FI83768B - Foerfarande foer framstaellning av farmakologiskt aktiva substituerade bensamidderivat. - Google Patents

Foerfarande foer framstaellning av farmakologiskt aktiva substituerade bensamidderivat. Download PDF

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FI83768B
FI83768B FI852512A FI852512A FI83768B FI 83768 B FI83768 B FI 83768B FI 852512 A FI852512 A FI 852512A FI 852512 A FI852512 A FI 852512A FI 83768 B FI83768 B FI 83768B
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amino
chloro
ethyl
diethylamino
compound
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FI852512A
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Finnish (fi)
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FI852512A0 (fi
FI852512L (fi
FI83768C (sv
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Ivo Monkovic
David Willner
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Bristol Myers Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • 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
    • C07D211/40—Oxygen atoms
    • C07D211/42—Oxygen atoms attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D233/22—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Hydrogenated Pyridines (AREA)

Claims (2)

1. Förfarande för framställning av farmakologiskt aktiva substituerade bensamidderivat med formeln I 5 CONHR1 /^y-O-R2
10 C1 NHj väri R1 är 15 r7 CH30_ -»>>·<„ -O— n är ett helt tai inom omrädet 1-4;
20 R7 är R8 samma eller oiikä och betecknar lägre alkyl; R17 är halogen; X I # R2 är -CHjOCHjCHjOR9, -CH2CH2ORl\ -C - C R9 R14 R9 R13 O- or I / -CH-C-R9 , -CH2CH2-CH , -CH2(CH2)qB, ''''OR15 cJ R9 0 N -CH-CN, -CH2-<1 ^R9 eller-CH2-CH — CH2; X/ o 'o
30 C^CHj X är syre eller =N0R9; a o (O), o .Η’ ^ΝΊ m t „ " n 'S B är -NHCR9, -S-R , -C-N , ^ R9 N-l pyridyl eller oxosubstituerad oxazolidinyl; 35 p är 0 eller 1; II 83 83768 q är ett helt tai inom omrädet 0-4; R9 är väte eller lägre alkyl; R11 är väte, lägre alkyl, (lägre)alkoxi(lägre)alkyl eller acetyl;
5 R12 är väte, lägre alkyl, lägre alkenyl eller fenyl och R14 är lägre alkyl, lägre alkoxi, hydrazino, acetyl-hydrazino, tienyl, fenyl, bensyl, amino, lägre alkylami-no, di(lägre)alkylamino eller pyrrolidino, eller R12 och R14 tillsammans med kolatomerna, vid vilka de är bundna, 10 bildar en cyklohexanring; R13 är lägre alkyl, lägre alkoxi eller fenyl; och R15 är väte eller lägre alkyl, kännetecknat därav, att a) en förening med formeln II 15 i CONHR1 i T Cl 20 nh2 väri R1 är som ovan definierats, omsätts med en förening med formeln R2-L, väri R2 är som ovan definierats och L är en konventionell avgäende grupp, in närvaro av en bas 25 som syrabindande medel, eller b) för framställning av en förening med formeln I, väri R2 är -CH2( CH2 )q-S-R9, en förening med formeln II omsätts med en förening med formeln Hal-CH2(CH2)q-Hal, väri vardera Hai är en halogenatom, varvid dessa tvä halogen- 30 atomer kan vara samma eller olika, och därefter med en förening med formeln HSR9, eller c) för framställning av en förening med formeln I, väri R2 är /CH3
35 -CH2-C-CH3, en förening med formeln II omsätts med \>H 84 8 3 768 l-klor-2,3-epoxi-2-metylpropan och den sä erhällna före-ningen reduceras, och om sä öskas, i) en förening med formeln I, väri R2 är
5 -CH2( CH2 )qB och B är -S-R9, oxideras till en motsvarande förening, väri 0 f B är -S-R9, eller 10 ii) en förening med formeln I, väri R2 är R12 X) 1 ^ 9 -C-C , omsätts med en förening med formeln H2N0R R9 ^R14 för erhällande av en motsvarande förening, väri X är 15 =N0R9, eller iii ) en förening med formeln I, väri R2 är R12 o -C-C och den ena eller bäda tvä av radikalerna R9
20 R9 ^R14 och R12 är väte, omsätts med ett halogenalkan eller halogenalken i närvaro av natriumhydrid för erhällande av en motsvarande förening, väri bäda tvä eller den ena av radikalerna R9 och R12 är lägre alkyl eller lägre alkenyl, 25 eller iv) en förening med formeln I, väri R2 är R9 0 I X -CH-C och R är lägre alkyl, reduceras tili en ^R14 R9 ^OH 30 motsvarande förening, väri R är -CH-CH , \r14 eller v) en förening med formeln I, väri R2 är R12 .0 I ^
