CA1082710A - Preparation d'amides aromatiques - Google Patents

Preparation d'amides aromatiques

Info

Publication number: CA1082710A
Authority: CA; Canada
Prior art keywords: amino; group; methoxy; chloro; hydrogen
Prior art date: 1976-03-19
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

CA248,237A

Other languages

English (en)

Inventor

Jacinto Moragues Mauri

Robert G.W. Spickett

Armando Vega Noverola

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.)

1976-03-19

Filing date

1976-03-19

Publication date

1980-07-29

1976-03-19 Application filed by Anphar SA filed Critical Anphar SA

1976-03-19 Priority to CA248,237A priority Critical patent/CA1082710A/fr

1980-07-29 Application granted granted Critical

1980-07-29 Publication of CA1082710A publication Critical patent/CA1082710A/fr

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 10
150000008430 aromatic amides Chemical class 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 93
238000000034 method Methods 0.000 claims abstract description 41
239000001257 hydrogen Substances 0.000 claims abstract description 25
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
150000003839 salts Chemical class 0.000 claims abstract description 20
229910052736 halogen Inorganic materials 0.000 claims abstract description 15
150000002431 hydrogen Chemical class 0.000 claims abstract description 14
125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims abstract description 12
125000003118 aryl group Chemical group 0.000 claims abstract description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000004442 acylamino group Chemical group 0.000 claims abstract description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 5
-1 sulphonamido Chemical group 0.000 claims description 44
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 17
239000005711 Benzoic acid Substances 0.000 claims description 15
235000010233 benzoic acid Nutrition 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 9
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
150000008064 anhydrides Chemical class 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
239000002585 base Substances 0.000 claims description 6
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 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
150000004820 halides Chemical class 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000001246 bromo group Chemical group Br* 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 3
150000001558 benzoic acid derivatives Chemical class 0.000 claims description 3
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 3
125000006331 halo benzoyl group Chemical group 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
239000000126 substance Substances 0.000 claims 3
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims 2
230000002152 alkylating effect Effects 0.000 claims 1
239000012458 free base Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 23
238000011282 treatment Methods 0.000 abstract description 8
241000124008 Mammalia Species 0.000 abstract description 2
230000002490 cerebral effect Effects 0.000 abstract description 2
230000002496 gastric effect Effects 0.000 abstract description 2
230000007257 malfunction Effects 0.000 abstract description 2
125000003282 alkyl amino group Chemical group 0.000 abstract 1
125000005422 alkyl sulfonamido group Chemical group 0.000 abstract 1
125000003435 aroyl group Chemical group 0.000 abstract 1
125000004663 dialkyl amino group Chemical group 0.000 abstract 1
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 abstract 1
239000000243 solution Substances 0.000 description 42
239000000203 mixture Substances 0.000 description 39
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
125000005936 piperidyl group Chemical group 0.000 description 28
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
239000002253 acid Substances 0.000 description 22
239000000047 product Substances 0.000 description 22
229960001791 clebopride Drugs 0.000 description 21
235000013350 formula milk Nutrition 0.000 description 21
BVPWJMCABCPUQY-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-N-[1-(phenylmethyl)-4-piperidinyl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NC1CCN(CC=2C=CC=CC=2)CC1 BVPWJMCABCPUQY-UHFFFAOYSA-N 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
229940049920 malate Drugs 0.000 description 18
239000007787 solid Substances 0.000 description 18
BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 17
TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 17
229960004503 metoclopramide Drugs 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
230000000875 corresponding effect Effects 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
239000012442 inert solvent Substances 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
229960001701 chloroform Drugs 0.000 description 12
241000700159 Rattus Species 0.000 description 11
238000012360 testing method Methods 0.000 description 9
239000003826 tablet Substances 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
YUBDLZGUSSWQSS-UHFFFAOYSA-N 1-benzylpiperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CC=C1 YUBDLZGUSSWQSS-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
229940076134 benzene Drugs 0.000 description 6
239000000460 chlorine Substances 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
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
238000010992 reflux Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
206010047700 Vomiting Diseases 0.000 description 5
125000005907 alkyl ester group Chemical group 0.000 description 5
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
150000004292 cyclic ethers Chemical class 0.000 description 5
239000000725 suspension Substances 0.000 description 5
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 4
241000282472 Canis lupus familiaris Species 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
208000032140 Sleepiness Diseases 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
206010041349 Somnolence Diseases 0.000 description 4
230000003474 anti-emetic effect Effects 0.000 description 4
239000002111 antiemetic agent Substances 0.000 description 4
229940054066 benzamide antipsychotics Drugs 0.000 description 4
239000002775 capsule Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
206010007776 catatonia Diseases 0.000 description 4
210000003169 central nervous system Anatomy 0.000 description 4
239000002026 chloroform extract Substances 0.000 description 4
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 4
229960001076 chlorpromazine Drugs 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
238000007918 intramuscular administration Methods 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
239000008101 lactose Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
230000037321 sleepiness Effects 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
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 3
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 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
206010010904 Convulsion Diseases 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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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 3
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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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 3
229960004046 apomorphine Drugs 0.000 description 3
SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 description 3
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 3
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
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150000007529 inorganic bases Chemical class 0.000 description 3
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235000019359 magnesium stearate Nutrition 0.000 description 3
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 3
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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239000003054 catalyst Substances 0.000 description 2
229940116592 central nervous system diagnostic radiopharmaceuticals Drugs 0.000 description 2
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YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000035900 sweating Effects 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
230000003867 tiredness Effects 0.000 description 1
208000016255 tiredness Diseases 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000027 toxicology Toxicity 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
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA248,237A 1976-03-19 1976-03-19 Preparation d'amides aromatiques Expired CA1082710A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA248,237A CA1082710A (fr)	1976-03-19	1976-03-19	Preparation d'amides aromatiques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA248,237A CA1082710A (fr)	1976-03-19	1976-03-19	Preparation d'amides aromatiques

Publications (1)

Publication Number	Publication Date
CA1082710A true CA1082710A (fr)	1980-07-29

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ID=4105491

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Application Number	Title	Priority Date	Filing Date
CA248,237A Expired CA1082710A (fr)	1976-03-19	1976-03-19	Preparation d'amides aromatiques

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CA (1)	CA1082710A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5760035A (en) *	1993-09-22	1998-06-02	Knoll Aktiengesellschaft	Therapeutic agents

1976
- 1976-03-19 CA CA248,237A patent/CA1082710A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5760035A (en) *	1993-09-22	1998-06-02	Knoll Aktiengesellschaft	Therapeutic agents

Legal Events

Date	Code	Title	Description
1997-07-29	MKEX	Expiry

Publication	Publication Date	Title
US4138492A (en)	1979-02-06	Aromatic amides of heterocyclic compounds and therapeutic compositions containing same
CA1095044A (fr)	1981-02-03	Composes de n-piperid-4-yl benzamide
US3931195A (en)	1976-01-06	Substituted piperidines
US4797406A (en)	1989-01-10	Amides and esters containing bridged piperidines and use as serotonin M antagonists
GB1575310A (en)	1980-09-17	Piperidine derivatives
US4289772A (en)	1981-09-15	1-Piperidinophthalazines as cardiac stimulants
CA1094072A (fr)	1981-01-20	Derives cycloalkenyl des n-piperid-4-y1 benzamides
JPH02243688A (ja)	1990-09-27	新規キヌクリジン類、該化合物を含有する医薬組成物、及びその製造方法
EP0510129A1 (fr)	1992-10-28	Antagonistes de recepteurs muscariniques
US4069223A (en)	1978-01-17	4-Aminomethyl-1-(3,3,3-triarylpropyl)-4-arylpiperidine and derivatives thereof
NZ199162A (en)	1984-11-09	8-(3-arylpropyl)-3-phenylnortropan-3-ols
CA1097648A (fr)	1981-03-17	Traduction non-disponible
EP0014997A1 (fr)	1980-09-03	Dérivés de 4-aryloxy- et 4-arylthio-3-phénylpipéridine, procédé pour la préparation de tels composés et compositions pharmaceutiques les contenant
WO1993008192A1 (fr)	1993-04-29	Oximes d'arylenyne et d'arylacetylene azabicyclo utilises comme agents cholinergiques, et procedes de traitement
FI60200B (fi)	1981-08-31	Foerfarande foer framstaellning av farmakologiskt vaerdefulla n-arylalkylpiperidylsubstituerade bensamider
IE43819B1 (en)	1981-06-03	1-naphthalene and 4-quinolinecarbomaxides
CA1082710A (fr)	1980-07-29	Preparation d'amides aromatiques
CA1142516A (fr)	1983-03-08	10,11-dihydro-5h-dibenzo(a,d) cycloheptene-5,10-imines
CA1100136A (fr)	1981-04-28	Traduction non-disponible
IE46442B1 (en)	1983-06-15	Morphine derivatives
AU593220B2 (en)	1990-02-08	Spasmolytically active tertiary amine derivatives and method of preparing the same
US3509166A (en)	1970-04-28	Tetrahydro-pyridine derivatives of benzamide
WO1992006958A1 (fr)	1992-04-30	Derives de 4-acetoxy-piperidine, procede servant a leur preparation, et leur utilisation comme antagonistes de recepteur m3 de muscarine
US4032640A (en)	1977-06-28	4H-Benzo[4,5]cyclohepta[1,2-b]thiophenes
JPH02279660A (ja)	1990-11-15	テトラヒドロナフタレン誘導体

CA1082710A - Preparation d'amides aromatiques - Google Patents

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Applications Claiming Priority (1)

Publications (1)

Family

ID=4105491

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Country Status (1)

Cited By (1)

Cited By (1)

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