DD293353A5 - Verfahren zur herstellung von phenylen-7-oxabicyloheptyl-substituierten heterocycloamid-prostaglandinanalogen - Google Patents

Verfahren zur herstellung von phenylen-7-oxabicyloheptyl-substituierten heterocycloamid-prostaglandinanalogen Download PDF

Info

Publication number: DD293353A5
Authority: DD; German Democratic Republic
Prior art keywords: mmol; acid; solution; general formula; methyl
Prior art date: 1989-04-03

Application number

DD90339392A

Other languages

German (de)

English (en)

Inventor

Raj N Misra

Original Assignee

�K@�K@��@�K@��k��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.)

1989-04-03

Filing date

1990-04-03

Publication date

1991-08-29

1990-04-03 Application filed by �K@�K@��@�K@��k��Kk�� filed Critical �K@�K@��@�K@��k��Kk��

1991-08-29 Publication of DD293353A5 publication Critical patent/DD293353A5/de

Links

238000004519 manufacturing process Methods 0.000 title 1
-1 5-tetrazolyl Chemical group 0.000 claims abstract description 119
125000000217 alkyl group Chemical group 0.000 claims abstract description 52
125000003118 aryl group Chemical group 0.000 claims abstract description 17
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 10
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 4
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 4
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
125000003435 aroyl group Chemical group 0.000 claims abstract description 3
125000000304 alkynyl group Chemical group 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 142
239000002253 acid Substances 0.000 claims description 70
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
238000000034 method Methods 0.000 claims description 37
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 28
150000002148 esters Chemical class 0.000 claims description 27
150000001412 amines Chemical class 0.000 claims description 21
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
125000004430 oxygen atom Chemical group O* 0.000 claims description 12
229910052783 alkali metal Inorganic materials 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
230000008569 process Effects 0.000 claims description 11
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
229960003424 phenylacetic acid Drugs 0.000 claims description 3
239000003279 phenylacetic acid Substances 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims 1
239000001257 hydrogen Substances 0.000 abstract description 19
229910052739 hydrogen Inorganic materials 0.000 abstract description 19
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 8
230000001732 thrombotic effect Effects 0.000 abstract description 6
201000010099 disease Diseases 0.000 abstract description 4
125000000623 heterocyclic group Chemical group 0.000 abstract description 4
230000002455 vasospastic effect Effects 0.000 abstract description 4
DYWAPFDKPAHSED-UHFFFAOYSA-N 2-cycloheptyloxepane Chemical group C1CCCCCC1C1OCCCCC1 DYWAPFDKPAHSED-UHFFFAOYSA-N 0.000 abstract description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
229920002554 vinyl polymer Polymers 0.000 abstract description 2
125000003368 amide group Chemical group 0.000 abstract 1
125000005343 heterocyclic alkyl group Chemical group 0.000 abstract 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
239000002184 metal Substances 0.000 abstract 1
150000003180 prostaglandins Chemical class 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 357
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 210
239000000243 solution Substances 0.000 description 170
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 138
230000002829 reductive effect Effects 0.000 description 131
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 124
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 114
239000000203 mixture Substances 0.000 description 111
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 102
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 83
239000003921 oil Substances 0.000 description 82
235000019198 oils Nutrition 0.000 description 81
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 79
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 79
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
239000011541 reaction mixture Substances 0.000 description 69
239000012074 organic phase Substances 0.000 description 67
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 63
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 62
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 62
229910052943 magnesium sulfate Inorganic materials 0.000 description 57
235000019341 magnesium sulphate Nutrition 0.000 description 57
239000000741 silica gel Substances 0.000 description 54
229910002027 silica gel Inorganic materials 0.000 description 54
125000000896 monocarboxylic acid group Chemical group 0.000 description 50
238000003818 flash chromatography Methods 0.000 description 46
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
238000006243 chemical reaction Methods 0.000 description 40
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
239000007787 solid Substances 0.000 description 35
239000000706 filtrate Substances 0.000 description 33
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 27
239000008346 aqueous phase Substances 0.000 description 26
239000012267 brine Substances 0.000 description 26
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 26
239000012043 crude product Substances 0.000 description 25
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
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 22
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
239000003208 petroleum Substances 0.000 description 21
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 20
150000001408 amides Chemical class 0.000 description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
239000002002 slurry Substances 0.000 description 18
239000003054 catalyst Substances 0.000 description 17
239000000284 extract Substances 0.000 description 17
125000006239 protecting group Chemical group 0.000 description 17
238000003756 stirring Methods 0.000 description 17
BYROZNMXSZTVRN-UHFFFAOYSA-N 7,7-dimethyloctan-1-amine Chemical compound CC(C)(C)CCCCCCN BYROZNMXSZTVRN-UHFFFAOYSA-N 0.000 description 16
229960000583 acetic acid Drugs 0.000 description 16
239000012230 colorless oil Substances 0.000 description 16
229920006395 saturated elastomer Polymers 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
239000012298 atmosphere Substances 0.000 description 15
239000000460 chlorine Substances 0.000 description 15
239000002585 base Substances 0.000 description 14
239000003153 chemical reaction reagent Substances 0.000 description 14
238000011282 treatment Methods 0.000 description 14
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 13
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 13
150000001298 alcohols Chemical class 0.000 description 13
239000007800 oxidant agent Substances 0.000 description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 13
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
239000010779 crude oil Substances 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
229910052786 argon Inorganic materials 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
239000006260 foam Substances 0.000 description 10
150000002825 nitriles Chemical class 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
239000003810 Jones reagent Substances 0.000 description 9
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 9
239000012362 glacial acetic acid Substances 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 9
239000004417 polycarbonate Substances 0.000 description 9
229920000515 polycarbonate Polymers 0.000 description 9
239000011591 potassium Substances 0.000 description 9
229910052700 potassium Inorganic materials 0.000 description 9
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 9
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
239000007789 gas Substances 0.000 description 8
239000012528 membrane Substances 0.000 description 8
229910052759 nickel Inorganic materials 0.000 description 8
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
238000006809 Jones oxidation reaction Methods 0.000 description 7
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 7
239000012965 benzophenone Substances 0.000 description 7
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
229950005499 carbon tetrachloride Drugs 0.000 description 6
150000002009 diols Chemical class 0.000 description 6
239000012259 ether extract Substances 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
239000010410 layer Substances 0.000 description 6
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 6
229940040692 lithium hydroxide monohydrate Drugs 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 6
PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 5
HJSBKANKLRDTKH-UHFFFAOYSA-N 4-cyclohexylbutan-1-amine;hydrochloride Chemical compound Cl.NCCCCC1CCCCC1 HJSBKANKLRDTKH-UHFFFAOYSA-N 0.000 description 5
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 5
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 5
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 5
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000012071 phase Substances 0.000 description 5
229910052698 phosphorus Inorganic materials 0.000 description 5
239000011574 phosphorus Substances 0.000 description 5
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 5
VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 4
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
102000003938 Thromboxane Receptors Human genes 0.000 description 4
108090000300 Thromboxane Receptors Proteins 0.000 description 4
206010047249 Venous thrombosis Diseases 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
239000011609 ammonium molybdate Substances 0.000 description 4
235000018660 ammonium molybdate Nutrition 0.000 description 4
APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 4
229940010552 ammonium molybdate Drugs 0.000 description 4
150000001450 anions Chemical class 0.000 description 4
239000012300 argon atmosphere Substances 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000001509 sodium citrate Substances 0.000 description 4
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
238000002560 therapeutic procedure Methods 0.000 description 4
238000005406 washing Methods 0.000 description 4
LTITXVXGJJQFJC-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)pyrrolidine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1NCCC1 LTITXVXGJJQFJC-UHFFFAOYSA-N 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000005557 antagonist Substances 0.000 description 3
235000010233 benzoic acid Nutrition 0.000 description 3
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QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 1
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239000003085 diluting agent Substances 0.000 description 1
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239000002547 new drug Substances 0.000 description 1
RRIWRJBSCGCBID-UHFFFAOYSA-L nickel sulfate hexahydrate Chemical compound O.O.O.O.O.O.[Ni+2].[O-]S([O-])(=O)=O RRIWRJBSCGCBID-UHFFFAOYSA-L 0.000 description 1
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230000036961 partial effect Effects 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
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CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
230000010118 platelet activation Effects 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
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XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 1
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239000012279 sodium borohydride Substances 0.000 description 1
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QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
239000008259 solid foam Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
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125000001424 substituent group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
150000003549 thiazolines Chemical class 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
239000002396 thromboxane receptor blocking agent Substances 0.000 description 1
230000000451 tissue damage Effects 0.000 description 1
231100000827 tissue damage Toxicity 0.000 description 1
LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
201000010875 transient cerebral ischemia Diseases 0.000 description 1
230000000472 traumatic effect Effects 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
UEWNEQVNIYYFFF-UHFFFAOYSA-N triphenylphosphanium;dibromide Chemical compound [Br-].[Br-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 UEWNEQVNIYYFFF-UHFFFAOYSA-N 0.000 description 1
125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229960005356 urokinase Drugs 0.000 description 1
230000003639 vasoconstrictive effect Effects 0.000 description 1
230000029663 wound healing Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Diabetes (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD90339392A 1989-04-03 1990-04-03 Verfahren zur herstellung von phenylen-7-oxabicyloheptyl-substituierten heterocycloamid-prostaglandinanalogen DD293353A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US33407089A	1989-04-03	1989-04-03

Publications (1)

Publication Number	Publication Date
DD293353A5 true DD293353A5 (de)	1991-08-29

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ID=23305449

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Application Number	Title	Priority Date	Filing Date
DD90339392A DD293353A5 (de)	1989-04-03	1990-04-03	Verfahren zur herstellung von phenylen-7-oxabicyloheptyl-substituierten heterocycloamid-prostaglandinanalogen

Country Status (28)

Country	Link
EP (1)	EP0391652B1 (fr)
JP (1)	JP2989213B2 (fr)
KR (1)	KR0160508B1 (fr)
CN (1)	CN1028529C (fr)
AT (1)	ATE119903T1 (fr)
AU (1)	AU632797B2 (fr)
CA (1)	CA2012267C (fr)
CY (1)	CY1851A (fr)
CZ (1)	CZ285656B6 (fr)
DD (1)	DD293353A5 (fr)
DE (1)	DE69017735T2 (fr)
DK (1)	DK0391652T3 (fr)
EG (1)	EG19080A (fr)
ES (1)	ES2069682T3 (fr)
FI (1)	FI97543C (fr)
HK (1)	HK110495A (fr)
HU (2)	HUT54368A (fr)
IE (1)	IE67274B1 (fr)
IL (1)	IL93771A (fr)
MX (1)	MX20132A (fr)
MY (1)	MY106245A (fr)
NO (1)	NO177425C (fr)
NZ (1)	NZ232897A (fr)
PL (1)	PL164345B1 (fr)
PT (1)	PT93641B (fr)
RU (1)	RU2059618C1 (fr)
SK (1)	SK158290A3 (fr)
ZA (1)	ZA902559B (fr)

Families Citing this family (25)

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Publication number	Priority date	Publication date	Assignee	Title
NZ233600A (en) *	1989-06-12	1992-10-28	Squibb & Sons Inc	7-oxabicyclo(2.2.1)heptane imidazole prostaglandin analogs and pharmaceutical compositions
US4977174A (en) *	1989-06-12	1990-12-11	E. R. Squibb & Sons, Inc.	7-oxabicycloheptane imidazole prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease
ZA911453B (en) *	1990-03-19	1991-11-27	Squibb & Sons Inc	Method of protecting against and/or treating ulcerative gastrointestinal conditions using a thromoboxane,a2 receptor antagonist and combination useful in preventing and/or treating ulcers and/or inflammation
US5290799A (en) *	1990-09-19	1994-03-01	E. R. Squibb & Sons, Inc.	7-oxabicycloheptyl substituted heterocyclic thioamide prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease
US5550248A (en) *	1990-11-29	1996-08-27	E.R. Squibb & Sons, Inc.	Substituted stryl heterocyclic amido prostaglandin analogs
US5135939A (en) *	1991-01-28	1992-08-04	E. R. Squibb & Sons, Inc.	Heterocyclic ketone prostaglandin analogs
US5238951A (en) *	1991-02-01	1993-08-24	E. R. Squibb & Sons, Inc.	Heterocyclic amido prostaglandin analogs
IE920039A1 (en) *	1991-02-01	1992-08-12	Squibb & Sons Inc	Heterocyclic amido prostaglandin analogs
US5158967A (en) *	1991-06-12	1992-10-27	E. R. Squibb & Sons, Inc.	7-oxabicycloheptyl substituted heterocyclic amide prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease
US5162352A (en) *	1991-08-22	1992-11-10	E. R. Squibb & Sons, Inc.	7-oxabicycloheptyl substituted heterocyclic amide prostaglandin analogs
CA2081679A1 (fr) *	1991-11-27	1993-05-28	Raj N. Misra	Analogues de prostaglandines amidiques heterocycliques de type pem-dialkyl-7-oxabicycloheptyle substitues utiles dans le traitement des thromboses et des spasmes vasculaires
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1990
- 1990-03-13 NZ NZ232897A patent/NZ232897A/xx unknown
- 1990-03-15 CA CA002012267A patent/CA2012267C/fr not_active Expired - Lifetime
- 1990-03-16 IL IL9377190A patent/IL93771A/en not_active IP Right Cessation
- 1990-03-19 MY MYPI90000427A patent/MY106245A/en unknown
- 1990-03-21 AU AU52064/90A patent/AU632797B2/en not_active Ceased
- 1990-03-26 IE IE109590A patent/IE67274B1/en not_active IP Right Cessation
- 1990-03-30 CZ CS901582A patent/CZ285656B6/cs not_active IP Right Cessation
- 1990-03-30 MX MX2013290A patent/MX20132A/es unknown
- 1990-03-30 SK SK1582-90A patent/SK158290A3/sk unknown
- 1990-04-02 KR KR1019900004487A patent/KR0160508B1/ko not_active Expired - Fee Related
- 1990-04-02 DE DE69017735T patent/DE69017735T2/de not_active Expired - Fee Related
- 1990-04-02 NO NO901494A patent/NO177425C/no unknown
- 1990-04-02 EP EP90303537A patent/EP0391652B1/fr not_active Expired - Lifetime
- 1990-04-02 PT PT93641A patent/PT93641B/pt not_active IP Right Cessation
- 1990-04-02 ES ES90303537T patent/ES2069682T3/es not_active Expired - Lifetime
- 1990-04-02 HU HU902048A patent/HUT54368A/hu unknown
- 1990-04-02 FI FI901645A patent/FI97543C/fi not_active IP Right Cessation
- 1990-04-02 DK DK90303537.6T patent/DK0391652T3/da active
- 1990-04-02 AT AT90303537T patent/ATE119903T1/de not_active IP Right Cessation
- 1990-04-03 EG EG20890A patent/EG19080A/xx active
- 1990-04-03 DD DD90339392A patent/DD293353A5/de not_active IP Right Cessation
- 1990-04-03 PL PL90284600A patent/PL164345B1/pl unknown
- 1990-04-03 CN CN90101837A patent/CN1028529C/zh not_active Expired - Lifetime
- 1990-04-03 ZA ZA902559A patent/ZA902559B/xx unknown
- 1990-04-03 JP JP2090070A patent/JP2989213B2/ja not_active Expired - Fee Related
1992
- 1992-01-14 RU SU925010525A patent/RU2059618C1/ru not_active IP Right Cessation
1994
- 1994-12-15 HU HU94P/P00057P patent/HU210713A9/hu unknown
1995
- 1995-07-06 HK HK110495A patent/HK110495A/en not_active IP Right Cessation
1996
- 1996-03-08 CY CY185196A patent/CY1851A/xx unknown

Also Published As

Publication number	Publication date
CA2012267C (fr)	2001-02-27
ATE119903T1 (de)	1995-04-15
EP0391652A1 (fr)	1990-10-10
IE67274B1 (en)	1996-03-20
DE69017735D1 (de)	1995-04-20
IE901095L (en)	1990-10-03
SK278865B6 (sk)	1998-04-08
IL93771A0 (en)	1990-12-23
EG19080A (en)	1994-07-30
CZ285656B6 (cs)	1999-10-13
HK110495A (en)	1995-07-14
NO177425C (no)	1995-09-20
CZ158290A3 (cs)	1999-06-16
PL284600A1 (en)	1991-01-14
HU9002048D0 (en)	1990-08-28
MX20132A (es)	1994-01-31
DE69017735T2 (de)	1995-08-17
HUT54368A (en)	1991-02-28
JP2989213B2 (ja)	1999-12-13
RU2059618C1 (ru)	1996-05-10
JPH02289579A (ja)	1990-11-29
DK0391652T3 (da)	1995-04-03
MY106245A (en)	1995-04-29
KR0160508B1 (ko)	1998-12-01
PL164345B1 (pl)	1994-07-29
IL93771A (en)	1995-06-29
EP0391652B1 (fr)	1995-03-15
NO901494L (no)	1990-10-04
FI97543B (fi)	1996-09-30
CN1028529C (zh)	1995-05-24
NO177425B (no)	1995-06-06
FI901645A0 (fi)	1990-04-02
HU210713A9 (en)	1995-06-28
NO901494D0 (no)	1990-04-02
SK158290A3 (en)	1998-04-08
ES2069682T3 (es)	1995-05-16
ZA902559B (en)	1991-01-30
FI97543C (fi)	1997-01-10
KR900016197A (ko)	1990-11-12
AU5206490A (en)	1990-10-04
CA2012267A1 (fr)	1990-10-03
PT93641A (pt)	1990-11-20
CY1851A (en)	1996-03-08
AU632797B2 (en)	1993-01-14
CN1046163A (zh)	1990-10-17
NZ232897A (en)	1992-12-23
PT93641B (pt)	1996-06-28

Legal Events

Date	Code	Title	Description
1996-04-25	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69017735T2 (de)	1995-08-17	Interphenylen-7-oxabicycloheptyl substituierte heterocyclische Amid-Prostaglandin-Analoge, geeignet bei der Behandlung von thrombotischen und vasopastischen Leiden.
EP0332008A2 (fr)	1989-09-13	Dérivés d'aminoacide du genre peptide
CA2079705A1 (fr)	1993-04-08	Analogues de la prostaglandine
US4977174A (en)	1990-12-11	7-oxabicycloheptane imidazole prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease
EP0374952A2 (fr)	1990-06-27	Analogues de prostaglandine du type amide hétérocyclique substitué par un groupe 7-oxybicycloheptyle utiles dans le traitement des maladies vasospastiques et thrombotiques
DE3625870A1 (de)	1987-02-05	7-oxabicycloheptansubstituierte amid-thioamid-prostaglandin-analoge
DE3441660A1 (de)	1985-05-23	7-oxabicycloheptanthioaether und arzneimittel mit einem gehalt an diesen verbindungen
US5153327A (en)	1992-10-06	7-Oxabicycloheptyl substituted heterocyclic amide or ester prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease
US4638012A (en)	1987-01-20	7-oxabicycloheptane α-substituted ketone prostaglandin analogs useful in the treatment of thrombotic disease
DE3735128A1 (de)	1988-04-21	7-oxabicycloheptan-derivate und diese verbindungen enthaltende arzneimittel
US5290799A (en)	1994-03-01	7-oxabicycloheptyl substituted heterocyclic thioamide prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease
DE3613719A1 (de)	1986-10-30	7-oxabicycloheptanaether
DE3621449A1 (de)	1987-01-02	5,6-epoxy-7-oxabicycloheptansubstituierte aminoprostaglandin-analoga und diese enthaltende arzneimittel
DD207379A5 (de)	1984-02-29	Verfahren zur herstellung 1,1-alkandioldicarboxylatverknuepfter antibakterieller mittel
DD299186A5 (de)	1992-04-02	Phenylen-7-oxabicycloheptyl-substituierte heterocycloamid-prostaglandinanaloga
DE3606431A1 (de)	1986-08-28	Thiabicycloheptan-substituierte aminoprostaglandin-analoge
DE3715208A1 (de)	1987-11-12	7-oxabicycloheptan-substituierte amido-carbamoyl-prostaglandin-analoge
US5135939A (en)	1992-08-04	Heterocyclic ketone prostaglandin analogs
AU629932B2 (en)	1992-10-15	7-oxabicycloheptane imidazole prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease
US5550248A (en)	1996-08-27	Substituted stryl heterocyclic amido prostaglandin analogs
EP0497629A1 (fr)	1992-08-05	Amides hétérocycliques analogues des prostaglandines
EP0419411A2 (fr)	1991-03-27	Alkanophénones additionnels