HRP20010867A2 - 5-phenyl-pyrimidine derivatives - Google Patents
5-phenyl-pyrimidine derivatives Download PDFInfo
- Publication number
- HRP20010867A2 HRP20010867A2 HR20010867A HRP20010867A HRP20010867A2 HR P20010867 A2 HRP20010867 A2 HR P20010867A2 HR 20010867 A HR20010867 A HR 20010867A HR P20010867 A HRP20010867 A HR P20010867A HR P20010867 A2 HRP20010867 A2 HR P20010867A2
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- trifluoromethyl
- bis
- pyrimidine
- phenyl
- Prior art date
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- LVXOXXGCJHYEOS-UHFFFAOYSA-N 5-phenylpyrimidine Chemical class C1=CC=CC=C1C1=CN=CN=C1 LVXOXXGCJHYEOS-UHFFFAOYSA-N 0.000 title 1
- -1 amino, hydroxy Chemical group 0.000 claims description 88
- 150000001875 compounds Chemical class 0.000 claims description 69
- 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 38
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 229910052736 halogen Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 claims description 6
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 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 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- MHCBCPKFIVQLDP-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n,2-dimethyl-n-[5-(2-methylphenyl)-2-(4-methylpiperazin-1-yl)pyrimidin-4-yl]propanamide Chemical compound N=1C(N2CCN(C)CC2)=NC=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 MHCBCPKFIVQLDP-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005322 morpholin-1-yl group Chemical group 0.000 claims description 4
- UDRXMUSKHDXOJG-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-(2-chlorophenyl)-n-methyl-2-[(4-methylpiperazin-1-yl)methyl]pyrimidine-4-carboxamide Chemical compound N=1C(CN2CCN(C)CC2)=NC=C(C=2C(=CC=CC=2)Cl)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UDRXMUSKHDXOJG-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
- DEVPSDQVGIWSKN-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-N-methylmethanamine 2-[2-(dimethylamino)ethylamino]-5-(4-fluoro-2-methylphenyl)pyrimidine-4-carboxylic acid Chemical compound CC(C=C(C=C1)F)=C1C1=CN=C(NCCN(C)C)N=C1C(O)=O.CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DEVPSDQVGIWSKN-UHFFFAOYSA-N 0.000 claims description 3
- SFZQAYUWUVVNKG-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n-[2-[2-(dimethylamino)ethoxy]-5-(2-methylphenyl)pyrimidin-4-yl]-n,2-dimethylpropanamide Chemical compound N=1C(OCCN(C)C)=NC=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 SFZQAYUWUVVNKG-UHFFFAOYSA-N 0.000 claims description 3
- RVUNJRONZOPCII-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n-[2-[2-(dimethylamino)ethylamino]-5-(2-methylphenyl)pyrimidin-4-yl]-n,2-dimethylpropanamide Chemical compound N=1C(NCCN(C)C)=NC=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 RVUNJRONZOPCII-UHFFFAOYSA-N 0.000 claims description 3
- SZLYUSKDQJHNRQ-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n-[5-(2-chlorophenyl)-2-[2-(dimethylamino)ethylamino]pyrimidin-4-yl]-n,2-dimethylpropanamide Chemical compound N=1C(NCCN(C)C)=NC=C(C=2C(=CC=CC=2)Cl)C=1N(C)C(=O)C(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SZLYUSKDQJHNRQ-UHFFFAOYSA-N 0.000 claims description 3
- ZKVUFOVKOGJDRN-UHFFFAOYSA-N CC(C=C(C=C1)F)=C1C(C(C(O)=O)=N1)=CN=C1OCCCN(C)C.CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 Chemical compound CC(C=C(C=C1)F)=C1C(C(C(O)=O)=N1)=CN=C1OCCCN(C)C.CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ZKVUFOVKOGJDRN-UHFFFAOYSA-N 0.000 claims description 3
- LSRYMDNKLXDLJR-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[2-(dimethylamino)ethoxy]-5-(4-fluoro-2-methylphenyl)-n-methylpyrimidine-4-carboxamide Chemical compound N=1C(OCCN(C)C)=NC=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 LSRYMDNKLXDLJR-UHFFFAOYSA-N 0.000 claims description 3
- ONGNPPCOCAGOPG-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[2-(dimethylamino)propoxy]-5-(2-methoxyphenyl)-n-methylpyrimidine-4-carboxamide Chemical compound COC1=CC=CC=C1C1=CN=C(OCC(C)N(C)C)N=C1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ONGNPPCOCAGOPG-UHFFFAOYSA-N 0.000 claims description 3
- LSKKBONJQDIOLM-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[3-(dimethylamino)propoxy]-n-methyl-5-naphthalen-1-ylpyrimidine-4-carboxamide Chemical compound N=1C(OCCCN(C)C)=NC=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 LSKKBONJQDIOLM-UHFFFAOYSA-N 0.000 claims description 3
- IWDGCXSJAXWAAQ-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-(2-chlorophenyl)-2-[2-(dimethylamino)ethoxy]-n-methylpyrimidine-4-carboxamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C)C(=O)C1=NC(OCCN(C)C)=NC=C1C1=CC=CC=C1Cl IWDGCXSJAXWAAQ-UHFFFAOYSA-N 0.000 claims description 3
- YGNKYTPWQFKQCC-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-(2-chlorophenyl)-2-[3-(dimethylamino)propoxy]-n-methylpyrimidine-4-carboxamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C)C(=O)C1=NC(OCCCN(C)C)=NC=C1C1=CC=CC=C1Cl YGNKYTPWQFKQCC-UHFFFAOYSA-N 0.000 claims description 3
- KFXSMLUPVREIBI-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-(2-chlorophenyl)-2-[[2-(dimethylamino)ethylamino]methyl]-n-methylpyrimidine-4-carboxamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1CN(C)C(=O)C1=NC(CNCCN(C)C)=NC=C1C1=CC=CC=C1Cl KFXSMLUPVREIBI-UHFFFAOYSA-N 0.000 claims description 3
- RPANOJYUVQWJJF-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-(2-chlorophenyl)-n-methyl-2-(4-methylpiperazin-1-yl)pyrimidine-4-carboxamide Chemical compound N=1C(N2CCN(C)CC2)=NC=C(C=2C(=CC=CC=2)Cl)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 RPANOJYUVQWJJF-UHFFFAOYSA-N 0.000 claims description 3
- QADIQMNKFQHMAC-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-(4-fluoro-2-methylphenyl)-n-methyl-2-(4-methylpiperazin-1-yl)pyrimidine-4-carboxamide Chemical compound N=1C(N2CCN(C)CC2)=NC=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 QADIQMNKFQHMAC-UHFFFAOYSA-N 0.000 claims description 3
- ROMJHCFBYGSFRP-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-5-(4-fluoro-2-methylphenyl)-n-methyl-2-methylsulfanylpyrimidine-4-carboxamide Chemical compound N=1C(SC)=NC=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 ROMJHCFBYGSFRP-UHFFFAOYSA-N 0.000 claims description 3
- GDKOIHXLULPCFD-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-2-(2-morpholin-4-ylethoxy)-5-naphthalen-1-ylpyrimidine-4-carboxamide Chemical compound N=1C(OCCN2CCOCC2)=NC=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 GDKOIHXLULPCFD-UHFFFAOYSA-N 0.000 claims description 3
- POVJXZDVWZIMHW-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-5-(2-methylphenyl)-2-methylsulfanylpyrimidine-4-carboxamide Chemical compound N=1C(SC)=NC=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 POVJXZDVWZIMHW-UHFFFAOYSA-N 0.000 claims description 3
- 229940044551 receptor antagonist Drugs 0.000 claims description 3
- 239000002464 receptor antagonist Substances 0.000 claims description 3
- LKFTVVIBFRWGQF-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-N-methylmethanamine 2-[2-(dimethylamino)ethylamino]-5-(4-fluorophenyl)pyrimidine-4-carboxylic acid Chemical compound CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1.CN(C)CCNC1=NC=C(C(C=C2)=CC=C2F)C(C(O)=O)=N1 LKFTVVIBFRWGQF-UHFFFAOYSA-N 0.000 claims description 2
- DBJLECUAJPMFFN-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-N-methylmethanamine 5-(2-chlorophenyl)-2-[2-(dimethylamino)ethylamino]pyrimidine-4-carboxylic acid Chemical compound CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1.CN(C)CCNC1=NC=C(C(C=CC=C2)=C2Cl)C(C(O)=O)=N1 DBJLECUAJPMFFN-UHFFFAOYSA-N 0.000 claims description 2
- XVRXDNPXQFMNGO-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n,2-dimethyl-n-[5-(2-methylphenyl)-2-morpholin-4-ylpyrimidin-4-yl]propanamide Chemical compound N=1C(N2CCOCC2)=NC=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 XVRXDNPXQFMNGO-UHFFFAOYSA-N 0.000 claims description 2
- CDZDHHFJJTZBEJ-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n,2-dimethyl-n-[5-(2-methylphenyl)-2-piperazin-1-ylpyrimidin-4-yl]propanamide Chemical compound N=1C(N2CCNCC2)=NC=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 CDZDHHFJJTZBEJ-UHFFFAOYSA-N 0.000 claims description 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 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
- LFEOXKWJSLYLAO-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[2-(dimethylamino)ethoxy]-n-methyl-5-(2-methylphenyl)pyrimidine-4-carboxamide Chemical compound N=1C(OCCN(C)C)=NC=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 LFEOXKWJSLYLAO-UHFFFAOYSA-N 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
- PECNBXZZHVWXGL-UHFFFAOYSA-N 5-(2-chlorophenyl)-2-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxylic acid Chemical group N=1C=C(C=2C(=CC=CC=2)Cl)C(C(=O)O)=NC=1OCCN1CCOCC1 PECNBXZZHVWXGL-UHFFFAOYSA-N 0.000 claims 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 303
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- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
- BYLIJEYRQCCRNV-UHFFFAOYSA-N tert-butyl n-[5-(2-methylphenyl)-2-methylsulfanylpyrimidin-4-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=NC(SC)=NC=C1C1=CC=CC=C1C BYLIJEYRQCCRNV-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychology (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Addiction (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99110482 | 1999-05-31 | ||
| PCT/EP2000/004702 WO2000073278A2 (en) | 1999-05-31 | 2000-05-24 | 5-phenyl-pyrimidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20010867A2 true HRP20010867A2 (en) | 2003-04-30 |
Family
ID=8238270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20010867A HRP20010867A2 (en) | 1999-05-31 | 2001-11-22 | 5-phenyl-pyrimidine derivatives |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US6756380B1 (es) |
| EP (1) | EP1187814B1 (es) |
| JP (1) | JP3590591B2 (es) |
| KR (1) | KR100478369B1 (es) |
| CN (1) | CN1187338C (es) |
| AR (1) | AR024145A1 (es) |
| AT (1) | ATE273962T1 (es) |
| AU (1) | AU769265B2 (es) |
| BR (1) | BR0011097A (es) |
| CA (1) | CA2375670C (es) |
| CO (1) | CO5170529A1 (es) |
| CZ (1) | CZ20014273A3 (es) |
| DE (1) | DE60013127T2 (es) |
| DK (1) | DK1187814T3 (es) |
| ES (1) | ES2225144T3 (es) |
| GC (1) | GC0000338A (es) |
| HK (1) | HK1046411B (es) |
| HR (1) | HRP20010867A2 (es) |
| HU (1) | HU225016B1 (es) |
| IL (2) | IL146519A0 (es) |
| JO (1) | JO2308B1 (es) |
| MA (1) | MA26794A1 (es) |
| MX (1) | MXPA01011704A (es) |
| MY (1) | MY136258A (es) |
| NO (1) | NO321334B1 (es) |
| NZ (1) | NZ515408A (es) |
| PE (1) | PE20010203A1 (es) |
| PL (1) | PL353492A1 (es) |
| PT (1) | PT1187814E (es) |
| RU (1) | RU2244710C2 (es) |
| SI (1) | SI1187814T1 (es) |
| TR (1) | TR200103460T2 (es) |
| TW (1) | TWI263638B (es) |
| WO (1) | WO2000073278A2 (es) |
| YU (1) | YU85001A (es) |
| ZA (1) | ZA200109496B (es) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPQ514600A0 (en) | 2000-01-18 | 2000-02-10 | James Cook University | Brain injury treatment |
| AU778913B2 (en) * | 2000-06-13 | 2004-12-23 | Basf Aktiengesellschaft | Fungicidal 5-phenyl substituted 2-(cyanoamino) pyrimidines |
| JP4092203B2 (ja) | 2000-12-21 | 2008-05-28 | ニトロメッド，インク． | 新規のシクロオキシゲナーゼ２選択的阻害剤としての置換アリール化合物、組成物、および使用方法 |
| PL375263A1 (en) | 2002-07-02 | 2005-11-28 | F.Hoffmann-La Roche Ag | 2,5-substituted pyrimidine derivatives as ccr-3 receptor antagonists |
| US7935698B2 (en) * | 2003-11-10 | 2011-05-03 | Synta Pharmaceuticals Corporation | Heteroaryl-hydrazone compounds |
| JP2007217282A (ja) * | 2004-03-04 | 2007-08-30 | Astellas Pharma Inc | 置換ピリミジン誘導体 |
| US7696202B2 (en) * | 2004-11-10 | 2010-04-13 | Synta Pharmaceuticals Corp. | IL-12 modulatory compounds |
| CA2598762A1 (en) | 2005-02-25 | 2006-08-31 | F. Hoffmann-La Roche Ag | Tablets with improved drug substance dispersibility |
| US9013997B2 (en) | 2012-06-01 | 2015-04-21 | Broadcom Corporation | System for performing distributed data cut-through |
| US10000459B2 (en) | 2013-03-15 | 2018-06-19 | Epigen Biosciences, Inc. | Heterocyclic compounds useful in the treatment of disease |
| GB201316600D0 (en) * | 2013-09-18 | 2013-10-30 | Redx Pharma Ltd | Agricultural chemicals |
| WO2016021562A1 (ja) * | 2014-08-06 | 2016-02-11 | キッセイ薬品工業株式会社 | シアノチオフェン誘導体 |
| US10420341B2 (en) | 2015-01-30 | 2019-09-24 | Basf Se | Herbicidal phenylpyrimidines |
| US10966426B2 (en) | 2016-07-20 | 2021-04-06 | Basf Se | Herbicidal compositions comprising phenylpyrimidines |
| CA3030082A1 (en) * | 2016-07-25 | 2018-02-01 | Basf Se | Herbicidal pyrimidine compounds |
| EA201990335A1 (ru) | 2016-07-25 | 2019-07-31 | Басф Се | Гербицидные пиримидиновые соединения |
| US11178871B2 (en) | 2016-07-26 | 2021-11-23 | Basf Se | Herbicidal pyrimidine compounds |
| WO2018019765A1 (en) | 2016-07-27 | 2018-02-01 | Basf Se | Herbicidal pyrimidine compounds |
| WO2018019574A1 (en) | 2016-07-28 | 2018-02-01 | Basf Se | Herbicidal pyrimidine compounds |
| WO2018229041A1 (en) | 2017-06-14 | 2018-12-20 | Basf Se | Herbicidal pyrimidine compounds |
| WO2019121374A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Herbicidal pyrimidine compounds |
| WO2019121373A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Herbicidal pyrimidine compounds |
| WO2019121408A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Herbicidal pyrimidine compounds |
| WO2019121352A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Herbicidal pyrimidine compounds |
| WO2020058062A1 (de) | 2018-09-19 | 2020-03-26 | Bayer Aktiengesellschaft | Herbizid wirksame substituierte phenylpyrimidinhydrazide |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR208171A1 (es) | 1972-09-29 | 1976-12-09 | Ciba Geigy Ag | Procedimiento para la obtencion de nuevos derivados del acido cef-3-em-4-carboxilico |
| PL181214B1 (pl) | 1993-12-29 | 2001-06-29 | Merck Sharp & Dohme | Podstawione związki morfolinowe, sposób ich wytwarzania oraz zawierające je kompozycje farmaceutyczne |
| WO1997009315A1 (en) | 1995-09-01 | 1997-03-13 | Signal Pharmaceuticals, Inc. | Pyrimidine carboxamides and related compounds and methods for treating inflammatory conditions |
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2000
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- 2000-05-24 DE DE60013127T patent/DE60013127T2/de not_active Expired - Fee Related
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- 2000-05-24 BR BR0011097-3A patent/BR0011097A/pt not_active Application Discontinuation
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2001
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- 2001-11-16 ZA ZA200109496A patent/ZA200109496B/en unknown
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- 2001-11-26 MA MA26425A patent/MA26794A1/fr unknown
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2002
- 2002-11-05 HK HK02108020.5A patent/HK1046411B/zh not_active IP Right Cessation
Also Published As
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| HRP20010871A2 (en) | 4-phenyl-pyrimidine derivatives | |
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| AU2002227921A1 (en) | Pyrimidine derivatives |
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