KR850004479A - 이미다조〔4,5-c〕피리딘-온의 제조방법 - Google Patents
이미다조〔4,5-c〕피리딘-온의 제조방법 Download PDFInfo
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- KR850004479A KR850004479A KR1019840008221A KR840008221A KR850004479A KR 850004479 A KR850004479 A KR 850004479A KR 1019840008221 A KR1019840008221 A KR 1019840008221A KR 840008221 A KR840008221 A KR 840008221A KR 850004479 A KR850004479 A KR 850004479A
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- South Korea
- Prior art keywords
- group
- compound
- acid addition
- general formula
- reaction
- Prior art date
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- 238000000034 method Methods 0.000 title claims 8
- CTIRNXGIOKPVOM-UHFFFAOYSA-N imidazo[4,5-c]pyridin-2-one Chemical compound C1=CN=CC2=NC(=O)N=C21 CTIRNXGIOKPVOM-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- -1 2-methoxy-4-methyl-mercaptophenyl Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
-
- 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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
-
- 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
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- a) 반응물중에서 임의로 제조된 하기 일반식(Ⅱ)의 화합물을 고리화 시키고, 라디칼 A 또는 B중하나가 알콕시메틴 그룹인 화합물이 수득될 경우, 이어서 이를 가수분해 시키거나, b) R이 알킬설피닐 또는 알킬설포닐인 일반식(Ⅰ)의 화합물을 제조하기 위하여, 하기 일반식(Ⅲ)의 화합물을 산화시키고, 경우에 따라서, 이어서 수득된 일반식(Ⅰ)의 의 화합물을 이의 산부가염, 특히 무기 또는 유기산과의 생리학적으로 허용가능한 산부가염으로 전환시킴을 특징으로 하여, 하기 일반식(Ⅰ)의 화합물 및 이의 토오토머 및 산부가염을 제조하는 방법.그룹 A 또는 B중 하나는 메틴그룹을 나타내고, 다른 하나는 카르보닐 그룹을 나타내며, R1은 알킬메르캅토, 알킬설피닐 또는 알킬설포닐그룹을 나타내며, R2는 알킬 잔기의 탄소수가 1내지 3인 알콕시그룹을 나타내고, 그룹 A′또는 B′중 하나는 메틴룹을 나타내고 다른 하나는 카르보닐그룹 또는 알콕시 메틴그룹(여기서 알콕시부위는 C1―C3를 함유할 수 있음)을 나타내며, 그룹 X 또는 Y중 하나는 수소원자를 나타내고 다른 하나는 하기 일반식(A)의 그룹을 나타내거나, X 및 Y 모두가 일반식(A)의 그룹을 나타내고,상기식에서, Z1및 Z2는 동일하거나 상이할 수 있으며, 할로겐원자, 임의로 치환된 아미노그룹 이거나, 저급알킬 그룹에 의해 임의 치환된 하이드록시 또는 메르캅토그룹을 나타내거나, Z1및 Z2는 함께 산소 또는 황원자; C1―C3알킬 그룹에 의해 임의로 단일―또는 이 치환된 이미노그룹; C2―C3알킬렌 디옥시 또는 C2―C3알킬렌디티오그룹을 나타내고, R1′는 C1―C3알킬메르캅토 또는 C1―C3알킬―설피닐그룹을 나타낸다.
- 제1항에 있어서, A,B,R1및 R2는 제1항에 정의한 바와 같으며 R1이ㅣ 페닐핵의 4―위치에 있고 R2가 2―위치에 있는 일반식(Ⅰ)의 이미다조[4,5―c] 피리딘―은, 이의 토오토머 및 산부가염의 제조방법.
- 제1항에 있어서, 2―(2―메톡시―4―메틸―메르캅토―페닐)―5H―이미다조 [,5―c]피리딘―6―은, 이의 토오토머 및 산부가염의 제조방법.
- 제1항에 있어서, 기술된 화합물의 생리학적으로 허용되는 산부가염의 제조방법.
- 제1항에 있어서, 반응을 용매중에서 수행함을 특징으로 하는 방법.
- 제1a항 또는 5항에 있어서 반응하는 동안 또는 반응후에, 사용된 일반식(Ⅱ)의 화합물중에 함유된 알콕시메틴 그룹을 카르보닐그룹으로 전환시킴을 특징으로 하는 방법.
- 제1a항에 있어서, 반응을 아실화제, 축합제 또는 염기중에서 수행함을 특징으로 하는 방법.
- 제1a항, 제5항, 6항 또는 7항에 있어서, 반응을 0내지 250℃, 바람직하게는 반응혼합물의 비점에서 수행함을 특징으로 하는 방법.
- 제1a항 또는 5항에 있어서, 산화반응을 ―80°내지 100℃, 바람직하게는 0내지 60℃에서 수행함을 특징으로 하는 방법.
