BE714408A - - Google Patents
Info
- Publication number
- BE714408A BE714408A BE714408DA BE714408A BE 714408 A BE714408 A BE 714408A BE 714408D A BE714408D A BE 714408DA BE 714408 A BE714408 A BE 714408A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- sydnone
- dimethylamino
- compound according
- namely
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 description 41
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- NVRSPIKUPKOSIY-UHFFFAOYSA-N chembl1743348 Chemical class CC=1N=NOC=1O NVRSPIKUPKOSIY-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- -1 cyclic radical Chemical class 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 229940075930 picrate Drugs 0.000 description 6
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 206010010904 Convulsion Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 230000036461 convulsion Effects 0.000 description 3
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical compound I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- NUWZDEVIHXSGHY-UHFFFAOYSA-N 3-(dimethylamino)-4-(morpholin-4-ylmethyl)oxadiazol-3-ium-5-olate Chemical compound CN(C)[N+]1=NOC([O-])=C1CN1CCOCC1 NUWZDEVIHXSGHY-UHFFFAOYSA-N 0.000 description 2
- JOOWOECVJKSBAQ-UHFFFAOYSA-N 3-morpholin-4-yl-4-(morpholin-4-ylmethyl)oxadiazol-3-ium-5-olate Chemical compound O1CCN(CC1)[N+]=1[N-]OC(C1CN1CCOCC1)=O JOOWOECVJKSBAQ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 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
- 238000001816 cooling Methods 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- CKFAJJJSDYAUBI-UHFFFAOYSA-N 3-(dimethylamino)-4-(piperidin-1-ylmethyl)oxadiazol-3-ium-5-olate Chemical compound CN(C)[N+]1=NOC([O-])=C1CN1CCCCC1 CKFAJJJSDYAUBI-UHFFFAOYSA-N 0.000 description 1
- IZXGAKGRZXAUCQ-UHFFFAOYSA-N 3-(dimethylamino)-4-(pyrrolidin-1-ylmethyl)oxadiazol-3-ium-5-olate Chemical compound CN(C)[N+]1=NOC([O-])=C1CN1CCCC1 IZXGAKGRZXAUCQ-UHFFFAOYSA-N 0.000 description 1
- YEAYDKSHCSWWGW-UHFFFAOYSA-N 3-(dimethylamino)-4-[(dimethylamino)methyl]oxadiazol-3-ium-5-olate Chemical compound CN(C)CC1=C([O-])ON=[N+]1N(C)C YEAYDKSHCSWWGW-UHFFFAOYSA-N 0.000 description 1
- RZZRVUXBHIPLHR-UHFFFAOYSA-N 3-(dimethylamino)oxadiazol-3-ium-5-olate Chemical compound CN(C)[N+]=1C=C([O-])ON=1 RZZRVUXBHIPLHR-UHFFFAOYSA-N 0.000 description 1
- KUYNWZKDWRYCIH-UHFFFAOYSA-N 3-methyloxadiazol-3-ium-5-olate Chemical compound C[N+]=1C=C([O-])ON=1 KUYNWZKDWRYCIH-UHFFFAOYSA-N 0.000 description 1
- SNYYAQOZQVWIDC-UHFFFAOYSA-N 3-morpholin-4-yloxadiazol-3-ium-5-olate Chemical compound O1C([O-])=C[N+](N2CCOCC2)=N1 SNYYAQOZQVWIDC-UHFFFAOYSA-N 0.000 description 1
- DNAPHMQKYGSRPZ-UHFFFAOYSA-N 4-(diethylaminomethyl)-3-morpholin-4-yloxadiazol-3-ium-5-olate Chemical compound O1CCN(CC1)[N+]=1[N-]OC(C1CN(CC)CC)=O DNAPHMQKYGSRPZ-UHFFFAOYSA-N 0.000 description 1
- AXZZZFKKJLVIFG-UHFFFAOYSA-N 4-(morpholin-4-ylmethyl)-3-piperidin-1-yloxadiazol-3-ium-5-olate Chemical compound N1(CCCCC1)[N+]=1[N-]OC(C1CN1CCOCC1)=O AXZZZFKKJLVIFG-UHFFFAOYSA-N 0.000 description 1
- WJWODGPIEJIBJN-UHFFFAOYSA-N 4-[(dibutylamino)methyl]-3-(dimethylamino)oxadiazol-3-ium-5-olate Chemical compound CCCCN(CCCC)CC1=C([O-])ON=[N+]1N(C)C WJWODGPIEJIBJN-UHFFFAOYSA-N 0.000 description 1
- ULMAZPPGLNOPRU-UHFFFAOYSA-N 4-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-3-(dimethylamino)oxadiazol-3-ium-5-olate Chemical compound CN([N+]=1[N-]OC(C=1CN1CCN(CC1)C1=CC=C(C=C1)Cl)=O)C ULMAZPPGLNOPRU-UHFFFAOYSA-N 0.000 description 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
- MPVLOBDWKLNKOA-UHFFFAOYSA-N CN([N+]=1[N-]OC(C1CN(CC)CC)=O)C Chemical compound CN([N+]=1[N-]OC(C1CN(CC)CC)=O)C MPVLOBDWKLNKOA-UHFFFAOYSA-N 0.000 description 1
- 241000459479 Capsula Species 0.000 description 1
- QIVDXSBQVQUEDE-UHFFFAOYSA-N Cl.Cl.CN([N+]=1[N-]OC(C1CN1CCNCC1)=O)C Chemical compound Cl.Cl.CN([N+]=1[N-]OC(C1CN1CCNCC1)=O)C QIVDXSBQVQUEDE-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- IJZNOLWKANIROC-FQVYYFBESA-N N-[(3Z,5E)-3,5-bis(hydroxyimino)-2,2,6,6-tetramethylpiperidin-4-ylidene]hydroxylamine Chemical compound CC1(/C(=N/O)/C(=NO)/C(=N/O)/C(N1)(C)C)C IJZNOLWKANIROC-FQVYYFBESA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 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
- 229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940042126 oral powder Drugs 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE714408 | 1968-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE714408A true BE714408A (enrdf_load_html_response) | 1968-09-16 |
Family
ID=3852825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE714408D BE714408A (enrdf_load_html_response) | 1968-04-29 | 1968-04-29 |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE714408A (enrdf_load_html_response) |
-
1968
- 1968-04-29 BE BE714408D patent/BE714408A/fr unknown
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