FI66864C - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 4-oxo-4h-pyrido(1,2-a)pyrimidinderivat - Google Patents
Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 4-oxo-4h-pyrido(1,2-a)pyrimidinderivat Download PDFInfo
- Publication number
- FI66864C FI66864C FI782527A FI782527A FI66864C FI 66864 C FI66864 C FI 66864C FI 782527 A FI782527 A FI 782527A FI 782527 A FI782527 A FI 782527A FI 66864 C FI66864 C FI 66864C
- Authority
- FI
- Finland
- Prior art keywords
- ethyl
- oxo
- pyrido
- pyrimidine
- methyl
- Prior art date
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- 230000001225 therapeutic effect Effects 0.000 title description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- NYJWYCAHJRGKMI-UHFFFAOYSA-N pyrido[1,2-a]pyrimidin-4-one Chemical class C1=CC=CN2C(=O)C=CN=C21 NYJWYCAHJRGKMI-UHFFFAOYSA-N 0.000 claims description 3
- VFTOHJFKIJLYKN-UHFFFAOYSA-N 7-nitro-9h-fluoren-2-ol Chemical group [O-][N+](=O)C1=CC=C2C3=CC=C(O)C=C3CC2=C1 VFTOHJFKIJLYKN-UHFFFAOYSA-N 0.000 claims description 2
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
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- 238000004458 analytical method Methods 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 30
- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
- 239000000203 mixture Substances 0.000 description 25
- 238000001953 recrystallisation Methods 0.000 description 25
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 15
- 239000000155 melt Substances 0.000 description 15
- 239000013078 crystal Substances 0.000 description 14
- -1 cyclohexylethyl Chemical group 0.000 description 14
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- 238000012360 testing method Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- BMTSZVZQNMNPCT-UHFFFAOYSA-N 2-aminopyridin-3-ol Chemical compound NC1=NC=CC=C1O BMTSZVZQNMNPCT-UHFFFAOYSA-N 0.000 description 3
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- UGSBCCAHDVCHGI-UHFFFAOYSA-N 5-nitropyridin-2-amine Chemical compound NC1=CC=C([N+]([O-])=O)C=N1 UGSBCCAHDVCHGI-UHFFFAOYSA-N 0.000 description 3
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- PGQGXTDGOHDTNW-UHFFFAOYSA-N 3-benzyl-2,6-dimethylpyrido[1,2-a]pyrimidin-4-one;hydrochloride Chemical compound Cl.CC=1N=C2C=CC=C(C)N2C(=O)C=1CC1=CC=CC=C1 PGQGXTDGOHDTNW-UHFFFAOYSA-N 0.000 description 1
- DFNXHNBRQIABNY-UHFFFAOYSA-N 3-ethyl-2,6,8-trimethylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(C)C=C(C)N2C(=O)C(CC)=C(C)N=C21 DFNXHNBRQIABNY-UHFFFAOYSA-N 0.000 description 1
- XFYIIXTWGSQBFN-UHFFFAOYSA-N 3-ethyl-2,7-dimethylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC(C)=CN2C(=O)C(CC)=C(C)N=C21 XFYIIXTWGSQBFN-UHFFFAOYSA-N 0.000 description 1
- AAIZLBJGGDQXFD-UHFFFAOYSA-N 3-ethyl-2,8-dimethylpyrido[1,2-a]pyrimidin-4-one Chemical group C1=C(C)C=CN2C(=O)C(CC)=C(C)N=C21 AAIZLBJGGDQXFD-UHFFFAOYSA-N 0.000 description 1
