KR830006200A - 아미드 유도체의 제조방법 - Google Patents
아미드 유도체의 제조방법 Download PDFInfo
- Publication number
- KR830006200A KR830006200A KR1019810002687A KR810002687A KR830006200A KR 830006200 A KR830006200 A KR 830006200A KR 1019810002687 A KR1019810002687 A KR 1019810002687A KR 810002687 A KR810002687 A KR 810002687A KR 830006200 A KR830006200 A KR 830006200A
- Authority
- KR
- South Korea
- Prior art keywords
- carbon atoms
- aryl
- alkyl
- hydrogen
- hydroxy
- Prior art date
Links
- 150000001408 amides Chemical class 0.000 title claims 9
- 238000000034 method Methods 0.000 title claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 21
- 125000003118 aryl group Chemical group 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 10
- -1 COOH compound Chemical class 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 6
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 125000004450 alkenylene group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000002431 aminoalkoxy group Chemical group 0.000 claims 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical group NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- 229940100389 Sulfonylurea Drugs 0.000 claims 1
- 241000534944 Thia Species 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000005122 aminoalkylamino group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 150000001718 carbodiimides Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 1
- 125000006301 indolyl methyl group Chemical group 0.000 claims 1
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical class 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/04—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D263/36—One oxygen atom
- C07D263/42—One oxygen atom attached in position 5
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/02—1,2-Oxazines; Hydrogenated 1,2-oxazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음
Description
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Claims (1)
- 본문에 상술한 바와 같이 1) 다음 일반식(2)의 산을 다음 일반식(3)의 아민과 반으시키거나 또는 2) X1이 카보닐 또는 티오카보닐기인 다음 일반식(4)의 아민을 일반식 R1-Y-Z1(식중 Z1은 치환 가능한 할로겐, 알칸설포닐 또는 아렌설포닐이거나 또는 하이드록시(이 경우 반응은 카보디이미드 또는 알킬클로로 포르메이트의 존재하에 수행된다) 또는 Y가 아미노일 때 일반식 R1NCO 화합물과, Y가 티오카보닐일 때 일반식 R1(S-SCH2COOH 화합물과)과 화합물과 반응시켜 R2가 수소이고 X가 카보닐 또는 티오카보닐인 아미드 유도체를 제조하거나, 또는 3) 다음 일반식 (5)의 화합물을 다음 일반식(6)의 화합물과 반응시켜, R2가 수소이고 X가 카보닐인 아미드 유도체를 제조하는 바, R2가 알킬, 아릴 알킬 또는 아릴인 아미드 유도체(R10=R12)는 R2가 수소인 상응하는 아미드 유도체(R10=R12)를 일반식 R2Z 화합물(Z는 치환가능한 할로겐, 알칸설포닐 또는 마렌설포닐이다)과 반응시켜 얻을 수 있으며, R3가 비치환 또는 치환 알킬인 아미드유도체는 R3가 비치환 또는 치환 알케닐인 상응하는 화합물을 수소 첨가하여 얻을 수 있으며, R10이 하이드록시가 아닐때(즉, -Q-R10이 에스테르 또는 아미드기를 형성한다)의 아미드 유도체는 에스테르 또는 아미드를 형성하는 통상적인 방법으로 -Q-R10이 -COOH인 상응하는 산으로부터 유도체를 얻을 수 있으며, Q가 카보닐이고 R10이 하이드록시인 아미드 유도체는 R10이이 알콕시인 상응하는 아미드 유도체를 가수분해하거나 또는 R10이 t-부톡시일때 상술한 화합물을 산 접촉 분해하여 얻을 수 있으며, X가 하이드록시메틸렌인 아미드 유도체는 X가 카보닐인 상응하는 아미드 유도체를 환원시켜 얻을 수 있으며, X가 옥시이미드 메틸렌인 아미드 유도체는 X가 카보닐인 상응하는 아미드 유도체를 하이드록시 아민 또는 0-치환 하이드록시아민 유도체와 반응시켜 얻을 수 있는, 다음 일반식(1)의 아미드 유도체의 제조방법.R1-Y-NR2-CHR3-X-CHR11-CHR4-CO-NR5-CR6R16-Q-R10(1)R1-Y-NR2-CHR3-X-CHR11CHR4-COOH (2)HNR5-CR6R16-Q-R12(3)H2NCH3-X1-CHR11CHR4CONR5-CR6R16-Q-R12(4)식중,R1은 수소, 또는, 불포화되거나, 또는 아미노, 벤질옥시 카보닐아미노,하이드록시, 알콕시, 알킬티오 및 각 5개까지의 탄소 원자를 갖는 알콕시카보닐 및 아릴, 아릴옥시 및 아릴티오 치환기로부터 선택된 하나의 치환기를 내포하거나 또는 하나가 아릴, 다른 하나가 아릴, 하이드록시, 아미노, 벤질옥시 카보닐아미노, 트리플루오로메틸, 아릴옥시 또는 5개까지 탄소의 알콕시이며, 세개의 치환기가 존재할 경우, 또 다른 하나가 아릴 또는 트리플루오로 메틸기인 둘 또는 세개의 치환기를 내포하는 15개 까지 탄소원자의 알킬이고, 또는,R1은 아릴, 또는, Y가 카보닐 또는 티오카보닐일 때 아릴옥시, 알콕시 또는 알콕시가 5개까지 탄소원자를 갖는 아릴알콕시이며, 또는,R1은 6개 탄소원자까지의 할로게노 알킬 또는 불포화하거나 아릴치환기를 내포하는 각 6개까지 탄소원자의 알케닐, 할로게노 알케닐 또는 사이클로 알킬이고 또는,R1은 일반식 R8CONHCHR9- 또는 R8COCH2CHR9의 치환기인바, 식중,R8은 알킬 또는 각 10개 탄소원자의 사이클로알킬, 또는 아릴이고,R9은 수소, 불포화되거나 또는 아릴치환기를 내포하는 5개 탄소원자까지의 알킬이거나, 또는,R9는 화합물 H2NCHR9COOH가 공통아미노산일 정도로 상기 정의된 이외의 기이다.R2은 수소, 불포화되거나 또는 아릴치환기를 내포하는 5개 탄소원자까지의 알킬기, 또는, 알릴기이며,R3은 불포화되거나 또는 아릴 치환기를 내포하는 각 5개까지의 탄소원자의 알킬, 또는 알케닐이거나 또는, R3은 아릴 또는 인돌릴 메틸기이고,R4은 수소, 또는 불포화되거나 또는 아릴치환기를 내포하는 5개까지 탄소원자의 알킬이며,R5은 수소이거나, 또는 불포화되거나 또는 아릴 치환기를 내포하는 각 5개까지의 탄소원자의 알킬기이거나, 또는 ,R5는 다음에 정의되는 R6와 함께 결합된다.R6는 수소, 아릴 또는 헤테로사이클 또는 하이드록시, 아릴 또는 헤테로사이클 치환기를 내포하는 5개가지 탄소원자의 알킬이거나, 또는 R6및 R5는 함께 결합하여 2-5개 탄소원자의 알킬렌 또는 알케닐렌을 형성하거나 또는 상술한 알킬렌, 또는 알케닐렌의 옥사, 티아 또는 아자 유도체, 또는 상술한 알킬렌 또는 알케닐렌의 하이드록시-또는 옥소-치환 유도체이며, R6및 R16또는 R6,R16및 R5또는 R6및 R10은 후술한 바와 같이 함께 결합된다.R16은 수소 또는 5개까지 탄소원자의 알킬기이며, 또는 R6및 R16은 함께 결합하여 2-5 탄소원자의 알킬렌을 형성하거나, (즉, 스피로사이클로알킬기를 형성함) 또는 R16은 R6이 상술한 바와는 다른 알킬 또는 다른 치환 알킬기인 R6의 제1탄소원자와 함께 이중결합을 형성하거나 또는 R6및 R5는 상술한 바와는 달리 함께 결합된다(즉, R5,R6및 R16은 함께 알킬리덴을 형성할 수 있다).Q는 카보닐(-CO-) 또는 메틸렌(-CH2-)이고,R10은 하이드록시, 아미노, 아릴옥시, 아릴티오, 알콕시, 사이클로알콕시, 알킬아미노, 디알킬아미노, 사이클아미노, 하이드록시알콕시, 아실옥시알콕시, 아미노알콕시, 알킬아미노알콕시, 디알칼아미노알콕시, 사이클아미노알콕시, 아미노알킬아미노, 알킬아미노알킬아미노, 디알킬아미노알킬아미노, 사이클아미노알킬아미노 또는 아릴알콕시(이중 각 알킬 또는 알콕시 5개까지의 탄소원자를 가지며, 사이클로아미노는 6개까지의 탄소원자를 갖는다)이거나, 또는 R10및 R6는 R10이 R6는 알킬일때 이의 탄소원자에 결합된 산소(-0-)일정도로 함께 결합되며,R11은 수소 또는 3개까지 탄소원자의 알킬기이고,X는 카보닐(-CO-), 하이드록시메틸렌(-CHOH-), 티오카보닐(-CS) 또는 옥시미노 메틸렌(-C=N-OR20, 식중 R20은 수소 또는 불포화되거나 아릴 치환기를 내포하는 5개까지 탄소원자의 알킬기)이며,Y는 카보닐, 티오카보닐, 설포닐(-SO2-) 또는 아미노(-NHCO-)이고,R12는 유리하이드록시 또는 아미노기를 포함하는 외에 R10에 대한 정의와 같다.※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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KR1019810002687A KR830006200A (ko) | 1981-07-24 | 1981-07-24 | 아미드 유도체의 제조방법 |
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KR1019810002687A KR830006200A (ko) | 1981-07-24 | 1981-07-24 | 아미드 유도체의 제조방법 |
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KR100670210B1 (ko) * | 2004-12-14 | 2007-01-16 | 한국전자통신연구원 | 관계형 데이터베이스를 기반으로 하는 XML데이터베이스에서 XQuery 트리거를 지원하는 방법 및시스템 |
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1981
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KR100670210B1 (ko) * | 2004-12-14 | 2007-01-16 | 한국전자통신연구원 | 관계형 데이터베이스를 기반으로 하는 XML데이터베이스에서 XQuery 트리거를 지원하는 방법 및시스템 |
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