ZA200308637B - 4-[Phenyl-(piperidin-4-yl)-amino]-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders. - Google Patents
4-[Phenyl-(piperidin-4-yl)-amino]-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders. Download PDFInfo
- Publication number
- ZA200308637B ZA200308637B ZA200308637A ZA200308637A ZA200308637B ZA 200308637 B ZA200308637 B ZA 200308637B ZA 200308637 A ZA200308637 A ZA 200308637A ZA 200308637 A ZA200308637 A ZA 200308637A ZA 200308637 B ZA200308637 B ZA 200308637B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- piperidin
- amino
- compound
- benzamide
- Prior art date
Links
- 230000036407 pain Effects 0.000 title claims description 11
- 208000018522 Gastrointestinal disease Diseases 0.000 title claims description 8
- 208000019901 Anxiety disease Diseases 0.000 title claims description 7
- 230000036506 anxiety Effects 0.000 title claims description 7
- 208000027520 Somatoform disease Diseases 0.000 title claims description 4
- 208000027753 pain disease Diseases 0.000 title claims description 4
- YFKZHFPNQFEPHF-UHFFFAOYSA-N 4-(n-piperidin-4-ylanilino)benzamide Chemical class C1=CC(C(=O)N)=CC=C1N(C=1C=CC=CC=1)C1CCNCC1 YFKZHFPNQFEPHF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 62
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- -1 NOy Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 208000002193 Pain Diseases 0.000 claims description 9
- LDUPVXSXLZOQAF-UHFFFAOYSA-N 4-bromo-n,n-diethylbenzamide Chemical compound CCN(CC)C(=O)C1=CC=C(Br)C=C1 LDUPVXSXLZOQAF-UHFFFAOYSA-N 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 7
- STXAVEHFKAXGOX-UHFFFAOYSA-N 3-bromobenzonitrile Chemical compound BrC1=CC=CC(C#N)=C1 STXAVEHFKAXGOX-UHFFFAOYSA-N 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000002346 iodo group Chemical group I* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 11
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 230000002829 reductive effect Effects 0.000 claims 2
- HSZIVHLCQPNQOE-UHFFFAOYSA-N 3-[4-(diethylcarbamoyl)-n-[1-(1h-imidazol-2-ylmethyl)piperidin-4-yl]anilino]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(C=CC=1)C(N)=O)C1CCN(CC=2NC=CN=2)CC1 HSZIVHLCQPNQOE-UHFFFAOYSA-N 0.000 claims 1
- YUWAIKLSVXKDQM-UHFFFAOYSA-N 3-[4-(diethylcarbamoyl)-n-[1-(1h-imidazol-5-ylmethyl)piperidin-4-yl]anilino]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(C=CC=1)C(N)=O)C1CCN(CC=2NC=NC=2)CC1 YUWAIKLSVXKDQM-UHFFFAOYSA-N 0.000 claims 1
- SKZXILXJTUIGSZ-UHFFFAOYSA-N 3-[4-(diethylcarbamoyl)-n-[1-(furan-2-ylmethyl)piperidin-4-yl]anilino]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(C=CC=1)C(N)=O)C1CCN(CC=2OC=CC=2)CC1 SKZXILXJTUIGSZ-UHFFFAOYSA-N 0.000 claims 1
- GRGQARAXZATPBE-UHFFFAOYSA-N 3-[4-(diethylcarbamoyl)-n-[1-(pyridin-2-ylmethyl)piperidin-4-yl]anilino]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(C=CC=1)C(N)=O)C1CCN(CC=2N=CC=CC=2)CC1 GRGQARAXZATPBE-UHFFFAOYSA-N 0.000 claims 1
- JZJSPCADPUUUEJ-UHFFFAOYSA-N 3-[4-(diethylcarbamoyl)-n-[1-(pyridin-3-ylmethyl)piperidin-4-yl]anilino]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(C=CC=1)C(N)=O)C1CCN(CC=2C=NC=CC=2)CC1 JZJSPCADPUUUEJ-UHFFFAOYSA-N 0.000 claims 1
- GZJALTYZCKYWTC-UHFFFAOYSA-N 3-[4-(diethylcarbamoyl)-n-[1-(pyridin-4-ylmethyl)piperidin-4-yl]anilino]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(C=CC=1)C(N)=O)C1CCN(CC=2C=CN=CC=2)CC1 GZJALTYZCKYWTC-UHFFFAOYSA-N 0.000 claims 1
