CS262662B2 - Process for preparing new racemic and optical active derivatives of interfuranylenprostacycline - Google Patents

Process for preparing new racemic and optical active derivatives of interfuranylenprostacycline Download PDF

Info

Publication number: CS262662B2
Authority: CS; Czechoslovakia
Prior art keywords: group; formula; compound; hydrogen; alkyl group
Prior art date: 1985-01-17

Application number

CS86343A

Other languages

Czech (cs)

English (en)

Other versions

CS34386A2 (en

Inventor

Geza Dr Galambos

Jozsef Dr Ivanics

Gyorgy Dorman

Karoly Kanay

Istvan Dr Tomoskozy

Gabor Dr Kovacs

Istvan Dr Stadler

Peter Dr Kormoczi

Pal Dr Hadhazy

Sandor Dr Virag

Miklos Dr Kiss

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-01-17

Filing date

1986-01-16

Publication date

1989-03-14

1986-01-16 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1987-08-31 Priority to CS876342A priority Critical patent/CS262696B2/cs

1987-08-31 Priority to CS876343A priority patent/CS262697B2/cs

1988-08-16 Publication of CS34386A2 publication Critical patent/CS34386A2/cs

1989-03-14 Publication of CS262662B2 publication Critical patent/CS262662B2/cs

Links

238000004519 manufacturing process Methods 0.000 title 1
230000003287 optical effect Effects 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 67
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
239000001257 hydrogen Substances 0.000 claims abstract description 23
239000000126 substance Substances 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
150000001767 cationic compounds Chemical class 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
229910001411 inorganic cation Inorganic materials 0.000 claims abstract description 3
150000002367 halogens Chemical group 0.000 claims abstract 4
238000002360 preparation method Methods 0.000 claims description 13
238000000034 method Methods 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
239000007800 oxidant agent Substances 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 abstract description 15
-1 monosubstituted benzoyl Chemical group 0.000 abstract description 5
208000010110 spontaneous platelet aggregation Diseases 0.000 abstract description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 3
230000002401 inhibitory effect Effects 0.000 abstract description 3
239000003795 chemical substances by application Substances 0.000 abstract description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
239000005977 Ethylene Substances 0.000 abstract 1
208000001953 Hypotension Diseases 0.000 abstract 1
125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
125000003277 amino group Chemical group 0.000 abstract 1
230000002959 anti-hypotensive effect Effects 0.000 abstract 1
230000002785 anti-thrombosis Effects 0.000 abstract 1
239000003146 anticoagulant agent Substances 0.000 abstract 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
125000001072 heteroaryl group Chemical group 0.000 abstract 1
208000021822 hypotensive Diseases 0.000 abstract 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
150000003815 prostacyclins Chemical class 0.000 abstract 1
125000004665 trialkylsilyl group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 41
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
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 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
229960001123 epoprostenol Drugs 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000203 mixture Substances 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 10
239000002904 solvent Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
235000019441 ethanol Nutrition 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
239000013078 crystal Substances 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
150000004702 methyl esters Chemical class 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
WJCXADMLESSGRI-UHFFFAOYSA-N phenyl selenohypochlorite Chemical compound Cl[Se]C1=CC=CC=C1 WJCXADMLESSGRI-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 4
101000862089 Clarkia lewisii Glucose-6-phosphate isomerase, cytosolic 1A Proteins 0.000 description 3
101710129448 Glucose-6-phosphate isomerase 2 Proteins 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000009471 action Effects 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
230000001120 cytoprotective effect Effects 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000005055 short column chromatography Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 2
XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 2
206010002383 Angina Pectoris Diseases 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229910000342 sodium bisulfate Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
238000003756 stirring Methods 0.000 description 2
210000002784 stomach Anatomy 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical class CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
206010053567 Coagulopathies Diseases 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
241000021559 Dicerandra Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
206010018910 Haemolysis Diseases 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
208000000857 Hepatic Insufficiency Diseases 0.000 description 1
206010019663 Hepatic failure Diseases 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
235000010654 Melissa officinalis Nutrition 0.000 description 1
206010027476 Metastases Diseases 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
208000018262 Peripheral vascular disease Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
230000002612 cardiopulmonary effect Effects 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
230000035602 clotting Effects 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000001066 destructive effect Effects 0.000 description 1
201000009101 diabetic angiopathy Diseases 0.000 description 1
201000002249 diabetic peripheral angiopathy Diseases 0.000 description 1
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
POCFBDFTJMJWLG-UHFFFAOYSA-N dihydrosinapic acid methyl ester Natural products COC(=O)CCC1=CC(OC)=C(O)C(OC)=C1 POCFBDFTJMJWLG-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
125000003500 enol ether group Chemical group 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical group CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
230000029142 excretion Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
229940001440 flolan Drugs 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
238000001631 haemodialysis Methods 0.000 description 1
235000015220 hamburgers Nutrition 0.000 description 1
210000002216 heart Anatomy 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000008588 hemolysis Effects 0.000 description 1
229960002897 heparin Drugs 0.000 description 1
229920000669 heparin Polymers 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical class CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000000865 liniment Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
208000019423 liver disease Diseases 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
239000005445 natural material Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000008816 organ damage Effects 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
150000003962 selenoxides Chemical class 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
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239000003826 tablet Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A61P35/00—Antineoplastic agents
- 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
- A61P9/12—Antihypertensives
- 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
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers

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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
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CS86343A 1985-01-17 1986-01-16 Process for preparing new racemic and optical active derivatives of interfuranylenprostacycline CS262662B2 (en)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CS876342A CS262696B2 (cs)	1985-01-17	1987-08-31	Způsob výroby nových racemických a opticky aktivních derivátů interfuranylenprostacyklinu
CS876343A CS262697B2 (cs)	1985-01-17	1987-08-31	Zpusob výroby nových racemických a opticky aktivních derivátů interfuranylenprostacyklinu

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU85195A HU192909B (en)	1985-01-17	1985-01-17	Process for producing interfuranylene-prostacycline derivatives

Publications (2)

Publication Number	Publication Date
CS34386A2 CS34386A2 (en)	1988-08-16
CS262662B2 true CS262662B2 (en)	1989-03-14

Family

ID=10948415

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS86343A CS262662B2 (en)	1985-01-17	1986-01-16	Process for preparing new racemic and optical active derivatives of interfuranylenprostacycline

Country Status (10)

Country	Link
US (1)	US4740523A (pl)
EP (1)	EP0193260A3 (pl)
JP (1)	JPS61218588A (pl)
AU (1)	AU589591B2 (pl)
CS (1)	CS262662B2 (pl)
DD (1)	DD244343A5 (pl)
HU (1)	HU192909B (pl)
IL (1)	IL77614A (pl)
PL (3)	PL147351B1 (pl)
SU (2)	SU1470189A3 (pl)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK1059092T3 (da) *	1999-06-08	2006-03-27	Gentium Spa	Anvendelse af komplekser af kationiske liposomer og polydeoxyribonukleotider som medikamenter
TW201540711A (zh) *	2014-02-27	2015-11-01	Ono Pharmaceutical Co	具有選擇性ｅｐ２促效劑活性的化合物
EP3327018B1 (en) *	2015-07-23	2020-11-25	ONO Pharmaceutical Co., Ltd.	2-(octahydrocyclopenta[b]pyran-2-yl)1,3-thiazole-4-carboxylic acid derivatives and related compounds as ep2 agonists with intraocular pressure lowering activity

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4312810A (en) *	1978-11-22	1982-01-26	The Upjohn Company	2,5-Inter-o-phenylene-3,4-dinor-5,9α-epoxy-9-deoxy-PGF1 compounds
US4337203A (en) *	1979-07-31	1982-06-29	The Upjohn Company	2,5-Inter-o-phenylene-3,4-dinor-5,9α-epoxy PGF1 amides

1985
- 1985-01-17 HU HU85195A patent/HU192909B/hu not_active IP Right Cessation
1986
- 1986-01-15 IL IL77614A patent/IL77614A/xx unknown
- 1986-01-16 CS CS86343A patent/CS262662B2/cs unknown
- 1986-01-16 DD DD86286252A patent/DD244343A5/de unknown
- 1986-01-17 US US06/820,434 patent/US4740523A/en not_active Expired - Fee Related
- 1986-01-17 PL PL1986264566A patent/PL147351B1/pl unknown
- 1986-01-17 PL PL1986257532A patent/PL147313B1/pl unknown
- 1986-01-17 AU AU52514/86A patent/AU589591B2/en not_active Ceased
- 1986-01-17 JP JP61007828A patent/JPS61218588A/ja active Pending
- 1986-01-17 PL PL1986264567A patent/PL147352B1/pl unknown
- 1986-01-17 SU SU864015072A patent/SU1470189A3/ru active
- 1986-01-17 EP EP86300306A patent/EP0193260A3/en not_active Withdrawn
- 1986-05-26 SU SU864027504A patent/SU1467056A1/ru active

Also Published As

Publication number	Publication date
IL77614A (en)	1991-01-31
CS34386A2 (en)	1988-08-16
SU1467056A1 (ru)	1989-03-23
PL147352B1 (en)	1989-05-31
PL147313B1 (en)	1989-05-31
JPS61218588A (ja)	1986-09-29
AU5251486A (en)	1986-07-24
PL264567A1 (en)	1988-01-21
US4740523A (en)	1988-04-26
AU589591B2 (en)	1989-10-19
EP0193260A2 (en)	1986-09-03
PL257532A1 (en)	1987-07-27
IL77614A0 (en)	1986-08-31
HU192909B (en)	1987-07-28
PL147351B1 (en)	1989-05-31
PL264566A1 (en)	1988-01-21
DD244343A5 (de)	1987-04-01
SU1470189A3 (ru)	1989-03-30
EP0193260A3 (en)	1987-05-13
HUT38928A (en)	1986-07-28

Publication	Publication Date	Title
EP0816338B1 (en)	2003-02-12	3-(bis-substituted-phenylmethylene)oxindole derivatives
FI73206C (fi)	1987-09-10	Foerfarande foer framstaellning av terapeutiskt anvaendbara alkyltiofenoxipropylaminer.
CS262662B2 (en)	1989-03-14	Process for preparing new racemic and optical active derivatives of interfuranylenprostacycline
EP0157623B1 (en)	1989-03-22	Optically active isomers of benzopyran derivatives useful for treating cardiovascular disease
SU910118A3 (ru)	1982-02-28	Способ получени N @ -глюкофуранозид-6-ил-N @ -нитрозомочевины
JPH0460980B2 (pl)	1992-09-29
JPS58198467A (ja)	1983-11-18	新規プロスタグランデイン誘導体類
KR850000388B1 (ko)	1985-03-25	복소환 화합물 및 이의 이성체의 제조방법
EP0718307A2 (fr)	1996-06-26	Dérivés de 1-oxo-2-(phénylsulfonyl-amino)pentylpipéridine, leur préparation et leur application en thérapeutique
US4588713A (en)	1986-05-13	Selective biologically active 7-oxo-prostacyclin derivatives and pharmaceutical compositions containing same
FI78064B (fi)	1989-02-28	Foerfarande foer framstaellning av terapeutiskt anvaendbara karbacyklinderivat.
SU904516A3 (ru)	1982-02-07	Способ получени производных дифенилметана или смеси их изомеров
CS262697B2 (cs)	1989-03-14	Zpusob výroby nových racemických a opticky aktivních derivátů interfuranylenprostacyklinu
US4235803A (en)	1980-11-25	1,6-Dimesyl-3,4-dimethyl-D-mannitol and a process for the preparation thereof
FI82690B (fi)	1990-12-31	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 7-oxo-pg12-efedrinsalter.
CA1202968A (en)	1986-04-08	Process for the preparation of new cis-bi- cyclo[3.3.0]octane derivatives
KR870000890B1 (ko)	1987-05-02	선택적으로 생리활성인 7-옥소-프로스타사이클린 유도체의 제조 방법
KR940010294B1 (ko)	1994-10-22	신규한 피롤리딘유도체
FI83645B (fi)	1991-04-30	Foerfarande foer framstaellning av terapeutiskt anvaenbara racemiska eller optiskt aktiva 7-oxo- prostacyklin-derivat.
JPH036145B2 (pl)	1991-01-29
KR940010293B1 (ko)	1994-10-22	신규한 피롤리딘유도체
CS228923B2 (en)	1984-05-14	Method of preparing 4-oxo-pgi2 and analogues thereof
CS228922B2 (en)	1984-05-14	Method of preparing 4-oxoprostacycline-1 derivatives substituted in position 5
HU191216B (en)	1987-01-28	Process for the synthesis of stable 4,4-dioxo-4-thia-prostacycline derivatives
JPH0623107B2 (ja)	1994-03-30	プロスタサイクリン類を有効成分とする薬学的組成物