KR970702278A - (1H-테트라졸-5-일)테트라졸로[1, 5-a]퀴놀린 및 나프티리딘의 제조방법(Process for preparing (1H-tetrazol-5-yl)tetrazolo[1, 5-a]quinolines and naphthyridines) - Google Patents
(1H-테트라졸-5-일)테트라졸로[1, 5-a]퀴놀린 및 나프티리딘의 제조방법(Process for preparing (1H-tetrazol-5-yl)tetrazolo[1, 5-a]quinolines and naphthyridines) Download PDFInfo
- Publication number
- KR970702278A KR970702278A KR1019960705348A KR19960705348A KR970702278A KR 970702278 A KR970702278 A KR 970702278A KR 1019960705348 A KR1019960705348 A KR 1019960705348A KR 19960705348 A KR19960705348 A KR 19960705348A KR 970702278 A KR970702278 A KR 970702278A
- Authority
- KR
- South Korea
- Prior art keywords
- azide
- tetrazol
- tetrazolo
- compound
- ammonium
- Prior art date
Links
- LIRHINFDFZWXPL-UHFFFAOYSA-N 4-(2h-tetrazol-5-yl)tetrazolo[1,5-a]quinoline Chemical class C=1C=CC=C(N2N=NN=C22)C=1C=C2C=1N=NNN=1 LIRHINFDFZWXPL-UHFFFAOYSA-N 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000005054 naphthyridines Chemical class 0.000 title 1
- -1 methylmercapto Chemical class 0.000 claims abstract 12
- 238000000034 method Methods 0.000 claims abstract 9
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 5
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- 239000000010 aprotic solvent Substances 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims 2
- WWVDTQLJALTWPC-UHFFFAOYSA-N 7,8-dimethyl-4-(2h-tetrazol-5-yl)tetrazolo[1,5-a]quinoline Chemical compound C12=NN=NN2C=2C=C(C)C(C)=CC=2C=C1C1=NN=NN1 WWVDTQLJALTWPC-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 claims 1
- 229910005965 SO 2 Inorganic materials 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- YUQDKWMEURJZAL-UHFFFAOYSA-N diethyl(dimethyl)azanium;azide Chemical compound [N-]=[N+]=[N-].CC[N+](C)(C)CC YUQDKWMEURJZAL-UHFFFAOYSA-N 0.000 claims 1
- KTUFXYYOGZUOFG-UHFFFAOYSA-N ethyl(trimethyl)azanium;azide Chemical compound [N-]=[N+]=[N-].CC[N+](C)(C)C KTUFXYYOGZUOFG-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
- GMRIOAVKKGNMMV-UHFFFAOYSA-N tetrabutylazanium;azide Chemical compound [N-]=[N+]=[N-].CCCC[N+](CCCC)(CCCC)CCCC GMRIOAVKKGNMMV-UHFFFAOYSA-N 0.000 claims 1
- HEYWXOWEALDDOL-UHFFFAOYSA-N tetraethylazanium;azide Chemical compound [N-]=[N+]=[N-].CC[N+](CC)(CC)CC HEYWXOWEALDDOL-UHFFFAOYSA-N 0.000 claims 1
- SUBUUGVBEKEFGW-UHFFFAOYSA-N tetramethylazanium;azide Chemical group [N-]=[N+]=[N-].C[N+](C)(C)C SUBUUGVBEKEFGW-UHFFFAOYSA-N 0.000 claims 1
- VLAZRPPUHJCXHY-UHFFFAOYSA-N triethyl(methyl)azanium;azide Chemical compound [N-]=[N+]=[N-].CC[N+](C)(CC)CC VLAZRPPUHJCXHY-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Paper (AREA)
- Luminescent Compositions (AREA)
Abstract
본 발명은 하기의 반응식 (1)에 따른 방법에 관한 것이다.
상기 반응식에서, n은 0,1 또는 2이고, R은 C1-4알킬, C1-4알콕시, 할로겐, 메틸머캅토 또는 메틸설포닐이거나, 2개의 R이 결합하여 메틸렌디옥시를 형성하고, B는 질소 또는 CH이고, X는 적합한 이탈 그룹이고, M은 저급 알칼리 금속 양이온이고, 단 R이 메틸렌머캅토 또는 메틸렌설포닐인 경우 n은 1이어야만 한다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 3 또는 4 위치에서 니트릴로 치환된 화학식 (2)의 비사이클릭 화합물을 적합한 용매 중에서 적합한 양의 적절한 알칼리 금슥 아지드 또는 테트라알킬 암모늄 아지드와 반응시킴을 포함하는, 화학식 (1)의 화합물의 제조방법.상기 화학식에서, n은 0,1 또는 2이고, R은 C1-4알킬, C1-4알콕시, 저급 할로겐, 메틸머캅토 또는 메틸설포닐이거나, 2개의 R이 결합하여 메틸렌디옥시를 형성하고, B는 질소 또는 CH이고, X는 염소, 불소, 브롬 또는 SO2R1과 같은 적합한 이탈그룹이며, 여기서, R1은직쇄 알킬 또는-CF3이고, X1은 H, -CH3, Br 또는 C1이고, 단 R이 메틸렌머캅토 또는 메틸렌설포닐인 경우 n은 1이어야만 한다.
- 제1항에 있어서, 합성된 화합물이 다음 화학식 (1)인 화합물인 방법.
- 제2항에 있어서, 적합한 용매가 쌍극성 비양성자성 용매인 방법.
- 제3항에 있어서, 쌍극성 비양성자성 용매가 필수적으로 디에틸포름아미드, 디메틸설폭사이드, 디메틸아세트아미드, N-메틸피롤리디논 및 테트라메틸렌 설폰으로 이루어진 그룹 중에서 선택되는 방법.
- 제2항에 있어서, 합성된 화합물이 4-(lH-테트라졸-5-일) 테트라졸로[1,5-a]퀴놀린인 방법.
- 제2항에 있어서, 합성된 화합물이 7,8-디메틸-4-(lH-테트라졸-5-일)테트라졸로[1,5-a]퀴놀린인 방법.
- 제2항에 있어서, 알칼리 금속 아지드가 필수적으로 리튬 아지드, 나트륨 아지드 및 칼륨 아지드로 이루어진 그룹 중에서 선택되는 방법.
- 제7항에 있어서, 알칼리 금속 아지드가 나트륨 아지드인 방법.
- 제2항에 있어서, 테트라알킬 암모늄 아지드가 테트라-메틸 암모늄 아지드, 테트라에틸 암모늄 아지드, 트리-메틸-에틸 암모늄 아지드, 트리-에틸-메틸 암모늄 아지드, 디메틸-디에틸 암모늄 아지드 및 테트라 부틸 암모늄 아지드로 이루어진 그룹 중에서 선택되는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US21828094A | 1994-03-25 | 1994-03-25 | |
US08/218,280 | 1994-03-25 | ||
PCT/US1995/001967 WO1995026348A1 (en) | 1994-03-25 | 1995-02-16 | PROCESS FOR PREPARING (1H-TETRAZOL-5-yl)TETRAZOLO [1,5-a] QUINOLINES AND NAPHTHYRIDINES |
Publications (1)
Publication Number | Publication Date |
---|---|
KR970702278A true KR970702278A (ko) | 1997-05-13 |
Family
ID=22814477
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019960705348A KR970702278A (ko) | 1994-03-25 | 1995-02-16 | (1H-테트라졸-5-일)테트라졸로[1, 5-a]퀴놀린 및 나프티리딘의 제조방법(Process for preparing (1H-tetrazol-5-yl)tetrazolo[1, 5-a]quinolines and naphthyridines) |
Country Status (18)
Country | Link |
---|---|
EP (1) | EP0751945B1 (ko) |
JP (1) | JPH09510968A (ko) |
KR (1) | KR970702278A (ko) |
CN (1) | CN1043644C (ko) |
AT (1) | ATE167863T1 (ko) |
AU (1) | AU686761B2 (ko) |
CA (1) | CA2184694A1 (ko) |
DE (1) | DE69503229T2 (ko) |
DK (1) | DK0751945T3 (ko) |
ES (1) | ES2120185T3 (ko) |
FI (1) | FI963808A (ko) |
GR (1) | GR3027563T3 (ko) |
HU (1) | HUP9774612A2 (ko) |
IL (1) | IL113075A0 (ko) |
NO (1) | NO964009L (ko) |
NZ (1) | NZ281496A (ko) |
WO (1) | WO1995026348A1 (ko) |
ZA (1) | ZA952287B (ko) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08325248A (ja) * | 1995-05-26 | 1996-12-10 | Chugoku Kayaku Kk | テトラゾール類の新規な合成試薬及びそれを用いたテトラゾール類の製造方法 |
GB0316546D0 (en) | 2003-07-15 | 2003-08-20 | Novartis Ag | Process for the manufacture of organic compounds |
US7358259B2 (en) | 2003-09-26 | 2008-04-15 | Rigel Pharmaceuticals, Inc. | HCV inhibitors and methods of using them |
WO2005121138A2 (en) * | 2004-06-03 | 2005-12-22 | Rigel Pharmaceuticals, Inc. | Heterotricyclic compounds for use as hcv inhibitors |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3764681A (en) * | 1970-07-08 | 1973-10-09 | Lilly Co Eli | Certain tetrazolo-(1,5-a) quinoline compounds as fungus control agents |
US4496569A (en) * | 1983-03-25 | 1985-01-29 | The Dow Chemical Company | Antiallergic (1H-tetrazol-5-yl)tetrazolo[1,5-a]quinolines and derivatives thereof |
US4581455A (en) * | 1984-10-10 | 1986-04-08 | Merrell Dow Pharmaceuticals Inc. | Tetrazolothienopyridines |
-
1995
- 1995-02-16 CA CA002184694A patent/CA2184694A1/en not_active Abandoned
- 1995-02-16 ES ES95910282T patent/ES2120185T3/es not_active Expired - Lifetime
- 1995-02-16 KR KR1019960705348A patent/KR970702278A/ko not_active Application Discontinuation
- 1995-02-16 JP JP7525156A patent/JPH09510968A/ja active Pending
- 1995-02-16 AT AT95910282T patent/ATE167863T1/de not_active IP Right Cessation
- 1995-02-16 NZ NZ281496A patent/NZ281496A/en unknown
- 1995-02-16 HU HU9602614A patent/HUP9774612A2/hu unknown
- 1995-02-16 AU AU18454/95A patent/AU686761B2/en not_active Ceased
- 1995-02-16 DE DE69503229T patent/DE69503229T2/de not_active Expired - Fee Related
- 1995-02-16 WO PCT/US1995/001967 patent/WO1995026348A1/en active IP Right Grant
- 1995-02-16 EP EP95910282A patent/EP0751945B1/en not_active Expired - Lifetime
- 1995-02-16 CN CN95192231A patent/CN1043644C/zh not_active Expired - Fee Related
- 1995-02-16 DK DK95910282T patent/DK0751945T3/da active
- 1995-03-20 ZA ZA952287A patent/ZA952287B/xx unknown
- 1995-03-22 IL IL11307595A patent/IL113075A0/xx unknown
-
1996
- 1996-09-24 NO NO964009A patent/NO964009L/no unknown
- 1996-09-24 FI FI963808A patent/FI963808A/fi unknown
-
1998
- 1998-08-04 GR GR980401747T patent/GR3027563T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
IL113075A0 (en) | 1995-06-29 |
ATE167863T1 (de) | 1998-07-15 |
EP0751945A1 (en) | 1997-01-08 |
FI963808A0 (fi) | 1996-09-24 |
FI963808A (fi) | 1996-09-24 |
WO1995026348A1 (en) | 1995-10-05 |
CN1043644C (zh) | 1999-06-16 |
AU1845495A (en) | 1995-10-17 |
NO964009L (no) | 1996-11-22 |
NO964009D0 (no) | 1996-09-24 |
CN1144527A (zh) | 1997-03-05 |
DE69503229T2 (de) | 1998-12-24 |
AU686761B2 (en) | 1998-02-12 |
HUP9774612A2 (en) | 1997-01-28 |
DE69503229D1 (de) | 1998-08-06 |
HU9602614D0 (en) | 1996-11-28 |
JPH09510968A (ja) | 1997-11-04 |
CA2184694A1 (en) | 1995-10-05 |
GR3027563T3 (en) | 1998-11-30 |
ES2120185T3 (es) | 1998-10-16 |
ZA952287B (en) | 1996-01-09 |
EP0751945B1 (en) | 1998-07-01 |
NZ281496A (en) | 1998-02-26 |
DK0751945T3 (da) | 1999-04-12 |
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