ES2319300T3 - Derivados de 2-piridona como inhibidores de elastasa neutrofila y su uso. - Google Patents
Derivados de 2-piridona como inhibidores de elastasa neutrofila y su uso. Download PDFInfo
- Publication number
- ES2319300T3 ES2319300T3 ES04775439T ES04775439T ES2319300T3 ES 2319300 T3 ES2319300 T3 ES 2319300T3 ES 04775439 T ES04775439 T ES 04775439T ES 04775439 T ES04775439 T ES 04775439T ES 2319300 T3 ES2319300 T3 ES 2319300T3
- Authority
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- Spain
- Prior art keywords
- alkyl
- phenyl
- oxo
- methyl
- trifluoromethyl
- 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.)
- Expired - Lifetime
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- 239000003112 inhibitor Substances 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 202
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 165
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 79
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 78
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 78
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 68
- -1 R 21 Chemical compound 0.000 claims abstract description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 58
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 31
- 150000002367 halogens Chemical class 0.000 claims abstract description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 22
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 21
- 125000004429 atom Chemical group 0.000 claims abstract description 20
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 16
- 125000001424 substituent group Chemical group 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000005647 linker group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 87
- 238000000034 method Methods 0.000 claims description 51
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- 201000010099 disease Diseases 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical group [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 12
- 229910002091 carbon monoxide Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
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- 206010039083 rhinitis Diseases 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
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- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 125000002355 alkine group Chemical group 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 abstract description 2
- 238000000668 atmospheric pressure chemical ionisation mass spectrometry Methods 0.000 description 167
- 239000000203 mixture Substances 0.000 description 79
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- 239000007787 solid Substances 0.000 description 55
- VMNXLLDFGVEBLE-UHFFFAOYSA-N (4-methylsulfonylphenyl)methanamine Chemical compound CS(=O)(=O)C1=CC=C(CN)C=C1 VMNXLLDFGVEBLE-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 50
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 44
- 238000002953 preparative HPLC Methods 0.000 description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
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- 239000011541 reaction mixture Substances 0.000 description 37
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- USMWDGUFWSUYSK-UHFFFAOYSA-N 2-methyl-6-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3,5-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=C(C(O)=O)C(=O)N1C1=CC=CC(C(F)(F)F)=C1 USMWDGUFWSUYSK-UHFFFAOYSA-N 0.000 description 20
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- 230000008569 process Effects 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 239000000843 powder Substances 0.000 description 13
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 210000000440 neutrophil Anatomy 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- SDUGJSSOHAJLSC-UHFFFAOYSA-N 5-iodo-6-methyl-n-[(4-methylsulfonylphenyl)methyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(I)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 SDUGJSSOHAJLSC-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- OVRLMTPOWFEQPO-UHFFFAOYSA-N 2-methyl-5-[(4-methylsulfonylphenyl)methylcarbamoyl]-6-oxo-1-[3-(trifluoromethyl)phenyl]pyridine-3-carboxylic acid Chemical compound O=C1N(C=2C=C(C=CC=2)C(F)(F)F)C(C)=C(C(O)=O)C=C1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 OVRLMTPOWFEQPO-UHFFFAOYSA-N 0.000 description 8
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- 238000007792 addition Methods 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 8
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
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- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
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- 235000017281 sodium acetate Nutrition 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
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- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (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)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE2003102487 | 2003-09-18 | ||
| SE0302487A SE0302487D0 (sv) | 2003-09-18 | 2003-09-18 | Novel compounds |
Publications (1)
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|---|---|
| ES2319300T3 true ES2319300T3 (es) | 2009-05-06 |
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| ES04775439T Expired - Lifetime ES2319300T3 (es) | 2003-09-18 | 2004-09-15 | Derivados de 2-piridona como inhibidores de elastasa neutrofila y su uso. |
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| EP (1) | EP1663974B1 (enExample) |
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| AR (1) | AR046083A1 (enExample) |
| AT (1) | ATE420861T1 (enExample) |
| AU (1) | AU2004272485B2 (enExample) |
| BR (1) | BRPI0414570A (enExample) |
| CA (1) | CA2538410A1 (enExample) |
| CO (1) | CO5670357A2 (enExample) |
| DE (1) | DE602004019110D1 (enExample) |
| ES (1) | ES2319300T3 (enExample) |
| IL (1) | IL173986A0 (enExample) |
| IS (1) | IS8394A (enExample) |
| MX (1) | MXPA06002723A (enExample) |
| NO (1) | NO20061700L (enExample) |
| RU (1) | RU2348617C2 (enExample) |
| SA (1) | SA04250300B1 (enExample) |
| SE (1) | SE0302487D0 (enExample) |
| TW (1) | TW200526579A (enExample) |
| UA (1) | UA84878C2 (enExample) |
| UY (1) | UY28513A1 (enExample) |
| WO (1) | WO2005026124A1 (enExample) |
| ZA (1) | ZA200602262B (enExample) |
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| SE0302486D0 (sv) * | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | Novel compounds |
| US7459562B2 (en) | 2004-04-23 | 2008-12-02 | Bristol-Myers Squibb Company | Monocyclic heterocycles as kinase inhibitors |
| TW200538453A (en) | 2004-04-26 | 2005-12-01 | Bristol Myers Squibb Co | Bicyclic heterocycles as kinase inhibitors |
| US7432373B2 (en) | 2004-06-28 | 2008-10-07 | Bristol-Meyers Squibb Company | Processes and intermediates useful for preparing fused heterocyclic kinase inhibitors |
| US7439246B2 (en) | 2004-06-28 | 2008-10-21 | Bristol-Myers Squibb Company | Fused heterocyclic kinase inhibitors |
| US20050288290A1 (en) | 2004-06-28 | 2005-12-29 | Borzilleri Robert M | Fused heterocyclic kinase inhibitors |
| TW200700392A (en) * | 2005-03-16 | 2007-01-01 | Astrazeneca Ab | Novel compounds |
| PH12012502411A1 (en) | 2005-05-10 | 2019-07-17 | Intermune Inc | Method of modulating stress-activated protein kinase system |
| GB0516313D0 (en) | 2005-08-08 | 2005-09-14 | Argenta Discovery Ltd | Azole derivatives and their uses |
| KR20080036632A (ko) | 2005-08-08 | 2008-04-28 | 아젠터 디스커버리 리미티드 | 바이시클로[2.2.1]헵트-7-일아민 유도체 및 이들의 용도 |
| EP1940458A4 (en) * | 2005-09-29 | 2010-03-03 | Univ Alberta | COMPOSITIONS AND METHODS OF INHIBITING GRANZYME B |
| GB0605469D0 (en) * | 2006-03-17 | 2006-04-26 | Argenta Discovery Ltd | Multimers of heterocyclic compounds and their use |
| TW200808771A (en) * | 2006-05-08 | 2008-02-16 | Astrazeneca Ab | Novel compounds II |
| TW200808763A (en) * | 2006-05-08 | 2008-02-16 | Astrazeneca Ab | Novel compounds I |
| EP2077262A4 (en) | 2006-10-23 | 2011-12-28 | Takeda Pharmaceutical | IMINOPYRIDINE DERIVATIVE AND USE THEREOF |
| CL2007003226A1 (es) | 2006-11-08 | 2008-02-08 | Bristol Myers Squibb Co | Compuestos derivados de piridinona; composicion farmaceutica; y uso para tratar el cancer. |
| CL2008003301A1 (es) * | 2007-11-06 | 2009-10-16 | Astrazeneca Ab | Compuestos derivados de 3,4-dihidropirazina-2-carboxamida, inhibidores de la elastasa de neutrofilos humanos; composiciones farmacéuticas; procesos de preparación de compuestos y composición farmacéutica; y uso en el tratamiento de síndrome de dificultad respiratoria de los adultos, fibrosis quística, cáncer, entre otras. |
| AU2008337342B2 (en) | 2007-12-14 | 2012-05-24 | Pulmagen Therapeutics (Asthma) Limited | Indoles and their therapeutic use |
| WO2009094417A1 (en) | 2008-01-23 | 2009-07-30 | Bristol-Myers Squibb Company | 4-pyridinone compounds and their use for cancer |
| US8481569B2 (en) | 2008-04-23 | 2013-07-09 | Takeda Pharmaceutical Company Limited | Iminopyridine derivatives and use thereof |
| CA3034994A1 (en) | 2008-06-03 | 2009-12-10 | Intermune, Inc. | Substituted aryl-2 pyridone compounds and use thereof for treating inflammatory and fibrotic disorders |
| GB0902648D0 (en) | 2009-02-17 | 2009-04-01 | Argenta Discovery Ltd | Pharmaceutical compounds and compositions |
| EA201190119A1 (ru) | 2009-02-17 | 2012-05-30 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | ПРОИЗВОДНЫЕ ТРИАЗОЛОПИРИДИНА В КАЧЕСТВЕ ИНГИБИТОРОВ МАР-КИНАЗЫ p38 |
| TW201036957A (en) * | 2009-02-20 | 2010-10-16 | Astrazeneca Ab | Novel salt 628 |
| KR20120099639A (ko) * | 2009-10-02 | 2012-09-11 | 아스트라제네카 아베 | 호중구 엘라스타제의 억제제로서 사용되는 2-피리돈 화합물 |
| GB0918922D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Aminopyridine derivatives |
| GB0918923D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Aminothiazole derivatives |
| GB0918924D0 (en) | 2009-10-28 | 2009-12-16 | Vantia Ltd | Azaindole derivatives |
| IN2012DN05081A (enExample) * | 2009-12-08 | 2015-10-09 | Boehringer Ingelheim Int | |
| GB201009731D0 (en) | 2010-06-10 | 2010-07-21 | Pulmagen Therapeutics Inflamma | Kinase inhibitors |
| EP2740728A4 (en) | 2011-08-01 | 2015-04-01 | Sumitomo Dainippon Pharma Co Ltd | URACIL DERIVATIVE AND ITS USE FOR MEDICAL PURPOSES |
| CN105968110B (zh) | 2011-12-09 | 2018-04-27 | 奇斯药制品公司 | 激酶抑制剂 |
| CA2858420A1 (en) | 2011-12-09 | 2013-06-13 | Chiesi Farmaceutici S.P.A. | Derivatives of 4-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl urea and their use in the treatment of, inter alia, diseases of the respiratory tract |
| MY167216A (en) | 2011-12-09 | 2018-08-14 | Chiesi Farm Spa | Kinase inhibitors |
| US20140057920A1 (en) | 2012-08-23 | 2014-02-27 | Boehringer Ingelheim International Gmbh | Substituted 4-pyridones and their use as inhibitors of neutrophil elastase activity |
| US20140057926A1 (en) | 2012-08-23 | 2014-02-27 | Boehringer Ingelheim International Gmbh | Substituted 4-pyridones and their use as inhibitors of neutrophil elastase activity |
| US9102624B2 (en) | 2012-08-23 | 2015-08-11 | Boehringer Ingelheim International Gmbh | Substituted 4-pyridones and their use as inhibitors of neutrophil elastase activity |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| US9181242B2 (en) | 2013-06-06 | 2015-11-10 | Chiesi Farmaceutici S.P.A. | Kinase inhibitors |
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| GB9207145D0 (en) * | 1991-04-18 | 1992-05-13 | Ici Plc | Heterocyclic amides |
| US5521179A (en) * | 1991-04-18 | 1996-05-28 | Zeneca Limited | Heterocyclic amides |
| FR2687674B1 (fr) * | 1992-02-07 | 1995-05-19 | Roussel Uclaf | Nouveaux derives de la pyridone, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant. |
| WO1995014012A1 (en) * | 1993-11-19 | 1995-05-26 | Parke, Davis & Company | 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents |
| RU2067579C1 (ru) * | 1994-10-07 | 1996-10-10 | Пермский фармацевтический институт | 3-(2'-нафтоилметилен)-пиперазинон-2 и 1-n-фенил-3-фенацилиденпиперазинон-2, проявляющие противовоспалительную активность |
| ATE438624T1 (de) * | 2000-12-28 | 2009-08-15 | Shionogi & Co | 2-pyridonderivate mit affinität für den cannabinoid-typ-2-rezeptor |
| GB0129260D0 (en) * | 2001-12-06 | 2002-01-23 | Eisai London Res Lab Ltd | Pharmaceutical compositions and their uses |
| JP4486817B2 (ja) * | 2001-12-20 | 2010-06-23 | バイエル・シェーリング・ファルマ・アクチェンゲゼルシャフト | １，４−ジヒドロ−１，４−ジフェニルピリジン誘導体 |
| GB2383326A (en) * | 2001-12-20 | 2003-06-25 | Bayer Ag | Antiinflammatory dihydropyridines |
| TW200500341A (en) * | 2002-11-12 | 2005-01-01 | Astrazeneca Ab | Novel compounds |
| SE0302486D0 (sv) * | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | Novel compounds |
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2003
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2004
- 2004-09-13 TW TW093127678A patent/TW200526579A/zh unknown
- 2004-09-15 CA CA002538410A patent/CA2538410A1/en not_active Abandoned
- 2004-09-15 AU AU2004272485A patent/AU2004272485B2/en not_active Ceased
- 2004-09-15 BR BRPI0414570-4A patent/BRPI0414570A/pt not_active IP Right Cessation
- 2004-09-15 RU RU2006112427/04A patent/RU2348617C2/ru not_active IP Right Cessation
- 2004-09-15 EP EP04775439A patent/EP1663974B1/en not_active Expired - Lifetime
- 2004-09-15 DE DE602004019110T patent/DE602004019110D1/de not_active Expired - Fee Related
- 2004-09-15 US US10/572,640 patent/US20070043036A1/en not_active Abandoned
- 2004-09-15 UY UY28513A patent/UY28513A1/es unknown
- 2004-09-15 ES ES04775439T patent/ES2319300T3/es not_active Expired - Lifetime
- 2004-09-15 UA UAA200602252A patent/UA84878C2/ru unknown
- 2004-09-15 KR KR1020067005458A patent/KR20060096995A/ko not_active Withdrawn
- 2004-09-15 AT AT04775439T patent/ATE420861T1/de not_active IP Right Cessation
- 2004-09-15 MX MXPA06002723A patent/MXPA06002723A/es unknown
- 2004-09-15 WO PCT/SE2004/001336 patent/WO2005026124A1/en not_active Ceased
- 2004-09-15 CN CNB2004800275174A patent/CN100439339C/zh not_active Expired - Fee Related
- 2004-09-15 JP JP2006526856A patent/JP2007505902A/ja active Pending
- 2004-09-17 AR ARP040103354A patent/AR046083A1/es not_active Application Discontinuation
- 2004-09-18 SA SA4250300A patent/SA04250300B1/ar unknown
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2006
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- 2006-03-15 CO CO06026211A patent/CO5670357A2/es not_active Application Discontinuation
- 2006-03-17 ZA ZA200602262A patent/ZA200602262B/xx unknown
- 2006-03-31 IS IS8394A patent/IS8394A/is unknown
- 2006-04-18 NO NO20061700A patent/NO20061700L/no not_active Application Discontinuation
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| RU2006112427A (ru) | 2007-11-10 |
| UY28513A1 (es) | 2005-04-29 |
| AU2004272485A1 (en) | 2005-03-24 |
| DE602004019110D1 (de) | 2009-03-05 |
| TW200526579A (en) | 2005-08-16 |
| ATE420861T1 (de) | 2009-01-15 |
| UA84878C2 (ru) | 2008-12-10 |
| IS8394A (is) | 2006-03-31 |
| SA04250300B1 (ar) | 2008-09-07 |
| HK1089167A1 (en) | 2006-11-24 |
| IL173986A0 (en) | 2006-07-05 |
| MXPA06002723A (es) | 2006-06-06 |
| AR046083A1 (es) | 2005-11-23 |
| KR20060096995A (ko) | 2006-09-13 |
| RU2348617C2 (ru) | 2009-03-10 |
| WO2005026124A1 (en) | 2005-03-24 |
| CA2538410A1 (en) | 2005-03-24 |
| US20070043036A1 (en) | 2007-02-22 |
| NO20061700L (no) | 2006-04-18 |
| BRPI0414570A (pt) | 2006-11-07 |
| JP2007505902A (ja) | 2007-03-15 |
| AU2004272485B2 (en) | 2008-03-13 |
| CO5670357A2 (es) | 2006-08-31 |
| CN100439339C (zh) | 2008-12-03 |
| SE0302487D0 (sv) | 2003-09-18 |
| EP1663974B1 (en) | 2009-01-14 |
| ZA200602262B (en) | 2007-07-25 |
| CN1856467A (zh) | 2006-11-01 |
| EP1663974A1 (en) | 2006-06-07 |
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