JP2016028032A5 - - Google Patents
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- Publication number
- JP2016028032A5 JP2016028032A5 JP2015157760A JP2015157760A JP2016028032A5 JP 2016028032 A5 JP2016028032 A5 JP 2016028032A5 JP 2015157760 A JP2015157760 A JP 2015157760A JP 2015157760 A JP2015157760 A JP 2015157760A JP 2016028032 A5 JP2016028032 A5 JP 2016028032A5
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- methoxyphenyl
- tumor
- hydroxyl
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 alkylammonium ion Chemical class 0.000 description 127
- 229910052739 hydrogen Inorganic materials 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 27
- 239000001257 hydrogen Substances 0.000 description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 24
- 206010028980 Neoplasm Diseases 0.000 description 22
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 13
- 150000002431 hydrogen Chemical group 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 231100000135 cytotoxicity Toxicity 0.000 description 10
- 230000003013 cytotoxicity Effects 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 229960004679 doxorubicin Drugs 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 230000000259 anti-tumor effect Effects 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 238000013298 xenograft nude mouse model Methods 0.000 description 7
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 6
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 6
- 231100000844 hepatocellular carcinoma Toxicity 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 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 description 5
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 5
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- 230000004614 tumor growth Effects 0.000 description 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 3
- 125000004442 acylamino group Chemical group 0.000 description 3
- 125000004450 alkenylene group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000001589 carboacyl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 229940127271 compound 49 Drugs 0.000 description 3
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 3
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 210000005260 human cell Anatomy 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 description 3
- 230000005917 in vivo anti-tumor Effects 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- JGMSVHVTXWPXGD-UHFFFAOYSA-N 2-phenyl-3h-quinolin-4-one Chemical class N=1C2=CC=CC=C2C(=O)CC=1C1=CC=CC=C1 JGMSVHVTXWPXGD-UHFFFAOYSA-N 0.000 description 2
- 238000011729 BALB/c nude mouse Methods 0.000 description 2
- 208000031648 Body Weight Changes Diseases 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000004579 body weight change Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002579 carboxylato group Chemical group [O-]C(*)=O 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000012091 fetal bovine serum Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 229960005322 streptomycin Drugs 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 230000036962 time dependent Effects 0.000 description 2
- ZCVAUOOENVFIMS-UHFFFAOYSA-N 2-(2-fluorophenyl)-3h-quinolin-4-one Chemical class FC1=CC=CC=C1C1=NC2=CC=CC=C2C(=O)C1 ZCVAUOOENVFIMS-UHFFFAOYSA-N 0.000 description 1
- 125000004937 4H-carbazolyl group Chemical group C=1(C=CCC2=C3C=CC=CC3=NC12)* 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940127573 compound 38 Drugs 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical class [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000004362 fungal culture Methods 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004932 phenoxathinyl group Chemical group 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 230000005760 tumorsuppression Effects 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36476010P | 2010-07-15 | 2010-07-15 | |
| US61/364,760 | 2010-07-15 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013519818A Division JP2013532634A (ja) | 2010-07-15 | 2011-07-14 | アリール及びヘテロアリール−キノリン誘導体の合成及び抗癌活性 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017102672A Division JP6457584B2 (ja) | 2010-07-15 | 2017-05-24 | アリール及びヘテロアリール−キノリン誘導体の合成及び抗癌活性 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016028032A JP2016028032A (ja) | 2016-02-25 |
| JP2016028032A5 true JP2016028032A5 (enExample) | 2016-06-23 |
| JP6371741B2 JP6371741B2 (ja) | 2018-08-08 |
Family
ID=44533096
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013519818A Pending JP2013532634A (ja) | 2010-07-15 | 2011-07-14 | アリール及びヘテロアリール−キノリン誘導体の合成及び抗癌活性 |
| JP2015157760A Active JP6371741B2 (ja) | 2010-07-15 | 2015-08-07 | アリール及びヘテロアリール−キノリン誘導体の合成及び抗癌活性 |
| JP2017102672A Active JP6457584B2 (ja) | 2010-07-15 | 2017-05-24 | アリール及びヘテロアリール−キノリン誘導体の合成及び抗癌活性 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013519818A Pending JP2013532634A (ja) | 2010-07-15 | 2011-07-14 | アリール及びヘテロアリール−キノリン誘導体の合成及び抗癌活性 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017102672A Active JP6457584B2 (ja) | 2010-07-15 | 2017-05-24 | アリール及びヘテロアリール−キノリン誘導体の合成及び抗癌活性 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8524740B2 (enExample) |
| EP (2) | EP2593435B1 (enExample) |
| JP (3) | JP2013532634A (enExample) |
| KR (2) | KR101913194B1 (enExample) |
| CN (1) | CN103347859B (enExample) |
| AU (1) | AU2011279118B2 (enExample) |
| BR (1) | BR112013000716B1 (enExample) |
| CA (2) | CA2805590C (enExample) |
| RU (1) | RU2584688C2 (enExample) |
| TW (1) | TWI499417B (enExample) |
| WO (1) | WO2012009519A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150370707A1 (en) * | 2014-06-24 | 2015-12-24 | Qualcomm Incorporated | Disunited shared-information and private-information caches |
| EP3302488B1 (en) * | 2015-06-03 | 2020-09-30 | Tairx, Inc. | Novel use of aryl-quinolin derivatives as inhibitors of vasculogenic mimicry |
| CN108911967A (zh) * | 2018-08-03 | 2018-11-30 | 上海华堇生物技术有限责任公司 | 2,5–二甲氧基苯甲酰氯的制备方法 |
| CN112358462B (zh) * | 2020-11-10 | 2023-11-10 | 成都伊诺达博医药科技有限公司 | 一种胡椒环衍生物的合成方法 |
| AU2022380979A1 (en) | 2021-11-02 | 2024-06-06 | Flare Therapeutics Inc. | Pparg inverse agonists and uses thereof |
| CN116789567A (zh) * | 2023-05-18 | 2023-09-22 | 福建凯昕药业有限公司 | 抗血小板减少症药芦曲泊帕中间体及其制备方法 |
| CN120695016B (zh) * | 2025-08-29 | 2025-12-02 | 北京大学 | 一种二氢喹啉衍生物在制备预防或治疗脂肪肝产品中的用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994002145A2 (en) | 1992-07-22 | 1994-02-03 | Genelabs Technologies, Inc. | 2-aryl-4-quinolones as antitumor compounds |
| JPH0733743A (ja) * | 1993-07-22 | 1995-02-03 | Kyorin Pharmaceut Co Ltd | ２−アリール−４−キノリノール誘導体 |
| US5571822A (en) * | 1994-09-30 | 1996-11-05 | The University Of North Carolina At Chapel Hill | Antitumor compounds |
| US6569870B1 (en) * | 2000-09-25 | 2003-05-27 | The University Of North Carolina At Chapel Hill | Fluorinated quinolones as antimitotic and antitumor agents |
| SE0103648D0 (sv) * | 2001-11-01 | 2001-11-01 | Astrazeneca Ab | Therapeutic quinolone compounds |
| US6916831B2 (en) * | 2003-02-24 | 2005-07-12 | The University Of North Carolina At Chapel Hill | Flavone acetic acid analogs and methods of use thereof |
| US6897316B2 (en) * | 2003-08-08 | 2005-05-24 | China Medical University | Substituted 2-phenyl-4-quinolone-3-carboxylic acid compounds and their use as antitumor agents |
| CN101583280B (zh) * | 2006-12-07 | 2013-04-24 | 中国医药大学 | 作为抗癌剂的2-芳基-4-喹诺酮的亲水性衍生物 |
| AU2008345225A1 (en) * | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
-
2011
- 2011-07-13 US US13/181,978 patent/US8524740B2/en active Active
- 2011-07-14 KR KR1020177029236A patent/KR101913194B1/ko active Active
- 2011-07-14 KR KR1020137003810A patent/KR20130043194A/ko not_active Ceased
- 2011-07-14 CA CA2805590A patent/CA2805590C/en active Active
- 2011-07-14 AU AU2011279118A patent/AU2011279118B2/en active Active
- 2011-07-14 JP JP2013519818A patent/JP2013532634A/ja active Pending
- 2011-07-14 WO PCT/US2011/043985 patent/WO2012009519A1/en not_active Ceased
- 2011-07-14 BR BR112013000716-8A patent/BR112013000716B1/pt active IP Right Grant
- 2011-07-14 RU RU2013105151/04A patent/RU2584688C2/ru active
- 2011-07-14 CA CA2963390A patent/CA2963390C/en active Active
- 2011-07-14 EP EP11740761.9A patent/EP2593435B1/en active Active
- 2011-07-14 EP EP16181738.2A patent/EP3112348A1/en not_active Withdrawn
- 2011-07-14 CN CN201180033144.1A patent/CN103347859B/zh active Active
- 2011-07-15 TW TW100125130A patent/TWI499417B/zh active
-
2015
- 2015-08-07 JP JP2015157760A patent/JP6371741B2/ja active Active
-
2017
- 2017-05-24 JP JP2017102672A patent/JP6457584B2/ja active Active
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