WO2001025204A1 - Novel trisubstituted pyridine compounds - Google Patents
Novel trisubstituted pyridine compounds Download PDFInfo
- Publication number
- WO2001025204A1 WO2001025204A1 PCT/SE2000/001859 SE0001859W WO0125204A1 WO 2001025204 A1 WO2001025204 A1 WO 2001025204A1 SE 0001859 W SE0001859 W SE 0001859W WO 0125204 A1 WO0125204 A1 WO 0125204A1
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- WIPO (PCT)
- Prior art keywords
- alkyl
- carbon atoms
- compound according
- atpase
- vacuolar
- Prior art date
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—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
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
-
- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- 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
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
Definitions
- the present invention relates to a selective inhibitor of mammalian osteoclast cell activity, processes for its preparation and pharmaceutical compositions comprising the same as well as methods of treatment, where said selective inhibitor is administered to a human or animal patient. More specifically, the present invention relates to a selective inhibitor of vacuolar FT-ATPase in mammalian osteoclast cells.
- novel compounds with excellent therapeutical effect against physiological disorders involving inter alia bone resorption have now been found. More specifically, said compounds comprise a selective inhibitor of mammalian osteoclast cell activ it , wherein said inhibitor comprises a trisubstituted pyridine compound. Since the selectiv e inhibitor of the present invention has been found to inhibit vacuolar FT-ATPase, such as vacuolar H - ATPase in osteoclast cells, it is thereby therapeutically efficient against physiological disorders involving bone resorption.
- R ⁇ is selected from the group consisting of (a) H,
- R ⁇ + R ? form a fi membered ring containing at least one O, S and/or ⁇ .
- alkyl hav ing 1 -3 carbon atoms and
- R2 is selected from the group consisting of (a) H,
- R12R-13, v herein R and R13 are either independently selected from the group consisting of H. a straight chain, branched or cyclic saturated or unsaturated alkyl having 1-6 carbon atoms, optionally substituted with O-alkyl, NH-alkyl, N-dialkyl, N- pyrrolidinyl, N-pipe ⁇ dinyl, N-morphohnyl or N-piperazinyl, and aryl selected from the group consisting of phenyl, imidazolyl, py ⁇ dinyl or pyrrolyl, or together form a five or six membered saturated or unsaturated ⁇ ng, optionally containing O, S, and/ or N, (d) straight chain, branched or cyclic saturated or unsaturated O-alkyl having 1-6 carbon atoms optionally substituted with O-alkyl, NH-alkyl, N-dialkyl, N-pyrrohdinyl, N- pipe ⁇ dinyl, N
- R3-R1 1 are selected from the group consisting of
- R2 is S-Me, NRpRp. O-alkyl or alkyl having 1-6 carbon atoms; R [ . R-;. R4 and Rg are H; and R5. Rg, R7, R9. i ⁇ and R ⁇ ⁇ are straight chain, branched or cyclic saturated or unsaturated O-alkyl having 1-3 carbon atoms.
- R2 is S-Me, NRpRp, O-alkyl or alkyl having 1-6 carbon atoms; R ⁇ . R3.
- R5, Rg and R9 are H; and
- Rg. R7, R [ Q and R are straight chain, branched or cyclic saturated or unsaturated O-alkyl having 1-3 carbon atoms.
- R2 is S-Me, NRpRp, O-alkyl or alkyl having 1-6 carbon atoms; Ri , R3. R5, Rg, R7, R9. R ⁇ Q, R ⁇ ⁇ are H; and R4 and Rg are straight chain, branched or cyclic saturated or unsaturated O-alkyl having 1-3 carbon atoms.
- said trisubstituted pyridine compound is selected from the group consisting of: 4-(4-pyrrolidin-l-yl-phenyl)-2,6-bis-(3,4,5-trimethoxy-phenyl)-pyridine;
- the present invention also relates to a process for the preparation of a tnsubstituted pyridine compound according to any one of the embodiments set forth above.
- a suitably substituted benzaldehyde is heated with ammonium acetate and a suitably substituted acetophenone, optionally in the presence of a solvent, during 2-24 h.
- a suitably substituted chalcone is heated with ammonium acetate and a suitably substituted acetophenone, optionally in the presence of a solvent, during
- a suitably substituted aromatic aldehyde or chalcone is reacted with a suitably substituted N-(d ⁇ phenylphosph ⁇ nyl)- l-phen lethane ⁇ m ⁇ ne in the presence of a base, preferably t-BuOK. in an aprotic solvent
- a suitably substituted benz ⁇ ldehyde and a suitably substituted acetophenone (molar ratio 2.1) are heated with ammonium acetate in acetic acid for 2-24 h.
- the desired compound may be isolated by cr stallisation or column chromatogtraphy on silica gel
- a suitably substituted chalcone prepared by standard methods, and a suitably substituted acetophenone derivativ e (molar ratio 1 1), such as e g. phenacyl-py ⁇ dinium bromide, phenacyl-dimethylsulfomum bromide or d ⁇ methyl-(2-oxo-2-phenyl-ethyl)-sulfomum betaine), are heated with ammonium acetate in acetic acid for 2-24 h.
- the desired compound may be isolated by crystallisation or column chromatography on silica gel.
- N-(d ⁇ phenylphosph ⁇ nyl)-2-phenyl-l-azaallyl anion generated from N-(d ⁇ phenylphosph ⁇ n l)- l-phenylethane ⁇ m ⁇ ne under basic conditions (t-BuOK), is reacted with an aromatic aldehyde (molar ratio 2.1) or a chalcone (molar ratio 1.1)
- the desired compound may be isolated by crystallisation or column chromatogtraphy on silica gel
- the present inv ention relates to a trisubstituted pyridine compound with the general formula I for use as a pharmaceutical
- the present invention also relates to a pharmaceutical composition
- a pharmaceutical composition comprising a trisubstituted pyridine compound according to any one of the embodiments set forth above as activ e ingredient in association with a pharmaceutically acceptable adjuvant, diluent or carrier
- the amount of said active ingredient per dosage unit is generally within the range of about 1 to I 000 mg, preferably 1-300 mg Moreover, the amount of said activ e ingredient is typically within the range of about 0 1 to 95% by weight of said pharmaceutical composition
- the present invention is also related to the use of a t ⁇ substituted pyridine compound according to any one of the previously outlined embodiments in the manufacture of a medicament for use in therapeutic or prophylactic treatment of a human or animal body
- said use is related to a medicament intended for treatment involving inhibition of vacuolar H-r-ATPase, preferably vacuolar H+-ATPase in osteoclast cells
- the medicament is intended for treatment involving inhibition of vacuolar H+-ATPase containing the isoform a3, said vacuolar H-t-- ATPase preferably being present in osteoclast cells
- said medicament is intended for treatment involving inhibition of bone resorption, or is intended for treatment and or prevention of diseases related to increased bone resorption, preferably osteoporosis
- the medicament is intended for treatment of Paget s disease of bone, hyperparathyroidism, malignant neoplasms, parodontal diseases, prosthetic and or implant related bone loss, tumours, AIDS and disorders related thereto, Alzheimer's disease, angiogenesis, atherosclerosis, rheumatoid arthritis, diabetic retinopathy, psoriasis or diabetes.
- the present invention is also related to a method for inhibiting vacuolar H -ATPase, preferably vacuolar H " - ATPase in osteoclast cells, or to a method for inhibiting vacuolar H " -ATPase containing the isoform a3, said vacuolar H-r-ATPase preferably being present in osteoclast cells, wherein any one of said methods comprises administering to a human or animal patient a therapeutically effective amount of a trisubstituted pyridine compound according to any one of the embodiments outlined above
- the present invention is related to a method for inhibiting bone resorption. or to a method for treatment and or prevention of diseases related to increased bone resorption, preferably osteoporosis, wherein any one of said methods comprises admmiste ⁇ ng to a human or animal patient a therapeutically effective amount of a trisubstituted py ⁇ dine compound according to any one of the embodiments set forth above
- the present invention concerns a method for treatment of Paget s disease of bone, hyperparathyroidism, malignant neoplasms, parodontal diseases, prosthetic and or implant related bone loss, tumours, AIDS and disorders related thereto, Alzheimer ' s disease, angiogenesis. atherosclerosis, rheumatoid arthritis, diabetic ret ⁇ nopath> , psoriasis or diabetes, wherein said method comprises administering to a human or animal patient a
- the typical daily dose of the active ingredient vanes within a wide range and will depend on various factors such as e g the individual requirement of each patient, the route of
- oral and parenteral doses will usually be in the range of 1 to 1000 mg, preferably 1-300 mg, per day of the active ingredient
- the present invention relates to pharmaceutical compositions containing at least one compound according to the invention, or a therapeutically acceptable salt thereof, as active ingredient.
