CH641164A5 - Lactates de 1- et de d,1-glaucine. - Google Patents

Lactates de 1- et de d,1-glaucine. Download PDF

Info

Publication number: CH641164A5
Authority: CH; Switzerland
Prior art keywords: glaucine; lactate; cough; lactates; doses
Prior art date: 1978-08-21

Application number

CH759579A

Other languages

English (en)

French (fr)

Inventor

Samuel S M Wang

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.)

1978-08-21

Filing date

1979-08-20

Publication date

1984-02-15

1979-08-20 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1984-02-15 Publication of CH641164A5 publication Critical patent/CH641164A5/fr

Links

150000003893 lactate salts Chemical class 0.000 title claims description 7
229940113086 glaucine Drugs 0.000 claims description 59
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 48
RUZIUYOSRDWYQF-HNNXBMFYSA-N (S)-glaucine Chemical class CN1CCC2=CC(OC)=C(OC)C3=C2[C@@H]1CC1=C3C=C(OC)C(OC)=C1 RUZIUYOSRDWYQF-HNNXBMFYSA-N 0.000 claims description 27
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 description 27
239000000203 mixture Substances 0.000 claims description 25
229930004041 glaucine Natural products 0.000 claims description 23
150000001875 compounds Chemical class 0.000 claims description 10
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 claims description 8
239000003434 antitussive agent Substances 0.000 claims description 3
206010011224 Cough Diseases 0.000 description 31
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
239000006188 syrup Substances 0.000 description 13
235000020357 syrup Nutrition 0.000 description 13
239000000243 solution Substances 0.000 description 12
241000699670 Mus sp. Species 0.000 description 10
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 10
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
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 8
229960004415 codeine phosphate Drugs 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000007928 intraperitoneal injection Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
239000002775 capsule Substances 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
-1 hydrocodone Chemical class 0.000 description 7
238000000034 method Methods 0.000 description 7
239000003826 tablet Substances 0.000 description 7
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
238000009472 formulation Methods 0.000 description 6
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
241000700198 Cavia Species 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
230000000202 analgesic effect Effects 0.000 description 5
229960004126 codeine Drugs 0.000 description 5
239000004310 lactic acid Substances 0.000 description 5
235000014655 lactic acid Nutrition 0.000 description 5
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 class Br.CN1CCC2=CC(OC)=C(OC)C3=C2[C@@H]1CC1=C3C=C(OC)C(OC)=C1 DFFLCVRJWUOGPN-RSAXXLAASA-N 0.000 description 4
206010012335 Dependence Diseases 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
239000002585 base Substances 0.000 description 4
239000010432 diamond Substances 0.000 description 4
239000000796 flavoring agent Substances 0.000 description 4
235000019634 flavors Nutrition 0.000 description 4
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
229940124641 pain reliever Drugs 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
235000019640 taste Nutrition 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 3
229960004127 naloxone Drugs 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
229930013930 alkaloid Natural products 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
229940124584 antitussives Drugs 0.000 description 2
235000019658 bitter taste Nutrition 0.000 description 2
239000003937 drug carrier Substances 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
239000012458 free base Substances 0.000 description 2
238000005469 granulation Methods 0.000 description 2
230000003179 granulation Effects 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229960005181 morphine Drugs 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000003960 organic solvent Substances 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
229940124531 pharmaceutical excipient Drugs 0.000 description 2
SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
230000000638 stimulation Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
208000024891 symptom Diseases 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
MBDOYVRWFFCFHM-SNAWJCMRSA-N (2E)-hexenal Chemical compound CCC\C=C\C=O MBDOYVRWFFCFHM-SNAWJCMRSA-N 0.000 description 1
KRMYOICRUJJKEZ-RSAXXLAASA-N (6as)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline;hydrochloride Chemical compound [Cl-].C[NH+]1CCC2=CC(OC)=C(OC)C3=C2[C@@H]1CC1=C3C=C(OC)C(OC)=C1 KRMYOICRUJJKEZ-RSAXXLAASA-N 0.000 description 1
229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 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
235000000629 Glaucium flavum Nutrition 0.000 description 1
240000005086 Glaucium flavum Species 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
239000004368 Modified starch Substances 0.000 description 1
206010070834 Sensitisation Diseases 0.000 description 1
229920002472 Starch Polymers 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
241000906446 Theraps Species 0.000 description 1
YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000002908 adrenolytic effect Effects 0.000 description 1
150000003797 alkaloid derivatives Chemical class 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
229960002327 chloral hydrate Drugs 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
229940075614 colloidal silicon dioxide Drugs 0.000 description 1
230000036461 convulsion Effects 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
229910003460 diamond Inorganic materials 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
239000007911 effervescent powder Substances 0.000 description 1
238000000921 elemental analysis Methods 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
239000005308 flint glass 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
235000011187 glycerol Nutrition 0.000 description 1
LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 description 1
229960000240 hydrocodone Drugs 0.000 description 1
239000008172 hydrogenated vegetable oil Substances 0.000 description 1
239000007972 injectable composition Substances 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
MKXZASYAUGDDCJ-CGTJXYLNSA-N levomethorphan Chemical compound C([C@H]12)CCC[C@@]11CCN(C)[C@@H]2CC2=CC=C(OC)C=C21 MKXZASYAUGDDCJ-CGTJXYLNSA-N 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
229960005015 local anesthetics Drugs 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
235000019656 metallic taste Nutrition 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
229960004715 morphine sulfate Drugs 0.000 description 1
GRVOTVYEFDAHCL-RTSZDRIGSA-N morphine sulfate pentahydrate Chemical compound O.O.O.O.O.OS(O)(=O)=O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O GRVOTVYEFDAHCL-RTSZDRIGSA-N 0.000 description 1
230000000510 mucolytic effect Effects 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
229940127240 opiate Drugs 0.000 description 1
239000000668 oral spray Substances 0.000 description 1
229940041678 oral spray Drugs 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229940066366 other cough suppressants in atc Drugs 0.000 description 1
229960001789 papaverine Drugs 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
229940081310 piperonal Drugs 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
239000008213 purified water Substances 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
230000008313 sensitization Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 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

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Pain & Pain Management (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Other In-Based Heterocyclic Compounds (AREA)

CH759579A 1978-08-21 1979-08-20 Lactates de 1- et de d,1-glaucine. CH641164A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US93522078A	1978-08-21	1978-08-21

Publications (1)

Publication Number	Publication Date
CH641164A5 true CH641164A5 (fr)	1984-02-15

Family

ID=25466733

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH759579A CH641164A5 (fr)	1978-08-21	1979-08-20	Lactates de 1- et de d,1-glaucine.

Country Status (22)

Country	Link
JP (1)	JPS5540672A (it)
AT (1)	AT372374B (it)
AU (1)	AU529554B2 (it)
BE (1)	BE878355A (it)
CA (1)	CA1109473A (it)
CH (1)	CH641164A5 (it)
DE (1)	DE2932833A1 (it)
DK (1)	DK347279A (it)
ES (1)	ES483500A1 (it)
FI (1)	FI68812C (it)
FR (1)	FR2434152A1 (it)
GB (1)	GB2028323B (it)
GR (1)	GR69851B (it)
IE (1)	IE49057B1 (it)
IL (1)	IL57934A (it)
IT (1)	IT1123511B (it)
NL (1)	NL7906216A (it)
NO (1)	NO150001C (it)
NZ (1)	NZ191171A (it)
PT (1)	PT70097A (it)
SE (1)	SE7906940L (it)
ZA (1)	ZA794134B (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2130531A1 (en) *	2008-06-04	2009-12-09	Rolf Kullgren AB	Vaginal suppository comprising lactic acid

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2717001C2 (de) *	1977-04-18	1984-06-20	Karl O. Helm Ag, 2000 Hamburg	Arzneimittel mit antithrombotischer Wirkung
DE2717062C2 (de) *	1977-04-18	1982-11-25	Karl O. Helm Ag, 2000 Hamburg	Arzneimittel mit antitussiver Wirkung

1979
- 1979-07-27 FI FI792357A patent/FI68812C/fi not_active IP Right Cessation
- 1979-07-30 AU AU49358/79A patent/AU529554B2/en not_active Ceased
- 1979-07-30 GR GR59729A patent/GR69851B/el unknown
- 1979-07-31 IT IT24782/79A patent/IT1123511B/it active
- 1979-07-31 NZ NZ191171A patent/NZ191171A/en unknown
- 1979-07-31 IL IL57934A patent/IL57934A/xx unknown
- 1979-08-03 GB GB7927228A patent/GB2028323B/en not_active Expired
- 1979-08-08 ZA ZA00794134A patent/ZA794134B/xx unknown
- 1979-08-14 DE DE19792932833 patent/DE2932833A1/de not_active Withdrawn
- 1979-08-15 NL NL7906216A patent/NL7906216A/nl not_active Application Discontinuation
- 1979-08-17 AT AT0558479A patent/AT372374B/de active
- 1979-08-20 SE SE7906940A patent/SE7906940L/xx not_active Application Discontinuation
- 1979-08-20 NO NO792704A patent/NO150001C/no unknown
- 1979-08-20 IE IE1597/79A patent/IE49057B1/en unknown
- 1979-08-20 CH CH759579A patent/CH641164A5/fr not_active IP Right Cessation
- 1979-08-20 ES ES483500A patent/ES483500A1/es not_active Expired
- 1979-08-20 CA CA334,096A patent/CA1109473A/en not_active Expired
- 1979-08-20 JP JP10584079A patent/JPS5540672A/ja active Pending
- 1979-08-20 DK DK347279A patent/DK347279A/da unknown
- 1979-08-21 BE BE0/196821A patent/BE878355A/fr not_active IP Right Cessation
- 1979-08-21 PT PT70097A patent/PT70097A/pt unknown
- 1979-08-21 FR FR7921097A patent/FR2434152A1/fr active Granted

Also Published As

Publication number	Publication date
AU529554B2 (en)	1983-06-09
GR69851B (it)	1982-07-19
FI68812C (fi)	1985-11-11
FI792357A7 (fi)	1980-02-22
CA1109473A (en)	1981-09-22
JPS5540672A (en)	1980-03-22
IL57934A (en)	1983-12-30
ZA794134B (en)	1980-08-27
ES483500A1 (es)	1980-04-16
NO150001C (no)	1984-08-01
AU4935879A (en)	1981-02-26
NL7906216A (nl)	1980-02-25
NO150001B (no)	1984-04-24
IE791597L (en)	1980-02-21
ATA558479A (de)	1983-02-15
NZ191171A (en)	1984-05-31
SE7906940L (sv)	1980-02-22
PT70097A (en)	1979-09-01
IT1123511B (it)	1986-04-30
GB2028323B (en)	1982-12-15
FI68812B (fi)	1985-07-31
IL57934A0 (en)	1979-11-30
AT372374B (de)	1983-09-26
DK347279A (da)	1980-02-22
NO792704L (no)	1980-02-22
FR2434152A1 (fr)	1980-03-21
IE49057B1 (en)	1985-07-24
IT7924782A0 (it)	1979-07-31
GB2028323A (en)	1980-03-05
DE2932833A1 (de)	1980-03-06
FR2434152B1 (it)	1982-11-19
BE878355A (fr)	1980-02-21

Legal Events

Date	Code	Title	Description
1989-04-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0003199A2 (fr)	1979-07-25	Nouveaux dérivés du tétrahydro pyridinyl indole et leurs sels, le procédé de préparation, l'application à titre de médicaments de ces nouveaux produits et les compositions pharmaceutiques les renfermant
EP0003445B1 (fr)	1981-11-25	Dérivés d'aza-1 bicyclo(2,2,2)octane, leur procédé de préparation et produits intermédiaires, et médicaments les contenant
EP0255415B1 (fr)	1993-04-14	Utilisation de phényléthanolamines pour la préparation de médicaments agissant sur les troubles gastro-intestinaux
EP0192521A1 (fr)	1986-08-27	Dérivés de 3-phényl-tétrahydropyridine, procédé de préparation et utilisation en thérapeutique
EP0060179A1 (fr)	1982-09-15	Compositions pharmaceutiques à action anorexigène
EP0173597B1 (fr)	1989-12-27	Nouveaux éther-oxydes dérivés de cyclopropylphénols
WO1999048501A1 (fr)	1999-09-30	Voacamine en tant qu'agent anti-paludeen et agent anti-paludeen contenant de la voacamine
CH641164A5 (fr)	1984-02-15	Lactates de 1- et de d,1-glaucine.
EP0143711B1 (fr)	1987-08-12	Dérivés de N-(méthoxyphénacyl)-amine, utilisation notamment en thérapeutique et procédé de préparation
EP0080940B1 (fr)	1986-02-19	Nouveaux dérivés de 2-phényl-morpholine et compositions thérapeutiques
FR2547822A1 (fr)	1984-12-28	Acylpiperazinoquinazolines substituees utiles comme medicaments et procede pour leur preparation
CH642067A5 (fr)	1984-03-30	Sels phosphates de la 1- et de la d,1-glaucine, leur utilisation dans des compositions pharmaceutiques et procede pour leur preparation.
EP0065907B1 (fr)	1984-12-05	((Tétra- et hexahydro pyridyl-4)-2 éthyl)-3 indoles et leur utilisation comme médicaments
EP0061406B1 (fr)	1984-06-13	Dérivés d'acide benzamido-alkyl-hydroxamique, procédé de préparation et composition thérapeutique
EP0384088B1 (fr)	1993-03-31	La (+) 1-[(3,4,5-triméthoxy) benzyloxyméthyl]-1-phényl-N,N-diméthyl-n-propylamine, son procédé de préparation et son application en thérapeutique
EP1873139A1 (fr)	2008-01-02	Nouveaux dérivés naphtaleniques, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
EP0034521B1 (fr)	1983-03-23	Médicament analgésique contenant de la 1-(3'benzofuryl)-4-benzylpipérazine et son procédé de préparation
US4265912A (en)	1981-05-05	Glaucine lactate salts
EP0135402B1 (fr)	1987-10-28	Antagonistes périphériques des opiacés, procédé d'obtention et compositions pharmaceutiques les contenant
WO1998015551A1 (fr)	1998-04-16	Derives de quinuclidine en tant qu'antagonistes des recepteurs muscariniques
BE881709A (fr)	1980-08-13	Phosphate de d-glaucine, sa preparation et son utilisation
FR2583047A1 (fr)	1986-12-12	Procede de preparation de derives du 4-phenylpropyl indole, et intermediaires
EP0743063A1 (fr)	1996-11-20	Utilisation de dérivés d'alpha-aminométhyl-3-4-dichlorobenzyl thioacétamide pour la fabrication d'un médicament inhibant la recapture de la dopamine et nouveaux composés pour cette utilisation
BE897281A (fr)	1983-11-03	Le 2 (hexahydroazepine)-n-(2,6-dimethylphenyle)-acetamide son derive chlorhydrate, procede pour leur obtention et compositions pharmaceutique les contenant
FR2482968A1 (fr)	1981-11-27	Derives nicotiniques de glucosamine, leur procede de preparation et compositions pharmaceutiques correspondantes