DK169032B1 - 5,6-dihydro-2-(substitueret phenyl)-1,2,4-triazin-3,5(2H, 4H)-dioner, fremgangsmåde til fremstilling deraf og præparater indeholdende disse forbindelser - Google Patents
5,6-dihydro-2-(substitueret phenyl)-1,2,4-triazin-3,5(2H, 4H)-dioner, fremgangsmåde til fremstilling deraf og præparater indeholdende disse forbindelser Download PDFInfo
- Publication number
- DK169032B1 DK169032B1 DK048187A DK48187A DK169032B1 DK 169032 B1 DK169032 B1 DK 169032B1 DK 048187 A DK048187 A DK 048187A DK 48187 A DK48187 A DK 48187A DK 169032 B1 DK169032 B1 DK 169032B1
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- parts
- hydrogen
- triazine
- compounds
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 74
- 238000000034 method Methods 0.000 title claims abstract description 48
- -1 5,6-Dihydro-2- (substituted phenyl) -1,2,4-triazine-3,5 (2H, 4H) -diones Chemical class 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 239000002253 acid Substances 0.000 claims abstract description 28
- 239000004480 active ingredient Substances 0.000 claims abstract description 6
- 239000003904 antiprotozoal agent Substances 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 64
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 30
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 24
- 150000002431 hydrogen Chemical group 0.000 claims description 22
- 150000001412 amines Chemical group 0.000 claims description 20
- 229910052751 metal Inorganic materials 0.000 claims description 18
- 239000002184 metal Chemical group 0.000 claims description 18
- 238000006467 substitution reaction Methods 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
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- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
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- QHVOLRFHKYFVDD-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-[2,6-dichloro-4-(3,5-dioxo-1,2,4-triazinan-2-yl)phenyl]acetonitrile Chemical compound C1=CC(Cl)=CC=C1C(C#N)C1=C(Cl)C=C(N2C(NC(=O)CN2)=O)C=C1Cl QHVOLRFHKYFVDD-UHFFFAOYSA-N 0.000 claims description 3
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- 150000002148 esters Chemical class 0.000 description 6
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 6
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
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- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SQMCFUSVGSBKFK-UHFFFAOYSA-N sodium;5-(cyclohexen-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound [Na+].O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 SQMCFUSVGSBKFK-UHFFFAOYSA-N 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fodder In General (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8602342 | 1986-01-30 | ||
| GB868602342A GB8602342D0 (en) | 1986-01-30 | 1986-01-30 | 5 6-dihydro-2-(substituted phenyl)-1 2 4-triazine-3 5(2h 4h)-diones |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK48187D0 DK48187D0 (da) | 1987-01-29 |
| DK48187A DK48187A (da) | 1987-07-31 |
| DK169032B1 true DK169032B1 (da) | 1994-08-01 |
Family
ID=10592258
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK048187A DK169032B1 (da) | 1986-01-30 | 1987-01-29 | 5,6-dihydro-2-(substitueret phenyl)-1,2,4-triazin-3,5(2H, 4H)-dioner, fremgangsmåde til fremstilling deraf og præparater indeholdende disse forbindelser |
| DK93651A DK65193D0 (da) | 1986-01-30 | 1993-06-04 | 4,5-dihydro-2-(substitueret phenyl)-1,2,4-triazin-3,5(3h)-dionforbindelser, fremgangsmaade til fremstilling deraf samt praeparater indeholdende disse forbindelser |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK93651A DK65193D0 (da) | 1986-01-30 | 1993-06-04 | 4,5-dihydro-2-(substitueret phenyl)-1,2,4-triazin-3,5(3h)-dionforbindelser, fremgangsmaade til fremstilling deraf samt praeparater indeholdende disse forbindelser |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US4767760A (es) |
