KR19980015378A - New piperidine derivatives - Google Patents
New piperidine derivatives Download PDFInfo
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- KR19980015378A KR19980015378A KR1019960034677A KR19960034677A KR19980015378A KR 19980015378 A KR19980015378 A KR 19980015378A KR 1019960034677 A KR1019960034677 A KR 1019960034677A KR 19960034677 A KR19960034677 A KR 19960034677A KR 19980015378 A KR19980015378 A KR 19980015378A
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- piperidine derivatives
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- 150000003053 piperidines Chemical class 0.000 title claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 230000000845 anti-microbial effect Effects 0.000 abstract description 6
- 239000004599 antimicrobial Substances 0.000 abstract description 6
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 4
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 abstract description 4
- 241000894006 Bacteria Species 0.000 abstract description 3
- 230000000295 complement effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- -1 benzyl halide Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- BPPZXJZYCOETDA-UHFFFAOYSA-N 1-benzylpiperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC=CC=C1 BPPZXJZYCOETDA-UHFFFAOYSA-N 0.000 description 2
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000006242 amine protecting group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 125000005604 azodicarboxylate group Chemical group 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 229960002549 enoxacin Drugs 0.000 description 1
- IDYZIJYBMGIQMJ-UHFFFAOYSA-N enoxacin Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 IDYZIJYBMGIQMJ-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- YRSXSSQUWLJVDE-UHFFFAOYSA-N o-piperidin-3-ylhydroxylamine Chemical compound NOC1CCCNC1 YRSXSSQUWLJVDE-UHFFFAOYSA-N 0.000 description 1
- XNSMUWSVCDBVDD-UHFFFAOYSA-N o-piperidin-4-ylhydroxylamine Chemical compound NOC1CCNCC1 XNSMUWSVCDBVDD-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 229940072132 quinolone antibacterials Drugs 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
본 발명은 다음의 일반식(I)으로 표시되는 피페리딘 유도체로서, 그람음성균에 대해서는 탁월한 항균력을 보여주지만 그람양성균에 대해서는 그 항균력이 현저히 떨어지는 퀴놀론계 항균제의 단점을 보완하기 위해 퀴놀론계 항균화합물에 도입되는 매우 유용한 중간체를 제공하는 피폐리딘 유도체를 제공하는 새로운 피페리딘 유도체에 관한 것이다.The present invention relates to a piperidine derivative represented by the following general formula (I), which has excellent antimicrobial activity against Gram-negative bacteria but, in order to complement the disadvantage of quinolone antimicrobial agents having a remarkably low antibacterial activity against Gram- To a novel piperidine derivative which provides a pyridinedi derivative which provides a very useful intermediate.
상기식 중에서 R1, R2는 서로 같거나 다르며 각각 수소원자 또는 탄소수 1-3개의 저급 알킬기를 나타내며 n은 1 또는 2의 정수이고 m은 0 또는 1의 정수이다. n이 1일 때 m은 1이고 n이 2일 때 m은 0이다.R 1 and R 2 are the same or different and each represents a hydrogen atom or a lower alkyl group having 1 to 3 carbon atoms, n is an integer of 1 or 2, and m is an integer of 0 or 1. When n is 1, m is 1 and when n is 2, m is 0.
Description
본 발명은 다음 일반식(I)으로 표시되는 새로운 피페리딘 유도체에 관한 것이다The present invention relates to novel piperidine derivatives represented by the following general formula (I)
상기식 중에서 R1, R2는 같거나 다르며 각각 수소원자 또는 탄소수 1-3개의 저급 알킬기를 나타내며 n은 1 또는 2의 정수이고 m은 0 또는 1의 정수이다. n이 1일 때 m은 1이고 n이 2일 때 m은 0이다. 일반식(I)으로 표시된 화합물은 3번 또는 4번 위치의 비대칭탄소로 인한 광학적 이성질체를 포함한다. 따라서 모든 광학 이성질체 및 그들의 혼합물은 편리상 단일 구조식으로 표기한다.R 1 and R 2 are the same or different and each represents a hydrogen atom or a lower alkyl group having 1 to 3 carbon atoms, n is an integer of 1 or 2, and m is an integer of 0 or 1. When n is 1, m is 1 and when n is 2, m is 0. The compounds represented by the general formula (I) include optical isomers due to asymmetric carbons at the 3 or 4 positions. Thus, all optical isomers and mixtures thereof are conveniently referred to as monomers.
일반적으로 퀴놀론 카르복실산 항균제는 뛰어난 항균력과 광범위한 항균활성화합물로서 이미 널리 사용되고 있으며 그 대표적인 예로서 노플로사신, 에녹사신, 위 및 오플록사신 등이 현재 시판중에 있다. 그러나 이들 항균제의 경우 그람음성균에 대해서는 탁월한 항균력을 보여주지만 그람양성균에 대해서는 그 항균력이 현저히 떨어지고 또한 내성균 발현으로 인하여 새로운 항균제 개발이 요구되어져 왔다.In general, quinolone carboxylic acid antimicrobial agents are already widely used as antimicrobial active compounds having broad antibacterial activity and broad antibacterial activity. Typical examples of such antimicrobial active agents include noflosacin, enoxacin, stomach and oproxacin. However, these antimicrobial agents show excellent antimicrobial activity against Gram-negative bacteria, but their antimicrobial activity against Gram-positive bacteria is remarkably decreased and development of new antimicrobial agents due to the expression of resistant bacteria has been demanded.
이에 본 발명자들은 상술한 바와 같은 퀴놀론계 항균제의 단점을 보완하기 위해 기존의 퀴놀론 모핵의 C-7위치에 새로운 도입기를 찾아내려는 연구 결과 본 발명을 완성하게 되었다.Accordingly, the present inventors have completed the present invention as a result of finding out a new introducer at the C-7 position of the existing quinolone probes in order to supplement the disadvantages of the above-mentioned quinolone antimicrobial agents.
따라서 본 발명은 퀴놀론계 항균화합물에 도입되는 매우 유용한 중간체를 제공하는데 그 목적이 있다.Accordingly, it is an object of the present invention to provide a highly useful intermediate which is introduced into a quinolone antimicrobial compound.
이러한 본 발명의 상기 일반식(I)의 화합물 제조방법을 살펴보면 공지의 화합물(II)를 출발물질로 하여 다음의 반응과정을 거쳐 제조할 수 있다.The method for preparing the compound of formula (I) of the present invention can be prepared by using the known compound (II) as a starting material in the following reaction process.
상기식 중에서 R1, R2는 같거나 다르며 각각 수소원자 또는 탄소수 1-3개의 저급 알킬기를 나타내며 n은 1 또는 2의 정수이고 m은 0 또는 1의 정수이다. n이 1일 때 m은 1이고 n이 2일 때 m은 0이다. R3는 벤질 또는 벤질옥시카르보닐과 같은 아민보호기이다.R 1 and R 2 are the same or different and each represents a hydrogen atom or a lower alkyl group having 1 to 3 carbon atoms, n is an integer of 1 or 2, and m is an integer of 0 or 1. When n is 1, m is 1 and when n is 2, m is 0. R3 is an amine protecting group such as benzyl or benzyloxycarbonyl.
상기 반응과정에서 화합물(III)는 화합물(II)로부터 트리에틸아민, 디이소프로필에틸아민 등과 같은 적당한 염기 존재하에 벤질할라이드, 벤질클로로포메이트와 같은 아민보호기를 사용하여 제조할 수 있고 이것을 디에틸 아조디카로복실레이트와 트리페닐포스핀 존재하에 N-히드록시 프탈리미드와 반응시켜 화합물(IV)를 얻는다.Compound (III) can be prepared from compound (II) by using an amine protecting group such as benzyl halide or benzyl chloroformate in the presence of a suitable base such as triethylamine, diisopropylethylamine or the like, Is reacted with N-hydroxyphthalimide in the presence of azodicarboxylate and triphenylphosphine to give compound (IV).
