KR830005215A - 피라졸로 피리딘온 및 피리딘일 니코틴산염 제조방법 - Google Patents
피라졸로 피리딘온 및 피리딘일 니코틴산염 제조방법 Download PDFInfo
- Publication number
- KR830005215A KR830005215A KR1019810000849A KR810000849A KR830005215A KR 830005215 A KR830005215 A KR 830005215A KR 1019810000849 A KR1019810000849 A KR 1019810000849A KR 810000849 A KR810000849 A KR 810000849A KR 830005215 A KR830005215 A KR 830005215A
- Authority
- KR
- South Korea
- Prior art keywords
- pyridinyl
- group
- lower alkyl
- hydrogen
- acid addition
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 5
- TUPZMLLDXCWVKH-UHFFFAOYSA-N pyrazolo[4,3-b]pyridin-3-one Chemical compound C1=CN=C2C(=O)N=NC2=C1 TUPZMLLDXCWVKH-UHFFFAOYSA-N 0.000 title 1
- POKRAHUBNKIFGZ-UHFFFAOYSA-N pyridin-2-yl pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC1=CC=CC=N1 POKRAHUBNKIFGZ-UHFFFAOYSA-N 0.000 title 1
- -1 2,3-dihydroxypropyl group Chemical group 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 3
- 239000011664 nicotinic acid Substances 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 229960003512 nicotinic acid Drugs 0.000 claims 2
- 235000001968 nicotinic acid Nutrition 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- 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
-
- 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
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- 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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- 저급알킬 2-할로-5-PY-6-Q-니코틴산염과 1-R-히드라진을 반응시키고, 필요에 따라서는 생성된 유리염기를 산첨가염으로 전환시킴을 특징으로하는 구조식 Ⅰ을 가진 피라졸로 피리딘온 및 이것의 산 첨가염 제조방법.단, 위의 식에서 R은 저급알킬기, 저급히드록시알킬기, 2,3-디하이드록시프로필기 또는 저급알콕시알킬기이고, Q는 수소 또는 저급알킬기이며 PY는 4-피리딘일 또는 3-피리딘일, 혹은 한개 또는 두개의 저급알킬 치환요소를 가진 4-피리딘일 또는 3-피리딘일.
- 청구범위 1과 관련하여 R을 메틸기, 에틸기 또는 α-히드록시에틸기로 함을 특징으로 하는 방법.
- 청구범위 1 또는 2와 관련하여 Q를 수소, 메틸기 또는 에틸기로 함을 특징으로 하는 방법.
- 2-할로-6-Q-5-5-PY-니코티노알 할로겐화물과 저급알칸올을 반은시키고, 필요에 따라서는 생성된 유리염기를 산첨가염으로 전환시킴을 특징으로 하는 구조식Ⅱ를 가진 니코틴산 피리딘일 및 이것의 산첨가염 제조방법.단, 위의식에서 Q는 수소 또는 수소 또는 저급알킬기, R'는 저급알킬기, X는 클로로 또는 브로모이고 PY는 4-피리딘일 또는 3-피리딘일, 혹은 한개 또는 두개의 저급알킬치환요소를 가진 4-피리딘일 또는 -피리딘일,
- 청구범위 4와 관련하여 1,2-디히드로-6-Q-2-옥소-5-PY-니코티노이트릴을 가수분해하여 1,2-디히드로-6-Q-2-옥소-5-PY-니코틴산을 만들어 이것을 무기할로겐화제와 반응시키므로 2-할로-6-Q-5-PY-니코티노일 할로겐화물을 제조함을 특징으로 하는 방법.
- 청구범위 4 또는 5와 관련하여 Q을 수소, 메틸기 또는 에틸기로하고 X를 클로로(chloro)로 함을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US130623 | 1980-03-17 | ||
| US06/130,623 US4265895A (en) | 1980-03-17 | 1980-03-17 | 1,2-Dihydro-5-pyridinyl-3H-pyrazolo[3,4-b]pyridin-3-ones and their use as cardiotonics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR830005215A true KR830005215A (ko) | 1983-08-03 |
Family
ID=22445558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810000849A KR830005215A (ko) | 1980-03-17 | 1981-03-16 | 피라졸로 피리딘온 및 피리딘일 니코틴산염 제조방법 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4265895A (ko) |
| JP (1) | JPS56140993A (ko) |
| KR (1) | KR830005215A (ko) |
| BE (1) | BE887953A (ko) |
| ZA (1) | ZA811538B (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4361568A (en) * | 1981-04-28 | 1982-11-30 | Sterling Drug Inc. | 5-(Pyridinyl)-1H-pyrazolo[3,4-b]pyridin-3-amines and their cardiotonic use |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3423414A (en) * | 1966-01-13 | 1969-01-21 | Ciba Geigy Corp | Pyrazolopyridines |
| US4004012A (en) * | 1975-10-14 | 1977-01-18 | Sterling Drug Inc. | 3-Cyano-5-(pyridinyl)-2(1H)-pyridinones |
| US4072746A (en) * | 1975-10-14 | 1978-02-07 | Sterling Drug Inc. | 3-Amino-5-(pyridinyl)-2(1H)-pyridinones |
-
1980
- 1980-03-17 US US06/130,623 patent/US4265895A/en not_active Expired - Lifetime
-
1981
- 1981-03-09 ZA ZA00811538A patent/ZA811538B/xx unknown
- 1981-03-16 KR KR1019810000849A patent/KR830005215A/ko unknown
- 1981-03-16 BE BE1/10175A patent/BE887953A/fr not_active IP Right Cessation
- 1981-03-17 JP JP3860881A patent/JPS56140993A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US4265895A (en) | 1981-05-05 |
| ZA811538B (en) | 1982-03-31 |
| JPS56140993A (en) | 1981-11-04 |
| BE887953A (fr) | 1981-09-16 |
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