PT2958888T - Compostos bicíclicos - Google Patents

Info

Publication number

PT2958888T

PT2958888T PT147098222T PT14709822T PT2958888T PT 2958888 T PT2958888 T PT 2958888T PT 147098222 T PT147098222 T PT 147098222T PT 14709822 T PT14709822 T PT 14709822T PT 2958888 T PT2958888 T PT 2958888T

Authority

PT

Portugal

Prior art keywords

compound

salt

mmol

compounds

formula

Prior art date

2013-02-21

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• 125000002619 bicyclic group Chemical group 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims description 246
• 150000003839 salts Chemical class 0.000 claims description 135
• 239000007787 solid Substances 0.000 claims description 56
• 230000000694 effects Effects 0.000 claims description 33
• 238000011282 treatment Methods 0.000 claims description 31
• 239000008194 pharmaceutical composition Substances 0.000 claims description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
• 239000003937 drug carrier Substances 0.000 claims description 19
• 208000023275 Autoimmune disease Diseases 0.000 claims description 18
• 201000010099 disease Diseases 0.000 claims description 18
• 201000006417 multiple sclerosis Diseases 0.000 claims description 14
• 206010025135 lupus erythematosus Diseases 0.000 claims description 13
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 11
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
• 238000002560 therapeutic procedure Methods 0.000 claims description 8
• 208000035475 disorder Diseases 0.000 claims description 4
• 208000037976 chronic inflammation Diseases 0.000 claims description 3
• 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 3
• 108091006027 G proteins Proteins 0.000 claims description 2
• 102000030782 GTP binding Human genes 0.000 claims description 2
• 108091000058 GTP-Binding Proteins 0.000 claims description 2
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 187
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 159
• 235000002639 sodium chloride Nutrition 0.000 description 134
• 239000000203 mixture Substances 0.000 description 95
• 239000000243 solution Substances 0.000 description 94
• -1 EDG-5 Proteins 0.000 description 85
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• 229910001868 water Inorganic materials 0.000 description 73
• 238000000634 powder X-ray diffraction Methods 0.000 description 61
• 235000019439 ethyl acetate Nutrition 0.000 description 60
• 210000004027 cell Anatomy 0.000 description 57
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 55
• 239000000543 intermediate Substances 0.000 description 47
• 150000003840 hydrochlorides Chemical class 0.000 description 42
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
• 239000011541 reaction mixture Substances 0.000 description 35
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
• 239000002253 acid Substances 0.000 description 30
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
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• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical class OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 24
• 238000005481 NMR spectroscopy Methods 0.000 description 23
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical class OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 22
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• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
• 238000006243 chemical reaction Methods 0.000 description 20
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• 235000021317 phosphate Nutrition 0.000 description 20
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• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
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• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
• 238000003556 assay Methods 0.000 description 16
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 15
• 239000007788 liquid Substances 0.000 description 15
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• PDBXHPORMXSXKO-UHFFFAOYSA-N 8-benzyl-7-[2-[ethyl(2-hydroxyethyl)amino]ethyl]-1,3-dimethylpurine-2,6-dione;hydron;chloride Chemical class Cl.N=1C=2N(C)C(=O)N(C)C(=O)C=2N(CCN(CCO)CC)C=1CC1=CC=CC=C1 PDBXHPORMXSXKO-UHFFFAOYSA-N 0.000 description 14
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• 239000003981 vehicle Substances 0.000 description 14
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
• 150000003016 phosphoric acids Chemical class 0.000 description 13
• 230000009467 reduction Effects 0.000 description 13
• 229920006395 saturated elastomer Polymers 0.000 description 13
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• 102000005962 receptors Human genes 0.000 description 12
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• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
• 238000002347 injection Methods 0.000 description 11
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• 238000010828 elution Methods 0.000 description 10
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• 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
• 235000019341 magnesium sulphate Nutrition 0.000 description 10
• 239000003826 tablet Substances 0.000 description 10
• 210000001519 tissue Anatomy 0.000 description 10
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 9
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 9
• 239000013058 crude material Substances 0.000 description 9
• 229940116298 l- malic acid Drugs 0.000 description 9
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• 235000011090 malic acid Nutrition 0.000 description 9
• 239000000463 material Substances 0.000 description 9
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
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• DUYSYHSSBDVJSM-KRWOKUGFSA-N sphingosine 1-phosphate Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O DUYSYHSSBDVJSM-KRWOKUGFSA-N 0.000 description 8
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• BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 6
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• YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 5
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