NZ521860A - Phenylethylamines and condensed rings variants as drugs of catecholamines, preparation process and their use - Google Patents
Phenylethylamines and condensed rings variants as drugs of catecholamines, preparation process and their useInfo
- Publication number
- NZ521860A NZ521860A NZ521860A NZ52186001A NZ521860A NZ 521860 A NZ521860 A NZ 521860A NZ 521860 A NZ521860 A NZ 521860A NZ 52186001 A NZ52186001 A NZ 52186001A NZ 521860 A NZ521860 A NZ 521860A
- Authority
- NZ
- New Zealand
- Prior art keywords
- formula
- acceptable salts
- compounds
- carbon atoms
- pct
- Prior art date
Links
- 229940079593 drug Drugs 0.000 title claims description 5
- 239000003814 drug Substances 0.000 title claims description 5
- 150000003943 catecholamines Chemical class 0.000 title description 5
- 150000007925 phenylethylamine derivatives Chemical class 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- -1 dimethylamino, N-methyl-N-ethylamino Chemical group 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 238000011282 treatment Methods 0.000 claims abstract description 9
- 201000001881 impotence Diseases 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 208000023105 Huntington disease Diseases 0.000 claims abstract description 6
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 206010020772 Hypertension Diseases 0.000 claims abstract description 4
- 208000001647 Renal Insufficiency Diseases 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims abstract description 4
- 201000006370 kidney failure Diseases 0.000 claims abstract description 4
- 206010019280 Heart failures Diseases 0.000 claims abstract description 3
- 150000007513 acids Chemical class 0.000 claims abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000005418 aryl aryl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims abstract description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 32
- 101100095563 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) SEO1 gene Proteins 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 241000700159 Rattus Species 0.000 claims description 11
- 230000003291 dopaminomimetic effect Effects 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000003542 behavioural effect Effects 0.000 claims description 4
- VPXJSTOFWHBSEJ-UHFFFAOYSA-N 5h-quinolin-6-one Chemical compound C1=CN=C2C=CC(=O)CC2=C1 VPXJSTOFWHBSEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- KUCLACXWWALUKV-UHFFFAOYSA-N 3-(1-propylpiperidin-3-yl)cyclohex-2-en-1-one Chemical compound C1N(CCC)CCCC1C1=CC(=O)CCC1 KUCLACXWWALUKV-UHFFFAOYSA-N 0.000 claims description 2
- JEWACJPKCDOKGQ-UHFFFAOYSA-N 3-[2-(dibutylamino)ethyl]cyclohex-2-en-1-one Chemical compound CCCCN(CCCC)CCC1=CC(=O)CCC1 JEWACJPKCDOKGQ-UHFFFAOYSA-N 0.000 claims description 2
- VZBOPKJNIJVHFU-UHFFFAOYSA-N 3-[2-(diethylamino)ethyl]cyclohex-2-en-1-one Chemical compound CCN(CC)CCC1=CC(=O)CCC1 VZBOPKJNIJVHFU-UHFFFAOYSA-N 0.000 claims description 2
- DSZTXYDABZMVOG-UHFFFAOYSA-N 3-[2-(dipropylamino)ethyl]cyclohex-2-en-1-one Chemical compound CCCN(CCC)CCC1=CC(=O)CCC1 DSZTXYDABZMVOG-UHFFFAOYSA-N 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 206010042008 Stereotypy Diseases 0.000 claims 3
- 230000003370 grooming effect Effects 0.000 claims 2
- 238000005303 weighing Methods 0.000 claims 2
- WTLNFOABUHAWEJ-UHFFFAOYSA-N 3-[2-[2-phenylethyl(propyl)amino]ethyl]cyclohex-2-en-1-one Chemical compound C=1C=CC=CC=1CCN(CCC)CCC1=CC(=O)CCC1 WTLNFOABUHAWEJ-UHFFFAOYSA-N 0.000 claims 1
- 101000956900 Mesobuthus martensii HMG-CoA reductase inhibitor bumarsin Proteins 0.000 claims 1
- 230000004071 biological effect Effects 0.000 claims 1
- 230000001055 chewing effect Effects 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- 230000000284 resting effect Effects 0.000 claims 1
- 238000011179 visual inspection Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 16
- 201000000980 schizophrenia Diseases 0.000 abstract description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000651 prodrug Substances 0.000 description 15
- 229940002612 prodrug Drugs 0.000 description 15
- 229960003638 dopamine Drugs 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 108020003175 receptors Proteins 0.000 description 11
- 102000005962 receptors Human genes 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 101150041968 CDC13 gene Proteins 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 229960004132 diethyl ether Drugs 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 230000001242 postsynaptic effect Effects 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 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
- 102000007527 Autoreceptors Human genes 0.000 description 6
- 108010071131 Autoreceptors Proteins 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000000638 stimulation Effects 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
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- 239000000843 powder Substances 0.000 description 5
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
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- HPMWHVMJEUBHPB-UHFFFAOYSA-N 3-ethynylcyclohex-2-en-1-one Chemical compound O=C1CCCC(C#C)=C1 HPMWHVMJEUBHPB-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 4
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- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- QDNVQQPKBRGLSF-UHFFFAOYSA-N 3-chloro-n-propylpropan-1-amine Chemical compound CCCNCCCCl QDNVQQPKBRGLSF-UHFFFAOYSA-N 0.000 description 3
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
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- 239000003039 volatile agent Substances 0.000 description 3
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/20—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
-
- 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
- C07D211/30—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/08—Aza-anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
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- Organic Chemistry (AREA)
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- Engineering & Computer Science (AREA)
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- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Endocrinology (AREA)
- Gynecology & Obstetrics (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Hydrogenated Pyridines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0001438A SE0001438D0 (sv) | 2000-04-18 | 2000-04-18 | New chemical compounds and their use in therapy |
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| WO (1) | WO2001078713A1 (enExample) |
| ZA (1) | ZA200207919B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7910623B2 (en) * | 2005-07-22 | 2011-03-22 | Sloan-Kettering Institute For Cancer Research | Synthesis of scabronines and analogues thereof |
| WO2007013965A2 (en) * | 2005-07-22 | 2007-02-01 | Sloan-Kettering Institute For Cancer Research | Synthesis of scabronines and analogues thereof |
| US8168793B2 (en) | 2005-07-26 | 2012-05-01 | Portela & Ca., S.A. | Nitrocatechol derivatives as COMT inhibitors |
| EP1845097A1 (en) * | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| PL2481410T3 (pl) | 2007-01-31 | 2017-03-31 | Bial - Portela & Ca., S.A. | Pochodne nitrokatecholu jako inhibitory COMT podawane w określonym schemacie dawkowania |
| US8129530B2 (en) | 2007-08-31 | 2012-03-06 | H. Lundbeck A/S | Catecholamine derivatives and prodrugs thereof |
| CL2009000628A1 (es) | 2008-03-17 | 2010-04-09 | Bial Portela & Companhia S A | Forma cristalina de 5-[3-(2,5-dicloro-4,6-dimetil-1-oxi-piridin-3-il)-[1,2,4]oxadiazol-5-il]-3-nitrobenceno-1,2-diol, composicion farmaceutica que la comprende, proceso para obtenerla y su uso para tratar trastornos del animo, enfermedad de parkinson y trastornos parkinsonianos, alteraciones gastrointestinales, entre otros. |
| TW201036949A (en) * | 2009-02-27 | 2010-10-16 | Lundbeck & Co As H | Treatment of dyskinesia related disorders |
| US9132094B2 (en) | 2009-04-01 | 2015-09-15 | Bial—Portela & Ca, S.A. | Pharmaceutical formulations comprising nitrocatechol derivatives and methods of making thereof |
| US8492538B1 (en) * | 2009-06-04 | 2013-07-23 | Jose R. Matos | Cyclodextrin derivative salts |
| JP5641494B2 (ja) * | 2009-09-18 | 2014-12-17 | 株式会社Riverson | ポリフェノール誘導体及びそれの産生方法 |
| US20140045900A1 (en) | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| PT2791134T (pt) | 2011-12-13 | 2019-12-18 | BIAL PORTELA & Cª S A | Composto químico útil como intermediário para a preparação de um inibidor de catecol-o-metiltransferase |
| RU2017120184A (ru) | 2014-11-28 | 2018-12-28 | БИАЛ - ПОРТЕЛА ЭНД Ка, С.А. | Лекарства для замедления течения болезни паркинсона |
| US10729710B2 (en) | 2017-11-24 | 2020-08-04 | H. Lundbeck A/S | Catecholamine prodrugs for use in the treatment of Parkinson's disease |
| US11130775B2 (en) | 2019-05-20 | 2021-09-28 | H. Lundbeck A/S | Solid forms of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4A,5,10,10A-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid |
| US11104697B2 (en) | 2019-05-20 | 2021-08-31 | H. Lundbeck A/S | Process for the manufacture of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4AR,10AR)-7-hydroxy-1- propyl-1,2,3,4,4A,5,10,10A-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid |
| US11168056B2 (en) | 2019-05-20 | 2021-11-09 | H. Lundbeck A/S | Process for the manufacturing of (6aR,10aR)-7-propyl-6,6a,7,8,9,10,10a,11-octahydro-[1,3]dioxolo[4′,5′:5,6]benzo[1,2-G]quinoline and (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[G]quinoline-6,7-diol |
| US11111263B2 (en) | 2019-05-20 | 2021-09-07 | H. Lundbeck A/S | Process for the manufacture of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid |
| EP3972600A1 (en) | 2019-05-21 | 2022-03-30 | H. Lundbeck A/S | Catecholamine carbamate prodrugs for use in the treatment of parkinson s disease |
| US12319710B2 (en) | 2019-05-21 | 2025-06-03 | H. Lundbeck A/S | Catecholamine prodrugs for use in the treatment of Parkinson's diseases |
| EP3972959A1 (en) | 2019-05-21 | 2022-03-30 | H. Lundbeck A/S | New catecholamine prodrugs for use in the treatment of parkinson's disease |
| WO2020234274A1 (en) | 2019-05-21 | 2020-11-26 | H. Lundbeck A/S | New catecholamine prodrugs for use in the treatment of parkinson's disease |
| EP4247793A1 (en) | 2020-11-17 | 2023-09-27 | H. Lundbeck A/S | New catecholamine prodrugs for use in the treatment of parkinson's disease |
| WO2023208867A1 (en) | 2022-04-25 | 2023-11-02 | Integrative Research Laboratories Sweden Ab | NOVEL 1,2,3,4,4a,5,8,9,10,10a-DECAHYDROBENZO[G]QUINOLIN-6(7H)-ONE COMPOUNDS AND USES THEREOF |
| US20250282733A1 (en) | 2022-04-25 | 2025-09-11 | Integrative Research Laboratories Sweden Ab | Novel 1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydrobenzo[g]quinolin-6-ol compounds and uses thereof |
| CA3249364A1 (en) | 2022-04-25 | 2023-11-02 | Integrative Res Laboratories Sweden Ab | NEW ESTERS OF COMPOUNDS 1, 2, 3, 4, 4A, 5, 6, 7, 8, 9, 10, 10A-DODECAHYDROBENZO [G]QUINOLIN-6-OL AND THEIR USES |
| WO2025078574A1 (en) | 2023-10-12 | 2025-04-17 | Integrative Research Laboratories Sweden Ab | NOVEL ESTERS OF 1,2,3,4,4a,5,6,7,8,9,10,10a-DODECAHYDROBENZO[g]QUINOLIN-6-OL COMPOUNDS AND USES THEREOF |
| WO2025078571A1 (en) | 2023-10-12 | 2025-04-17 | Integrative Research Laboratories Sweden Ab | NOVEL CARBONATES AND CARBAMATES OF 1,2,3,4,4a,5,6,7,8,9,10,10a- DODECAHYDROBENZO[g]QUINOLIN-6-OL COMPOUNDS AND USES THEREOF |
