CZ300532B6 - Adicní soli morfinových alkaloidu s kyselinami a jejich použití - Google Patents
Adicní soli morfinových alkaloidu s kyselinami a jejich použití Download PDFInfo
- Publication number
- CZ300532B6 CZ300532B6 CZ20001048A CZ20001048A CZ300532B6 CZ 300532 B6 CZ300532 B6 CZ 300532B6 CZ 20001048 A CZ20001048 A CZ 20001048A CZ 20001048 A CZ20001048 A CZ 20001048A CZ 300532 B6 CZ300532 B6 CZ 300532B6
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- Prior art keywords
- acid
- substituted
- acids
- group
- alkyl
- Prior art date
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- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical class 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 title claims abstract description 75
- 239000002253 acid Substances 0.000 title claims abstract description 42
- 150000003839 salts Chemical class 0.000 title claims abstract description 39
- 229930013053 morphinan alkaloid Natural products 0.000 title claims abstract description 29
- -1 hydroxy- Chemical class 0.000 claims abstract description 59
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 23
- 150000001559 benzoic acids Chemical class 0.000 claims abstract description 23
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 150000007524 organic acids Chemical class 0.000 claims abstract description 16
- 125000003277 amino group Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 150000007513 acids Chemical class 0.000 claims abstract description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 6
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- 229960005181 morphine Drugs 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- HDIJZFORGDBEKL-UHFFFAOYSA-N 2,3,4-trimethylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(C)=C1C HDIJZFORGDBEKL-UHFFFAOYSA-N 0.000 claims description 6
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical group O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229960004050 aminobenzoic acid Drugs 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 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 claims description 4
- FYAQQULBLMNGAH-UHFFFAOYSA-N hexane-1-sulfonic acid Chemical compound CCCCCCS(O)(=O)=O FYAQQULBLMNGAH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- QENJZWZWAWWESF-UHFFFAOYSA-N tri-methylbenzoic acid Natural products CC1=CC(C)=C(C(O)=O)C=C1C QENJZWZWAWWESF-UHFFFAOYSA-N 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- 229960003512 nicotinic acid Drugs 0.000 claims description 3
- 235000001968 nicotinic acid Nutrition 0.000 claims description 3
- 239000011664 nicotinic acid Substances 0.000 claims description 3
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- GRJDSDYCDCWOJW-UHFFFAOYSA-N 4-oxodec-2-enoic acid Chemical compound CCCCCCC(=O)C=CC(O)=O GRJDSDYCDCWOJW-UHFFFAOYSA-N 0.000 claims description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 2
- OGDVEMNWJVYAJL-LEPYJNQMSA-N Ethyl morphine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OCC OGDVEMNWJVYAJL-LEPYJNQMSA-N 0.000 claims description 2
- OGDVEMNWJVYAJL-UHFFFAOYSA-N Ethylmorphine Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OCC OGDVEMNWJVYAJL-UHFFFAOYSA-N 0.000 claims description 2
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims description 2
- JAQUASYNZVUNQP-USXIJHARSA-N Levorphanol Chemical compound C1C2=CC=C(O)C=C2[C@]23CCN(C)[C@H]1[C@@H]2CCCC3 JAQUASYNZVUNQP-USXIJHARSA-N 0.000 claims description 2
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 claims description 2
- 229960004126 codeine Drugs 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 229960002069 diamorphine Drugs 0.000 claims description 2
- 206010013663 drug dependence Diseases 0.000 claims description 2
- 229960004578 ethylmorphine Drugs 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims description 2
- WVLOADHCBXTIJK-YNHQPCIGSA-N hydromorphone Chemical compound O([C@H]1C(CC[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O WVLOADHCBXTIJK-YNHQPCIGSA-N 0.000 claims description 2
- 229960001410 hydromorphone Drugs 0.000 claims description 2
- 229960003406 levorphanol Drugs 0.000 claims description 2
- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims description 2
- 239000006210 lotion Substances 0.000 claims description 2
- 239000002674 ointment Substances 0.000 claims description 2
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical group OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- 208000011117 substance-related disease Diseases 0.000 claims description 2
- ODHCTXKNWHHXJC-UHFFFAOYSA-N 5-oxoproline Chemical compound OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 2
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 2
- MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 claims 1
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
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- 150000003330 sebacic acids Chemical class 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 6
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- 238000002360 preparation method Methods 0.000 description 23
- OSYQOBUUFRGFNG-UHFFFAOYSA-N Sebacic acid monomethyl ester Chemical compound COC(=O)CCCCCCCCC(O)=O OSYQOBUUFRGFNG-UHFFFAOYSA-N 0.000 description 17
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- 239000002313 adhesive film Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- AQIHMSVIAGNIDM-UHFFFAOYSA-N benzoyl bromide Chemical class BrC(=O)C1=CC=CC=C1 AQIHMSVIAGNIDM-UHFFFAOYSA-N 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical class OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229940050526 hydroxyethylstarch Drugs 0.000 description 1
- 229960002591 hydroxyproline Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid 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
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003232 mucoadhesive effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000004728 pyruvic acid derivatives Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 231100000245 skin permeability Toxicity 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-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
- 229940100640 transdermal system Drugs 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical class CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
- C07D489/04—Salts; Organic complexes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
- A61P23/02—Local anaesthetics
-
- 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
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Anesthesiology (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742296 | 1997-09-25 | ||
| DE19834005A DE19834005A1 (de) | 1997-09-25 | 1998-07-29 | Säureadditionssalze von Morphin-Alkaloiden und deren Verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ20001048A3 CZ20001048A3 (cs) | 2000-08-16 |
| CZ300532B6 true CZ300532B6 (cs) | 2009-06-10 |
Family
ID=26040297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20001048A CZ300532B6 (cs) | 1997-09-25 | 1998-09-05 | Adicní soli morfinových alkaloidu s kyselinami a jejich použití |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP1017696B1 (enExample) |
| JP (1) | JP2001517669A (enExample) |
| AT (1) | ATE214702T1 (enExample) |
| AU (1) | AU741434B2 (enExample) |
| CA (1) | CA2304722C (enExample) |
| CZ (1) | CZ300532B6 (enExample) |
| DK (1) | DK1017696T3 (enExample) |
| ES (1) | ES2174490T3 (enExample) |
| HU (1) | HUP0003686A3 (enExample) |
| ID (1) | ID26296A (enExample) |
| IL (1) | IL134787A (enExample) |
| MX (1) | MXPA00002658A (enExample) |
| NO (1) | NO20001465L (enExample) |
| NZ (1) | NZ503459A (enExample) |
| PL (1) | PL193321B1 (enExample) |
| PT (1) | PT1017696E (enExample) |
| SK (1) | SK4322000A3 (enExample) |
| TR (1) | TR200000653T2 (enExample) |
| TW (1) | TW576836B (enExample) |
| WO (1) | WO1999015528A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9924797D0 (en) | 1999-10-20 | 1999-12-22 | West Pharm Serv Drug Res Ltd | Compound |
| GB0218811D0 (en) * | 2002-08-14 | 2002-09-18 | Cenes Ltd | Salts of morphine-6-glucuronide |
| DE102006054732B4 (de) | 2006-11-21 | 2010-12-30 | Lts Lohmann Therapie-Systeme Ag | Transdermales therapeutisches System mit Ionenpaar-Mikroreservoiren |
| EP2311498A4 (en) * | 2008-08-05 | 2013-07-24 | Medrx Co Ltd | EXTERNAL PREPARATION COMPRISING A FATTY ACID SALT OR A BENZOIC ACID SALT OF A PHARMACOLOGICALLY ACTIVE BASIC COMPONENT, AND PROCESS FOR PRODUCTION THEREOF |
| CA2842370C (en) * | 2011-08-02 | 2020-03-24 | Mallinckrodt Llc | Stepwise process for the production of alkaloid salts |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE524639C (de) * | 1929-05-25 | 1931-05-09 | Chem Fab Vorm Sandoz | Verfahren zur Darstellung von leichtloeslichen Salzen des Benzylmorphons |
| DE1172267B (de) * | 1961-09-19 | 1964-06-18 | Dausse S A Lab | Verfahren zur Herstellung des bis-guajakol-sulfonsauren Salzes des Morphin-ª‰-morpholyl-aethylaethers |
