GB1149639A - 3-amino-6-halopyrazinonitriles and their preparation - Google Patents
3-amino-6-halopyrazinonitriles and their preparationInfo
- Publication number
- GB1149639A GB1149639A GB43400/66A GB4340066A GB1149639A GB 1149639 A GB1149639 A GB 1149639A GB 43400/66 A GB43400/66 A GB 43400/66A GB 4340066 A GB4340066 A GB 4340066A GB 1149639 A GB1149639 A GB 1149639A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- bromo
- chloro
- alkyl
- alkoxy
- 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
Links
- 125000001246 bromo group Chemical group Br* 0.000 abstract 7
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- 125000004414 alkyl thio group Chemical group 0.000 abstract 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- GPIZLEHIVRHDAW-UHFFFAOYSA-N 3-aminopyrazine-2-carbonitrile Chemical compound NC1=NC=CN=C1C#N GPIZLEHIVRHDAW-UHFFFAOYSA-N 0.000 abstract 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 abstract 1
- DBPRLIBYSBDJSQ-UHFFFAOYSA-N NC=1C(=NC(=C[N+]1[O-])Br)C(=O)OC Chemical compound NC=1C(=NC(=C[N+]1[O-])Br)C(=O)OC DBPRLIBYSBDJSQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001339 alkali metal compounds Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- -1 bromo- Chemical class 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- SZBZQXNUHNQIJV-UHFFFAOYSA-N methyl 3-amino-5,6-dibromopyrazine-2-carboxylate Chemical compound NC=1C(=NC(=C(N1)Br)Br)C(=O)OC SZBZQXNUHNQIJV-UHFFFAOYSA-N 0.000 abstract 1
- MEYTYCRWYBFDOW-UHFFFAOYSA-N methyl 3-amino-6-bromo-5-chloropyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Br)=C(Cl)N=C1N MEYTYCRWYBFDOW-UHFFFAOYSA-N 0.000 abstract 1
- CNXSIRHOIFRMOB-UHFFFAOYSA-N methyl 3-amino-6-bromopyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Br)=CN=C1N CNXSIRHOIFRMOB-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 abstract 1
- 229960005206 pyrazinamide Drugs 0.000 abstract 1
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 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 |
|---|---|
| GB1149639A true GB1149639A (en) | 1969-04-23 |
Family
ID=23957913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB43400/66A Expired GB1149639A (en) | 1965-10-04 | 1966-09-28 | 3-amino-6-halopyrazinonitriles and their preparation |
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 |
| US4518599A (en) * | 1982-09-30 | 1985-05-21 | Merck & Co., Inc. | 2-Amino-3-cyano-5-halo-6-(substituted)pyrazine |
| US4517186A (en) * | 1982-09-30 | 1985-05-14 | Merck & Co., Inc. | 2-Amino-3,5-dicyano-6-(substituted)pyrazine antimicrobial compounds |
| 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 |
| US4512991A (en) * | 1982-12-27 | 1985-04-23 | Merck & Co., Inc. | 3-Acyl-2-amino-5-halo-6-(substituted)pyrazine 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 |
| 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 |
| US4481202A (en) * | 1982-12-27 | 1984-11-06 | Merek & Co., Inc. | 2-Amino-3-carboxylate-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 |
| 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 |
| RU2018138195A (ru) | 2012-12-17 | 2018-12-18 | Пэрион Сайенсиз, Инк. | Соединения 3,5-диамино-6-хлор-n-(n-(4- фенилбутил)карбамимидоил)пиразин-2-карбоксамида |
| AU2013363218B2 (en) | 2012-12-17 | 2018-03-15 | Parion Sciences, Inc. | Chloro-pyrazine carboxamide derivatives useful for the treatment of diseases favoured by insufficient mucosal hydration |
| 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 CH CH1397566A patent/CH478128A/de not_active IP Right Cessation
- 1966-09-28 GB GB43400/66A patent/GB1149639A/en not_active Expired
- 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 |
| DE1620035A1 (de) | 1970-02-12 |
| US3341540A (en) | 1967-09-12 |
| CH478128A (de) | 1969-09-15 |
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