CA1054150A - Derives alkyl d'acides prostanoique et leur preparation - Google Patents

Derives alkyl d'acides prostanoique et leur preparation

Info

Publication number: CA1054150A
Authority: CA; Canada
Prior art keywords: formula; compound; methyl; octenyl; trans
Prior art date: 1973-04-16
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.): Expired

Application number

CA293,305A

Other languages

English (en)

Inventor

Nedumparambil A. Abraham

Jehan F. Bagli

Tibor Bogri

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth LLC

Original Assignee

American Home Products Corp

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.)

1973-04-16

Filing date

1977-12-19

Publication date

1979-05-08

1973-04-16 Priority claimed from US351381A external-priority patent/US3917668A/en

1977-12-19 Application filed by American Home Products Corp filed Critical American Home Products Corp

1979-05-08 Application granted granted Critical

1979-05-08 Publication of CA1054150A publication Critical patent/CA1054150A/fr

Status Expired legal-status Critical Current

Links

125000000217 alkyl group Chemical group 0.000 title claims description 115
239000002253 acid Substances 0.000 title description 34
238000002360 preparation method Methods 0.000 title description 9
150000007513 acids Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 284
238000000034 method Methods 0.000 claims abstract description 108
238000004519 manufacturing process Methods 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 95
239000001257 hydrogen Substances 0.000 claims description 92
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 78
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 77
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 69
-1 dimethyl 3,3-dimethyl-2-oxoheptyl Chemical group 0.000 claims description 61
230000008569 process Effects 0.000 claims description 60
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 55
150000001299 aldehydes Chemical class 0.000 claims description 45
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
239000003153 chemical reaction reagent Substances 0.000 claims description 34
230000002633 protecting effect Effects 0.000 claims description 32
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 30
125000004432 carbon atom Chemical group C* 0.000 claims description 25
239000003795 chemical substances by application Substances 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
150000004791 alkyl magnesium halides Chemical class 0.000 claims description 18
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical class CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 claims description 17
150000002431 hydrogen Chemical group 0.000 claims description 16
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 16
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical group [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 claims description 12
MWLAEDWMBJEXGH-UHFFFAOYSA-N diethyl 2-formylcyclopropane-1,1-dicarboxylate Chemical group CCOC(=O)C1(C(=O)OCC)CC1C=O MWLAEDWMBJEXGH-UHFFFAOYSA-N 0.000 claims description 11
229910052751 metal Inorganic materials 0.000 claims description 11
239000002184 metal Substances 0.000 claims description 11
CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical group CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 8
238000009833 condensation Methods 0.000 claims description 7
230000005494 condensation Effects 0.000 claims description 7
WIYMDOCSCMPUJI-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3,3-dimethylheptan-2-one Chemical group CCCCC(C)(C)C(=O)CP(=O)(OC)OC WIYMDOCSCMPUJI-UHFFFAOYSA-N 0.000 claims description 6
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims description 5
CYSOCLBOALSZAK-ZHACJKMWSA-N diethyl 2-[(e)-3-oxooct-1-enyl]cyclopropane-1,1-dicarboxylate Chemical compound CCCCCC(=O)\C=C\C1CC1(C(=O)OCC)C(=O)OCC CYSOCLBOALSZAK-ZHACJKMWSA-N 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
RYCSYYMZXSIBJI-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-methylheptan-2-one Chemical group CCCCC(C)C(=O)CP(=O)(OC)OC RYCSYYMZXSIBJI-UHFFFAOYSA-N 0.000 claims description 4
LQZCYXCHWNQBKX-UHFFFAOYSA-N 1-dimethoxyphosphorylheptan-2-one Chemical group CCCCCC(=O)CP(=O)(OC)OC LQZCYXCHWNQBKX-UHFFFAOYSA-N 0.000 claims description 4
LZYFWTACPYSNJW-AEACUUAWSA-N diethyl (3s,5r)-1-(7-ethoxy-7-oxoheptyl)-5-(3-hydroxy-3-methyloct-1-enyl)-2-oxocyclopentane-1,3-dicarboxylate Chemical compound CCCCCC(C)(O)C=C[C@H]1C[C@H](C(=O)OCC)C(=O)C1(CCCCCCC(=O)OCC)C(=O)OCC LZYFWTACPYSNJW-AEACUUAWSA-N 0.000 claims description 4
125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 claims description 4
229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
239000012279 sodium borohydride Substances 0.000 claims description 4
XWCQLLDGXBLGMD-UHFFFAOYSA-M magnesium;pentane;bromide Chemical group [Mg+2].[Br-].CCCC[CH2-] XWCQLLDGXBLGMD-UHFFFAOYSA-M 0.000 claims description 2
239000000126 substance Substances 0.000 claims 20
OMZUGMIZWHBMBW-ZRDIBKRKSA-N diethyl 2-[(e)-3-hydroxy-3-methyloct-1-enyl]cyclopropane-1,1-dicarboxylate Chemical compound CCCCCC(C)(O)\C=C\C1CC1(C(=O)OCC)C(=O)OCC OMZUGMIZWHBMBW-ZRDIBKRKSA-N 0.000 claims 4
ROGPFMJXELVDPA-FYWRMAATSA-N diethyl 2-[(e)-3-methyl-3-(oxan-2-yloxy)oct-1-enyl]cyclopropane-1,1-dicarboxylate Chemical compound C1C(C(=O)OCC)(C(=O)OCC)C1/C=C/C(C)(CCCCC)OC1CCCCO1 ROGPFMJXELVDPA-FYWRMAATSA-N 0.000 claims 4
QUTKOHNTFQAIET-ZHACJKMWSA-N diethyl 2-[(e)-4-methyl-3-oxooct-1-enyl]cyclopropane-1,1-dicarboxylate Chemical compound CCCCC(C)C(=O)\C=C\C1CC1(C(=O)OCC)C(=O)OCC QUTKOHNTFQAIET-ZHACJKMWSA-N 0.000 claims 3
PBBMNURYVYNZKG-GAGVLJRPSA-N diethyl (3S,5R)-1-(7-ethoxy-7-oxoheptyl)-5-[3-methyl-3-(oxan-2-yloxy)oct-1-enyl]-2-oxocyclopentane-1,3-dicarboxylate Chemical compound C(=O)(OCC)CCCCCCC1(C([C@H](C[C@@H]1C=CC(CCCCC)(C)OC1OCCCC1)C(=O)OCC)=O)C(=O)OCC PBBMNURYVYNZKG-GAGVLJRPSA-N 0.000 claims 2
UMNBUNNDDHANEP-ZHACJKMWSA-N diethyl 2-[(e)-3-hydroxy-4,4-dimethyloct-1-enyl]cyclopropane-1,1-dicarboxylate Chemical compound CCCCC(C)(C)C(O)\C=C\C1CC1(C(=O)OCC)C(=O)OCC UMNBUNNDDHANEP-ZHACJKMWSA-N 0.000 claims 2
PEVWOXOTAMJHMF-ZHACJKMWSA-N diethyl 2-[(e)-3-hydroxy-4-methyloct-1-enyl]cyclopropane-1,1-dicarboxylate Chemical compound CCCCC(C)C(O)\C=C\C1CC1(C(=O)OCC)C(=O)OCC PEVWOXOTAMJHMF-ZHACJKMWSA-N 0.000 claims 2
SIIOUNUHIJOKTG-ZHACJKMWSA-N diethyl 2-[(e)-4,4-dimethyl-3-oxooct-1-enyl]cyclopropane-1,1-dicarboxylate Chemical compound CCCCC(C)(C)C(=O)\C=C\C1CC1(C(=O)OCC)C(=O)OCC SIIOUNUHIJOKTG-ZHACJKMWSA-N 0.000 claims 2
IJNAKDWRBXDIQZ-BUHFOSPRSA-N diethyl 2-[(e)-4-methyl-3-(oxan-2-yloxy)oct-1-enyl]cyclopropane-1,1-dicarboxylate Chemical compound C1C(C(=O)OCC)(C(=O)OCC)C1/C=C/C(C(C)CCCC)OC1CCCCO1 IJNAKDWRBXDIQZ-BUHFOSPRSA-N 0.000 claims 2
IOUMAJDQFPUUDH-CMDGGOBGSA-N dimethyl 2-[(e)-4,4-dimethyl-3-oxooct-1-enyl]cyclopropane-1,1-dicarboxylate Chemical compound CCCCC(C)(C)C(=O)\C=C\C1CC1(C(=O)OC)C(=O)OC IOUMAJDQFPUUDH-CMDGGOBGSA-N 0.000 claims 2
YUNCXLSNVIKKDW-UHFFFAOYSA-N triethyl heptane-1,1,7-tricarboxylate Chemical group CCOC(=O)CCCCCCC(C(=O)OCC)C(=O)OCC YUNCXLSNVIKKDW-UHFFFAOYSA-N 0.000 claims 2
YZFOGXKZTWZVFN-UHFFFAOYSA-N cyclopentane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1 YZFOGXKZTWZVFN-UHFFFAOYSA-N 0.000 claims 1
OHALNUYYAWUYOB-CMDGGOBGSA-N dimethyl 2-[(e)-3-hydroxy-4,4-dimethyloct-1-enyl]cyclopropane-1,1-dicarboxylate Chemical compound CCCCC(C)(C)C(O)\C=C\C1CC1(C(=O)OC)C(=O)OC OHALNUYYAWUYOB-CMDGGOBGSA-N 0.000 claims 1
COYGTUCJQDTEEG-UHFFFAOYSA-N dimethyl 2-formylcyclopropane-1,1-dicarboxylate Chemical group COC(=O)C1(C(=O)OC)CC1C=O COYGTUCJQDTEEG-UHFFFAOYSA-N 0.000 claims 1
230000012173 estrus Effects 0.000 abstract description 13
125000005907 alkyl ester group Chemical group 0.000 abstract description 11
230000016087 ovulation Effects 0.000 abstract description 9
208000001953 Hypotension Diseases 0.000 abstract description 6
208000021822 hypotensive Diseases 0.000 abstract description 6
230000001077 hypotensive effect Effects 0.000 abstract description 6
230000000572 bronchospasmolytic effect Effects 0.000 abstract description 4
230000002401 inhibitory effect Effects 0.000 abstract description 4
230000003276 anti-hypertensive effect Effects 0.000 abstract description 3
239000004015 abortifacient agent Substances 0.000 abstract description 2
231100000641 abortifacient agent Toxicity 0.000 abstract description 2
230000002776 aggregation Effects 0.000 abstract description 2
238000004220 aggregation Methods 0.000 abstract description 2
230000027119 gastric acid secretion Effects 0.000 abstract description 2
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 abstract 1
230000001105 regulatory effect Effects 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 91
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
239000000203 mixture Substances 0.000 description 62
230000000875 corresponding effect Effects 0.000 description 58
150000003254 radicals Chemical class 0.000 description 49
239000000243 solution Substances 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 40
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
239000000047 product Substances 0.000 description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
238000011282 treatment Methods 0.000 description 27
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
239000002904 solvent Substances 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000000741 silica gel Substances 0.000 description 21
229910002027 silica gel Inorganic materials 0.000 description 21
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 16
239000007858 starting material Substances 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000002585 base Substances 0.000 description 15
235000019441 ethanol Nutrition 0.000 description 15
238000004587 chromatography analysis Methods 0.000 description 14
239000012071 phase Substances 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 12
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 12
239000011734 sodium Substances 0.000 description 12
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 11
241001465754 Metazoa Species 0.000 description 11
150000003839 salts Chemical class 0.000 description 11
229910052708 sodium Inorganic materials 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
