DE1620035A1 - 3-Amino-5-X-6-halogenpyrazinonitrile und Verfahren zu deren Herstellung - Google Patents
3-Amino-5-X-6-halogenpyrazinonitrile und Verfahren zu deren HerstellungInfo
- Publication number
- DE1620035A1 DE1620035A1 DE19661620035 DE1620035A DE1620035A1 DE 1620035 A1 DE1620035 A1 DE 1620035A1 DE 19661620035 DE19661620035 DE 19661620035 DE 1620035 A DE1620035 A DE 1620035A DE 1620035 A1 DE1620035 A1 DE 1620035A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- dimethyl
- radical
- bromine
- general formula
- 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 19
- 238000002360 preparation method Methods 0.000 title claims description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 3
- GPIZLEHIVRHDAW-UHFFFAOYSA-N 3-aminopyrazine-2-carbonitrile Chemical compound NC1=NC=CN=C1C#N GPIZLEHIVRHDAW-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 21
- -1 chlorine ions Chemical class 0.000 description 17
- 238000001953 recrystallisation Methods 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- OKSPUZDERJZNPO-UHFFFAOYSA-N 3-amino-6-chloropyrazine-2-carbonitrile Chemical compound NC1=NC=C(Cl)N=C1C#N OKSPUZDERJZNPO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- SDTCGHLDTSGIRR-UHFFFAOYSA-N 3,5-dichloropyrazine-2-carbonitrile Chemical compound ClC1=CN=C(C#N)C(Cl)=N1 SDTCGHLDTSGIRR-UHFFFAOYSA-N 0.000 description 2
- YRLKALFVUYUKGQ-UHFFFAOYSA-N 3-amino-6-chloropyrazine-2-carboxamide Chemical compound NC(=O)C1=NC(Cl)=CN=C1N YRLKALFVUYUKGQ-UHFFFAOYSA-N 0.000 description 2
- SDLFAEGTVBPHBK-UHFFFAOYSA-N 3-chloropyrazine-2-carbonitrile Chemical compound ClC1=NC=CN=C1C#N SDLFAEGTVBPHBK-UHFFFAOYSA-N 0.000 description 2
- YHPMRHPLAQSPHJ-UHFFFAOYSA-N 3-chloropyrazine-2-carboxamide Chemical compound NC(=O)C1=NC=CN=C1Cl YHPMRHPLAQSPHJ-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 101150046432 Tril gene Proteins 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229960005206 pyrazinamide Drugs 0.000 description 2
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical group NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ISJBQSJDQZLCSF-UHFFFAOYSA-N (4-chlorophenyl)azanium;chloride Chemical compound [Cl-].[NH3+]C1=CC=C(Cl)C=C1 ISJBQSJDQZLCSF-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- GELVZYOEQVJIRR-UHFFFAOYSA-N 2-chloropyrazine Chemical compound ClC1=CN=CC=N1 GELVZYOEQVJIRR-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- KRRTXVSBTPCDOS-UHFFFAOYSA-N 5-bromopyrazin-2-amine Chemical compound NC1=CN=C(Br)C=N1 KRRTXVSBTPCDOS-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 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
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 239000002775 capsule Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229960001448 chloropyramine Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- JGAJCAJHSHUPGH-UHFFFAOYSA-N methyl 3-amino-6-chloropyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=CN=C1N JGAJCAJHSHUPGH-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical compound [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 229940086542 triethylamine Drugs 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)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US492862A US3341540A (en) | 1965-10-04 | 1965-10-04 | 3-amino-6-halopyrazinonitriles and their syntheses |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1620035A1 true DE1620035A1 (de) | 1970-02-12 |
Family
ID=23957913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661620035 Pending DE1620035A1 (de) | 1965-10-04 | 1966-10-03 | 3-Amino-5-X-6-halogenpyrazinonitrile und Verfahren zu deren Herstellung |
Country Status (6)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4402959A (en) * | 1980-06-02 | 1983-09-06 | Merck & Co., Inc. | Antimicrobial compositions |
| US4517186A (en) * | 1982-09-30 | 1985-05-14 | Merck & Co., Inc. | 2-Amino-3,5-dicyano-6-(substituted)pyrazine antimicrobial compounds |
| US4518599A (en) * | 1982-09-30 | 1985-05-21 | Merck & Co., Inc. | 2-Amino-3-cyano-5-halo-6-(substituted)pyrazine |
| US4512991A (en) * | 1982-12-27 | 1985-04-23 | Merck & Co., Inc. | 3-Acyl-2-amino-5-halo-6-(substituted)pyrazine antimicrobial compounds |
| US4507299A (en) * | 1982-12-27 | 1985-03-26 | Merck & Co., Inc. | N-[2-amino-5-halo-6-(substituted)-3-pyrazinyl)-methylene]amine antimicrobial compounds |
| US4442097A (en) * | 1982-12-27 | 1984-04-10 | Merck & Co., Inc. | 3-Acyl-2-(substituted) amino-5-halo-6-(substituted) pyrazine antimicrobial compounds, compositions and use |
| US4442096A (en) * | 1982-12-27 | 1984-04-10 | Merck & Co., Inc. | 2-(Substituted)amino-3-cyano-5-halo-6-(substituted)-pyrazine antimicrobial compounds, compositions and use |
