CA1119600A - Derives des acides (2-oxo-pyrrolidine-1) et (2-oxo-piperidine-1) carboxyliques; procede pour leur fabrication et preparations pharmaceutiques qui en contiennent - Google Patents

Derives des acides (2-oxo-pyrrolidine-1) et (2-oxo-piperidine-1) carboxyliques; procede pour leur fabrication et preparations pharmaceutiques qui en contiennent

Info

Publication number: CA1119600A
Authority: CA; Canada
Prior art keywords: hydrazide; formula; defined above; oxo; methyl
Prior art date: 1979-04-10
Legal status (The legal status 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 status listed.): Expired

Application number

CA000325263A

Other languages

English (en)

Inventor

Fritz-Walter Lange

Jens Muller

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ics Consulting & Service Co AG

Original Assignee

Ics Consulting & Service Co AG

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.)

1979-04-10

Filing date

1979-04-10

Publication date

1982-03-09

1979-04-10 Application filed by Ics Consulting & Service Co AG filed Critical Ics Consulting & Service Co AG

1979-04-10 Priority to CA000325263A priority Critical patent/CA1119600A/fr

1982-03-09 Application granted granted Critical

1982-03-09 Publication of CA1119600A publication Critical patent/CA1119600A/fr

Status Expired legal-status Critical Current

Links

239000000825 pharmaceutical preparation Substances 0.000 title description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 title description 2
238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 34
150000003839 salts Chemical class 0.000 claims abstract description 23
238000000034 method Methods 0.000 claims description 46
229910052757 nitrogen Inorganic materials 0.000 claims description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 24
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 18
239000002904 solvent Substances 0.000 claims description 17
239000000126 substance Substances 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 11
229940095574 propionic acid Drugs 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 8
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 8
238000006798 ring closing metathesis reaction Methods 0.000 claims description 8
229960002449 glycine Drugs 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 5
150000002596 lactones Chemical class 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
235000013905 glycine and its sodium salt Nutrition 0.000 claims description 3
150000002429 hydrazines Chemical class 0.000 claims description 3
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 3
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims description 3
229940106681 chloroacetic acid Drugs 0.000 claims description 2
125000004494 ethyl ester group Chemical group 0.000 claims description 2
GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
LRTRXDSAJLSRTG-UHFFFAOYSA-N 4-bromobutanoyl chloride Chemical compound ClC(=O)CCCBr LRTRXDSAJLSRTG-UHFFFAOYSA-N 0.000 claims 1
101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 abstract description 11
230000000144 pharmacologic effect Effects 0.000 abstract description 3
208000004793 anterograde amnesia Diseases 0.000 abstract description 2
208000028867 ischemia Diseases 0.000 abstract description 2
231100000053 low toxicity Toxicity 0.000 abstract description 2
230000001777 nootropic effect Effects 0.000 abstract description 2
201000009570 retrograde amnesia Diseases 0.000 abstract description 2
150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 33
239000000203 mixture Substances 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
229960000583 acetic acid Drugs 0.000 description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000013543 active substance Substances 0.000 description 12
-1 x~lcne Chemical compound 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
238000004821 distillation Methods 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
239000000047 product Substances 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
125000003277 amino group Chemical group 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
230000001681 protective effect Effects 0.000 description 7
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
150000007529 inorganic bases Chemical class 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000006187 pill Substances 0.000 description 4
JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical class CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
150000007942 carboxylates Chemical class 0.000 description 3
239000008187 granular material Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000000725 suspension Substances 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000008298 dragée Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000945 filler Substances 0.000 description 2
YVIVRJLWYJGJTJ-UHFFFAOYSA-N gamma-Valerolactam Chemical compound CC1CCC(=O)N1 YVIVRJLWYJGJTJ-UHFFFAOYSA-N 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000012071 phase Substances 0.000 description 2
229960004526 piracetam Drugs 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
229940086066 potassium hydrogencarbonate Drugs 0.000 description 2
235000011118 potassium hydroxide Nutrition 0.000 description 2
229940093932 potassium hydroxide Drugs 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
RFMDTFSTIGPYJH-UHFFFAOYSA-N 2-(2-methyl-5-oxopyrrolidin-1-yl)acetic acid Chemical compound CC1CCC(=O)N1CC(O)=O RFMDTFSTIGPYJH-UHFFFAOYSA-N 0.000 description 1
UZUIMBZZRAGUEW-UHFFFAOYSA-N 2-(2-oxopiperidin-1-yl)acetohydrazide Chemical compound NNC(=O)CN1CCCCC1=O UZUIMBZZRAGUEW-UHFFFAOYSA-N 0.000 description 1
BJNAWORPAZFXKF-UHFFFAOYSA-N 2-(3-methyl-2-oxopyrrolidin-1-yl)acetohydrazide Chemical compound CC1C(N(CC1)CC(=O)NN)=O BJNAWORPAZFXKF-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
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 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
208000007848 Alcoholism Diseases 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
241000243251 Hydra Species 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
208000034189 Sclerosis Diseases 0.000 description 1
208000037175 Travel-Related Illness Diseases 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
201000007930 alcohol dependence Diseases 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000036770 blood supply Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000007767 bonding agent Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
230000009172 bursting Effects 0.000 description 1
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
ICXXXLGATNSZAV-UHFFFAOYSA-N butylazanium;chloride Chemical compound [Cl-].CCCC[NH3+] ICXXXLGATNSZAV-UHFFFAOYSA-N 0.000 description 1
229930188620 butyrolactone Natural products 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
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238000000354 decomposition reaction Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
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150000002170 ethers Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
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150000002222 fluorine compounds Chemical class 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
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239000013067 intermediate product Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
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MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
WFZFJWWGEDTHMC-UHFFFAOYSA-N methyl 2-(2-methyl-5-oxopyrrolidin-1-yl)acetate Chemical compound COC(=O)CN1C(C)CCC1=O WFZFJWWGEDTHMC-UHFFFAOYSA-N 0.000 description 1
JINDIQSUVPHDLL-UHFFFAOYSA-N methyl 2-(2-methyl-6-oxopiperidin-1-yl)acetate Chemical compound COC(CN1C(CCCC1C)=O)=O JINDIQSUVPHDLL-UHFFFAOYSA-N 0.000 description 1
DONDKWZGQCXXMI-UHFFFAOYSA-N methyl 2-(2-oxopiperidin-1-yl)acetate Chemical compound COC(=O)CN1CCCCC1=O DONDKWZGQCXXMI-UHFFFAOYSA-N 0.000 description 1
NFEVAVUZWQEORA-UHFFFAOYSA-N methyl 2-(3,5-dimethyl-2-oxopyrrolidin-1-yl)acetate Chemical compound COC(CN1C(C(CC1C)C)=O)=O NFEVAVUZWQEORA-UHFFFAOYSA-N 0.000 description 1
DYKDFWVHAYOAOM-UHFFFAOYSA-N methyl 2-(4,4-dimethyl-2-oxopyrrolidin-1-yl)acetate Chemical compound COC(CN1C(CC(C1)(C)C)=O)=O DYKDFWVHAYOAOM-UHFFFAOYSA-N 0.000 description 1
BHZBHIAKPCRXRJ-UHFFFAOYSA-N methyl 2-(4-methyl-2-oxopyrrolidin-1-yl)acetate Chemical compound COC(=O)CN1CC(C)CC1=O BHZBHIAKPCRXRJ-UHFFFAOYSA-N 0.000 description 1
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
201000003152 motion sickness Diseases 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000002664 nootropic agent Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
229940072033 potash Drugs 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
QFYXSLAAXZTRLG-UHFFFAOYSA-N pyrrolidine-2,3-dione Chemical class O=C1CCNC1=O QFYXSLAAXZTRLG-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229940083542 sodium Drugs 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
230000008733 trauma Effects 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
APIJEMVKVKFXMI-UHFFFAOYSA-N trioctylphosphanium;chloride Chemical compound [Cl-].CCCCCCCC[PH+](CCCCCCCC)CCCCCCCC APIJEMVKVKFXMI-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000325263A 1979-04-10 1979-04-10 Derives des acides (2-oxo-pyrrolidine-1) et (2-oxo-piperidine-1) carboxyliques; procede pour leur fabrication et preparations pharmaceutiques qui en contiennent Expired CA1119600A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000325263A CA1119600A (fr)	1979-04-10	1979-04-10	Derives des acides (2-oxo-pyrrolidine-1) et (2-oxo-piperidine-1) carboxyliques; procede pour leur fabrication et preparations pharmaceutiques qui en contiennent

