CA2772697A1 - Utilisation de derives d'indole comme activateurs de nurr-1, pour leur application en tant que medicament pour le traitement de la maladie de parkinson - Google Patents
Utilisation de derives d'indole comme activateurs de nurr-1, pour leur application en tant que medicament pour le traitement de la maladie de parkinson Download PDFInfo
- Publication number
- CA2772697A1 CA2772697A1 CA2772697A CA2772697A CA2772697A1 CA 2772697 A1 CA2772697 A1 CA 2772697A1 CA 2772697 A CA2772697 A CA 2772697A CA 2772697 A CA2772697 A CA 2772697A CA 2772697 A1 CA2772697 A1 CA 2772697A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- methyl
- indol
- phenyl
- sulfonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003814 drug Substances 0.000 title claims description 10
- 208000018737 Parkinson disease Diseases 0.000 title claims description 9
- 239000012190 activator Substances 0.000 title description 3
- 150000002475 indoles Chemical class 0.000 title description 3
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 230
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 7
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 205
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 137
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 129
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 121
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 117
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 80
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 78
- -1 atom hydrogen Chemical class 0.000 claims description 73
- 125000004432 carbon atom Chemical group C* 0.000 claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 47
- 229910052799 carbon Inorganic materials 0.000 claims description 46
- 150000004702 methyl esters Chemical class 0.000 claims description 42
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 37
- 150000002148 esters Chemical class 0.000 claims description 33
- 239000005711 Benzoic acid Substances 0.000 claims description 32
- 125000004429 atom Chemical group 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 28
- 235000010233 benzoic acid Nutrition 0.000 claims description 27
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 13
- 150000001721 carbon Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000004494 ethyl ester group Chemical group 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- WQVUCKLUDWXZHH-UHFFFAOYSA-N 4-[1-(benzenesulfonyl)-1h-indene-2-carbonyl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C(=O)C1=CC2=CC=CC=C2C1S(=O)(=O)C1=CC=CC=C1 WQVUCKLUDWXZHH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004586 dihydrobenzopyranyl group Chemical group O1C(CCC2=C1C=CC=C2)* 0.000 claims description 3
- 125000005434 dihydrobenzoxazinyl group Chemical class O1N(CCC2=C1C=CC=C2)* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
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- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical group O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- JDFZAAWPRQCXHK-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)indole-2-carbonyl]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1C(=O)C1=CC2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 JDFZAAWPRQCXHK-UHFFFAOYSA-N 0.000 claims description 2
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- TZGSLWYXBFXORX-UHFFFAOYSA-N 5-[[1-(3-tert-butylphenyl)sulfonyl-5-(trifluoromethyl)indol-2-yl]methyl]furan-2-carboxylic acid Chemical compound CC(C)(C)C1=CC=CC(S(=O)(=O)N2C3=CC=C(C=C3C=C2CC=2OC(=CC=2)C(O)=O)C(F)(F)F)=C1 TZGSLWYXBFXORX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 3
- 239000005977 Ethylene Substances 0.000 claims 3
- ROSKYXAZUFLFLR-UHFFFAOYSA-N 4-[[1-(3-propan-2-ylphenyl)sulfonyl-5-(trifluoromethyl)indol-2-yl]methyl]benzoic acid Chemical compound CC(C)C1=CC=CC(S(=O)(=O)N2C3=CC=C(C=C3C=C2CC=2C=CC(=CC=2)C(O)=O)C(F)(F)F)=C1 ROSKYXAZUFLFLR-UHFFFAOYSA-N 0.000 claims 2
- FUOSTELFLYZQCW-UHFFFAOYSA-N 1,2-oxazol-3-one Chemical group OC=1C=CON=1 FUOSTELFLYZQCW-UHFFFAOYSA-N 0.000 claims 1
- WELNSIYTQJSNRP-UHFFFAOYSA-N 2-fluoro-6-methylbenzoic acid Chemical compound CC1=CC=CC(F)=C1C(O)=O WELNSIYTQJSNRP-UHFFFAOYSA-N 0.000 claims 1
