CN1272496A - 手性咪唑啉酮除草剂的制备方法 - Google Patents

手性咪唑啉酮除草剂的制备方法 Download PDF

Info

Publication number: CN1272496A
Authority: CN; China
Prior art keywords: formula; methyl; tetrahydroglyoxaline; acid; sec
Prior art date: 1999-05-03
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

CN00108177A

Other languages

English (en)

Chinese (zh)

Inventor

T·W·德拉布

P·J·韦普罗

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.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

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.)

1999-05-03

Filing date

2000-04-27

Publication date

2000-11-08

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=23174474&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CN1272496(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2000-04-27 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

2000-11-08 Publication of CN1272496A publication Critical patent/CN1272496A/zh

Status Pending legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 11
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 title description 10
238000000034 method Methods 0.000 claims abstract description 33
-1 dimethyl butyrate Chemical compound 0.000 claims description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 20
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 12
239000001301 oxygen Substances 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 8
239000003513 alkali Substances 0.000 claims description 7
229960003512 nicotinic acid Drugs 0.000 claims description 7
235000001968 nicotinic acid Nutrition 0.000 claims description 7
239000011664 nicotinic acid Substances 0.000 claims description 7
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 5
229910052728 basic metal Inorganic materials 0.000 claims description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
239000011260 aqueous acid Substances 0.000 claims description 4
150000005690 diesters Chemical class 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
238000010306 acid treatment Methods 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
150000003818 basic metals Chemical class 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
150000002430 hydrocarbons Chemical class 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000005826 halohydrocarbons Chemical class 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
YCPQUHCGFDFLSI-ZCFIWIBFSA-N (2r)-2-amino-2,3-dimethylbutanamide Chemical compound CC(C)[C@@](C)(N)C(N)=O YCPQUHCGFDFLSI-ZCFIWIBFSA-N 0.000 abstract 1
CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 abstract 1
239000004009 herbicide Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000009333 weeding Methods 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000004445 quantitative analysis Methods 0.000 description 2
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
229910004298 SiO 2 Inorganic materials 0.000 description 1
GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
239000002027 dichloromethane extract Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
235000014347 soups Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/06—Nitrogen directly attached to an aromatic ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CN00108177A 1999-05-03 2000-04-27 手性咪唑啉酮除草剂的制备方法 Pending CN1272496A (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US09/303,967 US5973154A (en)	1999-05-03	1999-05-03	Process for the preparation of chiral imidazolinone herbicides
US09/303,967		1999-05-03

Publications (1)

Publication Number	Publication Date
CN1272496A true CN1272496A (zh)	2000-11-08

Family

ID=23174474

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN00108177A Pending CN1272496A (zh)	1999-05-03	2000-04-27	手性咪唑啉酮除草剂的制备方法

Country Status (18)

Country	Link
US (1)	US5973154A (2)
EP (1)	EP1050533A1 (2)
JP (1)	JP2000319276A (2)
KR (1)	KR20010029680A (2)
CN (1)	CN1272496A (2)
AR (1)	AR025522A1 (2)
AU (1)	AU3024300A (2)
BR (1)	BR0002073A (2)
CA (1)	CA2307391C (2)
HU (1)	HUP0001710A3 (2)
IL (1)	IL135795A (2)
IN (1)	IN187740B (2)
MX (1)	MXPA00004111A (2)
NZ (1)	NZ504204A (2)
PL (1)	PL339971A1 (2)
SK (1)	SK6002000A3 (2)
TW (1)	TWI223650B (2)
ZA (1)	ZA200002131B (2)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2021115400A1 (zh) *	2019-12-13	2021-06-17	沈阳中化农药化工研发有限公司	一种咪唑啉酮化合物的制备方法

