JPS591279B2 - 新規ヘレブリゲニンアシル誘導体、その製法及び該誘導体を含有する陽性走心筋作用医薬 - Google Patents

新規ヘレブリゲニンアシル誘導体、その製法及び該誘導体を含有する陽性走心筋作用医薬

Info

Publication number: JPS591279B2
Authority: JP; Japan
Prior art keywords: group; formula; substituted; alkyl; hellebrigenin
Prior art date: 1976-12-17
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.): Expired

Application number

JP52152295A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5395956A (en

Inventor

オツト−・イザ−ク

クラウス・ポツセルト

ホルスト・ウ−テマン

クラウス・テイ−マ−

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Evonik Operations GmbH

Original Assignee

Degussa GmbH

Priority date (The priority date 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 date listed.)

1976-12-17

Filing date

1977-12-16

Publication date

1984-01-11

1977-12-16 Application filed by Degussa GmbH filed Critical Degussa GmbH

1978-08-22 Publication of JPS5395956A publication Critical patent/JPS5395956A/ja

1984-01-11 Publication of JPS591279B2 publication Critical patent/JPS591279B2/ja

Status Expired legal-status Critical Current

Links

AXUYMUBJXHVZEL-UHFFFAOYSA-N Hellebrigenin Natural products C1=CC(=O)OC=C1C1CCC2(O)C1(C)CCC(C1(CC3)C=O)C2CCC1(O)CC3OC1OC(CO)C(O)C(O)C1O AXUYMUBJXHVZEL-UHFFFAOYSA-N 0.000 title claims description 24
239000003814 drug Substances 0.000 title claims description 9
238000004519 manufacturing process Methods 0.000 title claims description 9
229940079593 drug Drugs 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 51
-1 dinitrophenyl group Chemical group 0.000 claims description 32
125000004432 carbon atom Chemical group C* 0.000 claims description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
239000000126 substance Substances 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
229920006395 saturated elastomer Polymers 0.000 claims description 14
TVKPTWJPKVSGJB-XHCIOXAKSA-N (3s,5s,8r,9s,10s,13r,14s,17r)-3,5,14-trihydroxy-13-methyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene-10-carbaldehyde Chemical class C=1([C@H]2CC[C@]3(O)[C@H]4[C@@H]([C@]5(CC[C@H](O)C[C@@]5(O)CC4)C=O)CC[C@@]32C)C=CC(=O)OC=1 TVKPTWJPKVSGJB-XHCIOXAKSA-N 0.000 claims description 11
239000007795 chemical reaction product Substances 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 11
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 9
125000004430 oxygen atom Chemical group O* 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 7
238000000034 method Methods 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
229910052757 nitrogen Chemical group 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 2
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
239000008024 pharmaceutical diluent Substances 0.000 claims 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
238000010992 reflux Methods 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000013543 active substance Substances 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
239000002585 base Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
239000000203 mixture Substances 0.000 description 11
239000000047 product Substances 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
241000282326 Felis catus Species 0.000 description 8
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
238000010521 absorption reaction Methods 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000012043 crude product Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
238000003756 stirring Methods 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
230000031891 intestinal absorption Effects 0.000 description 5
238000001990 intravenous administration Methods 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 5
235000012239 silicon dioxide Nutrition 0.000 description 5
239000000375 suspending agent Substances 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
230000001476 alcoholic effect Effects 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
239000001913 cellulose Chemical class 0.000 description 4
229920002678 cellulose Chemical class 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000499 gel Substances 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
210000000936 intestine Anatomy 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
230000002107 myocardial effect Effects 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000007858 starting material Substances 0.000 description 4
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
150000002148 esters Chemical group 0.000 description 3
LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 3
239000000787 lecithin Substances 0.000 description 3
235000010445 lecithin Nutrition 0.000 description 3
229940067606 lecithin Drugs 0.000 description 3
239000000155 melt Substances 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
229930003799 tocopherol Natural products 0.000 description 3
239000011732 tocopherol Substances 0.000 description 3
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
208000010496 Heart Arrest Diseases 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
235000019483 Peanut oil Nutrition 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
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229910052783 alkali metal Inorganic materials 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
238000010171 animal model Methods 0.000 description 2
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235000010323 ascorbic acid Nutrition 0.000 description 2
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125000004429 atom Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
239000000872 buffer Substances 0.000 description 2
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230000000747 cardiac effect Effects 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
235000005687 corn oil Nutrition 0.000 description 2
239000002285 corn oil Substances 0.000 description 2
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GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
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230000037406 food intake Effects 0.000 description 2
235000004515 gallic acid Nutrition 0.000 description 2
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229910052739 hydrogen Inorganic materials 0.000 description 2
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TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 2
231100000636 lethal dose Toxicity 0.000 description 2
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VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
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PIYNUZCGMLCXKJ-UHFFFAOYSA-N 1,4-dioxane-2,6-dione Chemical compound O=C1COCC(=O)O1 PIYNUZCGMLCXKJ-UHFFFAOYSA-N 0.000 description 1
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238000009495 sugar coating Methods 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
235000020238 sunflower seed Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000013076 target substance Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
235000019149 tocopherols Nutrition 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
231100000816 toxic dose Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
238000011282 treatment Methods 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000010497 wheat germ oil Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Hospice & Palliative Care (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Hydrogenated Pyridines (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Peptides Or Proteins (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)

JP52152295A 1976-12-17 1977-12-16 新規ヘレブリゲニンアシル誘導体、その製法及び該誘導体を含有する陽性走心筋作用医薬 Expired JPS591279B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB000052759/76		1976-12-17
GB52759/76A GB1577633A (en)	1976-12-17	1976-12-17	Acyl derivatives of hellebrigenin

Publications (2)

Publication Number	Publication Date
JPS5395956A JPS5395956A (en)	1978-08-22
JPS591279B2 true JPS591279B2 (ja)	1984-01-11

Family

ID=10465185

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP52152295A Expired JPS591279B2 (ja)	1976-12-17	1977-12-16	新規ヘレブリゲニンアシル誘導体、その製法及び該誘導体を含有する陽性走心筋作用医薬

Country Status (15)

Country	Link
JP (1)	JPS591279B2 (fr)
AT (1)	AT372391B (fr)
BE (1)	BE861968A (fr)
CH (1)	CH639107A5 (fr)
DD (1)	DD133151A5 (fr)
DE (1)	DE2755122C2 (fr)
ES (2)	ES465135A1 (fr)
FI (1)	FI58135C (fr)
FR (1)	FR2374336A1 (fr)
GB (1)	GB1577633A (fr)
HU (1)	HU176767B (fr)
IT (1)	IT1113251B (fr)
PL (1)	PL110178B1 (fr)
SU (2)	SU751328A3 (fr)
ZA (1)	ZA777494B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS61158784U (fr) *	1985-03-25	1986-10-01

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1108702A1 (fr) *	1999-12-13	2001-06-20	Kvaerner Process Technology Limited	Procédé pour la coproduction de diols aliphatiques et d'éthers cycliques
WO2010102673A1 (fr) *	2009-03-13	2010-09-16	Unibioscreen S.A.	Hellébrine et dérivés d'hellébrigénine
SI2563803T1 (sl) *	2010-04-27	2016-06-30	Pharma Mar S.A.	Na položaju 7 (8) nenasičeni steroidni lakton proti raku

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1901484A1 (de) *	1969-01-14	1970-10-29	Hoechst Ag	Herzwirksame Oxyester von Steroid-Cardenoliden und -Bufandienoliden und Verfahren zu ihrer Herstellung

1976
- 1976-12-17 GB GB52759/76A patent/GB1577633A/en not_active Expired
1977
- 1977-12-10 DE DE2755122A patent/DE2755122C2/de not_active Expired
- 1977-12-13 IT IT52184/77A patent/IT1113251B/it active
- 1977-12-15 ZA ZA00777494A patent/ZA777494B/xx unknown
- 1977-12-15 SU SU772553849A patent/SU751328A3/ru active
- 1977-12-15 FR FR7737795A patent/FR2374336A1/fr active Granted
- 1977-12-16 BE BE6046270A patent/BE861968A/fr not_active IP Right Cessation
- 1977-12-16 AT AT0903877A patent/AT372391B/de not_active IP Right Cessation
- 1977-12-16 JP JP52152295A patent/JPS591279B2/ja not_active Expired
- 1977-12-16 ES ES465135A patent/ES465135A1/es not_active Expired
- 1977-12-16 DD DD7700202719A patent/DD133151A5/xx unknown
- 1977-12-16 FI FI773814A patent/FI58135C/fi not_active IP Right Cessation
- 1977-12-16 PL PL1977203030A patent/PL110178B1/pl not_active IP Right Cessation
- 1977-12-16 HU HU77DE947A patent/HU176767B/hu unknown
- 1977-12-16 ES ES465136A patent/ES465136A1/es not_active Expired
1978
- 1978-01-01 CH CH1554377A patent/CH639107A5/de not_active IP Right Cessation
- 1978-12-25 SU SU782701599A patent/SU795487A3/ru active

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS61158784U (fr) *	1985-03-25	1986-10-01

Also Published As

Publication number	Publication date
SU795487A3 (ru)	1981-01-07
DE2755122C2 (de)	1983-06-30
FI58135C (fi)	1980-12-10
CH639107A5 (de)	1983-10-31
DD133151A5 (de)	1978-12-13
BE861968A (fr)	1978-06-16
FR2374336B1 (fr)	1980-11-07
FR2374336A1 (fr)	1978-07-13
HU176767B (en)	1981-05-28
JPS5395956A (en)	1978-08-22
ZA777494B (en)	1979-02-28
AT372391B (de)	1983-09-26
FI58135B (fi)	1980-08-29
ES465136A1 (es)	1979-01-01
ATA903877A (de)	1983-02-15
PL203030A1 (pl)	1979-03-26
SU751328A3 (ru)	1980-07-23
ES465135A1 (es)	1978-10-01
PL110178B1 (en)	1980-07-31
DE2755122A1 (de)	1978-06-22
GB1577633A (en)	1980-10-29
IT1113251B (it)	1986-01-20
FI773814A7 (fi)	1978-06-18

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DE68917129T2 (de)	1995-03-02	Wasserlösliche antineoplastische taxolderivate.
US4554281A (en)	1985-11-19	2-Amino-3-acylamino-6-benzylamino-pyridine-derivative having antiepileptic action
RU2049771C1 (ru)	1995-12-10	Хиноновые производные и их фармакологически приемлемые соли
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PL120661B1 (en)	1982-03-31	Process for preparing novel derivatives of 9-aminodibenzo(b,d)pyran pirana
CH648553A5 (de)	1985-03-29	Neue 3,4-dihydro-5h-2,3-benzodiazepin-derivate und verfahren zur herstellung derselben.
DE60031705T2 (de)	2007-10-04	Salicylamid-derivate
PT85594B (pt)	1990-05-31	Processo para a preparacao de novos derivados de xantina
AU607100B2 (en)	1991-02-21	New androstane 17-carboxylic acid ester, process for their preparation and drugs containing them
JPH0369910B2 (fr)	1991-11-05
WO1996000236A1 (fr)	1996-01-04	Derive du triterpene et preparation medicinale associee
PT1142885E (pt)	2007-02-28	Derivados de 2-(n-cianoimino)tiazolidin-4-ona
JPH0253795A (ja)	1990-02-22	新規なエステル
CN101863786B (zh)	2013-05-01	水溶性紫草素萘茜母核氧烷基化衍生物及其制备和应用方法
JPH02124884A (ja)	1990-05-14	Ｎ―置換アミド誘導体
JPS591279B2 (ja)	1984-01-11	新規ヘレブリゲニンアシル誘導体、その製法及び該誘導体を含有する陽性走心筋作用医薬
EP0152868B1 (fr)	1989-06-21	Dérivés d'isoxazole, procédé de préparation et médicaments contenant ces composés
SU1391495A3 (ru)	1988-04-23	Способ получени производных 3-фенил-2-пропенамина в виде Z-изомеров или их терапевтически совместимых солей
US4897423A (en)	1990-01-30	Dinitrobenzenesulfonamides
US3987175A (en)	1976-10-19	Derivatives of phenoxy isobutyric acid having hypolipemizing and hypocholesterolemizing action
US4218447A (en)	1980-08-19	Acyl derivatives of hellebrigenin
NZ197073A (en)	1984-07-06	Certain benz(oxa or thia)zol-2-ylcarboxylic acid esters
EP0000693A1 (fr)	1979-02-21	Dérivés d'aminophénoxyméthyl-2-morpholine, procédé pour leur préparation et médicaments les contenant
JPH04368359A (ja)	1992-12-21	カプサイシン誘導体又はその酸エステルを有効成分とする鎮痛剤、血管拡張剤
CN113214238A (zh)	2021-08-06	一类具有酰化哌嗪结构的吲哚恶二唑衍生物的制备和用途

JPS591279B2 - 新規ヘレブリゲニンアシル誘導体、その製法及び該誘導体を含有する陽性走心筋作用医薬 - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (2)

Publications (2)

Family

ID=10465185

Family Applications (1)

Country Status (15)

Cited By (1)

Families Citing this family (3)

Family Cites Families (1)

Cited By (1)

Also Published As

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