RU2361865C2 - Производные пиримидина, обладающие свойствами антагониста сrth2 (варианты) - Google Patents

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Publication number

RU2361865C2

RU2361865C2 RU2005136655/04A RU2005136655A RU2361865C2 RU 2361865 C2 RU2361865 C2 RU 2361865C2 RU 2005136655/04 A RU2005136655/04 A RU 2005136655/04A RU 2005136655 A RU2005136655 A RU 2005136655A RU 2361865 C2 RU2361865 C2 RU 2361865C2

Authority

RU

Russia

Prior art keywords

amino

benzyl

acetic acid

dimethylamino

chloro

Prior art date

2003-04-25

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• 150000003230 pyrimidines Chemical class 0.000 title claims abstract description 40
• 239000005557 antagonist Substances 0.000 title abstract description 5
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title abstract description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 200
• -1 C1-6alkyl ester Chemical class 0.000 claims abstract description 186
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 52
• 150000002367 halogens Chemical class 0.000 claims abstract description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
• 239000001257 hydrogen Substances 0.000 claims abstract description 39
• 150000003839 salts Chemical class 0.000 claims abstract description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 34
• 230000000694 effects Effects 0.000 claims abstract description 26
• 102000009389 Prostaglandin D receptors Human genes 0.000 claims abstract description 24
• 108050000258 Prostaglandin D receptors Proteins 0.000 claims abstract description 24
• 208000026935 allergic disease Diseases 0.000 claims abstract description 17
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 14
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 13
• 201000010099 disease Diseases 0.000 claims abstract description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 12
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims abstract description 11
• 210000003979 eosinophil Anatomy 0.000 claims abstract description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
• 150000002825 nitriles Chemical group 0.000 claims abstract description 11
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 9
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 9
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
• 206010012438 Dermatitis atopic Diseases 0.000 claims abstract description 6
• 206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 6
• 201000010105 allergic rhinitis Diseases 0.000 claims abstract description 6
• 208000006673 asthma Diseases 0.000 claims abstract description 6
• 201000008937 atopic dermatitis Diseases 0.000 claims abstract description 6
• 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 6
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims abstract description 4
• SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical group NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims abstract description 3
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 20
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 4
• 239000001301 oxygen Substances 0.000 claims abstract 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 204
• 125000000217 alkyl group Chemical group 0.000 claims description 79
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 62
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 47
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 47
• 239000002904 solvent Substances 0.000 claims description 37
• 125000003545 alkoxy group Chemical group 0.000 claims description 31