- HUSCFKNTULOKOT-UHFFFAOYSA-N 3-[4-(diethylcarbamoyl)-n-[1-(thiophen-3-ylmethyl)piperidin-4-yl]anilino]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(C=CC=1)C(N)=O)C1CCN(CC2=CSC=C2)CC1 HUSCFKNTULOKOT-UHFFFAOYSA-N 0.000 claims 1
- SJBURJKJEJSVCV-UHFFFAOYSA-N 3-[4-(diethylcarbamoyl)-n-[1-[(1-methylimidazol-2-yl)methyl]piperidin-4-yl]anilino]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(C=CC=1)C(N)=O)C1CCN(CC=2N(C=CN=2)C)CC1 SJBURJKJEJSVCV-UHFFFAOYSA-N 0.000 claims 1
- KDIDFELALMETAT-UHFFFAOYSA-N 3-[4-(diethylcarbamoyl)-n-[1-[(4-fluorophenyl)methyl]piperidin-4-yl]anilino]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(C=CC=1)C(N)=O)C1CCN(CC=2C=CC(F)=CC=2)CC1 KDIDFELALMETAT-UHFFFAOYSA-N 0.000 claims 1
- QFSXVMVWFGFILE-UHFFFAOYSA-N 3-[4-(diethylcarbamoyl)-n-[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]anilino]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(C=CC=1)C(N)=O)C1CCN(CC=2C=CC(OC)=CC=2)CC1 QFSXVMVWFGFILE-UHFFFAOYSA-N 0.000 claims 1
- JTJXQWZJBAJVGH-UHFFFAOYSA-N 3-[4-(diethylcarbamoyl)-n-[1-[(4-methylphenyl)methyl]piperidin-4-yl]anilino]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(C=CC=1)C(N)=O)C1CCN(CC=2C=CC(C)=CC=2)CC1 JTJXQWZJBAJVGH-UHFFFAOYSA-N 0.000 claims 1
- YCKPFIZUVGRVLD-UHFFFAOYSA-N 3-[n-(1-benzylpiperidin-4-yl)-4-(diethylcarbamoyl)anilino]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(C=CC=1)C(N)=O)C1CCN(CC=2C=CC=CC=2)CC1 YCKPFIZUVGRVLD-UHFFFAOYSA-N 0.000 claims 1
- ASVFDTYOAIGRTG-UHFFFAOYSA-N 3-[n-[1-[(2,4-dichlorophenyl)methyl]piperidin-4-yl]-4-(diethylcarbamoyl)anilino]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(C=CC=1)C(N)=O)C1CCN(CC=2C(=CC(Cl)=CC=2)Cl)CC1 ASVFDTYOAIGRTG-UHFFFAOYSA-N 0.000 claims 1
- RTYGKHNAXMRHOM-UHFFFAOYSA-N 3-[n-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-4-(diethylcarbamoyl)anilino]benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(C=CC=1)C(N)=O)C1CCN(CC=2C=CC(Cl)=CC=2)CC1 RTYGKHNAXMRHOM-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 101710198144 Endopolygalacturonase I Proteins 0.000 claims 1
- 208000014540 Functional gastrointestinal disease Diseases 0.000 claims 1
- 101710191566 Probable endopolygalacturonase I Proteins 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001860 citric acid derivatives Chemical class 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 20
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000003818 flash chromatography Methods 0.000 description 8
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000000556 agonist Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229960005235 piperonyl butoxide Drugs 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000730 antalgic agent Substances 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940035676 analgesics Drugs 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- QQQZEFAUOMUXLS-UHFFFAOYSA-N (1-diphenylphosphanyl-9,9-dimethylxanthen-2-yl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C1=C2C(C)(C)C3=CC=CC=C3OC2=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QQQZEFAUOMUXLS-UHFFFAOYSA-N 0.000 description 2
- YUBDLZGUSSWQSS-UHFFFAOYSA-N 1-benzylpiperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CC=C1 YUBDLZGUSSWQSS-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 102000003840 Opioid Receptors Human genes 0.000 description 2
- 108090000137 Opioid Receptors Proteins 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000009435 amidation Effects 0.000 description 2
- 238000007112 amidation reaction Methods 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 238000001949 anaesthesia Methods 0.000 description 2
- 230000003444 anaesthetic effect Effects 0.000 description 2
- 230000036592 analgesia Effects 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003140 primary amides Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 208000011117 substance-related disease Diseases 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- VYPYKCPWNPPBBX-UHFFFAOYSA-N 2-(3-bromophenyl)-1,3-dioxolane Chemical compound BrC1=CC=CC(C2OCCO2)=C1 VYPYKCPWNPPBBX-UHFFFAOYSA-N 0.000 description 1
- OMTPSHFALNVEHI-UHFFFAOYSA-N 2-(3-cyano-n-piperidin-4-ylanilino)-n,n-diethylbenzamide Chemical compound CCN(CC)C(=O)C1=CC=CC=C1N(C=1C=C(C=CC=1)C#N)C1CCNCC1 OMTPSHFALNVEHI-UHFFFAOYSA-N 0.000 description 1
- LSSMSUXPIUTNMG-UHFFFAOYSA-N 4-[(1-benzylpiperidin-4-yl)amino]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1NC1CCN(CC=2C=CC=CC=2)CC1 LSSMSUXPIUTNMG-UHFFFAOYSA-N 0.000 description 1
- KQWVAUSXZDRQPZ-UMTXDNHDSA-N 4-[(R)-[(2S,5R)-2,5-dimethyl-4-prop-2-enyl-1-piperazinyl]-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide Chemical group C1=CC(C(=O)N(CC)CC)=CC=C1[C@H](C=1C=C(OC)C=CC=1)N1[C@@H](C)CN(CC=C)[C@H](C)C1 KQWVAUSXZDRQPZ-UMTXDNHDSA-N 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 208000031091 Amnestic disease Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010058019 Cancer Pain Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 208000027932 Collagen disease Diseases 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 206010013654 Drug abuse Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000011688 Generalised anxiety disease Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010021118 Hypotonia Diseases 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000019430 Motor disease Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 206010037423 Pulmonary oedema Diseases 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 206010041250 Social phobia Diseases 0.000 description 1
- 208000020339 Spinal injury Diseases 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 208000030886 Traumatic Brain injury Diseases 0.000 description 1
- 206010046543 Urinary incontinence Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 230000006986 amnesia Effects 0.000 description 1
- 229940124326 anaesthetic agent Drugs 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 229940005530 anxiolytics Drugs 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000005961 cardioprotection Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000002920 convulsive effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 238000002059 diagnostic imaging Methods 0.000 description 1
- 238000012631 diagnostic technique Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 108010092028 endopolygalacturonase II Proteins 0.000 description 1
- 208000029364 generalized anxiety disease Diseases 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 239000000842 neuromuscular blocking agent Substances 0.000 description 1
- 208000021722 neuropathic pain Diseases 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- CZWWGGWJPUUXTN-UHFFFAOYSA-N tert-butyl 4-(3-cyanoanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC=CC(C#N)=C1 CZWWGGWJPUUXTN-UHFFFAOYSA-N 0.000 description 1
- YMTIORAJSSFAOY-UHFFFAOYSA-N tert-butyl 4-[4-(diethylcarbamoyl)anilino]piperidine-1-carboxylate Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1NC1CCN(C(=O)OC(C)(C)C)CC1 YMTIORAJSSFAOY-UHFFFAOYSA-N 0.000 description 1
- ZKOPTHLZDBWWIB-UHFFFAOYSA-N tert-butyl 4-[n-(3-cyanophenyl)-4-(diethylcarbamoyl)anilino]piperidine-1-carboxylate Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(C=CC=1)C#N)C1CCN(C(=O)OC(C)(C)C)CC1 ZKOPTHLZDBWWIB-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009529 traumatic brain injury Effects 0.000 description 1
- 208000009935 visceral pain Diseases 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
- C07D401/06—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 only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—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
- 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
-
- 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
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Anesthesiology (AREA)
- Psychology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Vascular Medicine (AREA)
- Nutrition Science (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE0101770A SE0101770D0 (sv) | 2001-05-18 | 2001-05-18 | Novel compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200308637B true ZA200308637B (en) | 2005-02-07 |
Family
ID=20284173
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200308637A ZA200308637B (en) | 2001-05-18 | 2003-11-05 | 4-[Phenyl-(piperidin-4-yl)-amino]-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders. |
Country Status (25)
Country | Link |
---|---|
US (1) | US7064137B2 (sk) |
EP (1) | EP1395558B1 (sk) |
JP (1) | JP2005510456A (sk) |
KR (1) | KR20040000469A (sk) |
CN (1) | CN1620435A (sk) |
AR (1) | AR033759A1 (sk) |
AT (1) | ATE313529T1 (sk) |
BG (1) | BG108331A (sk) |
BR (1) | BR0209669A (sk) |
CA (1) | CA2446313A1 (sk) |
CO (1) | CO5540319A2 (sk) |
CZ (1) | CZ20033090A3 (sk) |
DE (1) | DE60208193T2 (sk) |
EE (1) | EE200300534A (sk) |
HU (1) | HUP0401608A2 (sk) |
IL (1) | IL158629A0 (sk) |
IS (1) | IS7031A (sk) |
MX (1) | MXPA03010441A (sk) |
NO (1) | NO20035112D0 (sk) |
PL (1) | PL366390A1 (sk) |
RU (1) | RU2003131967A (sk) |
SE (1) | SE0101770D0 (sk) |
SK (1) | SK13922003A3 (sk) |
WO (1) | WO2002094783A1 (sk) |
ZA (1) | ZA200308637B (sk) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE0300987D0 (sv) * | 2003-04-03 | 2003-04-03 | Astrazeneca Ab | Diarylmethylidene piperidine derivatives, preparations thereof and uses thereof |
CN100549004C (zh) | 2003-10-01 | 2009-10-14 | 阿得罗公司 | 螺环杂环衍生物及其应用方法 |
US7598261B2 (en) | 2005-03-31 | 2009-10-06 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
US7576207B2 (en) | 2006-04-06 | 2009-08-18 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
WO2016099394A1 (en) * | 2014-12-19 | 2016-06-23 | Pharmnovo Ab | Novel selective delta-opioid receptor agonists useful for the treatment of pain, anxiety and depression. |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4091096A (en) * | 1976-03-19 | 1978-05-23 | Eli Lilly And Company | Dinitroanilines for the control of phytopathogens |
EG12406A (en) * | 1976-08-12 | 1979-03-31 | Janssen Pharmaceutica Nv | Process for preparing of novel n-aryl-n-(1-l-4-piperidinyl)-arylacetamides |
US4252812A (en) * | 1977-05-23 | 1981-02-24 | Pfizer Inc. | 2-Substituted-trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles |
SE441448B (sv) | 1977-05-23 | 1985-10-07 | Pfizer | Sett att framstella hexahydro-gamma-karbolinforeningar |
