KR830007634A - N-피롤릴 피리다진아민의 제조법 - Google Patents
N-피롤릴 피리다진아민의 제조법 Download PDFInfo
- Publication number
- KR830007634A KR830007634A KR1019810005072A KR810005072A KR830007634A KR 830007634 A KR830007634 A KR 830007634A KR 1019810005072 A KR1019810005072 A KR 1019810005072A KR 810005072 A KR810005072 A KR 810005072A KR 830007634 A KR830007634 A KR 830007634A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- hydroxy
- formula
- acid
- hydrogen
- Prior art date
Links
- PXYUEEJAXOCGBZ-UHFFFAOYSA-N n-(1h-pyrrol-2-yl)pyridazin-3-amine Chemical compound C=1C=CN=NC=1NC1=CC=CN1 PXYUEEJAXOCGBZ-UHFFFAOYSA-N 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
- -1 dicarbonyl compound Chemical class 0.000 claims 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 239000003054 catalyst Substances 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000005605 benzo 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
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims 1
- 150000002429 hydrazines Chemical class 0.000 claims 1
- 150000007857 hydrazones Chemical class 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- JBVCSNJKVNKDHK-UHFFFAOYSA-N n-(2,5-dimethylpyrrol-1-yl)-6-morpholin-4-ylpyridazin-3-amine Chemical compound CC1=CC=C(C)N1NC1=CC=C(N2CCOCC2)N=N1 JBVCSNJKVNKDHK-UHFFFAOYSA-N 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
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 150000004892 pyridazines Chemical class 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D237/20—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (8)
- 구조식(Ⅱ)의 화합물과 히드라진 하이드레이트 혹은 구조식 NH2NHR4의 히드라진 유도체를 수소 헬라이트 수용체에서 바응시켜서 구조식(Ⅲ)의 6-할로겐-3-히드라지노 피리다진 유도체를 제조하고, 이것을 구조식(Ⅳ)의 디카르보닐 화합물 반몰랄양과 반응시켜서 알칸디온-비스-[6-할로-3-피리다지닐] 히드라존(구조식 Ⅴ)을 제조하고, 이것을 동몰랄양의 디카르보닐 화합물(Ⅳ)과 산성 촉매와 용매에서 반응시키고, 이후 구조식(Ⅵ)의 6-할로-3-피롤릴피리다진 아민유도체를 과량의 R5R6NH와 알맞는 산성 촉매에서 반응시키는 것을 특징으로 하는 하기 구조식(I)의 화합물 및 이것의 산부가염의 제조방법.윗식에서 R,R1,R2및 R3는 동일하거나 서로 다른 것으로서 각각 수소와(C1-C4)알킬에서 선택하고, R4는 수소, (C1-C4)알킬, 모노-혹은 디-(C1-C4)알킬아미노 (C1-C4)알킬, 할로(C1-C4)알카노일, 카르보(C1-C4)알콕시, 카르보벤질옥시이고, R5와 R6는 각각 수소 (C1-C6)알킬, (C3-C6)알케닐(C3-C6)알키닐, 히드록시(C1-C6)알킬, (C1-C4)알콕시 (C1-C6)알킬, (C2-C6)알카노일옥시 (C1-C6)알킬, 페닐 혹은 페닐(C1-C4)알킬, 단 페닐은 클로로-브로모, 플루오로, (C1-C4)알킬, (C1-C4)알콕시, 히드록시 및 하이드록시(C1-C4)알킬, 혹은 메틸렌디옥시기로 1-3치환물로 치환된 것임, R5와 R6는 질소원자에 근접한 것으로서 전체 혹은 부분적으로 수소화된 5-7원소의 헤토로시클릭환으로서, O,N 및 S에서 선택된 이원자이며 (C1-C4)알킬, 히드록시, 히드록시(C1-C4)알킬, (C1-C4)알콕시 페닐에서 선택된 1-2치환물을 지닐 수 있는 것임. R7과 R8은 수소원자 혹은 피리다진 혹은 피리다진 환으로 용융된 벤조계를 형성하는 1,3-부타디에닐렌기를 뜻함.
- 청구범위 1에 있어서 R과 R1은 수소이고, R과 R3는 동일하거나 서로 다른 것으로서(C1-C4)알킬이고 R5와 R6는 각기 (C1-C6)알킬,히드록시(C1-C6)알킬 혹은 (C1-C4)알콕시 (C1-C6)알킬이고 혹은 R5와 R6는 질소원자에 근접한 것으로서 O,N 및 S에서 선택된 이원자를 지니고 (C1-C4)알킬, 히드록시, 히드록시(C1-C4)알킬 및 클로로, 브로모, 플루오로, 히드록시(C1-C4) 알킬 및 (C1-C4)알콕시에서 선택된 1-3치환물로 치환된 페닐에서 선택된 5-7원자이고리환을 나타내느 구조식(I)의 화합물 제조방법.
- 청구범위 1 혹은 2에 있어서 3,6-디할로겐 피리다진 및 히드라진 하이드래이트 유도체 사이의 반응이 고압솥 혹은 파르용기에서 100°-190℃로 가열하여 행하는 방법.
- 청구범위 1-3에 있어서 구조식(Ⅳ)의 디카르보닐 화합물이 구조식(Ⅵ)의 유도체가 직접 산출되도록 3,6-디할로겐 피리다진 유도체에 가하는 방법.
- 청구범위 1-4에 있어서 알칸디온-비스-6-할로겐-3-피리다지닐히드라존과 디카르보닐 화합물(Ⅳ)의 반응용 용매가 물, (C1-C4)알카놀, 아세틱 혹은 프로피온산, 벤젠, 톨로엔, 테트라히드로푸란, 디옥산 및 그 혼합물에서 선택하고, 산촉매는 할로겐화수소산, 설푸릭산, p-톨루엔설폰산 및 루이스산인 방법.
- 청구버위 1-5중 하나에서 아세틱산이 용매와 촉매로 활용되는 방법.
- 청구범위 1-6에 있어서 R5R6NH의 아민 첨가가 산성촉매로 활동하는 아민의 산부가염의 존재하에 행하는 방법.
- 청구범위 1-7중 어느 하나에 있어서 N-(2,5-디메틸-1H-피롤-1-일)-6-(4-모포리닐)-3-피리다진아민의 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT26846/80A IT1150070B (it) | 1980-12-22 | 1980-12-22 | Procedimento per preparare derivati n-pirrolipiridazinamminici |
| IT26846A/80 | 1980-12-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830007634A true KR830007634A (ko) | 1983-11-04 |
| KR870001625B1 KR870001625B1 (ko) | 1987-09-17 |
Family
ID=11220359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810005072A KR870001625B1 (ko) | 1980-12-22 | 1981-12-22 | N-피롤릴 피리다진아민 유도체의 제조방법 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4385179A (ko) |
| EP (1) | EP0054816B1 (ko) |
| JP (1) | JPS57128686A (ko) |
| KR (1) | KR870001625B1 (ko) |
| AT (1) | ATE14729T1 (ko) |
| CA (1) | CA1173442A (ko) |
| DE (1) | DE3171737D1 (ko) |
| DK (1) | DK566181A (ko) |
| ES (1) | ES8300751A1 (ko) |
| GR (1) | GR74708B (ko) |
| IE (1) | IE52085B1 (ko) |
| IT (1) | IT1150070B (ko) |
| PT (1) | PT74178B (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1252788A (en) * | 1985-03-12 | 1989-04-18 | William J. Coates | Pyridazinone derivatives |
| US5622948A (en) * | 1994-12-01 | 1997-04-22 | Syntex (U.S.A.) Inc. | Pyrrole pyridazine and pyridazinone anti-inflammatory agents |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE3294T1 (de) * | 1978-10-02 | 1983-05-15 | Gruppo Lepetit S.P.A. | 6-aminosubstituierte n-pyrrolyl-3-pyridazinamine, deren herstellung und sie enthaltende pharmazeutische antihypertensive zusammensetzungen. |
| HU179191B (en) * | 1979-05-07 | 1982-09-28 | Gyogyszerkutato Intezet | New process for preparing 6-/substituted amino/-3-pyridazinyl-hydrazines and salts thereof |
-
1980
- 1980-12-22 IT IT26846/80A patent/IT1150070B/it active
-
1981
- 1981-12-06 AT AT81110203T patent/ATE14729T1/de not_active IP Right Cessation
- 1981-12-06 DE DE8181110203T patent/DE3171737D1/de not_active Expired
- 1981-12-06 EP EP81110203A patent/EP0054816B1/en not_active Expired
- 1981-12-08 GR GR66737A patent/GR74708B/el unknown
- 1981-12-18 US US06/332,272 patent/US4385179A/en not_active Expired - Fee Related
- 1981-12-21 DK DK566181A patent/DK566181A/da not_active Application Discontinuation
- 1981-12-21 ES ES508175A patent/ES8300751A1/es not_active Expired
- 1981-12-21 IE IE3005/81A patent/IE52085B1/en unknown
- 1981-12-21 PT PT74178A patent/PT74178B/pt unknown
- 1981-12-21 CA CA000392819A patent/CA1173442A/en not_active Expired
- 1981-12-22 JP JP56206272A patent/JPS57128686A/ja active Granted
- 1981-12-22 KR KR1019810005072A patent/KR870001625B1/ko active
Also Published As
| Publication number | Publication date |
|---|---|
| KR870001625B1 (ko) | 1987-09-17 |
| ES508175A0 (es) | 1982-11-01 |
| IT8026846A0 (it) | 1980-12-22 |
| GR74708B (ko) | 1984-07-06 |
| PT74178B (en) | 1983-05-18 |
| JPS57128686A (en) | 1982-08-10 |
| DE3171737D1 (en) | 1985-09-12 |
| CA1173442A (en) | 1984-08-28 |
| JPH0328432B2 (ko) | 1991-04-19 |
| US4385179A (en) | 1983-05-24 |
| DK566181A (da) | 1982-06-23 |
| IE52085B1 (en) | 1987-06-10 |
| IE813005L (en) | 1982-06-22 |
| ATE14729T1 (de) | 1985-08-15 |
| ES8300751A1 (es) | 1982-11-01 |
| EP0054816A1 (en) | 1982-06-30 |
| EP0054816B1 (en) | 1985-08-07 |
| IT1150070B (it) | 1986-12-10 |
| PT74178A (en) | 1982-01-01 |
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