KR840004411A - 치환된 2-아미노벤즈 이미다졸의 제조방법 - Google Patents
치환된 2-아미노벤즈 이미다졸의 제조방법 Download PDFInfo
- Publication number
- KR840004411A KR840004411A KR1019830001418A KR830001418A KR840004411A KR 840004411 A KR840004411 A KR 840004411A KR 1019830001418 A KR1019830001418 A KR 1019830001418A KR 830001418 A KR830001418 A KR 830001418A KR 840004411 A KR840004411 A KR 840004411A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- phenyl
- cycloalkyl
- alkoxy
- nitro
- Prior art date
Links
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical class C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 title 1
- -1 hydrazinocarbonyl Chemical group 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 239000000376 reactant Substances 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- RIUVKCFFZBZEHS-UHFFFAOYSA-N 1-bromo-3-isothiocyanatopropane Chemical group BrCCCN=C=S RIUVKCFFZBZEHS-UHFFFAOYSA-N 0.000 claims 1
- ZUWFBQUHBOUPFK-UHFFFAOYSA-N 1-chloro-2-isothiocyanatoethane Chemical group ClCCN=C=S ZUWFBQUHBOUPFK-UHFFFAOYSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- DRINJBFRTLBHNF-UHFFFAOYSA-N propane-2-sulfonyl chloride Chemical group CC(C)S(Cl)(=O)=O DRINJBFRTLBHNF-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/28—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (12)
- 다음 일반식(Ⅱ)의 호변이성체 벤즈이미다졸을 약 0℃ 내지 약 75℃의 온도에서 산수용체 염기를 및 수혼화성비하이드록실성 용매 존재하에, 탄소체인 상에서 R5로 임의 치환된 일반식 R2SO2X 또는 X(CH2)nNCS으 제2반응물과 반응시킴을 특징으로 하여, 다음 일반식(Ⅰ)의 2-아미노-1,5(6)-치환된-벤즈이미다졸을 제조하는 방법상기 식에서, R1은 R2SO2- 또는이며: R2는 C1내지 C5알킬 C3내지 C7사이클로알킬, 페닐, 푸릴 또는 티에닐이고: R3는 5- 또는 6-위치에 있으며, 하이드라지노카보닐, 카복시, 카복스아미도, N-(C1내지 C2알킬)-카복스아미도, 하이드록시메틸, 시아노, 니트로, C1내지 C4알킬, C1내지 C4알콕시, C1내지C4-알킬티오, 메틸설포닐, 페닐티오, 페닐설피닐, 펜옥시, 트리플루오로메틸, C1내지 C8-알콕시카보닐, 알릴옥시카보닐, 프로파길옥시카보닐, C3내지 C7-사이클로알킬)옥시카보닐, (C3내지 C7사이클로알킬)메톡시카보닐, 1-(C3내지 C7사이클로알킬)에톡시카보닐, 벤질옥시카보닐, α-메틸벤질옥시카보닐, 펜옥시카보닐, C1내지 C8알콕시카보닐메틸, 1-(C1내지 C8알콕시카보닐)에틸,이고; R4는 수소, C1내지 C7알킬, C3내지 C7사이클로알킬 ,(C3내지 C7사이클로알킬)메틸, 1-(C3내지 C7-사이클로알킬)에틸, 티에닐, 벤질, 페닐 또는 일치환된 페닐(여기에서, 치환체는 C1내지 C4-알킬, C1내지 C4알콕시, 클로로, 브로모, 요오도, 니트로 또는 트리플루오로메틸이다.)이며: R5는 수소, C1내지 C3알킬, 벤질 또는 페닐이고: R6는 수소, C1내지 C7알킬, C3내지 C7사이클로알킬,(C3내지 C7사이클로알킬)메틸, 1-(C3내지 C7-사이클로알킬)에틸, 페닐 또는 일치환된 페닐(여기에서, 페닐 치환체는 C1내지 C4알킬, C1내지 C4알콕시, 츨로로, 브로모, 요오도, 니트로 또는 트리플루오로메틸이다.)이며: R7및 R8은 독립적으로 수소, 할로, 시아노, 하이드록시메틸, 니트로내지 C4-알킬, CH2R9, COR9, 페닐 또는 일치환된 페닐(여기에서, 페닐 치환체는 C1내지 C4-알킬, C1내지 C4-알콕시, 클로로, 브로모, 요오도, 니트로 또는 트리플루오로메틸이다.)이고: R9는 하이드록시, C1내지 C4알콕시, C3내지 C6- 사이클로알킬 - C1내지 C4-알콕시 또는 (O-C1내지 C4알킬)pNR10R11이며: R10및 R11은 독립적으로 수소 또는 C1내지 C4알킬이고: Z는 산소, C1내지 C4알콕시이미노 또는 C1내지 C7알킬리덴이며: Y는 수소이고 w는 하이드록시이거나, 또는 Y와 w가 함께 결합을 형성하며: m은 0,1 또는 2이고 : n은 2 또는 3이며:p는 0 또는 1이고: x는 클로로 또는 브로모이다.
- 제1항에 있어서, 수혼화성 비하이드록실성 용매가 아세톤인 방법
- 제1항에 있어서, 산수용체 염기가 알칼리 금속 수산화물 또는 탄산염인 방법
- 제1항에 또는 제3항에 있어서, 산수용체 염기가 수산화 나트륨인 방법
- 제1항에 있어서, 온도가 약 20℃ 내지 약 30℃인 방법
- 제1항 내지 5항중의 어느 하나에 있어서, 제2반응물이 이소프로필설포닐 클로라이드인 방법
- 제1항 내지 5항중의 어느 하나에 있어서, 제2 반응물이 3-브로모프로필이소티오시아네이트인 방법
- 제1항 내지 5항중의 어느 하나에 있어서, 제2반응물이 2-클로로에틸이소티오시아네이트인 방법
- 제1,6,7 또는 8항에 있어서, R3가[여기에서, R4는 페닐이며 Z는 산소이다.〕인 방법
- 제1,6,7, 또는 8항에 있어서, R3가〔여기에서, R4는 페닐이며, Z는 C1내지 C7알킬리데이다.〕인 방법
- 제10항에 있어서 Z가 에틸리덴인 방법
- 제1,6,7, 또는 8항에 있어서, R3가〔여기에서, R6는 페닐이며, Y 및 W는 함께 결합을 형성한다〕인방법※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US366883 | 1982-04-08 | ||
| US366,883 | 1982-04-08 | ||
| US06/366,883 US4434288A (en) | 1982-04-08 | 1982-04-08 | Preparation of substituted 1-thiazinyl or 1-thiazolyl-2-aminobenzimidazoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840004411A true KR840004411A (ko) | 1984-10-15 |
| KR860001582B1 KR860001582B1 (ko) | 1986-10-10 |
Family
ID=23444984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830001418A KR860001582B1 (ko) | 1982-04-08 | 1983-04-06 | 치환된 2-아미노벤즈이미다졸의 제조방법 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4434288A (ko) |
| EP (1) | EP0091794B1 (ko) |
| JP (1) | JPS58188866A (ko) |
| KR (1) | KR860001582B1 (ko) |
| AT (1) | ATE38986T1 (ko) |
| CA (1) | CA1187874A (ko) |
| CS (2) | CS127784A2 (ko) |
| DD (1) | DD209623A5 (ko) |
| DE (1) | DE3378578D1 (ko) |
| DK (1) | DK152983A (ko) |
| ES (1) | ES8405376A1 (ko) |
| FI (1) | FI831192L (ko) |
| GB (1) | GB2118550B (ko) |
| GR (1) | GR78170B (ko) |
| HU (1) | HU193501B (ko) |
| IE (1) | IE54836B1 (ko) |
| IL (1) | IL68298A (ko) |
| PL (1) | PL241386A1 (ko) |
| PT (1) | PT76500B (ko) |
| RO (1) | RO86853B (ko) |
| SU (1) | SU1189338A3 (ko) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4435418A (en) * | 1982-12-13 | 1984-03-06 | Smithkline Beckman Corporation | 5-Phenylethenylbenzimidazoles |
| JPS62221672A (ja) * | 1986-03-20 | 1987-09-29 | Nippon Tokushu Noyaku Seizo Kk | 新規スルホニルアゾ−ル |
| US5545653A (en) * | 1995-06-07 | 1996-08-13 | Eli Lilly And Company | Anti-viral compounds |
| US5693661A (en) * | 1995-06-07 | 1997-12-02 | Eli Lilly And Company | Anti-viral compounds |
| CN1220601A (zh) * | 1996-06-05 | 1999-06-23 | 伊莱利利公司 | 抗病毒化合物 |
| US5891874A (en) * | 1996-06-05 | 1999-04-06 | Eli Lilly And Company | Anti-viral compound |
| US5821242A (en) * | 1996-06-06 | 1998-10-13 | Eli Lilly And Company | Anti-viral compounds |
| AU741772B2 (en) | 1997-02-25 | 2001-12-06 | Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, The | Substituted benzimidazoles as non-nucleoside inhibitors of reverse transcriptase |
| AU7715198A (en) * | 1997-06-04 | 1998-12-21 | Eli Lilly And Company | Anti-viral compounds |
| US10292390B2 (en) | 2011-11-04 | 2019-05-21 | Wisconsin Alumni Research Foundation | Inhibition and dispersion of bacterial biofilms with 2-aminobenzimidazole derivatives |
| CN108997158B (zh) * | 2018-07-16 | 2020-12-15 | 青岛科技大学 | 一种实现二取代酰胺与二苯基甲酮偶联的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4243813A (en) * | 1974-07-01 | 1981-01-06 | Eli Lilly And Company | Substituted 1-sulfonylbenzimidazoles |
| US4018790A (en) * | 1975-05-08 | 1977-04-19 | Eli Lilly And Company | Substituted 1-sulfonylbenzimidazoles |
| GR61627B (en) * | 1975-08-28 | 1978-12-04 | Lilly Co Eli | Preparation process of carbonyl-substituted 1-sulfonylbenzimidazoles |
| US4174454A (en) * | 1975-08-28 | 1979-11-13 | Eli Lilly And Company | Alkylidenylmethyl-substituted 1-sulfonylbenzimidazoles |
| CA1076582A (en) * | 1975-10-28 | 1980-04-29 | Charles J. Paget | Antiviral thiazolinyl or thiazinyl ketobenzimidazoles |
| US4008243A (en) * | 1975-11-19 | 1977-02-15 | Eli Lilly And Company | Antiviral thiazolinyl or thiazinyl benzimidazole esters |
| US4118573A (en) * | 1975-11-24 | 1978-10-03 | Eli Lilly And Company | Substituted 1-sulfonylbenzimidazoles |
-
1982
- 1982-04-08 US US06/366,883 patent/US4434288A/en not_active Expired - Fee Related
-
1983
- 1983-04-05 IL IL68298A patent/IL68298A/xx unknown
- 1983-04-05 PT PT76500A patent/PT76500B/pt unknown
- 1983-04-06 CA CA000425308A patent/CA1187874A/en not_active Expired
- 1983-04-06 GR GR71007A patent/GR78170B/el unknown
- 1983-04-06 DK DK152983A patent/DK152983A/da not_active IP Right Cessation
- 1983-04-06 KR KR1019830001418A patent/KR860001582B1/ko not_active IP Right Cessation
- 1983-04-06 SU SU833573206A patent/SU1189338A3/ru active
- 1983-04-06 RO RO110575A patent/RO86853B/ro unknown
- 1983-04-07 ES ES521319A patent/ES8405376A1/es not_active Expired
- 1983-04-07 PL PL24138683A patent/PL241386A1/xx unknown
- 1983-04-07 IE IE795/83A patent/IE54836B1/en unknown
- 1983-04-07 AT AT83301975T patent/ATE38986T1/de active
- 1983-04-07 DE DE8383301975T patent/DE3378578D1/de not_active Expired
- 1983-04-07 HU HU831204A patent/HU193501B/hu not_active IP Right Cessation
- 1983-04-07 EP EP83301975A patent/EP0091794B1/en not_active Expired
- 1983-04-07 GB GB08309387A patent/GB2118550B/en not_active Expired
- 1983-04-08 JP JP58062904A patent/JPS58188866A/ja active Pending
- 1983-04-08 DD DD83249692A patent/DD209623A5/de unknown
- 1983-04-08 CS CS841277A patent/CS127784A2/cs unknown
- 1983-04-08 FI FI831192A patent/FI831192L/fi not_active Application Discontinuation
- 1983-04-08 CS CS832539A patent/CS253983A2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD209623A5 (de) | 1984-05-16 |
| PT76500A (en) | 1983-05-01 |
| GR78170B (ko) | 1984-09-26 |
| DK152983A (da) | 1983-10-09 |
| HU193501B (en) | 1987-10-28 |
| ES521319A0 (es) | 1984-06-01 |
| KR860001582B1 (ko) | 1986-10-10 |
| RO86853B (ro) | 1985-05-31 |
| IE830795L (en) | 1983-10-08 |
| PT76500B (en) | 1986-02-06 |
| RO86853A (ro) | 1985-05-20 |
| CA1187874A (en) | 1985-05-28 |
| ATE38986T1 (de) | 1988-12-15 |
| CS127784A2 (cs) | 1984-12-14 |
| GB2118550A (en) | 1983-11-02 |
| US4434288A (en) | 1984-02-28 |
| FI831192A0 (fi) | 1983-04-08 |
| ES8405376A1 (es) | 1984-06-01 |
| IL68298A (en) | 1986-09-30 |
| DE3378578D1 (en) | 1989-01-05 |
| JPS58188866A (ja) | 1983-11-04 |
| GB2118550B (en) | 1985-08-29 |
| EP0091794B1 (en) | 1988-11-30 |
| DK152983D0 (da) | 1983-04-06 |
| FI831192L (fi) | 1983-10-09 |
| EP0091794A1 (en) | 1983-10-19 |
| SU1189338A3 (ru) | 1985-10-30 |
| CS253983A2 (en) | 1984-12-14 |
| IE54836B1 (en) | 1990-02-28 |
| PL241386A1 (en) | 1983-11-21 |
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