NZ524682A - A method for treating allergies using substituted pyrazoles - Google Patents

Info

Publication number

NZ524682A

NZ524682A NZ524682A NZ52468201A NZ524682A NZ 524682 A NZ524682 A NZ 524682A NZ 524682 A NZ524682 A NZ 524682A NZ 52468201 A NZ52468201 A NZ 52468201A NZ 524682 A NZ524682 A NZ 524682A

Authority

NZ

New Zealand

Prior art keywords

phenyl

alkyl

pyridin

piperidin

hydrogen

Prior art date

2000-09-06

Links

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• 150000003217 pyrazoles Chemical class 0.000 title abstract description 6
• 238000000034 method Methods 0.000 title description 23
• 206010020751 Hypersensitivity Diseases 0.000 title description 12
• 230000007815 allergy Effects 0.000 title description 11
• 206010027654 Allergic conditions Diseases 0.000 claims abstract description 18
• 238000011282 treatment Methods 0.000 claims abstract description 16
• -1 cyano, nitro, amino Chemical group 0.000 claims description 235
• 125000000217 alkyl group Chemical group 0.000 claims description 137
• 229910052739 hydrogen Inorganic materials 0.000 claims description 110
• 125000000623 heterocyclic group Chemical group 0.000 claims description 107
• 239000001257 hydrogen Substances 0.000 claims description 101
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
• 150000001875 compounds Chemical class 0.000 claims description 64
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
• 125000003118 aryl group Chemical group 0.000 claims description 42
• 125000002947 alkylene group Chemical group 0.000 claims description 39
• 229910052736 halogen Inorganic materials 0.000 claims description 38
• 150000002367 halogens Chemical class 0.000 claims description 38
• 125000003545 alkoxy group Chemical group 0.000 claims description 36
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 32
• 229910052757 nitrogen Inorganic materials 0.000 claims description 32
• 125000002252 acyl group Chemical group 0.000 claims description 31
• 229920006395 saturated elastomer Polymers 0.000 claims description 31
• 239000002253 acid Substances 0.000 claims description 27
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
• 125000003435 aroyl group Chemical group 0.000 claims description 20
• 150000002148 esters Chemical class 0.000 claims description 20
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 17
• 125000003342 alkenyl group Chemical group 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 15
• 150000001408 amides Chemical class 0.000 claims description 14
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 12
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 12
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 9
• 125000002757 morpholinyl group Chemical group 0.000 claims description 9
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
• 102100028701 General vesicular transport factor p115 Human genes 0.000 claims description 8
• 101000767151 Homo sapiens General vesicular transport factor p115 Proteins 0.000 claims description 8
• 125000002950 monocyclic group Chemical group 0.000 claims description 8
• DYSJMQABFPKAQM-UHFFFAOYSA-N 1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)=CC2=C1 DYSJMQABFPKAQM-UHFFFAOYSA-N 0.000 claims description 7
• 125000004193 piperazinyl group Chemical group 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 7
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 5
• 102200029256 rs121964925 Human genes 0.000 claims description 5
• 125000004423 acyloxy group Chemical group 0.000 claims description 4
• 125000005605 benzo group Chemical group 0.000 claims description 4
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
• 125000001188 haloalkyl group Chemical group 0.000 claims description 4
• 150000004702 methyl esters Chemical class 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 125000005936 piperidyl group Chemical group 0.000 claims description 4
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 3
• JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 3
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 3
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• 125000004970 halomethyl group Chemical group 0.000 claims description 3
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 claims description 3
• 125000004043 oxo group Chemical group O=* 0.000 claims description 3
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
• 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
• 102220535958 Dynein axonemal intermediate chain 4_R17S_mutation Human genes 0.000 claims description 2
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
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• 229910052701 rubidium Inorganic materials 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 26
• 125000001475 halogen functional group Chemical group 0.000 claims 2
• 102220094037 rs864622206 Human genes 0.000 claims 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• CWZXXCKXNWRADB-UHFFFAOYSA-N 1-[5-methylsulfonyl-3-[4-(trifluoromethyl)phenyl]-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-1-yl]-3-[4-(1h-pyrrolo[2,3-b]pyridin-3-yl)piperidin-1-yl]propan-2-ol Chemical compound C1N(S(=O)(=O)C)CCC(N(N=2)CC(O)CN3CCC(CC3)C=3C4=CC=CN=C4NC=3)=C1C=2C1=CC=C(C(F)(F)F)C=C1 CWZXXCKXNWRADB-UHFFFAOYSA-N 0.000 claims 1
• OPJLJQPNIKHAJC-UHFFFAOYSA-N 1-[5-methylsulfonyl-3-[4-(trifluoromethyl)phenyl]-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-1-yl]-3-[4-(6-morpholin-4-yl-1h-pyrrolo[3,2-c]pyridin-3-yl)piperidin-1-yl]propan-2-ol Chemical compound C1N(S(=O)(=O)C)CCC2=C1C(C=1C=CC(=CC=1)C(F)(F)F)=NN2CC(O)CN(CC1)CCC1C(C1=CN=2)=CNC1=CC=2N1CCOCC1 OPJLJQPNIKHAJC-UHFFFAOYSA-N 0.000 claims 1
• NIINAQIZMZPQPH-UHFFFAOYSA-N 3-[1-[2-hydroxy-3-[5-methylsulfonyl-3-[4-(trifluoromethyl)phenyl]-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-1-yl]propyl]piperidin-4-yl]-1h-indole-5-carbonitrile Chemical compound C1N(S(=O)(=O)C)CCC(N(N=2)CC(O)CN3CCC(CC3)C=3C4=CC(=CC=C4NC=3)C#N)=C1C=2C1=CC=C(C(F)(F)F)C=C1 NIINAQIZMZPQPH-UHFFFAOYSA-N 0.000 claims 1
• 101000831272 Oryza sativa subsp. japonica Cysteine proteinase inhibitor 5 Proteins 0.000 claims 1
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
• 102200031660 rs730880032 Human genes 0.000 claims 1
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 276
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• 239000000203 mixture Substances 0.000 description 63
• 238000005160 1H NMR spectroscopy Methods 0.000 description 47
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
• 239000011541 reaction mixture Substances 0.000 description 40
• 239000000243 solution Substances 0.000 description 34
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