DE1245967B - Verfahren zur Herstellung von S.S-Diamino-o-chlor-pyrazincarbonsäurealkylestern - Google Patents
Verfahren zur Herstellung von S.S-Diamino-o-chlor-pyrazincarbonsäurealkylesternInfo
- Publication number
- DE1245967B DE1245967B DENDAT1245967D DE1245967DA DE1245967B DE 1245967 B DE1245967 B DE 1245967B DE NDAT1245967 D DENDAT1245967 D DE NDAT1245967D DE 1245967D A DE1245967D A DE 1245967DA DE 1245967 B DE1245967 B DE 1245967B
- Authority
- DE
- Germany
- Prior art keywords
- pyrazine
- chloro
- diamino
- carboxylic acid
- acid alkyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 11
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- USYMCUGEGUFUBI-UHFFFAOYSA-N methyl 3-amino-5,6-dichloropyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=C(Cl)N=C1N USYMCUGEGUFUBI-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- UFOUSHWZVOIJKK-UHFFFAOYSA-N 3-amino-5,6-dichloropyrazine-2-carboxylic acid Chemical compound NC1=NC(Cl)=C(Cl)N=C1C(O)=O UFOUSHWZVOIJKK-UHFFFAOYSA-N 0.000 description 1
- -1 B. Dimethylsulfoxyd Chemical class 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- KOOBYHRLTYIPTH-UHFFFAOYSA-N methyl 3,5-diamino-6-chloropyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=C(N)N=C1N KOOBYHRLTYIPTH-UHFFFAOYSA-N 0.000 description 1
- INCSQLZZXBPATR-UHFFFAOYSA-N methyl 3-aminopyrazine-2-carboxylate Chemical compound COC(=O)C1=NC=CN=C1N INCSQLZZXBPATR-UHFFFAOYSA-N 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings 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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US356038A US3290311A (en) | 1964-03-31 | 1964-03-31 | Derivatives of 3, 5-diamino-6-chloropyrazinoic acid esters and a process for making them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1245967B true DE1245967B (de) | 1967-08-03 |
Family
ID=23399854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1245967D Pending DE1245967B (de) | 1964-03-31 | Verfahren zur Herstellung von S.S-Diamino-o-chlor-pyrazincarbonsäurealkylestern |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3290311A (en, 2012) |
| BE (1) | BE653477A (en, 2012) |
| CH (1) | CH488709A (en, 2012) |
| DE (1) | DE1245967B (en, 2012) |
| FR (1) | FR94601E (en, 2012) |
| NL (1) | NL6409712A (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6858615B2 (en) | 2002-02-19 | 2005-02-22 | Parion Sciences, Inc. | Phenyl guanidine sodium channel blockers |
| US6903105B2 (en) | 2003-02-19 | 2005-06-07 | Parion Sciences, Inc. | Sodium channel blockers |
| AR086745A1 (es) | 2011-06-27 | 2014-01-22 | Parion Sciences Inc | 3,5-diamino-6-cloro-n-(n-(4-(4-(2-(hexil(2,3,4,5,6-pentahidroxihexil)amino)etoxi)fenil)butil)carbamimidoil)pirazina-2-carboxamida |
| CN104995178B (zh) | 2012-12-17 | 2018-06-26 | 帕里昂科学公司 | 3，5-二氨基-6-氯-n-(n-(4-苯基丁基)甲脒基)吡嗪-2-甲酰胺化合物 |
| HRP20170060T1 (hr) | 2012-12-17 | 2017-03-10 | Parion Sciences, Inc. | Derivati klor-pirazin karboksamida korisni za liječenje bolesti kojima pogoduje nedovoljna hidratacija sluznice |
| US9102633B2 (en) | 2013-12-13 | 2015-08-11 | Parion Sciences, Inc. | Arylalkyl- and aryloxyalkyl-substituted epithelial sodium channel blocking compounds |
| CN107533217A (zh) | 2015-03-13 | 2018-01-02 | 格尼亚Ip控股私人有限公司 | 用于显微技术的方法与装置 |
-
0
- DE DENDAT1245967D patent/DE1245967B/de active Pending
-
1964
- 1964-03-31 US US356038A patent/US3290311A/en not_active Expired - Lifetime
- 1964-08-21 NL NL6409712A patent/NL6409712A/xx unknown
- 1964-08-25 FR FR986155A patent/FR94601E/fr not_active Expired
- 1964-09-23 BE BE653477D patent/BE653477A/xx unknown
-
1965
- 1965-02-04 CH CH153065A patent/CH488709A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR94601E (fr) | 1969-09-19 |
| CH488709A (de) | 1970-04-15 |
| NL6409712A (en, 2012) | 1965-10-01 |
| BE653477A (en, 2012) | 1965-03-23 |
| US3290311A (en) | 1966-12-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1245967B (de) | Verfahren zur Herstellung von S.S-Diamino-o-chlor-pyrazincarbonsäurealkylestern | |
| DE3104644A1 (de) | Verfahren zur herstellung von dimethylsuccinylosuccinat, dessen dinatriumsalz, dianilinodihydroterephthalsaeuren, deren dimethylestern und salzen sowie von dianilinoterephthalsaeuren, deren dimethylestern und salzen | |
| CH626352A5 (en) | Process for the preparation of 2,6-disubstituted 2-phenyliminoimidazolidines and their acid addition salts | |
| DE1238478B (de) | Verfahren zur Herstellung von 3-Amino-pyrazin-carbonsaeurederivaten | |
| DE3235372C2 (en, 2012) | ||
| DE1620286B1 (de) | Verfahren zur Herstellung von Pyrrolderivaten | |
| CH640835A5 (de) | Verfahren zur herstellung von 3-hydroxy-5-halogenpyridinen. | |
| CH610330A5 (en) | Process for the preparation of novel ergopeptins | |
| CH626332A5 (en, 2012) | ||
| DE3320089A1 (de) | Verfahren zur herstellung von fluorphtsaeureimiden | |
| DE1158500B (de) | Verfahren zur Herstellung von Polyisonitrilen | |
| AT249682B (de) | Verfahren zur Herstellung von 3,5-Diamino-6-chlor-pyrazincarbonsäureestern | |
| DE1670296A1 (de) | Verfahren zur Herstellung von substituierten Phosphiniminen und entsprechenden Amidophosphoniumhalogeniden | |
| DE2708184A1 (de) | Verfahren zur herstellung von alpha- ketocarbonsaeureamiden (a) | |
| DE2943125A1 (de) | Verfahren zur herstellung von 1-(4-chlorbenzoyl)-5-methoxy-2-methyl-3-indol acetoxyessigsaeure | |
| DE1545941C3 (de) | Verfahren zur Herstellung von 5-Phenyl-7-nitro-3H-1,4-benzodiazepin-2(1H)-on | |
| DE2660213C2 (de) | Verfahren zur Herstellung von Acylcyaniden | |
| DE1199756B (de) | Verfahren zur Herstellung von 1, 3, 5-Trifluor-2, 4, 6-tricyan-benzol | |
| AT372939B (de) | Verfahren zur herstellung von (d)-(-)-phydroxyphenylglycylchlorid-hydrochlorid | |
| CH602766A5 (en) | 10-Alpha-methoxy-di:hydro-beta-ergosine derivs. | |
| AT372940B (de) | Verfahren zur herstellung von (d)-(-)-phydroxyphenylglycylchlorid-hydrochlorid | |
| DE3144765A1 (de) | Verfahren zur herstellung von chlorlactonen aus ungesaettigten carbonsaeuren | |
| DE911493C (de) | Verfahren zur Herstellung von 2-(1, 4-Diamino-2-anthrachinonyl)-1, 3, 4-oxydiazolen | |
| AT227690B (de) | Verfahren zur Herstellung neuer, basisch substituierter Succinimide | |
| DE2640616B2 (de) | Verfahren zur Herstellung von N-Acyl-2-arylglycinen |