BE539515A - - Google Patents
Info
- Publication number
- BE539515A BE539515A BE539515DA BE539515A BE 539515 A BE539515 A BE 539515A BE 539515D A BE539515D A BE 539515DA BE 539515 A BE539515 A BE 539515A
- Authority
- BE
- Belgium
- Prior art keywords
- choline
- xanthine
- product
- alkoxy
- carbon atoms
- Prior art date
Links
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 66
- 239000000047 product Substances 0.000 claims description 38
- -1 methoxy choline Chemical compound 0.000 claims description 36
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims description 34
- 229960001231 choline Drugs 0.000 claims description 29
- 229940075420 xanthine Drugs 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 19
- 229960000278 theophylline Drugs 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- 238000000926 separation method Methods 0.000 claims description 13
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims description 11
- 235000019743 Choline chloride Nutrition 0.000 claims description 11
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 11
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims description 11
- 229960003178 choline chloride Drugs 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 claims description 10
- 150000001340 alkali metals Chemical class 0.000 claims description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 7
- 229910052700 potassium Chemical group 0.000 claims description 7
- 239000011591 potassium Chemical group 0.000 claims description 7
- 150000003248 quinolines Chemical class 0.000 claims description 6
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims description 5
- 229960004559 theobromine Drugs 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 229910001510 metal chloride Inorganic materials 0.000 claims 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims 1
- RLANKEDHRWMNRO-UHFFFAOYSA-M oxtriphylline Chemical compound C[N+](C)(C)CCO.O=C1N(C)C(=O)N(C)C2=C1[N-]C=N2 RLANKEDHRWMNRO-UHFFFAOYSA-M 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- SOELXOBIIIBLRJ-UHFFFAOYSA-M choline theophyllinate Chemical compound C[N+](C)(C)CCO.CN1C(=O)N(C)C([O-])=C2N=CN=C21 SOELXOBIIIBLRJ-UHFFFAOYSA-M 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- 125000004429 atom Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- MGUBQPRSQWCLCX-UHFFFAOYSA-N 3,7-dimethylpurine-2,6-dione Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C.CN1C(=O)NC(=O)C2=C1N=CN2C MGUBQPRSQWCLCX-UHFFFAOYSA-N 0.000 description 1
- CBWONQBNYZSEKY-UHFFFAOYSA-N 8-propan-2-yl-3,7-dihydropurine-2,6-dione Chemical compound C(C)(C)C1=NC=2NC(NC(C=2N1)=O)=O CBWONQBNYZSEKY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- 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)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE539515A true BE539515A (enrdf_load_stackoverflow) |
Family
ID=169198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE539515D BE539515A (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE539515A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2420774A1 (de) * | 1973-07-09 | 1975-01-30 | Air Prod & Chem | Quartaere hydroxyalkylammoniumalkylate und -phenolate und verfahren zu deren herstellung |
-
0
- BE BE539515D patent/BE539515A/fr unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2420774A1 (de) * | 1973-07-09 | 1975-01-30 | Air Prod & Chem | Quartaere hydroxyalkylammoniumalkylate und -phenolate und verfahren zu deren herstellung |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0018342A1 (fr) | Nouveaux dérivés du glycerol, leurs procédés de préparation ainsi que les compositions pharmaceutiques les contenant | |
| EP1229073A2 (fr) | Beta-dicetones et utilisation en tant que stabilisant du pvc | |
| WO2011154661A1 (fr) | Procede de preparation de composes esteramides | |
| EP0195734A2 (fr) | Préparation d'herbicides à groupe phosphonates et d'intermédiaires à partir de benzoxazines | |
| JPH05310640A (ja) | ヒドロキシフェニルカルボキシレートの製造方法 | |
| BE539515A (enrdf_load_stackoverflow) | ||
| EP0173597A1 (fr) | Nouveaux éther-oxydes dérivés de cyclopropylphénols | |
| EP0122827A1 (fr) | (Carbéthoxy-2 benzalkylamido-4 phénoxy)-1 amino-3 propanols-2, leurs préparations et leurs utilisations en thérapeutique | |
| EP2376496B1 (fr) | Synthese de morphine-6-glucuronide ou de l'un de ses derives | |
| EP0685473B1 (fr) | Composés benzohétérocycliques, en tant qu'antioxydants | |
| EP0216659B1 (fr) | Nouveaux halogénoformiates de dihalogéno-2,2 vinyle, leur procédé de préparation et leurs applications | |
| BE653101A (enrdf_load_stackoverflow) | ||
| FR3011839A1 (fr) | Procede de preparation de derives d'acetamidophenyle | |
| EP1242439B1 (fr) | Procede pour preparer et isoler la 9-deoxo-9(z)-hydroxyiminoerythromycine a | |
| EP0022022B1 (fr) | Nouveaux dérivés acylés de la taurine et leurs sels et procédé pour leur préparation | |
| EP3530662B1 (fr) | Procédé de préparation d'heptazines | |
| EP0994846A1 (fr) | Procede de preparation de composes de type 4-(alkyl)-3-alcoxy-anilines | |
| WO2016207261A1 (fr) | Procédé de synthèse d'oximes aromatiques | |
| WO1999011602A1 (fr) | Procede de preparation de composes de type arylaminoalkylidenemalonates | |
| FR2607497A1 (fr) | Procede de preparation d'imines cycliques mono et disubstituees | |
| BE630012A (enrdf_load_stackoverflow) | ||
| FR2530245A1 (fr) | Nouveaux 1-(2-carbalkoxy 4-(thienyl-alkylamido)phenoxy) 3-amino 2-propanols, leur preparation et leurs applications en therapeutique | |
| BE632152A (enrdf_load_stackoverflow) | ||
| FR3055627A1 (fr) | Methode de preparation du compose cdb-3877 | |
| WO1999031080A1 (fr) | Nouveaux derives du furane, leurs procedes de synthese et leur utilisation comme exhausteur d'aromes |