BE532805A - - Google Patents
Info
- Publication number
- BE532805A BE532805A BE532805DA BE532805A BE 532805 A BE532805 A BE 532805A BE 532805D A BE532805D A BE 532805DA BE 532805 A BE532805 A BE 532805A
- Authority
- BE
- Belgium
- Prior art keywords
- group
- bis
- ene
- water
- solution
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-Butyne Chemical group CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 5
- ZQDPJFUHLCOCRG-AATRIKPKSA-N (E)-hex-3-ene Chemical compound CC\C=C\CC ZQDPJFUHLCOCRG-AATRIKPKSA-N 0.000 claims description 3
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- IZZOKZMGQDMCAE-XQZFLANJSA-N α-L-Rhap-(1->2)-[β-D-GlcpNAc-(1->3)]-α-L-Rhap-(1->3)-α-L-Rhap-(1->2)-[β-D-GlcpNAc-(1->3)]-α-L-Rhap Chemical group O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](C)O[C@H]2O)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)NC(C)=O)O[C@@H](C)[C@@H]1O IZZOKZMGQDMCAE-XQZFLANJSA-N 0.000 claims description 3
- WZHKDGJSXCTSCK-FNORWQNLSA-N (E)-hept-3-ene Chemical compound CCC\C=C\CC WZHKDGJSXCTSCK-FNORWQNLSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- -1 alkyl radical Chemical class 0.000 description 27
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 238000002844 melting Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 125000004432 carbon atoms Chemical group C* 0.000 description 12
- 230000004927 fusion Effects 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N Nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M Potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000005712 crystallization Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000002829 nitrogen Chemical group 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N Octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atoms Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000008079 hexane Substances 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- DIOQZVSQGTUSAI-UHFFFAOYSA-N Decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- 210000004185 Liver Anatomy 0.000 description 1
- 210000001758 Mesenteric Veins Anatomy 0.000 description 1
- 206010057249 Phagocytosis Diseases 0.000 description 1
- 210000003240 Portal Vein Anatomy 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241000242680 Schistosoma mansoni Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 201000009910 diseases by infectious agent Diseases 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- KIMVTSGNCBGHES-UHFFFAOYSA-N octane;dihydrochloride Chemical compound Cl.Cl.CCCCCCCC KIMVTSGNCBGHES-UHFFFAOYSA-N 0.000 description 1
- 230000008782 phagocytosis Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 229940013123 stannous chloride Drugs 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin dichloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE532805A true BE532805A (nl) |
Family
ID=164701
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE532805D BE532805A (nl) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE532805A (nl) |
-
0
- BE BE532805D patent/BE532805A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0591057B1 (fr) | Arylalkyl(thio)amides ayant une affinité sélective pour les récepteurs de la mélatonine et leur procédé de préparation | |
| EP0526313A1 (fr) | Nouveaux dérivés de l'urée, leur préparation et leur application en thérapeutique | |
| EP0002978B1 (fr) | Dérivés de thiazolidinedione-2,4, leur préparation et leur application en thérapeutique | |
| EP0021940A1 (fr) | Nouveaux dérivés aminés du benzothiazole, leur procédé de préparation et leur application en thérapeutique | |
| BE532805A (nl) | ||
| EP0354078B1 (fr) | Nouveaux dérivés du benzocycloheptène, leur procédé de préparation et les compositions pharmaceutiques les renfermant | |
| JPH01313457A (ja) | Ｎ‐（３’，４’‐ジメトキシ−シンナモイル）‐アンスラニル酸の製造方法 | |
| EP0069012A1 (fr) | Dérivés de benzoyl-phényl-pipéridine, procédé de préparation et application en thérapeutique | |
| BE514410A (nl) | ||
| BE525695A (nl) | ||
| BE536589A (nl) | ||
| BE503348A (nl) | ||
| BE536553A (nl) | ||
| CA1097682A (fr) | Procede d'obtention de derives de l'acide phenylacetique | |
| BE532806A (nl) | ||
| BE525394A (nl) | ||
| BE488997A (nl) | ||
| CH422762A (fr) | Procédé de préparation d'esters d'acides di-tert-butyl-naphtalène-4-sulfonique | |
| FR2473512A1 (fr) | Nouveaux 2-aminomethyl-6-halogeno-phenols, leur preparation et leur application comme medicaments | |
| CH313377A (fr) | Procédé de préparation de nouveaux dérivés de la phénothiazine | |
| BE524653A (nl) | ||
| CH275969A (fr) | Procédé de préparation d'une sulfanilamido-quinoxaline substituée. | |
| CH333012A (fr) | Procédé de préparation de nouveaux dérivés de la phénothiazine | |
| CH321872A (fr) | Procédé de préparation d'halogéno-2-amino-2'-diphénylsulfures | |
| WO1993012099A1 (fr) | Procede de preparation d'amino-2 nitro-7 benzothiazoles |