CH666686A5 - Verfahren zur herstellung eines aminolactons. - Google Patents

Verfahren zur herstellung eines aminolactons. Download PDF

Info

Publication number: CH666686A5
Authority: CH; Switzerland
Prior art keywords: residue; mixture; water; methyl; solution
Prior art date: 1984-08-15

Application number

CH320285A

Other languages

German (de)

English (en)

Inventor

Karoly Dr Lempert

Gabor Dr Doleschall

Jozsef Dr Fetter

Gyula Dr Hornyak

Jozsef Dr Nyitrai

Gyula Dr Simig

Karoly Dr Zauer

Original Assignee

Richter Gedeon Vegyeszet

Biogal Gyogyszergyar

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.)

1984-08-15

Filing date

1985-07-24

Publication date

1988-08-15

1985-07-24 Application filed by Richter Gedeon Vegyeszet, Biogal Gyogyszergyar filed Critical Richter Gedeon Vegyeszet

1988-08-15 Publication of CH666686A5 publication Critical patent/CH666686A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 3
238000000034 method Methods 0.000 claims description 12
150000004678 hydrides Chemical class 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
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 5
239000011734 sodium Substances 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
150000001875 compounds Chemical class 0.000 description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 19
239000000203 mixture Substances 0.000 description 17
-1 alkane carboxylic acid Chemical class 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 11
238000005481 NMR spectroscopy Methods 0.000 description 9
239000012071 phase Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
239000012074 organic phase Substances 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
238000003756 stirring Methods 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
238000009835 boiling Methods 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
KSFLJMSEFARLTK-WYMLVPIESA-N C(C)(=O)/C(/C(=O)OCCCC)=C(/CC(=O)OCCCC)N Chemical compound C(C)(=O)/C(/C(=O)OCCCC)=C(/CC(=O)OCCCC)N KSFLJMSEFARLTK-WYMLVPIESA-N 0.000 description 2
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000007789 gas Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
150000002545 isoxazoles Chemical class 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
238000000746 purification Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
NUJNTWROJOXVNY-UHFFFAOYSA-N 3-(5-methyl-1,2-oxazol-4-yl)-4h-1,2-oxazol-5-one Chemical compound O1N=CC(C=2CC(=O)ON=2)=C1C NUJNTWROJOXVNY-UHFFFAOYSA-N 0.000 description 1
UHNBTCAVNNUNKB-UHFFFAOYSA-N 4-amino-2-methyl-6-oxooxane-3-carboxylic acid;hydrochloride Chemical compound Cl.CC1OC(=O)CC(N)C1C(O)=O UHNBTCAVNNUNKB-UHFFFAOYSA-N 0.000 description 1
ZKAQPVQEYCFRTK-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carbonyl chloride Chemical compound CC=1ON=CC=1C(Cl)=O ZKAQPVQEYCFRTK-UHFFFAOYSA-N 0.000 description 1
VQBXUKGMJCPBMF-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound CC=1ON=CC=1C(O)=O VQBXUKGMJCPBMF-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
JQXWKUNNCUTQQN-BMRADRMJSA-N C(C)(=O)/C(/C(=O)OCC)=C(/CC(=O)OCC)NCC1=CC=CC=C1 Chemical compound C(C)(=O)/C(/C(=O)OCC)=C(/CC(=O)OCC)NCC1=CC=CC=C1 JQXWKUNNCUTQQN-BMRADRMJSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 description 1
WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000006264 debenzylation reaction Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
KOMSQTMQKWSQDW-UHFFFAOYSA-N ethyl 5-methyl-1,2-oxazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NOC=1C KOMSQTMQKWSQDW-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000037361 pathway Effects 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/12—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings 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
- C07D309/30—Oxygen atoms, e.g. delta-lactones

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pyrane Compounds (AREA)

CH320285A 1984-08-15 1985-07-24 Verfahren zur herstellung eines aminolactons. CH666686A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU309084A HU194203B (en)	1984-08-15	1984-08-15	Process for producing amino-lactone

Publications (1)

Publication Number	Publication Date
CH666686A5 true CH666686A5 (de)	1988-08-15

Family

ID=10962501

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH320285A CH666686A5 (de)	1984-08-15	1985-07-24	Verfahren zur herstellung eines aminolactons.

Country Status (10)

Country	Link
JP (1)	JPS61246176A (fr)
BE (1)	BE903069A (fr)
CH (1)	CH666686A5 (fr)
DE (1)	DE3529159A1 (fr)
ES (1)	ES8609297A1 (fr)
FR (1)	FR2569194B3 (fr)
GB (1)	GB2163160A (fr)
HU (1)	HU194203B (fr)
PT (1)	PT80959B (fr)
SE (1)	SE453193B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8531638D0 (en) *	1985-12-23	1986-02-05	Ici Plc	Chemical compounds
ATE384038T1 (de)	2002-10-18	2008-02-15	Tohru Yokozawa	Verfahren zur herstellung optisch aktiver aminoalkohole
WO2007086076A2 (fr) *	2006-01-24	2007-08-02	Unichem Laboratories Limited	Procede ameliore de preparation de leflunomide

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4287123A (en) *	1980-01-14	1981-09-01	Merck & Co., Inc.	Synthesis of thienamycin via (3SR, 4RS)-3-((RS)-1-acyloxyethyl)-2-oxo-4-azetidineacetate
US4360684A (en) *	1981-04-08	1982-11-23	Merck & Co., Inc.	Process for the preparation of (2S)-tetrahydro-2α-methyl-6-oxo-4βα-carboxylic acid

1984
- 1984-08-15 HU HU309084A patent/HU194203B/hu not_active IP Right Cessation
1985
- 1985-07-24 CH CH320285A patent/CH666686A5/de not_active IP Right Cessation
- 1985-08-14 FR FR8512410A patent/FR2569194B3/fr not_active Expired
- 1985-08-14 DE DE19853529159 patent/DE3529159A1/de not_active Withdrawn
- 1985-08-14 JP JP17775885A patent/JPS61246176A/ja active Pending
- 1985-08-14 BE BE0/215472A patent/BE903069A/fr not_active IP Right Cessation
- 1985-08-14 SE SE8503811A patent/SE453193B/sv not_active IP Right Cessation
- 1985-08-14 ES ES546140A patent/ES8609297A1/es not_active Expired
- 1985-08-14 PT PT8095985A patent/PT80959B/pt unknown
- 1985-08-14 GB GB08520403A patent/GB2163160A/en not_active Withdrawn

Also Published As

Publication number	Publication date
FR2569194A1 (fr)	1986-02-21
BE903069A (fr)	1986-02-14
ES8609297A1 (es)	1986-09-01
HU194203B (en)	1988-01-28
PT80959A (en)	1985-09-01
SE8503811L (sv)	1986-02-16
HUT37777A (en)	1986-02-28
ES546140A0 (es)	1986-09-01
SE453193B (sv)	1988-01-18
PT80959B (en)	1987-02-06
JPS61246176A (ja)	1986-11-01
FR2569194B3 (fr)	1987-06-26
GB2163160A (en)	1986-02-19
SE8503811D0 (sv)	1985-08-14
GB8520403D0 (en)	1985-09-18
DE3529159A1 (de)	1986-02-27

Legal Events

Date	Code	Title	Description
1989-03-31	PL	Patent ceased
2024-10-31	PLX	Patent declared invalid from date of grant onwards

Publication	Publication Date	Title
DE3010195C2 (fr)	1990-10-25
DE2314636C2 (de)	1986-09-11	Indanderivate, deren Herstellung und diese enthaltende pharmazeutische Mittel
DE2149070C3 (de)	1978-03-23	Phenoxyalkylcarbonsäurederivate und deren Salze, Verfahren zu deren Herstellung und Arzneimittel
DE2903891C2 (fr)	1992-02-06
CH666686A5 (de)	1988-08-15	Verfahren zur herstellung eines aminolactons.
CH653996A5 (de)	1986-01-31	Tryptaminderivate und verfahren zu deren herstellung.
DE69516396T2 (de)	2000-08-31	Verfahren zur herstellung von 3-isoxazol carbonsäure
DE69804853T2 (de)	2002-11-14	Verfahren zur herstellung von mequitazin und zwischenprodukt der synthese
DE2525852C2 (fr)	1989-03-09
CH644122A5 (de)	1984-07-13	14-oxo-15-halogen-e-homoeburnanderivate, verfahren zu deren herstellung und deren verwendung.
DE1768582C3 (fr)	1973-01-04
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DE2164662A1 (de)	1972-07-27	Indanderivate und Verfahren zu ihrer Herstellung
CH623574A5 (fr)	1981-06-15
EP0014478A1 (fr)	1980-08-20	Procédé pour la préparation de 4,10-dihydro-10-oxo-thiéno (3,2-c) (1) benzoxépine-8-acétate d'alcoyle
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EP0069880B1 (fr)	1984-09-12	Dérivés de la cyclopentanone et procédé pour leur isomérisation
CH652127A5 (en)	1985-10-31	Halovincaminic acid derivatives, a process for their preparation and drugs containing these compounds
AT216495B (de)	1961-07-25	Verfahren zur Herstellung von neuen Phenylalaninderivaten und deren Salzen
CH652126A5 (en)	1985-10-31	Process for preparing halovincaminic acid and haloapovincaminic acid ester derivatives
DE861839C (de)	1953-01-05	Verfahren zur Herstellung von threo-1-(4'-Nitrophenyl)-2-dichloracetylamino-1, 3-dichlorpropanen
DE2222186C3 (de)	1978-02-16	Verfahren zur Herstellung von Vincamin und analogen Verbindungen
AT222116B (de)	1962-07-10	Verfahren zur Herstellung von neuen, 4-substituierten 1,2-Diaryl-3,5-dioxo-pyrazolidinen
DE1445858C3 (de)	1976-02-26	7-Cyan-5-phenyl-1,2-dihydro-3H-l,4benzodiazepin-2-on-Derivate