HRP20010871A2 - 4-phenyl-pyrimidine derivatives - Google Patents
4-phenyl-pyrimidine derivatives Download PDFInfo
- Publication number
- HRP20010871A2 HRP20010871A2 HR20010871A HRP20010871A HRP20010871A2 HR P20010871 A2 HRP20010871 A2 HR P20010871A2 HR 20010871 A HR20010871 A HR 20010871A HR P20010871 A HRP20010871 A HR P20010871A HR P20010871 A2 HRP20010871 A2 HR P20010871A2
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- pyrimidine
- trifluoromethyl
- bis
- benzyl
- Prior art date
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- MKLQPIYLZMLAER-UHFFFAOYSA-N 4-phenylpyrimidine Chemical class C1=CC=CC=C1C1=CC=NC=N1 MKLQPIYLZMLAER-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 61
- -1 amino, phenyl Chemical group 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 claims description 7
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- MKCGSOVKTLWSKE-OEEJBDNKSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-N-methylmethanamine 2-[(3S,5R)-3,5-dimethylpiperazin-1-yl]-4-(2-methylphenyl)pyrimidine-5-carboxylic acid Chemical compound C[C@H](C1)N[C@@H](C)CN1C1=NC=C(C(O)=O)C(C2=C(C)C=CC=C2)=N1.CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 MKCGSOVKTLWSKE-OEEJBDNKSA-N 0.000 claims description 4
- UHYRUIDFKYAJKZ-KAECKJJSSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-N-methylmethanamine 2-[(3S,5R)-3,5-dimethylpiperazin-1-yl]-4-naphthalen-1-ylpyrimidine-5-carboxylic acid Chemical compound C[C@H](C1)N[C@@H](C)CN1C1=NC=C(C(O)=O)C(C2=CC=CC3=CC=CC=C23)=N1.CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UHYRUIDFKYAJKZ-KAECKJJSSA-N 0.000 claims description 4
- XBFMATCYYBERSR-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n,2-dimethyl-n-[4-(2-methylphenyl)-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]propanamide Chemical compound C=1N=C(N2CCN(C)CC2)N=C(C=2C(=CC=CC=2)C)C=1N(C)C(=O)C(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XBFMATCYYBERSR-UHFFFAOYSA-N 0.000 claims description 4
- ONQLQNSIWJUKOU-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n,2-dimethyl-n-[4-(2-methylphenyl)-2-morpholin-4-ylpyrimidin-5-yl]propanamide Chemical compound C=1N=C(N2CCOCC2)N=C(C=2C(=CC=CC=2)C)C=1N(C)C(=O)C(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ONQLQNSIWJUKOU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000005322 morpholin-1-yl group Chemical group 0.000 claims description 4
- VEKHDODULNWLFV-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-chlorophenyl)-n-methyl-2-(2-morpholin-4-ylethoxy)pyrimidine-5-carboxamide Chemical compound C=1N=C(OCCN2CCOCC2)N=C(C=2C(=CC=CC=2)Cl)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VEKHDODULNWLFV-UHFFFAOYSA-N 0.000 claims description 4
- JPNMFOZCAUEOEP-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(4-fluorophenyl)-n-methyl-2-piperazin-1-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCNCC2)N=C(C=2C=CC(F)=CC=2)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JPNMFOZCAUEOEP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229940044551 receptor antagonist Drugs 0.000 claims description 4
- 239000002464 receptor antagonist Substances 0.000 claims description 4
- CEYUUWOJAANHPT-IWKKHLOMSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-N-methylmethanamine 2-[(3S,5R)-3,5-dimethylpiperazin-1-yl]-4-(4-fluoro-2-methylphenyl)pyrimidine-5-carboxylic acid Chemical class C[C@H](C1)N[C@@H](C)CN1C1=NC=C(C(O)=O)C(C(C=C2)=C(C)C=C2F)=N1.CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CEYUUWOJAANHPT-IWKKHLOMSA-N 0.000 claims description 3
- PSSFAHZSJPCROM-NJJJQDLFSA-N C[C@H](C1)N[C@@H](C)CN1C1=NC=C(C(O)=O)C(C(C=CC=C2)=C2Br)=N1.CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 Chemical class C[C@H](C1)N[C@@H](C)CN1C1=NC=C(C(O)=O)C(C(C=CC=C2)=C2Br)=N1.CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 PSSFAHZSJPCROM-NJJJQDLFSA-N 0.000 claims description 3
- IZXHFBMOXVPZRJ-NJJJQDLFSA-N C[C@H](C1)N[C@@H](C)CN1C1=NC=C(C(O)=O)C(C(C=CC=C2)=C2Cl)=N1.CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 Chemical class C[C@H](C1)N[C@@H](C)CN1C1=NC=C(C(O)=O)C(C(C=CC=C2)=C2Cl)=N1.CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 IZXHFBMOXVPZRJ-NJJJQDLFSA-N 0.000 claims description 3
- YVKIVDUZGQEHIT-IWKKHLOMSA-N C[C@H](C1)N[C@@H](C)CN1C1=NC=C(C(O)=O)C(C(C=CC=C2)=C2OC)=N1.CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 Chemical class C[C@H](C1)N[C@@H](C)CN1C1=NC=C(C(O)=O)C(C(C=CC=C2)=C2OC)=N1.CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 YVKIVDUZGQEHIT-IWKKHLOMSA-N 0.000 claims description 3
- ISHGLRQBBCOHMY-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[2-(dimethylamino)ethoxy]-n-methyl-4-(2-methylphenyl)pyrimidine-5-carboxamide Chemical compound C=1C=CC=C(C)C=1C1=NC(OCCN(C)C)=NC=C1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ISHGLRQBBCOHMY-UHFFFAOYSA-N 0.000 claims description 3
- ANBVZLAKTIPPGV-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[3-(dimethylamino)propoxy]-n-methyl-4-(2-methylphenyl)pyrimidine-5-carboxamide Chemical compound C=1C=CC=C(C)C=1C1=NC(OCCCN(C)C)=NC=C1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ANBVZLAKTIPPGV-UHFFFAOYSA-N 0.000 claims description 3
- BIQMOXOJPSQULJ-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-bromophenyl)-n-methyl-2-(4-methylpiperazin-1-yl)pyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCN(C)CC2)N=C(C=2C(=CC=CC=2)Br)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BIQMOXOJPSQULJ-UHFFFAOYSA-N 0.000 claims description 3
- VSLUOQFTZGUBHP-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-bromophenyl)-n-methyl-2-morpholin-4-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCOCC2)N=C(C=2C(=CC=CC=2)Br)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VSLUOQFTZGUBHP-UHFFFAOYSA-N 0.000 claims description 3
- LZDIQCIFBXYNCQ-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-bromophenyl)-n-methyl-2-piperazin-1-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCNCC2)N=C(C=2C(=CC=CC=2)Br)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 LZDIQCIFBXYNCQ-UHFFFAOYSA-N 0.000 claims description 3
- YXUODTHFWOUPJK-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-chloro-4-fluorophenyl)-n-methyl-2-(4-methylpiperazin-1-yl)pyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCN(C)CC2)N=C(C=2C(=CC(F)=CC=2)Cl)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 YXUODTHFWOUPJK-UHFFFAOYSA-N 0.000 claims description 3
- TUXFGFJYPPJRNJ-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-chloro-4-fluorophenyl)-n-methyl-2-morpholin-4-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCOCC2)N=C(C=2C(=CC(F)=CC=2)Cl)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 TUXFGFJYPPJRNJ-UHFFFAOYSA-N 0.000 claims description 3
- BZVRGKQBBOXGST-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-chloro-4-fluorophenyl)-n-methyl-2-piperazin-1-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCNCC2)N=C(C=2C(=CC(F)=CC=2)Cl)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BZVRGKQBBOXGST-UHFFFAOYSA-N 0.000 claims description 3
- DBXDZQTZBIQLHO-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-chlorophenyl)-2-[2-(dimethylamino)ethylamino]-n-methylpyrimidine-5-carboxamide Chemical compound C=1C=CC=C(Cl)C=1C1=NC(NCCN(C)C)=NC=C1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DBXDZQTZBIQLHO-UHFFFAOYSA-N 0.000 claims description 3
- CAPPLWYXJSOETP-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-chlorophenyl)-2-[3-(dimethylamino)propoxy]-n-methylpyrimidine-5-carboxamide Chemical compound C=1C=CC=C(Cl)C=1C1=NC(OCCCN(C)C)=NC=C1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CAPPLWYXJSOETP-UHFFFAOYSA-N 0.000 claims description 3
- OAPRKIFHDPIMEB-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-chlorophenyl)-n-methyl-2-morpholin-4-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCOCC2)N=C(C=2C(=CC=CC=2)Cl)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OAPRKIFHDPIMEB-UHFFFAOYSA-N 0.000 claims description 3
