CA2489723C - Nouveaux derives d'aryl-{4-halogeno-4-[(heteroaryl-methylamino)-methyl]-piperidin-1-yl}-methanone, leur procede de preparation et leur utilisation a titre de medicaments - Google Patents
Nouveaux derives d'aryl-{4-halogeno-4-[(heteroaryl-methylamino)-methyl]-piperidin-1-yl}-methanone, leur procede de preparation et leur utilisation a titre de medicaments Download PDFInfo
- Publication number
- CA2489723C CA2489723C CA2489723A CA2489723A CA2489723C CA 2489723 C CA2489723 C CA 2489723C CA 2489723 A CA2489723 A CA 2489723A CA 2489723 A CA2489723 A CA 2489723A CA 2489723 C CA2489723 C CA 2489723C
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- fluoro
- piperidin
- methanone
- phenyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 239000003814 drug Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 238000000034 method Methods 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- -1 cyano, hydroxyl Chemical group 0.000 claims abstract description 34
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 22
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 20
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims abstract description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011737 fluorine Substances 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 150000004677 hydrates Chemical class 0.000 claims description 4
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- 150000007513 acids Chemical class 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
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- CLSFKOVAEVOMBN-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-fluoro-4-[[(5-methylpyrimidin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound N1=CC(C)=CN=C1CNCC1(F)CCN(C(=O)C=2C=C(Cl)C(Cl)=CC=2)CC1 CLSFKOVAEVOMBN-UHFFFAOYSA-N 0.000 claims 1
- AJEWINCTRQUEBR-UHFFFAOYSA-N (3,4-dichlorophenyl)-[4-fluoro-4-[[(6-methylpyridazin-3-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound N1=NC(C)=CC=C1CNCC1(F)CCN(C(=O)C=2C=C(Cl)C(Cl)=CC=2)CC1 AJEWINCTRQUEBR-UHFFFAOYSA-N 0.000 claims 1
- RCNYUDQCXUKYBA-UHFFFAOYSA-N (3,4-difluorophenyl)-[4-fluoro-4-[[(5-methylpyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound N1=CC(C)=CC=C1CNCC1(F)CCN(C(=O)C=2C=C(F)C(F)=CC=2)CC1 RCNYUDQCXUKYBA-UHFFFAOYSA-N 0.000 claims 1
- SALDQMKGRXMXGW-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-[4-[[(5-chloropyridin-2-yl)methylamino]methyl]-4-fluoropiperidin-1-yl]methanone Chemical compound C1=C(Cl)C(F)=CC=C1C(=O)N1CCC(F)(CNCC=2N=CC(Cl)=CC=2)CC1 SALDQMKGRXMXGW-UHFFFAOYSA-N 0.000 claims 1
- SVCRXGVDWDIMLL-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-[4-fluoro-4-[[(5-hydroxypyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound N1=CC(O)=CC=C1CNCC1(F)CCN(C(=O)C=2C=C(Cl)C(F)=CC=2)CC1 SVCRXGVDWDIMLL-UHFFFAOYSA-N 0.000 claims 1
- WAAXKNFGOFTGLP-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-[4-fluoro-4-[[(5-methylpyrimidin-2-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound N1=CC(C)=CN=C1CNCC1(F)CCN(C(=O)C=2C=C(Cl)C(F)=CC=2)CC1 WAAXKNFGOFTGLP-UHFFFAOYSA-N 0.000 claims 1
- UDSFREKDDUDKDN-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-[4-fluoro-4-[[(6-methylpyridazin-3-yl)methylamino]methyl]piperidin-1-yl]methanone Chemical compound N1=NC(C)=CC=C1CNCC1(F)CCN(C(=O)C=2C=C(Cl)C(F)=CC=2)CC1 UDSFREKDDUDKDN-UHFFFAOYSA-N 0.000 claims 1
- XPMHHHJWQFUFAU-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)-[4-fluoro-4-[[[5-(fluoromethyl)pyridin-2-yl]methylamino]methyl]piperidin-1-yl]methanone Chemical compound N1=CC(CF)=CC=C1CNCC1(F)CCN(C(=O)C=2C=C(Cl)C(F)=CC=2)CC1 XPMHHHJWQFUFAU-UHFFFAOYSA-N 0.000 claims 1
- CKPPJYLPMTUPAS-UHFFFAOYSA-N 2-fluoro-5-[4-fluoro-4-[[(5-methylpyridin-2-yl)methylamino]methyl]piperidine-1-carbonyl]benzonitrile Chemical compound N1=CC(C)=CC=C1CNCC1(F)CCN(C(=O)C=2C=C(C(F)=CC=2)C#N)CC1 CKPPJYLPMTUPAS-UHFFFAOYSA-N 0.000 claims 1
- QFNPKPKDVHIBAU-UHFFFAOYSA-N [4-fluoro-4-[[(5-methylpyridin-2-yl)methylamino]methyl]piperidin-1-yl]-(4-fluorophenyl)methanone Chemical compound N1=CC(C)=CC=C1CNCC1(F)CCN(C(=O)C=2C=CC(F)=CC=2)CC1 QFNPKPKDVHIBAU-UHFFFAOYSA-N 0.000 claims 1
- PTJQZFWLRCSHOS-UHFFFAOYSA-N [4-fluoro-4-[[(5-methylpyridin-2-yl)methylamino]methyl]piperidin-1-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound N1=CC(C)=CC=C1CNCC1(F)CCN(C(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 PTJQZFWLRCSHOS-UHFFFAOYSA-N 0.000 claims 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
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- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 description 28
- 238000002360 preparation method Methods 0.000 description 28
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- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 14
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- 150000001412 amines Chemical class 0.000 description 8
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 8
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- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- RELMGALDUYBFJF-UHFFFAOYSA-N [4-(aminomethyl)-4-fluoropiperidin-1-yl]-(4-fluorophenyl)methanone Chemical compound C1CC(CN)(F)CCN1C(=O)C1=CC=C(F)C=C1 RELMGALDUYBFJF-UHFFFAOYSA-N 0.000 description 1
- BIJPUEBJPVFNFK-UHFFFAOYSA-N [5-(fluoromethyl)pyridin-2-yl]methanol Chemical compound OCC1=CC=C(CF)C=N1 BIJPUEBJPVFNFK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- RDSGPHNFOMPILP-UHFFFAOYSA-N ethyl 6-(hydroxymethyl)pyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=C(CO)N=C1 RDSGPHNFOMPILP-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical compound COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229960001779 pargyline Drugs 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003138 primary alcohols Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011535 reaction buffer Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 230000002295 serotoninergic effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 229940082787 spirulina Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CEIJFEGBUDEYSX-FZDBZEDMSA-N tandospirone Chemical compound O=C([C@@H]1[C@H]2CC[C@H](C2)[C@@H]1C1=O)N1CCCCN(CC1)CCN1C1=NC=CC=N1 CEIJFEGBUDEYSX-FZDBZEDMSA-N 0.000 description 1
- 229950000505 tandospirone Drugs 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- UFXIRMVZNARBDL-UHFFFAOYSA-N trifluoro(morpholin-4-yl)-$l^{4}-sulfane Chemical compound FS(F)(F)N1CCOCC1 UFXIRMVZNARBDL-UHFFFAOYSA-N 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 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
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR02/07470 | 2002-06-18 | ||
| FR0207470A FR2840900B1 (fr) | 2002-06-18 | 2002-06-18 | Nouveaux derives d'aryl[4-halogeno-4- [(heteroaryl-methylamino)-methyl]-piperidin-1-yl]-methanone, leur procede de preparation et leur utilisation a titre de medicaments |
| PCT/FR2003/001873 WO2003106449A1 (fr) | 2002-06-18 | 2003-06-18 | Nouveaux derives d'aryl-{4-halogeno-4-[heteroaryl-methylamino)-methyl]-piperidin-1-yl}-methanone, leur procede de preparation et leur utilisation a titre de medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2489723A1 CA2489723A1 (fr) | 2003-12-24 |
| CA2489723C true CA2489723C (fr) | 2011-08-02 |
Family
ID=29595331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2489723A Expired - Lifetime CA2489723C (fr) | 2002-06-18 | 2003-06-18 | Nouveaux derives d'aryl-{4-halogeno-4-[(heteroaryl-methylamino)-methyl]-piperidin-1-yl}-methanone, leur procede de preparation et leur utilisation a titre de medicaments |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7547700B2 (enExample) |
| EP (1) | EP1539738B1 (enExample) |
| JP (1) | JP4699027B2 (enExample) |
| CN (1) | CN1308325C (enExample) |
| AT (1) | ATE424396T1 (enExample) |
| AU (1) | AU2003258816B2 (enExample) |
| BR (1) | BRPI0311976B8 (enExample) |
| CA (1) | CA2489723C (enExample) |
| DE (1) | DE60326468D1 (enExample) |
| ES (1) | ES2321927T3 (enExample) |
| FR (1) | FR2840900B1 (enExample) |
| MX (1) | MXPA05000024A (enExample) |
| WO (1) | WO2003106449A1 (enExample) |
| ZA (1) | ZA200500467B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2852244B1 (fr) | 2003-03-13 | 2007-09-07 | Pf Medicament | Utilisation de derives de pyridin-2-yl-methylamine pour la preparation d'un medicament destine au traitement des symptomes de la douleur chronique d'origine neuropathique ou psychogene |
| FR2891274B1 (fr) * | 2005-09-27 | 2007-11-23 | Pierre Fabre Medicament Sa | Procede de preparation du (3-chloro-4-fluoro-phenyl)-(4- fluoro-4-{[(5-methyl-pyrimidin-2-ylmethyl)-amino]-methyl}- piperidin-1-yl)-methanone et nouveaux derives pyrimidiniques intermediaires. |
| US8389534B2 (en) * | 2008-05-19 | 2013-03-05 | The University Of Tennessee Research Foundation | Pyrimidine non-classical cannabinoid compounds and related methods of use |
| CA2724737A1 (en) * | 2008-05-19 | 2009-11-26 | The University Of Tennessee Research Foundation | Pyrimidine non-classical cannabinoid compounds and related methods of use |
| FR2946344B1 (fr) | 2009-06-05 | 2012-05-25 | Pf Medicament | Nouveaux derives d'aryl-{4-halogeno-4-[aminomethyl]-piperidin-1-yl} methanone, leur procede de preparation et leur utilisation a titre de medicaments |
| EP2338873A1 (en) | 2009-12-22 | 2011-06-29 | Gmeiner, Peter | New aminotetraline derivatives |
| WO2018057576A1 (en) * | 2016-09-22 | 2018-03-29 | Auspex Pharmaceuticals, Inc. | Deuterium-substituted pyridin- and pyrimidin-2-yl-methylamine compounds |
| US11191758B2 (en) | 2017-07-20 | 2021-12-07 | Neurolixis | Use of selective serotonin 5-HT1A receptor agonists for treating side-effects of VMAT inhibitors |
| WO2023144166A1 (en) | 2022-01-26 | 2023-08-03 | Neurolixis | Use of serotonin 5-ht1a receptor agonists to treat diseases associated with sudden unexpected death in epilepsy |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN169588B (enExample) * | 1986-10-07 | 1991-11-16 | Pfizer Hospital Prod | |
| FR2755967B1 (fr) * | 1996-11-21 | 1999-01-29 | Pf Medicament | Derives de la pyridin-2-yl-methylamine, leur procede de preparation et leur application comme medicaments |
| FR2784378B1 (fr) * | 1998-10-09 | 2000-12-29 | Pf Medicament | Nouveaux derives d'aryl-(4-fluoro-4-[(2-pyridin-2-yl- ethylamino)-methyl]-piperidin-1-yl)-methanone, leur procede de preparation et leur utilisation a titre de medicaments |
| FR2820743B1 (fr) * | 2001-02-09 | 2005-02-25 | Pf Medicament | Procede et intermediaires de synthese pour la preparation de derives de pyridin-2-yl-methylamine |
-
2002
- 2002-06-18 FR FR0207470A patent/FR2840900B1/fr not_active Expired - Lifetime
-
2003
- 2003-06-18 CA CA2489723A patent/CA2489723C/fr not_active Expired - Lifetime
- 2003-06-18 MX MXPA05000024A patent/MXPA05000024A/es active IP Right Grant
- 2003-06-18 US US10/518,394 patent/US7547700B2/en active Active
- 2003-06-18 AU AU2003258816A patent/AU2003258816B2/en not_active Expired
- 2003-06-18 CN CNB038186047A patent/CN1308325C/zh not_active Expired - Lifetime
- 2003-06-18 DE DE60326468T patent/DE60326468D1/de not_active Expired - Lifetime
- 2003-06-18 BR BRPI0311976A patent/BRPI0311976B8/pt not_active IP Right Cessation
- 2003-06-18 ES ES03760060T patent/ES2321927T3/es not_active Expired - Lifetime
- 2003-06-18 EP EP03760060A patent/EP1539738B1/fr not_active Expired - Lifetime
- 2003-06-18 WO PCT/FR2003/001873 patent/WO2003106449A1/fr not_active Ceased
- 2003-06-18 AT AT03760060T patent/ATE424396T1/de not_active IP Right Cessation
- 2003-06-18 JP JP2004513281A patent/JP4699027B2/ja not_active Expired - Lifetime
-
2005
- 2005-01-18 ZA ZA2005/00467A patent/ZA200500467B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2489723A1 (fr) | 2003-12-24 |
| HK1075452A1 (en) | 2005-12-16 |
| DE60326468D1 (de) | 2009-04-16 |
| ZA200500467B (en) | 2005-12-28 |
| JP4699027B2 (ja) | 2011-06-08 |
| ES2321927T3 (es) | 2009-06-15 |
| BRPI0311976B1 (pt) | 2015-08-18 |
| EP1539738B1 (fr) | 2009-03-04 |
| AU2003258816A1 (en) | 2003-12-31 |
| BR0311976A (pt) | 2005-03-29 |
| AU2003258816B2 (en) | 2008-08-21 |
| US7547700B2 (en) | 2009-06-16 |
| WO2003106449A1 (fr) | 2003-12-24 |
| CN1308325C (zh) | 2007-04-04 |
| EP1539738A1 (fr) | 2005-06-15 |
| US20060100244A1 (en) | 2006-05-11 |
| BRPI0311976B8 (pt) | 2021-05-25 |
| ATE424396T1 (de) | 2009-03-15 |
| CN1675194A (zh) | 2005-09-28 |
| WO2003106449A8 (fr) | 2005-02-17 |
| FR2840900A1 (fr) | 2003-12-19 |
| JP2005534668A (ja) | 2005-11-17 |
| FR2840900B1 (fr) | 2005-02-25 |
| MXPA05000024A (es) | 2005-04-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20230619 |