DD234414A5 - Verfahren zur herstellung neuer carbacycline - Google Patents

Verfahren zur herstellung neuer carbacycline Download PDF

Info

Publication number: DD234414A5
Authority: DD; German Democratic Republic
Prior art keywords: group; alkyl; aryl; free; atoms
Prior art date: 1984-03-08

Application number

DD85273815A

Other languages

German (de)

English (en)

Inventor

Werner Skuballa

Bernd Raduechel

Helmut Vorbrueggen

Ekkehard Schillinger

Claus-Steffen Stuerzebecher

Original Assignee

��@��k��

��@��@��k��

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.)

1984-03-08

Filing date

1985-03-06

Publication date

1986-04-02

1985-03-06 Application filed by ��@��k��, ��@��@��k�� filed Critical ��@��k��

1986-04-02 Publication of DD234414A5 publication Critical patent/DD234414A5/de

Links

238000000034 method Methods 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 6
230000008569 process Effects 0.000 title claims description 5
-1 C3-C10-cycloalkyl Chemical group 0.000 claims abstract description 35
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
125000000217 alkyl group Chemical group 0.000 claims abstract description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 9
125000005843 halogen group Chemical group 0.000 claims abstract description 8
125000002947 alkylene group Chemical group 0.000 claims abstract description 7
229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 33
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 6
150000001299 aldehydes Chemical class 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
238000006266 etherification reaction Methods 0.000 claims description 3
150000002902 organometallic compounds Chemical class 0.000 claims description 3
229920000858 Cyclodextrin Polymers 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 2
XZFRIPGNUQRGPI-WLPVIMDJSA-N Carbacyclin Chemical class C1\C(=C\CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 XZFRIPGNUQRGPI-WLPVIMDJSA-N 0.000 abstract description 6
239000003795 chemical substances by application Substances 0.000 abstract description 3
229910052736 halogen Inorganic materials 0.000 abstract description 2
229910052739 hydrogen Inorganic materials 0.000 abstract 4
239000001257 hydrogen Substances 0.000 abstract 4
125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 3
125000000041 C6-C10 aryl group Chemical group 0.000 abstract 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
239000000243 solution Substances 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000012230 colorless oil Substances 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
239000002904 solvent Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000000203 mixture Substances 0.000 description 6
150000003180 prostaglandins Chemical class 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
239000002253 acid Substances 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound 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 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
208000001953 Hypotension Diseases 0.000 description 4
230000009471 action Effects 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
238000003776 cleavage reaction Methods 0.000 description 4
229960001123 epoprostenol Drugs 0.000 description 4
208000021822 hypotensive Diseases 0.000 description 4
230000001077 hypotensive effect Effects 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
210000000056 organ Anatomy 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229940094443 oxytocics prostaglandins Drugs 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
230000007017 scission Effects 0.000 description 4
238000002560 therapeutic procedure Methods 0.000 description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
208000007536 Thrombosis Diseases 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000036772 blood pressure Effects 0.000 description 3
239000012267 brine Substances 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
150000004679 hydroxides Chemical class 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
210000003734 kidney Anatomy 0.000 description 3
210000004185 liver Anatomy 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
210000000496 pancreas Anatomy 0.000 description 3
238000011321 prophylaxis Methods 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
210000002784 stomach Anatomy 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
208000024172 Cardiovascular disease Diseases 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
206010061216 Infarction Diseases 0.000 description 2
239000003810 Jones reagent Substances 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
208000030831 Peripheral arterial occlusive disease Diseases 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
230000003182 bronchodilatating effect Effects 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
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 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
230000027119 gastric acid secretion Effects 0.000 description 2
210000002216 heart Anatomy 0.000 description 2
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
230000007574 infarction Effects 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
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238000007127 saponification reaction Methods 0.000 description 2
210000002460 smooth muscle Anatomy 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
238000011282 treatment Methods 0.000 description 2
XZWJHHQHUFJOJD-UHFFFAOYSA-N (3-carboxyphenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].OC(=O)C1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 XZWJHHQHUFJOJD-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
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 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
BLADNFHEWKFLCZ-QEWJQUTHSA-N 3-[(E)-[(3aS,4S,5R,6aS)-4-[(E,3S)-4-methyl-3-(oxan-2-yloxy)oct-1-en-6-ynyl]-5-(oxan-2-yloxy)-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]methyl]benzaldehyde Chemical compound O([C@@H](C(C)CC#CC)\C=C\[C@H]1[C@H]2CC(/C[C@H]2C[C@H]1OC1OCCCC1)=C/C=1C=C(C=O)C=CC=1)C1CCCCO1 BLADNFHEWKFLCZ-QEWJQUTHSA-N 0.000 description 1
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
206010006482 Bronchospasm Diseases 0.000 description 1
UECYEABIFWIQSI-UHFFFAOYSA-N C[S-]=O.[K+] Chemical compound C[S-]=O.[K+] UECYEABIFWIQSI-UHFFFAOYSA-N 0.000 description 1
229940127291 Calcium channel antagonist Drugs 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
101000862089 Clarkia lewisii Glucose-6-phosphate isomerase, cytosolic 1A Proteins 0.000 description 1
239000012027 Collins reagent Substances 0.000 description 1
206010011091 Coronary artery thrombosis Diseases 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
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 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
RXHGEVVEDSUNHM-UHFFFAOYSA-N OCC(N)(CO)CO.N1CCOCC1 Chemical compound OCC(N)(CO)CO.N1CCOCC1 RXHGEVVEDSUNHM-UHFFFAOYSA-N 0.000 description 1
208000005764 Peripheral Arterial Disease Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
238000007295 Wittig olefination reaction Methods 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 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
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000003266 anti-allergic effect Effects 0.000 description 1
230000001142 anti-diarrhea Effects 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
230000001028 anti-proliverative effect Effects 0.000 description 1
229940127218 antiplatelet drug Drugs 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
230000007885 bronchoconstriction Effects 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
208000029078 coronary artery disease Diseases 0.000 description 1
208000002528 coronary thrombosis Diseases 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000001120 cytoprotective effect Effects 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
WHFKIZXBVFEJGA-UHFFFAOYSA-L dihydroxy(dioxo)chromium;pyridine Chemical compound O[Cr](O)(=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 WHFKIZXBVFEJGA-UHFFFAOYSA-L 0.000 description 1
150000004656 dimethylamines Chemical class 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
210000001156 gastric mucosa Anatomy 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000002615 hemofiltration Methods 0.000 description 1
229960002897 heparin Drugs 0.000 description 1
229920000669 heparin Polymers 0.000 description 1
125000006038 hexenyl group Chemical group 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
210000003405 ileum Anatomy 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
210000004347 intestinal mucosa Anatomy 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000003199 leukotriene receptor blocking agent Substances 0.000 description 1
150000002617 leukotrienes Chemical class 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
SOHCYNFHNYKSTM-UHFFFAOYSA-N methylsulfinylmethane;oxolane Chemical compound CS(C)=O.C1CCOC1 SOHCYNFHNYKSTM-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
239000000106 platelet aggregation inhibitor Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000004321 preservation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003174 prostaglandin I2 derivatives Chemical class 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
230000036593 pulmonary vascular resistance Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000008327 renal blood flow Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000035939 shock Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
CWXOAQXKPAENDI-UHFFFAOYSA-N sodium methylsulfinylmethylide Chemical compound [Na+].CS([CH2-])=O CWXOAQXKPAENDI-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
230000002792 vascular Effects 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
238000004383 yellowing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/005—Analogues or derivatives having the five membered ring replaced by other rings
- C07C405/0075—Analogues or derivatives having the five membered ring replaced by other rings having the side-chains or their analogues or derivatives attached to a condensed ring system
- C07C405/0083—Analogues or derivatives having the five membered ring replaced by other rings having the side-chains or their analogues or derivatives attached to a condensed ring system which is only ortho or peri condensed, e.g. carbacyclins
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- 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
- 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
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Hematology (AREA)
Diabetes (AREA)
Pulmonology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Indole Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Ink Jet Recording Methods And Recording Media Thereof (AREA)
Drawers Of Furniture (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pyrane Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DD85273815A 1984-03-08 1985-03-06 Verfahren zur herstellung neuer carbacycline DD234414A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19843408699 DE3408699A1 (de)	1984-03-08	1984-03-08	Neue carbacycline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel

Publications (1)

Publication Number	Publication Date
DD234414A5 true DD234414A5 (de)	1986-04-02

Family

ID=6230046

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD85273815A DD234414A5 (de)	1984-03-08	1985-03-06	Verfahren zur herstellung neuer carbacycline

Country Status (20)

Country	Link
US (1)	US4827017A (fi)
EP (1)	EP0155901B1 (fi)
JP (1)	JPH0723336B2 (fi)
AT (1)	ATE63305T1 (fi)
AU (1)	AU577097B2 (fi)
CA (1)	CA1263382A (fi)
CS (1)	CS250247B2 (fi)
DD (1)	DD234414A5 (fi)
DE (2)	DE3408699A1 (fi)
DK (1)	DK101085A (fi)
ES (1)	ES540852A0 (fi)
FI (1)	FI850885L (fi)
GR (1)	GR850567B (fi)
HU (1)	HU195481B (fi)
IE (1)	IE58007B1 (fi)
IL (1)	IL74542A0 (fi)
NO (1)	NO160438C (fi)
NZ (1)	NZ211291A (fi)
PH (1)	PH23067A (fi)
ZA (1)	ZA851771B (fi)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3428266A1 (de) *	1984-07-27	1986-01-30	Schering AG, 1000 Berlin und 4709 Bergkamen	Neue carbacycline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2845770A1 (de) *	1978-10-19	1980-04-30	Schering Ag	Neue prostacyclin-derivate und verfahren zu ihrer herstellung
CA1201712A (en) *	1980-02-28	1986-03-11	Paul A. Aristoff	Carbacyclin analogs
IL65387A0 (en) *	1981-04-14	1982-05-31	Chinoin Gyogyszer Es Vegyeszet	2,3,4-trinor-m-inter-phenylene-prostaglandin derivatives and a process for the preparation thereof
DE3146278C2 (de) *	1981-11-21	1984-10-31	Grünenthal GmbH, 5190 Stolberg	cis-Bicyclo[3.3.0]octanderivate, diese enthaltende Arzneimittel und Verfahren zur Herstellung dieser Verbindungen
IL67332A (en) *	1981-12-01	1985-12-31	Chinoin Gyogyszer Es Vegyeszet	Inter-m-phenylene-prostacyclin analogues,process for the preparation thereof and pharmaceutical compositions containing them
DE3204443A1 (de) *	1982-02-08	1983-08-18	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Neue carbacycline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
HU190007B (en) *	1982-05-06	1986-08-28	Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu	Process for producing new aromatic prostacylin analogues

1984
- 1984-03-08 DE DE19843408699 patent/DE3408699A1/de not_active Ceased
1985
- 1985-03-01 ES ES540852A patent/ES540852A0/es active Granted
- 1985-03-04 NZ NZ211291A patent/NZ211291A/xx unknown
- 1985-03-05 DK DK101085A patent/DK101085A/da not_active Application Discontinuation
- 1985-03-05 CS CS851538A patent/CS250247B2/cs unknown
- 1985-03-05 FI FI850885A patent/FI850885L/fi not_active Application Discontinuation
- 1985-03-06 GR GR850567A patent/GR850567B/el unknown
- 1985-03-06 AT AT85730037T patent/ATE63305T1/de not_active IP Right Cessation
- 1985-03-06 DD DD85273815A patent/DD234414A5/de unknown
- 1985-03-06 EP EP85730037A patent/EP0155901B1/de not_active Expired - Lifetime
- 1985-03-06 DE DE8585730037T patent/DE3582742D1/de not_active Expired - Lifetime
- 1985-03-07 CA CA000475928A patent/CA1263382A/en not_active Expired
- 1985-03-07 HU HU85865A patent/HU195481B/hu not_active IP Right Cessation
- 1985-03-07 NO NO850906A patent/NO160438C/no unknown
- 1985-03-07 IE IE576/85A patent/IE58007B1/en not_active IP Right Cessation
- 1985-03-08 ZA ZA851771A patent/ZA851771B/xx unknown
- 1985-03-08 PH PH31961A patent/PH23067A/en unknown
- 1985-03-08 IL IL74542A patent/IL74542A0/xx unknown
- 1985-03-08 AU AU39734/85A patent/AU577097B2/en not_active Ceased
- 1985-03-08 JP JP60045001A patent/JPH0723336B2/ja not_active Expired - Lifetime
1987
- 1987-03-03 US US07/021,102 patent/US4827017A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0155901B1 (de)	1991-05-08
NO850906L (no)	1985-09-09
DE3408699A1 (de)	1985-09-12
NZ211291A (en)	1988-10-28
DE3582742D1 (de)	1991-06-13
US4827017A (en)	1989-05-02
JPS60204737A (ja)	1985-10-16
ZA851771B (en)	1985-10-30
AU3973485A (en)	1985-09-12
ATE63305T1 (de)	1991-05-15
IL74542A0 (en)	1985-06-30
AU577097B2 (en)	1988-09-15
HUT37120A (en)	1985-11-28
JPH0723336B2 (ja)	1995-03-15
GR850567B (fi)	1985-07-03
DK101085A (da)	1985-09-09
CS250247B2 (en)	1987-04-16
EP0155901A1 (de)	1985-09-25
IE850576L (en)	1985-09-08
IE58007B1 (en)	1993-06-02
DK101085D0 (da)	1985-03-05
ES8601840A1 (es)	1985-12-01
FI850885A0 (fi)	1985-03-05
NO160438B (no)	1989-01-09
ES540852A0 (es)	1985-12-01
NO160438C (no)	1989-04-19
HU195481B (en)	1988-05-30
FI850885L (fi)	1985-09-09
CA1263382A (en)	1989-11-28
PH23067A (en)	1989-03-27

Publication	Publication Date	Title
EP0055208B1 (de)	1985-03-13	Neue Carbacycline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0119949B1 (de)	1988-11-23	Neue Carbacycline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0099538B1 (de)	1991-09-11	Neue Carbacycline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0069692B1 (de)	1988-03-02	Neue Carbacycline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0105288B1 (de)	1985-12-11	Carbacycline, herstellung und verwendung
EP0057660B1 (de)	1985-08-21	Neue Prostacyclin-Derivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
EP0086404B1 (de)	1986-12-30	Neue Carbacycline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0098794B1 (de)	1988-04-27	Neue Carbacycline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE3428266A1 (de)	1986-01-30	Neue carbacycline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
EP0324815B1 (de)	1992-01-29	Neue 9-substituierte carbacyclinderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DD234414A5 (de)	1986-04-02	Verfahren zur herstellung neuer carbacycline
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EP0051557A1 (de)	1982-05-12	5-Cyan-prostacyclinderivate, Verfahren zu ihrer Herstellung und ihrer Verwendung als Arzneimittel
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