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2413629T3 (es)	2004-04-01	2013-07-17	Basf Agrochemical Products, B.V.	Mezclas herbicidas de acción sinérgica
US9210930B2 (en) *	2005-12-23	2015-12-15	Basf Se	Control of submerged aquatic vegetation
KR20080081979A (ko) *	2005-12-23	2008-09-10	바스프 에스이	수생 잡초의 억제 방법
DE602006009704D1 (de) *	2005-12-23	2009-11-19	Basf Se	Verfahren zur bekämpfung des wasserunkrauts hydrilla verticillata
US20090176648A1 (en) *	2006-04-07	2009-07-09	Thomas Byrne	Herbicidal Mixture, Comprising an Imidazolinone Herbicide and an Adjuvant
HUE036021T2 (hu)	2008-06-18	2018-06-28	Basf Se	Aminopiralidot és imazamoxot tartalmazó háromkomponensû herbicid készítmények
WO2010055042A1 (en) *	2008-11-13	2010-05-20	Basf Se	2-[(1-cyanopropyl)carbamoyl]-5-methoxymethyl nicotinic acids and the use thereof in manufacturing herbicidal imidazolinones
WO2010054954A1 (en) *	2008-11-13	2010-05-20	Basf Se	Process for manufacturing 5-chloromethyl-2,3-pyridine dicarboxylic acid anhydrides
US8563734B2 (en) *	2008-11-13	2013-10-22	Basf Se	2-[1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids and the use thereof in manufacturing herbicidal imidazolinones
US8389731B2 (en)	2009-05-15	2013-03-05	Northwestern University	Chiral pyrrolidine core compounds en route to inhibitors of nitric oxide synthase
WO2012025472A1 (en)	2010-08-24	2012-03-01	Basf Se	Agrochemical mixtures for increasing the health of a plant
SI2787814T1 (en)	2011-12-05	2018-03-30	Basf Agrochemical Products B.V.	METHODS OF CONTROL OF UNAUTHORIZED VEGETATION WITH IMAGE AND ADDITIVES IN HERBICIDIC RESISTANT INDUSTRIAL PLANTS
EP3541787A1 (en)	2016-11-21	2019-09-25	Adama Agan Ltd.	Process for preparing methoxy methyl pyridine dicarboxylate
EP3897151B1 (en)	2018-12-18	2026-04-22	BASF Agrochemical Products B.V.	Herbicidal composition
EP3897138A1 (en)	2018-12-18	2021-10-27	BASF Agrochemical Products B.V.	Herbicidal combinations
EP3897140A1 (en)	2018-12-18	2021-10-27	BASF Agrochemical Products B.V.	Herbicidal combinations
EA202191654A1 (ru)	2018-12-18	2021-11-01	Басф Агрокемикэл Продактс Б.В.	Гербицидные комбинации
EA202191606A1 (ru)	2018-12-18	2021-10-26	Басф Агрокемикэл Продактс Б.В.	Гербицидные комбинации
EP3897141A1 (en)	2018-12-18	2021-10-27	BASF Agrochemical Products B.V.	Herbicidal combinations
RU2707043C1 (ru) *	2019-03-25	2019-11-21	Акционерное общество "Щелково Агрохим"	Способ получения гербицида имазамокса
CN113620928A (zh) *	2021-08-16	2021-11-09	辽宁先达农业科学有限公司	一种甲氧咪草烟钠盐的合成方法
US20250169499A1 (en)	2021-09-28	2025-05-29	Basf Agrochemical Products B.V.	Imazamox and glyphosate for controlling digitaria insularis

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4683324A (en) *	1982-05-25	1987-07-28	American Cyanamid Company	Process for the resolution of certain racemic amino nitriles
ATE43845T1 (de) *	1983-06-02	1989-06-15	American Cyanamid Co	(2-imidazolin-2-yl)thieno-und furo(2,3-b)-und (3,2-b)-pyridine und zwischenprodukte, ihre herstellung und ihre verwendung als herbizide mittel.
ATE82279T1 (de) *	1986-02-10	1992-11-15	Ciba Geigy Ag	Verfahren zur herstellung von 2-(imidazolin-2-yl)-pyridin- und -chinolin-3-carbonsaeuren.
EP0296109A3 (de) *	1987-06-18	1989-12-20	Ciba-Geigy Ag	2-(Imidazolin-2-yl)nicotinsäurederivate
US4925944A (en) *	1989-03-21	1990-05-15	American Cyanamid Company	Process for the preparation of o-carboxypyridyl- and o-carboxyquinolylimidazolinones

1999
- 1999-05-03 US US09/303,967 patent/US5973154A/en not_active Expired - Fee Related
2000
- 2000-04-24 IL IL13579500A patent/IL135795A/en active IP Right Grant
- 2000-04-25 JP JP2000123949A patent/JP2000319276A/ja not_active Withdrawn
- 2000-04-26 SK SK600-2000A patent/SK6002000A3/sk unknown
- 2000-04-27 CN CN00108177A patent/CN1272496A/zh active Pending
- 2000-04-27 NZ NZ504204A patent/NZ504204A/en unknown
- 2000-04-27 MX MXPA00004111A patent/MXPA00004111A/es unknown
- 2000-04-28 EP EP00303585A patent/EP1050533A1/en not_active Ceased
- 2000-04-28 PL PL00339971A patent/PL339971A1/xx not_active Application Discontinuation
- 2000-05-01 CA CA002307391A patent/CA2307391C/en not_active Expired - Fee Related
- 2000-05-01 IN IN257CA2000 patent/IN187740B/en unknown
- 2000-05-01 KR KR1020000023246A patent/KR20010029680A/ko not_active Ceased
- 2000-05-02 TW TW089108313A patent/TWI223650B/zh not_active IP Right Cessation
- 2000-05-02 AU AU30243/00A patent/AU3024300A/en not_active Abandoned
- 2000-05-02 ZA ZA200002131A patent/ZA200002131B/xx unknown
- 2000-05-02 AR ARP000102094A patent/AR025522A1/es unknown
- 2000-05-02 BR BR0002073-7A patent/BR0002073A/pt not_active Application Discontinuation
- 2000-05-02 HU HU0001710A patent/HUP0001710A3/hu unknown

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2021115400A1 (zh) *	2019-12-13	2021-06-17	沈阳中化农药化工研发有限公司	一种咪唑啉酮化合物的制备方法
CN113061125A (zh) *	2019-12-13	2021-07-02	沈阳中化农药化工研发有限公司	一种咪唑啉酮化合物的制备方法

Also Published As

Publication number	Publication date
HUP0001710A3 (en)	2002-12-28
KR20010029680A (ko)	2001-04-06
HUP0001710A2 (hu)	2001-05-28
MXPA00004111A (es)	2002-07-22
IL135795A (en)	2004-05-12
EP1050533A1 (en)	2000-11-08
HU0001710D0 (en)	2000-06-28
TWI223650B (en)	2004-11-11
JP2000319276A (ja)	2000-11-21
PL339971A1 (en)	2000-11-06
CA2307391C (en)	2008-07-08
BR0002073A (pt)	2001-01-02
AR025522A1 (es)	2002-12-04
CA2307391A1 (en)	2000-11-03
US5973154A (en)	1999-10-26
ZA200002131B (en)	2000-11-07
SK6002000A3 (en)	2000-12-11
AU3024300A (en)	2000-11-09
IN187740B (2)	2002-06-15
IL135795A0 (en)	2001-05-20
NZ504204A (en)	2001-09-28

Legal Events

Date	Code	Title
2000-11-08	C06	Publication
2000-11-08	PB01	Publication
2002-07-03	C10	Entry into substantive examination
2002-07-03	SE01	Entry into force of request for substantive examination
2004-07-14	C02	Deemed withdrawal of patent application after publication (patent law 2001)
2004-07-14	WD01	Invention patent application deemed withdrawn after publication

Publication	Publication Date	Title
RU2140909C1 (ru)	1999-11-10	Способ получения антагонистов лейкотриена, дициклогексиламиновая соль, способы получения кристаллической натриевой соли и 1-/меркаптометил/- циклопропануксусной кислоты, кристаллическое соединение
US6339158B1 (en)	2002-01-15	Process for the preparation of chiral nicotinic, quinolinic or benzoic acid imidazolinone herbicides
US5973154A (en)	1999-10-26	Process for the preparation of chiral imidazolinone herbicides
CN1256275A (zh)	2000-06-14	亚砜化合物和丙酮的络合物,及其生产方法
CN1189155A (zh)	1998-07-29	2－(6－取代吡啶－2－基氧甲基)苯乙酸酯的制备方法
KR20020058071A (ko)	2002-07-12	신규 방법
JPS60500499A (ja)	1985-04-11	メバロノラクトン同族体とその誘導体、それらの製造法、それらを含む製薬学的組成物、及びその製薬剤としての使用法
EP1153919A1 (en)	2001-11-14	Substituted acetylpyridine derivatives and process for the preparation of intermediates for optically active beta3 agonist by the use of the same
EP0474129B1 (en)	1996-12-18	1,4-Dihydropyridine derivatives and process for preparing the same
EP2066638B1 (en)	2011-02-23	Process for the purification of montelukast
CA2339357A1 (en)	2000-12-14	Processes for the preparation of 5-hydroxy-3-oxopentanoic acid derivatives
US5336774A (en)	1994-08-09	1,4-dihydropyridine 3,5 carboxyl compounds
CN108530416B (zh)	2020-05-12	一种瑞舒伐他汀中间体的制备方法
NZ542025A (en)	2009-03-31	Method for producing the enantiomeric forms of cis 1,3-cyclohexanediol derivatives using stereoselective enzymatic ester formation or enzymatic ester hydrolysis
WO2002012221A1 (en)	2002-02-14	Method for optical resolution of (±)-6-hydroxy-2,5,7,8-tetramethylcoumarone-2-carboxylic acid
CN101003820A (zh)	2007-07-25	用于制备光学活性环戊烯酮化物的方法及由其制得的环戊烯酮化物
CN101056857A (zh)	2007-10-17	异烟酸衍生物的制备方法
CN116947768B (zh)	2025-08-01	一种对映体纯的平面手性二苯并二氮芳辛二酮化合物及其制备方法和应用
EP1163223A1 (en)	2001-12-19	Synthesis of 3-amino-3-aryl propanoates
CN102586356B (zh)	2014-06-04	一种酶催化合成喹啉杂环衍生物的方法
JP5787399B2 (ja)	2015-09-30	新規不斉触媒、並びに光学活性カルボン酸エステル、光学活性アルコール、及び光学活性カルボン酸の製造方法
KR100915174B1 (ko)	2009-09-03	신규한 2-옥소이미다졸리딘 유도체의 제조방법
CN115678936A (zh)	2023-02-03	一种选择性合成手性醇及环氧化合物的方法
JPH085840B2 (ja)	1996-01-24	ジャスモン酸の光学分割方法
JPH10182559A (ja)	1998-07-07	ジアルキルオキサルアセテート類の製造方法