CS239943B2 - Processing of benzoamide derivatives - Google Patents
Processing of benzoamide derivatives Download PDFInfo
- Publication number
- CS239943B2 CS239943B2 CS836362A CS636283A CS239943B2 CS 239943 B2 CS239943 B2 CS 239943B2 CS 836362 A CS836362 A CS 836362A CS 636283 A CS636283 A CS 636283A CS 239943 B2 CS239943 B2 CS 239943B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- compounds
- fla
- compound
- carbon atoms
- bromine
- Prior art date
Links
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 238000000034 method Methods 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 239000000460 chlorine Chemical group 0.000 claims abstract description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 230000003287 optical effect Effects 0.000 claims abstract description 3
- 230000008569 process Effects 0.000 claims description 8
- 150000003936 benzamides Chemical class 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 101100022176 Mus musculus Gstz1 gene Proteins 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 abstract description 4
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 2
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 238000009472 formulation Methods 0.000 description 9
- 230000033001 locomotion Effects 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- 102000015554 Dopamine receptor Human genes 0.000 description 8
- 108050004812 Dopamine receptor Proteins 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 210000004556 brain Anatomy 0.000 description 6
- -1 depression Chemical class 0.000 description 6
- 229960003638 dopamine Drugs 0.000 description 6
- 229920000159 gelatin Polymers 0.000 description 6
- 235000019322 gelatine Nutrition 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- WAOQONBSWFLFPE-VIFPVBQESA-N 3,5-dichloro-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2-hydroxy-6-methoxybenzamide Chemical compound CCN1CCC[C@H]1CNC(=O)C1=C(O)C(Cl)=CC(Cl)=C1OC WAOQONBSWFLFPE-VIFPVBQESA-N 0.000 description 5
- 108010010803 Gelatin Proteins 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 230000000561 anti-psychotic effect Effects 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000008273 gelatin Substances 0.000 description 5
- 239000007903 gelatin capsule Substances 0.000 description 5
- 235000011852 gelatine desserts Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229960004940 sulpiride Drugs 0.000 description 5
- BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 description 4
- GUJRSXAPGDDABA-NSHDSACASA-N 3-bromo-N-[[(2S)-1-ethyl-2-pyrrolidinyl]methyl]-2,6-dimethoxybenzamide Chemical compound CCN1CCC[C@H]1CNC(=O)C1=C(OC)C=CC(Br)=C1OC GUJRSXAPGDDABA-NSHDSACASA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 208000028017 Psychotic disease Diseases 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 229960004046 apomorphine Drugs 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 229920001592 potato starch Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- SPFVHFBNXPARTR-IDMXKUIJSA-N 3-bromo-n-[[(2s)-1-ethylpyrrolidin-2-yl]methyl]-2,6-dimethoxybenzamide;hydron;chloride;hydrate Chemical compound O.Cl.CCN1CCC[C@H]1CNC(=O)C1=C(OC)C=CC(Br)=C1OC SPFVHFBNXPARTR-IDMXKUIJSA-N 0.000 description 2
- PWEZBNRZEHPIIQ-JTQLQIEISA-N 3-bromo-n-[[(2s)-1-ethylpyrrolidin-2-yl]methyl]-2-hydroxy-6-methoxybenzamide Chemical compound CCN1CCC[C@H]1CNC(=O)C1=C(O)C(Br)=CC=C1OC PWEZBNRZEHPIIQ-JTQLQIEISA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000000164 antipsychotic agent Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 230000001055 chewing effect Effects 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 208000013403 hyperactivity Diseases 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 230000002197 limbic effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002858 neurotransmitter agent Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 206010041232 sneezing Diseases 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 230000008673 vomiting Effects 0.000 description 2
