RO84097B - Procedeu pentru prepararea unor derivati de pirolidina - Google Patents
Procedeu pentru prepararea unor derivati de pirolidinaInfo
- Publication number
- RO84097B RO84097B RO108194A RO10819482A RO84097B RO 84097 B RO84097 B RO 84097B RO 108194 A RO108194 A RO 108194A RO 10819482 A RO10819482 A RO 10819482A RO 84097 B RO84097 B RO 84097B
- Authority
- RO
- Romania
- Prior art keywords
- hydrogen
- lower alkyl
- formula
- general formula
- formula iii
- Prior art date
Links
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000001257 hydrogen Substances 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- -1 hept-1-yl Chemical group 0.000 abstract 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003235 pyrrolidines Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C07D207/273—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Peptides Or Proteins (AREA)
- Electronic Switches (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Inventia se refera la un procedeu pentru prepararea unor derivati de pirolidina cu formula generala I (vezi formula în pag.1 a descrierii) în care R1 este hidrogen sau alcanoil inferior, R2 este hidrogen sau alchil inferior si R3 este hidrogen, alchil inferior sau un radical cu formula -(CH2)n-NR4R5, n este un numar întreg de la 2 la 4, iar R4 si R5 sînt, independent unul de celalalt, hidrogen sau alchil inferior sau împreuna cu atomul de azot formeaza un radical de pirolidina, piperidina, piperazina sau morfolina care poate fi, eventual, mono sau disubstituit cu alchil inferior, constînd din aceea ca un compus cu formula generala II: H2N-R3 în care R3 are semnificatiile de mai sus, se trateaza cu un acid carboxilic cu formula generala III (vezi formula în pag.1 a descrierii) în care R2 are semnificatiile de mai sus, iar R11 este hidrogen sau alcanoil inferior sau, daca R3 din formula II este hidrogen, R11 reprezinta (3-oxo-4,7,7-trimet 1-2-oxabiciclo [2,2,1]hept-1-il)-carbonil sau cu un derivat reactiv al compusului cu formula III, ales dintre un ester alchilic inferior, o halogenura acida, o imidazolida si o anhidrida, la o temperatura cuprinsa între temperatura camerei si 100 degree C, în prezenta unui solvent ales între apa, clorura de metilen, cloroform, tetrahidrofuran, metanol, dimetilformamida, acetonitril sau un exces din amina cu formula II utilizata în reactie, în prezenta diciclohexil-carbodiimidei singura sau în amestec cu N-hidroxisuccinimida sau 1-(alchil inferior)-2-halogen-piridiniu ca agent de condensare, în cazul în care se foloseste în reactie cu acid carboxilic liber cu formula III, iar în cazul în care se foloseste d
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH4849/81A CH647234A5 (en) | 1981-07-24 | 1981-07-24 | Pyrrolidine derivatives |
CH276882 | 1982-05-05 |
Publications (2)
Publication Number | Publication Date |
---|---|
RO84097A RO84097A (ro) | 1984-05-12 |
RO84097B true RO84097B (ro) | 1984-06-30 |
Family
ID=25691358
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RO108194A RO84097B (ro) | 1981-07-24 | 1982-07-19 | Procedeu pentru prepararea unor derivati de pirolidina |
Country Status (34)
Country | Link |
---|---|
US (3) | US4476308A (ro) |
EP (1) | EP0071216B1 (ro) |
AT (2) | AT384424B (ro) |
AU (1) | AU557651B2 (ro) |
BG (1) | BG38334A3 (ro) |
CA (1) | CA1176251A (ro) |
CS (1) | CS226746B2 (ro) |
DD (1) | DD202540A5 (ro) |
DE (2) | DE3227649A1 (ro) |
DK (1) | DK157848C (ro) |
EG (1) | EG15921A (ro) |
ES (1) | ES514267A0 (ro) |
FI (1) | FI75158C (ro) |
FR (1) | FR2515179A1 (ro) |
GB (2) | GB2110207B (ro) |
HK (1) | HK53788A (ro) |
HU (1) | HU187777B (ro) |
IE (1) | IE53428B1 (ro) |
IL (1) | IL66341A (ro) |
IT (1) | IT1152287B (ro) |
LU (1) | LU84294A1 (ro) |
MC (1) | MC1476A1 (ro) |
MT (1) | MTP915B (ro) |
NL (1) | NL8202922A (ro) |
NO (1) | NO159592C (ro) |
NZ (1) | NZ201297A (ro) |
OA (1) | OA07151A (ro) |
PH (1) | PH19149A (ro) |
PT (1) | PT75314B (ro) |
RO (1) | RO84097B (ro) |
SE (1) | SE8204445L (ro) |
SG (1) | SG22788G (ro) |
SU (1) | SU1281172A3 (ro) |
ZW (1) | ZW14482A1 (ro) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2515179A1 (fr) * | 1981-07-24 | 1983-04-29 | Hoffmann La Roche | Derives de pyrrolidine, leur procede de preparation, les intermediaires pour leur synthese et leur application therapeutique |
IT1206699B (it) * | 1984-02-27 | 1989-04-27 | Isf Spa | Procedimento per preparare derivati di pirrolidone. |
IT1173763B (it) * | 1984-03-30 | 1987-06-24 | Proter Spa | Derivati dell'acido 3-mercapto-2-oxo-1-pirrolidinacetico,procedimento di preparazione e composizioni farmaceutiche che li contengono |
IT1190378B (it) * | 1985-06-21 | 1988-02-16 | Isf Spa | Derivati pirrolidonici |
US4758585A (en) * | 1985-08-16 | 1988-07-19 | Warner-Lambert Company | Saturated cycloalkyl (B) pyrrol-1 (2H)- acetic acid amides and derivatives thereof |
IT1224168B (it) * | 1986-08-01 | 1990-09-26 | Finanziaria R F Spa Ora Finanz | Derivati del pirrolidin-2-one ad attivita' nootropa |
CA1322199C (en) * | 1987-07-15 | 1993-09-14 | Masami Eigyo | N-¬(2-oxopyrrolidin-1-yl) acetyl)| piperazine derivatives and drug for senile dementia |
JPS6422883A (en) * | 1987-07-17 | 1989-01-25 | Sanwa Kagaku Kenkyusho Co | 1-pyrrolidine acetamide derivative, its salt, production thereof and prophylactic and remedial agent for cereral dysfunction containing said derivative and salt as active ingredient |
DE3813416A1 (de) * | 1988-04-21 | 1989-11-02 | Hoechst Ag | 3,4-dihydroxypyrrolidin-2-on-derivate, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung sowie die bei der herstellung anfallenden neuen zwischenprodukte |
WO1989010359A1 (en) * | 1988-04-22 | 1989-11-02 | 2 Moskovsky Gosudarstvenny Meditsinsky Institut Im | Carbalkoxymethyl ethers of lactam-1-acetic acid and method of obtaining them |
IT1245870B (it) * | 1991-06-05 | 1994-10-25 | Sigma Tau Ind Farmaceuti | 3-acilammino-2-pirrolidinoni quali attivatori dei processi di appremdimento e della memoria e composizioni farmaceutiche comprendenti tali composti |
DE4127404A1 (de) * | 1991-08-19 | 1993-02-25 | Thomae Gmbh Dr K | Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
CA2100641A1 (en) * | 1992-07-23 | 1994-01-24 | Hiromu Matsumura | Novel piperidine derivatives and process for preparation thereof |
EP0951468A4 (en) * | 1996-11-22 | 2001-06-06 | Mona Industries Inc | SILICONE MONOMERS AND OLIGOMERS CONTAINING A CARBOXYL FUNCTIONAL GROUP |
US5679798A (en) * | 1996-11-22 | 1997-10-21 | Mona Industries, Inc. | Silicone monomers having a carboxyl functional group thereon |
US6686477B2 (en) | 2000-09-29 | 2004-02-03 | Eastman Chemical Company | Highly enantiomerically pure lactam-substituted propanoic acid derivatives and methods of making and using same |
CN102227217A (zh) | 2008-10-16 | 2011-10-26 | 约翰斯.霍普金斯大学 | 改善认知功能的方法和组合物 |
EP2533645B1 (en) * | 2010-02-09 | 2016-07-27 | The Johns Hopkins University | Methods and compositions for improving cognitive function |
EP2919788A4 (en) | 2012-11-14 | 2016-05-25 | Univ Johns Hopkins | METHODS AND COMPOSITIONS FOR THE TREATMENT OF SCHIZOPHRENIA |
EP2968237A4 (en) | 2013-03-15 | 2016-08-31 | Univ Johns Hopkins | METHOD AND COMPOSITIONS FOR IMPROVING COGNITIVE FUNCTION |
DK2968220T3 (da) | 2013-03-15 | 2021-06-14 | Agenebio Inc | Fremgangsmåder og sammensætninger til forbedring af kognitiv funktion |
BR112017025031B1 (pt) | 2015-05-22 | 2023-03-21 | Agenebio, Inc | Composições farmacêuticas de liberação prolongada de levetiracetam |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1309692A (en) * | 1970-02-13 | 1973-03-14 | Ucb Sa | N-substituted lactams |
GB1039113A (en) * | 1964-08-06 | 1966-08-17 | Ucb Sa | New n-substituted lactams |
IT1045043B (it) * | 1975-08-13 | 1980-04-21 | Isf Spa | Derivati pirrolidinici |
IT1075280B (it) * | 1977-02-11 | 1985-04-22 | Isf Spa | Procedimento per la preparazione di derivati pirrolidinici |
IT1075564B (it) * | 1977-02-11 | 1985-04-22 | Isf Spa | Procedimento per la preparazione di derivati pirrolidinici |
BE864269A (fr) * | 1977-03-03 | 1978-06-16 | Parke Davis & Co | Nouveaux n-(aminoalkyl substitue)-2-oxo-1-pyrrolidine-acetamides et procedes pour les produire |
DE2923975A1 (de) * | 1979-06-13 | 1980-12-18 | Nattermann A & Cie | Pyrrolidinone, verfahren zu deren herstellung und diese enthaltende arzneimittel |
IT1141287B (it) * | 1979-06-13 | 1986-10-01 | Nattermann A & Cie | Ammidi di acidi pirrolidin-(2)-on-(1)-ilalchil-carbossilici,procedimento per la loro preparazione e prodotti medicinali che le contengono |
DE2924011C2 (de) * | 1979-06-13 | 1982-04-08 | A. Nattermann & Cie GmbH, 5000 Köln | Pyrrolidin-(2)-on-(1)-ylessigsäure-2,6,-dimethylanilid, Verfahren zur Herstellung und Arzneimittel, welche diese Verbindung enthalten |
NL8004025A (nl) * | 1979-08-09 | 1981-02-11 | Hoffmann La Roche | Pyrrolidinederivaten en werkwijze voor het bereiden daarvan alsmede geneesmiddel. |
CH657527A5 (de) * | 1980-02-13 | 1986-09-15 | Ciba Geigy Ag | Verwendung von zentralnervoes-wirksamen verbindungen in einem mittel, welches zur verhinderung oder linderung von nebenwirkungen bestimmt ist. |
US4372960A (en) * | 1980-12-12 | 1983-02-08 | Warner-Lambert Company | Quaternary derivatives of N-(substituted-aminoalkyl)-2-oxo-1-pyrrolidine-acetamides as cognition activators |
CH646149A5 (de) * | 1981-02-05 | 1984-11-15 | Hoffmann La Roche | Pyrrolidin-derivat. |
FR2515179A1 (fr) * | 1981-07-24 | 1983-04-29 | Hoffmann La Roche | Derives de pyrrolidine, leur procede de preparation, les intermediaires pour leur synthese et leur application therapeutique |
BE892942A (fr) * | 1982-04-23 | 1982-10-25 | Ucb Sa | Procede pour prevenir ou attenuer les psychoses iatrogenes causees par les medicaments a activite cytostatique. |
-
1982
- 1982-06-22 FR FR8210861A patent/FR2515179A1/fr active Granted
- 1982-06-29 NO NO822222A patent/NO159592C/no unknown
- 1982-07-09 IT IT22335/82A patent/IT1152287B/it active
- 1982-07-09 CA CA000407012A patent/CA1176251A/en not_active Expired
- 1982-07-14 DK DK317382A patent/DK157848C/da not_active IP Right Cessation
- 1982-07-16 ZW ZW144/82A patent/ZW14482A1/xx unknown
- 1982-07-16 NZ NZ201297A patent/NZ201297A/en unknown
- 1982-07-16 IL IL66341A patent/IL66341A/xx unknown
- 1982-07-17 EG EG430/82A patent/EG15921A/xx active
- 1982-07-19 FI FI822543A patent/FI75158C/fi not_active IP Right Cessation
- 1982-07-19 RO RO108194A patent/RO84097B/ro unknown
- 1982-07-19 OA OA57742A patent/OA07151A/xx unknown
- 1982-07-19 AU AU86158/82A patent/AU557651B2/en not_active Ceased
- 1982-07-20 MT MT915A patent/MTP915B/xx unknown
- 1982-07-20 NL NL8202922A patent/NL8202922A/nl not_active Application Discontinuation
- 1982-07-21 HU HU822357A patent/HU187777B/hu not_active IP Right Cessation
- 1982-07-21 CS CS825575A patent/CS226746B2/cs unknown
- 1982-07-21 DD DD82241833A patent/DD202540A5/de unknown
- 1982-07-22 MC MC821598A patent/MC1476A1/xx unknown
- 1982-07-22 SU SU823466582A patent/SU1281172A3/ru active
- 1982-07-23 SE SE8204445A patent/SE8204445L/xx not_active Application Discontinuation
- 1982-07-23 DE DE19823227649 patent/DE3227649A1/de not_active Withdrawn
- 1982-07-23 LU LU84294A patent/LU84294A1/de unknown
- 1982-07-23 EP EP82106690A patent/EP0071216B1/de not_active Expired
- 1982-07-23 DE DE8282106690T patent/DE3274851D1/de not_active Expired
- 1982-07-23 ES ES514267A patent/ES514267A0/es active Granted
- 1982-07-23 PH PH27623A patent/PH19149A/en unknown
- 1982-07-23 GB GB08221446A patent/GB2110207B/en not_active Expired
- 1982-07-23 IE IE1768/82A patent/IE53428B1/en not_active IP Right Cessation
- 1982-07-23 AT AT0286382A patent/AT384424B/de not_active IP Right Cessation
- 1982-07-23 PT PT75314A patent/PT75314B/pt unknown
- 1982-07-23 BG BG057520A patent/BG38334A3/xx unknown
- 1982-07-23 AT AT82106690T patent/ATE24488T1/de active
-
1983
- 1983-06-20 US US06/506,147 patent/US4476308A/en not_active Expired - Fee Related
-
1984
- 1984-06-25 US US06/624,303 patent/US4650878A/en not_active Expired - Fee Related
- 1984-10-16 GB GB08426076A patent/GB2152038B/en not_active Expired
-
1988
- 1988-04-05 SG SG227/88A patent/SG22788G/en unknown
- 1988-07-14 HK HK537/88A patent/HK53788A/xx unknown
-
1990
- 1990-04-12 US US07/508,675 patent/US5034402A/en not_active Expired - Fee Related
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