| US4481202A (en) * | 1982-12-27 | 1984-11-06 | Merek & Co., Inc. | 2-Amino-3-carboxylate-5-halo-6-(substituted)pyrazine antimicrobial compounds |
| US4442095A (en) * | 1982-12-27 | 1984-04-10 | Merck & Co., Inc. | N-[(5-Halo-2,6-(substituted)pyrazinyl)methylene]amine antimicrobial compounds, compositions and use |
| EP0132476B1 (en) * | 1983-07-28 | 1987-07-15 | Merck & Co. Inc. | Antimicrobial compositions |
| US4479953A (en) * | 1983-08-25 | 1984-10-30 | Merck & Co., Inc. | Pyrazine aldimine compounds as antimicrobial agents |
| 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 |
| US7745442B2 (en) | 2003-08-20 | 2010-06-29 | Parion Sciences, Inc. | Methods of reducing risk of infection from pathogens |
| 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 |
| JP6392242B2 (ja) | 2012-12-17 | 2018-09-19 | パリオン・サイエンシィズ・インコーポレーテッド | 粘膜への水分付与が不十分であることが好都合である疾患の治療に有用なクロロ−ピラジンカルボキサミド誘導体 |
| AU2013363215B2 (en) | 2012-12-17 | 2018-03-01 | Parion Sciences, Inc. | 3,5-diamino-6-chloro-N-(N-(4-phenylbutyl)carbamimidoyl) pyrazine-2- carboxamide compounds |
| US9102633B2 (en) | 2013-12-13 | 2015-08-11 | Parion Sciences, Inc. | Arylalkyl- and aryloxyalkyl-substituted epithelial sodium channel blocking compounds |
-
1965
- 1965-10-04 US US492862A patent/US3341540A/en not_active Expired - Lifetime
-
1966
- 1966-09-28 GB GB43400/66A patent/GB1149639A/en not_active Expired
- 1966-09-28 CH CH1397566A patent/CH478128A/de not_active IP Right Cessation
- 1966-09-29 BR BR183284/66A patent/BR6683284D0/pt unknown
- 1966-10-03 NL NL6613934A patent/NL6613934A/xx unknown
- 1966-10-03 DE DE19661620035 patent/DE1620035A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BR6683284D0 (pt) | 1973-12-26 |
| NL6613934A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-04-05 |
| CH478128A (de) | 1969-09-15 |
| GB1149639A (en) | 1969-04-23 |
| US3341540A (en) | 1967-09-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0427765B1 (de) | Alkoxy-4(1h)-pyridon-derivative, verfahren zu deren herstellung und deren verwendung als arzneimittel | |
| DE1620035A1 (de) | 3-Amino-5-X-6-halogenpyrazinonitrile und Verfahren zu deren Herstellung | |
| EP0726899A1 (de) | Neue pyrazincarboxamidderivate, ihre herstellung und ihre verwendung in arzneimitteln | |
| DE2505297C3 (de) | Verfahren zur Herstellung von in 2- und 6-Stellung des Phenylkerns substituierten 2-Phenylamino-2-imidazoun-Derivaten | |
| DE60006054T2 (de) | Herstellungsverfahren für Pyridinderivate | |
| DE3688004T2 (de) | Verfahren zur herstellung herbizider 2-(4,4-disubstituierter-5-oxo-2-imidazolin-2yl)benzoesaeuren, -nicotinsaeuren und chinolin-3-carbonsaeuren, ester und salze. | |
| DE1670753A1 (de) | Verfahren zur Herstellung von 2-Cycloalkylaminooxazolinen | |
| DE2356903A1 (de) | Verfahren zur herstellung substituierter chromon-3-carbonitrile, -carboxamide und -carbonsaeuren | |
| DE68922760T2 (de) | Verfahren zur Herstellung von (3,5-Dioxopiperazinyl)-alkanen oder -alkenen. | |
| DE2446254C2 (de) | 5-Substituierte Niedrigalkyl-1,3,4-thiadiazol-2-thiol-Verbindungen und Verfahren zu ihrer Herstellung | |
| DE2225149C2 (de) | Oxofurylesterderivate der 6-(ą-Aminophenylacetamido)penicillansäure, Verfahren zu deren Herstellung und ihre Verwendung | |
| CH638516A5 (en) | Process for preparing substituted aminoquinazoline derivatives | |
| DE2427503C3 (de) | Halogenfusarsäureamide, Verfahren zur Herstellung derselben und Mittel mit einem Gehalt derselben | |
| DE2720915C2 (de) | N↓1↓-Acyl-2-hydroxy-1,3-diaminopropane und Arzneimittel mit diesen Verbindungen als Wirkstoff | |
| AT250338B (de) | Verfahren zur Herstellung neuer, basischer Derivate von substituierten Benzofuran-2-carbonsäuren und deren Salzen | |
| DE3530061A1 (de) | Verfahren zur herstellung von guanidinothiazolderivaten | |
| DD150057A5 (de) | Verfahren zur herstellung von 2-aminopyrazinen | |
| EP0004904B1 (de) | 2-Amino-3a,4,5,6-tetrahydro-perimidin-Derivate, diese enthaltende Arzneimittel und Verfahren zu ihrer Herstellung | |
| DE1620128A1 (de) | Verfahren zur Herstellung von neuen organischen Amiden | |
| CH493535A (de) | Verfahren zur Herstellung von Pyrazinoylguanidinen und Pyrazinamidoguanidinen | |
| AT258916B (de) | Verfahren zur Herstellung von neuen Alkyl-3-amino-5-chlor-6-X-pyrazinoaten | |
| DE2728870C2 (de) | Verfahren zur Herstellung von D-Penicillamin und dessen Salzen | |
| CH630625A5 (en) | Process for the preparation of antihypertensive 6,7-dimethoxy-4-amino-2-[4-(2-furoyl)-1-piperazinyl]quinazoline | |
| DE3710254A1 (de) | Antiulcusmittel | |
| AT362353B (de) | Verfahren zur herstellung von neuen in 4- -stellung substituierten 3-sulfamoyl-5-pyrrolyl - oder -5-pyrrolylalkylbenzoesaeuren und ihren salzen |