CA2635580A1 - Substituted bis-amide metalloprotease inhibitors - Google Patents
Substituted bis-amide metalloprotease inhibitors Download PDFInfo
- Publication number
- CA2635580A1 CA2635580A1 CA002635580A CA2635580A CA2635580A1 CA 2635580 A1 CA2635580 A1 CA 2635580A1 CA 002635580 A CA002635580 A CA 002635580A CA 2635580 A CA2635580 A CA 2635580A CA 2635580 A1 CA2635580 A1 CA 2635580A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- group
- cycloalkyl
- aryl
- heteroaryl
- 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
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical class CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 title description 25
- 239000003475 metalloproteinase inhibitor Substances 0.000 title description 4
- -1 bis-amide pyrimidine compounds Chemical class 0.000 claims abstract description 63
- 102000005741 Metalloproteases Human genes 0.000 claims abstract description 37
- 108010006035 Metalloproteases Proteins 0.000 claims abstract description 37
- 102100027995 Collagenase 3 Human genes 0.000 claims abstract description 27
- 108050005238 Collagenase 3 Proteins 0.000 claims abstract description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 20
- 201000010099 disease Diseases 0.000 claims abstract description 19
- 230000001404 mediated effect Effects 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims description 233
- 125000000217 alkyl group Chemical group 0.000 claims description 163
- 239000000203 mixture Substances 0.000 claims description 131
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 113
- 125000003118 aryl group Chemical group 0.000 claims description 101
- 125000001072 heteroaryl group Chemical group 0.000 claims description 98
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 80
- 125000001188 haloalkyl group Chemical group 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 54
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 52
- 125000000304 alkynyl group Chemical group 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 230000002401 inhibitory effect Effects 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 19
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 102000004190 Enzymes Human genes 0.000 claims description 13
- 108090000790 Enzymes Proteins 0.000 claims description 13
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
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- 239000003260 cyclooxygenase 1 inhibitor Substances 0.000 claims description 9
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- 229940079593 drug Drugs 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 150000003431 steroids Chemical class 0.000 claims description 8
- 230000001225 therapeutic effect Effects 0.000 claims description 8
- 229940123907 Disease modifying antirheumatic drug Drugs 0.000 claims description 7
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 7
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 7
- 230000008512 biological response Effects 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 7
- 230000001506 immunosuppresive effect Effects 0.000 claims description 7
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- 102000019034 Chemokines Human genes 0.000 claims description 6
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
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- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 6
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- 150000001204 N-oxides Chemical class 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims description 5
- 229960002702 piroxicam Drugs 0.000 claims description 5
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 4
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 4
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 4
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
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- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 208000006820 Arthralgia Diseases 0.000 claims description 3
- 206010006002 Bone pain Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 206010065390 Inflammatory pain Diseases 0.000 claims description 3
- 108010002352 Interleukin-1 Proteins 0.000 claims description 3
- 208000002193 Pain Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 229960000590 celecoxib Drugs 0.000 claims description 3
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims description 3
- 230000016396 cytokine production Effects 0.000 claims description 3
- 230000000770 proinflammatory effect Effects 0.000 claims description 3
- 229960000371 rofecoxib Drugs 0.000 claims description 3
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical group C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims description 3
- 150000003384 small molecules Chemical class 0.000 claims description 3
- 229960002004 valdecoxib Drugs 0.000 claims description 3
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims description 3
