BE548074A - - Google Patents
Info
- Publication number
- BE548074A BE548074A BE548074DA BE548074A BE 548074 A BE548074 A BE 548074A BE 548074D A BE548074D A BE 548074DA BE 548074 A BE548074 A BE 548074A
- Authority
- BE
- Belgium
- Prior art keywords
- acid
- imide
- formula
- residue
- carbon atoms
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 description 16
- 150000003949 imides Chemical group 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 11
- 125000004432 carbon atoms Chemical group C* 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 238000007363 ring formation reaction Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 150000001991 dicarboxylic acids Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- FEFFSKLJNYRHQN-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)pentanedioic acid Chemical compound C1=CC=C2C(=O)N(C(CCC(=O)O)C(O)=O)C(=O)C2=C1 FEFFSKLJNYRHQN-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- -1 dicarboxylic acid imide Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical class OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PAMWIQZMLLUFBP-UHFFFAOYSA-N 1-aminopiperidine-2,6-dione Chemical class NN1C(=O)CCCC1=O PAMWIQZMLLUFBP-UHFFFAOYSA-N 0.000 description 2
- 229960002989 Glutamic Acid Drugs 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N Thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 239000004220 glutamic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 206010003840 Autonomic nervous system imbalance Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 101700076142 ERL1 Proteins 0.000 description 1
- 229940083094 Guanine derivatives acting on arteriolar smooth muscle Drugs 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000036740 Metabolism Effects 0.000 description 1
- 206010054808 Peripheral paralysis Diseases 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N Phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N Propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000002921 anti-spasmodic Effects 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 150000001912 cyanamides Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 230000000147 hypnotic Effects 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000035786 metabolism Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940083145 peripherally acting antiadrenergic agents Guanine derivatives Drugs 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001624 sedative Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000002048 spasmolytic Effects 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000001131 transforming Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE548074A true BE548074A (pt) |
Family
ID=174794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE548074D BE548074A (pt) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE548074A (pt) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0166692A2 (de) * | 1984-06-20 | 1986-01-02 | Ciba-Geigy Ag | Substituierte Azabicycloheptane, ihre Verwendung, pharmazeutische Präparate, welche diese Verbindungen enthalten, und Verfahren zur Herstellung dieser Verbindungen |
| US4839379A (en) * | 1982-12-21 | 1989-06-13 | Ciba-Geigy Corporation | Substituted azabicycloalkanes, the use thereof, pharmaceutical compositions containing them |
-
0
- BE BE548074D patent/BE548074A/fr unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4839379A (en) * | 1982-12-21 | 1989-06-13 | Ciba-Geigy Corporation | Substituted azabicycloalkanes, the use thereof, pharmaceutical compositions containing them |
| EP0166692A2 (de) * | 1984-06-20 | 1986-01-02 | Ciba-Geigy Ag | Substituierte Azabicycloheptane, ihre Verwendung, pharmazeutische Präparate, welche diese Verbindungen enthalten, und Verfahren zur Herstellung dieser Verbindungen |
| EP0166692A3 (en) * | 1984-06-20 | 1986-11-12 | Ciba-Geigy Ag | Substituted azabicycloheptanes, their use, pharmaceutical compositions comprising them and process for the preparation of the compounds |
| US4764640A (en) * | 1984-06-20 | 1988-08-16 | Ciba-Geigy Corporation | Substituted azabicycloheptanes, the use thereof, pharmaceutical preparations that contain these compounds, and processes for the manufacture of these compounds |
| US4857660A (en) * | 1984-06-20 | 1989-08-15 | Ciba-Geigy Corporation | Certain 1-phenyl-cyclobutane-1,3-dicarboxylic acid type compounds |
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