GB875562A - Improvements in and relating to pyrimidine derivatives and the preparation thereof - Google Patents
Improvements in and relating to pyrimidine derivatives and the preparation thereofInfo
- Publication number
- GB875562A GB875562A GB5871/57A GB587157A GB875562A GB 875562 A GB875562 A GB 875562A GB 5871/57 A GB5871/57 A GB 5871/57A GB 587157 A GB587157 A GB 587157A GB 875562 A GB875562 A GB 875562A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethoxy
- ethyl
- pyrimidine
- formula
- trimethoxyhydrocinnamate
- 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
- 238000002360 preparation method Methods 0.000 title abstract 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract 2
- AYBWQZGGKFGQLB-UHFFFAOYSA-N ethyl 3-(3,4,5-trimethoxyphenyl)propanoate Chemical compound CCOC(=O)CCC1=CC(OC)=C(OC)C(OC)=C1 AYBWQZGGKFGQLB-UHFFFAOYSA-N 0.000 abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 2
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- ZKFZTBRMADDRMK-UHFFFAOYSA-N 2-amino-5-[(3,4,5-trimethoxyphenyl)methyl]-1h-pyrimidin-6-one Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(NC(N)=NC=2)=O)=C1 ZKFZTBRMADDRMK-UHFFFAOYSA-N 0.000 abstract 1
- JRPWGXPLAZQYJX-UHFFFAOYSA-N 2-amino-5-benzyl-1h-pyrimidin-6-one Chemical compound O=C1NC(N)=NC=C1CC1=CC=CC=C1 JRPWGXPLAZQYJX-UHFFFAOYSA-N 0.000 abstract 1
- YTFVRYKNXDADBI-SNAWJCMRSA-N 3,4,5-trimethoxycinnamic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC YTFVRYKNXDADBI-SNAWJCMRSA-N 0.000 abstract 1
- PKFSBHDSRKLLNP-UHFFFAOYSA-N 4-butoxy-3,5-dimethoxybenzaldehyde Chemical compound CCCCOC1=C(OC)C=C(C=O)C=C1OC PKFSBHDSRKLLNP-UHFFFAOYSA-N 0.000 abstract 1
- LMMYRVSIBONOSJ-UHFFFAOYSA-N 5-[(4-butoxy-3,5-dimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical group C1=C(OC)C(OCCCC)=C(OC)C=C1CC1=CN=C(N)N=C1N LMMYRVSIBONOSJ-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- YTFVRYKNXDADBI-UHFFFAOYSA-N O-Methylsinapic acid Natural products COC1=CC(C=CC(O)=O)=CC(OC)=C1OC YTFVRYKNXDADBI-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000000842 anti-protozoal effect Effects 0.000 abstract 1
- 239000003904 antiprotozoal agent Substances 0.000 abstract 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 230000000973 chemotherapeutic effect Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- QGNVXQKNARYODX-UHFFFAOYSA-N ethyl 3-(4-butoxy-3,5-dimethoxyphenyl)propanoate Chemical compound COC=1C=C(CCC(=O)OCC)C=C(C1OCCCC)OC QGNVXQKNARYODX-UHFFFAOYSA-N 0.000 abstract 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- BRBKOPJOKNSWSG-UHFFFAOYSA-N sulfaguanidine Chemical compound NC(=N)NS(=O)(=O)C1=CC=C(N)C=C1 BRBKOPJOKNSWSG-UHFFFAOYSA-N 0.000 abstract 1
- 229960004257 sulfaguanidine Drugs 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 abstract 1
- COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the formula: <FORM:0875562/IV (b)/1> (wherein R1, R2, R3 are alkyl groups with one to four carbon atoms and may be the same or different); the preparation thereof by formylating a hydrocinnamic ester of the formula: <FORM:0875562/IV (b)/2> condensing the formyl derivative with guanidine, and chlorinating and subsequently aminating the intermediate 2 - amino - 4 - hydroxy - 5 - benzylpyrimidine; and pharmaceutical preparations containing the products (see Group VI). In Example (1), ethyl-3,4,5-trimethoxyhydrocinnamate is reacted with ethyl formate and the formyl derivative condensed with guanidine to give 