DD244977A5 - Verfahren zur herstellung von neuen 7-oxo-pgi tief 2-ephedrin-salz-analogen - Google Patents

Verfahren zur herstellung von neuen 7-oxo-pgi tief 2-ephedrin-salz-analogen Download PDF

Info

Publication number: DD244977A5
Authority: DD; German Democratic Republic
Prior art keywords: general formula; oxo; hydrogen; compound; ephedrine
Prior art date: 1985-05-29

Application number

DD86290679A

Other languages

German (de)

English (en)

Inventor

Gabor Kovacs

Geza Galambos

Istvan Toemoeskoezi

Karoly Kanai

Peter Gyoery

Peter Koermoeczy

Istvan Stadler

Laszlo Szekeres

Gyula Papp

Eva Udvary

Pal Hadhazy

Jenoe Marton

Gyoergy Dorman

Original Assignee

��@��@��@��@��@��@��Kk��

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.)

1985-05-29

Filing date

1986-05-28

Publication date

1987-04-22

1986-05-28 Application filed by ��@��@��@��@��@��@��Kk�� filed Critical ��@��@��@��@��@��@��Kk��

1987-04-22 Publication of DD244977A5 publication Critical patent/DD244977A5/de

Links

238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 50
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical class CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims abstract description 18
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
238000000034 method Methods 0.000 claims abstract description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims abstract description 8
230000008569 process Effects 0.000 claims abstract description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
239000001301 oxygen Substances 0.000 claims abstract description 3
150000003839 salts Chemical class 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 12
239000011541 reaction mixture Substances 0.000 claims description 11
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims description 10
230000015572 biosynthetic process Effects 0.000 claims description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
-1 C ^ Aikenyl Chemical group 0.000 claims description 8
229960002179 ephedrine Drugs 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
125000004185 ester group Chemical group 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
125000001589 carboacyl group Chemical group 0.000 claims description 3
239000002798 polar solvent Substances 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
125000001072 heteroaryl group Chemical group 0.000 claims description 2
208000018262 Peripheral vascular disease Diseases 0.000 abstract description 2
208000010125 myocardial infarction Diseases 0.000 abstract description 2
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 abstract 1
101150065749 Churc1 gene Proteins 0.000 abstract 1
206010028980 Neoplasm Diseases 0.000 abstract 1
102100038239 Protein Churchill Human genes 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 8
239000002585 base Substances 0.000 description 7
238000005755 formation reaction Methods 0.000 description 7
230000000144 pharmacologic effect Effects 0.000 description 7
159000000000 sodium salts Chemical class 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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 6
229960001123 epoprostenol Drugs 0.000 description 6
239000000825 pharmaceutical preparation Substances 0.000 description 6
ZHIHHYNLWRXTTN-GJUFTPBXSA-N (5z)-5-[(3ar,4r,5r,6as)-5-hydroxy-4-[(e,3s)-3-hydroxyoct-1-enyl]-3-oxo-4,5,6,6a-tetrahydro-3ah-cyclopenta[b]furan-2-ylidene]pentanoic acid Chemical class O1\C(=C/CCCC(O)=O)C(=O)[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 ZHIHHYNLWRXTTN-GJUFTPBXSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
206010010904 Convulsion Diseases 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
230000000694 effects Effects 0.000 description 4
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
230000020477 pH reduction Effects 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 4
229910000342 sodium bisulfate Inorganic materials 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000009471 action Effects 0.000 description 3
239000013078 crystal Substances 0.000 description 3
201000010099 disease Diseases 0.000 description 3
239000000047 product Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LMHIPJMTZHDKEW-XQYLJSSYSA-M Epoprostenol sodium Chemical compound [Na+].O1\C(=C/CCCC([O-])=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 LMHIPJMTZHDKEW-XQYLJSSYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
208000025865 Ulcer Diseases 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000001120 cytoprotective effect Effects 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000706 filtrate Substances 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
230000002401 inhibitory effect Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HFWWEMPLBCKNNM-UHFFFAOYSA-N n-[bis(hydroxyamino)methyl]hydroxylamine Chemical compound ONC(NO)NO HFWWEMPLBCKNNM-UHFFFAOYSA-N 0.000 description 2
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000002265 prevention Effects 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
FGOJCPKOOGIRPA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-oxoazepane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O FGOJCPKOOGIRPA-UHFFFAOYSA-N 0.000 description 1
229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
206010061459 Gastrointestinal ulcer Diseases 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
206010067125 Liver injury Diseases 0.000 description 1
206010027476 Metastases Diseases 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
235000010357 aspartame Nutrition 0.000 description 1
230000008901 benefit Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
230000004087 circulation Effects 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000001924 cycloalkanes Chemical class 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000003500 enol ether group Chemical group 0.000 description 1
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000945 filler Substances 0.000 description 1
230000027119 gastric acid secretion Effects 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
230000000004 hemodynamic effect Effects 0.000 description 1
231100000234 hepatic damage Toxicity 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
238000011835 investigation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000003902 lesion Effects 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000008818 liver damage Effects 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
230000036284 oxygen consumption Effects 0.000 description 1
229960001789 papaverine Drugs 0.000 description 1
239000012071 phase Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
150000003815 prostacyclins Chemical class 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000005740 tumor formation Effects 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
- C07D307/937—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans with hydrocarbon or substituted hydrocarbon radicals directly attached in position 2, e.g. prostacyclins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- A61P9/12—Antihypertensives

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Gastroenterology & Hepatology (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Diabetes (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Analysing Materials By The Use Of Radiation (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Furan Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Steroid Compounds (AREA)
Saccharide Compounds (AREA)

DD86290679A 1985-05-29 1986-05-28 Verfahren zur herstellung von neuen 7-oxo-pgi tief 2-ephedrin-salz-analogen DD244977A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU852050A HU197733B (en)	1985-05-29	1985-05-29	Process for producing ephedrin-salts of 7-oxo-prosta-cyclin derivatives

Publications (1)

Publication Number	Publication Date
DD244977A5 true DD244977A5 (de)	1987-04-22

Family

ID=10957509

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86290679A DD244977A5 (de)	1985-05-29	1986-05-28	Verfahren zur herstellung von neuen 7-oxo-pgi tief 2-ephedrin-salz-analogen

Country Status (23)

Country	Link
US (1)	US4735965A (cs)
EP (1)	EP0205969B1 (cs)
JP (1)	JPS61277650A (cs)
KR (1)	KR860009031A (cs)
CN (1)	CN1010587B (cs)
AT (1)	ATE71093T1 (cs)
AU (1)	AU588761B2 (cs)
CS (1)	CS261894B2 (cs)
DD (1)	DD244977A5 (cs)
DE (1)	DE3683192D1 (cs)
DK (1)	DK249686A (cs)
ES (1)	ES8706624A1 (cs)
FI (1)	FI82690C (cs)
GR (1)	GR861390B (cs)
HU (1)	HU197733B (cs)
IL (1)	IL78849A (cs)
NO (1)	NO171677C (cs)
NZ (1)	NZ216339A (cs)
PL (1)	PL148718B1 (cs)
PT (1)	PT82657B (cs)
SU (2)	SU1454250A3 (cs)
YU (1)	YU46169B (cs)
ZA (1)	ZA863801B (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8729153D0 (en) *	1987-12-14	1988-01-27	Efamol Ltd	Fatty acid compositions
HU227157B1 (en) *	2001-07-30	2010-09-28	Chinoin Gyogyszer Es Vegyeszet	Production of beraprost ester by selective oxidation

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU502731B2 (en) *	1975-09-17	1979-08-09	The Upjohn Company	Prostaglandin analogues
IT1088036B (it) *	1977-11-25	1985-06-04	Erba Carlo Spa	15-epi-prostaciclina e prostaciclina analoghi
US4258199A (en) *	1978-03-13	1981-03-24	Research Corporation	Method for preparing cyclic ethers and thioethers including oxygen isomers and sulfur analogs of prostacyclin
US4330553A (en) *	1979-11-12	1982-05-18	Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T.	7-Oxo-PGI2 -derivatives and process for the preparation thereof and pharmaceutical compositions containing same
HU182012B (en) *	1979-11-12	1983-12-28	Chinoin Gyogyszer Es Vegyeszet	Process for preparing 6-substituted-7-oxo-pgi down 1 derivatives
DE3035454A1 (de) *	1980-09-18	1982-04-22	Schering Ag, 1000 Berlin Und 4619 Bergkamen	7-oxoprostacyclinderivate und verfahren zu ihrer herstellung
HU191264B (en) *	1984-01-13	1987-01-28	Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu	Process for production of derivatives of 7-oxo-prostacyclin with selective biological effect

1985
- 1985-05-29 HU HU852050A patent/HU197733B/hu not_active IP Right Cessation
1986
- 1986-05-20 IL IL78849A patent/IL78849A/xx not_active IP Right Cessation
- 1986-05-21 ZA ZA863801A patent/ZA863801B/xx unknown
- 1986-05-22 FI FI862159A patent/FI82690C/fi not_active IP Right Cessation
- 1986-05-27 CS CS863877A patent/CS261894B2/cs unknown
- 1986-05-28 PT PT82657A patent/PT82657B/pt not_active IP Right Cessation
- 1986-05-28 DD DD86290679A patent/DD244977A5/de not_active IP Right Cessation
- 1986-05-28 DK DK249686A patent/DK249686A/da not_active Application Discontinuation
- 1986-05-28 US US06/868,772 patent/US4735965A/en not_active Expired - Fee Related
- 1986-05-28 GR GR861390A patent/GR861390B/el unknown
- 1986-05-28 DE DE8686107223T patent/DE3683192D1/de not_active Expired - Lifetime
- 1986-05-28 NZ NZ216339A patent/NZ216339A/xx unknown
- 1986-05-28 NO NO862112A patent/NO171677C/no unknown
- 1986-05-28 EP EP19860107223 patent/EP0205969B1/de not_active Expired - Lifetime
- 1986-05-28 AU AU58001/86A patent/AU588761B2/en not_active Ceased
- 1986-05-28 YU YU90986A patent/YU46169B/sh unknown
- 1986-05-28 AT AT86107223T patent/ATE71093T1/de not_active IP Right Cessation
- 1986-05-28 PL PL1986259759A patent/PL148718B1/pl unknown
- 1986-05-28 JP JP61121394A patent/JPS61277650A/ja active Pending
- 1986-05-29 CN CN86103741A patent/CN1010587B/zh not_active Expired
- 1986-05-29 ES ES555454A patent/ES8706624A1/es not_active Expired
- 1986-05-29 KR KR1019860004241A patent/KR860009031A/ko not_active Abandoned
- 1986-05-29 SU SU864027565A patent/SU1454250A3/ru active
- 1986-09-18 SU SU864028148A patent/SU1447823A1/ru active

Also Published As

Publication number	Publication date
PT82657B (pt)	1988-03-03
ES555454A0 (es)	1987-07-01
SU1447823A1 (ru)	1988-12-30
CS261894B2 (en)	1989-02-10
ATE71093T1 (de)	1992-01-15
IL78849A (en)	1990-01-18
NO171677C (no)	1993-04-21
KR860009031A (ko)	1986-12-19
NO862112L (no)	1986-12-01
FI82690B (fi)	1990-12-31
YU90986A (en)	1988-02-29
ES8706624A1 (es)	1987-07-01
CN1010587B (zh)	1990-11-28
DE3683192D1 (de)	1992-02-13
AU588761B2 (en)	1989-09-21
CN86103741A (zh)	1987-02-18
YU46169B (sh)	1993-05-28
JPS61277650A (ja)	1986-12-08
AU5800186A (en)	1986-12-04
FI862159A7 (fi)	1986-11-30
NO171677B (no)	1993-01-11
PL148718B1 (en)	1989-11-30
ZA863801B (en)	1987-01-28
GR861390B (en)	1986-09-17
FI862159A0 (fi)	1986-05-22
HUT40635A (en)	1987-01-28
NZ216339A (en)	1989-08-29
IL78849A0 (en)	1986-09-30
PT82657A (en)	1986-06-01
EP0205969A2 (de)	1986-12-30
DK249686A (da)	1986-11-30
DK249686D0 (da)	1986-05-28
US4735965A (en)	1988-04-05
FI82690C (fi)	1991-04-10
SU1454250A3 (ru)	1989-01-23
HU197733B (en)	1989-05-29
EP0205969B1 (de)	1992-01-02
EP0205969A3 (en)	1989-04-19

Legal Events

Date	Code	Title	Description
2000-01-05	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
AT392964B (de)	1991-07-25	Verfahren zur herstellung neuer optisch aktiver oder racemischer prostaglandinderivate
EP0111873A1 (de)	1984-06-27	Derivate der cis, endo-2-Azabicyclo-(5.3.0)-decan-3-carbonsäure, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und deren Verwendung
EP0600949A1 (de)	1994-06-15	Neue 3,5-di-tert.butyl-4-hydroxyphenyl-derivate, verfahren zu ihrer herstellung und arzneimittel.
EP0215860A1 (de)	1987-04-01	9-halogenprostaglandine, verfahren zu ihrer herstellung.
DE3925496C2 (cs)	1992-04-30
DE2941288C2 (cs)	1990-05-17
CH638510A5 (de)	1983-09-30	Prostacyclinanaloga.
DE2346706A1 (de)	1975-04-03	Neue, nicht natuerlich vorkommende analoga von prostansaeuren und verfahren zu ihrer herstellung
DE3029984C2 (de)	1983-12-15	2-Oxabicyclo [3.3.0] octanderivate und diese enthaltende Arzneimittel
EP0205969B1 (de)	1992-01-02	7-Oxo-PGI2-Ephedrinsalze, deren Herstellung und diese Verbindungen enthaltende pharmazeutsche Präparate
DE3149009A1 (de)	1983-06-23	(-)-2-(1-(2,6-dichlorphenoxy)-ethyl)-1,3-diazacyclopent-2-en, dessen herstellung und seine verwendung in pharmazeutischen praeparaten
DE2618936C3 (de)	1979-05-03	N-Acyl-glutamine, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
DE2716172C2 (de)	1985-09-05	Bis(6-[(hexahydro-1H-azepin-1-yl)-methylenamino]-penicillanoyloxy)-methan, seine Herstellung und dieses enthaltendes Arzneimittel
DE2440381A1 (de)	1976-01-22	Substituierte phenoxyalkancarbonsaeuren, salze hiervon sowie verfahren zu ihrer herstellung
DE2350230C2 (de)	1984-01-19	Verfahren zur Herstellung von Cephalosporinestern
CH483397A (de)	1969-12-31	Verfahren zur Herstellung von Phenylalaninderivaten
DE69018741T2 (de)	1995-10-12	Konjugierte gamma-Hydroxybutenolid-Derivate und sie als aktiver Wirkstoff enthaltende Mittel gegen Magengeschwüre.
DE2414345C3 (de)	1980-02-21	(Z)-(3-Methyl-4-oxo-5-piperidinothiazolidin-2-yIiden)-esssigsäure und Verfahren zur Herstellung von Thiazolidinessigsäure-Derivaten
DE3426720A1 (de)	1986-01-23	Benzthiazepinon- und benzthiazocinon-derivate, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung, sowie zwischenprodukte bei ihrer herstellung
DE68907032T2 (de)	1994-01-20	Verfahren zur Herstellung von 1,4-Überbrückten-Cyclohexancarbonsäure-Derivaten und ihre Verwendung.
DE2141357C3 (de)	1976-02-19	Bis-(4-chlorphenoxy)-essigsäureester, Verfahren zu ihrer Herstellung diese Verbindungen enthaltende Arzneimittel
DE1962493C3 (de)	1977-01-27	Thiazolylbenzoesäurederivate und Verfahren zu ihrer Herstellung
AT352738B (de)	1979-10-10	Verfahren zur herstellung von neuen 6,11- dihydrodibenzothiepin-11-on-verbindungen
DE2031360A1 (de)	1971-01-21	Neue cyclische Verbindungen und Ver fahren zu ihrer Herstellung
DE2243574A1 (de)	1974-03-14	Aryloxy-essigsaeure-derivate und verfahren zur herstellung derselben