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
• 150000002431 hydrogen Chemical class 0.000 claims description 15
• 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 11
• 125000001424 substituent group Chemical group 0.000 claims description 11
• 125000003118 aryl group Chemical group 0.000 claims description 10
• 239000003795 chemical substances by application Substances 0.000 claims description 9
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 125000001041 indolyl group Chemical group 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000005493 quinolyl group Chemical group 0.000 claims description 7
• 239000003826 tablet Substances 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 6
• 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 5
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 5
• 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 5
• 208000002205 allergic conjunctivitis Diseases 0.000 claims description 5
• 208000024998 atopic conjunctivitis Diseases 0.000 claims description 5
• YPFWOLUEYTWRKX-UHFFFAOYSA-N n-[4-[[5-(2-amino-2-oxoethyl)-4-chloro-6-(dimethylamino)pyrimidin-2-yl]methyl]phenyl]naphthalene-2-carboxamide Chemical compound ClC1=C(CC(N)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 YPFWOLUEYTWRKX-UHFFFAOYSA-N 0.000 claims description 5
• SETQVYMZHIVBRU-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-(phenylmethoxycarbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound C1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)OCC=3C=CC=CC=3)=CC=2)=N1 SETQVYMZHIVBRU-UHFFFAOYSA-N 0.000 claims description 4
• OGZNYVIPIIDZLY-UHFFFAOYSA-N 2-[4-(dimethylamino)-6-morpholin-4-yl-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-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=1N1CCOCC1 OGZNYVIPIIDZLY-UHFFFAOYSA-N 0.000 claims description 4
• OCXZEAWOZHRQKP-UHFFFAOYSA-N 2-[4-chloro-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]-6-pyrrolidin-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=C1N1CCCC1 OCXZEAWOZHRQKP-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
• 239000003085 diluting agent Substances 0.000 claims description 4
• PVIKTFHVHUGOLM-UHFFFAOYSA-N n-[4-[[4-chloro-5-(cyanomethyl)-6-(dimethylamino)pyrimidin-2-yl]methyl]phenyl]naphthalene-2-carboxamide Chemical compound ClC1=C(CC#N)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 PVIKTFHVHUGOLM-UHFFFAOYSA-N 0.000 claims description 4
• WNSNYYLIQITQFJ-UHFFFAOYSA-N n-[4-[[4-chloro-6-(dimethylamino)-5-(2h-tetrazol-5-ylmethyl)pyrimidin-2-yl]methyl]phenyl]naphthalene-2-carboxamide Chemical compound CN(C)C1=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=NC(Cl)=C1CC1=NN=NN1 WNSNYYLIQITQFJ-UHFFFAOYSA-N 0.000 claims description 4
• 230000002265 prevention Effects 0.000 claims description 4
• XEOSTBFUCNZKGS-UHFFFAOYSA-N 2-[4,6-bis(dimethylamino)-2-[[4-[[4-(trifluoromethyl)benzoyl]amino]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=CC(=CC=3)C(F)(F)F)=CC=2)=N1 XEOSTBFUCNZKGS-UHFFFAOYSA-N 0.000 claims description 3
• LAPHHRQYUAOFGX-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(4-chlorobenzoyl)-methylamino]phenyl]methyl]-6-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(=CC=2)N(C)C(=O)C=2C=CC(Cl)=CC=2)=N1 LAPHHRQYUAOFGX-UHFFFAOYSA-N 0.000 claims description 3
• UUEHKVXKFVUOKF-UHFFFAOYSA-N 2-[4-chloro-6-(dimethylamino)-2-[[4-(phenylmethoxycarbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)OCC=3C=CC=CC=3)=CC=2)=N1 UUEHKVXKFVUOKF-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 3
• 239000011230 binding agent Substances 0.000 claims description 3
• 229940079593 drug Drugs 0.000 claims description 3
