CH620678A5 - Process for the preparation of a derivative of piperidine - Google Patents

Process for the preparation of a derivative of piperidine Download PDF

Info

Publication number: CH620678A5
Authority: CH; Switzerland
Prior art keywords: group; general formula; amino; acid; derivative
Prior art date: 1976-02-17

Application number

CH179877A

Other languages

English (en)

French (fr)

Inventor

Jacinto Moragues Dr Mauri

Armando Vega Dr Noverola

Robert Geoffrey Willi Spickett

Jose Boix Dr Iglesias

Jose Prieto Soto

Original Assignee

Gallardo Antonio Sa

Priority date (The priority date 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 date listed.)

1976-02-17

Filing date

1977-02-14

Publication date

1980-12-15

1977-02-14 Application filed by Gallardo Antonio Sa filed Critical Gallardo Antonio Sa

1980-12-15 Publication of CH620678A5 publication Critical patent/CH620678A5/fr

Links

150000003053 piperidines Chemical class 0.000 title claims description 26
238000000034 method Methods 0.000 title claims description 22
238000002360 preparation method Methods 0.000 title claims description 9
239000002253 acid Substances 0.000 claims description 20
-1 amino, sulfonamido Chemical group 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 11
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
235000010233 benzoic acid Nutrition 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 6
150000008064 anhydrides Chemical class 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
239000005711 Benzoic acid Substances 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
150000001559 benzoic acids Chemical class 0.000 claims description 5
125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
239000012024 dehydrating agents‎ Substances 0.000 claims description 5
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
125000004442 acylamino group Chemical group 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000004450 alkenylene group Chemical group 0.000 claims description 3
125000003302 alkenyloxy group Chemical group 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 3
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 claims description 2
VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical group C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
125000005907 alkyl ester group Chemical group 0.000 claims description 2
125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 2
125000005336 allyloxy group Chemical group 0.000 claims description 2
150000001540 azides Chemical class 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
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 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
239000005049 silicon tetrachloride Substances 0.000 claims description 2
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 2
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 description 26
239000000243 solution Substances 0.000 description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
150000001875 compounds Chemical class 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 8
239000007788 liquid Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000003277 amino group Chemical group 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
238000009835 boiling Methods 0.000 description 5
239000000155 melt Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
WYDUUQNGNSXLRC-UHFFFAOYSA-N 1-(cyclohexylmethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CC1CCCCC1 WYDUUQNGNSXLRC-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 4
125000001453 quaternary ammonium group Chemical group 0.000 description 4
239000007787 solid Substances 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000012047 saturated solution Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
208000018522 Gastrointestinal disease Diseases 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
206010047700 Vomiting Diseases 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
239000003136 dopamine receptor stimulating agent Substances 0.000 description 2
229940005501 dopaminergic agent Drugs 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 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
239000008096 xylene Substances 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
INQFAVVNLUMSGT-UHFFFAOYSA-N 1-(cycloheptylmethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CC1CCCCCC1 INQFAVVNLUMSGT-UHFFFAOYSA-N 0.000 description 1
NDBCDBUOZCCWQQ-UHFFFAOYSA-N 1-(cyclohexylmethyl)piperidin-4-one Chemical compound C1CC(=O)CCN1CC1CCCCC1 NDBCDBUOZCCWQQ-UHFFFAOYSA-N 0.000 description 1
FIOGPFKVASGFMG-UHFFFAOYSA-N 1-[(4-methylcyclohexyl)methyl]piperidin-4-amine Chemical compound C1CC(C)CCC1CN1CCC(N)CC1 FIOGPFKVASGFMG-UHFFFAOYSA-N 0.000 description 1
GOXCIWMHHSVOKW-UHFFFAOYSA-N 4-acetamido-5-chloro-2-methoxybenzoic acid Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1C(O)=O GOXCIWMHHSVOKW-UHFFFAOYSA-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
MWHMLNGOYSYTFL-UHFFFAOYSA-N 4-amino-5-bromo-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Br)C=C1C(N)=O MWHMLNGOYSYTFL-UHFFFAOYSA-N 0.000 description 1
ASQGSHOSTVLLHK-UHFFFAOYSA-N 4-amino-5-chloro-2-ethoxybenzamide Chemical compound CCOC1=CC(N)=C(Cl)C=C1C(N)=O ASQGSHOSTVLLHK-UHFFFAOYSA-N 0.000 description 1
IAUUVRIECRBWIH-UHFFFAOYSA-N 5-chloro-2-methoxy-4-(methylamino)benzamide Chemical compound CNC1=CC(OC)=C(C(N)=O)C=C1Cl IAUUVRIECRBWIH-UHFFFAOYSA-N 0.000 description 1
206010001022 Acute psychosis Diseases 0.000 description 1
239000004135 Bone phosphate Substances 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
206010007559 Cardiac failure congestive Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
208000007882 Gastritis Diseases 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
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 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
206010026749 Mania Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
208000008469 Peptic Ulcer Diseases 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
206010067171 Regurgitation Diseases 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000005236 alkanoylamino group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
230000001539 anorectic effect Effects 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
230000001458 anti-acid effect Effects 0.000 description 1
230000000767 anti-ulcer Effects 0.000 description 1
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
229960004046 apomorphine Drugs 0.000 description 1
239000002830 appetite depressant Substances 0.000 description 1
159000000032 aromatic acids Chemical class 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
210000004556 brain Anatomy 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
125000001589 carboacyl group Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
239000010432 diamond Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
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229960003638 dopamine Drugs 0.000 description 1
239000002804 dopamine agent Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
206010013864 duodenitis Diseases 0.000 description 1
201000006549 dyspepsia Diseases 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
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125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
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239000000796 flavoring agent Substances 0.000 description 1
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239000012530 fluid Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000010410 layer Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
230000007257 malfunction Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
OUEXNQRVYGYGIK-UHFFFAOYSA-N methyl 4-acetamido-5-chloro-2-methoxybenzoate Chemical compound COC(=O)C1=CC(Cl)=C(NC(C)=O)C=C1OC OUEXNQRVYGYGIK-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000003176 neuroleptic agent Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
208000011906 peptic ulcer disease Diseases 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical class N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
DGMKFQYCZXERLX-UHFFFAOYSA-N proglumide Chemical compound CCCN(CCC)C(=O)C(CCC(O)=O)NC(=O)C1=CC=CC=C1 DGMKFQYCZXERLX-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1

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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)

CH179877A 1976-02-17 1977-02-14 Process for the preparation of a derivative of piperidine CH620678A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB6207/76A GB1513631A (en)	1976-02-17	1976-02-17	Piperidine derivatives

Publications (1)

Publication Number	Publication Date
CH620678A5 true CH620678A5 (en)	1980-12-15

Family

ID=9810379

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH179877A CH620678A5 (en)	1976-02-17	1977-02-14	Process for the preparation of a derivative of piperidine
CH179977A CH605751A5 (de)	1976-02-17	1977-02-14

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH179977A CH605751A5 (de)	1976-02-17	1977-02-14

Country Status (13)

Country	Link
JP (2)	JPS596851B2 (de)
AT (2)	AT356105B (de)
AU (1)	AU509216B2 (de)
BE (2)	BE851509A (de)
CA (2)	CA1094075A (de)
CH (2)	CH620678A5 (de)
DE (2)	DE2706038A1 (de)
ES (5)	ES455832A1 (de)
FR (2)	FR2342963A1 (de)
GB (1)	GB1513631A (de)
IE (2)	IE44611B1 (de)
NL (2)	NL7701630A (de)
ZA (2)	ZA77562B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1574418A (en) *	1976-11-16	1980-09-03	Anphar Sa	Piperidine derivatives
FR2584401B1 (fr) *	1985-07-04	1987-11-20	Ile De France	Nouveau benzamide, son procede de preparation et son application dans le domaine therapeutique
TW243449B (de) *	1991-02-15	1995-03-21	Hokuriku Pharmaceutical
US5395832A (en) *	1991-02-15	1995-03-07	Hokuriku Seiyaku Co., Ltd.	Benzamide derivatives

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MC965A1 (fr) *	1972-06-01	1974-02-01	Soc Et Scient Et Ind De L Ile	Nouvelle methode de préparation de 2-alcoxy-4,5-substitues benzamides
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

1976
- 1976-02-17 GB GB6207/76A patent/GB1513631A/en not_active Expired
1977
- 1977-02-01 ZA ZA770562A patent/ZA77562B/xx unknown
- 1977-02-01 ZA ZA00770563A patent/ZA77563B/xx unknown
- 1977-02-03 AU AU21925/77A patent/AU509216B2/en not_active Expired
- 1977-02-11 ES ES455832A patent/ES455832A1/es not_active Expired
- 1977-02-11 ES ES455831A patent/ES455831A1/es not_active Expired
- 1977-02-11 ES ES455835A patent/ES455835A1/es not_active Expired
- 1977-02-11 ES ES455834A patent/ES455834A1/es not_active Expired
- 1977-02-11 ES ES455833A patent/ES455833A1/es not_active Expired
- 1977-02-12 DE DE19772706038 patent/DE2706038A1/de not_active Ceased
- 1977-02-12 DE DE2705949A patent/DE2705949C2/de not_active Expired
- 1977-02-14 CH CH179877A patent/CH620678A5/fr not_active IP Right Cessation
- 1977-02-14 AT AT97877A patent/AT356105B/de not_active IP Right Cessation
- 1977-02-14 CH CH179977A patent/CH605751A5/xx not_active IP Right Cessation
- 1977-02-14 AT AT98577A patent/AT356106B/de not_active IP Right Cessation
- 1977-02-15 FR FR7704988A patent/FR2342963A1/fr active Granted
- 1977-02-16 IE IE328/77A patent/IE44611B1/en unknown
- 1977-02-16 BE BE175001A patent/BE851509A/xx not_active IP Right Cessation
- 1977-02-16 CA CA271,917A patent/CA1094075A/en not_active Expired
- 1977-02-16 FR FR7705169A patent/FR2341570A1/fr active Granted
- 1977-02-16 NL NL7701630A patent/NL7701630A/xx not_active Application Discontinuation
- 1977-02-16 CA CA271,918A patent/CA1094059A/en not_active Expired
- 1977-02-16 IE IE327/77A patent/IE44610B1/en unknown
- 1977-02-16 BE BE175000A patent/BE851508A/xx not_active IP Right Cessation
- 1977-02-16 NL NL7701631A patent/NL7701631A/xx not_active Application Discontinuation
- 1977-02-17 JP JP52016656A patent/JPS596851B2/ja not_active Expired
- 1977-02-17 JP JP1665577A patent/JPS52122378A/ja active Pending

Also Published As

Publication number	Publication date
ATA98577A (de)	1979-09-15
FR2342963A1 (fr)	1977-09-30
JPS52122378A (en)	1977-10-14
DE2706038A1 (de)	1977-08-18
GB1513631A (en)	1978-06-07
CA1094059A (en)	1981-01-20
ES455833A1 (es)	1978-01-01
ATA97877A (de)	1979-09-15
JPS52122379A (en)	1977-10-14
ES455831A1 (es)	1978-01-16
CH605751A5 (de)	1978-10-13
AU509216B2 (en)	1980-05-01
AU2192577A (en)	1978-08-10
BE851508A (de)	1977-06-16
ES455835A1 (es)	1978-01-01
ES455832A1 (es)	1978-01-01
AT356105B (de)	1980-04-10
CA1094075A (en)	1981-01-20
IE44610L (en)	1977-08-17
ES455834A1 (es)	1978-01-01
ZA77563B (en)	1978-04-26
DE2705949C2 (de)	1983-04-21
BE851509A (fr)	1977-06-16
FR2342963B1 (de)	1980-10-03
JPS596851B2 (ja)	1984-02-15
ZA77562B (en)	1977-12-28
FR2341570A1 (fr)	1977-09-16
IE44611B1 (en)	1982-01-27
IE44610B1 (en)	1982-01-27
DE2705949A1 (de)	1977-08-25
NL7701631A (nl)	1977-08-19
NL7701630A (nl)	1977-08-19
IE44611L (en)	1977-08-17
FR2341570B1 (de)	1981-10-30
AT356106B (de)	1980-04-10

Legal Events

Date	Code	Title	Description
1984-10-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0172096A1 (de)	1986-02-19	3-Acylaminomethylimidazo [1,2-a] pyridine, dessen Herstellung und therapeutische Anwendung
FR2530625A1 (fr)	1984-01-27	Derives d'indole, procedes pour leur preparation et compositions pharmaceutiques les contenant
FR2676055A1 (fr)	1992-11-06	Composes polycycliques amines et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant.
FR2673427A1 (fr)	1992-09-04	Derives heterocycliques diazotes n-substitues par un groupement biphenylmethyle, leur preparation, les compositions pharmaceutiques en contenant.
EP0307303B1 (de)	1991-12-04	1-[(2-Pyrimidinyl)-aminoalkyl]-piperidine, deren Herstellung und Verwendung als Heilmittel
EP0611766A1 (de)	1994-08-24	Polysubstituierte 2-Amidothiazole-Derivate, Verfahren zu ihrer Herstellung, pharmazeutische Zusammenstellungen die sie enthalten und ihre Anwendung für die Bereitung eines Arzneimittels
FR2681067A1 (fr)	1993-03-12	Derives heterocycliques n-substitues, leur preparation, les compositions pharmaceutiques en contenant.
EP0008249B1 (de)	1981-08-26	Fluoren- und Fluoranthenderivate, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung
EP0429344A1 (de)	1991-05-29	Pyridazin-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
FR2468601A1 (fr)	1981-05-08	Nouveaux derives de flavanne utiles notamment comme anticonvulsivants
EP0021857B1 (de)	1982-12-22	Indolderivate, ihre Herstellung und diese Verbindungen enthaltende Arzneimittel
FR2500833A1 (fr)	1982-09-03	Nouveaux derives de l'acide (pyrrolidinyl-1)-7 fluoro-6 dihydro-1,4 oxo-4 naphtyridine-1, 8 carboxylique-3 et leur utilisation comme medicament
EP0002978B1 (de)	1982-10-06	Thiazolidindion-2,4 Derivate, deren Herstellung und Verwendung als Arzneimittel
EP0500443B1 (de)	1995-04-26	Phenylethanolamino- und Phenylethanolaminomethyltetraline, Verfahren zu deren Herstellung Zwischenprodukte davon und diese enthaltende pharmazeutische Zusammensetzungen
EP0301936B1 (de)	1992-12-16	Piperidin-Derivate, deren Herstellung und deren Verwendung als Heilmittel
EP0077427A1 (de)	1983-04-27	Piperidin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
CH644124A5 (fr)	1984-07-13	Oxoimidazoquinoxalines et leurs sels, leurs procedes de preparation et les medicaments les renfermant.
EP0063084B1 (de)	1984-09-12	Phenethanolamin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
CH620678A5 (en)	1980-12-15	Process for the preparation of a derivative of piperidine
EP0062580B1 (de)	1985-11-06	Imidazo(1,2-a)chinolinderivate
CH628885A5 (en)	1982-03-31	Piperidine derivative
CA1167444A (fr)	1984-05-15	Derives de la chloro-3 quinoleine, procedes pour leur preparation, et leur utilisation comme medicaments
MC1135A1 (fr)	1977-11-18	Derives de thiazine
EP0275762B1 (de)	1993-11-18	Indol-Carboxamid-Derivate und ihre Salze, Verfahren und Zwischenprodukte zur Herstellung, Anwendung als Heilmittel und Zusammenstellungen, die sie enthalten
FR2648135A1 (fr)	1990-12-14	Derives de phenyl-1-dihydro-1,4 amino-3 oxo-4 pyridazines, leur preparation et leur application en therapeutique