DK141120B - Analogifremgangsmåde til fremstilling af terapeutisk aktive amidoximderivater eller salte deraf. - Google Patents
Analogifremgangsmåde til fremstilling af terapeutisk aktive amidoximderivater eller salte deraf. Download PDFInfo
- Publication number
- DK141120B DK141120B DK256768AA DK256768A DK141120B DK 141120 B DK141120 B DK 141120B DK 256768A A DK256768A A DK 256768AA DK 256768 A DK256768 A DK 256768A DK 141120 B DK141120 B DK 141120B
- Authority
- DK
- Denmark
- Prior art keywords
- group
- formula
- salts
- general formula
- compound
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 14
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical class C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 17
- -1 pyrimidoimidazolyl Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical group O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001391 thioamide group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 19
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 15
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- 206010037660 Pyrexia Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000001741 anti-phlogistic effect Effects 0.000 description 3
- 230000001754 anti-pyretic effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- BYXYCUABYHCYLY-UHFFFAOYSA-N isoindole-1,3-dione;potassium Chemical compound [K].C1=CC=C2C(=O)NC(=O)C2=C1 BYXYCUABYHCYLY-UHFFFAOYSA-N 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 229920002307 Dextran Polymers 0.000 description 2
- 206010015150 Erythema Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 231100000321 erythema Toxicity 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Chemical class 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- FIIFYAUIXKFDEZ-UHFFFAOYSA-N 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile Chemical compound C1CN=C(CC#N)C2=C1C=C(OC)C(OC)=C2 FIIFYAUIXKFDEZ-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- HJHLJOZNQCGLDE-UHFFFAOYSA-N 3-(2-methyl-4-oxoquinazolin-3-yl)propanenitrile Chemical compound C1=CC=C2C(=O)N(CCC#N)C(C)=NC2=C1 HJHLJOZNQCGLDE-UHFFFAOYSA-N 0.000 description 1
- KDPNJVQOQIXMSF-UHFFFAOYSA-N 3-(5-chloro-2-oxo-1,3-benzoxazol-3-yl)propanenitrile Chemical compound ClC1=CC=C2OC(=O)N(CCC#N)C2=C1 KDPNJVQOQIXMSF-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- OGIKVKIRSFKOGM-UHFFFAOYSA-N N'-hydroxy-2-(3-hydroxy-2-quinoxalin-2-ylphenyl)ethanimidamide Chemical compound OC=1C(=C(C=CC1)CC(N)=NO)C1=NC2=CC=CC=C2N=C1 OGIKVKIRSFKOGM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 206010030124 Oedema peripheral Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003326 anti-histaminergic effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- YWNRATDDUSMBPR-UHFFFAOYSA-N ethyl 3-cyano-2-oxo-3-phenylpropanoate Chemical compound CCOC(=O)C(=O)C(C#N)C1=CC=CC=C1 YWNRATDDUSMBPR-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 244000144993 groups of animals Species 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 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
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 125000005493 quinolyl group Chemical group 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000002277 temperature effect Effects 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI000714 | 1967-06-06 | ||
| HUCI000714 | 1967-06-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK141120B true DK141120B (da) | 1980-01-21 |
| DK141120C DK141120C (OSRAM) | 1980-07-14 |
Family
ID=10994338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK256768AA DK141120B (da) | 1967-06-06 | 1968-05-31 | Analogifremgangsmåde til fremstilling af terapeutisk aktive amidoximderivater eller salte deraf. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3673188A (OSRAM) |
| AT (1) | AT277234B (OSRAM) |
| BE (1) | BE716174A (OSRAM) |
| BR (1) | BR6899612D0 (OSRAM) |
| CA (1) | CA925869A (OSRAM) |
| CH (1) | CH526539A (OSRAM) |
| CS (1) | CS168502B2 (OSRAM) |
| DE (1) | DE1670497C3 (OSRAM) |
| DK (1) | DK141120B (OSRAM) |
| FI (1) | FI52857C (OSRAM) |
| FR (1) | FR7892M (OSRAM) |
| GB (1) | GB1187348A (OSRAM) |
| IL (1) | IL29976A (OSRAM) |
| NL (1) | NL139238B (OSRAM) |
| NO (1) | NO127054B (OSRAM) |
| SE (1) | SE335128B (OSRAM) |
| YU (1) | YU33285B (OSRAM) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3948928A (en) * | 1972-03-17 | 1976-04-06 | Dainippon Pharmaceutical Co., Ltd. | 3-Substituted-1,2-benzisoxazoles and pharmaceutically acceptable acid addition salts thereof |
| US3907822A (en) * | 1973-06-11 | 1975-09-23 | Squibb & Sons Inc | Anti-inflammatory (2-benzimidazoylthio)alkylamidoximes |
| US4112111A (en) * | 1975-02-26 | 1978-09-05 | Sandoz Ltd. | Indolinylguanidines |
| US4048176A (en) * | 1976-07-23 | 1977-09-13 | Morton-Norwich Products, Inc. | 2-(3-Methyl-4-phenyl-1,2,3,4-tetrahydro-2-isoquinolyl)-acetamidoxime dihydrochloride |
| FR2506767A1 (fr) | 1981-05-26 | 1982-12-03 | Synthelabo | Derives heterocycliques d'amidoximes, leur preparation et leur application en therapeutique |
| HU190377B (en) * | 1982-03-12 | 1986-08-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing theophyllinyl-alkyl-oxadiazoles |
| US4833153A (en) * | 1985-11-08 | 1989-05-23 | Glaxo Group Limited | Indole derivatives |
| EP0275260B1 (en) * | 1986-07-24 | 1993-11-18 | Tropix, Inc. | Method of detecting a substance using enzymatically-induced decomposition of dioxetanes |
| HU207988B (en) * | 1988-10-20 | 1993-07-28 | Biorex Kutato Fejlesztoe Kft | Process for producing halogenides of o-/3-amino-2-hydroxy-propyl/hydroximic acid and pharmaceutical compositions containing them as active components |
| WO1997010221A1 (en) * | 1995-09-15 | 1997-03-20 | Torrey Pines Institute For Molecular Studies | Synthesis of quinazolinone libraries |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3150135A (en) * | 1962-11-13 | 1964-09-22 | Fmc Corp | Preparation of oximes |
| US3354174A (en) * | 1964-02-19 | 1967-11-21 | Sterling Drug Inc | 1-and 2-benzimidazolyl-lower-alkylamidoximes, amidines-, and guanidines |
| US3472872A (en) * | 1964-02-19 | 1969-10-14 | Sterling Drug Inc | Indolyl-lower-alkyl-amidoximes |
| US3420847A (en) * | 1964-02-19 | 1969-01-07 | Sterling Drug Inc | Pyrrolyl-lower-alkyl-amidoximes |
| US3539576A (en) * | 1967-07-17 | 1970-11-10 | American Home Prod | 1,2,3,7,8,12b-hexahydrobenzo(1,2)cyclohepta(3,4,5 - d,e) isoquinolinomethyleneamidoximes and esters thereof |
| US3505336A (en) * | 1968-05-06 | 1970-04-07 | Sterling Drug Inc | 3,4-dihydro-2-(1h)-isoquinolinecarboxamidoximes and lower-alkanoates |
-
1968
- 1968-01-03 DE DE1670497A patent/DE1670497C3/de not_active Expired
- 1968-05-13 IL IL29976A patent/IL29976A/xx unknown
- 1968-05-14 GB GB22891/68A patent/GB1187348A/en not_active Expired
- 1968-05-15 CA CA020072A patent/CA925869A/en not_active Expired
- 1968-05-16 AT AT469968A patent/AT277234B/de not_active IP Right Cessation
- 1968-05-28 CH CH788868A patent/CH526539A/de not_active IP Right Cessation
- 1968-05-29 US US732845A patent/US3673188A/en not_active Expired - Lifetime
- 1968-05-31 FR FR153515A patent/FR7892M/fr not_active Expired
- 1968-05-31 DK DK256768AA patent/DK141120B/da not_active IP Right Cessation
- 1968-06-04 CS CS4122A patent/CS168502B2/cs unknown
- 1968-06-04 SE SE07469/68A patent/SE335128B/xx unknown
- 1968-06-04 YU YU1285/68A patent/YU33285B/xx unknown
- 1968-06-05 NO NO02188/68A patent/NO127054B/no unknown
- 1968-06-05 FI FI681576A patent/FI52857C/fi active
- 1968-06-05 BR BR199612/68A patent/BR6899612D0/pt unknown
- 1968-06-06 NL NL686807919A patent/NL139238B/xx not_active IP Right Cessation
- 1968-06-06 BE BE716174D patent/BE716174A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CS168502B2 (OSRAM) | 1976-06-29 |
| DK141120C (OSRAM) | 1980-07-14 |
| IL29976A (en) | 1971-11-29 |
| BR6899612D0 (pt) | 1973-05-10 |
| FI52857B (OSRAM) | 1977-08-31 |
| NL6807919A (OSRAM) | 1968-12-09 |
| FI52857C (fi) | 1977-12-12 |
| IL29976A0 (en) | 1968-07-25 |
| NL139238B (nl) | 1973-07-16 |
| SE335128B (OSRAM) | 1971-05-17 |
| NO127054B (OSRAM) | 1973-04-30 |
| CA925869A (en) | 1973-05-08 |
| BE716174A (OSRAM) | 1968-11-04 |
| FR7892M (OSRAM) | 1970-05-04 |
| DE1670497B2 (de) | 1973-05-24 |
| CH526539A (de) | 1972-08-15 |
| US3673188A (en) | 1972-06-27 |
| DE1670497C3 (de) | 1973-12-20 |
| AT277234B (de) | 1969-12-10 |
| YU33285B (en) | 1976-08-31 |
| DE1670497A1 (de) | 1972-01-27 |
| GB1187348A (en) | 1970-04-08 |
| YU128568A (en) | 1976-03-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Godefroi et al. | DL-1-(1-arylalkyl) imidazole-5-carboxylate esters. A novel type of hypnotic agents | |
| US6965036B2 (en) | Intermediates for guanidine mimics as factor Xa inhibitors | |
| DK141122B (da) | Analogifremgangsmåde til fremstilling af substituerede benzimidazoler eller syreadditionssalte deraf. | |
| SU450398A3 (ru) | Способ получени -арил-2аминоалкоксистиролов | |
| US3705153A (en) | Novel thiazolyacetic acids and salts thereof | |
| Shaw et al. | iso Oxazolones. Part VI. The hydrogenation of 5-amino iso oxazoles. A new synthesis of pyrimidines | |
| US3673188A (en) | Heterocyclic amidoximes | |
| SU475768A3 (ru) | Способ получени (5-нитрофурил-2) -пиридинов | |
| GB937724A (en) | New pyrazolo-pyrimidines and process for the preparation thereof | |
| US3001992A (en) | S-niteo-z-fubftjewdene | |
| US3231574A (en) | Piperazine derivatives | |
| SU461505A3 (ru) | Способ получени 2-(5-нитро-2тиазолил) бенззимидазолов | |
| NO126624B (OSRAM) | ||
| US3194808A (en) | Preparation of 1-(aromatic-alkyl)-2, 4-dioxohexahydropyrimidines | |
| SU470959A3 (ru) | Способ получени 3-амино- 2-пиразолиновых производных или их солей | |
| US3127420A (en) | N1-[(5-nitro-2-furyl)alkylidene]-n-substituted n-(n-substituted carbamoylalkyl) hydrazines | |
| GB2024815A (en) | Imidazolylethoxy derivatives of pyrazolo-(o,4-b)pyridine-5-methanols | |
| SE441923B (sv) | 1-acyl-2-imidazolin till anvendning som mellanprodukt vid framstellning av 1-osubstituerad-2-imidazolin samt forfarande for dess framstellning | |
| GB703273A (en) | Manufacture of new derivatives of imidazole | |
| US3244593A (en) | Pharmaceutically active substituted 5-pyrazolones | |
| DK170043B1 (da) | 5-phenyl-1,4,5,6-tetrahydropyrimidinderivater, fremgangsmåde til fremstilling heraf, farmaceutisk middel indeholdende disse samt anvendelse af derivaterne til fremstilling af et farmaceutisk middel | |
| US3206461A (en) | 1-acyl-1-[2-(azacyclyl) ethyl]-2-(5-nitrofurfurylidene)hydrazines | |
| US2733244A (en) | G-tetrahydropyrimidine and imidaz- | |
| AT238188B (de) | Verfahren zur Herstellung von neuen, substituierten Hydrazinverbindungen | |
| US3091611A (en) | Alkylalkoxyalkylhydrazones |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |