DE2334945A1 - Neue prostaglandinanaloge und verfahren zu deren herstellung - Google Patents
Neue prostaglandinanaloge und verfahren zu deren herstellungInfo
- Publication number
- DE2334945A1 DE2334945A1 DE19732334945 DE2334945A DE2334945A1 DE 2334945 A1 DE2334945 A1 DE 2334945A1 DE 19732334945 DE19732334945 DE 19732334945 DE 2334945 A DE2334945 A DE 2334945A DE 2334945 A1 DE2334945 A1 DE 2334945A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- radical
- compound
- lower alkyl
- double bond
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 108
- 150000003180 prostaglandins Chemical class 0.000 title claims description 55
- 230000008569 process Effects 0.000 title claims description 34
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- -1 alkyl radical Chemical class 0.000 claims description 356
- 150000001875 compounds Chemical class 0.000 claims description 321
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 124
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 116
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 107
- 239000002253 acid Substances 0.000 claims description 77
- 229910052757 nitrogen Inorganic materials 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 58
- 238000006243 chemical reaction Methods 0.000 claims description 56
- 125000001424 substituent group Chemical group 0.000 claims description 54
- 125000005843 halogen group Chemical group 0.000 claims description 51
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 33
- 150000003254 radicals Chemical class 0.000 claims description 33
- 230000002829 reductive effect Effects 0.000 claims description 31
- 238000002360 preparation method Methods 0.000 claims description 28
- SXXLKZCNJHJYFL-UHFFFAOYSA-N 4,5,6,7-tetrahydro-[1,2]oxazolo[4,5-c]pyridin-5-ium-3-olate Chemical compound C1CNCC2=C1ONC2=O SXXLKZCNJHJYFL-UHFFFAOYSA-N 0.000 claims description 22
- 101000799461 Homo sapiens Thrombopoietin Proteins 0.000 claims description 22
- 102100034195 Thrombopoietin Human genes 0.000 claims description 22
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims description 14
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 11
- 229930194542 Keto Natural products 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 125000000468 ketone group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 229910014033 C-OH Inorganic materials 0.000 claims description 4
- 229910014570 C—OH Inorganic materials 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000012024 dehydrating agents Substances 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 2
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 27
- 125000001589 carboacyl group Chemical group 0.000 claims 7
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims 2
- 101000831254 Oryza sativa subsp. japonica Cysteine proteinase inhibitor 2 Proteins 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 292
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 249
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 148
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 136
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 127
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 106
- 239000011541 reaction mixture Substances 0.000 description 91
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
- 239000000047 product Substances 0.000 description 86
- 230000009102 absorption Effects 0.000 description 77
- 238000010521 absorption reaction Methods 0.000 description 77
- 229960000583 acetic acid Drugs 0.000 description 77
- 239000000203 mixture Substances 0.000 description 71
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 70
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 67
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 60
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 53
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 51
- 238000002329 infrared spectrum Methods 0.000 description 51
- 239000000741 silica gel Substances 0.000 description 50
- 229910002027 silica gel Inorganic materials 0.000 description 50
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 46
- 235000019341 magnesium sulphate Nutrition 0.000 description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 238000004440 column chromatography Methods 0.000 description 42
- 238000003756 stirring Methods 0.000 description 42
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 40
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 39
- 239000007787 solid Substances 0.000 description 38
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 239000012299 nitrogen atmosphere Substances 0.000 description 32
- 239000000284 extract Substances 0.000 description 31
- 239000012535 impurity Substances 0.000 description 30
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 29
- 239000003153 chemical reaction reagent Substances 0.000 description 29
- 239000003480 eluent Substances 0.000 description 26
- 239000012362 glacial acetic acid Substances 0.000 description 26
- 150000002596 lactones Chemical class 0.000 description 25
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 24
- 229920006395 saturated elastomer Polymers 0.000 description 24
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 23
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 20
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- 235000019198 oils Nutrition 0.000 description 19
- 239000011734 sodium Substances 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- 238000001228 spectrum Methods 0.000 description 18
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 17
- 239000012043 crude product Substances 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 17
- 238000002390 rotary evaporation Methods 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- 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 15
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 15
- 229910052708 sodium Inorganic materials 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 14
- 239000007789 gas Substances 0.000 description 14
- 239000005457 ice water Substances 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 12
- 239000002245 particle Substances 0.000 description 12
- 230000009467 reduction Effects 0.000 description 12
- 238000006722 reduction reaction Methods 0.000 description 12
- 239000011701 zinc Substances 0.000 description 12
- 241000700199 Cavia porcellus Species 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 239000008241 heterogeneous mixture Substances 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 239000011780 sodium chloride Substances 0.000 description 11
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 10
- 239000010779 crude oil Substances 0.000 description 10
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 10
- 239000001476 sodium potassium tartrate Substances 0.000 description 10
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 10
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 9
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 9
- 150000002373 hemiacetals Chemical class 0.000 description 9
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 9
- 210000002460 smooth muscle Anatomy 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 210000001519 tissue Anatomy 0.000 description 9
- 229910052725 zinc Inorganic materials 0.000 description 9
- 239000003810 Jones reagent Substances 0.000 description 8
- 150000001241 acetals Chemical class 0.000 description 8
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- 238000004566 IR spectroscopy Methods 0.000 description 7
- 229940124630 bronchodilator Drugs 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000000499 gel Substances 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- GATUGNVDXMYTJX-UHFFFAOYSA-N methyl 4-phenylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=CC=C1 GATUGNVDXMYTJX-UHFFFAOYSA-N 0.000 description 7
- 230000001766 physiological effect Effects 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000003929 acidic solution Substances 0.000 description 6
- 239000000443 aerosol Substances 0.000 description 6
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- 230000002401 inhibitory effect Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
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- 125000006239 protecting group Chemical group 0.000 description 6
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- 210000004291 uterus Anatomy 0.000 description 6
- NTJPVVKEZMOHNU-UHFFFAOYSA-N 6-(oxan-4-yl)-1h-indazole Chemical compound C1COCCC1C1=CC=C(C=NN2)C2=C1 NTJPVVKEZMOHNU-UHFFFAOYSA-N 0.000 description 5
- 206010000210 abortion Diseases 0.000 description 5
- 231100000176 abortion Toxicity 0.000 description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
- 230000036772 blood pressure Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000013065 commercial product Substances 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
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- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 230000035558 fertility Effects 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- HQJAUSGLWRLGOI-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-phenylpropan-2-one Chemical compound COP(=O)(OC)CC(=O)CC1=CC=CC=C1 HQJAUSGLWRLGOI-UHFFFAOYSA-N 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 4
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- 125000002252 acyl group Chemical group 0.000 description 4
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- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
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- 238000000746 purification Methods 0.000 description 4
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- 230000004044 response Effects 0.000 description 4
- 230000004936 stimulating effect Effects 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
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- 150000001298 alcohols Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
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- 239000002775 capsule Substances 0.000 description 3
- YCXVDEMHEKQQCI-UHFFFAOYSA-N chloro-dimethyl-propan-2-ylsilane Chemical compound CC(C)[Si](C)(C)Cl YCXVDEMHEKQQCI-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 230000027119 gastric acid secretion Effects 0.000 description 3
- 230000001077 hypotensive effect Effects 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 3
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- MBYFZYKLKDLPEU-UHFFFAOYSA-N 2-dimethoxyphosphoryl-1-phenylethanone Chemical compound COP(=O)(OC)CC(=O)C1=CC=CC=C1 MBYFZYKLKDLPEU-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-L phosphonate(2-) Chemical compound [O-]P([O-])=O ABLZXFCXXLZCGV-UHFFFAOYSA-L 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- KYKNRZGSIGMXFH-ZVGUSBNCSA-M potassium bitartrate Chemical compound [K+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O KYKNRZGSIGMXFH-ZVGUSBNCSA-M 0.000 description 1
- 239000001472 potassium tartrate Substances 0.000 description 1
- 229940111695 potassium tartrate Drugs 0.000 description 1
- 235000011005 potassium tartrates Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- NRTYMEPCRDJMPZ-UHFFFAOYSA-N pyridine;2,2,2-trifluoroacetic acid Chemical compound C1=CC=NC=C1.OC(=O)C(F)(F)F NRTYMEPCRDJMPZ-UHFFFAOYSA-N 0.000 description 1
- 108700022737 rat Fat1 Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 230000035884 vasodepression Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
- C07F9/4059—Compounds containing the structure (RY)2P(=X)-(CH2)n-C(=O)-(CH2)m-Ar, (X, Y = O, S, Se; n>=1, m>=0)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B63—SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
- B63B—SHIPS OR OTHER WATERBORNE VESSELS; EQUIPMENT FOR SHIPPING
- B63B2211/00—Applications
- B63B2211/02—Oceanography
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Compounds Of Unknown Constitution (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732353159 DE2353159A1 (de) | 1972-07-13 | 1973-07-10 | Ketophosphonate und verfahren zu deren herstellung |
| DE19732365767 DE2365767A1 (de) | 1972-07-13 | 1973-07-10 | Neue prostaglandinanaloge und verfahren zu deren herstellung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27122072A | 1972-07-13 | 1972-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2334945A1 true DE2334945A1 (de) | 1974-03-07 |
Family
ID=23034697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732334945 Withdrawn DE2334945A1 (de) | 1972-07-13 | 1973-07-10 | Neue prostaglandinanaloge und verfahren zu deren herstellung |
Country Status (25)
| Country | Link |
|---|---|
| JP (4) | JPS5241257B2 (xx) |
| AR (2) | AR209064A1 (xx) |
| AT (1) | AT367033B (xx) |
| BE (1) | BE802231A (xx) |
| CA (1) | CA1041495A (xx) |
| CH (1) | CH593254A5 (xx) |
| CS (1) | CS201027B2 (xx) |
| DD (2) | DD116459A5 (xx) |
| DE (1) | DE2334945A1 (xx) |
| ES (4) | ES416865A1 (xx) |
| FI (1) | FI57583C (xx) |
| FR (1) | FR2192834B1 (xx) |
| GB (1) | GB1446341A (xx) |
| HU (4) | HU171156B (xx) |
| IE (1) | IE37909B1 (xx) |
| IL (2) | IL42691A (xx) |
| IN (1) | IN138789B (xx) |
| LU (1) | LU68015A1 (xx) |
| NL (1) | NL7309792A (xx) |
| NO (2) | NO143741C (xx) |
| PH (1) | PH11461A (xx) |
| SE (3) | SE7705946L (xx) |
| SU (4) | SU644384A3 (xx) |
| YU (1) | YU187773A (xx) |
| ZA (1) | ZA734769B (xx) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2416193A1 (de) | 1974-04-03 | 1975-10-23 | Hoechst Ag | Neue prostaglandin-analoge und verfahren zu ihrer herstellung |
| DE2463432C2 (xx) * | 1974-04-03 | 1987-06-19 | Hoechst Ag, 6230 Frankfurt, De | |
| WO1992002496A1 (en) * | 1990-08-08 | 1992-02-20 | Kabi Pharmacia Ab | A method for synthesis of prostaglandin derivatives |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1386146A (en) * | 1972-05-03 | 1975-03-05 | Ici Ltd | Cyclopentane derivatives |
| ZA747723B (en) * | 1974-12-11 | 1976-11-24 | Pfizer | 11-desoxy-15-substituted-omega-pentanor prostaglandins |
| US4149006A (en) * | 1977-01-24 | 1979-04-10 | G. D. Searle & Co. | Prostaglandin derivatives having alkynyl, hydroxy and aryloxy junctions in the 2β side chain |
| GB8329559D0 (en) * | 1983-11-04 | 1983-12-07 | Erba Farmitalia | Furyl derivatives of 16-substituted prostaglandins preparations |
| US6602900B2 (en) | 1992-09-21 | 2003-08-05 | Allergan, Inc. | Cyclopentane heptan(ENE)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
| US5972991A (en) * | 1992-09-21 | 1999-10-26 | Allergan | Cyclopentane heptan(ene) oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
| KR100578616B1 (ko) * | 2004-07-23 | 2006-05-10 | 한미약품 주식회사 | Ｄ-에리트로-2,2-다이플루오로-2-데옥시-1-옥소라이보스화합물의 제조방법 |
| EP3080096A1 (en) * | 2013-12-13 | 2016-10-19 | Allergan, Inc. | Solid forms of an alpha, omega di-substituted dihydroxy cyclopentyl compound and methods for the preparation and use thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1324737A (en) * | 1970-11-02 | 1973-07-25 | Upjohn Co | Prostaglandins and the preparation thereof |
| GB1386146A (en) * | 1972-05-03 | 1975-03-05 | Ici Ltd | Cyclopentane derivatives |
| IL42373A (en) * | 1972-06-02 | 1977-08-31 | Pfizer | Oxaprostagliandins and their preparation |
-
1973
- 1973-07-03 ES ES416865A patent/ES416865A1/es not_active Expired
- 1973-07-03 NO NO2724/73A patent/NO143741C/no unknown
- 1973-07-05 FI FI2162/73A patent/FI57583C/fi active
- 1973-07-06 IN IN1575/CAL/73A patent/IN138789B/en unknown
- 1973-07-09 IL IL42691A patent/IL42691A/xx unknown
- 1973-07-09 PH PH14802A patent/PH11461A/en unknown
- 1973-07-10 DE DE19732334945 patent/DE2334945A1/de not_active Withdrawn
- 1973-07-11 CS CS734994A patent/CS201027B2/cs unknown
- 1973-07-12 DD DD180811*A patent/DD116459A5/xx unknown
- 1973-07-12 BE BE1005234A patent/BE802231A/xx unknown
- 1973-07-12 CH CH1020673A patent/CH593254A5/xx not_active IP Right Cessation
- 1973-07-12 HU HU73PI00000387A patent/HU171156B/hu unknown
- 1973-07-12 HU HU73PI00000480A patent/HU171158B/hu unknown
- 1973-07-12 DD DD172243A patent/DD109210A5/xx unknown
- 1973-07-12 SU SU731948945A patent/SU644384A3/ru active
- 1973-07-12 HU HU73PI00000481A patent/HU171946B/hu unknown
- 1973-07-12 CA CA176,270A patent/CA1041495A/en not_active Expired
- 1973-07-12 HU HU73PI00000482A patent/HU172058B/hu unknown
- 1973-07-13 AT AT0620773A patent/AT367033B/de not_active IP Right Cessation
- 1973-07-13 FR FR7325835A patent/FR2192834B1/fr not_active Expired
- 1973-07-13 ZA ZA734769A patent/ZA734769B/xx unknown
- 1973-07-13 IE IE1186/73A patent/IE37909B1/xx unknown
- 1973-07-13 GB GB3121773A patent/GB1446341A/en not_active Expired
- 1973-07-13 NL NL7309792A patent/NL7309792A/xx not_active Application Discontinuation
- 1973-07-13 JP JP48079214A patent/JPS5241257B2/ja not_active Expired
- 1973-07-13 AR AR249095A patent/AR209064A1/es active
- 1973-07-13 LU LU68015A patent/LU68015A1/xx unknown
- 1973-11-07 YU YU01877/73A patent/YU187773A/xx unknown
-
1974
- 1974-05-06 AR AR253775A patent/AR214383A1/es active
- 1974-09-26 NO NO743492A patent/NO144830C/no unknown
-
1975
- 1975-04-26 ES ES437037A patent/ES437037A1/es not_active Expired
- 1975-04-26 ES ES437039A patent/ES437039A1/es not_active Expired
- 1975-04-26 ES ES437038A patent/ES437038A1/es not_active Expired
- 1975-09-05 SU SU752169008A patent/SU645563A3/ru active
- 1975-09-09 SU SU7502170659A patent/SU584791A3/ru active
- 1975-09-11 SU SU752171155A patent/SU645564A3/ru active
-
1976
- 1976-08-19 IL IL50308A patent/IL50308A0/xx unknown
- 1976-11-22 JP JP14060676A patent/JPS52122349A/ja active Pending
- 1976-11-22 JP JP14060576A patent/JPS5297958A/ja active Pending
- 1976-11-22 JP JP14060776A patent/JPS5293753A/ja active Pending
-
1977
- 1977-05-20 SE SE7705946A patent/SE7705946L/xx unknown
- 1977-05-20 SE SE7705947A patent/SE7705947L/xx not_active Application Discontinuation
- 1977-05-20 SE SE7705945A patent/SE7705945L/xx not_active Application Discontinuation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2416193A1 (de) | 1974-04-03 | 1975-10-23 | Hoechst Ag | Neue prostaglandin-analoge und verfahren zu ihrer herstellung |
| DE2463432C2 (xx) * | 1974-04-03 | 1987-06-19 | Hoechst Ag, 6230 Frankfurt, De | |
| WO1992002496A1 (en) * | 1990-08-08 | 1992-02-20 | Kabi Pharmacia Ab | A method for synthesis of prostaglandin derivatives |
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Legal Events
| Date | Code | Title | Description |
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| 8130 | Withdrawal |