- STBPTJAEFRRWTP-UHFFFAOYSA-N 3-ethyl-2-methyl-4-oxopyrido[1,2-a]pyrimidine-7-carboxamide Chemical compound NC(=O)C=1C=CC=2N(C(C(=C(N=2)C)CC)=O)C=1 STBPTJAEFRRWTP-UHFFFAOYSA-N 0.000 description 1
- RGDQRXPEZUNWHX-UHFFFAOYSA-N 3-methylpyridin-2-amine Chemical compound CC1=CC=CN=C1N RGDQRXPEZUNWHX-UHFFFAOYSA-N 0.000 description 1
- BRBUBVKGJRPRRD-UHFFFAOYSA-N 4,6-dimethylpyridin-2-amine Chemical compound CC1=CC(C)=NC(N)=C1 BRBUBVKGJRPRRD-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 description 1
- VFMCUTPRJLZEEW-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine Chemical group C1=CC=CN2CC=CN=C21 VFMCUTPRJLZEEW-UHFFFAOYSA-N 0.000 description 1
- MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 description 1
- IVILGUFRMDBUEQ-UHFFFAOYSA-N 5-iodopyridin-2-amine Chemical group NC1=CC=C(I)C=N1 IVILGUFRMDBUEQ-UHFFFAOYSA-N 0.000 description 1
- CMBSSVKZOPZBKW-UHFFFAOYSA-N 5-methylpyridin-2-amine Chemical compound CC1=CC=C(N)N=C1 CMBSSVKZOPZBKW-UHFFFAOYSA-N 0.000 description 1
- FBSYYXXCZITRCC-UHFFFAOYSA-N 7-chloro-3-ethyl-2-methylpyrido[1,2-a]pyrimidin-4-one;hydrochloride Chemical compound Cl.C1=CC(Cl)=CN2C(=O)C(CC)=C(C)N=C21 FBSYYXXCZITRCC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- LOWVMOAJOXTLEA-UHFFFAOYSA-N CCC1=C(N=C2C=CC(=CN2C1=O)C#N)C Chemical compound CCC1=C(N=C2C=CC(=CN2C1=O)C#N)C LOWVMOAJOXTLEA-UHFFFAOYSA-N 0.000 description 1
- USMGXXUQFZFPJV-UHFFFAOYSA-N CCC1=C(N=C2C=CC(=CN2C1=O)I)C Chemical compound CCC1=C(N=C2C=CC(=CN2C1=O)I)C USMGXXUQFZFPJV-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 241000282560 Macaca mulatta Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 102000003840 Opioid Receptors Human genes 0.000 description 1
- 108090000137 Opioid Receptors Proteins 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229950011175 aminopicoline Drugs 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 238000009227 behaviour therapy Methods 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- ZGULNKYAODXSCS-UHFFFAOYSA-N ethyl 2-acetyl-4-methylpentanoate Chemical compound CCOC(=O)C(C(C)=O)CC(C)C ZGULNKYAODXSCS-UHFFFAOYSA-N 0.000 description 1
- XTIHUENEZQMZSG-UHFFFAOYSA-N ethyl 2-acetyldodecanoate Chemical compound CCCCCCCCCCC(C(C)=O)C(=O)OCC XTIHUENEZQMZSG-UHFFFAOYSA-N 0.000 description 1
- ZTOQBHVLCJERBS-UHFFFAOYSA-N ethyl 2-acetylhexanoate Chemical group CCCCC(C(C)=O)C(=O)OCC ZTOQBHVLCJERBS-UHFFFAOYSA-N 0.000 description 1
- VHOACUZAQKMOEQ-UHFFFAOYSA-N ethyl 2-acetylpentanoate Chemical compound CCCC(C(C)=O)C(=O)OCC VHOACUZAQKMOEQ-UHFFFAOYSA-N 0.000 description 1
- DSLNDNBTFISZHG-UHFFFAOYSA-N ethyl 2-ethyl-3-oxodecanoate Chemical compound CCCCCCCC(=O)C(CC)C(=O)OCC DSLNDNBTFISZHG-UHFFFAOYSA-N 0.000 description 1
- YXZUMIRYUCTIGL-UHFFFAOYSA-N ethyl 2-methyl-3-oxopentanoate Chemical compound CCOC(=O)C(C)C(=O)CC YXZUMIRYUCTIGL-UHFFFAOYSA-N 0.000 description 1
