UA73587C2 - A method for the preparation of quinoline derivatives - Google Patents

A method for the preparation of quinoline derivatives Download PDF

Info

Publication number: UA73587C2
Authority: UA; Ukraine
Prior art keywords: formula; compound; amount; water; temperature
Prior art date: 2000-06-28

Application number

UA2003010722A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Syngenta Participations Ag

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.)

2000-06-28

Filing date

2001-06-26

Publication date

2005-08-15

2001-06-26 Application filed by Syngenta Participations Ag filed Critical Syngenta Participations Ag

2005-08-15 Publication of UA73587C2 publication Critical patent/UA73587C2/uk

Links

238000000034 method Methods 0.000 title description 10
238000002360 preparation method Methods 0.000 title description 2
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title 1
125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
150000001875 compounds Chemical class 0.000 abstract description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 10
239000011541 reaction mixture Substances 0.000 abstract description 3
238000010533 azeotropic distillation Methods 0.000 abstract description 2
239000002904 solvent Substances 0.000 abstract description 2
239000001257 hydrogen Substances 0.000 abstract 2
229910052739 hydrogen Inorganic materials 0.000 abstract 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
239000000460 chlorine Substances 0.000 abstract 1
229910052801 chlorine Inorganic materials 0.000 abstract 1
150000002431 hydrogen Chemical class 0.000 abstract 1
239000003960 organic solvent Substances 0.000 abstract 1
239000011877 solvent mixture Substances 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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 description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 5
239000000155 melt Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
CTQMJYWDVABFRZ-UHFFFAOYSA-N cloxiquine Chemical compound C1=CN=C2C(O)=CC=C(Cl)C2=C1 CTQMJYWDVABFRZ-UHFFFAOYSA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000000203 mixture 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
150000003839 salts Chemical class 0.000 description 2
238000000926 separation method Methods 0.000 description 2
VIQBLZHDBUVBDS-UHFFFAOYSA-N 2-heptan-2-yloxyheptane Chemical compound CCCCCC(C)OC(C)CCCCC VIQBLZHDBUVBDS-UHFFFAOYSA-N 0.000 description 1
DLVFCDXDWGFLQN-UHFFFAOYSA-N ClC1=C2C=CC=NC2=C(C=C1)OC(C(C)OC(C(CCCC)OC=1C=CC(=C2C=CC=NC12)Cl)C)CCCC Chemical compound ClC1=C2C=CC=NC2=C(C=C1)OC(C(C)OC(C(CCCC)OC=1C=CC(=C2C=CC=NC12)Cl)C)CCCC DLVFCDXDWGFLQN-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
-1 hydroxyl ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002994 raw material Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000009466 transformation Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/28—Alcohols; Ethers thereof with halogen atoms or nitro radicals in positions 5, 6 or 7
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Plural Heterocyclic Compounds (AREA)
Quinoline Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

UA2003010722A 2000-06-28 2001-06-26 A method for the preparation of quinoline derivatives UA73587C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH12742000		2000-06-28
PCT/EP2001/007258 WO2002000625A2 (en)	2000-06-28	2001-06-26	Process for the preparation of quinoline derivatives

Publications (1)

Publication Number	Publication Date
UA73587C2 true UA73587C2 (en)	2005-08-15

Family

ID=4565202

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2003010722A UA73587C2 (en)	2000-06-28	2001-06-26	A method for the preparation of quinoline derivatives

Country Status (23)

Country	Link
US (1)	US6660865B2 (de)
EP (1)	EP1294694B1 (de)
JP (1)	JP3955814B2 (de)
KR (1)	KR100572818B1 (de)
CN (1)	CN1256327C (de)
AR (1)	AR029283A1 (de)
AT (1)	ATE280760T1 (de)
AU (1)	AU780534B2 (de)
BR (2)	BR0112064B1 (de)
CA (1)	CA2412543C (de)
DE (1)	DE60106760T2 (de)
DK (1)	DK1294694T3 (de)
ES (1)	ES2228923T3 (de)
HU (1)	HU230214B1 (de)
IL (2)	IL153424A0 (de)
MX (1)	MXPA02012398A (de)
PL (1)	PL200447B1 (de)
PT (1)	PT1294694E (de)
RU (1)	RU2263110C2 (de)
TW (1)	TWI230154B (de)
UA (1)	UA73587C2 (de)
WO (1)	WO2002000625A2 (de)
ZA (1)	ZA200300328B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2010042163A2 (en) *	2008-10-06	2010-04-15	The Johns Hopkins University	Quinoline compounds as inhibitors of angiogenesis, human methionine aminopeptidase, and sirt1, and methods of treating disorders
CN101805288A (zh) *	2010-04-21	2010-08-18	新沂市永诚化工有限公司	一种合成解毒喹的新方法
GB201119690D0 (en) *	2011-11-14	2011-12-28	Syngenta Participations Ag	Process for the preparation of compounds
CN102718706B (zh) *	2012-05-31	2014-05-07	绍兴文理学院	一种2-(5-氯-8-喹啉氧基)乙酸的制备方法
CN103524411B (zh) *	2013-10-21	2015-03-04	哈尔滨理工大学	一种5-氯-8-喹啉氧基乙酸的合成方法
CN105001158B (zh) *	2015-07-09	2018-02-02	北京颖泰嘉和生物科技股份有限公司	一种合成解草酯的方法
CN113135851B (zh) *	2021-04-26	2024-10-01	甘肃联凯生物科技有限公司	一种解毒喹的合成方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2934609A1 (de) *	1979-08-28	1981-03-12	Cassella Ag, 6000 Frankfurt	Tetrahydrochinolinderivate, verfahren zu ihrer herstellung, ihre verwendung und sie enthaltende pharmazeutische zubereitungen.
ATE103902T1 (de)	1982-05-07	1994-04-15	Ciba Geigy Ag	Verwendung von chinolinderivaten zum schuetzen von kulturpflanzen.
DE59108636D1 (de) *	1990-12-21	1997-04-30	Hoechst Schering Agrevo Gmbh	Neue 5-Chlorchinolin-8-oxyalkancarbonsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Antidots von Herbiziden

2001
- 2001-06-26 AU AU79689/01A patent/AU780534B2/en not_active Expired
- 2001-06-26 TW TW090115381A patent/TWI230154B/zh not_active IP Right Cessation
- 2001-06-26 AR ARP010103033A patent/AR029283A1/es active IP Right Grant
- 2001-06-26 EP EP01957889A patent/EP1294694B1/de not_active Expired - Lifetime
- 2001-06-26 DK DK01957889T patent/DK1294694T3/da active
- 2001-06-26 MX MXPA02012398A patent/MXPA02012398A/es active IP Right Grant
- 2001-06-26 KR KR1020027017703A patent/KR100572818B1/ko not_active Expired - Fee Related
- 2001-06-26 JP JP2002505373A patent/JP3955814B2/ja not_active Expired - Lifetime
- 2001-06-26 US US10/312,122 patent/US6660865B2/en not_active Expired - Lifetime
- 2001-06-26 DE DE60106760T patent/DE60106760T2/de not_active Expired - Lifetime
- 2001-06-26 UA UA2003010722A patent/UA73587C2/uk unknown
- 2001-06-26 BR BRPI0112064-6A patent/BR0112064B1/pt not_active IP Right Cessation
- 2001-06-26 ES ES01957889T patent/ES2228923T3/es not_active Expired - Lifetime
- 2001-06-26 HU HU0300703A patent/HU230214B1/hu unknown
- 2001-06-26 IL IL15342401A patent/IL153424A0/xx active IP Right Grant
- 2001-06-26 BR BRPI0112064A patent/BRPI0112064B8/pt unknown
- 2001-06-26 AT AT01957889T patent/ATE280760T1/de active
- 2001-06-26 CA CA2412543A patent/CA2412543C/en not_active Expired - Lifetime
- 2001-06-26 CN CNB018119549A patent/CN1256327C/zh not_active Expired - Lifetime
- 2001-06-26 WO PCT/EP2001/007258 patent/WO2002000625A2/en not_active Ceased
- 2001-06-26 PT PT01957889T patent/PT1294694E/pt unknown
- 2001-06-26 PL PL363224A patent/PL200447B1/pl unknown
- 2001-06-26 RU RU2003100505/04A patent/RU2263110C2/ru active
2002
- 2002-12-12 IL IL153424A patent/IL153424A/en unknown
2003
- 2003-01-13 ZA ZA200300328A patent/ZA200300328B/en unknown

Also Published As

Publication number	Publication date
ES2228923T3 (es)	2005-04-16
HUP0300703A2 (hu)	2003-07-28
HUP0300703A3 (en)	2005-01-28
US20030181724A1 (en)	2003-09-25
HU230214B1 (hu)	2015-10-28
BRPI0112064B8 (pt)	2018-08-14
ZA200300328B (en)	2004-03-31
CN1256327C (zh)	2006-05-17
BR0112064A (pt)	2003-05-13
CA2412543A1 (en)	2002-01-03
DE60106760T2 (de)	2005-11-03
KR100572818B1 (ko)	2006-04-25
DK1294694T3 (da)	2004-12-27
AR029283A1 (es)	2003-06-18
CA2412543C (en)	2010-05-25
PL200447B1 (pl)	2009-01-30
BR0112064B1 (pt)	2012-12-25
EP1294694B1 (de)	2004-10-27
TWI230154B (en)	2005-04-01
DE60106760D1 (de)	2004-12-02
US6660865B2 (en)	2003-12-09
AU7968901A (en)	2002-01-08
JP2004501898A (ja)	2004-01-22
PT1294694E (pt)	2005-02-28
IL153424A (en)	2007-08-19
WO2002000625A3 (en)	2002-07-18
AU780534B2 (en)	2005-03-24
PL363224A1 (en)	2004-11-15
JP3955814B2 (ja)	2007-08-08
WO2002000625A2 (en)	2002-01-03
CN1568314A (zh)	2005-01-19
KR20030036245A (ko)	2003-05-09
EP1294694A2 (de)	2003-03-26
RU2263110C2 (ru)	2005-10-27
MXPA02012398A (es)	2003-04-25
IL153424A0 (en)	2003-07-06
ATE280760T1 (de)	2004-11-15

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HU198437B (en)	1989-10-30	Process for producing mono- or bis-carbonyl-compounds
KR101813089B1 (ko)	2018-01-30	2-하이드록시부티로락톤의 제조 방법
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JPS6357416B2 (de)	1988-11-11
JPS56127360A (en)	1981-10-06	Preparation of 4-benzoyl-5-hydroxypyrazole compound
JPH10130220A (ja)	1998-05-19	Ｏ−アルキル−ｎ−シアノイミデートの製造法
YU187290A (sh)	1992-09-07	Postopek za proizvodnjo optično aktivnega 2-(tetrahidropiran-2-iloksi)-1-propano ol, nov intermediat, uporabljen pri tem postopku, ter njegova priprava
JPH083126A (ja)	1996-01-09	Ｎ，ｏ−ジメチルヒドロキシルアミンの製造方法
JPS5663949A (en)	1981-05-30	Preparation of nitrile compound
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CZ169592A3 (en)	1994-01-19	Process for preparing 2-propenyl ester of (e,e)-2,4-hexadienic acid