AU2005297138A1 - Novel dicarboxylic acid derivatives - Google Patents

Info

Publication number

AU2005297138A1

AU2005297138A1 AU2005297138A AU2005297138A AU2005297138A1 AU 2005297138 A1 AU2005297138 A1 AU 2005297138A1 AU 2005297138 A AU2005297138 A AU 2005297138A AU 2005297138 A AU2005297138 A AU 2005297138A AU 2005297138 A1 AU2005297138 A1 AU 2005297138A1

Authority

AU

Australia

Prior art keywords

dicarboxylic acid

cyclopentane

alkyl

acid

decyl

Prior art date

2004-10-22

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.)

Abandoned

Links

• Espacenet
• Global Dossier
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• 150000001990 dicarboxylic acid derivatives Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 143
• -1 polyfluoroalkyl Chemical group 0.000 claims description 77
• 239000000203 mixture Substances 0.000 claims description 53
• 125000000217 alkyl group Chemical group 0.000 claims description 43
• 238000002360 preparation method Methods 0.000 claims description 43
• 230000002829 reductive effect Effects 0.000 claims description 43
• 238000000034 method Methods 0.000 claims description 39
• 239000002253 acid Substances 0.000 claims description 29
• 125000003118 aryl group Chemical group 0.000 claims description 28
• 238000006243 chemical reaction Methods 0.000 claims description 28
• 125000004429 atom Chemical group 0.000 claims description 25
• 125000005842 heteroatom Chemical group 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 25
• 125000001072 heteroaryl group Chemical group 0.000 claims description 22
• 150000002148 esters Chemical class 0.000 claims description 20
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 claims description 18
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
• 230000008569 process Effects 0.000 claims description 16
• NXXNOAZWICKDFY-UHFFFAOYSA-N 3-[2-(4-decyl-2,3-difluorophenyl)ethylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound FC1=C(F)C(CCCCCCCCCC)=CC=C1CCNC1CC(C(O)=O)(C(O)=O)CC1 NXXNOAZWICKDFY-UHFFFAOYSA-N 0.000 claims description 15
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 12
• 125000005843 halogen group Chemical group 0.000 claims description 12
• 125000000623 heterocyclic group Chemical group 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 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 description 11
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 11
• 150000004677 hydrates Chemical class 0.000 claims description 11
• 239000012453 solvate Substances 0.000 claims description 11
• GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 claims description 10
• 125000004494 ethyl ester group Chemical group 0.000 claims description 10
• 102000005962 receptors Human genes 0.000 claims description 10
• 108020003175 receptors Proteins 0.000 claims description 10
• XWYNJZPDWLFBBL-UHFFFAOYSA-N 3-[(4-decyl-2,3-difluorophenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound FC1=C(F)C(CCCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 XWYNJZPDWLFBBL-UHFFFAOYSA-N 0.000 claims description 9
• 239000000556 agonist Substances 0.000 claims description 9
• 125000004122 cyclic group Chemical group 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 206010052779 Transplant rejections Diseases 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 7
• 238000006268 reductive amination reaction Methods 0.000 claims description 7
• FXMLDXSQLDHJNV-UHFFFAOYSA-N 1-(ethylcarbamoyl)-3-[(4-nonylphenyl)methylamino]cyclopentane-1-carboxylic acid Chemical compound C1=CC(CCCCCCCCC)=CC=C1CNC1CC(C(=O)NCC)(C(O)=O)CC1 FXMLDXSQLDHJNV-UHFFFAOYSA-N 0.000 claims description 6
• WLNVEUFDXFOUFR-UHFFFAOYSA-N 1-(ethylcarbamoyl)-3-[(4-octylphenyl)methylamino]cyclopentane-1-carboxylic acid Chemical compound C1=CC(CCCCCCCC)=CC=C1CNC1CC(C(=O)NCC)(C(O)=O)CC1 WLNVEUFDXFOUFR-UHFFFAOYSA-N 0.000 claims description 6
• INIRJJMZHLBTND-UHFFFAOYSA-N 1-(methylcarbamoyl)-3-[(4-octylphenyl)methylamino]cyclopentane-1-carboxylic acid Chemical compound C1=CC(CCCCCCCC)=CC=C1CNC1CC(C(=O)NC)(C(O)=O)CC1 INIRJJMZHLBTND-UHFFFAOYSA-N 0.000 claims description 6
• FBDDPQRVQWBJRV-UHFFFAOYSA-N 3-[(4-decylphenyl)methylamino]-1-ethoxycarbonylcyclopentane-1-carboxylic acid Chemical compound C1=CC(CCCCCCCCCC)=CC=C1CNC1CC(C(=O)OCC)(C(O)=O)CC1 FBDDPQRVQWBJRV-UHFFFAOYSA-N 0.000 claims description 6
• PKILXMOKFDNUJX-UHFFFAOYSA-N 3-[(4-decylphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical class C1=CC(CCCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 PKILXMOKFDNUJX-UHFFFAOYSA-N 0.000 claims description 6
• JDQJBWYUHNQOFT-UHFFFAOYSA-N 3-[3-(4-decyl-2,3-difluorophenyl)propoxycarbonylamino]-1-ethoxycarbonylcyclopentane-1-carboxylic acid Chemical compound FC1=C(F)C(CCCCCCCCCC)=CC=C1CCCOC(=O)NC1CC(C(=O)OCC)(C(O)=O)CC1 JDQJBWYUHNQOFT-UHFFFAOYSA-N 0.000 claims description 6
• YZFOGXKZTWZVFN-UHFFFAOYSA-N cyclopentane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1 YZFOGXKZTWZVFN-UHFFFAOYSA-N 0.000 claims description 6
• 210000004698 lymphocyte Anatomy 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• RCJRRIILAXMWSC-UHFFFAOYSA-N 1-[(4-decylphenyl)methyl]piperidine-4,4-dicarboxylic acid Chemical compound C1=CC(CCCCCCCCCC)=CC=C1CN1CCC(C(O)=O)(C(O)=O)CC1 RCJRRIILAXMWSC-UHFFFAOYSA-N 0.000 claims description 5
• HJBLEOMQDLLYAZ-UHFFFAOYSA-N 3-[2-(2,3-difluoro-4-nonylphenyl)ethylamino]-1-(methylcarbamoyl)cyclopentane-1-carboxylic acid Chemical compound FC1=C(F)C(CCCCCCCCC)=CC=C1CCNC1CC(C(=O)NC)(C(O)=O)CC1 HJBLEOMQDLLYAZ-UHFFFAOYSA-N 0.000 claims description 5
• SRDAKPLZSVHLAY-UHFFFAOYSA-N 3-[3-(4-decyl-2,3-difluorophenyl)propoxycarbonylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound FC1=C(F)C(CCCCCCCCCC)=CC=C1CCCOC(=O)NC1CC(C(O)=O)(C(O)=O)CC1 SRDAKPLZSVHLAY-UHFFFAOYSA-N 0.000 claims description 5
• 208000023275 Autoimmune disease Diseases 0.000 claims description 5
• 238000005859 coupling reaction Methods 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• VUUYOWYIYIOAHU-UHFFFAOYSA-N 1-[(2,3-difluoro-4-nonylphenyl)methyl]-4-(ethylcarbamoyl)piperidine-4-carboxylic acid Chemical compound FC1=C(F)C(CCCCCCCCC)=CC=C1CN1CCC(C(=O)NCC)(C(O)=O)CC1 VUUYOWYIYIOAHU-UHFFFAOYSA-N 0.000 claims description 4
• QWXWHOXOSGRQMZ-UHFFFAOYSA-N 1-carbamoyl-3-[(4-nonylphenyl)methylamino]cyclopentane-1-carboxylic acid Chemical compound C1=CC(CCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(N)=O)CC1 QWXWHOXOSGRQMZ-UHFFFAOYSA-N 0.000 claims description 4
• IXGMNCZFCJNURQ-UHFFFAOYSA-N 3-[(4-nonylphenyl)methylamino]-1-(propan-2-ylcarbamoyl)cyclopentane-1-carboxylic acid Chemical compound C1=CC(CCCCCCCCC)=CC=C1CNC1CC(C(=O)NC(C)C)(C(O)=O)CC1 IXGMNCZFCJNURQ-UHFFFAOYSA-N 0.000 claims description 4
• FGERXQYSFOUIDO-UHFFFAOYSA-N 3-[[3-fluoro-4-(4-heptylphenyl)phenyl]methylamino]-1-(methylcarbamoyl)cyclobutane-1-carboxylic acid Chemical compound C1=CC(CCCCCCC)=CC=C1C(C(=C1)F)=CC=C1CNC1CC(C(=O)NC)(C(O)=O)C1 FGERXQYSFOUIDO-UHFFFAOYSA-N 0.000 claims description 4
• ZQCSXWIJERKDER-UHFFFAOYSA-N 3-[[3-fluoro-4-(4-heptylphenyl)phenyl]methylamino]cyclopentane-1,1-dicarboxylic acid Chemical class C1=CC(CCCCCCC)=CC=C1C(C(=C1)F)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 ZQCSXWIJERKDER-UHFFFAOYSA-N 0.000 claims description 4
• NOLDYNRZFYWFPP-UHFFFAOYSA-N 4-[2-(2,3-difluoro-4-nonylphenyl)ethylamino]cyclohexane-1,1-dicarboxylic acid Chemical compound FC1=C(F)C(CCCCCCCCC)=CC=C1CCNC1CCC(C(O)=O)(C(O)=O)CC1 NOLDYNRZFYWFPP-UHFFFAOYSA-N 0.000 claims description 4
• 150000001413 amino acids Chemical class 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
• JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims description 4
• 208000035475 disorder Diseases 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 201000006417 multiple sclerosis Diseases 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• WWUZIQQURGPMPG-UHFFFAOYSA-N (-)-D-erythro-Sphingosine Natural products CCCCCCCCCCCCCC=CC(O)C(N)CO WWUZIQQURGPMPG-UHFFFAOYSA-N 0.000 claims description 3
• CDABZWDDEZMOIV-UHFFFAOYSA-N 1-(dimethylcarbamoyl)-3-[(4-nonylphenyl)methylamino]cyclopentane-1-carboxylic acid Chemical compound C1=CC(CCCCCCCCC)=CC=C1CNC1CC(C(=O)N(C)C)(C(O)=O)CC1 CDABZWDDEZMOIV-UHFFFAOYSA-N 0.000 claims description 3
• GQWNIQYSMBHSDC-UHFFFAOYSA-N 1-[(4-decylphenyl)methyl]-4-ethoxycarbonylpiperidine-4-carboxylic acid Chemical compound C1=CC(CCCCCCCCCC)=CC=C1CN1CCC(C(=O)OCC)(C(O)=O)CC1 GQWNIQYSMBHSDC-UHFFFAOYSA-N 0.000 claims description 3
• XPIOWKBMQNEIOW-UHFFFAOYSA-N 2-[4-[2-(3-chloro-4-nonoxyphenyl)ethylamino]but-2-ynyl]-2-methylpropanedioic acid Chemical compound CCCCCCCCCOC1=CC=C(CCNCC#CCC(C)(C(O)=O)C(O)=O)C=C1Cl XPIOWKBMQNEIOW-UHFFFAOYSA-N 0.000 claims description 3
• KPAYUJDHZKSQQC-UHFFFAOYSA-N 2-[4-[cyclopropyl-[(4-nonylphenyl)methyl]amino]but-2-ynyl]-2-methylpropanedioic acid Chemical compound C1=CC(CCCCCCCCC)=CC=C1CN(CC#CCC(C)(C(O)=O)C(O)=O)C1CC1 KPAYUJDHZKSQQC-UHFFFAOYSA-N 0.000 claims description 3
• ASDHRIBAVDPPLH-UHFFFAOYSA-N 3-[(2,3-difluoro-4-nonylphenyl)methylamino]-1-ethoxycarbonylcyclopentane-1-carboxylic acid Chemical compound FC1=C(F)C(CCCCCCCCC)=CC=C1CNC1CC(C(=O)OCC)(C(O)=O)CC1 ASDHRIBAVDPPLH-UHFFFAOYSA-N 0.000 claims description 3
• SZDKMLJDXRJFTI-UHFFFAOYSA-N 3-[(4-decyl-2,3-difluorophenyl)methylamino]-1-propan-2-yloxycarbonylcyclopentane-1-carboxylic acid Chemical compound FC1=C(F)C(CCCCCCCCCC)=CC=C1CNC1CC(C(=O)OC(C)C)(C(O)=O)CC1 SZDKMLJDXRJFTI-UHFFFAOYSA-N 0.000 claims description 3
• VHPIXEGBIFHBRT-UHFFFAOYSA-N 3-[(4-decyl-2,3-difluorophenyl)methylamino]cyclobutane-1,1-dicarboxylic acid Chemical compound FC1=C(F)C(CCCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)C1 VHPIXEGBIFHBRT-UHFFFAOYSA-N 0.000 claims description 3
