DE2004713A1 - Nitrofuryl triazolo pyrimidine und Verfahren zu ihrer Herstellung - Google Patents
Nitrofuryl triazolo pyrimidine und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2004713A1 DE2004713A1 DE19702004713 DE2004713A DE2004713A1 DE 2004713 A1 DE2004713 A1 DE 2004713A1 DE 19702004713 DE19702004713 DE 19702004713 DE 2004713 A DE2004713 A DE 2004713A DE 2004713 A1 DE2004713 A1 DE 2004713A1
- Authority
- DE
- Germany
- Prior art keywords
- triazolo
- pyrimidine
- furyl
- nitro
- methyl
- 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.)
- Pending
Links
- ZKQULCJUFSCMNK-UHFFFAOYSA-N [N+](=O)([O-])C1=NC(=NC2=C1NN=N2)C=2OC=CC2 Chemical compound [N+](=O)([O-])C1=NC(=NC2=C1NN=N2)C=2OC=CC2 ZKQULCJUFSCMNK-UHFFFAOYSA-N 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- -1 nitrofuryl group Chemical group 0.000 claims description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 150000007857 hydrazones Chemical class 0.000 claims description 19
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 claims description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000000845 anti-microbial effect Effects 0.000 claims description 3
- 229940058936 antimalarials diaminopyrimidines Drugs 0.000 claims description 3
- 230000008030 elimination Effects 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical class NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 claims description 3
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical group BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
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- 239000000203 mixture Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
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- 239000012362 glacial acetic acid Substances 0.000 description 29
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 27
- 239000013078 crystal Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 22
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- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 description 12
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- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
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- 235000010355 mannitol Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- QDGHXQFTWKRQTG-UHFFFAOYSA-N pyrimidin-2-ylhydrazine Chemical compound NNC1=NC=CC=N1 QDGHXQFTWKRQTG-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702004713 DE2004713A1 (de) | 1970-02-03 | 1970-02-03 | Nitrofuryl triazolo pyrimidine und Verfahren zu ihrer Herstellung |
| AT1124271A AT303036B (de) | 1970-02-03 | 1971-02-02 | Verfahren zur Herstellung von neuen Nitrofuryl-triazolo-pyrimidinen |
| AT87471A AT304543B (de) | 1970-02-03 | 1971-02-02 | Verfahren zur Herstellung von neuen Nitrofuryl-triazolo-pyrimidinen |
| AT1124371A AT304545B (de) | 1970-02-03 | 1971-02-02 | Verfahren zur Herstellung von neuen Nitrofuryl-triazolo-pyrimidinen |
| AT1124471A AT306010B (de) | 1970-02-03 | 1971-02-02 | Verfahren zur Herstellung von neuen Nitrofuryl-triazolo-pyrimidinen |
| FR7103557A FR2081487B1 (enrdf_load_stackoverflow) | 1970-02-03 | 1971-02-03 | |
| GB20778/71A GB1291417A (en) | 1970-02-03 | 1971-04-19 | Nitrofuryl-triazole-pyrimidines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702004713 DE2004713A1 (de) | 1970-02-03 | 1970-02-03 | Nitrofuryl triazolo pyrimidine und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2004713A1 true DE2004713A1 (de) | 1971-08-12 |
Family
ID=5761246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702004713 Pending DE2004713A1 (de) | 1970-02-03 | 1970-02-03 | Nitrofuryl triazolo pyrimidine und Verfahren zu ihrer Herstellung |
Country Status (4)
| Country | Link |
|---|---|
| AT (4) | AT303036B (enrdf_load_stackoverflow) |
| DE (1) | DE2004713A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2081487B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1291417A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110077268A1 (en) * | 2008-03-14 | 2011-03-31 | Yi Liu | Kinase inhibitors and methods of use |
| US8343977B2 (en) | 2009-12-30 | 2013-01-01 | Arqule, Inc. | Substituted triazolo-pyrimidine compounds |
| US8476431B2 (en) | 2008-11-03 | 2013-07-02 | Itellikine LLC | Benzoxazole kinase inhibitors and methods of use |
| US8993580B2 (en) | 2008-03-14 | 2015-03-31 | Intellikine Llc | Benzothiazole kinase inhibitors and methods of use |
| US9096611B2 (en) | 2008-07-08 | 2015-08-04 | Intellikine Llc | Kinase inhibitors and methods of use |
| US9295673B2 (en) | 2011-02-23 | 2016-03-29 | Intellikine Llc | Combination of mTOR inhibitors and P13-kinase inhibitors, and uses thereof |
| US9359349B2 (en) | 2007-10-04 | 2016-06-07 | Intellikine Llc | Substituted quinazolines as kinase inhibitors |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK135184A (da) * | 1983-03-03 | 1984-10-10 | Riker Laboratories Inc | Triazol(4,3-c)- og triazol(1,5-c)pyrimidiner |
| US4532242A (en) * | 1983-05-02 | 1985-07-30 | Riker Laboratories, Inc. | Substituted triazolo[4,3-c]pyrimidines |
| US7452892B2 (en) | 2005-06-17 | 2008-11-18 | Bristol-Myers Squibb Company | Triazolopyrimidine cannabinoid receptor 1 antagonists |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH460035A (de) * | 1963-10-24 | 1968-07-31 | Norwich Pharma Co | Verfahren zur Herstellung von in 4-Stellung substituierten 6-(5-Nitro-2-furyl)-1H-pyrazolo(3,4-d) pyrimidinen |
| NL128809C (enrdf_load_stackoverflow) * | 1966-06-18 |
-
1970
- 1970-02-03 DE DE19702004713 patent/DE2004713A1/de active Pending
-
1971
- 1971-02-02 AT AT1124271A patent/AT303036B/de not_active IP Right Cessation
- 1971-02-02 AT AT1124471A patent/AT306010B/de not_active IP Right Cessation
- 1971-02-02 AT AT1124371A patent/AT304545B/de not_active IP Right Cessation
- 1971-02-02 AT AT87471A patent/AT304543B/de not_active IP Right Cessation
- 1971-02-03 FR FR7103557A patent/FR2081487B1/fr not_active Expired
- 1971-04-19 GB GB20778/71A patent/GB1291417A/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9359349B2 (en) | 2007-10-04 | 2016-06-07 | Intellikine Llc | Substituted quinazolines as kinase inhibitors |
| US20110077268A1 (en) * | 2008-03-14 | 2011-03-31 | Yi Liu | Kinase inhibitors and methods of use |
| US8637542B2 (en) * | 2008-03-14 | 2014-01-28 | Intellikine, Inc. | Kinase inhibitors and methods of use |
| US8993580B2 (en) | 2008-03-14 | 2015-03-31 | Intellikine Llc | Benzothiazole kinase inhibitors and methods of use |
| US9637492B2 (en) | 2008-03-14 | 2017-05-02 | Intellikine Llc | Benzothiazole kinase inhibitors and methods of use |
| US9096611B2 (en) | 2008-07-08 | 2015-08-04 | Intellikine Llc | Kinase inhibitors and methods of use |
| US9828378B2 (en) | 2008-07-08 | 2017-11-28 | Intellikine Llc | Kinase inhibitors and methods of use |
| US8476431B2 (en) | 2008-11-03 | 2013-07-02 | Itellikine LLC | Benzoxazole kinase inhibitors and methods of use |
| US8476282B2 (en) | 2008-11-03 | 2013-07-02 | Intellikine Llc | Benzoxazole kinase inhibitors and methods of use |
| US8343977B2 (en) | 2009-12-30 | 2013-01-01 | Arqule, Inc. | Substituted triazolo-pyrimidine compounds |
| US9295673B2 (en) | 2011-02-23 | 2016-03-29 | Intellikine Llc | Combination of mTOR inhibitors and P13-kinase inhibitors, and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| AT304545B (de) | 1973-01-10 |
| GB1291417A (en) | 1972-10-04 |
| AT303036B (de) | 1972-11-10 |
| AT306010B (de) | 1973-03-26 |
| FR2081487B1 (enrdf_load_stackoverflow) | 1974-08-02 |
| FR2081487A1 (enrdf_load_stackoverflow) | 1971-12-03 |
| AT304543B (de) | 1973-01-10 |
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