CN1170722A - 新的香豆素衍生物、其制备方法和应用 - Google Patents
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- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- 238000000034 method Methods 0.000 title abstract description 9
- 150000001893 coumarin derivatives Chemical class 0.000 title abstract 3
- 230000031018 biological processes and functions Effects 0.000 claims abstract 2
- 150000004775 coumarins Chemical class 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 9
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 8
- -1 ethoxy methylene diethyl Chemical group 0.000 claims description 4
- 230000000845 anti-microbial effect Effects 0.000 claims description 3
- 230000000259 anti-tumor effect Effects 0.000 claims description 3
- 230000002155 anti-virotic effect Effects 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- NHNUFAASKXPOQA-UHFFFAOYSA-N (3-acetamido-2-hydroxyphenyl)arsonic acid Chemical compound C(C)(=O)NC=1C(=C(C=CC1)[As](O)(=O)O)O NHNUFAASKXPOQA-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- QWZHDKGQKYEBKK-UHFFFAOYSA-N 3-aminochromen-2-one Chemical class C1=CC=C2OC(=O)C(N)=CC2=C1 QWZHDKGQKYEBKK-UHFFFAOYSA-N 0.000 description 1
- LALNOCKWGFCEEB-UHFFFAOYSA-N 6-amino-3-hydroxychromen-2-one Chemical compound O1C(=O)C(O)=CC2=CC(N)=CC=C21 LALNOCKWGFCEEB-UHFFFAOYSA-N 0.000 description 1
- ZOJAINJCZSVZGW-UHFFFAOYSA-N 6-aminochromen-2-one Chemical compound O1C(=O)C=CC2=CC(N)=CC=C21 ZOJAINJCZSVZGW-UHFFFAOYSA-N 0.000 description 1
- FMAGIQPFINOMCX-UHFFFAOYSA-N 8-amino-3-hydroxychromen-2-one Chemical compound C1=C(O)C(=O)OC2=C1C=CC=C2N FMAGIQPFINOMCX-UHFFFAOYSA-N 0.000 description 1
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
- PQMOXTJVIYEOQL-UHFFFAOYSA-N Cumarin Natural products CC(C)=CCC1=C(O)C(C(=O)C(C)CC)=C(O)C2=C1OC(=O)C=C2CCC PQMOXTJVIYEOQL-UHFFFAOYSA-N 0.000 description 1
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- GLNDAGDHSLMOKX-UHFFFAOYSA-N coumarin 120 Chemical compound C1=C(N)C=CC2=C1OC(=O)C=C2C GLNDAGDHSLMOKX-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
