IL43832A - (8rs,12rs,15sr (zeta))-(5z,13e)-15-hydroxy-9-oxo prosta-5,13-dienoic (or9-alkoxy-prosta 5,9,13-trienoic) acid derivatives,process for preparing them and pharmaceutical compositions containing them - Google Patents

(8rs,12rs,15sr (zeta))-(5z,13e)-15-hydroxy-9-oxo prosta-5,13-dienoic (or9-alkoxy-prosta 5,9,13-trienoic) acid derivatives,process for preparing them and pharmaceutical compositions containing them

Info

Publication number: IL43832A
Authority: IL; Israel
Prior art keywords: formula; mixture; radical; products; carbon atoms
Prior art date: 1972-12-27

Application number

IL43832A

Other languages

English (en)

Other versions

IL43832A0 (en

Original Assignee

Roussel Uclaf

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.)

1972-12-27

Filing date

1973-12-17

Publication date

1977-03-31

1973-12-17 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1974-03-14 Publication of IL43832A0 publication Critical patent/IL43832A0/xx

1977-03-31 Publication of IL43832A publication Critical patent/IL43832A/en

Links

239000002253 acid Substances 0.000 title claims description 16
238000004519 manufacturing process Methods 0.000 title claims description 5
239000008194 pharmaceutical composition Substances 0.000 title claims description 3
239000000203 mixture Substances 0.000 claims description 52
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
125000004432 carbon atom Chemical group C* 0.000 claims description 26
239000000470 constituent Substances 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
238000000034 method Methods 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
229910052760 oxygen Inorganic materials 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
239000011707 mineral Substances 0.000 claims description 7
239000002585 base Substances 0.000 claims description 6
150000007530 organic bases Chemical class 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
238000006114 decarboxylation reaction Methods 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
229910052709 silver Inorganic materials 0.000 claims description 2
239000004332 silver Substances 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
230000020477 pH reduction Effects 0.000 claims 1
WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 claims 1
GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical compound C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 claims 1
239000000047 product Substances 0.000 description 49
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
-1 alkynyl radical Chemical class 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 5
241000786363 Rhampholeon spectrum Species 0.000 description 5
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 5
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
235000010755 mineral Nutrition 0.000 description 5
229920002554 vinyl polymer Polymers 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000000284 extract Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000000694 effects Effects 0.000 description 3
230000001077 hypotensive effect Effects 0.000 description 3
239000011777 magnesium Chemical class 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
239000003814 drug Substances 0.000 description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229930014626 natural product Natural products 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
238000000053 physical method Methods 0.000 description 2
239000011591 potassium Chemical class 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000003180 prostaglandins Chemical class 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011734 sodium Chemical class 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 1
PFJVIOBMBDFBCJ-UHFFFAOYSA-N (1z)-1-diazobutane Chemical compound CCCC=[N+]=[N-] PFJVIOBMBDFBCJ-UHFFFAOYSA-N 0.000 description 1
IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 1
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 1
NJJNWEJOWXWBBX-OALUTQOASA-N 7-[(1r,2s)-2-oct-1-enylcyclopentyl]hept-5-enoic acid Chemical compound CCCCCCC=C[C@H]1CCC[C@@H]1CC=CCCCC(O)=O NJJNWEJOWXWBBX-OALUTQOASA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
241001136792 Alle Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
101100091482 Caenorhabditis elegans rop-1 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical class O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
125000004429 atom Chemical class 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
KOAVNZURYJRNDR-UHFFFAOYSA-N bromoethene;magnesium Chemical compound [Mg].BrC=C KOAVNZURYJRNDR-UHFFFAOYSA-N 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
239000011575 calcium Chemical class 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000007891 compressed tablet Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000010586 diagram Methods 0.000 description 1
WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
238000007519 figuring Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
LROBJRRFCPYLIT-UHFFFAOYSA-M magnesium;ethyne;bromide Chemical compound [Mg+2].[Br-].[C-]#C LROBJRRFCPYLIT-UHFFFAOYSA-M 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
DITHIFQMPPCBCU-UHFFFAOYSA-N propa-1,2-diene Chemical compound [CH]=C=C DITHIFQMPPCBCU-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000009291 secondary effect Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

