NL8702881A - Nieuwe prostacyclinen, werkwijzen ter bereiding ervan, farmaceutische preparaten, die de nieuwe prostacyclinen bevatten alsmede de toepassing daarvan. - Google Patents

Nieuwe prostacyclinen, werkwijzen ter bereiding ervan, farmaceutische preparaten, die de nieuwe prostacyclinen bevatten alsmede de toepassing daarvan. Download PDF

Info

Publication number: NL8702881A
Authority: NL; Netherlands
Prior art keywords: hydroxy; furan; cyclopenta; formula; propenyl
Prior art date: 1986-12-01

Application number

NL8702881A

Other languages

English (en)

Dutch (nl)

Original Assignee

Hoffmann La Roche

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.)

1986-12-01

Filing date

1987-12-01

Publication date

1988-07-01

1987-12-01 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1988-07-01 Publication of NL8702881A publication Critical patent/NL8702881A/nl

Links

239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
238000000034 method Methods 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims description 141
-1 1-fluoro-cyclohexyl Chemical group 0.000 claims description 96
150000004702 methyl esters Chemical class 0.000 claims description 57
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 41
239000000203 mixture Substances 0.000 claims description 41
125000000217 alkyl group Chemical group 0.000 claims description 37
150000003839 salts Chemical class 0.000 claims description 27
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 9
125000001153 fluoro group Chemical group F* 0.000 claims description 9
229920006395 saturated elastomer Polymers 0.000 claims description 9
230000000699 topical effect Effects 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
230000003287 optical effect Effects 0.000 claims description 7
150000002148 esters Chemical group 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
UNIUENXBJDVLTK-UHFFFAOYSA-N CCCC(=C1CC=CO1)C(=O)O Chemical compound CCCC(=C1CC=CO1)C(=O)O UNIUENXBJDVLTK-UHFFFAOYSA-N 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
208000018262 Peripheral vascular disease Diseases 0.000 claims description 4
125000001589 carboacyl group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
150000002431 hydrogen Chemical group 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims 2
239000003814 drug Substances 0.000 claims 2
KHSMUFXNCQTISP-UHFFFAOYSA-N 2-[3-fluoro-5-[3-(1-fluorocyclohexyl)-3-hydroxyprop-1-enyl]-5-hydroxy-3a,4,6,6a-tetrahydro-3h-cyclopenta[b]furan-2-ylidene]pentanoic acid Chemical compound C1C2C(F)C(=C(C(O)=O)CCC)OC2CC1(O)C=CC(O)C1(F)CCCCC1 KHSMUFXNCQTISP-UHFFFAOYSA-N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 58
238000006243 chemical reaction Methods 0.000 description 49
239000000243 solution Substances 0.000 description 49
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
235000002639 sodium chloride Nutrition 0.000 description 34
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
125000003118 aryl group Chemical group 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
239000002904 solvent Substances 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
210000003743 erythrocyte Anatomy 0.000 description 12
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 11
239000007787 solid Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
WXTKIFAAJBAEEH-UHFFFAOYSA-N 5-(furan-2-yl)pentanoic acid Chemical compound OC(=O)CCCCC1=CC=CO1 WXTKIFAAJBAEEH-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
239000012043 crude product Substances 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
238000001816 cooling Methods 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
239000012300 argon atmosphere Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000012230 colorless oil Substances 0.000 description 6
239000000284 extract Substances 0.000 description 6
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 6
239000011541 reaction mixture Substances 0.000 description 6
239000012047 saturated solution Substances 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 5
239000013543 active substance Substances 0.000 description 5
239000002775 capsule Substances 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
238000003776 cleavage reaction Methods 0.000 description 5
239000006071 cream Substances 0.000 description 5
125000004494 ethyl ester group Chemical group 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
XHFXMNZYIKFCPN-UHFFFAOYSA-N perchloryl fluoride Chemical compound FCl(=O)(=O)=O XHFXMNZYIKFCPN-UHFFFAOYSA-N 0.000 description 5
230000007017 scission Effects 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
DICZUTMNXOMHQD-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one Chemical compound C1CCC2OC(=O)CC21 DICZUTMNXOMHQD-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
