NO325241B1 - Pyrimidinderivat, fremgangsmate for fremstilling og anvendelse derav, samt farmasoytisk sammensetning - Google Patents

Info

Publication number

NO325241B1

NO325241B1 NO20024154A NO20024154A NO325241B1 NO 325241 B1 NO325241 B1 NO 325241B1 NO 20024154 A NO20024154 A NO 20024154A NO 20024154 A NO20024154 A NO 20024154A NO 325241 B1 NO325241 B1 NO 325241B1

Authority

NO

Norway

Prior art keywords

formula

pharmaceutically acceptable

4alkyl

alkyl

acceptable salt

Prior art date

2000-03-01

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• 238000000034 method Methods 0.000 title claims abstract description 66
• 150000003230 pyrimidines Chemical class 0.000 title claims abstract description 44
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
• 230000008569 process Effects 0.000 title claims abstract description 5
• 238000002360 preparation method Methods 0.000 title claims description 8
• -1 sulphamoyl Chemical group 0.000 claims abstract description 107
• 150000003839 salts Chemical class 0.000 claims abstract description 43
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 42
• 125000001424 substituent group Chemical group 0.000 claims abstract description 26
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 25
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 20
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 18
• 238000004519 manufacturing process Methods 0.000 claims abstract description 9
• 150000001875 compounds Chemical class 0.000 claims description 78
• 238000006243 chemical reaction Methods 0.000 claims description 26
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 23
• 150000002367 halogens Chemical class 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 23
• 238000011282 treatment Methods 0.000 claims description 20
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• 230000000694 effects Effects 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 150000001412 amines Chemical class 0.000 claims description 13
• 230000022131 cell cycle Effects 0.000 claims description 13
• 230000002401 inhibitory effect Effects 0.000 claims description 13
• 241001465754 Metazoa Species 0.000 claims description 11
• 125000006239 protecting group Chemical group 0.000 claims description 11
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 9
• 241000282414 Homo sapiens Species 0.000 claims description 8
• 239000001257 hydrogen Substances 0.000 claims description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 230000001093 anti-cancer Effects 0.000 claims description 6
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• 230000001225 therapeutic effect Effects 0.000 claims description 5
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• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
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• 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
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• 230000000069 prophylactic effect Effects 0.000 claims description 3
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• 150000002431 hydrogen Chemical class 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
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• LMSIABUZAAAUME-UHFFFAOYSA-N 4-[[5-bromo-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC1=NC=C(Br)C(NC=2C=CC(=CC=2)S(N)(=O)=O)=N1 LMSIABUZAAAUME-UHFFFAOYSA-N 0.000 claims 1
• HYZQKSBAKZLJFT-UHFFFAOYSA-N 4-[[5-chloro-4-(4-methoxyphenoxy)pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1OC1=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=C1Cl HYZQKSBAKZLJFT-UHFFFAOYSA-N 0.000 claims 1
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• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
• YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 14
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• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
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