KR840005809A - 5-(저급-알킬)-1,6-나프티리딘-2(1h)-온류의 제조방법 - Google Patents
5-(저급-알킬)-1,6-나프티리딘-2(1h)-온류의 제조방법 Download PDFInfo
- Publication number
- KR840005809A KR840005809A KR1019830003601A KR830003601A KR840005809A KR 840005809 A KR840005809 A KR 840005809A KR 1019830003601 A KR1019830003601 A KR 1019830003601A KR 830003601 A KR830003601 A KR 830003601A KR 840005809 A KR840005809 A KR 840005809A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- amino
- necessary
- hydrogen
- prepare
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims 16
- 229910052739 hydrogen Chemical group 0.000 claims 7
- 239000001257 hydrogen Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- -1 amino carbamyl Chemical group 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- JTLWXFRVOPSNEH-UHFFFAOYSA-N 5-acetyl-6-methyl-1h-pyridin-2-one Chemical compound CC(=O)C=1C=CC(=O)NC=1C JTLWXFRVOPSNEH-UHFFFAOYSA-N 0.000 claims 1
- OCCZJXAHSUCJSA-UHFFFAOYSA-N 5-methyl-1h-1,6-naphthyridin-2-one Chemical compound N1C(=O)C=CC2=C1C=CN=C2C OCCZJXAHSUCJSA-UHFFFAOYSA-N 0.000 claims 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims 1
- 239000005695 Ammonium acetate Substances 0.000 claims 1
- KHEPBQUHHKSYDU-UHFFFAOYSA-N C(C)(=O)C=1C=CC(NC1C#CN(C)C)=O Chemical compound C(C)(=O)C=1C=CC(NC1C#CN(C)C)=O KHEPBQUHHKSYDU-UHFFFAOYSA-N 0.000 claims 1
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 claims 1
- 241000209140 Triticum Species 0.000 claims 1
- 235000021307 Triticum Nutrition 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 229940043376 ammonium acetate Drugs 0.000 claims 1
- 235000019257 ammonium acetate Nutrition 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000006114 decarboxylation reaction Methods 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 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
- C07D213/60—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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
- C07D213/60—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
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides 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)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (4)
- 다음 일반식(Ⅱ)화합물을 포름아미딘, 암모니아, 또는 이의 염과 반응시켜, Q가 시아노 또는 수소이고 또 R˝가 수소인 일반식(Ⅰ)의 상응화합물을 제조하고, 필요한 경우 Q가 시아노인 제조화합물을 가수분해시켜 Q가 카복시인 상응 화합물을 제조하고 필요한 경우, Q가 카복시인 제조화합물을 탈카복시 반응시켜 Q가 수소인 상응 화합물을 제조하며 필요한 경우 Q가 시아노인 제조 화합물을 가수분해시켜 Q가 카바밀인 상응 화합물을 제조하고 필요한 경우 Q가 카바밀인 제조화합물을 히드라진과 반응시켜 Q가 아미노 카바밀인 상응 화합물을 제조하며 필요한 경우 Q가 카바밀인 제조화합물을 카바밀을 아미노로 변환시킬 수 있는 시약과 반응시키거나, 또는 3－아미노 카바밀 화합물을 카복실산 하이드라지드를 아미노로 변환시킬 수 있는 시약과 반응시켜서 Q가 아미노인 상응 화합물을 제조하고 필요한 경우 Q가 아미노인 제조 화합물을 알카리 수용액과 가열하여 Q가 하이드록시인 상응 화합물을 제조하며 필요한 경우, R″가 수소인 제조 화합물을 알킬화 반응시켜 R″가 저급 알킬인 상응 화합물을 제조하고 필요한 경우 제조된 5－메틸－1, 6－나프틸리딘－2(1H)－온을 4－메틸벤젠 설폰에이트 4급 염으로 변환시키고 또 필요한 경우 제조된 유리염기를 부가염으로 변환시키거나 또는 Q가 하이드록시 또는 카복시이고 또는 R″가 수소인 제조 화합물을 양이온염으로 변환시키는 것을 특징으로 하여 다음 일반식(1)화합물, 또는 4급 암모늄염 1, 2－염디하이드로－5, 6－디메틸－2－옥소－1, 6－나프틸리디늄－4－메틸벤젠 설폰에이트를 제조하는 방법.상기 일반식(Ⅰ)및 (Ⅱ)에서 R, R1및 R2는 저급 알킬이고 R´는 수소 또는 메틸이며 R″는 수소 또는 저급 알킬이고 Q는 수소, 하이드록시, 아미노, 시아노, 카바밀, 카복시, 또는 아미노 카바밀이며, Q´는 수소 또는 시아노이다.
- 제1항에 있어서 5－아세틸－6－(2－디메틸아미노 에텐일)－2(1H) 피리딘－온을 포름아미딘 또는 암모늄 아세테이트와 반응시켜 5－메틸－1, 6－나프틸리딘－2 (1H)－온을 제조함을 특징으로 하는 제법.
- 상응 6－메틸 화합물을 디(저급－알킬)포름아미드 디－(저급－알킬)아세탈과 반응시키고, 또 필요한 경우 제조된 유리염기를 산부가염으로 변환시키는 것을 특징으로 하여 다음 일반식(Ⅱ)화합물을 제조하는 방법.상기 일반식(Ⅰ)에서R, R1, R2, R´및 Q´는 상기 1항의 정의와 동일하다.
- 제3항에 있어서, 5－아세틸－6－메틸－2(1H)－피리디논을 디메틸 포름아미드 디메틸 아세탈과 반응시켜 5－아세탈－6－(2－디메틸－아미노 에테닐)－2(1H)－피리디논을 제조함을 특징으로하는 제법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US404454 | 1982-08-02 | ||
| US404,454 | 1982-08-02 | ||
| US06/404,454 US4415580A (en) | 1982-08-02 | 1982-08-02 | Certain 2-(1H)-pyridinones cardiotonic compositions containing same and method of using same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840005809A true KR840005809A (ko) | 1984-11-19 |
| KR870000959B1 KR870000959B1 (ko) | 1987-05-14 |
Family
ID=23599673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830003601A KR870000959B1 (ko) | 1982-08-02 | 1983-08-01 | 5-(저급-알킬)-1,6-나프티리딘-2(1h)-온류의 제조방법 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4415580A (ko) |
| EP (2) | EP0101952B1 (ko) |
| JP (1) | JPS5944387A (ko) |
| KR (1) | KR870000959B1 (ko) |
| AT (1) | ATE29883T1 (ko) |
| AU (1) | AU561679B2 (ko) |
| DE (1) | DE3373813D1 (ko) |
| DK (2) | DK350983A (ko) |
| EG (1) | EG16284A (ko) |
| ES (2) | ES8605515A1 (ko) |
| FI (1) | FI74001C (ko) |
| GR (1) | GR79370B (ko) |
| GT (1) | GT198303012A (ko) |
| IL (1) | IL69325A (ko) |
| MY (1) | MY102475A (ko) |
| NO (1) | NO160077C (ko) |
| NZ (1) | NZ204969A (ko) |
| PH (1) | PH19871A (ko) |
| PT (1) | PT77118B (ko) |
| ZA (1) | ZA835446B (ko) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4595762A (en) * | 1982-08-25 | 1986-06-17 | Sterling Drug Inc. | 5-α-bromoalkanoyl-2-oxo-3-pyridinecarbonitriles |
| US4532247A (en) * | 1983-08-08 | 1985-07-30 | Sterling Drug Inc. | 5-(Hydroxyalkyl or alkanoyloxymethyl)-1,6-naphthyridin-2(1H)-one and cardiotonic use thereof |
| US4560691A (en) * | 1984-07-13 | 1985-12-24 | Sterling Drug Inc. | 5-(Phenyl)-1,6-naphthyridin-2(1H)-ones, their cardiotonic use and preparation |
| US4657919A (en) * | 1984-08-03 | 1987-04-14 | E. I. Du Pont De Nemours & Co. | Pyridone esters as inotropic agents |
| DE3431303A1 (de) * | 1984-08-25 | 1986-02-27 | Goedecke Ag | 1,6-naphthyridin-derivate, verfahren zu deren herstellung und deren verwendung |
| US4650806A (en) * | 1985-01-14 | 1987-03-17 | Sterling Drug Inc. | Cardiotonic 5-(heterylcarbonyl)-pyridones |
| US4567186A (en) * | 1985-01-14 | 1986-01-28 | Sterling Drug Inc. | 5-Heteryl-1,6-naphthyridin-2(1H)-ones, cardiotonic use thereof and intermediates therefor |
| NZ214837A (en) * | 1985-01-28 | 1988-10-28 | Sterling Drug Inc | 5-substituted 1,6 naphthyridin-2(1h)-ones |
| US4634772A (en) * | 1985-01-28 | 1987-01-06 | Sterling Drug Inc. | 2-[2-(di-lower-alkylamino)-1-propenyl]-6-methoxy-3-pyridinecarbonitriles, intermediates for cardiotonic agents |
| US4697021A (en) * | 1985-01-28 | 1987-09-29 | Sterling Drug Inc. | 1,6-dihydro-6-oxo-3-pyridinecarbonitriles, intermediates for cardiotonic agents |
| US4716170A (en) * | 1985-01-28 | 1987-12-29 | Sterling Drug Inc. | 5-[1H-(5-membered-N-aromatic heteryl)-1-yl]-1,6-naphthyridin-2(1H)-ones and their cardiotonic use |
| US4657915A (en) * | 1985-01-28 | 1987-04-14 | Sterling Drug Inc. | 1,6-naphthyridine-2(1H)-ones and their use as cardiotonic agents |
| TW486479B (en) | 1997-07-15 | 2002-05-11 | Dainippon Pharmaceutical Co | 5-substituted-3-oxadiazolyl-1,6-naphthyridin-2(1H)-one derivatives |
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 |
| US4363911A (en) * | 1981-09-03 | 1982-12-14 | Sterling Drug Inc. | 1,2-Dihydro-6-[2-(dimethylamino)ethenyl]-2-oxo-5-(pyridinyl) nicotinonitriles |
-
1982
- 1982-08-02 US US06/404,454 patent/US4415580A/en not_active Expired - Fee Related
-
1983
- 1983-07-20 NZ NZ204969A patent/NZ204969A/xx unknown
- 1983-07-25 IL IL69325A patent/IL69325A/xx unknown
- 1983-07-26 ZA ZA835446A patent/ZA835446B/xx unknown
- 1983-07-26 AU AU17291/83A patent/AU561679B2/en not_active Ceased
- 1983-07-27 PT PT77118A patent/PT77118B/pt not_active IP Right Cessation
- 1983-07-28 AT AT83107465T patent/ATE29883T1/de active
- 1983-07-28 FI FI832739A patent/FI74001C/fi not_active IP Right Cessation
- 1983-07-28 GR GR72074A patent/GR79370B/el unknown
- 1983-07-28 EP EP83107465A patent/EP0101952B1/en not_active Expired
- 1983-07-28 EP EP86107627A patent/EP0204335A3/en not_active Ceased
- 1983-07-28 DE DE8383107465T patent/DE3373813D1/de not_active Expired
- 1983-07-29 GT GT198303012A patent/GT198303012A/es unknown
- 1983-08-01 DK DK350983A patent/DK350983A/da not_active Application Discontinuation
- 1983-08-01 KR KR1019830003601A patent/KR870000959B1/ko not_active IP Right Cessation
- 1983-08-01 NO NO832784A patent/NO160077C/no unknown
- 1983-08-01 ES ES524642A patent/ES8605515A1/es not_active Expired
