PT2066628E - 2-fenil-indoles como antagonistas do receptor da prostaglandina d2 - Google Patents

Info

Publication number

PT2066628E

PT2066628E PT07799729T PT07799729T PT2066628E PT 2066628 E PT2066628 E PT 2066628E PT 07799729 T PT07799729 T PT 07799729T PT 07799729 T PT07799729 T PT 07799729T PT 2066628 E PT2066628 E PT 2066628E

Authority

PT

Portugal

Prior art keywords

chloro

phenyl

indol

pharmaceutically acceptable

quot

Prior art date

2006-07-25

Links

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• 102000009389 Prostaglandin D receptors Human genes 0.000 title description 7
• 108050000258 Prostaglandin D receptors Proteins 0.000 title description 7
• 229940044551 receptor antagonist Drugs 0.000 title description 5
• 239000002464 receptor antagonist Substances 0.000 title description 5
• KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical class N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 title description 3
• -1 2-hydroxy, 2-hydroxy, Dichloro-benzyl Chemical group 0.000 claims description 121
• 150000001875 compounds Chemical class 0.000 claims description 112
• 150000003839 salts Chemical class 0.000 claims description 88
• 229940002612 prodrug Drugs 0.000 claims description 53
• 239000000651 prodrug Substances 0.000 claims description 53
• 239000012453 solvate Substances 0.000 claims description 45
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 34
• 150000002148 esters Chemical class 0.000 claims description 31
• 238000011282 treatment Methods 0.000 claims description 20
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• 208000006673 asthma Diseases 0.000 claims description 14
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• 239000001257 hydrogen Substances 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 12
• 208000002205 allergic conjunctivitis Diseases 0.000 claims description 12
• 208000024998 atopic conjunctivitis Diseases 0.000 claims description 12
• 201000010099 disease Diseases 0.000 claims description 12
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• 201000010105 allergic rhinitis Diseases 0.000 claims description 11
• 208000026935 allergic disease Diseases 0.000 claims description 10
• 208000010668 atopic eczema Diseases 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 8
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 7
• 208000003251 Pruritus Diseases 0.000 claims description 7
• 239000005557 antagonist Substances 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 7
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• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• 150000002431 hydrogen Chemical class 0.000 claims description 6
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• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 5
• 125000000286 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 5
• YZHLQIDOXFFHIC-UHFFFAOYSA-N 2-[2-[3-(cyclohexylsulfamoyl)-4-ethylphenyl]-1h-indol-3-yl]acetic acid Chemical compound CCC1=CC=C(C2=C(C3=CC=CC=C3N2)CC(O)=O)C=C1S(=O)(=O)NC1CCCCC1 YZHLQIDOXFFHIC-UHFFFAOYSA-N 0.000 claims description 4
• ACORQNNZIIDWOY-UHFFFAOYSA-N 2-[2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-1h-indol-3-yl]propanoic acid Chemical compound N1C2=CC=CC=C2C(C(C(O)=O)C)=C1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 ACORQNNZIIDWOY-UHFFFAOYSA-N 0.000 claims description 4
• 125000000940 2-methoxyphenyl ethyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
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• SPDHCHUIPQCJIT-UHFFFAOYSA-N 2-[2-[4-chloro-3-[(3-chlorophenyl)methylsulfonyl]phenyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=CC=C2C(CC(=O)O)=C1C(C=1)=CC=C(Cl)C=1S(=O)(=O)CC1=CC=CC(Cl)=C1 SPDHCHUIPQCJIT-UHFFFAOYSA-N 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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• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 3
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• JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 claims description 3
• 208000008423 pleurisy Diseases 0.000 claims description 3
• LAQBCLQGRLKEME-UHFFFAOYSA-M potassium 2-[4-chloro-2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-1H-indol-3-yl]acetate Chemical compound [K+].N1C2=CC=CC(Cl)=C2C(CC(=O)[O-])=C1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 LAQBCLQGRLKEME-UHFFFAOYSA-M 0.000 claims description 3
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• XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims description 2
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