TW201034667A - N-[(6-azabicyclo[3.2.1]oct-1-yl)arylmethyl]benzamide derivatives, preparation and therapeutic use thereof - Google Patents

N-[(6-azabicyclo[3.2.1]oct-1-yl)arylmethyl]benzamide derivatives, preparation and therapeutic use thereof Download PDF

Info

Publication number: TW201034667A
Authority: TW; Taiwan
Prior art keywords: group; compound; azabicyclo; formula; trifluoromethyl
Prior art date: 2009-02-10

Application number

TW099104006A

Other languages

English (en)

Chinese (zh)

Inventor

Gihad Dargazanli

Genevieve Estenne-Bouhtou

Florence Medaisko

Original Assignee

Sanofi Aventis

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2009-02-10

Filing date

2010-02-09

Publication date

2010-10-01

2010-02-09 Application filed by Sanofi Aventis filed Critical Sanofi Aventis

2010-10-01 Publication of TW201034667A publication Critical patent/TW201034667A/zh

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-1 6-azabicyclo[3.2.1]oct-1-yl Chemical group 0.000 title claims abstract description 30
238000002360 preparation method Methods 0.000 title claims description 11
125000005002 aryl methyl group Chemical group 0.000 title abstract description 3
230000001225 therapeutic effect Effects 0.000 title abstract description 3
125000005843 halogen group Chemical group 0.000 claims abstract description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
238000000034 method Methods 0.000 claims abstract description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 10
150000002367 halogens Chemical class 0.000 claims abstract description 10
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims abstract description 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 5
125000001624 naphthyl group Chemical group 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 111
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 66
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 46
125000000217 alkyl group Chemical group 0.000 claims description 36
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 28
125000003545 alkoxy group Chemical group 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 14
150000001412 amines Chemical class 0.000 claims description 13
125000004429 atom Chemical group 0.000 claims description 11
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 7
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 7
GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 claims description 6
125000001041 indolyl group Chemical group 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
108020004021 3-ketosteroid receptors Proteins 0.000 claims description 5
239000005711 Benzoic acid Substances 0.000 claims description 5
206010036790 Productive cough Diseases 0.000 claims description 5
235000010233 benzoic acid Nutrition 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
208000035475 disorder Diseases 0.000 claims description 5
239000007789 gas Chemical group 0.000 claims description 5
210000003802 sputum Anatomy 0.000 claims description 5
208000024794 sputum Diseases 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
206010012289 Dementia Diseases 0.000 claims description 3
208000030814 Eating disease Diseases 0.000 claims description 3
208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
208000019695 Migraine disease Diseases 0.000 claims description 3
208000019022 Mood disease Diseases 0.000 claims description 3
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 3
208000002193 Pain Diseases 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
230000003542 behavioural effect Effects 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 3
235000014632 disordered eating Nutrition 0.000 claims description 3
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
230000004770 neurodegeneration Effects 0.000 claims description 3
208000015122 neurodegenerative disease Diseases 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
208000020016 psychiatric disease Diseases 0.000 claims description 3
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230000009329 sexual behaviour Effects 0.000 claims description 3
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208000020925 Bipolar disease Diseases 0.000 claims description 2
208000028017 Psychotic disease Diseases 0.000 claims description 2
206010041235 Snoring Diseases 0.000 claims description 2
230000001154 acute effect Effects 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
230000001684 chronic effect Effects 0.000 claims description 2
230000001149 cognitive effect Effects 0.000 claims description 2
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
239000003814 drug Substances 0.000 claims 5
125000004414 alkyl thio group Chemical group 0.000 claims 3
208000019901 Anxiety disease Diseases 0.000 claims 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
206010033664 Panic attack Diseases 0.000 claims 2
229940037003 alum Drugs 0.000 claims 2
230000036506 anxiety Effects 0.000 claims 2
208000019906 panic disease Diseases 0.000 claims 2
238000006467 substitution reaction Methods 0.000 claims 2
YMMCBGIHBVKZGD-UHFFFAOYSA-N (4-fluorophenyl)methylhydrazine Chemical compound NNCC1=CC=C(F)C=C1 YMMCBGIHBVKZGD-UHFFFAOYSA-N 0.000 claims 1
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 1
QUFBKANNFIKCBB-UHFFFAOYSA-N 2,6-dichloro-1h-indole Chemical compound C1=C(Cl)C=C2NC(Cl)=CC2=C1 QUFBKANNFIKCBB-UHFFFAOYSA-N 0.000 claims 1
JBMBVWROWJGFMG-UHFFFAOYSA-N 2-chloro-7h-purine Chemical compound ClC1=NC=C2NC=NC2=N1 JBMBVWROWJGFMG-UHFFFAOYSA-N 0.000 claims 1
206010000117 Abnormal behaviour Diseases 0.000 claims 1
241000219198 Brassica Species 0.000 claims 1
235000003351 Brassica cretica Nutrition 0.000 claims 1
235000003343 Brassica rupestris Nutrition 0.000 claims 1
208000020401 Depressive disease Diseases 0.000 claims 1
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
239000005864 Sulphur Substances 0.000 claims 1
208000029650 alcohol withdrawal Diseases 0.000 claims 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
230000002950 deficient Effects 0.000 claims 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
201000003102 mental depression Diseases 0.000 claims 1
235000010460 mustard Nutrition 0.000 claims 1
150000002923 oximes Chemical class 0.000 claims 1
239000008177 pharmaceutical agent Substances 0.000 claims 1
239000004089 psychotropic agent Substances 0.000 claims 1
208000020685 sleep-wake disease Diseases 0.000 claims 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
230000015572 biosynthetic process Effects 0.000 abstract description 2
239000011737 fluorine Substances 0.000 abstract description 2
229910052731 fluorine Inorganic materials 0.000 abstract description 2
239000001257 hydrogen Substances 0.000 abstract description 2
229910052739 hydrogen Inorganic materials 0.000 abstract description 2
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 abstract description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
125000004399 C1-C4 alkenyl group Chemical group 0.000 abstract 1
125000002785 azepinyl group Chemical group 0.000 abstract 1
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
238000003786 synthesis reaction Methods 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 22
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
230000002829 reductive effect Effects 0.000 description 16
238000005481 NMR spectroscopy Methods 0.000 description 15
239000000243 solution Substances 0.000 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 13
239000000460 chlorine Substances 0.000 description 11
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
235000011114 ammonium hydroxide Nutrition 0.000 description 6
238000000605 extraction Methods 0.000 description 6
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
150000002825 nitriles Chemical class 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000002904 solvent Substances 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000012429 reaction media Substances 0.000 description 5
229910052707 ruthenium Inorganic materials 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
239000004471 Glycine Substances 0.000 description 4
102000010726 Glycine Plasma Membrane Transport Proteins Human genes 0.000 description 4
108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
238000004949 mass spectrometry Methods 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
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 3
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 3
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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238000010521 absorption reaction Methods 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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QSMUZDZBKFISDF-UHFFFAOYSA-N n-benzyl-6-azabicyclo[3.2.1]octan-5-amine Chemical compound C1C(CCC2)CNC12NCC1=CC=CC=C1 QSMUZDZBKFISDF-UHFFFAOYSA-N 0.000 description 3
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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Classifications

- 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
- C07D487/08—Bridged systems
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
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Pain & Pain Management (AREA)
Psychiatry (AREA)
Addiction (AREA)
Epidemiology (AREA)
Anesthesiology (AREA)
Hospice & Palliative Care (AREA)
Rheumatology (AREA)
Psychology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Indole Compounds (AREA)

TW099104006A 2009-02-10 2010-02-09 N-[(6-azabicyclo[3.2.1]oct-1-yl)arylmethyl]benzamide derivatives, preparation and therapeutic use thereof TW201034667A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR0900579A FR2941954B1 (fr)	2009-02-10	2009-02-10	Derives de n-°(6-aza-bicyclo°3.2.1!oct-1-yl)-aryl-methyl! benzamide, leur preparation et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
TW201034667A true TW201034667A (en)	2010-10-01

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ID=40935769

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW099104006A TW201034667A (en)	2009-02-10	2010-02-09	N-[(6-azabicyclo[3.2.1]oct-1-yl)arylmethyl]benzamide derivatives, preparation and therapeutic use thereof

Country Status (15)

Country	Link
EP (1)	EP2396335A1 (de)
JP (1)	JP2012517412A (de)
KR (1)	KR20110118813A (de)
CN (1)	CN102388050A (de)
AR (1)	AR075380A1 (de)
AU (1)	AU2010212703A1 (de)
BR (1)	BRPI1008544A2 (de)
CA (1)	CA2751866A1 (de)
FR (1)	FR2941954B1 (de)
IL (1)	IL214487A0 (de)
MX (1)	MX2011008459A (de)
SG (1)	SG173607A1 (de)
TW (1)	TW201034667A (de)
UY (1)	UY32429A (de)
WO (1)	WO2010092287A1 (de)

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2861070B1 (fr) *	2003-10-17	2006-01-06	Sanofi Synthelabo	Derives de n-[phenyl(pyrrolidin-2-yl)methyl]benzamide et n-[(azepan-2-yl)phenylmethyl]benzamide, leur preparation et leur application en therapeutique
FR2861076B1 (fr) *	2003-10-17	2006-01-06	Sanofi Synthelabo	Derives de n-heterocyclymethylbenzamide, leur preparation et leur application en therapeutique
WO2005058317A1 (en) *	2003-12-18	2005-06-30	Glaxo Group Limited	Glycine transporter-1 inhibirors
JP5175736B2 (ja) *	2005-10-28	2013-04-03	メルク・シャープ・エンド・ドーム・コーポレイション	ピペリジングリシン輸送体阻害剤
KR20090100360A (ko) *	2006-11-30	2009-09-23	세넉스 바이오파마, 인크.	중추신경계 장애 치료제로서의 피바가빈의 디알킬아미노 알킬 에스테르
TW200911808A (en) *	2007-07-23	2009-03-16	Astrazeneca Ab	Novel compounds

2009
- 2009-02-10 FR FR0900579A patent/FR2941954B1/fr not_active Expired - Fee Related
2010
- 2010-02-09 KR KR1020117021204A patent/KR20110118813A/ko not_active Withdrawn
- 2010-02-09 CA CA2751866A patent/CA2751866A1/fr not_active Abandoned
- 2010-02-09 AU AU2010212703A patent/AU2010212703A1/en not_active Abandoned
- 2010-02-09 JP JP2011548759A patent/JP2012517412A/ja not_active Withdrawn
- 2010-02-09 CN CN2010800156289A patent/CN102388050A/zh active Pending
- 2010-02-09 BR BRPI1008544A patent/BRPI1008544A2/pt not_active Application Discontinuation
- 2010-02-09 MX MX2011008459A patent/MX2011008459A/es not_active Application Discontinuation
- 2010-02-09 SG SG2011057213A patent/SG173607A1/en unknown
- 2010-02-09 AR ARP100100345A patent/AR075380A1/es unknown
- 2010-02-09 EP EP10708304A patent/EP2396335A1/de not_active Withdrawn
- 2010-02-09 WO PCT/FR2010/050204 patent/WO2010092287A1/fr not_active Ceased
- 2010-02-09 TW TW099104006A patent/TW201034667A/zh unknown
- 2010-02-10 UY UY0001032429A patent/UY32429A/es not_active Application Discontinuation
2011
- 2011-08-07 IL IL214487A patent/IL214487A0/en unknown

Also Published As

Publication number	Publication date
FR2941954B1 (fr)	2011-04-08
JP2012517412A (ja)	2012-08-02
BRPI1008544A2 (pt)	2016-03-15
CN102388050A (zh)	2012-03-21
CA2751866A1 (fr)	2010-08-19
KR20110118813A (ko)	2011-11-01
AU2010212703A1 (en)	2011-09-01
MX2011008459A (es)	2011-12-16
SG173607A1 (en)	2011-09-29
AR075380A1 (es)	2011-03-30
WO2010092287A1 (fr)	2010-08-19
UY32429A (es)	2010-09-30
EP2396335A1 (de)	2011-12-21
FR2941954A1 (fr)	2010-08-13
IL214487A0 (en)	2011-09-27

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