CA1094075A - Derives de la piperidine - Google Patents

Derives de la piperidine

Info

Publication number: CA1094075A
Authority: CA; Canada
Prior art keywords: amino; cyclohexa; methoxy; chlorobenzamide; preparation
Prior art date: 1976-02-17
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

Application number

CA271,917A

Other languages

English (en)

Inventor

Jacinto Moragues Mauri

Armando Vega Noverola

Robert Geoffrey William Spickett

Jose Boix Iglesias

Jose-Manuel Prieto Soto

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Antonio Gallardo SA

Original Assignee

Antonio Gallardo 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

1977-02-16

Publication date

1981-01-20

1977-02-16 Application filed by Antonio Gallardo SA filed Critical Antonio Gallardo SA

1981-01-20 Application granted granted Critical

1981-01-20 Publication of CA1094075A publication Critical patent/CA1094075A/fr

Status Expired legal-status Critical Current

Links

150000003053 piperidines Chemical class 0.000 title claims description 15
238000000034 method Methods 0.000 claims abstract description 57
239000002253 acid Substances 0.000 claims abstract description 23
150000001875 compounds Chemical class 0.000 claims abstract description 21
238000002360 preparation method Methods 0.000 claims abstract description 21
150000003839 salts Chemical class 0.000 claims abstract description 20
-1 sulphamoyl Chemical group 0.000 claims abstract description 14
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
125000005843 halogen group Chemical group 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
150000001204 N-oxides Chemical class 0.000 claims abstract description 8
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
125000002252 acyl group Chemical group 0.000 claims abstract description 6
125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims abstract description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
125000004442 acylamino group Chemical group 0.000 claims abstract description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 5
125000005336 allyloxy group Chemical group 0.000 claims abstract description 5
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 14
235000010233 benzoic acid Nutrition 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 9
JMQDNLCNCDSHNC-UHFFFAOYSA-N n-piperidin-4-ylbenzamide Chemical class C=1C=CC=CC=1C(=O)NC1CCNCC1 JMQDNLCNCDSHNC-UHFFFAOYSA-N 0.000 claims description 9
239000005711 Benzoic acid Substances 0.000 claims description 7
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
150000008064 anhydrides Chemical class 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
239000012024 dehydrating agents‎ Substances 0.000 claims description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 4
150000001540 azides Chemical class 0.000 claims description 3
150000004820 halides Chemical class 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
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 2
125000005907 alkyl ester group Chemical group 0.000 claims description 2
229960001760 dimethyl sulfoxide Drugs 0.000 claims description 2
BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 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
125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
239000000126 substance Substances 0.000 claims 13
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 4
XWGYOMHQGQZRLC-UHFFFAOYSA-N 4-amino-5-chloro-2-ethoxybenzoic acid Chemical compound CCOC1=CC(N)=C(Cl)C=C1C(O)=O XWGYOMHQGQZRLC-UHFFFAOYSA-N 0.000 claims 2
RCGRDMKGESMQHQ-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-[1-[(4-methylcyclohexa-1,4-dien-1-yl)methyl]piperidin-4-yl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NC1CCN(CC=2CC=C(C)CC=2)CC1 RCGRDMKGESMQHQ-UHFFFAOYSA-N 0.000 claims 2
DLKWUDHEMGNRCF-UHFFFAOYSA-N 1-[(4-methylcyclohexa-1,4-dien-1-yl)methyl]piperidin-4-amine Chemical compound C1C(C)=CCC(CN2CCC(N)CC2)=C1 DLKWUDHEMGNRCF-UHFFFAOYSA-N 0.000 claims 1
BXWLVQXAFBWKSR-UHFFFAOYSA-N 2-methoxy-5-methylsulfonylbenzoic acid Chemical compound COC1=CC=C(S(C)(=O)=O)C=C1C(O)=O BXWLVQXAFBWKSR-UHFFFAOYSA-N 0.000 claims 1
SQAILWDRVDGLGY-UHFFFAOYSA-N 2-methoxy-5-sulfamoylbenzoic acid Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(O)=O SQAILWDRVDGLGY-UHFFFAOYSA-N 0.000 claims 1
WHXLHIGUTBQVOF-UHFFFAOYSA-N 4-amino-5-bromo-2-methoxybenzoic acid Chemical compound COC1=CC(N)=C(Br)C=C1C(O)=O WHXLHIGUTBQVOF-UHFFFAOYSA-N 0.000 claims 1
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 1
TXJMYISJXPBNCC-UHFFFAOYSA-N 5-chloro-2-methoxy-4-(methylamino)benzoic acid Chemical compound CNC1=CC(OC)=C(C(O)=O)C=C1Cl TXJMYISJXPBNCC-UHFFFAOYSA-N 0.000 claims 1
230000004048 modification Effects 0.000 claims 1
238000012986 modification Methods 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 4
239000003795 chemical substances by application Substances 0.000 abstract description 3
125000004429 atom Chemical group 0.000 abstract 1
235000013350 formula milk Nutrition 0.000 description 30
239000000203 mixture Substances 0.000 description 20
239000000243 solution Substances 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 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
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
239000003826 tablet Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
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 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
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
239000000155 melt Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
229960001701 chloroform Drugs 0.000 description 3
MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 3
238000009472 formulation Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
239000007787 solid 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
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
208000028017 Psychotic disease Diseases 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
238000005903 acid hydrolysis reaction Methods 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
125000005236 alkanoylamino group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
238000004090 dissolution Methods 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
239000003937 drug carrier Substances 0.000 description 2
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
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231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000003921 oil Substances 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
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238000001953 recrystallisation Methods 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
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HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000004334 sorbic acid Substances 0.000 description 2
235000010199 sorbic acid Nutrition 0.000 description 2
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239000006188 syrup Substances 0.000 description 2
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229940086542 triethylamine Drugs 0.000 description 2
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VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical class O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 1
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MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 1
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150000008282 halocarbons Chemical class 0.000 description 1
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
230000007257 malfunction Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
YAZGADZUKMSMOV-UHFFFAOYSA-N n-piperidin-4-ylidenehydroxylamine Chemical class ON=C1CCNCC1 YAZGADZUKMSMOV-UHFFFAOYSA-N 0.000 description 1
239000003176 neuroleptic agent Substances 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000001477 organic nitrogen group Chemical group 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
239000000546 pharmaceutical excipient Substances 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
229910052697 platinum Inorganic materials 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000012797 qualification Methods 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940045902 sodium stearyl fumarate Drugs 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 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)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (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)

CA271,917A 1976-02-17 1977-02-16 Derives de la piperidine Expired CA1094075A (fr)

Applications Claiming Priority (2)

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

Publications (1)

Publication Number	Publication Date
CA1094075A true CA1094075A (fr)	1981-01-20

Family

ID=9810379

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA271,917A Expired CA1094075A (fr)	1976-02-17	1977-02-16	Derives de la piperidine
CA271,918A Expired CA1094059A (fr)	1976-02-17	1977-02-16	Derives de la piperidine

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CA271,918A Expired CA1094059A (fr)	1976-02-17	1977-02-16	Derives de la piperidine

Country Status (13)

Country	Link
JP (2)	JPS596851B2 (fr)
AT (2)	AT356106B (fr)
AU (1)	AU509216B2 (fr)
BE (2)	BE851509A (fr)
CA (2)	CA1094075A (fr)
CH (2)	CH605751A5 (fr)
DE (2)	DE2705949C2 (fr)
ES (5)	ES455834A1 (fr)
FR (2)	FR2342963A1 (fr)
GB (1)	GB1513631A (fr)
IE (2)	IE44611B1 (fr)
NL (2)	NL7701630A (fr)
ZA (2)	ZA77563B (fr)

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
US5395832A (en) *	1991-02-15	1995-03-07	Hokuriku Seiyaku Co., Ltd.	Benzamide derivatives
TW243449B (fr) *	1991-02-15	1995-03-21	Hokuriku Pharmaceutical

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BG21213A3 (bg) *	1972-06-01	1976-03-20	Societe D'etudes Scientifiques Et Industriellesde L'ile-De-France	Метод за получаване на 2-алкокси субституирани бензамиди
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 ZA00770563A patent/ZA77563B/xx unknown
- 1977-02-01 ZA ZA770562A patent/ZA77562B/xx unknown
- 1977-02-03 AU AU21925/77A patent/AU509216B2/en 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
- 1977-02-11 ES ES455831A patent/ES455831A1/es not_active Expired
- 1977-02-11 ES ES455832A patent/ES455832A1/es not_active Expired
- 1977-02-11 ES ES455835A patent/ES455835A1/es not_active Expired
- 1977-02-12 DE DE2705949A patent/DE2705949C2/de not_active Expired
- 1977-02-12 DE DE19772706038 patent/DE2706038A1/de not_active Ceased
- 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
- 1977-02-14 AT AT97877A patent/AT356105B/de not_active IP Right Cessation
- 1977-02-14 CH CH179877A patent/CH620678A5/fr 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 CA CA271,917A patent/CA1094075A/fr not_active Expired
- 1977-02-16 CA CA271,918A patent/CA1094059A/fr not_active Expired
- 1977-02-16 NL NL7701630A patent/NL7701630A/xx not_active Application Discontinuation
- 1977-02-16 BE BE175001A patent/BE851509A/fr not_active IP Right Cessation
- 1977-02-16 NL NL7701631A patent/NL7701631A/xx not_active Application Discontinuation
- 1977-02-16 FR FR7705169A patent/FR2341570A1/fr active Granted
- 1977-02-16 IE IE327/77A patent/IE44610B1/en unknown
- 1977-02-16 BE BE175000A patent/BE851508A/xx not_active IP Right Cessation
- 1977-02-17 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
IE44610B1 (en)	1982-01-27
IE44611L (en)	1977-08-17
DE2706038A1 (de)	1977-08-18
JPS596851B2 (ja)	1984-02-15
ZA77562B (en)	1977-12-28
ES455835A1 (es)	1978-01-01
JPS52122378A (en)	1977-10-14
ATA97877A (de)	1979-09-15
BE851509A (fr)	1977-06-16
NL7701630A (nl)	1977-08-19
DE2705949A1 (de)	1977-08-25
CA1094059A (fr)	1981-01-20
NL7701631A (nl)	1977-08-19
FR2342963B1 (fr)	1980-10-03
ATA98577A (de)	1979-09-15
JPS52122379A (en)	1977-10-14
DE2705949C2 (de)	1983-04-21
ZA77563B (en)	1978-04-26
BE851508A (fr)	1977-06-16
GB1513631A (en)	1978-06-07
AT356105B (de)	1980-04-10
AU509216B2 (en)	1980-05-01
ES455833A1 (es)	1978-01-01
IE44611B1 (en)	1982-01-27
ES455832A1 (es)	1978-01-01
CH605751A5 (fr)	1978-10-13
FR2342963A1 (fr)	1977-09-30
FR2341570A1 (fr)	1977-09-16
AT356106B (de)	1980-04-10
ES455831A1 (es)	1978-01-16
CH620678A5 (en)	1980-12-15
FR2341570B1 (fr)	1981-10-30
AU2192577A (en)	1978-08-10
ES455834A1 (es)	1978-01-01
IE44610L (en)	1977-08-17

Legal Events

Date	Code	Title	Description
1998-01-20	MKEX	Expiry

Publication	Publication Date	Title
CA1095044A (fr)	1981-02-03	Composes de n-piperid-4-yl benzamide
CA1095046A (fr)	1981-02-03	Composes de n-piperid-4-yl benzamide
GB1575310A (en)	1980-09-17	Piperidine derivatives
US4289772A (en)	1981-09-15	1-Piperidinophthalazines as cardiac stimulants
IE45833B1 (en)	1982-12-15	Octahydro-quinolizinyl benzamide derivatives
US3813400A (en)	1974-05-28	Derivatives of 3-amino-1,2,4-triazoles
US4207327A (en)	1980-06-10	N-(4-Pyrazolidinyl)benzamides and their amino precursors
US3875165A (en)	1975-04-01	(4-Quinolylamino)-(N-piperidyl)benzamides and N-{8 (quinolylamino)-benzoyl{9 piperidines
DE69215694T2 (de)	1997-05-28	Benzamid-derivate
US4087428A (en)	1978-05-02	N-(1-substituted-3-pyrrolidinyl)-4-quinoline carboxamides
CA1097648A (fr)	1981-03-17	Traduction non-disponible
EP0116347B1 (fr)	1987-07-29	1-Azaspiro(4.5)-décanes et 1-azaspiro(5.5)-undécanes substitués, intermédiaires, procédé de préparation et utilisation comme médicaments
US3479346A (en)	1969-11-18	N-acyl-n- (and n,n-bis-) ((1-piperidyl)-lower-alkyl)amines
US4163789A (en)	1979-08-07	Anti-psychotic (cycloalkenylalkylpiperidino) benzamides
CA1094059A (fr)	1981-01-20	Derives de la piperidine
US3515725A (en)	1970-06-02	2,3a-diazahydrindanone and 3h-pyrido-(1,2-c)pyrimidin-3-one derivatives
US3936459A (en)	1976-02-03	1',4'-Dihydro-1-methyl-spiro [piperidine and pyrrolidine-2,3'(2'H)quinoline]-2'-one compounds
US4039678A (en)	1977-08-02	N-(substituted-3-pyrrolidinyl)-1-naphthalene carboxamides
CA1105037A (fr)	1981-07-14	Traduction non-disponible
GB1574419A (en)	1980-09-03	Piperidine compounds
US3031455A (en)	1962-04-24	1-phenethyl-4-piperidyl carbamates
US4959375A (en)	1990-09-25	Piperidine derivatives useful as 5-HT3 antagonists
US3907811A (en)	1975-09-23	Stereoisomeric forms of 4-anilido-3-methyl-piperidine-1-carboxylates
US4279822A (en)	1981-07-21	N-(1-Substituted-3-pyrrolidinyl)benzamides
US2701797A (en)	1955-02-08	- indolylmethyl