ES2621932T3 - Agentes antineoplásicos novedosos - Google Patents
Agentes antineoplásicos novedosos Download PDFInfo
- Publication number
- ES2621932T3 ES2621932T3 ES11835350.7T ES11835350T ES2621932T3 ES 2621932 T3 ES2621932 T3 ES 2621932T3 ES 11835350 T ES11835350 T ES 11835350T ES 2621932 T3 ES2621932 T3 ES 2621932T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- compound
- group
- formula
- phosphate
- 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.)
- Active
Links
- 229940034982 antineoplastic agent Drugs 0.000 title description 5
- 239000002246 antineoplastic agent Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 104
- 125000001424 substituent group Chemical group 0.000 claims abstract description 46
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 40
- 239000000651 prodrug Substances 0.000 claims abstract description 35
- 229940002612 prodrug Drugs 0.000 claims abstract description 35
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 30
- -1 amino, hydroxyl Chemical group 0.000 claims abstract description 30
- 239000010452 phosphate Substances 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 20
- 125000000539 amino acid group Chemical group 0.000 claims abstract description 20
- 125000002843 carboxylic acid group Chemical group 0.000 claims abstract description 20
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 20
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims abstract description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 11
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 10
- 150000001408 amides Chemical class 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 10
- 229920001184 polypeptide Chemical group 0.000 claims abstract description 10
- 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 10
- 108090000765 processed proteins & peptides Chemical group 0.000 claims abstract description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 10
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 7
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 94
- 206010028980 Neoplasm Diseases 0.000 claims description 19
- 229940125782 compound 2 Drugs 0.000 claims description 13
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 8
- 239000003981 vehicle Substances 0.000 claims description 8
- 108090000704 Tubulin Proteins 0.000 claims description 6
- 102000004243 Tubulin Human genes 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- RKTOMAMYOZZYEV-UHFFFAOYSA-N 1-[[4-[[4-(aminomethyl)phenyl]methylamino]-6-[(4-methoxyphenyl)methylamino]-1,3,5-triazin-2-yl]amino]imidazolidine-2,4-dione Chemical compound C1=CC(OC)=CC=C1CNC1=NC(NCC=2C=CC(CN)=CC=2)=NC(NN2C(NC(=O)C2)=O)=N1 RKTOMAMYOZZYEV-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical group N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 208000021550 spleen neoplasm Diseases 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 8
- REQFUGYVPAQCTH-UHFFFAOYSA-N 5-[[5-[(4-hydroxyphenyl)methyl]-4-[(4-methoxyphenyl)methyl]-1-methylimidazol-2-yl]amino]-3-methylimidazole-2,4-dione Chemical compound C1=CC(OC)=CC=C1CC1=C(CC=2C=CC(O)=CC=2)N(C)C(NC=2C(N(C)C(=O)N=2)=O)=N1 REQFUGYVPAQCTH-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- 239000002207 metabolite Substances 0.000 description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
- 241000699660 Mus musculus Species 0.000 description 3
- 125000005910 alkyl carbonate group Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000011580 nude mouse model Methods 0.000 description 3
- 230000004614 tumor growth Effects 0.000 description 3
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 3
- 206010009944 Colon cancer Diseases 0.000 description 2
- 102000001301 EGF receptor Human genes 0.000 description 2
- 108060006698 EGF receptor Proteins 0.000 description 2
- 102400001368 Epidermal growth factor Human genes 0.000 description 2