35 -C-C ^ och R14 är lägre alkoxi, omsätts med R9 ^R14 II 85. o768 ammoniak, mono- eller di(lägre)alkylamin, pyrrolidin el-ler hydrazin för framställning av en motsvarande före-ning, väri R14 är respektive amino, lägre alkylamino, di-(lägre)alkylamino, pyrrolidino eller hydrazino, och om sä 5 önskas acetyleras hydrazinogruppen R14, eller vi) i en förening med formeln I oxideras R9 R2-gruppen -CHCN 10 R9 tili en grupp -CHCH2NH2 och omsätts denna med ett acyle- ringsmedel för framställning av en förening med formeln I, väri R9 0 I "
15 R2 är -CHCH2NHC-R9' och R9' är lägre alkyl, eller R9 , I vii) en förening med formeln I, väri R är -CHCN, omsätts med 1,2-diaminoetan för framställning av en före- 20 ning med formeln I, väri R2 är R9 xN—i 1 / ‘“X ' \N—» och om sä önskas, omvandlas en förening med for-25 mein I tili ett giftfritt farmaceutiskt godtagbart sait, hydrat, soivat eller kvartärt ammoniumsalt därav.
2. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att man framställer därmed en av följande föreningar 1-30 eller ett giftfritt farma-30 ceutiskt godtagbart sait, hydrat, soivat eller kvartärt ammoniumsalt därav: 1) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-(2-metoxi-etoxi)bensamid, 2) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-(2-hydroxi- 35 etoxi)bensamid, 86 85 7 68 3) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-(2,2-dimet-oxietoxi)bensamid, 4) 4-amino-5-klor-N-[2-(dietylamino)etyl]2-[(2-metoxi-etoxi)metyloxi]bensamid, 5 5) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-(2-propanon- 1-yl)oxibensamid, 6) 4-amino-2-bensoylmetyloxi-5-klor-N-[2-(dietylamino)-etyl]bensamid, 7) 4-amino-2-(butan-2-on-3-yl)oxi-5-klor-N-[2-(di-10 etylamino)etyl]bensamid, 8) 4-amino-5-klor-2-(cyklohexanon-2-y1)oxi-N-[2-(dietylamino)etyl]bensamid, 9) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-(5-hexen-2-on-3-yl)oxibensamid, 15 10) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-[(2-hydroxi- imino)propan-1-y1]oxibensamid, 11) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-[(2-metoxi-imino)propan-1-yl]oxibensamid, 12) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-(2-hydroxi- 20 propan-l-yl)oxibensamid, 13 ) 4-amino-5-klor-2-cyanmetyloxi-N-[2-(dietylamino)- etyl]bensamid, 14) 4-amino-2-(karboxamidmetyloxi)-5-klor-N-[2-(dietyl amino )etyl] bensamidacetat, 25 15) 4-amino-2-(2-butyn-l-yl)oxi-5-klor-N-[2-(dietyl amino )etyl]bensamid, 16 ) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-[2- (metylsulfinyl)etoxi]bensamid, 17) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-(pentan-2- 30 on-yl)oxibensamid, 18) 4-amino-2-(2-butanon-l-yl)oxi-5-klor-N-[2-(dietylamino )etyl]bensamid, 19) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-(pentan-2-on-l-yl)oxibensamid, 35 20) 4-amino-5-klor-2-(pentan-3-on-2-yl)oxi-N-(2-dietyl- II 87 8 5 768 aminoetyl)bensamid, 21) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-(2-hydrazin- 2-oxo-etoxi)bensamid, 22. treo-4-amino-5-klor-N-[2-(dietylamino)etyl]-2-hydr-5 oxibut-3-yl)oxibensamid, 23. erytro-4-amino-5-klor-N-[2-(dietylamino)etyl]-2-(2-hydroxibut-3-yl)oxibensamdi, 24) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-[(2-metyl-amino)-2-oxoetyl]bensamid, 10 25) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-(etyl-3-met- oxi-kroton-4-yl)oxibensamid, 26) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-(1,3-di-oxolan-2-yl)oxibensamid, 27) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-(oxazoli- 15 din)-2-oni-5-ylmetyl)oxibensamid, 28) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-(2-pyridin-metyl)oxibensamid, 29) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-tetrahydro-furfuryl-oxibensamid, och 20 30) 4-amino-5-klor-N-[2-(dietylamino)etyl]-2-(2-metoxi- etoxietyl)oxibensamid.
FI852512A 1984-06-28 1985-06-25 Förfarande för framställning av farmakologiskt aktiva substituerade be nsamidderivat FI83768C (sv)

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Application Number Priority Date Filing Date Title
US62574284A 1984-06-28 1984-06-28
US62574284 1984-06-28
US06/729,513 US4808624A (en) 1984-06-28 1985-05-06 Pharmacologically active substituted benzamides
US72951385 1985-05-06

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FI852512A0 FI852512A0 (fi) 1985-06-25
FI852512L FI852512L (fi) 1985-12-29
FI83768B true FI83768B (fi) 1991-05-15
FI83768C FI83768C (sv) 1991-08-26

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AR (1) AR244677A1 (sv)
AT (1) AT394363B (sv)
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DE (1) DE3523076C2 (sv)
DK (1) DK170332B1 (sv)
ES (5) ES8609218A1 (sv)
FI (1) FI83768C (sv)
FR (1) FR2566773B1 (sv)
GB (1) GB2160871B (sv)
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Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH653670A5 (de) * 1983-03-03 1986-01-15 Hoffmann La Roche Benzamid-derivate.
US4820715A (en) * 1984-06-28 1989-04-11 Bristol-Myers Company Anti-emetic quinuclidinyl benzamides
US4772630A (en) * 1984-11-23 1988-09-20 Ciba-Geigy Corp. Benzamides and their salts
US4882356A (en) * 1987-03-10 1989-11-21 Nassar Munir N Stable injectable antiemetic compositions
FI871447A (fi) * 1986-04-07 1987-10-08 Bristol Myers Co Stabila injicerbara antivomitiva kompositioner.
US4772459A (en) * 1986-09-09 1988-09-20 Erbamont, Inc. Method for controlling emesis caused by chemotherapeutic agents and antiemetic agents useful therein
FR2618149B1 (fr) * 1987-07-16 1989-09-22 Synthelabo Derives de n-aminoalkyl n-phenyl arylamides, leur preparation et leur application en therapeutique
GB8718346D0 (en) * 1987-08-03 1987-09-09 Fordonal Sa Substituted benzamides
GB8718345D0 (en) * 1987-08-03 1987-09-09 Fordonal Sa N-substituted benzamides
IT1216120B (it) * 1988-03-17 1990-02-22 Poli Ind Chimica Spa Derivati n_cicloalchilaminoetilbenzamidici, loro preparazione e composizioni farmaceutiche che li contengono.
US5374637A (en) * 1989-03-22 1994-12-20 Janssen Pharmaceutica N.V. N-(3-hydroxy-4-piperidinyl)(dihydrobenzofuran, dihydro-2H-benzopyran or dihydrobenzodioxin)carboxamide derivatives
US5126343A (en) * 1989-09-11 1992-06-30 G. D. Searle & Co. N-azabicyclo [3.3.0]octane amides of aromatic acids
GB9005014D0 (en) * 1990-03-06 1990-05-02 Janssen Pharmaceutica Nv N.(4.piperidinyl)(dihydrobenzofuran or dihydro.2h.benzopyran)carboxamide derivatives
US5395832A (en) * 1991-02-15 1995-03-07 Hokuriku Seiyaku Co., Ltd. Benzamide derivatives
CA2074061A1 (en) * 1991-08-26 1993-02-27 Ivo Monkovic Benzamide multidrug resistance reversing agents
US5723103A (en) * 1994-12-09 1998-03-03 Vanderbilt University Substituted benzamides and radioligand analogs and methods of use
JP3933244B2 (ja) * 1997-04-04 2007-06-20 株式会社資生堂 アルキレンジアミン誘導体及び抗潰瘍剤、抗菌剤
EP2253316B1 (en) 2009-05-20 2013-08-14 INSERM (Institut National de la Santé et de la Recherche Médicale) Serotonin 5-HT3 receptor antagonists for use in the treatment or prevention of an inner ear pathology with vestibular deficits
JP5955767B2 (ja) 2009-05-20 2016-07-20 インセルム（インスティチュート ナショナル デ ラ サンテ エ デ ラ リシェルシェ メディカル） 損傷性前庭障害の処置における使用のためのセロトニン５−ｈｔ３受容体拮抗薬
KR101641836B1 (ko) 2015-06-25 2016-07-22 (주)유경 세균방지를 위한 복수형 우유냉각장치

Family Cites Families (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1139272A (fr) * 1954-06-29 1957-06-27 Thomae Gmbh Dr K Perfectionnements apportés aux procédés pour fabriquer des dérivés de l'acide benzoïque
DE1078581B (de) * 1958-03-15 1960-03-31 Riedel De Haeen Ag Verfahren zur Herstellung von 1, 3-Dioxolanyl-(4)-methylaethern von o-Vanillinsaeureamiden
FR1525M (fr) * 1961-07-25 1962-11-16 Ile De France Médicaments antiémétiques nouveaux.
FR1526M (fr) * 1961-07-25 1962-10-15 Ile De France Nouveaux médicaments antiémétiques.
NL281394A (sv) * 1961-07-25
FR1407055A (fr) * 1963-03-05 1965-07-30 Ile De France Nouveau procédé de préparation de benzamides substitués
GB1019781A (sv) * 1963-03-05
GB1047028A (en) * 1963-11-15 1966-11-02 Rech S Et D Applic Scient Et M Improvements in or relating to 5-acetamido-salicylamide derivatives
ES336000A1 (es) * 1966-01-22 1968-04-01 Ile De France Nuevo procedimiento de preparacion de 2-alcoxi-5-halogeno- benzamidas n-aminoalquil sustituidas.
CH505852A (de) * 1968-03-21 1971-04-15 Ciba Geigy Ag Verfahren zur Herstellung von neuen Benzoxazepinonen
US3891671A (en) * 1968-08-01 1975-06-24 Ile De France N-(2-pyrrolidyl or piperidyl alkyl)-4-hydroxy benzamides
CA988534A (en) * 1969-02-26 1976-05-04 John Krapcho Benzamide derivatives and processes for their manufacture
FR2313935A1 (fr) * 1975-06-10 1977-01-07 Ile De France Nouveaux benzamides substitues, leurs derives et leur procede de preparation
US3963745A (en) * 1972-04-03 1976-06-15 A. H. Robins Company, Incorporated Method for controlling emesis with N-(1-substituted-3-pyrrolidinyl)benzamides and thiobenzamides
US3966957A (en) * 1972-04-03 1976-06-29 A. H. Robins Company, Incorporated Method for controlling emesis with N-(1-substituted-3-pyrrolidinyl)benzamides and thiobenzamides
FR2277815A1 (fr) * 1972-06-20 1976-02-06 Ile De France Nouveau procede de preparation du n(diethylaminoethyl) 2-methoxy 4-amino 5-chlorobenzamide
FR2281353A1 (fr) * 1972-06-22 1976-03-05 Ile De France Nouveau procede de preparation du n(diethylaminoethyl) 2-methoxy 4-amino 5-chlorobenzamide
JPS4969627A (sv) * 1972-10-31 1974-07-05
JPS5035125A (sv) * 1973-07-24 1975-04-03
FR2243933B1 (sv) * 1973-09-17 1978-06-30 Ile De France
JPS5126840A (en) * 1974-08-26 1976-03-05 Ile De France Nn jiarukiruaminoarukiru 22 arukokishi 44 chikan 55 harobenzuamido no seizoho
GB1574418A (en) * 1976-11-16 1980-09-03 Anphar Sa Piperidine derivatives
DE2721643A1 (de) * 1977-05-13 1978-11-23 Heumann Ludwig & Co Gmbh Verfahren zur herstellung von eckige klammer auf n,n-dialkylamino-alkyl eckige klammer zu -2-alkoxy-5-sulfamoylbenzamiden
US4207327A (en) * 1977-08-19 1980-06-10 A. H. Robins Company, Inc. N-(4-Pyrazolidinyl)benzamides and their amino precursors
CA1183847A (en) * 1981-10-01 1985-03-12 Georges Van Daele N-(3-hydroxy-4-piperidinyl)benzamide derivatives

