FI67695C - Foerfarande foer framstaellning av 4-hydroxi-2-oxo-1-pyrrolidinalkanamider - Google Patents

Foerfarande foer framstaellning av 4-hydroxi-2-oxo-1-pyrrolidinalkanamider Download PDF

Info

Publication number: FI67695C
Authority: FI; Finland
Prior art keywords: enantiomers; hydroxy; general formula; oxo; process according
Prior art date: 1977-02-11

Application number

FI780407A

Other languages

English (en)

Finnish (fi)

Other versions

FI780407A7 (fi

FI67695B (fi

Inventor

Silvano Banfi

Renato Pellegata

Giorgio Pifferi

Mario Pinza

Original Assignee

Isf Spa

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.)

1977-02-11

Filing date

1978-02-08

Publication date

1985-05-10

1978-02-08 Application filed by Isf Spa filed Critical Isf Spa

1978-08-12 Publication of FI780407A7 publication Critical patent/FI780407A7/fi

1985-01-31 Publication of FI67695B publication Critical patent/FI67695B/fi

1985-05-10 Application granted granted Critical

1985-05-10 Publication of FI67695C publication Critical patent/FI67695C/fi

Links

239000007858 starting material Substances 0.000 title description 3
FMAZDWQTWSHRSZ-UHFFFAOYSA-N OC1CN(C=O)C(=O)C1 Chemical compound OC1CN(C=O)C(=O)C1 FMAZDWQTWSHRSZ-UHFFFAOYSA-N 0.000 title 1
-1 alkyl radicals Chemical class 0.000 claims description 15
238000000034 method Methods 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 7
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical group C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 3
239000005051 trimethylchlorosilane Substances 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
MASDFXZJIDNRTR-UHFFFAOYSA-N 1,3-bis(trimethylsilyl)urea Chemical compound C[Si](C)(C)NC(=O)N[Si](C)(C)C MASDFXZJIDNRTR-UHFFFAOYSA-N 0.000 claims description 2
NDVMCQUOSYOQMZ-UHFFFAOYSA-N 2,2-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)C(C(N)=O)[Si](C)(C)C NDVMCQUOSYOQMZ-UHFFFAOYSA-N 0.000 claims description 2
229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
239000000543 intermediate Substances 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000006501 nitrophenyl group Chemical group 0.000 claims description 2
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
238000010438 heat treatment Methods 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
238000007363 ring formation reaction Methods 0.000 claims 1
238000006884 silylation reaction Methods 0.000 claims 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
238000009835 boiling Methods 0.000 description 5
239000003480 eluent Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 3
IHLAQQPQKRMGSS-UHFFFAOYSA-N oxiracetam Chemical compound NC(=O)CN1CC(O)CC1=O IHLAQQPQKRMGSS-UHFFFAOYSA-N 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
URSOMCJSYBJWSF-UHFFFAOYSA-N 3-(4-hydroxy-2-oxopyrrolidin-1-yl)propanamide Chemical compound NC(=O)CCN1CC(O)CC1=O URSOMCJSYBJWSF-UHFFFAOYSA-N 0.000 description 2
TTZGVIABNGWVEG-UHFFFAOYSA-N 4-trimethylsilyloxypyrrolidin-2-one Chemical compound C[Si](C)(C)OC1CNC(=O)C1 TTZGVIABNGWVEG-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
YDBONCLBTWFUPF-UHFFFAOYSA-N ethyl 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetate Chemical compound CCOC(=O)CN1CC(O)CC1=O YDBONCLBTWFUPF-UHFFFAOYSA-N 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
DYWUUBKSRAUHLC-UHFFFAOYSA-N (2,3,4-trichlorophenyl) 2-bromoacetate Chemical compound ClC1=CC=C(OC(=O)CBr)C(Cl)=C1Cl DYWUUBKSRAUHLC-UHFFFAOYSA-N 0.000 description 1
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
IVUOMFWNDGNLBJ-UHFFFAOYSA-N 4-azaniumyl-2-hydroxybutanoate Chemical compound NCCC(O)C(O)=O IVUOMFWNDGNLBJ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229960002298 aminohydroxybutyric acid Drugs 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
238000005915 ammonolysis reaction Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000004181 carboxyalkyl group Chemical group 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
CANCDNHHCCJIGO-UHFFFAOYSA-N ethyl 2-(2-oxo-4-trimethylsilyloxypyrrolidin-1-yl)acetate Chemical compound CCOC(=O)CN1CC(O[Si](C)(C)C)CC1=O CANCDNHHCCJIGO-UHFFFAOYSA-N 0.000 description 1
FQTIYMRSUOADDK-UHFFFAOYSA-N ethyl 3-bromopropanoate Chemical compound CCOC(=O)CCBr FQTIYMRSUOADDK-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
YQGDEPYYFWUPGO-UHFFFAOYSA-N gamma-amino-beta-hydroxybutyric acid Chemical compound [NH3+]CC(O)CC([O-])=O YQGDEPYYFWUPGO-UHFFFAOYSA-N 0.000 description 1
239000000499 gel Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
150000002641 lithium Chemical group 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
150000002690 malonic acid derivatives Chemical class 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
ZGLPAIFNKIKEEL-UHFFFAOYSA-N n-ethyl-2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetamide Chemical compound CCNC(=O)CN1CC(O)CC1=O ZGLPAIFNKIKEEL-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
150000003235 pyrrolidines Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
150000003443 succinic acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction 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
- C07D207/18—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
- B—PERFORMING OPERATIONS; TRANSPORTING
- B43—WRITING OR DRAWING IMPLEMENTS; BUREAU ACCESSORIES
- B43K—IMPLEMENTS FOR WRITING OR DRAWING
- B43K24/00—Mechanisms for selecting, projecting, retracting or locking writing units
- B43K24/02—Mechanisms for selecting, projecting, retracting or locking writing units for locking a single writing unit in only fully projected or retracted positions
- B43K24/08—Mechanisms for selecting, projecting, retracting or locking writing units for locking a single writing unit in only fully projected or retracted positions operated by push-buttons
- B43K24/084—Mechanisms for selecting, projecting, retracting or locking writing units for locking a single writing unit in only fully projected or retracted positions operated by push-buttons with saw-like or analogous cams
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J115/00—Adhesives based on rubber derivatives

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

FI780407A 1977-02-11 1978-02-08 Foerfarande foer framstaellning av 4-hydroxi-2-oxo-1-pyrrolidinalkanamider FI67695C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT20227/77A IT1075280B (it)	1977-02-11	1977-02-11	Procedimento per la preparazione di derivati pirrolidinici
IT2022777		1977-02-11

Publications (3)

Publication Number	Publication Date
FI780407A7 FI780407A7 (fi)	1978-08-12
FI67695B FI67695B (fi)	1985-01-31
FI67695C true FI67695C (fi)	1985-05-10

Family

ID=11164931

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI780407A FI67695C (fi)	1977-02-11	1978-02-08	Foerfarande foer framstaellning av 4-hydroxi-2-oxo-1-pyrrolidinalkanamider

Country Status (26)

Country	Link
US (1)	US4173569A (fr)
JP (1)	JPS53101367A (fr)
AR (1)	AR223958A1 (fr)
AT (1)	AT362782B (fr)
AU (1)	AU513992B2 (fr)
BE (1)	BE863883A (fr)
CA (1)	CA1087200A (fr)
CH (1)	CH637928A5 (fr)
CS (1)	CS214800B2 (fr)
DE (2)	DE2758939A1 (fr)
DK (1)	DK155733C (fr)
ES (1)	ES466856A1 (fr)
FI (1)	FI67695C (fr)
FR (1)	FR2380257A1 (fr)
GB (1)	GB1588075A (fr)
HU (1)	HU178587B (fr)
IN (1)	IN148327B (fr)
IT (1)	IT1075280B (fr)
MX (1)	MX5950E (fr)
NL (1)	NL190412C (fr)
NO (1)	NO148148C (fr)
NZ (1)	NZ186431A (fr)
PL (1)	PL112858B1 (fr)
PT (1)	PT67642A (fr)
SU (1)	SU755195A3 (fr)
YU (1)	YU40321B (fr)

Families Citing this family (40)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
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.
IT1173768B (it) *	1984-04-02	1987-06-24	Isf Spa	Procedimento di preparazione di derivati 1-carbamoilmetilici di 4-idrossi-2-osso-pirrolidina nonche' di intermedi per ottenere tali composti
CH666483A5 (de) *	1985-01-16	1988-07-29	Lonza Ag	Verfahren zur herstellung von thiotetronsaeure.
US4686296A (en) *	1985-07-26	1987-08-11	Denki Kagaku Kogyo Kabushiki Kaisha	Process for producing oxiracetam
IL80071A0 (en) *	1985-09-24	1986-12-31	Lonza Ag	Pyrrolidine acetamide derivatives
CH668423A5 (de) *	1986-06-19	1988-12-30	Lonza Ag	Verfahren zur herstellung von 4-alkoxy-3-pyrrolin-2-onen.
HU195773B (en) *	1985-09-24	1988-07-28	Lonza Ag	Process for preparing alkyl esters of 4-alkoxy-3-pyrrolin-2-on-1-yl-acetic acid
CH666891A5 (de) *	1985-11-26	1988-08-31	Lonza Ag	4-alkoxy-2-oxo-pyrrolidin-1-yl-essigsaeure-c(1)-c(4)-alkylester, deren herstellung und verwendung.
CH668424A5 (de) *	1986-06-26	1988-12-30	Lonza Ag	4-benzyloxy-3-pyrrolin-2-on-l-yl-acetamid, dessen herstellung und verwendung.
CH668422A5 (de) *	1986-06-26	1988-12-30	Lonza Ag	4-benzyloxy-3-pyrrolin-2-on, dessen herstellung und verwendung zur synthese von tetramsaeure.
CH667655A5 (de) *	1986-09-24	1988-10-31	Lonza Ag	Verfahren zur herstellung von 4-alkoxy-2(5h)-thiophenonen.
CH670644A5 (fr) *	1986-12-18	1989-06-30	Lonza Ag
IT1215581B (it) *	1987-06-25	1990-02-14	Roussel Maestretti Spa	Derivati della 1-benzil 2-oxo 5-alcossi pirrolidina, loro procedimento di preparazione e loro applicazione come prodotti medicinali.
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
ATE124396T1 (de) *	1988-09-06	1995-07-15	Lonza Ag	Verfahren zur herstellung von 5- alkyltetramsäuren.
FI95034C (fi) *	1989-03-15	1995-12-11	Lonza Ag	Menetelmä 1,3-substituoidun tetrahydro-1H-tieno/3,4-d/-imidatsol-2(3H)-on-4-ylideenipentaanihappoesterin valmistamiseksi
CH680293A5 (fr) *	1990-06-26	1992-07-31	Lonza Ag
GB9121289D0 (en) *	1991-10-08	1991-11-20	Isf Spa	Composition and use
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
AU729287B2 (en) *	1996-11-22	2001-02-01	Mona Industries, Inc.	Silicone monomers and oligomers having a carboxyl functional group thereon
US5679798A (en) *	1996-11-22	1997-10-21	Mona Industries, Inc.	Silicone monomers having a carboxyl functional group thereon
KR100424393B1 (ko) *	2001-11-26	2004-03-24	한국화학연구원	옥시라세탐의 제조방법
JP4378326B2 (ja) *	2005-07-26	2009-12-02	キヤノン株式会社	駆動装置及び光量調節装置
EP3260118B1 (fr)	2008-10-16	2021-03-24	The Johns Hopkins University	Procédés et compositions pour améliorer la fonction cognitive
CN101747259B (zh) *	2008-12-18	2012-02-15	北京大学	氮杂糖类化合物及其合成方法及应用
CN101575309B (zh) *	2009-04-28	2011-05-18	中国医药集团总公司四川抗菌素工业研究所	合成(s)-奥拉西坦的方法
CN101704778B (zh) *	2009-09-30	2012-10-17	厦门市华兴化工有限公司	一种制备4-羟基吡咯烷酮-2-乙酰胺的方法
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IT1045043B (it)	1975-08-13	1980-04-21	Isf Spa	Derivati pirrolidinici
NZ181727A (en)	1975-08-13	1978-03-06	Isf Spa	Pyrroline-2-one derivatives and pharmaceutical compositions

