JP4542264B2 - Ｃｎｓ障害を処置するためのアゼチジンカルボキサミド誘導体 - Google Patents
Ｃｎｓ障害を処置するためのアゼチジンカルボキサミド誘導体 Download PDFInfo
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- JP4542264B2 JP4542264B2 JP2000528537A JP2000528537A JP4542264B2 JP 4542264 B2 JP4542264 B2 JP 4542264B2 JP 2000528537 A JP2000528537 A JP 2000528537A JP 2000528537 A JP2000528537 A JP 2000528537A JP 4542264 B2 JP4542264 B2 JP 4542264B2
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- Prior art keywords
- compound
- azetidine
- compound according
- phenyl
- trifluoromethyl
- 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
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- 208000015114 central nervous system disease Diseases 0.000 title claims abstract description 7
- PVXOUGHWLCBJOW-UHFFFAOYSA-N azetidine-1-carboxamide Chemical class NC(=O)N1CCC1 PVXOUGHWLCBJOW-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 145
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 22
- 238000011282 treatment Methods 0.000 claims abstract description 21
- 230000036506 anxiety Effects 0.000 claims abstract description 19
- 206010015037 epilepsy Diseases 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 238000011321 prophylaxis Methods 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 3
- -1 (trifluoromethyl) phenyl Chemical group 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 16
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 15
- 206010022437 insomnia Diseases 0.000 claims description 15
- 238000001356 surgical procedure Methods 0.000 claims description 15
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
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- 125000004122 cyclic group Chemical group 0.000 claims description 5
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- 238000009101 premedication Methods 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 208000008238 Muscle Spasticity Diseases 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 208000018198 spasticity Diseases 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
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- IYGJPNAEMKBWCF-UHFFFAOYSA-N 1-benzhydryl-3-(4-fluorophenyl)azetidine Chemical compound C1=CC(F)=CC=C1C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 IYGJPNAEMKBWCF-UHFFFAOYSA-N 0.000 description 12
- AVUDXLOVIBJFQA-UHFFFAOYSA-N 1-benzhydrylazetidin-3-one Chemical compound C1C(=O)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 AVUDXLOVIBJFQA-UHFFFAOYSA-N 0.000 description 12
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
- LKPALSUBQRWDMZ-UHFFFAOYSA-N 1-benzhydryl-3-(4-tert-butylphenyl)azetidine Chemical compound C1=CC(C(C)(C)C)=CC=C1C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 LKPALSUBQRWDMZ-UHFFFAOYSA-N 0.000 description 11
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
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- HYMUREYQKUJWIQ-UHFFFAOYSA-N 1-benzhydryl-3-[4-(trifluoromethyl)phenyl]azetidine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 HYMUREYQKUJWIQ-UHFFFAOYSA-N 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- YFUOIHFQICAKTD-UHFFFAOYSA-N 1-benzhydryl-3-(4-chlorophenyl)azetidine Chemical compound C1=CC(Cl)=CC=C1C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 YFUOIHFQICAKTD-UHFFFAOYSA-N 0.000 description 7
- DMDDOOGJRZVTPH-UHFFFAOYSA-N 1-benzhydryl-3-(4-fluorophenyl)azetidin-3-ol Chemical compound C1C(O)(C=2C=CC(F)=CC=2)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 DMDDOOGJRZVTPH-UHFFFAOYSA-N 0.000 description 7
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- HXKKHQJGJAFBHI-GSVOUGTGSA-N (2R)-1-aminopropan-2-ol Chemical compound C[C@@H](O)CN HXKKHQJGJAFBHI-GSVOUGTGSA-N 0.000 description 6
- VDECBPZVCMSIKK-UHFFFAOYSA-N 1-benzhydryl-3-(4-tert-butylphenyl)-3-chloroazetidine Chemical compound C1=CC(C(C)(C)C)=CC=C1C1(Cl)CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 VDECBPZVCMSIKK-UHFFFAOYSA-N 0.000 description 6
- BMELHQNFXXRNIQ-UHFFFAOYSA-N 1-benzhydryl-3-(4-tert-butylphenyl)azetidin-3-ol Chemical compound C1=CC(C(C)(C)C)=CC=C1C1(O)CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 BMELHQNFXXRNIQ-UHFFFAOYSA-N 0.000 description 6
- IRPMIKJQQYLTLF-UHFFFAOYSA-N 1-benzhydryl-3-chloro-3-(4-fluorophenyl)azetidine Chemical compound C1=CC(F)=CC=C1C1(Cl)CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 IRPMIKJQQYLTLF-UHFFFAOYSA-N 0.000 description 6
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- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 6
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000003151 isocoumarinyl group Chemical group C1(=O)OC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 125000005438 isoindazolyl group Chemical group 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000008263 liquid aerosol Substances 0.000 description 1
- 125000001288 lysyl group Chemical group 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- RMXGWLUCCKWPGK-UHFFFAOYSA-M magnesium;1,2-dichlorobenzene-5-ide;bromide Chemical compound [Mg+2].[Br-].ClC1=CC=[C-]C=C1Cl RMXGWLUCCKWPGK-UHFFFAOYSA-M 0.000 description 1
- BRKADVNLTRCLOW-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=[C-]C=C1 BRKADVNLTRCLOW-UHFFFAOYSA-M 0.000 description 1
- JFWSITPEDQPZNZ-UHFFFAOYSA-M magnesium;tert-butylbenzene;bromide Chemical compound [Mg+2].[Br-].CC(C)(C)C1=CC=[C-]C=C1 JFWSITPEDQPZNZ-UHFFFAOYSA-M 0.000 description 1
- 210000005171 mammalian brain Anatomy 0.000 description 1
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- 230000001404 mediated effect Effects 0.000 description 1
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- 125000002950 monocyclic group Chemical group 0.000 description 1
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- 230000037023 motor activity Effects 0.000 description 1
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- 239000003158 myorelaxant agent Substances 0.000 description 1
- JRHGEHVPXIJESH-SECBINFHSA-N n-[(2r)-2-hydroxypropyl]-3-[4-(trifluoromethyl)phenyl]azetidine-1-carboxamide Chemical compound C1N(C(=O)NC[C@H](O)C)CC1C1=CC=C(C(F)(F)F)C=C1 JRHGEHVPXIJESH-SECBINFHSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 230000000508 neurotrophic effect Effects 0.000 description 1
- 230000002276 neurotropic effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000002474 noradrenergic effect Effects 0.000 description 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N o-hydroxybenzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
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- 235000008390 olive oil Nutrition 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- RLXDCJUIXHSXQD-UHFFFAOYSA-N oxalic acid;hydrate Chemical compound O.OC(=O)C(O)=O.OC(=O)C(O)=O RLXDCJUIXHSXQD-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229960005152 pentetrazol Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006042 reductive dechlorination reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000028527 righting reflex Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- 230000007428 synaptic transmission, GABAergic Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 231100000889 vertigo Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9801499.6A GB9801499D0 (en) | 1998-01-23 | 1998-01-23 | Chemical compounds iii |
| GB9801499.6 | 1998-01-23 | ||
| GB9824458.5 | 1998-11-06 | ||
| GBGB9824458.5A GB9824458D0 (en) | 1998-11-06 | 1998-11-06 | Chemical compounds II |
| PCT/GB1999/000223 WO1999037613A1 (en) | 1998-01-23 | 1999-01-22 | Azetidinecarboxamide derivatives for treating cns disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002501046A JP2002501046A (ja) | 2002-01-15 |
| JP2002501046A5 JP2002501046A5 (https=) | 2006-02-23 |
| JP4542264B2 true JP4542264B2 (ja) | 2010-09-08 |
Family
ID=26313009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000528537A Expired - Lifetime JP4542264B2 (ja) | 1998-01-23 | 1999-01-22 | Ｃｎｓ障害を処置するためのアゼチジンカルボキサミド誘導体 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6831078B1 (https=) |
| EP (1) | EP1049670B1 (https=) |
| JP (1) | JP4542264B2 (https=) |
| AT (1) | ATE220665T1 (https=) |
| AU (1) | AU2178099A (https=) |
| DE (1) | DE69902142T2 (https=) |
| DK (1) | DK1049670T3 (https=) |
| ES (1) | ES2181387T3 (https=) |
| PT (1) | PT1049670E (https=) |
| WO (1) | WO1999037613A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9917384D0 (en) * | 1999-07-23 | 1999-09-22 | Cerebrus Ltd | Chemical compounds-III |
| CN102224135A (zh) * | 2008-11-24 | 2011-10-19 | Nsab神经研究瑞典公司分公司 | 用作皮质儿茶酚胺能神经传递调节剂的新3-苯基-氮杂环丁烷衍生物 |
| CN115650893B (zh) * | 2022-10-24 | 2024-08-06 | 南通华祥医药科技有限公司 | 一种1-二苯甲基氮杂环丁烷-3-酮的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB872447A (en) * | 1958-12-23 | 1961-07-12 | Lepetit Spa | 1-carbamyl-3-substituted azetidines |
| US4226861A (en) | 1978-04-18 | 1980-10-07 | A. H. Robins Company, Inc. | N-Lower-alkyl 3-phenoxy-1-azetidinecarboxamides |
| IL68699A (en) | 1982-08-19 | 1986-08-31 | Robins Co Inc A H | 3-phenoxy-1-azetidine-carboxamides,their preparation and pharmaceutical compositions containing them |
| US4505907A (en) | 1982-09-02 | 1985-03-19 | A. H. Robins Company, Inc. | N-Formyl and N-hydroxymethyl-3-phenoxy-1-azetidinecarboxamides |
| US4956359A (en) * | 1985-02-28 | 1990-09-11 | A. H. Robins Company, Inc. | 3-aryloxy and 3-arylthioazetidinecarboxamides as anticonvulsants and antiepileptics |
| IE58943B1 (en) | 1985-02-28 | 1993-12-01 | Robins Co Inc A H | 3-Aryloxy-azetidine-carboxamides |
-
1999
- 1999-01-22 AU AU21780/99A patent/AU2178099A/en not_active Abandoned
- 1999-01-22 DK DK99901781T patent/DK1049670T3/da active
- 1999-01-22 DE DE69902142T patent/DE69902142T2/de not_active Expired - Lifetime
- 1999-01-22 AT AT99901781T patent/ATE220665T1/de not_active IP Right Cessation
- 1999-01-22 WO PCT/GB1999/000223 patent/WO1999037613A1/en not_active Ceased
- 1999-01-22 PT PT99901781T patent/PT1049670E/pt unknown
- 1999-01-22 EP EP99901781A patent/EP1049670B1/en not_active Expired - Lifetime
- 1999-01-22 JP JP2000528537A patent/JP4542264B2/ja not_active Expired - Lifetime
- 1999-01-22 ES ES99901781T patent/ES2181387T3/es not_active Expired - Lifetime
- 1999-01-22 US US09/600,631 patent/US6831078B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2181387T3 (es) | 2003-02-16 |
| JP2002501046A (ja) | 2002-01-15 |
| WO1999037613A1 (en) | 1999-07-29 |
| PT1049670E (pt) | 2002-12-31 |
| ATE220665T1 (de) | 2002-08-15 |
| EP1049670A1 (en) | 2000-11-08 |
| DE69902142D1 (de) | 2002-08-22 |
| DE69902142T2 (de) | 2003-01-09 |
| DK1049670T3 (da) | 2002-11-11 |
| AU2178099A (en) | 1999-08-09 |
| EP1049670B1 (en) | 2002-07-17 |
| US6831078B1 (en) | 2004-12-14 |
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