- the pharmaceutically acceptable salts include acid addition salts
- Acids that form therapeutically acceptable salts are e g hydrohalogen acids, such as hydrochloric acid, sulphuric acid, phospho ⁇ c acid, nitric acid, aliphatic, alicychc, aromatic or heterocyc c carboxyl or sufphonic acids, such as formic acid, acetic ac d, propionic acid, succimc acid.
- glyco c acid lactic acid, malic acid, tarta ⁇ c acid, citric acid, ascorbic acid, maleic acid, hydroxymaleic acid, pyruvic acid, -hydroxybensoic acid, embonic acid, methanesulphonic acid, ethanesulphonic acid, hydroxyethanesulphonic acid, halogenbenquentphonic acid, toluenesulphonic acid and naphtalenesulphonic acid.
- a trisubstituted pyridine compound for use as a pharmaceutical.
- it may be used in pharmaceutical compositions for oral, intravenous, topical, intraperitoneal or subcutaneous administration, in association with one or more pharmaceutically acceptable carriers, diluents or adjuvants that are well known in the art.
- composition of the invention may be administered topically, in the form of solutions, suspensions or systemically, e.g. by oral administration in the form of tablets, capsules, syrups, powders or granules or by parenteral administration in the form of solutions or suspensions, or by subcutaneous administration or by rectal administration in the form of suppositories or transdermally.
- Example 4 Synthesis of 4-(4-Ethyl-phenyl)-2,6-b ⁇ s-(3,4,5-t ⁇ methoxy-phenyl)-py ⁇ dme was performed according to example 1 The crude compound was purified by column chromatography on silica gel.
- Membrane vesicles were prepared from egg-laying hens after 14 days of calcium-deprived diet, as previously desc ⁇ bed (Mattsson, J.P., Lorentzon, P., Wallmark, B., and Keeling, D.J., Biochim. Biophys. Acta, 1 146( 1), 106- 12 ( 1993)), with some modifications.
- the medullary bone scraped from the long bones was resuspended in isolation buffer (1 ml/g medullary bone) containing 5 mM Hepes/T ⁇ s, pH 7.4, 250 mM sucrose and 1 mM EGTA, minced using a pair of scissors, diluted 1 : 10 (vv/v) in isolation buffer and homogenised in a polytron homogeniser The homogenate was filtered through a 250 ⁇ m nylon mesh. Membrane vesicles were then obtained by differential centrifugation (2000 x g for 10 mm, 10,000 x g for 20 mm and 40,000 x g for 1 h).
- the final pellet was resuspended in isolation buffer (0.4 ml/g medullary bone) by 20 passes using a teflon/glass homogenizer, snap frozen in MeOH/dry ice and then stored at -70°C.
- Bovine brain 0.4 ml/g medullary bone
- Membrane vesicles were prepared from whole brain exactly as described for the medullary bone membrane vesicles.
- Proton transport in membrane vesicles was measured in a 96-well plate reader using the weak base acridine orange (Mattsson, J.P., Lorentzon, P., Wallmark, B., and Keeling, D.J., Biochim. Biophys. Acta, 1 146(1), 106-12 (1993)).
- Test substances dissolved in DMSO
- DMSO control
- 220 ⁇ l acridine-orange buffer final concentrations: 5 mM Hepes/Tris, pH 7.4.
- the calvaria pieces were placed in petri dishes containing incubation medium ( 1 mM L-glutamine, 100 U/ml penicillin, 100 ⁇ g/ml streptomycin. 1 mg/ml albumin and 1 ⁇ M indomethacin) with or without 10 nM PTH and preincubated in a CO incubator (5% CO; in air) for 20-24 h at 37°C.
- incubation medium 1 mM L-glutamine, 100 U/ml penicillin, 100 ⁇ g/ml streptomycin. 1 mg/ml albumin and 1 ⁇ M indomethacin
- the calvaria pieces were then transferred to a 24-vvell plate containing fresh incubation medium.
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2001528151A JP2003511367A (en) | 1999-10-06 | 2000-09-26 | New trisubstituted pyridine compounds |
AU79763/00A AU7976300A (en) | 1999-10-06 | 2000-09-26 | Novel trisubstituted pyridine compounds |
CA002385210A CA2385210A1 (en) | 1999-10-06 | 2000-09-26 | Novel trisubstituted pyridine compounds |
EP00970371A EP1222169A1 (en) | 1999-10-06 | 2000-09-26 | Novel trisubstituted pyridine compounds |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9903610-5 | 1999-10-06 | ||
SE9903610A SE9903610D0 (en) | 1999-10-06 | 1999-10-06 | Novel compounds II |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001025204A1 true WO2001025204A1 (en) | 2001-04-12 |
Family
ID=20417270
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/SE2000/001859 WO2001025204A1 (en) | 1999-10-06 | 2000-09-26 | Novel trisubstituted pyridine compounds |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP1222169A1 (en) |
JP (1) | JP2003511367A (en) |
AU (1) | AU7976300A (en) |
CA (1) | CA2385210A1 (en) |
SE (1) | SE9903610D0 (en) |
WO (1) | WO2001025204A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1805142A2 (en) * | 2004-09-23 | 2007-07-11 | Reddy US Therapeutics, Inc. | Novel pyridine compounds, process for their preparation and compositions containing them |
US9409882B2 (en) | 2012-08-21 | 2016-08-09 | Hoffmann-La Roche Inc. | Pyridine derivatives |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994027604A1 (en) * | 1993-05-28 | 1994-12-08 | Taisho Pharmaceutical Co., Ltd. | Medicinal use of pyridine derivative |
EP0795545A1 (en) * | 1994-11-28 | 1997-09-17 | Taisho Pharmaceutical Co. Ltd | Pyridine derivatives |
WO1998001443A1 (en) * | 1996-07-09 | 1998-01-15 | Smithkline Beecham S.P.A. | Indole derivatives for the treatment of osteoporosis |
WO1999032447A2 (en) * | 1997-12-11 | 1999-07-01 | American Home Products Corporation | 2,4,6-trisubstituted pyridines with estrogenic activity and methods for the solid phase synthesis thereof |
-
1999
- 1999-10-06 SE SE9903610A patent/SE9903610D0/en unknown
-
2000
- 2000-09-26 JP JP2001528151A patent/JP2003511367A/en active Pending
- 2000-09-26 CA CA002385210A patent/CA2385210A1/en not_active Abandoned
- 2000-09-26 EP EP00970371A patent/EP1222169A1/en not_active Withdrawn
- 2000-09-26 WO PCT/SE2000/001859 patent/WO2001025204A1/en not_active Application Discontinuation
- 2000-09-26 AU AU79763/00A patent/AU7976300A/en not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994027604A1 (en) * | 1993-05-28 | 1994-12-08 | Taisho Pharmaceutical Co., Ltd. | Medicinal use of pyridine derivative |
EP0795545A1 (en) * | 1994-11-28 | 1997-09-17 | Taisho Pharmaceutical Co. Ltd | Pyridine derivatives |
WO1998001443A1 (en) * | 1996-07-09 | 1998-01-15 | Smithkline Beecham S.P.A. | Indole derivatives for the treatment of osteoporosis |
WO1999032447A2 (en) * | 1997-12-11 | 1999-07-01 | American Home Products Corporation | 2,4,6-trisubstituted pyridines with estrogenic activity and methods for the solid phase synthesis thereof |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1805142A2 (en) * | 2004-09-23 | 2007-07-11 | Reddy US Therapeutics, Inc. | Novel pyridine compounds, process for their preparation and compositions containing them |
EP1805142A4 (en) * | 2004-09-23 | 2009-06-10 | Reddy Us Therapeutics Inc | Novel pyridine compounds, process for their preparation and compositions containing them |
US9409882B2 (en) | 2012-08-21 | 2016-08-09 | Hoffmann-La Roche Inc. | Pyridine derivatives |
Also Published As
Publication number | Publication date |
---|---|
EP1222169A1 (en) | 2002-07-17 |
AU7976300A (en) | 2001-05-10 |
JP2003511367A (en) | 2003-03-25 |
SE9903610D0 (en) | 1999-10-06 |
CA2385210A1 (en) | 2001-04-12 |
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