IL132077A - Process for the production of 1-chlorocarbonyl-4-piperidinopipridine or its hydrochloride - Google Patents

Process for the production of 1-chlorocarbonyl-4-piperidinopipridine or its hydrochloride

Info

Publication number: IL132077A
Authority: IL; Israel
Prior art keywords: piperidinopiperidine; chlorocarbonyl; hydrochloride; represented; reacting
Prior art date: 1997-04-11

Application number

IL13207798A

Other languages

English (en)

Hebrew (he)

Other versions

IL132077A0 (en

Original Assignee

Yakult Honsha Kk

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.)

1997-04-11

Filing date

1998-03-31

Publication date

2002-11-10

1998-03-31 Application filed by Yakult Honsha Kk filed Critical Yakult Honsha Kk

2001-03-19 Publication of IL132077A0 publication Critical patent/IL132077A0/xx

2002-11-10 Publication of IL132077A publication Critical patent/IL132077A/en

Links

238000000034 method Methods 0.000 title claims abstract description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title abstract description 21
YDNSNQRKIINKPV-UHFFFAOYSA-N 4-piperidin-1-ylpiperidine-1-carbonyl chloride Chemical compound C1CN(C(=O)Cl)CCC1N1CCCCC1 YDNSNQRKIINKPV-UHFFFAOYSA-N 0.000 title abstract description 9
-1 trialkylsilyl halide Chemical class 0.000 claims abstract description 17
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 12
QDVBKXJMLILLLB-UHFFFAOYSA-N 1,4'-bipiperidine Chemical compound C1CCCCN1C1CCNCC1 QDVBKXJMLILLLB-UHFFFAOYSA-N 0.000 claims abstract description 10
239000001569 carbon dioxide Substances 0.000 claims abstract description 6
229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 6
AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 claims abstract description 4
125000004665 trialkylsilyl group Chemical group 0.000 claims abstract description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 4
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 3
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 3
VBXXNCHZAMNCBX-UHFFFAOYSA-N 4-piperidin-1-ylpiperidine-1-carbonyl chloride;hydrochloride Chemical compound Cl.C1CN(C(=O)Cl)CCC1N1CCCCC1 VBXXNCHZAMNCBX-UHFFFAOYSA-N 0.000 abstract description 5
239000000243 solution Substances 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 4
239000007789 gas Substances 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
PCQUGYRNPPGYRK-UHFFFAOYSA-N 1-piperidin-4-ylpiperidine;hydrochloride Chemical compound Cl.C1CCCCN1C1CCNCC1 PCQUGYRNPPGYRK-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
244000309464 bull Species 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000011835 investigation Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000004448 titration Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
235000020138 yakult Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)

IL13207798A 1997-04-11 1998-03-31 Process for the production of 1-chlorocarbonyl-4-piperidinopipridine or its hydrochloride IL132077A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP9093723A JP3046258B2 (ja)	1997-04-11	1997-04-11	１−クロロカルボニル−４−ピペリジノピペリジンまたはその塩酸塩の製造方法
PCT/JP1998/001465 WO1998046568A1 (en)	1997-04-11	1998-03-31	Process for producing 1-chlorocarbonyl-4-piperidinopiperidine or hydrochloride thereof

Publications (2)

Publication Number	Publication Date
IL132077A0 IL132077A0 (en)	2001-03-19
IL132077A true IL132077A (en)	2002-11-10

Family

ID=14090343

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL13207798A IL132077A (en)	1997-04-11	1998-03-31	Process for the production of 1-chlorocarbonyl-4-piperidinopipridine or its hydrochloride

Country Status (16)

Country	Link
US (1)	US6147215A (da)
EP (1)	EP0976733B1 (da)
JP (1)	JP3046258B2 (da)
CN (1)	CN1110479C (da)
AT (1)	ATE232517T1 (da)
AU (1)	AU723133B2 (da)
BR (1)	BR9808105B1 (da)
CA (1)	CA2286914C (da)
DE (1)	DE69811358T2 (da)
DK (1)	DK0976733T3 (da)
EA (1)	EA001696B1 (da)
ES (1)	ES2192765T3 (da)
IL (1)	IL132077A (da)
TW (1)	TW419476B (da)
WO (1)	WO1998046568A1 (da)
ZA (1)	ZA982960B (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP3046258B2 (ja)	1997-04-11	2000-05-29	株式会社ヤクルト本社	１−クロロカルボニル−４−ピペリジノピペリジンまたはその塩酸塩の製造方法
CA2591071C (en) *	2005-02-08	2014-04-29	Fermion Oy	Process for producing [1,4'] bipiperidinyl-1'-carbonyl chloride or hydrochloride thereof
US8546573B2 (en) *	2009-11-18	2013-10-01	Cadila Healthcare Limited	Process for the preparation of 7-ethyl-10-[4-(1-piperidino)-1-piperdino] carbonyloxy-camptothecin hydrochloride trihydrate
CN102869747B (zh)	2009-12-30	2017-06-30	普拉德研究及开发股份有限公司	在井下应用中的流体系统内流体段塞固结的方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5540754A (en) *	1978-09-19	1980-03-22	Mitsubishi Electric Corp	Electrodeposition coating
JPS6019790A (ja) *	1983-07-14	1985-01-31	Yakult Honsha Co Ltd	新規なカンプトテシン誘導体
JPS6150984A (ja) *	1984-07-05	1986-03-13	Yakult Honsha Co Ltd	新規なカンプトテシン誘導体
IE913790A1 (en) *	1990-10-31	1992-05-22	Smithkline Beecham Corp	SUBSTITUTED INDOLIZINO [1,2-b]QUINOLINONES
JP3046258B2 (ja)	1997-04-11	2000-05-29	株式会社ヤクルト本社	１−クロロカルボニル−４−ピペリジノピペリジンまたはその塩酸塩の製造方法

1997
- 1997-04-11 JP JP9093723A patent/JP3046258B2/ja not_active Expired - Fee Related
1998
- 1998-03-31 ES ES98911123T patent/ES2192765T3/es not_active Expired - Lifetime
- 1998-03-31 WO PCT/JP1998/001465 patent/WO1998046568A1/ja not_active Ceased
- 1998-03-31 CN CN98804019A patent/CN1110479C/zh not_active Expired - Fee Related
- 1998-03-31 DE DE69811358T patent/DE69811358T2/de not_active Expired - Lifetime
- 1998-03-31 DK DK98911123T patent/DK0976733T3/da active
- 1998-03-31 AT AT98911123T patent/ATE232517T1/de active
- 1998-03-31 US US09/402,470 patent/US6147215A/en not_active Expired - Lifetime
- 1998-03-31 BR BRPI9808105-5A patent/BR9808105B1/pt not_active IP Right Cessation
- 1998-03-31 EP EP98911123A patent/EP0976733B1/en not_active Expired - Lifetime
- 1998-03-31 IL IL13207798A patent/IL132077A/en not_active IP Right Cessation
- 1998-03-31 AU AU65206/98A patent/AU723133B2/en not_active Ceased
- 1998-03-31 CA CA002286914A patent/CA2286914C/en not_active Expired - Fee Related
- 1998-03-31 EA EA199900926A patent/EA001696B1/ru not_active IP Right Cessation
- 1998-04-02 TW TW087105000A patent/TW419476B/zh not_active IP Right Cessation
- 1998-04-07 ZA ZA982960A patent/ZA982960B/xx unknown

Also Published As

Publication number	Publication date
ZA982960B (en)	1998-10-09
EP0976733A1 (en)	2000-02-02
IL132077A0 (en)	2001-03-19
JP3046258B2 (ja)	2000-05-29
CA2286914C (en)	2005-07-26
EP0976733A4 (en)	2001-05-09
TW419476B (en)	2001-01-21
ES2192765T3 (es)	2003-10-16
AU6520698A (en)	1998-11-11
JPH10287650A (ja)	1998-10-27
DE69811358D1 (de)	2003-03-20
EA199900926A1 (ru)	2000-04-24
DE69811358T2 (de)	2003-10-16
BR9808105B1 (pt)	2008-11-18
ATE232517T1 (de)	2003-02-15
WO1998046568A1 (en)	1998-10-22
EP0976733B1 (en)	2003-02-12
AU723133B2 (en)	2000-08-17
CA2286914A1 (en)	1998-10-22
EA001696B1 (ru)	2001-06-25
BR9808105A (pt)	2000-03-08
US6147215A (en)	2000-11-14
DK0976733T3 (da)	2003-03-31
CN1252055A (zh)	2000-05-03
CN1110479C (zh)	2003-06-04

Legal Events

Date	Code	Title
2003-04-10	FF	Patent granted
2003-07-06	KB	Patent renewed
2004-06-01	KB	Patent renewed
2008-04-13	KB	Patent renewed
2012-03-29	KB	Patent renewed
2016-11-30	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
IE44472B1 (en)	1981-12-16	Prodution of aromatic urethanes
EP0976733B1 (en)	2003-02-12	Process for producing 1-chlorocarbonyl-4-piperidinopiperidine or hydrochloride thereof
US5274166A (en)	1993-12-28	Dithiocarbamic acid salt, process for production thereof, and process for production of isothiocyanate using said dithiocarbamic acid salt
US5574155A (en)	1996-11-12	Process for the synthesis of the disodium salt hemiheptahydrate of ceftriaxone
MXPA99009263A (en)	2001-12-04	Process for producing 1-chlorocarbonyl-4-piperidinopiperidine or hydrochloride thereof
US4321402A (en)	1982-03-23	Carbamate process
KR100498894B1 (ko)	2005-07-04	1-클로로카르보닐-4-피페리디노피페리딘 또는 그의 염산염 제조방법
JP4986343B2 (ja)	2012-07-25	１−クロロカルボニルピペリジン誘導体塩酸塩の処理方法
EP0070467B1 (en)	1985-09-18	Process for synthesising n-isopropyl-n'-o-carbomethoxyphenylsulphamide
JPH0737440B2 (ja)	1995-04-26	スルホニウム化合物の製造方法
CA1058198A (en)	1979-07-10	Carbonic acid esters, and the preparation thereof and their use
KR0173084B1 (ko)	1999-03-30	트리아민 화합물의 정제방법
US4375554A (en)	1983-03-01	Process for preparing amidinecarboxylic acids
JPH0446175A (ja)	1992-02-17	５―ヒドロキシ―３，４―メチレンジオキシ安息香酸誘導体の製造法
US5047573A (en)	1991-09-10	Process for the production of peptides using diacylamines
JP3740783B2 (ja)	2006-02-01	４−（２−アルケニル）−２，５−オキサゾリジンジオン類の製造法
KR940009935B1 (ko)	1994-10-19	N-벤조일-c-티오펜옥시이미도일 클로라이드 유도체 및 그 제조방법
KR820000881B1 (ko)	1982-05-20	치아졸리딘 유도체의 제조방법
US5001239A (en)	1991-03-19	Formation of reissert compound of benzoyl benzimidazole
US5227509A (en)	1993-07-13	Process for manufacture of organic esters of strong acids
JPS5888372A (ja)	1983-05-26	Ｎ−カルバモイル安息香酸スルフイミド誘導体の製法
JPS6029380B2 (ja)	1985-07-10	Ｎ，ｎ′−カルボニル−ビスアミノ酸エステルの製造法
JPH0786102B2 (ja)	1995-09-20	光学活性な６−（４−イミダゾリルメチル）−３−置換−２，５−ピペラジンジオンの製造法
JPH06145112A (ja)	1994-05-24	ジ炭酸ジアルキルエステルの製造方法
WO1996008465A1 (en)	1996-03-21	Ring-opening amidation process