화합물(IV)를 에탄올 용매하에 히드라진 하이드레이트와 반응시켜 화합물(V)를 만들고 이것을 팔라듐 존재하에 수소 반응시켜 상기 구조식(I)의 화합물을 얻을 수 있다.Compound (IV) can be reacted with hydrazine hydrate in an ethanol solvent to give compound (V), which can be hydrogenated in the presence of palladium to give compound of formula (I).
이와 같이 본 발명에 따라 제조된 상기 일반식(I)의 새로운 피페리딘 유도체는 항균활성을 갖는 각종 퀴놀론 유도체 화합물 제조시 도입기로 이용되는 원료화합물인 중간체로서 매우 유용하며 이러한 본 발명의 신규 화합물을 모핵에 도입한 퀴놀론 항균제는 뛰어난 항균활성을 나타낸다.As described above, the novel piperidine derivatives of the general formula (I) prepared according to the present invention are very useful as intermediates which are raw compounds used as a feeder for preparing various quinolone derivative compounds having antimicrobial activity. The quinolone antibacterial agent introduced into the mother nucleus shows excellent antibacterial activity.
이하 본 발명을 실시예로서 상세히 설명하는 바 본 발명이 다음의 실시예에 의해 한정되어지는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to Examples. However, the present invention is not limited by the following Examples.
실시예 1 : 1-벤질-4-히드록시피페리딘Example 1: Preparation of 1-benzyl-4-hydroxypiperidine
4-히드록시피페리딘 5g(50mmol)을 무수 디클로로메탄 100ml에 묽히고 트리에틸아민 8.18(60mmol)을 가한 후 0℃에서 벤질브로마이드 5.93ml(50mmol)를 천천히 첨가한 후 온도를 서서히 높혀 상온에서 4시간동안 교반시킨다.(50 mmol) of 4-hydroxypiperidine was diluted with 100 ml of anhydrous dichloromethane, and 8.18 (60 mmol) of triethylamine was added thereto. Then, 5.93 ml (50 mmol) of benzyl bromide was gradually added at 0 ° C, Stir for 4 hours.
반응액을 물과 소금물로서 차례로 씻어준 후 무수 MgSO4로 건조한 후 농축화여 목적화합물 10.05g(수율95%)을 얻었다.The reaction solution was washed successively with water and brine, dried over anhydrous MgSO 4 and concentrated to obtain 10.05 g (yield 95%) of the target compound.
1H-NMR(CDCl3, ppm) : 1.57(2H, m) 1.82(2H, m) 2.05(2H, m) 2.66(2H, m) 3.42(2H, s) 3.51(1H, s) 3.51(1H, m) 4.60(1H, s) 7.26(5H, s)2.51 (1H, m), 2.66 (2H, m), 3.42 (2H, s), 3.51 ) 4.60 (1H, s), 7.26 (5H, s)
실시예 2 : 3-(1-벤질-4-피페리디녹시)프탈리미드Example 2: Preparation of 3- (1-benzyl-4-piperidinoxy) phthalimide
무수 테트라히드로퓨란 200ml에 1-벤질-4-히드록시피페리딘 7.92g(36mmol), 트리페닐포스핀 9.44g(36mmol)과 N-히드록시프탈리미드 5.92g(35mmol)을 차례로 가하여 녹인 후 0℃에서 디에틸 아조디카로복실레이트 6.23ml(39.6mmol)을 천천히 첨가한 후 생성되는 트리페닐포스핀옥사이드를 거른 다음 칼럼크로마토그래피를 사용하여 목적화합물을 7.15g을 분리하였다.(수율55%)7.92 g (36 mmol) of 1-benzyl-4-hydroxypiperidine, 9.44 g (36 mmol) of triphenylphosphine and 5.92 g (35 mmol) of N-hydroxyphthalimide were dissolved in 200 ml of anhydrous tetrahydrofuran After 6.23 ml (39.6 mmol) of diethyl azodicarboxylate was added slowly at 0 ° C, the resulting triphenylphosphine oxide was filtered off and 7.15 g of the target compound was isolated by column chromatography (yield: 55% )
1H-NMR(CDCl3, ppm) : 1.85(2H, m) 2.10(4H, m) 2.69(2H, m) 3.45(2H, s) 3.57(1H, m) 7.27(5H, s) 7.81(4H, m)(2H, m), 2.47 (2H, s), 3.45 (2H, s), 3.57 (1H, )
실시예 3 : O-[4-(1-벤질피페리디닐)]히드록시아민Example 3: Synthesis of O- [4- (1-benzylpiperidinyl)] hydroxyamine
3-(1-벤질피페리디녹시)프탈리미드 6.56g(18mmol)을 50ml에탄올에 묽히고 히드라진 하이드레이트 1.1ml(18mmol)를 가해 2시간 동안 상온에서 교반시킨 후 포화탄산수소나트륨 30ml를 반응용기에 붓고 10분간 저어준후 디에틸에네르로 3번 추출한다.(18 mmol) of 3- (1-benzylpiperidinooxy) phthalimide was diluted with 50 ml of ethanol, and 1.1 ml (18 mmol) of hydrazine hydrate was added thereto. The mixture was stirred at room temperature for 2 hours. 30 ml of saturated sodium hydrogen carbonate Pour in water, stir for 10 minutes and extract 3 times with diethylenether.
1H-NMR(CDCl3, ppm) : 1.85(2H, m) 2.11(4H, m) 2.67(2H, m) 3.45(2H, s) 3.57(1H, m) 7.26(5H, S)(2H, s), 3.57 (1H, m), 7.26 (5H, s), 1.48 (2H,
실시예 4 : O-(4-피페리디닐)히드록시아민의 제조Example 4: Preparation of O- (4-piperidinyl) hydroxyamine
O-[3-(1-벤질피페리디닐]히드록시아민 2.3g(9.7mmol)을 100, ml에탄올레 묽히고 10% 팔라듐 0.2g을 현탁시킨다음 상온에서 6시간동안 60psi의 수소압력을 가하여 교반시킨 후 여과하여 여과액을 농축시켜 목적화합물을 700mg을 얻었다.(수율70%)2.3 g (9.7 mmol) of O- [3- (1-benzylpiperidinyl) hydroxyamine was diluted with 100 ml of ethanol, suspended in 0.2 g of 10% palladium, and hydrogen pressure of 60 psi was applied at room temperature for 6 hours After stirring, the mixture was filtered and the filtrate was concentrated to obtain 700 mg of the target compound (yield: 70%).
1H-NMR(CDCl3, ppm) : 1.31-1.55(2H, m) 1.86(2H, m) 2.55-2.65(2H, m) 3.04-3.10(2H, m) 3.42(1H, m)(2H, m), 3.42 (1H, m), 2.45 (2H, m)
실시예 5 : O-(3-피페리디닐)히드록시아민의 제조Example 5: Preparation of O- (3-piperidinyl) hydroxyamine
3-히드록시피페리딘 4g을 출발물로 하여 실시예 1,2,3,4와 동일한 방법으로 반응시켜 상기의 목적화합물 870mg을 얻었다.4 g of 3-hydroxypiperidine were used as starting materials and reacted in the same manner as in Examples 1, 2, 3 and 4 to obtain the desired compound (870 mg).
1H-NMR(CDCl3, ppm) : 1.12(2H, m) 1.47(2H, m) 2.44-2.70(4H, m) 3.65(1H, m)(2H, m), 2.44-2.70 (4H, m), 3.65 (1H, m)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019960034677A KR19980015378A (en) | 1996-08-21 | 1996-08-21 | New piperidine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019960034677A KR19980015378A (en) | 1996-08-21 | 1996-08-21 | New piperidine derivatives |
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| Publication Number | Publication Date |
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| KR19980015378A true KR19980015378A (en) | 1998-05-25 |
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| Application Number | Title | Priority Date | Filing Date |
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| KR1019960034677A Withdrawn KR19980015378A (en) | 1996-08-21 | 1996-08-21 | New piperidine derivatives |
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| KR (1) | KR19980015378A (en) |
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1996
- 1996-08-21 KR KR1019960034677A patent/KR19980015378A/en not_active Withdrawn
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