HRP20161167T1 - Spoj akrilamida kao ligandi histaminskog h3 receptora - Google Patents
Spoj akrilamida kao ligandi histaminskog h3 receptora Download PDFInfo
- Publication number
- HRP20161167T1 HRP20161167T1 HRP20161167TT HRP20161167T HRP20161167T1 HR P20161167 T1 HRP20161167 T1 HR P20161167T1 HR P20161167T T HRP20161167T T HR P20161167TT HR P20161167 T HRP20161167 T HR P20161167T HR P20161167 T1 HRP20161167 T1 HR P20161167T1
- Authority
- HR
- Croatia
- Prior art keywords
- yloxy
- prop
- morpholin
- phenyl
- piperidin
- Prior art date
Links
- 102000004384 Histamine H3 receptors Human genes 0.000 title claims 3
- 108090000981 Histamine H3 receptors Proteins 0.000 title claims 3
- 150000003926 acrylamides Chemical class 0.000 title 1
- 239000003446 ligand Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 11
- 239000003814 drug Substances 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 230000007278 cognition impairment Effects 0.000 claims 3
- 201000003631 narcolepsy Diseases 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 208000027753 pain disease Diseases 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- GBDFXSACZDZMOS-WLHGVMLRSA-N (e)-but-2-enedioic acid;3-[4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]-1-morpholin-4-ylprop-2-en-1-one Chemical compound OC(=O)\C=C\C(O)=O.C1COCCN1C(=O)C=CC(C=C1)=CC=C1OC(CC1)CCN1C1CCC1 GBDFXSACZDZMOS-WLHGVMLRSA-N 0.000 claims 1
- OGJBFXCMERITRK-UHFFFAOYSA-N 3-[2-chloro-4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]-1-morpholin-4-ylprop-2-en-1-one Chemical compound ClC1=C(C=CC(=C1)OC1CCN(CC1)C1CCC1)C=CC(=O)N1CCOCC1 OGJBFXCMERITRK-UHFFFAOYSA-N 0.000 claims 1
- QTKLDMSWPQDZKW-UHFFFAOYSA-N 3-[2-chloro-4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]-1-morpholin-4-ylprop-2-en-1-one Chemical compound ClC1=C(C=CC(=C1)OC1CCN(CC1)C(C)C)C=CC(=O)N1CCOCC1 QTKLDMSWPQDZKW-UHFFFAOYSA-N 0.000 claims 1
- DGOQFTGSVKGCSM-UHFFFAOYSA-N 3-[2-chloro-4-[1-(2-methylpropyl)piperidin-4-yl]oxyphenyl]-1-morpholin-4-ylprop-2-en-1-one Chemical compound C1CN(CC(C)C)CCC1OC(C=C1Cl)=CC=C1C=CC(=O)N1CCOCC1 DGOQFTGSVKGCSM-UHFFFAOYSA-N 0.000 claims 1
- UULMRPIWZVLKTG-UHFFFAOYSA-N 3-[2-chloro-4-[1-(cyclopropylmethyl)piperidin-4-yl]oxyphenyl]-1-morpholin-4-ylprop-2-en-1-one Chemical compound ClC1=C(C=CC(=C1)OC1CCN(CC1)CC1CC1)C=CC(=O)N1CCOCC1 UULMRPIWZVLKTG-UHFFFAOYSA-N 0.000 claims 1
- XNTHZBAJYZHXFM-UHFFFAOYSA-N 3-[3-bromo-4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]-1-morpholin-4-ylprop-2-en-1-one Chemical compound BrC=1C=C(C=CC1OC1CCN(CC1)C1CCC1)C=CC(=O)N1CCOCC1 XNTHZBAJYZHXFM-UHFFFAOYSA-N 0.000 claims 1
- HKWXHIZNOVQYNL-UHFFFAOYSA-N 3-[3-bromo-4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]-1-morpholin-4-ylprop-2-en-1-one Chemical compound C1CN(C(C)C)CCC1OC(C(=C1)Br)=CC=C1C=CC(=O)N1CCOCC1 HKWXHIZNOVQYNL-UHFFFAOYSA-N 0.000 claims 1
- GDXFOUXSJGLSTE-UHFFFAOYSA-N 3-[3-bromo-4-[1-(2-methylpropyl)piperidin-4-yl]oxyphenyl]-1-morpholin-4-ylprop-2-en-1-one Chemical compound C1CN(CC(C)C)CCC1OC(C(=C1)Br)=CC=C1C=CC(=O)N1CCOCC1 GDXFOUXSJGLSTE-UHFFFAOYSA-N 0.000 claims 1
- QAVUXJXDLAHBCF-UHFFFAOYSA-N 3-[3-bromo-4-[1-(cyclopropylmethyl)piperidin-4-yl]oxyphenyl]-1-morpholin-4-ylprop-2-en-1-one Chemical compound BrC=1C=C(C=CC1OC1CCN(CC1)CC1CC1)C=CC(=O)N1CCOCC1 QAVUXJXDLAHBCF-UHFFFAOYSA-N 0.000 claims 1
- LVARVMBBEQZFAL-UHFFFAOYSA-N 3-[4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]-1-(1,1-dioxo-1,4-thiazinan-4-yl)prop-2-en-1-one hydrochloride Chemical compound Cl.O=C(C=CC1=CC=C(OC2CCN(CC2)C2CCC2)C=C1)N1CCS(=O)(=O)CC1 LVARVMBBEQZFAL-UHFFFAOYSA-N 0.000 claims 1
- HQCFXPBSJDLTSO-UHFFFAOYSA-N 3-[4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]-1-piperidin-1-ylprop-2-en-1-one;hydrochloride Chemical compound Cl.C1CCCCN1C(=O)C=CC(C=C1)=CC=C1OC(CC1)CCN1C1CCC1 HQCFXPBSJDLTSO-UHFFFAOYSA-N 0.000 claims 1
- RVIAYRYBDZAGKD-UHFFFAOYSA-N 3-[4-[1-(2-methylpropyl)piperidin-4-yl]oxyphenyl]-1-morpholin-4-ylprop-2-en-1-one Chemical compound C1CN(CC(C)C)CCC1OC(C=C1)=CC=C1C=CC(=O)N1CCOCC1 RVIAYRYBDZAGKD-UHFFFAOYSA-N 0.000 claims 1
- MWZFLLNBCMITOR-UHFFFAOYSA-N 3-[4-[1-(cyclopropylmethyl)piperidin-4-yl]oxyphenyl]-1-morpholin-4-ylprop-2-en-1-one Chemical compound O=C(C=Cc1ccc(OC2CCN(CC3CC3)CC2)cc1)N1CCOCC1 MWZFLLNBCMITOR-UHFFFAOYSA-N 0.000 claims 1
- RXJPFERMABJLGF-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C(C(C)C)N1CCC(CC1)OC1=C(C=C(C=C1)C=CC(=O)N1CCOCC1)OC Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C(C(C)C)N1CCC(CC1)OC1=C(C=C(C=C1)C=CC(=O)N1CCOCC1)OC RXJPFERMABJLGF-LREBCSMRSA-N 0.000 claims 1
- IZFSPAPTVUGJGJ-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C(C(C)C)N1CCC(CC1)OC1=CC=C(C=N1)C=CC(=O)N1CCOCC1 Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C(C(C)C)N1CCC(CC1)OC1=CC=C(C=N1)C=CC(=O)N1CCOCC1 IZFSPAPTVUGJGJ-LREBCSMRSA-N 0.000 claims 1
- SKSZEMDNTDTFAG-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C(C)(C)N1CCC(CC1)OC1=C(C=C(C=C1)C=CC(=O)N1CCCCC1)OC Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C(C)(C)N1CCC(CC1)OC1=C(C=C(C=C1)C=CC(=O)N1CCCCC1)OC SKSZEMDNTDTFAG-LREBCSMRSA-N 0.000 claims 1
- UKMBSPBAOMHITI-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C(C)(C)N1CCC(CC1)OC1=C(C=C(C=C1)C=CC(=O)N1CCOCC1)OC Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C(C)(C)N1CCC(CC1)OC1=C(C=C(C=C1)C=CC(=O)N1CCOCC1)OC UKMBSPBAOMHITI-LREBCSMRSA-N 0.000 claims 1
- RHZXIVPTJVWGQX-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C(C)(C)N1CCC(CC1)OC1=CC(=C(C=C1)C=CC(=O)N1CCOCC1)C Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C(C)(C)N1CCC(CC1)OC1=CC(=C(C=C1)C=CC(=O)N1CCOCC1)C RHZXIVPTJVWGQX-LREBCSMRSA-N 0.000 claims 1
- XUQCDRVFHYYKQR-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1(CC1)CN1CCC(CC1)OC1=C(C=C(C=C1)C=CC(=O)N1CCOCC1)OC Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1(CC1)CN1CCC(CC1)OC1=C(C=C(C=C1)C=CC(=O)N1CCOCC1)OC XUQCDRVFHYYKQR-LREBCSMRSA-N 0.000 claims 1
- AQQZANISWWPPIN-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1(CC1)CN1CCC(CC1)OC1=CC=C(C=N1)C=CC(=O)N1CCOCC1 Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1(CC1)CN1CCC(CC1)OC1=CC=C(C=N1)C=CC(=O)N1CCOCC1 AQQZANISWWPPIN-LREBCSMRSA-N 0.000 claims 1
- UTNZWYDYJGQTDR-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1(CCC1)N1CCC(CC1)OC1=C(C=C(C=C1)C=CC(=O)N1CCCCC1)OC Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1(CCC1)N1CCC(CC1)OC1=C(C=C(C=C1)C=CC(=O)N1CCCCC1)OC UTNZWYDYJGQTDR-LREBCSMRSA-N 0.000 claims 1
- VVTGVIBDUDEQOS-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1(CCC1)N1CCC(CC1)OC1=C(C=C(C=C1)C=CC(=O)N1CCOCC1)OC Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1(CCC1)N1CCC(CC1)OC1=C(C=C(C=C1)C=CC(=O)N1CCOCC1)OC VVTGVIBDUDEQOS-LREBCSMRSA-N 0.000 claims 1
- AUYMIMMPZVLDSY-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1(CCC1)N1CCC(CC1)OC1=CC(=C(C=C1)C=CC(=O)N1CCOCC1)C Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1(CCC1)N1CCC(CC1)OC1=CC(=C(C=C1)C=CC(=O)N1CCOCC1)C AUYMIMMPZVLDSY-LREBCSMRSA-N 0.000 claims 1
- GPTNMYFICRWZSO-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1(CCC1)N1CCC(CC1)OC1=CC=C(C=C1)C=CC(=O)N1CCOCC1 Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1(CCC1)N1CCC(CC1)OC1=CC=C(C=C1)C=CC(=O)N1CCOCC1 GPTNMYFICRWZSO-LREBCSMRSA-N 0.000 claims 1
- KFFFUDPJKDFYEC-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1(CCC1)N1CCC(CC1)OC1=NC=C(C=C1)C=CC(=O)N1CCCCC1 Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1(CCC1)N1CCC(CC1)OC1=NC=C(C=C1)C=CC(=O)N1CCCCC1 KFFFUDPJKDFYEC-LREBCSMRSA-N 0.000 claims 1
- RIRIHBJVVLMMCL-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1(CCC1)N1CCC(CC1)OC1=NC=C(C=C1)C=CC(=O)N1CCOCC1 Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1(CCC1)N1CCC(CC1)OC1=NC=C(C=C1)C=CC(=O)N1CCOCC1 RIRIHBJVVLMMCL-LREBCSMRSA-N 0.000 claims 1
- JBFAZGPPVTXRBL-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.FC1=C(C=CC(=C1)OC1CCN(CC1)C1CCC1)C=CC(=O)N1CCOCC1 Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.FC1=C(C=CC(=C1)OC1CCN(CC1)C1CCC1)C=CC(=O)N1CCOCC1 JBFAZGPPVTXRBL-LREBCSMRSA-N 0.000 claims 1
- FOYGNANQZZLXDH-LREBCSMRSA-N O[C@H]([C@@H](O)C(O)=O)C(O)=O.CC(C)N1CCC(CC1)Oc1ccc(C=CC(=O)N2CCOCC2)c(F)c1 Chemical compound O[C@H]([C@@H](O)C(O)=O)C(O)=O.CC(C)N1CCC(CC1)Oc1ccc(C=CC(=O)N2CCOCC2)c(F)c1 FOYGNANQZZLXDH-LREBCSMRSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
Classifications
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/28—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Claims (8)
1. Spoj opće formule (I):
[image]
pri čemu,
R1 se neovisno izabire iz vodika, halogena, alkila ili alkoksija; "A" je alkil, cikloalkil ili cikloalkilalkil;
"X" je CH ili N;
"Y" je CH2, O ili
[image]
ili njegove farmaceutski prihvatljive soli.
2. Spoj prema patentnom zahtjevu 1, izabrano iz grupe koja se sastoji od:
3-[4-(1-ciklobutil piperidin-4-iloksi) fenil]-1-(morfolin-4-il) prop-2-en-1-on fumarat sol;
3-[4-(1-ciklobutil piperidin-4-iloksi) fenil]-1-(piperidin-1-il) prop-2-en-1-on hIdrohloridna sol;
3-[4-(1-ciklobutil piperidin-4-iloksi) fenil]-1-(1,1-diokso tiomorfolin-4-il) prop-2-en-1-on hidrokloridna sol;
3-[2-(1-ciklobutil piperidin-4-iloksi) piridin-5-il]-1-(piperidin-1-il) prop-2-en-1-on L(+)-tartarat sol;
3-[2-(1-ciklobutil piperidin-4-iloksi) piridin-5-il]-1-(morfolin-4-il) prop-2-en-1-on L(+)-tartarat sol;
3-[2-fluoro-4-(1-izopropil piperidin-4-iloksi) fenil]-1-(morfolin-4-il) prop-2-en-1-on L(+)-tartarat sol;
3-[2-fluoro-4-(1-ciklobutil piperidin-4-iloksi) fenil]-1-(morfolin-4-il) prop-2-en-1-on L(+)-tartarat sol;
3-[4-(1-ciklobutil piperidin-4-iloksi)-2-metil fenil]-1-(morfolin-4-il) prop-2-en-1-on L(+)-tartarat sol;
3-[4-(1-izopropil piperidin-4-iloksi)-2-metil fenil]-1-(morfolin-4-il) prop-2-en-1-on L(+)-tartarat sol;
3-[4-(1-ciklobutil piperidin-4-iloksi) fenil]-1-(morfolin-4-il) prop-2-en-1-on L(+)-tartarat sol;
3-[4-(1-ciklobutil piperidin-4-iloksi)-3-metoksi fenil]-1-(morfolin-4-il) prop-2-en-1-on L(+)-tartarat sol;
3-[4-(1-ciklopropilmetil piperidin-4-iloksi)-3-metoksi fenil]-1-(morfolin-4-il) prop-2-en-1-on L(+)-tartarat sol;
3-[4-(1-izobutil piperidin-4-iloksi)-3-metoksi fenil]-1-(morfolin-4-il) prop-2-en-1-on L(+)-tartarat sol;
3-[4-(1-izopropil piperidin-4-iloksi)-3-metoksi fenil]-1-(morfolin-4-il) prop-2-en-1-on L(+)-tartarat sol;
3-[4-(1-izopropil piperidin-4-iloksi)-3-metoksi fenil]-1-(piperidin-1-il) prop-2-en-1-on L(+)-tartarat sol;
3-[4-(1-ciklobutil piperidin-4-iloksi)-3-metoki fenil]-1-(piperidin-1-il) prop-2-en-1-on L(+)-tartarat sol;
3-[4-(1-ciklopropilmetil piperidin-4-iloksi) fenil]-1-(morfolin-4-il) prop-2-en-1-on;
3-[4-(1-izobutil piperidin-4-iloksi) fenil]-1-(morfolin-4-il) prop-2-en-1-on;
3-[3-bromo-4-(1-izopropil piperidin-4-iloksi) fenil]-1-(morfolin-4-il) prop-2-en-1-on;
3-[3-bromo-4-(1-ciklobutil piperidin-4-iloksi) fenil]-1-(morfolin-4-il) prop-2-en-1-on;
3-[3-bromo-4-(1-izobutil piperidin-4-iloksi) fenil]-1-(morfolin-4-il) prop-2-en-1-on;
3-[3-bromo-4-(1-ciklopropilmetil piperidin-4-iloksi) fenil]-1-(morfolin-4-il) prop-2-en-1-on;
3-[6-(1-ciklopropilmetil piperidin-4-iloksi) piridin-3-il]-1-(morfolin-4-il) prop-2-en-1-on L(+)-tartarat sol;
3-[6-(1-izobutil piperidin-4-iloksi) piridin-3-il]-1-(morfolin-4-il) prop-2-en-1-on L(+)-tartarat sol;
3-[2-kloro-4-(1-ciklobutil piperidin-4-iloksi) fenil]-1-(morfolin-4-il) prop-2-en-1-on;
3-[2-kloro-4-(1-izopropil piperidin-4-iloksi) fenil]-1-(morfolin-4-il) prop-2-en-1-on;
3-[2-kloro-4-(1-ciklopropilmetil piperidin-4-iloksi) fenil]-1-(morfolin-4-il) prop-2-en-1-on; i
3-[2-kloro-4-(1-izobutil piperidin-4-iloksi) fenil]-1-(morfolin-4-il) prop-2-en-1-on;
ili njihove farmaceutski prihvatljive soli.
3. Postupak za pripremu spoja prema formuli (I) kao se tvrdi u patentnom zahtjevu 1, koji obuhvaća:
(a) reduktivnu aminaciju spoja prema formuli (1) sa spojem iz formule (2)
[image]
uz prisutnost pogodnoga rastvarača i reduktirajućeg agensa da se formira spoj iz formule (I), pri čemu sve supstitucije kako je definirano u patentnom zahtjevu 1,
(b) opciono pretvaraju spoj iz formule (I) u njihove farmaceutski prihvatljive soli.
4. Farmaceutska supstanca obuhvaća spoj prema patentnom zahtjevu 1 farmaceutski prihvatljive ekscipijente.
5. Farmaceutska supstanca prema patentnom zahtjevu 4, za uporabu u liječenju kliničkih stanja izazvanih putem H3 receptora izabranog iz kognitivinh nedostataka u shizofreniji, narkolepsiji, pretilosti, poremećaju hiperaktivnosti i deficita pažnje (ADHD), boli ili Alzheimerovoj bolesti.
6. Spoj kako se tvrdi u bilo kojem od patentnih zahtjeva 1 ili 2 za uporabu u liječenju kognitivnih nedostataka u shizofreniji, narkolepsiji, pretilosti, poremećaju hiperaktivnosti i deficita pažnje (ADHD), boli ili Alzheimerovoj bolesti.
7. Uporaba spoja prema patentnom zahtjevu 1 u proizvodnji lijeka za liječenje bolesti koja se odnosi na histaminske H3 receptore.
8. Uporaba spoja u proizvodnji lijeka prema patentnom zahtjevu 7, za liječenje kliničkih stanja izabranih iz kognitivnih nedostataka u shizofreniji, narkolepsiji, pretilosti, poremećaju hiperaktivnosti i deficita pažnje (ADHD), boli ili Alzheimerovoj bolesti.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN3464CH2012 | 2012-08-23 | ||
| PCT/IN2012/000796 WO2014030170A1 (en) | 2012-08-23 | 2012-12-05 | Acrylamide compounds as histamine h3 receptor ligands |
| EP12844650.7A EP2888243B1 (en) | 2012-08-23 | 2012-12-05 | Acrylamide compounds as histamine h3 receptor ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20161167T1 true HRP20161167T1 (hr) | 2016-11-04 |
Family
ID=54187093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20161167TT HRP20161167T1 (hr) | 2012-08-23 | 2016-09-13 | Spoj akrilamida kao ligandi histaminskog h3 receptora |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US9328092B2 (hr) |
| EP (1) | EP2888243B1 (hr) |
| JP (1) | JP5981654B2 (hr) |
| KR (1) | KR101707343B1 (hr) |
| CN (1) | CN104540812B (hr) |
| AP (1) | AP2014008139A0 (hr) |
| AU (1) | AU2012388383C1 (hr) |
| BR (1) | BR112015001524B1 (hr) |
| CA (1) | CA2878217C (hr) |
| CY (1) | CY1118035T1 (hr) |
| DK (1) | DK2888243T3 (hr) |
| EA (1) | EA025136B1 (hr) |
| ES (1) | ES2592819T3 (hr) |
| HK (1) | HK1204620A1 (hr) |
| HR (1) | HRP20161167T1 (hr) |
| HU (1) | HUE030901T2 (hr) |
| IL (1) | IL236437A (hr) |
| LT (1) | LT2888243T (hr) |
| ME (1) | ME02519B (hr) |
| MX (1) | MX360001B (hr) |
| PL (1) | PL2888243T3 (hr) |
| PT (1) | PT2888243T (hr) |
| RS (1) | RS55158B1 (hr) |
| SG (1) | SG11201408423XA (hr) |
| SI (1) | SI2888243T1 (hr) |
| SM (1) | SMT201600336B (hr) |
| WO (1) | WO2014030170A1 (hr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11313246B2 (en) * | 2016-11-30 | 2022-04-26 | General Electric Company | Gas turbine engine wash system |
| WO2022113008A1 (en) | 2020-11-27 | 2022-06-02 | Richter Gedeon Nyrt. | Histamine h3 receptor antagonists/inverse agonists for the treatment of autism spectrum disorder |
| WO2023166351A1 (zh) * | 2022-03-02 | 2023-09-07 | 杭州百诚医药科技股份有限公司 | 组胺h3受体抑制剂及其医药用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0410657A (pt) * | 2003-06-12 | 2006-06-20 | Novo Nordisk As | composto, composição farmacêutica, uso de um composto, método para tratar um distúrbio de um paciente, e, processo para a preparação de um composto |
| US8008301B2 (en) | 2004-04-01 | 2011-08-30 | Eli Lilly And Company | Histamine H3 receptor agents, preparation and therapeutic uses |
| EP1755593B1 (en) * | 2004-06-02 | 2008-01-16 | F.Hoffmann-La Roche Ag | Naphthalene derivatives useful as histamine-3-receptor ligands |
| AU2005254658B2 (en) | 2004-06-21 | 2011-06-16 | F. Hoffmann-La Roche Ag | Indole derivatives as histamine receptor antagonists |
| CA2577061C (en) | 2004-08-23 | 2014-02-18 | Eli Lilly And Company | Histamine h3 receptor agents, preparation and therapeutic uses |
| WO2007062997A1 (en) * | 2005-11-30 | 2007-06-07 | F. Hoffmann-La Roche Ag | 1,1-dioxo-thiomorpholinyl indolyl methanone derivatives for use as h3 modulators |
| KR20090015098A (ko) | 2006-05-30 | 2009-02-11 | 에프. 호프만-라 로슈 아게 | 피페리디닐 피리미딘 유도체 |
| KR20100027231A (ko) | 2007-07-25 | 2010-03-10 | 에프. 호프만-라 로슈 아게 | 벤조퓨란- 및 벤조[ｂ]티오펜-2-카복실산 아마이드 유도체 및 이의 히스타민 3 수용체 조절제로서의 용도 |
| CA2697941A1 (en) | 2007-09-06 | 2009-03-12 | Glaxo Group Limited | Piperazine derivative having affinity for the histamine h3 receptor |
| WO2009100120A2 (en) | 2008-02-04 | 2009-08-13 | Neurogen Corporation | Pyridinyl-substituted piperazinyl oxoethyl tetrahydropyrazolopyridines |
| WO2009121812A1 (en) | 2008-03-31 | 2009-10-08 | Evotec Neurosciences Gmbh | Tetrahydronaphthyridines and aza derivatives thereof as histamine h3 receptor antagonists |
| CN102015636B (zh) | 2008-05-08 | 2014-08-13 | 埃沃特克股份有限公司 | 作为组胺h3受体拮抗剂的氮杂环丁烷类和环丁烷类化合物 |
| SG188212A1 (en) * | 2010-09-02 | 2013-04-30 | Suven Life Sciences Ltd | Heterocyclyl compounds as histamine h3 receptor ligands |
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- 2012-12-05 AU AU2012388383A patent/AU2012388383C1/en active Active
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