NO118171B - - Google Patents

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Info

Publication number: NO118171B
Authority: NO; Norway
Prior art keywords: compound; formula; ether; mol; compounds
Prior art date: 1966-12-30

Application number

NO17122567A

Other languages

English (en)

Norwegian (no)

Inventor

J Dahlbom

B Karlen

Original Assignee

Astra Ab

Priority date (The priority date 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 date listed.)

1966-12-30

Filing date

1967-12-30

Publication date

1969-11-24

1967-12-30 Application filed by Astra Ab filed Critical Astra Ab

1969-11-24 Publication of NO118171B publication Critical patent/NO118171B/no

Links

150000001875 compounds Chemical class 0.000 claims description 70
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 21
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
238000000034 method Methods 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 8
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
150000008064 anhydrides Chemical class 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
239000001632 sodium acetate Substances 0.000 claims description 5
235000017281 sodium acetate Nutrition 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
-1 N-substituted succinimides Chemical class 0.000 description 27
239000000203 mixture Substances 0.000 description 18
238000002844 melting Methods 0.000 description 17
230000008018 melting Effects 0.000 description 17
239000000243 solution Substances 0.000 description 15
RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
230000000694 effects Effects 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
238000003756 stirring Methods 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
230000002911 mydriatic effect Effects 0.000 description 8
230000002093 peripheral effect Effects 0.000 description 7
239000011734 sodium Substances 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
230000001713 cholinergic effect Effects 0.000 description 6
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
206010010904 Convulsion Diseases 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 5
239000005557 antagonist Substances 0.000 description 5
230000001078 anti-cholinergic effect Effects 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
229940014800 succinic anhydride Drugs 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
238000004566 IR spectroscopy Methods 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000000812 cholinergic antagonist Substances 0.000 description 4
230000036461 convulsion Effects 0.000 description 4
239000012259 ether extract Substances 0.000 description 4
239000005457 ice water Substances 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
229960002317 succinimide Drugs 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
JSUAJTLKVREZHV-UHFFFAOYSA-N 1-[4-(1-pyrrolidinyl)but-2-ynyl]pyrrolidine Chemical compound C1CCCN1CC#CCN1CCCC1 JSUAJTLKVREZHV-UHFFFAOYSA-N 0.000 description 3
229930003347 Atropine Natural products 0.000 description 3
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 3
229960000396 atropine Drugs 0.000 description 3
XSBPYGDBXQXSCU-UHFFFAOYSA-N but-3-yn-1-amine Chemical compound NCCC#C XSBPYGDBXQXSCU-UHFFFAOYSA-N 0.000 description 3
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
XINSCWBHVQVKQT-UHFFFAOYSA-N 1-(5-pyrrolidin-1-ylpent-3-yn-2-yl)pyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1C(C)C#CCN1CCCC1 XINSCWBHVQVKQT-UHFFFAOYSA-N 0.000 description 2
IUHLDFUCIBLTSP-UHFFFAOYSA-N 1-but-3-yn-2-ylpyrrolidine-2,5-dione Chemical compound CC(C#C)N1C(CCC1=O)=O IUHLDFUCIBLTSP-UHFFFAOYSA-N 0.000 description 2
CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 2
VKFVDYACCHOPEV-UHFFFAOYSA-N 4-(but-3-ynylamino)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)NCCC#C VKFVDYACCHOPEV-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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 2
241001465754 Metazoa Species 0.000 description 2
208000007101 Muscle Cramp Diseases 0.000 description 2
229930040373 Paraformaldehyde Natural products 0.000 description 2
208000018737 Parkinson disease Diseases 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
208000005392 Spasm Diseases 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
229940040526 anhydrous sodium acetate Drugs 0.000 description 2
ZZRMYOZQUCUWFT-UHFFFAOYSA-N but-3-yn-2-amine Chemical compound CC(N)C#C ZZRMYOZQUCUWFT-UHFFFAOYSA-N 0.000 description 2
OFAIGZWCDGNZGT-UHFFFAOYSA-N caramiphen Chemical compound C=1C=CC=CC=1C1(C(=O)OCCN(CC)CC)CCCC1 OFAIGZWCDGNZGT-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000005259 measurement Methods 0.000 description 2
239000002207 metabolite Substances 0.000 description 2
229920002866 paraformaldehyde Polymers 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
210000001747 pupil Anatomy 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-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
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
NXAFJDDDPHVQDC-UHFFFAOYSA-N 1-(5-pyrrolidin-1-ylpent-3-ynyl)pyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1CCC#CCN1CCCC1 NXAFJDDDPHVQDC-UHFFFAOYSA-N 0.000 description 1
ZVKVRXMDTPYHHX-UHFFFAOYSA-N 1-but-3-ynylpyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1CCC#C ZVKVRXMDTPYHHX-UHFFFAOYSA-N 0.000 description 1
HLMHCDKXKXBKQK-UHFFFAOYSA-N 2-bromoethyl(diethyl)azanium;bromide Chemical compound Br.CCN(CC)CCBr HLMHCDKXKXBKQK-UHFFFAOYSA-N 0.000 description 1
VUGCBIWQHSRQBZ-UHFFFAOYSA-N 2-methylbut-3-yn-2-amine Chemical compound CC(C)(N)C#C VUGCBIWQHSRQBZ-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
QSILYWCNPOLKPN-UHFFFAOYSA-N 3-chloro-3-methylbut-1-yne Chemical compound CC(C)(Cl)C#C QSILYWCNPOLKPN-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
208000006083 Hypokinesia Diseases 0.000 description 1
229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
208000006550 Mydriasis Diseases 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
206010039424 Salivary hypersecretion Diseases 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
206010044565 Tremor Diseases 0.000 description 1
LOPQJRXCVHBKKN-UHFFFAOYSA-N acetylene;azane Chemical compound N.C#C LOPQJRXCVHBKKN-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000010171 animal model Methods 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
XWRDBUBKBUYLQI-UHFFFAOYSA-N but-3-yn-2-yl 4-methylbenzenesulfonate Chemical compound C#CC(C)OS(=O)(=O)C1=CC=C(C)C=C1 XWRDBUBKBUYLQI-UHFFFAOYSA-N 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
KDKYADYSIPSCCQ-UHFFFAOYSA-N ethyl acetylene Natural products CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
IKXNIQJDNKPPCH-UHFFFAOYSA-N hydron;prop-2-yn-1-amine;chloride Chemical compound [Cl-].[NH3+]CC#C IKXNIQJDNKPPCH-UHFFFAOYSA-N 0.000 description 1
230000003483 hypokinetic effect Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
229940046892 lead acetate Drugs 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 description 1
VLFIKWATQCJNSZ-UHFFFAOYSA-N n',n'-diethylpent-2-yne-1,5-diamine Chemical compound CCN(CC)CCC#CCN VLFIKWATQCJNSZ-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000001499 parasympathomimetic effect Effects 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
230000010344 pupil dilation Effects 0.000 description 1
ZUTNAPRHBFFUBV-UHFFFAOYSA-N pyrrolidine-2,5-dione;hydrochloride Chemical compound Cl.O=C1CCC(=O)N1 ZUTNAPRHBFFUBV-UHFFFAOYSA-N 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
208000026451 salivation Diseases 0.000 description 1
238000005185 salting out Methods 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
- C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyrrole Compounds (AREA)
Hydrogenated Pyridines (AREA)

NO17122567A 1966-12-30 1967-12-30 NO118171B (da)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US60606366A	1966-12-30	1966-12-30

Publications (1)

Publication Number	Publication Date
NO118171B true NO118171B (da)	1969-11-24

Family

ID=24426373

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO17122567A NO118171B (da)	1966-12-30	1967-12-30

Country Status (5)

Country	Link
DK (1)	DK124403B (da)
FI (1)	FI48925C (da)
NL (1)	NL6717671A (da)
NO (1)	NO118171B (da)
SE (1)	SE323374B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2059985A1 (en) *	1969-08-29	1971-06-11	Synthelabo	4-benzyl piperidine 2,6-dione derivs

1967
- 1967-12-11 SE SE1702167A patent/SE323374B/xx unknown
- 1967-12-22 DK DK648267A patent/DK124403B/da unknown
- 1967-12-27 NL NL6717671A patent/NL6717671A/xx not_active Application Discontinuation
- 1967-12-29 FI FI351267A patent/FI48925C/fi active
- 1967-12-30 NO NO17122567A patent/NO118171B/no unknown

Also Published As

Publication number	Publication date
SE323374B (da)	1970-05-04
FI48925C (fi)	1975-02-10
NL6717671A (da)	1968-07-01
FI48925B (da)	1974-10-31
DK124403B (da)	1972-10-16

Publication	Publication Date	Title
NO158419B (no)	1988-05-30	Analogifremgangsmaate til fremstilling av terapeutisk aktive 1,2-diaminocyklobuten-3,4-dioner.
US4818764A (en)	1989-04-04	Imidazoline derivative and method of treating depression therewith
SU1156593A3 (ru)	1985-05-15	Способ получени производных бензамида или их кислотно-аддитивных солей,или оптических изомеров
KR850000216B1 (ko)	1985-03-06	피페라진 유도체의 제조방법
NO123034B (da)	1971-09-20
US4499286A (en)	1985-02-12	Derivatives of thienylacetic acid amides and their pharmaceutically acceptable acid salts and a process for the preparation thereof
NO127670B (da)	1973-07-30
US4397860A (en)	1983-08-09	Benzodioxanyl imidazoline compounds, compositions and use
NO118171B (da)	1969-11-24
KR870001681B1 (ko)	1987-09-22	히단토인 유도체의 제조방법
SU784763A3 (ru)	1980-11-30	Способ получени производных 6- метокси-2-ацетилнафтилоксима или их хлоргидратов
EP0232675B1 (de)	1990-11-22	5-Aminoalkyl-Beta-Carbolinderivate, ihre Herstellung und Verwendung als Arzneimittel
NO155056B (no)	1986-10-27	Sprengstoff.
US4173636A (en)	1979-11-06	Decahydroquinolines, pharmaceutical compositions and methods of use
US4758563A (en)	1988-07-19	3-alkoxy-2-aminopropyamines, cardiovascular compositions and use
US2928835A (en)	1960-03-15	New esters
NO133670B (da)	1976-03-01
SU833157A3 (ru)	1981-05-23	Способ получени производных циклододекана или их оптическиАКТиВНыХ изОМЕРОВ B СВОбОдНОМ ВидЕ,B ВидЕ СОли или чЕТВЕРТич-НыХ АММОНиЕВыХ пРОизВОдНыХ
US3998965A (en)	1976-12-21	4-Aminoalkyl-4-cyano-4-phenyl-butanoic acid esters
NO138804B (no)	1978-08-07	Analogifremgangsmaater til fremstilling av aminosyrederivater med antidepressiv virkning
NO126693B (da)	1973-03-12
US3946018A (en)	1976-03-23	1,4-Dihydro-3 (2H)-isoquinolinone derivatives
KR830001838B1 (ko)	1983-09-14	페닐-퀴놀리지딘의 제조방법
EP0000693A1 (de)	1979-02-21	Aminophenoxymethyl-2-morpholinderivate, ihre Herstellung und sie enthaltende Arzneimittel
NO137893B (no)	1978-02-06	Analogifremgangsm}te for fremstilling av terapeutisk aktive 1-m-trifluormetylfenyl-2-cyanoalkylaminopropaner