NO330043B1 - Heterocykliske forbindelser, farmasoytiske preparater innholdende slike samt anvendelse av slike for fremstilling av farmasoytisk preparat for behandling av sykdom - Google Patents

Info

Publication number

NO330043B1

NO330043B1 NO20045220A NO20045220A NO330043B1 NO 330043 B1 NO330043 B1 NO 330043B1 NO 20045220 A NO20045220 A NO 20045220A NO 20045220 A NO20045220 A NO 20045220A NO 330043 B1 NO330043 B1 NO 330043B1

Authority

NO

Norway

Prior art keywords

substituted

amino

ylamino

thiazol

pyridin

Prior art date

2002-06-20

Links

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• 238000011282 treatment Methods 0.000 title claims abstract description 23
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 14
• 201000010099 disease Diseases 0.000 title claims abstract description 13
• 239000000825 pharmaceutical preparation Substances 0.000 title claims description 17
• 238000002360 preparation method Methods 0.000 title description 32
• 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
• 239000008194 pharmaceutical composition Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 115
• 230000000694 effects Effects 0.000 claims abstract description 19
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims abstract description 15
• 150000003839 salts Chemical class 0.000 claims abstract description 15
• 239000002246 antineoplastic agent Substances 0.000 claims abstract description 8
• 102000009465 Growth Factor Receptors Human genes 0.000 claims abstract description 7
• 108010009202 Growth Factor Receptors Proteins 0.000 claims abstract description 7
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 7
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 7
• 125000003118 aryl group Chemical group 0.000 claims description 36
• 125000000217 alkyl group Chemical group 0.000 claims description 32
• -1 nitro, cyano, carboxy, carbamyl Chemical group 0.000 claims description 32
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 26
• 206010028980 Neoplasm Diseases 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 22
• 125000000623 heterocyclic group Chemical group 0.000 claims description 22
• 125000001424 substituent group Chemical group 0.000 claims description 22
• 125000003545 alkoxy group Chemical group 0.000 claims description 14
• 239000003112 inhibitor Substances 0.000 claims description 13
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
• 125000003107 substituted aryl group Chemical group 0.000 claims description 13
• 201000011510 cancer Diseases 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 11
• 239000000460 chlorine Substances 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 11
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 11
• 125000002619 bicyclic group Chemical group 0.000 claims description 9
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 125000004122 cyclic group Chemical group 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 125000004423 acyloxy group Chemical group 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 8
• 125000001589 carboacyl group Chemical group 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 239000003102 growth factor Substances 0.000 claims description 7
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
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• 241000124008 Mammalia Species 0.000 claims description 6
• NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims description 6
• NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 6
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• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 150000001412 amines Chemical class 0.000 claims description 6
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 6
• 125000001769 aryl amino group Chemical group 0.000 claims description 6
• 125000004104 aryloxy group Chemical group 0.000 claims description 6
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• 229940127089 cytotoxic agent Drugs 0.000 claims description 6
• 231100000599 cytotoxic agent Toxicity 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 229920006395 saturated elastomer Polymers 0.000 claims description 6
• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical class O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 5
• GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 claims description 5
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
• 239000001257 hydrogen Substances 0.000 claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 5
• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 230000002062 proliferating effect Effects 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 102000001253 Protein Kinase Human genes 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 4
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
• 230000002401 inhibitory effect Effects 0.000 claims description 4
• 108060006633 protein kinase Proteins 0.000 claims description 4
• LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 claims description 3
• JIMHRVUJVAYWAR-UHFFFAOYSA-N 2,4-difluoro-n-methyl-5-[[2-(pyridin-2-ylamino)-1,3-thiazol-5-yl]methylamino]benzamide Chemical compound C1=C(F)C(C(=O)NC)=CC(NCC=2SC(NC=3N=CC=CC=3)=NC=2)=C1F JIMHRVUJVAYWAR-UHFFFAOYSA-N 0.000 claims description 3
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• STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims description 3
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• BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 claims description 3
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