AR088256A1 - Derivados de carbamato / urea como antagonistas del receptor h3 - Google Patents
Derivados de carbamato / urea como antagonistas del receptor h3Info
- Publication number
- AR088256A1 AR088256A1 ARP120103727A ARP120103727A AR088256A1 AR 088256 A1 AR088256 A1 AR 088256A1 AR P120103727 A ARP120103727 A AR P120103727A AR P120103727 A ARP120103727 A AR P120103727A AR 088256 A1 AR088256 A1 AR 088256A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- amino
- cycloalkyl
- alkoxy
- once
- Prior art date
Links
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title 1
- 239000005557 antagonist Substances 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 25
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 14
- 229910052736 halogen Inorganic materials 0.000 abstract 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 8
- 229910052760 oxygen Inorganic materials 0.000 abstract 8
- 239000001301 oxygen Substances 0.000 abstract 8
- 125000004432 carbon atom Chemical group C* 0.000 abstract 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 6
- 229910052799 carbon Inorganic materials 0.000 abstract 6
- 125000005843 halogen group Chemical group 0.000 abstract 6
- 229910052717 sulfur Chemical group 0.000 abstract 6
- 239000011593 sulfur Chemical group 0.000 abstract 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 5
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 5
- 125000002947 alkylene group Chemical group 0.000 abstract 4
- 125000004122 cyclic group Chemical class 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 125000005842 heteroatom Chemical group 0.000 abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 3
- 125000000232 haloalkynyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- 125000006413 ring segment Chemical group 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 abstract 2
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 239000003814 drug Substances 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- 125000002950 monocyclic group Chemical group 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 abstract 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 1
- 125000006642 (C1-C6) cyanoalkyl group Chemical group 0.000 abstract 1
- NGBGTFQTPCVKCY-UHFFFAOYSA-N 4-(2,2-difluoroethyl)-n-(1-pyrimidin-2-ylpiperidin-4-yl)piperazine-1-carboxamide Chemical compound C1CN(CC(F)F)CCN1C(=O)NC1CCN(C=2N=CC=CN=2)CC1 NGBGTFQTPCVKCY-UHFFFAOYSA-N 0.000 abstract 1
- PRLRVBKZUSBHQS-UHFFFAOYSA-N 4-cyclopentyl-n-[1-[5-(trifluoromethyl)pyridin-2-yl]azetidin-3-yl]piperazine-1-carboxamide Chemical compound N1=CC(C(F)(F)F)=CC=C1N1CC(NC(=O)N2CCN(CC2)C2CCCC2)C1 PRLRVBKZUSBHQS-UHFFFAOYSA-N 0.000 abstract 1
- JTWWOAVUJKLMEY-UHFFFAOYSA-N 4-cyclopentyl-n-[1-[5-(trifluoromethyl)pyridin-2-yl]pyrrolidin-3-yl]piperazine-1-carboxamide Chemical compound N1=CC(C(F)(F)F)=CC=C1N1CC(NC(=O)N2CCN(CC2)C2CCCC2)CC1 JTWWOAVUJKLMEY-UHFFFAOYSA-N 0.000 abstract 1
