NO321354B1 - 4-fenyl-pyrimidinderivater, fremgangsmate for deres fremstilling samt anvendelse av disse for tillaging av medikamenter for behandling av sykdom. - Google Patents
4-fenyl-pyrimidinderivater, fremgangsmate for deres fremstilling samt anvendelse av disse for tillaging av medikamenter for behandling av sykdom. Download PDFInfo
- Publication number
- NO321354B1 NO321354B1 NO20015700A NO20015700A NO321354B1 NO 321354 B1 NO321354 B1 NO 321354B1 NO 20015700 A NO20015700 A NO 20015700A NO 20015700 A NO20015700 A NO 20015700A NO 321354 B1 NO321354 B1 NO 321354B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- phenyl
- amide
- carboxylic acid
- bis
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 239000003814 drug Substances 0.000 title claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 6
- 201000010099 disease Diseases 0.000 title claims 3
- 230000008569 process Effects 0.000 title description 2
- 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 59
- -1 carbamoyl-Ci-6-alkyl Chemical group 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 18
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 229940047889 isobutyramide Drugs 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 claims description 5
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 claims description 5
- 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 4
- 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 4
- 239000002464 receptor antagonist Substances 0.000 claims description 4
- 229940044551 receptor antagonist Drugs 0.000 claims description 4
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 claims description 4
- MYUVEMKMWKWVEH-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-[2-(dimethylamino)ethoxy]pyrimidine-5-carboxylic acid Chemical compound CN(C)CCOC1=NC=C(C(O)=O)C(C=2C(=CC=CC=2)Cl)=N1 MYUVEMKMWKWVEH-UHFFFAOYSA-N 0.000 claims description 3
- OAAKRBLQBYRSNR-PHIMTYICSA-N 4-(2-chlorophenyl)-2-[(3r,5s)-3,5-dimethylpiperazin-1-yl]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)Cl)=N1 OAAKRBLQBYRSNR-PHIMTYICSA-N 0.000 claims description 2
- FSODCEMWIIAEDV-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-piperazin-1-ylpyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(N2CCNCC2)N=C1C1=CC=CC=C1Cl FSODCEMWIIAEDV-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 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
- 229940079593 drug Drugs 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 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
- QCJDYYBZLFZODE-CALCHBBNSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-4-(2-methoxyphenyl)-n-methylpyrimidine-5-carboxamide Chemical compound COC1=CC=CC=C1C1=NC(N2C[C@@H](C)N[C@@H](C)C2)=NC=C1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 QCJDYYBZLFZODE-CALCHBBNSA-N 0.000 claims description 2
- 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 2
- 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 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
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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 12
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- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 description 8
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Classifications
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- C07D239/34—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
- C07D239/38—One sulfur 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
- C07D239/48—Two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Addiction (AREA)
- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Otolaryngology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99110483 | 1999-05-31 | ||
PCT/EP2000/004701 WO2000073279A1 (en) | 1999-05-31 | 2000-05-24 | 4-phenyl-pyrimidine derivatives |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20015700D0 NO20015700D0 (no) | 2001-11-22 |
NO20015700L NO20015700L (no) | 2001-11-22 |
NO321354B1 true NO321354B1 (no) | 2006-05-02 |
Family
ID=8238271
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20015700A NO321354B1 (no) | 1999-05-31 | 2001-11-22 | 4-fenyl-pyrimidinderivater, fremgangsmate for deres fremstilling samt anvendelse av disse for tillaging av medikamenter for behandling av sykdom. |
Country Status (36)
Country | Link |
---|---|
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) |
ZA (1) | ZA200109163B (de) |
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 |
AU2001284504A1 (en) * | 2000-09-14 | 2002-03-26 | Ajinomoto Co., Inc. | Novel pyrimidine derivative and novel pyridine derivative |
CA2438231A1 (en) * | 2001-02-20 | 2002-08-29 | Gene G. Kinney | 2,4-disubstituted pyrimidine-5-carboxamide derivatives as kcnq potassium channel modulators |
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. |
RU2007129642A (ru) | 2005-02-25 | 2009-03-27 | Ф.Хоффманн-Ля Рош Аг (Ch) | Таблетки с улучшенным распределением лекарственного вещества |
WO2006138304A2 (en) | 2005-06-14 | 2006-12-28 | Taigen Biotechnology | Pyrimidine compounds |
ES2545731T3 (es) | 2008-04-21 | 2015-09-15 | Taigen Biotechnology Co., Ltd. | Compuestos heterocíclicos |
US8580805B2 (en) * | 2010-08-31 | 2013-11-12 | Hubert Maehr | Pyrimidine carboxamide derivatives |
MX2017009843A (es) * | 2015-01-30 | 2017-11-02 | Basf Se | Fenilpirimidinas herbicidas. |
CN110381949B (zh) * | 2017-01-10 | 2023-12-08 | 财团法人卫生研究院 | 杂环化合物及其用途 |
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 |
EP0737192B1 (de) | 1993-12-29 | 2001-10-31 | Merck Sharp & Dohme Ltd. | Substituierte morpholinderivate und ihre verwendung als arzneimittel |
WO1997009315A1 (en) | 1995-09-01 | 1997-03-13 | 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 |
-
2000
- 2000-05-22 TW TW089109829A patent/TW550258B/zh not_active IP Right Cessation
- 2000-05-22 US US09/575,382 patent/US6274588B1/en not_active Expired - Fee Related
- 2000-05-24 HU HU0201315A patent/HUP0201315A3/hu unknown
- 2000-05-24 MX MXPA01012089A patent/MXPA01012089A/es active IP Right Grant
- 2000-05-24 EP EP00927234A patent/EP1187815B1/de not_active Expired - Lifetime
- 2000-05-24 AT AT00927234T patent/ATE317389T1/de not_active IP Right Cessation
- 2000-05-24 CZ CZ20014271A patent/CZ20014271A3/cs unknown
- 2000-05-24 PT PT00927234T patent/PT1187815E/pt unknown
- 2000-05-24 AU AU45677/00A patent/AU770786B2/en not_active Ceased
- 2000-05-24 ES ES00927234T patent/ES2257294T3/es not_active Expired - Lifetime
- 2000-05-24 PL PL00353441A patent/PL353441A1/xx unknown
- 2000-05-24 TR TR2001/03457T patent/TR200103457T2/xx unknown
- 2000-05-24 JP JP2000621345A patent/JP3590592B2/ja not_active Expired - Fee Related
- 2000-05-24 NZ NZ515407A patent/NZ515407A/xx unknown
- 2000-05-24 RU RU2001133458/04A patent/RU2243221C2/ru not_active IP Right Cessation
- 2000-05-24 WO PCT/EP2000/004701 patent/WO2000073279A1/en active IP Right Grant
- 2000-05-24 CA CA002375671A patent/CA2375671C/en not_active Expired - Fee Related
- 2000-05-24 DE DE60025918T patent/DE60025918T2/de not_active Expired - Fee Related
- 2000-05-24 KR KR10-2001-7015393A patent/KR100440106B1/ko not_active IP Right Cessation
- 2000-05-24 SI SI200030813T patent/SI1187815T1/sl unknown
- 2000-05-24 YU YU84901A patent/YU84901A/sh unknown
- 2000-05-24 BR BR0011127-9A patent/BR0011127A/pt not_active Application Discontinuation
- 2000-05-24 DK DK00927234T patent/DK1187815T3/da active
- 2000-05-24 CN CNB008082758A patent/CN1166643C/zh not_active Expired - Fee Related
- 2000-05-24 IL IL14646000A patent/IL146460A0/xx active IP Right Grant
- 2000-05-26 PE PE2000000508A patent/PE20010153A1/es not_active Application Discontinuation
- 2000-05-28 JO JO200083A patent/JO2261B1/en active
- 2000-05-29 AR ARP000102643A patent/AR024146A1/es not_active Application Discontinuation
- 2000-05-29 MY MYPI20002384A patent/MY122731A/en unknown
- 2000-05-29 CO CO00039590A patent/CO5170520A1/es not_active Application Discontinuation
- 2000-05-30 GC GCP2000684 patent/GC0000191A/en active
-
2001
- 2001-11-06 ZA ZA200109163A patent/ZA200109163B/en unknown
- 2001-11-12 IL IL146460A patent/IL146460A/en not_active IP Right Cessation
- 2001-11-22 HR HR20010871A patent/HRP20010871A2/hr not_active Application Discontinuation
- 2001-11-22 NO NO20015700A patent/NO321354B1/no unknown
- 2001-11-26 MA MA26424A patent/MA26793A1/fr unknown
-
2002
- 2002-10-22 HK HK02107643.4A patent/HK1046528B/zh not_active IP Right Cessation
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