IE42966B1 - 8-azaprostaglandins and process for the preparation thereof - Google Patents

8-azaprostaglandins and process for the preparation thereof

Info

Publication number: IE42966B1
Authority: IE; Ireland
Prior art keywords: ethyl; methyl; oxo; mixture; isomers
Prior art date: 1975-03-21

Application number

IE545/76A

Other languages

English (en)

Other versions

IE42966L (en

Inventor

Jean Alain

P Eymard

C Pigerol

J Simiand

Original Assignee

Labaz

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.)

1975-03-21

Filing date

1976-03-15

Publication date

1980-11-19

1976-03-15 Application filed by Labaz filed Critical Labaz

1976-09-21 Publication of IE42966L publication Critical patent/IE42966L/xx

1980-11-19 Publication of IE42966B1 publication Critical patent/IE42966B1/en

Links

238000002360 preparation method Methods 0.000 title claims abstract description 18
238000000034 method Methods 0.000 title claims description 42
230000008569 process Effects 0.000 title claims description 11
150000001875 compounds Chemical class 0.000 claims abstract description 68
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 42
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 34
239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 11
231100000252 nontoxic Toxicity 0.000 claims abstract description 8
230000003000 nontoxic effect Effects 0.000 claims abstract description 8
239000000203 mixture Substances 0.000 claims description 55
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
150000003180 prostaglandins Chemical class 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 19
-1 alkali metal salt Chemical class 0.000 claims description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
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 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 6
208000006673 asthma Diseases 0.000 claims description 6
210000002345 respiratory system Anatomy 0.000 claims description 6
239000012279 sodium borohydride Substances 0.000 claims description 6
229910000033 sodium borohydride Inorganic materials 0.000 claims description 6
241001465754 Metazoa Species 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 claims description 5
230000001575 pathological effect Effects 0.000 claims description 5
239000000443 aerosol Substances 0.000 claims description 4
230000007883 bronchodilation Effects 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
230000009467 reduction Effects 0.000 claims description 4
230000001476 alcoholic effect Effects 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
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 claims description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 12
DERLEQYHZCMIPL-UHFFFAOYSA-N 1-(triphenyl-$l^{5}-phosphanylidene)heptan-2-one Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)CCCCC)C1=CC=CC=C1 DERLEQYHZCMIPL-UHFFFAOYSA-N 0.000 abstract description 8
SNVVZCPNLVAKLC-UHFFFAOYSA-N 1-chloroheptan-2-one Chemical compound CCCCCC(=O)CCl SNVVZCPNLVAKLC-UHFFFAOYSA-N 0.000 abstract description 7
230000000144 pharmacologic effect Effects 0.000 abstract description 7
229910000027 potassium carbonate Inorganic materials 0.000 abstract description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract description 6
YGRJFGCEOYRREO-UHFFFAOYSA-N ethyl 3-oxooctanoate Chemical compound CCCCCC(=O)CC(=O)OCC YGRJFGCEOYRREO-UHFFFAOYSA-N 0.000 abstract description 4
VCRAOJUOQXBKSE-UHFFFAOYSA-M silver 8-methoxy-8-oxooctanoate Chemical compound C(CCCCCCC(=O)[O-])(=O)OC.[Ag+] VCRAOJUOQXBKSE-UHFFFAOYSA-M 0.000 abstract description 4
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 abstract description 3
WYTAKZKWHVWTEA-UHFFFAOYSA-N diethyl 2-(5-acetyloxypentyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)CCCCCOC(C)=O WYTAKZKWHVWTEA-UHFFFAOYSA-N 0.000 abstract description 3
QYJOOVQLTTVTJY-UHFFFAOYSA-N ethyl 5-oxopyrrolidine-2-carboxylate Chemical compound CCOC(=O)C1CCC(=O)N1 QYJOOVQLTTVTJY-UHFFFAOYSA-N 0.000 abstract description 3
YDARFNBVDDWMBQ-UHFFFAOYSA-N ethyl 7-[2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]heptanoate Chemical compound CCOC(=O)CCCCCCN1C(CO)CCC1=O YDARFNBVDDWMBQ-UHFFFAOYSA-N 0.000 abstract description 3
125000004494 ethyl ester group Chemical group 0.000 abstract description 3
VKUXHMUEOAJNNB-UHFFFAOYSA-M 2-oxoheptyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC(=O)CCCCC)C1=CC=CC=C1 VKUXHMUEOAJNNB-UHFFFAOYSA-M 0.000 abstract description 2
JLPQXFFMVVPIRW-UHFFFAOYSA-N 7-bromoheptanoic acid Chemical compound OC(=O)CCCCCCBr JLPQXFFMVVPIRW-UHFFFAOYSA-N 0.000 abstract description 2
COYUAWIJCNCEKE-UHFFFAOYSA-N methyl 7-(2-formyl-5-oxopyrrolidin-1-yl)heptanoate Chemical compound COC(=O)CCCCCCN1C(C=O)CCC1=O COYUAWIJCNCEKE-UHFFFAOYSA-N 0.000 abstract description 2
239000000969 carrier Substances 0.000 abstract 1
AHMWONZNKYSQBH-FYWRMAATSA-N ethyl 7-[2-oxo-5-[(E)-3-oxooct-1-enyl]pyrrolidin-1-yl]heptanoate Chemical compound O=C(/C=C/C1N(C(CC1)=O)CCCCCCC(=O)OCC)CCCCC AHMWONZNKYSQBH-FYWRMAATSA-N 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
239000008194 pharmaceutical composition Substances 0.000 abstract 1
238000010561 standard procedure Methods 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 76
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 37
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
239000002904 solvent Substances 0.000 description 30
241000786363 Rhampholeon spectrum Species 0.000 description 26
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
239000007864 aqueous solution Substances 0.000 description 17
239000000047 product Substances 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
238000004587 chromatography analysis Methods 0.000 description 14
150000002148 esters Chemical class 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
229920006395 saturated elastomer Polymers 0.000 description 14
GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 description 13
229960000711 alprostadil Drugs 0.000 description 13
239000011780 sodium chloride Substances 0.000 description 13
230000009471 action Effects 0.000 description 12
GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 12
239000012074 organic phase Substances 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
238000001035 drying Methods 0.000 description 10
230000000694 effects Effects 0.000 description 10
239000012429 reaction media Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
238000010992 reflux Methods 0.000 description 9
238000001816 cooling Methods 0.000 description 8
230000002496 gastric effect Effects 0.000 description 8
230000028327 secretion Effects 0.000 description 8
MJHBDPVPHGKDQB-UHFFFAOYSA-N 7-pyrrolidin-1-ylheptanoic acid Chemical compound OC(=O)CCCCCCN1CCCC1 MJHBDPVPHGKDQB-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-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
239000001110 calcium chloride Substances 0.000 description 6
229910001628 calcium chloride Inorganic materials 0.000 description 6
239000002609 medium Substances 0.000 description 6
229940094443 oxytocics prostaglandins Drugs 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
238000004821 distillation Methods 0.000 description 5
OOBFNDGMAGSNKA-UHFFFAOYSA-N ethyl 7-bromoheptanoate Chemical compound CCOC(=O)CCCCCCBr OOBFNDGMAGSNKA-UHFFFAOYSA-N 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000000843 powder Substances 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000010409 thin film Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
ZTTWQKYKGNLCCA-UHFFFAOYSA-N 2-methyl-10H-thieno[2,3-b][1,5]benzodiazepin-4-amine Chemical compound N1C2=CC=CC=C2N=C(N)C2=C1SC(C)=C2 ZTTWQKYKGNLCCA-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
208000005392 Spasm Diseases 0.000 description 4
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
230000003182 bronchodilatating effect Effects 0.000 description 4
YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
229960001760 dimethyl sulfoxide Drugs 0.000 description 4
238000010828 elution Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
230000000968 intestinal effect Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000010408 film Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000012535 impurity Substances 0.000 description 3
XTHVSPVWRPWTCO-UHFFFAOYSA-N methyl 7-[2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]heptanoate Chemical compound COC(=O)CCCCCCN1C(CO)CCC1=O XTHVSPVWRPWTCO-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
230000003033 spasmogenic effect Effects 0.000 description 3
239000001117 sulphuric acid Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
210000004291 uterus Anatomy 0.000 description 3
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
HOBJEFOCIRXQKH-UHFFFAOYSA-N 5-(hydroxymethyl)pyrrolidin-2-one Chemical compound OCC1CCC(=O)N1 HOBJEFOCIRXQKH-UHFFFAOYSA-N 0.000 description 2
ODHCTXKNWHHXJC-UHFFFAOYSA-N 5-oxoproline Chemical compound OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
208000009079 Bronchial Spasm Diseases 0.000 description 2
208000014181 Bronchial disease Diseases 0.000 description 2
206010006482 Bronchospasm Diseases 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
208000001953 Hypotension Diseases 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
229960004373 acetylcholine Drugs 0.000 description 2
125000003172 aldehyde group Chemical group 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
VFURZFXINHLLBT-UHFFFAOYSA-N ethyl 7-(2-formyl-5-oxopyrrolidin-1-yl)heptanoate Chemical compound CCOC(=O)CCCCCCN1C(C=O)CCC1=O VFURZFXINHLLBT-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
210000003405 ileum Anatomy 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
210000000754 myometrium Anatomy 0.000 description 2
229930014626 natural product Natural products 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical class O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
230000009291 secondary effect Effects 0.000 description 2
229910001961 silver nitrate Inorganic materials 0.000 description 2
210000002460 smooth muscle Anatomy 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
230000004936 stimulating effect Effects 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
230000002792 vascular Effects 0.000 description 2
230000000304 vasodilatating effect Effects 0.000 description 2
239000003071 vasodilator agent Substances 0.000 description 2
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
ZCYVIAZIVJNAMO-UHFFFAOYSA-N 5-chloropentyl acetate Chemical compound CC(=O)OCCCCCCl ZCYVIAZIVJNAMO-UHFFFAOYSA-N 0.000 description 1
ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
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238000006073 displacement reaction Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
230000008693 nausea Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229960001789 papaverine Drugs 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
229940043131 pyroglutamate Drugs 0.000 description 1
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150000003839 salts Chemical class 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
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238000000926 separation method Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pulmonology (AREA)
Oil, Petroleum & Natural Gas (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

