KR20120065345A - 파킨슨 질환 치료용 약제로서의 적용을 위한 nurr-1 활성화제로서의 인돌 유도체의 용도 - Google Patents
파킨슨 질환 치료용 약제로서의 적용을 위한 nurr-1 활성화제로서의 인돌 유도체의 용도 Download PDFInfo
- Publication number
- KR20120065345A KR20120065345A KR1020127006186A KR20127006186A KR20120065345A KR 20120065345 A KR20120065345 A KR 20120065345A KR 1020127006186 A KR1020127006186 A KR 1020127006186A KR 20127006186 A KR20127006186 A KR 20127006186A KR 20120065345 A KR20120065345 A KR 20120065345A
- Authority
- KR
- South Korea
- 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.)
- Withdrawn
Links
- 238000011282 treatment Methods 0.000 title claims description 25
- 208000018737 Parkinson disease Diseases 0.000 title claims description 22
- 239000003814 drug Substances 0.000 title abstract description 4
- 239000012190 activator Substances 0.000 title description 4
- 150000002475 indoles Chemical class 0.000 title description 4
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 382
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 228
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 206
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 197
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 162
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 128
- 125000004432 carbon atom Chemical group C* 0.000 claims description 122
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 109
- 239000005711 Benzoic acid Substances 0.000 claims description 104
- 235000010233 benzoic acid Nutrition 0.000 claims description 97
- 125000000217 alkyl group Chemical group 0.000 claims description 80
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 76
- 238000004519 manufacturing process Methods 0.000 claims description 61
- -1 sulfonylcarbamoyl group Chemical group 0.000 claims description 59
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 54
- 125000005843 halogen group Chemical group 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 44
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 42
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 150000004702 methyl esters Chemical class 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 230000004770 neurodegeneration Effects 0.000 claims description 12
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 229910052757 nitrogen Chemical group 0.000 claims description 10
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 150000001735 carboxylic acids Chemical group 0.000 claims description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical group O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 229940127557 pharmaceutical product Drugs 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- NWCDECRXMSNFFO-UHFFFAOYSA-N 3-[[1-(3-tert-butylphenyl)sulfonyl-5-(trifluoromethyl)indol-2-yl]methyl]-5-fluorobenzoic acid Chemical compound CC(C)(C)C1=CC=CC(S(=O)(=O)N2C3=CC=C(C=C3C=C2CC=2C=C(C=C(F)C=2)C(O)=O)C(F)(F)F)=C1 NWCDECRXMSNFFO-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- RPKJDBOESOOANU-UHFFFAOYSA-N 4-[[1-(3-tert-butylphenyl)sulfonyl-3-fluoro-5-(trifluoromethyl)indol-2-yl]methyl]benzoic acid Chemical compound CC(C)(C)C1=CC=CC(S(=O)(=O)N2C3=CC=C(C=C3C(F)=C2CC=2C=CC(=CC=2)C(O)=O)C(F)(F)F)=C1 RPKJDBOESOOANU-UHFFFAOYSA-N 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004494 ethyl ester group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 238000011321 prophylaxis Methods 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- VHFMKMQEMKDRLN-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-5-methoxyindole-2-carbonyl]pyridine-3-carboxylic acid Chemical compound C=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=1C(=O)C1=NC=CC=C1C(O)=O VHFMKMQEMKDRLN-UHFFFAOYSA-N 0.000 claims description 3
