RU2007132166A - 2-фенил-индолы как антагонисты рецепторов простагландина d2 - Google Patents
2-фенил-индолы как антагонисты рецепторов простагландина d2 Download PDFInfo
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- RU2007132166A RU2007132166A RU2007132166/04A RU2007132166A RU2007132166A RU 2007132166 A RU2007132166 A RU 2007132166A RU 2007132166/04 A RU2007132166/04 A RU 2007132166/04A RU 2007132166 A RU2007132166 A RU 2007132166A RU 2007132166 A RU2007132166 A RU 2007132166A
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- RU
- Russia
- Prior art keywords
- pharmaceutically acceptable
- hydrate
- solvate
- alkyl
- prodrug
- Prior art date
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- 239000005557 antagonist Substances 0.000 title claims 2
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical class N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 title 1
- 102000009389 Prostaglandin D receptors Human genes 0.000 title 1
- 108050000258 Prostaglandin D receptors Proteins 0.000 title 1
- 229940002612 prodrug Drugs 0.000 claims 105
- 239000000651 prodrug Substances 0.000 claims 105
- 150000003839 salts Chemical class 0.000 claims 105
- 239000012453 solvate Substances 0.000 claims 101
- 125000000217 alkyl group Chemical group 0.000 claims 81
- 229910052739 hydrogen Inorganic materials 0.000 claims 75
- 239000001257 hydrogen Substances 0.000 claims 75
- 150000001875 compounds Chemical class 0.000 claims 59
- 150000002431 hydrogen Chemical class 0.000 claims 51
- 125000003545 alkoxy group Chemical group 0.000 claims 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 24
- 229910052736 halogen Inorganic materials 0.000 claims 24
- 150000002367 halogens Chemical class 0.000 claims 24
- -1 cyano, carboxy Chemical group 0.000 claims 22
- 125000003118 aryl group Chemical group 0.000 claims 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims 21
- 125000003342 alkenyl group Chemical group 0.000 claims 19
- 125000000304 alkynyl group Chemical group 0.000 claims 18
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 17
- 125000001188 haloalkyl group Chemical group 0.000 claims 15
- 230000002378 acidificating effect Effects 0.000 claims 12
- 125000002252 acyl group Chemical group 0.000 claims 12
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims 11
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims 10
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 10
- 229910052801 chlorine Inorganic materials 0.000 claims 10
- 239000000460 chlorine Substances 0.000 claims 10
- 125000004438 haloalkoxy group Chemical group 0.000 claims 10
- 238000000034 method Methods 0.000 claims 9
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 8
- 125000003282 alkyl amino group Chemical group 0.000 claims 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims 4
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims 4
- 125000001769 aryl amino group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- RLPXAKVDWHODPX-UHFFFAOYSA-N cyclohexane;ethene Chemical group C=C.C1CCCCC1 RLPXAKVDWHODPX-UHFFFAOYSA-N 0.000 claims 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 4
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 4
- 208000003251 Pruritus Diseases 0.000 claims 3
- 125000003435 aroyl group Chemical group 0.000 claims 3
- 201000008937 atopic dermatitis Diseases 0.000 claims 3
