WO2003086396A1 - Inhibiteur de phosphodiesterase iv contenant un derive de pyridylacrylamide - Google Patents
Inhibiteur de phosphodiesterase iv contenant un derive de pyridylacrylamide Download PDFInfo
- Publication number
- WO2003086396A1 WO2003086396A1 PCT/JP2003/004227 JP0304227W WO03086396A1 WO 2003086396 A1 WO2003086396 A1 WO 2003086396A1 JP 0304227 W JP0304227 W JP 0304227W WO 03086396 A1 WO03086396 A1 WO 03086396A1
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- group
- substituted
- alkoxy
- alkyl
- phosphodiesterase
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- 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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
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- 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
- A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
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- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/443—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
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- A—HUMAN NECESSITIES
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- A61P27/00—Drugs for disorders of the senses
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
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- 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
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
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- 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
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/59—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with at least one of the bonds being to sulfur
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- 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
- C07D213/60—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 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
- C07D213/61—Halogen atoms or nitro radicals
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- 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
- C07D213/60—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 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
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- 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
Definitions
- Compound 136 was obtained by a method according to Production Example 52.
- Compound 163 was obtained by a method according to Production Example 64.
- Phosphodiesterase IV was isolated from U-937 cells (Torphy, T. J. et al., J. Pharmacol. Exp. Ther., 263, 1195-1205 (1992)).
- [ 3 H] cAMP and CAMP (1 M) were used as substrate tracers and incubated for 30 minutes at 30 minutes.
- the [3 ⁇ ] 5'-AMP was measured by liquid scintillation one Chillon.
- the inhibitory activity was represented by the inhibition rate of the test substance relative to the control group without the test substance, and calculated by the following formula.
- Inhibitory activity 100 X (control group value-test substance added group value) Z control group value
- a phosphodiesterase IV inhibitor containing a pyridylacrylamide derivative as an active ingredient can be provided.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Otolaryngology (AREA)
- Ophthalmology & Optometry (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Communicable Diseases (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/510,053 US20050187264A1 (en) | 2002-04-02 | 2003-04-02 | Phosphodiesterase iv inhibitor containing pyridylacrylamide derivative |
KR10-2004-7015717A KR20050007453A (ko) | 2002-04-02 | 2003-04-02 | 피리딜아크릴산아미드 유도체를 함유하는포스포디에스테라아제 ⅳ 저해제 |
CA002481178A CA2481178A1 (en) | 2002-04-02 | 2003-04-02 | Phosphodiesterase iv inhibitor containing pyridylacrylamide derivative |
EP03746165A EP1495757A1 (en) | 2002-04-02 | 2003-04-02 | Phosphodiesterase iv inhibitor containing pyridylacrylamide derivative |
AU2003236340A AU2003236340A1 (en) | 2002-04-02 | 2003-04-02 | Phosphodiesterase iv inhibitor containing pyridylacrylamide derivative |
MXPA04009580A MXPA04009580A (es) | 2002-04-02 | 2003-04-02 | Inhibidor de fosfodiesterasa iv que contiene un derivado de piridilacrilamida. |
JP2003583415A JPWO2003086396A1 (ja) | 2002-04-02 | 2003-04-02 | ピリジルアクリル酸アミド誘導体を含有するホスホジエステラーゼiv阻害剤 |
BR0308935-5A BR0308935A (pt) | 2002-04-02 | 2003-04-02 | Inibidor de fosfodiesterase iv contendo derivado de piridilacrilamida |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2002-99491 | 2002-04-02 | ||
JP2002099491 | 2002-04-02 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2003086396A1 true WO2003086396A1 (fr) | 2003-10-23 |
WO2003086396A9 WO2003086396A9 (fr) | 2003-12-24 |
Family
ID=29240909
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2003/004227 WO2003086396A1 (fr) | 2002-04-02 | 2003-04-02 | Inhibiteur de phosphodiesterase iv contenant un derive de pyridylacrylamide |
Country Status (12)
Country | Link |
---|---|
US (1) | US20050187264A1 (ja) |
EP (1) | EP1495757A1 (ja) |
JP (1) | JPWO2003086396A1 (ja) |
KR (1) | KR20050007453A (ja) |
CN (1) | CN1655783A (ja) |
AU (1) | AU2003236340A1 (ja) |
BR (1) | BR0308935A (ja) |
CA (1) | CA2481178A1 (ja) |
MX (1) | MXPA04009580A (ja) |
RU (1) | RU2004131879A (ja) |
TW (1) | TW200306195A (ja) |
WO (1) | WO2003086396A1 (ja) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004052890A1 (en) * | 2002-12-06 | 2004-06-24 | Affinium Pharmaceuticals, Inc. | Heterocyclic compounds, methods of making them and their use in therapy |
JP2006523718A (ja) * | 2003-04-18 | 2006-10-19 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | チロナミン誘導体およびチロナミンアナログならびにこれらを使用する方法 |
US8143412B2 (en) | 2008-07-08 | 2012-03-27 | Board Of Regents, The University Of Texas System | Inhibitors of proliferation and activation of signal transducer and activator of transcription (STATs) |
US8450337B2 (en) | 2008-09-30 | 2013-05-28 | Moleculin, Llc | Methods of treating skin disorders with caffeic acid analogs |
US8895545B2 (en) | 2006-07-20 | 2014-11-25 | Debiopharm International Sa | Acrylamide derivatives as Fab I inhibitors |
US8901105B2 (en) | 2012-06-19 | 2014-12-02 | Debiopharm International Sa | Prodrug derivatives of (E)-N-methyl-N-((3-M ethylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide |
US9862737B2 (en) | 2007-02-16 | 2018-01-09 | Debiopharm International Sa | Salts, prodrugs and polymorphs of fab I inhibitors |
US10751351B2 (en) | 2016-02-26 | 2020-08-25 | Debiopharm International S.A. | Medicament for treatment of diabetic foot infections |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993004035A1 (de) * | 1991-08-13 | 1993-03-04 | Boehringer Mannheim Gmbh | Neue 3,5-di-tert.butyl-4-hydroxyphenyl-derivate, verfahren zu ihrer herstellung und arzneimittel |
WO1998045268A1 (en) * | 1997-04-04 | 1998-10-15 | Pfizer Products Inc. | Nicotinamide derivatives |
EP0882714A1 (en) * | 1996-09-25 | 1998-12-09 | SS Pharmaceutical Co., Ltd. | Substituted vinylpyridine derivatives and drugs containing the same |
WO1999005109A1 (fr) * | 1997-07-25 | 1999-02-04 | Tsumura & Co. | Derives de pyridylacrylamide, remedes contre la nephrite et inhibiteurs de tgf-beta contenant lesdits elements |
-
2003
- 2003-04-02 TW TW092107448A patent/TW200306195A/zh unknown
- 2003-04-02 US US10/510,053 patent/US20050187264A1/en not_active Abandoned
- 2003-04-02 BR BR0308935-5A patent/BR0308935A/pt not_active IP Right Cessation
- 2003-04-02 CN CNA038122375A patent/CN1655783A/zh active Pending
- 2003-04-02 EP EP03746165A patent/EP1495757A1/en not_active Withdrawn
- 2003-04-02 KR KR10-2004-7015717A patent/KR20050007453A/ko not_active Application Discontinuation
- 2003-04-02 RU RU2004131879/04A patent/RU2004131879A/ru not_active Application Discontinuation
- 2003-04-02 CA CA002481178A patent/CA2481178A1/en not_active Abandoned
- 2003-04-02 WO PCT/JP2003/004227 patent/WO2003086396A1/ja not_active Application Discontinuation
- 2003-04-02 JP JP2003583415A patent/JPWO2003086396A1/ja active Pending
- 2003-04-02 MX MXPA04009580A patent/MXPA04009580A/es not_active Application Discontinuation
- 2003-04-02 AU AU2003236340A patent/AU2003236340A1/en not_active Abandoned
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WO1993004035A1 (de) * | 1991-08-13 | 1993-03-04 | Boehringer Mannheim Gmbh | Neue 3,5-di-tert.butyl-4-hydroxyphenyl-derivate, verfahren zu ihrer herstellung und arzneimittel |
EP0882714A1 (en) * | 1996-09-25 | 1998-12-09 | SS Pharmaceutical Co., Ltd. | Substituted vinylpyridine derivatives and drugs containing the same |
WO1998045268A1 (en) * | 1997-04-04 | 1998-10-15 | Pfizer Products Inc. | Nicotinamide derivatives |
WO1999005109A1 (fr) * | 1997-07-25 | 1999-02-04 | Tsumura & Co. | Derives de pyridylacrylamide, remedes contre la nephrite et inhibiteurs de tgf-beta contenant lesdits elements |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2004052890A1 (en) * | 2002-12-06 | 2004-06-24 | Affinium Pharmaceuticals, Inc. | Heterocyclic compounds, methods of making them and their use in therapy |
JP2006513262A (ja) * | 2002-12-06 | 2006-04-20 | アフィニウム ファーマシューティカルズ, インク. | ヘテロ環化合物、その製造方法および治療におけるその使用 |
JP4859460B2 (ja) * | 2002-12-06 | 2012-01-25 | アフィニウム ファーマシューティカルズ, インク. | ヘテロ環化合物、その製造方法および治療におけるその使用 |
JP2006523718A (ja) * | 2003-04-18 | 2006-10-19 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | チロナミン誘導体およびチロナミンアナログならびにこれらを使用する方法 |
US8895545B2 (en) | 2006-07-20 | 2014-11-25 | Debiopharm International Sa | Acrylamide derivatives as Fab I inhibitors |
US9862737B2 (en) | 2007-02-16 | 2018-01-09 | Debiopharm International Sa | Salts, prodrugs and polymorphs of fab I inhibitors |
US8637675B2 (en) | 2008-07-08 | 2014-01-28 | Board Of Regents, The University Of Texas System | Inhibitors of proliferation and activation of signal transducer and activators of transcription (STATS) |
US9000179B2 (en) | 2008-07-08 | 2015-04-07 | Board Of Regents, The University Of Texas System | Inhibitors of proliferation and activation of signal transducer and activator of transcription (STATs) |
US8143412B2 (en) | 2008-07-08 | 2012-03-27 | Board Of Regents, The University Of Texas System | Inhibitors of proliferation and activation of signal transducer and activator of transcription (STATs) |
US8450337B2 (en) | 2008-09-30 | 2013-05-28 | Moleculin, Llc | Methods of treating skin disorders with caffeic acid analogs |
US8901105B2 (en) | 2012-06-19 | 2014-12-02 | Debiopharm International Sa | Prodrug derivatives of (E)-N-methyl-N-((3-M ethylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide |
US10035813B2 (en) | 2012-06-19 | 2018-07-31 | Debiopharm International Sa | Prodrug derivatives of (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide |
US10751351B2 (en) | 2016-02-26 | 2020-08-25 | Debiopharm International S.A. | Medicament for treatment of diabetic foot infections |
Also Published As
Publication number | Publication date |
---|---|
CN1655783A (zh) | 2005-08-17 |
US20050187264A1 (en) | 2005-08-25 |
RU2004131879A (ru) | 2005-04-20 |
TW200306195A (en) | 2003-11-16 |
EP1495757A1 (en) | 2005-01-12 |
KR20050007453A (ko) | 2005-01-18 |
CA2481178A1 (en) | 2003-10-23 |
AU2003236340A1 (en) | 2003-10-27 |
JPWO2003086396A1 (ja) | 2005-08-18 |
BR0308935A (pt) | 2005-01-04 |
MXPA04009580A (es) | 2005-05-27 |
WO2003086396A9 (fr) | 2003-12-24 |
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