2-amino-4-hydroxy-5-(3,4,5-trimethoxybenzyl)-pyrimidine, which on treatment with phosphoryl chloride followed by ethanolic ammonia gives 2,4-diamino-5-(3,4,5-trimethoxybenzyl)-pyrimidine. Similarly made is 2,4-diamino - 5 - (3,5-dimethoxy-4-n-butoxybenzyl)-pyrimidine. Ethyl 3,4,5-trimethoxyhydrocinnamate is made by hydrogenating in the presence of Raney nickel ethyl 3,4,5-trimethoxycinnamate, itself made by reacting 3,4,5-trimethoxycinnamic acid with absolute ethanol in the presence of conc. H2SO4. Ethyl 3,5 - dimethoxy-4-n-butoxyhydrocinnamate is similarly made from 3,5-dimethoxy-4-n-butoxy cinnamic acid, itself made from malonic acid and 3,5 - dimethoxy-4-n-butoxybenzaldehyde, which is made from n-butyl iodide and 3,5-dimethoxy-4-hydroxybenzaldehyde. Specifications 687,032 and 734,801 are referred to.ALSO:Antibacterial and antiprotozoal pharmaceutical preparations comprise a compound of the general formula <FORM:0875562/VI/1> (wherein R1, R2 and R3 represent identical or different C1-4 alkyl groups), together with a carrier therefor. They may take the form of tablets, capsules or suspensions in liquids, and may additionally contain chemotherapeutic sulphonamides (e.g. sulphaguanidine). Specifications 687,032 and 734,801 are referred to.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5871/57A GB875562A (en) | 1957-02-21 | 1957-02-21 | Improvements in and relating to pyrimidine derivatives and the preparation thereof |
| CH5610458A CH366835A (en) | 1957-02-21 | 1958-02-20 | Process for the production of new, therapeutically effective pyrimidines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5871/57A GB875562A (en) | 1957-02-21 | 1957-02-21 | Improvements in and relating to pyrimidine derivatives and the preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB875562A true GB875562A (en) | 1961-08-23 |
Family
ID=9804169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5871/57A Expired GB875562A (en) | 1957-02-21 | 1957-02-21 | Improvements in and relating to pyrimidine derivatives and the preparation thereof |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH366835A (en) |
| GB (1) | GB875562A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0006987A1 (en) * | 1978-05-24 | 1980-01-23 | The Wellcome Foundation Limited | 2,4-Diamino-5-benzylpyrimidines, especially for the treatment of microbial infections, pharmaceutical compositions containing these compounds and processes for preparing these compounds |
| US4992430A (en) * | 1984-05-22 | 1991-02-12 | Dr. Karl Thomae Gmbh | Anti-bacterial compositions comprising a substituted bis-(4-aminophenyl)-sulfone and a dihydro-folic acid reductase |
| WO2002010156A1 (en) * | 2000-07-29 | 2002-02-07 | Arpida Ag | Benzofuran derivatives and their use as antibacterial agents |
| WO2005005418A1 (en) | 2003-07-11 | 2005-01-20 | Arpida Ag | Benzofuran derivatives and their use in the treatment of microbial infections |
| US7524855B2 (en) | 2005-01-07 | 2009-04-28 | Arpida Ag | Selected benzofuran derivatives |
-
1957
- 1957-02-21 GB GB5871/57A patent/GB875562A/en not_active Expired
-
1958
- 1958-02-20 CH CH5610458A patent/CH366835A/en unknown
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0006987A1 (en) * | 1978-05-24 | 1980-01-23 | The Wellcome Foundation Limited | 2,4-Diamino-5-benzylpyrimidines, especially for the treatment of microbial infections, pharmaceutical compositions containing these compounds and processes for preparing these compounds |
| US4992430A (en) * | 1984-05-22 | 1991-02-12 | Dr. Karl Thomae Gmbh | Anti-bacterial compositions comprising a substituted bis-(4-aminophenyl)-sulfone and a dihydro-folic acid reductase |
| US5084449A (en) * | 1984-05-22 | 1992-01-28 | Dr. Karl Thomae Gmbh | Anti-bacterial compositions comprising a substituted bis-(4-aminophenyl)-sulfone and a dihydro-folic acid reductase |
| WO2002010156A1 (en) * | 2000-07-29 | 2002-02-07 | Arpida Ag | Benzofuran derivatives and their use as antibacterial agents |
| WO2002010157A1 (en) * | 2000-07-29 | 2002-02-07 | Arpida Ag | Benzofuran derivatives and their use as antibacterial agents |
| US7030130B2 (en) | 2000-07-29 | 2006-04-18 | Arpida Ag | Benzofuran derivatives and their use as antibacterial agents |
| CN1317277C (en) * | 2000-07-29 | 2007-05-23 | 阿皮德公开股份有限公司 | Benzofuran derivatives and their use as antibacterial agents |
| WO2005005418A1 (en) | 2003-07-11 | 2005-01-20 | Arpida Ag | Benzofuran derivatives and their use in the treatment of microbial infections |
| US7524855B2 (en) | 2005-01-07 | 2009-04-28 | Arpida Ag | Selected benzofuran derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CH366835A (en) | 1963-01-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB875562A (en) | Improvements in and relating to pyrimidine derivatives and the preparation thereof | |
| GB1016071A (en) | New guanidine derivatives and process for preparing the same | |
| GB1364294A (en) | 2-styrylquinazoline compounds | |
| ES245448A1 (en) | Improvements in or relating to novel amidines and the preparation thereof | |
| US2978482A (en) | Sulfamoylacetonitrile | |
| IE47022B1 (en) | Novel amidino-benzylpyrimidines, processes for their manufacture and drugs containing the said compounds | |
| US2719846A (en) | 4[n-(beta-diethylaminoethyl) anilino]-pyrimidine and acid addition salts thereof | |
| GB1167097A (en) | Guanidine Derivatives | |
| GB1244514A (en) | Process for preparing 1-alkyl-(or alkenyl)-2-aminoalkylpyrrolidines and intermediates thereof | |
| US3687953A (en) | Derivatives of dipropylacetamido-2-pyrimidine | |
| GB897693A (en) | New substituted 3:3:3-triphenyl-propylamines and process for their manufacture | |
| US2477409A (en) | Preparation of 2-chloropyrimidines | |
| Fanshawe et al. | Synthesis of 3, 5-Diaminopyrazole Hydrochlorides | |
| GB859716A (en) | New pyrimidines and their salts and a process for their production | |
| Vida et al. | Anticonvulsants. 1. Alkoxymethyl derivatives of barbiturates and diphenylhydantoin | |
| GB1023218A (en) | Substituted pyrido [2,3-e]-triazine 1-oxides | |
| GB937722A (en) | New pyrazolopyrimidines and process for the preparation thereof | |
| GB922321A (en) | Improvements in and relating to quaternary ammonium compounds and the preparation thereof | |
| GB734801A (en) | Improvements in and relating to derivatives of pyrimidine and the manufacture thereof | |
| Ziegler et al. | Synthesis of Isotopically Labeled Medicinals. I. 2-Thiouracil-S35 | |
| GB619915A (en) | New pyrimidine derivatives | |
| SE8203914L (en) | PROCESS FOR THE PREPARATION OF 2,4-DIAMINO-5-(3ს,4ს,5ს-TRIMETHOXYBENZYL)-PYRIMIDINE | |
| GB899404A (en) | Triazine derivatives, the manufacture thereof, and pharmaceutical preparations thereof | |
| Bansal | The synthesis and properties of N-hydroxymethylated cyclic amides and imides. | |
| GB1325787A (en) | 6-aminomethyl-pyrimidines and a process for their production |