BE525394A - - Google Patents
Info
- Publication number
- BE525394A BE525394A BE525394DA BE525394A BE 525394 A BE525394 A BE 525394A BE 525394D A BE525394D A BE 525394DA BE 525394 A BE525394 A BE 525394A
- Authority
- BE
- Belgium
- Prior art keywords
- pyrimidine
- aralkyl
- mercapto
- pyrido
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 17
- -1 pyrido- (2,3-d) -pyrimidine compound Chemical class 0.000 claims description 14
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- HJBCFHXEOPQFGF-UHFFFAOYSA-N 4-chloropyrido[2,3-d]pyrimidine Chemical compound C1=CC=C2C(Cl)=NC=NC2=N1 HJBCFHXEOPQFGF-UHFFFAOYSA-N 0.000 claims description 7
- XKEBMWRWBWRQAO-UHFFFAOYSA-N 1H-pyrido[2,3-d]pyrimidin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=N1 XKEBMWRWBWRQAO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- KPIVDNYJNOPGBE-UHFFFAOYSA-N 2-aminonicotinic acid Chemical compound NC1=NC=CC=C1C(O)=O KPIVDNYJNOPGBE-UHFFFAOYSA-N 0.000 claims description 4
- 239000007868 Raney catalyst Substances 0.000 claims description 4
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 238000005576 amination reaction Methods 0.000 claims 3
- 238000005660 chlorination reaction Methods 0.000 claims 3
- 125000001769 aryl amino group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
- RCJVRSBWZCNNQT-UHFFFAOYSA-N Dichlorine monoxide Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000155 melt Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000002844 melting Methods 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000003230 pyrimidines Chemical class 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- CYQAYERJWZKYML-UHFFFAOYSA-N Phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N Tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XITZJLJVSFQXLV-UHFFFAOYSA-N 2-amino-4,6-dimethylpyridine-3-carboxylic acid Chemical compound CC1=CC(C)=C(C(O)=O)C(N)=N1 XITZJLJVSFQXLV-UHFFFAOYSA-N 0.000 description 1
- XQBYYQRWYONQLM-UHFFFAOYSA-N 2-amino-6-methylpyridine-3-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)C(N)=N1 XQBYYQRWYONQLM-UHFFFAOYSA-N 0.000 description 1
- CMOJBVDQMMHOIC-UHFFFAOYSA-N 2-methyl-8H-pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(=O)NC2=NC(C)=NC=C21 CMOJBVDQMMHOIC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-M 4-hydroxybutyrate Chemical group OCCCC([O-])=O SJZRECIVHVDYJC-UHFFFAOYSA-M 0.000 description 1
- DKJAKIZLQMJGDV-UHFFFAOYSA-N 6-methyl-7-phenyl-2-sulfanylidene-1H-pyrido[2,3-d]pyrimidin-4-one Chemical compound CC1=CC(C(NC(=S)N2)=O)=C2N=C1C1=CC=CC=C1 DKJAKIZLQMJGDV-UHFFFAOYSA-N 0.000 description 1
- 229960000583 Acetic Acid Drugs 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- XPPFVDHAOLXNQL-UHFFFAOYSA-N C1=CC=C2C(N)=NC(=S)NC2=N1 Chemical compound C1=CC=C2C(N)=NC(=S)NC2=N1 XPPFVDHAOLXNQL-UHFFFAOYSA-N 0.000 description 1
- OZRYXKBVXCHTDP-UHFFFAOYSA-N SC=1N=C(C2=C(N1)N=C(C(=C2)C)C)O Chemical compound SC=1N=C(C2=C(N1)N=C(C(=C2)C)C)O OZRYXKBVXCHTDP-UHFFFAOYSA-N 0.000 description 1
- AWXCWJNJONXHQZ-UHFFFAOYSA-N SC=1N=C(C2=C(N1)N=C(C(=C2)C)CC)O Chemical compound SC=1N=C(C2=C(N1)N=C(C(=C2)C)CC)O AWXCWJNJONXHQZ-UHFFFAOYSA-N 0.000 description 1
- GIOJEOHGYFQXQD-UHFFFAOYSA-N SC=1N=C(C2=C(N1)N=C(C(=C2)C)CCCC)O Chemical compound SC=1N=C(C2=C(N1)N=C(C(=C2)C)CCCC)O GIOJEOHGYFQXQD-UHFFFAOYSA-N 0.000 description 1
- JNXSURMNMWYJGP-UHFFFAOYSA-N SC=1N=C(C2=C(N1)N=C(C(=C2)C2=CC=CC=C2)CC2=CC=CC=C2)O Chemical compound SC=1N=C(C2=C(N1)N=C(C(=C2)C2=CC=CC=C2)CC2=CC=CC=C2)O JNXSURMNMWYJGP-UHFFFAOYSA-N 0.000 description 1
- SNVNFPLKKXTWHT-UHFFFAOYSA-N SC=1N=C(C2=C(N1)N=C(C(=C2)CC)CCC)O Chemical compound SC=1N=C(C2=C(N1)N=C(C(=C2)CC)CCC)O SNVNFPLKKXTWHT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- HDITUCONWLWUJR-UHFFFAOYSA-N diethylazanium;chloride Chemical compound [Cl-].CC[NH2+]CC HDITUCONWLWUJR-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- QZILSYOEHMXZBE-UHFFFAOYSA-N pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=N1 QZILSYOEHMXZBE-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE525394A true BE525394A (ko) |
Family
ID=159704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE525394D BE525394A (ko) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE525394A (ko) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0180833A1 (de) * | 1984-10-19 | 1986-05-14 | Gödecke Aktiengesellschaft | 4-Oxo-pyrido[2,3]pyrimidin-Derivate, Verfahren zur deren Herstellung und diese ethaltende Arzneimittel |
| EP0180834A1 (de) * | 1984-10-19 | 1986-05-14 | Gödecke Aktiengesellschaft | 4-Alkoxy-pyrido[2,3-d]pyrimidin-Derivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
-
0
- BE BE525394D patent/BE525394A/fr unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0180833A1 (de) * | 1984-10-19 | 1986-05-14 | Gödecke Aktiengesellschaft | 4-Oxo-pyrido[2,3]pyrimidin-Derivate, Verfahren zur deren Herstellung und diese ethaltende Arzneimittel |
| EP0180834A1 (de) * | 1984-10-19 | 1986-05-14 | Gödecke Aktiengesellschaft | 4-Alkoxy-pyrido[2,3-d]pyrimidin-Derivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
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