TW201803869A - 作為RORγT調節劑之6-胺基吡啶-3-基噻唑 - Google Patents
作為RORγT調節劑之6-胺基吡啶-3-基噻唑 Download PDFInfo
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- TW201803869A TW201803869A TW106113710A TW106113710A TW201803869A TW 201803869 A TW201803869 A TW 201803869A TW 106113710 A TW106113710 A TW 106113710A TW 106113710 A TW106113710 A TW 106113710A TW 201803869 A TW201803869 A TW 201803869A
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- Taiwan
- Prior art keywords
- carbonyl
- bromo
- pyridin
- amine
- trifluoromethyl
- Prior art date
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- XVBMWWFKZCBVPR-UHFFFAOYSA-N 5-(1,3-thiazol-2-yl)pyridin-2-amine Chemical class C1=NC(N)=CC=C1C1=NC=CS1 XVBMWWFKZCBVPR-UHFFFAOYSA-N 0.000 title 1
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 16
- 201000006417 multiple sclerosis Diseases 0.000 claims description 370
- 239000000203 mixture Substances 0.000 claims description 131
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 238000006467 substitution reaction Methods 0.000 claims description 50
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- 150000003839 salts Chemical class 0.000 claims description 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- 239000003814 drug Substances 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 25
- 125000001153 fluoro group Chemical group F* 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 108091008778 RORγ2 Proteins 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 85
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
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- JISGUPQXTPAKHP-VIFPVBQESA-N N-(2-hydroxy-2-methylpropyl)-4-[(2S)-2-methylpyrrolidine-1-carbonyl]-1,3-thiazole-2-carboxamide Chemical class OC(CNC(=O)C=1SC=C(N=1)C(=O)N1[C@H](CCC1)C)(C)C JISGUPQXTPAKHP-VIFPVBQESA-N 0.000 description 19
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- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
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