CN1199044A - New compound and its derivatives and their use - Google Patents
New compound and its derivatives and their use Download PDFInfo
- Publication number
- CN1199044A CN1199044A CN 97111758 CN97111758A CN1199044A CN 1199044 A CN1199044 A CN 1199044A CN 97111758 CN97111758 CN 97111758 CN 97111758 A CN97111758 A CN 97111758A CN 1199044 A CN1199044 A CN 1199044A
- Authority
- CN
- China
- Prior art keywords
- compound
- medicine
- new compound
- derivative
- derivatives
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 20
- 239000003814 drug Substances 0.000 claims abstract description 11
- ASCWBYZMMHUZMQ-UHFFFAOYSA-N bis(2-propoxyethyl) 4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCCOCCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOCCC)C1C1=CC=CC=C1OC(F)F ASCWBYZMMHUZMQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 abstract description 4
- 230000003042 antagnostic effect Effects 0.000 abstract description 2
- 229910001424 calcium ion Inorganic materials 0.000 abstract description 2
- 244000020518 Carthamus tinctorius Species 0.000 description 6
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 241000628997 Flos Species 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 241000208838 Asteraceae Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003130 cardiopathic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000002175 menstrual effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
A new compound is extracted from safflowr. Said compound and its derivatives have Ca-ion antagonistic activity, so they can be used to prepare the medicine for cardiovascular disease.
Description
A kind of new compound and the derivative thereof that the present invention relates to extract from safflower the invention still further relates to this compound and derivative thereof the purposes aspect the preparation medicine, the particularly purposes aspect the medicine of preparation treatment cardiovascular disorder.
Safflower is the dried floral of composite family (Compositae) plant Carthamus tinctorius, has the promoting blood circulation to restore menstrual flow effect, is widely used for gynaecopathia and cardiopathic treatment clinically.According to the record of modern Clinical Application and Chinese medicine book on Chinese herbal medicine usage, we have selected neonatal rat myocardial cell to cultivate is the pharmacologically active index, and the effective constituent of safflower has been carried out detailed tracking separation and successfully obtained its effective constituent.Six kinds of new compounds are arranged in these compositions, 15 kinds of isolated compounds from safflower first, comprising new compound of the present invention, but also found that this compound and derivative thereof have powerful calcium antagonism activity, thereby be accomplished the present invention.
One of purpose of the present invention provides new compound and the derivative thereof of a kind of general formula for (1):
Formula (1) wherein R can be H ,-CH
3Or
Preferred R is H.
Two of purpose of the present invention provides new compound and the purposes of derivative aspect the preparation medicine thereof that a kind of general formula is (1).
Three of purpose of the present invention provides a kind of general formula and is the new compound of (1) and derivative thereof the purposes at preparation cerebrocrast and treating cardiovascular disease prescription face.
According to the present invention, preferred R is the effective constituent of formula (1) compound of H as disease treatment, can become medicine to them and/or excipient combined preparation, and this medicine has the antagonistic action of calcium ion, can be used for the treatment of cardiovascular disorder.
In order to set forth the present invention better, be exemplified below, but this example is not used for scope of the present invention is limited.The extraction of embodiment 1 formula (1) compound with separate
1) extracts flos carthami with 50% aqueous ethanolic solution, reclaim the aqueous solution that obtains this extract behind the ethanol.
2) behind the aqueous solution with the ethyl acetate extraction Flos Carthami extract, adopt macroporous resin and sephadex lh-20 chromatography method to make with extra care as eluent with 50% second alcohol and water respectively its water-soluble portion, obtain the formula that R is H (1) compound, claim safflower alkali B again.The physical and chemical parameter of this compound is: molecular composition: C
27H
29NO
13Molecular weight: 575: high resolution mass spectrometry hrfabms:m/z598.1544|M+Na|
+(calcd 598.1537); Mass spectrum hrfabms:m/z598|M+Na|
+, 576|M+1|
+, 414; Infrared spectra ir (KBr): υ max 3431cm
-1, 1636cm
-1UV spectrum uv: λ max (MeOH) nm (log ε): 250 (3.38), 220 (3.61); | α |
25 D-297 (c=0.1, MeOH): proton nmr spectra
1H-nmr (in DMSO-d
6): δ 7.35 (1H, d, 15.7, H-8), 7.67 (1H, d, 15.7, H-9), 7.55 (2H, d, 8.6, H-11,15), 6.84 (2H, d, 8.6, H-12,14), 6.25 (1H, d, 2.1, H-17), 5.0～3.0 (sugar ' s protons, and H-18,19,20,21), 5.70 (1H, 4-OH), 10.05 (1H, 13-OH), 11.30 (1H, 16-OH), 18.01 (1H, 5-OH); Carbon-13 nmr spectra
13C-nmr (in DMSO-d
6): δ 185.7 (s, C-1), 114.7 (s, C-2), 141.2 (s, C-3), 77.9 (s, C-4), 196.0 (s, C-5), 109.4 (s, C-6), 180.6 (s, C-7), 119.0 (d, C-8), 140.9 (d, C-9), 126.4 (s, C-10), 130.3 (d, C-11,15), 115.7 (d, C-12,14), 160.1 (s, C-13), 138.1 (s, C-16), 101.3 (d, C-17), 74.1 (d, C-18), 78.5 (d, C-19), 71.0 (d, C-20), 63.22 (t, C-21), 84.2 (d, C-1 '), (69.1 d, C-2 '), 78.2 (d, C-3 '), 7) .0 (d, C-4 '), 78.8 (d, C-5 '), 60.8 (t, C-6 ').
Claims (5)
1. new compound and derivative thereof, its chemical structure of general formula is:
Wherein R can be H ,-CH
3Or
2. according to the compound and the derivative thereof of claim 1, the R in its formula of is H.
3. claim 1 or 2 compound and derivative thereof the purposes that is used to prepare medicine.
4. according to the purposes described in the claim 3, medicine wherein is a cerebrocrast.
5. according to the purposes described in the claim 3, medicine wherein is the cardiovascular medicine of treatment.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 97111758 CN1100039C (en) | 1997-05-08 | 1997-05-08 | New compound and its derivatives and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 97111758 CN1100039C (en) | 1997-05-08 | 1997-05-08 | New compound and its derivatives and their use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1199044A true CN1199044A (en) | 1998-11-18 |
| CN1100039C CN1100039C (en) | 2003-01-29 |
Family
ID=5171850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 97111758 Expired - Fee Related CN1100039C (en) | 1997-05-08 | 1997-05-08 | New compound and its derivatives and their use |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1100039C (en) |
-
1997
- 1997-05-08 CN CN 97111758 patent/CN1100039C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1100039C (en) | 2003-01-29 |
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|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |