DE60303238T2 - Pyrimidin-Essigsäure Derivate geeignet zur Behandlung von CRTH2-bedingten Krankheiten - Google Patents

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Publication number

DE60303238T2

DE60303238T2 DE60303238T DE60303238T DE60303238T2 DE 60303238 T2 DE60303238 T2 DE 60303238T2 DE 60303238 T DE60303238 T DE 60303238T DE 60303238 T DE60303238 T DE 60303238T DE 60303238 T2 DE60303238 T2 DE 60303238T2

Authority

DE

Germany

Prior art keywords

pyrimidinyl

amino

benzyl

acetic acid

chloro

Prior art date

2003-04-25

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.)

Expired - Lifetime

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• 102000009389 Prostaglandin D receptors Human genes 0.000 title claims description 24
• 108050000258 Prostaglandin D receptors Proteins 0.000 title claims description 24
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 13
• 238000011282 treatment Methods 0.000 title claims description 13
• NRRCYZPJUABYHL-UHFFFAOYSA-N 2-Pyrimidine Acetic Acid Chemical class OC(=O)CC1=NC=CC=N1 NRRCYZPJUABYHL-UHFFFAOYSA-N 0.000 title claims description 12
• 201000010099 disease Diseases 0.000 title claims description 11
• -1 nitro, guanidino, pyrrolyl Chemical group 0.000 claims description 178
• 150000001875 compounds Chemical class 0.000 claims description 136
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 50
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 42
• 125000000217 alkyl group Chemical group 0.000 claims description 39
• 238000002360 preparation method Methods 0.000 claims description 23
• 230000000694 effects Effects 0.000 claims description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 17
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 16
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 125000001072 heteroaryl group Chemical group 0.000 claims description 9
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 8
• 150000002431 hydrogen Chemical group 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 5
• 208000032671 Allergic granulomatous angiitis Diseases 0.000 claims description 5
• 208000006344 Churg-Strauss Syndrome Diseases 0.000 claims description 5
• 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 5
• 208000018428 Eosinophilic granulomatosis with polyangiitis Diseases 0.000 claims description 5
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 5
• 208000002205 allergic conjunctivitis Diseases 0.000 claims description 5
• 201000010105 allergic rhinitis Diseases 0.000 claims description 5
• 208000006673 asthma Diseases 0.000 claims description 5
• 208000024998 atopic conjunctivitis Diseases 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 201000009890 sinusitis Diseases 0.000 claims description 5
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
• 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 4
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• KXPAVCJDTRYMRP-UHFFFAOYSA-N 2-[4,6-dichloro-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N1=C(Cl)C(CC(=O)O)=C(Cl)N=C1CC(C=C1)=CC=C1NC(=O)C1=CC=C(C=CC=C2)C2=C1 KXPAVCJDTRYMRP-UHFFFAOYSA-N 0.000 claims description 4
• XSGQONMWVRQSTD-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 XSGQONMWVRQSTD-UHFFFAOYSA-N 0.000 claims description 4
• CUNNBJJEJUDKNN-UHFFFAOYSA-N 2-[4-chloro-6-(dimethylamino)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 CUNNBJJEJUDKNN-UHFFFAOYSA-N 0.000 claims description 4
• BRLNZHPNOSUQCK-UHFFFAOYSA-N 2-[4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]-2-[[4-(phenylcarbamoylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)NC=3C=CC=CC=3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 BRLNZHPNOSUQCK-UHFFFAOYSA-N 0.000 claims description 4
• NNTXSGFBNMXPTD-UHFFFAOYSA-N 2-[4-methyl-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound OC(=O)CC=1C(C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=NC=1N1CCCC1 NNTXSGFBNMXPTD-UHFFFAOYSA-N 0.000 claims description 4
• 208000016557 Acute basophilic leukemia Diseases 0.000 claims description 4
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
• 206010052568 Urticaria chronic Diseases 0.000 claims description 4
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
• 201000008937 atopic dermatitis Diseases 0.000 claims description 4
• 208000024376 chronic urticaria Diseases 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 4
• 206010024378 leukocytosis Diseases 0.000 claims description 4
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
• 230000002265 prevention Effects 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 2
• BRAVLCWGFGRYAJ-UHFFFAOYSA-N 2-[2-[(4-benzamidophenyl)methyl]-4-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)C=3C=CC=CC=3)=CC=2)=NC=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 BRAVLCWGFGRYAJ-UHFFFAOYSA-N 0.000 claims description 2
• YBKWXSXHGJHDKJ-UHFFFAOYSA-N 2-[2-[(4-benzamidophenyl)methyl]-4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)C=3C=CC=CC=3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 YBKWXSXHGJHDKJ-UHFFFAOYSA-N 0.000 claims description 2
• HSJTTYZHQSKFMU-UHFFFAOYSA-N 2-[2-[[4-(1-benzofuran-2-carbonylamino)phenyl]methyl]-4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)C=3OC4=CC=CC=C4C=3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 HSJTTYZHQSKFMU-UHFFFAOYSA-N 0.000 claims description 2
• BLYDFBFHXASRNY-UHFFFAOYSA-N 2-[2-[[4-(benzylcarbamoylamino)phenyl]methyl]-4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)NCC=3C=CC=CC=3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 BLYDFBFHXASRNY-UHFFFAOYSA-N 0.000 claims description 2
• WULJEVKZTZYJFW-UHFFFAOYSA-N 2-[2-[[4-[(3,4-dichlorobenzoyl)amino]phenyl]methyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C(Cl)C(Cl)=CC=3)=CC=2)=N1 WULJEVKZTZYJFW-UHFFFAOYSA-N 0.000 claims description 2
• OXZAIUCHPIZYDI-UHFFFAOYSA-N 2-[2-[[4-[(3,4-dichlorobenzoyl)amino]phenyl]methyl]-4-methyl-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N=1C(N2CCCC2)=C(CC(O)=O)C(C)=NC=1CC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 OXZAIUCHPIZYDI-UHFFFAOYSA-N 0.000 claims description 2
• LOCILIUQLADHQZ-UHFFFAOYSA-N 2-[2-[[4-[(3-chlorobenzoyl)amino]phenyl]methyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C(Cl)C=CC=3)=CC=2)=N1 LOCILIUQLADHQZ-UHFFFAOYSA-N 0.000 claims description 2
• QBCSHZVZVUKCQO-UHFFFAOYSA-N 2-[2-[[4-[(4-acetamidobenzoyl)amino]phenyl]methyl]-4-chloro-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)NC(C=C1)=CC=C1CC1=NC(Cl)=C(CC(O)=O)C(N2CCCC2)=N1 QBCSHZVZVUKCQO-UHFFFAOYSA-N 0.000 claims description 2
• WDYCRZAIFVIUEV-UHFFFAOYSA-N 2-[2-[[4-[(4-bromobenzoyl)amino]phenyl]methyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=CC(Br)=CC=3)=CC=2)=N1 WDYCRZAIFVIUEV-UHFFFAOYSA-N 0.000 claims description 2
• AARBEQQNTOZBTL-UHFFFAOYSA-N 2-[2-[[4-[(4-bromobenzoyl)amino]phenyl]methyl]-4-chloro-6-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=CC(Br)=CC=3)=CC=2)=N1 AARBEQQNTOZBTL-UHFFFAOYSA-N 0.000 claims description 2
• LACBHKONDFDLLO-UHFFFAOYSA-N 2-[2-[[4-[(4-chlorobenzoyl)amino]phenyl]methyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=N1 LACBHKONDFDLLO-UHFFFAOYSA-N 0.000 claims description 2
• YAUYYYFLGPQZJN-UHFFFAOYSA-N 2-[2-[[4-[(4-tert-butylcyclohexanecarbonyl)amino]phenyl]methyl]-4-chloro-6-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C3CCC(CC3)C(C)(C)C)=CC=2)=N1 YAUYYYFLGPQZJN-UHFFFAOYSA-N 0.000 claims description 2
• FLVDJNIFQHPSAB-KPKJPENVSA-N 2-[2-[[4-[[(e)-3-(4-chlorophenyl)prop-2-enoyl]amino]phenyl]methyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)\C=C\C=3C=CC(Cl)=CC=3)=CC=2)=N1 FLVDJNIFQHPSAB-KPKJPENVSA-N 0.000 claims description 2
• HRFIBVDUAZPDBR-UHFFFAOYSA-N 2-[4,6-bis(dimethylamino)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound CN(C)C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 HRFIBVDUAZPDBR-UHFFFAOYSA-N 0.000 claims description 2
• BJWSMNONLBPUSX-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]-6-piperidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound OC(=O)CC=1C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=NC=1N1CCCCC1 BJWSMNONLBPUSX-UHFFFAOYSA-N 0.000 claims description 2
• VZQIUAMJIMFSOW-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound OC(=O)CC=1C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=NC=1N1CCCC1 VZQIUAMJIMFSOW-UHFFFAOYSA-N 0.000 claims description 2
• WZQHWHBFSVGSTJ-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-(quinoline-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3N=C4C=CC=CC4=CC=3)=CC=2)=N1 WZQHWHBFSVGSTJ-UHFFFAOYSA-N 0.000 claims description 2
• ZSKOFFLYTKCEIM-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-[(3-methoxybenzoyl)amino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound COC1=CC=CC(C(=O)NC=2C=CC(CC=3N=C(C(CC(O)=O)=CN=3)N(C)C)=CC=2)=C1 ZSKOFFLYTKCEIM-UHFFFAOYSA-N 0.000 claims description 2
• WIOSZSAVCVGCRK-JLHYYAGUSA-N 2-[4-(dimethylamino)-2-[[4-[[(e)-3-phenylprop-2-enoyl]amino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)\C=C\C=3C=CC=CC=3)=CC=2)=N1 WIOSZSAVCVGCRK-JLHYYAGUSA-N 0.000 claims description 2
• DJSYVPDFYKAFFR-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-[[4-(trifluoromethyl)benzoyl]amino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=CC(=CC=3)C(F)(F)F)=CC=2)=N1 DJSYVPDFYKAFFR-UHFFFAOYSA-N 0.000 claims description 2
• FZZZSCVAJSHOTP-UHFFFAOYSA-N 2-[4-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=NC=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 FZZZSCVAJSHOTP-UHFFFAOYSA-N 0.000 claims description 2
• BUVUXCNBRMWLTA-DTQAZKPQSA-N 2-[4-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]-2-[[4-[[(e)-3-phenylprop-2-enoyl]amino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)\C=C\C=3C=CC=CC=3)=CC=2)=NC=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 BUVUXCNBRMWLTA-DTQAZKPQSA-N 0.000 claims description 2
• OXWLKJXZSSGDRN-UHFFFAOYSA-N 2-[4-[carboxymethyl(methyl)amino]-6-chloro-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(CC(O)=O)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 OXWLKJXZSSGDRN-UHFFFAOYSA-N 0.000 claims description 2
• MGOYNGXEMSANKG-UHFFFAOYSA-N 2-[4-[methyl-(2-oxo-2-pyrrolidin-1-ylethyl)amino]-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=NC=C(CC(O)=O)C=1N(C)CC(=O)N1CCCC1 MGOYNGXEMSANKG-UHFFFAOYSA-N 0.000 claims description 2
• WEUSPEBVRKDRLM-UHFFFAOYSA-N 2-[4-chloro-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]-6-piperidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound OC(=O)CC1=C(Cl)N=C(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)N=C1N1CCCCC1 WEUSPEBVRKDRLM-UHFFFAOYSA-N 0.000 claims description 2
• UAPLHVKACQBFRY-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(2,5-dichlorobenzoyl)amino]phenyl]methyl]-6-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C(=CC=C(Cl)C=3)Cl)=CC=2)=N1 UAPLHVKACQBFRY-UHFFFAOYSA-N 0.000 claims description 2
• ZNTGLJGJOQBPOJ-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(2-cyclohexylacetyl)amino]phenyl]methyl]-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)CC3CCCCC3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 ZNTGLJGJOQBPOJ-UHFFFAOYSA-N 0.000 claims description 2
• JCPPYXISAHHCPF-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(3,4-dichlorobenzoyl)amino]phenyl]methyl]-6-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C(Cl)C(Cl)=CC=3)=CC=2)=N1 JCPPYXISAHHCPF-UHFFFAOYSA-N 0.000 claims description 2
• YGFDDDQXTSQSQN-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(3,4-dichlorobenzoyl)amino]phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N1=C(N2CCCC2)C(CC(=O)O)=C(Cl)N=C1CC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 YGFDDDQXTSQSQN-UHFFFAOYSA-N 0.000 claims description 2
• PICHTDWCXIURKN-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(3,4-difluorobenzoyl)amino]phenyl]methyl]-6-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C(F)C(F)=CC=3)=CC=2)=N1 PICHTDWCXIURKN-UHFFFAOYSA-N 0.000 claims description 2
• DOHVYOHYPAGMAF-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(3,4-dimethoxybenzoyl)amino]phenyl]methyl]-6-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NC(C=C1)=CC=C1CC1=NC(Cl)=C(CC(O)=O)C(N(C)C)=N1 DOHVYOHYPAGMAF-UHFFFAOYSA-N 0.000 claims description 2
• SFKVETIQAWQTMS-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(3,5-dichlorobenzoyl)amino]phenyl]methyl]-6-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C(Cl)C=C(Cl)C=3)=CC=2)=N1 SFKVETIQAWQTMS-UHFFFAOYSA-N 0.000 claims description 2
• QKSKYWATPYQNRY-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(3-chloro-4-methoxybenzoyl)amino]phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC=C1C(=O)NC(C=C1)=CC=C1CC1=NC(Cl)=C(CC(O)=O)C(N2CCCC2)=N1 QKSKYWATPYQNRY-UHFFFAOYSA-N 0.000 claims description 2
• GXRGQPPSNFDVRG-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(3-chlorobenzoyl)amino]phenyl]methyl]-6-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C(Cl)C=CC=3)=CC=2)=N1 GXRGQPPSNFDVRG-UHFFFAOYSA-N 0.000 claims description 2
• DJZFUDKILTZUGL-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(4-chlorobenzoyl)amino]phenyl]methyl]-6-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=N1 DJZFUDKILTZUGL-UHFFFAOYSA-N 0.000 claims description 2
• SLPMFCFFPOSDJT-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(4-methoxy-3,5-dimethylbenzoyl)amino]phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound C1=C(C)C(OC)=C(C)C=C1C(=O)NC(C=C1)=CC=C1CC1=NC(Cl)=C(CC(O)=O)C(N2CCCC2)=N1 SLPMFCFFPOSDJT-UHFFFAOYSA-N 0.000 claims description 2
• MADNSGWBZDSODE-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(4-methoxy-3-nitrobenzoyl)amino]phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound C1=C([N+]([O-])=O)C(OC)=CC=C1C(=O)NC(C=C1)=CC=C1CC1=NC(Cl)=C(CC(O)=O)C(N2CCCC2)=N1 MADNSGWBZDSODE-UHFFFAOYSA-N 0.000 claims description 2
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