
- 150000001875 compounds Chemical class 0.000 claims description 109
- 229910052736 halogen Inorganic materials 0.000 claims description 96
- 229920006395 saturated elastomer Polymers 0.000 claims description 86
- 150000002367 halogens Chemical group 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 68
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 36
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- 125000001153 fluoro group Chemical group F* 0.000 claims description 25
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 25
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 229910020008 S(O) Inorganic materials 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 18
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 18
- 208000035475 disorder Diseases 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- 125000001589 carboacyl group Chemical group 0.000 claims description 9
- 210000004072 lung Anatomy 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 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
- 230000007170 pathology Effects 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- SWZVWZBDHFNTLD-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-4-pyrrolidin-1-ylpiperidine Chemical compound C1CC(N2CCCC2)CCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1 SWZVWZBDHFNTLD-UHFFFAOYSA-N 0.000 claims description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 5
- 208000026935 allergic disease Diseases 0.000 claims description 5
- 230000001363 autoimmune Effects 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 230000004957 immunoregulator effect Effects 0.000 claims description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- GKHAHZQMENAZHG-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1 GKHAHZQMENAZHG-UHFFFAOYSA-N 0.000 claims description 4
- SYVJNCBQBAPSCK-UHFFFAOYSA-N 3-(1,4-diazepan-1-ylsulfonyl)-4-(3,5-dichlorophenyl)sulfanylbenzonitrile Chemical compound ClC1=CC(Cl)=CC(SC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCNCCC2)=C1 SYVJNCBQBAPSCK-UHFFFAOYSA-N 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 206010018691 Granuloma Diseases 0.000 claims description 4
- 208000003807 Graves Disease Diseases 0.000 claims description 4
- 208000015023 Graves' disease Diseases 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- SNNMYKHACBYNPF-SFHVURJKSA-N (2s)-1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-2-(pyrrolidin-1-ylmethyl)pyrrolidine Chemical compound N1([C@@H](CCC1)CN1CCCC1)S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1 SNNMYKHACBYNPF-SFHVURJKSA-N 0.000 claims description 3
- CXMDVJPSBFHFAZ-UHFFFAOYSA-N 1-[2-(3,5-dibromophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Br)=CC(Br)=C1 CXMDVJPSBFHFAZ-UHFFFAOYSA-N 0.000 claims description 3
- MWURPJRFLFHBRA-UHFFFAOYSA-N 1-[2-(3,5-dichloro-2-fluorophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1F MWURPJRFLFHBRA-UHFFFAOYSA-N 0.000 claims description 3
- YOUXJSFJQJOEAR-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-1,4-diazepane Chemical compound C1CCNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1 YOUXJSFJQJOEAR-UHFFFAOYSA-N 0.000 claims description 3
- DJXLHVLRWFRMAX-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-n,n-diethylpyrrolidin-3-amine Chemical compound C1C(N(CC)CC)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 DJXLHVLRWFRMAX-UHFFFAOYSA-N 0.000 claims description 3
- UZEKJXMJLMPEHG-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonylpiperazine-2-carboxylic acid Chemical compound OC(=O)C1CNCCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 UZEKJXMJLMPEHG-UHFFFAOYSA-N 0.000 claims description 3
- UGKSLSUMQNVYAW-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-1,4-diazepane Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCCC2)=C1 UGKSLSUMQNVYAW-UHFFFAOYSA-N 0.000 claims description 3
