JP2011529049A5 - - Google Patents
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- Publication number
- JP2011529049A5 JP2011529049A5 JP2011520040A JP2011520040A JP2011529049A5 JP 2011529049 A5 JP2011529049 A5 JP 2011529049A5 JP 2011520040 A JP2011520040 A JP 2011520040A JP 2011520040 A JP2011520040 A JP 2011520040A JP 2011529049 A5 JP2011529049 A5 JP 2011529049A5
- Authority
- JP
- Japan
- Prior art keywords
- solvate
- hydrate
- compound
- trifluoromethyl
- tetrahydrocyclopenta
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 161
- 150000003839 salts Chemical class 0.000 claims description 146
- 239000012453 solvate Substances 0.000 claims description 143
- -1 chloro, cyano, cyclobutyl Chemical group 0.000 claims description 59
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 54
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 44
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 43
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 208000035475 disorder Diseases 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 claims description 20
- 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 150000003857 carboxamides Chemical class 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 15
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 14
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 150000004677 hydrates Chemical class 0.000 claims description 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 208000027866 inflammatory disease Diseases 0.000 claims description 9
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 208000015181 infectious disease Diseases 0.000 claims description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004512 1,2,3-thiadiazol-4-yl group Chemical group S1N=NC(=C1)* 0.000 claims description 7
- MVGWUTBTXDYMND-QGZVFWFLSA-N 2-[(3r)-7-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound C([C@@H]1CC(=O)O)CC(C2=C3)=C1NC2=CC=C3OCC(C=C1C(F)(F)F)=CC=C1C1CCCC1 MVGWUTBTXDYMND-QGZVFWFLSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- RYNLYBXICSFSBE-MRXNPFEDSA-N 2-[(3r)-7-[(3-cyano-4-propan-2-yloxyphenyl)methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1COC1=CC=C(NC2=C3CC[C@@H]2CC(O)=O)C3=C1 RYNLYBXICSFSBE-MRXNPFEDSA-N 0.000 claims description 5
- RYNLYBXICSFSBE-INIZCTEOSA-N 2-[(3s)-7-[(3-cyano-4-propan-2-yloxyphenyl)methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1COC1=CC=C(NC2=C3CC[C@H]2CC(O)=O)C3=C1 RYNLYBXICSFSBE-INIZCTEOSA-N 0.000 claims description 5
- MVGWUTBTXDYMND-KRWDZBQOSA-N 2-[(3s)-7-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound C([C@H]1CC(=O)O)CC(C2=C3)=C1NC2=CC=C3OCC(C=C1C(F)(F)F)=CC=C1C1CCCC1 MVGWUTBTXDYMND-KRWDZBQOSA-N 0.000 claims description 5
- MXDFMHPXBSLFHN-UHFFFAOYSA-N 2-[7-[(3-cyano-4-cyclohexylphenyl)methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC(C=C1C#N)=CC=C1C1CCCCC1 MXDFMHPXBSLFHN-UHFFFAOYSA-N 0.000 claims description 5
- FFNDSFPWGHUHMV-UHFFFAOYSA-N 2-[7-[[3-cyano-4-(trifluoromethoxy)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC1=CC=C(OC(F)(F)F)C(C#N)=C1 FFNDSFPWGHUHMV-UHFFFAOYSA-N 0.000 claims description 5
- BMVPECILWDOWNB-UHFFFAOYSA-N 2-[7-[[3-cyano-5-(trifluoromethoxy)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC1=CC(OC(F)(F)F)=CC(C#N)=C1 BMVPECILWDOWNB-UHFFFAOYSA-N 0.000 claims description 5
- YSILKVHRNQMQSY-UHFFFAOYSA-N 2-[7-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 YSILKVHRNQMQSY-UHFFFAOYSA-N 0.000 claims description 5
- APVNJQIQAVRXPY-UHFFFAOYSA-N 2-[7-[[6-cyclopentyl-5-(trifluoromethyl)pyridin-3-yl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC(C=C1C(F)(F)F)=CN=C1C1CCCC1 APVNJQIQAVRXPY-UHFFFAOYSA-N 0.000 claims description 5
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 5
- 208000023275 Autoimmune disease Diseases 0.000 claims description 5
- 208000011231 Crohn disease Diseases 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 206010052779 Transplant rejections Diseases 0.000 claims description 5
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 5
- 206010000496 acne Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 210000004698 lymphocyte Anatomy 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- RYNLYBXICSFSBE-UHFFFAOYSA-N 2-[7-[(3-cyano-4-propan-2-yloxyphenyl)methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=C(C#N)C(OC(C)C)=CC=C1COC1=CC=C(NC2=C3CCC2CC(O)=O)C3=C1 RYNLYBXICSFSBE-UHFFFAOYSA-N 0.000 claims description 4
- LPWPURJTTZWRJT-UHFFFAOYSA-N 2-[7-[(5-propan-2-yloxypyrazin-2-yl)methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=NC(OC(C)C)=CN=C1COC1=CC=C(NC2=C3CCC2CC(O)=O)C3=C1 LPWPURJTTZWRJT-UHFFFAOYSA-N 0.000 claims description 4
- UGZHLLUJQTZGSW-UHFFFAOYSA-N 2-[7-[[2,4-bis(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC1=CC=C(C(F)(F)F)C=C1C(F)(F)F UGZHLLUJQTZGSW-UHFFFAOYSA-N 0.000 claims description 4
- QVSUOKLIQJKAQR-UHFFFAOYSA-N 2-[7-[[3,5-bis(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 QVSUOKLIQJKAQR-UHFFFAOYSA-N 0.000 claims description 4
- AOTKRAFWIFBWNY-UHFFFAOYSA-N 2-[7-[[4-(2,2-dimethylpropyl)-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=C(C(F)(F)F)C(CC(C)(C)C)=CC=C1COC1=CC=C(NC2=C3CCC2CC(O)=O)C3=C1 AOTKRAFWIFBWNY-UHFFFAOYSA-N 0.000 claims description 4
- FAOCLURRKANLDM-UHFFFAOYSA-N 2-[7-[[4-(2-methylpropyl)-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=C(C(F)(F)F)C(CC(C)C)=CC=C1COC1=CC=C(NC2=C3CCC2CC(O)=O)C3=C1 FAOCLURRKANLDM-UHFFFAOYSA-N 0.000 claims description 4
- RTUNBEZDQHTOCR-UHFFFAOYSA-N 2-[7-[[4-chloro-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC1=CC=C(Cl)C(C(F)(F)F)=C1 RTUNBEZDQHTOCR-UHFFFAOYSA-N 0.000 claims description 4
- YDRZHJUJQIICPF-UHFFFAOYSA-N 2-[7-[[4-cyclobutyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC(C=C1C(F)(F)F)=CC=C1C1CCC1 YDRZHJUJQIICPF-UHFFFAOYSA-N 0.000 claims description 4
- MVGWUTBTXDYMND-UHFFFAOYSA-N 2-[7-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC(C=C1C(F)(F)F)=CC=C1C1CCCC1 MVGWUTBTXDYMND-UHFFFAOYSA-N 0.000 claims description 4
- BLJGNRHRVSPDNF-UHFFFAOYSA-N 2-[7-[[4-cyclopropyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC(C=C1C(F)(F)F)=CC=C1C1CC1 BLJGNRHRVSPDNF-UHFFFAOYSA-N 0.000 claims description 4
- ZVIVSGXTURPMNI-UHFFFAOYSA-N 2-[7-[[4-propyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=C(C(F)(F)F)C(CCC)=CC=C1COC1=CC=C(NC2=C3CCC2CC(O)=O)C3=C1 ZVIVSGXTURPMNI-UHFFFAOYSA-N 0.000 claims description 4
- JQQCGIGLXLKJEG-UHFFFAOYSA-N 2-[7-[[4-pyrrolidin-1-yl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC(C=C1C(F)(F)F)=CC=C1N1CCCC1 JQQCGIGLXLKJEG-UHFFFAOYSA-N 0.000 claims description 4
- XNHGJIORIYOSDG-UHFFFAOYSA-N 2-[7-[[6-(3,3-difluoropyrrolidin-1-yl)-5-(trifluoromethyl)pyridin-3-yl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC(C=C1C(F)(F)F)=CN=C1N1CCC(F)(F)C1 XNHGJIORIYOSDG-UHFFFAOYSA-N 0.000 claims description 4
- VWGAQWBCQIFVIG-UHFFFAOYSA-N 2-[7-[[6-pyrrolidin-1-yl-5-(trifluoromethyl)pyridin-3-yl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC(C=C1C(F)(F)F)=CN=C1N1CCCC1 VWGAQWBCQIFVIG-UHFFFAOYSA-N 0.000 claims description 4
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
- GSCYUSMVQCCJLM-UHFFFAOYSA-N 2-[7-[[4-cyclopentyloxy-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC(C=C1C(F)(F)F)=CC=C1OC1CCCC1 GSCYUSMVQCCJLM-UHFFFAOYSA-N 0.000 claims description 3
- 230000000813 microbial effect Effects 0.000 claims description 3
- RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical class C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 claims description 2
- AMPGOENIMLXHEV-UHFFFAOYSA-N 2-[7-[(4-methylsulfonylphenyl)methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1COC1=CC=C(NC2=C3CCC2CC(O)=O)C3=C1 AMPGOENIMLXHEV-UHFFFAOYSA-N 0.000 claims description 2
- KPCBFGSKFILKOJ-UHFFFAOYSA-N 2-[7-[(4-pyrazin-2-ylphenyl)methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC(C=C1)=CC=C1C1=CN=CC=N1 KPCBFGSKFILKOJ-UHFFFAOYSA-N 0.000 claims description 2
- PKJRFLUNQGZFRN-UHFFFAOYSA-N 2-[7-[[4-(cyclohexylmethyl)-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC(C=C1C(F)(F)F)=CC=C1CC1CCCCC1 PKJRFLUNQGZFRN-UHFFFAOYSA-N 0.000 claims description 2
- SHHOLILTTDNTMS-UHFFFAOYSA-N 2-[7-[[4-(cyclopropylmethoxy)-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC(C=C1C(F)(F)F)=CC=C1OCC1CC1 SHHOLILTTDNTMS-UHFFFAOYSA-N 0.000 claims description 2
- LQTHHFBBBSJUPL-UHFFFAOYSA-N 2-[7-[[4-(ethylamino)-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=C(C(F)(F)F)C(NCC)=CC=C1COC1=CC=C(NC2=C3CCC2CC(O)=O)C3=C1 LQTHHFBBBSJUPL-UHFFFAOYSA-N 0.000 claims description 2
- VUGVJWOKFZUXOP-UHFFFAOYSA-N 2-[7-[[4-carbamoyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=C(C(F)(F)F)C(C(=O)N)=CC=C1COC1=CC=C(NC2=C3CCC2CC(O)=O)C3=C1 VUGVJWOKFZUXOP-UHFFFAOYSA-N 0.000 claims description 2
- GQSQSTSCDLGWQJ-UHFFFAOYSA-N 2-[7-[[4-cyano-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC1=CC=C(C#N)C(C(F)(F)F)=C1 GQSQSTSCDLGWQJ-UHFFFAOYSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 2
- 229930064664 L-arginine Natural products 0.000 claims description 2
- 235000014852 L-arginine Nutrition 0.000 claims description 2
- 208000036142 Viral infection Diseases 0.000 claims description 2
- SCYWZHVBFXFLCZ-NCTGSHGJSA-L [Ca+2].C1(CCCC1)C1=C(C=C(COC2=CC=3C4=C(NC3C=C2)[C@H](CC4)CC(=O)[O-])C=C1)C(F)(F)F.C1(CCCC1)C1=C(C=C(COC4=CC=2C3=C(NC2C=C4)[C@H](CC3)CC(=O)[O-])C=C1)C(F)(F)F Chemical compound [Ca+2].C1(CCCC1)C1=C(C=C(COC2=CC=3C4=C(NC3C=C2)[C@H](CC4)CC(=O)[O-])C=C1)C(F)(F)F.C1(CCCC1)C1=C(C=C(COC4=CC=2C3=C(NC2C=C4)[C@H](CC3)CC(=O)[O-])C=C1)C(F)(F)F SCYWZHVBFXFLCZ-NCTGSHGJSA-L 0.000 claims description 2
- QSMCONBMMZYAOB-LMOVPXPDSA-N acetonitrile;2-[(3s)-7-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound CC#N.C([C@H]1CC(=O)O)CC(C2=C3)=C1NC2=CC=C3OCC(C=C1C(F)(F)F)=CC=C1C1CCCC1 QSMCONBMMZYAOB-LMOVPXPDSA-N 0.000 claims description 2
- 230000009385 viral infection Effects 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 24
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 17
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 102100025750 Sphingosine 1-phosphate receptor 1 Human genes 0.000 claims 3
- 101710155454 Sphingosine 1-phosphate receptor 1 Proteins 0.000 claims 3
- 102000005962 receptors Human genes 0.000 claims 3
- 108020003175 receptors Proteins 0.000 claims 3
- 230000036571 hydration Effects 0.000 claims 2
- 238000006703 hydration reaction Methods 0.000 claims 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 description 24
- 125000004438 haloalkoxy group Chemical group 0.000 description 17
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 14
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- YTEXYZJAKTXZLQ-LMOVPXPDSA-N 2-[(3s)-7-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid;hydrate Chemical compound O.C([C@H]1CC(=O)O)CC(C2=C3)=C1NC2=CC=C3OCC(C=C1C(F)(F)F)=CC=C1C1CCCC1 YTEXYZJAKTXZLQ-LMOVPXPDSA-N 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- QVDGRCAASDHNEC-UHFFFAOYSA-N 2-[7-[[4-(thiadiazol-4-yl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid Chemical compound OC(=O)CC1CCC(C2=C3)=C1NC2=CC=C3OCC(C=C1)=CC=C1C1=CSN=N1 QVDGRCAASDHNEC-UHFFFAOYSA-N 0.000 description 1
- 150000008564 D-lysines Chemical class 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 208000037979 autoimmune inflammatory disease Diseases 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13567208P | 2008-07-23 | 2008-07-23 | |
| US61/135,672 | 2008-07-23 | ||
| US20937409P | 2009-03-06 | 2009-03-06 | |
| US61/209,374 | 2009-03-06 | ||
| PCT/US2009/004265 WO2010011316A1 (en) | 2008-07-23 | 2009-07-22 | SUBSTITUTED 1,2,3,4- TETRAHYDROCYCLOPENTA[b]INDOL-3-YL) ACETIC ACID DERIVATIVES USEFUL IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISORDERS |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013265453A Division JP2014144948A (ja) | 2008-07-23 | 2013-12-24 | 自己免疫障害および炎症性障害の処置において有用な置換型１，２，３，４−テトラヒドロシクロペンタ［ｂ］インドル−３−イル）酢酸誘導体 |
Publications (3)
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