SE443978B - Prostaglandin-i?712-derivat - Google Patents

Prostaglandin-i?712-derivat

Info

Publication number: SE443978B
Authority: SE; Sweden
Prior art keywords: hydroxy; butyl; octane; compound according; oxabicyclo
Prior art date: 1977-07-29

Application number

SE7808184A

Other languages

English (en)

Swedish (sv)

Other versions

SE7808184L (sv

Inventor

W Skuballa

B Raduchel

N Schwarz

H Vorbruggen

B Muller

G Mannesmann

O Loge

E Schillinger

J Casals-Stenzel

Original Assignee

Schering Ag

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.)

1977-07-29

Filing date

1978-07-27

Publication date

1986-03-17

1978-07-27 Application filed by Schering Ag filed Critical Schering Ag

1979-01-30 Publication of SE7808184L publication Critical patent/SE7808184L/xx

1986-03-17 Publication of SE443978B publication Critical patent/SE443978B/sv

Links

150000003180 prostaglandins Chemical class 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims description 161
-1 hydroxymethylene group Chemical group 0.000 claims description 117
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 63
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
UKVVPDHLUHAJNZ-PMACEKPBSA-N prostane Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC UKVVPDHLUHAJNZ-PMACEKPBSA-N 0.000 claims description 4
125000001589 carboacyl group Chemical group 0.000 claims description 3
101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims 1
QHINYJQPBCMLCJ-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan Chemical compound C1COC2CCCC21 QHINYJQPBCMLCJ-UHFFFAOYSA-N 0.000 claims 1
239000000243 solution Substances 0.000 description 91
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 85
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 83
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
239000003921 oil Substances 0.000 description 62
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 56
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
239000000203 mixture Substances 0.000 description 53
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 49
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 44
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 37
238000003756 stirring Methods 0.000 description 34
239000000284 extract Substances 0.000 description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
229910052943 magnesium sulfate Inorganic materials 0.000 description 28
235000019341 magnesium sulphate Nutrition 0.000 description 28
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
239000000741 silica gel Substances 0.000 description 24
229910002027 silica gel Inorganic materials 0.000 description 24
229960000583 acetic acid Drugs 0.000 description 19
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 18
229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
235000017557 sodium bicarbonate Nutrition 0.000 description 18
239000012279 sodium borohydride Substances 0.000 description 18
229910000033 sodium borohydride Inorganic materials 0.000 description 18
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000012230 colorless oil Substances 0.000 description 14
239000007858 starting material Substances 0.000 description 14
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 13
150000002576 ketones Chemical class 0.000 description 13
230000007935 neutral effect Effects 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000012362 glacial acetic acid Substances 0.000 description 10
239000000725 suspension Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
238000004440 column chromatography Methods 0.000 description 9
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
229910052786 argon Inorganic materials 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
238000000034 method Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
239000002904 solvent Substances 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
238000013375 chromatographic separation Methods 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
229960004592 isopropanol Drugs 0.000 description 5
238000000746 purification Methods 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
125000002252 acyl group Chemical group 0.000 description 4
229910000019 calcium carbonate Inorganic materials 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
235000019439 ethyl acetate Nutrition 0.000 description 4
238000001914 filtration Methods 0.000 description 4
230000009467 reduction Effects 0.000 description 4
239000000052 vinegar Substances 0.000 description 4
235000021419 vinegar Nutrition 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
150000004653 carbonic acids Chemical class 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000004927 clay Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
239000000499 gel Substances 0.000 description 3
BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical class [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229940094443 oxytocics prostaglandins Drugs 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
230000007306 turnover Effects 0.000 description 3
239000011701 zinc Substances 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
GYTDJCTUFWFXBE-UHFFFAOYSA-M (2,2,2-trifluoroacetyl)oxymercury Chemical compound [Hg+].[O-]C(=O)C(F)(F)F GYTDJCTUFWFXBE-UHFFFAOYSA-M 0.000 description 2
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
FPRITVHPAICIAA-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3,6-dimethylhept-5-en-2-one Chemical compound COP(=O)(OC)CC(=O)C(C)CC=C(C)C FPRITVHPAICIAA-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical class OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
FHJOKULWJSXCKI-UHFFFAOYSA-N 6-methyl-1-(triphenyl-$l^{5}-phosphanylidene)hept-5-en-2-one Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)CCC=C(C)C)C1=CC=CC=C1 FHJOKULWJSXCKI-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
101100310593 Candida albicans (strain SC5314 / ATCC MYA-2876) SOD4 gene Proteins 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N Lactic Acid Natural products CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
MYHXHCUNDDAEOZ-UHFFFAOYSA-N Prostaglandin A&2% Natural products CCCCCC(O)C=CC1C=CC(=O)C1CC=CCCCC(O)=O MYHXHCUNDDAEOZ-UHFFFAOYSA-N 0.000 description 2
101100190148 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PGA2 gene Proteins 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
206010003119 arrhythmia Diseases 0.000 description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
235000014121 butter Nutrition 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
239000006227 byproduct Substances 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
239000000306 component Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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 2
229960002986 dinoprostone Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical class OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
229940100892 mercury compound Drugs 0.000 description 2
150000002731 mercury compounds Chemical class 0.000 description 2
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
238000002156 mixing Methods 0.000 description 2
OUPLTJDZPQZRBW-UHFFFAOYSA-N n-(oxomethylidene)methanesulfonamide Chemical compound CS(=O)(=O)N=C=O OUPLTJDZPQZRBW-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
239000000047 product Substances 0.000 description 2
MYHXHCUNDDAEOZ-FOSBLDSVSA-N prostaglandin A2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O MYHXHCUNDDAEOZ-FOSBLDSVSA-N 0.000 description 2
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 2
210000002307 prostate Anatomy 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 1
IQKOVLZJPVVLOZ-UHFFFAOYSA-N 1-o-tert-butyl 3-o-ethyl piperazine-1,3-dicarboxylate Chemical compound CCOC(=O)C1CN(C(=O)OC(C)(C)C)CCN1 IQKOVLZJPVVLOZ-UHFFFAOYSA-N 0.000 description 1
VRDBIJCCXDEZJN-UHFFFAOYSA-N 2-piperidin-1-ylacetic acid Chemical compound OC(=O)CN1CCCCC1 VRDBIJCCXDEZJN-UHFFFAOYSA-N 0.000 description 1
IRGLXUPKBNSARU-UHFFFAOYSA-N 3,3,6-trimethyl-1-(triphenyl-$l^{5}-phosphanylidene)hept-5-en-2-one Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)C(C)(C)CC=C(C)C)C1=CC=CC=C1 IRGLXUPKBNSARU-UHFFFAOYSA-N 0.000 description 1
ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical class OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
RJADQDXZYFCVHV-JQMWNLLFSA-N 5-[(2s,4r,5r,6ar)-5-hydroxy-4-[(e,3s)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoic acid Chemical compound O1[C@@H](CCCCC(O)=O)CC2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@H]21 RJADQDXZYFCVHV-JQMWNLLFSA-N 0.000 description 1
229910000497 Amalgam Inorganic materials 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
241001123248 Arma Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
241001560893 Cycloes Species 0.000 description 1
241000065675 Cyclops Species 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SGXDXUYKISDCAZ-UHFFFAOYSA-N N,N-diethylglycine Chemical compound CCN(CC)CC(O)=O SGXDXUYKISDCAZ-UHFFFAOYSA-N 0.000 description 1
VIWZVFVJPXTXPA-UHFFFAOYSA-N N-(2-Carboxymethyl)-morpholine Chemical compound OC(=O)CN1CCOCC1 VIWZVFVJPXTXPA-UHFFFAOYSA-N 0.000 description 1
JHXIYTBRMRGFGN-UHFFFAOYSA-N N-[bis(2-methylpropyl)sulfamoyl]-2-methyl-N-(2-methylpropyl)propan-1-amine Chemical compound C(C(C)C)N(CC(C)C)S(=O)(=O)N(CC(C)C)CC(C)C JHXIYTBRMRGFGN-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
229920002292 Nylon 6 Polymers 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
244000269722 Thea sinensis Species 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
244000126014 Valeriana officinalis Species 0.000 description 1
235000013832 Valeriana officinalis Nutrition 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000009471 action Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000729 antidote Substances 0.000 description 1
229940006138 antiglaucoma drug and miotics prostaglandin analogues Drugs 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
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230000037396 body weight Effects 0.000 description 1
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150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
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239000000969 carrier Substances 0.000 description 1
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239000007979 citrate buffer Substances 0.000 description 1
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239000000356 contaminant Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical group C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
YLFBFPXKTIQSSY-UHFFFAOYSA-N dimethoxy(oxo)phosphanium Chemical compound CO[P+](=O)OC YLFBFPXKTIQSSY-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
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239000008298 dragée Substances 0.000 description 1
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JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
229940031098 ethanolamine Drugs 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
RAQDACVRFCEPDA-UHFFFAOYSA-L ferrous carbonate Chemical compound [Fe+2].[O-]C([O-])=O RAQDACVRFCEPDA-UHFFFAOYSA-L 0.000 description 1
230000005021 gait Effects 0.000 description 1
230000027119 gastric acid secretion Effects 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
150000001261 hydroxy acids Chemical class 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
HTBVGZAVHBZXMS-UHFFFAOYSA-N lithium;tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Li].[Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] HTBVGZAVHBZXMS-UHFFFAOYSA-N 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000035800 maturation Effects 0.000 description 1
VYHBEEBFCKLRAZ-UHFFFAOYSA-M mercury(1+);propanoate Chemical compound [Hg+].CCC([O-])=O VYHBEEBFCKLRAZ-UHFFFAOYSA-M 0.000 description 1
XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
MTNBPDPOOLWXLN-LILSUDLASA-N methyl 5-[(2s,3ar,4r,5r,6as)-5-acetyloxy-4-(phenylmethoxymethyl)-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@@H]1[C@H](OC(C)=O)C[C@H]2[C@@H]1C[C@@H](O2)CCCCC(=O)OC)OCC1=CC=CC=C1 MTNBPDPOOLWXLN-LILSUDLASA-N 0.000 description 1
MAUQLEOPGOXIOT-CJNQNQSTSA-N methyl 5-[(2s,3ar,4r,5r,6as)-5-acetyloxy-4-[(1e)-7-methyl-3-oxoocta-1,6-dienyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoate Chemical compound C([C@@H](O1)CCCCC(=O)OC)[C@H]2[C@@H]1C[C@@H](OC(C)=O)[C@@H]2\C=C\C(=O)CCC=C(C)C MAUQLEOPGOXIOT-CJNQNQSTSA-N 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
GLGNSAPAWZUDRT-UHFFFAOYSA-N morpholine-4-sulfonic acid Chemical compound OS(=O)(=O)N1CCOCC1 GLGNSAPAWZUDRT-UHFFFAOYSA-N 0.000 description 1
IYIAWAACGTUPCC-UHFFFAOYSA-N n-(diethylsulfamoyl)-n-ethylethanamine Chemical compound CCN(CC)S(=O)(=O)N(CC)CC IYIAWAACGTUPCC-UHFFFAOYSA-N 0.000 description 1
WIOVVBRSQYYSMV-UHFFFAOYSA-N n-(dimethylsulfamoyl)-n-methylmethanamine Chemical compound CN(C)S(=O)(=O)N(C)C WIOVVBRSQYYSMV-UHFFFAOYSA-N 0.000 description 1
RFKJDNYRWYHJBE-UHFFFAOYSA-N n-[bis(2-chloroethyl)sulfamoyl]-2-chloro-n-(2-chloroethyl)ethanamine Chemical compound ClCCN(CCCl)S(=O)(=O)N(CCCl)CCCl RFKJDNYRWYHJBE-UHFFFAOYSA-N 0.000 description 1
HGHOXDYBAXZUDE-UHFFFAOYSA-N n-butyl-n-(dibutylsulfamoyl)butan-1-amine Chemical compound CCCCN(CCCC)S(=O)(=O)N(CCCC)CCCC HGHOXDYBAXZUDE-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000011664 nicotinic acid Chemical class 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
210000004197 pelvis Anatomy 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 1
230000001012 protector Effects 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000006894 reductive elimination reaction Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
POECFFCNUXZPJT-UHFFFAOYSA-M sodium;carbonic acid;hydrogen carbonate Chemical compound [Na+].OC(O)=O.OC([O-])=O POECFFCNUXZPJT-UHFFFAOYSA-M 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
238000010186 staining Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
238000003786 synthesis reaction Methods 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
150000003512 tertiary amines Chemical class 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
235000016788 valerian Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
- C07D307/937—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans with hydrocarbon or substituted hydrocarbon radicals directly attached in position 2, e.g. prostacyclins
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- 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
- A61P9/06—Antiarrhythmics
- 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
- 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

Landscapes

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

SE7808184A 1977-07-29 1978-07-27 Prostaglandin-i?712-derivat SE443978B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772734791 DE2734791A1 (de)	1977-07-29	1977-07-29	Neue prostaglandin-i tief 2 -derivate und verfahren zu ihrer herstellung

Publications (2)

Publication Number	Publication Date
SE7808184L SE7808184L (sv)	1979-01-30
SE443978B true SE443978B (sv)	1986-03-17

Family

ID=6015442

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7808184A SE443978B (sv)	1977-07-29	1978-07-27	Prostaglandin-i?712-derivat

Country Status (26)

Country	Link
US (1)	US4191694A (de)
JP (1)	JPS5427556A (de)
AT (1)	AT371454B (de)
AU (1)	AU523593B2 (de)
BE (1)	BE869372A (de)
CA (1)	CA1180700A (de)
CH (1)	CH636354A5 (de)
CS (1)	CS207640B2 (de)
DD (1)	DD138904A5 (de)
DE (1)	DE2734791A1 (de)
DK (1)	DK149954C (de)
ES (1)	ES472099A1 (de)
FR (1)	FR2398741A1 (de)
GB (1)	GB2001650B (de)
GR (1)	GR72256B (de)
HU (1)	HU179346B (de)
IE (1)	IE47304B1 (de)
IL (1)	IL55236A (de)
IT (1)	IT1097554B (de)
LU (1)	LU80043A1 (de)
NL (1)	NL7806861A (de)
NZ (1)	NZ187849A (de)
SE (1)	SE443978B (de)
SU (1)	SU921465A3 (de)
YU (1)	YU41595B (de)
ZA (1)	ZA784307B (de)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4264524A (en) *	1979-04-02	1981-04-28	The Upjohn Company	19,20-Didehydro-PG1 amides
US4281191A (en) *	1979-04-02	1981-07-28	The Upjohn Company	19-Hydroxy-19-methyl-PG amides
US4264523A (en) *	1979-04-02	1981-04-28	The Upjohn Company	19,20-Didehydro-13,14-dihydro-PG1 amides
US4283350A (en) *	1979-04-02	1981-08-11	The Upjohn Company	19,20-Didehydro-PG2 amides
US4283351A (en) *	1979-04-02	1981-08-11	The Upjohn Company	19,20-Didehydro-13,14-dihydro-PG2 amides
US4276436A (en) *	1979-04-02	1981-06-30	The Upjohn Company	19-Keto-PG sulfonylamides
US4278815A (en) *	1979-04-02	1981-07-14	The Upjohn Company	19-Keto-PG amides
US4312997A (en) *	1979-07-05	1982-01-26	The Upjohn Company	19-Hydroxy-6-oxo-PGF1 amides
US4289904A (en) *	1979-07-05	1981-09-15	The Upjohn Company	19-Hydroxy-6a-carba-PGI2 sulfonylamides
US4267371A (en) *	1979-07-05	1981-05-12	The Upjohn Company	19-Hydroxy-6a-carba-PGI2 amides
US4281150A (en) *	1979-07-05	1981-07-28	The Upjohn Company	19-Hydroxy-19-methyl-6a-carba-PGI2 sulfonylamides
US4267352A (en) *	1979-07-05	1981-05-12	The Upjohn Company	19-Hydroxy-19-methyl-6-oxo-PGF1 sulfonylamides
JPS6033429B2 (ja) *	1980-04-28	1985-08-02	小野薬品工業株式会社	プロスタグランジン類似化合物
DE3041602A1 (de) *	1980-10-31	1982-06-16	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Neue 5-cyan-prostacyclinderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE3107100A1 (de) *	1981-02-20	1982-09-09	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Azaprostacycline, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung
JPS58124778A (ja) *	1982-01-20	1983-07-25	Toray Ind Inc	５，６，７−トリノル−４，８−インタ−ｍ−フエニレンＰＧＩ↓２誘導体
US4539433A (en) *	1982-11-24	1985-09-03	Tdk Corporation	Electromagnetic shield
JPH0284398U (de) *	1988-12-20	1990-06-29
JPH0397493U (de) *	1990-01-23	1991-10-07
JPH0726876Y2 (ja) *	1990-07-02	1995-06-14	日立フェライト株式会社	電波暗室用電波吸収体
KR930011548B1 (ko) *	1991-08-13	1993-12-10	한국과학기술연구원	적층형 전파흡수체
JP3340732B1 (ja) *	2001-10-05	2002-11-05	日本医薬品工業株式会社	シクロペンタベンゾフラン誘導体の製造方法及びその製造原料となる新規化合物