- POXBBRWJVCVKOB-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-chlorophenyl)-n-methyl-2-piperazin-1-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCNCC2)N=C(C=2C(=CC=CC=2)Cl)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 POXBBRWJVCVKOB-UHFFFAOYSA-N 0.000 claims description 3
- HVDBRSFKHSRXIC-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-methoxyphenyl)-n-methyl-2-(4-methylpiperazin-1-yl)pyrimidine-5-carboxamide Chemical compound COC1=CC=CC=C1C1=NC(N2CCN(C)CC2)=NC=C1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HVDBRSFKHSRXIC-UHFFFAOYSA-N 0.000 claims description 3
- OXLXGKAREJVFPF-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-methoxyphenyl)-n-methyl-2-morpholin-4-ylpyrimidine-5-carboxamide Chemical compound COC1=CC=CC=C1C1=NC(N2CCOCC2)=NC=C1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OXLXGKAREJVFPF-UHFFFAOYSA-N 0.000 claims description 3
- UNSXBVOHYQSJKH-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-methoxyphenyl)-n-methyl-2-piperazin-1-ylpyrimidine-5-carboxamide Chemical compound COC1=CC=CC=C1C1=NC(N2CCNCC2)=NC=C1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UNSXBVOHYQSJKH-UHFFFAOYSA-N 0.000 claims description 3
- YRAGOJXJAMCZPC-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(4-fluoro-2-methylphenyl)-n-methyl-2-morpholin-4-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCOCC2)N=C(C=2C(=CC(F)=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 YRAGOJXJAMCZPC-UHFFFAOYSA-N 0.000 claims description 3
- MDUBZGVJCWXUQT-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(4-fluoro-2-methylphenyl)-n-methyl-2-piperazin-1-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCNCC2)N=C(C=2C(=CC(F)=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 MDUBZGVJCWXUQT-UHFFFAOYSA-N 0.000 claims description 3
- UNNTXNANCHCAFK-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(4-fluorophenyl)-n-methyl-2-(4-methylpiperazin-1-yl)pyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCN(C)CC2)N=C(C=2C=CC(F)=CC=2)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UNNTXNANCHCAFK-UHFFFAOYSA-N 0.000 claims description 3
- NVEAXNDODACIIB-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-2-(4-methylpiperazin-1-yl)-4-naphthalen-1-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCN(C)CC2)N=C(C=2C3=CC=CC=C3C=CC=2)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 NVEAXNDODACIIB-UHFFFAOYSA-N 0.000 claims description 3
- XEUJEJWVDFCNHU-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-2-morpholin-4-yl-4-naphthalen-1-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCOCC2)N=C(C=2C3=CC=CC=C3C=CC=2)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XEUJEJWVDFCNHU-UHFFFAOYSA-N 0.000 claims description 3
- SONFWIYUKIBJQD-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-4-(2-methylphenyl)-2-(4-methylpiperazin-1-yl)pyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCN(C)CC2)N=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SONFWIYUKIBJQD-UHFFFAOYSA-N 0.000 claims description 3
- XSHMSXWJIZVKKK-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-4-(2-methylphenyl)-2-morpholin-4-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCOCC2)N=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XSHMSXWJIZVKKK-UHFFFAOYSA-N 0.000 claims description 3
- ONJXZCYBQZZQIV-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-4-(2-methylphenyl)-2-piperazin-1-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCNCC2)N=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ONJXZCYBQZZQIV-UHFFFAOYSA-N 0.000 claims description 3
- GALOMJNOFVXOEH-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-4-naphthalen-1-yl-2-piperazin-1-ylpyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCNCC2)N=C(C=2C3=CC=CC=C3C=CC=2)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 GALOMJNOFVXOEH-UHFFFAOYSA-N 0.000 claims description 3
- TYYWRDWBUZAXGW-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-N-methylmethanamine 4-(2-fluorophenyl)-2-(4-methylpiperazin-1-yl)pyrimidine-5-carboxylic acid Chemical compound CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1.CN(CC1)CCN1C1=NC=C(C(O)=O)C(C(C=CC=C2)=C2F)=N1 TYYWRDWBUZAXGW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 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
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 2
- XIDOXZIEDHPPTQ-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(4-fluoro-2-methylphenyl)-n-methyl-2-(4-methylpiperazin-1-yl)pyrimidine-5-carboxamide Chemical compound C=1N=C(N2CCN(C)CC2)N=C(C=2C(=CC(F)=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XIDOXZIEDHPPTQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims 3
- QLHLFYLRIYRMFY-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-N-methylmethanamine 4-(2-chlorophenyl)-2-(4-methylpiperazin-1-yl)pyrimidine-5-carboxylic acid Chemical compound CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1.CN(CC1)CCN1C1=NC=C(C(O)=O)C(C(C=CC=C2)=C2Cl)=N1 QLHLFYLRIYRMFY-UHFFFAOYSA-N 0.000 claims 1
- WPNBQQHIXXXQOK-PHIMTYICSA-N 2-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-4-(2-fluorophenyl)pyrimidine-5-carboxylic acid Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=NC=C(C(O)=O)C(C=2C(=CC=CC=2)F)=N1 WPNBQQHIXXXQOK-PHIMTYICSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 238
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 88
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 72
- 239000006260 foam Substances 0.000 description 67
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- ADTNSTHKMIPKIJ-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ADTNSTHKMIPKIJ-UHFFFAOYSA-N 0.000 description 54
- 238000004587 chromatography analysis Methods 0.000 description 45
- 229910052681 coesite Inorganic materials 0.000 description 44
- 229910052906 cristobalite Inorganic materials 0.000 description 44
- 239000000377 silicon dioxide Substances 0.000 description 44
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- 239000007787 solid Substances 0.000 description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 239000012044 organic layer Substances 0.000 description 42
- 239000002244 precipitate Substances 0.000 description 40
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 36
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Health & Medical Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Orthopedic Medicine & Surgery (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99110483 | 1999-05-31 | ||
PCT/EP2000/004701 WO2000073279A1 (fr) | 1999-05-31 | 2000-05-24 | Derives de 4-phenyle-pyrimidine |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20010871A2 true HRP20010871A2 (en) | 2003-04-30 |
Family
ID=8238271
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20010871A HRP20010871A2 (en) | 1999-05-31 | 2001-11-22 | 4-phenyl-pyrimidine derivatives |
Country Status (36)
Country | Link |
---|---|
US (1) | US6274588B1 (fr) |
EP (1) | EP1187815B1 (fr) |
JP (1) | JP3590592B2 (fr) |
KR (1) | KR100440106B1 (fr) |
CN (1) | CN1166643C (fr) |
AR (1) | AR024146A1 (fr) |
AT (1) | ATE317389T1 (fr) |
AU (1) | AU770786B2 (fr) |
BR (1) | BR0011127A (fr) |
CA (1) | CA2375671C (fr) |
CO (1) | CO5170520A1 (fr) |
CZ (1) | CZ20014271A3 (fr) |
DE (1) | DE60025918T2 (fr) |
DK (1) | DK1187815T3 (fr) |
ES (1) | ES2257294T3 (fr) |
GC (1) | GC0000191A (fr) |
HK (1) | HK1046528B (fr) |
HR (1) | HRP20010871A2 (fr) |
HU (1) | HUP0201315A3 (fr) |
IL (2) | IL146460A0 (fr) |
JO (1) | JO2261B1 (fr) |
MA (1) | MA26793A1 (fr) |
MX (1) | MXPA01012089A (fr) |
MY (1) | MY122731A (fr) |
NO (1) | NO321354B1 (fr) |
NZ (1) | NZ515407A (fr) |
PE (1) | PE20010153A1 (fr) |
PL (1) | PL353441A1 (fr) |
PT (1) | PT1187815E (fr) |
RU (1) | RU2243221C2 (fr) |
SI (1) | SI1187815T1 (fr) |
TR (1) | TR200103457T2 (fr) |
TW (1) | TW550258B (fr) |
WO (1) | WO2000073279A1 (fr) |
YU (1) | YU84901A (fr) |
ZA (1) | ZA200109163B (fr) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AUPQ514600A0 (en) | 2000-01-18 | 2000-02-10 | James Cook University | Brain injury treatment |
WO2002022588A1 (fr) * | 2000-09-14 | 2002-03-21 | Ajinomoto Co.,Inc. | Nouveau derive de pyrimidine et nouveau derive de pyridine |
HUP0303841A2 (hu) * | 2001-02-20 | 2004-03-01 | Bristol-Myers Squibb Company | 2,4-Diszubsztituált-5-pirimidinkarboxamid-származékok mint KCNQ káliumcsatorna modulátorok és ezeket tartalmazó gyógyszerkészítmények és előállításuk |
US20070099938A1 (en) * | 2003-10-24 | 2007-05-03 | Ono Pharmaceutical Co., Ltd. | Antistress drug and medical use thereof |
HUP0400405A3 (en) * | 2004-02-10 | 2009-03-30 | Sanofi Synthelabo | Pyrimidine derivatives, process for producing them, their use, pharmaceutical compositions containing them and their intermediates |
WO2006050476A2 (fr) | 2004-11-03 | 2006-05-11 | Vertex Pharmaceuticals Incorporated | Modulateurs de canaux ioniques et leurs methodes d'utilisation |
US7176205B2 (en) * | 2005-02-22 | 2007-02-13 | Hoffmann-La Roche Inc. | Bi-pyridinyl derivatives as NK-1 antagonists |
CN101128189A (zh) | 2005-02-25 | 2008-02-20 | 弗·哈夫曼-拉罗切有限公司 | 药物物质分散性改善的片剂 |
AU2006259525B2 (en) * | 2005-06-14 | 2012-05-24 | Gpcr Therapeutics, Inc | Pyrimidine compounds |
CA2720229C (fr) | 2008-04-21 | 2015-02-17 | Taigen Biotechnology Co., Ltd. | Composes heterocycliques |
US8580805B2 (en) * | 2010-08-31 | 2013-11-12 | Hubert Maehr | Pyrimidine carboxamide derivatives |
CR20170387A (es) * | 2015-01-30 | 2018-02-16 | Basf Se | Fenilpirimidinas herbicidas |
RU2756055C2 (ru) * | 2017-01-10 | 2021-09-24 | Нэшнл Хелт Рисерч Инститьютс | Гетероциклические соединения и их применение |
KR102006547B1 (ko) * | 2017-11-16 | 2019-08-01 | 서울대학교산학협력단 | 벤즈아미드 유도체 화합물, 이의 제조방법 및 이를 유효성분으로 함유하는 염증질환의 치료 또는 예방용 약학적 조성물 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4698340A (en) | 1984-07-19 | 1987-10-06 | Fujisawa Pharmaceutical Co., Ltd. | Pyrimidine derivatives, processes for preparation thereof and composition containing the same |
DE3614060A1 (de) * | 1986-04-23 | 1987-10-29 | Schering Ag | Pyrimidin-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
US5516775A (en) * | 1992-08-31 | 1996-05-14 | Ciba-Geigy Corporation | Further use of pyrimidine derivatives |
DE69428913T2 (de) | 1993-12-29 | 2002-05-29 | Merck Sharp & Dohme | Substituierte morpholinderivate und ihre verwendung als arzneimittel |
AU726522B2 (en) | 1995-09-01 | 2000-11-09 | Signal Pharmaceuticals, Inc. | Pyrimidine carboxamides and related compounds and methods for treating inflammatory conditions |
US5972938A (en) | 1997-12-01 | 1999-10-26 | Merck & Co., Inc. | Method for treating or preventing psychoimmunological disorders |
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2000
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- 2000-05-24 WO PCT/EP2000/004701 patent/WO2000073279A1/fr active IP Right Grant
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- 2000-05-24 MX MXPA01012089A patent/MXPA01012089A/es active IP Right Grant
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- 2000-05-26 PE PE2000000508A patent/PE20010153A1/es not_active Application Discontinuation
- 2000-05-28 JO JO200083A patent/JO2261B1/en active
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- 2001-11-26 MA MA26424A patent/MA26793A1/fr unknown
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Also Published As
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EP1187814B1 (fr) | Derives de 5-phenyle-pyrimidine | |
HRP20010871A2 (en) | 4-phenyl-pyrimidine derivatives | |
US6787539B2 (en) | 2,4,5,-trisubstituted pyrimidine derivatives | |
AU2002227921A1 (en) | Pyrimidine derivatives |
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