OA11504A - Isothiazole derivatives useful as anticancer agents. - Google Patents

Info

Publication number

OA11504A

OA11504A OA1200000289A OA1200000289A OA11504A OA 11504 A OA11504 A OA 11504A OA 1200000289 A OA1200000289 A OA 1200000289A OA 1200000289 A OA1200000289 A OA 1200000289A OA 11504 A OA11504 A OA 11504A

Authority

OA

OAPI

Prior art keywords

ureido

isothiazole

acid amide

carboxylic acid

benzyloxy

Prior art date

1998-06-04

Links

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• 239000002246 antineoplastic agent Substances 0.000 title claims description 4
• 150000003854 isothiazoles Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 229
• 238000000034 method Methods 0.000 claims abstract description 89
• 150000003839 salts Chemical class 0.000 claims abstract description 27
• 241000124008 Mammalia Species 0.000 claims abstract description 19
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 12
• 229940002612 prodrug Drugs 0.000 claims abstract description 11
• 239000000651 prodrug Substances 0.000 claims abstract description 11
• 150000001408 amides Chemical class 0.000 claims description 135
• BEPMYBTTZSNHPS-UHFFFAOYSA-N 1,2-thiazole-4-carboxamide Chemical compound NC(=O)C=1C=NSC=1 BEPMYBTTZSNHPS-UHFFFAOYSA-N 0.000 claims description 60
• -1 dimethylamino, hydroxy Chemical group 0.000 claims description 57
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 55
• 125000000623 heterocyclic group Chemical group 0.000 claims description 52
• 125000003118 aryl group Chemical group 0.000 claims description 41
• 206010028980 Neoplasm Diseases 0.000 claims description 33
• 125000000217 alkyl group Chemical group 0.000 claims description 32
• 229910052799 carbon Inorganic materials 0.000 claims description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
• 229910052760 oxygen Inorganic materials 0.000 claims description 23
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 22
• 125000004434 sulfur atom Chemical group 0.000 claims description 21
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
• 201000011510 cancer Diseases 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 17
• 208000035475 disorder Diseases 0.000 claims description 16
• 229910052717 sulfur Inorganic materials 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 125000004122 cyclic group Chemical group 0.000 claims description 13
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
• 210000002307 prostate Anatomy 0.000 claims description 10
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 229920006395 saturated elastomer Polymers 0.000 claims description 9
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 210000000481 breast Anatomy 0.000 claims description 8
• 210000004072 lung Anatomy 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 239000004202 carbamide Substances 0.000 claims description 7
• 239000003112 inhibitor Substances 0.000 claims description 7
• 230000002611 ovarian Effects 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 6
• 125000001072 heteroaryl group Chemical group 0.000 claims description 6
• DYTGJDKRYVLILD-UHFFFAOYSA-N 3-[(2,6-difluoro-4-methylphenyl)methoxy]-5-(4-pyrrolidin-1-ylbutylcarbamoylamino)-1,2-thiazole-4-carboxamide Chemical compound FC1=CC(C)=CC(F)=C1COC1=NSC(NC(=O)NCCCCN2CCCC2)=C1C(N)=O DYTGJDKRYVLILD-UHFFFAOYSA-N 0.000 claims description 5
• GVJSWBMFVKGXAE-UHFFFAOYSA-N 3-[(2,6-difluoro-4-methylphenyl)methoxy]-5-[3-(dimethylamino)propylcarbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound NC(=O)C1=C(NC(=O)NCCCN(C)C)SN=C1OCC1=C(F)C=C(C)C=C1F GVJSWBMFVKGXAE-UHFFFAOYSA-N 0.000 claims description 5
• HFCXEWPMPAOGBM-UHFFFAOYSA-N 3-[(2-fluoro-4-methylphenyl)methoxy]-5-[3-(4-methylpiperazin-1-yl)propylcarbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound C1CN(C)CCN1CCCNC(=O)NC1=C(C(N)=O)C(OCC=2C(=CC(C)=CC=2)F)=NS1 HFCXEWPMPAOGBM-UHFFFAOYSA-N 0.000 claims description 5
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 102000004190 Enzymes Human genes 0.000 claims description 5
• 108090000790 Enzymes Proteins 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 210000004556 brain Anatomy 0.000 claims description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 230000002496 gastric effect Effects 0.000 claims description 5
• 239000003102 growth factor Substances 0.000 claims description 5
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• AMLIAESKGXHWSE-UHFFFAOYSA-N 3-[(2-fluoro-4-methylphenyl)methoxy]-5-[5-(propan-2-ylamino)pentylcarbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound NC(=O)C1=C(NC(=O)NCCCCCNC(C)C)SN=C1OCC1=CC=C(C)C=C1F AMLIAESKGXHWSE-UHFFFAOYSA-N 0.000 claims description 4
• HCYLBNPHRUPOIC-UHFFFAOYSA-N 3-[(4-bromo-2,3,6-trifluorophenyl)methoxy]-5-(4-pyrrolidin-1-ylbutylcarbamoylamino)-1,2-thiazole-4-carboxamide Chemical compound S1N=C(OCC=2C(=C(F)C(Br)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCCCN1CCCC1 HCYLBNPHRUPOIC-UHFFFAOYSA-N 0.000 claims description 4
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 230000000340 anti-metabolite Effects 0.000 claims description 4
• 229940100197 antimetabolite Drugs 0.000 claims description 4
• 239000002256 antimetabolite Substances 0.000 claims description 4
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000001153 fluoro group Chemical group F* 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• QIMZMNAVSSZUFG-UHFFFAOYSA-N 3-[(2,5-difluoro-4-methylphenyl)methoxy]-5-[6-(dimethylamino)hexylcarbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound NC(=O)C1=C(NC(=O)NCCCCCCN(C)C)SN=C1OCC1=CC(F)=C(C)C=C1F QIMZMNAVSSZUFG-UHFFFAOYSA-N 0.000 claims description 3
• KOZFIMSVPMYVSF-UHFFFAOYSA-N 3-[(2,6-difluoro-4-methylphenyl)methoxy]-5-[4-(dimethylamino)butylcarbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound NC(=O)C1=C(NC(=O)NCCCCN(C)C)SN=C1OCC1=C(F)C=C(C)C=C1F KOZFIMSVPMYVSF-UHFFFAOYSA-N 0.000 claims description 3
• HXHAJRMTJXHJJZ-UHFFFAOYSA-N 3-[(4-bromo-2,6-difluorophenyl)methoxy]-5-(4-pyrrolidin-1-ylbutylcarbamoylamino)-1,2-thiazole-4-carboxamide Chemical compound S1N=C(OCC=2C(=CC(Br)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCCCN1CCCC1 HXHAJRMTJXHJJZ-UHFFFAOYSA-N 0.000 claims description 3
• AHTAYKWZFAVPQM-UHFFFAOYSA-N 5-(3-pyrrolidin-1-ylpropylcarbamoylamino)-3-[(2,3,6-trifluoro-4-methylphenyl)methoxy]-1,2-thiazole-4-carboxamide Chemical compound FC1=C(F)C(C)=CC(F)=C1COC1=NSC(NC(=O)NCCCN2CCCC2)=C1C(N)=O AHTAYKWZFAVPQM-UHFFFAOYSA-N 0.000 claims description 3
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
• 229940123587 Cell cycle inhibitor Drugs 0.000 claims description 3
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
• 239000002168 alkylating agent Substances 0.000 claims description 3
• 229940100198 alkylating agent Drugs 0.000 claims description 3
• 230000003388 anti-hormonal effect Effects 0.000 claims description 3
• 206010020718 hyperplasia Diseases 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 230000000394 mitotic effect Effects 0.000 claims description 3
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 201000002510 thyroid cancer Diseases 0.000 claims description 3
• QYQQDBQNTUOFJL-UHFFFAOYSA-N 3-[(2,6-difluoro-4-methylphenyl)methoxy]-5-(3-pyrrolidin-1-ylpropylcarbamoylamino)-1,2-thiazole-4-carboxamide Chemical compound FC1=CC(C)=CC(F)=C1COC1=NSC(NC(=O)NCCCN2CCCC2)=C1C(N)=O QYQQDBQNTUOFJL-UHFFFAOYSA-N 0.000 claims description 2
