KR20070097418A - 신규 디카르복시산 유도체 - Google Patents

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Publication number

KR20070097418A

KR20070097418A KR1020077011042A KR20077011042A KR20070097418A KR 20070097418 A KR20070097418 A KR 20070097418A KR 1020077011042 A KR1020077011042 A KR 1020077011042A KR 20077011042 A KR20077011042 A KR 20077011042A KR 20070097418 A KR20070097418 A KR 20070097418A

Authority

KR

South Korea

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.)

Ceased

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• 150000001990 dicarboxylic acid derivatives Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 136
• 238000002360 preparation method Methods 0.000 claims abstract description 36
• 239000000556 agonist Substances 0.000 claims abstract description 8
• 229910019142 PO4 Inorganic materials 0.000 claims abstract description 6
• 239000010452 phosphate Substances 0.000 claims abstract description 6
• -1 polyfluoroalkyl Chemical group 0.000 claims description 70
• 239000000203 mixture Substances 0.000 claims description 49
• 125000000217 alkyl group Chemical group 0.000 claims description 45
• 238000000034 method Methods 0.000 claims description 41
• 238000006243 chemical reaction Methods 0.000 claims description 28
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 125000005842 heteroatom Chemical group 0.000 claims description 25
• 150000003839 salts Chemical class 0.000 claims description 25
• 125000004429 atom Chemical group 0.000 claims description 24
• 125000001072 heteroaryl group Chemical group 0.000 claims description 21
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
• 150000002148 esters Chemical class 0.000 claims description 17
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
• 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 claims description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
• 125000005843 halogen group Chemical group 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 13
• 201000010099 disease Diseases 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 13
• 239000002253 acid Substances 0.000 claims description 12
• 125000000623 heterocyclic group Chemical group 0.000 claims description 12
• NXXNOAZWICKDFY-UHFFFAOYSA-N 3-[2-(4-decyl-2,3-difluorophenyl)ethylamino]cyclopentane-1,1-dicarboxylic acid Chemical class FC1=C(F)C(CCCCCCCCCC)=CC=C1CCNC1CC(C(O)=O)(C(O)=O)CC1 NXXNOAZWICKDFY-UHFFFAOYSA-N 0.000 claims description 10
• 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 10
• 150000004677 hydrates Chemical class 0.000 claims description 10
• 239000012453 solvate Substances 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• XWYNJZPDWLFBBL-UHFFFAOYSA-N 3-[(4-decyl-2,3-difluorophenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical class FC1=C(F)C(CCCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 XWYNJZPDWLFBBL-UHFFFAOYSA-N 0.000 claims description 9
• 238000004519 manufacturing process Methods 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
• 102000005962 receptors Human genes 0.000 claims description 9
• 108020003175 receptors Proteins 0.000 claims description 9
• 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 8
• 229940079593 drug Drugs 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 230000008569 process Effects 0.000 claims description 8
• 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 7
• 206010052779 Transplant rejections Diseases 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
• 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
• 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 6
• OTFHAFRJBUWXLS-UHFFFAOYSA-N 3-[(2,3-difluoro-4-nonylphenyl)methylamino]-1-(methylcarbamoyl)cyclopentane-1-carboxylic acid Chemical compound FC1=C(F)C(CCCCCCCCC)=CC=C1CNC1CC(C(=O)NC)(C(O)=O)CC1 OTFHAFRJBUWXLS-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• BUPTZRZGUIGPQW-UHFFFAOYSA-N 3-[(4-nonylphenyl)methylamino]-1-(propylcarbamoyl)cyclopentane-1-carboxylic acid Chemical compound C1=CC(CCCCCCCCC)=CC=C1CNC1CC(C(=O)NCCC)(C(O)=O)CC1 BUPTZRZGUIGPQW-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• 210000004698 lymphocyte Anatomy 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 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 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 5
• DPEWOKOZTYDKCQ-UHFFFAOYSA-N 3-[(4-decylphenyl)methylamino]-1-(methylcarbamoyl)cyclopentane-1-carboxylic acid Chemical compound C1=CC(CCCCCCCCCC)=CC=C1CNC1CC(C(=O)NC)(C(O)=O)CC1 DPEWOKOZTYDKCQ-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• 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 5
• 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 5
• 208000023275 Autoimmune disease Diseases 0.000 claims description 5
• 239000003795 chemical substances by application Substances 0.000 claims description 5
• 238000005859 coupling reaction Methods 0.000 claims description 5
• 125000004122 cyclic group Chemical group 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• XYYBWJQQKIGHHX-UHFFFAOYSA-N 3-[2-(4-decyl-2,3-difluorophenyl)ethylamino]-1-ethoxycarbonylcyclobutane-1-carboxylic acid Chemical compound FC1=C(F)C(CCCCCCCCCC)=CC=C1CCNC1CC(C(=O)OCC)(C(O)=O)C1 XYYBWJQQKIGHHX-UHFFFAOYSA-N 0.000 claims description 4
• 150000001413 amino acids Chemical class 0.000 claims description 4
• 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 4
• 201000006417 multiple sclerosis Diseases 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 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 3
• JRCDLOBAFRRAGB-UHFFFAOYSA-N 1-[(1-carboxy-2-phenylethyl)carbamoyl]-3-[(4-nonylphenyl)methylamino]cyclopentane-1-carboxylic acid Chemical compound C1=CC(CCCCCCCCC)=CC=C1CNC1CC(C(=O)NC(CC=2C=CC=CC=2)C(O)=O)(C(O)=O)CC1 JRCDLOBAFRRAGB-UHFFFAOYSA-N 0.000 claims description 3
• VECZWVAFRLSZQS-UHFFFAOYSA-N 1-[(4-decylphenyl)methyl]-4-(propylcarbamoyl)piperidine-4-carboxylic acid Chemical compound C1=CC(CCCCCCCCCC)=CC=C1CN1CCC(C(=O)NCCC)(C(O)=O)CC1 VECZWVAFRLSZQS-UHFFFAOYSA-N 0.000 claims description 3
• PNZQYJNWRIJSQC-UHFFFAOYSA-N 1-ethoxycarbonyl-3-[(4-nonylphenyl)methylamino]cyclopentane-1-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCCC)=CC=C1CNC1CC(C(=O)OCC)(C(O)=O)CC1 PNZQYJNWRIJSQC-UHFFFAOYSA-N 0.000 claims description 3
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 3
• 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 3
• ZTGOZIIIMUXWQU-UHFFFAOYSA-N 2-methyl-2-[4-[[4-[[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]methoxy]phenyl]methylamino]but-2-ynyl]propanedioic acid Chemical compound C1=CC(CNCC#CCC(C)(C(O)=O)C(O)=O)=CC=C1OCC1=CC(C=2C=CC=CC=2)=C(C(F)(F)F)S1 ZTGOZIIIMUXWQU-UHFFFAOYSA-N 0.000 claims description 3
• 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 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
• ZRPVIWMWKJZNRQ-UHFFFAOYSA-N 3-[[4-[5-(3-chloro-4-ethoxyphenyl)pentoxy]phenyl]methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=C(Cl)C(OCC)=CC=C1CCCCCOC(C=C1)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 ZRPVIWMWKJZNRQ-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
• UHXBPACYWJLMNL-UHFFFAOYSA-N 3-[methyl-[[4-[[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]methoxy]phenyl]methyl]amino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1CC(C(O)=O)(C(O)=O)CC1N(C)CC(C=C1)=CC=C1OCC(SC=1C(F)(F)F)=CC=1C1=CC=CC=C1 UHXBPACYWJLMNL-UHFFFAOYSA-N 0.000 claims description 3
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
• 206010015150 Erythema Diseases 0.000 claims description 3
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
• 208000009525 Myocarditis Diseases 0.000 claims description 3
• 206010035664 Pneumonia Diseases 0.000 claims description 3
• 201000004681 Psoriasis Diseases 0.000 claims description 3
• 230000009471 action Effects 0.000 claims description 3
• 238000005576 amination reaction Methods 0.000 claims description 3
• 208000006673 asthma Diseases 0.000 claims description 3
• 201000008937 atopic dermatitis Diseases 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 230000001684 chronic effect Effects 0.000 claims description 3
• 230000006378 damage Effects 0.000 claims description 3
• 231100000321 erythema Toxicity 0.000 claims description 3
• 206010025135 lupus erythematosus Diseases 0.000 claims description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
• 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 claims description 2
• 206010018364 Glomerulonephritis Diseases 0.000 claims description 2
• 101000693265 Homo sapiens Sphingosine 1-phosphate receptor 1 Proteins 0.000 claims description 2
• 229930194542 Keto Natural products 0.000 claims description 2
• 208000028018 Lymphocytic leukaemia Diseases 0.000 claims description 2
• 206010025323 Lymphomas Diseases 0.000 claims description 2
• 230000033115 angiogenesis Effects 0.000 claims description 2
• 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 2
• 210000004369 blood Anatomy 0.000 claims description 2
• 239000008280 blood Substances 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• 206010012601 diabetes mellitus Diseases 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 230000001771 impaired effect Effects 0.000 claims description 2
• 230000004968 inflammatory condition Effects 0.000 claims description 2
• 230000002757 inflammatory effect Effects 0.000 claims description 2
• 125000000468 ketone group Chemical group 0.000 claims description 2
• 208000003747 lymphoid leukemia Diseases 0.000 claims description 2
• 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• 125000001424 substituent group Chemical group 0.000 claims description 2
• 230000002792 vascular Effects 0.000 claims description 2
• COYWNGNOEKTXJJ-UHFFFAOYSA-N 1-[(4-decylphenyl)methyl]-4-ethoxycarbonylpiperidine-4-carboxylic acid;1-[[3-fluoro-4-(4-heptylphenyl)phenyl]methyl]piperidine-4,4-dicarboxylic acid Chemical compound C1=CC(CCCCCCCCCC)=CC=C1CN1CCC(C(=O)OCC)(C(O)=O)CC1.C1=CC(CCCCCCC)=CC=C1C(C(=C1)F)=CC=C1CN1CCC(C(O)=O)(C(O)=O)CC1 COYWNGNOEKTXJJ-UHFFFAOYSA-N 0.000 claims 1
• ZKDXECBUNOJWIN-UHFFFAOYSA-N 1-[(4-decylphenyl)methyl]azetidine-3,3-dicarboxylic acid 1-[[4-[[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]methoxy]phenyl]methyl]piperidine-4,4-dicarboxylic acid Chemical compound C(CCCCCCCCC)C1=CC=C(CN2CC(C2)(C(=O)O)C(=O)O)C=C1.C1(=CC=CC=C1)C=1C=C(SC1C(F)(F)F)COC1=CC=C(CN2CCC(CC2)(C(=O)O)C(=O)O)C=C1 ZKDXECBUNOJWIN-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• KRYDWUHYIWAFNC-UHFFFAOYSA-N 3-[(4-decoxyphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid;1-(methylcarbamoyl)-3-[(4-nonylphenyl)methylamino]cyclopentane-1-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.C1=CC(CCCCCCCCC)=CC=C1CNC1CC(C(=O)NC)(C(O)=O)CC1.C1=CC(OCCCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 KRYDWUHYIWAFNC-UHFFFAOYSA-N 0.000 claims 1
• QTQNIKYFEFQETB-UHFFFAOYSA-N 3-[(4-decyl-2,3-difluorophenyl)methylamino]cyclopentane-1,1-dicarboxylic acid;3-[(4-decylphenyl)methylamino]-1-(methylcarbamoyl)cyclopentane-1-carboxylic acid Chemical compound C1=CC(CCCCCCCCCC)=CC=C1CNC1CC(C(=O)NC)(C(O)=O)CC1.FC1=C(F)C(CCCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 QTQNIKYFEFQETB-UHFFFAOYSA-N 0.000 claims 1
• JNHULPHBVGVKEY-UHFFFAOYSA-N 3-[(4-decylphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid 3-[(4-nonylphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound 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 JNHULPHBVGVKEY-UHFFFAOYSA-N 0.000 claims 1
• CHJONQYEEQAUPG-UHFFFAOYSA-N 3-[2-(4-decyl-2,3-difluorophenyl)ethylamino]cyclopentane-1,1-dicarboxylic acid;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.FC1=C(F)C(CCCCCCCCCC)=CC=C1CCNC1CC(C(O)=O)(C(O)=O)CC1 CHJONQYEEQAUPG-UHFFFAOYSA-N 0.000 claims 1
• GCSKOGKPWFCKIU-UHFFFAOYSA-N 3-[2-(4-decyl-2,3-difluorophenyl)ethylamino]cyclopentane-1,1-dicarboxylic acid;3-[2-(4-decylphenyl)ethylamino]-1-ethoxycarbonylcyclopentane-1-carboxylic acid Chemical class C1=CC(CCCCCCCCCC)=CC=C1CCNC1CC(C(=O)OCC)(C(O)=O)CC1.FC1=C(F)C(CCCCCCCCCC)=CC=C1CCNC1CC(C(O)=O)(C(O)=O)CC1 GCSKOGKPWFCKIU-UHFFFAOYSA-N 0.000 claims 1
• RYJSLJUODDKCPV-UHFFFAOYSA-N 3-[[3-fluoro-4-(4-heptylphenyl)phenyl]methylamino]cyclobutane-1,1-dicarboxylic acid;3-[(4-nonylphenyl)methylamino]cyclobutane-1,1-dicarboxylic acid Chemical compound C1=CC(CCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)C1.C1=CC(CCCCCCC)=CC=C1C(C(=C1)F)=CC=C1CNC1CC(C(O)=O)(C(O)=O)C1 RYJSLJUODDKCPV-UHFFFAOYSA-N 0.000 claims 1
• KCCXPBBPGJTACM-UHFFFAOYSA-N 3-[cyclopropyl-[(4-nonylphenyl)methyl]amino]cyclopentane-1,1-dicarboxylic acid 3-[[3-fluoro-4-(4-heptylphenyl)phenyl]methyl-methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound FC1=C(C=CC(=C1)CN(C1CC(CC1)(C(=O)O)C(=O)O)C)C1=CC=C(C=C1)CCCCCCC.C1(CC1)N(C1CC(CC1)(C(=O)O)C(=O)O)CC1=CC=C(C=C1)CCCCCCCCC KCCXPBBPGJTACM-UHFFFAOYSA-N 0.000 claims 1
• CTNMXIHOXOZSDA-UHFFFAOYSA-N 4-[2-(2,3-difluoro-4-nonylphenyl)ethylamino]-1-ethoxycarbonylcyclohexane-1-carboxylic acid 4-[(2,3-difluoro-4-nonylphenyl)methylamino]cyclohexane-1,1-dicarboxylic acid Chemical compound FC1=C(F)C(CCCCCCCCC)=CC=C1CNC1CCC(C(O)=O)(C(O)=O)CC1.FC1=C(F)C(CCCCCCCCC)=CC=C1CCNC1CCC(C(=O)OCC)(C(O)=O)CC1 CTNMXIHOXOZSDA-UHFFFAOYSA-N 0.000 claims 1
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