DE60309739T2 - Pyridinderivate als modulatoren des cb2-rezeptors - Google Patents
Pyridinderivate als modulatoren des cb2-rezeptors Download PDFInfo
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- DE60309739T2 DE60309739T2 DE60309739T DE60309739T DE60309739T2 DE 60309739 T2 DE60309739 T2 DE 60309739T2 DE 60309739 T DE60309739 T DE 60309739T DE 60309739 T DE60309739 T DE 60309739T DE 60309739 T2 DE60309739 T2 DE 60309739T2
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- Germany
- Prior art keywords
- fluorobenzyl
- isopropylnicotinamide
- chlorophenylamino
- trifluoromethylnicotinamide
- alkyl
- 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.)
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- 150000003222 pyridines Chemical class 0.000 title abstract description 4
- 102000009135 CB2 Cannabinoid Receptor Human genes 0.000 title description 15
- 108010073376 CB2 Cannabinoid Receptor Proteins 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 187
- 208000002193 Pain Diseases 0.000 claims abstract description 40
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 47
- -1 pyrizinyl Chemical group 0.000 claims description 39
- 239000007787 solid Substances 0.000 claims description 31
- 239000003814 drug Substances 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 20
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 229940079593 drug Drugs 0.000 claims description 16
- 239000002245 particle Substances 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 12
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 12
- 239000000725 suspension Substances 0.000 claims description 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000001238 wet grinding Methods 0.000 claims description 8
- 201000008482 osteoarthritis Diseases 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 238000001694 spray drying Methods 0.000 claims description 7
- 229940124597 therapeutic agent Drugs 0.000 claims description 7
- 206010065390 Inflammatory pain Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- 125000004306 triazinyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 206010027599 migraine Diseases 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 208000001132 Osteoporosis Diseases 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 208000026278 immune system disease Diseases 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
- VIDYNNZIYZXSRO-UHFFFAOYSA-N 6-(2-cyano-3-methylanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(C)=C1C#N VIDYNNZIYZXSRO-UHFFFAOYSA-N 0.000 claims description 3
- DHUGSUNSVLTDTM-UHFFFAOYSA-N 6-(3-chloro-4-fluoroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(F)C(Cl)=C1 DHUGSUNSVLTDTM-UHFFFAOYSA-N 0.000 claims description 3
- HRFSPRYAKFJJPT-UHFFFAOYSA-N 6-(3-chloroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 HRFSPRYAKFJJPT-UHFFFAOYSA-N 0.000 claims description 3
- 206010058019 Cancer Pain Diseases 0.000 claims description 3
- 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 3
- 125000004276 dioxalanyl group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- ZPBVSCOBIZAMAY-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-propan-2-yl-6-[3-(trifluoromethyl)anilino]pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(C(F)(F)F)=C1 ZPBVSCOBIZAMAY-UHFFFAOYSA-N 0.000 claims description 3
- KBSXHWIDXFAPHZ-UHFFFAOYSA-N n-benzyl-6-(3-chloroanilino)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC=CC=2)C(C(F)(F)F)=CC=1NC1=CC=CC(Cl)=C1 KBSXHWIDXFAPHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 3
- WDMOKDLVCSTFNC-UHFFFAOYSA-N 6-(2,4-dichloroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(Cl)C=C1Cl WDMOKDLVCSTFNC-UHFFFAOYSA-N 0.000 claims description 2
- ZNMDBXTURIVJPF-UHFFFAOYSA-N 6-(2-chloro-4-fluoroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(F)C=C1Cl ZNMDBXTURIVJPF-UHFFFAOYSA-N 0.000 claims description 2
- QMUGRIITPDZHKX-UHFFFAOYSA-N 6-(3-chloroanilino)-4-propan-2-yl-n-(pyrazin-2-ylmethyl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2N=CC=NC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 QMUGRIITPDZHKX-UHFFFAOYSA-N 0.000 claims description 2
- SDKISIZAFVGWHD-UHFFFAOYSA-N 6-(3-chloroanilino)-4-propan-2-yl-n-(pyrimidin-4-ylmethyl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2N=CN=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 SDKISIZAFVGWHD-UHFFFAOYSA-N 0.000 claims description 2
- DUKBDMDUKNYYRA-UHFFFAOYSA-N 6-(3-chloroanilino)-n-(1h-imidazol-2-ylmethyl)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2NC=CN=2)C(C(F)(F)F)=CC=1NC1=CC=CC(Cl)=C1 DUKBDMDUKNYYRA-UHFFFAOYSA-N 0.000 claims description 2
- JPJVFDVMKSDSDG-UHFFFAOYSA-N 6-(3-chloroanilino)-n-(pyridin-4-ylmethyl)-2-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C=1C=C(C(=O)NCC=2C=CN=CC=2)C(C(F)(F)F)=NC=1NC1=CC=CC(Cl)=C1 JPJVFDVMKSDSDG-UHFFFAOYSA-N 0.000 claims description 2
- VEUHPKLXFLZXHS-UHFFFAOYSA-N 6-(3-chloroanilino)-n-(pyridin-4-ylmethyl)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CN=CC=2)C(C(F)(F)F)=CC=1NC1=CC=CC(Cl)=C1 VEUHPKLXFLZXHS-UHFFFAOYSA-N 0.000 claims description 2
- BTNCAWGVLHXQOR-UHFFFAOYSA-N 6-(3-chloroanilino)-n-[(4-cyanophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(=CC=2)C#N)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 BTNCAWGVLHXQOR-UHFFFAOYSA-N 0.000 claims description 2
- KCHREVSBHQMREC-UHFFFAOYSA-N 6-(3-cyanoanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(C#N)=C1 KCHREVSBHQMREC-UHFFFAOYSA-N 0.000 claims description 2
- PRIPEPDGNHKGME-UHFFFAOYSA-N 6-(4-bromo-2-chloroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(Br)C=C1Cl PRIPEPDGNHKGME-UHFFFAOYSA-N 0.000 claims description 2
- TWRHLZHSWILHMW-UHFFFAOYSA-N 6-(4-cyano-2-methylanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=C(C#N)C=C1C TWRHLZHSWILHMW-UHFFFAOYSA-N 0.000 claims description 2
- ILBFOAHHEOOKIN-UHFFFAOYSA-N 6-(5-chloro-2-fluoroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC(Cl)=CC=C1F ILBFOAHHEOOKIN-UHFFFAOYSA-N 0.000 claims description 2
- 208000005298 acute pain Diseases 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- JAXKYWPPYAKTOY-UHFFFAOYSA-N n-benzyl-6-(3-chloroanilino)-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1 JAXKYWPPYAKTOY-UHFFFAOYSA-N 0.000 claims description 2
- 208000009935 visceral pain Diseases 0.000 claims description 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- AGFUWYJKOBBRAQ-UHFFFAOYSA-N 6-(2,3-dichloroanilino)-n-[(2-fluoropyridin-4-yl)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=NC(F)=CC(CNC(=O)C=2C(=CC(NC=3C(=C(Cl)C=CC=3)Cl)=NC=2)C(F)(F)F)=C1 AGFUWYJKOBBRAQ-UHFFFAOYSA-N 0.000 claims 1
- QEELEYIYYNZWHY-UHFFFAOYSA-N 6-(2,3-dichloroanilino)-n-[(4-fluorophenyl)methyl]-4-propan-2-ylpyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCC=2C=CC(F)=CC=2)C(C(C)C)=CC=1NC1=CC=CC(Cl)=C1Cl QEELEYIYYNZWHY-UHFFFAOYSA-N 0.000 claims 1
- IQZVRLBNWINOEK-UHFFFAOYSA-N 6-(2,4-dichloroanilino)-n-[(2-fluoropyridin-4-yl)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=NC(F)=CC(CNC(=O)C=2C(=CC(NC=3C(=CC(Cl)=CC=3)Cl)=NC=2)C(F)(F)F)=C1 IQZVRLBNWINOEK-UHFFFAOYSA-N 0.000 claims 1
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- NRDXXGDBTKBXNH-UHFFFAOYSA-N 6-(2,4-dichloroanilino)-n-[(5-methyl-1h-1,2,4-triazol-3-yl)methyl]-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound N1C(C)=NN=C1CNC(=O)C(C(=C1)C(F)(F)F)=CN=C1NC1=CC=C(Cl)C=C1Cl NRDXXGDBTKBXNH-UHFFFAOYSA-N 0.000 claims 1
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- AVTVSPSKCYLHFQ-UHFFFAOYSA-N 6-(3,4-dichloroanilino)-n-(2-phenylethyl)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound N=1C=C(C(=O)NCCC=2C=CC=CC=2)C(C(F)(F)F)=CC=1NC1=CC=C(Cl)C(Cl)=C1 AVTVSPSKCYLHFQ-UHFFFAOYSA-N 0.000 claims 1
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- 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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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0222495 | 2002-09-27 | ||
| GBGB0222495.4A GB0222495D0 (en) | 2002-09-27 | 2002-09-27 | Compounds |
| PCT/EP2003/010935 WO2004029027A1 (en) | 2002-09-27 | 2003-09-25 | Pyridine derivatives as cb2 receptor modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60309739D1 DE60309739D1 (de) | 2006-12-28 |
| DE60309739T2 true DE60309739T2 (de) | 2007-10-31 |
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| Application Number | Title | Priority Date | Filing Date |
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| DE60309739T Expired - Fee Related DE60309739T2 (de) | 2002-09-27 | 2003-09-25 | Pyridinderivate als modulatoren des cb2-rezeptors |
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| EP (1) | EP1562907B1 (enExample) |
| JP (1) | JP2006508065A (enExample) |
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| ES (1) | ES2277149T3 (enExample) |
| GB (1) | GB0222495D0 (enExample) |
| WO (1) | WO2004029027A1 (enExample) |
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| WO2003082191A2 (en) | 2002-03-28 | 2003-10-09 | Merck & Co., Inc. | Substituted 2,3-diphenyl pyridines |
| UY27939A1 (es) | 2002-08-21 | 2004-03-31 | Glaxo Group Ltd | Compuestos |
| TW200505902A (en) | 2003-03-20 | 2005-02-16 | Schering Corp | Cannabinoid receptor ligands |
| EP1669348A4 (en) | 2003-09-30 | 2009-03-11 | Eisai R&D Man Co Ltd | NEW ANTIPILIC AGENT CONTAINING A HETEROCYCLIC COMPOUND |
| GB0402356D0 (en) * | 2004-02-03 | 2004-03-10 | Glaxo Group Ltd | Novel compounds |
| GB0402357D0 (en) * | 2004-02-03 | 2004-03-10 | Glaxo Group Ltd | Novel compounds |
| GB0402355D0 (en) * | 2004-02-03 | 2004-03-10 | Glaxo Group Ltd | Novel compounds |
| JP4874958B2 (ja) | 2005-03-30 | 2012-02-15 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ピリジン誘導体を含有する抗真菌剤 |
| JPWO2006129609A1 (ja) * | 2005-05-30 | 2009-01-08 | 塩野義製薬株式会社 | 2−ナフチルイミノ−5,5−ジ置換−1,3−チアジン誘導体 |
| TWI385169B (zh) | 2005-10-31 | 2013-02-11 | Eisai R&D Man Co Ltd | 經雜環取代之吡啶衍生物及含有彼之抗真菌劑 |
| WO2007118041A1 (en) * | 2006-04-07 | 2007-10-18 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| EP2081905B1 (en) | 2006-07-28 | 2012-09-12 | Boehringer Ingelheim International GmbH | Sulfonyl compounds which modulate the cb2 receptor |
| EP2065377B1 (en) | 2006-09-21 | 2011-11-23 | Eisai R&D Management Co., Ltd. | Pyridine derivative substituted by heteroaryl ring, and antifungal agent comprising the same |
| MX2009002888A (es) | 2006-09-25 | 2009-03-31 | Boehringer Ingelheim Int | Compuestos que modulan el receptor cb2. |
| FR2907784B1 (fr) * | 2006-10-27 | 2009-02-13 | Sod Conseils Rech Applic | Derives phenyliques et leur utilisation comme medicament |
| US9422235B2 (en) | 2006-12-19 | 2016-08-23 | Pharmos Corporation | Sulfonamide derivatives with therapeutic indications |
| TW200841879A (en) | 2007-04-27 | 2008-11-01 | Eisai R&D Man Co Ltd | Pyridine derivatives substituted by heterocyclic ring and phosphonoamino group, and anti-fungal agent containing same |
| CN102702185A (zh) | 2007-04-27 | 2012-10-03 | 卫材R&D管理有限公司 | 杂环取代吡啶衍生物的盐的结晶 |
| JP5300225B2 (ja) | 2007-08-03 | 2013-09-25 | バイエル・クロップサイエンス・アーゲー | 除草剤トリアゾリルピリジンケトン類 |
| WO2009061652A1 (en) | 2007-11-07 | 2009-05-14 | Boehringer Ingelheim International Gmbh | Compounds which modulate the cb2 receptor |
| US8513287B2 (en) | 2007-12-27 | 2013-08-20 | Eisai R&D Management Co., Ltd. | Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same |
| JP2011520975A (ja) * | 2008-05-19 | 2011-07-21 | ユニヴァーシティ オブ テネシー リサーチ ファウンデーション,ザ | ピリミジンの非古典的カンナビノイド化合物及び関連する使用方法 |
| EP2299819A4 (en) * | 2008-05-19 | 2011-07-20 | Univ Tennessee Res Foundation | NONCLASSICAL PYRIDINE CANNABINOID COMPOUNDS AND ASSOCIATED METHODS FOR THEIR USE |
| WO2009143182A1 (en) * | 2008-05-19 | 2009-11-26 | University Of Tennessee Research Foundation, The | Pyrimidine classical cannabinoid compounds and related methods of use |
| US8349876B2 (en) * | 2008-05-19 | 2013-01-08 | The University Of Tennesee Research Foundation | Pyridine non-classical cannabinoid compounds and related methods of use |
| EP2299817A1 (en) * | 2008-05-19 | 2011-03-30 | The University of Tennessee Research Foundation | Pyridine classical cannabinoid compounds and related methods of use |
| US8476439B2 (en) | 2008-05-19 | 2013-07-02 | The University Of Tennessee Research Foundation | Pyridine classical cannabinoid compounds and related methods of use |
| EP2326629B1 (en) | 2008-07-10 | 2013-10-02 | Boehringer Ingelheim International GmbH | Sulfone compounds which modulate the cb2 receptor |
| NZ591111A (en) | 2008-09-25 | 2013-08-30 | Boehringer Ingelheim Int | Sulfonyl compounds which selectively modulate the cb2 receptor |
| US8188119B2 (en) | 2008-10-24 | 2012-05-29 | Eisai R&D Management Co., Ltd | Pyridine derivatives substituted with heterocyclic ring and γ-glutamylamino group, and antifungal agents containing same |
| MX2011010396A (es) | 2009-03-30 | 2011-10-24 | Astellas Pharma Inc | Compuesto de pirimidina. |
| US8299103B2 (en) | 2009-06-15 | 2012-10-30 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the CB2 receptor |
| US8383615B2 (en) | 2009-06-16 | 2013-02-26 | Boehringer Ingelheim International Gmbh | Azetidine 2-carboxamide derivatives which modulate the CB2 receptor |
| US8541386B2 (en) | 2009-08-19 | 2013-09-24 | University Of South Florida | Cannabinoid 2 (CB2) receptor gene promoter and unique RNA transcripts in B cells and methods of use |
| EP2480544A1 (en) | 2009-09-22 | 2012-08-01 | Boehringer Ingelheim International GmbH | Compounds which selectively modulate the cb2 receptor |
| EP2523936A1 (en) | 2010-01-15 | 2012-11-21 | Boehringer Ingelheim International GmbH | Compounds which modulate the cb2 receptor |
| WO2011109324A1 (en) | 2010-03-05 | 2011-09-09 | Boehringer Ingelheim International Gmbh | Tetrazole compounds which selectively modulate the cb2 receptor |
| JP5746764B2 (ja) | 2010-07-22 | 2015-07-08 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Cb2受容体を調節する化合物 |
| WO2012031817A1 (en) * | 2010-09-09 | 2012-03-15 | F. Hoffmann-La Roche Ag | Determination of abca1 protein levels in cells |
| US8552200B2 (en) * | 2010-10-20 | 2013-10-08 | Gruenenthal Gmbh | Substituted 6-amino-nicotinamides as KCNQ2/3 modulators |
| AU2013351552A1 (en) * | 2012-11-28 | 2015-07-16 | Grünenthal GmbH | Substituted Amino-arylcarboxamides as KCNQ2/3 modulators |
| EP2803668A1 (en) | 2013-05-17 | 2014-11-19 | Boehringer Ingelheim International Gmbh | Novel (cyano-dimethyl-methyl)-isoxazoles and -[1,3,4]thiadiazoles |
| CN106565517B (zh) * | 2016-10-18 | 2018-08-17 | 湖南大学 | 一种由芳基甲烷衍生物和腈制备酰胺的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5112820A (en) * | 1990-03-05 | 1992-05-12 | Sterling Drug Inc. | Anti-glaucoma compositions containing 2- and 3-aminomethyl-6-arylcarbonyl- or 6-phenylthio-2,3-dihydropyrrolo-(1,2,3-de)-1,4-benzoxazines and method of use thereof |
| CZ101496A3 (en) * | 1993-10-12 | 1996-11-13 | Du Pont Merck Pharma | N-alkyl-n-aryl-pyrimidinamines and derivatives thereof |
| FR2742148B1 (fr) * | 1995-12-08 | 1999-10-22 | Sanofi Sa | Nouveaux derives du pyrazole-3-carboxamide, procede pour leur preparation et compositions pharmaceutiques les contenant |
| US6022884A (en) * | 1997-11-07 | 2000-02-08 | Amgen Inc. | Substituted pyridine compounds and methods of use |
| US7507767B2 (en) * | 2001-02-08 | 2009-03-24 | Schering Corporation | Cannabinoid receptor ligands |
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2004029027A1 (en) | 2004-04-08 |
| EP1562907B1 (en) | 2006-11-15 |
| DE60309739D1 (de) | 2006-12-28 |
| US20070129367A1 (en) | 2007-06-07 |
| AU2003276028A1 (en) | 2004-04-19 |
| ES2277149T3 (es) | 2007-07-01 |
| EP1562907A1 (en) | 2005-08-17 |
| JP2006508065A (ja) | 2006-03-09 |
| ATE345329T1 (de) | 2006-12-15 |
| GB0222495D0 (en) | 2002-11-06 |
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| 8381 | Inventor (new situation) |
Inventor name: EATHERTON, ANDREW JOHN, HARLOW, ESSEX CM19 5AW, GB Inventor name: GIBLIN, GERARD MARTIN PAUL, HARLOW, ESSEX CM19, GB Inventor name: GREEN, HOWARD DECEASED, HOWARD, HARLOW, ESSEX , GB Inventor name: JANDU, KARAMJIT SINGH, HARLOW, ESSEX CM19 5AW, GB Inventor name: MITCHELL, WILLIAM LEONARD, HARLOW, ESSEX CM19 , GB Inventor name: NAYLOR, ALAN, HARLOW, ESSEX CM19 5AW, GB Inventor name: PALOMBI, C/O NIKEM RESEARCH S.R.L., GIOVANNI, , IT Inventor name: RAWLINGS, DEREK ANTHONY, HARLOW, ESSEX CM19 5A, GB Inventor name: SLINGSBY, BRIAN PETER, HARLOW, ESSEX CM19 5AW, GB Inventor name: WHITTINGTON, ANDREW RICHARD, STEVENAGE, HERTFO, GB |
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| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |