KR840000541A - N-디히드로티아졸릴-3-퀴놀린 카복사미드 유도체의 제조방법 - Google Patents
N-디히드로티아졸릴-3-퀴놀린 카복사미드 유도체의 제조방법 Download PDFInfo
- Publication number
- KR840000541A KR840000541A KR1019820002613A KR820002613A KR840000541A KR 840000541 A KR840000541 A KR 840000541A KR 1019820002613 A KR1019820002613 A KR 1019820002613A KR 820002613 A KR820002613 A KR 820002613A KR 840000541 A KR840000541 A KR 840000541A
- Authority
- KR
- South Korea
- Prior art keywords
- product
- formula
- starting material
- hydrogen
- atom
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 8
- MDAGYRZLIQAJPW-UHFFFAOYSA-N n-(2,3-dihydro-1,3-thiazol-2-yl)quinoline-3-carboxamide Chemical class C=1N=C2C=CC=CC2=CC=1C(=O)NC1NC=CS1 MDAGYRZLIQAJPW-UHFFFAOYSA-N 0.000 title 1
- -1 alkyl radical Chemical class 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 239000007858 starting material Substances 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 2
- REGFWZVTTFGQOJ-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-amine Chemical compound NC1=NCCS1 REGFWZVTTFGQOJ-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (12)
- 다음 구조식(Ⅱ)의 생성물을 2-아미노티아졸린과 반응시키고 필요하다면 분리하고 염화함을 특징으로 하여 다음 구조식(Ⅰ)의-디히드로티아졸릴-3-퀴놀린 카볼사미드의 신규 유도체 뿐만 아니라 무기 또는 유기산으로 된 그들의 부가염을 제조하는 방법.
-
- 상기 구조식에서 R은 수소원자 또는 1내지 4 탄소원자의 알킬 래디칼을 나타내고, R1은 6 또는 7 위치에 수소 또는 할로겐 원자, 1 내지 4 탄소원자의 즉쇄 알킬 래디칼, 1내지 4 탄소원자의 알콕시 래디칼, 또는 트리플루오로메틸티오메틸티오, 트리플루오로메톡시 또는 트리플루오로메틸 래디칼을 나타내고 X는 염소 또는 브롬원자 또는 1내지 5 탄소원자의 히드록시 또는 알콕시래디칼을 나타낸다.
- 1항에 있어 X는 염소 또는 브롬원자인 구조식(Ⅱ)의 생성물을 출발물질로 하고 히드라시드-고정약제의 존재하에 반응이 수행됨을 특징으로 하는 상기 1항의 제조방법
- 1항에 있어 X는 1내지 5 탄소원자의 알콕시래디칼을 나타내는 구조식(Ⅱ)의 생성물을 출발 물질로 하고 알루미늄의 알킬화 유도체의 존재하에 반응이 수행됨을 특징으로 하는 상기 1항의 제조방법.
- 1항에 있어 R은 수소원자 또는 메틸 래디칼을 나타내고 R은 수소 또는 염소원자 또는 메톡시 래디칼을 나타내거나 6은 위치에 불소원자, 또는 메틸, 에틸, 이소프로필, 메틸티오 또는 트리플루오로 메틸 래디칼을 나타내는 구조식(Ⅱ)의 생성물을 출발물질로 함을 특징으로 상기 1내지 3항의 하나의 제조방법.
- 4항에 있어 R이 수소원자인 구조식(Ⅱ)의 생성물을 출발물질로 사용함을 특징으로 하는 4항의 제조방법.
- R 및 R1이 수소원자인 구조식(Ⅱ)의 생성물을 출발물질로 사용함을 특징으로 하는 1내지 5항의 하나의 제조방법.
- R은 수소원자이고 R1은 6 위치에 에틸 래디칼을 나타내는 구조식(Ⅱ)의 생성물을 출발물질로 사용함을 특징으로 하는 1내지 5항의 하나의 제조방법.
- R은 수소원자이고 R1은 6 위치에 염소원자를 나타내는 구조식(Ⅱ)의 생성물을 출발물질로 사용함을 특징으로 하는 1내지 5항의 하나의 제조방법.
- R은 메틸 래디칼을 나타내고 R1은 수소원자를 나타내는 구조식(Ⅱ)의 생성물을 출발물질로 사용함을 특징으로 하는 1내지 5항의 하나의 제조방법.
- ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR81-11607 | 1981-06-12 | ||
FR8111607A FR2507602A1 (fr) | 1981-06-12 | 1981-06-12 | Nouveau derive dihydrothiazole de la quinoleine, ses sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
FR82-04331 | 1982-03-15 | ||
FR8204331A FR2523130A1 (fr) | 1982-03-15 | 1982-03-15 | Nouveaux derives de la n-dihydrothiazolyl-3-quinoleine carboxamide, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
Publications (2)
Publication Number | Publication Date |
---|---|
KR840000541A true KR840000541A (ko) | 1984-02-25 |
KR880000808B1 KR880000808B1 (ko) | 1988-05-11 |
Family
ID=26222434
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR8202613A KR880000808B1 (ko) | 1981-06-12 | 1982-06-11 | N-디히드로티아졸릴-3-퀴놀린카복사미드 유도체의 제조방법 |
Country Status (16)
Country | Link |
---|---|
US (1) | US4450166A (ko) |
EP (1) | EP0067772B1 (ko) |
KR (1) | KR880000808B1 (ko) |
AU (1) | AU552029B2 (ko) |
CA (1) | CA1216795A (ko) |
DE (1) | DE3262536D1 (ko) |
DK (1) | DK150070C (ko) |
ES (1) | ES512852A0 (ko) |
FI (1) | FI78087C (ko) |
GR (1) | GR77201B (ko) |
HU (1) | HU190796B (ko) |
IE (1) | IE53520B1 (ko) |
IL (1) | IL65943A (ko) |
MA (1) | MA19488A1 (ko) |
NZ (1) | NZ200931A (ko) |
PT (1) | PT75023B (ko) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2557570B1 (fr) * | 1984-01-04 | 1986-04-18 | Adir | Nouveaux derives de la quinoleine, leur procede de preparation et les compositions pharmaceutiques les renfermant |
FR2566405B1 (fr) * | 1984-06-25 | 1986-09-26 | Roussel Uclaf | Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2 par une fonction aminee, leur preparation, leur application comme medicaments, les compositions les renfermant et les intermediaires nouveaux obtenus |
US4602014A (en) * | 1984-07-09 | 1986-07-22 | Ciba-Geigy Corporation | Ring-fused pyrazolo[3,4-d]-pyridin-3-one derivatives as benzodiazepine receptor modulators |
US4560692A (en) * | 1984-07-18 | 1985-12-24 | Hoffmann-La Roche Inc. | 4-Piperidino-2-phenylquinolines |
US4786644A (en) * | 1987-11-27 | 1988-11-22 | Hoechst-Roussel Pharmaceuticals Inc. | 1-aryl-3-quinolinecarboxamide |
BR9908321A (pt) | 1998-02-26 | 2001-12-18 | Neurogen Corp | Composto |
ES2235883T3 (es) * | 1999-05-06 | 2005-07-16 | Neurogen Corporation | 4-oxo-quinolino-3-carboxamidas sustituidas: ligandos de receptores cerebrales gaba. |
US20100074949A1 (en) | 2008-08-13 | 2010-03-25 | William Rowe | Pharmaceutical composition and administration thereof |
MX2007000095A (es) | 2004-06-24 | 2007-03-21 | Vertex Pharma | Moduladores de transportadores con casete de union con atp. |
US8354427B2 (en) | 2004-06-24 | 2013-01-15 | Vertex Pharmaceutical Incorporated | Modulators of ATP-binding cassette transporters |
CA2634113A1 (en) * | 2005-12-24 | 2007-07-05 | Vertex Pharmaceuticals Incorporated | Quinolin- 4 - one derivatives as modulators of abc transporters |
SI3219705T1 (sl) | 2005-12-28 | 2020-08-31 | Vertex Pharmaceuticals Incorporated | Farmacevtski sestavki amorfne oblike N-(2,4-bis(1,1-dimetiletil)-5- hidroksifenil)-1,4-dihidro-4-oksokinolin-3-karboksamid |
LT2821400T (lt) | 2009-03-20 | 2018-02-12 | Vertex Pharmaceuticals Incorporated | Cistinės fibrozės transmembraninio laidumo reguliatoriaus moduliatorių gamybos būdas |
US8802700B2 (en) | 2010-12-10 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
RU2692779C2 (ru) | 2012-02-27 | 2019-06-27 | Вертекс Фармасьютикалз Инкорпорейтед | Фармацевтическая композиция и ее введения |
EP3204358B1 (en) | 2014-10-07 | 2018-09-19 | Vertex Pharmaceuticals Incorporated | Co-crystals of modulators of cystic fibrosis transmembrane conductance regulator |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1364605A (fr) * | 1962-03-01 | 1964-06-26 | Procédé de préparation d'amides des acides carboxyliques | |
FR2281761A1 (fr) * | 1974-08-13 | 1976-03-12 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
FR2324304A2 (fr) * | 1975-09-22 | 1977-04-15 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
FR2340735A1 (fr) * | 1976-02-11 | 1977-09-09 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
FR2377400A2 (fr) * | 1977-01-18 | 1978-08-11 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
FR2443467A1 (fr) * | 1978-12-08 | 1980-07-04 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
FR2482596A1 (fr) * | 1980-05-19 | 1981-11-20 | Roussel Uclaf | Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2, leur procede de preparation et leur application comme medicament |
-
1982
- 1982-05-24 HU HU821657A patent/HU190796B/hu not_active IP Right Cessation
- 1982-05-26 MA MA19695A patent/MA19488A1/fr unknown
- 1982-06-01 IL IL65943A patent/IL65943A/xx unknown
- 1982-06-04 ES ES512852A patent/ES512852A0/es active Granted
- 1982-06-08 PT PT75023A patent/PT75023B/pt not_active IP Right Cessation
- 1982-06-09 US US06/386,597 patent/US4450166A/en not_active Expired - Fee Related
- 1982-06-10 GR GR68384A patent/GR77201B/el unknown
- 1982-06-10 FI FI822067A patent/FI78087C/fi not_active IP Right Cessation
- 1982-06-11 AU AU84827/82A patent/AU552029B2/en not_active Ceased
- 1982-06-11 IE IE1394/82A patent/IE53520B1/en unknown
- 1982-06-11 DE DE8282401062T patent/DE3262536D1/de not_active Expired
- 1982-06-11 CA CA000405006A patent/CA1216795A/fr not_active Expired
- 1982-06-11 KR KR8202613A patent/KR880000808B1/ko active
- 1982-06-11 EP EP82401062A patent/EP0067772B1/fr not_active Expired
- 1982-06-11 DK DK262782A patent/DK150070C/da not_active IP Right Cessation
- 1982-06-11 NZ NZ200931A patent/NZ200931A/en unknown
Also Published As
Publication number | Publication date |
---|---|
ES8304567A1 (es) | 1983-03-01 |
GR77201B (ko) | 1984-09-11 |
DK150070B (da) | 1986-12-01 |
IL65943A0 (en) | 1982-09-30 |
DK262782A (da) | 1982-12-13 |
FI78087B (fi) | 1989-02-28 |
PT75023A (fr) | 1982-07-01 |
KR880000808B1 (ko) | 1988-05-11 |
CA1216795A (fr) | 1987-01-20 |
EP0067772B1 (fr) | 1985-03-13 |
ES512852A0 (es) | 1983-03-01 |
MA19488A1 (fr) | 1982-12-31 |
DE3262536D1 (en) | 1985-04-18 |
IE53520B1 (en) | 1988-12-07 |
NZ200931A (en) | 1984-12-14 |
FI822067A0 (fi) | 1982-06-10 |
AU552029B2 (en) | 1986-05-22 |
HU190796B (en) | 1986-11-28 |
IE821394L (en) | 1982-12-12 |
FI78087C (fi) | 1989-06-12 |
US4450166A (en) | 1984-05-22 |
IL65943A (en) | 1985-12-31 |
PT75023B (fr) | 1985-05-17 |
AU8482782A (en) | 1982-12-16 |
EP0067772A1 (fr) | 1982-12-22 |
DK150070C (da) | 1987-11-09 |
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