• YGNJUQIUVOACOQ-UHFFFAOYSA-N 3-[(4-nonylphenyl)methylamino]-1-(2,2,2-trifluoroethylcarbamoyl)cyclopentane-1-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCCC)=CC=C1CNC1CC(C(=O)NCC(F)(F)F)(C(O)=O)CC1 YGNJUQIUVOACOQ-UHFFFAOYSA-N 0.000 claims description 3
• IHDDWUCLSGQAIB-UHFFFAOYSA-N 3-[(4-nonylphenyl)methylamino]-1-propan-2-yloxycarbonylcyclopentane-1-carboxylic acid Chemical compound C1=CC(CCCCCCCCC)=CC=C1CNC1CC(C(=O)OC(C)C)(C(O)=O)CC1 IHDDWUCLSGQAIB-UHFFFAOYSA-N 0.000 claims description 3
• YWJZUMRCKRAZQA-UHFFFAOYSA-N 3-[(4-octylphenyl)methylamino]-1-propan-2-yloxycarbonylcyclopentane-1-carboxylic acid Chemical compound C1=CC(CCCCCCCC)=CC=C1CNC1CC(C(=O)OC(C)C)(C(O)=O)CC1 YWJZUMRCKRAZQA-UHFFFAOYSA-N 0.000 claims description 3
• IKJTUPWCEYLRLG-UHFFFAOYSA-N 3-[2-(4-octylphenyl)ethylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=CC(CCCCCCCC)=CC=C1CCNC1CC(C(O)=O)(C(O)=O)CC1 IKJTUPWCEYLRLG-UHFFFAOYSA-N 0.000 claims description 3
• JZTMRPLECHFTNQ-UHFFFAOYSA-N 3-[[3-fluoro-4-(4-heptylphenyl)phenyl]methylamino]-1-(methylcarbamoyl)cyclopentane-1-carboxylic acid Chemical compound C1=CC(CCCCCCC)=CC=C1C(C(=C1)F)=CC=C1CNC1CC(C(=O)NC)(C(O)=O)CC1 JZTMRPLECHFTNQ-UHFFFAOYSA-N 0.000 claims description 3
• JPEITTCRYGFZBO-UHFFFAOYSA-N 3-[[4-[[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]methoxy]phenyl]methylamino]cyclopentane-1,1-dicarboxylic acid Chemical class C1C(C(=O)O)(C(O)=O)CCC1NCC(C=C1)=CC=C1OCC1=CC(C=2C=CC=CC=2)=C(C(F)(F)F)S1 JPEITTCRYGFZBO-UHFFFAOYSA-N 0.000 claims description 3
• 201000001320 Atherosclerosis Diseases 0.000 claims description 3
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
• 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
• 206010025323 Lymphomas Diseases 0.000 claims description 3
• 208000034486 Multi-organ failure Diseases 0.000 claims description 3
• 208000009525 Myocarditis Diseases 0.000 claims description 3
• 229910019142 PO4 Inorganic materials 0.000 claims description 3
• 206010035664 Pneumonia Diseases 0.000 claims description 3
• 201000004681 Psoriasis Diseases 0.000 claims description 3
• 206010040047 Sepsis Diseases 0.000 claims description 3
• 208000006673 asthma Diseases 0.000 claims description 3
• 201000008937 atopic dermatitis Diseases 0.000 claims description 3
• 230000001684 chronic effect Effects 0.000 claims description 3
• 150000002367 halogens Chemical class 0.000 claims description 3
• 206010025135 lupus erythematosus Diseases 0.000 claims description 3
• 208000003747 lymphoid leukemia Diseases 0.000 claims description 3
• 208000029744 multiple organ dysfunction syndrome Diseases 0.000 claims description 3
• 239000010452 phosphate Substances 0.000 claims description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
• WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 claims description 3
• OVSQGRPUVXCGGX-UHFFFAOYSA-N 1-(methylcarbamoyl)-3-[(4-nonylphenyl)methylamino]cyclopentane-1-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCCC)=CC=C1CNC1CC(C(=O)NC)(C(O)=O)CC1 OVSQGRPUVXCGGX-UHFFFAOYSA-N 0.000 claims description 2
• FMRUUBKNZCITHU-UHFFFAOYSA-N 1-(methylcarbamoyl)cyclobutane-1-carboxylic acid Chemical compound CNC(=O)C1(C(O)=O)CCC1 FMRUUBKNZCITHU-UHFFFAOYSA-N 0.000 claims description 2
• LVNMEDFRUGYQEB-UHFFFAOYSA-N 1-butoxycarbonyl-3-[(4-nonylphenyl)methylamino]cyclopentane-1-carboxylic acid 3-[2-(4-decylphenyl)ethylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C(CCC)OC(=O)C1(CC(CC1)NCC1=CC=C(C=C1)CCCCCCCCC)C(=O)O.C(CCCCCCCCC)C1=CC=C(CCNC2CC(CC2)(C(=O)O)C(=O)O)C=C1 LVNMEDFRUGYQEB-UHFFFAOYSA-N 0.000 claims description 2
• SYDWIQWRKXMXLM-UHFFFAOYSA-N 2-ethyl-2-[4-[[3-fluoro-4-(4-hexylphenyl)phenyl]methylamino]but-2-ynyl]propanedioic acid Chemical compound C1=CC(CCCCCC)=CC=C1C1=CC=C(CNCC#CCC(CC)(C(O)=O)C(O)=O)C=C1F SYDWIQWRKXMXLM-UHFFFAOYSA-N 0.000 claims description 2
• AHMDGQWRYBPXAN-UHFFFAOYSA-N 3-[(2,3-difluoro-4-nonylphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound FC1=C(F)C(CCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 AHMDGQWRYBPXAN-UHFFFAOYSA-N 0.000 claims description 2
• VRSWWYHLIPOFEI-UHFFFAOYSA-N 3-[(4-decyl-2,3-difluorophenyl)methylamino]-1-(methylcarbamoyl)cyclopentane-1-carboxylic acid Chemical compound FC1=C(F)C(CCCCCCCCCC)=CC=C1CNC1CC(C(=O)NC)(C(O)=O)CC1 VRSWWYHLIPOFEI-UHFFFAOYSA-N 0.000 claims description 2
• OXZHODBHYXDTIV-UHFFFAOYSA-N 3-[(4-decylphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid 3-[methyl-[(4-nonylphenyl)methyl]amino]cyclopentane-1,1-dicarboxylic acid 3-[(4-nonylphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid hydrochloride Chemical compound Cl.CN(C1CC(CC1)(C(=O)O)C(=O)O)CC1=CC=C(C=C1)CCCCCCCCC.C(CCCCCCCCC)C1=CC=C(CNC2CC(CC2)(C(=O)O)C(=O)O)C=C1.C(CCCCCCCC)C1=CC=C(CNC2CC(CC2)(C(=O)O)C(=O)O)C=C1 OXZHODBHYXDTIV-UHFFFAOYSA-N 0.000 claims description 2
• ZHTWBXYWJCQEMU-UHFFFAOYSA-N 3-[2-(3-chloro-4-decoxyphenyl)ethylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=C(Cl)C(OCCCCCCCCCC)=CC=C1CCNC1CC(C(O)=O)(C(O)=O)CC1 ZHTWBXYWJCQEMU-UHFFFAOYSA-N 0.000 claims description 2
• AAPPHGSJLUGCOI-UHFFFAOYSA-N 3-[2-(4-decyl-2,3-difluorophenyl)ethylamino]-1-ethoxycarbonylcyclobutane-1-carboxylic acid 3-[[4-[[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]methoxy]phenyl]methylamino]cyclobutane-1,1-dicarboxylic acid Chemical compound C1(=CC=CC=C1)C=1C=C(SC1C(F)(F)F)COC1=CC=C(CNC2CC(C2)(C(=O)O)C(=O)O)C=C1.C(C)OC(=O)C1(CC(C1)NCCC1=C(C(=C(C=C1)CCCCCCCCCC)F)F)C(=O)O AAPPHGSJLUGCOI-UHFFFAOYSA-N 0.000 claims description 2
• GCIXQGMXSZKIFG-UHFFFAOYSA-N 3-[2-(4-decyl-2,3-difluorophenyl)ethylamino]-1-ethoxycarbonylcyclopentane-1-carboxylic acid Chemical class FC1=C(F)C(CCCCCCCCCC)=CC=C1CCNC1CC(C(=O)OCC)(C(O)=O)CC1 GCIXQGMXSZKIFG-UHFFFAOYSA-N 0.000 claims description 2
• OBRJBBWYUXYRHR-UHFFFAOYSA-N 3-[cyclopropyl-[[3-fluoro-4-(4-heptylphenyl)phenyl]methyl]amino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=CC(CCCCCCC)=CC=C1C(C(=C1)F)=CC=C1CN(C1CC(CC1)(C(O)=O)C(O)=O)C1CC1 OBRJBBWYUXYRHR-UHFFFAOYSA-N 0.000 claims description 2
• 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 claims description 2
• GHGVAMDADNSSMW-UHFFFAOYSA-N C(C)OC(=O)C1(CCN(CC1)CC1=C(C(=C(C=C1)CCCCCCCCCC)F)F)C(=O)O.C(C)OC(=O)C1(CCN(CC1)CC1=CC(=C(C=C1)OCCCCCCCCCC)Cl)C(=O)O Chemical compound C(C)OC(=O)C1(CCN(CC1)CC1=C(C(=C(C=C1)CCCCCCCCCC)F)F)C(=O)O.C(C)OC(=O)C1(CCN(CC1)CC1=CC(=C(C=C1)OCCCCCCCCCC)Cl)C(=O)O GHGVAMDADNSSMW-UHFFFAOYSA-N 0.000 claims description 2
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