ES357877A1 - 3,5-diamino-6-halo-pyrazinamide derivatives - Google Patents
3,5-diamino-6-halo-pyrazinamide derivativesInfo
- Publication number
- ES357877A1 ES357877A1 ES357877A ES357877A ES357877A1 ES 357877 A1 ES357877 A1 ES 357877A1 ES 357877 A ES357877 A ES 357877A ES 357877 A ES357877 A ES 357877A ES 357877 A1 ES357877 A1 ES 357877A1
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- phenyl
- group
- alkoxy
- amino
- 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
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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
3,5 - Diamino - 6 - halo - pyrazinamide derivatives of the general formula wherein R1 is a hydrogen atom or a C 1-5 alkyl, C 3-5 alkenyl, C 3-5 alkynyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-3 alkyl, di(C 1-3 alkyl)amino-methyl-C 1-3 alkyl, (hydroxy-C 1-5 alkyl)methyl, (polyhydroxy - C 1-5 alkyl) - methyl, #, #, # - trifluoro-C 1-3 alkyl, phenyl-C 1-3 alkyl, halophenyl- C 1-3 alkyl, heterocyclic-C 1-3 alkyl in which the heterocyclic moiety is a 5- or 6-membered ring containing oxygen or nitrogen or both, phenyl, halophenyl, C 1-3 alkyl-phenyl, C 1-3 alkoxy, phenyl-C 1-3 alkoxy or amino group and R2 is a hydrogen atom or a C 1-5 alkyl group or R1 and R2 are alkylene groups linked together directly or through a hetero atom to form a heterocyclic structure with the nitrogen atom to which they are attached Y is a chlorine, bromine or iodine atom and R6 is a C 1-5 alkyl, C 1-3 alkoxymethyl-C 1-5 alkyl, cyano.C 1-5 alkyl, (C 1-3 alkoxy)carbonyl-C 1-5 alkyl, phenyl-C 1-5 alkyl, di-(C 1-3 alkyl)aminomethyl-C 1-5 alkyl, 2 - (2 - imidazolinyl) - amino - methyl - C 1-5 alkyl, 1-pyrrolidinyl-C 1-5 alkyl, piperidino-C 1-5 alkyl, hexahydro-1-azepinyl-C 1-5 alkyl, morpholino-C 1-5 alkyl, 4-(C 1-3 alkyl)-1 -piperazinyl-C 1-5 alkyl, pyridyl-C 1-5 alkyl, faryl-C 1-5 alkyl, tetrahydropyranyl-C 1-5 alkyl, C 3-5 alkenyl, C 3-5 alkynyl, phenyl, halophenyl, C 1-3 alkyl-phenyl, C 1-3 alkoxy-phenyl, cyano, amino, di(C 1-3 alkyl)- amino, N-C 1-3 alkyl-N-(phenyl - C 1-3 alkyl)- amino, di[phenyl- (C 1-3 alkyl)]amino, pyridylamino, pyrimidinylamino, quinolinylamino, pyrrolidino, piperidino, hexahydro-1-azepinyl, morpholino or 4-(3,5-diamino- 1,2,4-triazolyl) group a group of the formula in which R7 is a C 1-5 alkyl, phenyl, halophenyl, C 1-3 alkyl-phenyl or C 1-3 alkoxy-phenyl group a group of the formula in which R8 is a hydrogen atom or a phenyl or C 1-5 alkyl group, R9 is a hydrogen atom or a C 1-5 alkyl, hydroxy-C 1-5 alkyl, phenyl-C 1-5 alkyl, halophenyl-C 1-5 alkyl, (C 1-3 alkyl)-phenyl- C 1-5 alkyl, (C 1-3 alkoxy)-phenyl-C 1-5 alkyl, naphthyl-C 1-5 alkyl, balonaphthyl-C 1-5 alkyl, (C 1-3 alkyl) - naphthyl - C 1-5 alkyl, (C 1-3 alkoxy) - naphthyl - C 1-5 alkyl, pyridyl - C 1-5 alkyl, morpholino-C 1-5 alkyl, furyl-C 1-5 alkyl, 1 - pyrrolidyl - C 1-5 alkyl, C 1-3 alkoxy-C 1-5 alkyl, C 3-5 alkenyl, C 2-5 alkylideneamino, (phenyl - C 2-5 alkylidene)amino, hydroxy, phenyl, C 1-3 alkyl-phenyl, C 1-3 alkoxy-phenyl, halophenyl, C 1-3 alkoxy or phenyl-C 1-3 alkoxy group and R10 is a hydrogenation or a C 1-5 alkyl group, or R9 and R10 are alkylene groups linked together to form, with the nitrogen atom to which they are attached, a heterocyclic ring containing from 5 to 8 atoms, optionally including a further heteroatom, or R8 and R9 are alkylene groups linked together to form, with the nitrogen atom to which they are attached, a heterocyclic ring containing from 5 to 7 ring atoms a group of the formula in which R11 is an hydrogen atom or a C 1-5 alkyl group, R12 is a hydrogen atom or a C 1-5 alkyl, hydroxy-C 1-5 alkyl, phenyl-C 1-5 alkyl, halophenyl-C 1-5 alkyl, (C 1-3 alkyl)-phenyl-C 1-5 alkyl, phenyl, halophenyl, C 1-3 alkyl-phenyl, C 1-3 alkoxy-phenyl or amino group and R13 is a hydrogen atom, or R11 and R13 are alkylene groups linked together to form a diazacyclic ring containing from 5 to 7 ring atoms with the nitrogen atoms to which they are attached are prepared by reaction of a 3,5-diamino-6-halopyrazinoyloxyacrylamide of the general formula wherein R3 is a methyl, ethyl, n-propyl, isopropyl, phenyl, (C 1-3 alkyl)-phenyl or sulphophenyl group, in which case an internal salt is formed with an amino group and R4 is a hydrogen atom or R3 and R4 are linked to form an o-phenylene group with the carbon atom to which R3 and R4 are attached R5 is a C 1-5 alkyl group with an amine of the general formula R6NH 2 . Certain of the 3,5-diamino-6- halo-pyrazinamide derivatives of the first general formula above are novel.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US66600467A | 1967-09-07 | 1967-09-07 | |
US71897668A | 1968-03-21 | 1968-03-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
ES357877A1 true ES357877A1 (en) | 1970-05-01 |
Family
ID=27099350
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES357877A Expired ES357877A1 (en) | 1967-09-07 | 1968-09-05 | 3,5-diamino-6-halo-pyrazinamide derivatives |
Country Status (15)
Country | Link |
---|---|
AT (1) | AT289123B (en) |
BE (1) | BE720233A (en) |
CA (1) | CA939345A (en) |
CH (1) | CH534168A (en) |
DK (1) | DK145892C (en) |
ES (1) | ES357877A1 (en) |
FI (1) | FI50975C (en) |
FR (1) | FR8490M (en) |
GB (2) | GB1214409A (en) |
IL (1) | IL30634A0 (en) |
NL (1) | NL6812003A (en) |
NO (1) | NO125678B (en) |
OA (1) | OA02886A (en) |
SE (1) | SE355811B (en) |
YU (2) | YU205268A (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104024244B (en) | 2011-11-02 | 2016-09-14 | 勃林格殷格翰国际有限公司 | Heterocyclic compound, medicine containing described compound and application thereof and its preparation method |
WO2013064451A1 (en) * | 2011-11-02 | 2013-05-10 | Boehringer Ingelheim International Gmbh | Novel process for the preparation of acylguanidines and acylthioureas |
US8859559B2 (en) | 2011-12-20 | 2014-10-14 | Boehringer Ingelheim International Gmbh | Substituted pyrazines and their use in the treatment of disease |
WO2013174757A1 (en) | 2012-05-25 | 2013-11-28 | Boehringer Ingelheim International Gmbh | Tertiary amines, medicaments containing said amines, use thereof and processes for the preparation thereof |
EP2897940B1 (en) | 2012-09-24 | 2019-05-01 | Boehringer Ingelheim International GmbH | Heterocyclic compounds, medicaments containing said compounds, use thereof and processes for the preparation thereof |
-
1968
- 1968-08-22 NL NL6812003A patent/NL6812003A/xx unknown
- 1968-08-26 IL IL30634A patent/IL30634A0/en unknown
- 1968-08-28 FI FI682412A patent/FI50975C/en active
- 1968-08-30 BE BE720233D patent/BE720233A/xx unknown
- 1968-08-31 CA CA028,994A patent/CA939345A/en not_active Expired
- 1968-09-02 YU YU02052/68A patent/YU205268A/en unknown
- 1968-09-03 GB GB53830/69A patent/GB1214409A/en not_active Expired
- 1968-09-03 GB GB41777/68A patent/GB1214408A/en not_active Expired
- 1968-09-04 OA OA53362A patent/OA02886A/en unknown
- 1968-09-05 ES ES357877A patent/ES357877A1/en not_active Expired
- 1968-09-05 SE SE11956/68A patent/SE355811B/xx unknown
- 1968-09-06 NO NO3467/68A patent/NO125678B/no unknown
- 1968-09-06 DK DK429268A patent/DK145892C/en active
- 1968-09-06 CH CH1340268A patent/CH534168A/en not_active IP Right Cessation
- 1968-09-06 AT AT872468A patent/AT289123B/en not_active IP Right Cessation
- 1968-12-06 FR FR176992A patent/FR8490M/fr not_active Expired
-
1969
- 1969-09-02 YU YU2052/68A patent/YU34082B/en unknown
Also Published As
Publication number | Publication date |
---|---|
CH534168A (en) | 1973-02-28 |
OA02886A (en) | 1970-12-15 |
DK145892B (en) | 1983-04-05 |
SE355811B (en) | 1973-05-07 |
FI50975B (en) | 1976-05-31 |
YU205268A (en) | 1978-06-30 |
YU34082B (en) | 1978-12-31 |
GB1214409A (en) | 1970-12-02 |
BE720233A (en) | 1969-02-28 |
AT289123B (en) | 1971-04-13 |
NO125678B (en) | 1972-10-16 |
FI50975C (en) | 1976-09-10 |
CA939345A (en) | 1974-01-01 |
FR8490M (en) | 1973-07-27 |
NL6812003A (en) | 1969-03-11 |
DK145892C (en) | 1983-09-12 |
GB1214408A (en) | 1970-12-02 |
IL30634A0 (en) | 1968-10-24 |
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