CA2425283A1 - Inhibiteurs de metalloproteinase spiro-pyrimidine-2,4,6-trione - Google Patents
Inhibiteurs de metalloproteinase spiro-pyrimidine-2,4,6-trione Download PDFInfo
- Publication number
- CA2425283A1 CA2425283A1 CA002425283A CA2425283A CA2425283A1 CA 2425283 A1 CA2425283 A1 CA 2425283A1 CA 002425283 A CA002425283 A CA 002425283A CA 2425283 A CA2425283 A CA 2425283A CA 2425283 A1 CA2425283 A1 CA 2425283A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- group
- pyridin
- spiro
- triaza
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003475 metalloproteinase inhibitor Substances 0.000 title abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 96
- 238000000034 method Methods 0.000 claims abstract description 29
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 231
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 79
- 229910052760 oxygen Inorganic materials 0.000 claims description 79
- 239000001301 oxygen Substances 0.000 claims description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 76
- 125000001424 substituent group Chemical group 0.000 claims description 56
- 229910052799 carbon Inorganic materials 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 42
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 39
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 34
- 239000011593 sulfur Substances 0.000 claims description 33
- 229910052717 sulfur Inorganic materials 0.000 claims description 33
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 32
- 208000035475 disorder Diseases 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 230000005764 inhibitory process Effects 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 102000002274 Matrix Metalloproteinases Human genes 0.000 claims description 21
- 108010000684 Matrix Metalloproteinases Proteins 0.000 claims description 21
- 229920001774 Perfluoroether Polymers 0.000 claims description 21
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 21
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 241000124008 Mammalia Species 0.000 claims description 12
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
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- 208000017169 kidney disease Diseases 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 208000023504 respiratory system disease Diseases 0.000 claims description 6
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- 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
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- 239000003937 drug carrier Substances 0.000 claims description 4
- FPGLDNOEDDIHDV-UHFFFAOYSA-N 1-[6-(4-bromophenoxy)pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C1=CC(Br)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2=O)C=N1 FPGLDNOEDDIHDV-UHFFFAOYSA-N 0.000 claims description 3
- COHKACKHFIJNRE-UHFFFAOYSA-N 1-[6-[4-(1,3,4-oxadiazol-2-yl)phenoxy]pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C=1C=C(OC=2C=CC(=CC=2)C=2OC=NN=2)N=CC=1N1C(=O)CCC21C(=O)NC(=O)NC2=O COHKACKHFIJNRE-UHFFFAOYSA-N 0.000 claims description 3
- XTGSXSLCZLEGOR-UHFFFAOYSA-N 1-[6-(4-fluorophenoxy)pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C1=CC(F)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2=O)C=N1 XTGSXSLCZLEGOR-UHFFFAOYSA-N 0.000 claims description 2
- PPPWURMAIMIOFT-UHFFFAOYSA-N 1-[6-[4-(pyrazol-1-ylmethyl)phenoxy]pyridin-3-yl]-1,7,9-triazaspiro[4.5]decane-2,6,8,10-tetrone Chemical compound C=1C=C(OC=2C=CC(CN3N=CC=C3)=CC=2)N=CC=1N1C(=O)CCC21C(=O)NC(=O)NC2=O PPPWURMAIMIOFT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
- KPXPFHIVDNBNJV-UHFFFAOYSA-N n-[[4-[5-(2,6,8,10-tetraoxo-1,7,9-triazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]butanamide Chemical compound C1=CC(CNC(=O)CCC)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2=O)C=N1 KPXPFHIVDNBNJV-UHFFFAOYSA-N 0.000 claims description 2
- ZYRVUKSWVPEYJR-UHFFFAOYSA-N n-[[4-[5-(2,6,8,10-tetraoxo-1,7,9-triazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCC(C=C1)=CC=C1OC(N=C1)=CC=C1N1C(=O)CCC11C(=O)NC(=O)NC1=O ZYRVUKSWVPEYJR-UHFFFAOYSA-N 0.000 claims description 2
- NEAOVPZGCKZONB-UHFFFAOYSA-N n-[[4-[5-(2,6,8,10-tetraoxo-1,7,9-triazaspiro[4.5]decan-1-yl)pyridin-2-yl]oxyphenyl]methyl]pentanamide Chemical compound C1=CC(CNC(=O)CCCC)=CC=C1OC1=CC=C(N2C3(C(NC(=O)NC3=O)=O)CCC2=O)C=N1 NEAOVPZGCKZONB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 14
- 125000006573 (C1-C10) heteroaryl group Chemical group 0.000 claims 11
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 9
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 229940080818 propionamide Drugs 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 8
- 201000011510 cancer Diseases 0.000 abstract description 4
- 206010061218 Inflammation Diseases 0.000 abstract description 3
- 230000004054 inflammatory process Effects 0.000 abstract description 3
- -1 i.e. Chemical class 0.000 description 102
- 125000004076 pyridyl group Chemical group 0.000 description 73
- 239000002585 base Substances 0.000 description 64
- 125000001072 heteroaryl group Chemical group 0.000 description 64
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
- 239000003112 inhibitor Substances 0.000 description 61
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
- 239000002904 solvent Substances 0.000 description 49
- 102000004190 Enzymes Human genes 0.000 description 48
- 108090000790 Enzymes Proteins 0.000 description 48
- 229940088598 enzyme Drugs 0.000 description 48
- 239000000203 mixture Substances 0.000 description 48
- 125000003373 pyrazinyl group Chemical group 0.000 description 48
- 125000002098 pyridazinyl group Chemical group 0.000 description 46
- 125000000714 pyrimidinyl group Chemical group 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 43
- 238000003556 assay Methods 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000011575 calcium Substances 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 35
- 125000003118 aryl group Chemical group 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 125000005843 halogen group Chemical group 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 29
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
- 125000001715 oxadiazolyl group Chemical group 0.000 description 27
- 125000003226 pyrazolyl group Chemical group 0.000 description 27
- 125000003545 alkoxy group Chemical group 0.000 description 26
- 125000002883 imidazolyl group Chemical group 0.000 description 26
- 108010002352 Interleukin-1 Proteins 0.000 description 25
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- 125000001786 isothiazolyl group Chemical group 0.000 description 25
- 125000000842 isoxazolyl group Chemical group 0.000 description 25
- 125000002971 oxazolyl group Chemical group 0.000 description 24
- 102100027995 Collagenase 3 Human genes 0.000 description 23
- 108050005238 Collagenase 3 Proteins 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 102000000380 Matrix Metalloproteinase 1 Human genes 0.000 description 20
- 108010016113 Matrix Metalloproteinase 1 Proteins 0.000 description 20
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- 230000000694 effects Effects 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 18
- 238000007792 addition Methods 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
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- 238000010790 dilution Methods 0.000 description 17
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 229910052791 calcium Inorganic materials 0.000 description 16
- 125000001309 chloro group Chemical group Cl* 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
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- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
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Abstract
La présente invention concerne des inhibiteurs de métalloprotéinase 5-spiro-pyrimidine-2,4,6-trione selon la formule (I), où "A" est un noyau hétérocyclique à 5-7 éléments, tel qu'il est défini dans la spécification, ainsi que des compositions et des procédés pharmaceutiques pour traiter des inflammations, le cancer et d'autres maladies.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24338900P | 2000-10-26 | 2000-10-26 | |
| US60/243,389 | 2000-10-26 | ||
| PCT/IB2001/001986 WO2002034753A2 (fr) | 2000-10-26 | 2001-10-23 | Inhibiteurs de metalloproteinase spiro-pyrimidine-2,4,6-trione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2425283A1 true CA2425283A1 (fr) | 2002-05-02 |
Family
ID=22918584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002425283A Abandoned CA2425283A1 (fr) | 2000-10-26 | 2001-10-23 | Inhibiteurs de metalloproteinase spiro-pyrimidine-2,4,6-trione |
Country Status (32)
| Country | Link |
|---|---|
| EP (1) | EP1332146A2 (fr) |
| JP (1) | JP2004518635A (fr) |
| KR (1) | KR20040004412A (fr) |
| CN (1) | CN1501937A (fr) |
| AP (1) | AP2001002318A0 (fr) |
| AR (1) | AR035069A1 (fr) |
| AU (1) | AU2002210813A1 (fr) |
| BG (1) | BG107653A (fr) |
| BR (1) | BR0114913A (fr) |
| CA (1) | CA2425283A1 (fr) |
| CZ (1) | CZ20031083A3 (fr) |
| EA (1) | EA005762B1 (fr) |
| EC (1) | ECSP034567A (fr) |
| EE (1) | EE200300196A (fr) |
| GT (1) | GT200100213A (fr) |
| HN (1) | HN2001000244A (fr) |
| HR (1) | HRP20030332A2 (fr) |
| HU (1) | HUP0301577A3 (fr) |
| IL (1) | IL154948A0 (fr) |
| IS (1) | IS6762A (fr) |
| MA (1) | MA26957A1 (fr) |
| MX (1) | MXPA03003735A (fr) |
| NO (1) | NO20031853L (fr) |
| OA (1) | OA12529A (fr) |
| PA (1) | PA8531401A1 (fr) |
| PE (1) | PE20020589A1 (fr) |
| PL (1) | PL366201A1 (fr) |
| SK (1) | SK4972003A3 (fr) |
| SV (1) | SV2003000705A (fr) |
| TN (1) | TNSN01149A1 (fr) |
| WO (1) | WO2002034753A2 (fr) |
| ZA (1) | ZA200302190B (fr) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002064571A1 (fr) | 2001-02-14 | 2002-08-22 | Warner-Lambert Company Llc | Pyrimidine comme inhibiteurs de la métalloprotéinase de matrice |
| PA8539501A1 (es) | 2001-02-14 | 2002-09-30 | Warner Lambert Co | Compuestos triazolo como inhibidores de mmp |
| DOP2002000332A (es) | 2001-02-14 | 2002-08-30 | Warner Lambert Co | Inhibidores de piridina de metaloproteinasas de la matriz |
| CA2433075A1 (fr) | 2001-02-14 | 2002-08-22 | Michael William Wilson | Benzo-thiadiazines inhibitrices des metalloproteinases matricielles |
| DOP2002000333A (es) | 2001-02-14 | 2002-09-30 | Warner Lambert Co | Derivados de acido isoftalico como inhibidores de metaloproteinasas de la matriz |
| US6924276B2 (en) | 2001-09-10 | 2005-08-02 | Warner-Lambert Company | Diacid-substituted heteroaryl derivatives as matrix metalloproteinase inhibitors |
| US6962922B2 (en) | 2001-10-12 | 2005-11-08 | Warner-Lambert Company Llc | Alkynylated quinazoline compounds |
| EP1434585A1 (fr) | 2001-10-12 | 2004-07-07 | Warner-Lambert Company LLC | Inhibiteurs de metalloproteinase matricielle (mmp) a base d'alkyne |
| US6894057B2 (en) | 2002-03-08 | 2005-05-17 | Warner-Lambert Company | Oxo-azabicyclic compounds |
| AU2003228701A1 (en) * | 2002-04-25 | 2003-11-10 | Bristol-Myers Squibb Company | Spirobarbituric acid derivatives useful as inhibitors of matrix metalloproteases |
| DE60301574T2 (de) * | 2002-04-26 | 2006-01-12 | Pfizer Products Inc., Groton | Triaryl-oxy-aryl-spiro-pyrimidin-2, 4, 6-trion metalloproteinase inhibitoren |
| WO2003091258A1 (fr) * | 2002-04-26 | 2003-11-06 | Pfizer Products Inc. | Inhibiteurs de la metalloproteinase n-substitues-heteroaryloxy-aryl-spiro-pyrimidine-2,4,6-trione |
| AU2003250466A1 (en) | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | 3-isoquinolinone derivatives as matrix metalloproteinase inhiitors |
| JP2006500351A (ja) | 2002-08-13 | 2006-01-05 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | マトリックスメタロプロテアーゼ−13阻害剤としてのピリミジン−2,4−ジオン誘導体 |
| PA8578101A1 (es) | 2002-08-13 | 2004-05-07 | Warner Lambert Co | Derivados de heterobiarilo como inhibidores de metaloproteinasa de la matriz |
| EP1537090A1 (fr) | 2002-08-13 | 2005-06-08 | Warner-Lambert Company Llc | Derives de chromone inhibiteurs de metalloproteinase de matrice |
| WO2004014923A1 (fr) | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | Inhibiteurs de metalloprotease bicycliques condenses avec la pyrimidinone |
| WO2004014866A1 (fr) | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | Derives d'azaisoquinoline utilises comme inhibiteurs de metalloproteases matricielles |
| WO2004014908A1 (fr) | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | Inhibiteurs de metalloproteinases heterobicycliques |
| AU2003249540A1 (en) | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | Fused bicyclic metalloproteinase inhibitors |
| BR0313459A (pt) | 2002-08-13 | 2005-06-21 | Warner Lambert Co | Derivados monocìclicos como inibidores de metaloproteinases de matriz |
| AU2003253186A1 (en) | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | Fused tetrahydropyridine derivatives as matrix metalloproteinase inhibitors |
| US7208490B2 (en) | 2002-10-07 | 2007-04-24 | Pharmacia & Upjohn Company Llc | Tricyclic tetrahydroquinoline antibacterial agents |
| GB0223249D0 (en) * | 2002-10-08 | 2002-11-13 | Amersham Plc | Improved imaging agents |
| WO2004084903A1 (fr) * | 2003-03-27 | 2004-10-07 | F. Hoffmann-La Roche Ag | Utilisation d'une trioxopyrimidine pour le traitement et la prevention de l'angiogenese pathologique oculaire |
| WO2004084902A1 (fr) * | 2003-03-28 | 2004-10-07 | F. Hoffmann-La Roche Ag | Utilisation d'une trioxopyrimidine dans le traitement de lesions chroniques |
| FR2858232B1 (fr) * | 2003-07-29 | 2006-03-03 | Pierre Potier | Utilisation d'un derive de biguanide pour proteger la peau des radiations uvb |
| MXPA06011030A (es) * | 2004-04-01 | 2007-03-21 | Hoffmann La Roche | Uso de una trioxopirimidina para el tratamiento y prevencion de enfermedades inflamatorias bronquiales. |
| DOP2006000268A (es) | 2005-12-22 | 2007-07-31 | Pfizer Prod Inc | Agentes antibacterianos |
| US8153166B2 (en) * | 2006-06-08 | 2012-04-10 | Chih-Hsiung Lin | Composition for prophylaxis or treatment of urinary system infection and method thereof |
| CN102285934B (zh) * | 2009-01-08 | 2013-08-14 | 四川大学 | 螺环二烯酮衍生物及其制备方法和用途 |
| RS57190B1 (sr) * | 2012-12-10 | 2018-07-31 | Chugai Pharmaceutical Co Ltd | Derivat hidantoina |
| KR101594506B1 (ko) * | 2014-03-20 | 2016-02-17 | 한국화학연구원 | 골 관련 질환 치료용 조성물 |
| WO2015189901A1 (fr) | 2014-06-09 | 2015-12-17 | 中外製薬株式会社 | Composition pharmaceutique contenant un dérivé d'hydantoïne |
| WO2020113088A1 (fr) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Composés diarylhydantoine et leurs procédés d'utilisation |
| CN110092790B (zh) * | 2019-06-11 | 2020-07-24 | 东北农业大学 | 一种生物碱类化合物及其制备方法和应用 |
| WO2025226892A1 (fr) * | 2024-04-24 | 2025-10-30 | Septerna, Inc. | Agonistes de diaminométhylène pyrimidine-2,4,6-trione contenant un spirocycle de récepteurs 1 de l'hormone parathyroïdienne et de l'incrétine |
| WO2025226895A1 (fr) * | 2024-04-24 | 2025-10-30 | Septerna, Inc. | Agonistes de l'hormone parathyroïdienne 1 et récepteurs d'incrétine comprenant des diaminométhylène pyrimidine-2,4,6-triones substituées ou modifiées |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3714093A (en) * | 1970-05-19 | 1973-01-30 | American Home Prod | Spiro [heterocycloalkyl-2'(1'h)-quinazoline]-4'(3'h)-ones |
| CN1295227C (zh) * | 1997-06-21 | 2007-01-17 | 罗赫诊断器材股份有限公司 | 具有抗转移和抗肿瘤活性的巴比土酸衍生物 |
| US6265578B1 (en) * | 1999-02-12 | 2001-07-24 | Hoffmann-La Roche Inc. | Pyrimidine-2,4,6-triones |
| PA8498701A1 (es) * | 1999-08-12 | 2002-08-26 | Pfizer Prod Inc | Pirimidina-2,4,6-trionas inhibidores de metaloproteinasas |
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2001
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