DD281382A5 - Verfahren zur herstellung von 4-alkoxy-2(5h)-thiophenonen - Google Patents

Verfahren zur herstellung von 4-alkoxy-2(5h)-thiophenonen Download PDF

Info

Publication number: DD281382A5
Authority: DD; German Democratic Republic
Prior art keywords: acid; alkoxy; reaction; alkali metal; hydrogen sulfide
Prior art date: 1986-09-24

Application number

DD87307049A

Other languages

German (de)

English (en)

Inventor

Thomas Meul

Original Assignee

��@��k��

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.)

1986-09-24

Filing date

1987-09-18

Publication date

1990-08-08

1987-09-18 Application filed by ��@��k�� filed Critical ��@��k��

1990-08-08 Publication of DD281382A5 publication Critical patent/DD281382A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 22
238000002360 preparation method Methods 0.000 title claims abstract description 14
KJLXVAPBVMFHOL-UHFFFAOYSA-N thiolane-2,4-dione Chemical compound O=C1CSC(=O)C1 KJLXVAPBVMFHOL-UHFFFAOYSA-N 0.000 claims abstract description 19
238000006243 chemical reaction Methods 0.000 claims description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
229910052783 alkali metal Inorganic materials 0.000 claims description 11
-1 alkali metal salt Chemical class 0.000 claims description 11
229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 7
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 claims description 7
AUKPMQUAYVMURI-UHFFFAOYSA-N 2,5-dihydrothiophene 1-oxide Chemical class O=S1CC=CC1 AUKPMQUAYVMURI-UHFFFAOYSA-N 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 5
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 5
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
229910001854 alkali hydroxide Inorganic materials 0.000 claims 2
239000012467 final product Substances 0.000 claims 2
RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical compound OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 6
238000004519 manufacturing process Methods 0.000 abstract description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000000047 product Substances 0.000 description 6
239000002253 acid Substances 0.000 description 5
DJKPLEJCYVMHGI-UHFFFAOYSA-N 3-methoxy-2h-thiophen-5-one Chemical compound COC1=CC(=O)SC1 DJKPLEJCYVMHGI-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000007858 starting material Substances 0.000 description 4
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 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000001875 compounds Chemical group 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
JNYMRXDQVPIONI-HWKANZROSA-N methyl (e)-4-chloro-3-methoxybut-2-enoate Chemical compound COC(=O)\C=C(/CCl)OC JNYMRXDQVPIONI-HWKANZROSA-N 0.000 description 2
MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical compound COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
OFPOZFQPVIOMTN-UHFFFAOYSA-N s-[(2-chloro-2-oxoethyl)amino] ethanethioate Chemical compound CC(=O)SNCC(Cl)=O OFPOZFQPVIOMTN-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
CQWZJQSPYYJZJP-UHFFFAOYSA-N (4-acetyloxythiophen-2-yl) acetate Chemical compound CC(=O)OC1=CSC(OC(C)=O)=C1 CQWZJQSPYYJZJP-UHFFFAOYSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
SIWVGXQOXWGJCI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;2-ethenylbenzenesulfonic acid Chemical compound C=CC1=CC=CC=C1C=C.OS(=O)(=O)C1=CC=CC=C1C=C SIWVGXQOXWGJCI-UHFFFAOYSA-N 0.000 description 1
WAQFYSJKIRRXLP-UHFFFAOYSA-N 2,4-dibromothiophene Chemical compound BrC1=CSC(Br)=C1 WAQFYSJKIRRXLP-UHFFFAOYSA-N 0.000 description 1
WSHVQVCBPLNREW-UHFFFAOYSA-N 4-chloro-3-oxobutanoyl chloride Chemical compound ClCC(=O)CC(Cl)=O WSHVQVCBPLNREW-UHFFFAOYSA-N 0.000 description 1
241000251730 Chondrichthyes Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
SRVNUCUVVNKTQM-UHFFFAOYSA-N methyl (E)-4-ethanethioyloxy-3-methoxybut-2-enoate Chemical compound COC(C=C(/COC(C)=S)OC)=O SRVNUCUVVNKTQM-UHFFFAOYSA-N 0.000 description 1
HFLMYYLFSNEOOT-UHFFFAOYSA-N methyl 4-chloro-3-oxobutanoate Chemical compound COC(=O)CC(=O)CCl HFLMYYLFSNEOOT-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
PRWXGRGLHYDWPS-UHFFFAOYSA-L sodium malonate Chemical compound [Na+].[Na+].[O-]C(=O)CC([O-])=O PRWXGRGLHYDWPS-UHFFFAOYSA-L 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
RBBWNXJFTBCLKT-UHFFFAOYSA-M sodium;ethanethioate Chemical compound [Na+].CC([S-])=O RBBWNXJFTBCLKT-UHFFFAOYSA-M 0.000 description 1
WRVHPSSSTBDGRK-UHFFFAOYSA-N sodium;sulfane;hydrate Chemical compound O.[Na].S WRVHPSSSTBDGRK-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Diaphragms For Electromechanical Transducers (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)

DD87307049A 1986-09-24 1987-09-18 Verfahren zur herstellung von 4-alkoxy-2(5h)-thiophenonen DD281382A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH3827/86A CH667655A5 (de)	1986-09-24	1986-09-24	Verfahren zur herstellung von 4-alkoxy-2(5h)-thiophenonen.

Publications (1)

Publication Number	Publication Date
DD281382A5 true DD281382A5 (de)	1990-08-08

Family

ID=4264314

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87307049A DD281382A5 (de)	1986-09-24	1987-09-18	Verfahren zur herstellung von 4-alkoxy-2(5h)-thiophenonen

Country Status (19)

Country	Link
US (3)	US4906759A (da)
EP (1)	EP0261668B1 (da)
JP (2)	JPH0830066B2 (da)
AT (1)	ATE53840T1 (da)
CA (2)	CA1304386C (da)
CH (1)	CH667655A5 (da)
DD (1)	DD281382A5 (da)
DE (1)	DE3762515D1 (da)
DK (2)	DK162767C (da)
ES (1)	ES2015561B3 (da)
FI (1)	FI87209C (da)
HU (1)	HU198469B (da)
IE (1)	IE61142B1 (da)
IL (1)	IL83926A (da)
NO (1)	NO169587C (da)
PT (1)	PT85788B (da)
SU (1)	SU1512481A3 (da)
TR (1)	TR23443A (da)
YU (1)	YU45832B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6121202A (en) *	1997-11-07	2000-09-19	American Cyanamid Company	Thienyloxypyridines and-pyrimidines useful as herbicidal agents
EA013371B1 (ru) *	2002-07-09	2010-04-30	Фасджен, Ллс.	Новые соединения, содержащие их фармацевтические композиции и способы их применения

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2784191A (en) *		1957-03-05		Process for the production of lactams
US2212141A (en) *	1939-04-11	1940-08-20	Du Pont	Esters and their preparation
US2453103A (en) *	1944-02-25	1948-11-02	Du Pont	Decarboxylation of 3,4-dihydroxy-2,5-dicarboxythiophene
US2535010A (en) *	1948-10-02	1950-12-19	Rohm & Haas	Transetherification of beta-ethersubstituted esters
DE850007C (de) *	1950-12-22	1952-09-22	Basf Ag	Verfahren zur Herstellung von N-Aryl-ª‡-pyrrolidonen
GB840658A (en) *	1955-09-20	1960-07-06	Goodrich Co B F	Improvements in the manufacture of thiolactones
DE2065550C2 (de) *	1969-05-29	1982-05-06	Firmenich S.A., 1211 Genève	Verfahren zur Herstellung von bicyclischen Äthern und 13-Oxa-Bicyclo[10.4.0]Hexadecen[1(12)]
CH557813A (de) *	1970-05-27	1975-01-15	Firmenich & Cie	Verfahren zur herstellung von lactonen.
DE2035901A1 (de) *	1969-07-22	1971-05-13	Firmenich & Cie , Genf (Schweiz)	Verfahren zur Herstellung eines Acyclischen Ketons
CH539631A (fr) *	1971-03-26	1973-07-31	Firmenich & Cie	Procédé pour la préparation de dérivés hétérocycliques
CH557644A (fr) *	1972-03-24	1975-01-15	Firmenich & Cie	Utilisation de derives heterocycliques comme ingredients aromatisants.
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
CH642611A5 (de) *	1979-11-01	1984-04-30	Lonza Ag	Verfahren zur herstellung von gamma-chloracetessigsaeurechlorid.
US4559178A (en) *	1980-10-06	1985-12-17	American Home Products Corporation	Resolution of 3-benzoylthio-2-methyl-propanoic acid with (+)-dehydroabietylamine
US4398033A (en) *	1981-03-17	1983-08-09	Ciba-Geigy Corporation	4-Chloro-4-chloromethyloxetan-2-one and a process for its production
JPS5812272B2 (ja) *	1981-04-28	1983-03-07	電気化学工業株式会社	４−ヒドロキシ−２−ピロリドンの製造法
CH663206A5 (de) *	1985-01-16	1987-11-30	Lonza Ag	Verfahren zur herstellung von thiotetronsaeure.
CH666483A5 (de) *	1985-01-16	1988-07-29	Lonza Ag	Verfahren zur herstellung von thiotetronsaeure.
FI83510C (fi) *	1985-02-22	1991-07-25	Ciba Geigy Ag	Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara bi-2h- pyrroli(di)ndioner.

1986
- 1986-09-24 CH CH3827/86A patent/CH667655A5/de not_active IP Right Cessation
1987
- 1987-08-17 FI FI873552A patent/FI87209C/fi not_active IP Right Cessation
- 1987-09-01 IE IE234087A patent/IE61142B1/en not_active IP Right Cessation
- 1987-09-15 DK DK482887A patent/DK162767C/da not_active IP Right Cessation
- 1987-09-16 US US07/097,109 patent/US4906759A/en not_active Expired - Fee Related
- 1987-09-16 IL IL83926A patent/IL83926A/xx unknown
- 1987-09-17 TR TR638/87A patent/TR23443A/xx unknown
- 1987-09-18 JP JP62234679A patent/JPH0830066B2/ja not_active Expired - Lifetime
- 1987-09-18 DD DD87307049A patent/DD281382A5/de not_active IP Right Cessation
- 1987-09-22 YU YU175287A patent/YU45832B/sh unknown
- 1987-09-23 CA CA000547638A patent/CA1304386C/en not_active Expired - Fee Related
- 1987-09-23 EP EP87113926A patent/EP0261668B1/de not_active Expired - Lifetime
- 1987-09-23 AT AT87113926T patent/ATE53840T1/de not_active IP Right Cessation
- 1987-09-23 NO NO873986A patent/NO169587C/no unknown
- 1987-09-23 DE DE8787113926T patent/DE3762515D1/de not_active Expired - Fee Related
- 1987-09-23 ES ES87113926T patent/ES2015561B3/es not_active Expired - Lifetime
- 1987-09-23 SU SU874203335A patent/SU1512481A3/ru active
- 1987-09-24 HU HU874297A patent/HU198469B/hu not_active IP Right Cessation
- 1987-09-24 PT PT85788A patent/PT85788B/pt not_active IP Right Cessation
1988
- 1988-10-14 US US07/258,071 patent/US4906765A/en not_active Expired - Fee Related
- 1988-10-14 US US07/258,072 patent/US4931570A/en not_active Expired - Fee Related
1991
- 1991-03-22 DK DK052291A patent/DK162096C/da not_active IP Right Cessation
- 1991-10-30 CA CA000616211A patent/CA1319698C/en not_active Expired - Fee Related
1995
- 1995-03-16 JP JP7057127A patent/JPH07285928A/ja active Pending

Also Published As

Publication number	Publication date
YU175287A (en)	1988-10-31
DK52291D0 (da)	1991-03-22
US4906759A (en)	1990-03-06
IE61142B1 (en)	1994-10-05
DK482887D0 (da)	1987-09-15
PT85788A (de)	1987-10-01
CA1304386C (en)	1992-06-30
ATE53840T1 (de)	1990-06-15
NO873986D0 (no)	1987-09-23
NO873986L (no)	1988-03-25
FI873552L (fi)	1988-03-25
JPH0830066B2 (ja)	1996-03-27
FI87209B (fi)	1992-08-31
DK162767B (da)	1991-12-09
US4906765A (en)	1990-03-06
US4931570A (en)	1990-06-05
ES2015561B3 (es)	1990-09-01
NO169587C (no)	1992-07-15
TR23443A (tr)	1989-12-29
HU198469B (en)	1989-10-30
IL83926A0 (en)	1988-02-29
IE872340L (en)	1988-03-24
IL83926A (en)	1992-05-25
EP0261668A1 (de)	1988-03-30
DK162767C (da)	1992-04-27
FI873552A0 (fi)	1987-08-17
DK162096C (da)	1992-02-24
HUT46902A (en)	1988-12-28
JPH07285928A (ja)	1995-10-31
EP0261668B1 (de)	1990-05-02
YU45832B (sh)	1992-07-20
DE3762515D1 (de)	1990-06-07
SU1512481A3 (ru)	1989-09-30
FI87209C (fi)	1992-12-10
PT85788B (pt)	1990-08-31
DK52291A (da)	1991-03-22
DK162096B (da)	1991-09-16
CA1319698C (en)	1993-06-29
DK482887A (da)	1988-03-25
JPS6391383A (ja)	1988-04-22
NO169587B (no)	1992-04-06
CH667655A5 (de)	1988-10-31

Legal Events

Date	Code	Title	Description
1997-05-22	ENJ	Ceased due to non-payment of renewal fee

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DE69623532T2 (de)	2003-03-20	Verfahren zur Herstellung von 4-Trifluormethylnicotinsäure
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EP0216324B1 (de)	1990-11-22	4-Alkoxy-3-pyrrolin-2-on-1-yl-essigsäurealkyl- bzw. -benzylester sowie deren Herstellung
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