DE2254564A1 - Neue organische verbindungen und verfahren zu deren herstellung - Google Patents
Neue organische verbindungen und verfahren zu deren herstellungInfo
- Publication number
- DE2254564A1 DE2254564A1 DE19722254564 DE2254564A DE2254564A1 DE 2254564 A1 DE2254564 A1 DE 2254564A1 DE 19722254564 DE19722254564 DE 19722254564 DE 2254564 A DE2254564 A DE 2254564A DE 2254564 A1 DE2254564 A1 DE 2254564A1
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- carbon atoms
- formula
- group
- hydrogen
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
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- 239000000126 substance Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 6
- 101150052863 THY1 gene Proteins 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- -1 nitrogen-containing heterocyclic group Radical Chemical class 0.000 description 43
- 239000000243 solution Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- 239000002253 acid Substances 0.000 description 5
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- 239000003054 catalyst Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 239000004480 active ingredient Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
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- 238000002347 injection Methods 0.000 description 3
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- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- ZGNIGUQLCBBYSR-UHFFFAOYSA-N 4-[amino(methyl)amino]-1h-pyridazin-6-one Chemical compound CN(N)C=1C=NNC(=O)C=1 ZGNIGUQLCBBYSR-UHFFFAOYSA-N 0.000 description 2
- GUVGKGYZPQVGAJ-UHFFFAOYSA-N 5-[amino(methyl)amino]-4-chloro-2-[3-(trifluoromethyl)phenyl]pyridazin-3-one Chemical compound O=C1C(Cl)=C(N(N)C)C=NN1C1=CC=CC(C(F)(F)F)=C1 GUVGKGYZPQVGAJ-UHFFFAOYSA-N 0.000 description 2
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- SCCLRAWMUKTDKT-UHFFFAOYSA-N C1=CC(=CC(=C1)Cl)N2C=C(C(=CN2)Cl)Cl Chemical compound C1=CC(=CC(=C1)Cl)N2C=C(C(=CN2)Cl)Cl SCCLRAWMUKTDKT-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000001914 calming effect Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000000147 hypnotic effect Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 230000035484 reaction time Effects 0.000 description 2
- 229940125723 sedative agent Drugs 0.000 description 2
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- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- BRFJZIHZLSBXLX-UHFFFAOYSA-N 2-(3-methylphenyl)pyridazin-3-one Chemical compound CC1=CC=CC(N2C(C=CC=N2)=O)=C1 BRFJZIHZLSBXLX-UHFFFAOYSA-N 0.000 description 1
- HPFRGEKQAFDJEN-UHFFFAOYSA-N 2-(4-methylphenyl)pyridazin-3-one Chemical compound C1(=CC=C(C=C1)N1N=CC=CC1=O)C HPFRGEKQAFDJEN-UHFFFAOYSA-N 0.000 description 1
- AJHBQZQCDCTOFD-UHFFFAOYSA-N 2-benzyl-4,5-dichloropyridazin-3-one Chemical compound O=C1C(Cl)=C(Cl)C=NN1CC1=CC=CC=C1 AJHBQZQCDCTOFD-UHFFFAOYSA-N 0.000 description 1
- GBHCABUWWQUMAJ-UHFFFAOYSA-N 2-hydrazinoethanol Chemical compound NNCCO GBHCABUWWQUMAJ-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- YHUPDXDIWROOHO-UHFFFAOYSA-N 4,5-dichloro-2-(2,5-dichlorophenyl)pyridazin-3-one Chemical compound ClC1=CC=C(Cl)C(N2C(C(Cl)=C(Cl)C=N2)=O)=C1 YHUPDXDIWROOHO-UHFFFAOYSA-N 0.000 description 1
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- QARILIFILZKMIE-UHFFFAOYSA-N 4,5-dichloro-2-(4-nitrophenyl)pyridazin-3-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1C(=O)C(Cl)=C(Cl)C=N1 QARILIFILZKMIE-UHFFFAOYSA-N 0.000 description 1
- WVDKLQRXAMTHTJ-UHFFFAOYSA-N 4,5-dichloro-2-[2-(trifluoromethyl)phenyl]pyridazin-3-one Chemical compound FC(F)(F)C1=CC=CC=C1N1C(=O)C(Cl)=C(Cl)C=N1 WVDKLQRXAMTHTJ-UHFFFAOYSA-N 0.000 description 1
- AGAUXSXAYBJHAY-UHFFFAOYSA-N 4,5-dichloro-2-[4-chloro-3-(trifluoromethyl)phenyl]pyridazin-3-one Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(N2C(C(Cl)=C(Cl)C=N2)=O)=C1 AGAUXSXAYBJHAY-UHFFFAOYSA-N 0.000 description 1
- VKWCOHVAHQOJGU-UHFFFAOYSA-N 4,5-dichloro-2-phenylpyridazin-3-one Chemical compound O=C1C(Cl)=C(Cl)C=NN1C1=CC=CC=C1 VKWCOHVAHQOJGU-UHFFFAOYSA-N 0.000 description 1
- XXRQNPZEVXZYPI-UHFFFAOYSA-N 5-[amino(methyl)amino]-2-[3-(trifluoromethyl)phenyl]pyridazin-3-one Chemical compound O=C1C=C(N(N)C)C=NN1C1=CC=CC(C(F)(F)F)=C1 XXRQNPZEVXZYPI-UHFFFAOYSA-N 0.000 description 1
- LZDDRZQNUFAWTO-UHFFFAOYSA-N 5-[amino(methyl)amino]-4-chloro-2-(2,3-dichlorophenyl)pyridazin-3-one Chemical compound O=C1C(Cl)=C(N(N)C)C=NN1C1=CC=CC(Cl)=C1Cl LZDDRZQNUFAWTO-UHFFFAOYSA-N 0.000 description 1
- GTUIWDANFISRCM-UHFFFAOYSA-N 5-[amino(methyl)amino]-4-chloro-2-(2,5-dichlorophenyl)pyridazin-3-one Chemical compound O=C1C(Cl)=C(N(N)C)C=NN1C1=CC(Cl)=CC=C1Cl GTUIWDANFISRCM-UHFFFAOYSA-N 0.000 description 1
- LNKSSVHNWYHXSM-UHFFFAOYSA-N 5-[amino(methyl)amino]-4-chloro-2-(2-chlorophenyl)pyridazin-3-one Chemical compound O=C1C(Cl)=C(N(N)C)C=NN1C1=CC=CC=C1Cl LNKSSVHNWYHXSM-UHFFFAOYSA-N 0.000 description 1
- BAWNUIKKPHPLGU-UHFFFAOYSA-N 5-[amino(methyl)amino]-4-chloro-2-(4-methylphenyl)pyridazin-3-one Chemical compound O=C1C(Cl)=C(N(N)C)C=NN1C1=CC=C(C)C=C1 BAWNUIKKPHPLGU-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
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- 239000006172 buffering agent Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
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- 239000003937 drug carrier Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
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- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
- 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 1
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- 229940067606 lecithin Drugs 0.000 description 1
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- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
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- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004799 sedative–hypnotic effect Effects 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
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- 239000008247 solid mixture Substances 0.000 description 1
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- 239000006188 syrup Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-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
- C07D237/22—Nitrogen and oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19740171A | 1971-11-10 | 1971-11-10 | |
| US22726972A | 1972-02-17 | 1972-02-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2254564A1 true DE2254564A1 (de) | 1973-05-17 |
Family
ID=26892821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722254564 Pending DE2254564A1 (de) | 1971-11-10 | 1972-11-08 | Neue organische verbindungen und verfahren zu deren herstellung |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4856690A (OSRAM) |
| AU (1) | AU4870872A (OSRAM) |
| BE (1) | BE791098A (OSRAM) |
| DD (1) | DD101675A5 (OSRAM) |
| DE (1) | DE2254564A1 (OSRAM) |
| FR (1) | FR2251330A1 (OSRAM) |
| HU (1) | HU164963B (OSRAM) |
| NL (1) | NL7214879A (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3229325A1 (de) * | 1982-08-06 | 1984-02-09 | Basf Ag, 6700 Ludwigshafen | Substituierte 4-fluorpyridaz-6-one |
| HU195645B (en) * | 1985-10-30 | 1988-06-28 | Gyogyszerkutato Intezet | Process for preparing novel 3(2h)-pyridazinone derivatives and pharmaceutical compositions comprising the same |
-
0
- BE BE791098D patent/BE791098A/xx unknown
-
1972
- 1972-11-03 NL NL7214879A patent/NL7214879A/xx unknown
- 1972-11-08 FR FR7239439A patent/FR2251330A1/fr active Granted
- 1972-11-08 DD DD16673272A patent/DD101675A5/xx unknown
- 1972-11-08 DE DE19722254564 patent/DE2254564A1/de active Pending
- 1972-11-08 JP JP11130372A patent/JPS4856690A/ja active Pending
- 1972-11-08 HU HUSA002417 patent/HU164963B/hu unknown
- 1972-11-09 AU AU48708/72A patent/AU4870872A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DD101675A5 (OSRAM) | 1973-11-12 |
| FR2251330B1 (OSRAM) | 1977-01-14 |
| JPS4856690A (OSRAM) | 1973-08-09 |
| AU4870872A (en) | 1974-05-09 |
| HU164963B (OSRAM) | 1974-05-28 |
| BE791098A (fr) | 1973-05-08 |
| NL7214879A (OSRAM) | 1973-05-14 |
| FR2251330A1 (en) | 1975-06-13 |
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