GB1561023A - 2-methoxy - 5 - chloro aniline derivatives - Google Patents
2-methoxy - 5 - chloro aniline derivatives Download PDFInfo
- Publication number
- GB1561023A GB1561023A GB16765/77A GB1676577A GB1561023A GB 1561023 A GB1561023 A GB 1561023A GB 16765/77 A GB16765/77 A GB 16765/77A GB 1676577 A GB1676577 A GB 1676577A GB 1561023 A GB1561023 A GB 1561023A
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- GB
- United Kingdom
- Prior art keywords
- compound
- formula
- group
- amino
- hydrogen atom
- Prior art date
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- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical class COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 115
- 239000000203 mixture Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 125000003277 amino group Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 16
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- -1 pchlorophenyl Chemical group 0.000 claims description 11
- 239000013543 active substance Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- CIOOCLHMBKBLRB-UHFFFAOYSA-N n-(4-amino-5-chloro-2-methoxyphenyl)-1-benzylpiperidine-4-carboxamide Chemical compound COC1=CC(N)=C(Cl)C=C1NC(=O)C1CCN(CC=2C=CC=CC=2)CC1 CIOOCLHMBKBLRB-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 230000000802 nitrating effect Effects 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 230000020176 deacylation Effects 0.000 claims description 2
- 238000005947 deacylation reaction Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 235000011167 hydrochloric acid Nutrition 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 125000003386 piperidinyl group Chemical group 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 206010042008 Stereotypy Diseases 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical class Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 3
- REUWUKCZROEOOZ-UHFFFAOYSA-N 1-benzyl-N-(5-chloro-2-methoxy-4-nitrophenyl)piperidine-4-carboxamide Chemical compound ClC1=CC(=C(C=C1[N+](=O)[O-])OC)NC(=O)C1CCN(CC1)CC1=CC=CC=C1 REUWUKCZROEOOZ-UHFFFAOYSA-N 0.000 description 3
- FNIOHKVYTWOWKM-UHFFFAOYSA-N 4-acetamido-5-chloro-2-methoxybenzoyl azide Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1C(=O)N=[N+]=[N-] FNIOHKVYTWOWKM-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 208000009132 Catalepsy Diseases 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 206010047853 Waxy flexibility Diseases 0.000 description 3
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 229940025084 amphetamine Drugs 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- XAHLYBZLHNHUJQ-UHFFFAOYSA-N 1-benzyl-n-(5-chloro-2-methoxyphenyl)piperidine-4-carboxamide Chemical compound COC1=CC=C(Cl)C=C1NC(=O)C1CCN(CC=2C=CC=CC=2)CC1 XAHLYBZLHNHUJQ-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N Lactic Acid Natural products CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- BNUHAJGCKIQFGE-UHFFFAOYSA-N Nitroanisol Chemical compound COC1=CC=C([N+]([O-])=O)C=C1 BNUHAJGCKIQFGE-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 2
- 229960001076 chlorpromazine Drugs 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229960003878 haloperidol Drugs 0.000 description 2
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- NBRTWKNQYCHEIN-UHFFFAOYSA-N n-(4-acetamido-5-chloro-2-methoxyphenyl)-4-benzylpiperazine-1-carboxamide Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1NC(=O)N1CCN(CC=2C=CC=CC=2)CC1 NBRTWKNQYCHEIN-UHFFFAOYSA-N 0.000 description 2
- SPCRVWLCXMVUBE-UHFFFAOYSA-N n-(5-chloro-2-methoxy-4-nitrophenyl)piperidine-4-carboxamide Chemical compound COC1=CC([N+]([O-])=O)=C(Cl)C=C1NC(=O)C1CCNCC1 SPCRVWLCXMVUBE-UHFFFAOYSA-N 0.000 description 2
- DBUZNXJVCBJPTE-UHFFFAOYSA-N n-(5-chloro-2-methoxyphenyl)piperidine-4-carboxamide Chemical compound COC1=CC=C(Cl)C=C1NC(=O)C1CCNCC1 DBUZNXJVCBJPTE-UHFFFAOYSA-N 0.000 description 2
- NCUHDZYHZGTHRZ-UHFFFAOYSA-N n-(5-chloro-2-methoxyphenyl)pyridine-4-carboxamide Chemical compound COC1=CC=C(Cl)C=C1NC(=O)C1=CC=NC=C1 NCUHDZYHZGTHRZ-UHFFFAOYSA-N 0.000 description 2
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical class ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 2
- 230000000701 neuroleptic effect Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
- 230000002936 tranquilizing effect Effects 0.000 description 2
- JRNJPYKJAIDHOP-UHFFFAOYSA-N 1-benzyl-n-(5-chloro-2-methoxyphenyl)pyridin-1-ium-4-carboxamide;chloride Chemical compound [Cl-].COC1=CC=C(Cl)C=C1NC(=O)C(C=C1)=CC=[N+]1CC1=CC=CC=C1 JRNJPYKJAIDHOP-UHFFFAOYSA-N 0.000 description 1
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 1
- YUBDLZGUSSWQSS-UHFFFAOYSA-N 1-benzylpiperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CC=C1 YUBDLZGUSSWQSS-UHFFFAOYSA-N 0.000 description 1
- NZVZVGPYTICZBZ-UHFFFAOYSA-N 1-benzylpiperidine Chemical compound C=1C=CC=CC=1CN1CCCCC1 NZVZVGPYTICZBZ-UHFFFAOYSA-N 0.000 description 1
- ZMVSVQMWFTZSJQ-UHFFFAOYSA-N 1-benzylpiperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC1=CC=CC=C1 ZMVSVQMWFTZSJQ-UHFFFAOYSA-N 0.000 description 1
- GNPSDJOWGWWXSS-UHFFFAOYSA-M 1-benzylpyridin-1-ium;chloride Chemical compound [Cl-].C=1C=CC=C[N+]=1CC1=CC=CC=C1 GNPSDJOWGWWXSS-UHFFFAOYSA-M 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- YBCOOGQGBVDQSB-UHFFFAOYSA-N 4-acetamido-5-chloro-2-methoxybenzoyl chloride Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1C(Cl)=O YBCOOGQGBVDQSB-UHFFFAOYSA-N 0.000 description 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YVBSAPDHRXHFHV-UHFFFAOYSA-N [chloro(methoxy)methyl]benzene Chemical compound COC(Cl)C1=CC=CC=C1 YVBSAPDHRXHFHV-UHFFFAOYSA-N 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- QTCANKDTWWSCMR-UHFFFAOYSA-N costic aldehyde Natural products C1CCC(=C)C2CC(C(=C)C=O)CCC21C QTCANKDTWWSCMR-UHFFFAOYSA-N 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000005095 gastrointestinal system Anatomy 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- ISTFUJWTQAMRGA-UHFFFAOYSA-N iso-beta-costal Natural products C1C(C(=C)C=O)CCC2(C)CCCC(C)=C21 ISTFUJWTQAMRGA-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 1
- 229960004503 metoclopramide Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- PUAXOMDNTGEJLE-UHFFFAOYSA-N n-(4-amino-5-chloro-2-methoxyphenyl)-1-(2-phenylethyl)piperidine-4-carboxamide Chemical compound COC1=CC(N)=C(Cl)C=C1NC(=O)C1CCN(CCC=2C=CC=CC=2)CC1 PUAXOMDNTGEJLE-UHFFFAOYSA-N 0.000 description 1
- FLNXMFQCJMTKJR-UHFFFAOYSA-N n-(4-amino-5-chloro-2-methoxyphenyl)-1-[(4-methoxyphenyl)methyl]piperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1CN1CCC(C(=O)NC=2C(=CC(N)=C(Cl)C=2)OC)CC1 FLNXMFQCJMTKJR-UHFFFAOYSA-N 0.000 description 1
- HDZBESGTKUCGOC-UHFFFAOYSA-N n-(4-amino-5-chloro-2-methoxyphenyl)-1-[(4-methylphenyl)methyl]piperidine-4-carboxamide Chemical compound COC1=CC(N)=C(Cl)C=C1NC(=O)C1CCN(CC=2C=CC(C)=CC=2)CC1 HDZBESGTKUCGOC-UHFFFAOYSA-N 0.000 description 1
- MUEXODFBEWCCLB-UHFFFAOYSA-N n-(4-amino-5-chloro-2-methoxyphenyl)-1-benzylpiperidine-4-carboxamide;dihydrochloride Chemical compound Cl.Cl.COC1=CC(N)=C(Cl)C=C1NC(=O)C1CCN(CC=2C=CC=CC=2)CC1 MUEXODFBEWCCLB-UHFFFAOYSA-N 0.000 description 1
- NSWYMTOMHQOHER-UHFFFAOYSA-N n-(4-amino-5-chloro-2-methoxyphenyl)-1-benzylpiperidine-4-carboxamide;hydrochloride Chemical compound Cl.COC1=CC(N)=C(Cl)C=C1NC(=O)C1CCN(CC=2C=CC=CC=2)CC1 NSWYMTOMHQOHER-UHFFFAOYSA-N 0.000 description 1
- SKGHABNHBHWRQM-UHFFFAOYSA-N n-(5-chloro-2-methoxy-4-nitrophenyl)-1-[(4-methoxyphenyl)methyl]piperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1CN1CCC(C(=O)NC=2C(=CC(=C(Cl)C=2)[N+]([O-])=O)OC)CC1 SKGHABNHBHWRQM-UHFFFAOYSA-N 0.000 description 1
- UXHMCSIJCCFQOZ-UHFFFAOYSA-N n-(5-chloro-2-methoxyphenyl)pyridine-4-carboxamide;hydrochloride Chemical compound Cl.COC1=CC=C(Cl)C=C1NC(=O)C1=CC=NC=C1 UXHMCSIJCCFQOZ-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012070 reactive reagent Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- 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
-
- 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
- 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16765/77A GB1561023A (en) | 1977-04-22 | 1977-04-22 | 2-methoxy - 5 - chloro aniline derivatives |
| ZA00781831A ZA781831B (en) | 1977-04-22 | 1978-03-30 | Aniline derivatives |
| IL54438A IL54438A (en) | 1977-04-22 | 1978-04-03 | Substituted anisole derivatives,their preparation and pharmaceutical compositions containing them |
| CA000300476A CA1136137A (en) | 1977-04-22 | 1978-04-05 | Aniline derivatives |
| US05/894,942 US4223034A (en) | 1977-04-22 | 1978-04-10 | Aniline derivatives |
| BE186853A BE866057A (fr) | 1977-04-22 | 1978-04-17 | Derives de l'aniline utilisables comme medicament |
| AU35169/78A AU518729B2 (en) | 1977-04-22 | 1978-04-17 | Aniline derivatives |
| FR7811309A FR2387955A1 (fr) | 1977-04-22 | 1978-04-18 | Derives de l'aniline utilisables comme medicament |
| DE19782816884 DE2816884A1 (de) | 1977-04-22 | 1978-04-18 | Anilinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |
| SE7804483A SE7804483L (sv) | 1977-04-22 | 1978-04-19 | Anilinderivat |
| ES469008A ES469008A1 (es) | 1977-04-22 | 1978-04-20 | Un procedimiento para la preparacion de nuevos derivados de anilina |
| NL7804203A NL7804203A (nl) | 1977-04-22 | 1978-04-20 | Chlooranilinederivaten met kalmerende werking, farma- ceutisch preparaat dat een dergelijke verbinding bevat alsmede werkwijzen ter bereiding van deze verbindingen. |
| DK172578A DK172578A (da) | 1977-04-22 | 1978-04-20 | Fremgangsmaade til fremstilling af anilinderivater |
| IE791/78A IE46802B1 (en) | 1977-04-22 | 1978-04-21 | 2-methoxy-5-chloro aniline derivatives |
| JP4763078A JPS53132533A (en) | 1977-04-22 | 1978-04-21 | Aniline derivative having mental stabilizing effect process for preparing same intermediate useful for preparation thereof and medical composition containing same |
| ES476862A ES476862A1 (es) | 1977-04-22 | 1979-01-15 | Un procedimiento para la preparacion de nuevos derivados de anilina. |
| ES476863A ES476863A1 (es) | 1977-04-22 | 1979-01-15 | Un procedimiento para la preparacion de nuevos derivados de anilina. |
| ES476864A ES476864A1 (es) | 1977-04-22 | 1979-01-15 | Un procedimiento para la preparacion de nuevos derivados de anilina |
| US06/149,182 US4329344A (en) | 1977-04-22 | 1980-05-12 | 4-(Phenylalkyl)piperazine-1-carboxamides |