IL43832A 1972-12-27 1973-12-17 (8rs,12rs,15sr (zeta))-(5z,13e)-15-hydroxy-9-oxo prosta-5,13-dienoic (or9-alkoxy-prosta 5,9,13-trienoic) acid derivatives,process for preparing them and pharmaceutical compositions containing them IL43832A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7246324A FR2211223B1 (fi)	1972-12-27	1972-12-27

Publications (2)

Publication Number	Publication Date
IL43832A0 IL43832A0 (en)	1974-03-14
IL43832A true IL43832A (en)	1977-03-31

Family

ID=9109325

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL43832A IL43832A (en)	1972-12-27	1973-12-17	(8rs,12rs,15sr (zeta))-(5z,13e)-15-hydroxy-9-oxo prosta-5,13-dienoic (or9-alkoxy-prosta 5,9,13-trienoic) acid derivatives,process for preparing them and pharmaceutical compositions containing them

Country Status (14)

Country	Link
JP (1)	JPS5724343B2 (fi)
BE (1)	BE808969A (fi)
CA (1)	CA1018972A (fi)
CH (2)	CH590226A5 (fi)
DD (1)	DD108268A5 (fi)
DE (1)	DE2364706C2 (fi)
ES (1)	ES421790A1 (fi)
FR (1)	FR2211223B1 (fi)
GB (1)	GB1438130A (fi)
IE (1)	IE38875B1 (fi)
IL (1)	IL43832A (fi)
NL (1)	NL7317745A (fi)
SU (1)	SU668597A3 (fi)
ZA (1)	ZA739650B (fi)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3922302A (en) *	1973-07-26	1975-11-25	American Home Prod	15-Ethynyl-11-deoxy PGE
US4091015A (en) *	1972-10-27	1978-05-23	American Home Products Corporation	15-Substituted prostanoic acids
US4022821A (en) *	1974-04-18	1977-05-10	American Home Products Corporation	15-Substituted prostanoic acid
US4065494A (en) *	1975-04-17	1977-12-27	American Home Products Corporation	15-Substituted prostanoic acids

1972
- 1972-12-27 FR FR7246324A patent/FR2211223B1/fr not_active Expired
1973
- 1973-12-17 IL IL43832A patent/IL43832A/en unknown
- 1973-12-21 DD DD175629A patent/DD108268A5/xx unknown
- 1973-12-21 ZA ZA00739650A patent/ZA739650B/xx unknown
- 1973-12-21 BE BE139155A patent/BE808969A/xx not_active IP Right Cessation
- 1973-12-24 CA CA188,897A patent/CA1018972A/fr not_active Expired
- 1973-12-24 SU SU731978756A patent/SU668597A3/ru active
- 1973-12-26 ES ES421790A patent/ES421790A1/es not_active Expired
- 1973-12-26 JP JP14414673A patent/JPS5724343B2/ja not_active Expired
- 1973-12-27 CH CH1435676A patent/CH590226A5/xx not_active IP Right Cessation
- 1973-12-27 DE DE2364706A patent/DE2364706C2/de not_active Expired
- 1973-12-27 CH CH1816573A patent/CH590225A5/xx not_active IP Right Cessation
- 1973-12-27 GB GB5981973A patent/GB1438130A/en not_active Expired
- 1973-12-27 NL NL7317745A patent/NL7317745A/xx not_active Application Discontinuation
- 1973-12-28 IE IE02339/73A patent/IE38875B1/xx unknown

Also Published As

Publication number	Publication date
JPS5046649A (fi)	1975-04-25
CH590225A5 (fi)	1977-07-29
DD108268A5 (fi)	1974-09-12
DE2364706A1 (de)	1974-07-04
IL43832A0 (en)	1974-03-14
CA1018972A (fr)	1977-10-11
DE2364706C2 (de)	1982-07-08
ES421790A1 (es)	1976-04-01
GB1438130A (fi)	1976-06-03
JPS5724343B2 (fi)	1982-05-24
AU6396873A (en)	1975-07-03
SU668597A3 (ru)	1979-06-15
NL7317745A (fi)	1974-07-01
IE38875L (en)	1974-06-27
ZA739650B (en)	1975-02-26
IE38875B1 (en)	1978-06-21
FR2211223B1 (fi)	1976-04-23
FR2211223A1 (fi)	1974-07-19
CH590226A5 (fi)	1977-07-29
BE808969A (fr)	1974-06-21

Publication	Publication Date	Title
US4307112A (en)	1981-12-22	9-Deoxy-9A-methylene isosteres of PGI2 and process for their preparation
US4230721A (en)	1980-10-28	Bicyclic prostaglandins
CA1079725A (en)	1980-06-17	Prostaglandin-acetylene analogues and process for their manufacture
GB2039909A (en)	1980-08-20	Prostaglandins
US4035414A (en)	1977-07-12	Prostanoic acid derivatives
NO148642B (no)	1983-08-08	Analogifremgangsmaate ved fremstilling av terapeutisk aktive, nye prostacyclinderivater
IL43832A (en)	1977-03-31	(8rs,12rs,15sr (zeta))-(5z,13e)-15-hydroxy-9-oxo prosta-5,13-dienoic (or9-alkoxy-prosta 5,9,13-trienoic) acid derivatives,process for preparing them and pharmaceutical compositions containing them
JPS609035B2 (ja)	1985-03-07	ビシクロオクタン誘導体の製造法
HU187466B (en)	1986-01-28	Process for producing new 5-cyano-prostacycline derivatives and pharmaceutical compositions containing them
McGuckin et al.	1952	Steroids Derived from Bile Acids. XVIII. Introduction of the 4, 5-Double Bond of Cortisone1, 2
US5731345A (en)	1998-03-24	Seco-D steroids active on the cardiovascular system and pharmaceutical compositions containing same
EP0107693A1 (en)	1984-05-09	ANALOGUE COMPOUNDS OF 2,3,4-TRINOR-1,5-INTER-M-PHENYLENE-PROSTACYCLINE-I2, THEIR PREPARATION PROCESS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
US4035415A (en)	1977-07-12	Omega-nor-cycloalkyl-13,14-dehydro-prostaglandins
PL101461B1 (pl)	1978-12-30	Sposob wytwarzania nowych podstawionych estradioli
US3932467A (en)	1976-01-13	Process for the production of 2β-formyl 3α-protected hydroxy-5-oxocyclopentane-1α-heptanoic acids and esters corresponding
SU942588A3 (ru)	1982-07-07	Способ получени производных 13,14-дегидропростагландина в виде рацематов или оптически активных антиподов
IL31973A (en)	1973-05-31	15beta,16beta-methylene pregnenes and their manufacture
Banerjee et al.	1981	Synthesis and anti-ulcer activity of 16-phenoxy analogues of (+)-11-deoxyprostaglandin E1
NO146280B (no)	1982-05-24	Bis-tetrahydropyranyleter for anvendelse som mellomprodukt for fremstilling av en fysiologisk aktiv p-bifenylester av en prostaglandinanalog av e- eller f-serien
CN115626947B (zh)	2024-07-02	五环三萜类天然产物的合成及其应用
IE43833B1 (en)	1981-06-03	Prostenoic acid derivatives,processes for their preparatioon and compositions containing them
US4061729A (en)	1977-12-06	Prostanoic acid derivatives and therapeutic compositions
NO752191L (fi)	1975-12-23
US4788299A (en)	1988-11-29	Ketolactones
JPH02167284A (ja)	1990-06-27	プロスタグランジン前駆体およびその製法