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GB8516320D0 (en) 1985-07-31
KR920000270B1 (ko) 1992-01-11
US4808624A (en) 1989-02-28
IT8521325A0 (it) 1985-06-27
ATA193185A (de) 1991-09-15
YU107085A (en) 1988-02-29
FI852512A0 (fi) 1985-06-25
SE8503207D0 (sv) 1985-06-27
SE502926C2 (sv) 1996-02-19
MY102080A (en) 1992-03-31
NO852561L (no) 1985-12-30
GB2160871B (en) 1988-07-27
AU592759B2 (en) 1990-01-25
CH663954A5 (de) 1988-01-29
YU45726B (sh) 1992-07-20
DK170332B1 (da) 1995-08-07
ES557365A0 (es) 1988-01-01
DE3523076C2 (de) 1994-09-22
NL8501856A (nl) 1986-01-16
NO169485C (no) 1992-07-01
FI852512L (fi) 1985-12-29
IL75621A (en) 1990-03-19
BE902760A (fr) 1985-12-30
IE851623L (en) 1985-12-28
PT80731B (en) 1987-04-23
ES8801190A1 (es) 1987-12-16
ES8801191A1 (es) 1988-01-01
GR851576B (sv) 1985-11-25
HU195475B (en) 1988-05-30
AT394363B (de) 1992-03-25
LU85978A1 (fr) 1986-01-24
FI83768C (sv) 1991-08-26
CY1597A (en) 1992-04-03
NZ212499A (en) 1989-11-28
ES557076A0 (es) 1987-12-16
ES8801192A1 (es) 1988-01-01
PT80731A (en) 1985-10-01
SG41691G (en) 1991-07-26
IT1200657B (it) 1989-01-27
IL75621A0 (en) 1985-10-31
AU4424285A (en) 1986-01-02
KR860000246A (ko) 1986-01-27
ES551393A0 (es) 1987-05-16
DK291385A (da) 1985-12-29
ES557364A0 (es) 1988-01-01
GB2160871A (en) 1986-01-02
HUT38897A (en) 1986-07-28
IE58705B1 (en) 1993-11-03
SE8503207L (sv) 1985-12-29
AR244677A1 (es) 1993-11-30
FR2566773A1 (fr) 1986-01-03
ES8705852A1 (es) 1987-05-16
ES8609218A1 (es) 1986-09-01
HK50991A (en) 1991-07-12
FR2566773B1 (fr) 1989-05-19
ES544527A0 (es) 1986-09-01
NO169485B (no) 1992-03-23
DE3523076A1 (de) 1986-01-09
DK291385D0 (da) 1985-06-27

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