GB971166A - Substituted triazino-pyrimidines - Google Patents
Substituted triazino-pyrimidinesInfo
- Publication number
- GB971166A GB971166A GB3697/61A GB369761A GB971166A GB 971166 A GB971166 A GB 971166A GB 3697/61 A GB3697/61 A GB 3697/61A GB 369761 A GB369761 A GB 369761A GB 971166 A GB971166 A GB 971166A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- substituted
- general formula
- hydroxy
- formula above
- 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
- 150000001875 compounds Chemical class 0.000 abstract 11
- 125000003277 amino group Chemical group 0.000 abstract 8
- 125000005842 heteroatom Chemical group 0.000 abstract 7
- 238000002360 preparation method Methods 0.000 abstract 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 6
- 125000005843 halogen group Chemical group 0.000 abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 5
- -1 hydroxy, mercapto Chemical class 0.000 abstract 5
- 238000000034 method Methods 0.000 abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 229910021529 ammonia Inorganic materials 0.000 abstract 3
- 125000001033 ether group Chemical group 0.000 abstract 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 3
- 125000004149 thio group Chemical group *S* 0.000 abstract 3
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 abstract 2
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 150000004679 hydroxides Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000000101 thioether group Chemical group 0.000 abstract 2
- 150000003568 thioethers Chemical class 0.000 abstract 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 239000012435 aralkylating agent Substances 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000008298 dragée Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 239000007937 lozenge Substances 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 1
- 150000003230 pyrimidines Chemical class 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 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
- C07D239/30—Halogen atoms or nitro radicals
-
- 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
-
- 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
-
- 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
- C07D239/50—Three nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
971,166. Substituted triazino [5,4-d]-pyrimidines. KARL THOMAE G.m.b.H. Jan. 31, 1961 [Feb. 2, 1960], No. 3697/61. Heading C2C. The invention comprises V-triazino [5,4-d]- pyrimidines of the general formula wherein R<SP>1</SP> and R<SP>2</SP> are the same or different and each represent a hydrogen or halogen atom, a substituted or unsubstituted amino group, a hydroxy or ether group or the corresponding thio group, or a nitrogen atom forming part of a heterocyclic ring which may contain a further hetero atom, and R<SP>3</SP> represents a hydroxy or ether group or the corresponding thio group, a substituted or unsubstituted amino group or a nitrogen atom forming a part of a heterocyclic ring which may contain a further hetero atom; and salts thereof; and tautomers thereof and their salts in which at least one of R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> represent hydroxy groups, said tautomers being compounds in which at least one of R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> represent oxo groups, and N-alkyl, N-alkenyl, N-hydroxyalkyl, N-aralkyl and N- aryl derivatives of said tautomers; and the preparation of the above V-triazino [5,4-d]- pyrimidines of the above general formula wherein R<SP>3</SP> represents a hydroxy, mercapto or amino group or a tautomer of such a compound in which R<SP>3</SP> represents a hydroxy group by reacting a substituted pyrimidine of the general formula wherein R<SP>1</SP> represents a hydrogen or halogen atom, a mono- or di-substituted amino group, a hydroxy or ether group or the corresponding thio group or a nitrogen atom forming part of a heterocyclic ring which may contain a further hetero atom, R<SP>2</SP> represents any of the groups which may be represented by R<SP>1</SP> except a monosubstituted amino group, and X represents a mono-substituted or unsubstituted amido, thioamido or amidino group, with a diazotising agent such as an organic or inorganic nitrite under conditions forming nitrous acid therefrom; a process for the preparation of the above N- alkylated, N-alkenylated or N-aralkylated tautomers by treating a compound of the first general formula above, wherein at least one of R<SP>1</SP>, R<SP>2</SP> and R 3 represent a hydroxy group, with an alkylating, alkenylating or aralkylating agent such as the required halide or sulphate; a process for the preparation of compounds of the first general formula above wherein one or more of the symbols R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> represent a substituted or unsubstituted amino group, by reacting compounds of the first general formula above, wherein one or more of the symbols R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> represent a hydroxy group and R<SP>2</SP> is other than an unsubstituted or monosubstituted amino group with ammonia or the required amine; a process for the preparation of compounds of the first general formula above, wherein at least one of the symbols R<SP>1</SP> and R<SP>2</SP> represents a halogen atom or a mercapto group, by treating a compound of the first general formula above wherein at least one of the symbols R<SP>1</SP> and R<SP>2</SP> represents a hydroxy group, with a phosphorus halide or phosphorus pentasulphide; a process for the preparation of compounds of the first general formula above, wherein at least one of the groups R<SP>1</SP> and R<SP>2</SP> represents a substituted or unsubstituted amino group, a mercapto group or an ether or thioether group, or a nitrogen atom forming part of a heterocyclic ring which may contain a further hetero atom, by reacting a compound of the first general formula above in which at least one of the symbols R<SP>1</SP> and R<SP>2</SP> represents a halogen atom with ammonia, an amine, or a sulphide, a substituted sulphide, or a substituted hydroxide such as an alkali metal sulphide or alkyl-, aralkyl- or aryl-sulphide or an alkali metal alkoxide, aralkoxide or aryloxide, or a heterocyclic compound containing an imino nitrogen atom and, if desired, a further hetero atom; and a process for the preparation of compounds of the first general formula above wherein R<SP>3</SP> represents a substituted or unsubstituted amino group, a mercapto group or an ether or thioether group, or a nitrogen atom forming part of a heterocyclic ring which may contain a further hetero atom, by reacting a compound of the first general formula above, wherein the symbol R<SP>3</SP> is replaced by a halogen atom, with ammonia, an amine, a heterocyclic compound containing an imino nitrogen atom and, if desired, a further hetero atom, a sulphide, a substituted sulphide or substituted hydroxide. Therapeutic compositions contain one or more V-triazino-[5,4-d]-pyrimidines of the first general formula above and a pharmaceutical carrier. The compositions may be in the form of tablets, dragees, capsules, lozenges, ampoules, suppositories, syrups, elixirs, or injectable preparations.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET0017821 | 1960-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB971166A true GB971166A (en) | 1964-09-30 |
Family
ID=7548726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3697/61A Expired GB971166A (en) | 1960-02-02 | 1961-01-31 | Substituted triazino-pyrimidines |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE1445155A1 (en) |
| FR (2) | FR1466213A (en) |
| GB (1) | GB971166A (en) |
| NL (2) | NL120687C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7618975B2 (en) | 2003-07-03 | 2009-11-17 | Myriad Pharmaceuticals, Inc. | 4-arylamino-quinazolines and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| US7989462B2 (en) | 2003-07-03 | 2011-08-02 | Myrexis, Inc. | 4-arylamin-or-4-heteroarylamino-quinazolines and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| US8258145B2 (en) | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
| US8309562B2 (en) | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
| US20160024022A1 (en) * | 2011-09-02 | 2016-01-28 | Purdue Pharma L.P. | Pyrimidines as sodium channel blockers |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3935277A1 (en) * | 1989-10-24 | 1991-05-02 | Hoechst Ag | SULPHONATED HETEROCYCLIC CARBOXAMIDES, METHOD FOR THE PRODUCTION THEREOF, THEIR SUBSTANCES AND THEIR USE AS HERBICIDES OR GROWTH REGULATORS |
-
0
- NL NL260746D patent/NL260746A/xx unknown
- NL NL120687D patent/NL120687C/xx active
-
1960
- 1960-02-02 DE DE19601445155 patent/DE1445155A1/en active Pending
-
1961
- 1961-01-31 GB GB3697/61A patent/GB971166A/en not_active Expired
- 1961-02-01 FR FR851377A patent/FR1466213A/en not_active Expired
- 1961-02-01 FR FR851378A patent/FR1466214A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7618975B2 (en) | 2003-07-03 | 2009-11-17 | Myriad Pharmaceuticals, Inc. | 4-arylamino-quinazolines and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| US7989462B2 (en) | 2003-07-03 | 2011-08-02 | Myrexis, Inc. | 4-arylamin-or-4-heteroarylamino-quinazolines and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| US8309562B2 (en) | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
| US8258145B2 (en) | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
| US20160024022A1 (en) * | 2011-09-02 | 2016-01-28 | Purdue Pharma L.P. | Pyrimidines as sodium channel blockers |
| JP2016175940A (en) * | 2011-09-02 | 2016-10-06 | パーデュー、ファーマ、リミテッド、パートナーシップ | Pyrimidines as sodium channel blockers |
| US9656968B2 (en) * | 2011-09-02 | 2017-05-23 | Purdue Pharma L.P | Pyrimidines as sodium channel blockers |
| US10059675B2 (en) | 2011-09-02 | 2018-08-28 | Purdue Pharma L.P. | Pyrimidines as sodium channel blockers |
| US10774050B2 (en) | 2011-09-02 | 2020-09-15 | Purdue Pharma, L.P. | Pyrimidines as sodium channel blockers |
Also Published As
| Publication number | Publication date |
|---|---|
| NL260746A (en) | |
| FR1466214A (en) | 1967-01-20 |
| DE1445155A1 (en) | 1968-10-24 |
| FR1466213A (en) | 1967-01-20 |
| NL120687C (en) |
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