CH596193A5 - Dihalobenzoguanamines with anti-ulcus activity - Google Patents
Dihalobenzoguanamines with anti-ulcus activityInfo
- Publication number
- CH596193A5 CH596193A5 CH1652175A CH1652175A CH596193A5 CH 596193 A5 CH596193 A5 CH 596193A5 CH 1652175 A CH1652175 A CH 1652175A CH 1652175 A CH1652175 A CH 1652175A CH 596193 A5 CH596193 A5 CH 596193A5
- Authority
- CH
- Switzerland
- Prior art keywords
- triazine
- ammonia
- dihalobenzoguanamines
- ulcus
- activity
- Prior art date
Links
- 230000000694 effects Effects 0.000 title abstract description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 9
- IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical class ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VCJQGRGZZDMYIR-UHFFFAOYSA-N 2,4-dichloro-6-(2,4-dichlorophenyl)-1,3,5-triazine Chemical compound ClC1=CC(Cl)=CC=C1C1=NC(Cl)=NC(Cl)=N1 VCJQGRGZZDMYIR-UHFFFAOYSA-N 0.000 description 1
- IVOPPANFWGHWEH-UHFFFAOYSA-N 2,4-dichloro-6-(2,5-dibromophenyl)-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C(=CC=C(Br)C=2)Br)=N1 IVOPPANFWGHWEH-UHFFFAOYSA-N 0.000 description 1
- YDMCWQDHUSEJBQ-UHFFFAOYSA-N 2,4-dichloro-6-(2,5-dichlorophenyl)-1,3,5-triazine Chemical compound ClC1=CC=C(Cl)C(C=2N=C(Cl)N=C(Cl)N=2)=C1 YDMCWQDHUSEJBQ-UHFFFAOYSA-N 0.000 description 1
- SSJULALZARBQAX-UHFFFAOYSA-N 2,4-dichloro-6-(3,4-dichlorophenyl)-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C=C(Cl)C(Cl)=CC=2)=N1 SSJULALZARBQAX-UHFFFAOYSA-N 0.000 description 1
- BODHMBNUPDISMO-UHFFFAOYSA-N 2,4-dichloro-6-(3,5-dichlorophenyl)-1,3,5-triazine Chemical compound ClC1=CC(Cl)=CC(C=2N=C(Cl)N=C(Cl)N=2)=C1 BODHMBNUPDISMO-UHFFFAOYSA-N 0.000 description 1
- CXIXABFFQFDTIA-UHFFFAOYSA-N 2-(5-bromo-2-chlorophenyl)-4,6-dichloro-1,3,5-triazine Chemical compound ClC1=CC=C(Br)C=C1C1=NC(Cl)=NC(Cl)=N1 CXIXABFFQFDTIA-UHFFFAOYSA-N 0.000 description 1
- QHHJLAYFGXSOBP-UHFFFAOYSA-N 6-(2,4-dichlorophenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C(=CC(Cl)=CC=2)Cl)=N1 QHHJLAYFGXSOBP-UHFFFAOYSA-N 0.000 description 1
- GZKVTJOEGGXBBF-UHFFFAOYSA-N 6-(2,5-dibromophenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C(=CC=C(Br)C=2)Br)=N1 GZKVTJOEGGXBBF-UHFFFAOYSA-N 0.000 description 1
- ATCGGEJZONJOCL-UHFFFAOYSA-N 6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C(=CC=C(Cl)C=2)Cl)=N1 ATCGGEJZONJOCL-UHFFFAOYSA-N 0.000 description 1
- DPLWHHAFNKDYDU-UHFFFAOYSA-N 6-(3,4-dichlorophenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=C(Cl)C(Cl)=CC=2)=N1 DPLWHHAFNKDYDU-UHFFFAOYSA-N 0.000 description 1
- NZHXBSDOZWURFJ-UHFFFAOYSA-N 6-(3,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=C(Cl)C=C(Cl)C=2)=N1 NZHXBSDOZWURFJ-UHFFFAOYSA-N 0.000 description 1
- RNXNJHBTMRPHBZ-UHFFFAOYSA-N 6-(5-bromo-2-chlorophenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C(=CC=C(Br)C=2)Cl)=N1 RNXNJHBTMRPHBZ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14660274A JPS554752B2 (enExample) | 1974-12-19 | 1974-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH596193A5 true CH596193A5 (en) | 1978-03-15 |
Family
ID=15411424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1652175A CH596193A5 (en) | 1974-12-19 | 1975-12-19 | Dihalobenzoguanamines with anti-ulcus activity |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS554752B2 (enExample) |
| AT (1) | AT343668B (enExample) |
| CH (1) | CH596193A5 (enExample) |
| NL (1) | NL156696B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4541809B2 (ja) * | 2004-09-08 | 2010-09-08 | キヤノン株式会社 | 有機化合物及び有機発光素子 |
| CN107924151B (zh) | 2015-09-17 | 2021-05-14 | 保土谷化学工业株式会社 | 使用了吡唑啉酮衍生物或该衍生物的盐的电荷控制剂及调色剂 |
| JP2017160144A (ja) * | 2016-03-08 | 2017-09-14 | 東ソー株式会社 | ４，６−ジクロロトリアジン化合物及びその製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4969688A (enExample) * | 1972-11-02 | 1974-07-05 |
-
1974
- 1974-12-19 JP JP14660274A patent/JPS554752B2/ja not_active Expired
-
1975
- 1975-12-03 NL NL7514062.A patent/NL156696B/xx not_active IP Right Cessation
- 1975-12-18 AT AT963175A patent/AT343668B/de not_active IP Right Cessation
- 1975-12-19 CH CH1652175A patent/CH596193A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5175083A (enExample) | 1976-06-29 |
| ATA963175A (de) | 1977-10-15 |
| AT343668B (de) | 1978-06-12 |
| NL156696B (nl) | 1978-05-16 |
| JPS554752B2 (enExample) | 1980-01-31 |
| NL7514062A (nl) | 1976-06-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |