GB1214408A - 3,5-diamino-6-halo-pyrazinamide derivatives - Google Patents
3,5-diamino-6-halo-pyrazinamide derivativesInfo
- Publication number
- GB1214408A GB1214408A GB41777/68A GB4177768A GB1214408A GB 1214408 A GB1214408 A GB 1214408A GB 41777/68 A GB41777/68 A GB 41777/68A GB 4177768 A GB4177768 A GB 4177768A GB 1214408 A GB1214408 A GB 1214408A
- Authority
- GB
- United Kingdom
- 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
1,214,408. 3,5 - Diamino - 6 - halo - pyrazinamide derivatives. MERCK & CO. Inc. 3 Sept., 1968 [7 Sept., 1967; 21 March, 1968], No. 41777/68. Heading C2C. [Also in Division A5] 3,5 - Diamino - 6 - halo - pyrazinamide derivatives of the general formula wherein R<SP>1</SP> 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 R<SP>2</SP> is a hydrogen atom or a C 1-5 alkyl group; or R<SP>1</SP> and R<SP>2</SP> 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 R<SP>6</SP> 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 R<SP>7</SP> 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 R<SP>8</SP> is a hydrogen atom or a phenyl or C 1-5 alkyl group, R<SP>9</SP> 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 R<SP>10</SP> is a hydrogenation or a C 1-5 alkyl group, or R<SP>9</SP> and R<SP>10</SP> 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 R<SP>8</SP> and R<SP>9</SP> 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 R<SP>11</SP> is an hydrogen atom or a C 1-5 alkyl group, R<SP>12</SP> 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 R<SP>13</SP> is a hydrogen atom, or R<SP>11</SP> and R<SP>13</SP> 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 R<SP>3</SP> 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 R<SP>4</SP> is a hydrogen atom; or R<SP>3</SP> and R<SP>4</SP> are linked to form an o-phenylene group with the carbon atom to which R<SP>3</SP> and R<SP>4</SP> are attached; R<SP>5</SP> is a C 1-5 alkyl group; with an amine of the general formula R<SP>6</SP>NH 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 |
|---|---|
| GB1214408A true GB1214408A (en) | 1970-12-02 |
Family
ID=27099350
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB41777/68A Expired GB1214408A (en) | 1967-09-07 | 1968-09-03 | 3,5-diamino-6-halo-pyrazinamide derivatives |
| GB53830/69A Expired GB1214409A (en) | 1967-09-07 | 1968-09-03 | Novel pyrazine derivatives and their preparation |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB53830/69A Expired GB1214409A (en) | 1967-09-07 | 1968-09-03 | Novel pyrazine derivatives and their preparation |
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) | GB1214408A (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) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013064451A1 (en) * | 2011-11-02 | 2013-05-10 | Boehringer Ingelheim International Gmbh | Novel process for the preparation of acylguanidines and acylthioureas |
| US8759349B2 (en) | 2011-11-02 | 2014-06-24 | Boehringer Ingelheim International Gmbh | Heterocyclic compounds, medicaments containing said compounds, use thereof and processes for the preparation thereof |
| US8841309B2 (en) | 2012-09-24 | 2014-09-23 | Boehringer Ingelheim International Gmbh | Substituted pyrazines and their use in the treatment of disease |
| US8859559B2 (en) | 2011-12-20 | 2014-10-14 | Boehringer Ingelheim International Gmbh | Substituted pyrazines and their use in the treatment of disease |
| US9078909B2 (en) | 2012-05-25 | 2015-07-14 | Boehringer Ingelheim International Gmbh | Tertiary amines, medicaments containing said amines, 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 GB41777/68A patent/GB1214408A/en not_active Expired
- 1968-09-03 GB GB53830/69A patent/GB1214409A/en not_active Expired
- 1968-09-04 OA OA53362A patent/OA02886A/en unknown
- 1968-09-05 SE SE11956/68A patent/SE355811B/xx unknown
- 1968-09-05 ES ES357877A patent/ES357877A1/en not_active Expired
- 1968-09-06 NO NO3467/68A patent/NO125678B/no unknown
- 1968-09-06 DK DK429268A patent/DK145892C/en active
- 1968-09-06 AT AT872468A patent/AT289123B/en not_active IP Right Cessation
- 1968-09-06 CH CH1340268A patent/CH534168A/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
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013064451A1 (en) * | 2011-11-02 | 2013-05-10 | Boehringer Ingelheim International Gmbh | Novel process for the preparation of acylguanidines and acylthioureas |
| US8759349B2 (en) | 2011-11-02 | 2014-06-24 | Boehringer Ingelheim International Gmbh | Heterocyclic compounds, medicaments containing said compounds, use thereof and processes for the preparation thereof |
| US8791260B2 (en) | 2011-11-02 | 2014-07-29 | Boehringer Ingelheim International Gmbh | Process for the preparation of acylguanidines and acylthioureas |
| CN104024231A (en) * | 2011-11-02 | 2014-09-03 | 勃林格殷格翰国际有限公司 | Novel process for the preparation of acylguanidines and acylthioureas |
| US9920035B2 (en) | 2011-11-02 | 2018-03-20 | Boehringer Ingelheim International Gmbh | Heterocyclic compounds, medicaments containing said compounds, use thereof and processes for the preparation thereof |
| US8859559B2 (en) | 2011-12-20 | 2014-10-14 | Boehringer Ingelheim International Gmbh | Substituted pyrazines and their use in the treatment of disease |
| US9078909B2 (en) | 2012-05-25 | 2015-07-14 | Boehringer Ingelheim International Gmbh | Tertiary amines, medicaments containing said amines, use thereof and processes for the preparation thereof |
| US8841309B2 (en) | 2012-09-24 | 2014-09-23 | Boehringer Ingelheim International Gmbh | Substituted pyrazines and their use in the treatment of disease |
Also Published As
| Publication number | Publication date |
|---|---|
| SE355811B (en) | 1973-05-07 |
| ES357877A1 (en) | 1970-05-01 |
| IL30634A0 (en) | 1968-10-24 |
| GB1214409A (en) | 1970-12-02 |
| YU34082B (en) | 1978-12-31 |
| NO125678B (en) | 1972-10-16 |
| DK145892B (en) | 1983-04-05 |
| DK145892C (en) | 1983-09-12 |
| YU205268A (en) | 1978-06-30 |
| FI50975C (en) | 1976-09-10 |
| CA939345A (en) | 1974-01-01 |
| BE720233A (en) | 1969-02-28 |
| AT289123B (en) | 1971-04-13 |
| FI50975B (en) | 1976-05-31 |
| NL6812003A (en) | 1969-03-11 |
| FR8490M (en) | 1973-07-27 |
| CH534168A (en) | 1973-02-28 |
| OA02886A (en) | 1970-12-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |