KR840008013A - 퀴놀론 카복실산의 제조방법 - Google Patents
퀴놀론 카복실산의 제조방법 Download PDFInfo
- Publication number
- KR840008013A KR840008013A KR1019840000914A KR840000914A KR840008013A KR 840008013 A KR840008013 A KR 840008013A KR 1019840000914 A KR1019840000914 A KR 1019840000914A KR 840000914 A KR840000914 A KR 840000914A KR 840008013 A KR840008013 A KR 840008013A
- Authority
- KR
- South Korea
- Prior art keywords
- carbon atoms
- compound
- formula
- cyano
- represents hydrogen
- Prior art date
Links
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 title claims 5
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- -1 alkali metal salts Chemical class 0.000 claims 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 150000003839 salts Chemical class 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
- 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
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Claims (5)
- 일반식(Ⅱ)의 화합물을 일반식(Ⅲ)의 화합물과 반응시키거나, 일반식(Ⅱ)의 화합물을 일반식(Ⅳ)의 화합물과 반응시키거나, 일반식(Ⅴ)의 화합물을 알칼리 또는 산 조건하에서, 또는 R′가 벤질인 경우에는 가수소분해조건하에서 처리함을 특징으로 하여 일반식(I)의 퀴놀론카복실산 및 그의 약제학적으로 유용한 산 부가염, 알칼리금속염, 알칼리 토금속염 및 수화물을 제조하는 방법.상기식서 A는 탄소수 1내지 6의 직쇄 또는 측쇄알킬렌 또는 라디칼을 나타내고; R1은 알킬부위가 탄소수 1내지 6인 알콕시카보닐, 벤질옥시카보닐, 카복실, 임의로 치환된 카바모일, 시아노, 디알콕시포스포닐 또는 알킬부위가 탄소수 1내지 4인 알킬설포닐을 나타내며, R2가 수소, 알킬부위가 탄소수 1내지 6인 알콕시카보닐, 벤질옥시카보닐, 임의로 치환된 카바모일, 시아노, 염소, 아성틸, 탄소수 1 내지 3의 알킬 또는 페닐을 나타내거나, R1및 R2와 이들이 치환된 탄소원자가 함께 2-옥소-테트라 하이드로 푸릴환을 형성할 수 있고; R3,R4,R5및 R6는 동일하거나 다르며, 수소, 메틸, 에틸 또는 n-또는 l-프로필을 나타내며;X는 수소, 할로겐(바람직하게는 불소 또는 염소), 또는 니트로를 나타내고; Y는 할로겐(바람직하게는 염소,브롬 또는 요오드), CH3O-SO2-O, C2H5O-SO2-O, 메톡시 또는에톡시를 나타내며; R′는 탄소수 1내지 6의 알킬 또는 벤질을 나타낸다.
- 제1항에 있어서, A가 탄소수 1내지 5의 직쇄 또는 측쇄 알킬렌 또는을 나타내고; R1이 알킬 부위가 탄소수 1 내지 5인 알콕시카보닐, 벤질옥시카보닐, 카복실, 1 또는 2개의 메틸 또는 에틸라디칼에 의해 임의로 치환된 카바모일, 시아노, 메틸 설포닐 또는 에틸설포닐을 나타내고, R2가 수소, 알킬부위가 탄소수 1 내지 5인 알콕시카보닐, 벤질옥시카보닐, 카바모일, 시아노, 염소, 아세틸, 탄소수 1또는 2인 알킬 또는 페닐을 나타내거나, R1및 R2와 이들이 치환된 탄소원자가 함께 2-옥소-테트라하이드로푸릴환을 형성할수 있음; R3,R4,R5및 R6가 수소, 메틸 또는 에틸을 나타내고; X가 수소, 불소 또는 니트로를 나타내는 일반식(I)의 퀴놀론카복실 산을 제조하는 방법.
