ES341317A1 - Un procedimiento para la preparacion de compuestos de pira-zinamida. - Google Patents
Un procedimiento para la preparacion de compuestos de pira-zinamida.Info
- Publication number
- ES341317A1 ES341317A1 ES341317A ES341317A ES341317A1 ES 341317 A1 ES341317 A1 ES 341317A1 ES 341317 A ES341317 A ES 341317A ES 341317 A ES341317 A ES 341317A ES 341317 A1 ES341317 A1 ES 341317A1
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- amino
- phenyl
- methyl
- chloropyrazinoate
- 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
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical class NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 39
- -1 chloro, bromo, iodo Chemical group 0.000 abstract 12
- 238000006243 chemical reaction Methods 0.000 abstract 10
- 239000001257 hydrogen Substances 0.000 abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 150000002431 hydrogen Chemical group 0.000 abstract 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 4
- 125000003282 alkyl amino group Chemical group 0.000 abstract 4
- NJAYXNFNZKQGNE-UHFFFAOYSA-N methyl 3-bromo-6-chloropyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=CN=C1Br NJAYXNFNZKQGNE-UHFFFAOYSA-N 0.000 abstract 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000005059 halophenyl group Chemical group 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- MHBZGKFJMRITHV-UHFFFAOYSA-N 3-amino-6-(trifluoromethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=CN1)C(F)(F)F)C(=O)N MHBZGKFJMRITHV-UHFFFAOYSA-N 0.000 abstract 2
- SFSMATGDLFHTHE-UHFFFAOYSA-N 3-aminopyrazine-2-carboxamide Chemical class NC(=O)C1=NC=CN=C1N SFSMATGDLFHTHE-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 1
- ZABBFAHZPHMIJC-UHFFFAOYSA-N 1,1-Dibromopropan-2-one Chemical compound CC(=O)C(Br)Br ZABBFAHZPHMIJC-UHFFFAOYSA-N 0.000 abstract 1
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 abstract 1
- IDBNECMSCRAUNU-UHFFFAOYSA-N 1-ethylpyrrolidin-3-ol Chemical compound CCN1CCC(O)C1 IDBNECMSCRAUNU-UHFFFAOYSA-N 0.000 abstract 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 abstract 1
- ZXCBLBWKVUMUBW-UHFFFAOYSA-N 3-amino-5-(trifluoromethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC=C(N1)C(F)(F)F)C(=O)N ZXCBLBWKVUMUBW-UHFFFAOYSA-N 0.000 abstract 1
- OZMUCSYTBBYNTK-UHFFFAOYSA-N 3-amino-5-(trifluoromethyl)pyrazine-2-carboxylic acid Chemical compound NC1=NC(C(F)(F)F)=CN=C1C(O)=O OZMUCSYTBBYNTK-UHFFFAOYSA-N 0.000 abstract 1
- HQYQZNRBJGOWFW-UHFFFAOYSA-N 3-amino-6-benzylsulfanylpyrazine-2-carboxylic acid Chemical compound NC=1C(=NC(=CN1)SCC1=CC=CC=C1)C(=O)O HQYQZNRBJGOWFW-UHFFFAOYSA-N 0.000 abstract 1
- WDBPDIQNBCWYOY-UHFFFAOYSA-N 3-chloro-1-ethylpyrrolidine Chemical compound CCN1CCC(Cl)C1 WDBPDIQNBCWYOY-UHFFFAOYSA-N 0.000 abstract 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 125000004799 bromophenyl group Chemical group 0.000 abstract 1
- 125000000068 chlorophenyl group Chemical group 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- RRKJFUSUDZZRGJ-UHFFFAOYSA-N ethyl 3-amino-6-(trifluoromethyl)pyrazine-2-carboxylate Chemical compound NC=1C(=NC(=CN1)C(F)(F)F)C(=O)OCC RRKJFUSUDZZRGJ-UHFFFAOYSA-N 0.000 abstract 1
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- ZRRKFICDIUCPIE-UHFFFAOYSA-N methyl 3-(benzylamino)-6-chloropyrazine-2-carboxylate Chemical compound C(C1=CC=CC=C1)NC=1C(=NC(=CN1)Cl)C(=O)OC ZRRKFICDIUCPIE-UHFFFAOYSA-N 0.000 abstract 1
- ZARHJADZMQHHQM-UHFFFAOYSA-N methyl 3-amino-5-(trifluoromethyl)pyrazine-2-carboxylate Chemical compound COC(=O)C1=NC=C(C(F)(F)F)N=C1N ZARHJADZMQHHQM-UHFFFAOYSA-N 0.000 abstract 1
- KRBPFWZEXJXVNU-UHFFFAOYSA-N methyl 3-amino-6-chloro-5-(ethylamino)pyrazine-2-carboxylate Chemical compound NC=1C(=NC(=C(N1)NCC)Cl)C(=O)OC KRBPFWZEXJXVNU-UHFFFAOYSA-N 0.000 abstract 1
- JFUCSIYDDKQAAT-UHFFFAOYSA-N methyl 3-bromo-6-chloro-5-(ethylamino)pyrazine-2-carboxylate Chemical compound CCNC1=NC(Br)=C(C(=O)OC)N=C1Cl JFUCSIYDDKQAAT-UHFFFAOYSA-N 0.000 abstract 1
- BYRBCXRBGPGOFL-UHFFFAOYSA-N methyl 6-chloro-3-[(4-chlorophenyl)methylamino]pyrazine-2-carboxylate Chemical compound ClC1=CC=C(CNC=2C(=NC(=CN2)Cl)C(=O)OC)C=C1 BYRBCXRBGPGOFL-UHFFFAOYSA-N 0.000 abstract 1
- NSMCAYXUTZQFCS-UHFFFAOYSA-N methyl 6-chloro-3-[(4-methoxyphenyl)methylamino]pyrazine-2-carboxylate Chemical compound COC1=CC=C(CNC=2C(=NC(=CN2)Cl)C(=O)OC)C=C1 NSMCAYXUTZQFCS-UHFFFAOYSA-N 0.000 abstract 1
- OKNXJFRSNAYEJQ-UHFFFAOYSA-N methyl 6-chloro-5-(ethylamino)-3-(2-methoxyethylamino)pyrazine-2-carboxylate Chemical compound COCCNC=1C(=NC(=C(N1)NCC)Cl)C(=O)OC OKNXJFRSNAYEJQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 239000012286 potassium permanganate Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- PUNNVBVTWAAWIJ-UHFFFAOYSA-N pyrazino[2,3-d][1,3]oxazin-4-one Chemical compound C1=CN=C2C(=O)OC=NC2=N1 PUNNVBVTWAAWIJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000894 saliuretic effect Effects 0.000 abstract 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 125000004417 unsaturated alkyl 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57344766A | 1966-08-17 | 1966-08-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES341317A1 true ES341317A1 (es) | 1968-10-01 |
Family
ID=24292032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES341317A Expired ES341317A1 (es) | 1966-08-17 | 1967-06-02 | Un procedimiento para la preparacion de compuestos de pira-zinamida. |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE699431A (enrdf_load_stackoverflow) |
| CH (1) | CH496713A (enrdf_load_stackoverflow) |
| DK (1) | DK116662B (enrdf_load_stackoverflow) |
| ES (1) | ES341317A1 (enrdf_load_stackoverflow) |
| FR (1) | FR6796M (enrdf_load_stackoverflow) |
| GB (1) | GB1181288A (enrdf_load_stackoverflow) |
| NL (1) | NL6707566A (enrdf_load_stackoverflow) |
| SE (1) | SE324367B (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1261335A (en) * | 1984-08-29 | 1989-09-26 | Hoffmann-La Roche Limited/Hoffmann-La Roche Limitee | Ethylenediamine monoamide derivatives |
| GB8810934D0 (en) * | 1987-05-26 | 1988-06-15 | Ici America Inc | Amides |
| GB8810933D0 (en) * | 1987-05-26 | 1988-06-15 | Ici America Inc | Heterocyclic compounds |
| GB8812342D0 (en) * | 1988-05-25 | 1988-06-29 | Ici America Inc | Bicyclic compounds |
| KR20180040699A (ko) * | 2015-08-20 | 2018-04-20 | 베링거 인겔하임 인터내셔날 게엠베하 | 신규한 어닐링된 벤즈아미드 |
-
1967
- 1967-05-31 NL NL6707566A patent/NL6707566A/xx unknown
- 1967-06-01 DK DK286667A patent/DK116662B/da unknown
- 1967-06-02 ES ES341317A patent/ES341317A1/es not_active Expired
- 1967-06-02 BE BE699431D patent/BE699431A/xx unknown
- 1967-06-07 GB GB2621067A patent/GB1181288A/en not_active Expired
- 1967-06-07 CH CH803767A patent/CH496713A/de not_active IP Right Cessation
- 1967-06-09 SE SE812567A patent/SE324367B/xx unknown
- 1967-09-04 FR FR119888A patent/FR6796M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6707566A (enrdf_load_stackoverflow) | 1968-02-19 |
| SE324367B (enrdf_load_stackoverflow) | 1970-06-01 |
| DK116662B (da) | 1970-02-02 |
| BE699431A (enrdf_load_stackoverflow) | 1967-12-04 |
| FR6796M (enrdf_load_stackoverflow) | 1969-03-17 |
| CH496713A (de) | 1970-09-30 |
| GB1181288A (en) | 1970-02-11 |
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