KR850003539A - 밀베마이신 5-카르보네이트 유도체의 제조방법 - Google Patents
밀베마이신 5-카르보네이트 유도체의 제조방법 Download PDFInfo
- Publication number
- KR850003539A KR850003539A KR1019840007147A KR840007147A KR850003539A KR 850003539 A KR850003539 A KR 850003539A KR 1019840007147 A KR1019840007147 A KR 1019840007147A KR 840007147 A KR840007147 A KR 840007147A KR 850003539 A KR850003539 A KR 850003539A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- compound
- formula
- milbemycin
- alkyl group
- Prior art date
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- 238000000034 method Methods 0.000 title claims 4
- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- BWCRYQGQPDBOAU-UHFFFAOYSA-N Milbemycin D Natural products C1CC(C)C(C(C)C)OC21OC(CC=C(C)CC(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 BWCRYQGQPDBOAU-UHFFFAOYSA-N 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- BWCRYQGQPDBOAU-WZBVPYLGSA-N milbemycin D Chemical compound C1C[C@H](C)[C@@H](C(C)C)O[C@@]21O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 BWCRYQGQPDBOAU-WZBVPYLGSA-N 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- VOZIAWLUULBIPN-LRBNAKOISA-N milbemycin A4 Chemical compound C1C[C@H](C)[C@@H](CC)O[C@@]21O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 VOZIAWLUULBIPN-LRBNAKOISA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 150000005846 sugar alcohols Chemical class 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- 125000001769 aryl amino group Chemical group 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (12)
- 하기 일반식(Ⅰ)의 화합물을 하기 일반식(Ⅳ)의 화합물과 반응시키고, 나아가 일반식(Ⅲ)의 화합물중 Z가 AY일 경우에는 생성된 생성물을 일반식 R7-H(식중, R7는 하기에 정의하는 바와 같다.)의 화합물과 반응시킴을 특징으로 하는 하기 일반식(Ⅱ)의 화합물의 제조방법.(상기 식중, R1은 메틸기, 에틸기 또는 이소프로필기를 나타내고; R3는 수소 또는 할로겐원자, -Q-R4기, -O. CO. R5기 또는 -NH. CO. R6기를 나타내고; Q는 산소 또는 황원자 또는 아미노기를 나타내고; R4는 수소원자, C1~C6알킬기 또는 치환 C1~C6알킬기를 나타내고; R5는 C1~C6알킬기, 치환 C1~C6알킬기,아릴기, 복소환기 또는 임의 보호된 알돈산 또는 우론산 또는 우론산에서 하나의 카르복시기를 제거하여 형성된 기를 나타내고; R6는 C1~C6알킬기 또는 아릴기를 나타내고; Z는 R2또는 AY를 나타내며; Z1는 R2또는 AR7을 나타내며; R2는 임의 보호된 당알코올, 당 또는 알돈산에서 ω-알코올성 히드록시기를 제거하여 형성된 기, 또는 -A-R3기를 나타내고; A는 알킬렌 또는 알킬리덴기를 나타내고; Y는 할로겐원자, 바람직하게는 브롬 또는 요오드원자를 나타내고; R7은 -Q-R4' 또는 -O. CO. R5(식중, Q 및 R5는 상기에서 정의한 바와 같으며, R4'는 C1~C6알킬기 또는 치환 C1~C6알킬기를 나타낸다.)기를 나타내며; X는 할로겐원자, 바람직하게는 염소 또는 브롬원자를 나타내며; 상기 치환 C1~C6알킬기에 있어서의 치환체는 히드록시, C1~C6알콕시, 아릴옥시, 아미노, 아실아미노, C1~C6알킬아미노, 디(C1~C6알킬)아미노, 아릴아미노, 메르캅토,(C1~C6알킬티오 및 아릴티오기 중에서 선택된 하나이상의 기이다.)
- 제1항에 있어서, 화합물에서 Z1가 의임의 보호된 당알코올에서 ω-알코올성 히드록시기를 제거하여 형성된 기를 나타냄을 특징으로 하는 방법.
- 제1항에 있어서, 화합물에서 Z1가 A-R3식중, A는 C1~C2알킬렌기를 나타내고, R3는 할로겐원자, -Q-R4(식중, Q는 산소 또는 황원자를 나타내고, R4는 C1~C3알킬기 또는 치환 C1-C3알킬기를 나타내며, 이때 치환체는 히드록시기, C1~C3알콕시기, 아미노기, 아세틸아미노기 및 모노-또는 디-(C1~C3알킬)아미노기를 나타낸다.)기 또는 -OCOR5(식중, R5는 C1~C3알킬기, 치환 C1~C3알킬기(이때 치환체는 상기 R4에서 정의한 바와 같다.), 산소원자를 함유하는 5- 또는 6-원복소환기 또는 임의 보호된 알돈산에서 카르복시기를 제거하여 형성된 기를 나타낸다)기를 나타냄을 특징으로 하는 방법.
- 제1 또는 2항에 있어서, 화합물에서 R1이 에틸 또는 이소프로필기를 나타냄을 특징으로 하는 방법.
- 제1항에 있어서, 일반식(Ⅱ)의 화합물이-(클로로메톡시카르보닐)밀베마이신 D임을 특징으로 하는 방법.
- 제1항에 있어서, 일반식(Ⅱ)의 화합물이-(3,4-디히드로--피란-2-일카르보닐옥시)메톡시카르보닐밀레마이신 D임을 특징으로 하는 방법.
- 제1항에 있어서, 일반식(Ⅱ)의 화합물이-(1,2,3,4-디--이소프로필리덴칼락투로닐옥시)메톡시카르보닐밀베마이신 D임을 특징으로 하는 방법.
- 제1항에 있어서, 일반식(Ⅱ)의 화합물이-(4-히드록시부티릴옥시메톡시카르보닐)밀베마이신 D임을 특징으로 하는 방법.
- 제1항에 있어서, 일반식(Ⅱ)의 화합물이-[2-(-디메틸아미노)에틸티오메톡시카르보닐]밀베마이신 D임을 특징으로 하는 방법.
- 제1항에 있어서, 일반식(Ⅱ)의 화합물이-(2,3-디히드록시카르보닐)밀베마이신 A4임을 특징으로 하는 방법.
- 제1항에 있어서, 일반식(Ⅱ)의 화합물이-(2,3-디히드록시프로폭시카르보닐)밀베마이신 D임을 특징으로 하는 방법.
- 제1항에 있어서, 일반식(Ⅱ)의 화합물이-(2,2-디메틸-1,3-디옥솔란-4-일메톡시카르보닐)밀베마이신 A4임을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP213588/83 | 1983-11-14 | ||
JP213588 | 1983-11-14 | ||
JP58213588A JPS60126289A (ja) | 1983-11-14 | 1983-11-14 | ミルベマイシン類の5−カ−ボネ−ト誘導体 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR850003539A true KR850003539A (ko) | 1985-06-20 |
KR910006443B1 KR910006443B1 (ko) | 1991-08-24 |
Family
ID=16641684
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019840007147A KR910006443B1 (ko) | 1983-11-14 | 1984-11-14 | 밀베마이신 5-카르보네이트 유도체의 제조방법 |
Country Status (12)
Country | Link |
---|---|
US (1) | US4760054A (ko) |
EP (1) | EP0142969B1 (ko) |
JP (1) | JPS60126289A (ko) |
KR (1) | KR910006443B1 (ko) |
AU (1) | AU573766B2 (ko) |
CA (1) | CA1235693A (ko) |
DE (1) | DE3478438D1 (ko) |
DK (1) | DK164912C (ko) |
ES (1) | ES8607266A1 (ko) |
IL (1) | IL73508A (ko) |
NZ (1) | NZ210210A (ko) |
ZA (1) | ZA848826B (ko) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60126289A (ja) * | 1983-11-14 | 1985-07-05 | Sankyo Co Ltd | ミルベマイシン類の5−カ−ボネ−ト誘導体 |
EP0165900A3 (de) * | 1984-06-08 | 1986-05-28 | Ciba-Geigy Ag | Neue Lactone, Verfahren zu ihrer Herstellung und ihre Verwendung in der Schädlingsbekämpfung |
IL78621A (en) * | 1985-04-30 | 1991-06-30 | American Cyanamid Co | Mylbemycin analogs,their preparation and pesticidal compositions containing them |
US4778809A (en) * | 1985-08-23 | 1988-10-18 | Ciba-Geigy Corporation | 5-esters of milbemycins for controlling parasitic pests |
JPH0678342B2 (ja) * | 1986-01-07 | 1994-10-05 | 三共株式会社 | 新規マクロライド化合物 |
EP0237482A1 (de) * | 1986-03-06 | 1987-09-16 | Ciba-Geigy Ag | C(29)-Carbonyloxi-milbemycin-Derivate zur Bekämpfung von tier- und pflanzenparasitären Schädlingen |
NZ219467A (en) * | 1986-03-07 | 1990-03-27 | Ciba Geigy Ag | 5-acyloxy 13b-alkyl milbemycins and parasiticidal compositions |
EP0237339B1 (en) * | 1986-03-12 | 1993-06-02 | American Cyanamid Company | Macrolide compounds |
EP0238259B1 (en) * | 1986-03-12 | 1993-09-29 | American Cyanamid Company | Macrolide compounds |
EP0245209A1 (de) * | 1986-05-07 | 1987-11-11 | Ciba-Geigy Ag | Milbemycin-Derivate, ihre Herstellung und ihre Verwendung zur Bekämpfung von Schädlingen |
CA1296329C (en) * | 1986-06-06 | 1992-02-25 | Derek R. Sutherland | Macrolide compounds |
JP2549558B2 (ja) * | 1989-04-13 | 1996-10-30 | 和夫 藤田 | 電動ステージ装置 |
JP2952265B2 (ja) * | 1993-11-29 | 1999-09-20 | 井筒屋化学産業株式会社 | 松類の枯損防止用組成物及び防止方法 |
DE19646720C2 (de) * | 1996-11-12 | 1999-02-18 | Ina Matallana Kielmann | Verfahren zum Vergleich von Peak-Darstellungen, insbesondere von Westernblot- oder Dot Blot-Streifen |
WO2012028556A1 (en) | 2010-08-31 | 2012-03-08 | Bayer Animal Health Gmbh | Macrocyclic lactones and their use and their combinations with other active substances |
DE102010064245A1 (de) | 2010-12-28 | 2012-06-28 | Bayer Animal Health Gmbh | Makrocylischen Lactone und deren Verwendung und deren Kombinationen mit anderen Wirkstoffen |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4134973A (en) * | 1977-04-11 | 1979-01-16 | Merck & Co., Inc. | Carbohydrate derivatives of milbemycin and processes therefor |
NZ186851A (en) * | 1977-04-11 | 1984-12-14 | Merck & Co Inc | Glycosyloxy derivatives of milbemycin and parasiticidal compositions |
NZ188459A (en) * | 1977-10-03 | 1982-09-07 | Merck & Co Inc | Derivatives of c-076 compounds and pesticidal compositions |
IL56149A (en) * | 1977-12-19 | 1989-09-28 | Merck & Co Inc | 13-halo and 13-deoxy derivatives of c-076 compounds,their preparation and method for the treatment of parasitic infections in animals therewith |
US4289760A (en) * | 1980-05-02 | 1981-09-15 | Merck & Co., Inc. | 23-Keto derivatives of C-076 compounds |
JPS57139081A (en) * | 1981-02-23 | 1982-08-27 | Sankyo Co Ltd | 5-alkylcarbamoyloxy and 5-alkanesulfonyloxy derivative of antibiotic substance b-41 and preparation thereof |
NZ201681A (en) * | 1981-09-03 | 1985-11-08 | Merck & Co Inc | Avermectin derivatives and parasiticidal compositions |
US4408059A (en) * | 1981-12-04 | 1983-10-04 | University Patents, Inc. | Spiroketals useful as intermediates in the synthesis of milbemycin and avermectin macrolides |
JPS5916894A (ja) * | 1982-07-21 | 1984-01-28 | Sankyo Co Ltd | ミルベマイシンdの5−アシルオキシ誘導体 |
JPS5920284A (ja) * | 1982-07-23 | 1984-02-01 | Sankyo Co Ltd | ミルベマイシンdの5−エ−テル誘導体及びその塩 |
JPS5920285A (ja) * | 1982-07-23 | 1984-02-01 | Sankyo Co Ltd | ミルベマイシンdの5−二塩基酸エステル誘導体及びその塩 |
US4582852A (en) * | 1983-11-02 | 1986-04-15 | Ciba-Geigy Corporation | 14- and 15-hydroxy milbemycin derivatives for controlling plant and animal parasites |
JPS60126289A (ja) * | 1983-11-14 | 1985-07-05 | Sankyo Co Ltd | ミルベマイシン類の5−カ−ボネ−ト誘導体 |
JPS60152490A (ja) * | 1984-01-20 | 1985-08-10 | Sankyo Co Ltd | ミルベマイシンa↓3,a↓4の5−二塩基酸エステル誘導体及びその塩 |
JPS60184085A (ja) * | 1984-03-02 | 1985-09-19 | Sankyo Co Ltd | ミルベマイシン類の5−アミノ酸エステル誘導体 |
US4547491A (en) * | 1984-07-18 | 1985-10-15 | Merck & Co., Inc. | C-8A-Oxo-avermectin and milbemycin derivatives, pharmaceutical compositions and method of use |
-
1983
- 1983-11-14 JP JP58213588A patent/JPS60126289A/ja active Pending
-
1984
- 1984-11-09 EP EP84307785A patent/EP0142969B1/en not_active Expired
- 1984-11-09 DE DE8484307785T patent/DE3478438D1/de not_active Expired
- 1984-11-13 ZA ZA848826A patent/ZA848826B/xx unknown
- 1984-11-14 CA CA000467778A patent/CA1235693A/en not_active Expired
- 1984-11-14 AU AU35409/84A patent/AU573766B2/en not_active Ceased
- 1984-11-14 ES ES537650A patent/ES8607266A1/es not_active Expired
- 1984-11-14 DK DK541584A patent/DK164912C/da not_active IP Right Cessation
- 1984-11-14 IL IL73508A patent/IL73508A/xx not_active IP Right Cessation
- 1984-11-14 NZ NZ210210A patent/NZ210210A/en unknown
- 1984-11-14 KR KR1019840007147A patent/KR910006443B1/ko not_active IP Right Cessation
-
1985
- 1985-09-26 US US06/780,391 patent/US4760054A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
IL73508A0 (en) | 1985-02-28 |
EP0142969B1 (en) | 1989-05-31 |
DK541584D0 (da) | 1984-11-14 |
EP0142969A1 (en) | 1985-05-29 |
ES537650A0 (es) | 1986-05-16 |
ZA848826B (en) | 1985-07-31 |
CA1235693A (en) | 1988-04-26 |
DK164912B (da) | 1992-09-07 |
IL73508A (en) | 1989-01-31 |
US4760054A (en) | 1988-07-26 |
NZ210210A (en) | 1987-04-30 |
AU3540984A (en) | 1985-05-23 |
DE3478438D1 (en) | 1989-07-06 |
ES8607266A1 (es) | 1986-05-16 |
DK164912C (da) | 1993-01-25 |
AU573766B2 (en) | 1988-06-23 |
KR910006443B1 (ko) | 1991-08-24 |
DK541584A (da) | 1985-05-15 |
JPS60126289A (ja) | 1985-07-05 |
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