- 101800003838 Epidermal growth factor Proteins 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 229930012538 Paclitaxel Natural products 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 230000022131 cell cycle Effects 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940116977 epidermal growth factor Drugs 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229960001592 paclitaxel Drugs 0.000 description 2
- 230000019491 signal transduction Effects 0.000 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 description 2
- IHPYMWDTONKSCO-UHFFFAOYSA-N 2,2'-piperazine-1,4-diylbisethanesulfonic acid Chemical compound OS(=O)(=O)CCN1CCN(CCS(O)(=O)=O)CC1 IHPYMWDTONKSCO-UHFFFAOYSA-N 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- 238000012413 Fluorescence activated cell sorting analysis Methods 0.000 description 1
- 230000010337 G2 phase Effects 0.000 description 1
- 241001622391 Leucetta Species 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000007990 PIPES buffer Substances 0.000 description 1
- 241000243142 Porifera Species 0.000 description 1
- 230000002927 anti-mitotic effect Effects 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229930005325 imidazole alkaloid Natural products 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000003119 immunoblot Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical compound [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 108010065304 tubulin S Proteins 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000012447 xenograft mouse model Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US407265P | 2002-08-29 | ||
| US40726510P | 2010-10-27 | 2010-10-27 | |
| PCT/AU2011/001376 WO2012054978A1 (en) | 2010-10-27 | 2011-10-27 | Novel anti-cancer agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2621932T3 true ES2621932T3 (es) | 2017-07-05 |
Family
ID=45992970
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11835350.7T Active ES2621932T3 (es) | 2010-10-27 | 2011-10-27 | Agentes antineoplásicos novedosos |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US8835629B2 (OSRAM) |
| EP (1) | EP2632916B1 (OSRAM) |
| JP (2) | JP6184866B2 (OSRAM) |
| KR (1) | KR101896924B1 (OSRAM) |
| CN (1) | CN103476769B (OSRAM) |
| AU (1) | AU2011320024B2 (OSRAM) |
| CA (1) | CA2814120C (OSRAM) |
| ES (1) | ES2621932T3 (OSRAM) |
| HU (1) | HUE032522T2 (OSRAM) |
| NZ (1) | NZ609186A (OSRAM) |
| PL (1) | PL2632916T3 (OSRAM) |
| WO (1) | WO2012054978A1 (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2632916B1 (en) * | 2010-10-27 | 2017-01-11 | The Walter and Eliza Hall Institute of Medical Research | Novel anti-cancer agents |
| KR101853785B1 (ko) | 2013-11-20 | 2018-05-02 | 주식회사 만도 | 3상모터 제어장치 및 그의 고토크 유지 방법 |
| WO2016070241A1 (en) * | 2014-11-03 | 2016-05-12 | Ctxt Pty Ltd | Triazine compounds, compositions and synthesis |
| US20200128829A1 (en) * | 2017-06-08 | 2020-04-30 | University Of South Alabama | Antimicrobial Compounds |
| CU24661B1 (es) | 2018-01-17 | 2023-05-11 | Aurigene Discovery Tech Ltd | Compuestos de alquinileno sustituidos como agentes anticancerígenos |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1035771A (OSRAM) | ||||
| US2742466A (en) | 1956-04-17 | Chx n nhx c c | ||
| US3145203A (en) | 1961-11-30 | 1964-08-18 | Geigy Chem Corp | Hydrazones of 5-nitro-2-furaldehyde |
| JPS5277163A (en) | 1975-12-24 | 1977-06-29 | Asahi Chem Ind Co Ltd | Stabilized polyurethane composition |
| FR2524467A1 (fr) | 1982-03-30 | 1983-10-07 | Adir | Polymethylene-imines disubstituees, leurs procedes de preparation et les compositions pharmaceutiques les renfermant |
| JPS62192474A (ja) | 1986-02-19 | 1987-08-24 | Canon Inc | 記録液 |
| US4932998A (en) | 1986-09-30 | 1990-06-12 | Idemitsu Kosan Company Limited | Triazine derivatives, and herbicides comprising the same as the effective ingredient |
| US4844731A (en) | 1986-12-27 | 1989-07-04 | Idemitsu Company Co., Ltd. | Triazine derivatives |
| US5187045A (en) | 1988-09-07 | 1993-02-16 | Minnesota Mining And Manufacturing Company | Halomethyl-1,3,5-triazines containing a sensitizer moiety |
| WO1990009378A1 (en) | 1989-02-20 | 1990-08-23 | Idemitsu Kosan Co. Ltd. | Triazine derivative and herbicide containing the same as active ingredient |
| HUT69722A (en) | 1991-11-12 | 1995-09-28 | Pfizer | Triazine derivatives for enhancing antitumor activity |
| WO1993017009A1 (fr) | 1992-02-28 | 1993-09-02 | Zenyaku Kogyo Kabushiki Kaisha | DERIVE DE s-TRIAZINE ET REMEDE CONTRE DES MALADIES DEPENDENTES DE L'×STROGENE LE CONTENANT COMME INGREDIENT ACTIF |
| US5574057A (en) * | 1993-02-03 | 1996-11-12 | University Of Utah Research Foundation | Naamidine A extracted from sea sponges and methods for its use as an anti-tumor agent |
| US6566384B1 (en) | 1996-08-07 | 2003-05-20 | Darwin Discovery Ltd. | Hydroxamic and carboxylic acid derivatives having MMP and TNF inhibitory activity |
| FR2757057A1 (fr) | 1996-12-17 | 1998-06-19 | Oreal | Compositions comprenant un derive de dibenzoylmethane, un derive de 1,3,5-triazine et un derive silicie a fonction benzalmalonate et utilisations |
| FR2757056B1 (fr) | 1996-12-17 | 2003-03-14 | Oreal | Compositions comprenant un derive de dibenzoylmethane, un derive de 1,3,5-triazine et un compose amide et utilisations |
| EP0945447A1 (en) | 1998-03-27 | 1999-09-29 | Janssen Pharmaceutica N.V. | Trisubstituted 1,3,5-triazine derivatives for treatment of HIV infections |
| US6262053B1 (en) | 1999-06-23 | 2001-07-17 | Parker Hughes Institute | Melamine derivatives as potent anti-cancer agents |
| CA2426654C (en) * | 2000-10-23 | 2010-12-21 | Smithkline Beecham Corporation | 2,4,8-trisubstituted-8h-pyrido[2,3-d}pyrimidin-7-one compounds |
| US7173032B2 (en) * | 2001-09-21 | 2007-02-06 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
| WO2003032903A2 (en) * | 2001-10-12 | 2003-04-24 | New York University | Trisubstituted triazines compounds with antitubulin activity |
| CN1697831A (zh) * | 2002-09-23 | 2005-11-16 | 雷迪美国治疗公司 | 新三嗪化合物的制备方法和组合物 |
| EP2632916B1 (en) * | 2010-10-27 | 2017-01-11 | The Walter and Eliza Hall Institute of Medical Research | Novel anti-cancer agents |
-
2011
- 2011-10-27 EP EP11835350.7A patent/EP2632916B1/en not_active Not-in-force
- 2011-10-27 AU AU2011320024A patent/AU2011320024B2/en not_active Ceased
- 2011-10-27 CN CN201180059899.9A patent/CN103476769B/zh not_active Expired - Fee Related
- 2011-10-27 HU HUE11835350A patent/HUE032522T2/en unknown
- 2011-10-27 NZ NZ609186A patent/NZ609186A/en not_active IP Right Cessation
- 2011-10-27 CA CA2814120A patent/CA2814120C/en active Active
- 2011-10-27 KR KR1020137013509A patent/KR101896924B1/ko not_active Expired - Fee Related
- 2011-10-27 JP JP2013535207A patent/JP6184866B2/ja not_active Expired - Fee Related
- 2011-10-27 WO PCT/AU2011/001376 patent/WO2012054978A1/en not_active Ceased
- 2011-10-27 US US13/878,557 patent/US8835629B2/en active Active
- 2011-10-27 ES ES11835350.7T patent/ES2621932T3/es active Active
- 2011-10-27 PL PL11835350T patent/PL2632916T3/pl unknown
-
2014
- 2014-08-06 US US14/453,502 patent/US9221799B2/en active Active
-
2015
- 2015-11-19 US US14/946,368 patent/US20160145243A1/en not_active Abandoned
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2017
- 2017-02-28 JP JP2017037462A patent/JP2017137323A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| KR101896924B1 (ko) | 2018-09-10 |
| US20150045365A1 (en) | 2015-02-12 |
| WO2012054978A1 (en) | 2012-05-03 |
| JP2013540778A (ja) | 2013-11-07 |
| JP6184866B2 (ja) | 2017-08-23 |
| AU2011320024B2 (en) | 2014-10-30 |
| US8835629B2 (en) | 2014-09-16 |
| AU2011320024A1 (en) | 2013-05-02 |
| NZ609186A (en) | 2015-08-28 |
| KR20130141554A (ko) | 2013-12-26 |
| JP2017137323A (ja) | 2017-08-10 |
| HUE032522T2 (en) | 2017-09-28 |
| EP2632916B1 (en) | 2017-01-11 |
| CN103476769B (zh) | 2016-06-01 |
| PL2632916T3 (pl) | 2017-07-31 |
| US20130261119A1 (en) | 2013-10-03 |
| US20160145243A1 (en) | 2016-05-26 |
| CA2814120A1 (en) | 2012-05-03 |
| CN103476769A (zh) | 2013-12-25 |
| US9221799B2 (en) | 2015-12-29 |
| EP2632916A4 (en) | 2014-04-23 |
| CA2814120C (en) | 2018-08-07 |
| EP2632916A1 (en) | 2013-09-04 |
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