SU439087A1 - - Google Patents

Info

Publication number: SU439087A1
Authority: SU; USSR - Soviet Union
Prior art keywords: optically active; formula; compound; acid; solution
Prior art date: 1974-08-05

Application number

SU1773037A

Other languages

English (en)

Russian (ru)

Other versions

SU439087A3 (ja

Original Assignee

Ииостраиец Барни Джон Магерлейн

Иностранна фирма

Апджон Комианн

Publication date

1974-08-05

1972-04-11 Application filed by Ииостраиец Барни Джон Магерлейн, Иностранна фирма, Апджон Комианн filed Critical Ииостраиец Барни Джон Магерлейн

1974-08-05 Application granted granted Critical

1974-08-05 Publication of SU439087A1 publication Critical patent/SU439087A1/ru

1974-08-05 Publication of SU439087A3 publication Critical patent/SU439087A3/ru

Links

150000001875 compounds Chemical class 0.000 description 20
239000000243 solution Substances 0.000 description 10
229910052739 hydrogen Inorganic materials 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 8
239000002253 acid Substances 0.000 description 6
230000000875 corresponding Effects 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
-1 alkaline earth metal salts Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
150000002596 lactones Chemical class 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Chemical compound [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 2
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 2
RRKTZKIUPZVBMF-IBTVXLQLSA-N Brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
QMGVPVSNSZLJIA-FVWCLLPLSA-N Strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
239000003480 eluent Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
150000003180 prostaglandins Chemical class 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WZUZROCCERRXFZ-UHFFFAOYSA-N sodium;bis(methylsulfinyl)methane Chemical compound [Na+].CS(=O)[CH-]S(C)=O WZUZROCCERRXFZ-UHFFFAOYSA-N 0.000 description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
BUDQDWGNQVEFAC-UHFFFAOYSA-N 3,4-dihydro-2H-pyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
229940100996 SODIUM BISULFATE Drugs 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M Sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
241001279009 Strychnos toxifera Species 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N Tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
CROBTXVXNQNKKO-UHFFFAOYSA-N borohydride Chemical compound [BH4-] CROBTXVXNQNKKO-UHFFFAOYSA-N 0.000 description 1
239000012267 brine Substances 0.000 description 1
125000004432 carbon atoms Chemical group C* 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
YZCKVEUIGOORGS-OUBTZVSYSA-N deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
229910052805 deuterium Inorganic materials 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
238000004810 partition chromatography Methods 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000003638 reducing agent Substances 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Substances [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
ODGROJYWQXFQOZ-UHFFFAOYSA-N sodium;boron(1-) Chemical compound [B-].[Na+] ODGROJYWQXFQOZ-UHFFFAOYSA-N 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229960005453 strychnine Drugs 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing Effects 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000004304 visual acuity Effects 0.000 description 1

SU1773037A 1971-04-12 1972-04-11 SU439087A3 (ja)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US13334271A	1971-04-12	1971-04-12

Publications (2)

Publication Number	Publication Date
SU439087A1 true SU439087A1 (ja)	1974-08-05
SU439087A3 SU439087A3 (ja)	1974-08-05

Family

ID=22458141

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SU1773037A SU439087A3 (ja)	1971-04-12	1972-04-11
SU721821458A SU628814A3 (ru)	1971-04-12	1972-08-21	Способ получени 16,16-дизамещенных аналогов простагландина

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SU721821458A SU628814A3 (ru)	1971-04-12	1972-08-21	Способ получени 16,16-дизамещенных аналогов простагландина

Country Status (11)

Country	Link
JP (1)	JPS5314551B1 (ja)
AR (2)	AR194589A1 (ja)
ES (1)	ES401665A1 (ja)
FI (1)	FI54293C (ja)
HU (2)	HU166656B (ja)
IL (3)	IL47150A (ja)
NO (3)	NO135936C (ja)
PH (1)	PH10946A (ja)
PL (2)	PL96861B1 (ja)
SU (2)	SU439087A3 (ja)
ZA (1)	ZA721936B (ja)

