JPH072726B2 - ベンゾグアナミン誘導体の製法 - Google Patents
ベンゾグアナミン誘導体の製法Info
- Publication number
- JPH072726B2 JPH072726B2 JP61135196A JP13519686A JPH072726B2 JP H072726 B2 JPH072726 B2 JP H072726B2 JP 61135196 A JP61135196 A JP 61135196A JP 13519686 A JP13519686 A JP 13519686A JP H072726 B2 JPH072726 B2 JP H072726B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- present
- dichlorobenzonitrile
- compound
- iii
- 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 - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical class NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 title claims description 3
- LNGWRTKJZCBXGT-UHFFFAOYSA-N 2,5-dichlorobenzonitrile Chemical compound ClC1=CC=C(Cl)C(C#N)=C1 LNGWRTKJZCBXGT-UHFFFAOYSA-N 0.000 claims description 12
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 9
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 239000007810 chemical reaction solvent Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 8
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000000767 anti-ulcer Effects 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- OHDYZVVLNPXKDX-UHFFFAOYSA-N 2,3-dichlorobenzonitrile Chemical compound ClC1=CC=CC(C#N)=C1Cl OHDYZVVLNPXKDX-UHFFFAOYSA-N 0.000 description 1
- -1 2,5-dichlorophenyl Chemical group 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- 150000008359 benzonitriles Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61135196A JPH072726B2 (ja) | 1986-06-10 | 1986-06-10 | ベンゾグアナミン誘導体の製法 |
| CA000538701A CA1290754C (en) | 1986-06-10 | 1987-06-03 | Method of manufacturing benzoguanamine derivatives |
| ES8701678A ES2005249A6 (es) | 1986-06-10 | 1987-06-08 | Un procedimiento para preparar derivados de benzoguanamina. |
| AT0144887A AT395713B (de) | 1986-06-10 | 1987-06-09 | Verfahren zur herstellung von 2,4-diamino-6-(2,5- dichlorphenyl)-s-triazin |
| KR1019870005855A KR950005204B1 (ko) | 1986-06-10 | 1987-06-10 | 벤조구아나민 유도체의 제법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61135196A JPH072726B2 (ja) | 1986-06-10 | 1986-06-10 | ベンゾグアナミン誘導体の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62292771A JPS62292771A (ja) | 1987-12-19 |
| JPH072726B2 true JPH072726B2 (ja) | 1995-01-18 |
Family
ID=15146092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61135196A Expired - Lifetime JPH072726B2 (ja) | 1986-06-10 | 1986-06-10 | ベンゾグアナミン誘導体の製法 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPH072726B2 (de) |
| KR (1) | KR950005204B1 (de) |
| AT (1) | AT395713B (de) |
| CA (1) | CA1290754C (de) |
| ES (1) | ES2005249A6 (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6150362A (en) * | 1997-12-12 | 2000-11-21 | Henkin; Jack | Triazine angiogenesis inhibitors |
| KR101289575B1 (ko) * | 2012-09-07 | 2013-07-24 | 박충만 | 로스트 치킨의 제조방법 |
| CN106187928B (zh) * | 2016-08-02 | 2019-06-07 | 安徽省逸欣铭医药科技有限公司 | 一种马来酸伊索拉定的制备方法 |
| KR101896105B1 (ko) * | 2017-08-28 | 2018-09-07 | 최용선 | 말이 형태의 식품 제형의 제조 방법 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1441904A (en) * | 1974-02-18 | 1976-07-07 | Nippon Shinyaku Co Ltd | Benzoguanamine derivatives |
| JPS5925765B2 (ja) * | 1981-08-04 | 1984-06-21 | 日本新薬株式会社 | 消化性潰瘍治療剤 |
-
1986
- 1986-06-10 JP JP61135196A patent/JPH072726B2/ja not_active Expired - Lifetime
-
1987
- 1987-06-03 CA CA000538701A patent/CA1290754C/en not_active Expired - Lifetime
- 1987-06-08 ES ES8701678A patent/ES2005249A6/es not_active Expired
- 1987-06-09 AT AT0144887A patent/AT395713B/de not_active IP Right Cessation
- 1987-06-10 KR KR1019870005855A patent/KR950005204B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AT395713B (de) | 1993-02-25 |
| CA1290754C (en) | 1991-10-15 |
| ES2005249A6 (es) | 1989-03-01 |
| KR950005204B1 (ko) | 1995-05-19 |
| KR880000411A (ko) | 1988-03-25 |
| ATA144887A (de) | 1992-07-15 |
| JPS62292771A (ja) | 1987-12-19 |
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