CA1085855A - Composes a base de benzamide de n-piperid-4-yle - Google Patents

Composes a base de benzamide de n-piperid-4-yle

Info

Publication number: CA1085855A
Authority: CA; Canada
Prior art keywords: methoxy; amino; piperid; chlorobenzamide; preparation
Prior art date: 1976-10-27
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

CA289,550A

Other languages

English (en)

Inventor

Armando Vega Noverola

Jose Boix Iglesias

Jacinto Moragues Mauri

Robert G.W. Spickett

Jose 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.)

Anphar SA

Original Assignee

Anphar 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.)

1976-10-27

Filing date

1977-10-26

Publication date

1980-09-16

1977-10-26 Application filed by Anphar SA filed Critical Anphar SA

1980-09-16 Application granted granted Critical

1980-09-16 Publication of CA1085855A publication Critical patent/CA1085855A/fr

Status Expired legal-status Critical Current

Links

JMQDNLCNCDSHNC-UHFFFAOYSA-N n-piperidin-4-ylbenzamide Chemical class C=1C=CC=CC=1C(=O)NC1CCNCC1 JMQDNLCNCDSHNC-UHFFFAOYSA-N 0.000 title claims description 4
-1 N-substituted benzamides Chemical class 0.000 claims abstract description 17
150000001875 compounds Chemical class 0.000 claims abstract description 15
238000000034 method Methods 0.000 claims description 51
238000002360 preparation method Methods 0.000 claims description 25
150000008064 anhydrides Chemical class 0.000 claims description 23
RVEATKYEARPWRE-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxybenzoic acid Chemical compound COC1=CC(N)=C(Cl)C=C1C(O)=O RVEATKYEARPWRE-UHFFFAOYSA-N 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
LEDAKUURWBSEEZ-UHFFFAOYSA-N 4,5-diamino-N-(1-benzylpiperidin-4-yl)-2-methoxybenzamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)NC(C1=C(C=C(C(=C1)N)N)OC)=O LEDAKUURWBSEEZ-UHFFFAOYSA-N 0.000 claims description 3
ROHNZSJJOBHGHY-UHFFFAOYSA-N 4-acetamido-5-amino-N-(1-benzylpiperidin-4-yl)-2-methoxybenzamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)NC(C1=C(C=C(C(=C1)N)NC(C)=O)OC)=O ROHNZSJJOBHGHY-UHFFFAOYSA-N 0.000 claims description 3
CHTSGIIIYFQURK-UHFFFAOYSA-N 4-amino-N-(1-benzylpiperidin-4-yl)-5-chloro-2-ethoxybenzamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)NC(C1=C(C=C(C(=C1)Cl)N)OCC)=O CHTSGIIIYFQURK-UHFFFAOYSA-N 0.000 claims description 3
LSBZVSYVMOFTCB-UHFFFAOYSA-N N-(1-benzylpiperidin-4-yl)-5-chloro-4-(dimethylamino)-2-methoxybenzamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)NC(C1=C(C=C(C(=C1)Cl)N(C)C)OC)=O LSBZVSYVMOFTCB-UHFFFAOYSA-N 0.000 claims description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
239000005711 Benzoic acid Substances 0.000 claims description 2
125000005336 allyloxy group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
235000010233 benzoic acid Nutrition 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
LGUNRSBYISSUIH-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-5-chloro-2-methoxy-4-(methylamino)benzamide Chemical compound C1=C(Cl)C(NC)=CC(OC)=C1C(=O)NC1CCN(CC=2C=CC=CC=2)CC1 LGUNRSBYISSUIH-UHFFFAOYSA-N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
150000003053 piperidines Chemical class 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
239000000126 substance Substances 0.000 claims 23
YUBDLZGUSSWQSS-UHFFFAOYSA-N 1-benzylpiperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CC=C1 YUBDLZGUSSWQSS-UHFFFAOYSA-N 0.000 claims 8
LXQZIGNTEIITSW-UHFFFAOYSA-N 4-acetamido-5-amino-2-methoxybenzoic acid Chemical compound COC1=CC(NC(C)=O)=C(N)C=C1C(O)=O LXQZIGNTEIITSW-UHFFFAOYSA-N 0.000 claims 4
PFQXDUKLHMLEHY-UHFFFAOYSA-N 1-(1-phenylethyl)piperidin-4-amine Chemical compound C=1C=CC=CC=1C(C)N1CCC(N)CC1 PFQXDUKLHMLEHY-UHFFFAOYSA-N 0.000 claims 3
BRUKSTGIAUDJQX-UHFFFAOYSA-N 1-[(4-methylphenyl)methyl]piperidin-4-amine Chemical compound C1=CC(C)=CC=C1CN1CCC(N)CC1 BRUKSTGIAUDJQX-UHFFFAOYSA-N 0.000 claims 2
DCMVADAFYLUQQW-UHFFFAOYSA-N 4,5-diamino-2-methoxy-N-[1-(1-phenylethyl)piperidin-4-yl]benzamide Chemical compound C1(=CC=CC=C1)C(C)N1CCC(CC1)NC(C1=C(C=C(C(=C1)N)N)OC)=O DCMVADAFYLUQQW-UHFFFAOYSA-N 0.000 claims 2
LYFZXIXVTGAHSZ-UHFFFAOYSA-N 4,5-diamino-2-methoxybenzoic acid Chemical compound COC1=CC(N)=C(N)C=C1C(O)=O LYFZXIXVTGAHSZ-UHFFFAOYSA-N 0.000 claims 2
SSJJZBQBCOVRON-UHFFFAOYSA-N 4-acetamido-5-amino-2-methoxy-N-[1-[(4-methylphenyl)methyl]piperidin-4-yl]benzamide Chemical compound COC1=C(C=C(N)C(NC(C)=O)=C1)C(=O)NC1CCN(CC2=CC=C(C)C=C2)CC1 SSJJZBQBCOVRON-UHFFFAOYSA-N 0.000 claims 2
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
IRYMDKBKQHLSSP-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-N-[1-[(4-nitrophenyl)methyl]piperidin-4-yl]benzamide Chemical compound [N+](=O)([O-])C1=CC=C(CN2CCC(CC2)NC(C2=C(C=C(C(=C2)Cl)N)OC)=O)C=C1 IRYMDKBKQHLSSP-UHFFFAOYSA-N 0.000 claims 2
VLJYXJPDUGAIGS-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-N-[1-[[3-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]benzamide Chemical compound FC(C=1C=C(CN2CCC(CC2)NC(C2=C(C=C(C(=C2)Cl)N)OC)=O)C=CC1)(F)F VLJYXJPDUGAIGS-UHFFFAOYSA-N 0.000 claims 2
HNWQAEISMMBONY-UHFFFAOYSA-N 4-amino-5-chloro-N-[1-[(5-chloro-2-methoxyphenyl)methyl]piperidin-4-yl]-2-methoxybenzamide Chemical compound COC1=C(CN2CCC(CC2)NC(=O)C2=C(OC)C=C(N)C(Cl)=C2)C=C(Cl)C=C1 HNWQAEISMMBONY-UHFFFAOYSA-N 0.000 claims 2
IJABAFIATAYTOA-UHFFFAOYSA-N N-(1-benzylpiperidin-4-yl)-5-chloro-2-ethoxy-4-(methylamino)benzamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)NC(C1=C(C=C(C(=C1)Cl)NC)OCC)=O IJABAFIATAYTOA-UHFFFAOYSA-N 0.000 claims 2
WFONBGLNOUINIL-UHFFFAOYSA-N 1-[(2-methylphenyl)methyl]piperidin-4-amine Chemical compound CC1=CC=CC=C1CN1CCC(N)CC1 WFONBGLNOUINIL-UHFFFAOYSA-N 0.000 claims 1
DFJQENRMQNZDNL-UHFFFAOYSA-N 1-[(3-methylphenyl)methyl]piperidin-4-amine Chemical compound CC1=CC=CC(CN2CCC(N)CC2)=C1 DFJQENRMQNZDNL-UHFFFAOYSA-N 0.000 claims 1
DDPNUBVUABSUEG-UHFFFAOYSA-N 1-[(4-bromophenyl)methyl]piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=C(Br)C=C1 DDPNUBVUABSUEG-UHFFFAOYSA-N 0.000 claims 1
KRIHULMCWJRKQE-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=C(F)C=C1 KRIHULMCWJRKQE-UHFFFAOYSA-N 0.000 claims 1
UHIQIZHKFBGXFN-UHFFFAOYSA-N 1-[(4-nitrophenyl)methyl]piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=C([N+]([O-])=O)C=C1 UHIQIZHKFBGXFN-UHFFFAOYSA-N 0.000 claims 1
BGXWETBTBPDHLX-UHFFFAOYSA-N 1-[[3-(trifluoromethyl)phenyl]methyl]piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CC(C(F)(F)F)=C1 BGXWETBTBPDHLX-UHFFFAOYSA-N 0.000 claims 1
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
MFFJRVXQMRMLFG-UHFFFAOYSA-N 4-acetamido-5-amino-2-methoxy-N-[1-(1-phenylethyl)piperidin-4-yl]benzamide Chemical compound C1(=CC=CC=C1)C(C)N1CCC(CC1)NC(C1=C(C=C(C(=C1)N)NC(C)=O)OC)=O MFFJRVXQMRMLFG-UHFFFAOYSA-N 0.000 claims 1
WVQQTDYDAOKFFU-UHFFFAOYSA-N 4-acetamido-5-amino-N-[1-[(5-chloro-2-methoxyphenyl)methyl]piperidin-4-yl]-2-methoxybenzamide Chemical compound COC1=C(CN2CCC(CC2)NC(C2=C(C=C(C(=C2)N)NC(C)=O)OC)=O)C=C(C=C1)Cl WVQQTDYDAOKFFU-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
ZNSAIFPUSGTITD-UHFFFAOYSA-N 4-amino-5-chloro-2-ethoxy-N-[1-(1-phenylethyl)piperidin-4-yl]benzamide Chemical compound C1(=CC=CC=C1)C(C)N1CCC(CC1)NC(C1=C(C=C(C(=C1)Cl)N)OCC)=O ZNSAIFPUSGTITD-UHFFFAOYSA-N 0.000 claims 1
HACDRDRPZJHBGW-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-N-[1-[(3-methylphenyl)methyl]piperidin-4-yl]benzamide Chemical compound CC=1C=C(CN2CCC(CC2)NC(C2=C(C=C(C(=C2)Cl)N)OC)=O)C=CC1 HACDRDRPZJHBGW-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
KZKOWXZFTMYRSE-UHFFFAOYSA-N 5-chloro-4-(dimethylamino)-2-methoxybenzoic acid Chemical compound COC1=CC(N(C)C)=C(Cl)C=C1C(O)=O KZKOWXZFTMYRSE-UHFFFAOYSA-N 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 abstract description 3
230000000144 pharmacologic effect Effects 0.000 abstract description 3
208000025865 Ulcer Diseases 0.000 abstract description 2
206010047141 Vasodilatation Diseases 0.000 abstract description 2
208000022531 anorexia Diseases 0.000 abstract description 2
206010061428 decreased appetite Diseases 0.000 abstract description 2
230000027119 gastric acid secretion Effects 0.000 abstract description 2
230000005764 inhibitory process Effects 0.000 abstract description 2
231100000397 ulcer Toxicity 0.000 abstract description 2
230000024883 vasodilation Effects 0.000 abstract description 2
230000015572 biosynthetic process Effects 0.000 abstract 1
239000000155 melt Substances 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
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
125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
125000003320 C2-C6 alkenyloxy group Chemical group 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
240000001307 Myosotis scorpioides Species 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000006278 bromobenzyl group Chemical group 0.000 description 1
239000002775 capsule Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA289,550A 1976-10-27 1977-10-26 Composes a base de benzamide de n-piperid-4-yle Expired CA1085855A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB4464976A GB1593851A (en)	1976-10-27	1976-10-27	N-(4-piperidyl)-benzamides and pharmaceutical compositions containing them
GB44649/76		1976-10-27

Publications (1)

Publication Number	Publication Date
CA1085855A true CA1085855A (fr)	1980-09-16

Family

ID=10434204

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA289,550A Expired CA1085855A (fr)	1976-10-27	1977-10-26	Composes a base de benzamide de n-piperid-4-yle

Country Status (8)

Country	Link
JP (1)	JPS5392783A (fr)
BE (1)	BE860139R (fr)
CA (1)	CA1085855A (fr)
CH (1)	CH625219A5 (fr)
ES (1)	ES463557A2 (fr)
FR (1)	FR2378762A2 (fr)
GB (1)	GB1593851A (fr)
NL (1)	NL7711690A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU1057101A (en) *	1999-11-17	2001-05-30	Kissei Pharmaceutical Co. Ltd.	Hydroxyethoxybenzamide derivatives and drugs containing the same
TW200800953A (en)	2002-10-30	2008-01-01	Theravance Inc	Intermediates for preparing substituted 4-amino-1-(pyridylmethyl) piperidine
JP2007524641A (ja)	2003-07-11	2007-08-30	セラヴァンス，インコーポレーテッド	置換４−アミノ−１−ベンジルピペリジン化合物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR5916M (fr) *	1966-01-21	1968-05-06
GB1345872A (en) *	1970-09-03	1974-02-06	Wyeth John & Brother Ltd	Amino-and acylamino-pyridine and hydropyridine derivatives

1976
- 1976-10-27 GB GB4464976A patent/GB1593851A/en not_active Expired
1977
- 1977-10-25 NL NL7711690A patent/NL7711690A/xx not_active Application Discontinuation
- 1977-10-25 CH CH1295177A patent/CH625219A5/fr not_active IP Right Cessation
- 1977-10-26 CA CA289,550A patent/CA1085855A/fr not_active Expired
- 1977-10-26 ES ES463557A patent/ES463557A2/es not_active Expired
- 1977-10-26 FR FR7733111A patent/FR2378762A2/fr active Granted
- 1977-10-26 BE BE182086A patent/BE860139R/fr not_active IP Right Cessation
- 1977-10-27 JP JP12915777A patent/JPS5392783A/ja active Pending

Also Published As

Publication number	Publication date
BE860139R (fr)	1978-02-15
GB1593851A (en)	1981-07-22
CH625219A5 (en)	1981-09-15
FR2378762B2 (fr)	1980-09-12
ES463557A2 (es)	1978-11-16
NL7711690A (nl)	1978-05-02
FR2378762A2 (fr)	1978-08-25
JPS5392783A (en)	1978-08-15

Legal Events

Date	Code	Title	Description
1997-09-16	MKEX	Expiry

Publication	Publication Date	Title
RU2154639C2 (ru)	2000-08-20	Производные пиперазинов, способы их получения и фармацевтическая композиция
EP0883613A1 (fr)	1998-12-16	Derives de sulfonamide en tant qu'antagonistes du recepteur de 5ht7
US5389630A (en)	1995-02-14	Diamine compound and brain protecting agent containing the same
JPS61152666A (ja)	1986-07-11	新規な二環式ヘテロアリールピペラジン誘導体、その製造方法およびその誘導体を有効成分とする向精神医薬組成物
IL104305A (en)	1998-04-05	Piperazine derivatives, their preparation and pharmaceutical compositions containing them
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CA1261335A (fr)	1989-09-26	Derives d'ethylenediamine-monoamides
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EP0395313A2 (fr)	1990-10-31	Dérivés de pipérazine avec une fonction alkyle tertiaire
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US7285664B2 (en)	2007-10-23	Heterocyclic or benzenic derivatives of lipoic acid, their preparation and their use as medicaments
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US5519025A (en)	1996-05-21	4-indolylpiperazinyl derivatives
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AU624978B2 (en)	1992-06-25	N,n'-bis(alkoxyalkyl)-pyridine-2,4-dicarboxylic acid diamides, preparation and their use
CS357891A3 (en)	1992-12-16	/2-(dimethylamino)ethyl/-/2-//2-(methylthio)phenyl/amino/-2-oxoethyl/carbamates or ureas thereof, process oftheir preparation and pharmaceutical compositions containing said carbamates orureas
US4183937A (en)	1980-01-15	Blood pressure lowering benzoquinolizines
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CA1252794A (fr)	1989-04-18	Derives de benzamide
CA1276639C (fr)	1990-11-20	Derives d'aminobenzamide
GB1593851A (en)	1981-07-22	N-(4-piperidyl)-benzamides and pharmaceutical compositions containing them
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US4153702A (en)	1979-05-08	Basically alkylated dithiosalicyclic acid amides and their use as medicaments
JPS584749A (ja)	1983-01-11	アミノベンジルアミン誘導体、その製法および薬剤としての用途