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000325263A CA1119600A (fr)	1979-04-10	1979-04-10	Derives des acides (2-oxo-pyrrolidine-1) et (2-oxo-piperidine-1) carboxyliques; procede pour leur fabrication et preparations pharmaceutiques qui en contiennent

Publications (1)

Publication Number	Publication Date
CA1119600A true CA1119600A (fr)	1982-03-09

Family

ID=4113950

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000325263A Expired CA1119600A (fr)	1979-04-10	1979-04-10	Derives des acides (2-oxo-pyrrolidine-1) et (2-oxo-piperidine-1) carboxyliques; procede pour leur fabrication et preparations pharmaceutiques qui en contiennent

Country Status (1)

Country	Link
CA (1)	CA1119600A (fr)

1979
- 1979-04-10 CA CA000325263A patent/CA1119600A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-03-09	MKEX	Expiry

Publication	Publication Date	Title
EP0608759B1 (fr)	2001-08-22	Dérivés de pipérazines
CN85105301A (zh)	1987-01-14	(S)-α-乙基-2-氧代-1-吡咯烷乙酰胺的制备方法
JPH04506222A (ja)	1992-10-29	Ｎ−置換複素環誘導体およびその製法
EP1566376A1 (fr)	2005-08-24	Préparation d'amides d'aminoacides
HU187777B (en)	1986-02-28	Process for preparing pyrrolidine derivatives
EP0190891A2 (fr)	1986-08-13	Dérivés d'acides aminés
FR2465712A1 (fr)	1981-03-27	N-propionylsarcosinanilides, leur procede de preparation et les medicaments qui les contiennent
DE2747369C2 (fr)	1987-11-12
CA1119600A (fr)	1982-03-09	Derives des acides (2-oxo-pyrrolidine-1) et (2-oxo-piperidine-1) carboxyliques; procede pour leur fabrication et preparations pharmaceutiques qui en contiennent
US4318915A (en)	1982-03-09	Substituted guandines and methods of preparation thereof
WO1996004277A1 (fr)	1996-02-15	Agents peptidomimetiques a base de pyrrolinones
US5489692A (en)	1996-02-06	Pyrrolinone-based compounds
JPH0346460B2 (fr)	1991-07-16
US5514814A (en)	1996-05-07	Pyrrolinone-based compounds
US5441973A (en)	1995-08-15	N-acyl-4-phenyl-pyrrolidin-2-ones and method for preparing
US5817815A (en)	1998-10-06	Pharmacologically active enantiomers
JPH0228143A (ja)	1990-01-30	アミド化合物，その製造法ならびにグルタミン酸レセプター阻害剤
EP0174136A1 (fr)	1986-03-12	Dérivés de dihydro-1H-pyrrolo[1,2-c]imidazole-3,5-dione comme activateurs de cognition
EP0236263B1 (fr)	1992-12-30	Pyrrolidinones substituées
CA1217200A (fr)	1987-01-27	Acides 1-acylamino-1-cyclopentanecarboxyliques et methode de preparation
EP0110484A1 (fr)	1984-06-13	Dérivés d'acides aminopyridinocarboxyliques, leur procédé de préparation et les compositions pharmaceutiques les contenant
HU193556B (en)	1987-10-28	Process for preparing benzamide derivatives
KR100192531B1 (ko)	1999-06-15	광학적 활성 알라닌아닐리드 화합물의 산부가염 및 그것을 함유하는 약학적 조성물
WO1987004348A1 (fr)	1987-07-30	Composition de cyanamide acyle
GB2128992A (en)	1984-05-10	2.(2, 6-dimethyl-3, 5-diethoxycarbonyl-1, 4-dihydropyridine-4-carboxamide) glutaricacid and its disodium salt