- 제1b항, 5항 또는 9항에 있어서, 일반식(Ⅰ)의 설피닐화합물을 제조하기 위한 산화반응을 사용된 산화제 1당량으로 수행함을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833346602 DE3346602A1 (de) | 1983-12-23 | 1983-12-23 | Neue imidazo(4,5-c)pyridin-one, deren herstellung und diese verbindungen enthaltende arzneimittel |
| DEP3346602.5 | 1983-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR850004479A true KR850004479A (ko) | 1985-07-15 |
Family
ID=6217813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840008221A KR850004479A (ko) | 1983-12-23 | 1984-12-21 | 이미다조〔4,5-c〕피리딘-온의 제조방법 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4568680A (ko) |
| EP (1) | EP0149131A3 (ko) |
| JP (1) | JPS60169478A (ko) |
| KR (1) | KR850004479A (ko) |
| AU (1) | AU3704584A (ko) |
| DD (1) | DD232918A5 (ko) |
| DE (1) | DE3346602A1 (ko) |
| DK (1) | DK597584A (ko) |
| ES (2) | ES537991A0 (ko) |
| FI (1) | FI845085L (ko) |
| HU (1) | HU193072B (ko) |
| IL (1) | IL73898A (ko) |
| NO (1) | NO845171L (ko) |
| NZ (1) | NZ210655A (ko) |
| PT (1) | PT79737B (ko) |
| ZA (1) | ZA849973B (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3347290A1 (de) * | 1983-12-28 | 1985-07-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue 2-phenyl-imidazole, ihre herstellung und diese verbindungen enthaltende arzneimittel |
| US4740599A (en) * | 1986-10-03 | 1988-04-26 | Eli Lilly And Company | Synthesis of alkylsulfinyl substituted 2-phenylimidazo(4,5-c)pyridines |
| DE68920998T2 (de) * | 1988-03-15 | 1995-06-22 | Searle & Co | 1H/3H-[4-(N,N-CYCLOALKYL UND/ODER VERZWEIGTES ALKYLCARBOXAMIDO)-BENZYL]IMDAZO[4,5-c]PYRIDINE ALS PAF-ANTAGONISTEN. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932428A (en) * | 1972-03-20 | 1976-01-13 | Eli Lilly And Company | 1H-imidazo(4,5,-b)-pyridine derivatives |
| DE3037464A1 (de) * | 1980-10-03 | 1982-05-19 | Dr. Karl Thomae Gmbh, 7950 Biberach | 6-hydroxy-2-phenyl-imidazo 4,5-b zu pyridine, ihre herstellung und diese sie enthaltende arzneimittel |
| ES8401486A1 (es) * | 1981-11-10 | 1983-12-01 | Wellcome Found | Un procedimiento para la preparacion de nuevos derivados de imidazo (4,5-c)piridina. |
| ZA832938B (en) * | 1982-05-03 | 1984-12-24 | Lilly Co Eli | 2-phenylimidazo(4,5-c)pyridines |
-
1983
- 1983-12-23 DE DE19833346602 patent/DE3346602A1/de not_active Withdrawn
-
1984
- 1984-11-27 ES ES537991A patent/ES537991A0/es active Granted
- 1984-12-05 US US06/678,235 patent/US4568680A/en not_active Expired - Fee Related
- 1984-12-11 EP EP84115157A patent/EP0149131A3/de not_active Withdrawn
- 1984-12-13 DK DK597584A patent/DK597584A/da not_active Application Discontinuation
- 1984-12-20 NZ NZ210655A patent/NZ210655A/en unknown
- 1984-12-21 KR KR1019840008221A patent/KR850004479A/ko not_active Application Discontinuation
- 1984-12-21 HU HU844807A patent/HU193072B/hu unknown
- 1984-12-21 NO NO845171A patent/NO845171L/no unknown
- 1984-12-21 ZA ZA849973A patent/ZA849973B/xx unknown
- 1984-12-21 FI FI845085A patent/FI845085L/fi not_active Application Discontinuation
- 1984-12-21 AU AU37045/84A patent/AU3704584A/en not_active Abandoned
- 1984-12-21 IL IL73898A patent/IL73898A/xx unknown
- 1984-12-21 PT PT79737A patent/PT79737B/pt unknown
- 1984-12-21 DD DD84271453A patent/DD232918A5/de unknown
- 1984-12-21 JP JP59270614A patent/JPS60169478A/ja active Pending
-
1985
- 1985-05-06 ES ES542849A patent/ES542849A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES8603481A1 (es) | 1985-12-16 |
| IL73898A (en) | 1988-03-31 |
| IL73898A0 (en) | 1985-03-31 |
| EP0149131A3 (de) | 1986-06-11 |
| EP0149131A2 (de) | 1985-07-24 |
| JPS60169478A (ja) | 1985-09-02 |
| FI845085L (fi) | 1985-06-24 |
| ES8601988A1 (es) | 1985-11-01 |
| DK597584D0 (da) | 1984-12-13 |
| NO845171L (no) | 1985-06-24 |
| HUT36791A (en) | 1985-10-28 |
| ES542849A0 (es) | 1985-12-16 |
| DE3346602A1 (de) | 1985-07-11 |
| NZ210655A (en) | 1988-02-29 |
| ES537991A0 (es) | 1985-11-01 |
| ZA849973B (en) | 1986-08-27 |
| DK597584A (da) | 1985-06-24 |
| PT79737B (de) | 1986-12-10 |
| DD232918A5 (de) | 1986-02-12 |
| US4568680A (en) | 1986-02-04 |
| AU3704584A (en) | 1985-07-04 |
| HU193072B (en) | 1987-08-28 |
| FI845085A0 (fi) | 1984-12-21 |
| PT79737A (de) | 1985-01-01 |
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