• 235000003599 food sweetener Nutrition 0.000 claims description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
• 239000000314 lubricant Substances 0.000 claims description 3
• 239000003765 sweetening agent Substances 0.000 claims description 3
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-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
• VNJYZANVNXLMBK-UHFFFAOYSA-N 2-[2-[1-[4-[(3,4-dichlorobenzoyl)amino]phenyl]ethyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound N=1C=C(CC(O)=O)C(N(C)C)=NC=1C(C)C(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 VNJYZANVNXLMBK-UHFFFAOYSA-N 0.000 claims description 2
• WFSKXLWLRRRIJO-UHFFFAOYSA-N 2-[2-[1-[4-[(4-chlorobenzoyl)amino]phenyl]ethyl]-4-(dimethylamino)pyrimidin-5-yl]acetic acid Chemical compound N=1C=C(CC(O)=O)C(N(C)C)=NC=1C(C)C(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 WFSKXLWLRRRIJO-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
• OQGHYGCQIHVPKX-UHFFFAOYSA-N 2-[2-[[4-(3,3-dimethylbutanoylamino)phenyl]methyl]-4-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound C1=CC(NC(=O)CC(C)(C)C)=CC=C1CC1=NC=C(CC(O)=O)C(N2CCCC2)=N1 OQGHYGCQIHVPKX-UHFFFAOYSA-N 0.000 claims description 2
• QWKZLHMASPOSDC-UHFFFAOYSA-N 2-[2-[[4-(benzylcarbamoylamino)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)NCC=3C=CC=CC=3)=CC=2)=N1 QWKZLHMASPOSDC-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
• VIACNMLRKMDHEV-UHFFFAOYSA-N 2-[2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]-4-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound OC(=O)CC1=CN=C(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)N=C1N1CCCC1 VIACNMLRKMDHEV-UHFFFAOYSA-N 0.000 claims description 2
• BLGFEKQGRRINTG-UHFFFAOYSA-N 2-[2-[[4-[(3,4-dichlorobenzoyl)amino]phenyl]methyl]-4,6-bis(dimethylamino)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=C(Cl)C(Cl)=CC=3)=CC=2)=N1 BLGFEKQGRRINTG-UHFFFAOYSA-N 0.000 claims description 2
• ANWJXEFKLMMCHP-UHFFFAOYSA-N 2-[2-[[4-[(3,4-dichlorobenzoyl)amino]phenyl]methyl]-4-(dimethylamino)-6-methylpyrimidin-5-yl]acetic acid Chemical compound CC1=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 ANWJXEFKLMMCHP-UHFFFAOYSA-N 0.000 claims description 2
• IVOAQFSTFIFFRD-UHFFFAOYSA-N 2-[2-[[4-[(3,4-dichlorobenzoyl)amino]phenyl]methyl]-4-(dimethylamino)-6-morpholin-4-ylpyrimidin-5-yl]acetic acid Chemical compound N=1C(N2CCOCC2)=C(CC(O)=O)C(N(C)C)=NC=1CC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 IVOAQFSTFIFFRD-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
• 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
• ZBWYVWIGXMTAMQ-UHFFFAOYSA-N 2-[2-[[4-[(4-chlorobenzoyl)amino]phenyl]methyl]-4-(dimethylamino)-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N=1C(N2CCCC2)=C(CC(O)=O)C(N(C)C)=NC=1CC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 ZBWYVWIGXMTAMQ-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
• YTMBTJPYTXLXLT-UHFFFAOYSA-N 2-[2-[[4-[(4-chlorobenzoyl)amino]phenyl]methyl]-4-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N1=C(N2CCCC2)C(CC(=O)O)=CN=C1CC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 YTMBTJPYTXLXLT-UHFFFAOYSA-N 0.000 claims description 2
• PTVJXKKBDDFIEH-UHFFFAOYSA-N 2-[2-[[4-[(4-fluorobenzoyl)amino]phenyl]methyl]-4-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N1=C(N2CCCC2)C(CC(=O)O)=CN=C1CC(C=C1)=CC=C1NC(=O)C1=CC=C(F)C=C1 PTVJXKKBDDFIEH-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
• VIADXYASLLIBBI-NTEUORMPSA-N 2-[2-[[4-[[(e)-3-(4-chlorophenyl)prop-2-enoyl]amino]phenyl]methyl]-4,6-bis(dimethylamino)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=C\C=3C=CC(Cl)=CC=3)=CC=2)=N1 VIADXYASLLIBBI-NTEUORMPSA-N 0.000 claims description 2
• ONUBVPYJYUPJMQ-NTEUORMPSA-N 2-[2-[[4-[[(e)-3-(4-chlorophenyl)prop-2-enoyl]amino]phenyl]methyl]-4-(dimethylamino)-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N=1C(N2CCCC2)=C(CC(O)=O)C(N(C)C)=NC=1CC(C=C1)=CC=C1NC(=O)\C=C\C1=CC=C(Cl)C=C1 ONUBVPYJYUPJMQ-NTEUORMPSA-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
• NRDKCQHKFLCXRT-UHFFFAOYSA-N 2-[2-[[4-[[benzyl(methyl)carbamoyl]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)N(C)CC=3C=CC=CC=3)=CC=2)=N1 NRDKCQHKFLCXRT-UHFFFAOYSA-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
• IEQWOVCCLCITJC-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[1-[4-(naphthalene-2-carbonylamino)phenyl]ethyl]pyrimidin-5-yl]acetic acid Chemical compound C=1C=C(NC(=O)C=2C=C3C=CC=CC3=CC=2)C=CC=1C(C)C1=NC=C(CC(O)=O)C(N(C)C)=N1 IEQWOVCCLCITJC-UHFFFAOYSA-N 0.000 claims description 2
• JBCJIXHGOBOQOI-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[1-[4-(quinoline-2-carbonylamino)phenyl]ethyl]pyrimidin-5-yl]acetic acid Chemical compound C=1C=C(NC(=O)C=2N=C3C=CC=CC3=CC=2)C=CC=1C(C)C1=NC=C(CC(O)=O)C(N(C)C)=N1 JBCJIXHGOBOQOI-UHFFFAOYSA-N 0.000 claims description 2
• IYJAOVLMZKODOB-NTEUORMPSA-N 2-[4-(dimethylamino)-2-[1-[4-[[(e)-3-phenylprop-2-enoyl]amino]phenyl]ethyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C=C(CC(O)=O)C(N(C)C)=NC=1C(C)C(C=C1)=CC=C1NC(=O)\C=C\C1=CC=CC=C1 IYJAOVLMZKODOB-NTEUORMPSA-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
• WXBFZIGGWGVNCY-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]-6-propan-2-ylpyrimidin-5-yl]acetic acid Chemical compound CN(C)C1=C(CC(O)=O)C(C(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 WXBFZIGGWGVNCY-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
• PBUBGDUPQPHGCQ-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-[(3-phenoxybenzoyl)amino]phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N=1C(N2CCCC2)=C(CC(O)=O)C(N(C)C)=NC=1CC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1OC1=CC=CC=C1 PBUBGDUPQPHGCQ-UHFFFAOYSA-N 0.000 claims description 2
• JAOFGXGCUKKDCF-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-[(4-fluorobenzoyl)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(F)=CC=3)=CC=2)=N1 JAOFGXGCUKKDCF-UHFFFAOYSA-N 0.000 claims description 2
• RQZCDOIOWMSAAL-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-[(4-phenoxybenzoyl)amino]phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N=1C(N2CCCC2)=C(CC(O)=O)C(N(C)C)=NC=1CC(C=C1)=CC=C1NC(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 RQZCDOIOWMSAAL-UHFFFAOYSA-N 0.000 claims description 2
• QAAHQJRWEYVWSL-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-[(4-phenylbenzoyl)amino]phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound N=1C(N2CCCC2)=C(CC(O)=O)C(N(C)C)=NC=1CC(C=C1)=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=CC=C1 QAAHQJRWEYVWSL-UHFFFAOYSA-N 0.000 claims description 2
• KZCGWNVWJRIYQZ-MDWZMJQESA-N 2-[4-(dimethylamino)-2-[[4-[[(e)-3-(4-methoxyphenyl)prop-2-enoyl]amino]phenyl]methyl]-6-morpholin-4-ylpyrimidin-5-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1\C=C\C(=O)NC(C=C1)=CC=C1CC1=NC(N(C)C)=C(CC(O)=O)C(N2CCOCC2)=N1 KZCGWNVWJRIYQZ-MDWZMJQESA-N 0.000 claims description 2
• DLPWHXJHKLBDDS-KPKJPENVSA-N 2-[4-(dimethylamino)-2-[[4-[[(e)-3-[4-(trifluoromethyl)phenyl]prop-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)C(F)(F)F)=CC=2)=N1 DLPWHXJHKLBDDS-KPKJPENVSA-N 0.000 claims description 2
• GSHAEHFCCIKSRP-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-[[4-[[4-(trifluoromethoxy)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(OC(F)(F)F)=CC=3)=CC=2)=N1 GSHAEHFCCIKSRP-UHFFFAOYSA-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
• QCPVMOCGIQWSRP-UHFFFAOYSA-N 2-[4-(dimethylamino)-6-(methoxymethyl)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound CN(C)C1=C(CC(O)=O)C(COC)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 QCPVMOCGIQWSRP-UHFFFAOYSA-N 0.000 claims description 2
• JOJTVPWAEDPARE-UHFFFAOYSA-N 2-[4-(dimethylamino)-6-(methoxymethyl)-2-[[4-[[4-(trifluoromethyl)benzoyl]amino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound CN(C)C1=C(CC(O)=O)C(COC)=NC(CC=2C=CC(NC(=O)C=3C=CC(=CC=3)C(F)(F)F)=CC=2)=N1 JOJTVPWAEDPARE-UHFFFAOYSA-N 0.000 claims description 2
• SBKQRLWONFKCFV-UHFFFAOYSA-N 2-[4-(dimethylamino)-6-ethyl-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound CN(C)C1=C(CC(O)=O)C(CC)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 SBKQRLWONFKCFV-UHFFFAOYSA-N 0.000 claims description 2
• PVUSLECUHKYKFI-UHFFFAOYSA-N 2-[4-(dimethylamino)-6-ethyl-2-[[4-[[4-(trifluoromethyl)benzoyl]amino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound CN(C)C1=C(CC(O)=O)C(CC)=NC(CC=2C=CC(NC(=O)C=3C=CC(=CC=3)C(F)(F)F)=CC=2)=N1 PVUSLECUHKYKFI-UHFFFAOYSA-N 0.000 claims description 2
• OMDIJQIRAXUPFB-UHFFFAOYSA-N 2-[4-(dimethylamino)-6-methyl-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C(N(C)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 OMDIJQIRAXUPFB-UHFFFAOYSA-N 0.000 claims description 2
• DINJPARSGWZJLN-JLHYYAGUSA-N 2-[4-(dimethylamino)-6-morpholin-4-yl-2-[[4-[[(e)-3-phenylprop-2-enoyl]amino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(N2CCOCC2)=C(CC(O)=O)C(N(C)C)=NC=1CC(C=C1)=CC=C1NC(=O)\C=C\C1=CC=CC=C1 DINJPARSGWZJLN-JLHYYAGUSA-N 0.000 claims description 2
• GEJHDNYRGZSUTQ-UHFFFAOYSA-N 2-[4-(dimethylamino)-6-morpholin-4-yl-2-[[4-[[4-(trifluoromethyl)benzoyl]amino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(N2CCOCC2)=C(CC(O)=O)C(N(C)C)=NC=1CC(C=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 GEJHDNYRGZSUTQ-UHFFFAOYSA-N 0.000 claims description 2
• MRMSMOWNKYPGHI-UHFFFAOYSA-N 2-[4-(dimethylamino)-6-propan-2-yl-2-[[4-[[4-(trifluoromethyl)benzoyl]amino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound CN(C)C1=C(CC(O)=O)C(C(C)C)=NC(CC=2C=CC(NC(=O)C=3C=CC(=CC=3)C(F)(F)F)=CC=2)=N1 MRMSMOWNKYPGHI-UHFFFAOYSA-N 0.000 claims description 2
• BKHLPFXCOHVKNA-UHFFFAOYSA-N 2-[4-(dimethylamino)-6-pyrrolidin-1-yl-2-[[4-[[4-(trifluoromethyl)benzoyl]amino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(N2CCCC2)=C(CC(O)=O)C(N(C)C)=NC=1CC(C=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 BKHLPFXCOHVKNA-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
• 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
• 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
• 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
• WXARHGJSLJJRPG-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(4-chlorobenzoyl)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=C1 WXARHGJSLJJRPG-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
• GYUDXTUDABEZFS-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(4-nitrobenzoyl)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([N+]([O-])=O)C=C1 GYUDXTUDABEZFS-UHFFFAOYSA-N 0.000 claims description 2
• RGPFGWBVFSTDOG-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(4-phenoxybenzoyl)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)C(C=C1)=CC=C1OC1=CC=CC=C1 RGPFGWBVFSTDOG-UHFFFAOYSA-N 0.000 claims description 2
• NCBINUVTUKRPQC-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[(4-propan-2-yloxybenzoyl)amino]phenyl]methyl]-6-pyrrolidin-1-ylpyrimidin-5-yl]acetic acid Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)NC(C=C1)=CC=C1CC1=NC(Cl)=C(CC(O)=O)C(N2CCCC2)=N1 NCBINUVTUKRPQC-UHFFFAOYSA-N 0.000 claims description 2
• FEQHBGJZYPBKBZ-UHFFFAOYSA-N 2-[4-chloro-6-(2,5-dihydropyrrol-1-yl)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-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=C1N1CC=CC1 FEQHBGJZYPBKBZ-UHFFFAOYSA-N 0.000 claims description 2
• JDIZIXSBVMDTGP-UHFFFAOYSA-N 2-[4-chloro-6-(3-hydroxypyrrolidin-1-yl)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound C1C(O)CCN1C1=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=NC(Cl)=C1CC(O)=O JDIZIXSBVMDTGP-UHFFFAOYSA-N 0.000 claims description 2
• VHSVZJXHYNEFJG-UHFFFAOYSA-N 2-[4-chloro-6-(diethylamino)-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(CC)CC)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 VHSVZJXHYNEFJG-UHFFFAOYSA-N 0.000 claims description 2
• YUCAAEGJPQENEU-UHFFFAOYSA-N 2-[4-chloro-6-(dimethylamino)-2-[[4-(quinoline-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=3N=C4C=CC=CC4=CC=3)=CC=2)=N1 YUCAAEGJPQENEU-UHFFFAOYSA-N 0.000 claims description 2
• XOYVUOXXCXNZOO-UHFFFAOYSA-N 2-[4-chloro-6-(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)=C(Cl)N=3)N(C)C)=CC=2)=C1 XOYVUOXXCXNZOO-UHFFFAOYSA-N 0.000 claims description 2
• SCBZDUVBOFIDSN-UHFFFAOYSA-N 2-[4-chloro-6-(dimethylamino)-2-[[4-[(4-methoxybenzoyl)amino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C(=O)NC(C=C1)=CC=C1CC1=NC(Cl)=C(CC(O)=O)C(N(C)C)=N1 SCBZDUVBOFIDSN-UHFFFAOYSA-N 0.000 claims description 2
• SRIRZKGHEYTTGC-UHFFFAOYSA-N 2-[4-chloro-6-(dimethylamino)-2-[[4-[[4-(dimethylamino)benzoyl]amino]phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound C1=CC(N(C)C)=CC=C1C(=O)NC(C=C1)=CC=C1CC1=NC(Cl)=C(CC(O)=O)C(N(C)C)=N1 SRIRZKGHEYTTGC-UHFFFAOYSA-N 0.000 claims description 2
• AQKMGBOJZABCHV-UHFFFAOYSA-N 2-[4-chloro-6-[2-hydroxyethyl(methyl)amino]-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(CCO)C)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 AQKMGBOJZABCHV-UHFFFAOYSA-N 0.000 claims description 2
• BKKCKMSIZYLPNF-UHFFFAOYSA-N 2-[4-chloro-6-[2-methoxyethyl(methyl)amino]-2-[[4-(naphthalene-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)C(N(C)CCOC)=NC(CC=2C=CC(NC(=O)C=3C=C4C=CC=CC4=CC=3)=CC=2)=N1 BKKCKMSIZYLPNF-UHFFFAOYSA-N 0.000 claims description 2
• CNQWNLPWQQBGDN-UHFFFAOYSA-N 2-[4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]-2-[[4-(1h-indole-2-carbonylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)C=3NC4=CC=CC=C4C=3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 CNQWNLPWQQBGDN-UHFFFAOYSA-N 0.000 claims description 2
• BZIIHAICJSLRJR-UHFFFAOYSA-N 2-[4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]-2-[[4-(2-phenylethylcarbamoylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)NCCC=3C=CC=CC=3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 BZIIHAICJSLRJR-UHFFFAOYSA-N 0.000 claims description 2
• AZOYPRLBVNQPKE-UHFFFAOYSA-N 2-[4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]-2-[[4-(3-phenylpropanoylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)CCC=3C=CC=CC=3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 AZOYPRLBVNQPKE-UHFFFAOYSA-N 0.000 claims description 2
• BSDWMUIIHHCWPD-UHFFFAOYSA-N 2-[4-chloro-6-[[2-(cyclopentylamino)-2-oxoethyl]-methylamino]-2-[[4-(naphthalen-2-ylcarbamoylamino)phenyl]methyl]pyrimidin-5-yl]acetic acid Chemical compound N=1C(CC=2C=CC(NC(=O)NC=3C=C4C=CC=CC4=CC=3)=CC=2)=NC(Cl)=C(CC(O)=O)C=1N(C)CC(=O)NC1CCCC1 BSDWMUIIHHCWPD-UHFFFAOYSA-N 0.000 claims description 2
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