| US06/148,778 US4331816A (en) | 1977-04-22 | 1980-05-12 | Aniline analeptics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16765/77A GB1561023A (en) | 1977-04-22 | 1977-04-22 | 2-methoxy - 5 - chloro aniline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1561023A true GB1561023A (en) | 1980-02-13 |
Family
ID=10083254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16765/77A Expired GB1561023A (en) | 1977-04-22 | 1977-04-22 | 2-methoxy - 5 - chloro aniline derivatives |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US4223034A (enExample) |
| JP (1) | JPS53132533A (enExample) |
| AU (1) | AU518729B2 (enExample) |
| BE (1) | BE866057A (enExample) |
| CA (1) | CA1136137A (enExample) |
| DE (1) | DE2816884A1 (enExample) |
| DK (1) | DK172578A (enExample) |
| ES (4) | ES469008A1 (enExample) |
| FR (1) | FR2387955A1 (enExample) |
| GB (1) | GB1561023A (enExample) |
| IE (1) | IE46802B1 (enExample) |
| IL (1) | IL54438A (enExample) |
| NL (1) | NL7804203A (enExample) |
| SE (1) | SE7804483L (enExample) |
| ZA (1) | ZA781831B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE431092B (sv) * | 1979-07-10 | 1984-01-16 | Thuresson Af Ekenstam Bo | Terapeutiskt aktiva, substituerade piperidinkarboxianilider |
| IL61972A0 (en) * | 1980-01-30 | 1981-02-27 | Beecham Group Ltd | Azabicyclic compounds,their preparation and pharmaceutical compositions containing them |
| PL128409B1 (en) | 1980-03-01 | 1984-01-31 | Wyeth John & Brother Ltd | Process for preparing novel derivatives of piperidine |
| ZA815668B (en) * | 1980-09-04 | 1982-08-25 | Westinghouse Brake & Signal | Swinging plug door |
| EP0047620B1 (en) * | 1980-09-10 | 1985-03-13 | Beecham Group Plc | Aryl diazabicyclyl amides, a process for their preparation and use |
| US4409225A (en) * | 1981-03-16 | 1983-10-11 | Beecham Group Limited | Substituted benzamides |
| US4585774A (en) * | 1981-05-08 | 1986-04-29 | Otsuka Pharmaceutical Co., Ltd. | Aniline derivatives and cardiotonic composition |
| GB8517854D0 (en) * | 1985-07-15 | 1985-08-21 | Roussell Lab Ltd | Chemical compounds |
| EP0343307A1 (en) * | 1988-05-26 | 1989-11-29 | Fabrica Espanola De Productos Quimicos Y Farmaceuticos, S.A. | 4-Piperidinealkanamine derivatives |
| EP0968200A1 (en) * | 1997-02-24 | 2000-01-05 | ZymoGenetics, Inc. | Calcitonin mimetics |
| FR2821356A1 (fr) * | 2001-02-23 | 2002-08-30 | Cerep | Nouveaux derives d'arylcarbamates et d'arylurees, preparations et utilisations |
| ATE440835T1 (de) | 2003-03-06 | 2009-09-15 | Glaxo Group Ltd | Heterozyklische harnstoff-derivate für die behandlung von schmerzen. |
| WO2004078744A2 (en) | 2003-03-07 | 2004-09-16 | Glaxo Group Limited | Urea derivatives and their use as vanilloid receptor antagonists in the treatment of pain |
| GB0305426D0 (en) * | 2003-03-08 | 2003-04-16 | Glaxo Group Ltd | Novel compounds |
| GB0319150D0 (en) * | 2003-08-14 | 2003-09-17 | Glaxo Group Ltd | Novel compounds |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1445672A1 (de) * | 1962-08-09 | 1968-12-12 | Degussa | Verfahren zur Herstellung neuer 2-Aryl-alkyl-1-Basen |
| DE1189553B (de) * | 1962-08-09 | 1965-03-25 | Degussa | Verfahren zur Herstellung von racemischen und optisch aktiven Piperazinderivaten |
| US3576810A (en) * | 1968-06-20 | 1971-04-27 | Robins Co Inc A H | 1-substituted-3-(-4)-aroylpiperidines |
| US3856857A (en) * | 1970-02-13 | 1974-12-24 | En Nom Collectif Science Union | Amino acids and their derivatives |
| US3647877A (en) * | 1970-04-13 | 1972-03-07 | Mead Johnson & Co | Aminopropionanilides |
| GB1459506A (en) * | 1974-02-18 | 1976-12-22 | Wyeth John & Brother Ltd | Piperidine derivatives |
| GB1458898A (en) * | 1974-03-18 | 1976-12-15 | Science Union & Cie | Ortho alkoxyanilides a process for their preparation and pharmaceutical compositions containing them |
| AR216043A1 (es) * | 1974-03-21 | 1979-11-30 | Anphar Sa | Procedimiento para la preparacion de 1-derivados de benzoilamino-4-piperidina y sus sales fisiologicamente aceptables |
| JPS518283A (en) * | 1974-07-09 | 1976-01-23 | Kyorin Seiyaku Kk | 11 * 33 fuenirupuropiru * 44 karubamoirupiperajinjudotaino seizoho |
| JPS5152176A (enExample) * | 1974-10-12 | 1976-05-08 | Yoshitomi Pharmaceutical | |
| GB1520584A (en) * | 1975-04-02 | 1978-08-09 | Yamanouchi Pharma Co Ltd | 2 - alkoxy - 5 substituted benzamide derivatives and their use in pharmaceutical compositions |
| GB1498884A (en) * | 1975-04-15 | 1978-01-25 | Wyeth John & Brother Ltd | Aminoacetamide-pyridyl-tetrahydropyridyl and-piperidyl derivatives |
-
1977
- 1977-04-22 GB GB16765/77A patent/GB1561023A/en not_active Expired
-
1978
- 1978-03-30 ZA ZA00781831A patent/ZA781831B/xx unknown
- 1978-04-03 IL IL54438A patent/IL54438A/xx unknown
- 1978-04-05 CA CA000300476A patent/CA1136137A/en not_active Expired
- 1978-04-10 US US05/894,942 patent/US4223034A/en not_active Expired - Lifetime
- 1978-04-17 BE BE186853A patent/BE866057A/xx unknown
- 1978-04-17 AU AU35169/78A patent/AU518729B2/en not_active Expired
- 1978-04-18 FR FR7811309A patent/FR2387955A1/fr active Granted
- 1978-04-18 DE DE19782816884 patent/DE2816884A1/de not_active Withdrawn
- 1978-04-19 SE SE7804483A patent/SE7804483L/xx unknown
- 1978-04-20 DK DK172578A patent/DK172578A/da not_active IP Right Cessation
- 1978-04-20 ES ES469008A patent/ES469008A1/es not_active Expired
- 1978-04-20 NL NL7804203A patent/NL7804203A/xx not_active Application Discontinuation
- 1978-04-21 JP JP4763078A patent/JPS53132533A/ja active Pending
- 1978-04-21 IE IE791/78A patent/IE46802B1/en unknown
-
1979
- 1979-01-15 ES ES476863A patent/ES476863A1/es not_active Expired
- 1979-01-15 ES ES476862A patent/ES476862A1/es not_active Expired
- 1979-01-15 ES ES476864A patent/ES476864A1/es not_active Expired
-
1980
- 1980-05-12 US US06/148,778 patent/US4331816A/en not_active Expired - Lifetime
- 1980-05-12 US US06/149,182 patent/US4329344A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4329344A (en) | 1982-05-11 |
| FR2387955A1 (fr) | 1978-11-17 |
| IE780791L (en) | 1978-10-22 |
| BE866057A (fr) | 1978-10-17 |
| DE2816884A1 (de) | 1978-11-02 |
| ES469008A1 (es) | 1979-09-01 |
| AU3516978A (en) | 1979-10-25 |
| IL54438A (en) | 1981-10-30 |
| ES476862A1 (es) | 1979-06-01 |
| US4223034A (en) | 1980-09-16 |
| FR2387955B1 (enExample) | 1982-05-14 |
| AU518729B2 (en) | 1981-10-15 |
| IL54438A0 (en) | 1978-07-31 |
| IE46802B1 (en) | 1983-09-21 |
| US4331816A (en) | 1982-05-25 |
| ES476863A1 (es) | 1979-06-01 |
| DK172578A (da) | 1978-10-23 |
| NL7804203A (nl) | 1978-10-24 |
| SE7804483L (sv) | 1978-10-23 |
| ZA781831B (en) | 1979-03-28 |
| ES476864A1 (es) | 1980-06-16 |
| JPS53132533A (en) | 1978-11-18 |
| CA1136137A (en) | 1982-11-23 |
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| Publication | Publication Date | Title |
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| Date | Code | Title | Description |
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| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |