GB1371907A - 2-phenyl-as-triazine-3,5-2h,4h-diones - Google Patents
2-phenyl-as-triazine-3,5-2h,4h-dionesInfo
- Publication number
- GB1371907A GB1371907A GB4174371A GB4174371A GB1371907A GB 1371907 A GB1371907 A GB 1371907A GB 4174371 A GB4174371 A GB 4174371A GB 4174371 A GB4174371 A GB 4174371A GB 1371907 A GB1371907 A GB 1371907A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- cyano
- alkyl
- phenyl
- triazine
- 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
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- -1 alkaline earth metal salts Chemical class 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- 150000002431 hydrogen Chemical class 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 125000001153 fluoro group Chemical group F* 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- SRQJWWHCFXOVIW-UHFFFAOYSA-N (2-cyanoacetyl)carbamoyl N-phenylethanehydrazonate Chemical compound C1(=CC=CC=C1)NN=C(OC(NC(CC#N)=O)=O)C SRQJWWHCFXOVIW-UHFFFAOYSA-N 0.000 abstract 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
- XGPCOQNUQVZURR-UHFFFAOYSA-N 2-phenyl-1,2,4-triazine-3,5-dione Chemical class O=C1NC(=O)C=NN1C1=CC=CC=C1 XGPCOQNUQVZURR-UHFFFAOYSA-N 0.000 abstract 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 abstract 1
- SSPYSWLZOPCOLO-UHFFFAOYSA-N 6-azauracil Chemical compound O=C1C=NNC(=O)N1 SSPYSWLZOPCOLO-UHFFFAOYSA-N 0.000 abstract 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 abstract 1
- 239000005695 Ammonium acetate Substances 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 229940043376 ammonium acetate Drugs 0.000 abstract 1
- 235000019257 ammonium acetate Nutrition 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical class N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000003224 coccidiostatic agent Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 239000003651 drinking water Substances 0.000 abstract 1
- 235000020188 drinking water Nutrition 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- HSOGVWWWGVFXGF-UHFFFAOYSA-N ethyl n-(2-cyanoacetyl)carbamate Chemical compound CCOC(=O)NC(=O)CC#N HSOGVWWWGVFXGF-UHFFFAOYSA-N 0.000 abstract 1
- 150000005171 halobenzenes Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000005887 phenylation reaction Methods 0.000 abstract 1
- 244000144977 poultry Species 0.000 abstract 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1371907 2 - Phenyl - as - triazine - 3,5- diones PFIZER Inc 7 Sept 1971 41743/71 Heading C2C Novel compounds of general formula (I) and their alkali metal and alkaline earth metal salts where R 2 and R 6 are hydrogen, fluoro, chloro, cyano or methyl with the proviso that at least one of R 2 or R 6 is hydrogen or fluoro; each of R 3 and R 5 is independently one of a first subgroup of hydrogen, cyano, trifluoromethyl, halogen or C 1-6 alkyl, a second subgroup consisting of C 1-6 alkoxy or C 1-6 alkylthio or a third sub-group consisting of nitro or thiocyanato; R 4 is cyano trifluoromethyl, halogen or C 1-6 alkyl, NR 7 R 8 alkvl sulphonyl, SO 2 -NRR, or C 1-6 alkanoyl with the proviso that when R 4 is SO 2 -NRR, or alkanoyl at least one of R 3 and R 5 is other than hydrogen; R and R 1 are either methyl, ethyl, alkyl or propargyl and R may also be either phenyl, benzyl or p-chlorobenzyl or R and R 1 together with nitrogen may be morpholino, thiomorpholino, pyrrolo, pyrrolino, pyrrolidino, piperdino, N-(C 1-6 alkyl) piperazino, hexamethylenimino, 3,4-dichloro-piperidino, thiazolidino, #<SP>3</SP>-tetrahydropyridino or piperazino; X is oxygen, sulphur, > C = 0, > NH, > SO, > SO 2 or > CHOH; Y and Y<SP>1</SP> are hydrogen, nitro, cyano, halogen or C 1-6 alkoxy; and R 7 and R 8 are C 1-4 alkyl or both together with the nitrogen they are attached to form one of the heterocyclic rings defined above except for 3,4-dichloropiperidino with the proviso that not all of R 2 , R 3 , R 4 , R 6 and R 6 are simultanously hydrogen, fluoro or chloro and that no more than two of these groups are hydrogen are prepared either by (1) reacting the appropriate phenyl diazonium salt with cyanoacetylurethan to provide the corresponding phenylhydrazono - cyanoacetylurethan which under the influence of alkali, sodium acetate/ acetic acid or ammonium acetate/acetic acid produces the 6 - cyano - 2 - phenyl - as - triazine- 3,5-(2H,4H) dione which is hydrolysed to the 6-carboxy derivative and decarboxylated, or (2) phenylation of the parent as-triazine-3,5(2H, 4H)-dione in a suitable solvent (water, ethylene glycol, N<SP>1</SP>,N-dimethyl formamide, dimethyl sulphoxide or alkanols) in the presence of an acid acceptor with the appropriate halobenzene. Compounds (I) are coccidiostats and form with a carrier or diluent a composition which may be administered orally, in poultry feed or via drinking water, or rectally.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN133131A IN133131B (en) | 1971-09-07 | 1971-10-06 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12913971A | 1971-03-29 | 1971-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1371907A true GB1371907A (en) | 1974-10-30 |
Family
ID=22438623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4174371A Expired GB1371907A (en) | 1971-03-29 | 1971-09-07 | 2-phenyl-as-triazine-3,5-2h,4h-diones |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB1371907A (en) |
| PL (1) | PL88946B1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4906287A (en) * | 1984-06-12 | 1990-03-06 | Fmc Corporation | Herbicidal compounds |
| US4956004A (en) * | 1989-05-10 | 1990-09-11 | Fmc Corporation | Herbicidal triazinediones |
| US4985065A (en) * | 1989-05-10 | 1991-01-15 | Fmc Corporation | Tetrazolinone herbicides |
| CN103554046A (en) * | 2013-11-08 | 2014-02-05 | 中国农业科学院上海兽医研究所 | Chicken coccidiosis preventing triazine compound |
-
1971
- 1971-09-07 GB GB4174371A patent/GB1371907A/en not_active Expired
- 1971-11-13 PL PL15157271A patent/PL88946B1/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4906287A (en) * | 1984-06-12 | 1990-03-06 | Fmc Corporation | Herbicidal compounds |
| US4956004A (en) * | 1989-05-10 | 1990-09-11 | Fmc Corporation | Herbicidal triazinediones |
| US4985065A (en) * | 1989-05-10 | 1991-01-15 | Fmc Corporation | Tetrazolinone herbicides |
| CN103554046A (en) * | 2013-11-08 | 2014-02-05 | 中国农业科学院上海兽医研究所 | Chicken coccidiosis preventing triazine compound |
Also Published As
| Publication number | Publication date |
|---|---|
| PL88946B1 (en) | 1976-10-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |