HRP20090523T1 - Novi piridinilaminoalkilen i piridiniloksialkilen ciklopropanamini, postupak njihove priprave i farmaceutski pripravci koji ih sadrže - Google Patents
Novi piridinilaminoalkilen i piridiniloksialkilen ciklopropanamini, postupak njihove priprave i farmaceutski pripravci koji ih sadrže Download PDFInfo
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- HRP20090523T1 HRP20090523T1 HR20090523T HRP20090523T HRP20090523T1 HR P20090523 T1 HRP20090523 T1 HR P20090523T1 HR 20090523 T HR20090523 T HR 20090523T HR P20090523 T HRP20090523 T HR P20090523T HR P20090523 T1 HRP20090523 T1 HR P20090523T1
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- 238000000034 method Methods 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title claims 2
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 8
- 125000004385 trihaloalkyl group Chemical group 0.000 claims abstract 7
- 125000002252 acyl group Chemical group 0.000 claims abstract 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 6
- 125000003118 aryl group Chemical group 0.000 claims abstract 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract 6
- 150000002367 halogens Chemical class 0.000 claims abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 4
- 125000002619 bicyclic group Chemical group 0.000 claims abstract 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
- 235000010290 biphenyl Nutrition 0.000 claims abstract 2
- 239000004305 biphenyl Substances 0.000 claims abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 2
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims abstract 2
- 125000005842 heteroatom Chemical group 0.000 claims abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims abstract 2
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 2
- UDYAQGAZMQKTNQ-UHFFFAOYSA-N nitro N-(sulfanylidenemethylidene)carbamate Chemical compound [O-][N+](=O)OC(=O)N=C=S UDYAQGAZMQKTNQ-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- 239000011593 sulfur Substances 0.000 claims abstract 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims abstract 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 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 claims 6
- 239000013543 active substance Substances 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims 4
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 208000026139 Memory disease Diseases 0.000 claims 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- UXHRXHNTYNSZSJ-UHFFFAOYSA-N 4-[2-chloro-5-[[1-(methylamino)cyclopropyl]methoxy]pyridin-3-yl]benzamide;hydrochloride Chemical compound Cl.C=1N=C(Cl)C(C=2C=CC(=CC=2)C(N)=O)=CC=1OCC1(NC)CC1 UXHRXHNTYNSZSJ-UHFFFAOYSA-N 0.000 claims 1
- DBVZPNFZEDEAMO-UHFFFAOYSA-N 4-[2-chloro-5-[[1-(methylamino)cyclopropyl]methoxy]pyridin-3-yl]benzoic acid;hydrochloride Chemical compound Cl.C=1N=C(Cl)C(C=2C=CC(=CC=2)C(O)=O)=CC=1OCC1(NC)CC1 DBVZPNFZEDEAMO-UHFFFAOYSA-N 0.000 claims 1
- SYTMIKZYAVIQFG-UHFFFAOYSA-N 5-(4-aminophenyl)-6-methyl-n-[[1-(methylamino)cyclopropyl]methyl]pyridin-3-amine;trihydrochloride Chemical compound Cl.Cl.Cl.C=1N=C(C)C(C=2C=CC(N)=CC=2)=CC=1NCC1(NC)CC1 SYTMIKZYAVIQFG-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 1
- 208000006264 Korsakoff syndrome Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 1
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims 1
- 208000000323 Tourette Syndrome Diseases 0.000 claims 1
- 208000016620 Tourette disease Diseases 0.000 claims 1
- QMPVMUYCUPGVOZ-UHFFFAOYSA-N [1-[(6-chloro-5-pyridin-4-ylpyridin-3-yl)oxymethyl]cyclopropyl]methanamine;dihydrochloride Chemical compound Cl.Cl.C=1N=C(Cl)C(C=2C=CN=CC=2)=CC=1OCC1(CN)CC1 QMPVMUYCUPGVOZ-UHFFFAOYSA-N 0.000 claims 1
- OZSPIIHMEDAPCW-UHFFFAOYSA-N [1-[[5,6-bis(4-chlorophenyl)pyridin-3-yl]oxymethyl]cyclopropyl]methanamine;dihydrochloride Chemical compound Cl.Cl.C=1N=C(C=2C=CC(Cl)=CC=2)C(C=2C=CC(Cl)=CC=2)=CC=1OCC1(CN)CC1 OZSPIIHMEDAPCW-UHFFFAOYSA-N 0.000 claims 1
- MANFXJFZOLAYOE-UHFFFAOYSA-N [1-[[5-(3-methoxyphenyl)pyridin-3-yl]oxymethyl]cyclopropyl]methanamine;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC(C=2C=C(OCC3(CN)CC3)C=NC=2)=C1 MANFXJFZOLAYOE-UHFFFAOYSA-N 0.000 claims 1
- AXMVUGKLWZGGAV-UHFFFAOYSA-N [1-[[5-(4-chlorophenyl)pyridin-3-yl]oxymethyl]cyclopropyl]methanamine;hydrochloride Chemical compound Cl.C=1N=CC(C=2C=CC(Cl)=CC=2)=CC=1OCC1(CN)CC1 AXMVUGKLWZGGAV-UHFFFAOYSA-N 0.000 claims 1
- JBGCTFVZFISAGP-UHFFFAOYSA-N [1-[[5-(4-methoxyphenyl)pyridin-3-yl]oxymethyl]cyclopropyl]methanamine;dihydrochloride Chemical compound Cl.Cl.C1=CC(OC)=CC=C1C1=CN=CC(OCC2(CN)CC2)=C1 JBGCTFVZFISAGP-UHFFFAOYSA-N 0.000 claims 1
- XWAFLFUZWVEZCD-UHFFFAOYSA-N [1-[[6-chloro-5-(3,5-dichlorophenyl)pyridin-3-yl]oxymethyl]cyclopropyl]methanamine;hydrochloride Chemical compound Cl.C=1N=C(Cl)C(C=2C=C(Cl)C=C(Cl)C=2)=CC=1OCC1(CN)CC1 XWAFLFUZWVEZCD-UHFFFAOYSA-N 0.000 claims 1
- MDKRFPVVOMETSO-UHFFFAOYSA-N [1-[[6-chloro-5-(3-methoxyphenyl)pyridin-3-yl]oxymethyl]cyclopropyl]methanamine;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC(C=2C(=NC=C(OCC3(CN)CC3)C=2)Cl)=C1 MDKRFPVVOMETSO-UHFFFAOYSA-N 0.000 claims 1
- OTTXJHOVAGSDQU-UHFFFAOYSA-N [1-[[6-chloro-5-(4-fluorophenyl)pyridin-3-yl]oxymethyl]cyclopropyl]methanamine;hydrochloride Chemical compound Cl.C=1N=C(Cl)C(C=2C=CC(F)=CC=2)=CC=1OCC1(CN)CC1 OTTXJHOVAGSDQU-UHFFFAOYSA-N 0.000 claims 1
- MBCCTXVXCIJSRZ-UHFFFAOYSA-N [1-[[6-chloro-5-(4-methylsulfanylphenyl)pyridin-3-yl]oxymethyl]cyclopropyl]methanamine;dihydrochloride Chemical compound Cl.Cl.C1=CC(SC)=CC=C1C1=CC(OCC2(CN)CC2)=CN=C1Cl MBCCTXVXCIJSRZ-UHFFFAOYSA-N 0.000 claims 1
- UVMSLCGNBJXMRX-UHFFFAOYSA-N [1-[[6-chloro-5-[4-(2h-tetrazol-5-yl)phenyl]pyridin-3-yl]oxymethyl]cyclopropyl]methanamine;dihydrochloride Chemical compound Cl.Cl.C=1N=C(Cl)C(C=2C=CC(=CC=2)C2=NNN=N2)=CC=1OCC1(CN)CC1 UVMSLCGNBJXMRX-UHFFFAOYSA-N 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- WJXNZPBALGUCOX-UHFFFAOYSA-N ethyl 4-[2-chloro-5-[[1-(methylamino)cyclopropyl]methoxy]pyridin-3-yl]benzoate;dihydrochloride Chemical compound Cl.Cl.C1=CC(C(=O)OCC)=CC=C1C1=CC(OCC2(CC2)NC)=CN=C1Cl WJXNZPBALGUCOX-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- VXESQMWLQKRDSH-UHFFFAOYSA-N n-[3-[2-chloro-5-[[1-(methylamino)cyclopropyl]methoxy]pyridin-3-yl]phenyl]acetamide;hydrochloride Chemical compound Cl.C=1N=C(Cl)C(C=2C=C(NC(C)=O)C=CC=2)=CC=1OCC1(NC)CC1 VXESQMWLQKRDSH-UHFFFAOYSA-N 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 230000005586 smoking cessation Effects 0.000 claims 1
- 230000002739 subcortical effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000004952 trihaloalkoxy group Chemical group 0.000 abstract 3
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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
- C07D401/10—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 carbon chain containing aromatic 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
- A61K31/435—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
- A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
-
- 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
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- 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
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- 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
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- 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
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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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- 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
- A61P25/34—Tobacco-abuse
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
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- Plural Heterocyclic Compounds (AREA)
Abstract
Spojevi formule (I): naznačeni time, da: n predstavlja cijeli broj u rasponu od uključivo 1 do 6, X predstavlja atom kisika ili skupinu NR6,Y predstavlja atom ugljika ili atom dušika, pri čemu se podrazumijeva da kada Y predstavlja atom dušika, Rd nije prisutan, Z predstavlja atom ugljika ili atom dušika, pri čemu se podrazumijeva da kada Z predstavlja atom dušika, Rc nije prisutan, R1 i R2, koji mogu biti identični ili različiti, neovisno jedan o drugom, predstavljaju atom vodika, ili skupinu ravni ili razgranani alkil (C1-C6) ili ravni ili razgranani arilalkil (C1-C6),R3 i R4, koji mogu biti identični ili različiti, neovisno jedan o drugom, predstavljaju atom vodika, ili skupinu ravni ili razgranani alkil (C1-C6),R5 predstavlja atom vodika, ili skupinu ravni ili razgranani alkil (C1-C6), halogen, hidroksi, ravni ili razgranani alkoksi (C1-C6), cijano, nitro, ravni ili razgranani acil (C2-C6), ravni ili razgranani alkoksikarbonil (C1-C6), ravni ili razgranani trihalogenalkil (C1-C6), ravni ilirazgranani trihalogenalkoksi (C1-C6), amino po izboru supstituiran s jednom ili dvije skupine ravni ili razgranani alkil (C1-C6), aril ili heteroaril, R6 predstavlja atom vodika, ili skupinu ravni ili razgranani alkil (C1-C6) ili ravni ili razgranani arilalkil (C1-C6),Ra, Rb, Rc, Rd i Re, koji mogu biti identični ili različiti, neovisno jedan o drugom, predstavljaju atom vodika, ili skupinu ravni ili razgranani alkil (C1-C6), halogen, ravni ili razgranani halogenalkil (C1-C6), hidroksi, ravni ili razgranani alkoksi (C1-C6), ravni ili razgranani hidroksialkil (C1-C6), cijano, nitro, karboksi, izotiocijanat, ravni ili razgranani acil (C2-C6), ravni ili razgranani alkoksikarbonil (C1-C6), ravni ili razgranani trihalogenalkil (C1-C6), ravni ili razgranani trihalogenalkoksi (C1-C6), ravni ili razgranani alkiltio (C1-C6), alkil (C1-C6) karbonilamino, pri čemu je alkilni dio ravan ili razgranan, halogenalkil (C1-C6)karbonilamino, pri čemu je alkilni dio ravan ili razgranan, aminokarbonil, amino po izboru supstituiran s jednom ili dvije skupine ravni ili razgranani alkil (C1-C6), tetrazolil, pod skupinom aril podrazumijeva se skupina fenil, bifenil, naftil, dihidronaftil, tetrahidronaftil, indanil i indenil, a svaka od navedenih skupina može biti supstituirana jednom ili više skupina, koje mogu biti identične ili različite, a odabrane su između sljedećih: halogen, ravni ili razgranani alkil (C1-C6), hidroksi, cijano, nitro, ravni ili razgranani alkoksi (C1-C6), ravni ili razgranani acil (C2-C7), ravni ili razgranani alkoksikarbonil (C1-C6), ravni ili razgranani trihalogenalkil (C1-C6), ravni ili razgranani trihalogenalkoksi (C1-C6) i amino, koji je po izboru supstituiran s jednom ili dvije skupine ravni ili razgranani alkil (C1-C6), pod skupinom heteroaril podrazumijeva se aromatski monociklički ili biciklički sustav s 5 do 12 članova, koji sadrže od jednog do tri heteroatoma, koji mogu biti identični ili različiti, odabranih između kisika, dušika i sumpora, od koj
Claims (15)
1. Spojevi formule (I):
[image]
naznačeni time, da:
n predstavlja cijeli broj u rasponu od uključivo 1 do 6,
X predstavlja atom kisika ili skupinu NR6,
Y predstavlja atom ugljika ili atom dušika, pri čemu se podrazumijeva da kada Y predstavlja atom dušika, Rd nije prisutan,
Z predstavlja atom ugljika ili atom dušika, pri čemu se podrazumijeva da kada Z predstavlja atom dušika, Rc nije prisutan,
R1 i R2, koji mogu biti identični ili različiti, neovisno jedan o drugom, predstavljaju atom vodika, ili skupinu ravni ili razgranani alkil (C1-C6) ili ravni ili razgranani arilalkil (C1-C6),
R3 i R4, koji mogu biti identični ili različiti, neovisno jedan o drugom, predstavljaju atom vodika, ili skupinu ravni ili razgranani alkil (C1-C6),
R5 predstavlja atom vodika, ili skupinu ravni ili razgranani alkil (C1-C6), halogen, hidroksi, ravni ili razgranani alkoksi (C1-C6), cijano, nitro, ravni ili razgranani acil (C2-C6), ravni ili razgranani alkoksikarbonil (C1-C6), ravni ili razgranani trihalogenalkil (C1-C6), ravni ilirazgranani trihalogenalkoksi (C1-C6), amino po izboru supstituiran s jednom ili dvije skupine ravni ili razgranani alkil (C1-C6), aril ili heteroaril,
R6 predstavlja atom vodika, ili skupinu ravni ili razgranani alkil (C1-C6) ili ravni ili razgranani arilalkil (C1-C6),
Ra, Rb, Rc, Rd i Re, koji mogu biti identični ili različiti, neovisno jedan o drugom, predstavljaju atom vodika, ili skupinu ravni ili razgranani alkil (C1-C6), halogen, ravni ili razgranani halogenalkil (C1-C6), hidroksi, ravni ili razgranani alkoksi (C1-C6), ravni ili razgranani hidroksialkil (C1-C6), cijano, nitro, karboksi, izotiocijanat, ravni ili razgranani acil (C2-C6), ravni ili razgranani alkoksikarbonil (C1-C6), ravni ili razgranani trihalogenalkil (C1-C6), ravni ili razgranani trihalogenalkoksi (C1-C6), ravni ili razgranani alkiltio (C1-C6), alkil (C1-C6) karbonilamino, pri čemu je alkilni dio ravan ili razgranan, halogenalkil (C1-C6)karbonilamino, pri čemu je alkilni dio ravan ili razgranan, aminokarbonil, amino po izboru supstituiran s jednom ili dvije skupine ravni ili razgranani alkil (C1-C6), tetrazolil,
pod skupinom aril podrazumijeva se skupina fenil, bifenil, naftil, dihidronaftil, tetrahidronaftil, indanil i indenil, a svaka od navedenih skupina može biti supstituirana jednom ili više skupina, koje mogu biti identične ili različite, a odabrane su između sljedećih: halogen, ravni ili razgranani alkil (C1-C6), hidroksi, cijano, nitro, ravni ili razgranani alkoksi (C1-C6), ravni ili razgranani acil (C2-C7), ravni ili razgranani alkoksikarbonil (C1-C6), ravni ili razgranani trihalogenalkil (C1-C6), ravni ili razgranani trihalogenalkoksi (C1-C6) i amino, koji je po izboru supstituiran s jednom ili dvije skupine ravni ili razgranani alkil (C1-C6), pod skupinom heteroaril podrazumijeva se aromatski monociklički ili biciklički sustav s 5 do 12 članova, koji sadrže od jednog do tri heteroatoma, koji mogu biti identični ili različiti, odabranih između kisika, dušika i sumpora, od kojih jedan prsten, kada se radi o bicikličkim sustavima, ima aromatske osobine, a drugi prsten može biti aromatski ili djelomično hidrogenirani, a svaka od navedenih skupina po izboru može biti supstituirana jednom ili više skupina koje mogu biti identične ili različite, a odabrane su između supstituenata koji su prethodno definirani za skupinu aril.
2. Spojevi formule (I) u skladu s patentnim zahtjevom 1, naznačeni time, da predstavljaju spojeve formule (I/A):
[image]
u kojoj su R1, R2, R3, R4, R5, Ra, Rb, Rc, Rd, Re, X i n definirani jednako kao gore.
3. Spojevi formule (I) u skladu s patentnim zahtjevom 1, naznačeni time, da predstavljaju spojeve formule (I/B):
[image]
u kojoj su R1, R2, R3, R4, R5, Ra, Rb, Rd, Re, X i n definirani jednako kao gore.
4. Spojevi formule (1) u skladu s patentnim zahtjevom 1, naznačeni time, da predstavljaju spojeve formule (I/C):
[image]
u kojoj su R1, R2, R3, R4, R5, Ra, Rb, Rc, Re, X i n definirani jednako kao gore.
5. Spojevi formule (I) u skladu s patentnim zahtjevom 1, naznačeni time, daje n cijeli broj čija je vrijednost 1, njihovi enantiomeri, dijastereoizomeri, kao i njihove adicijske soli s farmaceutski prihvatljivom kiselinom ili farmaceutski prihvatljivom bazom.
6. Spojevi formule (I) u skladu s patentnim zahtjevom 1, naznačeni time, da R1 i R2, koji mogu biti identični ili različiti, neovisno jedan o drugom, predstavljaju atom vodika i skupinu ravni ili razgranani alkil (C1-C6), njihovi enantiomeri, dijastereoizomeri, kao i njihove adicijske soli s farmaceutski prihvatljivom kiselinom ili farmaceutski prihvatljivom bazom.
7. Spojevi formule (I) u skladu s patentnim zahtjevom 1, naznačeni time, da R3 i R4, koji mogu biti identični ili različiti, predstavljaju svaki za sebe atom vodika ili skupinu metil, njihovi enantiomeri, dijastereoizomeri, kao i njihove adicijske soli s farmaceutski prihvatljivom kiselinom ili farmaceutski prihvatljivom bazom.
8. Spojevi formule (I) u skladu s patentnim zahtjevom 1, naznačeni time, da R5 predstavlja atom vodika, atom halogena ili skupinu metil, njihovi enantiomeri, dijastereoizomeri, kao i njihove adicijske soli s farmaceutski prihvatljivom kiselinom ili farmaceutski prihvatljivom bazom.
9. Spojevi formule (I) u skladu s patentnim zahtjevom 1, naznačeni time, da R6 predstavlja atom vodika i skupinu metil, njihovi enantiomeri, dijastereoizomeri, kao i njihove adicijske soli s farmaceutski prihvatljivom kiselinom ili farmaceutski prihvatljivom bazom.
10. Spojevi formule (I) u skladu s patentnim zahtjevom 1, naznačeni time, da su to sljedeći spojevi:
[1-({[5-(3-metoksifenil)piridin-3-il]oksi}metil)ciklopropil]metilamin dihidroklorid,
[1-({[6-kloro-5-(3-metoksifenil)piridin-3-il]oksi}metil)-ciklopropil]metilamin dihidroklorid,
[1-({[5-(4-metoksifenil)piridin-3-il]oksi}metil)ciklopropil]metilamin dihidroklorid,
[1-({[5-(4-klorfenil)piridin-3-il]oksi}metil)ciklopropil]metilamin hidroklorid,
[1-({[6-kloro-5-(4-fluorfenil)piridin-3-il]oksi}metil)-ciklopropil]metilamin hidroklorid,
{1-[({6-kloro-5-[4-(metiltio)fenil]piridin-3-il}oksi)metil]-ciklopropil}metilamin dihidroklorid,
[1-({[6-kloro-5-(3,5-diklorfenil)piridin-3-il]oksi}metil)-ciklopropil]metilamin hidroklorid,
N-[3-(2-kloro-5-{[1-(metilamino)ciklopropil]metoksi}piridin-3-il)-fenil]acetamid hidroklorid,
Etil 4-(2-kloro-5-{[1-(metilamino)ciklopropil]metoksi}-piridin-3-il)benzoat dihidroklorid,
4-(2-kloro-5-{[1-(metilamino)ciklopropil]metoksi}piridin-3-il)benzamid hidroklorid,
4-(2-kloro-5-{[1-(metilamino)ciklopropil]metoksi}piridin-3-il)benzojeva kiselina hidroklorid,
(1-{[(2-kloro-3,4'-bipiridin-5-il)oksi]metil}ciklopropil)metilamin dihidroklorid,
{1-[({6-kloro-5-[4-(2H-tetrazol-5-il)fenil]piridin-3-il}oksi)-metil]ciklopropil}metilamin dihidroklorid,
[1-({[5,6-bis(4-klorfenil)piridin-3-il]oksi}metil)ciklopropil]metilamin dihidroklorid,
5-(4-aminofenil)-6-metil-N-{[1-(metilamino)ciklopropil]-metil}piridin-3-amin trihidroklorid,
njihovi enantiomeri, dijastereoizomeri, kao i njihove adicijske soli s farmaceutski prihvatljivom kiselinom ili farmaceutski prihvatljivom bazom.
11. Postupak priprave spojeva formule (I), naznačen time, da se kao početna tvar koristi spoj formule (II):
[image]
u kojoj R'2 predstavlja atom vodika, skupinu metil ili skupinu tert-butoksikarbonil, a R1, R3, R4, R5, X i n su definirani jednako kao u formuli (I), spojevi formule (II) koji se izlažu reakciji sa spojem formule (III):
[image]
u kojoj W predstavlja skupinu -Sn(C4H9)3, -B(OH)2 i
[image]
a Ra, Rb, Rc, Rd, Re, Y i Z su definirani jednako kao u formuli (I), u nazočnosti Pd(PPh3)4 u bazičnoj sredini, čime se dobivaju spojevi formule (IV):
[image]
u kojoj su R1, R'2, R3, R4, R5, X, Y, Z, Ra, Rb, Rc, Rd, Re i n definirani jednako kao gore, spojevi formule (IV) koji se izlažu djelovanju klorovodične kiseline, u slučaju kada R'2 predstavlja skupinu tert-butoksikarbonil, čime se dobivaju spojevi formule (I/a), koji predstavljaju poseban slučaj spojeva formule (I):
[image]
u kojoj su R1, R3, R4, R5, X, Y, Z, Ra, Rb, Rc, Rd, Re i n definirani jednako kao gore, spojevi formule (I/a) koji se izlažu reakciji sa spojem formule (V):
R"2 – L2 (V)
u kojoj R"2 predstavlja skupinu ravni ili razgranani alkil (C1-C6) ili ravni ili razgranani arilalkil (C1-C6), a L2 predstavlja uobičajenu odlazeću skupinu u organskoj kemiji, u bazičnoj sredini, čime se dobivaju spojevi formule (I/b), koji predstavljaju poseban slučaj spojeva formule (I):
[image]
u kojoj su R1, R"2, R3, R4, R5, X, Y, Z, Ra, Rb, Rc, Rd, Re i n definirani jednako kao gore, skup spojeva formula (l/a) i (l/b) koji tvore skup spojeva sukladno predmetnom izumu koji se, prema potrebi, pročišćavaju klasičnim tehnikama pročišćavanja, koji se mogu razdvojiti na svoje različite izomere klasičnom tehnikom razdvajanja i koji se, prema potrebi, prevode u svoje adicijske soli s farmaceutski prihvatljivom kiselinom ili farmaceutski prihvatljivom bazom.
12. Farmaceutski pripravci, naznačeni time, da kao djelatnu tvar sadrže najmanje jedan spoj sukladno bilo kojem patentnom zahtjevu 1 do 10, sam ili u kombinaciji s jednim ili više inertnih, netoksičnih, farmaceutski prihvatljivih ekscipijensa ili vehikula.
13. Farmaceutski pripravci u skladu s patentnim zahtjevom 12, naznačeni time, da kao djelatnu tvar sadrže najmanje jedan spoj sukladno bilo kojem patentnom zahtjevu 1 do 10, a korisni su kao specifični nikotinski ligand receptora α4β2.
14. Farmaceutski pripravci u skladu s patentnim zahtjevom 12, naznačeni time, da kao djelatnu tvar sadrže najmanje jedan spoj sukladno bilo kojem patentnom zahtjevu 1 do 10, a korisni su u liječenju poremećaja pamćenja povezanih sa starenjem mozga i neurodegenerativnim bolestima te u liječenju poremećaja raspoloženja, Touretteovog sindroma, sindroma hiperaktivnosti s poremećajima pažnje, odvikavanja od pušenja i boli.
15. Farmaceutski pripravci u skladu s patentnim zahtjevom 12, naznačeni time, da kao djelatnu tvar sadrže najmanje jedan spoj sukladno bilo kojem patentnom zahtjevu 1 do 10, a korisni su u liječenju poremećaja pamćenja povezanih s Alzheimerovom bolesti, Parkinsonovom bolesti, Pickovom bolesti, Korsakoffljevom bolesti i frontotemporalnom demencijom i subkortikalnom demencijom.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0600784A FR2896800B1 (fr) | 2006-01-30 | 2006-01-30 | Nouveaux composes pyridinylaminoalkylene-et pyridinyloxyalkylene-cyclopropanamines polysubstitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| PCT/FR2007/000170 WO2007085750A1 (fr) | 2006-01-30 | 2007-01-30 | Nouveaux composes pyridinylaminoalkylene- et pyridinyloxyalkylene- cyclopropanamines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
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| EP (1) | EP1979321B9 (hr) |
| JP (1) | JP2009525311A (hr) |
| KR (1) | KR101050910B1 (hr) |
| CN (1) | CN101374814B (hr) |
| AR (1) | AR059221A1 (hr) |
| AT (1) | ATE437857T1 (hr) |
| AU (1) | AU2007209235B2 (hr) |
| BR (1) | BRPI0710443A2 (hr) |
| CA (1) | CA2640482C (hr) |
| CY (1) | CY1109477T1 (hr) |
| DE (1) | DE602007001779D1 (hr) |
| DK (1) | DK1979321T3 (hr) |
| EA (1) | EA015227B1 (hr) |
| ES (1) | ES2330899T3 (hr) |
| FR (1) | FR2896800B1 (hr) |
| GE (1) | GEP20105090B (hr) |
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| RS (1) | RS51065B (hr) |
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| US8975261B2 (en) | 2011-05-24 | 2015-03-10 | Merck Sharp & Dohme Corp. | Aryloxmethyl cyclopropane derivatives as PDE10 inhibitors |
| BR112017004334A2 (pt) * | 2014-09-05 | 2018-08-07 | Celgene Quanticel Res Inc | inibidores de desmetilase específica de lisina-1. |
| US20180311238A1 (en) * | 2017-04-28 | 2018-11-01 | Saniona A/S | Selective Agonist Of a6 Containing nAChRs |
| CN110483392A (zh) * | 2018-05-14 | 2019-11-22 | 上海海和药物研究开发有限公司 | 合成n-保护的喹啉-7-基氧基甲基环丙基胺衍生物的方法及合成中间体 |
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| JP2001261652A (ja) * | 2000-03-21 | 2001-09-26 | Suntory Ltd | 二置換イミノヘテロサイクリック化合物 |
| FR2810664B1 (fr) * | 2000-06-27 | 2004-12-24 | Adir | Nouveaux composes cyclopropaniques 1,1 et 1,2-dissubstitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US7098331B2 (en) * | 2003-03-05 | 2006-08-29 | Targacept, Inc. | Arylvinylazacycloalkane compounds and methods of preparation and use thereof |
| FR2889188B1 (fr) * | 2005-07-28 | 2007-09-07 | Servier Lab | Nouveaux composes 1,1-pyridinylaminocyclopropanamines polysubstitues, leur procede de preparation et les compositions phamaceutiques qui les contiennent |
| FR2889187B1 (fr) * | 2005-07-28 | 2007-09-07 | Servier Lab | Nouveaux composes 1,1-pyridinyloxycyclopropanamines polysusbstitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
-
2006
- 2006-01-30 FR FR0600784A patent/FR2896800B1/fr not_active Expired - Fee Related
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2007
- 2007-01-29 AR ARP070100362A patent/AR059221A1/es unknown
- 2007-01-30 RS RSP-2009/0450A patent/RS51065B/sr unknown
- 2007-01-30 DK DK07730888T patent/DK1979321T3/da active
- 2007-01-30 DE DE602007001779T patent/DE602007001779D1/de active Active
- 2007-01-30 UA UAA200810613A patent/UA88116C2/ru unknown
- 2007-01-30 AT AT07730888T patent/ATE437857T1/de active
- 2007-01-30 JP JP2008552845A patent/JP2009525311A/ja not_active Withdrawn
- 2007-01-30 PT PT07730888T patent/PT1979321E/pt unknown
- 2007-01-30 EA EA200801681A patent/EA015227B1/ru not_active IP Right Cessation
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- 2007-01-30 EP EP07730888A patent/EP1979321B9/fr active Active
- 2007-01-30 MY MYPI20082681A patent/MY149068A/en unknown
- 2007-01-30 WO PCT/FR2007/000170 patent/WO2007085750A1/fr active Application Filing
- 2007-01-30 US US12/223,311 patent/US20100317698A1/en not_active Abandoned
- 2007-01-30 AU AU2007209235A patent/AU2007209235B2/en not_active Ceased
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