DE10301788B4 - Pharmazeutische Verwendung von Pyrimido[5,4-e][1,2,4]triazin-5,7-dionen - Google Patents
Pharmazeutische Verwendung von Pyrimido[5,4-e][1,2,4]triazin-5,7-dionen Download PDFInfo
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- DE10301788B4 DE10301788B4 DE10301788A DE10301788A DE10301788B4 DE 10301788 B4 DE10301788 B4 DE 10301788B4 DE 10301788 A DE10301788 A DE 10301788A DE 10301788 A DE10301788 A DE 10301788A DE 10301788 B4 DE10301788 B4 DE 10301788B4
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- Prior art keywords
- alkyl
- phenyl
- aryl
- compounds
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- IDJLTUNWTSUIHO-UHFFFAOYSA-N 1,6-didemethyltoxoflavin Chemical class N1=CN=C2C(=O)NC(=O)NC2=N1 IDJLTUNWTSUIHO-UHFFFAOYSA-N 0.000 title description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- -1 bromo, hydroxy Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 90
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 13
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- 238000004519 manufacturing process Methods 0.000 claims description 8
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
- 125000006375 C2-C10 alkynyl group Chemical group 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 206010022489 Insulin Resistance Diseases 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract 5
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- 125000001246 bromo group Chemical group Br* 0.000 abstract 2
- GOYDWZOLBHAPQM-UHFFFAOYSA-N pyrimido[5,4-d]triazine-4,6-dione Chemical class N1=NC(=O)C2=NC(=O)N=CC2=N1 GOYDWZOLBHAPQM-UHFFFAOYSA-N 0.000 abstract 2
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000005108 alkenylthio group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000005133 alkynyloxy group Chemical group 0.000 abstract 1
- 125000005109 alkynylthio group Chemical group 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 19
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
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- RRUVAAGMWNDQDJ-UHFFFAOYSA-N 1-butyl-6-methyl-3-(3-phenoxyphenyl)pyrimido[5,4-e][1,2,4]triazine-5,7-dione Chemical compound N1=C(C(N(C)C(=O)N=2)=O)C=2N(CCCC)N=C1C(C=1)=CC=CC=1OC1=CC=CC=C1 RRUVAAGMWNDQDJ-UHFFFAOYSA-N 0.000 description 4
- AMKZMCLFJFIXMG-UHFFFAOYSA-N 1-ethyl-3,6-dimethylpyrimido[5,4-e][1,2,4]triazine-5,7-dione Chemical compound CCN1N=C(C)N=C2C1=NC(=O)N(C)C2=O AMKZMCLFJFIXMG-UHFFFAOYSA-N 0.000 description 4
- KUNDJCLYFUAOAM-UHFFFAOYSA-N 1-ethyl-3-phenyl-6-propylpyrimido[5,4-e][1,2,4]triazine-5,7-dione Chemical compound N1=C2C(=O)N(CCC)C(=O)N=C2N(CC)N=C1C1=CC=CC=C1 KUNDJCLYFUAOAM-UHFFFAOYSA-N 0.000 description 4
- XZKIHKMTEMTJQX-UHFFFAOYSA-N 4-Nitrophenyl Phosphate Chemical compound OP(O)(=O)OC1=CC=C([N+]([O-])=O)C=C1 XZKIHKMTEMTJQX-UHFFFAOYSA-N 0.000 description 4
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- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 4
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- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- AIDS & HIV (AREA)
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- Emergency Medicine (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10301788A DE10301788B4 (de) | 2003-01-20 | 2003-01-20 | Pharmazeutische Verwendung von Pyrimido[5,4-e][1,2,4]triazin-5,7-dionen |
| JP2006500522A JP2006515611A (ja) | 2003-01-20 | 2004-01-07 | ピリミド［５，４−ｅ］［１，２，４］トリアジン−５，７−ジオン、その製造方法及び使用 |
| MXPA05007201A MXPA05007201A (es) | 2003-01-20 | 2004-01-07 | Pirimido [5, 4 - e][1, 2, 4]triazin - 5, 7 - dionas, metodos para producirlas y su uso. |
| BR0406828-9A BRPI0406828A (pt) | 2003-01-20 | 2004-01-07 | Pirimido[5,4-e][1,2,4]triazin-5,7-dionas, processos para a sua preparação e sua aplicação |
| AT04700447T ATE414086T1 (de) | 2003-01-20 | 2004-01-07 | Pyrimido 5,4-e 1,2,4 triazin-5,7-dione, verf ahren zu deren herstellung und deren verwendung |
| CA002513285A CA2513285A1 (en) | 2003-01-20 | 2004-01-07 | Pyrimido[5,4-e][1,2,4]triazine-5,7-diones, methods for producing the same and their use |
| PCT/EP2004/000040 WO2004065387A1 (de) | 2003-01-20 | 2004-01-07 | PYRIMIDO[5,4-e][1,2,4]TRIAZIN-5,7-DIONE, VERFAHREN ZU DEREN HERSTELLUNG UND DEREN VERWENDUNG |
| EP04700447A EP1587806B1 (de) | 2003-01-20 | 2004-01-07 | PYRIMIDO 5,4-e 1,2,4 TRIAZIN-5,7-DIONE, VERF AHREN ZU DEREN HERSTELLUNG UND DEREN VERWENDUNG |
| DE502004008447T DE502004008447D1 (de) | 2003-01-20 | 2004-01-07 | PYRIMIDO 5,4-e 1,2,4 TRIAZIN-5,7-DIONE, VERF AHREN ZU DEREN HERSTELLUNG UND DEREN VERWENDUNG |
| AU2004205351A AU2004205351A1 (en) | 2003-01-20 | 2004-01-07 | Pyrimido(5,4-e)(1,2,4)triazine-5,7-diones, methods for producing the same and their use |
| US10/760,509 US20040242583A1 (en) | 2003-01-20 | 2004-01-20 | Pyrimido[5,4-e][1,2,4]triazine-5,7-diones, processes for preparing them and their use |
| US11/770,106 US7737144B2 (en) | 2003-01-20 | 2007-06-28 | Pyrimido[5,4-e][1,2,4]triazine-5-7-diones, processes for preparing them and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10301788A DE10301788B4 (de) | 2003-01-20 | 2003-01-20 | Pharmazeutische Verwendung von Pyrimido[5,4-e][1,2,4]triazin-5,7-dionen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE10301788A1 DE10301788A1 (de) | 2004-07-29 |
| DE10301788B4 true DE10301788B4 (de) | 2005-08-25 |
Family
ID=32602696
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10301788A Expired - Fee Related DE10301788B4 (de) | 2003-01-20 | 2003-01-20 | Pharmazeutische Verwendung von Pyrimido[5,4-e][1,2,4]triazin-5,7-dionen |
| DE502004008447T Expired - Lifetime DE502004008447D1 (de) | 2003-01-20 | 2004-01-07 | PYRIMIDO 5,4-e 1,2,4 TRIAZIN-5,7-DIONE, VERF AHREN ZU DEREN HERSTELLUNG UND DEREN VERWENDUNG |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE502004008447T Expired - Lifetime DE502004008447D1 (de) | 2003-01-20 | 2004-01-07 | PYRIMIDO 5,4-e 1,2,4 TRIAZIN-5,7-DIONE, VERF AHREN ZU DEREN HERSTELLUNG UND DEREN VERWENDUNG |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1587806B1 (https=) |
| JP (1) | JP2006515611A (https=) |
| AT (1) | ATE414086T1 (https=) |
| AU (1) | AU2004205351A1 (https=) |
| BR (1) | BRPI0406828A (https=) |
| CA (1) | CA2513285A1 (https=) |
| DE (2) | DE10301788B4 (https=) |
| MX (1) | MXPA05007201A (https=) |
| WO (1) | WO2004065387A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010047982A1 (en) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| JP5557845B2 (ja) | 2008-10-31 | 2014-07-23 | メルク・シャープ・アンド・ドーム・コーポレーション | 糖尿病用剤として有用な新規環状ベンゾイミダゾール誘導体 |
| BRPI0923373B8 (pt) * | 2008-12-12 | 2021-05-25 | Merck Patent Gmbh | composições farmacêuticas compreendendo uma combinação de insulina com derivados de triazina, e uso da dita combinação |
| WO2010072807A2 (en) | 2008-12-23 | 2010-07-01 | Fondation Jerome Lejeune | Inhibitors of cystathionine beta synthase to reduce the neurotoxic overproduction of endogenous hydrogen sulfide |
| US8895596B2 (en) | 2010-02-25 | 2014-11-25 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| BR112013021236B1 (pt) | 2011-02-25 | 2021-05-25 | Merck Sharp & Dohme Corp | composto derivado de benzimidazol, e, composição |
| US9527875B2 (en) | 2012-08-02 | 2016-12-27 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| RU2015140066A (ru) | 2013-02-22 | 2017-03-30 | Мерк Шарп И Доум Корп. | Противодиабетические бициклические соединения |
| WO2014139388A1 (en) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| WO2018118670A1 (en) | 2016-12-20 | 2018-06-28 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
| EP4613274A1 (en) | 2024-03-06 | 2025-09-10 | Freie Universität Berlin | Senolytic compounds |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09255681A (ja) * | 1996-03-25 | 1997-09-30 | Taisho Pharmaceut Co Ltd | 抗腫瘍剤 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0022079D0 (en) * | 2000-09-08 | 2000-10-25 | Inst Of Molecul & Cell Biology | Novel protein tyrosine phosphatase inhibitor |
-
2003
- 2003-01-20 DE DE10301788A patent/DE10301788B4/de not_active Expired - Fee Related
-
2004
- 2004-01-07 AT AT04700447T patent/ATE414086T1/de not_active IP Right Cessation
- 2004-01-07 MX MXPA05007201A patent/MXPA05007201A/es active IP Right Grant
- 2004-01-07 BR BR0406828-9A patent/BRPI0406828A/pt not_active IP Right Cessation
- 2004-01-07 WO PCT/EP2004/000040 patent/WO2004065387A1/de not_active Ceased
- 2004-01-07 EP EP04700447A patent/EP1587806B1/de not_active Expired - Lifetime
- 2004-01-07 JP JP2006500522A patent/JP2006515611A/ja not_active Abandoned
- 2004-01-07 AU AU2004205351A patent/AU2004205351A1/en not_active Abandoned
- 2004-01-07 CA CA002513285A patent/CA2513285A1/en not_active Abandoned
- 2004-01-07 DE DE502004008447T patent/DE502004008447D1/de not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09255681A (ja) * | 1996-03-25 | 1997-09-30 | Taisho Pharmaceut Co Ltd | 抗腫瘍剤 |
Non-Patent Citations (4)
| Title |
|---|
| F. Yoneda et al., Tetrahedron Letters, 1971, 851-854 * |
| JP 09-255681 A, zitiert als Abstr. Pat. Abstr. of Jp. |
| Pat. Abstr. of Jp. & JP 09255681 A * |
| T. Nagamatsu et al., Chem. Pharm. Bull. 1993, 41 (2), 362-8 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004065387A1 (de) | 2004-08-05 |
| CA2513285A1 (en) | 2004-08-05 |
| AU2004205351A1 (en) | 2004-08-05 |
| BRPI0406828A (pt) | 2005-12-27 |
| DE502004008447D1 (de) | 2008-12-24 |
| MXPA05007201A (es) | 2005-09-12 |
| EP1587806A1 (de) | 2005-10-26 |
| DE10301788A1 (de) | 2004-07-29 |
| EP1587806B1 (de) | 2008-11-12 |
| ATE414086T1 (de) | 2008-11-15 |
| JP2006515611A (ja) | 2006-06-01 |
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