CA2715138A1 - Nouveaux derives anti-infectieux, leur procede de preparation, compositions pharmaceutiques les contenant et leurs utilisations en therapeutique - Google Patents
Nouveaux derives anti-infectieux, leur procede de preparation, compositions pharmaceutiques les contenant et leurs utilisations en therapeutique Download PDFInfo
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- CA2715138A1 CA2715138A1 CA2715138A CA2715138A CA2715138A1 CA 2715138 A1 CA2715138 A1 CA 2715138A1 CA 2715138 A CA2715138 A CA 2715138A CA 2715138 A CA2715138 A CA 2715138A CA 2715138 A1 CA2715138 A1 CA 2715138A1
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- 230000002924 anti-infective effect Effects 0.000 title claims abstract description 10
- 238000011282 treatment Methods 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000002360 preparation method Methods 0.000 claims abstract description 19
- 201000008827 tuberculosis Diseases 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims abstract description 6
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229940079593 drug Drugs 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 132
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 26
- -1 3-dodecylphenyl Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000012453 solvate Substances 0.000 claims description 12
- 238000006467 substitution reaction Methods 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 102000004190 Enzymes Human genes 0.000 claims description 8
- 108090000790 Enzymes Proteins 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 101150009274 nhr-1 gene Proteins 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- KZVAAIRBJJYZOW-UHFFFAOYSA-N 2-(hydroxymethyl)oxolane-3,4-diol Chemical compound OCC1OCC(O)C1O KZVAAIRBJJYZOW-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 206010024229 Leprosy Diseases 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 241000186367 Mycobacterium avium Species 0.000 claims description 3
- 241000187492 Mycobacterium marinum Species 0.000 claims description 3
- 241000187917 Mycobacterium ulcerans Species 0.000 claims description 3
- 102000009105 Short Chain Dehydrogenase-Reductases Human genes 0.000 claims description 3
- 108010048287 Short Chain Dehydrogenase-Reductases Proteins 0.000 claims description 3
- 230000004927 fusion Effects 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- 201000004792 malaria Diseases 0.000 claims description 3
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- 230000001717 pathogenic effect Effects 0.000 claims description 3
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- AGYBMBFXBIXTJT-UHFFFAOYSA-N 1-(2-dodecoxyphenyl)-1-hydroxy-2h-pyrrolo[3,4-c]pyridin-3-one Chemical compound CCCCCCCCCCCCOC1=CC=CC=C1C1(O)C2=CC=NC=C2C(=O)N1 AGYBMBFXBIXTJT-UHFFFAOYSA-N 0.000 claims description 2
- WVOFXTMJBTXFSH-UHFFFAOYSA-N 1-(3-dodecoxyphenyl)-1-hydroxy-2h-pyrrolo[3,4-c]pyridin-3-one Chemical compound CCCCCCCCCCCCOC1=CC=CC(C2(O)C3=CC=NC=C3C(=O)N2)=C1 WVOFXTMJBTXFSH-UHFFFAOYSA-N 0.000 claims description 2
- GYRDHKFYUFZKCL-UHFFFAOYSA-N 1-(3-dodecoxyphenyl)-1-methoxy-2h-pyrrolo[3,4-c]pyridin-3-one Chemical compound CCCCCCCCCCCCOC1=CC=CC(C2(C3=CC=NC=C3C(=O)N2)OC)=C1 GYRDHKFYUFZKCL-UHFFFAOYSA-N 0.000 claims description 2
- NYWWSTLHGDABMI-UHFFFAOYSA-N 1-(3-dodecylphenyl)-1-hydroxy-2h-pyrrolo[3,4-c]pyridin-3-one Chemical compound CCCCCCCCCCCCC1=CC=CC(C2(O)C3=CC=NC=C3C(=O)N2)=C1 NYWWSTLHGDABMI-UHFFFAOYSA-N 0.000 claims description 2
- OGPFXDSJOOAYCF-UHFFFAOYSA-N 1-(3-dodecylsulfanylphenyl)-1-hydroxy-2h-pyrrolo[3,4-c]pyridin-3-one Chemical compound CCCCCCCCCCCCSC1=CC=CC(C2(O)C3=CC=NC=C3C(=O)N2)=C1 OGPFXDSJOOAYCF-UHFFFAOYSA-N 0.000 claims description 2
- KZNWFKKNAHKDFY-UHFFFAOYSA-N 1-hydroxy-1-(3-hydroxyphenyl)-2h-pyrrolo[3,4-c]pyridin-3-one Chemical compound OC1=CC=CC(C2(O)C3=CC=NC=C3C(=O)N2)=C1 KZNWFKKNAHKDFY-UHFFFAOYSA-N 0.000 claims description 2
- NAOWIHVYFYKGSP-UHFFFAOYSA-N 1-hydroxy-1-(3-octoxyphenyl)-2h-pyrrolo[3,4-c]pyridin-3-one Chemical compound CCCCCCCCOC1=CC=CC(C2(O)C3=CC=NC=C3C(=O)N2)=C1 NAOWIHVYFYKGSP-UHFFFAOYSA-N 0.000 claims description 2
- WIFFHZJLTINICL-UHFFFAOYSA-N 1-hydroxy-1-(3-octylphenyl)-2h-pyrrolo[3,4-c]pyridin-3-one Chemical compound CCCCCCCCC1=CC=CC(C2(O)C3=CC=NC=C3C(=O)N2)=C1 WIFFHZJLTINICL-UHFFFAOYSA-N 0.000 claims description 2
- BCDKKPMBBFVXGM-UHFFFAOYSA-N 1-hydroxy-1-(3-prop-2-enoxyphenyl)-2h-pyrrolo[3,4-c]pyridin-3-one Chemical compound N1C(=O)C2=CN=CC=C2C1(O)C1=CC=CC(OCC=C)=C1 BCDKKPMBBFVXGM-UHFFFAOYSA-N 0.000 claims description 2
- GGFIWIATBNCHQX-UHFFFAOYSA-N 1-hydroxy-1-[3-(4-nonylphenyl)phenyl]-2h-pyrrolo[3,4-c]pyridin-3-one Chemical compound C1=CC(CCCCCCCCC)=CC=C1C1=CC=CC(C2(O)C3=CC=NC=C3C(=O)N2)=C1 GGFIWIATBNCHQX-UHFFFAOYSA-N 0.000 claims description 2
- 241000186366 Mycobacterium bovis Species 0.000 claims description 2
- 108090000854 Oxidoreductases Proteins 0.000 claims description 2
- 102000004316 Oxidoreductases Human genes 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000027531 mycobacterial infectious disease Diseases 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 102000014914 Carrier Proteins Human genes 0.000 claims 1
- 108010078791 Carrier Proteins Proteins 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000002458 infectious effect Effects 0.000 claims 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical class NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 abstract description 16
- 239000000203 mixture Substances 0.000 abstract description 12
- 239000003112 inhibitor Substances 0.000 abstract description 10
- 239000000758 substrate Substances 0.000 abstract description 6
- 101001014220 Monascus pilosus Dehydrogenase mokE Proteins 0.000 abstract description 5
- 101000573542 Penicillium citrinum Compactin nonaketide synthase, enoyl reductase component Proteins 0.000 abstract description 5
- 230000002209 hydrophobic effect Effects 0.000 abstract description 3
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
- 229940127557 pharmaceutical product Drugs 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 37
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 101150005343 INHA gene Proteins 0.000 description 22
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 19
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- 241000186226 Corynebacterium glutamicum Species 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
- 239000003480 eluent Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
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- 235000011152 sodium sulphate Nutrition 0.000 description 11
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
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- SJSABZBUTDSWMJ-UHFFFAOYSA-N pyrrolo[3,4-c]pyridine-1,3-dione Chemical compound N1=CC=C2C(=O)NC(=O)C2=C1 SJSABZBUTDSWMJ-UHFFFAOYSA-N 0.000 description 4
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- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 239000000814 tuberculostatic agent Substances 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- 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
- A61P31/04—Antibacterial agents
- A61P31/08—Antibacterial agents for leprosy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0850778A FR2927331B1 (fr) | 2008-02-07 | 2008-02-07 | Nouveaux derives anti-infectieux, leur procede de preparation, compositions pharmaceutiques les contenant et leurs utilisations en therapeutique. |
| FR0850778 | 2008-02-07 | ||
| PCT/FR2009/050195 WO2009101345A1 (fr) | 2008-02-07 | 2009-02-06 | Nouveaux dérivés anti-infectieux, leur procédé de préparation, compositions pharmaceutiques les contenant et leurs utilisations en thérapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2715138A1 true CA2715138A1 (fr) | 2009-08-20 |
Family
ID=39745633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2715138A Abandoned CA2715138A1 (fr) | 2008-02-07 | 2009-02-06 | Nouveaux derives anti-infectieux, leur procede de preparation, compositions pharmaceutiques les contenant et leurs utilisations en therapeutique |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8710073B2 (https=) |
| EP (1) | EP2240449B1 (https=) |
| JP (1) | JP5677855B2 (https=) |
| CA (1) | CA2715138A1 (https=) |
| FR (1) | FR2927331B1 (https=) |
| WO (1) | WO2009101345A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR102012033811A8 (pt) * | 2012-12-28 | 2019-12-24 | Uniao Brasileira De Educacao E Assistencia Mantenedora Da Puc Rs | compostos, uso, composição farmacêutica inibidora de redutase em microorganismos, ligante de inha, e, método para obtenção de ligantes de inha |
| BR102013006007A2 (pt) * | 2013-03-13 | 2014-11-11 | Ubea | Compostos, uso, composição farmacêutica inibidora de redutase em microorganismos, ligante de inha, e, método para obtenção de ligantes de inha a partir de derivados de acetamida, ureia, fenol e carboxamida |
| GB201322334D0 (en) * | 2013-12-17 | 2014-01-29 | Agency Science Tech & Res | Maleimide derivatives as modulators of WNT pathway |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6291586B2 (en) | 1996-05-03 | 2001-09-18 | 3M Innovative Properties Company | Amide functional ultraviolet light absorbers for polyurethanes and polyureas |
| US6328793B1 (en) * | 2000-08-03 | 2001-12-11 | Xerox Corporation | Phase change inks |
| CN101534808A (zh) * | 2005-06-27 | 2009-09-16 | 拜维尔实验室国际有限公司 | 丁氨苯丙酮盐的改良释放配制品 |
| EP2687533B1 (en) * | 2006-07-20 | 2017-07-19 | Debiopharm International SA | Acrylamide derivatives as FAB I inhibitors |
-
2008
- 2008-02-07 FR FR0850778A patent/FR2927331B1/fr not_active Expired - Fee Related
-
2009
- 2009-02-06 JP JP2010545538A patent/JP5677855B2/ja not_active Expired - Fee Related
- 2009-02-06 WO PCT/FR2009/050195 patent/WO2009101345A1/fr not_active Ceased
- 2009-02-06 CA CA2715138A patent/CA2715138A1/fr not_active Abandoned
- 2009-02-06 EP EP09710826.0A patent/EP2240449B1/fr not_active Not-in-force
- 2009-02-06 US US12/866,645 patent/US8710073B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US8710073B2 (en) | 2014-04-29 |
| US20110092536A1 (en) | 2011-04-21 |
| FR2927331B1 (fr) | 2011-05-20 |
| JP5677855B2 (ja) | 2015-02-25 |
| JP2011511050A (ja) | 2011-04-07 |
| WO2009101345A1 (fr) | 2009-08-20 |
| EP2240449A1 (fr) | 2010-10-20 |
| FR2927331A1 (fr) | 2009-08-14 |
| EP2240449B1 (fr) | 2016-01-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20140107 |
|
| FZDE | Discontinued |
Effective date: 20170823 |