ES2329739T3 - Analogos de cocaina. - Google Patents
Analogos de cocaina. Download PDFInfo
- Publication number
- ES2329739T3 ES2329739T3 ES98915409T ES98915409T ES2329739T3 ES 2329739 T3 ES2329739 T3 ES 2329739T3 ES 98915409 T ES98915409 T ES 98915409T ES 98915409 T ES98915409 T ES 98915409T ES 2329739 T3 ES2329739 T3 ES 2329739T3
- Authority
- ES
- Spain
- Prior art keywords
- compound
- alkyl
- cocaine
- quad
- chlorophenyl
- 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.)
- Expired - Lifetime
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- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical class 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 133
- 150000001875 compounds Chemical class 0.000 claims abstract description 134
- -1 cyano, hydroxy Chemical group 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 14
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 2
- 229960003920 cocaine Drugs 0.000 claims description 66
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 43
- 239000003814 drug Substances 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 230000000694 effects Effects 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 20
- 229960003638 dopamine Drugs 0.000 claims description 19
- 229940079593 drug Drugs 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000001589 carboacyl group Chemical group 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 14
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229940076279 serotonin Drugs 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
- 238000002591 computed tomography Methods 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 238000003325 tomography Methods 0.000 claims description 2
- 238000011276 addition treatment Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 abstract description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 abstract 1
- MPVDXIMFBOLMNW-UHFFFAOYSA-N chembl1615565 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC1=CC=CC=C1 MPVDXIMFBOLMNW-UHFFFAOYSA-N 0.000 abstract 1
- 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 38
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- 239000000203 mixture Substances 0.000 description 29
- 238000005481 NMR spectroscopy Methods 0.000 description 27
- 230000027455 binding Effects 0.000 description 26
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 16
- 230000002829 reductive effect Effects 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 241000700159 Rattus Species 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
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- 102000006441 Dopamine Plasma Membrane Transport Proteins Human genes 0.000 description 11
- 108010044266 Dopamine Plasma Membrane Transport Proteins Proteins 0.000 description 11
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- 239000000460 chlorine Substances 0.000 description 11
- 238000001802 infusion Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 150000003053 piperidines Chemical class 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 229940126214 compound 3 Drugs 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 6
- 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 6
- 206010013654 Drug abuse Diseases 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- HJJPJSXJAXAIPN-UHFFFAOYSA-N arecoline Chemical compound COC(=O)C1=CCCN(C)C1 HJJPJSXJAXAIPN-UHFFFAOYSA-N 0.000 description 6
- 230000008033 biological extinction Effects 0.000 description 6
- 230000028436 dopamine uptake Effects 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 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
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 229940025084 amphetamine Drugs 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
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- SFLSHLFXELFNJZ-CMIMLBRMSA-N 4-[(1r)-2-amino-1-hydroxy-1-tritioethyl]benzene-1,2-diol Chemical compound NC[C@@](O)([3H])C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-CMIMLBRMSA-N 0.000 description 4
- 0 C[C@@](CN(*)CC1)C1(C)c1ccc(*)cc1 Chemical compound C[C@@](CN(*)CC1)C1(C)c1ccc(*)cc1 0.000 description 4
- 208000022497 Cocaine-Related disease Diseases 0.000 description 4
- 102000015554 Dopamine receptor Human genes 0.000 description 4
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
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- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 4
- 102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 description 4
- 108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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- 125000003118 aryl group Chemical group 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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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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
- Oscillators With Electromechanical Resonators (AREA)
Applications Claiming Priority (2)
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| US4277597P | 1997-04-07 | 1997-04-07 | |
| US42775P | 1997-04-07 |
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| ES2329739T3 true ES2329739T3 (es) | 2009-11-30 |
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| ES98915409T Expired - Lifetime ES2329739T3 (es) | 1997-04-07 | 1998-04-07 | Analogos de cocaina. |
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| CA (1) | CA2284732C (https=) |
| DE (1) | DE69840909D1 (https=) |
| DK (1) | DK0975595T3 (https=) |
| ES (1) | ES2329739T3 (https=) |
| WO (1) | WO1998045263A1 (https=) |
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| BR9809687A (pt) | 1997-05-29 | 2000-07-11 | Smithkline Beecham Corp | Processo novo |
| AU769260B2 (en) | 1998-10-07 | 2004-01-22 | Georgetown University | Monomeric and dimeric heterocycles, and therapeutic uses thereof |
| GB9924882D0 (en) * | 1999-10-20 | 1999-12-22 | Smithkline Beecham Plc | Novel process |
| WO2001029002A1 (en) * | 1999-10-20 | 2001-04-26 | Smithkline Beecham Plc | Process for the preparation of 4-(fluorophenyl)piperidine esters |
| WO2001044193A1 (en) * | 1999-12-16 | 2001-06-21 | Biostream Therapeutics | 1,3,4-substituted piperidine 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 |
| WO2005119025A2 (en) | 2004-06-01 | 2005-12-15 | Spectrum Dynamics Llc | Radioactive-emission-measurement optimization to specific body structures |
| AU2003277827A1 (en) * | 2002-11-01 | 2004-05-25 | Neurosearch A/S | Novel piperidine derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
| EP4101846B1 (en) | 2003-04-11 | 2023-08-02 | PTC Therapeutics, Inc. | 1,2,4-oxadiazole benzoic acid compounds and their use for nonsense suppression and the treatment of disease |
| US9470801B2 (en) | 2004-01-13 | 2016-10-18 | Spectrum Dynamics Llc | Gating with anatomically varying durations |
| US7968851B2 (en) | 2004-01-13 | 2011-06-28 | Spectrum Dynamics Llc | Dynamic spect camera |
| US8571881B2 (en) | 2004-11-09 | 2013-10-29 | Spectrum Dynamics, Llc | Radiopharmaceutical dispensing, administration, and imaging |
| US8586932B2 (en) | 2004-11-09 | 2013-11-19 | Spectrum Dynamics Llc | System and method for radioactive emission measurement |
| US9040016B2 (en) | 2004-01-13 | 2015-05-26 | Biosensors International Group, Ltd. | Diagnostic kit and methods for radioimaging myocardial perfusion |
| WO2005067383A2 (en) | 2004-01-13 | 2005-07-28 | Spectrum Dynamics Llc | Multi-dimensional image reconstruction |
| EP1827505A4 (en) | 2004-11-09 | 2017-07-12 | Biosensors International Group, Ltd. | Radioimaging |
| US9943274B2 (en) | 2004-11-09 | 2018-04-17 | Spectrum Dynamics Medical Limited | Radioimaging using low dose isotope |
| US8615405B2 (en) | 2004-11-09 | 2013-12-24 | Biosensors International Group, Ltd. | Imaging system customization using data from radiopharmaceutical-associated data carrier |
| US9316743B2 (en) | 2004-11-09 | 2016-04-19 | Biosensors International Group, Ltd. | System and method for radioactive emission measurement |
| US8423125B2 (en) * | 2004-11-09 | 2013-04-16 | Spectrum Dynamics Llc | Radioimaging |
| 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 |
| EP2387995A1 (en) | 2006-03-30 | 2011-11-23 | 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 |
| BRPI0716532A2 (pt) * | 2006-09-11 | 2013-09-24 | Glaxo Group Ltd | compostos azabicÍclios como inidores de reabsorÇço de monoaminas |
| 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 |
| TWI695717B (zh) | 2014-03-06 | 2020-06-11 | 美商 Ptc 治療公司 | １,２,４-二唑苯甲酸之鹽及醫藥組合物 |
| CN108348527A (zh) | 2015-10-30 | 2018-07-31 | Ptc医疗公司 | 用于治疗癫痫的方法 |
| ES2963613T3 (es) | 2018-10-22 | 2024-04-01 | C4X Discovery Ltd | Compuestos terapéuticos |
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 |
| EP0223334B1 (en) * | 1985-08-10 | 1991-07-10 | Beecham Group Plc | Process for the preparation of aryl-piperidine carbinols |
| GB8520154D0 (en) * | 1985-08-10 | 1985-09-18 | Beecham Group Plc | Chemical process |
| US5208232A (en) * | 1986-11-03 | 1993-05-04 | Novo Nordisk A/S | Piperidine compounds and their preparation and use |
| IE66332B1 (en) * | 1986-11-03 | 1995-12-27 | Novo Nordisk As | Piperidine compounds and their preparation and use |
| DK231088D0 (da) * | 1988-04-28 | 1988-04-28 | Ferrosan As | Piperidinforbindelser, deres fremstilling og anvendelse |
| DK715988D0 (da) | 1988-12-22 | 1988-12-22 | Ferrosan As | Etherifikation og dealkylering af piperidin-derivater samt intermediater |
| JPH07500333A (ja) * | 1991-10-24 | 1995-01-12 | ジ・アップジョン・カンパニー | ベンゾ−イソキノリン誘導体 |
| 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 ES ES98915409T patent/ES2329739T3/es not_active Expired - Lifetime
- 1998-04-07 US US09/056,727 patent/US6180648B1/en not_active Expired - Lifetime
- 1998-04-07 WO PCT/US1998/007081 patent/WO1998045263A1/en not_active Ceased
- 1998-04-07 CA CA002284732A patent/CA2284732C/en not_active Expired - Fee Related
- 1998-04-07 AT AT98915409T patent/ATE433959T1/de active
- 1998-04-07 DK DK98915409T patent/DK0975595T3/da active
- 1998-04-07 AU AU69601/98A patent/AU744259B2/en not_active Ceased
- 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 EP EP98915409A patent/EP0975595B9/en not_active Expired - Lifetime
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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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| JP4578580B2 (ja) | 2010-11-10 |
| EP0975595B9 (en) | 2009-09-16 |
| AU6960198A (en) | 1998-10-30 |
| EP0975595B1 (en) | 2009-06-17 |
| EP0975595A1 (en) | 2000-02-02 |
| WO1998045263A1 (en) | 1998-10-15 |
| US6180648B1 (en) | 2001-01-30 |
| AU744259B2 (en) | 2002-02-21 |
| US20020055521A1 (en) | 2002-05-09 |
| US20030144322A1 (en) | 2003-07-31 |
| US6472422B2 (en) | 2002-10-29 |
| US6806281B2 (en) | 2004-10-19 |
| JP2001524954A (ja) | 2001-12-04 |
| DE69840909D1 (de) | 2009-07-30 |
| CA2284732C (en) | 2008-06-17 |
| CA2284732A1 (en) | 1998-10-15 |
| ATE433959T1 (de) | 2009-07-15 |
| DK0975595T3 (da) | 2009-10-19 |
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