CA1108149A - Phosphate de d-glaucine - Google Patents

Phosphate de d-glaucine

Info

Publication number: CA1108149A
Authority: CA; Canada
Prior art keywords: glaucine; phosphate; phosphoric acid; salt; glaucine phosphate
Prior art date: 1979-12-31
Legal status (The legal status 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 status listed.): Expired

Application number

CA342,825A

Other languages

English (en)

Inventor

Samuel S. M. Wang

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Dow Chemical Co

Original Assignee

Dow Chemical 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.)

1979-12-31

Filing date

1979-12-31

Publication date

1981-09-01

1979-12-31 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1979-12-31 Priority to CA342,825A priority Critical patent/CA1108149A/fr

1981-09-01 Application granted granted Critical

1981-09-01 Publication of CA1108149A publication Critical patent/CA1108149A/fr

Status Expired legal-status Critical Current

Links

229940113086 glaucine Drugs 0.000 title claims description 32
DABPOQZSGVNAAS-UHFFFAOYSA-N Glaucocalactone Natural products O=CC12C3C(C4)OC(=O)C2C(C)(C)CCC1OC(=O)C13CC4C(=C)C1OC(=O)C DABPOQZSGVNAAS-UHFFFAOYSA-N 0.000 claims abstract description 49
RUZIUYOSRDWYQF-HNNXBMFYSA-N (S)-glaucine Chemical compound CN1CCC2=CC(OC)=C(OC)C3=C2[C@@H]1CC1=C3C=C(OC)C(OC)=C1 RUZIUYOSRDWYQF-HNNXBMFYSA-N 0.000 claims abstract description 44
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 38
229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 19
238000000034 method Methods 0.000 claims abstract description 14
229910019142 PO4 Inorganic materials 0.000 claims description 29
239000010452 phosphate Substances 0.000 claims description 28
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
-1 d-glaucine phosphate salt Chemical class 0.000 claims description 9
238000000354 decomposition reaction Methods 0.000 claims description 3
238000002844 melting Methods 0.000 claims description 3
230000008018 melting Effects 0.000 claims description 3
239000000126 substance Substances 0.000 claims 2
230000000954 anitussive effect Effects 0.000 abstract description 11
150000003013 phosphoric acid derivatives Chemical class 0.000 abstract description 8
230000000202 analgesic effect Effects 0.000 abstract description 5
239000000796 flavoring agent Substances 0.000 abstract description 3
235000019634 flavors Nutrition 0.000 abstract description 3
230000001976 improved effect Effects 0.000 abstract 1
239000008194 pharmaceutical composition Substances 0.000 abstract 1
235000021317 phosphate Nutrition 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
229930004041 glaucine Natural products 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 13
206010011224 Cough Diseases 0.000 description 11
239000000243 solution Substances 0.000 description 11
229940124584 antitussives Drugs 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
150000003839 salts Chemical class 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000003434 antitussive agent Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000006188 syrup Substances 0.000 description 6
235000020357 syrup Nutrition 0.000 description 6
239000002585 base Substances 0.000 description 5
239000002775 capsule Substances 0.000 description 5
PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
239000013078 crystal Substances 0.000 description 4
235000019629 palatability Nutrition 0.000 description 4
239000007787 solid Substances 0.000 description 4
DFFLCVRJWUOGPN-RSAXXLAASA-N (6as)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-6-ium;bromide Chemical compound Br.CN1CCC2=CC(OC)=C(OC)C3=C2[C@@H]1CC1=C3C=C(OC)C(OC)=C1 DFFLCVRJWUOGPN-RSAXXLAASA-N 0.000 description 3
241000700198 Cavia Species 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229960004126 codeine Drugs 0.000 description 3
238000001914 filtration Methods 0.000 description 3
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 3
239000007937 lozenge Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
DKSZLDSPXIWGFO-BLOJGBSASA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O.OP(O)(O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC DKSZLDSPXIWGFO-BLOJGBSASA-N 0.000 description 2
RUZIUYOSRDWYQF-OAHLLOKOSA-N (6ar)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline Chemical compound CN1CCC2=CC(OC)=C(OC)C3=C2[C@H]1CC1=C3C=C(OC)C(OC)=C1 RUZIUYOSRDWYQF-OAHLLOKOSA-N 0.000 description 2
241000380131 Ammophila arenaria Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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 2
241000699670 Mus sp. Species 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
229930013930 alkaloid Natural products 0.000 description 2
239000000730 antalgic agent Substances 0.000 description 2
BZKUYNBAFQJRDM-UHFFFAOYSA-N aporphine Chemical compound C12=CC=CC=C2CC2N(C)CCC3=CC=CC1=C32 BZKUYNBAFQJRDM-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229960004415 codeine phosphate Drugs 0.000 description 2
229960001270 d- tartaric acid Drugs 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 2
239000003172 expectorant agent Substances 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007928 intraperitoneal injection Substances 0.000 description 2
239000008101 lactose Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000003826 tablet Substances 0.000 description 2
229940095064 tartrate Drugs 0.000 description 2
NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 1
229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
206010013911 Dysgeusia Diseases 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
MKXZASYAUGDDCJ-SZMVWBNQSA-N LSM-2525 Chemical compound C1CCC[C@H]2[C@@]3([H])N(C)CC[C@]21C1=CC(OC)=CC=C1C3 MKXZASYAUGDDCJ-SZMVWBNQSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
241000557172 Stylophorum diphyllum Species 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
208000025371 Taste disease Diseases 0.000 description 1
QCMQEZNBBPGFKQ-UHFFFAOYSA-N Thalisopynine Natural products CN1CCC2=C(OC)C(OC)=C(OC)C3=C2C1CC1=C3C=C(OC)C(O)=C1 QCMQEZNBBPGFKQ-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000003797 alkaloid derivatives Chemical class 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
229940035674 anesthetics Drugs 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
235000019636 bitter flavor Nutrition 0.000 description 1
235000019658 bitter taste Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000007963 capsule composition Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229960001701 chloroform Drugs 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000010908 decantation Methods 0.000 description 1
239000000850 decongestant Substances 0.000 description 1
229940124581 decongestants Drugs 0.000 description 1
238000001739 density measurement Methods 0.000 description 1
229960001985 dextromethorphan Drugs 0.000 description 1
229960000920 dihydrocodeine Drugs 0.000 description 1
RBOXVHNMENFORY-DNJOTXNNSA-N dihydrocodeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC RBOXVHNMENFORY-DNJOTXNNSA-N 0.000 description 1
XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 description 1
231100000676 disease causative agent Toxicity 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000007911 effervescent powder Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229940093503 ethyl maltol Drugs 0.000 description 1
229940073505 ethyl vanillin Drugs 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000003419 expectorant effect Effects 0.000 description 1
229940066493 expectorants Drugs 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000011888 foil Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000003193 general anesthetic agent Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
239000007972 injectable composition Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
FVRABHGHBLRNNR-UHFFFAOYSA-N liriodenine Natural products O=C1C=CC=c2c1cc3nccc4cc5OCOc5c2c34 FVRABHGHBLRNNR-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
229940042813 menthol 7.5 mg Drugs 0.000 description 1
235000019656 metallic taste Nutrition 0.000 description 1
229940066491 mucolytics Drugs 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229960001789 papaverine Drugs 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
229940081310 piperonal Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000008213 purified water Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
230000001235 sensitizing effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
235000019640 taste Nutrition 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000002424 x-ray crystallography Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA342,825A 1979-12-31 1979-12-31 Phosphate de d-glaucine Expired CA1108149A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA342,825A CA1108149A (fr)	1979-12-31	1979-12-31	Phosphate de d-glaucine

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA342,825A CA1108149A (fr)	1979-12-31	1979-12-31	Phosphate de d-glaucine

Publications (1)

Publication Number	Publication Date
CA1108149A true CA1108149A (fr)	1981-09-01

Family

ID=4115939

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA342,825A Expired CA1108149A (fr)	1979-12-31	1979-12-31	Phosphate de d-glaucine

Country Status (1)

Country	Link
CA (1)	CA1108149A (fr)

1979
- 1979-12-31 CA CA342,825A patent/CA1108149A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-09-01	MKEX	Expiry

Publication	Publication Date	Title
CA1079733A (fr)	1980-06-17	OBTENTION DE BENZILATES QUATERNAIRES DE N-ALKYL-NORTROPINE SUBSTITUEE EN N-.beta.
IE46737B1 (en)	1983-09-07	2-(2,2-diarylalkyl)-1-azabicyclo (2.2.2)octane and related compounds
CA1108149A (fr)	1981-09-01	Phosphate de d-glaucine
US4279914A (en)	1981-07-21	Thrombocyte aggregation inhibiting composition and methods
CA1173852A (fr)	1984-09-04	Acides 2-amino-3-(halobenzoyl)-methylpheylacetiques; leurs esters et leurs sels
JPS6140268A (ja)	1986-02-26	イミダゾリン、その付加塩及びその製造方法並びにイミダゾリン又はその付加塩を有効成分とする医薬
US4315010A (en)	1982-02-09	Glaucine phosphate salts
GB2061258A (en)	1981-05-13	Glaucine phosphate salts
US4265912A (en)	1981-05-05	Glaucine lactate salts
EP0037187B1 (fr)	1986-12-10	Sels et solutions aqueuses de l'acide méthylamino-6 oxo-4 propyl-10 4H-pyranno(3,2-g)quinoléinedicarboxylique-2,8 et compositions pharmaceutiques contenant de tels sels et solutions
US4183939A (en)	1980-01-15	Glaucine analgesic method
CA1109473A (fr)	1981-09-22	Lactate de glaucine
EP1181290A1 (fr)	2002-02-27	Polymorphes d'un azabicyclo (2,2,2) octan-3-amine citrate crystallin et leurs compositions pharmaceutiques
US3005818A (en)	1961-10-24	1-phenyl-2, 3-dimethyl-4-morpholino methyl pyrazolone-(5) compounds
KR20020005055A (ko)	2002-01-16	엔케이-1 수용체 길항물질로서 사용하기 위한 결정성(2-벤즈하이드릴-1-아자비사이클로[2.2.2]옥트-3-일)-(5-이소프로필-2-메톡시벤질)-아민 시트레이트의 다형태
KR840000056B1 (ko)	1984-01-31	글라우신 락테이트 염의 제조방법
CA1117528A (fr)	1982-02-02	Phosphate de glaucine
US3274055A (en)	1966-09-20	Acid addition salts of morpholine ethanol
KR840000057B1 (ko)	1984-01-31	글라우신 포스페이트 염류의 제조방법
NL8001203A (nl)	1981-10-01	D-glaucinefosfaatzout.
US2753340A (en)	1956-07-03	Maleate salts of protoveratrine a and protoveratrine b
GB1587378A (en)	1981-04-01	Antitussic or anti-thrombotic pharmaceutical compositions and their preparation
BE881709A (fr)	1980-08-13	Phosphate de d-glaucine, sa preparation et son utilisation
DE3004084A1 (de)	1981-08-13	D-glaucin-phosphat und dieses enthaltende arzneimittel
JP2001527064A (ja)	2001-12-25	１−メチル−５−ｐ−トルオイルピロール−２−アセトアミド酢酸グアイアシルエステル（ＭＥＤ１５）の新規多形結晶