1977
- 1977-02-11 IT IT20227/77A patent/IT1075280B/it active Protection Beyond IP Right Term
- 1977-12-30 DE DE19772758939 patent/DE2758939A1/de not_active Withdrawn
- 1977-12-30 DE DE19772758937 patent/DE2758937A1/de active Granted
1978
- 1978-02-08 CS CS78816A patent/CS214800B2/cs unknown
- 1978-02-08 AU AU33091/78A patent/AU513992B2/en not_active Expired
- 1978-02-08 US US05/876,169 patent/US4173569A/en not_active Expired - Lifetime
- 1978-02-08 IN IN104/DEL/78A patent/IN148327B/en unknown
- 1978-02-08 GB GB5046/78A patent/GB1588075A/en not_active Expired
- 1978-02-08 FI FI780407A patent/FI67695C/fi not_active IP Right Cessation
- 1978-02-08 AR AR271030A patent/AR223958A1/es active
- 1978-02-08 AT AT0088878A patent/AT362782B/de not_active IP Right Cessation
- 1978-02-09 CH CH145778A patent/CH637928A5/de not_active IP Right Cessation
- 1978-02-09 YU YU302/78A patent/YU40321B/xx unknown
- 1978-02-09 NL NLAANVRAGE7801500,A patent/NL190412C/xx not_active IP Right Cessation
- 1978-02-09 CA CA296,540A patent/CA1087200A/fr not_active Expired
- 1978-02-09 MX MX786832U patent/MX5950E/es unknown
- 1978-02-09 NZ NZ186431A patent/NZ186431A/xx unknown
- 1978-02-09 PT PT67642A patent/PT67642A/pt unknown
- 1978-02-09 HU HU78IE824A patent/HU178587B/hu not_active IP Right Cessation
- 1978-02-10 DK DK063178A patent/DK155733C/da not_active IP Right Cessation
- 1978-02-10 PL PL1978204549A patent/PL112858B1/pl unknown
- 1978-02-10 JP JP1484478A patent/JPS53101367A/ja active Granted
- 1978-02-10 NO NO780464A patent/NO148148C/no unknown
- 1978-02-10 SU SU782577623A patent/SU755195A3/ru active
- 1978-02-10 BE BE185100A patent/BE863883A/fr not_active IP Right Cessation
- 1978-02-10 ES ES466856A patent/ES466856A1/es not_active Expired
- 1978-02-13 FR FR7803961A patent/FR2380257A1/fr active Granted

Also Published As

Publication number	Publication date
AU513992B2 (en)	1981-01-15
NO148148B (no)	1983-05-09
YU30278A (en)	1983-01-21
NO148148C (no)	1983-08-17
ATA88878A (de)	1980-11-15
AU3309178A (en)	1979-08-16
DE2758937A1 (de)	1978-08-17
IN148327B (fr)	1981-01-17
FI780407A7 (fi)	1978-08-12
FR2380257B1 (fr)	1981-11-20
NL7801500A (nl)	1978-08-15
ES466856A1 (es)	1978-10-01
DE2758939A1 (de)	1978-08-17
DE2758937C2 (fr)	1988-07-07
NL190412C (nl)	1994-02-16
PL204549A1 (pl)	1979-03-12
PT67642A (en)	1978-03-01
JPS6338348B2 (fr)	1988-07-29
SU755195A3 (en)	1980-08-07
NO780464L (no)	1978-08-14
NL190412B (nl)	1993-09-16
AT362782B (de)	1981-06-10
HU178587B (en)	1982-05-28
AR223958A1 (es)	1981-10-15
US4173569A (en)	1979-11-06
GB1588075A (en)	1981-04-15
DK63178A (da)	1978-08-12
FI67695B (fi)	1985-01-31
CH637928A5 (de)	1983-08-31
CS214800B2 (en)	1982-05-28
YU40321B (en)	1985-12-31
PL112858B1 (en)	1980-11-29
DK155733C (da)	1989-09-25
JPS53101367A (en)	1978-09-04
IT1075280B (it)	1985-04-22
BE863883A (fr)	1978-08-10
DK155733B (da)	1989-05-08
NZ186431A (en)	1979-08-31
MX5950E (es)	1984-09-06
FR2380257A1 (fr)	1978-09-08
CA1087200A (fr)	1980-10-07

Legal Events

Date	Code	Title	Description
1993-02-08	MM	Patent lapsed
2004-08-31	MM	Patent lapsed	Owner name: I.S.F SOCIETA PER AZIONI

Publication	Publication Date	Title
FI67695B (fi)	1985-01-31	Foerfarande foer framstaellning av 4-hydroxi-2-oxo-1-pyrrolidinalkanamider
FI66847B (fi)	1984-08-31	Foerfarande foer framstaellning av 4-hydroxi-2-oxo-pyrrolidinalkanamider
RU2727151C2 (ru)	2020-07-21	Способы получения цитотоксических производных бензодиазепина
IE852296L (en)	1986-03-19	Oxiranes and 2-acylamido-2-fluoro-1-arylpropanols.
KR950018008A (ko)	1995-07-22	3-퀴놀론카르복실산 유도체의 단일-반응기 제조 방법
CA2645191C (fr)	2014-05-06	Procede de production d'un derive pyrrolidine 3,4-disubstitue et intermediaire de production
WO1998007691A1 (fr)	1998-02-26	Procede de preparation stereoselective de trans-azetidinones
US5977381A (en)	1999-11-02	Process for making 3-amino-pyrolidine derivatives
EP2445870B1 (fr)	2018-10-31	1-(sulfonyl)-n-phénylpyrrolidine-2-carboxamides utilisées pour l'identification d'activités biologiques et pharmacologiques
EP0156655A2 (fr)	1985-10-02	Procédé de préparation de dérivés de pyrrolidone
JP7109056B2 (ja)	2022-07-29	Ｓ－ｉｃａリボシルホモシステインの製造方法
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US6825353B2 (en)	2004-11-30	Process for producing quinolonecarboxylic acids and intermediates thereof
WO2015110886A1 (fr)	2015-07-30	Procédé de préparation de (2s, 5r)-7-oxo-n-[(3s)-pyrrolidin-3-yloxy]-6-(sulfooxy)-1,6-diazabicyclo [3.2.1]octane-2-carboxamide
FI91253B (fi)	1994-02-28	Menetelmä 4-asyylioksi-2-atsetidinonijohdannaisten valmistamiseksi
KR20030050412A (ko)	2003-06-25	레바미피드의 제조방법
DE69332441T2 (de)	2003-08-14	Verfahren zur Herstellung von Halogenacetamidderivaten
CS244813B2 (en)	1986-08-14	Production method of 1-substituted azetidin-3-ole
CN109970668B (zh)	2021-12-07	一种制备3-硫代-1,2,4-三氮唑类化合物的方法
DE69315007T2 (de)	1998-03-26	Verfahren zur Herstellung von Carbapenem-Derivaten
FI107605B (fi)	2001-09-14	Optisesti aktiivinen 2-[1-(4-t-butyylifenyyli)-2-pyrrolidoni-4-yyli]metoksikarbonyylibentsoehapon alfa-fenyylietyyliamidi, välituote ja menetelmä sen valmistamiseksi
ZA200404741B (en)	2005-08-29	Neurotensin active 2,3-diaryl-pyrazolidine derivatives.
JP4352129B2 (ja)	2009-10-28	新規な１，３−ベンゾチアジン化合物とその製造方法
EP0081817B1 (fr)	1985-05-15	Diamides optiquement actives
HK1048119A1 (en)	2003-03-21	Process for producing quinolonecarboxylic acids and intermediates thereof