DE2714157A1 - Substituierte chinoxaline, verfahren zu deren herstellung und arzneimittel gegen cholera, welche diese verbindungen enthalten - Google Patents
Substituierte chinoxaline, verfahren zu deren herstellung und arzneimittel gegen cholera, welche diese verbindungen enthaltenInfo
- Publication number
- DE2714157A1 DE2714157A1 DE19772714157 DE2714157A DE2714157A1 DE 2714157 A1 DE2714157 A1 DE 2714157A1 DE 19772714157 DE19772714157 DE 19772714157 DE 2714157 A DE2714157 A DE 2714157A DE 2714157 A1 DE2714157 A1 DE 2714157A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- quinoxaline
- compounds
- amino
- substituted quinoxaline
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 27
- 206010008631 Cholera Diseases 0.000 title claims description 22
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical class N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229940126601 medicinal product Drugs 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 11
- 150000003252 quinoxalines Chemical class 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- -1 alkyl acetal Chemical class 0.000 claims description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical compound C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- IDQNBVFPZMCDDN-UHFFFAOYSA-N 2-Amino-4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC(N)=N1 IDQNBVFPZMCDDN-UHFFFAOYSA-N 0.000 claims description 2
- GHCFWKFREBNSPC-UHFFFAOYSA-N 2-Amino-4-methylpyrimidine Chemical compound CC1=CC=NC(N)=N1 GHCFWKFREBNSPC-UHFFFAOYSA-N 0.000 claims description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 37
- 241001465754 Metazoa Species 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 8
- 230000037396 body weight Effects 0.000 description 8
- 239000010865 sewage Substances 0.000 description 8
- 230000000069 prophylactic effect Effects 0.000 description 7
- 241000700159 Rattus Species 0.000 description 6
- 210000003754 fetus Anatomy 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 108010082126 Alanine transaminase Proteins 0.000 description 4
- 108010003415 Aspartate Aminotransferases Proteins 0.000 description 4
- 102000004625 Aspartate Aminotransferases Human genes 0.000 description 4
- 241000416162 Astragalus gummifer Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229920001615 Tragacanth Polymers 0.000 description 4
- 241000607626 Vibrio cholerae Species 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 230000007665 chronic toxicity Effects 0.000 description 4
- 231100000160 chronic toxicity Toxicity 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 210000003734 kidney Anatomy 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 229940116362 tragacanth Drugs 0.000 description 4
- 235000010487 tragacanth Nutrition 0.000 description 4
- 239000000196 tragacanth Substances 0.000 description 4
- 229940118696 vibrio cholerae Drugs 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000013068 control sample Substances 0.000 description 3
- 230000034994 death Effects 0.000 description 3
- 231100000517 death Toxicity 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 210000003238 esophagus Anatomy 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 231100000456 subacute toxicity Toxicity 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- 241000700198 Cavia Species 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 241000607598 Vibrio Species 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 238000011886 postmortem examination Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- JZJFIUXMPBVEFS-UHFFFAOYSA-N 1-oxido-4-oxoquinoxalin-4-ium-2-carbaldehyde Chemical compound C1=CC=C2N([O-])C(C=O)=C[N+](=O)C2=C1 JZJFIUXMPBVEFS-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 231100000369 acute toxicity data Toxicity 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67212376A | 1976-03-31 | 1976-03-31 | |
| US05/771,118 US4076815A (en) | 1976-03-31 | 1977-02-23 | Quinoxaline compound and composition, process for preparing compound, and method of combatting cholera therewith |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2714157A1 true DE2714157A1 (de) | 1977-10-27 |
Family
ID=27100689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772714157 Withdrawn DE2714157A1 (de) | 1976-03-31 | 1977-03-30 | Substituierte chinoxaline, verfahren zu deren herstellung und arzneimittel gegen cholera, welche diese verbindungen enthalten |
Country Status (14)
-
1977
- 1977-03-16 NZ NZ183626A patent/NZ183626A/xx unknown
- 1977-03-17 IN IN394/CAL/77A patent/IN144232B/en unknown
- 1977-03-18 GB GB11688/77A patent/GB1536393A/en not_active Expired
- 1977-03-24 MX MX775574U patent/MX4659E/es unknown
- 1977-03-25 BE BE176150A patent/BE852913A/xx not_active IP Right Cessation
- 1977-03-25 AR AR266981A patent/AR212615A1/es active
- 1977-03-29 CA CA275,024A patent/CA1069899A/en not_active Expired
- 1977-03-30 DE DE19772714157 patent/DE2714157A1/de not_active Withdrawn
- 1977-03-30 DK DK140377A patent/DK143701C/da not_active IP Right Cessation
- 1977-03-30 IE IE674/77A patent/IE45275B1/en unknown
- 1977-03-30 ES ES457359A patent/ES457359A1/es not_active Expired
- 1977-03-30 NL NL7703465A patent/NL7703465A/xx not_active Application Discontinuation
- 1977-03-31 JP JP3742177A patent/JPS52139087A/ja active Granted
- 1977-03-31 PH PH19616A patent/PH12676A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK140377A (da) | 1977-10-01 |
| NL7703465A (nl) | 1977-10-04 |
| IN144232B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-04-08 |
| NZ183626A (en) | 1978-11-13 |
| CA1069899A (en) | 1980-01-15 |
| AR212615A1 (es) | 1978-08-15 |
| IE45275B1 (en) | 1982-07-28 |
| JPS5437154B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-11-13 |
| PH12676A (en) | 1979-07-11 |
| GB1536393A (en) | 1978-12-20 |
| ES457359A1 (es) | 1978-06-16 |
| JPS52139087A (en) | 1977-11-19 |
| DK143701B (da) | 1981-09-28 |
| IE45275L (en) | 1977-09-30 |
| BE852913A (fr) | 1977-09-26 |
| DK143701C (da) | 1982-04-05 |
| MX4659E (es) | 1982-07-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |