GB1291417A - Nitrofuryl-triazole-pyrimidines - Google Patents
Nitrofuryl-triazole-pyrimidinesInfo
- Publication number
- GB1291417A GB1291417A GB20778/71A GB2077871A GB1291417A GB 1291417 A GB1291417 A GB 1291417A GB 20778/71 A GB20778/71 A GB 20778/71A GB 2077871 A GB2077871 A GB 2077871A GB 1291417 A GB1291417 A GB 1291417A
- Authority
- GB
- United Kingdom
- Prior art keywords
- furyl
- prepared
- formula
- pyrimidines
- pyrimidine
- 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.)
- Expired
Links
- -1 Nitrofuryl-triazole-pyrimidines Chemical class 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 238000007363 ring formation reaction Methods 0.000 abstract 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 abstract 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- NHFBZFVKHRICMJ-UHFFFAOYSA-N 2-(furan-2-yl)-5-nitro-[1,2,4]triazolo[1,5-a]pyrimidine Chemical class [N+](=O)([O-])C1=NC=2N(C=C1)N=C(N=2)C=1OC=CC=1 NHFBZFVKHRICMJ-UHFFFAOYSA-N 0.000 abstract 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 1
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 abstract 1
- DWCKLBAFXFRHIE-UHFFFAOYSA-N 4,5-diamino-2-(furan-2-yl)-1H-pyrimidin-6-one Chemical compound O1C(=CC=C1)C1=NC(=C(C(=N1)N)N)O DWCKLBAFXFRHIE-UHFFFAOYSA-N 0.000 abstract 1
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 abstract 1
- LJYSHWWASHJJSL-UHFFFAOYSA-N 6-(furan-2-yl)-1h-pyrimidin-4-one Chemical compound N1C=NC(=O)C=C1C1=CC=CO1 LJYSHWWASHJJSL-UHFFFAOYSA-N 0.000 abstract 1
- JBTDYJPIFGGRNA-UHFFFAOYSA-N 6-(furan-2-yl)-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound N1C(=S)NC(=O)C=C1C1=CC=CO1 JBTDYJPIFGGRNA-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- DOLWUAMIJZGVTC-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]pyrimidine Chemical class N1=CC=CN2C=NN=C21 DOLWUAMIJZGVTC-UHFFFAOYSA-N 0.000 abstract 1
- SEBAFCAGWOODAC-UHFFFAOYSA-N [6-(5-nitrofuran-2-yl)pyrimidin-4-yl]hydrazine Chemical compound [N+](=O)([O-])C1=CC=C(O1)C1=NC=NC(=C1)NN SEBAFCAGWOODAC-UHFFFAOYSA-N 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 229940058936 antimalarials diaminopyrimidines Drugs 0.000 abstract 1
- 229940027988 antiseptic and disinfectant nitrofuran derivative Drugs 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000005698 chloropyrimidines Chemical class 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 150000007857 hydrazones Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- DHVJXAIDYIEKIV-UHFFFAOYSA-N n-[6-(furan-2-yl)-5-methyl-4-oxo-1h-pyrimidin-2-yl]acetamide Chemical compound O=C1NC(NC(=O)C)=NC(C=2OC=CC=2)=C1C DHVJXAIDYIEKIV-UHFFFAOYSA-N 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 125000002560 nitrile group Chemical group 0.000 abstract 1
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical class NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 abstract 1
- 238000007243 oxidative cyclization reaction Methods 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 abstract 1
- QDGHXQFTWKRQTG-UHFFFAOYSA-N pyrimidin-2-ylhydrazine Chemical class NNC1=NC=CC=N1 QDGHXQFTWKRQTG-UHFFFAOYSA-N 0.000 abstract 1
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical class NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 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 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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)
Abstract
1291417 Nitrofuran derivatives BOEHRINGER MANNHEIM GmbH 19 April 1971 [3 Feb 1970] 20778/71 Heading C2C Novel compounds of Formula I (in which TP represents a triazolo-pyrimidine ring system, and each of R 1 , R 2 and R 3 is H, halogen, OH, NH 2 , alkyl, alkoxy, acyloxy, alkylamino, acylamino or haloacylamino) are prepared by (a) nitration of compounds of Formula II or (b) oxidative cyclization of hydrazones of Formulµ III and III<SP>1</SP> (in which Py, together with the -N = C< group, forms a pyrimidine ring) or (c) cyclization of hydrazides of Formulµ IV and IV<SP>1</SP> with the splitting off of water, or (d) condensation of aminotriazoles of Formula V (in which R 4 has the same meaning as R 1 or represents a 5-nitro-2-furyl group) with a 1,3- dicarbonyl compound of the formula (in which R 4 has the above given meaning but with the proviso that only one of the symbols R 4 represents a nitrofuryl group, or with a derivative of such a 1,3-dicarbonyl compound in which one of the -COR 4 groups is replaced by a nitrile group) or (e) cyclization of diaminopyrimidines of Formula VI with nitrous acid. In a resulting compound I the substituents R 1 , R 2 and R 3 may be converted into one another in known manner. The nitrofuryl-s-triazolo-[2,3-a]-pyrimidines may be prepared by rearrangement of the corresponding s-triazolo-[4,3-a]-pyrimidines. Compounds of Formula III<SP>1</SP> are prepared by reaction of 5-nitro-2-furan-aldehyde with appropriate hydrazino-pyrimidines, which are themselves prepared by reaction of the corresponding chloro-pyrimidines with hydrazine. Compounds of Formula II are prepared by cyclization of appropriate furyl-hydrazino-pyrimidines (themselves prepared by reaction of (chloro or alkylthio)-furyl-pyrimidines with hydrazine. 1H - 5 - (2 - furyl) - 7 - hydroxy - vtriazolo-[4,5-d]-pyrimidine is prepared by reaction of 2-(2-furyl)-4,5-diamino-6-hydroxypyrimidine with nitrous acid. 4 - (5 - Nitro - 2 - furyl) - 6 - hydrazino - pyrimidine is prepared by desulphurizing 2-mercapto - 4 - (2 - furyl) - 6 hydroxy - pyrimidine with Raney nickel to form 4-(2-furyl)-6-hydroxypyrimidine, reacting this with POCl 3 to form the chloro compound and treating this with hydrazine hydrate. 2 - Amino - 4 - (2 furyl) - 5 - methyl - 6 - chloropyrimidine is prepared by reacting 2-acetamido- 4 - (2 - furyl) - 5 - methyl - 6(1H) - pyrimidinone with thionyl chloride. Antibacterial compositions for oral or parenteral administration comprise a compound of Formula I together with a pharmaceutical carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702004713 DE2004713A1 (en) | 1970-02-03 | 1970-02-03 | Nitrofuryl triazolo pyrimidine and process for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1291417A true GB1291417A (en) | 1972-10-04 |
Family
ID=5761246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20778/71A Expired GB1291417A (en) | 1970-02-03 | 1971-04-19 | Nitrofuryl-triazole-pyrimidines |
Country Status (4)
| Country | Link |
|---|---|
| AT (4) | AT304543B (en) |
| DE (1) | DE2004713A1 (en) |
| FR (1) | FR2081487B1 (en) |
| GB (1) | GB1291417A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006138734A1 (en) * | 2005-06-17 | 2006-12-28 | Bristol-Myers Squibb Company | Triazolopyrimidine cannabinoid receptor 1 antagonists |
| US20110077268A1 (en) * | 2008-03-14 | 2011-03-31 | Yi Liu | Kinase inhibitors and methods of use |
| WO2011082271A3 (en) * | 2009-12-30 | 2011-11-17 | Arqule, Inc. | Substituted triazolo-pyrimidine compounds |
| US8476282B2 (en) | 2008-11-03 | 2013-07-02 | Intellikine 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 |
| 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 (en) * | 1983-03-03 | 1984-10-10 | Riker Laboratories Inc | TRIAZOL (4.3-C) - AND TRIAZOL (1.5-C) PYRIMIDINES |
| US4532242A (en) * | 1983-05-02 | 1985-07-30 | Riker Laboratories, Inc. | Substituted triazolo[4,3-c]pyrimidines |
| TWI592411B (en) | 2011-02-23 | 2017-07-21 | 英特爾立秦有限責任公司 | Combination of kinase inhibitors and uses thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH460035A (en) * | 1963-10-24 | 1968-07-31 | Norwich Pharma Co | Process for the preparation of 6- (5-nitro-2-furyl) -1H-pyrazolo (3,4-d) pyrimidines substituted in the 4-position |
| NL128809C (en) * | 1966-06-18 |
-
1970
- 1970-02-03 DE DE19702004713 patent/DE2004713A1/en active Pending
-
1971
- 1971-02-02 AT AT87471A patent/AT304543B/en not_active IP Right Cessation
- 1971-02-02 AT AT1124271A patent/AT303036B/en not_active IP Right Cessation
- 1971-02-02 AT AT1124371A patent/AT304545B/en not_active IP Right Cessation
- 1971-02-02 AT AT1124471A patent/AT306010B/en 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 (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006138734A1 (en) * | 2005-06-17 | 2006-12-28 | Bristol-Myers Squibb Company | Triazolopyrimidine cannabinoid receptor 1 antagonists |
| US7452892B2 (en) | 2005-06-17 | 2008-11-18 | Bristol-Myers Squibb Company | Triazolopyrimidine cannabinoid receptor 1 antagonists |
| US9359349B2 (en) | 2007-10-04 | 2016-06-07 | Intellikine Llc | Substituted quinazolines as kinase inhibitors |
| US8993580B2 (en) | 2008-03-14 | 2015-03-31 | Intellikine Llc | Benzothiazole kinase inhibitors and methods of use |
| US8637542B2 (en) * | 2008-03-14 | 2014-01-28 | Intellikine, Inc. | Kinase inhibitors and methods of use |
| JP2011514363A (en) * | 2008-03-14 | 2011-05-06 | インテリカイン， インコーポレイテッド | Kinase inhibitors and methods of use |
| US20110077268A1 (en) * | 2008-03-14 | 2011-03-31 | Yi Liu | 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 |
| US8476282B2 (en) | 2008-11-03 | 2013-07-02 | Intellikine Llc | Benzoxazole kinase inhibitors and methods of use |
| US8476431B2 (en) | 2008-11-03 | 2013-07-02 | Itellikine LLC | Benzoxazole kinase inhibitors and methods of use |
| WO2011082271A3 (en) * | 2009-12-30 | 2011-11-17 | Arqule, Inc. | Substituted triazolo-pyrimidine compounds |
| US8343977B2 (en) | 2009-12-30 | 2013-01-01 | Arqule, Inc. | Substituted triazolo-pyrimidine compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| AT303036B (en) | 1972-11-10 |
| AT304543B (en) | 1973-01-10 |
| AT304545B (en) | 1973-01-10 |
| FR2081487B1 (en) | 1974-08-02 |
| FR2081487A1 (en) | 1971-12-03 |
| AT306010B (en) | 1973-03-26 |
| DE2004713A1 (en) | 1971-08-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |