NZ523565A - Novel compounds and methods - Google Patents

Info

Publication number

NZ523565A

NZ523565A NZ523565A NZ52356501A NZ523565A NZ 523565 A NZ523565 A NZ 523565A NZ 523565 A NZ523565 A NZ 523565A NZ 52356501 A NZ52356501 A NZ 52356501A NZ 523565 A NZ523565 A NZ 523565A

Authority

NZ

New Zealand

Prior art keywords

alkyl

tetrahydro

group

aryl

pyran

Prior art date

2000-07-11

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims description 109
• 238000000034 method Methods 0.000 title description 48
• 210000001744 T-lymphocyte Anatomy 0.000 claims abstract description 70
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 47
• 201000010099 disease Diseases 0.000 claims abstract description 44
• 230000005012 migration Effects 0.000 claims abstract description 38
• 238000013508 migration Methods 0.000 claims abstract description 38
• 239000003814 drug Substances 0.000 claims abstract description 12
• 238000004519 manufacturing process Methods 0.000 claims abstract description 4
• -1 OPO3H2 Chemical group 0.000 claims description 119
• 239000000203 mixture Substances 0.000 claims description 106
• 210000004027 cell Anatomy 0.000 claims description 87
• 125000000217 alkyl group Chemical group 0.000 claims description 76
• 125000003118 aryl group Chemical group 0.000 claims description 47
• 125000003342 alkenyl group Chemical group 0.000 claims description 33
• 125000000304 alkynyl group Chemical group 0.000 claims description 31
• 125000001072 heteroaryl group Chemical group 0.000 claims description 30
• 125000002252 acyl group Chemical group 0.000 claims description 29
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 150000003839 salts Chemical class 0.000 claims description 22
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 230000001404 mediated effect Effects 0.000 claims description 18
• 150000001720 carbohydrates Chemical class 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 239000000651 prodrug Substances 0.000 claims description 9
• 229940002612 prodrug Drugs 0.000 claims description 9
• 201000006417 multiple sclerosis Diseases 0.000 claims description 8
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 208000027866 inflammatory disease Diseases 0.000 claims description 7
• 201000004681 Psoriasis Diseases 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 5
• JIQNWFBLYKVZFY-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=C[C]=CC=C1 JIQNWFBLYKVZFY-UHFFFAOYSA-N 0.000 claims description 5
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 208000002552 acute disseminated encephalomyelitis Diseases 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 3
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 3
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
• 208000011231 Crohn disease Diseases 0.000 claims description 2
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• 206010046851 Uveitis Diseases 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 208000001050 sialadenitis Diseases 0.000 claims description 2
• 208000025889 stromal keratitis Diseases 0.000 claims description 2
• 206010043778 thyroiditis Diseases 0.000 claims description 2
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
• 239000003937 drug carrier Substances 0.000 claims 1
• HOGAGKVTOGTBKP-UHFFFAOYSA-N O=P(=O)C1CCCCO1 Chemical class O=P(=O)C1CCCCO1 HOGAGKVTOGTBKP-UHFFFAOYSA-N 0.000 abstract description 9
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 357
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 226
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 171
• 235000019439 ethyl acetate Nutrition 0.000 description 122
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 121
• 229940093499 ethyl acetate Drugs 0.000 description 112
• 239000003208 petroleum Substances 0.000 description 112
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 107
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 88
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 84
• 239000000243 solution Substances 0.000 description 77
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• 230000002829 reductive effect Effects 0.000 description 69
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• 229910002027 silica gel Inorganic materials 0.000 description 56
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• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 51
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
• 241001465754 Metazoa Species 0.000 description 43
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
• 239000002904 solvent Substances 0.000 description 40
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 39
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
• 150000002148 esters Chemical class 0.000 description 38
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 35
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
• 238000003756 stirring Methods 0.000 description 31
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• 241000700159 Rattus Species 0.000 description 30
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
• 229910052938 sodium sulfate Inorganic materials 0.000 description 30
• 235000011152 sodium sulphate Nutrition 0.000 description 30
• 239000011541 reaction mixture Substances 0.000 description 29
• 210000001519 tissue Anatomy 0.000 description 29
• 210000004698 lymphocyte Anatomy 0.000 description 28
• 239000000463 material Substances 0.000 description 28
• 238000002474 experimental method Methods 0.000 description 27
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 26
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
• 238000002360 preparation method Methods 0.000 description 24
• 239000003795 chemical substances by application Substances 0.000 description 23
• 239000000706 filtrate Substances 0.000 description 22
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• 102000036639 antigens Human genes 0.000 description 21
• 229910052757 nitrogen Inorganic materials 0.000 description 21
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
• 230000000694 effects Effects 0.000 description 19
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 19
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• 239000012298 atmosphere Substances 0.000 description 16
• 238000011694 lewis rat Methods 0.000 description 16
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• 241000282414 Homo sapiens Species 0.000 description 15
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• KISWVXRQTGLFGD-UHFFFAOYSA-N 2-[[2-[[6-amino-2-[[2-[[2-[[5-amino-2-[[2-[[1-[2-[[6-amino-2-[(2,5-diamino-5-oxopentanoyl)amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-(diaminomethylideneamino)p Chemical compound C1CCN(C(=O)C(CCCN=C(N)N)NC(=O)C(CCCCN)NC(=O)C(N)CCC(N)=O)C1C(=O)NC(CO)C(=O)NC(CCC(N)=O)C(=O)NC(CCCN=C(N)N)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(C(=O)NC(CC(C)C)C(O)=O)CC1=CC=C(O)C=C1 KISWVXRQTGLFGD-UHFFFAOYSA-N 0.000 description 13
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• 159000000000 sodium salts Chemical class 0.000 description 12
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