- FLIQFYMILMDSAW-UHFFFAOYSA-N 1-[5-chloro-2-(3,5-dimethylphenoxy)phenyl]sulfonyl-4-ethylpiperazine Chemical compound C1CN(CC)CCN1S(=O)(=O)C1=CC(Cl)=CC=C1OC1=CC(C)=CC(C)=C1 FLIQFYMILMDSAW-UHFFFAOYSA-N 0.000 claims description 3
- QAAQMEREUWOLCE-UHFFFAOYSA-N 1-[5-cyano-2-(3,5-dichlorophenoxy)phenyl]sulfonylpiperazine-2-carboxylic acid Chemical compound OC(=O)C1CNCCN1S(=O)(=O)C1=CC(C#N)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 QAAQMEREUWOLCE-UHFFFAOYSA-N 0.000 claims description 3
- WRKKDSRZODVOKL-UHFFFAOYSA-N 3-(1,4-diazepan-1-ylsulfonyl)-4-(3,5-dichlorophenoxy)benzonitrile Chemical compound ClC1=CC(Cl)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCNCCC2)=C1 WRKKDSRZODVOKL-UHFFFAOYSA-N 0.000 claims description 3
- YGJRGROVYIAAEF-KDOFPFPSSA-N 3-[[(4ar,7ar)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]sulfonyl]-4-(3,5-dichlorophenoxy)benzonitrile Chemical compound ClC1=CC(Cl)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2C[C@@H]3NCCC[C@@H]3C2)=C1 YGJRGROVYIAAEF-KDOFPFPSSA-N 0.000 claims description 3
- JFVOTMZEFSIFQC-UHFFFAOYSA-N 4-(3,5-dichlorophenoxy)-3-(3-pyrrolidin-1-ylpyrrolidin-1-yl)sulfonylbenzonitrile Chemical compound ClC1=CC(Cl)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CC(CC2)N2CCCC2)=C1 JFVOTMZEFSIFQC-UHFFFAOYSA-N 0.000 claims description 3
- QBWFIHQVXQNTKR-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)sulfanyl-3-piperazin-1-ylsulfonylbenzonitrile Chemical compound ClC1=CC(Cl)=CC(SC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCNCC2)=C1 QBWFIHQVXQNTKR-UHFFFAOYSA-N 0.000 claims description 3
- FQQMTRHHBWAIOR-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)sulfinyl-3-piperazin-1-ylsulfonylbenzonitrile Chemical compound ClC1=CC(Cl)=CC(S(=O)C=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCNCC2)=C1 FQQMTRHHBWAIOR-UHFFFAOYSA-N 0.000 claims description 3
- GLOJZOGSKZSTGZ-UHFFFAOYSA-N 4-(3,5-dimethylphenoxy)-3-piperazin-1-ylsulfonylbenzonitrile Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCNCC2)=C1 GLOJZOGSKZSTGZ-UHFFFAOYSA-N 0.000 claims description 3
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- POXBXXTZUWRVJJ-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-4-ethylpiperazine Chemical compound C1CN(CC)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(C)=CC(C)=C1 POXBXXTZUWRVJJ-UHFFFAOYSA-N 0.000 claims description 2
- DALAEMNLGUGTHA-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)sulfanyl-5-nitro-n-(2-piperidin-1-ylethyl)benzenesulfonamide Chemical compound C1CCCCN1CCNS(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1SC1=CC(Cl)=CC(Cl)=C1 DALAEMNLGUGTHA-UHFFFAOYSA-N 0.000 claims description 2
- SOBDEZLUKQZUDH-UHFFFAOYSA-N 4-(3,5-dichloroanilino)-3-piperazin-1-ylsulfonylbenzonitrile Chemical compound ClC1=CC(Cl)=CC(NC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCNCC2)=C1 SOBDEZLUKQZUDH-UHFFFAOYSA-N 0.000 claims description 2
- SVJZYRLXAFKAGE-UHFFFAOYSA-N 4-(3,5-dichlorophenoxy)-3-(4-pyrrolidin-1-ylpiperidin-1-yl)sulfonylbenzonitrile Chemical compound ClC1=CC(Cl)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCC(CC2)N2CCCC2)=C1 SVJZYRLXAFKAGE-UHFFFAOYSA-N 0.000 claims description 2
- FCRPFAFVEWSZBJ-UHFFFAOYSA-N 4-(3,5-dichlorophenoxy)-3-piperazin-1-ylsulfonylbenzonitrile Chemical compound ClC1=CC(Cl)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCNCC2)=C1 FCRPFAFVEWSZBJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- HOJUVRBONHUFOC-UHFFFAOYSA-N methyl 4-(3,5-dimethylphenoxy)-3-piperazin-1-ylsulfonylbenzoate Chemical compound C1CNCCN1S(=O)(=O)C1=CC(C(=O)OC)=CC=C1OC1=CC(C)=CC(C)=C1 HOJUVRBONHUFOC-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 85
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 63
- LCDFCOUDXRXGBN-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-4-propan-2-ylpiperazine Chemical compound C1CN(C(C)C)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(C)=CC(C)=C1 LCDFCOUDXRXGBN-UHFFFAOYSA-N 0.000 claims 3
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- PZXBCZDWOYKAFB-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-3,5-dimethylpiperazine Chemical compound C1C(C)NC(C)CN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 PZXBCZDWOYKAFB-UHFFFAOYSA-N 0.000 claims 2
- LPTOUQBSQLGFOP-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-3-pyrrolidin-1-ylpyrrolidine Chemical compound C1CC(N2CCCC2)CN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1 LPTOUQBSQLGFOP-UHFFFAOYSA-N 0.000 claims 2
- UNTKZXYTPPOUHO-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenyl)sulfanyl-5-nitrophenyl]sulfonyl-4-pyrrolidin-1-ylpiperidine Chemical compound C1CC(N2CCCC2)CCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1SC1=CC(Cl)=CC(Cl)=C1 UNTKZXYTPPOUHO-UHFFFAOYSA-N 0.000 claims 2
- NFRVUXGKEBPMMO-UHFFFAOYSA-N 1-[2-(3-fluorophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC(F)=C1 NFRVUXGKEBPMMO-UHFFFAOYSA-N 0.000 claims 2
- IIZWKTPGUGWWCY-UHFFFAOYSA-N 1-[2-(3-methyl-5-propan-2-ylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC(C)C1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 IIZWKTPGUGWWCY-UHFFFAOYSA-N 0.000 claims 2
- JJCOLCAPAYHLMB-UHFFFAOYSA-N 1-[2-(3-methylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC1=CC=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 JJCOLCAPAYHLMB-UHFFFAOYSA-N 0.000 claims 2
- OCNYKXUWFGVIJA-UHFFFAOYSA-N 3-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-ylsulfonyl)-4-(3,5-dichlorophenoxy)benzonitrile Chemical compound ClC1=CC(Cl)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CC3CCCN3CC2)=C1 OCNYKXUWFGVIJA-UHFFFAOYSA-N 0.000 claims 2
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- CNZUBHUTQIKZHA-UHFFFAOYSA-N 1-(2-naphthalen-1-yloxy-5-nitrophenyl)sulfonylpiperazine Chemical compound C=1C([N+](=O)[O-])=CC=C(OC=2C3=CC=CC=C3C=CC=2)C=1S(=O)(=O)N1CCNCC1 CNZUBHUTQIKZHA-UHFFFAOYSA-N 0.000 claims 1
- HXRLXBUOLIUSRP-UHFFFAOYSA-N 1-(2-naphthalen-2-ylsulfanyl-5-nitrophenyl)sulfonylpiperazine Chemical compound C=1C([N+](=O)[O-])=CC=C(SC=2C=C3C=CC=CC3=CC=2)C=1S(=O)(=O)N1CCNCC1 HXRLXBUOLIUSRP-UHFFFAOYSA-N 0.000 claims 1
- NDZYPHLNJZSQJY-QNWVGRARSA-N 1-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-3-[(1r,2s)-2-[[(3s)-3-[(4-fluorophenyl)methyl]piperidin-1-yl]methyl]cyclohexyl]urea Chemical compound CC1=C(C(=O)C)SC(NC(=O)N[C@H]2[C@@H](CCCC2)CN2C[C@H](CC=3C=CC(F)=CC=3)CCC2)=N1 NDZYPHLNJZSQJY-QNWVGRARSA-N 0.000 claims 1
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- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000019254 respiratory burst Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000008275 solid aerosol Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000012058 sterile packaged powder Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- DJMBWMQBLUGTNR-UHFFFAOYSA-N tert-butyl 4-(4-chloropyridin-3-yl)sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1S(=O)(=O)C1=CN=CC=C1Cl DJMBWMQBLUGTNR-UHFFFAOYSA-N 0.000 description 1
- NFVFKZXFJALHTB-UHFFFAOYSA-N tert-butyl 4-(5-carbamoyl-2-fluorophenyl)sulfonyl-1,4-diazepane-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCCN1S(=O)(=O)C1=CC(C(N)=O)=CC=C1F NFVFKZXFJALHTB-UHFFFAOYSA-N 0.000 description 1
- AUMGJJYAHGULEY-UHFFFAOYSA-N tert-butyl 4-(5-cyano-2-fluorophenyl)sulfonyl-1,4-diazepane-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCCN1S(=O)(=O)C1=CC(C#N)=CC=C1F AUMGJJYAHGULEY-UHFFFAOYSA-N 0.000 description 1
- SSLSSQQAQXHHHX-UHFFFAOYSA-N tert-butyl 4-[2-(3,5-dimethylphenoxy)-4-methyl-5-nitrophenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=C(C)C=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 SSLSSQQAQXHHHX-UHFFFAOYSA-N 0.000 description 1
- IXBWTTXRCGKKEH-UHFFFAOYSA-N tert-butyl 4-[2-(3,5-dimethylphenoxy)-4-nitrophenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C(=CC=C(C=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 IXBWTTXRCGKKEH-UHFFFAOYSA-N 0.000 description 1
- UZHKEWQMAAUIJX-UHFFFAOYSA-N tert-butyl 4-[2-(3,5-dimethylphenoxy)-5-(hydroxymethyl)phenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C(=CC(CO)=CC=2)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 UZHKEWQMAAUIJX-UHFFFAOYSA-N 0.000 description 1
- WEKBRBQLFGPBQL-UHFFFAOYSA-N tert-butyl 4-[2-(3,5-dimethylphenyl)sulfanyl-5-nitrophenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(SC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 WEKBRBQLFGPBQL-UHFFFAOYSA-N 0.000 description 1
- SCTLMFUOSJUCIT-UHFFFAOYSA-N tert-butyl 4-[2-chloro-5-(dimethylcarbamoyl)phenyl]sulfonylpiperazine-1-carboxylate Chemical compound CN(C)C(=O)C1=CC=C(Cl)C(S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 SCTLMFUOSJUCIT-UHFFFAOYSA-N 0.000 description 1
- NPRGXPRWUYOUGX-UHFFFAOYSA-N tert-butyl 4-[3-bromo-5-(3,5-dimethylphenoxy)phenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C=C(C=C(Br)C=2)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 NPRGXPRWUYOUGX-UHFFFAOYSA-N 0.000 description 1
- OBWKZWTXDNULLX-UHFFFAOYSA-N tert-butyl 4-[4-(3,5-dimethylphenoxy)pyridin-3-yl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C(=CN=CC=2)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 OBWKZWTXDNULLX-UHFFFAOYSA-N 0.000 description 1
- SGQKNUSSFCVPID-UHFFFAOYSA-N tert-butyl 4-[5-chloro-2-(3,5-dimethylphenoxy)phenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C(=CC(Cl)=CC=2)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 SGQKNUSSFCVPID-UHFFFAOYSA-N 0.000 description 1
- HXKOCZAITVMTQI-UHFFFAOYSA-N tert-butyl 4-[5-cyano-2-(3,5-dichlorophenoxy)phenyl]sulfonyl-1,4-diazepane-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCCN1S(=O)(=O)C1=CC(C#N)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 HXKOCZAITVMTQI-UHFFFAOYSA-N 0.000 description 1
- XKXIQBVKMABYQJ-UHFFFAOYSA-M tert-butyl carbonate Chemical compound CC(C)(C)OC([O-])=O XKXIQBVKMABYQJ-UHFFFAOYSA-M 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
- 229960001600 xylazine Drugs 0.000 description 1
- 229930195724 β-lactose Natural products 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
- A61P5/16—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4 for decreasing, blocking or antagonising the activity of the thyroid hormones
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
- C07C323/67—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfonamide groups, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
- C07D211/28—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
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| MXPA05010055A (es) * | 2003-03-24 | 2005-11-23 | Actimis Pharmaceuticals Inc | Derivados de 2-fenoxi- y 2-fenil-sulfomamida con actividad antagonista del ccr3, para el tratamiento del asma y otros desordenes inflamatorios o inmunologicos. |
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| US8791264B2 (en) | 2006-04-13 | 2014-07-29 | Purdue Pharma L.P. | Benzenesulfonamide compounds and their use as blockers of calcium channels |
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| US8399486B2 (en) | 2007-04-09 | 2013-03-19 | Purdue Pharma L.P. | Benzenesulfonyl compounds and the use thereof |
| US7897776B2 (en) | 2007-04-23 | 2011-03-01 | Salutria Pharmaceuticals Llc | Sulfonamide containing compounds for treatment of inflammatory disorders |
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| NZ593473A (en) * | 2009-01-12 | 2013-02-22 | Pfizer Ltd | Sulfonamide derivatives |
| TW201036941A (en) * | 2009-03-30 | 2010-10-16 | Sumitomo Chemical Co | Method for producing sulfonamide compound |
| CN102448951B (zh) | 2009-04-06 | 2017-05-10 | 安吉奥斯医药品有限公司 | 丙酮酸激酶m2调节剂、治疗组合物和相关使用方法 |
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| AU2010239340B2 (en) | 2009-04-22 | 2015-07-02 | Axikin Pharmaceuticals, Inc. | 2,5-disubstituted arylsulfonamide CCR3 antagonists |
| WO2010129351A1 (en) | 2009-04-28 | 2010-11-11 | Schepens Eye Research Institute | Method to identify and treat age-related macular degeneration |
| NZ597379A (en) | 2009-06-29 | 2014-04-30 | Agios Pharmaceuticals Inc | Therapeutic compounds and compositions |
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| AU2011223873B2 (en) * | 2010-03-02 | 2015-06-25 | Axikin Pharmaceuticals, Inc. | Isotopically enriched arylsulfonamide CCR3 antagonists |
| EP2547655B1 (en) * | 2010-03-17 | 2016-03-09 | Axikin Pharmaceuticals, Inc. | Arylsulfonamide ccr3 antagonists |
| CA2803118C (en) | 2010-07-09 | 2015-11-03 | Pfizer Limited | Sulfonamide derivatives as nav 1.7 inhibitors |
| JP5872552B2 (ja) | 2010-07-09 | 2016-03-01 | ファイザー・リミテッドPfizer Limited | 化学化合物 |
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| EP2651898B1 (en) | 2010-12-17 | 2015-12-09 | Agios Pharmaceuticals, Inc. | Novel n-(4-(azetidine-1-carbonyl)phenyl)-(hetero-)arylsulfonamide derivatives as pyruvate kinase m2 (pmk2) modulators |
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| PH12017501176B1 (en) | 2011-05-03 | 2023-03-08 | Agios Pharmaceuticals Inc | Pyruvate kinase activators for use in therapy |
| US9181231B2 (en) | 2011-05-03 | 2015-11-10 | Agios Pharmaceuticals, Inc | Pyruvate kinase activators for use for increasing lifetime of the red blood cells and treating anemia |
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| US12221463B2 (en) | 2020-08-07 | 2025-02-11 | The Board Of Regents Of The University Of Oklahoma | Method of promoting wound healing by inhibiting CCR3 |
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| US2275354A (en) * | 1937-11-29 | 1942-03-03 | May & Baker Ltd | Preparation of new therapeutically useful heterocyclic compounds |
| GB1368948A (en) * | 1970-11-11 | 1974-10-02 | Manuf Prod Pharma | Pyridine derivatives |
| US4233409A (en) * | 1979-07-05 | 1980-11-11 | Monsanto Company | Polymeric blend |
| DE3751728T2 (de) | 1987-12-14 | 1996-10-31 | Dow Chemical Co | Abs-zusammensetzungen mit trimodalkautschukteilchenverteilungen |
| US5041498A (en) * | 1990-01-02 | 1991-08-20 | The Dow Chemical Company | Trimodal ABS compositions having good gloss and reduced gloss sensitivity |
| DE4404749A1 (de) * | 1994-02-15 | 1995-08-17 | Bayer Ag | ABS-Polymer-Zusammensetzungen mit gleichmäßiger matter Oberfläche |
| US6057322A (en) * | 1995-01-30 | 2000-05-02 | Hoechst Aktiengesellschaft | Basically-substituted benzoylguanidines, a process for preparing them, their use as a medicament or diagnostic agent, and a medicament containing them |
| DE19507749A1 (de) * | 1995-03-06 | 1996-09-12 | Bayer Ag | Thermoplastische Formmassen vom ABS-Typ |
| DE19518025A1 (de) * | 1995-05-17 | 1996-11-21 | Bayer Ag | Thermoplastische ABS-Formmassen |
| IL138027A (en) * | 1995-12-08 | 2004-08-31 | Agouron Pharma | Intermediates for the preparation and preparation of metalloproteinase inhibitors |
| GB9602166D0 (en) * | 1996-02-02 | 1996-04-03 | Zeneca Ltd | Aminoheterocyclic derivatives |
| US6262113B1 (en) * | 1996-03-20 | 2001-07-17 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| DE19649249A1 (de) * | 1996-11-28 | 1998-06-04 | Bayer Ag | Verbesserte thermoplastische Formmassen vom ABS-Typ |
| US6284923B1 (en) * | 1997-08-22 | 2001-09-04 | Tularik Inc | Substituted benzene compounds as antiproliferative and cholesterol lowering action |
| CA2329777A1 (en) * | 1998-04-27 | 1999-11-04 | Dashyant Dhanak | Ccr-3 receptor antagonists |
| ATE309205T1 (de) * | 1999-01-13 | 2005-11-15 | Warner Lambert Co | Benzenesulfonamid-derivative und ihre verwendung als mek-inhibitoren |
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| AU1161601A (en) | 1999-11-05 | 2001-05-14 | University College London | Activators of soluble guanylate cyclase |
| DE10008420A1 (de) | 2000-02-23 | 2001-08-30 | Bayer Ag | Polymerzusammensetzungen mit verbesserter Eigenschaftskonstanz |
| DE10008419A1 (de) | 2000-02-23 | 2001-08-30 | Bayer Ag | Polymerzusammensetzungen mit verbesserter Eigenschaftskonstanz |
| JP2003081937A (ja) | 2001-09-07 | 2003-03-19 | Bayer Ag | ベンゼンスルホンアミド誘導体 |
| DE10145773A1 (de) | 2001-09-17 | 2003-04-03 | Bayer Ag | ABS-Zusammensetzungen mit verbesserten Eigenschaftskombinationen |
| MXPA05010055A (es) * | 2003-03-24 | 2005-11-23 | Actimis Pharmaceuticals Inc | Derivados de 2-fenoxi- y 2-fenil-sulfomamida con actividad antagonista del ccr3, para el tratamiento del asma y otros desordenes inflamatorios o inmunologicos. |
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2001
- 2001-09-07 JP JP2001272327A patent/JP2003081937A/ja active Pending
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2002
- 2002-08-29 AR ARP020103259A patent/AR037235A1/es not_active Application Discontinuation
- 2002-09-04 EP EP07013793A patent/EP1849469B1/en not_active Expired - Lifetime
- 2002-09-04 EP EP02772265A patent/EP1461038B9/en not_active Expired - Lifetime
- 2002-09-04 JP JP2003526406A patent/JP4517047B2/ja not_active Expired - Fee Related
- 2002-09-04 US US10/489,029 patent/US7700586B2/en not_active Expired - Fee Related
- 2002-09-04 DE DE60221569T patent/DE60221569T2/de not_active Expired - Lifetime
- 2002-09-04 CA CA002459432A patent/CA2459432C/en not_active Expired - Fee Related
- 2002-09-04 WO PCT/EP2002/009873 patent/WO2003022277A1/en not_active Ceased
- 2002-09-04 ES ES07013793T patent/ES2354378T3/es not_active Expired - Lifetime
- 2002-09-04 DE DE60238149T patent/DE60238149D1/de not_active Expired - Lifetime
- 2002-09-04 ES ES02772265T patent/ES2294167T3/es not_active Expired - Lifetime
- 2002-09-05 TW TW091120389A patent/TWI262187B/zh not_active IP Right Cessation
- 2002-09-05 GT GT200200178A patent/GT200200178A/es unknown
- 2002-09-06 MY MYPI20023349A patent/MY133303A/en unknown
- 2002-09-06 SV SV2002001225A patent/SV2004001225A/es not_active Application Discontinuation
- 2002-09-06 HN HN2002000247A patent/HN2002000247A/es unknown
- 2002-09-06 PE PE2002000882A patent/PE20030440A1/es not_active Application Discontinuation
-
2010
- 2010-04-19 US US12/763,072 patent/US8242118B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2294167T3 (es) | 2008-04-01 |
| MY133303A (en) | 2007-11-30 |
| ES2354378T3 (es) | 2011-03-14 |
| HK1109867A1 (en) | 2008-06-27 |
| TWI262187B (en) | 2006-09-21 |
| GT200200178A (es) | 2003-05-23 |
| US8242118B2 (en) | 2012-08-14 |
| WO2003022277A1 (en) | 2003-03-20 |
| EP1461038A1 (en) | 2004-09-29 |
| JP2005519024A (ja) | 2005-06-30 |
| DE60221569D1 (de) | 2007-09-13 |
| EP1461038B9 (en) | 2009-09-23 |
| SV2004001225A (es) | 2004-02-24 |
| CA2459432A1 (en) | 2003-03-20 |
| PE20030440A1 (es) | 2003-06-26 |
| US7700586B2 (en) | 2010-04-20 |
| US20100204213A1 (en) | 2010-08-12 |
| JP4517047B2 (ja) | 2010-08-04 |
| AR037235A1 (es) | 2004-11-03 |
| US20050070582A1 (en) | 2005-03-31 |
| EP1461038B1 (en) | 2007-08-01 |
| DE60238149D1 (de) | 2010-12-09 |
| HN2002000247A (es) | 2003-11-24 |
| DE60221569T2 (de) | 2008-04-30 |
| EP1849469B1 (en) | 2010-10-27 |
| EP1849469A1 (en) | 2007-10-31 |
| JP2003081937A (ja) | 2003-03-19 |
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