ZA200201754B - New pyrimidine,2,4,6-trioe derivatives, processes for their production and pharmaceutical agents containing these compounds. - Google Patents
New pyrimidine,2,4,6-trioe derivatives, processes for their production and pharmaceutical agents containing these compounds. Download PDFInfo
- Publication number
- ZA200201754B ZA200201754B ZA200201754A ZA200201754A ZA200201754B ZA 200201754 B ZA200201754 B ZA 200201754B ZA 200201754 A ZA200201754 A ZA 200201754A ZA 200201754 A ZA200201754 A ZA 200201754A ZA 200201754 B ZA200201754 B ZA 200201754B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- phenoxy
- piperazin
- pyrimidin
- trioxo
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 51
- 238000000034 method Methods 0.000 title claims description 20
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000008177 pharmaceutical agent Substances 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 230000002001 anti-metastasis Effects 0.000 claims description 3
- 230000000259 anti-tumor effect Effects 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
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- 239000003814 drug Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 101710170181 Metalloproteinase inhibitor Proteins 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003475 metalloproteinase inhibitor Substances 0.000 claims 1
- 229940126170 metalloproteinase inhibitor Drugs 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- -1 5,5-disubstituted pyrimidine-2,4,6-triones Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical class O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 8
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- 150000003839 salts Chemical class 0.000 description 8
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- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000006193 alkinyl group Chemical group 0.000 description 3
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- 125000003118 aryl group Chemical group 0.000 description 3
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- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 description 2
- AUSICCHXDSOMHE-UHFFFAOYSA-N 2-piperazin-1-ylbenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1N1CCNCC1 AUSICCHXDSOMHE-UHFFFAOYSA-N 0.000 description 2
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
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- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
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- KHYPGPUUIKHUDQ-UHFFFAOYSA-N dimethyl 2-[4-(4-chlorophenoxy)phenyl]propanedioate Chemical compound C1=CC(C(C(=O)OC)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1 KHYPGPUUIKHUDQ-UHFFFAOYSA-N 0.000 description 1
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- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
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- RMLHLVGMOGCMMU-UHFFFAOYSA-N methyl 2-[4-(4-chlorophenoxy)phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1 RMLHLVGMOGCMMU-UHFFFAOYSA-N 0.000 description 1
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- QHUJTQAJBPYVQF-UHFFFAOYSA-N n-(2-hydroxyethyl)benzenesulfonamide Chemical compound OCCNS(=O)(=O)C1=CC=CC=C1 QHUJTQAJBPYVQF-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 201000008482 osteoarthritis Diseases 0.000 description 1
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- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
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- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
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- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
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- 230000004572 zinc-binding Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- 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
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
- A61K31/515—Barbituric acids; Derivatives thereof, e.g. sodium pentobarbital
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99119506 | 1999-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200201754B true ZA200201754B (en) | 2003-06-02 |
Family
ID=8239103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200201754A ZA200201754B (en) | 1999-10-01 | 2002-03-01 | New pyrimidine,2,4,6-trioe derivatives, processes for their production and pharmaceutical agents containing these compounds. |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6498252B1 (xx) |
| EP (1) | EP1226128B1 (xx) |
| JP (1) | JP3848160B2 (xx) |
| KR (1) | KR100459975B1 (xx) |
| CN (1) | CN1157382C (xx) |
| AR (1) | AR033651A1 (xx) |
| AT (1) | ATE289595T1 (xx) |
| AU (1) | AU768309B2 (xx) |
| BR (1) | BR0014678A (xx) |
| CA (1) | CA2385863C (xx) |
| CO (1) | CO5210860A1 (xx) |
| CZ (1) | CZ20021535A3 (xx) |
| DE (1) | DE60018301T2 (xx) |
| ES (1) | ES2235955T3 (xx) |
| HK (1) | HK1050198A1 (xx) |
| HU (1) | HUP0202832A3 (xx) |
| IL (1) | IL148573A0 (xx) |
| MA (1) | MA26823A1 (xx) |
| MX (1) | MXPA02003192A (xx) |
| NO (1) | NO20021380D0 (xx) |
| NZ (1) | NZ517635A (xx) |
| PE (1) | PE20010659A1 (xx) |
| PL (1) | PL202680B1 (xx) |
| RU (1) | RU2248971C2 (xx) |
| TR (1) | TR200200858T2 (xx) |
| UY (1) | UY26362A1 (xx) |
| WO (1) | WO2001025217A1 (xx) |
| YU (1) | YU22102A (xx) |
| ZA (1) | ZA200201754B (xx) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6716845B2 (en) * | 2001-03-30 | 2004-04-06 | Hoffmann-La Roche Inc. | Barbituric acid derivatives |
| WO2003053940A1 (en) | 2001-12-20 | 2003-07-03 | Bristol-Myers Squibb Company | Barbituric acid derivatives as inhibitors of tnf-$g(a) converting enzyme (tace) and/or matrix metalloproteinases |
| WO2004084903A1 (en) * | 2003-03-27 | 2004-10-07 | F. Hoffmann-La Roche Ag | Use of a trioxopyrimidine for the treatment and prevention of ocular pathologic angiogenesis |
| WO2004084902A1 (en) * | 2003-03-28 | 2004-10-07 | F. Hoffmann-La Roche Ag | Use of a trioxopyrimidine for the treatment of chronic wounds |
| EP1737464B1 (en) * | 2004-04-01 | 2008-07-23 | F. Hoffmann-La Roche AG | Use of a trioxopyrimidine for the treatment and prevention of bronchial inflammatory diseases |
| RU2411043C2 (ru) * | 2004-04-01 | 2011-02-10 | Юниверсите Де Льеж | Фармацевтические композиции пиримидин-2,4,6-трионов |
| EP1632489A1 (en) * | 2004-08-24 | 2006-03-08 | University of Liege | 5-(1,1'-Biphenyl)-4-yl-5-(4-(4-aminoacylphenyl)-piperazin)-1-yl-pyrimidine-2,4,6-trione derivatives, as inhibitors of zinc metallondopeptidases, their preparation and use. |
| RU2449994C1 (ru) * | 2011-03-10 | 2012-05-10 | Светлана Алексеевна Мещерякова | 6-(4-бензилпиперазино)-1,3-диметилурацила дигидрохлорид, проявляющий биологическую активность |
| RU2598607C1 (ru) * | 2015-07-16 | 2016-09-27 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Астраханский государственный университет" (Астраханский государственный университет) | Способ получения 5-гетарилметиленпиримидин-2,4,6-трионов |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1246743B (de) * | 1965-01-12 | 1967-08-10 | Dresden Arzneimittel | Verfahren zur Herstellung von 5-Phenyl-5-piperidinobarbitursaeuren |
| US4595700A (en) | 1984-12-21 | 1986-06-17 | G. D. Searle & Co. | Thiol based collagenase inhibitors |
| GB8726714D0 (en) | 1987-11-14 | 1987-12-16 | Beecham Group Plc | Compounds |
| GB8827305D0 (en) | 1988-11-23 | 1988-12-29 | British Bio Technology | Compounds |
| US5239078A (en) | 1990-11-21 | 1993-08-24 | Glycomed Incorporated | Matrix metalloprotease inhibitors |
| CA2073510A1 (en) | 1990-12-03 | 1992-06-04 | Celltech Therapeutics Limited | Peptidyl derivatives |
| CA2058797A1 (en) | 1991-02-01 | 1992-08-02 | Michael John Broadhurst | Amino acid derivatives |
| US5789434A (en) | 1994-11-15 | 1998-08-04 | Bayer Corporation | Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors |
| SI0874830T1 (en) | 1995-12-08 | 2003-08-31 | Agouron Pharmaceuticals, Inc. | A metalloproteinase inhibitor, a pharmaceutical composition containing it and the pharmaceutical use and method useful for the preparation thereof |
| DE19548624A1 (de) | 1995-12-23 | 1997-06-26 | Boehringer Mannheim Gmbh | Neue Barbitursäure-Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US6350786B1 (en) * | 1998-09-22 | 2002-02-26 | Hoffmann-La Roche Inc. | Stable complexes of poorly soluble compounds in ionic polymers |
-
2000
- 2000-09-27 CO CO00073355A patent/CO5210860A1/es not_active Application Discontinuation
- 2000-09-27 PE PE2000001013A patent/PE20010659A1/es not_active Application Discontinuation
- 2000-09-27 AR ARP000105063A patent/AR033651A1/es not_active Application Discontinuation
- 2000-09-29 US US09/675,935 patent/US6498252B1/en not_active Expired - Fee Related
- 2000-09-29 DE DE60018301T patent/DE60018301T2/de not_active Expired - Lifetime
- 2000-09-29 AT AT00967823T patent/ATE289595T1/de not_active IP Right Cessation
- 2000-09-29 CA CA002385863A patent/CA2385863C/en not_active Expired - Fee Related
- 2000-09-29 EP EP00967823A patent/EP1226128B1/en not_active Expired - Lifetime
- 2000-09-29 AU AU77849/00A patent/AU768309B2/en not_active Ceased
- 2000-09-29 BR BR0014678-1A patent/BR0014678A/pt not_active Application Discontinuation
- 2000-09-29 KR KR10-2002-7003979A patent/KR100459975B1/ko not_active IP Right Cessation
- 2000-09-29 ES ES00967823T patent/ES2235955T3/es not_active Expired - Lifetime
- 2000-09-29 MX MXPA02003192A patent/MXPA02003192A/es active IP Right Grant
- 2000-09-29 IL IL14857300A patent/IL148573A0/xx unknown
- 2000-09-29 HU HU0202832A patent/HUP0202832A3/hu unknown
- 2000-09-29 YU YU22102A patent/YU22102A/sh unknown
- 2000-09-29 TR TR2002/00858T patent/TR200200858T2/xx unknown
- 2000-09-29 RU RU2002110106/04A patent/RU2248971C2/ru not_active IP Right Cessation
- 2000-09-29 CZ CZ20021535A patent/CZ20021535A3/cs unknown
- 2000-09-29 NZ NZ517635A patent/NZ517635A/en unknown
- 2000-09-29 UY UY26362A patent/UY26362A1/es not_active Application Discontinuation
- 2000-09-29 PL PL357385A patent/PL202680B1/pl not_active IP Right Cessation
- 2000-09-29 WO PCT/EP2000/009535 patent/WO2001025217A1/en active IP Right Grant
- 2000-09-29 JP JP2001528163A patent/JP3848160B2/ja not_active Expired - Fee Related
- 2000-09-29 CN CNB00813006XA patent/CN1157382C/zh not_active Expired - Fee Related
-
2002
- 2002-03-01 ZA ZA200201754A patent/ZA200201754B/en unknown
- 2002-03-20 NO NO20021380A patent/NO20021380D0/no not_active Application Discontinuation
- 2002-04-01 MA MA26578A patent/MA26823A1/fr unknown
-
2003
- 2003-04-03 HK HK03102405A patent/HK1050198A1/xx not_active IP Right Cessation
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