- 1983-08-02 EG EG480/83A patent/EG16284A/xx active
- 1983-08-02 PH PH29344A patent/PH19871A/en unknown
- 1983-08-02 JP JP58141813A patent/JPS5944387A/ja active Pending
-
1984
- 1984-03-15 ES ES530632A patent/ES530632A0/es active Granted
-
1987
- 1987-09-29 MY MYPI87002238A patent/MY102475A/en unknown
-
1990
- 1990-07-25 DK DK176890A patent/DK176890D0/da not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR840005809A (ko) | 5-(저급-알킬)-1,6-나프티리딘-2(1h)-온류의 제조방법 | |
| KR870003989A (ko) | 치환 및 이치환 피리딘-2,3-디카르복실레이트의 제조방법과 치환된 니코티네이트의 제조방법 | |
| KR830005140A (ko) | 피페리딘 유도체의 제조방법 | |
| CA1130805A (en) | Pyrid (2, 1-b) quinazolinone derivatives and their manufacture and use | |
| KR100215702B1 (ko) | 클로로말레이트 또는 클로로푸마레이트 또는 이들의 혼합물로부터 치환 및 비치환 - 2,3 - 피리딘디카르복실레이트의 제조방법 및 이로써 얻어진 피리딘디카르복실레이트 화합물 | |
| KR860001109A (ko) | 1,6-나프 티리딘-2(1h)-온류의 제법 | |
| KR840006658A (ko) | 피리도[2,2-d]피리미딘-5-온류의 제법 | |
| KR840004072A (ko) | 3-q-4-r₂-5-(저급-알카노일)-6-(저급-알킬)-2(1h)-피리디논의 제조방법 | |
| GB989193A (en) | Process for the production of heterocyclic nitrogen compounds | |
| KR920006334A (ko) | 치환된 1,2,4-트리아진디온, 그의 제조방법, 그를 위한 중간체 및 그의 용도 | |
| KR850001193A (ko) | [(피리디닐)-2-피리미디닐]우레아의 제조방법 | |
| KR870000338A (ko) | 테트라하이드로 이미다조퀴나졸리논 유도체의 제조방법 | |
| KR840006625A (ko) | 3,4-디하이드로-3-r₁-4-r₂-5-q-6-r-2-(1h)-피리디논류의 제법 | |
| US3970662A (en) | 4-(3-Nitrophenyl)-2,3,5,6-pyridinetetracarboxylic acid and intermediates | |
| KR890014487A (ko) | 치환-피리딘-2,3-디카르복실산을 생성시키기 위한 치환-8-히드록시퀴놀린의 연속적 산화 방법 | |
| KR860003231A (ko) | 2-시아노벤즈 이미다졸 유도체의 제조방법 | |
| KR830005203A (ko) | 6-(피리디닐)-4-치환-3(2h)-피리다지논의 제조방법 | |
| KR840008151A (ko) | 피라졸로 [1,5-a] 피리딘 유도체의 제조방법 | |
| DK165832C (da) | Fremgangsmaade til fremstilling af 2-carboxy-pyrazin-4-oxider | |
| KR920006447A (ko) | 새로운 알파형 퀴나크리돈계 유도체 및 그 제조방법 | |
| US5597924A (en) | Coversion of substituted 8-chloroquinolines to substituted 8-hydroxyquinolines | |
| ES271134A1 (es) | Un metodo para la preparaciën de dibeno a,d ciclohepta 1,4 dienos y de sus sales por adiciën de acido | |
| KR860001112A (ko) | 니트로 아포빈카민 산 유도체의 제조방법 | |
| GB817745A (en) | 2-thiohydantoins | |
| US4055588A (en) | Tetra-(lower-alkyl)3-(3-nitrophenyl)-1,5-pentanedione-1,2,4,5-tetracarboxylates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| G160 | Decision to publish patent application | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| LAPS | Lapse due to unpaid annual fee |