NO743960L - - Google Patents

Info

Publication number: NO743960L
Authority: NO; Norway
Prior art keywords: hydroxy; acid; oxocyclopent; enheptanoic; parts
Prior art date: 1973-11-02

Application number

NO743960A

Other languages

English (en)

Norwegian (no)

Inventor

R Pappo

P W Collins

Original Assignee

Searle & Co

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.)

1973-11-02

Filing date

1974-11-04

Publication date

1975-05-26

1973-11-02 Priority claimed from US412428A external-priority patent/US3868413A/en

1974-11-04 Application filed by Searle & Co filed Critical Searle & Co

1975-05-26 Publication of NO743960L publication Critical patent/NO743960L/no

Links

239000000203 mixture Substances 0.000 claims description 33
239000002253 acid Substances 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
-1 2-(4(RS)-acetoxy-1-octynyl)-3-acetoxy-5-oxocyclopent-1-enheptanoic acid Chemical compound 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
LVXPDCZDLYJCST-UHFFFAOYSA-N 7-(4-hydroxy-2-methoxy-5-oxocyclopenten-1-yl)heptanoic acid Chemical compound COC1=C(CCCCCCC(O)=O)C(=O)C(O)C1 LVXPDCZDLYJCST-UHFFFAOYSA-N 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000002524 organometallic group Chemical group 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 5
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 5
RPTGFUMPTUKPDS-UHFFFAOYSA-N 7-[3-hydroxy-2-(4-hydroxyoct-1-ynyl)-5-oxocyclopenten-1-yl]heptanoic acid Chemical compound OC(CC#CC1=C(C(CC1O)=O)CCCCCCC(=O)O)CCCC RPTGFUMPTUKPDS-UHFFFAOYSA-N 0.000 claims description 3
230000032050 esterification Effects 0.000 claims description 3
238000005886 esterification reaction Methods 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
RPTGFUMPTUKPDS-FUKCDUGKSA-N 7-[3-hydroxy-2-[(4S)-4-hydroxyoct-1-ynyl]-5-oxocyclopenten-1-yl]heptanoic acid Chemical compound O[C@H](CC#CC1=C(C(CC1O)=O)CCCCCCC(=O)O)CCCC RPTGFUMPTUKPDS-FUKCDUGKSA-N 0.000 claims description 2
239000007818 Grignard reagent Substances 0.000 claims description 2
150000004795 grignard reagents Chemical class 0.000 claims description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
150000002902 organometallic compounds Chemical class 0.000 claims description 2
125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 3
230000021736 acetylation Effects 0.000 claims 1
238000006640 acetylation reaction Methods 0.000 claims 1
230000011987 methylation Effects 0.000 claims 1
238000007069 methylation reaction Methods 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
239000002904 solvent Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
238000010992 reflux Methods 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
238000004821 distillation Methods 0.000 description 7
239000000284 extract Substances 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 6
239000010410 layer Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 5
CNKOTDLNZPTGOY-UHFFFAOYSA-N oct-1-yn-4-ol Chemical compound CCCCC(O)CC#C CNKOTDLNZPTGOY-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
ASUMHSZQZHAHEA-UHFFFAOYSA-N 7-(3-hydroxy-2,5-dioxocyclopentyl)heptanoic acid Chemical compound OC1CC(=O)C(CCCCCCC(O)=O)C1=O ASUMHSZQZHAHEA-UHFFFAOYSA-N 0.000 description 4
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
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
GWJWJDLPXYCVTI-UHFFFAOYSA-N methyl 7-(4-hydroxy-2-methoxy-5-oxocyclopenten-1-yl)heptanoate Chemical compound COC(=O)CCCCCCC1=C(OC)CC(O)C1=O GWJWJDLPXYCVTI-UHFFFAOYSA-N 0.000 description 3
230000000580 secretagogue effect Effects 0.000 description 3
RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 2
CNKOTDLNZPTGOY-QMMMGPOBSA-N (4r)-oct-1-yn-4-ol Chemical compound CCCC[C@@H](O)CC#C CNKOTDLNZPTGOY-QMMMGPOBSA-N 0.000 description 2
CNKOTDLNZPTGOY-MRVPVSSYSA-N (4s)-oct-1-yn-4-ol Chemical compound CCCC[C@H](O)CC#C CNKOTDLNZPTGOY-MRVPVSSYSA-N 0.000 description 2
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 2
YNXXIKVLODBVEE-UHFFFAOYSA-N 7-(2,3,5-trioxocyclopentyl)heptanoic acid Chemical compound OC(=O)CCCCCCC1C(=O)CC(=O)C1=O YNXXIKVLODBVEE-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
230000001262 anti-secretory effect Effects 0.000 description 2
230000000026 anti-ulcerogenic effect Effects 0.000 description 2
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000010828 elution Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000000605 extraction Methods 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 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
WILBTFWIBAOWLN-UHFFFAOYSA-N triethyl(triethylsilyloxy)silane Chemical compound CC[Si](CC)(CC)O[Si](CC)(CC)CC WILBTFWIBAOWLN-UHFFFAOYSA-N 0.000 description 2
WOELJDRTPGDSEA-NIFFTEIASA-N (4s)-oct-1-yn-4-ol;phthalic acid Chemical compound CCCC[C@H](O)CC#C.OC(=O)C1=CC=CC=C1C(O)=O WOELJDRTPGDSEA-NIFFTEIASA-N 0.000 description 1
JBFDBSZCFDASAE-UHFFFAOYSA-N 2-oxodecanoic acid Chemical compound CCCCCCCCC(=O)C(O)=O JBFDBSZCFDASAE-UHFFFAOYSA-N 0.000 description 1
RPTGFUMPTUKPDS-NYRJJRHWSA-N 7-[3-hydroxy-2-[(4R)-4-hydroxyoct-1-ynyl]-5-oxocyclopenten-1-yl]heptanoic acid Chemical compound O[C@@H](CC#CC1=C(C(CC1O)=O)CCCCCCC(=O)O)CCCC RPTGFUMPTUKPDS-NYRJJRHWSA-N 0.000 description 1
BYFKKNYEIXWOQO-UHFFFAOYSA-N 9-oxo capric acid Chemical compound CC(=O)CCCCCCCC(O)=O BYFKKNYEIXWOQO-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
241000588699 Erwinia sp. Species 0.000 description 1
241000233866 Fungi Species 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
ZRKWMRDKSOPRRS-UHFFFAOYSA-N N-Methyl-N-nitrosourea Chemical compound O=NN(C)C(N)=O ZRKWMRDKSOPRRS-UHFFFAOYSA-N 0.000 description 1
108010079943 Pentagastrin Proteins 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000248418 Tetrahymena pyriformis Species 0.000 description 1
241000223238 Trichophyton Species 0.000 description 1
241001123669 Verticillium albo-atrum Species 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000004645 aluminates Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
230000000884 anti-protozoa Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
150000001940 cyclopentanes Chemical class 0.000 description 1
ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
150000002084 enol ethers Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000010985 leather Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910001623 magnesium bromide Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
HESHNEGWPWFJRX-UHFFFAOYSA-N methoxymethoxycyclopentane Chemical class COCOC1CCCC1 HESHNEGWPWFJRX-UHFFFAOYSA-N 0.000 description 1
OIMNNAXGHPCXMA-UHFFFAOYSA-N methyl 7-(3-hydroxy-2,5-dioxocyclopentyl)heptanoate Chemical compound COC(=O)CCCCCCC1C(=O)CC(O)C1=O OIMNNAXGHPCXMA-UHFFFAOYSA-N 0.000 description 1
ZWTFZHTWWSBTAB-UHFFFAOYSA-N methyl 7-(3-hydroxy-2-methoxy-5-oxocyclopenten-1-yl)heptanoate Chemical compound COC(=O)CCCCCCC1=C(OC)C(O)CC1=O ZWTFZHTWWSBTAB-UHFFFAOYSA-N 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000003901 oxalic acid esters Chemical class 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
229960000444 pentagastrin Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000011477 surgical intervention Methods 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
- 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
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO743960A 1973-11-02 1974-11-04 NO743960L (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US412428A US3868413A (en)	1970-06-04	1973-11-02	2-(4-Hydroxy-1-alkynyl)-5-oxocyclopent-1-enealkanoic acids, 3-hydroxy congeners corresponding and derivatives thereof

Publications (1)

Publication Number	Publication Date
NO743960L true NO743960L (fr)	1975-05-26

Family

ID=23632935

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO743960A NO743960L (fr)	1973-11-02	1974-11-04

Country Status (13)

Country	Link
JP (1)	JPS50111048A (fr)
AT (1)	AT336813B (fr)
AU (1)	AU7490774A (fr)
BE (1)	BE821817A (fr)
CA (1)	CA1042882A (fr)
DE (1)	DE2451798A1 (fr)
ES (1)	ES431553A1 (fr)
FR (1)	FR2249660B1 (fr)
GB (1)	GB1458245A (fr)
NL (1)	NL7414345A (fr)
NO (1)	NO743960L (fr)
SE (1)	SE7413813L (fr)
ZA (1)	ZA747066B (fr)

1974
- 1974-10-31 CA CA212,791A patent/CA1042882A/fr not_active Expired
- 1974-10-31 DE DE19742451798 patent/DE2451798A1/de active Pending
- 1974-10-31 ES ES431553A patent/ES431553A1/es not_active Expired
- 1974-10-31 AU AU74907/74A patent/AU7490774A/en not_active Expired
- 1974-10-31 AT AT875974A patent/AT336813B/de not_active IP Right Cessation
- 1974-10-31 FR FR7436465A patent/FR2249660B1/fr not_active Expired
- 1974-11-01 GB GB4735374A patent/GB1458245A/en not_active Expired
- 1974-11-01 JP JP49126507A patent/JPS50111048A/ja active Pending
- 1974-11-04 SE SE7413813A patent/SE7413813L/xx unknown
- 1974-11-04 NO NO743960A patent/NO743960L/no unknown
- 1974-11-04 BE BE150179A patent/BE821817A/fr unknown
- 1974-11-04 ZA ZA00747066A patent/ZA747066B/xx unknown
- 1974-11-04 NL NL7414345A patent/NL7414345A/xx unknown

Also Published As

Publication number	Publication date
FR2249660A1 (fr)	1975-05-30
GB1458245A (en)	1976-12-08
DE2451798A1 (de)	1975-05-07
NL7414345A (nl)	1975-05-07
ES431553A1 (es)	1976-11-01
BE821817A (fr)	1975-05-05
ZA747066B (en)	1975-12-31
CA1042882A (fr)	1978-11-21
FR2249660B1 (fr)	1977-09-09
SE7413813L (fr)	1975-05-05
ATA875974A (de)	1976-09-15
JPS50111048A (fr)	1975-09-01
AT336813B (de)	1977-05-25
AU7490774A (en)	1976-05-06

Publication	Publication Date	Title
US2359096A (en)	1944-09-26	beta-substituted-delta alpha, beta-gamma-butyrolactones and beta-substituted - beta - hydroxy-gamma-butyrolactones and methods of preparing them
NO800796L (no)	1980-09-22	Fremgangsmaate for fremstilling av terapeutisk virksomme kromonderivater
NO140977B (no)	1979-09-10	Analogifremgangsmaate til fremstilling av terapeutisk aktive 2-amino-1,4-dihydropyridiner
NO175714B (no)	1994-08-15	Analogifremgangsmåte for fremstilling av terapeutisk aktive, aromatiske estere
IL30735A (en)	1970-12-24	Process for preparing tetra and hexa hydroindane derivatives
US4673761A (en)	1987-06-16	Process for preparing anti-inflammatory cycloalkylidenemethylphenylacetic acid derivatives
NO140978B (no)	1979-09-10	Analogifremgangsmaate for fremstilling av terapeutisk aktive isokinolinderivater
US3524867A (en)	1970-08-18	Process for producing cyclopenta (b)pyrans
NO750819L (fr)	1975-09-23
Sheehan et al.	1954	The synthesis of substituted penicillins and simpler structural analogs. VIII. Phthalimidomalonaldehydic esters: Synthesis and condensation with penicillamine
NO743960L (fr)	1975-05-26
Salo et al.	1969	N-Acylenamines from oxazolines. New route to 2-acetamidogylcals
US3868413A (en)	1975-02-25	2-(4-Hydroxy-1-alkynyl)-5-oxocyclopent-1-enealkanoic acids, 3-hydroxy congeners corresponding and derivatives thereof
JPH10265441A5 (fr)	2005-02-17
NO175780B (no)	1994-08-29	Analogifremgangsmåte for fremstilling av terapeutisk aktive substituerte dibenzofuraner
US3836581A (en)	1974-09-17	1-alkoximino-2-(omega-substituted-alkyl)-2-cyclopentenes
Sudo et al.	1967	Synthesis of carolic acid
US4087621A (en)	1978-05-02	7-{3-Hydroxy-2β-[4-hydroxy-4-(lower alkyl)-trans-1-octen-1-yl]-5-oxocyclopent-1α-yl}hept-5-cis-enoic acids and related compounds
US2842559A (en)	1958-07-08	Synthesis of estrone intermediates
US4201870A (en)	1980-05-06	Process for the preparation of 2-(3-benzoylphenyl)-propionic acid
US3932496A (en)	1976-01-13	Mono- and dialkylated prostynoic acid derivatives
US2759013A (en)	1956-08-14	Steroid intermediates
US4162364A (en)	1979-07-24	Process for the preparation of 2-(3-benzoylphenyl)-propionic acid
US4172953A (en)	1979-10-30	2,3,5-Trisubstituted cyclopentanealkenoic acids, derivatives thereof and intermediates thereto
US3454601A (en)	1969-07-08	Cyclopentyl ethers of stilbene derivatives