CA1095044A - N-piperid-4-yl benzamide compounds - Google Patents
N-piperid-4-yl benzamide compoundsInfo
- Publication number
- CA1095044A CA1095044A CA289,825A CA289825A CA1095044A CA 1095044 A CA1095044 A CA 1095044A CA 289825 A CA289825 A CA 289825A CA 1095044 A CA1095044 A CA 1095044A
- Authority
- CA
- Canada
- Prior art keywords
- amino
- methoxy
- chlorobenzamide
- benzyl
- general formula
- 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
Links
- JMQDNLCNCDSHNC-UHFFFAOYSA-N n-piperidin-4-ylbenzamide Chemical class C=1C=CC=CC=1C(=O)NC1CCNCC1 JMQDNLCNCDSHNC-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 150000003053 piperidines Chemical class 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 230000008569 process Effects 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- -1 N-piperid-4-yl benzamide compound Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 235000010233 benzoic acid Nutrition 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- RVEATKYEARPWRE-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxybenzoic acid Chemical compound COC1=CC(N)=C(Cl)C=C1C(O)=O RVEATKYEARPWRE-UHFFFAOYSA-N 0.000 claims description 7
- 239000005711 Benzoic acid Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- VCTCFJIRGRQFRQ-UHFFFAOYSA-N 4-amino-5-chloro-n-[1-(cyclohexylmethyl)-3-methylpiperidin-4-yl]-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NC1C(C)CN(CC2CCCCC2)CC1 VCTCFJIRGRQFRQ-UHFFFAOYSA-N 0.000 claims description 3
- UEFSWPJORJOUCI-UHFFFAOYSA-N 4-amino-n-(1-benzyl-2,6-dimethylpiperidin-4-yl)-5-chloro-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NC1CC(C)N(CC=2C=CC=CC=2)C(C)C1 UEFSWPJORJOUCI-UHFFFAOYSA-N 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- SJWKLNGMIHLOJX-UHFFFAOYSA-N 1-benzyl-n-ethylpiperidin-4-amine Chemical compound C1CC(NCC)CCN1CC1=CC=CC=C1 SJWKLNGMIHLOJX-UHFFFAOYSA-N 0.000 claims description 2
- RGEQSTMITLEXKD-UHFFFAOYSA-N 1-benzyl-n-methylpiperidin-4-amine Chemical compound C1CC(NC)CCN1CC1=CC=CC=C1 RGEQSTMITLEXKD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 6
- XNUNIHJOMFCFRQ-UHFFFAOYSA-N 4-amino-n-(1-benzyl-3-methylpiperidin-4-yl)-5-chloro-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NC1C(C)CN(CC=2C=CC=CC=2)CC1 XNUNIHJOMFCFRQ-UHFFFAOYSA-N 0.000 claims 2
- FEARNSNCMCPAAZ-UHFFFAOYSA-N 4-amino-n-(1-benzylpiperidin-4-yl)-5-chloro-2-methoxy-n-methylbenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)N(C)C1CCN(CC=2C=CC=CC=2)CC1 FEARNSNCMCPAAZ-UHFFFAOYSA-N 0.000 claims 2
- YPVTZKCZJOGADO-UHFFFAOYSA-N 4-amino-n-(1-benzylpiperidin-4-yl)-5-chloro-n-ethyl-2-methoxybenzamide Chemical compound C=1C(Cl)=C(N)C=C(OC)C=1C(=O)N(CC)C(CC1)CCN1CC1=CC=CC=C1 YPVTZKCZJOGADO-UHFFFAOYSA-N 0.000 claims 2
- JDTXEYQOJHLZCZ-UHFFFAOYSA-N 1-(cyclohexylmethyl)-3-methylpiperidin-4-amine Chemical compound C1CC(N)C(C)CN1CC1CCCCC1 JDTXEYQOJHLZCZ-UHFFFAOYSA-N 0.000 claims 1
- VVQHCVRZYPYZNW-UHFFFAOYSA-N 1-benzyl-2,6-dimethylpiperidin-4-amine Chemical compound CC1CC(N)CC(C)N1CC1=CC=CC=C1 VVQHCVRZYPYZNW-UHFFFAOYSA-N 0.000 claims 1
- MGTFEKWKCLDVNN-UHFFFAOYSA-N 1-benzyl-3-methylpiperidin-4-amine Chemical compound C1CC(N)C(C)CN1CC1=CC=CC=C1 MGTFEKWKCLDVNN-UHFFFAOYSA-N 0.000 claims 1
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 4
- 239000003136 dopamine receptor stimulating agent Substances 0.000 abstract description 3
- 229940005501 dopaminergic agent Drugs 0.000 abstract description 3
- 229960003638 dopamine Drugs 0.000 abstract description 2
- 239000002804 dopamine agent Substances 0.000 abstract description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 29
- 235000013350 formula milk Nutrition 0.000 description 28
- 239000000155 melt Substances 0.000 description 28
- 239000000203 mixture Substances 0.000 description 27
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- 229940050411 fumarate Drugs 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000007792 addition Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CNHCVLKFUNTXQY-UHFFFAOYSA-N 4-amino-n-(1-benzyl-3-methylpiperidin-4-yl)-5-chloro-2-methoxybenzamide;hydrochloride Chemical compound Cl.COC1=CC(N)=C(Cl)C=C1C(=O)NC1C(C)CN(CC=2C=CC=CC=2)CC1 CNHCVLKFUNTXQY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001204 N-oxides Chemical class 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229960001701 chloroform Drugs 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- 239000007832 Na2SO4 Substances 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001559 benzoic acids Chemical class 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 235000013355 food flavoring agent Nutrition 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 230000002295 serotoninergic effect Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 description 2
- 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 2
- 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 2
- 208000008589 Obesity Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 241000219161 Theobroma Species 0.000 description 2
- 230000001539 anorectic effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 206010061428 decreased appetite Diseases 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004334 sorbic acid Substances 0.000 description 2
- 235000010199 sorbic acid Nutrition 0.000 description 2
- 229940075582 sorbic acid Drugs 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
- SYHDHOFHPIRFEL-UHFFFAOYSA-N 2-amino-5-chlorobenzamide;hydrochloride Chemical compound Cl.NC(=O)C1=CC(Cl)=CC=C1N SYHDHOFHPIRFEL-UHFFFAOYSA-N 0.000 description 1
- HKWCOYHYCBLUTR-UHFFFAOYSA-N 4,5-diamino-n-(1-benzylpiperidin-4-yl)-2-methoxy-n-methylbenzamide Chemical compound COC1=CC(N)=C(N)C=C1C(=O)N(C)C1CCN(CC=2C=CC=CC=2)CC1 HKWCOYHYCBLUTR-UHFFFAOYSA-N 0.000 description 1
- UXHQLGLGLZKHTC-CUNXSJBXSA-N 4-[(3s,3ar)-3-cyclopentyl-7-(4-hydroxypiperidine-1-carbonyl)-3,3a,4,5-tetrahydropyrazolo[3,4-f]quinolin-2-yl]-2-chlorobenzonitrile Chemical compound C1CC(O)CCN1C(=O)C1=CC=C(C=2[C@@H]([C@H](C3CCCC3)N(N=2)C=2C=C(Cl)C(C#N)=CC=2)CC2)C2=N1 UXHQLGLGLZKHTC-CUNXSJBXSA-N 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- ICYVNACPQODCBQ-UHFFFAOYSA-N 4-acetamido-5-chloro-n-[1-(cyclohexylmethyl)piperidin-4-yl]-2-methoxy-n-methylbenzamide Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1C(=O)N(C)C1CCN(CC2CCCCC2)CC1 ICYVNACPQODCBQ-UHFFFAOYSA-N 0.000 description 1
- CMRUKQFPGXLCRF-UHFFFAOYSA-N 4-acetamido-n-(1-benzylpiperidin-4-yl)-5-chloro-2-methoxy-n-methylbenzamide Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1C(=O)N(C)C1CCN(CC=2C=CC=CC=2)CC1 CMRUKQFPGXLCRF-UHFFFAOYSA-N 0.000 description 1
- HQTXSEBSCWTEPG-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-methyl-n-[1-(1-phenylethyl)piperidin-4-yl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)N(C)C1CCN(C(C)C=2C=CC=CC=2)CC1 HQTXSEBSCWTEPG-UHFFFAOYSA-N 0.000 description 1
- BRXXTVNYHGGBKP-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(N)=O BRXXTVNYHGGBKP-UHFFFAOYSA-N 0.000 description 1
- GKZNURXFMWOADX-UHFFFAOYSA-N 4-amino-5-chloro-n-[1-(cyclohexylmethyl)piperidin-4-yl]-2-methoxy-n-methylbenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)N(C)C1CCN(CC2CCCCC2)CC1 GKZNURXFMWOADX-UHFFFAOYSA-N 0.000 description 1
- YZLDMMVGLFWGAH-UHFFFAOYSA-N 4-amino-n-(1-benzhydrylpiperidin-4-yl)-5-chloro-2-methoxy-n-methylbenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)N(C)C1CCN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 YZLDMMVGLFWGAH-UHFFFAOYSA-N 0.000 description 1
- LNVQXFVOIFHRRE-UHFFFAOYSA-N 4-amino-n-(1-benzylpiperidin-4-yl)-2-methoxy-n-methylbenzamide Chemical compound COC1=CC(N)=CC=C1C(=O)N(C)C1CCN(CC=2C=CC=CC=2)CC1 LNVQXFVOIFHRRE-UHFFFAOYSA-N 0.000 description 1
- DIZHBOQIFXGXOD-UHFFFAOYSA-N 4-amino-n-(1-benzylpiperidin-4-yl)-5-bromo-2-methoxy-n-methylbenzamide Chemical compound COC1=CC(N)=C(Br)C=C1C(=O)N(C)C1CCN(CC=2C=CC=CC=2)CC1 DIZHBOQIFXGXOD-UHFFFAOYSA-N 0.000 description 1
- WVPWLIPIJPGAFO-WXXKFALUSA-N 4-amino-n-(1-benzylpiperidin-4-yl)-5-chloro-2-ethoxy-n-methylbenzamide;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.CCOC1=CC(N)=C(Cl)C=C1C(=O)N(C)C1CCN(CC=2C=CC=CC=2)CC1.CCOC1=CC(N)=C(Cl)C=C1C(=O)N(C)C1CCN(CC=2C=CC=CC=2)CC1 WVPWLIPIJPGAFO-WXXKFALUSA-N 0.000 description 1
- XKNIBVKYEGXGHF-UHFFFAOYSA-N 4-amino-n-(1-benzylpiperidin-4-yl)-5-chloro-n-ethyl-2-methoxybenzamide;hydrochloride Chemical compound Cl.C=1C(Cl)=C(N)C=C(OC)C=1C(=O)N(CC)C(CC1)CCN1CC1=CC=CC=C1 XKNIBVKYEGXGHF-UHFFFAOYSA-N 0.000 description 1
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical class O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 1
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- JBWUYNNIJUZQOY-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-2-methoxy-n-methyl-5-methylsulfonylbenzamide Chemical compound COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N(C)C1CCN(CC=2C=CC=CC=2)CC1 JBWUYNNIJUZQOY-UHFFFAOYSA-N 0.000 description 1
- VTXBGUAILJACMH-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-5-chloro-2-methoxy-n-methyl-4-(methylamino)benzamide Chemical compound C1=C(Cl)C(NC)=CC(OC)=C1C(=O)N(C)C1CCN(CC=2C=CC=CC=2)CC1 VTXBGUAILJACMH-UHFFFAOYSA-N 0.000 description 1
- HVAVTOMQLIHTQM-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-5-chloro-2-methoxy-n-methylbenzamide Chemical compound COC1=CC=C(Cl)C=C1C(=O)N(C)C1CCN(CC=2C=CC=CC=2)CC1 HVAVTOMQLIHTQM-UHFFFAOYSA-N 0.000 description 1
- QRCCUXYRRWIZBC-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-5-chloro-n-ethyl-2-methoxy-4-[(2,2,2-trifluoroacetyl)amino]benzamide Chemical compound C=1C(Cl)=C(NC(=O)C(F)(F)F)C=C(OC)C=1C(=O)N(CC)C(CC1)CCN1CC1=CC=CC=C1 QRCCUXYRRWIZBC-UHFFFAOYSA-N 0.000 description 1
- SKFQKIKDFWVWIR-UHFFFAOYSA-N n-benzyl-n-(1-benzylpiperidin-4-yl)-5-chloro-2-methoxybenzamide Chemical compound COC1=CC=C(Cl)C=C1C(=O)N(C1CCN(CC=2C=CC=CC=2)CC1)CC1=CC=CC=C1 SKFQKIKDFWVWIR-UHFFFAOYSA-N 0.000 description 1
- YAZGADZUKMSMOV-UHFFFAOYSA-N n-piperidin-4-ylidenehydroxylamine Chemical class ON=C1CCNCC1 YAZGADZUKMSMOV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
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Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB45146/76 | 1976-10-29 | ||
| GB45146/76A GB1586468A (en) | 1976-10-29 | 1976-10-29 | Piperidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1095044A true CA1095044A (en) | 1981-02-03 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA289,825A Expired CA1095044A (en) | 1976-10-29 | 1977-10-28 | N-piperid-4-yl benzamide compounds |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4367232A (enExample) |
| JP (1) | JPS5377069A (enExample) |
| CA (1) | CA1095044A (enExample) |
| DE (1) | DE2747960A1 (enExample) |
| ES (2) | ES463632A1 (enExample) |
| FR (1) | FR2369263A1 (enExample) |
| GB (1) | GB1586468A (enExample) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US4962115A (en) * | 1981-10-01 | 1990-10-09 | Janssen Pharmaceutica N.V. | Novel N-(3-hydroxy-4-piperidinyl)benzamide derivatives |
| US5137896A (en) * | 1981-10-01 | 1992-08-11 | Janssen Pharmaceutica N.V. | N-(3-hydroxy-4-piperidinyl)benzamide derivatives |
| US5057525A (en) * | 1981-10-01 | 1991-10-15 | Janssen Pharmaceutica N.V. | Novel N-(3-hydroxy-4-piperidinyl) benzamide derivatives |
| FR2534255B1 (fr) * | 1982-10-11 | 1985-07-12 | Delalande Sa | Nouveaux derives de la 4-aroylamino piperidine, leur procede de preparation et leur application en therapeutique |
| FR2546169B1 (fr) * | 1983-05-20 | 1986-03-21 | Delalande Sa | N-oxydes de derives aminocycliques, leur procede de preparation et leur application en therapeutique |
| GB8527052D0 (en) * | 1985-11-02 | 1985-12-04 | Beecham Group Plc | Compounds |
| FI95572C (fi) * | 1987-06-22 | 1996-02-26 | Eisai Co Ltd | Menetelmä lääkeaineena käyttökelpoisen piperidiinijohdannaisten tai sen farmaseuttisen suolan valmistamiseksi |
| GB9016581D0 (en) * | 1990-07-27 | 1990-09-12 | Ici Plc | Fungicides |
| GB9016580D0 (en) * | 1990-07-27 | 1990-09-12 | Ici Plc | Fungicides |
| TR27569A (tr) * | 1992-01-24 | 1995-06-13 | Ici Plc | Yeni fungisidal asilaminobenzamidler, bunlarin hazirlanis islemleri ve bitkilerdeki mantar enfeksiyonlariyla mücadelede kullanimlari. |
