JP4782337B2 - フラボン類、キサントン類およびクマリン類の新規誘導体 - Google Patents
フラボン類、キサントン類およびクマリン類の新規誘導体 Download PDFInfo
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- JP4782337B2 JP4782337B2 JP2001521732A JP2001521732A JP4782337B2 JP 4782337 B2 JP4782337 B2 JP 4782337B2 JP 2001521732 A JP2001521732 A JP 2001521732A JP 2001521732 A JP2001521732 A JP 2001521732A JP 4782337 B2 JP4782337 B2 JP 4782337B2
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- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Chemical class C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 title 1
- 235000001671 coumarin Nutrition 0.000 title 1
- 150000004775 coumarins Chemical class 0.000 title 1
- 229930003944 flavone Natural products 0.000 title 1
- 150000002213 flavones Chemical class 0.000 title 1
- 235000011949 flavones Nutrition 0.000 title 1
- 150000007964 xanthones Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 238000004519 manufacturing process Methods 0.000 claims abstract description 17
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 12
- 201000011510 cancer Diseases 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 230000001028 anti-proliverative effect Effects 0.000 claims abstract description 6
- 239000012453 solvate Substances 0.000 claims abstract description 5
- 238000002512 chemotherapy Methods 0.000 claims abstract description 3
- 125000006413 ring segment Chemical group 0.000 claims description 74
- 125000000623 heterocyclic group Chemical group 0.000 claims description 65
- 125000002837 carbocyclic group Chemical group 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 239000001257 hydrogen Substances 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000001424 substituent group Chemical group 0.000 claims description 51
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- 125000005842 heteroatom Chemical group 0.000 claims description 32
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 32
- 229920006395 saturated elastomer Polymers 0.000 claims description 32
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 26
- MQMWRJFAKZOCTL-UHFFFAOYSA-N 4-but-2-ynylmorpholine Chemical compound CC#CCN1CCOCC1 MQMWRJFAKZOCTL-UHFFFAOYSA-N 0.000 claims description 14
- 229930012538 Paclitaxel Natural products 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229960001592 paclitaxel Drugs 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 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 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- -1 4-Benzylpiperazin-1-yl Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 229940079593 drug Drugs 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 230000036457 multidrug resistance Effects 0.000 claims description 8
- 102100033350 ATP-dependent translocase ABCB1 Human genes 0.000 claims description 7
- 108010047230 Member 1 Subfamily B ATP Binding Cassette Transporter Proteins 0.000 claims description 7
- 229940034982 antineoplastic agent Drugs 0.000 claims description 7
- 239000002246 antineoplastic agent Substances 0.000 claims description 7
- 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 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229960003668 docetaxel Drugs 0.000 claims description 6
- GZDWCJZYZWTVCL-UHFFFAOYSA-N n,n-diethylbut-2-yn-1-amine Chemical compound CCN(CC)CC#CC GZDWCJZYZWTVCL-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000824 cytostatic agent Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 238000002648 combination therapy Methods 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 108010092160 Dactinomycin Proteins 0.000 claims description 3
- 229940122803 Vinca alkaloid Drugs 0.000 claims description 3
- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 claims description 3
- 229940045799 anthracyclines and related substance Drugs 0.000 claims description 3
- 229960000640 dactinomycin Drugs 0.000 claims description 3
- OMKIXVBYOLINDL-UHFFFAOYSA-N 1-but-2-ynylpiperidine Chemical compound CC#CCN1CCCCC1 OMKIXVBYOLINDL-UHFFFAOYSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- 230000000118 anti-neoplastic effect Effects 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 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 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 101150032584 oxy-4 gene Proteins 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims 2
- NZVZVGPYTICZBZ-UHFFFAOYSA-N 1-benzylpiperidine Chemical compound C=1C=CC=CC=1CN1CCCCC1 NZVZVGPYTICZBZ-UHFFFAOYSA-N 0.000 claims 1
- 230000002927 anti-mitotic effect Effects 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 6
- 208000001132 Osteoporosis Diseases 0.000 abstract description 2
- 230000002265 prevention Effects 0.000 abstract description 2
- 208000017657 Menopausal disease Diseases 0.000 abstract 1
- 206010048723 Multiple-drug resistance Diseases 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 93
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 80
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 64
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 60
- 239000000203 mixture Substances 0.000 description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 38
- 239000002904 solvent Substances 0.000 description 34
- 239000000126 substance Substances 0.000 description 22
- TURAMGVWNUTQKH-UHFFFAOYSA-N propa-1,2-dien-1-one Chemical class C=C=C=O TURAMGVWNUTQKH-UHFFFAOYSA-N 0.000 description 21
- 238000010828 elution Methods 0.000 description 20
- 238000001704 evaporation Methods 0.000 description 20
- 230000008020 evaporation Effects 0.000 description 20
- 238000003818 flash chromatography Methods 0.000 description 20
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
- 208000016691 refractory malignant neoplasm Diseases 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000003013 cytotoxicity Effects 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 2
- IOOMXAQUNPWDLL-UHFFFAOYSA-N 2-[6-(diethylamino)-3-(diethyliminiumyl)-3h-xanthen-9-yl]-5-sulfobenzene-1-sulfonate Chemical compound C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S(O)(=O)=O)C=C1S([O-])(=O)=O IOOMXAQUNPWDLL-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229960001338 colchicine Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- ITPDYQOUSLNIHG-UHFFFAOYSA-N Amiodarone hydrochloride Chemical compound [Cl-].CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCC[NH+](CC)CC)C(I)=C1 ITPDYQOUSLNIHG-UHFFFAOYSA-N 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 0 CC(C)(C=C1)C=C(*)C2=C1OC(C)=C(*)C2=O Chemical compound CC(C)(C=C1)C=C(*)C2=C1OC(C)=C(*)C2=O 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 208000002250 Hematologic Neoplasms Diseases 0.000 description 1
- 206010062016 Immunosuppression Diseases 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- RXFXBVLQMUUZEN-UHFFFAOYSA-N OC1=C2C(C(=COC2=CC(=C1)O)C1=CC=C(C=C1)OC)=O.C(#CC)OC1=CC(=C2C(C(=COC2=C1)C1=CC=C(C=C1)OC)=O)O Chemical compound OC1=C2C(C(=COC2=CC(=C1)O)C1=CC=C(C=C1)OC)=O.C(#CC)OC1=CC(=C2C(C(=COC2=C1)C1=CC=C(C=C1)OC)=O)O RXFXBVLQMUUZEN-UHFFFAOYSA-N 0.000 description 1
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- NWQBTHMIYYLAFG-UHFFFAOYSA-N OC1=CC=C2C(C(=C(OC2=C1)C1=CC=CC=C1)C)=O.C(#CC)OC1=CC=C2C(C(=C(OC2=C1)C1=CC=CC=C1)C)=O Chemical compound OC1=CC=C2C(C(=C(OC2=C1)C1=CC=CC=C1)C)=O.C(#CC)OC1=CC=C2C(C(=C(OC2=C1)C1=CC=CC=C1)C)=O NWQBTHMIYYLAFG-UHFFFAOYSA-N 0.000 description 1
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- OBDZWKINBKERQY-UHFFFAOYSA-N OC=1C=CC=2C(C3=CC=CC=C3OC2C1)=O.C(#CC)OC=1C=CC=2C(C3=CC=CC=C3OC2C1)=O Chemical compound OC=1C=CC=2C(C3=CC=CC=C3OC2C1)=O.C(#CC)OC=1C=CC=2C(C3=CC=CC=C3OC2C1)=O OBDZWKINBKERQY-UHFFFAOYSA-N 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229960005260 amiodarone Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000012925 biological evaluation Methods 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
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- 230000007694 nephrotoxicity Effects 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
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- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
- A61K31/37—Coumarins, e.g. psoralen
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
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- 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
- A61K31/52—Purines, e.g. adenine
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- A61K31/00—Medicinal preparations containing organic active ingredients
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
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- A—HUMAN NECESSITIES
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
- C07D311/36—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only not hydrogenated in the hetero ring, e.g. isoflavones
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- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Endocrinology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (3)
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|---|---|---|---|
| GB9920912.4 | 1999-09-03 | ||
| GBGB9920912.4A GB9920912D0 (en) | 1999-09-03 | 1999-09-03 | Novel derivatives of flavones,xanthones and coumarins |
| PCT/EP2000/008365 WO2001017985A1 (en) | 1999-09-03 | 2000-08-28 | Novel derivatives of flavones, xanthones and coumarins |
Publications (3)
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| JP2003508524A JP2003508524A (ja) | 2003-03-04 |
| JP2003508524A5 JP2003508524A5 (enExample) | 2007-10-11 |
| JP4782337B2 true JP4782337B2 (ja) | 2011-09-28 |
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| HU (1) | HUP0202578A3 (enExample) |
| NO (1) | NO327911B1 (enExample) |
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| SK (1) | SK286402B6 (enExample) |
| WO (1) | WO2001017985A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002020500A2 (en) | 2000-09-01 | 2002-03-14 | Icos Corporation | Materials and methods to potentiate cancer treatment |
| PL205635B1 (pl) * | 2001-04-09 | 2010-05-31 | Inst Farmaceutyczny | Nowe pochodne genisteiny i zawierające je środki farmaceutyczne |
| JP4664597B2 (ja) | 2002-04-17 | 2011-04-06 | サイトキネティクス・インコーポレーテッド | 化合物、組成物および方法 |
| ATE423110T1 (de) | 2002-07-17 | 2009-03-15 | Cytokinetics Inc | Verbindungen, zusammensetzungen und verfahren zur behandlung von zellulären proliferativen erkrankungen |
| EP1553911B1 (en) * | 2002-08-02 | 2010-06-23 | The Ohio State University Research Foundation | 2-heterosubstituted 3-aryl-4-h-1-benzopyran-4-ones as novel therapeutics in breast cancer |
| WO2004024086A2 (en) * | 2002-09-13 | 2004-03-25 | Cytokinetics, Inc. | Compounds, compositions and methods |
| KR20050095859A (ko) * | 2003-02-04 | 2005-10-04 | 가부시키가이샤 야쿠루트 혼샤 | 유방암 내성 단백 저해제 |
| US8404681B2 (en) | 2003-03-24 | 2013-03-26 | Luitpold Pharmaceuticals, Inc. | Xanthones, thioxanthones and acridinones as DNA-PK inhibitors |
| JP2007507539A (ja) * | 2003-10-06 | 2007-03-29 | サイトキネティクス・インコーポレーテッド | 化合物、組成物及び方法 |
| GB0412769D0 (en) | 2004-06-08 | 2004-07-07 | Novartis Ag | Organic compounds |
| GB0412768D0 (en) * | 2004-06-08 | 2004-07-07 | Novartis Ag | Organic compounds |
| FR2929276B1 (fr) * | 2008-04-01 | 2010-04-23 | Servier Lab | Nouveaux derives de diosmetine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CN101497593B (zh) * | 2009-03-18 | 2011-09-21 | 华南理工大学 | 5-羟基香豆素和吡喃型香豆素类化合物及合成方法与应用 |
| EP2560652A4 (en) * | 2010-04-23 | 2013-08-14 | Kineta Inc | ANTIVIRAL CONNECTIONS |
| CN101985449B (zh) * | 2010-09-28 | 2012-08-22 | 中山大学 | 一种香豆素衍生物及其制备方法和作为抗癌药物的用途 |
| CN103113340B (zh) * | 2013-01-21 | 2015-08-19 | 四川大学 | 一类金雀异黄酮烷基胺类化合物、其制备方法和用途 |
| CN103232462B (zh) * | 2013-05-13 | 2016-03-02 | 湖北科技学院 | 香豆素-吡咯类化合物的合成方法 |
| CN103408554B (zh) * | 2013-07-31 | 2015-07-08 | 西安交通大学 | 一种具有降高血压活性的吡咯香豆素类化合物及制备方法 |
| CN104274455B (zh) * | 2014-09-24 | 2018-04-27 | 山东理工大学 | 含苄基哌嗪槲皮素衍生物制法及其对胃黏膜保护作用 |
| CN107641109B (zh) * | 2017-10-16 | 2019-05-24 | 厦门大学 | 一种类黄酮化合物及其制备方法和应用 |
| CN107602520B (zh) * | 2017-10-16 | 2019-06-14 | 厦门大学 | 一种含哌嗪环的类异黄酮化合物及其制备方法和应用 |
| KR102109151B1 (ko) | 2018-06-28 | 2020-05-11 | 영남대학교 산학협력단 | 잔톤 유도체의 신규한 제조방법, 이로 제조된 신규한 잔톤 유도체 및 이들을 포함하는 조성물 |
| CN110156735B (zh) * | 2019-04-23 | 2023-05-12 | 天津国际生物医药联合研究院 | 芒柄花黄素衍生物及其制备方法和应用 |
| CN110240579B (zh) * | 2019-06-10 | 2023-03-31 | 中国科学院成都有机化学有限公司 | 一种多取代γ-丁内酯类化合物、制备方法及其应用 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03163017A (ja) * | 1989-08-24 | 1991-07-15 | Nisshin Flour Milling Co Ltd | 抗癌活性増強剤 |
| JPH0570348A (ja) * | 1991-09-14 | 1993-03-23 | Kureha Chem Ind Co Ltd | 多剤耐性抑制剤 |
| JPH08508974A (ja) * | 1992-07-10 | 1996-09-24 | ラボラトワール、グラクソ、ソシエテ、アノニム | アニリド誘導体 |
| JPH1036260A (ja) * | 1996-07-18 | 1998-02-10 | Mitsui Norin Kk | 抗ガン剤の効力増強方法 |
| JPH11508882A (ja) * | 1995-06-29 | 1999-08-03 | ファーマ マー，ソシエダッド アノニマ | ラメラリン−クラスアルカロイドの治療方法への使用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3513198A (en) * | 1965-10-22 | 1970-05-19 | Hoffmann La Roche | Aryloxy- and arylthio-acetylenic amines and the salts thereof |
| FR2378519B1 (enExample) * | 1976-11-24 | 1982-08-06 | Unicler | |
| US5023341A (en) | 1989-09-19 | 1991-06-11 | Allergan, Inc. | Compounds having a disubstituted acetylene moiety and retinoic acid-like biological activity |
| US5399561A (en) | 1989-09-19 | 1995-03-21 | Allergan, Inc. | Acetylenes disubstituted with a phenyl or heteroaryl group and a 2-oxochromanyl, 2-oxothiochromanyl or 2-oxo-1,2,3,4-tetrahydro-quinolinyl group having retinoid-like biological activity |
| US4996230A (en) * | 1990-02-16 | 1991-02-26 | Eli Lilly And Company | Leukotriene antagonists |
| DE4323409A1 (de) * | 1993-07-13 | 1995-01-19 | Boehringer Mannheim Gmbh | Verwendung von Cumarinen und Carbostyrilen als PLA¶2¶-Inhibitoren, neue Cumarine und Carbostyrile, Verfahren zu ihrer Herstellung und Arzneimittel |
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1999
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2000
- 2000-08-28 JP JP2001521732A patent/JP4782337B2/ja not_active Expired - Fee Related
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- 2000-08-28 HU HU0202578A patent/HUP0202578A3/hu unknown
- 2000-08-28 DK DK00958505T patent/DK1212312T3/da active
- 2000-08-28 CZ CZ20020785A patent/CZ300939B6/cs not_active IP Right Cessation
- 2000-08-28 AU AU70000/00A patent/AU775790B2/en not_active Ceased
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- 2000-08-28 SK SK309-2002A patent/SK286402B6/sk not_active IP Right Cessation
- 2000-08-28 PT PT00958505T patent/PT1212312E/pt unknown
- 2000-08-28 AT AT00958505T patent/ATE236147T1/de active
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- 2000-08-28 WO PCT/EP2000/008365 patent/WO2001017985A1/en not_active Ceased
- 2000-08-28 RU RU2002108565/04A patent/RU2252221C2/ru not_active IP Right Cessation
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2002
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- 2002-03-01 NO NO20021050A patent/NO327911B1/no not_active IP Right Cessation
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03163017A (ja) * | 1989-08-24 | 1991-07-15 | Nisshin Flour Milling Co Ltd | 抗癌活性増強剤 |
| JPH0570348A (ja) * | 1991-09-14 | 1993-03-23 | Kureha Chem Ind Co Ltd | 多剤耐性抑制剤 |
| JPH08508974A (ja) * | 1992-07-10 | 1996-09-24 | ラボラトワール、グラクソ、ソシエテ、アノニム | アニリド誘導体 |
| JPH11508882A (ja) * | 1995-06-29 | 1999-08-03 | ファーマ マー，ソシエダッド アノニマ | ラメラリン−クラスアルカロイドの治療方法への使用 |
| JPH1036260A (ja) * | 1996-07-18 | 1998-02-10 | Mitsui Norin Kk | 抗ガン剤の効力増強方法 |
Also Published As
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| CZ300939B6 (cs) | 2009-09-16 |
| DE60001974T2 (de) | 2004-02-19 |
| US6608089B2 (en) | 2003-08-19 |
| NO20021050L (no) | 2002-05-03 |
| PT1212312E (pt) | 2003-08-29 |
| PL211887B1 (pl) | 2012-07-31 |
| KR100819575B1 (ko) | 2008-04-04 |
| SK286402B6 (sk) | 2008-09-05 |
| DE60001974D1 (de) | 2003-05-08 |
| CA2382129A1 (en) | 2001-03-15 |
| AU7000000A (en) | 2001-04-10 |
| HUP0202578A2 (hu) | 2002-11-28 |
| ES2195933T3 (es) | 2003-12-16 |
| DK1212312T3 (da) | 2003-07-21 |
| EP1212312A1 (en) | 2002-06-12 |
| RU2252221C2 (ru) | 2005-05-20 |
| HUP0202578A3 (en) | 2005-02-28 |
| NO20021050D0 (no) | 2002-03-01 |
| CZ2002785A3 (cs) | 2002-06-12 |
| NO327911B1 (no) | 2009-10-19 |
| WO2001017985A1 (en) | 2001-03-15 |
| SK3092002A3 (en) | 2003-10-07 |
| US20020183318A1 (en) | 2002-12-05 |
| JP2003508524A (ja) | 2003-03-04 |
| KR20020030801A (ko) | 2002-04-25 |
| HK1043368A1 (en) | 2002-09-13 |
| PL356699A1 (en) | 2004-06-28 |
| ATE236147T1 (de) | 2003-04-15 |
| CA2382129C (en) | 2010-07-06 |
| EP1212312B1 (en) | 2003-04-02 |
| CN1229370C (zh) | 2005-11-30 |
| CN1371371A (zh) | 2002-09-25 |
| GB9920912D0 (en) | 1999-11-10 |
| AU775790B2 (en) | 2004-08-12 |
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