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 claims description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims description 2
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- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 claims description 2
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical group CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims description 2
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- 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
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- UOCLRXFKRLRMKV-UHFFFAOYSA-N trolnitrate phosphate Chemical compound OP(O)(O)=O.OP(O)(O)=O.[O-][N+](=O)OCCN(CCO[N+]([O-])=O)CCO[N+]([O-])=O UOCLRXFKRLRMKV-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61P11/00—Drugs for disorders of the respiratory system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
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- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Pulmonology (AREA)
- Vascular Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75553905P | 2005-12-30 | 2005-12-30 | |
| US60/755,539 | 2005-12-30 | ||
| PCT/US2006/049521 WO2007079199A2 (en) | 2005-12-30 | 2006-12-28 | Substituted bis-amide metalloprotease inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2635580A1 true CA2635580A1 (en) | 2007-07-12 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002635580A Abandoned CA2635580A1 (en) | 2005-12-30 | 2006-12-28 | Substituted bis-amide metalloprotease inhibitors |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20070155739A1 (https=) |
| EP (1) | EP1981855A2 (https=) |
| JP (1) | JP2009522295A (https=) |
| AU (1) | AU2006332694A1 (https=) |
| CA (1) | CA2635580A1 (https=) |
| WO (1) | WO2007079199A2 (https=) |
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| JP4800216B2 (ja) * | 2003-10-24 | 2011-10-26 | エグゼリクシス， インコーポレイテッド | ｐ７０Ｓ６キナーゼモジュレーターおよび使用方法 |
| CA2608890C (en) * | 2005-05-20 | 2011-08-02 | Alantos-Pharmaceuticals, Inc. | Heterobicyclic metalloprotease inhibitors |
| US20070155738A1 (en) * | 2005-05-20 | 2007-07-05 | Alantos Pharmaceuticals, Inc. | Heterobicyclic metalloprotease inhibitors |
| US20070155737A1 (en) * | 2005-05-20 | 2007-07-05 | Alantos Pharmaceuticals, Inc. | Heterobicyclic metalloprotease inhibitors |
| CA2658362A1 (en) * | 2006-06-29 | 2008-01-03 | Alantos Pharmaceuticals Holding, Inc. | Metalloprotease inhibitors |
| AU2008223348A1 (en) * | 2007-03-07 | 2008-09-12 | Alantos Pharmaceuticals Holding, Inc. | Metalloprotease inhibitors containing a heterocyclic moiety |
| AR067354A1 (es) | 2007-06-29 | 2009-10-07 | Sunesis Pharmaceuticals Inc | Compuestos utiles como inhibidores de la raf quinasa |
| AR068509A1 (es) * | 2007-09-19 | 2009-11-18 | Jerini Ag | Antagosnistas del receptor de bradiquinina b1 |
| CA2760655C (en) | 2009-06-04 | 2018-03-06 | Nissan Chemical Industries, Ltd. | Heterocyclic compounds and expansion agents for hematopoietic stem cells |
| WO2011049659A2 (en) * | 2009-08-05 | 2011-04-28 | The Government Of United States, As Represented By The Secretary Of The Army | Novel use and method of rapamycin to treat toxic shock |
| AR086113A1 (es) * | 2011-04-30 | 2013-11-20 | Abbott Lab | Isoxazolinas como agentes terapeuticos |
| CA2887420C (en) * | 2012-10-15 | 2019-01-08 | Aquilus Pharmaceuticals, Inc. | Matrix metalloproteinase inhibitors and methods for the treatment of pain and other diseases |
| US8865723B2 (en) | 2012-10-25 | 2014-10-21 | Tetra Discovery Partners Llc | Selective PDE4 B inhibition and improvement in cognition in subjects with brain injury |
| HUE050030T2 (hu) | 2015-10-02 | 2020-11-30 | Syngenta Participations Ag | Mikrobiocid oxadiazol-származékok |
| CN108289448B (zh) | 2015-12-02 | 2021-10-22 | 先正达参股股份有限公司 | 杀微生物的噁二唑衍生物 |
| JP2019514851A (ja) | 2016-03-24 | 2019-06-06 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物オキサジアゾール誘導体 |
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| JP7077313B2 (ja) | 2016-10-06 | 2022-05-30 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物オキサジアゾール誘導体 |
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| BR112019020734B1 (pt) | 2017-04-05 | 2023-12-05 | Syngenta Participations Ag | Compostos derivados de oxadiazol, composição agroquímica, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos e uso dos referidos compostos |
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| KR20200022452A (ko) | 2017-06-28 | 2020-03-03 | 신젠타 파티서페이션즈 아게 | 살진균 조성물 |
| WO2019011929A1 (en) | 2017-07-11 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
| WO2019011928A1 (en) | 2017-07-11 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
| WO2019011926A1 (en) | 2017-07-11 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
| BR112020000465B1 (pt) | 2017-07-11 | 2024-02-20 | Syngenta Participations Ag | Derivados oxadiazol microbiocidas |
| WO2019012011A1 (en) | 2017-07-12 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
| BR112020000414A2 (pt) | 2017-07-12 | 2020-07-21 | Syngenta Participations Ag | derivados de oxadiazol microbicidas |
| WO2019012003A1 (en) | 2017-07-13 | 2019-01-17 | Syngenta Participations Ag | MICROBIOCIDE OXADIAZOLE DERIVATIVES |
| WO2019097054A1 (en) | 2017-11-20 | 2019-05-23 | Syngenta Participations Ag | Microbiocidal oxadiazole derivatives |
| CN112020503A (zh) | 2018-04-26 | 2020-12-01 | 先正达参股股份有限公司 | 杀微生物的噁二唑衍生物 |
| EP3823966A1 (en) | 2018-07-16 | 2021-05-26 | Syngenta Crop Protection AG | Microbiocidal oxadiazole derivatives |
| AR118673A1 (es) | 2019-04-18 | 2021-10-20 | Syngenta Crop Protection Ag | Procedimiento para la preparación de derivados de oxadiazol microbiocidas |
| GB201908453D0 (en) | 2019-06-12 | 2019-07-24 | Enterprise Therapeutics Ltd | Compounds for treating respiratory disease |
| WO2025257413A1 (en) | 2024-06-13 | 2025-12-18 | Syngenta Crop Protection Ag | Pecticidally active dihydroazole derivatives |
| CN120097935A (zh) * | 2025-02-18 | 2025-06-06 | 贵州大学 | 一种含有1,2,4-噻二唑的酰胺类衍生物及其制备方法和用途 |
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| CA1338625C (en) * | 1988-06-09 | 1996-10-01 | Kyowa Hakko Kogyo Co., Ltd. | Tricyclic compounds |
| US5242931A (en) * | 1988-06-09 | 1993-09-07 | Kyowa Hakko Kogyo Co., Ltd. | Tricyclic compounds as TXA2 antagonists |
| DE3931432A1 (de) * | 1989-09-21 | 1991-04-04 | Hoechst Ag | Pyrimidin-4,6-dicarbonsaeurediamide, verfahren zu deren herstellung sowie verwendung derselben sowie arzneimittel auf basis dieser verbindungen |
| JP2000502704A (ja) * | 1995-12-29 | 2000-03-07 | スミスクライン・ビーチャム・コーポレイション | ビトロネクチン受容体拮抗物質 |
| US20010034445A1 (en) * | 1995-12-29 | 2001-10-25 | Smithkline Beecham Corporation | Vitronectin receptor antagonists |
| CA2256631A1 (en) * | 1996-09-04 | 1998-03-12 | Warner-Lambert Company | Compounds for and a method of inhibiting matrix metalloproteinases |
| US6476027B1 (en) * | 1997-03-04 | 2002-11-05 | Monsanto Company | N-hydroxy 4-sulfonyl butanamide compounds |
| WO2000038683A1 (en) * | 1998-12-23 | 2000-07-06 | Du Pont Pharmaceuticals Company | THROMBIN OR FACTOR Xa INHIBITORS |
| US6407256B1 (en) * | 1999-11-03 | 2002-06-18 | Bristol Myers Squibb Co | Cyano-pyrrole, cyano-imidazole, cyano-pyrazole, and cyano-triazole compounds as factor Xa inhibitors |
| WO2002064571A1 (en) * | 2001-02-14 | 2002-08-22 | Warner-Lambert Company Llc | Pyrimidine matrix metalloproteinase inhibitors |
| US6933298B2 (en) * | 2001-12-08 | 2005-08-23 | Aventis Pharma Deutschland Gmbh | Pyridine-2,4-dicarboxylic acid diamides and pyrimidine-4,6-dicarboxylic acid diamides and the use thereof for selectively inhibiting collagenases |
| US20030187026A1 (en) * | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
| US6747147B2 (en) * | 2002-03-08 | 2004-06-08 | Warner-Lambert Company | Oxo-azabicyclic compounds |
| AU2003245669A1 (en) * | 2002-06-21 | 2004-01-06 | Cellular Genomics, Inc. | Certain aromatic monocycles as kinase modulators |
| EP1394159A1 (fr) * | 2002-08-13 | 2004-03-03 | Warner-Lambert Company LLC | Nouveaux dérivés de thiophène, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent |
| PA8578101A1 (es) * | 2002-08-13 | 2004-05-07 | Warner Lambert Co | Derivados de heterobiarilo como inhibidores de metaloproteinasa de la matriz |
| US7166609B2 (en) * | 2002-11-02 | 2007-01-23 | Sanofi-Aventis Deutschland Gmbh | Pyrimidine-4,6-dicarboxylic acid diamides for selectively inhibiting collagenases |
| BR0317600A (pt) * | 2002-12-20 | 2005-11-29 | Pharmacia Corp | ácidos heteroarilalcanóicos como derivados de antagonistas de receptor de integrina |
| DE10300017A1 (de) * | 2003-01-03 | 2004-07-15 | Aventis Pharma Deutschland Gmbh | Selektive MMP 13 Inhibitoren |
| EP1603884A4 (en) * | 2003-02-28 | 2008-05-28 | Encysive Pharmaceuticals Inc | PYRIDINE, PYRIMIDINE, QUINOLINE, QUINAZOLINE AND NAPHTHALENE UROTENSIN II RECEPTOR ANTAGONISTS |
| US20060173183A1 (en) * | 2004-12-31 | 2006-08-03 | Alantos Pharmaceuticals, Inc., | Multicyclic bis-amide MMP inhibitors |
| US7636552B2 (en) * | 2005-04-08 | 2009-12-22 | The Boeing Company | Point-to-multipoint communications system and method |
-
2006
- 2006-12-28 AU AU2006332694A patent/AU2006332694A1/en not_active Abandoned
- 2006-12-28 JP JP2008548755A patent/JP2009522295A/ja not_active Withdrawn
- 2006-12-28 CA CA002635580A patent/CA2635580A1/en not_active Abandoned
- 2006-12-28 WO PCT/US2006/049521 patent/WO2007079199A2/en not_active Ceased
- 2006-12-28 EP EP06848299A patent/EP1981855A2/en not_active Withdrawn
- 2006-12-28 US US11/646,650 patent/US20070155739A1/en not_active Abandoned
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| US20070155739A1 (en) | 2007-07-05 |
| WO2007079199A3 (en) | 2007-09-13 |
| AU2006332694A1 (en) | 2007-07-12 |
| WO2007079199A2 (en) | 2007-07-12 |
| JP2009522295A (ja) | 2009-06-11 |
| EP1981855A2 (en) | 2008-10-22 |
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