JP2008528606A5 - - Google Patents
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- JP2008528606A5 JP2008528606A5 JP2007553221A JP2007553221A JP2008528606A5 JP 2008528606 A5 JP2008528606 A5 JP 2008528606A5 JP 2007553221 A JP2007553221 A JP 2007553221A JP 2007553221 A JP2007553221 A JP 2007553221A JP 2008528606 A5 JP2008528606 A5 JP 2008528606A5
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- JP
- Japan
- Prior art keywords
- pharmaceutically acceptable
- solvate
- acceptable salt
- prodrug
- alkyl
- 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.)
- Pending
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- 239000012453 solvate Substances 0.000 claims 119
- 150000003839 salts Chemical class 0.000 claims 110
- 229940002612 prodrug Drugs 0.000 claims 102
- 239000000651 prodrug Substances 0.000 claims 102
- 125000000217 alkyl group Chemical group 0.000 claims 84
- 229910052739 hydrogen Inorganic materials 0.000 claims 75
- 239000001257 hydrogen Substances 0.000 claims 75
- 150000001875 compounds Chemical class 0.000 claims 54
- 150000002431 hydrogen Chemical class 0.000 claims 51
- 125000003545 alkoxy group Chemical group 0.000 claims 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 26
- -1 heterocyclenyl Chemical group 0.000 claims 26
- 125000005843 halogen group Chemical group 0.000 claims 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims 22
- 125000003118 aryl group Chemical group 0.000 claims 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 20
- 125000000304 alkynyl group Chemical group 0.000 claims 19
- 125000003342 alkenyl 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 16
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 239000002253 acid Substances 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
- 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
- 239000003814 drug Substances 0.000 claims 11
- 150000004677 hydrates Chemical class 0.000 claims 11
- 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
- 125000004438 haloalkoxy group Chemical group 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 8
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000001309 chloro group Chemical group Cl* 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
- 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 4
- RWCJSIMCWSEALS-UHFFFAOYSA-N C=C.C1CCCCC1.C=C1CCCCC1 Chemical group C=C.C1CCCCC1.C=C1CCCCC1 RWCJSIMCWSEALS-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
- WCCDYNCDGZUTMV-UHFFFAOYSA-N cycloheptane methylidenecyclohexane Chemical compound C=C1CCCCC1.C1CCCCCC1 WCCDYNCDGZUTMV-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
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 3
- 206010061218 Inflammation Diseases 0.000 claims 3
- 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
- 125000000392 cycloalkenyl group Chemical group 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
- 230000004054 inflammatory process Effects 0.000 claims 3
- 125000003367 polycyclic group Chemical group 0.000 claims 3
- 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 2
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 2
- 206010002199 Anaphylactic shock Diseases 0.000 claims 2
- 206010006482 Bronchospasm Diseases 0.000 claims 2
- 229940124003 CRTH2 antagonist Drugs 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
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 2
- 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 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 206010039085 Rhinitis allergic 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
- 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
- 239000005557 antagonist Substances 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
- 229940125388 beta agonist Drugs 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 230000007885 bronchoconstriction Effects 0.000 claims 2
- 230000020411 cell activation Effects 0.000 claims 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims 2
- 125000005215 cycloalkylheteroaryl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims 2
