UA73587C2 - A method for the preparation of quinoline derivatives - Google Patents
A method for the preparation of quinoline derivatives Download PDFInfo
- Publication number
- UA73587C2 UA73587C2 UA2003010722A UA2003010722A UA73587C2 UA 73587 C2 UA73587 C2 UA 73587C2 UA 2003010722 A UA2003010722 A UA 2003010722A UA 2003010722 A UA2003010722 A UA 2003010722A UA 73587 C2 UA73587 C2 UA 73587C2
- Authority
- UA
- Ukraine
- Prior art keywords
- formula
- compound
- amount
- water
- temperature
- Prior art date
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)
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) | BRPI0112064B8 (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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102239149B (zh) * | 2008-10-06 | 2015-05-13 | 约翰·霍普金斯大学 | 喹啉化合物作为血管新生、人类甲硫氨酰氨肽酶、以及sirt1的抑制剂,以及治疗病症的方法 |
| 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 |
| CN113135851A (zh) * | 2021-04-26 | 2021-07-20 | 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 (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3382743D1 (de) * | 1982-05-07 | 1994-05-11 | Ciba Geigy | Verwendung von Chinolinderivaten zum Schützen 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 ES ES01957889T patent/ES2228923T3/es not_active Expired - Lifetime
- 2001-06-26 KR KR1020027017703A patent/KR100572818B1/ko not_active IP Right Cessation
- 2001-06-26 DK DK01957889T patent/DK1294694T3/da active
- 2001-06-26 HU HU0300703A patent/HU230214B1/hu unknown
- 2001-06-26 WO PCT/EP2001/007258 patent/WO2002000625A2/en active IP Right Grant
- 2001-06-26 AR ARP010103033A patent/AR029283A1/es active IP Right Grant
- 2001-06-26 BR BRPI0112064A patent/BRPI0112064B8/pt unknown
- 2001-06-26 TW TW090115381A patent/TWI230154B/zh not_active IP Right Cessation
- 2001-06-26 DE DE60106760T patent/DE60106760T2/de not_active Expired - Lifetime
- 2001-06-26 IL IL15342401A patent/IL153424A0/xx active IP Right Grant
- 2001-06-26 BR BRPI0112064-6A patent/BR0112064B1/pt not_active IP Right Cessation
- 2001-06-26 EP EP01957889A patent/EP1294694B1/de not_active Expired - Lifetime
- 2001-06-26 CA CA2412543A patent/CA2412543C/en not_active Expired - Lifetime
- 2001-06-26 MX MXPA02012398A patent/MXPA02012398A/es active IP Right Grant
- 2001-06-26 PL PL363224A patent/PL200447B1/pl unknown
- 2001-06-26 AU AU79689/01A patent/AU780534B2/en not_active Expired
- 2001-06-26 RU RU2003100505/04A patent/RU2263110C2/ru active
- 2001-06-26 JP JP2002505373A patent/JP3955814B2/ja not_active Expired - Lifetime
- 2001-06-26 PT PT01957889T patent/PT1294694E/pt unknown
- 2001-06-26 CN CNB018119549A patent/CN1256327C/zh not_active Expired - Lifetime
- 2001-06-26 AT AT01957889T patent/ATE280760T1/de active
- 2001-06-26 UA UA2003010722A patent/UA73587C2/uk unknown
- 2001-06-26 US US10/312,122 patent/US6660865B2/en not_active Expired - Lifetime
-
2002
- 2002-12-12 IL IL153424A patent/IL153424A/en unknown
-
2003
- 2003-01-13 ZA ZA200300328A patent/ZA200300328B/en unknown
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