239000012259 ether extract Substances 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
150000004702 methyl esters Chemical class 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
239000000284 extract Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
150000003180 prostaglandins Chemical class 0.000 description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 8
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
239000012442 inert solvent Substances 0.000 description 8
230000007935 neutral effect Effects 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
238000010992 reflux Methods 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 7
239000000499 gel Substances 0.000 description 7
229940094443 oxytocics prostaglandins Drugs 0.000 description 7
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
238000000605 extraction Methods 0.000 description 6
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
229930194542 Keto Natural products 0.000 description 5
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
206010000210 abortion Diseases 0.000 description 5
231100000176 abortion Toxicity 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
239000000010 aprotic solvent Substances 0.000 description 5
229910052744 lithium Inorganic materials 0.000 description 5
WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
238000003756 stirring Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
239000003377 acid catalyst Substances 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
125000000468 ketone group Chemical group 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
230000004048 modification Effects 0.000 description 4
238000012986 modification Methods 0.000 description 4
229930014626 natural product Natural products 0.000 description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
239000011591 potassium Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
230000002265 prevention Effects 0.000 description 4
230000028327 secretion Effects 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
238000012360 testing method Methods 0.000 description 4
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 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 3
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical class O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
101150065749 Churc1 gene Proteins 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
102100038239 Protein Churchill Human genes 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
208000007536 Thrombosis Diseases 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002220 antihypertensive agent Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 3
229960002986 dinoprostone Drugs 0.000 description 3
150000002440 hydroxy compounds Chemical class 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000002243 precursor Substances 0.000 description 3
230000035935 pregnancy Effects 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 3
238000000746 purification Methods 0.000 description 3
238000010998 test method Methods 0.000 description 3
150000005691 triesters Chemical class 0.000 description 3
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NOCQMYHWEFWPFZ-VAWYXSNFSA-N dimethyl 2-[(e)-3-oxo-4-propylnon-1-enyl]cyclopropane-1,1-dicarboxylate Chemical compound CCCCCC(CCC)C(=O)\C=C\C1CC1(C(=O)OC)C(=O)OC NOCQMYHWEFWPFZ-VAWYXSNFSA-N 0.000 description 1
MKNYIWCXNKHTHU-SNAWJCMRSA-N dimethyl 2-[(e)-3-oxobut-1-enyl]cyclopropane-1,1-dicarboxylate Chemical compound COC(=O)C1(C(=O)OC)CC1\C=C\C(C)=O MKNYIWCXNKHTHU-SNAWJCMRSA-N 0.000 description 1
NEMOJKROKMMQBQ-UHFFFAOYSA-N dimethyl 2-bromopropanedioate Chemical compound COC(=O)C(Br)C(=O)OC NEMOJKROKMMQBQ-UHFFFAOYSA-N 0.000 description 1
BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
HCSFNVNYMOUJLF-UHFFFAOYSA-N dipropyl 2-bromopropanedioate Chemical compound CCCOC(=O)C(Br)C(=O)OCCC HCSFNVNYMOUJLF-UHFFFAOYSA-N 0.000 description 1
YFFZFGWDYWOIHA-UHFFFAOYSA-N dipropyl 2-formylcyclopropane-1,1-dicarboxylate Chemical compound CCCOC(=O)C1(C(=O)OCCC)CC1C=O YFFZFGWDYWOIHA-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
VSOVASWDMQGFQU-UHFFFAOYSA-N ethyl 2,2-diethyloctanoate Chemical compound CCCCCCC(CC)(CC)C(=O)OCC VSOVASWDMQGFQU-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
230000004907 flux Effects 0.000 description 1
238000009472 formulation Methods 0.000 description 1
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 description 1
230000002068 genetic effect Effects 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
230000009027 insemination Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000005304 joining Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
229910001641 magnesium iodide Inorganic materials 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
UGVPKMAWLOMPRS-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].CC[CH2-] UGVPKMAWLOMPRS-UHFFFAOYSA-M 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
RFJMBJLXGJOOGI-OZIMOLPGSA-N methyl (E)-7-[2-hydroxy-5-(3-hydroxy-3-propyloct-1-enyl)cyclopentyl]hept-5-enoate Chemical compound OC(C=CC1C(C(CC1)O)C/C=C/CCCC(=O)OC)(CCCCC)CCC RFJMBJLXGJOOGI-OZIMOLPGSA-N 0.000 description 1
JDNKEFUGTQBAFR-YBKKZICASA-N methyl (E)-7-[2-hydroxy-5-[(Z)-3-hydroxy-3-methyloct-1-enyl]cyclopentyl]hept-5-enoate Chemical compound CCCCCC(C)(O)\C=C/C1CCC(O)C1C\C=C\CCCC(=O)OC JDNKEFUGTQBAFR-YBKKZICASA-N 0.000 description 1
KUJDKFRWBSVXGU-AFXRCSFLSA-N methyl (Z)-7-[(1S,2S)-2-(3-hydroxy-4,4-dimethyloct-1-enyl)-5-oxocyclopentyl]hept-5-enoate Chemical compound CCCCC(C)(C)C(O)C=C[C@@H]1CCC(=O)[C@H]1C\C=C/CCCC(=O)OC KUJDKFRWBSVXGU-AFXRCSFLSA-N 0.000 description 1
PHTOQMJHUYEXQG-WXXUWSOZSA-N methyl (Z)-7-[(1S,2S)-2-(4-ethyl-3-hydroxyoct-1-enyl)-5-oxocyclopentyl]hept-5-enoate Chemical compound CCCCC(CC)C(O)C=C[C@@H]1CCC(=O)[C@H]1C\C=C/CCCC(=O)OC PHTOQMJHUYEXQG-WXXUWSOZSA-N 0.000 description 1
HOJJZXINRFKRGT-NKLQCYAOSA-N methyl (z)-7-[(1r,2r,3r)-3-hydroxy-2-[(e)-3-hydroxy-4,4-dimethyloct-1-enyl]-5-oxocyclopentyl]hept-5-enoate Chemical compound CCCCC(C)(C)C(O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(=O)OC HOJJZXINRFKRGT-NKLQCYAOSA-N 0.000 description 1
RBPZFOFVKHYUNV-UHFFFAOYSA-N methyl 5-bromohexanoate Chemical compound COC(=O)CCCC(C)Br RBPZFOFVKHYUNV-UHFFFAOYSA-N 0.000 description 1
ICTLWQNQOIULKS-UHFFFAOYSA-N methyl 5-bromopent-2-enoate Chemical compound COC(=O)C=CCCBr ICTLWQNQOIULKS-UHFFFAOYSA-N 0.000 description 1
YTBXNIPJPAPVPW-UHFFFAOYSA-N methyl 5-bromopent-3-enoate Chemical compound COC(=O)CC=CCBr YTBXNIPJPAPVPW-UHFFFAOYSA-N 0.000 description 1
VXRBYWOPZSDWRI-UHFFFAOYSA-N methyl 6-bromohex-3-enoate Chemical compound COC(=O)CC=CCCBr VXRBYWOPZSDWRI-UHFFFAOYSA-N 0.000 description 1
IHUPKFSSCLSVHS-UHFFFAOYSA-N methyl 6-bromohex-4-enoate Chemical compound COC(=O)CCC=CCBr IHUPKFSSCLSVHS-UHFFFAOYSA-N 0.000 description 1
KYLVAMSNNZMHSX-UHFFFAOYSA-N methyl 6-bromohexanoate Chemical compound COC(=O)CCCCCBr KYLVAMSNNZMHSX-UHFFFAOYSA-N 0.000 description 1
UWOUYEZEPKVXAT-NVPCEHRXSA-N methyl 7-[(1s,2s)-2-(3-hydroxy-3-methyloct-1-enyl)-5-oxocyclopentyl]heptanoate Chemical compound CCCCCC(C)(O)C=C[C@@H]1CCC(=O)[C@H]1CCCCCCC(=O)OC UWOUYEZEPKVXAT-NVPCEHRXSA-N 0.000 description 1
VJVCYEISRIOVEG-BMRADRMJSA-N methyl 7-[2-hydroxy-5-[(e)-3-hydroxy-3-methyloct-1-enyl]cyclopentyl]heptanoate Chemical compound CCCCCC(C)(O)\C=C\C1CCC(O)C1CCCCCCC(=O)OC VJVCYEISRIOVEG-BMRADRMJSA-N 0.000 description 1
XPNANRSRZDKWKD-FYWRMAATSA-N methyl 7-[2-hydroxy-5-[(e)-3-oxooct-1-enyl]cyclopentyl]heptanoate Chemical compound CCCCCC(=O)\C=C\C1CCC(O)C1CCCCCCC(=O)OC XPNANRSRZDKWKD-FYWRMAATSA-N 0.000 description 1
BGMZLSGWGDLJPN-UHFFFAOYSA-N methyl 7-bromohept-4-enoate Chemical compound COC(=O)CCC=CCCBr BGMZLSGWGDLJPN-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
101150071136 mtxH gene Proteins 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
101150032584 oxy-4 gene Proteins 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000002559 palpation Methods 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
210000005227 renal system Anatomy 0.000 description 1
230000001850 reproductive effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
238000007157 ring contraction reaction Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
239000002002 slurry Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
NIDHFQDUBOVBKZ-NSCUHMNNSA-N trans-hex-4-enoic acid Chemical compound C\C=C\CCC(O)=O NIDHFQDUBOVBKZ-NSCUHMNNSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
WVTXXCGOGSDVRN-UHFFFAOYSA-N triethyl hex-4-ene-1,1,6-tricarboxylate Chemical compound CCOC(=O)CC=CCCC(C(=O)OCC)C(=O)OCC WVTXXCGOGSDVRN-UHFFFAOYSA-N 0.000 description 1
ZBQWJWZKCDBVHG-UHFFFAOYSA-N trimethyl hept-4-ene-1,1,7-tricarboxylate Chemical compound COC(=O)CCC=CCCC(C(=O)OC)C(=O)OC ZBQWJWZKCDBVHG-UHFFFAOYSA-N 0.000 description 1
BWXCIYFMXDIANK-UHFFFAOYSA-N trimethyl hex-4-ene-1,1,6-tricarboxylate Chemical compound COC(=O)CC=CCCC(C(=O)OC)C(=O)OC BWXCIYFMXDIANK-UHFFFAOYSA-N 0.000 description 1
MCUZRIPQQPHGSM-UHFFFAOYSA-N trimethyl hexane-1,1,6-tricarboxylate Chemical compound COC(=O)CCCCCC(C(=O)OC)C(=O)OC MCUZRIPQQPHGSM-UHFFFAOYSA-N 0.000 description 1
RQYUCFJJHXNUAH-UHFFFAOYSA-N trimethyl pent-3-ene-1,1,5-tricarboxylate Chemical compound COC(=O)CC=CCC(C(=O)OC)C(=O)OC RQYUCFJJHXNUAH-UHFFFAOYSA-N 0.000 description 1
UKYQGIVNQPUGQI-UHFFFAOYSA-N trimethyl pentane-1,1,5-tricarboxylate Chemical compound COC(=O)CCCCC(C(=O)OC)C(=O)OC UKYQGIVNQPUGQI-UHFFFAOYSA-N 0.000 description 1
IAPRTSNCZDPMNR-UHFFFAOYSA-N trimethyl-[4-[[2-trimethylsilyl-6,7-bis(trimethylsilyloxy)-3,4-dihydro-1h-isoquinolin-1-yl]methyl]-2-trimethylsilyloxyphenoxy]silane Chemical compound C1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC=C1CC1C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2CCN1[Si](C)(C)C IAPRTSNCZDPMNR-UHFFFAOYSA-N 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA293,305A 1973-04-16 1977-12-19 Derives alkyl d'acides prostanoique et leur preparation Expired CA1054150A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US351381A US3917668A (en)	1973-04-16	1973-04-16	Prostanoic acid intermediates
CA197,510A CA1034122A (fr)	1973-04-16	1974-04-11	Derives alkyles des acides prostanoiques et mode de preparation

Publications (1)

Publication Number	Publication Date
CA1054150A true CA1054150A (fr)	1979-05-08

Family

ID=25667543

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA293,305A Expired CA1054150A (fr)	1973-04-16	1977-12-19	Derives alkyl d'acides prostanoique et leur preparation

Country Status (1)

Country	Link
CA (1)	CA1054150A (fr)

1977
- 1977-12-19 CA CA293,305A patent/CA1054150A/fr not_active Expired

Publication	Publication Date	Title
FI71122C (fi)	1986-11-24	Foerfarande foer framstaellning av blodtrycksaenkande och trombosytaggregationshaemmande karbacyklinderivat
US5013758A (en)	1991-05-07	Novel carbacyclins, processes for their preparation and their use as medicinal agents
CA1241324A (fr)	1988-08-30	Derives d'interphenylene carbacycline
US3917668A (en)	1975-11-04	Prostanoic acid intermediates
US4638002A (en)	1987-01-20	2,3,4-trinor-1,5-inter-meta-phenylene-prostacyclin compounds useful in inhibiting thrombocyte aggregation
CA1156226A (fr)	1983-11-01	Derives de la prostaglandine des series delta -2,4-11-deoxy-peg
US3959263A (en)	1976-05-25	Prostaglandin intermediate
US4497830A (en)	1985-02-05	Carbacyclins, their preparation and pharmacological use
CA1054150A (fr)	1979-05-08	Derives alkyl d'acides prostanoique et leur preparation
DE2610718A1 (de)	1976-10-14	Neue 16-phenoxy-prostaglandin-verbindungen
CA1284654C (fr)	1991-06-04	Derives de bicyclo¬4.2.0\|octane possedant d'interessantes proprietes therapeutiques
US4007171A (en)	1977-02-08	Intermediates for prostanoic acids
US4048328A (en)	1977-09-13	Alkyl derivatives of 4,5-dehydro PGF1
Cooper et al.	1993	Synthesis of the four stereoisomers of enprostil
US4070482A (en)	1978-01-24	Prostaglandin antagonists
US4092427A (en)	1978-05-30	Method of inducing abortion using alkyl derivatives of prostanoic acids
US3987081A (en)	1976-10-19	Alkyl derivatives of prostanoic acids and preparation thereof
US4048329A (en)	1977-09-13	Alkyl derivatives of 4,5-dehydro PGE1
US4144251A (en)	1979-03-13	5-Unsaturated prostanoic acid derivatives
GB1568017A (en)	1980-05-21	Prostaglandins
US3922297A (en)	1975-11-25	Prostaglandin E{HD 1{B , F{HD 1{B , and A{HD 1 {B analogs
US4370343A (en)	1983-01-25	Method for controlling hypertension
FR2515642A1 (fr)	1983-05-06	Nouvelles (11r)-11-deoxy-11-alkyl-6-oxo-prostaglandines et compositions pharmaceutiques les contenant
DE3204443A1 (de)	1983-08-18	Neue carbacycline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
CA1041012A (fr)	1978-10-24	Methode pour diminuer l'incidence des effets secondaires d'ordre gastro-intestinal durant le traitement des affections inflammatoires a l'aide d'agents anti-inflammatoires et composes connexes