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- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/14—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 6 and unsubstituted in position 7
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/18—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
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Abstract
本发明涉及由通式Ⅰ表示的新的香豆素衍生物,式中:R1=NH2或－NHCH=C(CO2C2H5)2,R2=R3=R4=H,R5=F,R1=R3=NHCH=C(CO2C2H5)2,R2=R4=R5=H,R1=H或OH,R3=NHCH＝C(CO2C2H5)2,R2=R4=R5=H,R1=OH,R2=R3=R4=H,R5=NHCH=C(CO2C2H5)2,R1=R3=R5=H,R2=CH3或CF3,R4=NHCH=C(CO2C2H5)2,其制备方法和它们作为中间体用于合成具有潜在生物学作用的新的香豆素衍生物。
Description
本发明涉及由通式I表示的新的香豆素衍生物：
式中：R1＝NH2或-NHCH＝C(CO2C2H5)2，R2＝R3＝R4＝H，R5＝F，R1＝R3＝NHCH＝C(CO2C2H5)2，R2＝R4＝R5＝H，R1＝H或OH，R3＝NHCH＝C(CO2C2H5)2，R2＝R4＝R5＝H，R1＝OH，R2＝R3＝R4＝H，R5＝-NHCH＝C(CO2C2H5)2，R1＝R3＝R5＝H，R2＝CH3或CF3，R4＝-NHCH＝C(CO2C2H5)2，
本发明的这些通式I的新的香豆素衍生物通过化学式II所示的取代香豆素
式中：R1＝R3＝R4＝R5＝H，R2＝NH2，R1＝R3＝NH2，R2＝R4＝R5＝H，R1＝OH，R2＝R4＝R5＝H，R3＝NH2，R1＝OH，R2＝R3＝R4＝H，R5＝NH2，R1＝NH2，R2＝R3＝R4＝H，R5＝F，R1＝R3＝R5＝H，R2＝CH3或CF3，R4＝-NH2，与化学式III的乙氧基亚甲基丙二酸二乙酯
C2H5OCH＝C(CO2C2H5)2
III在120℃、在10分钟-27小时的期间内反应来制备，获得带有上述规定的取代基的通式I的香豆素丙二酸酯。
起始的通式II的被取代的氨基香豆素，除了R1＝NH2、R2＝R3＝R4＝H、R5＝F的化合物外，在以下的文献中已经作过说明：F.W.Linch，J.Chem.Soc.101(1912)1758；G.T.Morgan，F.M.G.Micklethwait，J.Chem.Soc.85(1904)1230；G.Kokotos，C.Tzougraki，J.Heterocyclic Chem.23(1986)87；I.C.Lvanov，S.K.Karagiosov，I.Manolov，Arch.Pharm.(Weinheim)324(1991)61。
通式I的新的香豆素衍生物对于合成具有潜在生物学作用，例如抗微生物、抗肿瘤和抗病毒作用的新的香豆素衍生物是有用的中间体。
本发明的方法用下面的实施例具体说明，但是本发明不仅限于这些实施例。实施例13-氨基-8-氟香豆素
将在浓硫酸(2.65g，0.027摩尔)中的3-乙酰氨基-8-氟香豆素(3.00g，0.014摩尔)溶液在70-80℃加热1小时。溶液冷却后倒入冰-水混合物中，用饱和NaHCO3水溶液碱化至pH＝6，随后在+4℃让它沉淀。所得到的3-氨基-8-氟香豆素在50％乙醇中重结晶(1.63g，67％)。熔点：173-174℃。分析：C9H6FNO2的计算值：C＝60.34；H＝3.38；N＝7.82。实测值：C＝59.97；H＝3.22；N＝7.72。1H-NMR(DMSO-d6)·δ/ppm：5.9(s，NH2)，6.7(s，H4)；7.1-7.2(m，H5-H7).m/z：178(M-)，151，141，134，127.实施例2{[(2-氧代-2H[1]-苯并吡喃-6-基)氨基]亚甲基}丙二酸二乙酯
将在乙氧基亚甲基丙二酸二乙酯(3.03g，0.014摩尔)的6-氨基香豆素(2.00g，0.012摩尔)溶液在120℃加热10分钟，反应混合物发生固化。得到的{[(2-氧代-2H[1]-苯并吡喃-6-基)氨基]亚甲基}丙二酸二乙酯(3.95g，96％)浅棕色沉淀在乙醇中进行再结晶。熔点：141-142℃。分析：C17H17NO6的计算值：C＝61.62；H＝5.17；N＝4.23。实测值：C＝61.87；H＝4.99；N＝4.17。1H-NMR(DMSO-d6)·δ/ppm：1.3(t，CH3)，4.3(q，CH2)；6.6(d，H3)；7.7(d，H8)；7.9(d，H7)，8.5(d；H5)；10.0(d；H4)；12.4(bs，NH).实施例3{[(2-氧代-2H[1]-苯并吡喃-3，6-二-基)二氨基]二亚甲基}丙二酸四乙酯
以3，6-二氨基香豆素(1.00g，5.676毫摩尔)和乙氧基亚甲基丙二酸二乙酯(2.81g，0.013摩尔)为原料，按照实施例2描述的方法制备这种化合物。反应时间：6小时。从乙醇中再结晶后得到{[(2-氧代-2H[1]-苯并吡喃-3，6-二-基)二氨基]-二亚甲基}丙二酸四乙酯(2.55g，87％)黄-绿色晶体。熔点：131-134℃。分析：C25H28N2O10的计算值：C＝58.13；H＝5.46；N＝5.43。实测值：C＝57.74；H＝5.19；N＝5.40。1H-NMR(DMSO-d6)·δ/ppm：1.2(t，CH3)，4.2(q，CH2)；7.4(m，CH)；7.6(s，H5)；7.9(s，H4)，8.2-8.5(m；H7-H8)；10.6-10.8(m，2NH).实施例4{[(3-羟基-2-氧代-2H[1]-苯并吡喃-6-基)氨基]亚甲基}丙二酸二乙酯
以6-氨基-3-羟基香豆素(0.88g，4.967毫摩尔)为原料按照实施例2描述的方法制备这种化合物。反应时间：1小时。冷却该溶液后得到黄-褐色{[(3-羟基-2-氧代-2H[1]-苯并吡喃-6-基)氨基]亚甲基}丙二酸二乙酯的沉淀，在冰醋酸中再结晶(1.52g，88％)。分析：C17H17NO7的计算值：C＝58.79；H＝4.93；N＝4.03。实测值：C＝58.64；H＝4.64；N＝4.25。1H-NMR(DMSO-d6)·δ/ppm：1.3(t，CH3)，4.2(q，CH2)；7.1-8.4(m，ArH)；10.5(s；NH)；10.8(d；OH).m/z：347(M+)，302，149，79，61，45，43.实施例5{[(3-羟基-2-氧代-2H[1]-苯并吡喃-8-基)氨基]亚甲基}丙二酸二乙酯
以8-氨基-3-羟基香豆素(1.93g，0.011摩尔)为原料，按照实施例2描述的方法制备这种化合物。反应时间：4小时。在冰醋酸中再结晶后得到的{[(3-羟基-2-氧代-2H[1]-苯并吡喃-8-基)氨基]亚甲基}丙二酸二乙酯沉淀呈棕色有闪光面的结晶(3.37g，89％)。分析：C17H17NO7的计算值：C＝58.79；H＝4.93；N＝4.03。实测值：C＝58.98；H＝4.89；N＝3.91。1H-NMR(DMSO-d6)·δ/ppm：1.3(t，CH3)，4.2(q，CH2)；7.1-8.5(m，ArH)；10.7(s；NH)；11.1(d；OH).m/z：347(M+)，302，273，199，177，70，61，47.实施例6{[(8-氟-2-氧代-2H[1]-苯并吡喃-3-基)氨基]亚甲基}丙二酸二乙酯
以3-氨基-8-氟-香豆素(2.00g，9.250毫摩尔)为原料，按照实施例2描述的方法制备这种化合物。反应时间：5小时。冷却该溶液后得到浅黄色的{[(8-氟-2-氧代-2H[1]-苯并吡喃-3-基)氨基]亚甲基}丙二酸二乙酯沉淀，在乙醇中再结晶(2.76g，95％)。熔点：175-177℃。分析：C17H16FNO6的计算值：C＝58.45；H＝4.62；N＝4.01。实测值：C＝58.38；H＝4.46；N＝3.98。实施例7{[(4-甲基-2-氧代-2H[1]-苯并吡喃-7-基)氨基]亚甲基}丙二酸二乙酯
以7-氨基-4-甲基香豆素(5.00g，0.029摩尔)为原料，按照实施例2所述的方法制备这种化合物。反应时间：30分钟。在乙醇中重结晶沉淀出的{[(4-甲基-2-氧代-2H[1]-苯并吡喃-7-基)氨基]亚甲基}丙二酸二乙酯(9.70g，98％)。熔点：139-140℃。分析：C18H19NO6的计算值：C＝62.60；H＝5.55；N＝4.06。实测值：C＝61.97；H＝5.05；N＝4.25。实施例8{[(4-(三氟甲基)-2-氧代-2H[1]-苯并吡喃-7-基)氨基]亚甲基}丙二酸二乙酯
以7-氨基-4-(三氟甲基)香豆素(3.00g，0.015摩尔)为原料，按照实施例2描述的方法制备这种化合物。反应时间：27小时。通过冷却沉淀出黄色{[(4-三氟甲基-2-氧代-2H[1]-苯并吡喃-7-基)氨基]亚甲基}丙二酸二乙酯，让它在乙醇中再结晶(4.83g，92％)。熔点：125-126℃。分析：C18H16F3NO6的计算值：C＝54.14；H＝4.04；N＝3.51。实测值：C＝54.12；H＝4.17；N＝3.46。1H-NMR(DMSO-d6)·δ/ppm：1.3(t，CH3)，4.2(q，CH2)；6.8(s，H3)，7.4-7.6(m；H6，H8，CH)；8.4(d，H5)；10.7(d；NH).
Claims (12)
1、通式I的新的香豆素衍生物，式中：R1＝NH2或-NHCH＝C(CO2C2H5)2，R2＝R3＝R4＝H，R5＝F，R1＝R3＝NHCH＝C(CO2C2H5)2，R2＝R4＝R5＝H，R1＝H或OH，R3＝NHCH＝C(CO2C2H5)2，R2＝R4＝R5＝H，R1＝OH，R2＝R3＝R4＝H，R5＝-NHCH＝C(CO2C2H5)2，R1＝R3＝R5＝H，R2＝CH3或CF3，R4＝-NHCH＝C(CO2C2H5)2。
2、权利要求1的通式I的香豆素衍生物，其特征在于R1＝NH2，R2＝R3＝R4＝H，R5＝F。
3、权利要求1的通式I的香豆素衍生物，其特征在于R1＝R2＝R4＝R5＝H，R3＝-NHCH＝C(CO2C2H5)2。
4、权利要求1的通式I的香豆素衍生物，其特征在于R2＝R4＝R5＝H，R1＝R3＝-NHCH＝C(CO2C2H5)2。
5、权利要求1的通式I的香豆素衍生物，其特征在于R1＝OH，R3＝-NHCH＝C(CO2C2H5)2，R2＝R3＝R4＝H。
6、权利要求1的通式I的香豆素衍生物，其特征在于R1＝OH，R2＝R3＝R4＝H，R5＝-NHCH＝C(CO2C2H5)2，。
7、权利要求1的通式I的香豆素衍生物，其特征在于R1＝-NHCH＝C(CO2C2H5)2，R2＝R3＝R4＝H，R5＝F。
8、权利要求1的通式I的香豆素衍生物，其特征在于R1＝R3＝R5＝H，R2＝CH3，R4＝-NHCH＝C(CO2C2H5)2。
9、权利要求1的通式I的香豆素衍生物，其特征在于R1＝R3＝R5＝H，R2＝CF3，R4＝-NHCH＝C(CO2C2H5)2。
10、权利要求1的通式I的化合物的制备方法，其特征在于将通式II的化合物
式中：R1＝R3＝R4＝R5＝H，R2＝NH2，R1＝R3＝NH2，R2＝R4＝R5＝H，R1＝OH，R2＝R4＝R5＝H，R3＝NH2，R1＝OH，R2＝R3＝R4＝H，R5＝NH2，R1＝NH2，R2＝R3＝R4＝H，R5＝F，R1＝R3＝R5＝H，R2＝CH3或CF3，R4＝-NH2，与通式III的乙氧基亚甲基丙二酸二乙酯
C2H5OCH＝C(CO2C2H5)2
III在120℃温度下加热10分钟至27小时，然后冷却，沉淀出香豆素丙二酸酯。
11、根据权利要求1的香豆素衍生物，其特征在于，它们可用作合成具有潜在生物学作用，例如抗微生物、抗肿瘤和抗病毒作用的新的香豆素衍生物的中间体。
12、权利要求1的新的香豆素衍生物的应用，作为中间体用于合成具有潜在的生物学作用，例如抗微生物、抗肿瘤和抗病毒作用的新的香豆素衍生物。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR960308A HRP960308A2 (en) | 1996-07-02 | 1996-07-02 | New coumarine derivatives, process for the preparation thereof and their use |
| HRP960308A | 1996-07-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1170722A true CN1170722A (zh) | 1998-01-21 |
Family
ID=10946423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97101199A Pending CN1170722A (zh) | 1996-07-02 | 1997-06-28 | 新的香豆素衍生物、其制备方法和应用 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5840922A (zh) |
| EP (1) | EP0816353B1 (zh) |
| JP (1) | JPH1067768A (zh) |
| CN (1) | CN1170722A (zh) |
| AT (1) | ATE211136T1 (zh) |
| BA (1) | BA97239A (zh) |
| BG (1) | BG63045B1 (zh) |
| CA (1) | CA2209404A1 (zh) |
| CZ (1) | CZ207397A3 (zh) |
| DE (1) | DE69709252T2 (zh) |
| HR (1) | HRP960308A2 (zh) |
| HU (1) | HUP9701134A3 (zh) |
| PL (1) | PL320912A1 (zh) |
| PT (1) | PT816353E (zh) |
| RU (1) | RU2135490C1 (zh) |
| SI (1) | SI9700176B (zh) |
| SK (1) | SK282106B6 (zh) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101747171A (zh) * | 2008-12-17 | 2010-06-23 | 上海药明康德新药开发有限公司 | 3-取代芳香基丙酸的快速合成方法 |
| CN101497593B (zh) * | 2009-03-18 | 2011-09-21 | 华南理工大学 | 5-羟基香豆素和吡喃型香豆素类化合物及合成方法与应用 |
| CN102898502A (zh) * | 2012-09-29 | 2013-01-30 | 首都医科大学 | 香豆素衍生物及其制备方法和应用 |
| CN104974122A (zh) * | 2015-07-02 | 2015-10-14 | 云南中烟工业有限责任公司 | 一种源自烟草的香豆素化合物、其制备方法和用途 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1281599C (zh) * | 2003-05-15 | 2006-10-25 | 中国科学院上海有机化学研究所 | 香豆素类化合物和合成方法 |
| CN104987328A (zh) * | 2012-05-23 | 2015-10-21 | 复旦大学 | 7-氧、硫或氮杂取代香豆素及其衍生物和用途 |
| RU2733731C1 (ru) * | 2019-07-04 | 2020-10-06 | Федеральное государственное автономное образовательное учреждение высшего образования "Уральский федеральный университет имени первого Президента России Б.Н. Ельцина" | Способ получения промежуточных продуктов для синтеза каланолидов и их аналогов |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3313818A (en) * | 1965-04-14 | 1967-04-11 | Sterling Drug Inc | 7, 10-dihydro-3, 10-dioxo-7-(lower-alkyl)-3h-pyrano[3, 2-f]quinoline-3-carboxylic acid derivatives |
| US4210758A (en) * | 1979-03-21 | 1980-07-01 | Warner-Lambert Company | 1,5-Dihydro-1,5-dioxo-N-1H-tetrazol-5-yl-4H-[1]benzopyrano[3,4-b]pyridine-2-carboxamides |
| HRP960352A2 (en) * | 1996-07-26 | 1998-08-31 | Pliva Pharm & Chem Works | Novel coumarin quinoline carboxylic acids |
-
1996
- 1996-07-02 HR HR960308A patent/HRP960308A2/hr not_active Application Discontinuation
-
1997
- 1997-06-27 SK SK875-97A patent/SK282106B6/sk unknown
- 1997-06-27 BA BA970239A patent/BA97239A/bs unknown
- 1997-06-28 CN CN97101199A patent/CN1170722A/zh active Pending
- 1997-06-30 JP JP9174453A patent/JPH1067768A/ja active Pending
- 1997-06-30 CA CA002209404A patent/CA2209404A1/en not_active Abandoned
- 1997-06-30 CZ CZ972073A patent/CZ207397A3/cs unknown
- 1997-07-01 BG BG101722A patent/BG63045B1/bg unknown
- 1997-07-01 EP EP97110824A patent/EP0816353B1/en not_active Expired - Lifetime
- 1997-07-01 PT PT97110824T patent/PT816353E/pt unknown
- 1997-07-01 AT AT97110824T patent/ATE211136T1/de not_active IP Right Cessation
- 1997-07-01 RU RU97111207A patent/RU2135490C1/ru active
- 1997-07-01 HU HU9701134A patent/HUP9701134A3/hu unknown
- 1997-07-01 DE DE69709252T patent/DE69709252T2/de not_active Expired - Fee Related
- 1997-07-02 SI SI9700176A patent/SI9700176B/sl unknown
- 1997-07-02 US US08/887,217 patent/US5840922A/en not_active Expired - Fee Related
- 1997-07-02 PL PL97320912A patent/PL320912A1/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101747171A (zh) * | 2008-12-17 | 2010-06-23 | 上海药明康德新药开发有限公司 | 3-取代芳香基丙酸的快速合成方法 |
| CN101497593B (zh) * | 2009-03-18 | 2011-09-21 | 华南理工大学 | 5-羟基香豆素和吡喃型香豆素类化合物及合成方法与应用 |
| CN102898502A (zh) * | 2012-09-29 | 2013-01-30 | 首都医科大学 | 香豆素衍生物及其制备方法和应用 |
| CN102898502B (zh) * | 2012-09-29 | 2014-07-23 | 首都医科大学 | 香豆素衍生物及其制备方法和应用 |
| CN104974122A (zh) * | 2015-07-02 | 2015-10-14 | 云南中烟工业有限责任公司 | 一种源自烟草的香豆素化合物、其制备方法和用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| BG101722A (en) | 1998-03-31 |
| EP0816353A3 (en) | 1998-03-04 |
| HUP9701134A3 (en) | 2001-02-28 |
| RU2135490C1 (ru) | 1999-08-27 |
| CZ207397A3 (cs) | 1998-01-14 |
| ATE211136T1 (de) | 2002-01-15 |
| SK87597A3 (en) | 1998-02-04 |
| HU9701134D0 (en) | 1997-08-28 |
| EP0816353B1 (en) | 2001-12-19 |
| HRP960308A2 (en) | 1998-08-31 |
| PT816353E (pt) | 2002-05-31 |
| CA2209404A1 (en) | 1998-01-02 |
| DE69709252D1 (de) | 2002-01-31 |
| SI9700176A (sl) | 1998-02-28 |
| HUP9701134A2 (hu) | 1998-12-28 |
| US5840922A (en) | 1998-11-24 |
| BA97239A (bs) | 2000-11-06 |
| SK282106B6 (sk) | 2001-11-06 |
| SI9700176B (sl) | 2002-02-28 |
| BG63045B1 (bg) | 2001-02-28 |
| PL320912A1 (en) | 1998-01-05 |
| DE69709252T2 (de) | 2002-07-25 |
| JPH1067768A (ja) | 1998-03-10 |
| EP0816353A2 (en) | 1998-01-07 |
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