- VHSDBNNLXMTJPC-UHFFFAOYSA-N 4-ethyl-n-(1-pyrimidin-2-ylpiperidin-4-yl)piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC1CCN(C=2N=CC=CN=2)CC1 VHSDBNNLXMTJPC-UHFFFAOYSA-N 0.000 abstract 1
- SVUPFMYARWDSBX-UHFFFAOYSA-N 4-methyl-n-(1-pyrimidin-2-ylpiperidin-4-yl)-1,4-diazepane-1-carboxamide Chemical compound C1CN(C)CCCN1C(=O)NC1CCN(C=2N=CC=CN=2)CC1 SVUPFMYARWDSBX-UHFFFAOYSA-N 0.000 abstract 1
- KJVOYEJHKBTTNU-UHFFFAOYSA-N 4-tert-butyl-n-(1-pyrimidin-2-ylpiperidin-4-yl)-1,4-diazepane-1-carboxamide Chemical compound C1CN(C(C)(C)C)CCCN1C(=O)NC1CCN(C=2N=CC=CN=2)CC1 KJVOYEJHKBTTNU-UHFFFAOYSA-N 0.000 abstract 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- KQHJKUJUVRHFIV-GOSISDBHSA-N n-[(3r)-1-[7-[(2,4-dichlorophenyl)methylamino]pyrazolo[1,5-a]pyrimidin-5-yl]pyrrolidin-3-yl]-4-methylpiperazine-1-carboxamide Chemical compound C1CN(C)CCN1C(=O)N[C@H]1CN(C2=NC3=CC=NN3C(NCC=3C(=CC(Cl)=CC=3)Cl)=C2)CC1 KQHJKUJUVRHFIV-GOSISDBHSA-N 0.000 abstract 1
- LICOLRZXACSNHY-UHFFFAOYSA-N n-[1-(4-acetylphenyl)piperidin-4-yl]-4-cyclobutylpiperazine-1-carboxamide Chemical compound C1=CC(C(=O)C)=CC=C1N1CCC(NC(=O)N2CCN(CC2)C2CCC2)CC1 LICOLRZXACSNHY-UHFFFAOYSA-N 0.000 abstract 1
- PHMPFCFETGRFRJ-UHFFFAOYSA-N n-[1-(4-acetylphenyl)piperidin-4-yl]-4-cyclopentylpiperazine-1-carboxamide Chemical compound C1=CC(C(=O)C)=CC=C1N1CCC(NC(=O)N2CCN(CC2)C2CCCC2)CC1 PHMPFCFETGRFRJ-UHFFFAOYSA-N 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- 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
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Un intermediario para su preparación, su uso como un medicamento, y a medicamentos que lo comprenden. Reivindicación 1: Un compuesto de la fórmula (1) o una sal del mismo, en donde: R¹ es alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₆, cicloalquenilo C₅₋₆ o cicloalquilo C₃₋₆-alquilo C₁₋₄; en donde este alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆ o cicloalquilo C₃₋₆-alquilo C₁₋₄ puede estar sustituido una vez o más de una vez por halógeno, hidroxilo, o alcoxilo C₁₋₄; y en donde el cicloalquilo C₃₋₆ o cicloalquenilo C₅₋₆ puede estar sustituido una vez o más de una vez por halógeno, hidroxilo, alquilo C₁₋₄, halo-alquilo C₁₋₄, hidroxi-alquilo C₁₋₄ o alcoxilo C₁₋₄; m es 1 ó 2; n es 0, 1, 2, 3 ó 4; cada R² es independientemente halógeno, hidroxilo, amino, ciano, nitro, alquilo C₁₋₆, halo-alquilo C₁₋₆, hidroxi-alquilo C₁₋₆, alcoxilo C₁₋₄-alquilo C₁₋₆, amino-alquilo C₁₋₆, alquilo C₁₋₄-amino-alquilo C₁₋₆, di-(alquilo C₁₋₄)-amino-alquilo C₁₋₆, alcoxilo C₁₋₆, haloalcoxilo C₁₋₆, alquilo C₁₋₆-amino, di-(alquilo C₁₋₆)-amino, alquenilo C₂₋₆, halo-alquenilo C₂₋₆, alquinilo C₂₋₆ o haloalquinilo C₂₋₆; o cicloalquilo C₃₋₆, en donde un átomo de carbono puede ser reemplazado por un átomo de oxígeno, en donde el cicloalquilo C₃₋₆ se puede unir directamente al metileno o por medio de un alquileno C₁₋₂, y en donde el cicloalquilo C₃₋₆ puede estar sustituido una vez o más de una vez por halógeno; o dos R² en el mismo átomo de carbono forman, junto con ese átomo de carbono, un cicloalquilo C₃₋₆; X¹ es oxígeno o -N(R⁴)-; R⁴ es hidrógeno, alquilo