JP2007500237A5

JP2007500237A5 -

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Publication number: JP2007500237A5
Authority: JP; Japan
Prior art keywords: substituted; compound; aryl; alkyl; hydrogen
Prior art date: 2004-05-27
Legal status : Pending

Application number

JP2006533499A

Other languages

English (en)

Japanese (ja)

Other versions

JP2007500237A (ja

Filing date

2004-05-27

Publication date

2007-08-23

2004-05-27 Application filed filed Critical

2004-05-27 Priority claimed from PCT/US2004/016954 external-priority patent/WO2004111058A1/en

2007-01-11 Publication of JP2007500237A publication Critical patent/JP2007500237A/ja

2007-08-23 Publication of JP2007500237A5 publication Critical patent/JP2007500237A5/ja

Status Pending legal-status Critical Current

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150000001875 compounds Chemical class 0.000 claims description 142
125000000217 alkyl group Chemical group 0.000 claims description 128
-1 aminocarboxy, aminocarbonyl Chemical group 0.000 claims description 127
125000003118 aryl group Chemical group 0.000 claims description 98
229910052739 hydrogen Inorganic materials 0.000 claims description 92
239000001257 hydrogen Substances 0.000 claims description 92
125000001072 heteroaryl group Chemical group 0.000 claims description 89
125000000623 heterocyclic group Chemical group 0.000 claims description 80
125000003342 alkenyl group Chemical group 0.000 claims description 64
125000000304 alkynyl group Chemical group 0.000 claims description 61
150000002431 hydrogen Chemical class 0.000 claims description 53
239000000203 mixture Substances 0.000 claims description 41
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 37
206010028980 Neoplasm Diseases 0.000 claims description 36
125000003710 aryl alkyl group Chemical group 0.000 claims description 32
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 31
229910052717 sulfur Inorganic materials 0.000 claims description 31
201000011510 cancer Diseases 0.000 claims description 30
229910052760 oxygen Inorganic materials 0.000 claims description 30
125000003545 alkoxy group Chemical group 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 24
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
238000011282 treatment Methods 0.000 claims description 22
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
125000003282 alkyl amino group Chemical group 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 21
125000004093 cyano group Chemical group *C#N 0.000 claims description 20
229940002612 prodrug Drugs 0.000 claims description 20
239000000651 prodrug Substances 0.000 claims description 20
125000004663 dialkyl amino group Chemical group 0.000 claims description 19
125000005157 alkyl carboxy group Chemical group 0.000 claims description 18
125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 18
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 18
125000004103 aminoalkyl group Chemical group 0.000 claims description 17
239000003795 chemical substances by application Substances 0.000 claims description 17
230000002062 proliferating effect Effects 0.000 claims description 16
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 16
241001465754 Metazoa Species 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 15
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
239000003814 drug Substances 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 14
125000004076 pyridyl group Chemical group 0.000 claims description 14
230000000694 effects Effects 0.000 claims description 13
125000001309 chloro group Chemical group Cl* 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
125000004438 haloalkoxy group Chemical group 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
125000004043 oxo group Chemical group O=* 0.000 claims description 11
125000004414 alkyl thio group Chemical group 0.000 claims description 10
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 10
230000002401 inhibitory effect Effects 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
229920006395 saturated elastomer Polymers 0.000 claims description 10
SPFPGSYLNIIQMG-UHFFFAOYSA-N (carboxyamino)carbamic acid Chemical compound OC(=O)NNC(O)=O SPFPGSYLNIIQMG-UHFFFAOYSA-N 0.000 claims description 9
239000005517 L01XE01 - Imatinib Substances 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims description 9
125000001246 bromo group Chemical group Br* 0.000 claims description 8
125000003373 pyrazinyl group Chemical group 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000000547 substituted alkyl group Chemical group 0.000 claims description 7
125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 6
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 6
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 6
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 6
125000002883 imidazolyl group Chemical group 0.000 claims description 6
UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
125000000335 thiazolyl group Chemical group 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 5
229940080856 gleevec Drugs 0.000 claims description 5
125000004193 piperazinyl group Chemical group 0.000 claims description 5
229940122803 Vinca alkaloid Drugs 0.000 claims description 4
125000002393 azetidinyl group Chemical group 0.000 claims description 4
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 4
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229960002411 imatinib Drugs 0.000 claims description 4
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238000004519 manufacturing process Methods 0.000 claims description 4
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229960000575 trastuzumab Drugs 0.000 claims description 4
VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 claims description 3
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 3
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 3
ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound 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 3
229940123237 Taxane Drugs 0.000 claims description 3
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235000008191 folinic acid Nutrition 0.000 claims description 3
239000011672 folinic acid Substances 0.000 claims description 3
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229960001691 leucovorin Drugs 0.000 claims description 3
UXJYIAKGHWMLGA-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-6-bromo-4-oxothieno[3,2-d]pyrimidin-2-yl)-2-(dimethylamino)-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C=2C=C(Br)SC=2C(=O)N(CC=2C=CC=CC=2)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 UXJYIAKGHWMLGA-UHFFFAOYSA-N 0.000 claims description 3
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
125000002098 pyridazinyl group Chemical group 0.000 claims description 3
229950006410 tezacitabine Drugs 0.000 claims description 3
GFFXZLZWLOBBLO-ASKVSEFXSA-N tezacitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 GFFXZLZWLOBBLO-ASKVSEFXSA-N 0.000 claims description 3
UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims description 3
229960000303 topotecan Drugs 0.000 claims description 3
125000001425 triazolyl group Chemical group 0.000 claims description 3
229930012538 Paclitaxel Natural products 0.000 claims description 2
229940045799 anthracyclines and related substance Drugs 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
229960001592 paclitaxel Drugs 0.000 claims description 2
DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims description 2
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 2
VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims 2
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BNSWQYSYARAGPL-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-6-bromo-4-oxothieno[3,2-d]pyrimidin-2-yl)-2-(dimethylamino)-2-oxoethyl]-6-methylpyridine-3-carboxamide Chemical compound N=1C=2C=C(Br)SC=2C(=O)N(CC=2C=CC=CC=2)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(C)N=C1 BNSWQYSYARAGPL-UHFFFAOYSA-N 0.000 claims 1
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ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
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JP2006533499A 2003-05-30 2004-05-27 抗癌剤としてのヘテロアリール縮合ピリミジニル化合物 Pending JP2007500237A (ja)