- FIKVWPJKNMTBBD-UHFFFAOYSA-N ethyl 6-aminopyridine-3-carboxylate Chemical group CCOC(=O)C1=CC=C(N)N=C1 FIKVWPJKNMTBBD-UHFFFAOYSA-N 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940116298 l- malic acid Drugs 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- CEAJFNBWKBTRQE-UHFFFAOYSA-N methanamine;methanol Chemical compound NC.OC CEAJFNBWKBTRQE-UHFFFAOYSA-N 0.000 description 1
- OYEVFSJZQTUDDN-UHFFFAOYSA-N methanol;n-methylmethanamine Chemical compound OC.CNC OYEVFSJZQTUDDN-UHFFFAOYSA-N 0.000 description 1
- 125000005528 methosulfate group Chemical group 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000862 numbness Toxicity 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- ZSIALBZCWCLSOG-UHFFFAOYSA-N pyrimidine;hydroiodide Chemical compound I.C1=CN=CN=C1 ZSIALBZCWCLSOG-UHFFFAOYSA-N 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ACWBQPMHZXGDFX-QFIPXVFZSA-N valsartan Chemical class C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001765 | 1977-08-19 | ||
| HU77CI1765A HU178910B (en) | 1977-08-19 | 1977-08-19 | Process for preparing 2,3-disubstituted-4-oxo-4h-pyrido/1,2-a/-pyrimidines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI782527A7 FI782527A7 (fi) | 1979-02-20 |
| FI66864B FI66864B (fi) | 1984-08-31 |
| FI66864C true FI66864C (fi) | 1984-12-10 |
Family
ID=10994667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI782527A FI66864C (fi) | 1977-08-19 | 1978-08-18 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 4-oxo-4h-pyrido(1,2-a)pyrimidinderivat |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US4219649A (cs) |
| JP (1) | JPS5448795A (cs) |
| AT (1) | AT368156B (cs) |
| AU (1) | AU518364B2 (cs) |
| BE (1) | BE869832A (cs) |
| CA (1) | CA1152989A (cs) |
| CH (1) | CH637541A5 (cs) |
| CS (1) | CS238901B1 (cs) |
| DD (1) | DD138320A5 (cs) |
| DE (1) | DE2835004A1 (cs) |
| DK (1) | DK160045C (cs) |
| ES (1) | ES473181A1 (cs) |
| FI (1) | FI66864C (cs) |
| FR (1) | FR2416892A1 (cs) |
| GB (1) | GB2006187B (cs) |
| GR (1) | GR64913B (cs) |
| HU (1) | HU178910B (cs) |
| IL (1) | IL55338A (cs) |
| NL (1) | NL7808570A (cs) |
| SE (1) | SE435383B (cs) |
| SU (1) | SU906378A3 (cs) |
| YU (1) | YU40985B (cs) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU180701B (en) * | 1977-12-29 | 1983-04-29 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing pyrido-/1,2-a/pyrimidines containing a carboxylic or ester group on the pirimidimering |
| HU179143B (en) * | 1977-12-29 | 1982-08-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing 9-hydroxy-groops-containing 6,7-dihydro-pyrido-square bracket-1,2-a-square bracket closed-pyrimidin derivatives and esters thereof |
| FR2449689A1 (fr) * | 1979-02-20 | 1980-09-19 | Logeais Labor Jacques | Nouveaux derives condenses de pyrrolidine ou de piperidine, leur procede de preparation et leurs applications en therapeutique |
| IL59802A (en) | 1979-05-08 | 1983-07-31 | Erba Farmitalia | Substituted pyrido(1,2-a)pyrimidine carboxylic acid derivatives,their preparation and pharmaceutical compositions containing them |
| PL129375B1 (en) * | 1980-07-24 | 1984-05-31 | Rhone Poulenc Ind | Process for preparing novel derivatives of 2,3,6,7-tetrahydro-thiazole-/3,2-a/-pyrimidin-5-one |
| HU183408B (en) * | 1981-04-28 | 1984-05-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing oral ratard pharmaceutical compositions |
| CA1211111A (en) * | 1982-02-15 | 1986-09-09 | Isao Yanagisawa | Process for preparing novel pyrimidone compounds |
| US5252572A (en) * | 1988-02-03 | 1993-10-12 | Chinoin Gyogyszer- Es Vegyeszeti Termekek Gyara Rt. | Pyridopyrimidine derivatives, pharmaceutical compositions containing them and process for preparing same |
| JP2514136B2 (ja) * | 1990-05-02 | 1996-07-10 | アボツト・ラボラトリーズ | キノリジノン型化合物 |
| DE10050662A1 (de) * | 2000-10-13 | 2002-04-18 | Gruenenthal Gmbh | Substituierte 3,4-Dihydro-pyrido[1,2-a]pyrimidine |
| DE10050661A1 (de) * | 2000-10-13 | 2002-04-18 | Gruenenthal Gmbh | Substituierte 3,4-Dihydro-pyrimido[1,2-a]pyrimidine und 3,4-Dihydro-pyrazino[1,2-a]pyrimidine |
| DE20202183U1 (de) | 2002-02-01 | 2002-06-06 | Kretzschmar, Michael, Dr., 22453 Hamburg | Baukasten |
| MXPA05003607A (es) * | 2002-10-04 | 2005-11-17 | Prana Biotechnology Ltd | Compuestos neurologicamente activos. |
| JP5290147B2 (ja) | 2006-04-14 | 2013-09-18 | プラナ バイオテクノロジー リミティッド | 加齢黄斑変性症（ａｍｄ）の処置方法 |
| US7955155B2 (en) | 2007-07-09 | 2011-06-07 | Mega Brands International | Magnetic and electronic toy construction systems and elements |
| WO2009063901A1 (ja) | 2007-11-13 | 2009-05-22 | The University Of Tokyo | クオラムセンシング阻害剤 |
| AU2009267519B2 (en) * | 2008-06-17 | 2014-11-27 | Institut National De La Sante Et De La Recherche Medicale | Pyridopyrimidine compounds as anti-tubercular agents |
| CN107001360B (zh) | 2014-12-02 | 2020-09-18 | 普拉纳生物技术有限公司 | 4H-吡啶并[1,2-a]嘧啶-4-酮化合物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT296996B (de) * | 1966-11-02 | 1972-03-10 | Chinoin Gyogyszer Es Vegyeszet | Verfahren zur Herstellung von Homopyrimidazolderivaten und deren Säureadditionssalzen und quaternären Ammoniumsalzen |
| HU169230B (cs) * | 1972-03-29 | 1976-10-28 | ||
| HU168014B (cs) * | 1973-03-30 | 1976-02-28 | ||
| US4209622A (en) * | 1973-03-30 | 1980-06-24 | Chinoin Gygyszer es Vegyeszeti Termekek Gyara Rt. | 3-(Ethoxycarbonyl-methyl)-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine |
| HU168541B (cs) * | 1973-11-24 | 1976-05-28 | ||
| US4022897A (en) * | 1974-03-04 | 1977-05-10 | E. R. Squibb & Sons, Inc. | CNS active compounds |
| US3898224A (en) * | 1974-09-09 | 1975-08-05 | Squibb & Sons Inc | 1,6,7,8-Tetrahydro-4-oxo-4H-pyrido {8 1,2-A{9 pyrimidine-9-carboalkoxy compounds |
| US3935197A (en) * | 1975-05-16 | 1976-01-27 | E. R. Squibb & Sons, Inc. | 2-Styryl-4H-pyrido(1,2-a)pyrimidin-4-ones |
-
1977
