CA1059137A - Process for the preparation of therapeutically valuable 2-oxo-1-pyrrolidinylacetamide - Google Patents

Process for the preparation of therapeutically valuable 2-oxo-1-pyrrolidinylacetamide

Info

Publication number: CA1059137A
Authority: CA; Canada
Prior art keywords: formula; preparation; compound; organic solvent; oxo
Prior art date: 1975-03-27
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

CA247,190A

Other languages

English (en)

French (fr)

Inventor

Ulf Wennstrom

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.)

Medipolar Oy

Original Assignee

Medipolar Oy

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.)

1975-03-27

Filing date

1976-03-05

Publication date

1979-07-24

1976-03-05 Application filed by Medipolar Oy filed Critical Medipolar Oy

1979-07-24 Application granted granted Critical

1979-07-24 Publication of CA1059137A publication Critical patent/CA1059137A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 22
GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 12
238000010438 heat treatment Methods 0.000 claims abstract description 10
238000006243 chemical reaction Methods 0.000 claims abstract description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 15
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
-1 amino acid ester Chemical class 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 9
WKNMKGVLOWGGOU-UHFFFAOYSA-N 2-aminoacetamide;hydron;chloride Chemical compound Cl.NCC(N)=O WKNMKGVLOWGGOU-UHFFFAOYSA-N 0.000 claims description 8
239000011230 binding agent Substances 0.000 claims description 8
OPXNFHAILOHHFO-UHFFFAOYSA-N ethyl 4-chlorobutanoate Chemical compound CCOC(=O)CCCCl OPXNFHAILOHHFO-UHFFFAOYSA-N 0.000 claims description 7
229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
230000003197 catalytic effect Effects 0.000 claims description 5
238000009835 boiling Methods 0.000 claims description 4
125000003158 alcohol group Chemical group 0.000 claims description 3
239000000126 substance Substances 0.000 claims 1
229960004526 piracetam Drugs 0.000 abstract description 11
125000004494 ethyl ester group Chemical group 0.000 abstract description 3
239000002994 raw material Substances 0.000 abstract description 3
150000002148 esters Chemical class 0.000 description 4
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 4
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000002955 isolation Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
IPLKGJHGWCVSOG-UHFFFAOYSA-N 4-chlorobutanoic acid Chemical compound OC(=O)CCCCl IPLKGJHGWCVSOG-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
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 1
208000037175 Travel-Related Illness Diseases 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
229960003692 gamma aminobutyric acid Drugs 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
201000003152 motion sickness Diseases 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002830 nitrogen compounds Chemical class 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyrrole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA247,190A 1975-03-27 1976-03-05 Process for the preparation of therapeutically valuable 2-oxo-1-pyrrolidinylacetamide Expired CA1059137A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FI750944A FI51098C (fi)	1975-03-27	1975-03-27	Menetelmä terapeuttisesti arvokkaan 2-okso-1-pyrrolidinyyliasetamidin valmistamiseksi.

Publications (1)

Publication Number	Publication Date
CA1059137A true CA1059137A (en)	1979-07-24

Family

ID=8509097

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA247,190A Expired CA1059137A (en)	1975-03-27	1976-03-05	Process for the preparation of therapeutically valuable 2-oxo-1-pyrrolidinylacetamide

Country Status (10)

Country	Link
JP (1)	JPS51113867A (de)
AT (1)	AT347447B (de)
CA (1)	CA1059137A (de)
CH (1)	CH599151A5 (de)
ES (1)	ES445762A1 (de)
FI (1)	FI51098C (de)
NL (1)	NL7602263A (de)
PT (1)	PT64933B (de)
SU (1)	SU655304A3 (de)
YU (1)	YU45476A (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0223328A1 (de)	1985-07-26	1987-05-27	Denki Kagaku Kogyo Kabushiki Kaisha	Verfahren zur Herstellung von Oxiracetam
US4797496A (en) *	1984-02-27	1989-01-10	I.S.F. Societa Per Azioni	Process for the preparation of pyrrolidone derivatives
WO2011049475A1 (en)	2009-10-23	2011-04-28	Uniwersytet Jagielloński	The new application of 2-pyrrolidone derivatives
RU2629117C1 (ru) *	2016-06-14	2017-08-24	Сизов Владимир Владимирович	Способ получения 4-замещенного 2-[2-оксо-1-пирролидинил] ацетамида

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT391134B (de) *	1979-03-22	1990-08-27	Continental Pharma	Verfahren zum herstellen von neuen glycinamidderivaten, deren additionssalzen und deren optischen isomeren
CH680293A5 (de) *	1990-06-26	1992-07-31	Lonza Ag
JP2969616B2 (ja) *	1994-11-24	1999-11-02	田辺製薬株式会社	４−メルカプトピロリジン化合物の製法

1975
- 1975-03-27 FI FI750944A patent/FI51098C/fi not_active IP Right Cessation
1976
- 1976-02-21 JP JP1838876A patent/JPS51113867A/ja active Granted
- 1976-02-24 YU YU45476A patent/YU45476A/xx unknown
- 1976-03-04 ES ES445762A patent/ES445762A1/es not_active Expired
- 1976-03-04 NL NL7602263A patent/NL7602263A/xx not_active Application Discontinuation
- 1976-03-05 CA CA247,190A patent/CA1059137A/en not_active Expired
- 1976-03-22 PT PT6493376A patent/PT64933B/pt unknown
- 1976-03-23 CH CH361876A patent/CH599151A5/de not_active IP Right Cessation
- 1976-03-26 AT AT223576A patent/AT347447B/de not_active IP Right Cessation
1977
- 1977-12-05 SU SU772549949A patent/SU655304A3/ru active

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4797496A (en) *	1984-02-27	1989-01-10	I.S.F. Societa Per Azioni	Process for the preparation of pyrrolidone derivatives
EP0223328A1 (de)	1985-07-26	1987-05-27	Denki Kagaku Kogyo Kabushiki Kaisha	Verfahren zur Herstellung von Oxiracetam
EP0223328B1 (de) *	1985-07-26	1992-01-29	Denki Kagaku Kogyo Kabushiki Kaisha	Verfahren zur Herstellung von Oxiracetam
WO2011049475A1 (en)	2009-10-23	2011-04-28	Uniwersytet Jagielloński	The new application of 2-pyrrolidone derivatives
RU2629117C1 (ru) *	2016-06-14	2017-08-24	Сизов Владимир Владимирович	Способ получения 4-замещенного 2-[2-оксо-1-пирролидинил] ацетамида

Also Published As

Publication number	Publication date
PT64933A (en)	1976-04-01
SU655304A3 (ru)	1979-03-30
YU45476A (en)	1982-05-31
ATA223576A (de)	1978-05-15
NL7602263A (nl)	1976-09-29
AT347447B (de)	1978-12-27
JPS51113867A (en)	1976-10-07
FI51098B (de)	1976-06-30
ES445762A1 (es)	1977-06-01
JPS5652017B2 (de)	1981-12-09
FI51098C (fi)	1976-10-11
PT64933B (en)	1977-08-24
CH599151A5 (en)	1978-05-12

Publication	Publication Date	Title
CA1076588A (en)	1980-04-29	Acyclic, alicyclic and aromatic n-substituted halo-substituted 2-pyrrolidinones and their utility as herbicides
Loudon et al.	1984	Conversion of aliphatic amides into amines with [I, I-bis (trifluoroacetoxy) iodo] benzene. 1. Scope of the reaction
FR2676053A1 (fr)	1992-11-06	Nouveaux composes dialkylenepiperidino et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant.
JPH03193745A (ja)	1991-08-23	アンギオテンシン２拮抗薬の改良
DE69101835T2 (de)	1994-08-18	N-phenyl-n-acetamidoglycinamide, ihre herstellung und medikamente, die sie enthalten.
CA1059137A (en)	1979-07-24	Process for the preparation of therapeutically valuable 2-oxo-1-pyrrolidinylacetamide
DE69216873T2 (de)	1997-08-21	Benzolderivate zum Fördern der Produktion des Nervenwachstumsfaktors
DE2624290A1 (de)	1977-04-14	Neue 2-aminocycloalkancarbonsaeuren, deren derivate und ein verfahren zu ihrer herstellung
DE69624582T2 (de)	2003-03-20	Ester und amide als pla2-inhibitoren
DE2613420A1 (de)	1976-10-21	Benzamidderivate
Basha	1988	Synthesis of N, N′-disubstituted Ureas from Carbamates
US4758575A (en)	1988-07-19	Bi-2H-pyrroli(di)nediones
DE2747369C2 (de)	1987-11-12
EP0320753A2 (de)	1989-06-21	Neue Derivate cyclischer Aminosäuren, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und deren Verwendung
DE2632396A1 (de)	1977-02-03	Bestatinderivate und verfahren zu ihrer herstellung
JP2009513697A (ja)	2009-04-02	ヒストンデアセチラーゼの阻害活性を有するアルキルカルバモイルナフタレニルオキシオクテノイルヒドロキシアミド誘導体およびその製造方法
US3109844A (en)	1963-11-05	3-(3-indolyl) pyrrolidines
US5565476A (en)	1996-10-15	N-(hydroxyethyl)butanediamide derivatives
US4443616A (en)	1984-04-17	Production of 3-pyrrolin-2-ones
Moreno-Mañas et al.	1999	Asymmetric synthesis of quaternary α-amino acids using d-ribonolactone acetonide as chiral auxiliary
DE68904395T2 (de)	1993-05-06	Verfahren zur synthese von 3-chlor-2,4,5-trifluorbenzoesaeure.
US3022293A (en)	1962-02-20	Novel ethylenic compounds
US3852287A (en)	1974-12-03	Preparation of thionamides
EP0338435A1 (de)	1989-10-25	3.4-Dihydroxypyrrolidin-2-on-Derivate, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und ihre Verwendung sowie die bei der Herstellung anfallenden Zwischenprodukte
US2698850A (en)	1955-01-04	N-substituted phthalimide compound and method for obtaining the same