JP5036002B2 - ２−アミノ−７，８−ジヒドロ−６Ｈ−ピリド［４，３−ｄ］ピリミジン−５−オン - Google Patents
２−アミノ−７，８−ジヒドロ−６Ｈ−ピリド［４，３−ｄ］ピリミジン−５−オン Download PDFInfo
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- JP5036002B2 JP5036002B2 JP2008533697A JP2008533697A JP5036002B2 JP 5036002 B2 JP5036002 B2 JP 5036002B2 JP 2008533697 A JP2008533697 A JP 2008533697A JP 2008533697 A JP2008533697 A JP 2008533697A JP 5036002 B2 JP5036002 B2 JP 5036002B2
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- Prior art keywords
- phenyl
- substituted
- methoxy
- pyridin
- methyl
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- CZOQBGHFZWUWPV-UHFFFAOYSA-N 2-amino-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound O=C1NCCC2=NC(N)=NC=C21 CZOQBGHFZWUWPV-UHFFFAOYSA-N 0.000 title description 17
- -1 C 6 alkyl thiol Chemical class 0.000 claims description 898
- 150000001875 compounds Chemical class 0.000 claims description 182
- 229910052739 hydrogen Inorganic materials 0.000 claims description 92
- 239000001257 hydrogen Substances 0.000 claims description 92
- 125000000217 alkyl group Chemical group 0.000 claims description 90
- 125000003118 aryl group Chemical group 0.000 claims description 72
- 125000001072 heteroaryl group Chemical group 0.000 claims description 65
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 58
- 125000000623 heterocyclic group Chemical group 0.000 claims description 49
- 150000003839 salts Chemical class 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 42
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 41
- 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 claims description 39
- 206010028980 Neoplasm Diseases 0.000 claims description 39
- 125000005843 halogen group Chemical group 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 38
- 150000002431 hydrogen Chemical group 0.000 claims description 36
- 101710113864 Heat shock protein 90 Proteins 0.000 claims description 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 201000011510 cancer Diseases 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 27
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 21
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 19
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 18
- 125000000335 thiazolyl group Chemical group 0.000 claims description 18
- 125000001041 indolyl group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000001544 thienyl group Chemical group 0.000 claims description 17
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 13
- 241001465754 Metazoa Species 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 12
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 11
- 125000002971 oxazolyl group Chemical group 0.000 claims description 11
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 11
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 11
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 125000001425 triazolyl group Chemical group 0.000 claims description 10
- RRXSYZFVDIRTFB-UHFFFAOYSA-N C[CH]C1=CC=C(OC)C=C1 Chemical group C[CH]C1=CC=C(OC)C=C1 RRXSYZFVDIRTFB-UHFFFAOYSA-N 0.000 claims description 9
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 9
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 9
- 150000003573 thiols Chemical class 0.000 claims description 9
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 8
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 8
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 8
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 8
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 8
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 8
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
- 239000005517 L01XE01 - Imatinib Substances 0.000 claims description 8
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 8
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000001475 halogen functional group Chemical group 0.000 claims description 7
- 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 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 6
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 6
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 6
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 229910052727 yttrium Inorganic materials 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 4
- 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 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 3
- 229960002949 fluorouracil Drugs 0.000 claims description 3
- 150000002357 guanidines Chemical class 0.000 claims description 3
- 229960002411 imatinib Drugs 0.000 claims description 3
- 229960004768 irinotecan Drugs 0.000 claims description 3
- 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 2
- MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 claims description 2
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 2
- 239000005411 L01XE02 - Gefitinib Substances 0.000 claims description 2
- 239000002147 L01XE04 - Sunitinib Substances 0.000 claims description 2
- 239000005511 L01XE05 - Sorafenib Substances 0.000 claims description 2
- 229940123237 Taxane Drugs 0.000 claims description 2
- 229940122803 Vinca alkaloid Drugs 0.000 claims description 2
- 229960004562 carboplatin Drugs 0.000 claims description 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 2
- 229960004316 cisplatin Drugs 0.000 claims description 2
- 229960004397 cyclophosphamide Drugs 0.000 claims description 2
- VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 claims description 2
- 235000008191 folinic acid Nutrition 0.000 claims description 2
- 239000011672 folinic acid Substances 0.000 claims description 2
- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 claims description 2
- 229960002584 gefitinib Drugs 0.000 claims description 2
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims description 2
- 229960005277 gemcitabine Drugs 0.000 claims description 2
- 229960001691 leucovorin Drugs 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 229960003787 sorafenib Drugs 0.000 claims description 2
- 229960001796 sunitinib Drugs 0.000 claims description 2
- WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 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
- 229950006410 tezacitabine Drugs 0.000 claims description 2
- 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 2
- 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 2
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- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 claims 1
- 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 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical class [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 34
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 10
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000007447 staining method Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000002198 surface plasmon resonance spectroscopy Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 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 description 1
- 229940063683 taxotere Drugs 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- 230000004222 uncontrolled growth Effects 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (5)
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| US60/722,796 | 2005-09-30 | ||
| US83688606P | 2006-08-09 | 2006-08-09 | |
| US60/836,886 | 2006-08-09 | ||
| PCT/US2006/038181 WO2007041362A1 (en) | 2005-09-30 | 2006-09-28 | 2-amino-7,8-dihydro-6h-pyrido[4,3-d] pyrimidin-5-ones |
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| JP2012119613A Withdrawn JP2012158611A (ja) | 2005-09-30 | 2012-05-25 | ２−アミノ−７，８−ジヒドロ−６Ｈ−ピリド［４，３−ｄ］ピリミジン−５−オン |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2012119613A Withdrawn JP2012158611A (ja) | 2005-09-30 | 2012-05-25 | ２−アミノ−７，８−ジヒドロ−６Ｈ−ピリド［４，３−ｄ］ピリミジン−５−オン |
Country Status (31)
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| JP (2) | JP5036002B2 (enExample) |
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| AU (1) | AU2006297124B2 (enExample) |
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| CA (1) | CA2624253C (enExample) |
| CR (1) | CR9846A (enExample) |
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| EC (1) | ECSP088324A (enExample) |
| GE (1) | GEP20115231B (enExample) |
| HR (1) | HRP20110655T1 (enExample) |
| IL (1) | IL190446A0 (enExample) |
| JO (1) | JO2783B1 (enExample) |
| MA (1) | MA29885B1 (enExample) |
| ME (1) | ME01952B (enExample) |
| MY (1) | MY143604A (enExample) |
| NO (1) | NO342258B1 (enExample) |
| NZ (1) | NZ566914A (enExample) |
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| PL (1) | PL1928875T3 (enExample) |
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| RS (1) | RS51795B (enExample) |
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| TW (1) | TWI373471B (enExample) |
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| CL2007002994A1 (es) * | 2006-10-19 | 2008-02-08 | Wyeth Corp | Compuestos derivados heterociclicos que contienen sulfamoilo, inhibidores de hsp90; composicion farmaceutica; y uso para el tratamiento del cancer, tal como cancer de mama, de colon y prostata, entre otros. |
| CN101225083A (zh) * | 2007-01-16 | 2008-07-23 | 北京摩力克科技有限公司 | 四氢喹唑啉酮类化合物及其用于制备治疗和预防病毒性疾病的药物的用途 |
| GB2449293A (en) * | 2007-05-17 | 2008-11-19 | Evotec | Compounds having Hsp90 inhibitory activity |
| WO2009097578A1 (en) * | 2008-02-01 | 2009-08-06 | Takeda Pharmaceutical Company Limited | Oxim derivatives as hsp90 inhibitors |
| CN102227237A (zh) * | 2008-09-26 | 2011-10-26 | 国家健康与医学研究院 | 作为针对hcv感染的抗病毒治疗的靶标的宿主细胞激酶 |
| RU2532375C2 (ru) * | 2008-11-28 | 2014-11-10 | Новартис Аг | ФАРМАЦЕВТИЧЕСКИЕ КОМБИНАЦИИ, ВКЛЮЧАЮЩИЕ ПРОИЗВОДНЫЕ ПИРИДО [4,3-d]ПИРИМИДИНА В КАЧЕСТВЕ ИНГИБИТОРА HSP90 И ИНГИБИТОРА HER2 |
| BRPI0922301A2 (pt) * | 2008-11-28 | 2019-02-26 | Novartis Ag | combinações de inibidor de hsp90 |
| US20110230499A1 (en) * | 2008-11-28 | 2011-09-22 | Novartis Ag | Hsp90 inhibitors for therapeutic treatment |
| AR075180A1 (es) * | 2009-01-29 | 2011-03-16 | Novartis Ag | Formulaciones orales solidas de una pirido-pirimidinona |
| AR077405A1 (es) | 2009-07-10 | 2011-08-24 | Sanofi Aventis | Derivados del indol inhibidores de hsp90, composiciones que los contienen y utilizacion de los mismos para el tratamiento del cancer |
| FR2949467B1 (fr) | 2009-09-03 | 2011-11-25 | Sanofi Aventis | Nouveaux derives de 5,6,7,8-tetrahydroindolizine inhibiteurs d'hsp90, compositions les contenant et utilisation |
| JP5993742B2 (ja) * | 2009-10-29 | 2016-09-14 | ジェノスコ | キナーゼ阻害剤 |
| WO2012104823A2 (en) | 2011-02-04 | 2012-08-09 | Novartis Ag | Pyridopyrimidinone compounds in the treatment of neurodegenerative diseases |
| RU2017119219A (ru) | 2011-10-14 | 2018-11-02 | Новартис Аг | 2-карбоксамид циклоамино производные мочевины в комбинации с ингибиторами hsp90 для лечения пролиферативных заболеваний |
| ITTO20111013A1 (it) | 2011-11-03 | 2013-05-04 | Dac Srl | Composti farmaceutici |
| CN103664938A (zh) * | 2012-09-12 | 2014-03-26 | 山东亨利医药科技有限责任公司 | 含有嘧啶并环的syk抑制剂 |
| AU2013341271A1 (en) | 2012-11-07 | 2015-05-14 | Novartis Ag | Combination therapy |
| US9677907B2 (en) * | 2013-03-14 | 2017-06-13 | Itron Inc | Intelligent receptacle |
| GB201306610D0 (en) * | 2013-04-11 | 2013-05-29 | Almac Discovery Ltd | Pharmaceutical compounds |
| PL3053578T3 (pl) | 2013-09-30 | 2021-06-14 | Taiho Pharmaceutical Co., Ltd. | Skojarzona terapia przeciwnowotworowa z zastosowaniem związku azabicyklicznego |
| BR112017003651A2 (pt) * | 2014-09-02 | 2017-12-05 | Pf Medicament | derivados de isoquinolinona úteis no tratamento de câncer |
| KR20160035411A (ko) * | 2014-09-23 | 2016-03-31 | 주식회사 오스코텍 | LRRK2 (Leucine Rich Repeat Kinase 2) 키나제 억제제로서의 피리도피리미딘 유도체 화합물 |
| KR101653560B1 (ko) * | 2016-02-02 | 2016-09-12 | 한국화학연구원 | 신규한 화합물 또는 이의 약학적으로 허용가능한 염, 및 이를 유효성분으로 함유하는 인플루엔자 바이러스 감염으로 인한 질환의 예방 또는 치료용 약학적 조성물 |
| RU2629599C1 (ru) * | 2016-09-28 | 2017-08-30 | Государственное бюджетное учреждение здравоохранения Московской области "Московский областной научно-исследовательский клинический институт им. М.Ф. Владимирского" (ГБУЗ МО МОНИКИ им. М.Ф. Владимирского) | Способ химиолучевого лечения опухолей прямой кишки и анального канала |
| EP3636656A4 (en) | 2017-06-09 | 2021-04-14 | Chugai Seiyaku Kabushiki Kaisha | METHOD OF SYNTHESIS OF PEPTIDE WITH N-SUBSTITUTED AMINO ACID |
| CN115916752B (zh) * | 2020-06-26 | 2025-05-06 | 日本农药株式会社 | 芳基四氢吡啶衍生物或其盐类、和含有该化合物的杀虫剂及其使用方法 |
| AU2022234998B2 (en) * | 2021-03-08 | 2025-04-10 | Jinan University | Pyridopyrimidine compounds and applications thereof |
| WO2026027375A1 (de) | 2024-07-29 | 2026-02-05 | Bayer Aktiengesellschaft | Hydroxy-dihydropyridinon carboxamide als schädlingsbekämpfungsmittel |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6165873A (ja) | 1984-09-07 | 1986-04-04 | Mitsui Petrochem Ind Ltd | ２−ピペラジノピリミジン誘導体 |
| US4734418A (en) | 1984-12-14 | 1988-03-29 | Mitsui Petrochemical Industries, Ltd. | Quinazoline compounds and antihypertensives |
| IL85347A0 (en) * | 1987-02-11 | 1988-07-31 | May & Baker Ltd | Cyclic diones |
| SK11322003A3 (en) * | 2001-02-12 | 2004-10-05 | Hoffmann La Roche | 6-Substituted pyrido-pyrimidines |
| DE102004018198A1 (de) * | 2004-04-15 | 2005-11-03 | Merck Patent Gmbh | Sulfonamide |
| US7846915B2 (en) | 2004-10-20 | 2010-12-07 | Resverlogix Corporation | Stilbenes and chalcones for the prevention and treatment of cardiovascular diseases |
| WO2006074293A2 (en) * | 2005-01-07 | 2006-07-13 | President And Fellows Of Harvard College | Bicyclic dihydropyrimidines as eg5 inhibitors |
| US20070027150A1 (en) | 2005-04-14 | 2007-02-01 | Bellamacina Cornelia R | 2-Amino-quinazolin-5-ones |
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- 2006-09-28 HR HR20110655T patent/HRP20110655T1/hr unknown
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- 2006-09-28 WO PCT/US2006/038181 patent/WO2007041362A1/en not_active Ceased
- 2006-09-28 US US11/541,462 patent/US7671059B2/en active Active
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- 2006-09-28 BR BRPI0616701-2A patent/BRPI0616701A2/pt not_active IP Right Cessation
- 2006-09-29 TW TW095136162A patent/TWI373471B/zh not_active IP Right Cessation
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2008
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- 2008-03-28 CR CR9846A patent/CR9846A/es unknown
- 2008-03-28 TN TNP2008000143A patent/TNSN08143A1/en unknown
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- 2008-04-24 MA MA30873A patent/MA29885B1/fr unknown
- 2008-04-30 NO NO20082069A patent/NO342258B1/no not_active IP Right Cessation
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2009
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2011
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2012
- 2012-05-25 JP JP2012119613A patent/JP2012158611A/ja not_active Withdrawn
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