DE3200304A1 (de) * | 1981-01-16 | 1982-08-26 | Sandoz-Patent-GmbH, 7850 Lörrach | 3-aminopropoxyaryl-derivate, ihre herstellung und sie enthaltende arzneimittel |
DE3563964D1 (en) * | 1984-10-16 | 1988-09-01 | Synthelabo | Piperidine derivatives, their preparation and their therapeutical application |
KR940003491B1 (ko) * | 1989-08-10 | 1994-04-23 | 리히터 게데온 베기에스제티 기아르 알.티 | 4,4-이중 치환된 피페리딘 유도체와 그 제조방법 및 상기 화합물을 함유하는 약제학적 조성물 |
YU150489A (sh) * | 1989-08-10 | 1992-12-21 | W.L. Gore & Co. Gmbh. | Uređaj za ispitivanje odevnih predmeta na nepromočivost |
US5854245A (en) * | 1996-06-28 | 1998-12-29 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
SE9604786D0 (sv) * | 1996-12-20 | 1996-12-20 | Astra Pharma Inc | New compounds |
TW548271B (en) * | 1996-12-20 | 2003-08-21 | Astra Pharma Inc | Novel piperidine derivatives having an exocyclic double bond with analgesic effects |
EP1049676B1 (en) | 1997-12-24 | 2005-10-12 | Ortho-Mcneil Pharmaceutical, Inc. | 4- aryl(piperidin-4-yl)] aminobenzamides which bind to the delta-opioid receptor |
JP4498602B2 (ja) | 1998-03-10 | 2010-07-07 | リサーチ・トライアングル・インスティチュート | 新規なオピエート化合物、その調製法及び使用法 |
SE9904675D0 (sv) * | 1999-12-20 | 1999-12-20 | Astra Pharma Inc | Novel compounds |
BR0108965A (pt) * | 2000-03-03 | 2002-11-26 | Ortho Mcneil Pharm Inc | Derivados de 3-(diarilmetileno)-8-azabiciclo[3,2,1]octano |
US6556387B1 (en) * | 2000-03-31 | 2003-04-29 | Seagate Technology Llc | Controlling mechanical response characteristics of a disc drive actuator by adjusting a fastener engaging the actuator shaft to vary axial force on the bearing assembly |
SE0001207D0 (sv) * | 2000-04-04 | 2000-04-04 | Astrazeneca Canada Inc | Novel compounds |
-
2001
- 2001-05-18 SE SE0101770A patent/SE0101770D0/xx unknown
-
2002
- 2002-05-16 HU HU0401608A patent/HUP0401608A2/hu unknown
- 2002-05-16 JP JP2002591456A patent/JP2005510456A/ja active Pending
- 2002-05-16 KR KR10-2003-7014948A patent/KR20040000469A/ko not_active Application Discontinuation
- 2002-05-16 CZ CZ20033090A patent/CZ20033090A3/cs unknown
- 2002-05-16 SK SK1392-2003A patent/SK13922003A3/sk unknown
- 2002-05-16 CA CA002446313A patent/CA2446313A1/en not_active Abandoned
- 2002-05-16 RU RU2003131967/04A patent/RU2003131967A/ru not_active Application Discontinuation
- 2002-05-16 EP EP02736338A patent/EP1395558B1/en not_active Expired - Lifetime
- 2002-05-16 BR BR0209669-2A patent/BR0209669A/pt not_active Application Discontinuation
- 2002-05-16 EE EEP200300534A patent/EE200300534A/xx unknown
- 2002-05-16 MX MXPA03010441A patent/MXPA03010441A/es unknown
- 2002-05-16 IL IL15862902A patent/IL158629A0/xx unknown
- 2002-05-16 WO PCT/SE2002/000945 patent/WO2002094783A1/en active IP Right Grant
- 2002-05-16 CN CNA028141709A patent/CN1620435A/zh active Pending
- 2002-05-16 DE DE60208193T patent/DE60208193T2/de not_active Expired - Fee Related
- 2002-05-16 US US10/477,853 patent/US7064137B2/en not_active Expired - Fee Related
- 2002-05-16 PL PL02366390A patent/PL366390A1/xx not_active Application Discontinuation
- 2002-05-16 AR ARP020101815A patent/AR033759A1/es unknown
- 2002-05-16 AT AT02736338T patent/ATE313529T1/de not_active IP Right Cessation
-
2003
- 2003-11-05 ZA ZA200308637A patent/ZA200308637B/en unknown
- 2003-11-07 BG BG108331A patent/BG108331A/bg unknown
- 2003-11-12 CO CO03100167A patent/CO5540319A2/es not_active Application Discontinuation
- 2003-11-13 IS IS7031A patent/IS7031A/is unknown
- 2003-11-17 NO NO20035112A patent/NO20035112D0/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
JP2005510456A (ja) | 2005-04-21 |
WO2002094783A1 (en) | 2002-11-28 |
NO20035112D0 (no) | 2003-11-17 |
PL366390A1 (en) | 2005-01-24 |
IS7031A (is) | 2003-11-13 |
EP1395558A1 (en) | 2004-03-10 |
KR20040000469A (ko) | 2004-01-03 |
ATE313529T1 (de) | 2006-01-15 |
US7064137B2 (en) | 2006-06-20 |
BG108331A (bg) | 2004-10-29 |
EE200300534A (et) | 2004-02-16 |
HUP0401608A2 (hu) | 2004-12-28 |
IL158629A0 (en) | 2004-05-12 |
SE0101770D0 (sv) | 2001-05-18 |
US20040152731A1 (en) | 2004-08-05 |
DE60208193T2 (de) | 2006-07-13 |
CA2446313A1 (en) | 2002-11-28 |
CN1620435A (zh) | 2005-05-25 |
EP1395558B1 (en) | 2005-12-21 |
BR0209669A (pt) | 2004-04-20 |
CZ20033090A3 (en) | 2004-06-16 |
SK13922003A3 (sk) | 2004-04-06 |
DE60208193D1 (de) | 2006-01-26 |
CO5540319A2 (es) | 2005-07-29 |
MXPA03010441A (es) | 2004-03-09 |
RU2003131967A (ru) | 2005-05-10 |
AR033759A1 (es) | 2004-01-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
RU2309154C9 (ru) | 3-фенилсульфонил-8-пиперазин-1-ил-хинолины, обладающие аффинностью к 5-нт6 рецептору, способы их получения (варианты) | |
US7232825B2 (en) | Phenylaminopyrimidine derivatives and methods of use | |
JP6211509B2 (ja) | 複素環化合物およびその用途 | |
EP0363963B1 (en) | Piperidinyl benzimidazoles as antihistamines | |
US5834493A (en) | Indole derivatives as 5-HT1A and/or 5-HT2 ligands | |
FI90980B (fi) | Menetelmä N-heterosyklisten N-(4-piperidyyli)-amidien valmistamiseksi | |
NZ520342A (en) | 1,3-Disubstituted pyrrolidines as alpha-2-adrenoceptor antagonists | |
ZA200603604B (en) | Substituted piperazines, (1,4) diaszepines, and 2,5-diazabicyclo (2.2.1) heptanes as histamine H1 and/or H3 antagonists of histamine H3 reverse antagonists | |
SK281418B6 (sk) | Deriváty piperazínu, spôsob ich prípravy, medziprodukt na ich prípravu, ich použitie ako 5ht1a antagonistov a farmaceutický prípravok s ich obsahom | |
BG64849B1 (bg) | Производни на ацил-пиперазинил-пиримидини, тяхното получаване и използването им като лекарствени средства | |
RU2444515C2 (ru) | Производное амида индазолакриловой кислоты | |
ZA200308633B (en) | 4-(phenyl-piperidin-4-ylidene-methyl)-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders. | |
ZA200308634B (en) | 4-(phenyl-piperidin-4-ylidene-methyl)-benzamide derivatives and their use for the treatment of pain anxiety or gastrointestinal disorders. | |
ZA200204256B (en) | Novel compounds. | |
JP2002517386A (ja) | 新規なニューロキニン拮抗物質、その調製方法及びその化合物を含む医薬組成物 | |
ZA200308637B (en) | 4-[Phenyl-(piperidin-4-yl)-amino]-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders. | |
KR102076820B1 (ko) | 신규한 항진균성 옥소다이하이드로피리딘카보하이드라자이드 유도체 | |
ZA200308641B (en) | 4-(Phenyl-(piperidin-4-yl)-amino)-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders. | |
US6645971B1 (en) | Quinazolinone derivatives | |
PL186851B1 (pl) | Pochodne piperazynodionu jako środki farmaceutyczne | |
ZA200308635B (en) | 4-(phenyl-piperidin-4-ylidene-methyl)-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders. | |
ZA200103251B (en) | 3-Tetrahydropyridin-4-YL indoles for treatment of psychotic disorders. | |
ZA200308642B (en) | 4-(Phenyl-(piperidin-4-yl)-amino)-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders. | |
JP2002534421A (ja) | 1−フェニル−4−(1−[2−アリール]シクロプロピル)メチルピペラジン:ドーパミン受容体リガンド | |
NZ529398A (en) | 4-(phenyl-(piperidin-4-yl)-amino)-benzamide derivatives as opiod receptor agonists and their use for the treatment of pain, anxiety or gastrointestinal disorders |