| US5739135A (en) * | 1993-09-03 | 1998-04-14 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| US5827875A (en) * | 1996-05-10 | 1998-10-27 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| US5885983A (en) * | 1996-05-10 | 1999-03-23 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| US5883109A (en) * | 1996-07-24 | 1999-03-16 | Bristol-Myers Squibb Company | Method for lowering serum lipid levels employing an MTP inhibitor in combination with another cholesterol lowering drug |
| SE9902987D0 (sv) * | 1999-08-24 | 1999-08-24 | Astra Pharma Prod | Novel compounds |
| IL151164A0 (en) * | 2000-03-06 | 2003-04-10 | Acadia Pharm Inc | Azacyclic compounds for use in the treatment of serotonin related diseases |
| CA2406652A1 (en) * | 2000-04-20 | 2001-11-01 | Nps Allelix Corp. | Aminopiperidines for use as glyt-1 inhibitors |
| GB0011838D0 (en) * | 2000-05-17 | 2000-07-05 | Astrazeneca Ab | Chemical compounds |
| RU2286801C2 (ru) * | 2001-05-01 | 2006-11-10 | Институт Нефтехимического Синтеза Имени А.В. Топчиева Российской Академии Наук | Двухфазные биоадгезионные композиции, абсорбирующие воду |
| KR20100008799A (ko) * | 2001-12-28 | 2010-01-26 | 아카디아 파마슈티칼스 인코포레이티드 | 모노아민 수용체 조정자로서의 스피로아자사이클릭 화합물 |
| US7538222B2 (en) * | 2002-06-24 | 2009-05-26 | Acadia Pharmaceuticals, Inc. | N-substituted piperidine derivatives as serotonin receptor agents |
| US7253186B2 (en) * | 2002-06-24 | 2007-08-07 | Carl-Magnus Andersson | N-substituted piperidine derivatives as serotonin receptor agents |
| BR0312217A (pt) * | 2002-06-24 | 2005-05-10 | Acadia Pharm Inc | Compostos, métodos de inibição da atividade/ativação de um receptor monoaminérgico e método de tratamento de condição doentia associada a um receptor de monoaminergético |
| MY139563A (en) * | 2002-09-04 | 2009-10-30 | Bristol Myers Squibb Co | Heterocyclic aromatic compounds useful as growth hormone secretagogues |
| CN101780080B (zh) | 2003-01-16 | 2014-06-04 | 阿卡蒂亚药品公司 | 用于神经退行性疾病的治疗的选择性五羟色胺2a/2c受体反向激动剂 |
| KR100697944B1 (ko) * | 2003-02-10 | 2007-03-20 | 니폰 쇼쿠바이 컴파니 리미티드 | 수분-흡수제 |
| SE0301369D0 (sv) * | 2003-05-09 | 2003-05-09 | Astrazeneca Ab | Chemical compounds |
| US7820695B2 (en) * | 2004-05-21 | 2010-10-26 | Acadia Pharmaceuticals, Inc. | Selective serotonin receptor inverse agonists as therapeutics for disease |
| US20050261278A1 (en) * | 2004-05-21 | 2005-11-24 | Weiner David M | Selective serotonin receptor inverse agonists as therapeutics for disease |
| US7790899B2 (en) * | 2004-09-27 | 2010-09-07 | Acadia Pharmaceuticals, Inc. | Synthesis of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N′-(4-(2-methylpropyloxy)phenylmethyl)carbamide and its tartrate salt and crystalline forms |
| ES2530258T3 (es) * | 2004-09-27 | 2015-02-27 | Acadia Pharmaceuticals Inc. | Síntesis de una forma cristalina de sal tartrato de N-(4-fluorobencil)-N-(1-metilpiperidin-4-il)-N'-(4-(2-metilpropiloxi)fenilmetil)carbamida |
| JP2008524276A (ja) * | 2004-12-20 | 2008-07-10 | エフ．ホフマン−ラ ロシュ アーゲー | ４−アミノピペリジン誘導体 |
| WO2008116024A2 (en) | 2007-03-19 | 2008-09-25 | Acadia Pharmaceuticals Inc. | Combinations of 5-ht2a inverse agonists and antagonists with antipsychotics |
| CA2700331A1 (en) * | 2007-09-21 | 2009-03-26 | Acadia Pharmaceuticals, Inc. | Co-administration of pimavanserin with other agents |
| DK3325444T3 (da) | 2015-07-20 | 2021-10-04 | Acadia Pharm Inc | Fremgangsmåder til fremstilling af n-(4-fluorbenzyl)-n-(1-methylpiperidin-4-yl)-n'-(4-(2-methylpropyloxy)phenylmethyl)carbamid og dets tartratsalt og polymorf form c |
| US10953000B2 (en) | 2016-03-25 | 2021-03-23 | Acadia Pharmaceuticals Inc. | Combination of pimavanserin and cytochrome P450 modulators |
| WO2017165635A1 (en) | 2016-03-25 | 2017-09-28 | Acadia Pharmaceuticals Inc. | Combination of pimavanserin and cytochrome p450 modulators |
| EP3558311A1 (en) | 2016-12-20 | 2019-10-30 | Acadia Pharmaceuticals Inc. | Pimavanserin alone or in combination for use in the treatment of alzheimer's disease psychosis |
| EP3615028A1 (en) | 2017-04-28 | 2020-03-04 | Acadia Pharmaceuticals Inc. | Pimavanserin for treating impulse control disorder |
| EP3675827A1 (en) | 2017-08-30 | 2020-07-08 | Acadia Pharmaceuticals Inc. | Formulations of pimavanserin |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2745837A (en) * | 1954-01-21 | 1956-05-15 | Schering Corp | Benzhydryl ethers of alkyl piperidinols |
| NL270803A (enExample) * | 1960-11-09 | |||
| US3342826A (en) * | 1964-01-13 | 1967-09-19 | Ile De France | Heterocyclic aminoalkyl benzamides |
| US3963745A (en) * | 1972-04-03 | 1976-06-15 | A. H. Robins Company, Incorporated | Method for controlling emesis with N-(1-substituted-3-pyrrolidinyl)benzamides and thiobenzamides |
| US3862139A (en) * | 1972-06-23 | 1975-01-21 | Delmar Chem | Heterocyclic benzamide compounds |
| CA1046066A (en) * | 1973-08-23 | 1979-01-09 | Tomio Muro | 1-(methylated piperidino (and pyrrolidin -1-yl)-3-(substituted phenoxy)-2-propanols |
| DE2513136C3 (de) | 1974-03-21 | 1981-04-30 | Anphar S.A., Madrid | N-(1-Benzylpiperid-4-yl)-benzamide, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate |
-
1976
- 1976-10-29 GB GB45146/76A patent/GB1586468A/en not_active Expired
-
1977
- 1977-10-26 DE DE19772747960 patent/DE2747960A1/de not_active Ceased
- 1977-10-27 US US05/845,958 patent/US4367232A/en not_active Expired - Lifetime
- 1977-10-28 CA CA289,825A patent/CA1095044A/en not_active Expired
- 1977-10-28 ES ES463632A patent/ES463632A1/es not_active Expired
- 1977-10-28 FR FR7733339A patent/FR2369263A1/fr active Granted
- 1977-10-28 ES ES463633A patent/ES463633A1/es not_active Expired
- 1977-10-29 JP JP13018677A patent/JPS5377069A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5377069A (en) | 1978-07-08 |
| FR2369263B1 (enExample) | 1980-06-13 |
| DE2747960A1 (de) | 1978-05-11 |
| US4367232A (en) | 1983-01-04 |
| ES463633A1 (es) | 1978-07-01 |
| ES463632A1 (es) | 1978-07-16 |
| GB1586468A (en) | 1981-03-18 |
| FR2369263A1 (fr) | 1978-05-26 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |