WO1998003166A1 - Thiol sulfonamide metalloprotease inhibitors - Google Patents

Thiol sulfonamide metalloprotease inhibitors Download PDF

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Publication number
WO1998003166A1
WO1998003166A1 PCT/US1997/012873 US9712873W WO9803166A1 WO 1998003166 A1 WO1998003166 A1 WO 1998003166A1 US 9712873 W US9712873 W US 9712873W WO 9803166 A1 WO9803166 A1 WO 9803166A1
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Prior art keywords
group
mmol
alkyl
heteroaryl
nitrogen
Prior art date
Application number
PCT/US1997/012873
Other languages
English (en)
French (fr)
Inventor
Gary Decrescenzo
Zaheer S. Abbas
John N. Freskos
Daniel P. Getman
Robert M. Heintz
Brent V. Mischke
Joseph J. Mcdonald
Original Assignee
Monsanto Company
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Monsanto Company filed Critical Monsanto Company
Priority to IL12808097A priority Critical patent/IL128080A0/xx
Priority to JP10507195A priority patent/JP2000515153A/ja
Priority to CA002260860A priority patent/CA2260860A1/en
Priority to EP97936168A priority patent/EP0939629A4/en
Priority to NZ333825A priority patent/NZ333825A/xx
Priority to BR9710752A priority patent/BR9710752A/pt
Priority to CZ99168A priority patent/CZ16899A3/cs
Priority to PL97331338A priority patent/PL331338A1/xx
Priority to AU38903/97A priority patent/AU740263C/en
Publication of WO1998003166A1 publication Critical patent/WO1998003166A1/en
Priority to NO19990247A priority patent/NO314035B1/no

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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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/18—Sulfonamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/17—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
    • C07C323/49—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C07D207/48—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/96—Sulfur atom
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
    • 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
    • C07D409/04—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 directly linked by a ring-member-to-ring-member bond

Definitions

  • R 3 and R 4 groups are independently selected.
  • substituents can be hydrogen (hydrido) , an alkyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, hydroxyalkyl, aryloxyalkyl, aralkoxyalkyl, aralkyl, aryl, heteroaryl, heteroaralkyl, hydroxycarbonylalkyl, alkoxycarbonylalkyl , aralkoxycarbonylalkyl , hydroxycarbonyl , alkoxycarbonyl, perfluoroalkyl , trifluoromethylalkyl, thioalkyl, alkylthioalkyl, arylthioalkyl, aralkylthioalkyl , heteroaralkylthioalkyl , or a sulfoxide or sulfone of any of the thio substituents, aminocarbonyl, aminocarbonylalkyl, N-
  • R 7 and R 8 substituents are also independently selected.
  • R 7 and R 8 substituents can also be a substituent that constitutes R-* and R , or R 8 and R 2 together with the atoms to which they are attached form a 6- to 8-membered ring (as above) , or R 7 and R 8 together with the atom to which they are attached form a 3- to 8-membered ring, or R 8 and R 4 together with the atom to which they are attached form a 5- to 8-membered ring (as above) , or R 8 and R 6 together with the atoms to which they are attached form a 4- to 8-membered ring (as above) .
  • R 8 and R 6 together with the atoms to which they are attached form a 4- to 8-membered ring (as above) .
  • a provision to the above definitions is provided that no carbon atom is geminally substituted with more than one sulfhydryl group.
  • starred substituent "R" groups and “x” of formula III are the same as or different from the unstarred "R” groups and "x” .
  • R 9 represents C; ⁇ _-C alkyl, C5-C8 cycloalkyl, aryl, C; ⁇ _-Cg alkoxy, heteroaryl, amino C ⁇ -Cg alkyl, N-monosubstituted amino C ⁇ -C alkyl and N,N-disubstituted amino C ⁇ _-Cg alkyl, wherein the substituents on nitrogen are chosen from C ⁇ -C alkyl, aralkyl, C5-C3 cycloalkyl and C ⁇ _-Cg alkanoyl, or wherein the two substituents and the nitrogen to which they are attached when taken together form a 5- to 8-membered heterocyclo or heteroaryl ring.
  • R 9 represents C ⁇ _-Cg alkyl, C3_-C alkoxy, a single-ringed aryl or heteroaryl.
  • 5- or 6-membered is itself preferably substituted at its own 4 -position when a 6-membered ring and at its own 3 -position when a 5 -membered ring with a substituent selected from the group consisting of one other single-ringed aryl or hetroaryl group, an alkyl or alkoxy group containing an umbranched chain of 3 to about 7 carbon atoms, a phenoxy group, a thiophenoxy group, a phenylazo group or a benzamido group .
  • An R 2 group is C ] _-Cg alkyl and particularly methyl, a C2-C3 alkyl cycloamino group having five or six atoms in the ring and zero or one additional heteroatom that is oxygen or nitrogen, and ⁇ - ⁇ alkyl single-ringed aryl or heteroaryl, wherein the single heteroaryl ring contains one or two nitrogen atoms.
  • Exemplary most preferred substituents in addition to methyl include 2- (4-morpholino) ethyl , 2- (1-piperidino) ethyl, 2- (1-pyrrolidino) ethyl and
  • R 3 group is hydrido
  • R 4 is hydroxyxcarbonyl , aminocarbonyl or C ⁇ -C alkyl.
  • perfluoroalkyl means an alkyl group wherein each hydrogen has been replaced by a fluorine atom.
  • perfluoroalkyl groups in addition to trifluoromethyl above, are perfluorobutyl , perfluoroisopropyl , perfluorododecyl and perfluorodecyl .
  • aromatic ring in combinations such as substituted-aromatic ring sulfonamide, substituted-aromatic ring sulfinamide or substituted- aromatic ring sulfenamide means aryl or heteroaryl as defined above.
  • M utilized in the reaction Schemes that follow represents a leaving group such as halogen, phosphate ester or sulfate ester.
  • solvents, solvent mixtures or solvent/reagent mixtures discussed above are satisfactory but non-protic or dipolar aprotic solvents such as acetone, acetonitrile, DMF, acetonitrile and the like are examples of a preferred class.
  • Bases can also be used as solvents as well as reagents. Mixtures of the above solvents or with a solvent and a base such as pyridine or triethylamine are also useful. These reactions are usually carried out under an inert atmosphere (nitrogen, argon) at temperatures varying from between about -10°C to about 80 °C. In many cases, room temperature is preferred due to cost or simplicity.
  • Step 4 in Scheme 2 involves the hydroxyl conversion step discussed in with regards to Step 1 in Scheme 1.
  • protection of a non- reactive group can be desirable.
  • the sulfamide can be alkylated or reductively alkylated to introduce the R 2 group (Step 5) if such is desired.
  • Optically active compound isomers as well as mixed or non-optically active compound isomers are specifically intended to be included in this discussion.
  • isomers are RS isomers, enantiomers, diastereomers , racemates, cis isomers, trans isomers, E isomers, Z isomers, syn- isomers, anti- isomers, tauto ers and the like.
  • Aryl, heterocyclo or heteroaryl tautomers, heteroatom isomers and ortho, meta or para substitution isomers are also included as isomers.
  • Part B To a solution of 4.0 g (12.4 mmol) of N- (2-hydroxyethyl) -N- (phenylmethyl) -4- methoxybenzenesulfonamide from Part A in 6 mL of anhydrous methylene chloride and 6 mL of anhydrous dimethyl sulfoxide, was added 17.1 mL of triethylamine, the solution cooled in an ice bath and 7.9 g (50 mmol) of sulfur trioxide/pyridme complex m 38 mL of DMSO was added over 15 minutes.
  • Part A To a solution of 15.5 mL (15.0 g, 200 mmol) of (S) -(+) -2-amino-l-propanol in 70 mL of THF and 18 mL of water, was added 36 mL (259 mmol) of triethylamine. After cooling in an ice bath, a solution of 37.1 g (179 mmol) of 4- methoxybenzenesulfonyl chloride in 30 mL of tetrahydrofuran was slowly added over 15 minutes.
  • Part B To a solution of 5.0 g (20 mmol) of N- (2-hydroxy-lS-methylethyl) 4- methoxybenzenesulfonamide from part A in 40 mL of anhydrous DMF, was added 8.5 g (61 mmol) of powdered potassium carbonate, followed by 3.2 mL (4.5 g, 27 mmol) of benzyl bromide. After 64 hours, the reaction was concentrated in vacuo, ethyl acetate and water were added, the organic layer was separated and washed 3xs with brine, dried with magnesium sulfate, filtered and concentrated to afford 7.0 g of crude product.
  • Part B To a solution of 4.88 g (12.5 mmol) of product from Part A in 50 mL of anhydrous THF at 0°C under nitrogen, was added 12.5 mL (12.5 mmol) of a 1.0 M solution of lithium aluminum hydride in diethyl ether.
  • Part A To a solution of 7.4 L (95.1 mmol) of (R) -(-) -2-amino-l-propanol in 31 mL of THF and 9 L of water, was added 17.2 mL (123 mmol) of triethylamine. After cooling in an ice bath, a solution of 24.4 g (86.5 mmol) of 4- (benzyloxy) - benzenesulfonyl chloride in 40 mL of tetrahydrofuran was slowly added over 15 minutes.
  • Part A To a solution of 1.72 g (6.95 mmol) of N- (2 -hydroxy- IR-methylethyl) -N-methyl-4- fluorobenzenesulfonamide from Example 40, part B, in 10 mL of anhydrous DMF, was added 7.03 g (21.5 mmol) of cesium carbonate, and then 1.0 mL (1.07 g, 9.73 mmol) of thiophenol. The reaction mixture was heated to 70 C for 15 hours, cooled and ethyl acetate and water added. The organic layer was separated and washed 3xs with brine, dried with sodium sulfate, filtered and stripped to afford 2.5 g of crude material.
PCT/US1997/012873 1996-07-22 1997-07-22 Thiol sulfonamide metalloprotease inhibitors WO1998003166A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
IL12808097A IL128080A0 (en) 1996-07-22 1997-07-22 Thiol sulfonamide metalloprotease inhibitors
JP10507195A JP2000515153A (ja) 1996-07-22 1997-07-22 チオールスルホンアミド メタロプロテアーゼインヒビター
CA002260860A CA2260860A1 (en) 1996-07-22 1997-07-22 Thiol sulfonamide metalloprotease inhibitors
EP97936168A EP0939629A4 (en) 1996-07-22 1997-07-22 THIOL-SULFONAMIDES AS METALLOPROTEINAS INHIBITORS
NZ333825A NZ333825A (en) 1996-07-22 1997-07-22 Metalloprotease inhibitors particularly MMP-13
BR9710752A BR9710752A (pt) 1996-07-22 1997-07-22 Inbidores de metaloprotease de sulfonamida de tiol
CZ99168A CZ16899A3 (cs) 1996-07-22 1997-07-22 Thiolsulfonamidové inhibitory metaloproteázy
PL97331338A PL331338A1 (en) 1996-07-22 1997-07-22 Thiosulphonamidic metaloprotease inhibitors
AU38903/97A AU740263C (en) 1996-07-22 1997-07-22 Thiol sulfonamide metalloprotease inhibitors
NO19990247A NO314035B1 (no) 1996-07-22 1999-01-20 Tiolsulfonamidmetalloproteaseinhibitorer, farmasöytisk sammensetning innbefattende samme og anvendelse av samme for fremstilling avmedikament

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US2204096P 1996-07-22 1996-07-22
US60/022,040 1996-07-22

Publications (1)

Publication Number Publication Date
WO1998003166A1 true WO1998003166A1 (en) 1998-01-29

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Country Status (14)

Country Link
EP (1) EP0939629A4 (ru)
JP (1) JP2000515153A (ru)
KR (1) KR20000067964A (ru)
CN (1) CN1238688A (ru)
AU (1) AU740263C (ru)
BR (1) BR9710752A (ru)
CA (1) CA2260860A1 (ru)
CZ (1) CZ16899A3 (ru)
IL (1) IL128080A0 (ru)
NO (1) NO314035B1 (ru)
NZ (1) NZ333825A (ru)
PL (1) PL331338A1 (ru)
RU (1) RU2202540C2 (ru)
WO (1) WO1998003166A1 (ru)

Cited By (55)

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WO1999004780A1 (fr) * 1997-07-22 1999-02-04 Shionogi & Co., Ltd. Agent therapeutique ou prophylactique de traitement de la glomerulopathie
WO2000044716A1 (en) * 1999-01-27 2000-08-03 American Cyanamid Company Acetylenic sulfonamide thiol tace inhibitors
WO2000050391A1 (en) * 1999-02-26 2000-08-31 Merck & Co., Inc. Novel sulfonamide compounds and uses thereof
WO2000063194A1 (fr) * 1999-04-19 2000-10-26 Shionogi & Co., Ltd. Derives de sulfonamide possedant des noyaux oxadiazole
WO2001005389A2 (en) * 1999-07-16 2001-01-25 G.D. Searle & Co. N-sulfonylaminiacid derivatives as inhibitors of metalloprteinase
US6200996B1 (en) 1999-01-27 2001-03-13 American Cyanamid Company Heteroaryl acetylenic sulfonamide and phosphinic acid amide hydroxamic acid tace inhibitors
EP1088815A1 (en) * 1999-09-28 2001-04-04 Applied Research Systems ARS Holding N.V. Pharmaceutically active sulfonyl amino acid derivatives
US6225311B1 (en) 1999-01-27 2001-05-01 American Cyanamid Company Acetylenic α-amino acid-based sulfonamide hydroxamic acid tace inhibitors
US6277885B1 (en) 1999-01-27 2001-08-21 American Cyanamid Company Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic acid TACE inhibitors
WO2001077092A1 (en) * 2000-04-07 2001-10-18 Samsung Electronics Co., Ltd. Sulfonamide derivative as a matrix metalloproteinase inhibitor
US6313123B1 (en) 1999-01-27 2001-11-06 American Cyanamid Company Acetylenic sulfonamide thiol tace inhibitors
US6326516B1 (en) 1999-01-27 2001-12-04 American Cyanamid Company Acetylenic β-sulfonamido and phosphinic acid amide hydroxamic acid TACE inhibitors
WO2002003994A1 (en) * 2000-07-12 2002-01-17 G.D. Searle & Co. N sulfonyl aminoacid derivatives as inhibitors of metalloproteinase
US6340691B1 (en) 1999-01-27 2002-01-22 American Cyanamid Company Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase and tace inhibitors
US6358980B1 (en) 1999-01-27 2002-03-19 American Cyanamid Company Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase/tace inhibitors
US6420415B1 (en) 1998-09-21 2002-07-16 Takeda Chemical Industries, Ltd. Thiol compounds, their production and use
WO2002100846A1 (en) * 2001-06-11 2002-12-19 Shire Biochem Inc. Compounds and methods for the treatment or prevention of flavivirus infections
WO2003053912A1 (en) * 2001-12-20 2003-07-03 Bristol-Myers Squibb Company α-(N-SULPHONAMIDO)ACETAMIDE DERIVATIVES AS β-AMYLOID INHIBITORS
US6610734B2 (en) 2000-12-13 2003-08-26 Wyeth Heterocyclic sulfonamide inhibitors of beta amyloid production
US6657070B2 (en) 2000-12-13 2003-12-02 Wyeth Production of chirally pure α-amino acids and N-sulfonyl α-amino acids
US6753337B2 (en) 1999-01-27 2004-06-22 Wyeth Holdings Corporation Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase/tace inhibitors
US6762178B2 (en) 1999-01-27 2004-07-13 Wyeth Holdings Corporation Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic acid TACE inhibitors
EP1493740A1 (fr) * 2003-07-03 2005-01-05 Warner-Lambert Company LLC Dérivés de 5-fluoro-thiophene, leur procédé de preparation, les compositions pharmaceutiques les contenant et leur utilisation comme inhibiteurs de métalloprotéinases
US6869951B1 (en) 1999-07-16 2005-03-22 Pharmacia Corporation Method of changing conformation of a matrix metalloproteinase
US6946473B2 (en) 1999-01-27 2005-09-20 Wyeth Holdings Corporation Preparation and use of acetylenic ortho-sulfonamido and phosphinic acid amido bicyclic heteroaryl hydroxamic acids as TACE inhibitors
WO2005118528A2 (en) * 2004-06-04 2005-12-15 The University Court Of The University Of Aberdeen Aryl alkyl sulfonamides as therapeutic agents for the treatment of bone conditions
JP2006518352A (ja) * 2003-02-21 2006-08-10 マックス−プランク−ゲゼルシャフト・ツア・フェルデルング・デア・ヴィッセンシャフテン・エー・ファオ Ｅｇｆレセプターシグナル伝達の調節のためのｔａｃｅまたはアンフィレグリンの阻害
US7199155B2 (en) 2002-12-23 2007-04-03 Wyeth Holdings Corporation Acetylenic aryl sulfonate hydroxamic acid TACE and matrix metalloproteinase inhibitors
US7282496B2 (en) 2001-11-01 2007-10-16 Wyeth Holdings Corporation Allenic aryl sulfonamide hydroxamic acids as matrix metalloproteinase and TACE inhibitors
US7300951B2 (en) 2003-03-31 2007-11-27 Wyeth Fluoro- and trifluoroalkyl-containing heterocyclic sulfonamide inhibitors of beta amyloid production and derivatives thereof
US7595327B2 (en) 2005-03-21 2009-09-29 Wyeth Beta-sulfonamide hydroxamic acid inhibitors of tace/matrix metalloproteinase
US7618960B2 (en) 2005-11-24 2009-11-17 Eisai R&D Management Co., Ltd. Morpholine type cinnamide compound
WO2010010080A1 (en) * 2008-07-22 2010-01-28 Bracco Imaging Spa Aryl-sulphonamidic dimers as metalloproteases inhibitors
US7671075B2 (en) 2002-06-11 2010-03-02 Wyeth Substituted phenylsulfonamide inhibitors of beta amyloid production
US7687640B2 (en) 2004-05-26 2010-03-30 Eisai R&D Management Co., Ltd. Cinnamide compound
US7713993B2 (en) 2006-03-09 2010-05-11 Eisai R&D Management Co., Ltd. Multi-cycle cinnamide derivatives
US7737141B2 (en) 2006-07-28 2010-06-15 Eisai R&D Management Co., Ltd. Prodrug of cinnamide compound
US7923563B2 (en) 2004-10-26 2011-04-12 Eisai R&D Management Co., Ltd. Amorphous object of cinnamide compound
US7935815B2 (en) 2007-08-31 2011-05-03 Eisai R&D Management Co., Ltd. Imidazoyl pyridine compounds and salts thereof
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IL128080A0 (en) 1999-11-30
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AU740263C (en) 2002-05-16
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