KR830005203A - 6-(피리디닐)-4-치환-3(2h)-피리다지논의 제조방법 - Google Patents
6-(피리디닐)-4-치환-3(2h)-피리다지논의 제조방법 Download PDFInfo
- Publication number
- KR830005203A KR830005203A KR1019810001437A KR810001437A KR830005203A KR 830005203 A KR830005203 A KR 830005203A KR 1019810001437 A KR1019810001437 A KR 1019810001437A KR 810001437 A KR810001437 A KR 810001437A KR 830005203 A KR830005203 A KR 830005203A
- Authority
- KR
- South Korea
- Prior art keywords
- pyridinyl
- compound
- lower alkyl
- necessary
- carbamyl
- Prior art date
Links
- -1 6- (pyridinyl) -4-substituted-3 (2H) -pyridazinone Chemical class 0.000 title claims 9
- 238000000034 method Methods 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims 10
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 239000012458 free base Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 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
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims 1
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000012320 chlorinating reagent Substances 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
- XEEVLJKYYUVTRC-UHFFFAOYSA-L oxomalonate(2-) Chemical compound [O-]C(=O)C(=O)C([O-])=O XEEVLJKYYUVTRC-UHFFFAOYSA-L 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229910052724 xenon Inorganic materials 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
- C07D401/02—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 containing two hetero rings
- C07D401/04—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 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- a. 2-R-6-PY-3(2H)-피리다지논을 히드라진과 반응시키고,b. 2,3-디하이드로-2-R-3-옥소-6-PY-4-피리다진 카르복사미드를 카르바밀을 아미노로 전환시킬 수 있는 시약과 반응시키거나 또는,c. 2,3-디하이드로-2-R-3-옥소-6-PY-4-피리다진 카르복실 산 히드라지드를 카르복실산 히드라지드를 아미노로 전환시킬 수 있는 시약과 반응시키고, 필요하다면, 얻어진 유리염기를 그의 산부가염으로 전환시키는 것을 특징으로 하여 하기 구조식Ⅰ을 갖는 3(2H)-피리다지논을 제조하는 방법.상기식에서, PY는 한두개의 저급알킬치환체를 갖는 4-혹은 3-피리디닐, 또는 4-혹은 3-피리디닐이고, R은 수소, 저급알킬 또는 저급 히드록시알킬이며, R'는 아미노이다.
- R이 수소, 메틸, 에틸 또는 2-히드록시에틸이고, PY가 4-피리디닐 또는 3-피리디닐인 것을 특징으로 하는 청구범위 1에 따른 방법.
- R'가 저급카르발콕시인 화합물을 생성하기 위해서 구조식 R-NHNH2. nHxAn (n은 1 또는 2이고 X는 1,2 또는 3이고, An은 무기강산 또는 유기 술폰산의 음이온임)의 히드라진 염과 디-(저급알킬)히드록시 [2-옥소-2-PY-에틸] 프로판디오에이트를 반응시키고, 필요하다면, R'가 저급카르발콕시인 상기 얻어진 화합물을 히드라진 수화물 또는 무수히드라진과 반응시켜 R'가 아미노카르 바밀인 화합물을 생성시키고, 필요하다면, R'가 카르바밀인 화합물을 화합물을 생성시키고, 필요하다면 R'가 카르바밀인 화합물은 얻기 위해서 R'가 저급 카르발콕시인 얻어진 화합물을 암모니아와 반응시키거나 R'가 카르복시인 화합물을 얻기 위해서 R'가 저급 카르발콕시인 얻어진 화합물을 가수분해하고, 필요하다면 산염화물을 생성시키기 위해서 R'가 카르복시인 얻어진 화합물을 염소화제와 반응시키고, 그리고 R'가 카르바밀인 화합물을 생성시키기 위해서 상기 산 염화물을 암모니아와 반응시키고, 필요하다면 얻어진 유리염기를 그의 산부가 염으로 전환시키는 것을 특징으로 하여 하기 구조식 I를 갖는 3(2H)-피리다지논을 제조하는 방법.상기식에서, PY는 한두개의 저급알킬 치환체를 갖는 4-혹은 3-피리디닐, 또는 4-혹은 -3피리디닐이고, R은 수소, 저급알킬 또는 저급 히드록시알킬이고, R'는 카르바밀, 카르복시, 아미노카르바밀 또는 저급카르발콕시이다.
- R이 수소, 메틸 또는 에틸이고, PY는 4-피리디닐 또는 3-피리디닐인 것을 특징으로 하는 청구범위 3에 따른 방법.
- 구조식 PY-COCH3의 아세틸피리딘을 디-(저급알킬) 옥소말로네이트와 반응시키고, 필요하다면 얻어진 유리염기를 그의 산부가염으로 전환시킴을 특징으로 하는 하기구조식 Ⅱ의 디-(저급알킬) 히드록시[2-옥소-2-PY-에틸] 프로판디오에이트 또는 그의 산부가염을 제조하는 방법.상기식에서, PY는 한두개의 저급 알킬 치환체를 갖는 4-혹은 3-피리디닐 또는 4-혹은 3-피리디닐이며, R1은 저급알킬이다.
- PY가 4-피리디닐 또는 3-피리디닐이고, R1이 메틸 또는 에틸인 것을 특징으로 하는 청구범위 5에 따른 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US144563 | 1980-04-28 | ||
| US06/144,563 US4305943A (en) | 1980-04-28 | 1980-04-28 | 4-Amino-6-(pyridinyl)-3(2H)-pyridazinones and their use as cardiotonics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR830005203A true KR830005203A (ko) | 1983-08-03 |
Family
ID=22509142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810001437A KR830005203A (ko) | 1980-04-28 | 1981-04-27 | 6-(피리디닐)-4-치환-3(2h)-피리다지논의 제조방법 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4305943A (ko) |
| JP (1) | JPS56167684A (ko) |
| KR (1) | KR830005203A (ko) |
| BE (1) | BE888566A (ko) |
| CA (1) | CA1166253A (ko) |
| PH (1) | PH16014A (ko) |
| ZA (1) | ZA812652B (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013097052A1 (en) | 2011-12-30 | 2013-07-04 | Abbott Laboratories | Bromodomain inhibitors |
| US10208024B2 (en) | 2015-10-23 | 2019-02-19 | Array Biopharma Inc. | 2-aryl- and 2-heteroaryl-substituted 2-pyridazin-3(2H)-one compounds as inhibitors of FGFR tyrosine kinases |
| MA44674B1 (fr) | 2016-04-15 | 2020-06-30 | Abbvie Inc | Inhibiteurs de bromodomaine |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4072746A (en) * | 1975-10-14 | 1978-02-07 | Sterling Drug Inc. | 3-Amino-5-(pyridinyl)-2(1H)-pyridinones |
| US4004012A (en) * | 1975-10-14 | 1977-01-18 | Sterling Drug Inc. | 3-Cyano-5-(pyridinyl)-2(1H)-pyridinones |
-
1980
- 1980-04-28 US US06/144,563 patent/US4305943A/en not_active Expired - Lifetime
-
1981
- 1981-04-22 PH PH25529A patent/PH16014A/en unknown
- 1981-04-23 ZA ZA00812652A patent/ZA812652B/xx unknown
- 1981-04-27 KR KR1019810001437A patent/KR830005203A/ko unknown
- 1981-04-27 CA CA000376309A patent/CA1166253A/en not_active Expired
- 1981-04-27 BE BE1/10209A patent/BE888566A/fr not_active IP Right Cessation
- 1981-04-28 JP JP6510381A patent/JPS56167684A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56167684A (en) | 1981-12-23 |
| ZA812652B (en) | 1982-05-26 |
| PH16014A (en) | 1983-05-20 |
| BE888566A (fr) | 1981-10-27 |
| US4305943A (en) | 1981-12-15 |
| CA1166253A (en) | 1984-04-24 |
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