DK142199B - Fremgangsmåde til fremstilling af pyrazinoylguanidiner. - Google Patents
Fremgangsmåde til fremstilling af pyrazinoylguanidiner. Download PDFInfo
- Publication number
- DK142199B DK142199B DK494664AA DK494664A DK142199B DK 142199 B DK142199 B DK 142199B DK 494664A A DK494664A A DK 494664AA DK 494664 A DK494664 A DK 494664A DK 142199 B DK142199 B DK 142199B
- Authority
- DK
- Denmark
- Prior art keywords
- carbon atoms
- group
- solution
- propanol
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 5
- WNBSDCKJFDZMHT-UHFFFAOYSA-N n-(diaminomethylidene)pyrazine-2-carboxamide Chemical class NC(N)=NC(=O)C1=CN=CC=N1 WNBSDCKJFDZMHT-UHFFFAOYSA-N 0.000 title claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- -1 3-Amino-6-chloropyrazinoyl Chemical group 0.000 claims description 11
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 5
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- BHGCNGDTJZDAEX-UHFFFAOYSA-N n,n-dimethylformamide;propan-2-ol Chemical compound CC(C)O.CN(C)C=O BHGCNGDTJZDAEX-UHFFFAOYSA-N 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- GPIMZXJMWKALDA-UHFFFAOYSA-N 6-chloro-2-methylpyrazino[2,3-d][1,3]oxazin-4-one Chemical compound C1=C(Cl)N=C2C(=O)OC(C)=NC2=N1 GPIMZXJMWKALDA-UHFFFAOYSA-N 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 2
- TZBHPYXJOJGKDT-UHFFFAOYSA-N 1,3-oxazin-4-one Chemical compound O=C1C=COC=N1 TZBHPYXJOJGKDT-UHFFFAOYSA-N 0.000 claims 1
- TYRQDINUUICQQU-UHFFFAOYSA-N 3-acetamido-N-(N-acetylcarbamimidoyl)-6-chloropyrazine-2-carboxamide Chemical compound C(C)(=O)NC=1C(=NC(=CN1)Cl)C(=O)NC(=N)NC(C)=O TYRQDINUUICQQU-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- CTBWJCKRJCPLKU-UHFFFAOYSA-N N-[3-[amino-(N-benzylidenecarbamimidoyl)carbamoyl]-5-chloropyrazin-2-yl]acetamide Chemical compound C(C)(=O)NC=1C(=NC(=CN1)Cl)C(=O)N(C(=N)N=CC1=CC=CC=C1)N CTBWJCKRJCPLKU-UHFFFAOYSA-N 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 229960004198 guanidine Drugs 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229960000789 guanidine hydrochloride Drugs 0.000 description 3
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- BGUZUBJJYOPBCV-UHFFFAOYSA-N 3-acetamido-N-(diaminomethylidene)-6-methylsulfanylpyrazine-2-carboxamide Chemical compound C(C)(=O)NC=1C(=NC(=CN1)SC)C(=O)NC(=N)N BGUZUBJJYOPBCV-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- WNPXUCYRKHVMAD-UHFFFAOYSA-N 2-(benzylideneamino)guanidine Chemical compound NC(N)=NN=CC1=CC=CC=C1 WNPXUCYRKHVMAD-UHFFFAOYSA-N 0.000 description 1
- WSVFXNHQEJCALK-UHFFFAOYSA-N 2-methyl-6-methylsulfanylpyrazino[2,3-d][1,3]oxazin-4-one Chemical compound CC=1OC(C2=C(N1)N=CC(=N2)SC)=O WSVFXNHQEJCALK-UHFFFAOYSA-N 0.000 description 1
- UNQXKENJIMAYTP-UHFFFAOYSA-N 2-methyl-6-methylsulfonylpyrazino[2,3-d][1,3]oxazin-4-one Chemical compound CC=1OC(C2=C(N1)N=CC(=N2)S(=O)(=O)C)=O UNQXKENJIMAYTP-UHFFFAOYSA-N 0.000 description 1
- ZENUANGUTQMBIY-UHFFFAOYSA-N 3-acetamido-6-chloro-N-(N,N'-diphenylcarbamimidoyl)pyrazine-2-carboxamide Chemical compound C(C)(=O)NC=1C(=NC(=CN1)Cl)C(=O)NC(=NC1=CC=CC=C1)NC1=CC=CC=C1 ZENUANGUTQMBIY-UHFFFAOYSA-N 0.000 description 1
- UVSWEQFMPXXSDK-UHFFFAOYSA-N 3-acetamido-N-(diaminomethylidene)-6-(dimethylamino)pyrazine-2-carboxamide nitric acid Chemical compound [N+](=O)(O)[O-].C(C)(=O)NC=1C(=NC(=CN1)N(C)C)C(=O)NC(=N)N UVSWEQFMPXXSDK-UHFFFAOYSA-N 0.000 description 1
- INSYKFUZLYMCSS-UHFFFAOYSA-N 3-amino-6-benzylsulfanyl-N-(diaminomethylidene)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=CN1)SCC1=CC=CC=C1)C(=O)NC(=N)N INSYKFUZLYMCSS-UHFFFAOYSA-N 0.000 description 1
- RXWACATVQOECDM-UHFFFAOYSA-N 3-amino-N-(diaminomethylidene)-6-methylsulfonylpyrazine-2-carboxamide Chemical compound NC=1C(=NC(=CN1)S(=O)(=O)C)C(=O)NC(=N)N RXWACATVQOECDM-UHFFFAOYSA-N 0.000 description 1
- LKOPZRPEDMVKBB-UHFFFAOYSA-N 6-(dimethylamino)-2-methylpyrazino[2,3-d][1,3]oxazin-4-one Chemical compound N1=C(C)OC(=O)C2=NC(N(C)C)=CN=C21 LKOPZRPEDMVKBB-UHFFFAOYSA-N 0.000 description 1
- RVTLOCROOSIIBC-UHFFFAOYSA-N 6-benzylsulfanyl-2-methylpyrazino[2,3-d][1,3]oxazin-4-one Chemical compound C(C1=CC=CC=C1)SC1=NC2=C(N=C(OC2=O)C)N=C1 RVTLOCROOSIIBC-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- NDEMNVPZDAFUKN-UHFFFAOYSA-N guanidine;nitric acid Chemical compound NC(N)=N.O[N+]([O-])=O.O[N+]([O-])=O NDEMNVPZDAFUKN-UHFFFAOYSA-N 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/02—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4
-
- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23423062A | 1962-10-30 | 1962-10-30 | |
| US23423062 | 1962-10-30 | ||
| US313315A US3313813A (en) | 1962-10-30 | 1963-10-07 | (3-amino-5, 6-disubstituted-pyrazinoyl) guanidines |
| US31331563 | 1963-10-07 | ||
| US35604264A | 1964-03-31 | 1964-03-31 | |
| US35604264 | 1964-03-31 | ||
| US35603864 | 1964-03-31 | ||
| US35603964 | 1964-03-31 | ||
| US356039A US3316266A (en) | 1964-03-31 | 1964-03-31 | 3-aminopyrazinoic acid derivatives and process for their preparation |
| US356038A US3290311A (en) | 1964-03-31 | 1964-03-31 | Derivatives of 3, 5-diamino-6-chloropyrazinoic acid esters and a process for making them |
| US35725664A | 1964-04-03 | 1964-04-03 | |
| US35725664 | 1964-04-03 | ||
| US509217A US3410850A (en) | 1962-10-30 | 1965-11-22 | 4h-pyrazino-[2, 3d][1, 3]oxazin-4-ones and their preparation |
| US50921765 | 1965-11-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK142199B true DK142199B (da) | 1980-09-22 |
| DK142199C DK142199C (en, 2012) | 1981-02-16 |
Family
ID=26999580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK494664AA DK142199B (da) | 1962-10-30 | 1964-10-07 | Fremgangsmåde til fremstilling af pyrazinoylguanidiner. |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3410850A (en, 2012) |
| BE (2) | BE651730A (en, 2012) |
| CH (2) | CH481939A (en, 2012) |
| DK (1) | DK142199B (en, 2012) |
| FR (1) | FR95657E (en, 2012) |
| NL (1) | NL6409717A (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3549627A (en) * | 1968-04-05 | 1970-12-22 | American Home Prod | 2,6-disubstituted-4h-pyrimido(5,4-d)(1,3)oxazin-4-0nes |
| US3549633A (en) * | 1968-11-20 | 1970-12-22 | Merck & Co Inc | Process for preparation of 1-h-imidazo (4,5-b)pyrazin-2-ones |
| US4140776A (en) * | 1977-09-16 | 1979-02-20 | Merck & Co., Inc. | N-pyrazinecarbonyl-N'-acylguanidines |
-
1964
- 1964-08-12 BE BE651730D patent/BE651730A/xx unknown
- 1964-08-12 BE BE651729D patent/BE651729A/xx unknown
- 1964-08-21 NL NL6409717A patent/NL6409717A/xx unknown
- 1964-08-25 FR FR986159A patent/FR95657E/fr not_active Expired
- 1964-08-25 CH CH1111464A patent/CH481939A/de not_active IP Right Cessation
- 1964-10-07 DK DK494664AA patent/DK142199B/da not_active IP Right Cessation
- 1964-12-18 CH CH1635164A patent/CH469721A/de unknown
-
1965
- 1965-11-22 US US509217A patent/US3410850A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK142199C (en, 2012) | 1981-02-16 |
| BE651729A (en, 2012) | 1965-02-12 |
| US3410850A (en) | 1968-11-12 |
| CH481939A (de) | 1969-11-30 |
| BE651730A (en, 2012) | 1965-02-12 |
| NL6409717A (en, 2012) | 1965-10-04 |
| CH469721A (de) | 1969-03-15 |
| FR95657E (fr) | 1971-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUP | Patent expired |