- 208000010668 atopic eczema Diseases 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims 3
- 125000000232 haloalkynyl group Chemical group 0.000 claims 3
- 125000005241 heteroarylamino group Chemical group 0.000 claims 3
- 230000007803 itching Effects 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- NNRBHTRLBOGMGJ-UHFFFAOYSA-N 2-[2-[4-chloro-3-(cyclohexylmethylsulfamoyl)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)NCC1CCCCC1 NNRBHTRLBOGMGJ-UHFFFAOYSA-N 0.000 claims 2
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims 2
- 206010002199 Anaphylactic shock Diseases 0.000 claims 2
- 206010006482 Bronchospasm Diseases 0.000 claims 2
- 206010008190 Cerebrovascular accident Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 2
- 201000004624 Dermatitis Diseases 0.000 claims 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 201000008736 Systemic mastocytosis Diseases 0.000 claims 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 208000024780 Urticaria Diseases 0.000 claims 2
- 230000004913 activation Effects 0.000 claims 2
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 208000003455 anaphylaxis Diseases 0.000 claims 2
- 230000001387 anti-histamine Effects 0.000 claims 2
- 239000000739 antihistaminic agent Substances 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 2
- 239000002876 beta blocker Substances 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 230000007885 bronchoconstriction Effects 0.000 claims 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims 2
- 125000005215 cycloalkylheteroaryl group Chemical group 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims 2
- 125000005292 haloalkynyloxy group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims 2
- 210000003630 histaminocyte Anatomy 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 208000037921 secondary disease Diseases 0.000 claims 2
- 230000009885 systemic effect Effects 0.000 claims 2
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims 1
- IROIAUAZJCXWMK-VWLOTQADSA-N (2s)-2-[[2-[2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-1h-indol-3-yl]acetyl]amino]-3-methylbutanoic acid Chemical compound N1C2=CC=CC=C2C(CC(=O)N[C@@H](C(C)C)C(O)=O)=C1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 IROIAUAZJCXWMK-VWLOTQADSA-N 0.000 claims 1
- WBOMXMVCPVYAJI-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-[2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-1h-indol-3-yl]acetate Chemical compound N1C2=CC=CC=C2C(CC(=O)OCCN(C)C)=C1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 WBOMXMVCPVYAJI-UHFFFAOYSA-N 0.000 claims 1
- TVJUMPPKCLEYHM-UHFFFAOYSA-N 2-[1-benzyl-2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]indol-3-yl]acetic acid Chemical compound C=1C=CC=CC=1CN1C2=CC=CC=C2C(CC(=O)O)=C1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 TVJUMPPKCLEYHM-UHFFFAOYSA-N 0.000 claims 1
- XHZNQCGZPFWXID-UHFFFAOYSA-N 2-[2-(4-chloro-3-piperidin-1-ylsulfonylphenyl)-1-methylindol-3-yl]acetic acid Chemical compound OC(=O)CC=1C2=CC=CC=C2N(C)C=1C(C=1)=CC=C(Cl)C=1S(=O)(=O)N1CCCCC1 XHZNQCGZPFWXID-UHFFFAOYSA-N 0.000 claims 1
- IDJQUDJODCXEQY-UHFFFAOYSA-N 2-[2-(4-chloro-3-piperidin-1-ylsulfonylphenyl)-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)N1CCCCC1 IDJQUDJODCXEQY-UHFFFAOYSA-N 0.000 claims 1
- CXCCZEPELUUFDD-UHFFFAOYSA-N 2-[2-(4-chloro-3-sulfamoylphenyl)-1h-indol-3-yl]acetic acid Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C2=C(C3=CC=CC=C3N2)CC(O)=O)=C1 CXCCZEPELUUFDD-UHFFFAOYSA-N 0.000 claims 1
- UYFNPUBOMDLHCV-UHFFFAOYSA-N 2-[2-[3-(1-adamantylmethylsulfamoyl)-4-chlorophenyl]-1h-indol-3-yl]acetic acid Chemical compound C1C(C2)CC(C3)CC2CC13CNS(=O)(=O)C1=CC(C2=C(C3=CC=CC=C3N2)CC(=O)O)=CC=C1Cl UYFNPUBOMDLHCV-UHFFFAOYSA-N 0.000 claims 1
- UICZFBZASXWXNF-UHFFFAOYSA-N 2-[2-[3-(3-bicyclo[2.2.1]heptanylsulfamoyl)-4-chlorophenyl]-1h-indol-3-yl]acetic acid Chemical compound C1=C(Cl)C(S(=O)(=O)NC2C3CCC(C3)C2)=CC(C2=C(C3=CC=CC=C3N2)CC(=O)O)=C1 UICZFBZASXWXNF-UHFFFAOYSA-N 0.000 claims 1
- RVWOCMSWEFASHI-UHFFFAOYSA-N 2-[2-[3-(benzenesulfonamido)-4-chlorophenyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=CC=C2C(CC(=O)O)=C1C(C=1)=CC=C(Cl)C=1NS(=O)(=O)C1=CC=CC=C1 RVWOCMSWEFASHI-UHFFFAOYSA-N 0.000 claims 1
- KZCCIJZBJRBWMG-UHFFFAOYSA-N 2-[2-[3-(benzylsulfamoyl)-4-chlorophenyl]-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)NCC1=CC=CC=C1 KZCCIJZBJRBWMG-UHFFFAOYSA-N 0.000 claims 1
- LSTFMDGUHBPESB-UHFFFAOYSA-N 2-[2-[3-(cyclohexylsulfamoyl)-4-methoxyphenyl]-1h-indol-3-yl]acetic acid Chemical compound COC1=CC=C(C2=C(C3=CC=CC=C3N2)CC(O)=O)C=C1S(=O)(=O)NC1CCCCC1 LSTFMDGUHBPESB-UHFFFAOYSA-N 0.000 claims 1
- RVSDWKUYNSUGQC-UHFFFAOYSA-N 2-[2-[3-(cyclohexylsulfamoyl)-4-methylphenyl]-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=C(C2=C(C3=CC=CC=C3N2)CC(O)=O)C=C1S(=O)(=O)NC1CCCCC1 RVSDWKUYNSUGQC-UHFFFAOYSA-N 0.000 claims 1
- VKMOKQSYAVVHEY-UHFFFAOYSA-N 2-[2-[3-(cyclohexylsulfamoyl)-5-(trifluoromethyl)phenyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=CC=C2C(CC(=O)O)=C1C(C=1)=CC(C(F)(F)F)=CC=1S(=O)(=O)NC1CCCCC1 VKMOKQSYAVVHEY-UHFFFAOYSA-N 0.000 claims 1
- JDEGCYUKNLKEKH-UHFFFAOYSA-N 2-[2-[3-(cyclohexylsulfamoyl)phenyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=CC=C2C(CC(=O)O)=C1C(C=1)=CC=CC=1S(=O)(=O)NC1CCCCC1 JDEGCYUKNLKEKH-UHFFFAOYSA-N 0.000 claims 1
- JXVFLISNIFHMNZ-UHFFFAOYSA-N 2-[2-[3-(cyclohexylsulfamoyl)phenyl]-1h-indol-3-yl]propanoic acid Chemical compound N1C2=CC=CC=C2C(C(C(O)=O)C)=C1C(C=1)=CC=CC=1S(=O)(=O)NC1CCCCC1 JXVFLISNIFHMNZ-UHFFFAOYSA-N 0.000 claims 1
- ODQRPEPELMKXOZ-UHFFFAOYSA-N 2-[2-[3-chloro-4-(cyclohexylsulfamoyl)phenyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=CC=C2C(CC(=O)O)=C1C(C=C1Cl)=CC=C1S(=O)(=O)NC1CCCCC1 ODQRPEPELMKXOZ-UHFFFAOYSA-N 0.000 claims 1
- YLTZBNUVCVPBCN-UHFFFAOYSA-N 2-[2-[4-(cyclohexylsulfamoyl)phenyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=CC=C2C(CC(=O)O)=C1C(C=C1)=CC=C1S(=O)(=O)NC1CCCCC1 YLTZBNUVCVPBCN-UHFFFAOYSA-N 0.000 claims 1
- KLPODWRSUGWCHI-UHFFFAOYSA-N 2-[2-[4-chloro-3-(2,2-dimethylpropylsulfamoyl)phenyl]-1h-indol-3-yl]acetic acid Chemical compound C1=C(Cl)C(S(=O)(=O)NCC(C)(C)C)=CC(C2=C(C3=CC=CC=C3N2)CC(O)=O)=C1 KLPODWRSUGWCHI-UHFFFAOYSA-N 0.000 claims 1
- NVNPJJOLMKGLRV-UHFFFAOYSA-N 2-[2-[4-chloro-3-(2,3-dihydro-1h-inden-2-ylsulfamoyl)phenyl]-1h-indol-3-yl]acetic acid Chemical compound C1C2=CC=CC=C2CC1NS(=O)(=O)C1=CC(C2=C(C3=CC=CC=C3N2)CC(=O)O)=CC=C1Cl NVNPJJOLMKGLRV-UHFFFAOYSA-N 0.000 claims 1
- HYGSXQRMICIGKD-UHFFFAOYSA-N 2-[2-[4-chloro-3-(2-cyclohexylethylsulfamoyl)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)NCCC1CCCCC1 HYGSXQRMICIGKD-UHFFFAOYSA-N 0.000 claims 1
- TXOMVBOEEPGYOD-UHFFFAOYSA-N 2-[2-[4-chloro-3-(cycloheptylmethylsulfamoyl)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)NCC1CCCCCC1 TXOMVBOEEPGYOD-UHFFFAOYSA-N 0.000 claims 1
- RTJZYWCMRYZVJT-UHFFFAOYSA-N 2-[2-[4-chloro-3-(cycloheptylsulfamoyl)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)NC1CCCCCC1 RTJZYWCMRYZVJT-UHFFFAOYSA-N 0.000 claims 1
- SJUVHMUFFWQPIY-UHFFFAOYSA-N 2-[2-[4-chloro-3-(cyclohexanecarbonylamino)phenyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=CC=C2C(CC(=O)O)=C1C(C=1)=CC=C(Cl)C=1NC(=O)C1CCCCC1 SJUVHMUFFWQPIY-UHFFFAOYSA-N 0.000 claims 1
- MVAZMSVBDYAXBI-UHFFFAOYSA-N 2-[2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-1-methylindol-3-yl]acetamide Chemical compound NC(=O)CC=1C2=CC=CC=C2N(C)C=1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 MVAZMSVBDYAXBI-UHFFFAOYSA-N 0.000 claims 1
- XLQRWCMKWOKBRB-UHFFFAOYSA-N 2-[2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-1-methylindol-3-yl]acetic acid Chemical compound OC(=O)CC=1C2=CC=CC=C2N(C)C=1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 XLQRWCMKWOKBRB-UHFFFAOYSA-N 0.000 claims 1
- RNNRQNNAMZCEHV-UHFFFAOYSA-N 2-[2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-1h-indol-3-yl]acetamide Chemical compound N1C2=CC=CC=C2C(CC(=O)N)=C1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 RNNRQNNAMZCEHV-UHFFFAOYSA-N 0.000 claims 1
- KIGUGIFQHCUKBU-UHFFFAOYSA-N 2-[2-[4-chloro-3-(cyclohexylsulfamoyl)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)NC1CCCCC1 KIGUGIFQHCUKBU-UHFFFAOYSA-N 0.000 claims 1
- UKCNHXSLUKIVLK-UHFFFAOYSA-N 2-[2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-5-(trifluoromethoxy)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=C(OC(F)(F)F)C=C2C(CC(=O)O)=C1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 UKCNHXSLUKIVLK-UHFFFAOYSA-N 0.000 claims 1
- NRCCDAGERPEEML-UHFFFAOYSA-N 2-[2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-5-hydroxy-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=C(O)C=C2C(CC(=O)O)=C1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 NRCCDAGERPEEML-UHFFFAOYSA-N 0.000 claims 1
- ZVTVOTKPLIIPCV-UHFFFAOYSA-N 2-[2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-5-methoxy-1h-indol-3-yl]acetic acid Chemical compound OC(=O)CC=1C2=CC(OC)=CC=C2NC=1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 ZVTVOTKPLIIPCV-UHFFFAOYSA-N 0.000 claims 1
- AHKWGWWFOOHMBE-UHFFFAOYSA-N 2-[2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-5-methyl-1h-indol-3-yl]acetic acid Chemical compound OC(=O)CC=1C2=CC(C)=CC=C2NC=1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 AHKWGWWFOOHMBE-UHFFFAOYSA-N 0.000 claims 1
- JYQQECGODKQQRF-UHFFFAOYSA-N 2-[2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-5-propan-2-yl-1h-indol-3-yl]acetic acid Chemical compound OC(=O)CC=1C2=CC(C(C)C)=CC=C2NC=1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 JYQQECGODKQQRF-UHFFFAOYSA-N 0.000 claims 1
- NQEPMFVZEBPBSE-UHFFFAOYSA-N 2-[2-[4-chloro-3-(cyclopentylsulfamoyl)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)NC1CCCC1 NQEPMFVZEBPBSE-UHFFFAOYSA-N 0.000 claims 1
- XWYJQVOFBMQLQF-UHFFFAOYSA-N 2-[2-[4-chloro-3-(hexylsulfamoyl)phenyl]-1h-indol-3-yl]acetic acid Chemical compound C1=C(Cl)C(S(=O)(=O)NCCCCCC)=CC(C2=C(C3=CC=CC=C3N2)CC(O)=O)=C1 XWYJQVOFBMQLQF-UHFFFAOYSA-N 0.000 claims 1
- KYIINTGTZURUIV-UHFFFAOYSA-N 2-[2-[4-chloro-3-(methylsulfamoyl)phenyl]-1h-indol-3-yl]acetic acid Chemical compound C1=C(Cl)C(S(=O)(=O)NC)=CC(C2=C(C3=CC=CC=C3N2)CC(O)=O)=C1 KYIINTGTZURUIV-UHFFFAOYSA-N 0.000 claims 1
- ZTDJOICEMVJPEP-UHFFFAOYSA-N 2-[2-[4-chloro-3-(oxan-4-ylsulfamoyl)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)NC1CCOCC1 ZTDJOICEMVJPEP-UHFFFAOYSA-N 0.000 claims 1
- YKFGWAAUPPWUQQ-UHFFFAOYSA-N 2-[2-[4-chloro-3-(pentan-3-ylsulfamoyl)phenyl]-1h-indol-3-yl]acetic acid Chemical compound C1=C(Cl)C(S(=O)(=O)NC(CC)CC)=CC(C2=C(C3=CC=CC=C3N2)CC(O)=O)=C1 YKFGWAAUPPWUQQ-UHFFFAOYSA-N 0.000 claims 1
- NXXKXKSPXZGLAG-UHFFFAOYSA-N 2-[2-[4-chloro-3-(phenylsulfamoyl)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)NC1=CC=CC=C1 NXXKXKSPXZGLAG-UHFFFAOYSA-N 0.000 claims 1
- XUHOVEDHEDNXIE-UHFFFAOYSA-N 2-[2-[4-chloro-3-(propan-2-ylsulfamoyl)phenyl]-1h-indol-3-yl]acetic acid Chemical compound C1=C(Cl)C(S(=O)(=O)NC(C)C)=CC(C2=C(C3=CC=CC=C3N2)CC(O)=O)=C1 XUHOVEDHEDNXIE-UHFFFAOYSA-N 0.000 claims 1
- YFITVMGBBFYHQK-UHFFFAOYSA-N 2-[2-[4-chloro-3-[[4-(trifluoromethyl)phenyl]methylsulfamoyl]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)NCC1=CC=C(C(F)(F)F)C=C1 YFITVMGBBFYHQK-UHFFFAOYSA-N 0.000 claims 1
- HFYOKXFTBGDLBE-UHFFFAOYSA-N 2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound N1C2=CC=CC=C2C(C(=O)O)=C1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 HFYOKXFTBGDLBE-UHFFFAOYSA-N 0.000 claims 1
- JEBAWCRMSLGTPK-UHFFFAOYSA-N 2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-1h-indole-6-carboxylic acid Chemical compound N1C2=CC(C(=O)O)=CC=C2C=C1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 JEBAWCRMSLGTPK-UHFFFAOYSA-N 0.000 claims 1
- XXYSFNXENYRKOH-UHFFFAOYSA-N 2-[5-chloro-2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)O)=C1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 XXYSFNXENYRKOH-UHFFFAOYSA-N 0.000 claims 1
- MACBWEBTXYKHKB-UHFFFAOYSA-N 2-[5-tert-butyl-2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-1h-indol-3-yl]acetic acid Chemical compound OC(=O)CC=1C2=CC(C(C)(C)C)=CC=C2NC=1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 MACBWEBTXYKHKB-UHFFFAOYSA-N 0.000 claims 1
- SAPPIBAOVDXZOO-UHFFFAOYSA-N 2-[6-chloro-2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 SAPPIBAOVDXZOO-UHFFFAOYSA-N 0.000 claims 1
- WDEKCKWZKZVGDZ-UHFFFAOYSA-N 2-chloro-n-cyclohexyl-5-[3-(2-hydroxyethyl)-1-methylindol-2-yl]benzenesulfonamide Chemical compound OCCC=1C2=CC=CC=C2N(C)C=1C(C=1)=CC=C(Cl)C=1S(=O)(=O)NC1CCCCC1 WDEKCKWZKZVGDZ-UHFFFAOYSA-N 0.000 claims 1
- LSUZHWAKISELOL-UHFFFAOYSA-N 2-chloro-n-cyclohexyl-5-[3-[(2-oxo-3h-1,3,4-oxadiazol-5-yl)methyl]-1h-indol-2-yl]benzenesulfonamide Chemical compound ClC1=CC=C(C2=C(C3=CC=CC=C3N2)CC=2OC(=O)NN=2)C=C1S(=O)(=O)NC1CCCCC1 LSUZHWAKISELOL-UHFFFAOYSA-N 0.000 claims 1
- 229940124003 CRTH2 antagonist Drugs 0.000 claims 1
- 208000002177 Cataract Diseases 0.000 claims 1
- 206010012434 Dermatitis allergic Diseases 0.000 claims 1
- 208000004262 Food Hypersensitivity Diseases 0.000 claims 1
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical group CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 claims 1
- 206010035664 Pneumonia Diseases 0.000 claims 1
- LDXDSHIEDAPSSA-OAHLLOKOSA-N Ramatroban Chemical group N([C@@H]1CCC=2N(C3=CC=CC=C3C=2C1)CCC(=O)O)S(=O)(=O)C1=CC=C(F)C=C1 LDXDSHIEDAPSSA-OAHLLOKOSA-N 0.000 claims 1
- 206010038848 Retinal detachment Diseases 0.000 claims 1
- YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical group CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 125000005157 alkyl carboxy group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229960003592 fexofenadine Drugs 0.000 claims 1
- 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 1
- 235000020932 food allergy Nutrition 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims 1
- 150000002617 leukotrienes Chemical class 0.000 claims 1
- 229960003088 loratadine Drugs 0.000 claims 1
- 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 1
- SIPSZKYFKUQDHU-UHFFFAOYSA-N methyl 2-(4-acetylphenyl)-1h-indole-3-carboxylate Chemical compound N1C2=CC=CC=C2C(C(=O)OC)=C1C1=CC=C(C(C)=O)C=C1 SIPSZKYFKUQDHU-UHFFFAOYSA-N 0.000 claims 1
- QMCBHLLJXYUPLP-UHFFFAOYSA-N methyl 2-[2-[3-(cyclohexylsulfamoyl)-5-(trifluoromethyl)phenyl]-1h-indol-3-yl]acetate Chemical compound N1C2=CC=CC=C2C(CC(=O)OC)=C1C(C=1)=CC(C(F)(F)F)=CC=1S(=O)(=O)NC1CCCCC1 QMCBHLLJXYUPLP-UHFFFAOYSA-N 0.000 claims 1
- 229960005127 montelukast Drugs 0.000 claims 1
- ZCHDPGBWXUORMD-UHFFFAOYSA-N n-(benzenesulfonyl)-2-[2-[4-chloro-3-(cyclohexylsulfamoyl)phenyl]-1h-indol-3-yl]acetamide Chemical compound ClC1=CC=C(C2=C(C3=CC=CC=C3N2)CC(=O)NS(=O)(=O)C=2C=CC=CC=2)C=C1S(=O)(=O)NC1CCCCC1 ZCHDPGBWXUORMD-UHFFFAOYSA-N 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 208000008423 pleurisy Diseases 0.000 claims 1
- 229950004496 ramatroban Drugs 0.000 claims 1
- 230000004264 retinal detachment Effects 0.000 claims 1
- 229960002052 salbutamol Drugs 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 208000022925 sleep disturbance Diseases 0.000 claims 1
- 229960000195 terbutaline Drugs 0.000 claims 1
- 229960004764 zafirlukast Drugs 0.000 claims 1
Classifications
-
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A61P11/08—Bronchodilators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/12—Ophthalmic agents for cataracts
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/22—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an aralkyl radical attached to the ring nitrogen atom
-
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Dermatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
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- Communicable Diseases (AREA)
- Anesthesiology (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
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| US64730705P | 2005-01-26 | 2005-01-26 | |
| US60/647,307 | 2005-01-26 |
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| RU2007132166A true RU2007132166A (ru) | 2009-03-10 |
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| RU2007132166/04A RU2007132166A (ru) | 2005-01-26 | 2006-01-25 | 2-фенил-индолы как антагонисты рецепторов простагландина d2 |
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| PE (1) | PE20060878A1 (enExample) |
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| AU2007276885A1 (en) * | 2006-07-25 | 2008-01-31 | Sanofi-Aventis | 2-phenyl-indoles as prostaglandin D2 receptor antagonists |
| CA2658986C (en) | 2006-08-07 | 2014-11-25 | Actelion Pharmaceuticals Ltd | (3-amino-1,2,3,4-tetrahydro-9h-carbazol-9-yl)-acetic acid derivatives |
| WO2008061006A1 (en) * | 2006-11-10 | 2008-05-22 | Wyeth | Substituted indan-2-yl, tetrahydronaphthalen-2-yl, or dihydr0-2h-chr0men-3-yl arylsulfonamides and methods of their use |
| WO2009061730A2 (en) * | 2007-11-05 | 2009-05-14 | Array Biopharma Inc. | 4-heteroaryl-substituted phenoxyphenylacetic acid |
| BR112012024114B1 (pt) | 2010-03-22 | 2021-02-09 | Idorsia Pharmaceuticals Ltd | Compostos derivados de 3-(heteroarilamino)-1,2,3,4-tetrahidro-9h-carbazol, uso dos mesmos, e, composição farmacêutica |
| EP2626349A4 (en) * | 2010-10-06 | 2014-03-12 | Kureha Corp | AMINE CONNECTION AND ITS USE |
| JP5964945B2 (ja) | 2011-04-14 | 2016-08-03 | アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | ７−（ヘテロアリ−ル−アミノ）−６，７，８，９−テトラヒドロピリド［１，２−ａ］インド−ル酢酸誘導体及びプロスタグランジンＤ２受容体調節剤としてのそれらの使用 |
| EP2548863A1 (en) * | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists. |
| JP5362151B2 (ja) * | 2011-09-29 | 2013-12-11 | 塩野義製薬株式会社 | Ｐｇｄ２拮抗剤及びヒスタミン拮抗剤からなるアレルギー性鼻炎治療用医薬 |
| ES2624379T3 (es) | 2011-12-21 | 2017-07-14 | Idorsia Pharmaceuticals Ltd | Derivados de heterociclilo y su uso como moduladores del receptor de prostaglandina D2 |
| US9169270B2 (en) | 2012-07-05 | 2015-10-27 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin D2 receptor modulators |
| EP2912458B1 (en) | 2012-10-24 | 2018-07-18 | NYU Winthrop Hospital | Non-invasive biomarker to identify subjects at risk of preterm delivery |
| JP6168520B2 (ja) * | 2013-09-17 | 2017-07-26 | 国立大学法人 千葉大学 | インドール化合物、ｄｐプロスタノイド受容体アンタゴニスト、それを用いた薬剤、及びｄｐプロスタノイド受容体アンタゴニストの使用。 |
| JP2015089886A (ja) * | 2013-11-06 | 2015-05-11 | 国立大学法人名古屋大学 | 嵩高い置換基を有する化合物を用いた植物成長調整剤 |
| TWI649321B (zh) | 2014-03-17 | 2019-02-01 | 瑞士商愛杜西亞製藥有限公司 | 氮雜吲哚乙酸衍生物及彼等作為前列腺素ｄ２受體調節劑之用途 |
| WO2015140701A1 (en) | 2014-03-18 | 2015-09-24 | Actelion Pharmaceuticals Ltd | Azaindole acetic acid derivatives and their use as prostaglandin d2 receptor modulators |
| AU2016323262B2 (en) | 2015-09-15 | 2020-11-19 | Idorsia Pharmaceuticals Ltd | Crystalline forms |
| JP2020533595A (ja) | 2017-09-13 | 2020-11-19 | プロジェニティ， インコーポレイテッド | 子癇前症バイオマーカならびに関連するシステムおよび方法 |
| US12030879B2 (en) | 2018-03-02 | 2024-07-09 | Inflazome Limited | Sulfonyl acetamides as NLRP3 inhibitors |
| EP4070113A4 (en) | 2019-12-04 | 2023-12-20 | Biora Therapeutics, Inc. | ASSESSMENT OF PREECAMPSIA USING FREE AND DISSOCIATE PLACENTAL GROWTH FACTOR ASSAYS |
| CN113173877B (zh) * | 2020-10-30 | 2023-10-27 | 江西师范大学 | 吲哚乙酰基亚氨基砜系列化合物及其制备方法 |
| CN115925606B (zh) * | 2023-01-05 | 2023-10-13 | 宁夏医科大学 | 一种5-（3-（磺酰胺基）苯基）-1h-吡咯-2-羧酸衍生物及其制备方法和应用 |
| CN117599052A (zh) * | 2023-07-25 | 2024-02-27 | 温州医科大学附属眼视光医院 | Ptgds的抑制剂在制备治疗白内障药物上的应用 |
| US12220411B1 (en) | 2023-07-25 | 2025-02-11 | The Eye Hospital Of Wenzhou Medical University | Application of PTGDS inhibitor in preparation of drug for treating cataracts |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU665690B2 (en) * | 1992-05-08 | 1996-01-11 | Otsuka Pharmaceutical Factory, Inc. | Indole derivative |
| FR2751966B1 (fr) * | 1996-08-01 | 1998-10-30 | Union Pharma Scient Appl | Nouveaux derives 1,2-diarylindoles, leurs procedes de preparation, et leurs utilisations en therapeutique |
| US6500853B1 (en) * | 1998-02-28 | 2002-12-31 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
| DE10204462A1 (de) * | 2002-02-05 | 2003-08-07 | Boehringer Ingelheim Pharma | Verwendung von Tyrosinkinase-Inhibitoren zur Behandlung inflammatorischer Prozesse |
| JP2004024655A (ja) * | 2002-06-27 | 2004-01-29 | Aruze Corp | 遊技機 |
| EP1600440A1 (en) * | 2003-03-06 | 2005-11-30 | Ono Pharmaceutical Co., Ltd. | Indole derivative compounds and drugs containing the compounds as the active ingredient |
| SE0301569D0 (sv) * | 2003-05-27 | 2003-05-27 | Astrazeneca Ab | Novel compounds |
| SE0303180D0 (sv) * | 2003-11-26 | 2003-11-26 | Astrazeneca Ab | Novel compounds |
| JP2008506702A (ja) * | 2004-07-14 | 2008-03-06 | ピーティーシー セラピューティクス，インコーポレーテッド | Ｃ型肝炎を治療するための方法 |
| US7868037B2 (en) * | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
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2006
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- 2006-01-24 PE PE2006000105A patent/PE20060878A1/es not_active Application Discontinuation
- 2006-01-25 SG SG201000540-3A patent/SG158918A1/en unknown
- 2006-01-25 MX MX2007008277A patent/MX2007008277A/es not_active Application Discontinuation
- 2006-01-25 CA CA002595728A patent/CA2595728A1/en not_active Abandoned
- 2006-01-25 AU AU2006209213A patent/AU2006209213A1/en not_active Abandoned
- 2006-01-25 BR BRPI0607079-5A patent/BRPI0607079A2/pt not_active IP Right Cessation
- 2006-01-25 RU RU2007132166/04A patent/RU2007132166A/ru not_active Application Discontinuation
- 2006-01-25 EP EP06719551A patent/EP1844011A1/en not_active Withdrawn
- 2006-01-25 JP JP2007553221A patent/JP2008528606A/ja active Pending
- 2006-01-25 WO PCT/US2006/002736 patent/WO2006081343A1/en not_active Ceased
- 2006-01-25 AR ARP060100278A patent/AR054726A1/es not_active Application Discontinuation
- 2006-01-25 GT GT200600030A patent/GT200600030A/es unknown
- 2006-01-25 CN CNA2006800097886A patent/CN101146770A/zh active Pending
- 2006-01-25 KR KR1020077017292A patent/KR20070110277A/ko not_active Withdrawn
- 2006-01-26 UY UY29346A patent/UY29346A1/es unknown
- 2006-01-26 PA PA20068661201A patent/PA8661201A1/es unknown
- 2006-01-26 TW TW095102967A patent/TW200639151A/zh unknown
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2007
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- 2007-07-03 TN TNP2007000251A patent/TNSN07251A1/en unknown
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- 2007-07-24 IL IL184816A patent/IL184816A0/en unknown
- 2007-07-25 US US11/782,890 patent/US20070265278A1/en not_active Abandoned
- 2007-08-17 MA MA30150A patent/MA29259B1/fr unknown
- 2007-08-24 NO NO20074336A patent/NO20074336L/no not_active Application Discontinuation
Also Published As
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|---|---|
| BRPI0607079A2 (pt) | 2009-08-04 |
| CN101146770A (zh) | 2008-03-19 |
| WO2006081343A1 (en) | 2006-08-03 |
| EP1844011A1 (en) | 2007-10-17 |
| JP2008528606A (ja) | 2008-07-31 |
| MA29259B1 (fr) | 2008-02-01 |
| DOP2006000016A (es) | 2006-07-31 |
| US20070265278A1 (en) | 2007-11-15 |
| NO20074336L (no) | 2007-10-23 |
| MX2007008277A (es) | 2007-09-07 |
| ZA200705449B (en) | 2009-01-28 |
| CA2595728A1 (en) | 2006-08-03 |
| CR9214A (es) | 2007-11-23 |
| IL184816A0 (en) | 2007-12-03 |
| KR20070110277A (ko) | 2007-11-16 |
| AR054726A1 (es) | 2007-07-11 |
| SG158918A1 (en) | 2010-02-26 |
| TNSN07251A1 (en) | 2008-12-31 |
| AU2006209213A1 (en) | 2006-08-03 |
| TW200639151A (en) | 2006-11-16 |
| GT200600030A (es) | 2006-09-27 |
| UY29346A1 (es) | 2006-08-31 |
| PE20060878A1 (es) | 2006-10-18 |
| PA8661201A1 (es) | 2006-09-08 |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20100701 |