- AILVULOTFQUVEJ-UHFFFAOYSA-N 4-[1-[1-(benzenesulfonyl)-5-methoxyindol-2-yl]-1-hydroxyethyl]pyridine-3-carboxylic acid Chemical compound C=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=1C(C)(O)C1=CC=NC=C1C(O)=O AILVULOTFQUVEJ-UHFFFAOYSA-N 0.000 claims 1
- ODVJZYUUPXIGFU-UHFFFAOYSA-N 4-[[1-(3-tert-butylphenyl)sulfonyl-5-(trifluoromethyl)indol-2-yl]-fluoromethyl]benzoic acid Chemical compound CC(C)(C)C1=CC=CC(S(=O)(=O)N2C3=CC=C(C=C3C=C2C(F)C=2C=CC(=CC=2)C(O)=O)C(F)(F)F)=C1 ODVJZYUUPXIGFU-UHFFFAOYSA-N 0.000 claims 1
- KKOQRXIKLQBFFG-UHFFFAOYSA-N 4a,5-dihydro-4h-1,2-benzoxazin-3-one Chemical group C1C=CC=C2ONC(=O)CC21 KKOQRXIKLQBFFG-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- PSFFGWHJJQTRPR-UHFFFAOYSA-N 6-[[1-(3-tert-butylphenyl)sulfonyl-5-(trifluoromethyl)indol-2-yl]-hydroxymethyl]pyridine-3-carboxylic acid Chemical compound CC(C)(C)C1=CC=CC(S(=O)(=O)N2C3=CC=C(C=C3C=C2C(O)C=2N=CC(=CC=2)C(O)=O)C(F)(F)F)=C1 PSFFGWHJJQTRPR-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
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- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
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- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
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- 238000012216 screening Methods 0.000 description 1
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- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- INHFVOVJYPSAPX-UHFFFAOYSA-N tert-butyl 4-formyl-1-methylpyrrole-2-carboxylate Chemical compound CN1C=C(C=O)C=C1C(=O)OC(C)(C)C INHFVOVJYPSAPX-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—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
- C07D209/26—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 an acyl radical attached to the ring nitrogen atom
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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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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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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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
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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
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- C07D409/06—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 carbon chain containing only aliphatic carbon atoms
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0956259A FR2950053B1 (fr) | 2009-09-11 | 2009-09-11 | Utilisation de derives d'indole benzoique comme activateurs de nurr-1, pour le traitement de la maladie de parkinson |
| FR0956259 | 2009-09-11 | ||
| FR1050107A FR2950058B1 (fr) | 2009-09-11 | 2010-01-08 | Utilisation de derives d'indole benzoique comme activateurs de nurr-1, pour le traitement de la maladie de parkinson |
| FR1050107 | 2010-01-08 | ||
| PCT/FR2010/051884 WO2011030068A1 (fr) | 2009-09-11 | 2010-09-10 | Utilisation de derives d'indole comme activateurs de nurr-1, pour leur application en tant que medicament pour le traitement de la maladie de parkinson |
Publications (1)
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| CA2772697A1 true CA2772697A1 (fr) | 2011-03-17 |
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| CA2772697A Abandoned CA2772697A1 (fr) | 2009-09-11 | 2010-09-10 | Utilisation de derives d'indole comme activateurs de nurr-1, pour leur application en tant que medicament pour le traitement de la maladie de parkinson |
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| CN105272975B (zh) * | 2014-06-10 | 2019-03-26 | 中国科学院上海药物研究所 | 一类具有1,2,4-恶二唑片段结构的吲哚生物碱及其制备方法和用途 |
| WO2018136575A1 (en) * | 2017-01-18 | 2018-07-26 | Albert Einstein College Of Medicine, Inc. | Pxr agonists and uses thereof for gut barrier dysfunction treatment and prevention |
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| GB0303503D0 (en) | 2003-02-14 | 2003-03-19 | Novartis Ag | Organic compounds |
| AR043633A1 (es) * | 2003-03-20 | 2005-08-03 | Schering Corp | Ligandos de receptores de canabinoides |
| WO2004108094A2 (en) * | 2003-06-06 | 2004-12-16 | Atherogenics, Inc. | Sulfonamide-substituted chalcone derivatives and their use to treat diseases |
| WO2005047268A2 (en) | 2003-11-10 | 2005-05-26 | X-Ceptor Therapeutics, Inc. | Substituted pyrimidine compositions and methods of use |
| WO2005056522A2 (en) | 2003-12-04 | 2005-06-23 | National Health Research Institutes | Indole compounds |
| DK1761519T3 (da) * | 2004-06-21 | 2008-07-21 | Hoffmann La Roche | Indolderivater som histaminreceptorantagonister |
| FR2890071B1 (fr) * | 2005-08-30 | 2007-11-09 | Fournier Sa Sa Lab | Nouveaux composes de l'indole |
| SG165362A1 (en) * | 2005-09-07 | 2010-10-28 | Plexxikon Inc | Ppar active compounds |
| FR2903107B1 (fr) | 2006-07-03 | 2008-08-22 | Sanofi Aventis Sa | Derives d'imidazopyridine-2-carboxamides, leur preparation et leur application en therapeutique |
| FR2903106B1 (fr) | 2006-07-03 | 2010-07-30 | Sanofi Aventis | Utilisations de 2-benzoyl-imidazopyridines en therapeutique |
| FR2903105A1 (fr) | 2006-07-03 | 2008-01-04 | Sanofi Aventis Sa | Derives de 2-benzoyl-imidazopyridines, leur preparation et leur application en therapeutique |
-
2009
- 2009-09-11 FR FR0956259A patent/FR2950053B1/fr active Active
-
2010
- 2010-01-08 FR FR1050107A patent/FR2950058B1/fr active Active
- 2010-09-10 SG SG2012010815A patent/SG178451A1/en unknown
- 2010-09-10 TW TW099130733A patent/TW201119650A/zh unknown
- 2010-09-10 RU RU2012110883/04A patent/RU2012110883A/ru not_active Application Discontinuation
- 2010-09-10 NZ NZ598576A patent/NZ598576A/en not_active IP Right Cessation
- 2010-09-10 EP EP10770545A patent/EP2475642A1/fr not_active Withdrawn
- 2010-09-10 PE PE2012000304A patent/PE20121346A1/es not_active Application Discontinuation
- 2010-09-10 PH PH1/2012/500390A patent/PH12012500390A1/en unknown
- 2010-09-10 CN CN2010800509223A patent/CN102596906A/zh active Pending
- 2010-09-10 CN CN201310415421.6A patent/CN103554006A/zh active Pending
- 2010-09-10 KR KR1020127006186A patent/KR20120065345A/ko not_active Withdrawn
- 2010-09-10 IN IN2005DEN2012 patent/IN2012DN02005A/en unknown
- 2010-09-10 MX MX2012003027A patent/MX2012003027A/es not_active Application Discontinuation
- 2010-09-10 JP JP2012528430A patent/JP2013504548A/ja active Pending
- 2010-09-10 CA CA2772697A patent/CA2772697A1/fr not_active Abandoned
- 2010-09-10 BR BR112012005480A patent/BR112012005480A2/pt not_active IP Right Cessation
- 2010-09-10 AU AU2010294018A patent/AU2010294018A1/en not_active Abandoned
- 2010-09-10 WO PCT/FR2010/051884 patent/WO2011030068A1/fr not_active Ceased
- 2010-09-10 AR ARP100103313A patent/AR078358A1/es unknown
- 2010-09-18 SA SA110310698A patent/SA110310698B1/ar unknown
-
2012
- 2012-02-24 ZA ZA2012/01400A patent/ZA201201400B/en unknown
- 2012-03-03 EC ECSP12011718 patent/ECSP12011718A/es unknown
- 2012-03-07 IL IL218526A patent/IL218526A0/en unknown
- 2012-03-07 DO DO2012000061A patent/DOP2012000061A/es unknown
- 2012-03-09 CO CO12041658A patent/CO6511224A2/es not_active Application Discontinuation
- 2012-03-09 US US13/416,018 patent/US20120232070A1/en not_active Abandoned
- 2012-03-09 CL CL2012000632A patent/CL2012000632A1/es unknown
- 2012-03-19 CR CR20120131A patent/CR20120131A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL218526A0 (en) | 2012-07-31 |
| MX2012003027A (es) | 2012-04-19 |
| US20120232070A1 (en) | 2012-09-13 |
| IN2012DN02005A (enExample) | 2015-07-24 |
| FR2950053B1 (fr) | 2014-08-01 |
| NZ598576A (en) | 2014-05-30 |
| TW201119650A (en) | 2011-06-16 |
| CL2012000632A1 (es) | 2012-10-19 |
| AR078358A1 (es) | 2011-11-02 |
| SG178451A1 (en) | 2012-03-29 |
| DOP2012000061A (es) | 2012-09-30 |
| EP2475642A1 (fr) | 2012-07-18 |
| AU2010294018A1 (en) | 2012-03-29 |
| SA110310698B1 (ar) | 2014-11-16 |
| CN103554006A (zh) | 2014-02-05 |
| CO6511224A2 (es) | 2012-08-31 |
| ECSP12011718A (es) | 2012-04-30 |
| FR2950058B1 (fr) | 2016-04-01 |
| CN102596906A (zh) | 2012-07-18 |
| FR2950053A1 (fr) | 2011-03-18 |
| WO2011030068A1 (fr) | 2011-03-17 |
| JP2013504548A (ja) | 2013-02-07 |
| PE20121346A1 (es) | 2012-10-15 |
| PH12012500390A1 (en) | 2012-10-22 |
| ZA201201400B (en) | 2013-05-29 |
| RU2012110883A (ru) | 2013-10-20 |
| KR20120065345A (ko) | 2012-06-20 |
| BR112012005480A2 (pt) | 2019-09-24 |
| CR20120131A (es) | 2012-07-27 |
| FR2950058A1 (fr) | 2011-03-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20160912 |