C₁₋₆, cicloalquilo C₃₋₆, o cicloalquilo C₃₋₆-alquilo C₁₋₂; p es 1 y q es 1; p es 0 y q es 1; o p es 0 y q es 0; r es 0, 1, 2, 3 ó 4; cada R³ es independientemente halógeno, hidroxilo, amino, ciano, nitro, alquilo C₁₋₆, halo-alquilo C₁₋₆, hidroxi-alquilo C₁₋₆, alcoxilo C₁₋₄-alquilo C₁₋₆, amino-alquilo C₁₋₆, alquilo C₁₋₄-amino-alquilo C₁₋₆, di-(alquilo C₁₋₄)-amino-alquilo C₁₋₆, alcoxilo C₁₋₆, haloalcoxilo C₁₋₆, alquilo C₁₋₆-amino, di-(alquilo C₁₋₆)-amino, alquenilo C₂₋₆, halo-alquenilo C₂₋₆, alquinilo C₂₋₆ o haloalquinilo C₂₋₆; o cicloalquilo C₃₋₆, en donde un átomo de carbono puede ser reemplazado por un átomo de oxígeno, en donde el cicloalquilo C₃₋₆ se puede unir directamente al metileno o por medio de un alquileno C₁₋₂, y en donde el cicloalquilo C₃₋₆ puede estar sustituido una vez o más de una vez por halógeno; o dos R³ en el mismo átomo de carbono forman, junto con ese átomo de carbono, un cicloalquilo C₃₋₆; A es un sistema de anillo aromático monocíclico de cinco a seis miembros o bicíclico fusionado de ocho a diez miembros, en donde este sistema de anillo puede contener de 1 a 4 heteroátomos seleccionados a partir de nitrógeno, oxígeno y azufre, y en donde este sistema de anillo puede estar sustituido una vez o más de una vez por R⁵; cada R⁵ es independientemente halógeno; ciano; nitro; hidroxilo; amino; -C(O)H; -C(O)NH₂; -C(O)OH; -X²-R⁶; o -X³-B¹; X² se selecciona a partir de un enlace; carbonilo; oxígeno; azufre; -S(O)-; -S(O)₂-; amino, el cual puede estar sustituido por alquilo C₁₋₄; -N(Rᵃ)-C(O)-; -C(O)-N(Rᵇ)-; -C(O)-O-; -O-C(O)-; -N(Rᶜ)-S(O)₂-; -S(O)₂-N(Rᵈ)-; y -NHC(O)NH-; Rᵃ, Rᵇ, Rᶜ y Rᵈ son cada uno independientemente hidrógeno o alquilo C₁₋₄; R⁶ es alquilo C₁₋₆; halo-alquilo C₁₋₆; cianoalquilo C₁₋₆; carboxi-alquilo C₁₋₆; hidroxialquilo C₁₋₆; alcoxilo C₁₋₄-alquilo C₁₋₆; alcoxilo C₁₋₄-alcoxilo C₁₋₄-alquilo C₁₋₆; alquilo C₁₋₄-carbonil-alquilo C₁₋₆; alcoxilo C₁₋₄-carbonil-alquilo C₁₋₆; alquilo C₁₋₄carboniloxialquilo C₁₋₆; amino-alquilo C₁₋₆; alquilo C₁₋₄-amino- alquilo C₁₋₆; di-(alquilo C₁₋₄)-amino-alquilo C₁₋₆; amino-carbonilalquilo C₁₋₆; alquilo C₁₋₄-amino-carbonil-alquilo C₁₋₆; di- (alquilo C₁₋₄)-amino-carbonil-alquilo C₁₋₆; alquilo C₁₋₄-carbonilamino-alquilo C₁₋₆; alquilo C₁₋₄-amino-sulfonil-alquilo C₁₋₆; di-(alquilo C₁₋₄)-amino-sulfonil-alquilo C₁₋₆; alquenilo C₂₋₆; halo-alquenilo C₂₋₆; alquinilo C₂₋₆; haloalquinilo C₂₋₆; X³ es un enlace o alquileno C₁₋₃, en donde un átomo de carbono del alquileno C₁₋₃ puede ser reemplazado por un grupo seleccionado a partir de carbonilo; oxígeno; azufre; -S(O)-; -S(O)₂-; amino, el cual puede estar sustituido por alquilo C₁₋₄; N(Rᵉ)-C(O)-; -C(O)-N(Rᶠ)-; -C(O)-O-; -O-C(O)-; -N(Rᵍ)-S(O)₂-; -S(O)₂-N(Rʰ)-; y -NHC(O)NH-; Rᵉ, Rᶠ, Rᵍ y Rʰ son cada uno independientemente hidrógeno o alquilo C₁₋₄; B¹ es un sistema de anillo monocíclico de tres a siete miembros, el cual puede ser aromático, saturado o insaturado no aromático, y el cual puede contener de 1 a 4 heteroátomos seleccionados a partir de nitrógeno, oxígeno y azufre, en donde el sistema de anillo a su vez puede estar sustituido una vez o más de una vez por R⁷; cada R⁷ es independientemente halógeno, ciano, alquilo C₁₋₄, halo-alquilo C₁₋₄, alcoxilo C₁₋₄, o halo-alcoxilo C₁₋₄; o dos R⁷ en el mismo átomo del anillo son juntos oxo; o dos R⁵ en átomos adyacentes del anillo forman, junto con esos átomos del anillo, un sistema de anillo monocíclico fusionado insaturado no aromático de cinco a siete miembros, el cual puede contener de 1 a 4 heteroátomos seleccionados a partir de nitrógeno, oxígeno y azufre, en donde el sistema de anillo a su vez puede estar sustituido una vez o más de una vez por R⁸, y en donde cada R⁸ es independientemente halógeno, alquilo C₁₋₄, o alcoxilo C₁₋₄, o dos R⁸ en el mismo átomo del anillo son juntos oxo; y en el entendido de que se excluyen los siguientes compuestos: N-[(3R)-1-[7-[[(2,4-dicloro-fenil)-metil]-amino]-pirazolo-[1,5-a]-pirimidin-5-il]-3-pirrolidinil]-4-metil-1-piperazin-carboxamida; 4-ciclopentil-N-[1-[5-(trifluoro-metil)-2-piridinil]-3-azetidinil]-1-piperazin-carboxamida; 4-ciclopentil-N-[1-[5-(trifluoro-metil)-2-piridinil]-3-pirrolidinil]-1-piperazin-carboxamida; 4-(1,1-dimetil-etil)-hexahidro-N-[1-(2-pirimidinil)-4-piperidinil]-1H-1,4-diazepin-1-carboxamida; 4-etil-N-[1-(2-pirimidinil)-4-piperidinil]-1-piperazin-carboxamida; hexahidro-4-metil-N-[1-(2-pirimidinil)-4-piperidinil]-1H-1,4-diazepin-1-carboxamida; 4-(2,2-difluoro-etil)-N-[1-(2-pirimidinil)-4-piperidinil]-1-piperazin-carboxamida; N-(1-(4-acetil-fenil)-piperidin-4-il)-4-ciclopentil-piperazin-1-carboxamida; y N-(1-(4-acetil-fenil)-piperidin-4-il)-4-ciclobutil-piperazin-1-carboxamida. Reivindicación 15: Un compuesto de la fórmula (2) o una sal del mismo; en donde p, q, r y R³ son como se definen bajo la fórmula (1); Rᵃ es un grupo saliente; A es un sistema de anillo aromático monocíclico de cinco a seis miembros, en donde este sistema de anillo puede contener de 1 a 3 heteroátomos seleccionados a partir de nitrógeno, oxígeno y azufre, y en donde este sistema de anillo puede estar sustituido una vez o más de una vez por R⁵; en donde cada R⁵ es independientemente halógeno; ciano; -C(O)NH₂ o -X²-R⁶; X² se selecciona a partir de un enlace; carbonilo; oxígeno; -C(O)-NH-; y -C(O)-O-; y R⁶ es alquilo C₁₋₆; halo-alquilo C₁₋₆; o alcoxilo C₁₋₄-alquilo C₁₋₆.
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US20190381056A1 (en) | 2018-06-17 | 2019-12-19 | Axsome Therapeutics, Inc. | Compositions for delivery of reboxetine |
US20200147093A1 (en) | 2018-10-15 | 2020-05-14 | Axsome Therapeutics, Inc. | Use of esreboxetine to treat nervous system disorders such as fibromyalgia |
US11020402B2 (en) | 2018-10-15 | 2021-06-01 | Axsome Therapeutics, Inc. | Use of reboxetine to treat narcolepsy |
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US5124457A (en) | 1986-05-21 | 1992-06-23 | Abbott Laboratories | Phencyclidine and phencyclidine metabolites assay, tracers, immunogens and antibodies |
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