- 제1항에 있어서, A가 탄소수 1내지 5의 직쇄 알킬렌 또는를 나타내고; R1이 알킬부위가 탄소수 1내지 4인 알콕시카보닐, 벤질옥시카보닐, 카복실, 카바모일, 시아노 또는 메틸설포닐을 나타내고, R2가 수소, 알킬부위가 탄소수 1내지 3인 알콕시카보닐, 시아노, 염소, 아세틸 또는 페닐을 나타내거나, R1및 R2와 이들이 치환된 탄소원자가 함께 2-옥소-테트라하이드로-3-푸릴환을 형성할 수 있으며; R3가 수소, 메틸 또는 에틸을 나타내고; R4가 수소를 나타내며; R5가 수소 또는 메틸을 나타내고; R6가 수소를 나타내며; X가 수소, 불소, 염소 또는 니트로를 나타내는 일반식(I)의 퀴놀론카복실산을 제조하는 방법.
- 제1항에 있어서, 1-사이클로프로필-6-플우오로-1,4-디하이드로-4-옥소-7-{4-[2-옥소-1-(메톡시카보닐)-1-프로필]-1-프로필-1-피페라지닐}-3-퀴놀린카복실 산을 제조하는 방법.
- 제1항에 있어서, 7-[4-(2-클로로-2-시아노-에틸)-1-피페라지닐]-1-사이클로프로필-6-플루오로-1,4-디하이드로-4-옥소-3-퀴놀린카복실 산을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019870002923A KR870001004B1 (ko) | 1983-02-25 | 1987-03-30 | 퀴놀론 카복실산의 제조방법 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP3306772.4 | 1983-02-25 | ||
DE19833306772 DE3306772A1 (de) | 1983-02-25 | 1983-02-25 | Chinolonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019870002923A Division KR870001004B1 (ko) | 1983-02-25 | 1987-03-30 | 퀴놀론 카복실산의 제조방법 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR840008013A true KR840008013A (ko) | 1984-12-12 |
KR870000891B1 KR870000891B1 (ko) | 1987-05-02 |
Family
ID=6191897
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019840000914A Expired KR870000891B1 (ko) | 1983-02-25 | 1984-02-24 | 퀴놀론 카복실산의 제조방법 |
Country Status (21)
Country | Link |
---|---|
US (1) | US4559342A (ko) |
EP (1) | EP0117474B1 (ko) |
JP (1) | JPS59157068A (ko) |
KR (1) | KR870000891B1 (ko) |
AR (1) | AR244669A1 (ko) |
AT (1) | ATE23152T1 (ko) |
AU (1) | AU562184B2 (ko) |
CA (1) | CA1216849A (ko) |
DE (2) | DE3306772A1 (ko) |
DK (1) | DK103284A (ko) |
ES (1) | ES530045A0 (ko) |
FI (1) | FI83955C (ko) |
GR (1) | GR79988B (ko) |
HU (1) | HU192398B (ko) |
IE (1) | IE56924B1 (ko) |
IL (1) | IL71036A (ko) |
NO (1) | NO840557L (ko) |
NZ (1) | NZ207238A (ko) |
PH (3) | PH21906A (ko) |
PT (1) | PT78114B (ko) |
ZA (1) | ZA841375B (ko) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3306771A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
DE3306772A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinolonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
DE3308908A1 (de) * | 1983-03-12 | 1984-09-13 | Bayer Ag, 5090 Leverkusen | Bakterizide mittel |
DE3318145A1 (de) * | 1983-05-18 | 1984-11-22 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-6,8-difluor-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
DE3420798A1 (de) * | 1984-06-04 | 1985-12-05 | Bayer Ag, 5090 Leverkusen | 7-(3-aryl-l-piperazinyl)- sowie 7-(3-cyclohexyl-l-piperazinyl)-3-chinoloncarbonsaeuren |
DE3504643A1 (de) * | 1985-02-12 | 1986-08-14 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-1,4-dihydro-4-oxo-7-(4-(2-oxo-1,3-dioxol-4-yl-methyl)-1-piperazinyl)-3-chinolin carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
IT1200470B (it) * | 1985-05-10 | 1989-01-18 | Schering Spa | Composti ad attivita' antibatterica,loro preparazione e composizioni farmaceutiche relative |
ATE72668T1 (de) * | 1985-09-24 | 1992-03-15 | Hoffmann La Roche | Chinolinderivate. |
EP0224121A3 (en) * | 1985-11-19 | 1987-11-11 | ROTTAPHARM S.p.A. | 7-[4-amino-piperazinyl]- or 7-[4-chloro-piperazinyl]quinolinone derivatives, a process for the preparation thereof and pharmaceutical compositions containing them |
DE3542002A1 (de) * | 1985-11-28 | 1987-06-04 | Bayer Ag | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7- (1-piperazinyl)-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
DE3705621C2 (de) * | 1986-02-25 | 1997-01-09 | Otsuka Pharma Co Ltd | Heterocyclisch substituierte Chinoloncarbonsäurederivate |
JPH0811749B2 (ja) * | 1986-03-06 | 1996-02-07 | 富山化学工業株式会社 | 新規なキノリン誘導体およびその塩 |
DE3902079A1 (de) * | 1988-04-15 | 1989-10-26 | Bayer Ag | I.m. injektionsformen von gyrase-inhibitoren |
EP0338372A3 (en) * | 1988-04-22 | 1991-10-09 | American Cyanamid Company | Solubilized pro-drugs |
US5262417A (en) * | 1988-12-06 | 1993-11-16 | The Upjohn Company | Antibacterial quinolone compounds |
JPH04502317A (ja) * | 1988-12-06 | 1992-04-23 | ジ・アップジョン・カンパニー | 抗菌性キノロン化合物 |
WO2004043496A1 (de) * | 2002-11-11 | 2004-05-27 | Austria Wirtschaftsservice Gesellschaft M.B.H. | Fluor-18-markierte fluorchinolone |
WO2010140562A1 (ja) | 2009-06-04 | 2010-12-09 | 新日本石油株式会社 | 潤滑油組成物 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3149104A (en) * | 1961-01-03 | 1964-09-15 | Sterling Drug Inc | 4-hydroxy-7-styryl-1, 8-naphthyridine-3-carboxylic acids and esters |
US3590036A (en) * | 1968-11-18 | 1971-06-29 | George Y Lesher | Naphthyridine-3-carboxylic acids,their derivatives and preparation thereof |
US4017622A (en) * | 1972-12-18 | 1977-04-12 | Dainippon Pharmaceutical Co., Ltd. | Piperazine derivatives |
SE444566B (sv) * | 1977-09-20 | 1986-04-21 | Bellon Labor Sa Roger | 7-dialkylamin-6-halogen-4-oxo-1,4-dihydrokinolin-3-karboxylsyra, forfarande for framstellning derav och farmaceutiskt preparat derav |
DE2808070A1 (de) * | 1978-02-24 | 1979-08-30 | Bayer Ag | Verfahren zur herstellung von 4-pyridon-3-carbonsaeuren und/oder deren derivaten |
JPS5845426B2 (ja) * | 1978-09-29 | 1983-10-08 | 杏林製薬株式会社 | 置換キノリンカルボン酸誘導体 |
DE3142854A1 (de) * | 1981-10-29 | 1983-05-11 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-piperazino-chinolin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
DE3033157A1 (de) * | 1980-09-03 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
DE3363711D1 (en) * | 1982-03-31 | 1986-07-03 | Sterling Drug Inc | New quinolone compounds and preparation thereof |
DE3248505A1 (de) * | 1982-12-29 | 1984-07-05 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7(4- (oxoalkyl)-1-piperazinyl/-3-chinolincarbonsaeuren und ihre derivate, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
DE3306771A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
DE3306772A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinolonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
-
1983
- 1983-02-25 DE DE19833306772 patent/DE3306772A1/de not_active Withdrawn
-
1984
- 1984-02-03 US US06/576,596 patent/US4559342A/en not_active Expired - Lifetime
- 1984-02-08 AU AU24283/84A patent/AU562184B2/en not_active Ceased
- 1984-02-13 AT AT84101443T patent/ATE23152T1/de not_active IP Right Cessation
- 1984-02-13 EP EP84101443A patent/EP0117474B1/de not_active Expired
- 1984-02-13 DE DE8484101443T patent/DE3461087D1/de not_active Expired
- 1984-02-15 NO NO840557A patent/NO840557L/no unknown
- 1984-02-15 PT PT78114A patent/PT78114B/pt not_active IP Right Cessation
- 1984-02-21 PH PH30274A patent/PH21906A/en unknown
- 1984-02-22 IL IL71036A patent/IL71036A/xx not_active IP Right Cessation
- 1984-02-22 JP JP59030467A patent/JPS59157068A/ja active Granted
- 1984-02-22 NZ NZ207238A patent/NZ207238A/en unknown
- 1984-02-23 GR GR73903A patent/GR79988B/el unknown
- 1984-02-23 CA CA000448123A patent/CA1216849A/en not_active Expired
- 1984-02-23 FI FI840747A patent/FI83955C/fi not_active IP Right Cessation
- 1984-02-24 HU HU84749A patent/HU192398B/hu not_active IP Right Cessation
- 1984-02-24 IE IE443/84A patent/IE56924B1/en not_active IP Right Cessation
- 1984-02-24 ZA ZA841375A patent/ZA841375B/xx unknown
- 1984-02-24 KR KR1019840000914A patent/KR870000891B1/ko not_active Expired
- 1984-02-24 ES ES530045A patent/ES530045A0/es active Granted
- 1984-02-24 DK DK103284A patent/DK103284A/da not_active Application Discontinuation
-
1985
- 1985-07-09 PH PH32498A patent/PH22443A/en unknown
- 1985-07-09 PH PH32499A patent/PH23079A/en unknown
-
1986
- 1986-06-03 AR AR86304202A patent/AR244669A1/es active
Also Published As
Publication number | Publication date |
---|---|
FI83955C (fi) | 1991-09-25 |
DE3461087D1 (en) | 1986-12-04 |
ES8500931A1 (es) | 1984-11-01 |
AU2428384A (en) | 1984-08-30 |
US4559342A (en) | 1985-12-17 |
PT78114A (en) | 1984-03-01 |
NO840557L (no) | 1984-08-27 |
KR870000891B1 (ko) | 1987-05-02 |
IL71036A (en) | 1987-12-31 |
PH22443A (en) | 1988-09-12 |
PT78114B (en) | 1986-04-30 |
DK103284A (da) | 1984-08-26 |
IE56924B1 (en) | 1992-01-29 |
IE840443L (en) | 1984-08-25 |
CA1216849A (en) | 1987-01-20 |
DE3306772A1 (de) | 1984-08-30 |
FI83955B (fi) | 1991-06-14 |
ATE23152T1 (de) | 1986-11-15 |
GR79988B (ko) | 1984-10-31 |
PH21906A (en) | 1988-04-08 |
PH23079A (en) | 1989-04-10 |
DK103284D0 (da) | 1984-02-24 |
JPH0430391B2 (ko) | 1992-05-21 |
FI840747L (fi) | 1984-08-26 |
IL71036A0 (en) | 1984-05-31 |
NZ207238A (en) | 1986-05-09 |
EP0117474A1 (de) | 1984-09-05 |
ES530045A0 (es) | 1984-11-01 |
HU192398B (en) | 1987-06-29 |
EP0117474B1 (de) | 1986-10-29 |
JPS59157068A (ja) | 1984-09-06 |
AU562184B2 (en) | 1987-06-04 |
ZA841375B (en) | 1984-10-31 |
AR244669A1 (es) | 1993-11-30 |
FI840747A0 (fi) | 1984-02-23 |
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