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| FR1179954A (fr) * | 1956-02-11 | 1959-05-29 | Rhone Poulenc Sa | -1 cyclohexène-1 ones-3 nu-disubstituées, leurs dérivés et leur préparation |
| US3991207A (en) * | 1971-03-18 | 1976-11-09 | Pfizer Inc. | Combination therapy for Parkinson's disease |
| GB1593888A (en) * | 1977-12-22 | 1981-07-22 | Wyeth John & Brother Ltd | Hexahydroazepine piperidine and pyrrolidine derivatives |
| DE3062971D1 (en) | 1979-09-14 | 1983-06-09 | Sandoz Ag | Derivatives of tetraline, their preparation and medicaments containing these compounds |
| ZA805648B (en) * | 1979-09-14 | 1982-04-28 | Sandoz Ltd | Tetraline derivatives, their production and pharmaceutical compositions containing them |
| ATE56958T1 (de) * | 1981-10-16 | 1990-10-15 | Sandoz Ag | 1,2,3,4,4a,5,10,10a-octahydrobenzo(g)chinolinderivate mit pharmazeutischer wirkung. |
| AU6072090A (en) * | 1989-07-05 | 1991-02-06 | Whitby Research, Inc. | Substituted 2-aminotetralins |
| DE69231854T2 (de) * | 1991-04-17 | 2001-10-04 | Pharmacia & Upjohn Co., Kalamazoo | Substituierte (s)-3-phenylpiperidin derivate, deren herstellung und deren verwendung als dopamin autorezeptor antagonisten |
| DE4114325A1 (de) | 1991-05-02 | 1992-11-05 | Sandoz Ag | Octahydrobenzo(g)chinolin, seine herstellung und verwendung |
| GB2260980A (en) * | 1991-10-31 | 1993-05-05 | Shell Int Research | Preparation of unsaturated cyclic ketones |
| GB9326010D0 (en) * | 1993-12-21 | 1994-02-23 | Sandoz Ltd | Improvements in or relating to organic compounds |
| CA2267315C (en) * | 1997-08-07 | 2008-01-08 | Fujimoto Brothers Co., Ltd. | Ethylamine derivatives |
| WO2000006536A1 (en) * | 1998-07-28 | 2000-02-10 | Warner-Lambert Company | Hexahydro-naphthalenone oximes and hydrazones |
| SV2001000202A (es) | 1999-10-20 | 2001-10-16 | Warner Lambert Co | Uso de (-)-5-ceto-2-n,n-d1-n-propilamino-tetrahidrotetralina para el tratamiento del mal de parkinson |
-
2000
- 2000-04-18 SE SE0001438A patent/SE0001438D0/xx unknown
-
2001
- 2001-04-17 EP EP01922208A patent/EP1274411B1/en not_active Expired - Lifetime
- 2001-04-17 NZ NZ521860A patent/NZ521860A/en not_active IP Right Cessation
- 2001-04-17 ES ES01922208T patent/ES2244604T3/es not_active Expired - Lifetime
- 2001-04-17 CA CA002406044A patent/CA2406044C/en not_active Expired - Fee Related
- 2001-04-17 AT AT01922208T patent/ATE300290T1/de active
- 2001-04-17 US US10/258,014 patent/US6683087B2/en not_active Expired - Fee Related
- 2001-04-17 CZ CZ20023455A patent/CZ20023455A3/cs unknown
- 2001-04-17 JP JP2001576014A patent/JP4819280B2/ja not_active Expired - Fee Related
- 2001-04-17 PL PL365113A patent/PL204661B1/pl unknown
- 2001-04-17 AU AU2001248982A patent/AU2001248982B2/en not_active Ceased
- 2001-04-17 DE DE60112269T patent/DE60112269T2/de not_active Expired - Lifetime
- 2001-04-17 CN CNB2005101253198A patent/CN100383126C/zh not_active Expired - Fee Related
- 2001-04-17 DK DK01922208T patent/DK1274411T3/da active
- 2001-04-17 PT PT01922208T patent/PT1274411E/pt unknown
- 2001-04-17 CN CNB018082858A patent/CN1234351C/zh not_active Expired - Fee Related
- 2001-04-17 HU HU0300543A patent/HU229794B1/hu not_active IP Right Cessation
- 2001-04-17 AU AU4898201A patent/AU4898201A/xx active Pending
- 2001-04-17 WO PCT/SE2001/000840 patent/WO2001078713A1/en not_active Ceased
- 2001-04-17 SI SI200130409T patent/SI1274411T1/sl unknown
-
2002
- 2002-10-02 ZA ZA200207919A patent/ZA200207919B/xx unknown
-
2003
- 2003-12-18 US US10/737,782 patent/US6998405B2/en not_active Ceased
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2007
- 2007-04-25 US US11/790,465 patent/USRE42802E1/en not_active Expired - Fee Related
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2010
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