MXPA06004440A - Inhibidores de catepsina-s. - Google Patents
Inhibidores de catepsina-s.Info
- Publication number
- MXPA06004440A MXPA06004440A MXPA06004440A MXPA06004440A MXPA06004440A MX PA06004440 A MXPA06004440 A MX PA06004440A MX PA06004440 A MXPA06004440 A MX PA06004440A MX PA06004440 A MXPA06004440 A MX PA06004440A MX PA06004440 A MXPA06004440 A MX PA06004440A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- group
- substituted
- amino
- independently
- Prior art date
Links
- 102000005600 Cathepsins Human genes 0.000 title abstract description 39
- 108010084457 Cathepsins Proteins 0.000 title abstract description 39
- 239000003112 inhibitor Substances 0.000 title description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 192
- 108090000613 Cathepsin S Proteins 0.000 claims abstract description 100
- 102100035654 Cathepsin S Human genes 0.000 claims abstract description 100
- 230000005764 inhibitory process Effects 0.000 claims abstract description 89
- 238000000034 method Methods 0.000 claims abstract description 58
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 292
- 125000000217 alkyl group Chemical group 0.000 claims description 113
- -1 = 0 Chemical group 0.000 claims description 103
- 229910052757 nitrogen Inorganic materials 0.000 claims description 60
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 52
- 125000001072 heteroaryl group Chemical group 0.000 claims description 48
- 229910052760 oxygen Inorganic materials 0.000 claims description 46
- 125000005842 heteroatom Chemical group 0.000 claims description 45
- 125000003545 alkoxy group Chemical group 0.000 claims description 44
- 229910052717 sulfur Inorganic materials 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 33
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 31
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 25
- 102000011727 Caspases Human genes 0.000 claims description 23
- 108010076667 Caspases Proteins 0.000 claims description 23
- 241000124008 Mammalia Species 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 18
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 18
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 18
- 125000002757 morpholinyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- 125000005936 piperidyl group Chemical group 0.000 claims description 9
- 229940002612 prodrug Drugs 0.000 claims description 9
- 239000000651 prodrug Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 229920001774 Perfluoroether Polymers 0.000 claims 1
- 108010044467 Isoenzymes Proteins 0.000 abstract description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 14
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- 238000006243 chemical reaction Methods 0.000 description 60
- 239000000758 substrate Substances 0.000 description 37
- 239000002904 solvent Substances 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 235000019439 ethyl acetate Nutrition 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 238000011282 treatment Methods 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 102000004190 Enzymes Human genes 0.000 description 19
- 108090000790 Enzymes Proteins 0.000 description 19
- 229940088598 enzyme Drugs 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 108090000625 Cathepsin K Proteins 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 230000001419 dependent effect Effects 0.000 description 12
- 108090000712 Cathepsin B Proteins 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
- 238000010494 dissociation reaction Methods 0.000 description 11
- 230000005593 dissociations Effects 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 102000004171 Cathepsin K Human genes 0.000 description 10
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 230000002860 competitive effect Effects 0.000 description 10
- 102000004225 Cathepsin B Human genes 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
- 102100035904 Caspase-1 Human genes 0.000 description 8
- 108090000426 Caspase-1 Proteins 0.000 description 8
- 102100029855 Caspase-3 Human genes 0.000 description 8
- 102000004091 Caspase-8 Human genes 0.000 description 8
- 108090000624 Cathepsin L Proteins 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 238000012544 monitoring process Methods 0.000 description 8
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- 239000007821 HATU Substances 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
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- 238000005259 measurement Methods 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 150000007659 semicarbazones Chemical class 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
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- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 6
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 6
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- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen atoms
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- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
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- Diabetes (AREA)
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- Pain & Pain Management (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51373503P | 2003-10-21 | 2003-10-21 | |
| US10/970,344 US7297714B2 (en) | 2003-10-21 | 2004-10-20 | Inhibitors of cathepsin S |
| PCT/US2004/035062 WO2005039496A2 (en) | 2003-10-21 | 2004-10-21 | Inhibitors of cathepsin s |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06004440A true MXPA06004440A (es) | 2006-06-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA06004440A MXPA06004440A (es) | 2003-10-21 | 2004-10-21 | Inhibidores de catepsina-s. |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7297714B2 (https=) |
| EP (1) | EP1677782A4 (https=) |
| JP (1) | JP2007527411A (https=) |
| AU (1) | AU2004283708B2 (https=) |
| BR (1) | BRPI0415824A (https=) |
| CA (1) | CA2542963A1 (https=) |
| MX (1) | MXPA06004440A (https=) |
| WO (1) | WO2005039496A2 (https=) |
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| KR20090064463A (ko) * | 2006-10-23 | 2009-06-18 | 아이알엠 엘엘씨 | 카텝신 프로테아제 억제제 |
| US20160038600A1 (en) | 2012-08-03 | 2016-02-11 | Neonc Technologies Inc. | Pharmaceutical compositions comprising poh derivatives |
| TWI402072B (zh) * | 2010-10-19 | 2013-07-21 | Lilly Co Eli | 組織蛋白酶ｓ抑制劑化合物 |
| ES3056006T3 (en) * | 2010-12-17 | 2026-02-17 | Univ Southern California | Methods and devices for using isoperillyl alcohol |
| AU2020250933A1 (en) | 2019-04-05 | 2021-10-28 | Centre Hospitalier Régional Et Universitaire De Brest | Protease-activated receptor-2 inhibitors for the treatment of sensory neuropathy induced by a marine neurotoxic poisoning |
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| US5756466A (en) * | 1994-06-17 | 1998-05-26 | Vertex Pharmaceuticals, Inc. | Inhibitors of interleukin-1β converting enzyme |
| KR20000036056A (ko) * | 1996-09-12 | 2000-06-26 | 아이디유엔 파마슈티칼즈, 인코포레이티드 | 인터루킨-1β 전환 효소 및 관련 프로테아제의 억제제로서의 Ｃ-말단 변형된 (Ｎ-치환된)-2-인돌릴 디펩티드 |
| ES2242394T3 (es) * | 1998-05-05 | 2005-11-01 | Warner-Lambert Company Llc | Inhibidores de tipo succinamida de la enzima convertidora de la interleuquina 1 beta. |
| EP1155010A1 (en) * | 1999-02-20 | 2001-11-21 | AstraZeneca AB | Acetamido acetonitrile derivatives as inhibitors of cathepsin l and/or cathepsin s |
| CN1362947A (zh) * | 1999-03-15 | 2002-08-07 | Axys药物公司 | 用作蛋白酶抑制剂的n－氰基甲基酰胺 |
| CN1176941C (zh) | 1999-04-09 | 2004-11-24 | 西托维亚公司 | Caspase抑制剂及其应用 |
| GB9911417D0 (en) * | 1999-05-18 | 1999-07-14 | Peptide Therapeutics Ltd | Furanone derivatives as inhibitors of cathepsin s |
| JP2003506364A (ja) * | 1999-07-30 | 2003-02-18 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | システインプロテアーゼインヒビターとして有益な新規スクシネート誘導体化合物 |
| YU17402A (sh) * | 1999-09-13 | 2004-11-25 | Boehringer Ingelheim Pharmaceuticals Inc. | Nova spiroheterociklična jedinjenja upotrebljiva kao reverzibilni inhibitori cisteinskih proteaza |
| CO5280088A1 (es) * | 2000-04-18 | 2003-05-30 | Smithkline Beecham Corp | Inhibidores de proteasa |
| JP2004513942A (ja) * | 2000-11-17 | 2004-05-13 | メディヴァー ユーケイ リミテッド | システインプロテアーゼインヒビター |
| AU2002232541A1 (en) | 2000-11-21 | 2002-06-03 | Vertex Pharmaceuticals Incorporated | Imidazole and benzimidazole caspase inhibitors and uses thereof |
| US6982263B2 (en) * | 2001-06-08 | 2006-01-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Nitriles useful as reversible inhibitors of cysteine proteases |
| US20030144234A1 (en) * | 2001-08-30 | 2003-07-31 | Buxton Francis Paul | Methods for the treatment of chronic pain and compositions therefor |
| US6900237B2 (en) * | 2001-09-14 | 2005-05-31 | Axys Pharmaceuticals, Inc. | Sulfonamide compounds as protease inhibitors |
| WO2003031437A1 (en) * | 2001-10-09 | 2003-04-17 | Smithkline Beecham Corporation | Propylcarbamate derivatives as inhibitors of serine and cysteine proteases |
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2004
- 2004-10-20 US US10/970,344 patent/US7297714B2/en not_active Expired - Fee Related
- 2004-10-21 CA CA002542963A patent/CA2542963A1/en not_active Abandoned
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2007
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Also Published As
| Publication number | Publication date |
|---|---|
| US20080021025A1 (en) | 2008-01-24 |
| WO2005039496A3 (en) | 2005-09-15 |
| EP1677782A4 (en) | 2010-11-17 |
| AU2004283708B2 (en) | 2007-08-16 |
| BRPI0415824A (pt) | 2007-01-02 |
| CA2542963A1 (en) | 2005-05-06 |
| AU2004283708A1 (en) | 2005-05-06 |
| US20050130959A1 (en) | 2005-06-16 |
| WO2005039496A2 (en) | 2005-05-06 |
| JP2007527411A (ja) | 2007-09-27 |
| EP1677782A2 (en) | 2006-07-12 |
| US7297714B2 (en) | 2007-11-20 |
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