GB2173500A - Benz (b)indeno (2, 1-d)pyran drugs - Google Patents
Benz (b)indeno (2, 1-d)pyran drugs Download PDFInfo
- Publication number
- GB2173500A GB2173500A GB08607817A GB8607817A GB2173500A GB 2173500 A GB2173500 A GB 2173500A GB 08607817 A GB08607817 A GB 08607817A GB 8607817 A GB8607817 A GB 8607817A GB 2173500 A GB2173500 A GB 2173500A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- extract
- effect
- drug
- caesalpinia
- 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.)
- Withdrawn
Links
- 239000003814 drug Substances 0.000 title claims description 60
- 229940079593 drug Drugs 0.000 title claims description 56
- QIZJDPLDPJMGOJ-UHFFFAOYSA-N indeno[1,2-c]chromene Chemical compound C12=COC3=CC=C[CH]C3=C2C=C2[C]1C=CC=C2 QIZJDPLDPJMGOJ-UHFFFAOYSA-N 0.000 title claims description 10
- UWHUTZOCTZJUKC-JKSUJKDBSA-N brazilin Chemical compound C12=CC(O)=C(O)C=C2C[C@]2(O)[C@H]1C1=CC=C(O)C=C1OC2 UWHUTZOCTZJUKC-JKSUJKDBSA-N 0.000 claims description 93
- UWHUTZOCTZJUKC-CVEARBPZSA-N brazilin Natural products C12=CC(O)=C(O)C=C2C[C@@]2(O)[C@@H]1C1=CC=C(O)C=C1OC2 UWHUTZOCTZJUKC-CVEARBPZSA-N 0.000 claims description 89
- 206010012601 diabetes mellitus Diseases 0.000 claims description 86
- 239000000284 extract Substances 0.000 claims description 70
- 230000000694 effects Effects 0.000 claims description 57
- 210000004369 blood Anatomy 0.000 claims description 54
- 239000008280 blood Substances 0.000 claims description 54
- WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical group C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 claims description 52
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 241000196324 Embryophyta Species 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 27
- 239000002023 wood Substances 0.000 claims description 25
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 24
- 230000002401 inhibitory effect Effects 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 210000003743 erythrocyte Anatomy 0.000 claims description 20
- 230000001965 increasing effect Effects 0.000 claims description 20
- 241000522234 Caesalpinia Species 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 235000015162 Caesalpinia sappan Nutrition 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 102000004190 Enzymes Human genes 0.000 claims description 14
- 108090000790 Enzymes Proteins 0.000 claims description 14
- HLUCICHZHWJHLL-UHFFFAOYSA-N hematein Chemical compound C12=CC=C(O)C(O)=C2OCC2(O)C1=C1C=C(O)C(=O)C=C1C2 HLUCICHZHWJHLL-UHFFFAOYSA-N 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 14
- 230000002132 lysosomal effect Effects 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 238000000605 extraction Methods 0.000 claims description 10
- 230000004060 metabolic process Effects 0.000 claims description 10
- 150000003180 prostaglandins Chemical class 0.000 claims description 10
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- MLWIYODOURBGPI-MRXNPFEDSA-N brazilein Chemical compound C12=CC=C(O)C=C2OC[C@@]2(O)C1=C1C=C(O)C(=O)C=C1C2 MLWIYODOURBGPI-MRXNPFEDSA-N 0.000 claims description 9
- MLWIYODOURBGPI-UHFFFAOYSA-N brazilein Natural products C12=CC=C(O)C=C2OCC2(O)C1=C1C=C(O)C(=O)C=C1C2 MLWIYODOURBGPI-UHFFFAOYSA-N 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 239000002775 capsule Substances 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- 235000007627 Caesalpinia Nutrition 0.000 claims description 5
- 235000009133 Caesalpinia coriaria Nutrition 0.000 claims description 5
- 235000002687 Caesalpinia echinata Nutrition 0.000 claims description 5
- 235000005082 Caesalpinia paraguariensis Nutrition 0.000 claims description 5
- 241001618206 Libidibia coriaria Species 0.000 claims description 5
- 241000127464 Paubrasilia echinata Species 0.000 claims description 5
- 230000003178 anti-diabetic effect Effects 0.000 claims description 5
- 230000000069 prophylactic effect Effects 0.000 claims description 5
- -1 aliphatic ketones Chemical class 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 241000209639 Biancaea sappan Species 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 50
- 241001465754 Metazoa Species 0.000 description 46
- 241000700159 Rattus Species 0.000 description 31
- 238000010171 animal model Methods 0.000 description 31
- 238000012360 testing method Methods 0.000 description 31
- 229940125396 insulin Drugs 0.000 description 26
- 102000004877 Insulin Human genes 0.000 description 24
- 108090001061 Insulin Proteins 0.000 description 24
- 238000011282 treatment Methods 0.000 description 14
- 230000037396 body weight Effects 0.000 description 13
- 230000005764 inhibitory process Effects 0.000 description 12
- 244000306301 Caesalpinia sappan Species 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 11
- 229940088598 enzyme Drugs 0.000 description 11
- 239000008103 glucose Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 10
- 239000003472 antidiabetic agent Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- 230000002776 aggregation Effects 0.000 description 8
- 238000004220 aggregation Methods 0.000 description 8
- HIMXGTXNXJYFGB-UHFFFAOYSA-N alloxan Chemical compound O=C1NC(=O)C(=O)C(=O)N1 HIMXGTXNXJYFGB-UHFFFAOYSA-N 0.000 description 8
- 229940126904 hypoglycaemic agent Drugs 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 6
- 235000021588 free fatty acids Nutrition 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 6
- 229960001052 streptozocin Drugs 0.000 description 6
- 241000282414 Homo sapiens Species 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 description 5
- 229960001123 epoprostenol Drugs 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000007446 glucose tolerance test Methods 0.000 description 5
- 150000002632 lipids Chemical class 0.000 description 5
- 230000002093 peripheral effect Effects 0.000 description 5
- 210000002381 plasma Anatomy 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- 102000003746 Insulin Receptor Human genes 0.000 description 4
- 108010001127 Insulin Receptor Proteins 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 108010069102 Thromboxane-A synthase Proteins 0.000 description 4
- 210000000577 adipose tissue Anatomy 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 230000001939 inductive effect Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 206010062198 microangiopathy Diseases 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 102000005744 Glycoside Hydrolases Human genes 0.000 description 3
- 108010031186 Glycoside Hydrolases Proteins 0.000 description 3
- 102000005237 Isophane Insulin Human genes 0.000 description 3
- 108010081368 Isophane Insulin Proteins 0.000 description 3
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 3
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 208000011775 arteriosclerosis disease Diseases 0.000 description 3
- 210000001772 blood platelet Anatomy 0.000 description 3
- LEMUFSYUPGXXCM-JNEQYSBXSA-N caninsulin Chemical group [Zn].C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC3N=CN=C3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1C=NC=N1 LEMUFSYUPGXXCM-JNEQYSBXSA-N 0.000 description 3
- 239000007979 citrate buffer Substances 0.000 description 3
- 239000000306 component Substances 0.000 description 3
- 230000004089 microcirculation Effects 0.000 description 3
- 238000010606 normalization Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000000291 postprandial effect Effects 0.000 description 3
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 3
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 2
- 102000002268 Hexosaminidases Human genes 0.000 description 2
- 108010000540 Hexosaminidases Proteins 0.000 description 2
- 206010022489 Insulin Resistance Diseases 0.000 description 2
- 206010054805 Macroangiopathy Diseases 0.000 description 2
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 2
- 102000015439 Phospholipases Human genes 0.000 description 2
- 108010064785 Phospholipases Proteins 0.000 description 2
- 229920001131 Pulp (paper) Polymers 0.000 description 2
- 241000786363 Rhampholeon spectrum Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 108090000190 Thrombin Proteins 0.000 description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000007775 late Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000011866 long-term treatment Methods 0.000 description 2
- 229940118019 malondialdehyde Drugs 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- 210000004623 platelet-rich plasma Anatomy 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 230000002250 progressing effect Effects 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- 206010059245 Angiopathy Diseases 0.000 description 1
- 235000014145 Caesalpinia bonduc Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102000004366 Glucosidases Human genes 0.000 description 1
- 108010056771 Glucosidases Proteins 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 240000007829 Haematoxylum campechianum Species 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 1
- BJXXCOMGRRCAGN-CLFAGFIQSA-N [2,2-bis(hydroxymethyl)-3-[(z)-octadec-9-enoyl]oxypropyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(CO)(CO)COC(=O)CCCCCCC\C=C/CCCCCCCC BJXXCOMGRRCAGN-CLFAGFIQSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000023852 carbohydrate metabolic process Effects 0.000 description 1
- 235000021256 carbohydrate metabolism Nutrition 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000001609 comparable effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000013399 early diagnosis Methods 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000007986 glycine-NaOH buffer Substances 0.000 description 1
- 230000003345 hyperglycaemic effect Effects 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000003859 lipid peroxidation Effects 0.000 description 1
- 230000004132 lipogenesis Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 108010064377 prostacyclin synthetase Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000005084 renal tissue Anatomy 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 239000010875 treated wood Substances 0.000 description 1
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- 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
- C07D311/94—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 condensed with rings other than six-membered or with ring systems containing such rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/331—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using water, e.g. cold water, infusion, tea, steam distillation or decoction
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Alternative & Traditional Medicine (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853511609 DE3511609A1 (de) | 1985-03-29 | 1985-03-29 | Arzneimittel, dessen herstellung und verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8607817D0 GB8607817D0 (en) | 1986-04-30 |
| GB2173500A true GB2173500A (en) | 1986-10-15 |
Family
ID=6266818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08607817A Withdrawn GB2173500A (en) | 1985-03-29 | 1986-03-27 | Benz (b)indeno (2, 1-d)pyran drugs |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4918099A (en:Method) |
| EP (1) | EP0205775A3 (en:Method) |
| KR (1) | KR870700358A (en:Method) |
| AU (1) | AU5527786A (en:Method) |
| DE (1) | DE3511609A1 (en:Method) |
| DK (1) | DK573386A (en:Method) |
| GB (1) | GB2173500A (en:Method) |
| GR (1) | GR860828B (en:Method) |
| NZ (1) | NZ215678A (en:Method) |
| WO (1) | WO1986005689A1 (en:Method) |
| ZA (1) | ZA862351B (en:Method) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2684378B1 (fr) * | 1991-11-29 | 1994-12-23 | Bioxytech | Procede de dosage de l'activite sod utilisant la braziline ou l'un de ses derives, necessaires pour sa mise en óoeuvre, composes derives de la braziline et leur preparation. |
| EP0625209B1 (fr) * | 1991-11-29 | 1996-07-17 | Oxis International S.A. | Procede de dosage de l'activite sod utilisant un compose autoxydable, necessaire pour sa mise en oeuvre, composes autoxydables et leur preparation |
| GB9704904D0 (en) * | 1997-03-10 | 1997-04-30 | Riley Fletcher Foundation The | Essential oil composition |
| KR100362941B1 (ko) * | 1999-05-17 | 2002-11-30 | 한국과학기술연구원 | 헤마테인을 함유하는 고지혈증 및 동맥경화증 예방 및 치료용 조성물 |
| US6238696B1 (en) | 2000-01-07 | 2001-05-29 | Gaia Herbs, Inc. | Process for providing herbal medicants in cellulose derivative capsules |
| EP1416948A1 (en) * | 2001-08-13 | 2004-05-12 | Riley, Michael Hargreaves | Compositions for removal of toxins |
| US6585998B2 (en) * | 2001-11-13 | 2003-07-01 | Rudolph Cartwright | Nutraceutical composition |
| KR100362940B1 (ko) * | 2002-05-17 | 2002-11-30 | 한국과학기술연구원 | 헤마테인을 함유하는 고지혈증 및 동맥경화증 예방 및치료용 조성물 |
| US20050118324A1 (en) * | 2003-12-02 | 2005-06-02 | Mathew Anna M. | Good living tea - a diabetic dietary supplement drink |
| KR100888840B1 (ko) * | 2008-08-25 | 2009-03-17 | (주)케이피티 | 광안정성을 향상시킨 천연색소를 염착한 셀룰로오스를 함유하는 화장료 원료용 조성물, 및 이를 포함하는 비쥬얼 운반 시스템 |
| TWI375671B (en) * | 2010-03-01 | 2012-11-01 | Univ China Medical | Pharmaceutical compositions containing brazilin for inhibiting expression of cytokines of t helper cell type ii and/or inhibiting expression of chemokines and uses of the same |
| KR102088768B1 (ko) * | 2018-05-15 | 2020-03-17 | 한림대학교 산학협력단 | 소목(Caesalpinia eriostachys Benth) 추출물을 유효성분으로 함유하는 통증 예방 또는 치료용 조성물 |
| US20220024944A1 (en) * | 2018-10-23 | 2022-01-27 | Myelopro Diagnostics And Research Gmbh | Compounds targeting mutant calreticulin |
| CN115252610B (zh) * | 2020-02-26 | 2024-03-26 | 上海科技大学 | 质子泵抑制剂在抗冠状病毒中的应用 |
| CN114133446A (zh) * | 2021-12-31 | 2022-03-04 | 方坦思(上海)生物医药有限公司 | 单克隆抗体的纯化方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1281526A (en) * | 1968-10-25 | 1972-07-12 | Lawson Tait Medical And Scient | Therapeutic compositions |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US637707A (en) * | 1898-01-06 | 1899-11-21 | Francis Emile Bucher | Process of treating logwood extracts. |
| FR319945A (fr) * | 1902-03-25 | 1902-11-27 | Jacquemin | Procédé de fabrication industrielle de l'hématéine, par oxydation directe de l'hématoxyline |
| GB190406428A (en) * | 1904-03-16 | 1904-04-21 | Roberto Lepetit | Improvements in and relating to the Manufacture of a Condensation Product from Haematoxylin and Formaldehyde. |
| US1720278A (en) * | 1920-04-19 | 1929-07-09 | Elmer H King | Chemical substance |
| US4147691A (en) * | 1977-03-31 | 1979-04-03 | University Of Iowa Research Foundation | Process for the extraction and purification of cesalin |
| US4363669A (en) * | 1979-12-05 | 1982-12-14 | Merck & Co., Inc. | Dispersible xanthan gum blends |
| LU83173A1 (fr) * | 1981-02-27 | 1981-06-05 | Oreal | Nouvelles compositions cosmetiques pour le traitement des cheveux et de la peau contenant une poudre resultant de la pulverisation d'au moins une plante et un agent de cohesion |
-
1985
- 1985-03-29 DE DE19853511609 patent/DE3511609A1/de active Granted
-
1986
- 1986-03-26 AU AU55277/86A patent/AU5527786A/en not_active Abandoned
- 1986-03-26 US US06/844,325 patent/US4918099A/en not_active Expired - Fee Related
- 1986-03-26 EP EP86104157A patent/EP0205775A3/de not_active Withdrawn
- 1986-03-27 ZA ZA862351A patent/ZA862351B/xx unknown
- 1986-03-27 GB GB08607817A patent/GB2173500A/en not_active Withdrawn
- 1986-03-28 GR GR860828A patent/GR860828B/el unknown
- 1986-03-29 WO PCT/KR1986/000008 patent/WO1986005689A1/en unknown
- 1986-04-02 NZ NZ215678A patent/NZ215678A/xx unknown
- 1986-11-28 DK DK573386A patent/DK573386A/da not_active Application Discontinuation
- 1986-11-29 KR KR860700853A patent/KR870700358A/ko not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1281526A (en) * | 1968-10-25 | 1972-07-12 | Lawson Tait Medical And Scient | Therapeutic compositions |
Non-Patent Citations (4)
| Title |
|---|
| CA 75 3647 A * |
| JP-A-60 061 525 * |
| PHOTOCHEMISTRY 24 2403-5 * |
| PLANTA MED. 66-7 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0205775A3 (de) | 1990-02-14 |
| DE3511609C2 (en:Method) | 1987-06-19 |
| DK573386A (da) | 1987-01-22 |
| US4918099A (en) | 1990-04-17 |
| WO1986005689A1 (en) | 1986-10-09 |
| DE3511609A1 (de) | 1986-10-02 |
| DK573386D0 (da) | 1986-11-28 |
| GR860828B (en) | 1986-07-28 |
| AU5527786A (en) | 1986-10-02 |
| NZ215678A (en) | 1988-11-29 |
| ZA862351B (en) | 1986-11-26 |
| KR870700358A (ko) | 1987-12-28 |
| GB8607817D0 (en) | 1986-04-30 |
| EP0205775A2 (de) | 1986-12-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4940725A (en) | Oxindole alkaloids having properties stimulating the immunologic system and preparation containing the same | |
| US4918099A (en) | Drug, preparation and use thereof | |
| EP3040328B1 (en) | New salvianolic acid compound t, preparation method therefor, and use thereof | |
| EP0677289A2 (en) | Pharmaceutical composition for treating osteoporosis | |
| US20030072824A1 (en) | Ume extract having medicinal effects and compositions containing the same | |
| DK172879B1 (da) | Silibininholdigt farmaceutisk præparat | |
| US6329000B1 (en) | Extract of pine needle and the use thereof | |
| JP3450080B2 (ja) | プロシアニジンを配合した健康食品および医薬品 | |
| NZ554762A (en) | Method of treating inflammation disorders using extracts of passion fruit | |
| US20080146659A1 (en) | Hypoglycemic agent, hepatoprotecting agent and anticancer agent containing lignans derived from hongdoushan | |
| JPS6112622A (ja) | 造血幹細胞の分化増殖促進剤 | |
| US5481043A (en) | Phenone compounds, manufacturing method and pharmaceutical preparations containing them | |
| US5789439A (en) | Pharmaceutical use of forskolin derivatives | |
| US5019580A (en) | Dioscoretine and its use as a hypoglycemic agent | |
| AU621058B2 (en) | Thiosulphinic acid derivatives, their use in the treatment of inflammatory diseases, and drugs containing them | |
| JP3243879B2 (ja) | 抗高脂血症剤 | |
| EP0014471A2 (en) | Acylated derivatives of a water extract of Anemarrhenae rhizoma and hypoglycemic agents containing said derivatives | |
| JP3159508B2 (ja) | ウーロン茎茶抽出物を配合した健康食品および医薬品 | |
| JPS62209023A (ja) | 抗アレルギ−剤 | |
| KR0139769B1 (ko) | 당뇨병성 또는 노인성(당) 백내장 예방치료제 | |
| US7740888B2 (en) | Extracts of passion fruit and uses thereof | |
| JPH06293654A (ja) | 活性酸素消去作用剤およびアルド−スリダクタ−ゼ阻害作用剤 | |
| Chandrakanth et al. | Evaluation of AntiDiabetic Potential of Aloe Vera Leaves Extract. | |
| KR100202757B1 (ko) | 당뇨병 치료제 조성물 | |
| JP3621483B2 (ja) | ヒスタミン遊離抑制剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |