NO326831B1 - Pyrimidinderivater samt anvendelse og fremgangsmate for fremstilling derav, og farmasoytisk preparat - Google Patents

Info

Publication number

NO326831B1

NO326831B1 NO20033635A NO20033635A NO326831B1 NO 326831 B1 NO326831 B1 NO 326831B1 NO 20033635 A NO20033635 A NO 20033635A NO 20033635 A NO20033635 A NO 20033635A NO 326831 B1 NO326831 B1 NO 326831B1

Authority

NO

Norway

Prior art keywords

sulfamoyl

formula

compound

pharmaceutically acceptable

acceptable salt

Prior art date

2001-02-17

Links

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• 238000000034 method Methods 0.000 title claims description 127
• 238000002360 preparation method Methods 0.000 title claims description 11
• 230000008569 process Effects 0.000 title claims description 8
• 150000003230 pyrimidines Chemical class 0.000 title description 6
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 3
• 239000008194 pharmaceutical composition Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 206
• -1 C 1-6 alkylS Chemical group 0.000 claims description 112
• 150000003839 salts Chemical class 0.000 claims description 61
• 150000002148 esters Chemical class 0.000 claims description 60
• 238000001727 in vivo Methods 0.000 claims description 59
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 58
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 55
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 47
• 125000000217 alkyl group Chemical group 0.000 claims description 41
• 238000011282 treatment Methods 0.000 claims description 36
• 229910052757 nitrogen Inorganic materials 0.000 claims description 32
• 206010028980 Neoplasm Diseases 0.000 claims description 31
• 241001465754 Metazoa Species 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 27
• 239000001257 hydrogen Substances 0.000 claims description 27
• 238000006243 chemical reaction Methods 0.000 claims description 23
• 230000000694 effects Effects 0.000 claims description 23
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 23
• 230000002401 inhibitory effect Effects 0.000 claims description 20
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 19
• 230000035755 proliferation Effects 0.000 claims description 19
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• 201000011510 cancer Diseases 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 16
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
• 150000002431 hydrogen Chemical group 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
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• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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• 125000004434 sulfur atom Chemical group 0.000 claims description 4
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
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• 150000001412 amines Chemical class 0.000 claims description 3
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• 125000002619 bicyclic group Chemical group 0.000 claims description 3
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• 125000002950 monocyclic group Chemical group 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
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• 208000015634 Rectal Neoplasms Diseases 0.000 claims description 2
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• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
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• 125000003282 alkyl amino group Chemical group 0.000 claims description 2
• 206010017758 gastric cancer Diseases 0.000 claims description 2
• RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 2
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• 210000002784 stomach Anatomy 0.000 claims description 2
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• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• 210000003932 urinary bladder Anatomy 0.000 claims description 2
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
• 210000003905 vulva Anatomy 0.000 claims description 2
• 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims 1
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
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