- NPAVQHSSIOKRJV-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-6-methoxyindole-2-carbonyl]pyridine-3-carboxylic acid Chemical compound C=1C=CC=CC=1S(=O)(=O)N1C2=CC(OC)=CC=C2C=C1C(=O)C1=NC=CC=C1C(O)=O NPAVQHSSIOKRJV-UHFFFAOYSA-N 0.000 claims description 3
- SWJRDSQAQIFKAB-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)indole-2-carbonyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 SWJRDSQAQIFKAB-UHFFFAOYSA-N 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 3
- NPYBNIDELUJPNF-UHFFFAOYSA-N 3-[1-(benzenesulfonyl)-5-methoxyindole-2-carbonyl]pyridine-4-carboxylic acid Chemical compound C=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=1C(=O)C1=CN=CC=C1C(O)=O NPYBNIDELUJPNF-UHFFFAOYSA-N 0.000 claims description 3
- IETSTSVPZSSTAR-UHFFFAOYSA-N 3-[1-(benzenesulfonyl)indole-2-carbonyl]pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=C1C(=O)C1=CC2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 IETSTSVPZSSTAR-UHFFFAOYSA-N 0.000 claims description 3
- 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
- GGTPEZBZYNMRAF-UHFFFAOYSA-N 4-[1-(benzenesulfonyl)-3-bromoindole-2-carbonyl]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC=C1C(=O)C1=C(Br)C2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 GGTPEZBZYNMRAF-UHFFFAOYSA-N 0.000 claims description 3
- SULRDKMRHDCHOW-UHFFFAOYSA-N 4-[1-(benzenesulfonyl)-3-chloroindole-2-carbonyl]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC=C1C(=O)C1=C(Cl)C2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 SULRDKMRHDCHOW-UHFFFAOYSA-N 0.000 claims description 3
- RVOBNJGKSCIECV-UHFFFAOYSA-N 4-[1-(benzenesulfonyl)-5-methoxyindole-2-carbonyl]pyridine-3-carboxylic acid Chemical compound C=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=1C(=O)C1=CC=NC=C1C(O)=O RVOBNJGKSCIECV-UHFFFAOYSA-N 0.000 claims description 3
- TXGXATKMVOFUEO-UHFFFAOYSA-N 4-[1-(benzenesulfonyl)indole-2-carbonyl]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC=C1C(=O)C1=CC2=CC=CC=C2N1S(=O)(=O)C1=CC=CC=C1 TXGXATKMVOFUEO-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- XEPQMZRDLOFEAE-UHFFFAOYSA-N 4-[1-[1-(benzenesulfonyl)-5-methoxyindol-2-yl]ethyl]pyridine-3-carboxylic acid Chemical compound C=1C2=CC(OC)=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=1C(C)C1=CC=NC=C1C(O)=O XEPQMZRDLOFEAE-UHFFFAOYSA-N 0.000 claims description 3
- XLBPLVNGWMPZCX-UHFFFAOYSA-N 4-[[1-(3-tert-butylphenyl)sulfonyl-5-(trifluoromethyl)indol-2-yl]methyl]-3-fluorobenzoic acid Chemical compound CC(C)(C)C1=CC=CC(S(=O)(=O)N2C3=CC=C(C=C3C=C2CC=2C(=CC(=CC=2)C(O)=O)F)C(F)(F)F)=C1 XLBPLVNGWMPZCX-UHFFFAOYSA-N 0.000 claims description 3
- WDLWDEPSQUIFRH-UHFFFAOYSA-N 4-[[1-(3-tert-butylphenyl)sulfonyl-5-(trifluoromethyl)indol-2-yl]methyl]thiophene-2-carboxylic acid Chemical compound CC(C)(C)C1=CC=CC(S(=O)(=O)N2C3=CC=C(C=C3C=C2CC=2C=C(SC=2)C(O)=O)C(F)(F)F)=C1 WDLWDEPSQUIFRH-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- UXWUJXLQYBCIOP-UHFFFAOYSA-N 5-[[1-(benzenesulfonyl)-5-methylsulfanylindol-2-yl]-hydroxymethyl]furan-2-carboxylic acid Chemical compound C=1C2=CC(SC)=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=1C(O)C1=CC=C(C(O)=O)O1 UXWUJXLQYBCIOP-UHFFFAOYSA-N 0.000 claims description 3
- BUEGANUUIFEUHP-UHFFFAOYSA-N 5-[[1-(benzenesulfonyl)-5-methylsulfanylindol-2-yl]methyl]furan-2-carboxylic acid Chemical compound C=1C2=CC(SC)=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=1CC1=CC=C(C(O)=O)O1 BUEGANUUIFEUHP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004586 dihydrobenzopyranyl group Chemical group O1C(CCC2=C1C=CC=C2)* 0.000 claims description 3