1977
- 1977-07-29 DE DE19772734791 patent/DE2734791A1/de active Granted
1978
- 1978-06-26 NL NL7806861A patent/NL7806861A/xx not_active Application Discontinuation
- 1978-07-17 SU SU782636446A patent/SU921465A3/ru active
- 1978-07-24 YU YU1762/78A patent/YU41595B/xx unknown
- 1978-07-25 CH CH801778A patent/CH636354A5/de not_active IP Right Cessation
- 1978-07-26 US US05/928,126 patent/US4191694A/en not_active Expired - Lifetime
- 1978-07-26 CS CS784966A patent/CS207640B2/cs unknown
- 1978-07-26 IT IT26113/78A patent/IT1097554B/it active
- 1978-07-27 DD DD78206979A patent/DD138904A5/de unknown
- 1978-07-27 GR GR56881A patent/GR72256B/el unknown
- 1978-07-27 SE SE7808184A patent/SE443978B/sv not_active IP Right Cessation
- 1978-07-27 LU LU80043A patent/LU80043A1/xx unknown
- 1978-07-27 ES ES472099A patent/ES472099A1/es not_active Expired
- 1978-07-27 IL IL55236A patent/IL55236A/xx unknown
- 1978-07-28 DK DK336878A patent/DK149954C/da not_active IP Right Cessation
- 1978-07-28 JP JP9308978A patent/JPS5427556A/ja active Granted
- 1978-07-28 GB GB787831581A patent/GB2001650B/en not_active Expired
- 1978-07-28 IE IE1538/78A patent/IE47304B1/en unknown
- 1978-07-28 CA CA000308336A patent/CA1180700A/en not_active Expired
- 1978-07-28 AU AU38439/78A patent/AU523593B2/en not_active Expired
- 1978-07-28 AT AT0551578A patent/AT371454B/de not_active IP Right Cessation
- 1978-07-28 ZA ZA00784307A patent/ZA784307B/xx unknown
- 1978-07-28 BE BE189587A patent/BE869372A/xx not_active IP Right Cessation
- 1978-07-28 HU HU78SCHE654A patent/HU179346B/hu unknown
- 1978-07-28 FR FR7822401A patent/FR2398741A1/fr active Granted
- 1978-07-29 NZ NZ187849A patent/NZ187849A/xx unknown

Also Published As

Publication number	Publication date
DK336878A (da)	1979-01-30
NL7806861A (nl)	1979-01-31
NZ187849A (en)	1981-01-23
ATA551578A (de)	1982-11-15
LU80043A1 (de)	1978-12-12
BE869372A (fr)	1979-01-29
IT7826113A0 (it)	1978-07-26
IE781538L (en)	1979-01-29
DK149954B (da)	1986-11-03
IL55236A0 (en)	1978-09-29
DK149954C (da)	1987-06-15
US4191694A (en)	1980-03-04
GR72256B (de)	1983-10-06
SE7808184L (sv)	1979-01-30
JPS6259700B2 (de)	1987-12-12
DD138904A5 (de)	1979-11-28
GB2001650B (en)	1982-03-03
CH636354A5 (de)	1983-05-31
ZA784307B (en)	1979-07-25
ES472099A1 (es)	1979-03-16
FR2398741B1 (de)	1980-10-31
CA1180700A (en)	1985-01-08
DE2734791C2 (de)	1990-09-06
YU176278A (en)	1983-01-21
GB2001650A (en)	1979-02-07
SU921465A3 (ru)	1982-04-15
IT1097554B (it)	1985-08-31
JPS5427556A (en)	1979-03-01
IL55236A (en)	1982-09-30
YU41595B (en)	1987-10-31
AU523593B2 (en)	1982-08-05
AT371454B (de)	1983-06-27
AU3843978A (en)	1980-01-31
HU179346B (en)	1982-10-28
DE2734791A1 (de)	1979-02-15
CS207640B2 (en)	1981-08-31
FR2398741A1 (fr)	1979-02-23
IE47304B1 (en)	1984-02-22

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