GB928151A - Pyrazine derivatives - Google Patents
Pyrazine derivativesInfo
- Publication number
- GB928151A GB928151A GB24146/59A GB2414659A GB928151A GB 928151 A GB928151 A GB 928151A GB 24146/59 A GB24146/59 A GB 24146/59A GB 2414659 A GB2414659 A GB 2414659A GB 928151 A GB928151 A GB 928151A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- amino
- treating
- aminobenzenesulphonyl
- acetylamino
- 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
- 150000003216 pyrazines Chemical class 0.000 title 1
- -1 p-nitro-benzenesulphonyl Chemical group 0.000 abstract 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 3
- MTMGQKFGZHMTTK-UHFFFAOYSA-N 3-methoxypyrazin-2-amine Chemical compound COC1=NC=CN=C1N MTMGQKFGZHMTTK-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 2
- 159000000000 sodium salts Chemical class 0.000 abstract 2
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 abstract 1
- LTQARFFNSMGMTC-UHFFFAOYSA-N 4-amino-n-(3-chloropyrazin-2-yl)benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CN=C1Cl LTQARFFNSMGMTC-UHFFFAOYSA-N 0.000 abstract 1
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 abstract 1
- 125000003047 N-acetyl group Chemical group 0.000 abstract 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 239000003651 drinking water Substances 0.000 abstract 1
- 235000020188 drinking water Nutrition 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- 239000003826 tablet Substances 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
- C07D241/20—Nitrogen atoms
- C07D241/22—Benzenesulfonamido pyrazines
-
- 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
- C07D241/20—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises (1) compounds of the general formula <FORM:0928151/IV(a)/1> (wherein X represents OCH3 or OC2H5, Y represents H or Br, R1 represents H or Acyl, and R2 represents a p-amino-, p-acetylamino-or p-nitro-benzenesulphonyl group); (2) the preparation of the compounds in which X = OCH3 by the following processes: (a) (when R1 = H and R2 is a p-acetylamino-or p-amino-benzenesulphonyl group) treating 2-amino-3-methoxypyrazine or its 5-bromo derivative with p-acetylaminobenzenesulphonyl chloride and, if desired, hydrolysing the acetylamino group with aqueous alkali; (b) (when Y = H, R1 = H or acetyl and R2 = p-nitrobenzenesulphonyl) treating 2-amino-3-methoxypyrazine with p-nitrobenzenesulphonyl chloride and, if desired, treating the product with acetic anhydride in the presence of pyridine; (c) (when Y = H, R1 = acetyl and R2 = p-aminobenzenesulphonyl) catalytically hydrogenating the acetylated product of (b); (d) when Y = R1 = H and R2 = p-aminobenzenesulphonyl) treating 2-(p-aminobenzenesulphonamido)- or 2-(bis-p-acetylaminobenzenesulphonamido)- 3-chloropyrazine with an alkali metal methoxide (3 molecular proportions thereof being used in the latter case); (3) the preparation of 2-(p-aminobenzenesulphonamido)- 3- chloropyrazine by alkaline hydrolysis of its N-acetyl derivative. The products are therapeutically useful substances or intermediates therefor (see Group VI). Specifications 612,385 and 928,152 are referred to.ALSO:Compounds of the general formula <FORM:0928151/VI/1> (wherein X represents OCH3 or OC2H5, Y represents H or Br, R1 represents H or acyl, and R2 represents a p-aminobenzenesulphonyl group) or their sodium salts are useful as antibacterial agents. They may be administered, alone or in combination with other sulphonamides or with antibiotics, in the form of powders, tablets or pills, or mixed with food or drinking water. Solutions of the sodium salts may also be administered intravenously. Specifications 612,385 and 928,152 are referred to.
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3726/62A GB928152A (en) | 1959-07-14 | 1959-07-14 | Pyrazine derivatives |
| GB24146/59A GB928151A (en) | 1959-07-14 | 1959-07-14 | Pyrazine derivatives |
| DE1620381*CA DE1620381C3 (en) | 1959-07-14 | 1960-07-12 | 2-Amino-3-methoxy-pyrazine and process for its preparation |
| DE19601445127 DE1445127A1 (en) | 1959-07-14 | 1960-07-12 | Process for the preparation of pyrazine derivatives |
| ES0259911A ES259911A1 (en) | 1959-07-14 | 1960-07-13 | PROCEDURE FOR OBTAINING 3- AND 3,5-SUBSTITUTED DERIVATIVES OF 2-AMINOPYRAZINE |
| CH800260A CH397692A (en) | 1959-07-14 | 1960-07-13 | Process for the preparation of new 3-alkoxy-2-sulfanilamidopyrazines |
| FR832877A FR33M (en) | 1959-07-14 | 1960-07-13 | 3-methoxy-2-sulfanilamidopyrazine. |
| US139347A US3185686A (en) | 1959-07-14 | 1961-09-20 | Pyrazine derivatives |
| US222949A US3098069A (en) | 1959-07-14 | 1962-09-11 | Pyrazine derivatives |
| CY33365A CY333A (en) | 1959-07-14 | 1965-12-13 | Pyrazine derivatives |
| NL6612172A NL6612172A (en) | 1959-07-14 | 1966-08-30 | |
| MY196632A MY6600032A (en) | 1959-07-14 | 1966-12-31 | Pyrazine derivatives |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24146/59A GB928151A (en) | 1959-07-14 | 1959-07-14 | Pyrazine derivatives |
| GB883160 | 1960-03-14 | ||
| GB1440060 | 1960-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB928151A true GB928151A (en) | 1963-06-06 |
Family
ID=27255264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24146/59A Expired GB928151A (en) | 1959-07-14 | 1959-07-14 | Pyrazine derivatives |
Country Status (2)
| Country | Link |
|---|---|
| CY (1) | CY333A (en) |
| GB (1) | GB928151A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007069978A1 (en) * | 2005-12-12 | 2007-06-21 | Astrazeneca Ab | Novel n-(fluoro-pyrazinyl)-phenylsulfonamid.es as moodulators of chemokine receptor ccr4. |
-
1959
- 1959-07-14 GB GB24146/59A patent/GB928151A/en not_active Expired
-
1965
- 1965-12-13 CY CY33365A patent/CY333A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007069978A1 (en) * | 2005-12-12 | 2007-06-21 | Astrazeneca Ab | Novel n-(fluoro-pyrazinyl)-phenylsulfonamid.es as moodulators of chemokine receptor ccr4. |
Also Published As
| Publication number | Publication date |
|---|---|
| CY333A (en) | 1965-12-13 |
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