KR890003703A - 치환된 2-페닐-4- 퀴놀린 카르복실산과 이의 제조방법 - Google Patents
치환된 2-페닐-4- 퀴놀린 카르복실산과 이의 제조방법 Download PDFInfo
- Publication number
- KR890003703A KR890003703A KR1019880011111A KR880011111A KR890003703A KR 890003703 A KR890003703 A KR 890003703A KR 1019880011111 A KR1019880011111 A KR 1019880011111A KR 880011111 A KR880011111 A KR 880011111A KR 890003703 A KR890003703 A KR 890003703A
- Authority
- KR
- South Korea
- Prior art keywords
- halogen
- hydroxy
- hydrogen
- alkyl
- phenyl
- Prior art date
Links
- YTRMTPPVNRALON-UHFFFAOYSA-N 2-phenyl-4-quinolinecarboxylic acid Chemical class N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1 YTRMTPPVNRALON-UHFFFAOYSA-N 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 9
- -1 phenoxy, phenylthio Chemical group 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims 2
- SBUKLPSBNFWJCU-UHFFFAOYSA-N ClIBr Chemical compound ClIBr SBUKLPSBNFWJCU-UHFFFAOYSA-N 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- MPEOPMFFJBITGE-UHFFFAOYSA-N 3-acetyloxy-2-(4-phenylphenyl)quinoline-4-carboxylic acid Chemical compound N1=C2C=CC=CC2=C(C(O)=O)C(OC(=O)C)=C1C(C=C1)=CC=C1C1=CC=CC=C1 MPEOPMFFJBITGE-UHFFFAOYSA-N 0.000 claims 1
- JHKHJFBQZJDOMG-UHFFFAOYSA-N 3-acetyloxy-6-bromo-2-(4-phenylphenyl)quinoline-4-carboxylic acid Chemical compound N1=C2C=CC(Br)=CC2=C(C(O)=O)C(OC(=O)C)=C1C(C=C1)=CC=C1C1=CC=CC=C1 JHKHJFBQZJDOMG-UHFFFAOYSA-N 0.000 claims 1
- VCJWBCAZGGEKHI-UHFFFAOYSA-N 3-hydroxy-8-methyl-2-(4-phenylphenyl)quinoline-4-carboxylic acid Chemical compound N1=C2C(C)=CC=CC2=C(C(O)=O)C(O)=C1C(C=C1)=CC=C1C1=CC=CC=C1 VCJWBCAZGGEKHI-UHFFFAOYSA-N 0.000 claims 1
- ZXMIFOJYMIDEPQ-UHFFFAOYSA-N 6,8-dichloro-2-(3,4-dichlorophenyl)-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=C(Cl)C=C(Cl)C=C2C(C(=O)O)=C(O)C=1C1=CC=C(Cl)C(Cl)=C1 ZXMIFOJYMIDEPQ-UHFFFAOYSA-N 0.000 claims 1
- HVOMQBZOFIMPOL-UHFFFAOYSA-N 6-fluoro-3-hydroxy-2-(4-phenylphenyl)quinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(F)C=C2C(C(=O)O)=C(O)C=1C(C=C1)=CC=C1C1=CC=CC=C1 HVOMQBZOFIMPOL-UHFFFAOYSA-N 0.000 claims 1
- CWPPFUMBASJMHB-UHFFFAOYSA-N 6-fluoro-3-hydroxy-2-[4-(4-methoxyphenyl)phenyl]quinoline-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=2C(=C(C(O)=O)C3=CC(F)=CC=C3N=2)O)C=C1 CWPPFUMBASJMHB-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (4)
- 하기 일반구조식(Ⅰ)의 화합물.상기식에서 R1은 수소, 할로겐 또는 알킬(C1-C3) ; R2는 수소, 할로겐, 트리플루오로메틸 또는 알킬(C1-C3) ; R3은 히드록시 또는 알카노일옥시(C2-C6); R4는 트리플루오로메틸, 할로겐, 히드록시, 알킬(C1--C6) ,페닐, 벤질, 페녹시, 페닐티오, 시클로알킬(C3-C6) 2,4 - 디클로로페녹시 또는 1 및 2-치환된 페닐(여기서 치환체는 할로겐 또는 알콕시(C1-C3) 임; R5는 수소 또는 할로겐이며; 단 R1이 수소이며, R2가 플루오로 이외의 것이며, R3이 히드록시일때 R4는 클로로, 브로모, 요오드, 메틸 또는 페닐일 수 없다.
- 제1항에 있어서, 화합물이 6-플루오로-3-히드록시-2-[1,1′비페닐]-4-일-4-퀴놀린카르복실산, 3-(아세틸옥시)-2-[1,1′-비페닐]-4-일-4-퀴놀린카르복실산, 3-히드록시-6-메틸-2-[1,1′-비페닐]-4-일-4-퀴놀린카르복실산 또는 6,8-디클로로-3-히드록시-2-[1,1′-비페닐]-4-퀴놀린카르복실산인 화합물.
- 제1항에 있어서, 화합물이 3-히드록시-8-메틸-2-[1,1′-비페닐]-4-일-4-퀴놀린카르복실산,6-플루오로-2-(2′-플루오로[1,1′-비페닐]-3-히드록시-4-퀴놀린카르복실산, 6,8-디클로로-2-(3,4-디클로로페닐)-3-히드록시-4-퀴놀린카르복실산,3-(아세틸옥시)-2-[1,1′-비페닐]-4-일-6-브로모-4-퀴놀린카르복실산 또는 6-플루오로-3-히드록시-2(4′-메톡시[1,1′-비페닐]-4-일)-4-퀴놀린카르복실산인 화합물.
- 반응 혼합물의 환류 온도하에 염기성 수성 용액내에서 하기 일반구조식(1)의 화합물을 하기 일반구조식(2)의 아세토페논의 저급알칸을 용액과 반응시키는 것을 포함하는 하기 일반구조식(Ⅰ)화합물의 제조방법:상기식에서 R1은 수소, 할로겐 또는 알킬(C1-C3) ; R2는 수소, 할로겐, 트리플루오로메틸 또는 알킬(C1-C3) 이다.상기식에서 R4는 트리푸루오로메틸, 할로겐, 히드록시, 알킬(C1-C6), 페닐, 벤질, 페녹시, 페닐티오, 시클로알킬(C3-C6) 2,4 - 디클로로페녹시 또는 1 및 2- 치환된 페닐(여기서 치환체는 할로겐 또는 알콕시(C1-C3) 임); R5는 수소 또는 할로겐이고; R 은 메틸 또는 -O-CO- 알킬(C1-C5) 이다.상기식에서 R1은 수소, 할로겐 또는 알킬(C1-C3); R2은 수소, 할로겐, 트리플루오로메틸 또는 알킬(C1-C3); R3은 히드록시 또는 알카노일옥시(C2-C6) ; R4는 트리플루오로메틸, 할로겐, 히드록시, 알킬(C1-C6), 페닐, 벤질, 페녹시, 페닐티오, 시클로알킬(C3-C6) 2,4-디클로로페녹시 또는/및 2- 치환된 페닐(여기서 치환체는 할로겐 또는 알콕시(C1-C3) 임); R5는 수소 또는 할로겐이며 ; 단 R1이 수소이며, R2가 플루오로 이외의 것이며 R3이 히드록시일때R4는 클로로, 브로모, 요오드, 메틸 또는 페닐일 수 없다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/090,996 US4847381A (en) | 1987-08-31 | 1987-08-31 | 2-Phenyl-4-quinoline carboxylic acids |
US07/090,996 | 1987-08-31 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR890003703A true KR890003703A (ko) | 1989-04-17 |
KR970005909B1 KR970005909B1 (ko) | 1997-04-22 |
Family
ID=22225261
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019880011111A KR970005909B1 (ko) | 1987-08-31 | 1988-08-30 | 치환된 2-페닐-4-퀴놀린카르복실산과 이의 제조방법 |
Country Status (24)
Country | Link |
---|---|
US (1) | US4847381A (ko) |
EP (1) | EP0305952B1 (ko) |
JP (1) | JP2760379B2 (ko) |
KR (1) | KR970005909B1 (ko) |
AR (1) | AR245698A1 (ko) |
AT (1) | ATE90079T1 (ko) |
AU (1) | AU613661B2 (ko) |
CA (1) | CA1333606C (ko) |
CS (1) | CS274434B2 (ko) |
DD (1) | DD282225A5 (ko) |
DE (1) | DE3881456T2 (ko) |
DK (1) | DK169473B1 (ko) |
ES (1) | ES2058191T3 (ko) |
FI (1) | FI92692C (ko) |
GR (1) | GR3008033T3 (ko) |
HU (1) | HU202498B (ko) |
IE (1) | IE65148B1 (ko) |
IL (1) | IL87457A (ko) |
NO (1) | NO174961C (ko) |
NZ (1) | NZ225924A (ko) |
PH (1) | PH26258A (ko) |
PL (1) | PL156232B1 (ko) |
PT (1) | PT88365B (ko) |
ZA (1) | ZA886443B (ko) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4968701A (en) * | 1988-04-26 | 1990-11-06 | E. I. Du Pont De Nemours And Company | 4-Quinoline carboxylic acid derivatives useful as immunosuppressive agents |
US4918077A (en) * | 1989-01-25 | 1990-04-17 | E. I. Du Pont De Nemours & Co., Inc. | 3-phenyl-5,6-dihydrobenz(c)acridine-7-carboxylic acids and related compounds as cancer chemotherapeutic agents |
US5204329A (en) * | 1990-06-11 | 1993-04-20 | Du Pont Merck Pharmaceutical Company | Treatment of organ transplantation rejection |
US5135934A (en) * | 1990-07-06 | 1992-08-04 | Du Pont Merck Pharmaceutical Company | 3-phenyl-5,6-dihydrobenz(c) acridine-7-carboxylic acids and related compounds as immunosuppressive agents |
US5409886A (en) * | 1993-02-18 | 1995-04-25 | Mitsui Toatsu Chemicals, Incorporated | 3-pyrroline-2-one derivatives and herbicidal compositions containing same |
US5428040A (en) * | 1993-08-31 | 1995-06-27 | The Du Pont Merck Pharmaceutical Company | Carbocyclic fused-ring quinolinecarboxylic acids useful as immunosuppressive agents |
US5578609A (en) * | 1994-03-25 | 1996-11-26 | The Dupont Merck Pharmaceutical Company | 2-carbocyclic and 2-heterocyclic quinoline-4-carboxylic acids and salts thereof useful as immunosuppressive agents |
ID18663A (id) | 1996-04-12 | 1998-04-30 | Novartis Ag | Komposisi farmasi berlapis enterik |
KR20010014030A (ko) | 1997-06-19 | 2001-02-26 | 더글라스이.리디치 | 퀴놀린-인돌 항균제, 이들의 용도 및 조성물 |
US6103905A (en) * | 1997-06-19 | 2000-08-15 | Sepracor, Inc. | Quinoline-indole antimicrobial agents, uses and compositions related thereto |
US6376670B1 (en) | 1997-06-19 | 2002-04-23 | Sepracor Inc. | Quinoline-indole antimicrobial agents, uses and compositions related thereto |
US6207679B1 (en) | 1997-06-19 | 2001-03-27 | Sepracor, Inc. | Antimicrobial agents uses and compositions related thereto |
WO1999038846A1 (en) * | 1998-01-30 | 1999-08-05 | Procept, Inc. | Immunosuppressive agents |
SE9901366D0 (sv) * | 1999-04-16 | 1999-04-16 | Pharmacia & Upjohn Ab | Injector device and method for its operation |
US20020121638A1 (en) * | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
WO2009016812A1 (ja) * | 2007-07-27 | 2009-02-05 | Kowa Company, Ltd. | 2-フェニルキノリン-4-カルボン酸誘導体を有効成分とする貧血の予防及び/又は治療剤 |
AU2014352920A1 (en) | 2013-11-22 | 2016-06-23 | Genzyme Corporation | Novel methods for treating neurodegenerative diseases |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
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US2776290A (en) * | 1957-01-01 | Hydroxy cevchoninates and carboxylic | ||
US2008923A (en) * | 1931-07-09 | 1935-07-23 | Graham Patmore L | Cinchoninic acid salts of piperazines |
US2077903A (en) * | 1933-12-15 | 1937-04-20 | Gen Aniline Works Inc | Process of preparing 3-amino-quinolines |
US2486440A (en) * | 1946-01-10 | 1949-11-01 | Gen Aniline & Film Corp | Production of phenazonium dyestuff images |
BE502610A (ko) * | 1950-04-18 | |||
US2888346A (en) * | 1955-08-22 | 1959-05-26 | Gen Aniline & Film Corp | Ultra-violet absorbing compounds |
DE1049701B (ko) * | 1957-02-21 | |||
FR6592M (ko) * | 1967-10-31 | 1968-12-30 | ||
BE794945A (fr) * | 1972-02-04 | 1973-08-02 | Sandoz Sa | Application de derives de la quinoleine pour stabiliser des matieres organiques contre les effets de la lumiere ultraviolette |
US4009020A (en) * | 1975-05-06 | 1977-02-22 | Amchem Products, Inc. | Method of regulating plant growth |
SU1109402A1 (ru) * | 1982-10-12 | 1984-08-23 | Предприятие П/Я Р-6496 | Способ получени производных 2-(хинолил-4)-5-арилоксазола |
ZA845594B (en) * | 1983-07-22 | 1986-03-26 | Du Pont | Phenylquinolinecarboxylic acids and derivatives as antitumor agents |
US4680299A (en) * | 1984-04-30 | 1987-07-14 | E.I. Du Pont De Nemours And Company | 2-phenyl-4-quinolinecarboxylic acids and pharmaceutical compositions thereof |
-
1987
- 1987-08-31 US US07/090,996 patent/US4847381A/en not_active Expired - Lifetime
-
1988
- 1988-08-15 IL IL8745788A patent/IL87457A/en not_active IP Right Cessation
- 1988-08-24 NZ NZ225924A patent/NZ225924A/en unknown
- 1988-08-29 ES ES88114061T patent/ES2058191T3/es not_active Expired - Lifetime
- 1988-08-29 PH PH37473A patent/PH26258A/en unknown
- 1988-08-29 PT PT88365A patent/PT88365B/pt not_active IP Right Cessation
- 1988-08-29 CA CA000575951A patent/CA1333606C/en not_active Expired - Fee Related
- 1988-08-29 EP EP88114061A patent/EP0305952B1/en not_active Expired - Lifetime
- 1988-08-29 DE DE88114061T patent/DE3881456T2/de not_active Expired - Fee Related
- 1988-08-29 AT AT88114061T patent/ATE90079T1/de active
- 1988-08-30 KR KR1019880011111A patent/KR970005909B1/ko not_active IP Right Cessation
- 1988-08-30 JP JP63213853A patent/JP2760379B2/ja not_active Expired - Lifetime
- 1988-08-30 HU HU884489A patent/HU202498B/hu not_active IP Right Cessation
- 1988-08-30 NO NO883865A patent/NO174961C/no not_active IP Right Cessation
- 1988-08-30 DK DK482688A patent/DK169473B1/da not_active IP Right Cessation
- 1988-08-30 IE IE262888A patent/IE65148B1/en not_active IP Right Cessation
- 1988-08-30 ZA ZA886443A patent/ZA886443B/xx unknown
- 1988-08-30 AR AR88311798A patent/AR245698A1/es active
- 1988-08-30 AU AU21678/88A patent/AU613661B2/en not_active Ceased
- 1988-08-30 FI FI883997A patent/FI92692C/fi not_active IP Right Cessation
- 1988-08-31 CS CS587588A patent/CS274434B2/cs unknown
- 1988-08-31 DD DD88319347A patent/DD282225A5/de not_active IP Right Cessation
- 1988-08-31 PL PL1988274471A patent/PL156232B1/pl unknown
-
1993
- 1993-06-03 GR GR930400370T patent/GR3008033T3/el unknown
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