• FLIJOUHDTCIKLC-UHFFFAOYSA-N 3-ethoxy-5-(methylcarbamoylamino)-1,2-thiazole-4-carboxamide Chemical compound CCOC1=NSC(NC(=O)NC)=C1C(N)=O FLIJOUHDTCIKLC-UHFFFAOYSA-N 0.000 claims description 2
• PNLQTLDEFBVYHM-UHFFFAOYSA-N 5-(4-pyrrolidin-1-ylbutylcarbamoylamino)-3-[(2,3,6-trifluoro-4-methylphenyl)methoxy]-1,2-thiazole-4-carboxamide Chemical compound FC1=C(F)C(C)=CC(F)=C1COC1=NSC(NC(=O)NCCCCN2CCCC2)=C1C(N)=O PNLQTLDEFBVYHM-UHFFFAOYSA-N 0.000 claims description 2
• XTOWBIWKPBDEQA-UHFFFAOYSA-N 5-(carbamoylamino)-3-ethylsulfanyl-1,2-thiazole-4-carboxamide Chemical compound C(N)(=O)C=1C(=NSC=1NC(N)=O)SCC XTOWBIWKPBDEQA-UHFFFAOYSA-N 0.000 claims description 2
• FDCBCMKGFSDXHM-UHFFFAOYSA-N 5-(dimethylcarbamoylamino)-3-ethoxy-1,2-thiazole-4-carboxamide Chemical compound CCOC1=NSC(NC(=O)N(C)C)=C1C(N)=O FDCBCMKGFSDXHM-UHFFFAOYSA-N 0.000 claims description 2
• MUMZOQWBQONBKS-UHFFFAOYSA-N 5-(methylcarbamoylamino)-3-propylsulfanyl-1,2-thiazole-4-carboxamide Chemical compound CCCSC1=NSC(NC(=O)NC)=C1C(N)=O MUMZOQWBQONBKS-UHFFFAOYSA-N 0.000 claims description 2
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 2
• 239000003534 dna topoisomerase inhibitor Substances 0.000 claims description 2
• 229940088598 enzyme Drugs 0.000 claims description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
• 239000000367 immunologic factor Substances 0.000 claims description 2
• 125000002950 monocyclic group Chemical group 0.000 claims description 2
• 125000003386 piperidinyl group Chemical group 0.000 claims description 2
• 125000003367 polycyclic group Chemical group 0.000 claims description 2
• UXAWXZDXVOYLII-UHFFFAOYSA-N tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C1C2N(C(=O)OC(C)(C)C)CC1NC2 UXAWXZDXVOYLII-UHFFFAOYSA-N 0.000 claims description 2
• 229940044693 topoisomerase inhibitor Drugs 0.000 claims description 2
• SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 3
• 229910006069 SO3H Inorganic materials 0.000 claims 2
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• NYYQETQHPXRWLV-UHFFFAOYSA-N 3-[(4-chloro-2,6-difluorophenyl)methoxy]-5-[2-(1-methylpyrrolidin-2-yl)ethylcarbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound CN1CCCC1CCNC(=O)NC1=C(C(N)=O)C(OCC=2C(=CC(Cl)=CC=2F)F)=NS1 NYYQETQHPXRWLV-UHFFFAOYSA-N 0.000 claims 1
• ZHELHOUQIKLLQE-UHFFFAOYSA-N 3-[(4-chloro-2,6-difluorophenyl)methoxy]-5-[4-(3,4-dihydroxypyrrolidin-1-yl)butylcarbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound S1N=C(OCC=2C(=CC(Cl)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCCCN1CC(O)C(O)C1 ZHELHOUQIKLLQE-UHFFFAOYSA-N 0.000 claims 1
• OXBJJTHWZCVWHV-UHFFFAOYSA-N 5-(methylcarbamoylamino)-3-propoxy-1,2-thiazole-4-carboxamide Chemical compound CCCOC1=NSC(NC(=O)NC)=C1C(N)=O OXBJJTHWZCVWHV-UHFFFAOYSA-N 0.000 claims 1
• 102000035037 5-HT3 receptors Human genes 0.000 claims 1
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• NYNDSKDUQMPEHX-UHFFFAOYSA-N 5-[4-(dimethylamino)butylcarbamoylamino]-3-[(2,3,6-trifluoro-4-methylphenyl)methoxy]-1,2-thiazole-4-carboxamide Chemical compound NC(=O)C1=C(NC(=O)NCCCCN(C)C)SN=C1OCC1=C(F)C=C(C)C(F)=C1F NYNDSKDUQMPEHX-UHFFFAOYSA-N 0.000 claims 1
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• 239000003242 anti bacterial agent Substances 0.000 claims 1
• 229940088710 antibiotic agent Drugs 0.000 claims 1
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• 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
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• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
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