BE712145A - - Google Patents

Info

Publication number: BE712145A
Authority: BE; Belgium
Prior art keywords: proscillaridin; carbon atoms; reaction; sep; process according
Prior art date: 1967-03-18

Application number

Other languages

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.)

1967-03-18

Filing date

1968-03-14

Publication date

1968-07-15

1968-03-14 Application filed filed Critical

1968-07-15 Publication of BE712145A publication Critical patent/BE712145A/fr

Links

229960003584 proscillaridin Drugs 0.000 claims description 30
MYEJFUXQJGHEQK-ALRJYLEOSA-N Proscillaridin Chemical class O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C=C2CC[C@H]3[C@@]4(O)CC[C@H](C5=COC(=O)C=C5)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 MYEJFUXQJGHEQK-ALRJYLEOSA-N 0.000 claims description 27
MYEJFUXQJGHEQK-UHFFFAOYSA-N proscillaridin A Natural products OC1C(O)C(O)C(C)OC1OC1C=C2CCC3C4(O)CCC(C5=COC(=O)C=C5)C4(C)CCC3C2(C)CC1 MYEJFUXQJGHEQK-UHFFFAOYSA-N 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 19
238000000034 method Methods 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 9
-1 alkylidene proscillaridin A Chemical compound 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical group C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 claims description 4
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
239000003377 acid catalyst Substances 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 2
101150031590 catJ gene Proteins 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
239000000047 product Substances 0.000 description 9
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
DHXYKQBZTQTODL-LJSSCIMDSA-N 5-[(3s,10r,13r,14s,17r)-14-hydroxy-3-[[(4s,7r)-7-hydroxy-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3ah-[1,3]dioxolo[4,5-c]pyran-4-yl]oxy]-10,13-dimethyl-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one Chemical compound C=1([C@@H]2[C@@]3(C)CCC4[C@@]5(C)CC[C@@H](C=C5CCC4[C@@]3(O)CC2)O[C@H]2OC([C@H](C3OC(C)(C)OC32)O)C)C=CC(=O)OC=1 DHXYKQBZTQTODL-LJSSCIMDSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000002904 solvent Substances 0.000 description 5
150000007513 acids Chemical class 0.000 description 4
239000000203 mixture Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000008298 dragée Substances 0.000 description 3
229930182470 glycoside Natural products 0.000 description 3
150000002338 glycosides Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229930190098 proscillaridin Natural products 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000000126 substance Substances 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
125000001118 alkylidene group Chemical group 0.000 description 2
239000011260 aqueous acid Substances 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010828 elution Methods 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000005303 weighing Methods 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
244000304921 Charybdis maritima Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
244000141359 Malus pumila Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
235000021016 apples Nutrition 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000004683 dihydrates Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000008389 polyethoxylated castor oil Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
229940066675 ricinoleate Drugs 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Landscapes

Saccharide Compounds (AREA)
Stringed Musical Instruments (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

BE712145D 1967-03-18 1968-03-14 BE712145A (da)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEA0055193		1967-03-18

Publications (1)

Publication Number	Publication Date
BE712145A true BE712145A (da)	1968-07-15

Family

ID=6939876

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE712145D BE712145A (da)	1967-03-18	1968-03-14

Country Status (5)

Country	Link
BE (1)	BE712145A (da)
ES (1)	ES351328A1 (da)
FR (1)	FR8473M (da)
LU (1)	LU55588A1 (da)
NL (1)	NL6803441A (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2034576A1 (da) *	1969-02-28	1970-12-11	Knoll Ag

1968
- 1968-02-29 LU LU55588D patent/LU55588A1/xx unknown
- 1968-03-07 ES ES351328A patent/ES351328A1/es not_active Expired
- 1968-03-11 NL NL6803441A patent/NL6803441A/xx unknown
- 1968-03-14 BE BE712145D patent/BE712145A/fr unknown
- 1968-03-18 FR FR144235A patent/FR8473M/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2034576A1 (da) *	1969-02-28	1970-12-11	Knoll Ag

Also Published As

Publication number	Publication date
LU55588A1 (da)	1968-05-06
FR8473M (da)	1972-06-09
NL6803441A (da)	1968-09-19
ES351328A1 (es)	1969-06-01

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BE712145A - - Google Patents

Info

Links

Landscapes

Applications Claiming Priority (1)

Publications (1)

Family

ID=6939876

Family Applications (1)

Country Status (5)

Cited By (1)

Cited By (1)

Also Published As

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