ZA200109163B - 4-Phenyl-pyrimidine derivatives. - Google Patents
4-Phenyl-pyrimidine derivatives. Download PDFInfo
- Publication number
- ZA200109163B ZA200109163B ZA200109163A ZA200109163A ZA200109163B ZA 200109163 B ZA200109163 B ZA 200109163B ZA 200109163 A ZA200109163 A ZA 200109163A ZA 200109163 A ZA200109163 A ZA 200109163A ZA 200109163 B ZA200109163 B ZA 200109163B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- pyrimidine
- bis
- carboxylic acid
- 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 description 2
- 150000001875 compounds Chemical class 0.000 claims description 68
- -1 amino, phenyl Chemical group 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 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 claims description 25
- 239000000126 substance Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 229910052736 halogen Chemical group 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 238000004519 manufacturing process Methods 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
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 claims description 6
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- PUTASRWHAHNFNY-IYBDPMFKSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-4-(2-fluorophenyl)-n-methylpyrimidine-5-carboxamide Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1C=2C(=CC=CC=2)F)=NC=C1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 PUTASRWHAHNFNY-IYBDPMFKSA-N 0.000 claims description 3
- CNFYAIAZBJHRKO-KDURUIRLSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-n-methyl-4-naphthalen-1-ylpyrimidine-5-carboxamide Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1C=2C3=CC=CC=C3C=CC=2)=NC=C1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CNFYAIAZBJHRKO-KDURUIRLSA-N 0.000 claims description 3
- CJQIPEMNRWAJPQ-CALCHBBNSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-4-(4-fluoro-2-methylphenyl)-n-methylpyrimidine-5-carboxamide Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1C=2C(=CC(F)=CC=2)C)=NC=C1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CJQIPEMNRWAJPQ-CALCHBBNSA-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
- VMSNVHLVUSVXPB-IYBDPMFKSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-chlorophenyl)-2-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-n-methylpyrimidine-5-carboxamide Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1C=2C(=CC=CC=2)Cl)=NC=C1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VMSNVHLVUSVXPB-IYBDPMFKSA-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
- DGUPVIHNWCPSAV-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-chlorophenyl)-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)Cl)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DGUPVIHNWCPSAV-UHFFFAOYSA-N 0.000 claims description 3
- YYUGJAKZOXRQSK-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-fluorophenyl)-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)F)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 YYUGJAKZOXRQSK-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
- 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 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
- 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 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
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
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- 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
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- PIDAXIZOYXIOST-IYBDPMFKSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-bromophenyl)-2-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-n-methylpyrimidine-5-carboxamide Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(N=C1C=2C(=CC=CC=2)Br)=NC=C1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 PIDAXIZOYXIOST-IYBDPMFKSA-N 0.000 claims description 2
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- 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 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims 5
- BASLGMRTOGKAPE-BETUJISGSA-N 2-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-4-(2-methylphenyl)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)C)=N1 BASLGMRTOGKAPE-BETUJISGSA-N 0.000 claims 1
- BGHKHQNMNQXVSJ-UHFFFAOYSA-N 4-(2-methoxyphenyl)-2-(4-methylpiperazin-1-yl)pyrimidine-5-carboxylic acid Chemical compound COC1=CC=CC=C1C1=NC(N2CCN(C)CC2)=NC=C1C(O)=O BGHKHQNMNQXVSJ-UHFFFAOYSA-N 0.000 claims 1
- QXVVVZCJESAQLW-UHFFFAOYSA-N 4-naphthalen-1-yl-2-piperazin-1-ylpyrimidine-5-carboxylic acid Chemical compound N1=C(C=2C3=CC=CC=C3C=CC=2)C(C(=O)O)=CN=C1N1CCNCC1 QXVVVZCJESAQLW-UHFFFAOYSA-N 0.000 claims 1
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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EP99110483 | 1999-05-31 |
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ZA200109163B true ZA200109163B (en) | 2003-02-06 |
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ZA200109163A ZA200109163B (en) | 1999-05-31 | 2001-11-06 | 4-Phenyl-pyrimidine derivatives. |
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US (1) | US6274588B1 (de) |
EP (1) | EP1187815B1 (de) |
JP (1) | JP3590592B2 (de) |
KR (1) | KR100440106B1 (de) |
CN (1) | CN1166643C (de) |
AR (1) | AR024146A1 (de) |
AT (1) | ATE317389T1 (de) |
AU (1) | AU770786B2 (de) |
BR (1) | BR0011127A (de) |
CA (1) | CA2375671C (de) |
CO (1) | CO5170520A1 (de) |
CZ (1) | CZ20014271A3 (de) |
DE (1) | DE60025918T2 (de) |
DK (1) | DK1187815T3 (de) |
ES (1) | ES2257294T3 (de) |
GC (1) | GC0000191A (de) |
HK (1) | HK1046528B (de) |
HR (1) | HRP20010871A2 (de) |
HU (1) | HUP0201315A3 (de) |
IL (2) | IL146460A0 (de) |
JO (1) | JO2261B1 (de) |
MA (1) | MA26793A1 (de) |
MX (1) | MXPA01012089A (de) |
MY (1) | MY122731A (de) |
NO (1) | NO321354B1 (de) |
NZ (1) | NZ515407A (de) |
PE (1) | PE20010153A1 (de) |
PL (1) | PL353441A1 (de) |
PT (1) | PT1187815E (de) |
RU (1) | RU2243221C2 (de) |
SI (1) | SI1187815T1 (de) |
TR (1) | TR200103457T2 (de) |
TW (1) | TW550258B (de) |
WO (1) | WO2000073279A1 (de) |
YU (1) | YU84901A (de) |
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---|---|---|---|---|
AUPQ514600A0 (en) | 2000-01-18 | 2000-02-10 | James Cook University | Brain injury treatment |
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WO2005040135A1 (ja) * | 2003-10-24 | 2005-05-06 | Ono Pharmaceutical Co., Ltd. | 抗ストレス薬およびその医薬用途 |
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 |
EP1809290A2 (de) * | 2004-11-03 | 2007-07-25 | Vertex Pharmaceuticals Incorporated | Pyrimidinderivate als ionenkanalmodulatoren und verwendungsverfahren |
ES2329827T3 (es) * | 2005-02-22 | 2009-12-01 | F. Hoffmann-La Roche Ag | Antagonistas de nk1. |
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ES2545731T3 (es) | 2008-04-21 | 2015-09-15 | Taigen Biotechnology Co., Ltd. | Compuestos heterocíclicos |
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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 |
EP0737192B1 (de) | 1993-12-29 | 2001-10-31 | Merck Sharp & Dohme Ltd. | Substituierte morpholinderivate und ihre verwendung als arzneimittel |
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