IE545/76A 1975-03-21 1976-03-15 8-azaprostaglandins and process for the preparation thereof IE42966B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB12034/75A GB1529852A (en)	1975-03-21	1975-03-21	8-azaprostaglandins and process for the preparation thereof

Publications (2)

Publication Number	Publication Date
IE42966L IE42966L (en)	1976-09-21
IE42966B1 true IE42966B1 (en)	1980-11-19

Family

ID=9997230

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE545/76A IE42966B1 (en)	1975-03-21	1976-03-15	8-azaprostaglandins and process for the preparation thereof

Country Status (26)

Country	Link
JP (1)	JPS607602B2 (fr)
AR (1)	AR213172A1 (fr)
AT (1)	AT348163B (fr)
AU (1)	AU501105B2 (fr)
BE (1)	BE839761A (fr)
CA (1)	CA1076587A (fr)
CH (2)	CH611604A5 (fr)
DE (1)	DE2612114A1 (fr)
DK (1)	DK140937B (fr)
ES (2)	ES446239A1 (fr)
FI (1)	FI61692C (fr)
FR (1)	FR2304340A1 (fr)
GB (1)	GB1529852A (fr)
HU (1)	HU173348B (fr)
IE (1)	IE42966B1 (fr)
IT (1)	IT1061011B (fr)
MX (1)	MX3301E (fr)
NL (1)	NL7602891A (fr)
NO (1)	NO144147C (fr)
NZ (1)	NZ180251A (fr)
OA (1)	OA05279A (fr)
PT (1)	PT64919B (fr)
SE (1)	SE418290B (fr)
SU (1)	SU614746A3 (fr)
YU (1)	YU73876A (fr)
ZA (1)	ZA761448B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4097489A (en) *	1977-06-17	1978-06-27	The Upjohn Company	9-Deoxy-9α,6-nitrilo or 6,9α-imino-PGF compounds
US5540618A (en) *	1994-10-28	1996-07-30	National University Of Singapore	Passive attenuator for shelter protection against explosions
US7402605B2 (en)	2002-03-05	2008-07-22	Ono Pharmaceutical Co., Ltd.	8-azaprostaglandin derivative compounds and drugs containing the compounds as the active ingredient

1975
- 1975-03-21 GB GB12034/75A patent/GB1529852A/en not_active Expired
1976
- 1976-03-02 DK DK88276AA patent/DK140937B/da not_active IP Right Cessation
- 1976-03-09 NZ NZ180251A patent/NZ180251A/xx unknown
- 1976-03-09 ZA ZA761448A patent/ZA761448B/xx unknown
- 1976-03-11 AU AU11899/76A patent/AU501105B2/en not_active Expired
- 1976-03-15 IE IE545/76A patent/IE42966B1/en unknown
- 1976-03-17 AT AT195676A patent/AT348163B/de not_active IP Right Cessation
- 1976-03-18 FR FR7607794A patent/FR2304340A1/fr active Granted
- 1976-03-18 SE SE7603400A patent/SE418290B/xx unknown
- 1976-03-18 PT PT64919A patent/PT64919B/pt unknown
- 1976-03-18 IT IT21346/76A patent/IT1061011B/it active
- 1976-03-19 MX MX000100U patent/MX3301E/es unknown
- 1976-03-19 CH CH350176A patent/CH611604A5/xx not_active IP Right Cessation
- 1976-03-19 BE BE165326A patent/BE839761A/fr not_active IP Right Cessation
- 1976-03-19 NO NO760994A patent/NO144147C/no unknown
- 1976-03-19 HU HU76LA885A patent/HU173348B/hu unknown
- 1976-03-19 YU YU00738/76A patent/YU73876A/xx unknown
- 1976-03-19 CA CA248,275A patent/CA1076587A/fr not_active Expired
- 1976-03-19 FI FI760744A patent/FI61692C/fi not_active IP Right Cessation
- 1976-03-19 NL NL7602891A patent/NL7602891A/xx not_active Application Discontinuation
- 1976-03-19 AR AR262630A patent/AR213172A1/es active
- 1976-03-19 CH CH844678A patent/CH611881A5/xx not_active IP Right Cessation
- 1976-03-19 SU SU762334454A patent/SU614746A3/ru active
- 1976-03-20 OA OA55774A patent/OA05279A/fr unknown
- 1976-03-20 ES ES446239A patent/ES446239A1/es not_active Expired
- 1976-03-22 JP JP51031889A patent/JPS607602B2/ja not_active Expired
- 1976-03-22 DE DE19762612114 patent/DE2612114A1/de not_active Withdrawn
1977
- 1977-05-03 ES ES458389A patent/ES458389A1/es not_active Expired

Also Published As

Publication number	Publication date
CH611604A5 (en)	1979-06-15
CH611881A5 (en)	1979-06-29
FR2304340A1 (fr)	1976-10-15
AT348163B (de)	1979-02-12
BE839761A (fr)	1976-09-20
SE418290B (sv)	1981-05-18
OA05279A (fr)	1981-02-28
ES446239A1 (es)	1977-07-01
ATA195676A (de)	1978-06-15
FI61692B (fi)	1982-05-31
PT64919A (en)	1976-04-01
ZA761448B (en)	1977-03-30
AU1189976A (en)	1977-09-15
IT1061011B (it)	1982-10-20
NZ180251A (en)	1978-07-28
NO144147B (no)	1981-03-23
IE42966L (en)	1976-09-21
FI61692C (fi)	1982-09-10
ES458389A1 (es)	1978-02-16
SE7603400L (sv)	1976-09-22
MX3301E (es)	1980-09-03
DK140937C (fr)	1980-05-19
JPS607602B2 (ja)	1985-02-26
DK140937B (da)	1979-12-10
FR2304340B1 (fr)	1979-06-29
YU73876A (en)	1982-10-31
AU501105B2 (en)	1979-06-14
FI760744A (fr)	1976-09-22
HU173348B (hu)	1979-04-28
JPS51138671A (en)	1976-11-30
AR213172A1 (es)	1978-12-29
DE2612114A1 (de)	1976-10-07
DK88276A (fr)	1976-09-22
PT64919B (en)	1977-08-24
NL7602891A (nl)	1976-09-23
GB1529852A (en)	1978-10-25
SU614746A3 (ru)	1978-07-05
NO144147C (no)	1981-07-15
NO760994L (fr)	1976-09-22
CA1076587A (fr)	1980-04-29

Publication	Publication Date	Title
US4248889A (en)	1981-02-03	3,5-Dihydroxypentanoic ester derivatives having antihyperlipaemic activity
CH636096A5 (de)	1983-05-13	Bicyclische prostaglandine, verfahren zu ihrer herstellung und pharmazeutische praeparate.
DE2858726C2 (de)	1992-10-01	Arzneimittel zur senkung des serumcholesterinspiegels
US4115401A (en)	1978-09-19	Prostaglandin derivatives and process for preparing the same
JPH04247082A (ja)	1992-09-03	新スピロ〔４．５〕デカン化合物および医薬品組成物
IE42966B1 (en)	1980-11-19	8-azaprostaglandins and process for the preparation thereof
FR2554448A1 (fr)	1985-05-10	Derives furyles de prostaglandines 16-substituees et procede pour leur fabrication
CH638510A5 (de)	1983-09-30	Prostacyclinanaloga.
DE2510818C2 (de)	1983-11-17	Neue Prostaglandin-Analoge sowie ein Verfahren zu deren Herstellung, sowie Arzneimittel die diese enthalten
DE2719901A1 (de)	1977-11-24	Pge- und 11-deoxy-pge-verbindungen mit einer methylengruppe am c-9
CH617186A5 (fr)	1980-05-14
KR880001028B1 (ko)	1988-06-15	세포 보호 유도방법
House et al.	1973	Perhydroindan derivatives. XV. Synthesis of a tetracyclic precursor to epiallogibberic acid
IE43689B1 (en)	1981-05-06	2-(w-haloalkenyl)-cyclopentane-1-heptanoic acids,methods for preparation thereof and their use
GB2024807A (en)	1980-01-16	An imidazole derivative
JPS5831352B2 (ja)	1983-07-05	新規なインド−ル誘導体、その製造方法及び医薬としての使用
SU899573A1 (ru)	1982-01-23	Способ получени рацемического 3-метилового эфира 18,D-бисгомоэстрадиола
US4355170A (en)	1982-10-19	1-Substituted imidazole derivatives
US3769316A (en)	1973-10-30	Prostaglandin intermediates
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