UY25143A1 - PROCEDURE FOR THE PREPARATION OF PROTEASE INHIBITORS. - Google Patents
PROCEDURE FOR THE PREPARATION OF PROTEASE INHIBITORS.Info
- Publication number
- UY25143A1 UY25143A1 UY25143A UY25143A UY25143A1 UY 25143 A1 UY25143 A1 UY 25143A1 UY 25143 A UY25143 A UY 25143A UY 25143 A UY25143 A UY 25143A UY 25143 A1 UY25143 A1 UY 25143A1
- Authority
- UY
- Uruguay
- Prior art keywords
- alkyl
- het
- alkenyl
- cysteine proteases
- inhibitors
- Prior art date
Links
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 title 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 title 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 102000005927 Cysteine Proteases Human genes 0.000 abstract 3
- 108010005843 Cysteine Proteases Proteins 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000003112 inhibitor Substances 0.000 abstract 2
- -1 3,4-dichlorobenzoyl Chemical group 0.000 abstract 1
- ZONXMMDPDDVDDH-UHFFFAOYSA-N 4-aminooxolan-3-one Chemical compound NC1COCC1=O ZONXMMDPDDVDDH-UHFFFAOYSA-N 0.000 abstract 1
- ZPZCGXUJKYTBDW-UHFFFAOYSA-N 4-aminothiolan-3-one Chemical compound NC1CSCC1=O ZPZCGXUJKYTBDW-UHFFFAOYSA-N 0.000 abstract 1
- 102000005600 Cathepsins Human genes 0.000 abstract 1
- 108010084457 Cathepsins Proteins 0.000 abstract 1
- BAGVCUUHECEEDZ-UHFFFAOYSA-N NC1CCOCC1=O Chemical compound NC1CCOCC1=O BAGVCUUHECEEDZ-UHFFFAOYSA-N 0.000 abstract 1
- 208000001132 Osteoporosis Diseases 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 206010003246 arthritis Diseases 0.000 abstract 1
- 210000000988 bone and bone Anatomy 0.000 abstract 1
- 210000000845 cartilage Anatomy 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 201000001245 periodontitis Diseases 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/99—Enzyme inactivation by chemical treatment
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/06—Anabolic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
- C07D307/22—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-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
- C07D309/28—Heterocyclic compounds containing six-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
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—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
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Genetics & Genomics (AREA)
- Biomedical Technology (AREA)
- Endocrinology (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- Immunology (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Neurology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrane Compounds (AREA)
- Peptides Or Proteins (AREA)
Abstract
Procedimiento para preparar compuestos derivados n-sustituidos de 4-amino-tetrahidrofuran-3-ona, 4-aminotetrahidropiran-3-ona y 4-aminotetrahidrotiofen-3-ona utilizados como inhibidores de cisteína proteasas, particularmente catepsina k. Son útiles en el tratamiento de enfermedades caracterizadas por la pérdida excesiva de hueso o cartílago, por ejemplo osteoporosis, periodontitis y artritis, en las que están implicadas cisteína proteasas. Es un compuesto de fórmula l en que: R1 es R'', R''C(O), R''C(S), R''OC(O), CH(R6)C(O); R2 es H, alquilo, alquenilo, Ar-alquilo, o Het-alquilo; R3 es H, alquilo, alquenilo, alquinilo, cicloalquil, Het-alquilo; R4 es H, alquilo, alquenilo, Ar-alquilo, Het-alquilo; R5 en cada caso, es independientemente H, alquilo, alquenilo, Ar-alquilo, Het-alquilo; X es O o S; y nes 1,2 o 3; o una sal farmacéuticamente aceptables, que son inhibidores de cisteína proteasas. Ejemplo de un compuesto de fórmula l sería: 4-(R, S)-Amino-N-[(3,4-diclorobenzoil)-S-leucina]-tetrahidrofuran-3-ona.Process for preparing n-substituted derivative compounds of 4-amino-tetrahydrofuran-3-one, 4-aminotetrahydropyran-3-one and 4-aminotetrahydrothiophen-3-one used as inhibitors of cysteine proteases, particularly cathepsin k. They are useful in the treatment of diseases characterized by excessive loss of bone or cartilage, for example osteoporosis, periodontitis and arthritis, in which cysteine proteases are involved. It is a compound of formula I in which: R1 is R ", R" C (O), R "C (S), R" OC (O), CH (R6) C (O); R2 is H, alkyl, alkenyl, Ar-alkyl, or Het-alkyl; R3 is H, alkyl, alkenyl, alkynyl, cycloalkyl, Het-alkyl; R4 is H, alkyl, alkenyl, Ar-alkyl, Het-alkyl; R5 at each occurrence is independently H, alkyl, alkenyl, Ar-alkyl, Het-alkyl; X is O or S; and nes 1,2 or 3; or a pharmaceutically acceptable salt, which are inhibitors of cysteine proteases. Example of a compound of formula I would be: 4- (R, S) -Amino-N - [(3,4-dichlorobenzoyl) -S-leucine] -tetrahydrofuran-3-one.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4575897P | 1997-05-06 | 1997-05-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UY25143A1 true UY25143A1 (en) | 1998-11-27 |
Family
ID=21939723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UY25143A UY25143A1 (en) | 1997-05-06 | 1998-08-17 | PROCEDURE FOR THE PREPARATION OF PROTEASE INHIBITORS. |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP1003846A4 (en) |
| JP (1) | JP2001525804A (en) |
| KR (1) | KR20010012256A (en) |
| CN (1) | CN1255161A (en) |
| AR (1) | AR013079A1 (en) |
| AU (1) | AU7562598A (en) |
| BR (1) | BR9809306A (en) |
| CA (1) | CA2288868A1 (en) |
| CO (1) | CO4950618A1 (en) |
| HU (1) | HUP0002247A3 (en) |
| IL (1) | IL132088A0 (en) |
| NO (1) | NO995434L (en) |
| NZ (1) | NZ337889A (en) |
| PE (1) | PE71599A1 (en) |
| PL (1) | PL336856A1 (en) |
| TR (1) | TR199902766T2 (en) |
| UY (1) | UY25143A1 (en) |
| WO (1) | WO1998050533A1 (en) |
| ZA (1) | ZA983762B (en) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CO5150165A1 (en) * | 1998-11-13 | 2002-04-29 | Smithkline Beecham Plc | PROTEASE INHIBITORS: KATEPSIN K TYPE |
| DZ3083A1 (en) * | 1999-02-19 | 2004-06-02 | Smithkline Beecham Corp | New protease inhibitor compounds, process for their preparation and pharmaceutical compositions containing them |
| GB9911417D0 (en) * | 1999-05-18 | 1999-07-14 | Peptide Therapeutics Ltd | Furanone derivatives as inhibitors of cathepsin s |
| AU1588901A (en) * | 1999-11-10 | 2001-06-06 | Smithkline Beecham Corporation | Protease inhibitors |
| US20040024000A1 (en) * | 2000-10-19 | 2004-02-05 | Rajeshwar Singh | Dihydropyrimidine derivatives as cysteine protease inhibitors |
| EP1345931A2 (en) * | 2000-11-17 | 2003-09-24 | Medivir UK Ltd | Cysteine protease inhibitors |
| WO2002088106A2 (en) * | 2000-11-17 | 2002-11-07 | Medivir Ab | Cysteine protease inhibitors |
| US6958358B2 (en) | 2001-01-17 | 2005-10-25 | Amura Therapeutics Limited | Inhibitors of cruzipain and other cysteine proteases |
| CN1269822C (en) * | 2001-01-17 | 2006-08-16 | 阿姆拉医疗有限公司 | Inhibitors of Cruz protease and other cysteine proteases |
| CA2435117A1 (en) * | 2001-01-17 | 2002-07-25 | Amura Therapeutics Limited | Cyclic 2-carbonylaminoketones as inhibitors of cruzipain and other cysteine proteases |
| US7132449B2 (en) | 2001-01-17 | 2006-11-07 | Amura Therapeutics Limited | Inhibitors of cruzipain and other cysteine proteases |
| WO2003037892A1 (en) * | 2001-10-29 | 2003-05-08 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as reversible inhibitors of cysteine proteases |
| WO2004007501A1 (en) * | 2002-07-16 | 2004-01-22 | Amura Therapeutics Limited | Biologically active compounds |
| KR100962972B1 (en) | 2002-07-26 | 2010-06-09 | 주식회사유한양행 | 1-phenylpiperidin-3-one derivatives and preparation method thereof |
| AU2016206281B2 (en) * | 2003-08-06 | 2017-11-30 | Senomyx, Inc. | Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| CA2535045A1 (en) | 2003-08-06 | 2005-02-17 | Senomyx, Inc. | T1r hetero-oligomeric taste receptors, cell lines that express said receptors, and taste compounds |
| EP1701960B1 (en) * | 2004-01-08 | 2010-03-17 | Medivir Aktiebolag | Cysteine protease inhibitors |
| WO2007022241A2 (en) * | 2005-08-17 | 2007-02-22 | Schering Corporation | Novel high affinity quinoline-based kinase ligands |
| GB0614042D0 (en) | 2006-07-14 | 2006-08-23 | Amura Therapeutics Ltd | Compounds |
| MX2009012847A (en) * | 2007-06-13 | 2009-12-08 | Bristol Myers Squibb Co | Dipeptide analogs as coagulation factor inhibitors. |
| US7893067B2 (en) | 2007-06-27 | 2011-02-22 | Medivir Ab | Cysteine protease inhibitors |
| WO2009087379A2 (en) | 2008-01-09 | 2009-07-16 | Amura Therapeutics Limited | Tetrahydrofuro (3, 2 -b) pyrrol- 3 -one derivatives as inhibitors of cysteine proteinases |
| GB0817424D0 (en) * | 2008-09-24 | 2008-10-29 | Medivir Ab | Protease inhibitors |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3190431B2 (en) * | 1991-07-01 | 2001-07-23 | 三菱化学株式会社 | Ketone derivatives |
| JPH05140063A (en) * | 1991-11-19 | 1993-06-08 | Suntory Ltd | Dipeptide derivative and medicine for preventing and improving osteopathy, containing the same compound as active component |
| CA2111930A1 (en) * | 1992-12-25 | 1994-06-26 | Ryoichi Ando | Aminoketone derivatives |
| JP2848232B2 (en) * | 1993-02-19 | 1999-01-20 | 武田薬品工業株式会社 | Aldehyde derivatives |
| JP3599287B2 (en) * | 1993-04-28 | 2004-12-08 | 三菱化学株式会社 | Sulfonamide derivative |
| US5403952A (en) * | 1993-10-08 | 1995-04-04 | Merck & Co., Inc. | Substituted cyclic derivatives as novel antidegenerative agents |
| SK88997A3 (en) * | 1995-10-30 | 1998-05-06 | Smithkline Beecham Corp | Method of inhibiting cathepsin k |
| TW448172B (en) * | 1996-03-08 | 2001-08-01 | Pharmacia & Upjohn Co Llc | Novel hydroxamic acid derivatives useful for the treatment of diseases related to connective tissue degradation |
| WO1998004539A1 (en) * | 1996-07-29 | 1998-02-05 | Mitsubishi Chemical Corporation | Oxygenic heterocyclic derivatives |
-
1998
- 1998-05-04 AR ARP980102069A patent/AR013079A1/en unknown
- 1998-05-05 PE PE1998000336A patent/PE71599A1/en not_active Application Discontinuation
- 1998-05-05 ZA ZA983762A patent/ZA983762B/en unknown
- 1998-05-06 BR BR9809306-1A patent/BR9809306A/en not_active Application Discontinuation
- 1998-05-06 CO CO98024945A patent/CO4950618A1/en unknown
- 1998-05-06 JP JP54804998A patent/JP2001525804A/en active Pending
- 1998-05-06 CN CN98804791A patent/CN1255161A/en active Pending
- 1998-05-06 NZ NZ337889A patent/NZ337889A/en unknown
- 1998-05-06 HU HU0002247A patent/HUP0002247A3/en unknown
- 1998-05-06 TR TR1999/02766T patent/TR199902766T2/en unknown
- 1998-05-06 AU AU75625/98A patent/AU7562598A/en not_active Abandoned
- 1998-05-06 WO PCT/US1998/003200 patent/WO1998050533A1/en not_active Ceased
- 1998-05-06 CA CA002288868A patent/CA2288868A1/en not_active Abandoned
- 1998-05-06 EP EP98923299A patent/EP1003846A4/en not_active Withdrawn
- 1998-05-06 IL IL13208898A patent/IL132088A0/en unknown
- 1998-05-06 PL PL98336856A patent/PL336856A1/en unknown
- 1998-05-06 KR KR1019997010207A patent/KR20010012256A/en not_active Withdrawn
- 1998-08-17 UY UY25143A patent/UY25143A1/en unknown
-
1999
- 1999-11-05 NO NO995434A patent/NO995434L/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1003846A1 (en) | 2000-05-31 |
| EP1003846A4 (en) | 2002-11-13 |
| NZ337889A (en) | 2001-09-28 |
| CA2288868A1 (en) | 1998-11-12 |
| AR013079A1 (en) | 2000-12-13 |
| CO4950618A1 (en) | 2000-09-01 |
| PL336856A1 (en) | 2000-07-17 |
| TR199902766T2 (en) | 2000-02-21 |
| WO1998050533A1 (en) | 1998-11-12 |
| IL132088A0 (en) | 2001-03-19 |
| HUP0002247A2 (en) | 2001-05-28 |
| CN1255161A (en) | 2000-05-31 |
| JP2001525804A (en) | 2001-12-11 |
| AU7562598A (en) | 1998-11-27 |
| KR20010012256A (en) | 2001-02-15 |
| HUP0002247A3 (en) | 2003-01-28 |
| BR9809306A (en) | 2000-07-04 |
| ZA983762B (en) | 1998-11-06 |
| NO995434D0 (en) | 1999-11-05 |
| NO995434L (en) | 1999-11-05 |
| PE71599A1 (en) | 1999-09-15 |
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