- 1977-08-19 HU HU77CI1765A patent/HU178910B/hu not_active IP Right Cessation
-
1978
- 1978-08-10 GR GR56973A patent/GR64913B/el unknown
- 1978-08-10 DE DE19782835004 patent/DE2835004A1/de active Granted
- 1978-08-11 IL IL55338A patent/IL55338A/xx unknown
- 1978-08-11 AT AT0585278A patent/AT368156B/de not_active IP Right Cessation
- 1978-08-17 US US05/934,801 patent/US4219649A/en not_active Expired - Lifetime
- 1978-08-17 FR FR7823980A patent/FR2416892A1/fr active Granted
- 1978-08-17 AU AU39009/78A patent/AU518364B2/en not_active Expired
- 1978-08-17 YU YU1966/78A patent/YU40985B/xx unknown
- 1978-08-17 DD DD78207349A patent/DD138320A5/xx not_active IP Right Cessation
- 1978-08-18 FI FI782527A patent/FI66864C/fi not_active IP Right Cessation
- 1978-08-18 SE SE7808770A patent/SE435383B/sv not_active IP Right Cessation
- 1978-08-18 SU SU782652353A patent/SU906378A3/ru active
- 1978-08-18 JP JP10085278A patent/JPS5448795A/ja active Granted
- 1978-08-18 NL NL7808570A patent/NL7808570A/xx not_active Application Discontinuation
- 1978-08-18 GB GB7833924A patent/GB2006187B/en not_active Expired
- 1978-08-18 DK DK367478A patent/DK160045C/da not_active IP Right Cessation
- 1978-08-18 CA CA000309620A patent/CA1152989A/en not_active Expired
- 1978-08-18 CS CS785417A patent/CS238901B1/cs unknown
- 1978-08-18 BE BE189954A patent/BE869832A/xx not_active IP Right Cessation
- 1978-08-18 CH CH881578A patent/CH637541A5/de not_active IP Right Cessation
- 1978-08-19 ES ES473181A patent/ES473181A1/es not_active Expired
-
1980
- 1980-03-14 US US06/130,371 patent/US4291036A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CS541778A1 (en) | 1985-05-15 |
| GR64913B (en) | 1980-06-09 |
| HU178910B (en) | 1982-07-28 |
| ES473181A1 (es) | 1979-04-01 |
| DK367478A (da) | 1979-02-20 |
| DE2835004C2 (cs) | 1989-06-29 |
| FR2416892B1 (cs) | 1983-11-18 |
| IL55338A (en) | 1985-10-31 |
| YU40985B (en) | 1986-10-31 |
| FR2416892A1 (fr) | 1979-09-07 |
| CH637541A5 (de) | 1983-08-15 |
| DK160045C (da) | 1991-06-10 |
| US4219649A (en) | 1980-08-26 |
| SE7808770L (sv) | 1979-02-20 |
| NL7808570A (nl) | 1979-02-21 |
| CS238901B1 (en) | 1985-12-16 |
| SU906378A3 (ru) | 1982-02-15 |
| US4291036A (en) | 1981-09-22 |
| DD138320A5 (de) | 1979-10-24 |
| FI782527A7 (fi) | 1979-02-20 |
| ATA585278A (de) | 1982-01-15 |
| DK160045B (da) | 1991-01-21 |
| AU518364B2 (en) | 1981-09-24 |
| YU196678A (en) | 1983-10-31 |
| GB2006187B (en) | 1982-10-06 |
| GB2006187A (en) | 1979-05-02 |
| DE2835004A1 (de) | 1979-03-01 |
| SE435383B (sv) | 1984-09-24 |
| AU3900978A (en) | 1980-02-21 |
| JPS5448795A (en) | 1979-04-17 |
| BE869832A (fr) | 1978-12-18 |
| FI66864B (fi) | 1984-08-31 |
| CA1152989A (en) | 1983-08-30 |
| JPS626554B2 (cs) | 1987-02-12 |
| IL55338A0 (en) | 1978-10-31 |
| AT368156B (de) | 1982-09-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: CHINOIN GYOGUSZER ES VEGYESZETI TERMEKEK |