1972
- 1972-03-21 ZA ZA721936A patent/ZA721936B/xx unknown
- 1972-03-26 IL IL4715072A patent/IL47150A/en unknown
- 1972-03-26 IL IL39079A patent/IL39079A/en unknown
- 1972-03-26 IL IL4715172A patent/IL47151A/en unknown
- 1972-04-03 PH PH13409A patent/PH10946A/en unknown
- 1972-04-05 JP JP3358872A patent/JPS5314551B1/ja active Pending
- 1972-04-06 AR AR24133772A patent/AR194589A1/es active
- 1972-04-10 PL PL15464272A patent/PL96861B1/pl unknown
- 1972-04-10 PL PL18399072A patent/PL96666B1/pl unknown
- 1972-04-11 SU SU1773037A patent/SU439087A3/ru active
- 1972-04-11 ES ES401665A patent/ES401665A1/es not_active Expired
- 1972-04-11 HU HUUO000081 patent/HU166656B/hu unknown
- 1972-04-11 HU HUUO000075 patent/HU165856B/hu unknown
- 1972-04-11 FI FI101772A patent/FI54293C/fi active
- 1972-04-11 NO NO122772A patent/NO135936C/no unknown
- 1972-08-21 SU SU721821458A patent/SU628814A3/ru active
- 1972-11-27 NO NO434172A patent/NO138252C/no unknown
- 1972-11-27 NO NO434272A patent/NO140423C/no unknown
1973
- 1973-02-27 AR AR24682173A patent/AR194784A1/es active

Publication	Publication Date	Title
SU662008A3 (ru)	1979-05-05	Способ получени оптически активных соединений р да простагландинов или их рацематов
SU1316555A3 (ru)	1987-06-07	Способ получени производных карбациклинов или их аддитивно-основных солей трис-(оксиметил)-аминометана
US3532721A (en)	1970-10-06	Cyclopentyl-alkanoic acids
US4271314A (en)	1981-06-02	4,5-Unsaturated prostanoic acid derivatives
EP0134246B1 (en)	1989-08-23	Prostacyclines and process for their preparation
JPS6234027B2 (ja)	1987-07-24
SU439087A1 (ja)	1974-08-05
CA2012081C (en)	2000-08-29	2,5,6,7-tetranor-4,8-inter-m-phenylene pgi 2 derivatives
GB1568017A (en)	1980-05-21	Prostaglandins
US4024181A (en)	1977-05-17	Analogues of prostanoic acids
JPS6341909B2 (ja)	1988-08-19
US4322543A (en)	1982-03-30	4,5-Unsaturated prostanoic acid derivatives
DK147070B (da)	1984-04-02	Analogifremgangsmaade til fremstilling af 13,14-dehydro-11-deoxy-prostaglandiner
US4277401A (en)	1981-07-07	Total synthesis of 1RS,4SR,5RS-4-(4,8-dimethyl)-5-hydroxy-7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-acetic acid
US4110532A (en)	1978-08-29	5-Hydroxy-PGI1 compounds
US4958037A (en)	1990-09-18	Precursors and synthesis of methyl-9-oxo-11α, 16-dihydroxy-16-vinyl-5-cis-13-trans-prostadienoates
US4202972A (en)	1980-05-13	Δ2 -Prostacyclin analogs
JPS5921864B2 (ja)	1984-05-22	フルオロプロスタグランジン及びその製造法
US3991080A (en)	1976-11-09	Prostaglandin intermediates
US3975406A (en)	1976-08-17	Hexahydro-5-oxy-2-loweralkoxy-2H-cyclopenta[b]-furan-4-carbonitrile intermediates for prostaglandins
US4985571A (en)	1991-01-15	6-membered lactones useful as intermediates for antilipemic mevalonic acid lactones
SU843736A3 (ru)	1981-06-30	Способ получени оптически активныхпРОСТАглАНдиНОВ или иХ ОпТичЕСКиХАНТипОдОВ, или иХ РАцЕМАТОВ
US3970674A (en)	1976-07-20	Certain hexahydro-2-loweralkoxy-5-oxycyclopenta [b] furans containing an olefinic substituent in the 4-position
US3974185A (en)	1976-08-10	Hexahydro-cyclopentano[b]furans having a 2-C.tbd.C containing substituent in the 4-position
CH659472A5 (de)	1987-01-30	Epoxycarbacyclinderivate, ihre herstellung und verwendung.