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 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 4
206010039710 Scleroderma Diseases 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
239000003480 eluent Substances 0.000 description 4
238000010828 elution Methods 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
125000001033 ether group Chemical group 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 4
238000000926 separation method Methods 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
229940126062 Compound A Drugs 0.000 description 3
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-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
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical group CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
210000000601 blood cell Anatomy 0.000 description 3
239000006285 cell suspension Substances 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
150000002191 fatty alcohols Chemical class 0.000 description 3
239000012025 fluorinating agent Substances 0.000 description 3
238000003682 fluorination reaction Methods 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
239000006210 lotion Substances 0.000 description 3
239000012528 membrane Substances 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
LHYPLJGBYPAQAK-UHFFFAOYSA-M sodium;pentanoate Chemical compound [Na+].CCCCC([O-])=O LHYPLJGBYPAQAK-UHFFFAOYSA-M 0.000 description 3
239000000725 suspension Substances 0.000 description 3
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 3
238000011200 topical administration Methods 0.000 description 3
BLIQUJLAJXRXSG-UHFFFAOYSA-N 1-benzyl-3-(trifluoromethyl)pyrrolidin-1-ium-3-carboxylate Chemical compound C1C(C(=O)O)(C(F)(F)F)CCN1CC1=CC=CC=C1 BLIQUJLAJXRXSG-UHFFFAOYSA-N 0.000 description 2
KPHYQWGKSTZREA-UHFFFAOYSA-N 1-fluorocyclohexane-1-carboxylic acid Chemical compound OC(=O)C1(F)CCCCC1 KPHYQWGKSTZREA-UHFFFAOYSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 2
DOBNBRNXWCUUQW-UHFFFAOYSA-N 2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-carbaldehyde Chemical compound O1C(=O)CC2C(C=O)CCC21 DOBNBRNXWCUUQW-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
238000006052 Horner reaction Methods 0.000 description 2
206010022562 Intermittent claudication Diseases 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
229920001214 Polysorbate 60 Polymers 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
238000007239 Wittig reaction Methods 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
150000004808 allyl alcohols Chemical class 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
239000007853 buffer solution Substances 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
239000000969 carrier Substances 0.000 description 2
208000024980 claudication Diseases 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000005661 deetherification reaction Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000005837 enolization reaction Methods 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
UWSJCCUODNDXOT-UHFFFAOYSA-N ethyl cyclopentanecarboxylate Chemical compound CCOC(=O)C1CCCC1 UWSJCCUODNDXOT-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
ICGWWCLWBPLPDF-UHFFFAOYSA-N furan-2-ol Chemical compound OC1=CC=CO1 ICGWWCLWBPLPDF-UHFFFAOYSA-N 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
230000002140 halogenating effect Effects 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
239000011777 magnesium Chemical class 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
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000002674 ointment Substances 0.000 description 2
239000002304 perfume Substances 0.000 description 2
235000019271 petrolatum Nutrition 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229960003975 potassium Drugs 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
150000003815 prostacyclins Chemical class 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000012266 salt solution Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
235000019345 sodium thiosulphate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
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239000012049 topical pharmaceutical composition Substances 0.000 description 1
229940117013 triethanolamine oleate Drugs 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
230000007306 turnover Effects 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 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
- 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- 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
- 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4018—Esters of cycloaliphatic acids

Landscapes

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

NL8702881A 1986-12-01 1987-12-01 Nieuwe prostacyclinen, werkwijzen ter bereiding ervan, farmaceutische preparaten, die de nieuwe prostacyclinen bevatten alsmede de toepassing daarvan. NL8702881A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/936,569 US4808734A (en)	1986-12-01	1986-12-01	16-cycloalkyl-7-fluoro-prostacyclins
US93656986		1986-12-01

Publications (1)

Publication Number	Publication Date
NL8702881A true NL8702881A (nl)	1988-07-01

Family

ID=25468824

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8702881A NL8702881A (nl)	1986-12-01	1987-12-01	Nieuwe prostacyclinen, werkwijzen ter bereiding ervan, farmaceutische preparaten, die de nieuwe prostacyclinen bevatten alsmede de toepassing daarvan.

Country Status (15)

Country	Link
US (1)	US4808734A (da)
JP (1)	JPS63145276A (da)
AT (1)	AT392071B (da)
AU (1)	AU604792B2 (da)
BE (1)	BE1001109A3 (da)
CH (1)	CH673650A5 (da)
DE (1)	DE3740596A1 (da)
DK (1)	DK627887A (da)
FR (1)	FR2607500A1 (da)
GB (1)	GB2198131B (da)
IT (1)	IT1223391B (da)
NL (1)	NL8702881A (da)
NZ (1)	NZ222724A (da)
SE (1)	SE8704771L (da)
ZA (1)	ZA878946B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW208001B (da) *	1990-09-07	1993-06-21	Asahi Glass Co Ltd

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1513913A (en) *	1975-06-20	1978-06-14	Ici Ltd	Prostane derivatives
US4565827A (en) *	1980-10-27	1986-01-21	Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T.	7-Substituted PGI2 -derivatives and pharmaceutical compositions containing them
EP0054795B1 (en) *	1980-12-09	1987-07-15	Teijin Limited	Novel halogenated prostacyclins, process for the production thereof, and pharmaceutical use thereof
US4558142A (en) *	1981-03-11	1985-12-10	Hoffmann-La Roche Inc.	7-Fluoro-prostacyclin analogs
CH651033A5 (de) *	1981-03-11	1985-08-30	Hoffmann La Roche	Fluorprostacycline.
JPS58150583A (ja) *	1982-03-04	1983-09-07	Teijin Ltd	新規なハロゲン化プロスタサイクリン類、それらの製造法およびそれらを活性成分とする薬学的組成物
JPS59227888A (ja) *	1983-06-10	1984-12-21	Asahi Glass Co Ltd	７−フルオロプロスタグランジン類の製造方法
HU191264B (en) *	1984-01-13	1987-01-28	Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu	Process for production of derivatives of 7-oxo-prostacyclin with selective biological effect
JPS60243079A (ja) *	1984-05-18	1985-12-03	Asahi Glass Co Ltd	７―フルオロプロスタグランジンｉ↓２類を有効成分とする薬剤
US4616034A (en) *	1985-02-28	1986-10-07	G. D. Searle & Co.	15(R)-5-fluoroprostacyclins, pharmaceutical compositions and anti-thrombotic method of use thereof
JPS61289034A (ja) *	1985-06-17	1986-12-19	Teijin Ltd	イソカルバサイクリン類脂肪乳剤
FR2583828B1 (fr) *	1985-06-21	1987-08-14	Kley France Sa	Appareil moteur fonctionnant par reprises successives
US4634782A (en) *	1985-06-24	1987-01-06	Hoffmann-La Roche Inc.	7-fluoro-dihydro PGI compounds

1986
- 1986-12-01 US US06/936,569 patent/US4808734A/en not_active Expired - Fee Related
1987
- 1987-11-13 CH CH4429/87A patent/CH673650A5/de not_active IP Right Cessation
- 1987-11-27 ZA ZA878946A patent/ZA878946B/xx unknown
- 1987-11-27 JP JP62297861A patent/JPS63145276A/ja active Pending
- 1987-11-27 NZ NZ222724A patent/NZ222724A/en unknown
- 1987-11-27 FR FR8716486A patent/FR2607500A1/fr not_active Withdrawn
- 1987-11-30 AT AT0313787A patent/AT392071B/de not_active IP Right Cessation
- 1987-11-30 SE SE8704771A patent/SE8704771L/xx not_active Application Discontinuation
- 1987-11-30 BE BE8701357A patent/BE1001109A3/fr not_active IP Right Cessation
- 1987-11-30 IT IT22815/87A patent/IT1223391B/it active
- 1987-11-30 DK DK627887A patent/DK627887A/da not_active Application Discontinuation
- 1987-11-30 AU AU81908/87A patent/AU604792B2/en not_active Expired - Fee Related
- 1987-11-30 DE DE19873740596 patent/DE3740596A1/de not_active Withdrawn
- 1987-11-30 GB GB8727992A patent/GB2198131B/en not_active Expired - Fee Related
- 1987-12-01 NL NL8702881A patent/NL8702881A/nl not_active Application Discontinuation

Also Published As

Publication number	Publication date
GB2198131A (en)	1988-06-08
IT8722815A0 (it)	1987-11-30
US4808734A (en)	1989-02-28
CH673650A5 (da)	1990-03-30
AT392071B (de)	1991-01-25
DK627887A (da)	1988-06-02
BE1001109A3 (fr)	1989-07-18
ZA878946B (en)	1988-06-01
NZ222724A (en)	1990-11-27
DK627887D0 (da)	1987-11-30
SE8704771L (sv)	1988-06-02
DE3740596A1 (de)	1988-06-16
GB2198131B (en)	1990-08-08
ATA313787A (de)	1990-07-15
GB8727992D0 (en)	1988-01-06
IT1223391B (it)	1990-09-19
AU604792B2 (en)	1991-01-03
JPS63145276A (ja)	1988-06-17
SE8704771D0 (sv)	1987-11-30
AU8190887A (en)	1988-06-02
FR2607500A1 (fr)	1988-06-03

Publication	Publication Date	Title
JPS6147459A (ja)	1986-03-07	１１−置換−１６−フエノキシプロスタトリエン酸誘導体
US3950406A (en)	1976-04-13	Hydroxylated 15-deoxy derivatives of 9-hydroxy-13-trans-prostenoic acid
IE48178B1 (en)	1984-10-17	Prostacyclin analogs
US3932479A (en)	1976-01-13	Lithium 3-triphenylmethoxy-1-trans-alkenyl-dialkyl alanates
US4060540A (en)	1977-11-29	Novel 3-triphenylmethoxy-1-alkynes, 3-triphenyl-methoxy-1-trans-alkenyl-dialkyl-alanes, and lithium 3-triphenylmethoxy-1-trans-alkenyl-dialkyl alanates
US5057621A (en)	1991-10-15	11-substituted-16-phenoxy and 16-substituted phenoxy-prostatrienoic acid derivatives
NL8702881A (nl)	1988-07-01	Nieuwe prostacyclinen, werkwijzen ter bereiding ervan, farmaceutische preparaten, die de nieuwe prostacyclinen bevatten alsmede de toepassing daarvan.
US4007210A (en)	1977-02-08	Novel 3-triphenylmethoxy-1-alkynes, 3-triphenylmethoxy-1-trans-alkenyl-dialkyl-alanes, and lithium 3-triphenyl-methoxy-1-trans-alkenyl-dialkyl-alanates
JPH0717597B2 (ja)	1995-03-01	フエノキシプロスタトリエン酸誘導体とその製造法
KR860002049B1 (ko)	1986-11-20	플루오로-프로스타사이클린의 제조방법
FR2515650A1 (fr)	1983-05-06	Derives de 3-fluoro cyclopenta (b) furan-2-one
JPS6143161A (ja)	1986-03-01	１６‐フエノキシテトラノルプロスタトリエン酸誘導体
US4123456A (en)	1978-10-31	Novel 11-hydroxy-9-keto-5,6-cis-13,14-cis-prostadienoic acid derivatives
US4060691A (en)	1977-11-29	7-{3-Hydroxy-2-[4-hydroxy-4-(lower alkyl)-trans-1-octen-1-yl]-5-oxocyclopent-1-yl}heptanoic acids and esters
US4181674A (en)	1980-01-01	5-Endo-protected hydroxyl-bicyclo[2,2,1]-heptan-2-ones and process for preparing same
US4179574A (en)	1979-12-18	Novel 2-substituted-3,4-epoxycyclopentan-1-ones, 2-substituted-3,4-epoxycyclopentan-1-ols, and various 2-substituted-cyclo-pentenones
AU595533B2 (en)	1990-04-05	6,9-epoxy-7-fluoro-11-hydroxy-prost-5-en-1-oic acid derivatives
US4343949A (en)	1982-08-10	Novel 2-substituted-3,4-epoxycyclopentan-1-ones, 2-substituted-3,4-epoxycyclopentan-1-ols, and various 2-substituted-cyclopentenones
US3966773A (en)	1976-06-29	2-Substituted-3,4-epoxycyclopentan-1-ones, and 2-substituted-3,4-epoxycyclopentan-1-ols
US4110368A (en)	1978-08-29	Hydro substituted prostanoic acids and esters
JPH11180949A (ja)	1999-07-06	プロスタグランジン誘導体、その製造方法、および医薬
US4439365A (en)	1984-03-27	Novel hydroxy substituted prostanoic acids, esters, congeners, intermediates and process
WO1991013869A1 (en)	1991-09-19	15-deoxyprostaglandin derivative
US4680415A (en)	1987-07-14	Intermediates for 7-fluoro dihydro PGI compounds
JPH0479330B2 (da)	1992-12-15

Legal Events

Date	Code	Title	Description
1990-01-16	CNR	Transfer of rights (patent application after its laying open for public inspection)	Free format text: HOFFMANN-LA ROCHE AG. F. -
1991-08-01	BV	The patent application has lapsed