| EP (1) | EP0232932B1 (es) |
| JP (2) | JPH0813806B2 (es) |
| CN (1) | CN1017049B (es) |
| AT (1) | ATE59644T1 (es) |
| AU (1) | AU586731B2 (es) |
| CA (2) | CA1288772C (es) |
| DE (1) | DE3766839D1 (es) |
| DK (2) | DK169032B1 (es) |
| ES (1) | ES2031876T3 (es) |
| FI (1) | FI94634C (es) |
| GB (1) | GB8602342D0 (es) |
| GR (1) | GR3001392T3 (es) |
| IE (1) | IE59510B1 (es) |
| IL (1) | IL81421A (es) |
| NO (1) | NO172690C (es) |
| NZ (1) | NZ218973A (es) |
| PT (1) | PT84218B (es) |
| RU (1) | RU2017736C1 (es) |
| SU (1) | SU1595339A3 (es) |
| ZA (1) | ZA87672B (es) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4097779A (en) * | 1976-04-05 | 1978-06-27 | Gte Sylvania Incorporated | Fluorescent lamp containing a cathode heater circuit disconnect device |
| US4156831A (en) * | 1978-05-24 | 1979-05-29 | Gte Sylvania Incorporated | Fluorescent lamp having heater circuit disconnect device |
| GB8602342D0 (en) * | 1986-01-30 | 1986-03-05 | Janssen Pharmaceutica Nv | 5 6-dihydro-2-(substituted phenyl)-1 2 4-triazine-3 5(2h 4h)-diones |
| DE3826058A1 (de) * | 1988-07-30 | 1990-02-08 | Bayer Ag | Mittel gegen fischparasiten |
| US5070091A (en) * | 1989-01-09 | 1991-12-03 | Bayer Aktiengesellschaft | Substituted 1,2,4-triazinediones useful against protozoa in insects |
| EP0377903A3 (de) * | 1989-01-09 | 1991-07-17 | Bayer Ag | Substituierte Hexahydro-1,2,4-triazindione, Verfahren zu ihrer Herstellung, Zwischenprodukte dafür und ihre Verwendung |
| CN1044905A (zh) * | 1989-02-16 | 1990-08-29 | 赫彻斯特股份公司 | 鱼和昆虫寄生虫对抗剂 |
| CA2012004A1 (en) * | 1989-03-15 | 1990-09-15 | Frank Ellis | Chemical compounds |
| EP0476439A1 (de) * | 1990-09-18 | 1992-03-25 | Bayer Ag | Substituierte 1,2,4-Triazindione, Verfahren zu ihrer Herstellung, Zwischenprodukte dafür und ihre Verwendung |
| DE4120138A1 (de) * | 1991-06-19 | 1992-12-24 | Bayer Ag | Substituierte hexahydro-1,2,4-triazindione, verfahren zu ihrer herstellung, zwischenprodukte dafuer und ihre verwendung |
| US5994355A (en) * | 1993-10-15 | 1999-11-30 | Takeda Chemical Industries, Ltd. | 1, 2, 4-Triazin-3-one derivatives, production and use thereof |
| DE69615601T2 (de) * | 1995-04-14 | 2002-07-11 | Takeda Schering Plough Animal | Verfahren zur Herstellung von Triazinderivate |
| US5747476A (en) * | 1996-07-17 | 1998-05-05 | Mortar & Pestle Veterinary Pharmacy, Inc. | Treatment of equine protozoal myeloencephalitis |
| KR19980019182A (ko) * | 1996-08-30 | 1998-06-05 | 다께다 구니오 | 1,2,4-트리아진-3,5-디온 유도체, 그의 생성법 및 그의 용도(1,2,4-triazine-3,5-dione derivatives, their production a nd use thereof) |
| US5883095A (en) * | 1997-08-07 | 1999-03-16 | University Of Kentucky Research Foundation | Formulations and methods to treat and prevent equine protozoal myeloencephalitis |
| BR9808114A (pt) * | 1997-03-31 | 2000-03-08 | David Granstrom | Formulação de ração para cavalos utilizável para tratar epm, processos para tratar pm em um cavalo que necessita deste tratamento, para prevenir infecção com s. neutrona em cavalos, e, para exterminar s. neurona em cavalos |
| US5830893A (en) * | 1997-04-23 | 1998-11-03 | Mortar & Pestle Veterinary Pharmacy, Inc. | Treatment of equine protozoan myeloencephalitis using triazinediones |
| CN1261881A (zh) * | 1997-07-10 | 2000-08-02 | 詹森药业有限公司 | 作为il－5－抑制剂的6－氮杂尿嘧啶衍生物 |
| ATE364597T1 (de) * | 1997-07-10 | 2007-07-15 | Janssen Pharmaceutica Nv | Il-5 hemmende 6-azauracilderivate |
| US6867207B2 (en) | 1997-07-10 | 2005-03-15 | Janssen Pharmaceutica N.V. | IL-5 inhibiting 6-azauracil derivatives |
| TW450964B (en) | 1997-08-29 | 2001-08-21 | Takeda Schering Plough Animal | Triazine derivatives, their production and use |
| WO2000006172A1 (en) * | 1998-07-27 | 2000-02-10 | Mortar & Pestle Veterinary Pharmacy, Inc. | Treatment of equine protozoan myeloencephalitis using triazinediones |
| EP0987265A1 (en) | 1998-09-18 | 2000-03-22 | Janssen Pharmaceutica N.V. | Interleukin-5 inhibiting 6-azauracil derivatives |
| WO2000019964A2 (en) * | 1998-10-08 | 2000-04-13 | New Ace Research Company | Novel compositions and methods for prevention and treatment of protozoal disease |
| BR9916366A (pt) * | 1998-12-18 | 2001-09-18 | Janssen Pharmaceutica Nv | Derivados de 6-azauracila, inibidores de il-5 |
| CN1188410C (zh) | 1999-08-06 | 2005-02-09 | 詹森药业有限公司 | 非类固醇类的il－5抑制剂,其制备的方法以及包含该抑制剂的医药组合物 |
| PA8591801A1 (es) * | 2002-12-31 | 2004-07-26 | Pfizer Prod Inc | Inhibidores benzamidicos del receptor p2x7. |
| GB0622472D0 (en) * | 2006-11-10 | 2006-12-20 | Addex Pharmaceuticals Sa | Novel heterocyclic derivatives |
| CN107746390B (zh) * | 2017-11-21 | 2021-03-16 | 连云港市亚晖医药化工有限公司 | 抗球虫药地克珠利的制备方法 |
| CN113999139A (zh) * | 2021-12-03 | 2022-02-01 | 杭州臻峰科技有限公司 | 制备2，6-二氯-α-（4-氯代苯基） -4-硝基苯乙腈的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3905971A (en) * | 1971-03-29 | 1975-09-16 | Pfizer | 2-Phenyl-as-triazine-3,5(2H,4H)diones |
| US3912723A (en) * | 1971-03-29 | 1975-10-14 | Pfizer | 2-Phenyl-as-triazine-3,5(2H,4H)diones |
| GB1448696A (en) * | 1973-05-29 | 1976-09-08 | Pfizer | 2-phqnyl-astriazine-3,4-2h,4h-diones |
| DE3408924A1 (de) * | 1984-03-12 | 1985-09-26 | Hoechst Ag, 6230 Frankfurt | Substituierte 2-phenyl-hexahydro-1,2,4-triazin-3,5-dione, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung |
| US4631278A (en) * | 1984-08-01 | 1986-12-23 | Janssen Pharmaceutica N.V. | Anti-protozoal α-aryl-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-benzeneacetonitrile derivatives, pharmaceutical compositions, and method of use therefor |
| CA1244024A (en) * | 1984-08-01 | 1988-11-01 | Gustaaf M. Boeckx | .alpha.- ARYL-4-(4,5-DIHYDRO-3,5-DIOXO-1,2,4-TRIAZIN- 2(3H)-YL)BENZENEACETONITRILES |
| GB8602342D0 (en) * | 1986-01-30 | 1986-03-05 | Janssen Pharmaceutica Nv | 5 6-dihydro-2-(substituted phenyl)-1 2 4-triazine-3 5(2h 4h)-diones |
-
1986
- 1986-01-30 GB GB868602342A patent/GB8602342D0/en active Pending
- 1986-12-29 CA CA000526395A patent/CA1288772C/en not_active Expired - Fee Related
-
1987
- 1987-01-16 RU SU874028812A patent/RU2017736C1/ru active
- 1987-01-16 NZ NZ218973A patent/NZ218973A/xx unknown
- 1987-01-21 EP EP87200088A patent/EP0232932B1/en not_active Expired - Lifetime
- 1987-01-21 AT AT87200088T patent/ATE59644T1/de not_active IP Right Cessation
- 1987-01-21 US US07/005,550 patent/US4767760A/en not_active Expired - Lifetime
- 1987-01-21 DE DE8787200088T patent/DE3766839D1/de not_active Expired - Fee Related
- 1987-01-21 ES ES198787200088T patent/ES2031876T3/es not_active Expired - Lifetime
- 1987-01-29 PT PT84218A patent/PT84218B/pt not_active IP Right Cessation
- 1987-01-29 AU AU68134/87A patent/AU586731B2/en not_active Ceased
- 1987-01-29 IL IL81421A patent/IL81421A/xx not_active IP Right Cessation
- 1987-01-29 NO NO870378A patent/NO172690C/no unknown
- 1987-01-29 DK DK048187A patent/DK169032B1/da not_active IP Right Cessation
- 1987-01-29 IE IE23187A patent/IE59510B1/en not_active IP Right Cessation
- 1987-01-29 ZA ZA87672A patent/ZA87672B/xx unknown
- 1987-01-30 JP JP62018748A patent/JPH0813806B2/ja not_active Expired - Lifetime
- 1987-01-30 FI FI870421A patent/FI94634C/fi not_active IP Right Cessation
- 1987-02-02 CN CN87100531A patent/CN1017049B/zh not_active Expired
-
1988
- 1988-04-22 US US07/184,740 patent/US4912106A/en not_active Expired - Lifetime
- 1988-06-09 SU SU884355878A patent/SU1595339A3/ru active
-
1989
- 1989-07-06 CA CA000604998A patent/CA1302411C/en not_active Expired - Fee Related
- 1989-11-24 US US07/440,828 patent/US4952570A/en not_active Expired - Lifetime
-
1991
- 1991-01-29 GR GR91400093T patent/GR3001392T3/el unknown
-
1993
- 1993-06-04 DK DK93651A patent/DK65193D0/da unknown
-
1995
- 1995-04-06 JP JP7104622A patent/JP2622510B2/ja not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |