JPS61246176A - アミノラクトンの調製方法 - Google Patents

アミノラクトンの調製方法

Info

Publication number: JPS61246176A
Authority: JP; Japan
Prior art keywords: formula; compound; aminolactone; residue; hydrochloric acid
Prior art date: 1984-08-15
Legal status (The legal status 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 status listed.): Pending

Application number

JP17775885A

Other languages

English (en)

Japanese (ja)

Inventor

カロリ　レンペルト

ガボル　ドレツシヤル

ヨセフ　フエツテル

ギユラ　ホルニヤク

ヨセフ　ニトライ

ギユラ　シミグ

カロリ　ザウエル

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Richter Gedeon Nyrt

Teva Pharmaceutical Works PLC

Richter Gedeon Vegyeszeti Gyar Nyrt

Original Assignee

Richter Gedeon Nyrt

Richter Gedeon Vegyeszeti Gyar RT

Biogal Gyogyszergyar Rt

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

1985-08-14

Publication date

1986-11-01

1985-08-14 Application filed by Richter Gedeon Nyrt, Richter Gedeon Vegyeszeti Gyar RT, Biogal Gyogyszergyar Rt filed Critical Richter Gedeon Nyrt

1986-11-01 Publication of JPS61246176A publication Critical patent/JPS61246176A/ja

Status Pending legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 35
150000001875 compounds Chemical class 0.000 claims description 22
238000000034 method Methods 0.000 claims description 19
-1 alkane carboxylic acid Chemical class 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
150000004678 hydrides Chemical class 0.000 claims description 7
150000001335 aliphatic alkanes Chemical group 0.000 claims description 5
239000012279 sodium borohydride Substances 0.000 claims description 4
229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
230000002829 reductive effect Effects 0.000 claims description 2
239000000126 substance Substances 0.000 claims 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims 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 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 38
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
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
239000011541 reaction mixture Substances 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
239000012074 organic phase Substances 0.000 description 14
238000005160 1H NMR spectroscopy Methods 0.000 description 10
229960000583 acetic acid Drugs 0.000 description 10
230000008018 melting Effects 0.000 description 9
238000002844 melting Methods 0.000 description 9
239000000203 mixture Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
239000012071 phase Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
238000009835 boiling Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
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
239000003610 charcoal Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
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
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-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
230000005587 bubbling Effects 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000000543 intermediate 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
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007787 solid 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
238000006257 total synthesis reaction Methods 0.000 description 2
XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
QSMYAUJWSXKKDS-UHFFFAOYSA-N 2-(1,2-oxazol-3-yl)acetic acid Chemical compound OC(=O)CC=1C=CON=1 QSMYAUJWSXKKDS-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
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
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
102000052583 Anaphase-Promoting Complex-Cyclosome Apc8 Subunit Human genes 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
102100024829 DNA polymerase delta catalytic subunit Human genes 0.000 description 1
101000912124 Homo sapiens Cell division cycle protein 23 homolog Proteins 0.000 description 1
101000868333 Homo sapiens Cyclin-dependent kinase 1 Proteins 0.000 description 1
101000909198 Homo sapiens DNA polymerase delta catalytic subunit Proteins 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
101100029577 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CDC43 gene Proteins 0.000 description 1
239000002253 acid Substances 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
230000003115 biocidal effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
YJHMZPLQGGTQHC-UHFFFAOYSA-N butyl 3-(2-butoxy-2-oxoethyl)-5-methyl-1,2-oxazole-4-carboxylate Chemical compound CCCCOC(=O)CC1=NOC(C)=C1C(=O)OCCCC YJHMZPLQGGTQHC-UHFFFAOYSA-N 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 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
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229940079826 hydrogen sulfite Drugs 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000005192 partition Methods 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [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
229910052705 radium Inorganic materials 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000006894 reductive elimination reaction Methods 0.000 description 1
239000013049 sediment Substances 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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)

JP17775885A 1984-08-15 1985-08-14 アミノラクトンの調製方法 Pending JPS61246176A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU2251/3090/84		1984-08-15
HU309084A HU194203B (en)	1984-08-15	1984-08-15	Process for producing amino-lactone

Publications (1)

Publication Number	Publication Date
JPS61246176A true JPS61246176A (ja)	1986-11-01

Family

ID=10962501

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP17775885A Pending JPS61246176A (ja)	1984-08-15	1985-08-14	アミノラクトンの調製方法

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)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6984738B2 (en)	2002-10-18	2006-01-10	Tohru Yokozawa	Process for production of optically active amino alcohols

Families Citing this family (2)

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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6984738B2 (en)	2002-10-18	2006-01-10	Tohru Yokozawa	Process for production of optically active amino alcohols

Also Published As

Publication number	Publication date
GB8520403D0 (en)	1985-09-18
DE3529159A1 (de)	1986-02-27
SE453193B (sv)	1988-01-18
FR2569194A1 (fr)	1986-02-21
SE8503811D0 (sv)	1985-08-14
PT80959A (en)	1985-09-01
HU194203B (en)	1988-01-28
CH666686A5 (de)	1988-08-15
ES8609297A1 (es)	1986-09-01
SE8503811L (sv)	1986-02-16
HUT37777A (en)	1986-02-28
FR2569194B3 (fr)	1987-06-26
BE903069A (fr)	1986-02-14
ES546140A0 (es)	1986-09-01
PT80959B (en)	1987-02-06
GB2163160A (en)	1986-02-19

Publication	Publication Date	Title
JPS61251650A (ja)	1986-11-08	（ｚ）−１−フエニル−１−ジエチルアミノカルボニル−２−アミノメチルシクロプロパン塩酸塩の製造方法
JPH04134077A (ja)	1992-05-07	イソオキサゾール化合物
US4189596A (en)	1980-02-19	Preparing 2-arylalkanoic acid derivatives
JP2001233870A (ja)	2001-08-28	３−（１−ヒドロキシ−ペンチリデン）−５−ニトロ−３ｈ−ベンゾフラン−２−オン、その製造方法及びその用途
JPS63104957A (ja)	1988-05-10	オクタヒドロインドール誘導体の製造方法
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JPS61246176A - アミノラクトンの調製方法 - Google Patents

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