- 125000005434 dihydrobenzoxazinyl group Chemical group O1N(CCC2=C1C=CC=C2)* 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- FUOSTELFLYZQCW-UHFFFAOYSA-N 1,2-oxazol-3-one Chemical group OC=1C=CON=1 FUOSTELFLYZQCW-UHFFFAOYSA-N 0.000 claims description 2
- YKNGNVVDJRQFTO-UHFFFAOYSA-N 2-[[1-(3-tert-butylphenyl)sulfonyl-5-(trifluoromethyl)indol-2-yl]methyl]-1,3-thiazole-4-carboxylic acid Chemical compound CC(C)(C)C1=CC=CC(S(=O)(=O)N2C3=CC=C(C=C3C=C2CC=2SC=C(N=2)C(O)=O)C(F)(F)F)=C1 YKNGNVVDJRQFTO-UHFFFAOYSA-N 0.000 claims description 2
- FGYZXXJIDMOPDF-UHFFFAOYSA-N 2-fluoro-5-[[1-[(4-methyl-2,3-dihydro-1,4-benzoxazin-6-yl)sulfonyl]-5-(trifluoromethyl)indol-2-yl]methyl]benzoic acid Chemical compound C1=C2N(C)CCOC2=CC=C1S(=O)(=O)N(C1=CC=C(C=C1C=1)C(F)(F)F)C=1CC1=CC=C(F)C(C(O)=O)=C1 FGYZXXJIDMOPDF-UHFFFAOYSA-N 0.000 claims description 2
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- HXDYYHACDATIGB-UHFFFAOYSA-N 4-[[1-(3-tert-butylphenyl)sulfonyl-3-methyl-5-(trifluoromethyl)indol-2-yl]methyl]benzoic acid Chemical compound C=1C=CC(C(C)(C)C)=CC=1S(=O)(=O)N1C2=CC=C(C(F)(F)F)C=C2C(C)=C1CC1=CC=C(C(O)=O)C=C1 HXDYYHACDATIGB-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- SRKPQSVRGGJMSK-UHFFFAOYSA-N 4-[[1-(3-tert-butylphenyl)sulfonyl-5-(trifluoromethyl)indol-2-yl]methyl]-2-chlorobenzoic acid Chemical compound CC(C)(C)C1=CC=CC(S(=O)(=O)N2C3=CC=C(C=C3C=C2CC=2C=C(Cl)C(C(O)=O)=CC=2)C(F)(F)F)=C1 SRKPQSVRGGJMSK-UHFFFAOYSA-N 0.000 claims description 2
- CUIOROJHMZFUHV-UHFFFAOYSA-N 4-[[1-(3-tert-butylphenyl)sulfonyl-5-(trifluoromethyl)indol-2-yl]methyl]benzoic acid Chemical compound CC(C)(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 CUIOROJHMZFUHV-UHFFFAOYSA-N 0.000 claims description 2
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- 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 description 2
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
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Images
Classifications
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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
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Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
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| 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 |
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| KR20120065345A true KR20120065345A (ko) | 2012-06-20 |
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| KR1020127006186A Withdrawn KR20120065345A (ko) | 2009-09-11 | 2010-09-10 | 파킨슨 질환 치료용 약제로서의 적용을 위한 nurr-1 활성화제로서의 인돌 유도체의 용도 |
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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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| GB9615441D0 (en) * | 1996-07-23 | 1996-09-04 | Pharmacia Spa | Benzoylpropionic acid ester derivatives |
| GB9716656D0 (en) | 1997-08-07 | 1997-10-15 | Zeneca Ltd | Chemical compounds |
| ATE482945T1 (de) * | 1998-05-26 | 2010-10-15 | Chugai Pharmaceutical Co Ltd | Heterozyklische indolderivate und mono- oder diazaindol-derivate |
| GB9902461D0 (en) | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| CZ20023544A3 (cs) * | 2000-04-28 | 2004-07-14 | Baxter Healthcare Sa | Deriváty 2-acylindolu a jejich použití jako protinádorové činidlo |
| GB0119911D0 (en) | 2001-08-15 | 2001-10-10 | Novartis Ag | Organic Compounds |
| GB0303503D0 (en) | 2003-02-14 | 2003-03-19 | Novartis Ag | Organic compounds |
| TW200505902A (en) * | 2003-03-20 | 2005-02-16 | Schering Corp | Cannabinoid receptor ligands |
| 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 |
| CN1886133B (zh) | 2003-12-04 | 2010-12-01 | 财团法人卫生研究院 | 吲哚化合物 |
| 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 |
| RU2419618C2 (ru) * | 2005-09-07 | 2011-05-27 | Плекссикон, Инк. | Соединения, активные в отношении ppar (рецепторов активаторов пролиферации пероксисом) |
| FR2903105A1 (fr) | 2006-07-03 | 2008-01-04 | Sanofi Aventis Sa | Derives de 2-benzoyl-imidazopyridines, leur preparation et leur application en therapeutique |
| FR2903106B1 (fr) | 2006-07-03 | 2010-07-30 | Sanofi Aventis | Utilisations de 2-benzoyl-imidazopyridines en therapeutique |
| FR2903107B1 (fr) | 2006-07-03 | 2008-08-22 | Sanofi Aventis Sa | Derives d'imidazopyridine-2-carboxamides, leur preparation et leur application en therapeutique |
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2009
- 2009-09-11 FR FR0956259A patent/FR2950053B1/fr active Active
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2010
- 2010-01-08 FR FR1050107A patent/FR2950058B1/fr active Active
- 2010-09-10 PE PE2012000304A patent/PE20121346A1/es not_active Application Discontinuation
- 2010-09-10 CN CN201310415421.6A patent/CN103554006A/zh active Pending
- 2010-09-10 RU RU2012110883/04A patent/RU2012110883A/ru not_active Application Discontinuation
- 2010-09-10 SG SG2012010815A patent/SG178451A1/en unknown
- 2010-09-10 PH PH1/2012/500390A patent/PH12012500390A1/en unknown
- 2010-09-10 KR KR1020127006186A patent/KR20120065345A/ko not_active Withdrawn
- 2010-09-10 MX MX2012003027A patent/MX2012003027A/es not_active Application Discontinuation
- 2010-09-10 CA CA2772697A patent/CA2772697A1/fr not_active Abandoned
- 2010-09-10 NZ NZ598576A patent/NZ598576A/en not_active IP Right Cessation
- 2010-09-10 BR BR112012005480A patent/BR112012005480A2/pt not_active IP Right Cessation
- 2010-09-10 WO PCT/FR2010/051884 patent/WO2011030068A1/fr not_active Ceased
- 2010-09-10 AU AU2010294018A patent/AU2010294018A1/en not_active Abandoned
- 2010-09-10 IN IN2005DEN2012 patent/IN2012DN02005A/en unknown
- 2010-09-10 AR ARP100103313A patent/AR078358A1/es unknown
- 2010-09-10 CN CN2010800509223A patent/CN102596906A/zh active Pending
- 2010-09-10 EP EP10770545A patent/EP2475642A1/fr not_active Withdrawn
- 2010-09-10 JP JP2012528430A patent/JP2013504548A/ja active Pending
- 2010-09-10 TW TW099130733A patent/TW201119650A/zh unknown
- 2010-09-18 SA SA110310698A patent/SA110310698B1/ar unknown
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- 2012-03-09 US US13/416,018 patent/US20120232070A1/en not_active Abandoned
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Also Published As
| Publication number | Publication date |
|---|---|
| FR2950058A1 (fr) | 2011-03-18 |
| PH12012500390A1 (en) | 2012-10-22 |
| IL218526A0 (en) | 2012-07-31 |
| MX2012003027A (es) | 2012-04-19 |
| JP2013504548A (ja) | 2013-02-07 |
| RU2012110883A (ru) | 2013-10-20 |
| AU2010294018A1 (en) | 2012-03-29 |
| CR20120131A (es) | 2012-07-27 |
| CL2012000632A1 (es) | 2012-10-19 |
| SA110310698B1 (ar) | 2014-11-16 |
| PE20121346A1 (es) | 2012-10-15 |
| FR2950053B1 (fr) | 2014-08-01 |
| US20120232070A1 (en) | 2012-09-13 |
| CO6511224A2 (es) | 2012-08-31 |
| IN2012DN02005A (https=) | 2015-07-24 |
| CA2772697A1 (fr) | 2011-03-17 |
| FR2950058B1 (fr) | 2016-04-01 |
| DOP2012000061A (es) | 2012-09-30 |
| CN103554006A (zh) | 2014-02-05 |
| BR112012005480A2 (pt) | 2019-09-24 |
| SG178451A1 (en) | 2012-03-29 |
| NZ598576A (en) | 2014-05-30 |
| CN102596906A (zh) | 2012-07-18 |
| EP2475642A1 (fr) | 2012-07-18 |
| WO2011030068A1 (fr) | 2011-03-17 |
| TW201119650A (en) | 2011-06-16 |
| FR2950053A1 (fr) | 2011-03-18 |
| AR078358A1 (es) | 2011-11-02 |
| ZA201201400B (en) | 2013-05-29 |
| ECSP12011718A (es) | 2012-04-30 |
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