- 125000005292 haloalkynyloxy 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
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- 230000007803 itching Effects 0.000 claims 2
- 239000003199 leukotriene receptor blocking agent Substances 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
- 208000008423 pleurisy Diseases 0.000 claims 2
- 229950004496 ramatroban Drugs 0.000 claims 2
- 206010039073 rheumatoid arthritis 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
- 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
- VWXVQSFJUQUYGN-UHFFFAOYSA-N 2-[2-[3-[cyclohexyl(methyl)sulfamoyl]phenyl]-1h-indol-3-yl]acetic acid Chemical compound C=1C=CC(C2=C(C3=CC=CC=C3N2)CC(O)=O)=CC=1S(=O)(=O)N(C)C1CCCCC1 VWXVQSFJUQUYGN-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
- 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 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
- 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
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- 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
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| EP2066628B1 (en) * | 2006-07-25 | 2010-10-20 | Sanofi-Aventis | 2-phenyl-indoles as prostaglandin d2 receptor antagonists |
| CN101500996B (zh) | 2006-08-07 | 2012-07-04 | 埃科特莱茵药品有限公司 | (3-胺基-1,2,3,4-四氢-9h-咔唑-9-基)-乙酸衍生物 |
| 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 |
| MX2012010820A (es) | 2010-03-22 | 2012-10-10 | Actelion Pharmaceuticals Ltd | Derivados de 3-(heteroaril-amino)-1, 2, 3, 4-tetrahidro-9h-carbazo l y sus uso como moduladores del receptor de prostaglandina d2. |
| WO2012046653A1 (ja) * | 2010-10-06 | 2012-04-12 | 株式会社クレハ | アミン系化合物とその用途 |
| WO2012140612A1 (en) | 2011-04-14 | 2012-10-18 | Actelion Pharmaceuticals Ltd | 7-(heteroaryl-amino)-6,7,8,9-tetrahydropyrido[1,2-a]indol acetic acid derivatives and their use as prostaglandin d2 receptor modulators |
| EP2548863A1 (en) * | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists. |
| AR088204A1 (es) * | 2011-09-29 | 2014-05-14 | Shionogi & Co | Medicamentos para el tratamiento de la rinitis alergica que comprenden un antagonista de pgd2 y un antagonista de histamina |
| US9255090B2 (en) | 2011-12-21 | 2016-02-09 | Actelion Pharmaceuticals Ltd. | Heterocyclyl derivatives and their use as prostaglandin D2 receptor modulators |
| 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 |
| UA117780C2 (uk) | 2014-03-17 | 2018-09-25 | Ідорсія Фармасьютікалз Лтд | Похідні азаіндолоцтової кислоти та їх застосування як модуляторів рецепторів простагландину d2 |
| RU2016140708A (ru) | 2014-03-18 | 2018-04-18 | Идорсиа Фармасьютиклз Лтд | Производные азаиндол уксусной кислоты и их применение в качестве модуляторов рецептора простагландина d2 |
| UA123156C2 (uk) | 2015-09-15 | 2021-02-24 | Ідорсія Фармасьютікалз Лтд | КРИСТАЛІЧНА ФОРМА (S)-2-(8-((5-ХЛОРПІРИМІДИН-2-ІЛ)(МЕТИЛ)АМІНО)-2-ФТОР-6,7,8,9-ТЕТРАГІДРО-5H-ПІРИДО[3,2-b]ІНДОЛ-5-ІЛ)ОЦТОВОЇ КИСЛОТИ, ЇЇ ЗАСТОСУВАННЯ ТА ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ, ЩО ЇЇ МІСТИТЬ |
| US20200264188A1 (en) | 2017-09-13 | 2020-08-20 | Progenity, Inc. | Preeclampsia biomarkers and related systems and methods |
| WO2019166629A1 (en) | 2018-03-02 | 2019-09-06 | Inflazome Limited | Novel compounds |
| 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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| KR950701317A (ko) * | 1992-05-08 | 1995-03-23 | 오오쓰까 아끼히꼬 | 인돌 유도체(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 |
| JPWO2004078719A1 (ja) * | 2003-03-06 | 2006-06-08 | 小野薬品工業株式会社 | インドール誘導体化合物およびその化合物を有効成分とする薬剤 |
| SE0301569D0 (sv) * | 2003-05-27 | 2003-05-27 | Astrazeneca Ab | Novel compounds |
| SE0303180D0 (sv) * | 2003-11-26 | 2003-11-26 | Astrazeneca Ab | Novel compounds |
| EA200700243A1 (ru) * | 2004-07-14 | 2007-08-31 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способы лечения гепатита с |
| US7868037B2 (en) * | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
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