DE19929787A1 - Neue 4-(2-Oxodihydrooxadiazinylphenyl)amide und ihre Verwendung - Google Patents
Neue 4-(2-Oxodihydrooxadiazinylphenyl)amide und ihre VerwendungInfo
- Publication number
- DE19929787A1 DE19929787A1 DE19929787A DE19929787A DE19929787A1 DE 19929787 A1 DE19929787 A1 DE 19929787A1 DE 19929787 A DE19929787 A DE 19929787A DE 19929787 A DE19929787 A DE 19929787A DE 19929787 A1 DE19929787 A1 DE 19929787A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- hydrogen
- substituted
- different
- anemia
- 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.)
- Withdrawn
Links
- 150000001408 amides Chemical class 0.000 title claims abstract description 15
- 208000007502 anemia Diseases 0.000 claims abstract description 64
- 239000003814 drug Substances 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 14
- 230000010437 erythropoiesis Effects 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- -1 nitro, hydroxy, carboxy Chemical group 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 102000003951 Erythropoietin Human genes 0.000 claims description 24
- 108090000394 Erythropoietin Proteins 0.000 claims description 24
- 229940105423 erythropoietin Drugs 0.000 claims description 24
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 239000011737 fluorine Substances 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 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 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 238000011321 prophylaxis Methods 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 210000004369 blood Anatomy 0.000 claims description 13
- 239000008280 blood Substances 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 11
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 238000002512 chemotherapy Methods 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 230000002028 premature Effects 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 208000020832 chronic kidney disease Diseases 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 208000022831 chronic renal failure syndrome Diseases 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000000638 stimulation Effects 0.000 claims description 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 208000001647 Renal Insufficiency Diseases 0.000 claims 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
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- 238000005534 hematocrit Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- 229910052742 iron Inorganic materials 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19929787A DE19929787A1 (de) | 1999-06-29 | 1999-06-29 | Neue 4-(2-Oxodihydrooxadiazinylphenyl)amide und ihre Verwendung |
| AU55333/00A AU5533300A (en) | 1999-06-29 | 2000-06-16 | Novel 4-(2-oxodihydrooxadiazinylphenyl)amides and the use thereof for treating anemia |
| PCT/EP2000/005570 WO2001000601A1 (fr) | 1999-06-29 | 2000-06-16 | Nouveaux 4-(2-oxodihydrooxadiazinylphenyl)amides et leur utilisation pour lutter contre les anemies |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19929787A DE19929787A1 (de) | 1999-06-29 | 1999-06-29 | Neue 4-(2-Oxodihydrooxadiazinylphenyl)amide und ihre Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19929787A1 true DE19929787A1 (de) | 2001-01-04 |
Family
ID=7912944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19929787A Withdrawn DE19929787A1 (de) | 1999-06-29 | 1999-06-29 | Neue 4-(2-Oxodihydrooxadiazinylphenyl)amide und ihre Verwendung |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU5533300A (fr) |
| DE (1) | DE19929787A1 (fr) |
| WO (1) | WO2001000601A1 (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002072558A1 (fr) * | 2001-03-13 | 2002-09-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Amides d'acide carboxylique antithrombotiques, leur production et leur utilisation comme medicaments |
| WO2019025562A1 (fr) * | 2017-08-04 | 2019-02-07 | Bayer Aktiengesellschaft | Dihydrooxadiazinones |
| US11897867B2 (en) | 2017-08-04 | 2024-02-13 | Bayer Aktiengesellschaft | 6-phenyl-4,5-dihydropyridazin-3(2H)-one derivatives as PDE3A and PDE3B inhibitors for treating cancer |
| US12427153B2 (en) | 2019-02-01 | 2025-09-30 | Bayer Aktiengesellschaft | 1,2,4-triazin-3(2H)-one compounds for the treatment of hyperproliferative diseases |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10010425A1 (de) * | 2000-03-03 | 2001-09-06 | Bayer Ag | Substituierte 5-Methyldihydropyridazinone und ihre Verwendung |
| US8614204B2 (en) | 2003-06-06 | 2013-12-24 | Fibrogen, Inc. | Enhanced erythropoiesis and iron metabolism |
| EP1852443A1 (fr) | 2006-05-05 | 2007-11-07 | Leukocare AG | Matrice tridimensionelle biocompatible pour la immobilisation de substances biologiques |
| US11046683B2 (en) | 2016-12-15 | 2021-06-29 | Ono Pharmaceutical Co., Ltd. | Activator of TREK (TWIK RElated K+ channels) channels |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5962578A (ja) * | 1982-10-04 | 1984-04-10 | Mitsui Toatsu Chem Inc | オキサジアジン誘導体およびそれを含有する医薬組成物 |
| JPH0676325B2 (ja) * | 1992-05-08 | 1994-09-28 | 三井東圧化学株式会社 | オキサジアジン誘導体を有効成分として含有する抗血栓剤 |
| EP0728482A3 (fr) * | 1995-02-10 | 1999-10-20 | Smithkline Beecham Corporation | Emploi de composés HCP spécifiques pour augmenter l'érythropoiese |
| CA2225666A1 (fr) * | 1995-06-30 | 1997-01-23 | Smithkline Beecham Corporation | Utilisation de composes se liant specifiquement au domaine stat 5 sh2 pour augmenter l'erythropoiese |
| IL125035A0 (en) * | 1995-12-29 | 1999-01-26 | Smithkline Beecham Corp | Thieno (2,3-b) pyrazolo (3,4-d) pyridin-3-ones to enhance erythropoiesis |
-
1999
- 1999-06-29 DE DE19929787A patent/DE19929787A1/de not_active Withdrawn
-
2000
- 2000-06-16 AU AU55333/00A patent/AU5533300A/en not_active Abandoned
- 2000-06-16 WO PCT/EP2000/005570 patent/WO2001000601A1/fr not_active Ceased
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002072558A1 (fr) * | 2001-03-13 | 2002-09-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Amides d'acide carboxylique antithrombotiques, leur production et leur utilisation comme medicaments |
| WO2019025562A1 (fr) * | 2017-08-04 | 2019-02-07 | Bayer Aktiengesellschaft | Dihydrooxadiazinones |
| US11427553B2 (en) | 2017-08-04 | 2022-08-30 | Bayer Aktiengesellschaft | Dihydrooxadiazinones |
| IL272098B1 (en) * | 2017-08-04 | 2023-03-01 | Bayer Ag | Dihydrooxadiazinones |
| IL272098B2 (en) * | 2017-08-04 | 2023-07-01 | Bayer Ag | Dihydrooxadiazinones |
| US11773070B2 (en) | 2017-08-04 | 2023-10-03 | Bayer Aktiengesellschaft | Dihydrooxadiazinones |
| US11897867B2 (en) | 2017-08-04 | 2024-02-13 | Bayer Aktiengesellschaft | 6-phenyl-4,5-dihydropyridazin-3(2H)-one derivatives as PDE3A and PDE3B inhibitors for treating cancer |
| US12258323B2 (en) | 2017-08-04 | 2025-03-25 | Bayer Aktiengesellschaft | Dihydrooxadiazinones |
| US12427153B2 (en) | 2019-02-01 | 2025-09-30 | Bayer Aktiengesellschaft | 1,2,4-triazin-3(2H)-one compounds for the treatment of hyperproliferative diseases |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001000601A1 (fr) | 2001-01-04 |
| AU5533300A (en) | 2001-01-31 |
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