AU2015239539A1 - Pyridine-2-amides useful as CB2 agonists - Google Patents
Pyridine-2-amides useful as CB2 agonists Download PDFInfo
- Publication number
- AU2015239539A1 AU2015239539A1 AU2015239539A AU2015239539A AU2015239539A1 AU 2015239539 A1 AU2015239539 A1 AU 2015239539A1 AU 2015239539 A AU2015239539 A AU 2015239539A AU 2015239539 A AU2015239539 A AU 2015239539A AU 2015239539 A1 AU2015239539 A1 AU 2015239539A1
- Authority
- AU
- Australia
- Prior art keywords
- carboxamide
- pyridine
- oxadiazol
- cyclopropylmethoxy
- methyl
- 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
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- 239000000556 agonist Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 221
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- 238000006243 chemical reaction Methods 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 46
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- 150000003839 salts Chemical class 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 16
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- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- PLGZAPJQMPAGQR-UHFFFAOYSA-N tert-butyl n-[5-bromo-3-(cyclopropylmethoxy)pyrazin-2-yl]-n-[(2-methylpropan-2-yl)oxycarbonyl]carbamate Chemical compound CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(Br)N=C1OCC1CC1 PLGZAPJQMPAGQR-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
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- 230000000699 topical effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
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- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
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Classifications
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- 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
- C07D401/02—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 containing two hetero rings
- C07D401/04—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 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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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
- C07D401/02—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 containing two hetero rings
- C07D401/12—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 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D417/02—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 containing two hetero rings
- C07D417/06—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 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Applications Claiming Priority (3)
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| EP14163555 | 2014-04-04 | ||
| EP14163555.7 | 2014-04-04 | ||
| PCT/EP2015/057151 WO2015150440A1 (en) | 2014-04-04 | 2015-04-01 | Pyridine-2-amides useful as cb2 agonists |
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| SG11201507994QA (en) | 2013-03-26 | 2015-10-29 | Hoffmann La Roche | Novel pyridine derivatives |
| EP3126354B1 (en) | 2014-04-04 | 2020-01-22 | H. Lundbeck A/S | Halogenated quinazolin-thf-amines as pde1 inhibitors |
| HRP20200606T1 (hr) | 2015-12-09 | 2020-07-10 | F. Hoffmann - La Roche Ag | Derivati fenila kao agonisti kanabinoidnog receptora 2 |
| TW201808906A (zh) | 2016-03-16 | 2018-03-16 | 拜耳作物科學股份有限公司 | 作為殺蟲劑之經取代吡啶化合物 |
| WO2018234284A1 (en) | 2017-06-20 | 2018-12-27 | F. Hoffmann-La Roche Ag | Pyridine derivatives |
| CN112638430B (zh) | 2018-06-27 | 2023-05-16 | 豪夫迈·罗氏有限公司 | 放射性标记的大麻素受体2配体 |
| SG11202009103WA (en) * | 2018-06-27 | 2020-10-29 | Hoffmann La Roche | Novel pyridine and pyrazine compounds as inhibitors of cannabinoid receptor 2 |
| EP3814328A1 (en) | 2018-06-27 | 2021-05-05 | F. Hoffmann-La Roche AG | Novel azetidine-substituted pyridine and pyrazine compounds as inhibitors of cannabinoid receptor 2 |
| CN112074513B (zh) * | 2018-06-27 | 2024-06-14 | 豪夫迈·罗氏有限公司 | 作为优先大麻素2激动剂的吡啶和吡嗪衍生物 |
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| EP1863778B1 (en) | 2005-03-31 | 2015-12-30 | Merck Sharp & Dohme Corp. | Spirocyclic thrombin receptor antagonists |
| FR2887550A1 (fr) | 2005-06-24 | 2006-12-29 | Sanofi Aventis Sa | Derives de 1-benzylpyrazole-3-acetamide, leur preparation et leur application en therapeutique |
| CN101855222A (zh) * | 2007-05-10 | 2010-10-06 | 通用电气健康护理有限公司 | 对大麻素cb2受体具有活性的咪唑并(1,2-a)吡啶和相关化合物 |
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| JP6654574B2 (ja) | 2020-02-26 |
| TW201623276A (zh) | 2016-07-01 |
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| PH12016501865A1 (en) | 2016-12-19 |
| US20180327396A1 (en) | 2018-11-15 |
| CN106132958A (zh) | 2016-11-16 |
| EA201691983A1 (ru) | 2017-01-30 |
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| EA030116B1 (ru) | 2018-06-29 |
| JP2017509676A (ja) | 2017-04-06 |
| CR20160448A (es) | 2016-12-14 |
| WO2015150440A1 (en) | 2015-10-08 |
| AR099933A1 (es) | 2016-08-31 |
| KR20160142365A (ko) | 2016-12-12 |
| US20160376262A1 (en) | 2016-12-29 |
| PE20161370A1 (es) | 2016-12-17 |
| SG10201809066TA (en) | 2018-11-29 |
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