AU744259B2 - Analogs of cocaine - Google Patents
Analogs of cocaine Download PDFInfo
- Publication number
- AU744259B2 AU744259B2 AU69601/98A AU6960198A AU744259B2 AU 744259 B2 AU744259 B2 AU 744259B2 AU 69601/98 A AU69601/98 A AU 69601/98A AU 6960198 A AU6960198 A AU 6960198A AU 744259 B2 AU744259 B2 AU 744259B2
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- alkanoyl
- hydrogen
- phenyl
- compound
- Prior art date
- 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.)
- Ceased
Links
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 title claims description 126
- 229960003920 cocaine Drugs 0.000 title claims description 63
- 150000001875 compounds Chemical class 0.000 claims abstract description 197
- 238000000034 method Methods 0.000 claims abstract description 70
- 241000124008 Mammalia Species 0.000 claims abstract description 31
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 208000011117 substance-related disease Diseases 0.000 claims abstract description 12
- 206010013663 drug dependence Diseases 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 150
- 229910052739 hydrogen Inorganic materials 0.000 claims description 136
- 239000001257 hydrogen Substances 0.000 claims description 133
- 229910052799 carbon Inorganic materials 0.000 claims description 119
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 116
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 74
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
- -1 4-methyiphenyl Chemical group 0.000 claims description 70
- 150000003839 salts Chemical class 0.000 claims description 69
- 125000003118 aryl group Chemical group 0.000 claims description 65
- 125000001589 carboacyl group Chemical group 0.000 claims description 60
- 125000000304 alkynyl group Chemical group 0.000 claims description 47
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 46
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 45
- 125000003342 alkenyl group Chemical group 0.000 claims description 45
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 38
- 229960003638 dopamine Drugs 0.000 claims description 37
- 230000000694 effects Effects 0.000 claims description 36
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 34
- 239000003814 drug Substances 0.000 claims description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
- 201000010099 disease Diseases 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 29
- 125000004423 acyloxy group Chemical group 0.000 claims description 28
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims description 22
- 229940079593 drug Drugs 0.000 claims description 21
- 229940076279 serotonin Drugs 0.000 claims description 19
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 19
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 16
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 230000000697 serotonin reuptake Effects 0.000 claims description 13
- 230000002825 dopamine reuptake Effects 0.000 claims description 12
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 12
- 210000004556 brain Anatomy 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 238000003384 imaging method Methods 0.000 claims description 6
- 238000002600 positron emission tomography Methods 0.000 claims description 6
- 206010012335 Dependence Diseases 0.000 claims description 5
- 102000015554 Dopamine receptor Human genes 0.000 claims description 5
- 108050004812 Dopamine receptor Proteins 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 238000003325 tomography Methods 0.000 claims description 4
- 208000012902 Nervous system disease Diseases 0.000 claims description 3
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
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- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 85
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims 33
- 125000001475 halogen functional group Chemical group 0.000 claims 29
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 10
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical class CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 6
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 3
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 3
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims 1
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims 1
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- 208000002972 Hepatolenticular Degeneration Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
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- 239000002671 adjuvant Substances 0.000 claims 1
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims 1
- 125000004492 methyl ester group Chemical group 0.000 claims 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 6
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 35
- 230000027455 binding Effects 0.000 description 33
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- 150000003053 piperidines Chemical class 0.000 description 17
- 230000002829 reductive effect Effects 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 102000006441 Dopamine Plasma Membrane Transport Proteins Human genes 0.000 description 13
- 108010044266 Dopamine Plasma Membrane Transport Proteins Proteins 0.000 description 13
- 241000700159 Rattus Species 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 238000001802 infusion Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000012230 colorless oil Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000028436 dopamine uptake Effects 0.000 description 9
- 239000012458 free base Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
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- HJJPJSXJAXAIPN-UHFFFAOYSA-N arecoline Chemical compound COC(=O)C1=CCCN(C)C1 HJJPJSXJAXAIPN-UHFFFAOYSA-N 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000012047 saturated solution Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
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- 206010013654 Drug abuse Diseases 0.000 description 6
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
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- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 102000008092 Norepinephrine Plasma Membrane Transport Proteins Human genes 0.000 description 4
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- 229940025084 amphetamine Drugs 0.000 description 4
- 230000003542 behavioural effect Effects 0.000 description 4
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 4
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- 229920002554 vinyl polymer Polymers 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/24—Antidepressants
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/12—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with only hydrogen atoms attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Oscillators With Electromechanical Resonators (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4277597P | 1997-04-07 | 1997-04-07 | |
| US60/042775 | 1997-04-07 | ||
| PCT/US1998/007081 WO1998045263A1 (en) | 1997-04-07 | 1998-04-07 | Analogs of cocaine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6960198A AU6960198A (en) | 1998-10-30 |
| AU744259B2 true AU744259B2 (en) | 2002-02-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU69601/98A Ceased AU744259B2 (en) | 1997-04-07 | 1998-04-07 | Analogs of cocaine |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US6180648B1 (enExample) |
| EP (1) | EP0975595B9 (enExample) |
| JP (1) | JP4578580B2 (enExample) |
| AT (1) | ATE433959T1 (enExample) |
| AU (1) | AU744259B2 (enExample) |
| CA (1) | CA2284732C (enExample) |
| DE (1) | DE69840909D1 (enExample) |
| DK (1) | DK0975595T3 (enExample) |
| ES (1) | ES2329739T3 (enExample) |
| WO (1) | WO1998045263A1 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US6489347B1 (en) | 1997-05-29 | 2002-12-03 | Smithkline Beecham Plc | Process |
| EP1119553A1 (en) | 1998-10-07 | 2001-08-01 | Georgetown University | Monomeric and dimeric heterocycles, and therapeutic uses thereof |
| GB9924882D0 (en) * | 1999-10-20 | 1999-12-22 | Smithkline Beecham Plc | Novel process |
| AU1037701A (en) * | 1999-10-20 | 2001-04-30 | Smithkline Beecham Plc | Process for the preparation of 4-(fluorophenyl)piperidine esters |
| US20020025967A1 (en) * | 1999-12-16 | 2002-02-28 | Smith Miles P. | N-alkylpiperdine analogs and uses thereof in treating addictions |
| US8909325B2 (en) | 2000-08-21 | 2014-12-09 | Biosensors International Group, Ltd. | Radioactive emission detector equipped with a position tracking system and utilization thereof with medical systems and in medical procedures |
| US8489176B1 (en) | 2000-08-21 | 2013-07-16 | Spectrum Dynamics Llc | Radioactive emission detector equipped with a position tracking system and utilization thereof with medical systems and in medical procedures |
| US8565860B2 (en) | 2000-08-21 | 2013-10-22 | Biosensors International Group, Ltd. | Radioactive emission detector equipped with a position tracking system |
| DE60331762D1 (de) * | 2002-11-01 | 2010-04-29 | Neurosearch As | Neue piperidinderivate und deren verwendung als monoaminneurotransmitter-wiederaufnahmehemmer |
| US6992096B2 (en) * | 2003-04-11 | 2006-01-31 | Ptc Therapeutics, Inc. | 1,2,4-oxadiazole benzoic acid compounds and their use for nonsense suppression and the treatment of disease |
| US7968851B2 (en) | 2004-01-13 | 2011-06-28 | Spectrum Dynamics Llc | Dynamic spect camera |
| US8586932B2 (en) | 2004-11-09 | 2013-11-19 | Spectrum Dynamics Llc | System and method for radioactive emission measurement |
| US8571881B2 (en) | 2004-11-09 | 2013-10-29 | Spectrum Dynamics, Llc | Radiopharmaceutical dispensing, administration, and imaging |
| EP1709585B1 (en) | 2004-01-13 | 2020-01-08 | Spectrum Dynamics Medical Limited | Multi-dimensional image reconstruction |
| US9470801B2 (en) | 2004-01-13 | 2016-10-18 | Spectrum Dynamics Llc | Gating with anatomically varying durations |
| US9040016B2 (en) | 2004-01-13 | 2015-05-26 | Biosensors International Group, Ltd. | Diagnostic kit and methods for radioimaging myocardial perfusion |
| EP1778957A4 (en) | 2004-06-01 | 2015-12-23 | Biosensors Int Group Ltd | OPTIMIZING THE MEASUREMENT OF RADIOACTIVE RADIATION ON SPECIAL BODY STRUCTURES |
| US9943274B2 (en) | 2004-11-09 | 2018-04-17 | Spectrum Dynamics Medical Limited | Radioimaging using low dose isotope |
| US9316743B2 (en) | 2004-11-09 | 2016-04-19 | Biosensors International Group, Ltd. | System and method for radioactive emission measurement |
| US8000773B2 (en) * | 2004-11-09 | 2011-08-16 | Spectrum Dynamics Llc | Radioimaging |
| EP1827505A4 (en) | 2004-11-09 | 2017-07-12 | Biosensors International Group, Ltd. | Radioimaging |
| US8615405B2 (en) | 2004-11-09 | 2013-12-24 | Biosensors International Group, Ltd. | Imaging system customization using data from radiopharmaceutical-associated data carrier |
| WO2008059489A2 (en) * | 2006-11-13 | 2008-05-22 | Spectrum Dynamics Llc | Radioimaging applications of and novel formulations of teboroxime |
| EP1909853B1 (en) | 2005-07-19 | 2015-03-18 | Biosensors International Group, Ltd. | Imaging protocols |
| US8837793B2 (en) | 2005-07-19 | 2014-09-16 | Biosensors International Group, Ltd. | Reconstruction stabilizer and active vision |
| SG170819A1 (en) | 2006-03-30 | 2011-05-30 | Ptc Therapeutics Inc | Methods for the production of functional protein from dna having a nonsense mutation and the treatment of disorders associated therewith |
| US8894974B2 (en) | 2006-05-11 | 2014-11-25 | Spectrum Dynamics Llc | Radiopharmaceuticals for diagnosis and therapy |
| EA200970266A1 (ru) | 2006-09-11 | 2009-08-28 | Глэксо Груп Лимитед | Азабициклические соединения в качестве ингибиторов повторного поглощения моноаминов |
| US9275451B2 (en) | 2006-12-20 | 2016-03-01 | Biosensors International Group, Ltd. | Method, a system, and an apparatus for using and processing multidimensional data |
| US8521253B2 (en) | 2007-10-29 | 2013-08-27 | Spectrum Dynamics Llc | Prostate imaging |
| US8338788B2 (en) | 2009-07-29 | 2012-12-25 | Spectrum Dynamics Llc | Method and system of optimized volumetric imaging |
| WO2012009263A1 (en) | 2010-07-12 | 2012-01-19 | Temple University-Of The Commonwealth System Of Higher Education | Cocaine analogs and methods of preparation and uses thereof |
| US9873677B2 (en) | 2014-03-06 | 2018-01-23 | Ptc Therapeutics, Inc. | Pharmaceutical compositions and salts of a 1,2,4-oxadiazole benzoic acid |
| MX2018005361A (es) | 2015-10-30 | 2018-06-07 | Ptc Therapeutics Inc | Metodos para tratar epilepsia. |
| DK3870578T3 (da) | 2018-10-22 | 2023-11-13 | C4X Discovery Ltd | Terapeutiske forbindelser |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1422263A (en) * | 1973-01-30 | 1976-01-21 | Ferrosan As | 4-phenyl-piperidine compounds |
| DE3441927A1 (de) | 1984-11-16 | 1986-05-28 | Basf Ag, 6700 Ludwigshafen | Am stickstoff substituierte 4-(p-tert.butyl-phenyl)-3-methyl-piperidine, dessen quartaere salze sowie deren anwendung als fungizide |
| DE3441929A1 (de) | 1984-11-16 | 1986-05-28 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von substituierten piperidinen |
| GB8520154D0 (en) * | 1985-08-10 | 1985-09-18 | Beecham Group Plc | Chemical process |
| EP0223334B1 (en) * | 1985-08-10 | 1991-07-10 | Beecham Group Plc | Process for the preparation of aryl-piperidine carbinols |
| US5208232A (en) * | 1986-11-03 | 1993-05-04 | Novo Nordisk A/S | Piperidine compounds and their preparation and use |
| DK231088D0 (da) | 1988-04-28 | 1988-04-28 | Ferrosan As | Piperidinforbindelser, deres fremstilling og anvendelse |
| IE66332B1 (en) * | 1986-11-03 | 1995-12-27 | Novo Nordisk As | Piperidine compounds and their preparation and use |
| DK715988D0 (da) * | 1988-12-22 | 1988-12-22 | Ferrosan As | Etherifikation og dealkylering af piperidin-derivater samt intermediater |
| AU2559392A (en) * | 1991-10-24 | 1993-05-21 | Upjohn Company, The | Benzo-isoquinoline derivatives and analogs and their use in therapeutics |
| DE4308788A1 (de) * | 1993-03-18 | 1994-09-22 | Bayer Ag | Hetero-tricyclisch-substituierte Phenyl-cyclohexan-carbonsäurederivate |
| DE19529858A1 (de) * | 1995-08-14 | 1997-02-20 | Bayer Ag | Substituierte 4H-Pyrane |
| CA2187257A1 (en) * | 1995-10-12 | 1997-04-13 | Enrique Luis Michelotti | Aryl-substituted cycloalkanes and cycloalkenes and herbicidal use thereof |
| GB9605828D0 (en) | 1996-03-20 | 1996-05-22 | Smithkline Beecham Plc | Treatment method |
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1998
- 1998-04-07 DK DK98915409T patent/DK0975595T3/da active
- 1998-04-07 AU AU69601/98A patent/AU744259B2/en not_active Ceased
- 1998-04-07 AT AT98915409T patent/ATE433959T1/de active
- 1998-04-07 DE DE69840909T patent/DE69840909D1/de not_active Expired - Lifetime
- 1998-04-07 JP JP54311498A patent/JP4578580B2/ja not_active Expired - Fee Related
- 1998-04-07 ES ES98915409T patent/ES2329739T3/es not_active Expired - Lifetime
- 1998-04-07 CA CA002284732A patent/CA2284732C/en not_active Expired - Fee Related
- 1998-04-07 WO PCT/US1998/007081 patent/WO1998045263A1/en not_active Ceased
- 1998-04-07 US US09/056,727 patent/US6180648B1/en not_active Expired - Lifetime
- 1998-04-07 EP EP98915409A patent/EP0975595B9/en not_active Expired - Lifetime
-
2001
- 2001-01-25 US US09/769,774 patent/US6472422B2/en not_active Expired - Fee Related
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2002
- 2002-10-23 US US10/278,758 patent/US6806281B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
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| EP0975595A1 (en) | 2000-02-02 |
| US6806281B2 (en) | 2004-10-19 |
| US6180648B1 (en) | 2001-01-30 |
| CA2284732A1 (en) | 1998-10-15 |
| AU6960198A (en) | 1998-10-30 |
| DE69840909D1 (de) | 2009-07-30 |
| CA2284732C (en) | 2008-06-17 |
| WO1998045263A1 (en) | 1998-10-15 |
| JP2001524954A (ja) | 2001-12-04 |
| US6472422B2 (en) | 2002-10-29 |
| US20020055521A1 (en) | 2002-05-09 |
| ATE433959T1 (de) | 2009-07-15 |
| US20030144322A1 (en) | 2003-07-31 |
| ES2329739T3 (es) | 2009-11-30 |
| EP0975595B1 (en) | 2009-06-17 |
| JP4578580B2 (ja) | 2010-11-10 |
| EP0975595B9 (en) | 2009-09-16 |
| DK0975595T3 (da) | 2009-10-19 |
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