PL105113B1 - Sposob wytwarzania winkameiny - Google Patents

Sposob wytwarzania winkameiny Download PDF

Info

Publication number: PL105113B1
Authority: PL; Poland
Prior art keywords: salt; formula; acid; vinamenine; acid addition
Prior art date: 1976-07-21

Application number

PL19977177A

Other languages

English (en)

Polish (pl)

Other versions

PL199771A1 (pl

Inventor

Otto Clauder

Arpad Kiraly

Jozsef Kokosi

Egon Karpati

Laszlo Szporny

Original Assignee

Richter Gedeon Vegyeszet

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.)

1976-07-21

Filing date

1977-07-20

Publication date

1979-09-29

1977-07-20 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1978-04-24 Publication of PL199771A1 publication Critical patent/PL199771A1/xx

1979-09-29 Publication of PL105113B1 publication Critical patent/PL105113B1/pl

Links

238000004519 manufacturing process Methods 0.000 title description 2
150000003839 salts Chemical class 0.000 claims description 36
239000002253 acid Substances 0.000 claims description 30
238000000034 method Methods 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 21
VKTOXAGUZWAECL-MOPGFXCFSA-N (-)-eburnamenine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=CN5C2=C1 VKTOXAGUZWAECL-MOPGFXCFSA-N 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 15
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
238000006297 dehydration reaction Methods 0.000 claims description 9
238000007669 thermal treatment Methods 0.000 claims description 9
239000012298 atmosphere Substances 0.000 claims description 8
230000018044 dehydration Effects 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 7
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
239000011261 inert gas Substances 0.000 claims description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
235000019253 formic acid Nutrition 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
239000000243 solution Substances 0.000 description 26
239000000047 product Substances 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000003921 oil Substances 0.000 description 15
235000019198 oils Nutrition 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000000956 alloy Substances 0.000 description 7
229910045601 alloy Inorganic materials 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
229910052739 hydrogen Inorganic materials 0.000 description 7
229940075930 picrate Drugs 0.000 description 7
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
210000001367 artery Anatomy 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 description 6
230000017531 blood circulation Effects 0.000 description 5
DDPMGIMJSRUULN-UHFFFAOYSA-N buphedrone Chemical compound CCC(NC)C(=O)C1=CC=CC=C1 DDPMGIMJSRUULN-UHFFFAOYSA-N 0.000 description 5
239000000155 melt Substances 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
102100030550 Menin Human genes 0.000 description 4
101710169972 Menin Proteins 0.000 description 4
UXMCFEBDJVHVNH-HOJAQTOUSA-N ac1l52id Chemical class C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(O)=O)N5C2=C1 UXMCFEBDJVHVNH-HOJAQTOUSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
ZFCQLDAGNBFMJQ-QUCCMNQESA-N apovincaminic acid Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=C(C(O)=O)N5C2=C1 ZFCQLDAGNBFMJQ-QUCCMNQESA-N 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000000052 vinegar Substances 0.000 description 4
235000021419 vinegar Nutrition 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000007127 saponification reaction Methods 0.000 description 3
229960002726 vincamine Drugs 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
OVFUUSPKWADLNJ-UHFFFAOYSA-N 5-methyl-4-nitro-2-(4-nitrophenyl)-4h-pyrazol-3-one Chemical compound O=C1C([N+]([O-])=O)C(C)=NN1C1=CC=C([N+]([O-])=O)C=C1 OVFUUSPKWADLNJ-UHFFFAOYSA-N 0.000 description 2
206010002091 Anaesthesia Diseases 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
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
239000001828 Gelatine Substances 0.000 description 2
240000004808 Saccharomyces cerevisiae Species 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
230000037005 anaesthesia Effects 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000004872 arterial blood pressure Effects 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
-1 drinks bumps Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
230000001435 haemodynamic effect Effects 0.000 description 2
239000005457 ice water Substances 0.000 description 2
230000001965 increasing effect Effects 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
239000000454 talc Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
229960001367 tartaric acid Drugs 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
230000002792 vascular Effects 0.000 description 2
HTEHILLCBQWTLP-UHFFFAOYSA-N 5-phenyl-1,3-diazinane-2,4,6-trione Chemical class O=C1NC(=O)NC(=O)C1C1=CC=CC=C1 HTEHILLCBQWTLP-UHFFFAOYSA-N 0.000 description 1
OZDNDGXASTWERN-CTNGQTDRSA-N Apovincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=C(C(=O)OC)N5C2=C1 OZDNDGXASTWERN-CTNGQTDRSA-N 0.000 description 1
241000282465 Canis Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
DIWRORZWFLOCLC-UHFFFAOYSA-N Lorazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000863480 Vinca Species 0.000 description 1
VLNTZJVJKUHBHN-UHFFFAOYSA-N Vincaminine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(C(C)=O)CC(C(=O)OC)(O)N5C2=C1 VLNTZJVJKUHBHN-UHFFFAOYSA-N 0.000 description 1
229930003268 Vitamin C Natural products 0.000 description 1
MTMHYQSOEUXDNR-UHFFFAOYSA-M [Na+].S.[Cl-].Cl.Cl Chemical compound [Na+].S.[Cl-].Cl.Cl MTMHYQSOEUXDNR-UHFFFAOYSA-M 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
150000003797 alkaloid derivatives Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
229950006936 apovincamine Drugs 0.000 description 1
OZDNDGXASTWERN-UHFFFAOYSA-N apovincamine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)C=C(C(=O)OC)N5C2=C1 OZDNDGXASTWERN-UHFFFAOYSA-N 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
235000019658 bitter taste Nutrition 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
230000004531 blood pressure lowering effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
MIURHJCJPVLLHQ-UHFFFAOYSA-N carbonic acid;chloromethane Chemical compound ClC.OC(O)=O MIURHJCJPVLLHQ-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
229960001270 d- tartaric acid Drugs 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
229960000878 docusate sodium Drugs 0.000 description 1
239000008298 dragée Substances 0.000 description 1
VKTOXAGUZWAECL-RBUKOAKNSA-N eburnamenine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@H]3[C@@]4(CC)C=CN5C2=C1 VKTOXAGUZWAECL-RBUKOAKNSA-N 0.000 description 1
VKTOXAGUZWAECL-OALUTQOASA-N eburnamenine Natural products C1=CC=C2C(CCN3CCC4)=C5[C@H]3[C@]4(CC)C=CN5C2=C1 VKTOXAGUZWAECL-OALUTQOASA-N 0.000 description 1
HONLKDDLTAZVQV-UHFFFAOYSA-N eburnamine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)N5C2=C1 HONLKDDLTAZVQV-UHFFFAOYSA-N 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000003344 environmental pollutant Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000037406 food intake Effects 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000000004 hemodynamic effect Effects 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
238000010409 ironing Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
238000002483 medication Methods 0.000 description 1
235000019837 monoammonium phosphate Nutrition 0.000 description 1
239000006012 monoammonium phosphate Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
239000005416 organic matter Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000003973 paint Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
231100000719 pollutant Toxicity 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
150000007519 polyprotic acids Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
238000007873 sieving Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
VKTOXAGUZWAECL-UHFFFAOYSA-N trans-eburnamenine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)C=CN5C2=C1 VKTOXAGUZWAECL-UHFFFAOYSA-N 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000019154 vitamin C Nutrition 0.000 description 1
239000011718 vitamin C Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

PL19977177A 1976-07-21 1977-07-20 Sposob wytwarzania winkameiny PL105113B1 (pl)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HURI009319		1976-07-21

Publications (2)

Publication Number	Publication Date
PL199771A1 PL199771A1 (pl)	1978-04-24
PL105113B1 true PL105113B1 (pl)	1979-09-29

Family

ID=11001129

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL19977177A PL105113B1 (pl)	1976-07-21	1977-07-20	Sposob wytwarzania winkameiny

Country Status (2)

Country	Link
PL (1)	PL105113B1 (fr)
RO (1)	RO73513A (fr)

1977
- 1977-07-20 PL PL19977177A patent/PL105113B1/pl unknown
- 1977-07-20 RO RO7791105A patent/RO73513A/fr unknown

Also Published As

Publication number	Publication date
PL199771A1 (pl)	1978-04-24
RO73513A (fr)	1980-11-30

Legal Events

Date	Code	Title	Description
2009-06-30	RECP	Rectifications of patent specification

Publication	Publication Date	Title
US4271189A (en)	1981-06-02	Lithium derivatives of taurine having reinforced neuro-muscular activity
SU1739849A3 (ru)	1992-06-07	Способ получени производных бензамида или их фармакологически приемлемых солей
CS274420B2 (en)	1991-04-11	Method of clock-wise isomer alpha-(4,5,6,7-tetrahydrothieno (3,2-c)-5-pyridyl)-)2-chlorphenyl) methylacetate production
JPS6350354B2 (fr)	1988-10-07
JPS60358B2 (ja)	1985-01-07	ベンゾモルフアン化合物の製法
CN101402565A (zh)	2009-04-08	卤代2－（a－羟基戊基）苯甲酸盐及其制法和用途
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PL85479B1 (en)	1976-04-30	Pyridine salt of 2,5-dihydroxy benzene sulfonate p-chlorophenoxy isobutyric ester and a method for the preparation thereof[us3876651a]
JPS61210086A (ja)	1986-09-18	強心薬として有用な１、６−ナフチリジン−２（ｉｈ）−オン類およびその製造方法
NZ229760A (en)	1991-06-25	3-(1-carboxymethyl-2-carboxypyrrol-4-yl)pentanedioic acid and the distrontium salt thereof as a pharmaceutical compound
PL105113B1 (pl)	1979-09-29	Sposob wytwarzania winkameiny
PL80112B1 (fr)	1975-08-30
JPS61106577A (ja)	1986-05-24	フロ−〔３，２−ｃ〕ピリジン誘導体、その製造法およびそれを含有する医薬組成物
CH645643A5 (de)	1984-10-15	Halogenvincamonderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate.
US4473571A (en)	1984-09-25	8-Substituted-2-(4-pyridinyl)-9H-purin-6-amines and their cardiotonic use
PL106888B1 (pl)	1980-01-31	Sposob wytwarzania nowych amin pochodnych 2-fenylodwucyklooktanu i oktenu
CH625789A5 (fr)	1981-10-15
DE2251559A1 (de)	1973-04-26	Neue pyrrolo eckige klammer auf 3,4-b eckige klammer zu pyridinderivate, ihre herstellung und die medizinischen zusammensetzungen, die sie enthalten
US4273780A (en)	1981-06-16	Anti-allergic anti-9,10-dihydro-4-(1-methyl-4-piperidylidene)-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-10(9H)-one oxime
US3925396A (en)	1975-12-09	{62 -Pyridyl-carbonamido-alkane-sulfonic acid salts
US3978081A (en)	1976-08-31	11H,12H-[1]benzopyrano[2,3-b][1]benzopyran-11,12-dione and derivatives
CS195338B2 (en)	1980-01-31	Process for preparing vincamine
JPH0154326B2 (fr)	1989-11-17
PL101823B1 (pl)	1979-02-28	A method of producing new derivatives of indoloquinolysidine
US3542927A (en)	1970-11-24	Reduction of blood sugar levels with aminomethylindoles