| EP0472501A2 (de) * | 1990-08-23 | 1992-02-26 | Ciba-Geigy Ag | Codeinsalz einer substituierten Carbonsäure, Verfahren zu seiner Herstellung, seine Verwendung und pharmazeutische Präparate |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE728804C (de) * | 1935-04-02 | 1942-12-03 | Jean Lucien Regnier | Verfahren zur Herstellung von Salzen des Morphins mit Aralkylcarbonsaeuren |
| FR6598M (enExample) * | 1967-07-28 | 1969-01-06 | ||
| US4626539A (en) * | 1984-08-10 | 1986-12-02 | E. I. Dupont De Nemours And Company | Trandermal delivery of opioids |
| US4908389A (en) * | 1986-08-27 | 1990-03-13 | Warner-Lambert Company | Penetration enhancement system |
| US4879297A (en) * | 1987-06-01 | 1989-11-07 | Warner-Lambert Company | Fatty acids and their small chain esters as penetration enhancers in aqueous systems |
| US5374645A (en) * | 1990-01-22 | 1994-12-20 | Ciba-Geigy Corporation | Transdermal administation of ionic pharmaceutically active agents via aqueous isopropanol |
| FR2708611B1 (fr) * | 1993-07-29 | 1995-10-27 | Meram Lab | Sel de codéine de l'acide 2-(3-benzoylphényl)propionique, procédé d'obtention et compositions pharmaceutiques le contenant. |
| DE19607395C2 (de) * | 1996-02-28 | 2002-11-21 | Lohmann Therapie Syst Lts | Salze aus einem kationischen narkotischen Analgetikum mit einem anionischen nichtnarkotischen Analgetikum, Verfahren zu deren Herstellung und die diese Salze enthaltenden pharmazeutischen Präparate |
-
1998
- 1998-09-05 AT AT98945312T patent/ATE214702T1/de active
- 1998-09-05 CA CA002304722A patent/CA2304722C/en not_active Expired - Fee Related
- 1998-09-05 CZ CZ20001048A patent/CZ300532B6/cs not_active IP Right Cessation
- 1998-09-05 JP JP2000512833A patent/JP2001517669A/ja active Pending
- 1998-09-05 HU HU0003686A patent/HUP0003686A3/hu unknown
- 1998-09-05 ES ES98945312T patent/ES2174490T3/es not_active Expired - Lifetime
- 1998-09-05 EP EP98945312A patent/EP1017696B1/de not_active Expired - Lifetime
- 1998-09-05 DK DK98945312T patent/DK1017696T3/da active
- 1998-09-05 NZ NZ503459A patent/NZ503459A/en not_active IP Right Cessation
- 1998-09-05 PL PL339516A patent/PL193321B1/pl not_active IP Right Cessation
- 1998-09-05 MX MXPA00002658A patent/MXPA00002658A/es active IP Right Grant
- 1998-09-05 SK SK432-2000A patent/SK4322000A3/sk unknown
- 1998-09-05 PT PT98945312T patent/PT1017696E/pt unknown
- 1998-09-05 WO PCT/EP1998/005652 patent/WO1999015528A1/de not_active Ceased
- 1998-09-05 IL IL134787A patent/IL134787A/en not_active IP Right Cessation
- 1998-09-05 TR TR2000/00653T patent/TR200000653T2/xx unknown
- 1998-09-05 ID IDW20000549A patent/ID26296A/id unknown
- 1998-09-05 AU AU92666/98A patent/AU741434B2/en not_active Ceased
- 1998-09-23 TW TW087115805A patent/TW576836B/zh not_active IP Right Cessation
-
2000
- 2000-03-21 NO NO20001465A patent/NO20001465L/no unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE524639C (de) * | 1929-05-25 | 1931-05-09 | Chem Fab Vorm Sandoz | Verfahren zur Darstellung von leichtloeslichen Salzen des Benzylmorphons |
| DE1172267B (de) * | 1961-09-19 | 1964-06-18 | Dausse S A Lab | Verfahren zur Herstellung des bis-guajakol-sulfonsauren Salzes des Morphin-ª‰-morpholyl-aethylaethers |
| EP0472501A2 (de) * | 1990-08-23 | 1992-02-26 | Ciba-Geigy Ag | Codeinsalz einer substituierten Carbonsäure, Verfahren zu seiner Herstellung, seine Verwendung und pharmazeutische Präparate |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE214702T1 (de) | 2002-04-15 |
| AU9266698A (en) | 1999-04-12 |
| AU741434B2 (en) | 2001-11-29 |
| TW576836B (en) | 2004-02-21 |
| NZ503459A (en) | 2001-12-21 |
| ES2174490T3 (es) | 2002-11-01 |
| IL134787A0 (en) | 2001-04-30 |
| PL339516A1 (en) | 2000-12-18 |
| EP1017696A1 (de) | 2000-07-12 |
| SK4322000A3 (en) | 2000-10-09 |
| JP2001517669A (ja) | 2001-10-09 |
| DK1017696T3 (da) | 2002-07-08 |
| EP1017696B1 (de) | 2002-03-20 |
| ID26296A (id) | 2000-12-14 |
| CZ20001048A3 (cs) | 2000-08-16 |
| PT1017696E (pt) | 2002-09-30 |
| MXPA00002658A (es) | 2004-03-10 |
| TR200000653T2 (tr) | 2000-07-21 |
| PL193321B1 (pl) | 2007-01-31 |
| HUP0003686A2 (hu) | 2001-09-28 |
| NO20001465D0 (no) | 2000-03-21 |
| CA2304722A1 (en) | 1999-04-01 |
| NO20001465L (no) | 2000-03-21 |
| WO1999015528A1 (de) | 1999-04-01 |
| CA2304722C (en) | 2005-11-22 |
| HUP0003686A3 (en) | 2003-04-28 |
| IL134787A (en) | 2007-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20120905 |