PL181824B1 - Sposób wytwarzania kwasu 3-(L-piroglutamylo)-L-tiazolidyno-4-karboksylowego i jego pochodnych PL - Google Patents

Sposób wytwarzania kwasu 3-(L-piroglutamylo)-L-tiazolidyno-4-karboksylowego i jego pochodnych PL

Info

Publication number: PL181824B1
Authority: PL; Poland
Prior art keywords: formula; compound; halide; hydrogen; acid
Prior art date: 1994-09-27

Application number

PL95319380A

Other languages

English (en)

Polish (pl)

Other versions

PL319380A1 (en

Inventor

Stefano Poli

Ambrogio Magni

Gianettore Bocchiola

Original Assignee

Polichem Sa

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.)

1994-09-27

Filing date

1995-09-21

Publication date

2001-09-28

1995-09-21 Application filed by Polichem Sa filed Critical Polichem Sa

1997-08-04 Publication of PL319380A1 publication Critical patent/PL319380A1/xx

2001-09-28 Publication of PL181824B1 publication Critical patent/PL181824B1/pl

Links

238000000034 method Methods 0.000 title claims abstract description 32
239000002253 acid Substances 0.000 title description 5
-1 3-(L-pyroglutamyl)-L-thiazolidyl Chemical group 0.000 claims abstract description 26
150000001875 compounds Chemical class 0.000 claims abstract description 17
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 8
239000000010 aprotic solvent Substances 0.000 claims abstract description 7
239000003444 phase transfer catalyst Substances 0.000 claims abstract description 6
125000004494 ethyl ester group Chemical group 0.000 claims abstract description 5
125000003118 aryl group Chemical group 0.000 claims abstract description 4
230000007062 hydrolysis Effects 0.000 claims abstract description 4
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 4
230000003213 activating effect Effects 0.000 claims abstract description 3
125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims abstract description 3
125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims description 8
ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 4
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 4
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 4
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
MJLQPFJGZTYCMH-LURJTMIESA-N (2s)-1-[(2-methylpropan-2-yl)oxycarbonyl]-5-oxopyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1[C@H](C(O)=O)CCC1=O MJLQPFJGZTYCMH-LURJTMIESA-N 0.000 claims description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 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 claims description 2
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
229960004830 cetylpyridinium Drugs 0.000 claims description 2
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
239000003208 petroleum Substances 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
NEUSVAOJNUQRTM-UHFFFAOYSA-N cetylpyridinium Chemical compound CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NEUSVAOJNUQRTM-UHFFFAOYSA-N 0.000 claims 1
MZMRZONIDDFOGF-UHFFFAOYSA-M hexadecyl(trimethyl)azanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CCCCCCCCCCCCCCCC[N+](C)(C)C MZMRZONIDDFOGF-UHFFFAOYSA-M 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
239000002904 solvent Substances 0.000 claims 1
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 abstract description 2
238000004519 manufacturing process Methods 0.000 abstract description 2
150000002500 ions Chemical class 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
150000002148 esters Chemical class 0.000 description 6
DZLNHFMRPBPULJ-GSVOUGTGSA-N D-thioproline Chemical compound OC(=O)[C@H]1CSCN1 DZLNHFMRPBPULJ-GSVOUGTGSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
RMHPSSGICDJKDR-VKHMYHEASA-N (2s)-5-oxopyrrolidine-2-carbonyl chloride Chemical compound ClC(=O)[C@@H]1CCC(=O)N1 RMHPSSGICDJKDR-VKHMYHEASA-N 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
ZRBNETYZYOXTLS-UHFFFAOYSA-N ethyl 1,3-thiazolidine-4-carboxylate Chemical compound CCOC(=O)C1CSCN1 ZRBNETYZYOXTLS-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
REACWASHYHDPSQ-UHFFFAOYSA-N 1-butylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1 REACWASHYHDPSQ-UHFFFAOYSA-N 0.000 description 1
XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 1
LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-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
CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
XXYNZSATHOXXBJ-UHFFFAOYSA-N 4-hydroxyisoindole-1,3-dione Chemical compound OC1=CC=CC2=C1C(=O)NC2=O XXYNZSATHOXXBJ-UHFFFAOYSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000003712 anti-aging effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000001147 anti-toxic effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
ZRBNETYZYOXTLS-YFKPBYRVSA-N ethyl (4r)-1,3-thiazolidine-4-carboxylate Chemical compound CCOC(=O)[C@@H]1CSCN1 ZRBNETYZYOXTLS-YFKPBYRVSA-N 0.000 description 1
SQRLNYSSTHJCIU-JEDNCBNOSA-N ethyl (4r)-1,3-thiazolidine-4-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)[C@@H]1CSCN1 SQRLNYSSTHJCIU-JEDNCBNOSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
230000003308 immunostimulating effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
239000000047 product Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical class OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06173—Dipeptides with the first amino acid being heterocyclic and Glp-amino acid; Derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Thiazole And Isothizaole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Pyrrole Compounds (AREA)

PL95319380A 1994-09-27 1995-09-21 Sposób wytwarzania kwasu 3-(L-piroglutamylo)-L-tiazolidyno-4-karboksylowego i jego pochodnych PL PL181824B1 (pl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ITMI941955A IT1270017B (it)	1994-09-27	1994-09-27	"sintesi quantitativa dell'acido 3-(l-piroglutamil)-l-tiazolidin-4- carbossilico e suoi derivati"
PCT/EP1995/003720 WO1996010036A1 (en)	1994-09-27	1995-09-21	A process for the quantitative synthesis of 3-(l-pyroglutamyl)-l-thiazolidine-4-carboxylic acid and derivatives thereof

Publications (2)

Publication Number	Publication Date
PL319380A1 PL319380A1 (en)	1997-08-04
PL181824B1 true PL181824B1 (pl)	2001-09-28

Family

ID=11369599

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL95319380A PL181824B1 (pl)	1994-09-27	1995-09-21	Sposób wytwarzania kwasu 3-(L-piroglutamylo)-L-tiazolidyno-4-karboksylowego i jego pochodnych PL

Country Status (10)

Country	Link
CN (1)	CN1143863C (it)
BG (1)	BG63895B1 (it)
BR (1)	BR9509087A (it)
CO (1)	CO4480030A1 (it)
CZ (1)	CZ91597A3 (it)
IT (1)	IT1270017B (it)
PL (1)	PL181824B1 (it)
RO (1)	RO115957B1 (it)
SK (1)	SK40097A3 (it)
WO (1)	WO1996010036A1 (it)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN108088936B (zh) *	2017-12-08	2020-05-22	常州寅盛药业有限公司	制备匹多莫德乙酯所得杂质及其质量检测方法
CN108715598A (zh) *	2018-06-13	2018-10-30	峨眉山宏昇药业股份有限公司	一种匹多莫德的制备方法
CN117088939A (zh) *	2022-05-11	2023-11-21	江苏吴中医药集团有限公司	一种匹多莫德的制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1202426B (it) *	1987-01-26	1989-02-09	Poli Ind Chimica Spa	Derivato di acido tiazolidin-4-carbossilico,sua preparazione e composizioni farmaceutiche che lo contengono
IT1239029B (it) *	1989-10-12	1993-09-20	Poli Ind Chimica Spa	Processo per la preparazione dell'acido 3-(l-piroglutamil)-l- tiazolidin-4-carbossilico e suoi derivati.

1994
- 1994-09-27 IT ITMI941955A patent/IT1270017B/it active IP Right Grant
1995
- 1995-09-21 CN CNB951953222A patent/CN1143863C/zh not_active Expired - Lifetime
- 1995-09-21 PL PL95319380A patent/PL181824B1/pl unknown
- 1995-09-21 CZ CZ97915A patent/CZ91597A3/cs unknown
- 1995-09-21 RO RO97-00611A patent/RO115957B1/ro unknown
- 1995-09-21 WO PCT/EP1995/003720 patent/WO1996010036A1/en not_active Ceased
- 1995-09-21 SK SK400-97A patent/SK40097A3/sk unknown
- 1995-09-21 BR BR9509087A patent/BR9509087A/pt not_active Application Discontinuation
- 1995-09-27 CO CO95044814A patent/CO4480030A1/es unknown
1997
- 1997-03-11 BG BG101310A patent/BG63895B1/bg unknown

Also Published As

Publication number	Publication date
CO4480030A1 (es)	1997-07-09
RO115957B1 (ro)	2000-08-30
CN1158620A (zh)	1997-09-03
BG63895B1 (bg)	2003-05-30
WO1996010036A1 (en)	1996-04-04
SK40097A3 (en)	1997-09-10
CZ91597A3 (en)	1997-09-17
BG101310A (en)	1997-12-30
IT1270017B (it)	1997-04-16
CN1143863C (zh)	2004-03-31
ITMI941955A1 (it)	1996-03-27
BR9509087A (pt)	1998-07-21
ITMI941955A0 (it)	1994-09-27
PL319380A1 (en)	1997-08-04

Publication	Publication Date	Title
RU2038350C1 (ru)	1995-06-27	Способ получения производных мутилина или их солей с кислотами
ATE206422T1 (de)	2001-10-15	Verfahren zur herstellung von aryl-piperazinyl- heterocyclischen derivaten
ATE187445T1 (de)	1999-12-15	Verfahren zur herstellung von chinazolinderivaten
ES2170732A1 (es)	2002-08-01	Procedimiento para preparar citalopram purificado
DE69719781D1 (de)	2003-04-17	Zwischenprodukte zur Herstellung von Duocarmycin SA und dessen Derivaten sowie ein Verfahren zur Herstellung der Zwischenprodukte
DE3872995D1 (de)	1992-08-27	Verfahren zur herstellung von androsta-1,4-dien-3,17-dion-methylen-derivaten.
US3705175A (en)	1972-12-05	Indazole-3-carboxylic amides
ATE519747T1 (de)	2011-08-15	Verfahren zur herstellung von cyclopentaägüchinazolin-derivaten
EA200000484A1 (ru)	2000-10-30	Способ получения производных тиазолидиндиона
FI95271B (fi)	1995-09-29	Menetelmä 3-(L-pyroglutamyyli)-L-tiatsolidiini-4-karboksyylihapon ja sen N-substituoitujen johdannaisten valmistamiseksi
FI62297C (fi)	1982-12-10	Foerfarande foer framstaellning av 3,4-dihydro-2-metyl-4-oxo-2h-1,2-bensotiazin-3-karboxylsyra-1,1-dioxid vilken foereningkan anvaendas saosom mellanprodukt vid framstaellning av taninflammatoriska 3,4-dihydro-2-metyl-4-oxo-2h-1,2-bensoti iaz-3-karboxamid-1,1-dioxider
US4497952A (en)	1985-02-05	Process for the production of (±)-4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinoline derivatives
DE60112091D1 (de)	2005-08-25	Verfahren zur herstellung von azacycloalkanoylaminothiazolen
US6005101A (en)	1999-12-21	Glutaryl 7-ACA derivatives and processes for obtaining them
DE69616719D1 (de)	2001-12-13	Verfahren zur herstellung von taxol und seiner derivate
US4128561A (en)	1978-12-05	Process for the preparation of 2-(2-thienyl)-ethylamine and derivatives thereof
ATE208378T1 (de)	2001-11-15	Verfahren zur herstellung von nicotinsäuren
ATE244224T1 (de)	2003-07-15	Verfahren zur umwandlung von 2,4-dichlorpyridinen in 2-aryloxy-4-chlorpyridine
SK40097A3 (en)	1997-09-10	A process for the quantitative synthesis of 3-(l-pyroglutamyl)-l- -thiazolidine-4-carboxylic acid and derivatives thereof
Rosen et al.	1975	The Synthesis of Spin Labeled Acetylcholine Analogs
DE69809888D1 (de)	2003-01-16	Verfahren zur Herstellung von alpha-Aminoketonen
EA199900528A1 (ru)	1999-12-29	Новые производные эритромицина, способ их получения и применения в качетве медикаментов
RS49832B (sr)	2008-08-07	Postupak za dobijanje aminskih derivata alkiloksifuranona, dobijanje jedinjenja i upotreba ovih jedinjenja
ATE277024T1 (de)	2004-10-15	Verfahren zur herstellung eines 4- thiazolylmethylderivates
KR0184037B1 (ko)	1999-05-01	세펨 유도체의 제조방법