AU665238B2 - S-triazine derivative and remedy for estrogen-dependent diseases containing the same as active ingredient - Google Patents
S-triazine derivative and remedy for estrogen-dependent diseases containing the same as active ingredient Download PDFInfo
- Publication number
- AU665238B2 AU665238B2 AU35751/93A AU3575193A AU665238B2 AU 665238 B2 AU665238 B2 AU 665238B2 AU 35751/93 A AU35751/93 A AU 35751/93A AU 3575193 A AU3575193 A AU 3575193A AU 665238 B2 AU665238 B2 AU 665238B2
- Authority
- AU
- Australia
- Prior art keywords
- substituted
- lower alkyl
- triazine
- imidazolyl
- morpholino
- 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.)
- Ceased
Links
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 title claims description 11
- 230000001419 dependent effect Effects 0.000 title claims description 9
- 239000000262 estrogen Substances 0.000 title description 10
- 229940011871 estrogen Drugs 0.000 title description 10
- 201000010099 disease Diseases 0.000 title description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 9
- 239000004480 active ingredient Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 83
- -1 1-piperazinyl Chemical group 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 230000002401 inhibitory effect Effects 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 102000014654 Aromatase Human genes 0.000 claims description 11
- 108010078554 Aromatase Proteins 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- SMXOHNCXXITEJT-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1.C1=NC=NC=N1 SMXOHNCXXITEJT-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 108091036429 KCNQ1OT1 Proteins 0.000 claims 1
- 229920000297 Rayon Polymers 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 238000002844 melting Methods 0.000 description 69
- 230000008018 melting Effects 0.000 description 69
- 239000013078 crystal Substances 0.000 description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 47
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 27
- 239000000203 mixture Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 238000002156 mixing Methods 0.000 description 17
- 239000012044 organic layer Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 238000010898 silica gel chromatography Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 230000000259 anti-tumor effect Effects 0.000 description 8
- 230000000144 pharmacologic effect Effects 0.000 description 8
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229960000473 altretamine Drugs 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical group C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- ITRGRVVBODKGCW-UHFFFAOYSA-N 4,6-dichloro-n,n-dimethyl-1,3,5-triazin-2-amine Chemical compound CN(C)C1=NC(Cl)=NC(Cl)=N1 ITRGRVVBODKGCW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 230000002255 enzymatic effect Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 4
- UQAMDAUJTXFNAD-UHFFFAOYSA-N 4-(4,6-dichloro-1,3,5-triazin-2-yl)morpholine Chemical compound ClC1=NC(Cl)=NC(N2CCOCC2)=N1 UQAMDAUJTXFNAD-UHFFFAOYSA-N 0.000 description 3
- MFGRHTOXRFZEMI-UHFFFAOYSA-N 4-[4-imidazol-1-yl-6-(1,3-thiazolidin-3-yl)-1,3,5-triazin-2-yl]morpholine Chemical compound C1SCCN1C1=NC(N2CCOCC2)=NC(N2C=NC=C2)=N1 MFGRHTOXRFZEMI-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 description 3
- AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 3
- 229950001353 tretamine Drugs 0.000 description 3
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- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 2
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4-78449 | 1992-02-28 | ||
| JP7844992 | 1992-02-28 | ||
| PCT/JP1993/000240 WO1993017009A1 (fr) | 1992-02-28 | 1993-02-26 | DERIVE DE s-TRIAZINE ET REMEDE CONTRE DES MALADIES DEPENDENTES DE L'×STROGENE LE CONTENANT COMME INGREDIENT ACTIF |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3575193A AU3575193A (en) | 1993-09-13 |
| AU665238B2 true AU665238B2 (en) | 1995-12-21 |
Family
ID=13662350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU35751/93A Ceased AU665238B2 (en) | 1992-02-28 | 1993-02-26 | S-triazine derivative and remedy for estrogen-dependent diseases containing the same as active ingredient |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5489591A (https=) |
| EP (1) | EP0629622B1 (https=) |
| KR (1) | KR950700282A (https=) |
| AU (1) | AU665238B2 (https=) |
| CA (1) | CA2131004A1 (https=) |
| DE (1) | DE69322076D1 (https=) |
| WO (1) | WO1993017009A1 (https=) |
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| US6432947B1 (en) * | 1997-02-19 | 2002-08-13 | Berlex Laboratories, Inc. | N-heterocyclic derivatives as NOS inhibitors |
| US6335339B1 (en) | 1998-01-13 | 2002-01-01 | Scriptgen Pharmaceuticals, Inc. | Triazine antiviral compounds |
| WO1999036410A1 (en) * | 1998-01-13 | 1999-07-22 | Scriptgen Pharmaceuticals, Inc. | Triazine antiviral compounds |
| US6943161B2 (en) * | 1999-12-28 | 2005-09-13 | Pharmacopela Drug Discovery, Inc. | Pyrimidine and triazine kinase inhibitors |
| US6525051B2 (en) | 2000-03-27 | 2003-02-25 | Schering Aktiengesellschaft | N-heterocyclic derivatives as NOS inhibitors |
| CN100494182C (zh) | 2000-05-12 | 2009-06-03 | 基酶有限公司 | 肿瘤坏死α因子信号的调节因子 |
| US6716851B2 (en) | 2000-12-12 | 2004-04-06 | Cytovia, Inc. | Substituted 2-aryl-4-arylaminopyrimidines and analogs as activators or caspases and inducers of apoptosis and the use thereof |
| AU2002228922A1 (en) * | 2000-12-12 | 2002-06-24 | Cytovia, Inc. | Substituted 2-aryl-4-arylaminopyrimidines and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| WO2002072561A1 (en) * | 2001-01-26 | 2002-09-19 | Smithkline Beecham Corporation | Piperazinyltriazines as estrogen receptor modulators |
| EP1389617B1 (en) * | 2001-04-27 | 2007-01-03 | Zenyaku Kogyo Kabushiki Kaisha | Heterocyclic compound and antitumor agent containing the same as active ingredient |
| US6982259B2 (en) * | 2002-04-30 | 2006-01-03 | Schering Aktiengesellschaft | N-heterocyclic derivatives as NOS inhibitors |
| KR101046015B1 (ko) * | 2002-10-25 | 2011-07-01 | 젠야쿠코교가부시키가이샤 | 헤테로고리 화합물 및 이것을 유효성분으로 하는 항종양제 |
| RU2265604C1 (ru) * | 2004-09-15 | 2005-12-10 | Кубанский государственный аграрный университет | 4,6-бис(морфолил)-2-[(2`-этоксиацетилтетразолил)-5`-ил]-1,3,5-триазин в качестве антидота |
| AU2005317176A1 (en) * | 2004-12-13 | 2006-06-22 | Neurogen Corporation | Piperazinyl-pyridine analogues |
| TWI381841B (zh) | 2005-03-11 | 2013-01-11 | Zenyaku Kogyo Kk | An immunosuppressive agent and an antitumor agent containing a heterocyclic compound as an active ingredient |
| US20070244110A1 (en) * | 2006-04-14 | 2007-10-18 | Zenyaku Kogyo Kabushiki Kaisha | Treatment of prostate cancer, melanoma or hepatic cancer |
| EP2276750A2 (en) * | 2008-03-27 | 2011-01-26 | Auckland Uniservices Limited | Substituted pyrimidines and triazines and their use in cancer therapy |
| US8575338B2 (en) | 2008-04-09 | 2013-11-05 | Mitsubishi Tanabe Pharma Corporation | Pyrimidine, pyridine and triazine derivatives as maxi-K channel openers |
| GB2465405A (en) * | 2008-11-10 | 2010-05-19 | Univ Basel | Triazine, pyrimidine and pyridine analogues and their use in therapy |
| AU2010223919B2 (en) | 2009-03-13 | 2016-03-31 | Les Laboratoires Servier | Methods and compositions for cell-proliferation-related disorders |
| RU2561132C2 (ru) | 2009-06-29 | 2015-08-20 | Аджиос Фармасьютикалз, Инк. | Производные хинолинсульфонамидов и их применение для модулирования пкм2 активности |
| AR077999A1 (es) * | 2009-09-02 | 2011-10-05 | Vifor Int Ag | Antagonistas de pirimidin y triazin-hepcidina |
| EP3561077B1 (en) | 2009-10-21 | 2022-12-21 | Les Laboratoires Servier | Methods for cell-proliferation-related disorders |
| EP2632916B1 (en) | 2010-10-27 | 2017-01-11 | The Walter and Eliza Hall Institute of Medical Research | Novel anti-cancer agents |
| SG194697A1 (en) | 2011-05-03 | 2013-12-30 | Agios Pharmaceuticals Inc | Pyruvate kinase activators for use in therapy |
| CN102827073A (zh) | 2011-06-17 | 2012-12-19 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
| CN102827170A (zh) | 2011-06-17 | 2012-12-19 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
| NZ627096A (en) | 2012-01-06 | 2017-02-24 | Agios Pharmaceuticals Inc | Triazinyl compounds and their methods of use |
| US9474779B2 (en) | 2012-01-19 | 2016-10-25 | Agios Pharmaceuticals, Inc. | Therapeutically active compositions and their methods of use |
| WO2014062511A1 (en) | 2012-10-15 | 2014-04-24 | Agios Pharmaceuticals, Inc. | Therapeutic compounds and compositions |
| US9579324B2 (en) | 2013-07-11 | 2017-02-28 | Agios Pharmaceuticals, Inc | Therapeutically active compounds and their methods of use |
| WO2015003360A2 (en) * | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| WO2015003355A2 (en) * | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| CN105593215B (zh) | 2013-07-11 | 2019-01-15 | 安吉奥斯医药品有限公司 | 用于治疗癌症的作为idh2突变体抑制剂的2,4-或4,6-二氨基嘧啶化合物 |
| MY185687A (en) | 2013-07-11 | 2021-05-30 | Agios Pharmaceuticals Inc | N,6-bis(aryl or heteroaryl)-1,3,5-triazine-2,4-diamine compounds as idh2 mutants inhibitors for the treatment of cancer |
| CN111087353B (zh) * | 2013-07-11 | 2023-10-24 | 法国施维雅药厂 | 治疗活性化合物及其使用方法 |
| US20150031627A1 (en) | 2013-07-25 | 2015-01-29 | Agios Pharmaceuticals, Inc | Therapeutically active compounds and their methods of use |
| KR20240010105A (ko) | 2014-03-14 | 2024-01-23 | 아지오스 파마슈티컬스 아이엔씨. | 치료적으로 활성인 화합물의 약제학적 조성물 |
| FI3307271T3 (fi) | 2015-06-11 | 2023-10-17 | Agios Pharmaceuticals Inc | Pyruvaattikinaasin aktivaattorien käyttämisen menetelmä |
| PT3362066T (pt) | 2015-10-15 | 2021-11-16 | Celgene Corp | Terapia de combinação para tratar malignidades |
| SG11201803088PA (en) | 2015-10-15 | 2018-05-30 | Agios Pharmaceuticals Inc | Combination therapy for treating malignancies |
| JP7039370B2 (ja) * | 2018-04-06 | 2022-03-22 | 四国化成工業株式会社 | イミダゾリルトリアジン化合物及びその利用 |
| US10980788B2 (en) | 2018-06-08 | 2021-04-20 | Agios Pharmaceuticals, Inc. | Therapy for treating malignancies |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3308122A (en) * | 1965-05-10 | 1967-03-07 | Dow Chemical Co | Trimidazolyl triazine compounds |
| JPS4917677B1 (https=) * | 1970-12-30 | 1974-05-02 | ||
| JPS5655302A (en) * | 1979-10-15 | 1981-05-15 | Hokko Chem Ind Co Ltd | Fungicide for agriculture and horticulture |
| DE3611427A1 (de) * | 1986-04-05 | 1987-10-08 | Hoechst Ag | Bis-tertiaerbutylamino-substituierte 1,3,5-triazinderivate, verfahren zu ihrer herstellung, diese verbindungen enthaltende arzneimittel und ihre verwendung |
-
1993
- 1993-02-26 CA CA002131004A patent/CA2131004A1/en not_active Abandoned
- 1993-02-26 WO PCT/JP1993/000240 patent/WO1993017009A1/ja not_active Ceased
- 1993-02-26 AU AU35751/93A patent/AU665238B2/en not_active Ceased
- 1993-02-26 EP EP93904356A patent/EP0629622B1/en not_active Expired - Lifetime
- 1993-02-26 DE DE69322076T patent/DE69322076D1/de not_active Expired - Lifetime
- 1993-02-26 US US08/290,870 patent/US5489591A/en not_active Expired - Fee Related
-
1994
- 1994-08-27 KR KR1019940703005A patent/KR950700282A/ko not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP0629622B1 (en) | 1998-11-11 |
| EP0629622A4 (https=) | 1995-01-18 |
| US5489591A (en) | 1996-02-06 |
| KR950700282A (ko) | 1995-01-16 |
| AU3575193A (en) | 1993-09-13 |
| CA2131004A1 (en) | 1993-09-02 |
| WO1993017009A1 (fr) | 1993-09-02 |
| EP0629622A1 (en) | 1994-12-21 |
| DE69322076D1 (de) | 1998-12-17 |
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