UA79558C2 - Heterocyclic compounds for treating inflammatory and allergic disorders, method for their production - Google Patents

Info

Publication number

UA79558C2

UA79558C2 UAA200510680A UAA200510680A UA79558C2 UA 79558 C2 UA79558 C2 UA 79558C2 UA A200510680 A UAA200510680 A UA A200510680A UA A200510680 A UAA200510680 A UA A200510680A UA 79558 C2 UA79558 C2 UA 79558C2

Authority

UA

Ukraine

Prior art keywords

substituted

unsubstituted

carboxamide

furan

dichloropyrid

Prior art date

2003-04-11

Links

• Espacenet
• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 36
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 32
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• 230000002757 inflammatory effect Effects 0.000 title claims description 10
• 230000000172 allergic effect Effects 0.000 title claims description 8
• 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 7
• 238000004519 manufacturing process Methods 0.000 title description 9
• 150000003839 salts Chemical class 0.000 claims abstract description 85
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• 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 abstract description 10
• 239000012453 solvate Substances 0.000 claims abstract description 8
• 150000001875 compounds Chemical class 0.000 claims description 120
• 235000002639 sodium chloride Nutrition 0.000 claims description 88
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 69
• -1 -OH Chemical group 0.000 claims description 60
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 47
• 239000000047 product Substances 0.000 claims description 44
• 125000000217 alkyl group Chemical group 0.000 claims description 43
• 238000006243 chemical reaction Methods 0.000 claims description 42
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 36
• 125000000623 heterocyclic group Chemical group 0.000 claims description 32
• 229910052736 halogen Inorganic materials 0.000 claims description 30
• 150000002367 halogens Chemical class 0.000 claims description 30
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 125000001072 heteroaryl group Chemical group 0.000 claims description 26
• 239000000543 intermediate Substances 0.000 claims description 26
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 24
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 239000001257 hydrogen Substances 0.000 claims description 23
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• 238000011282 treatment Methods 0.000 claims description 22
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
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• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 19
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• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 19
• 125000000304 alkynyl group Chemical group 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 18
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• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 15
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• 125000004122 cyclic group Chemical group 0.000 claims description 9
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• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 9
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• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
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• ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 5
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• 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
• QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 4
• 206010069698 Langerhans' cell histiocytosis Diseases 0.000 claims description 4
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 4
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• 239000010949 copper Substances 0.000 claims description 4
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 4
• 208000003401 eosinophilic granuloma Diseases 0.000 claims description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
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• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
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• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
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