- KWLNAROUVGOHDS-UHFFFAOYSA-N 1,2,2-triphenylpyrrolidine Chemical compound C=1C=CC=CC=1C1(C=2C=CC=CC=2)CCCN1C1=CC=CC=C1 KWLNAROUVGOHDS-UHFFFAOYSA-N 0.000 description 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- QRMZHEDLUQMLGK-JTQLQIEISA-N 3-bromo-n-[[(2s)-1-ethylpyrrolidin-2-yl]methyl]-6-hydroxy-2-methoxybenzamide Chemical compound CCN1CCC[C@H]1CNC(=O)C1=C(O)C=CC(Br)=C1OC QRMZHEDLUQMLGK-JTQLQIEISA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 208000009132 Catalepsy Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 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 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 208000012545 Psychophysiologic disease Diseases 0.000 description 1
- 208000035755 Psychosomatic disease Diseases 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 206010047853 Waxy flexibility Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000003943 catecholamines Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 239000007938 effervescent tablet Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000008522 spreadable oils and fats Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 230000002739 subcortical effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- BGRJTUBHPOOWDU-UHFFFAOYSA-N sulpiride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000007939 sustained release tablet Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
- Medicinal Preparation (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8205135A SE8205135D0 (sv) | 1982-09-09 | 1982-09-09 | Benzamido-derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS636283A2 CS636283A2 (en) | 1985-05-15 |
| CS239943B2 true CS239943B2 (en) | 1986-01-16 |
Family
ID=20347777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS836362A CS239943B2 (en) | 1982-09-09 | 1983-09-01 | Processing of benzoamide derivatives |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US4937260A (en]) |
| EP (1) | EP0117384B1 (en]) |
| JP (1) | JPS5967260A (en]) |
| KR (1) | KR900008316B1 (en]) |
| AT (1) | ATE39482T1 (en]) |
| BG (1) | BG37992A3 (en]) |
| CA (1) | CA1207776A (en]) |
| CS (1) | CS239943B2 (en]) |
| CY (1) | CY1461A (en]) |
| DD (1) | DD211552A5 (en]) |
| DE (1) | DE3378761D1 (en]) |
| DK (1) | DK157846C (en]) |
| ES (1) | ES8501748A1 (en]) |
| FI (1) | FI78905C (en]) |
| GB (1) | GB2126585B (en]) |
| GR (1) | GR79666B (en]) |
| HK (1) | HK14589A (en]) |
| HU (1) | HU189745B (en]) |
| IE (1) | IE55907B1 (en]) |
| IL (1) | IL69682A (en]) |
| MY (1) | MY8700304A (en]) |
| NO (1) | NO161853C (en]) |
| NZ (1) | NZ205527A (en]) |
| PH (1) | PH18900A (en]) |
| PL (1) | PL139342B1 (en]) |
| PT (1) | PT77310B (en]) |
| RO (1) | RO86674B (en]) |
| SE (1) | SE8205135D0 (en]) |
| SU (1) | SU1342412A3 (en]) |
| ZA (1) | ZA836280B (en]) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8400478D0 (sv) * | 1984-01-31 | 1984-01-31 | Astra Laekemedel Ab | Oxysalicylamido derivatives |
| US5240957A (en) * | 1984-01-31 | 1993-08-31 | Astra Lakemedel Akteibolag | Oxysalicylamido derivatives |
| US4772459A (en) * | 1986-09-09 | 1988-09-20 | Erbamont, Inc. | Method for controlling emesis caused by chemotherapeutic agents and antiemetic agents useful therein |
| US5122361A (en) * | 1989-04-17 | 1992-06-16 | Trustees Of The University Of Pennsylvania | Dopamine receptor ligands and imaging agents |
| US5186921A (en) * | 1989-04-17 | 1993-02-16 | Trustees Of The University Of Pennsylvania | Dopamine receptor ligands and image agents |
| US5993777A (en) * | 1993-05-06 | 1999-11-30 | Research Corporation Technologies, Inc. | Benzamide compounds for cancer imaging and therapy |
| US6517811B2 (en) | 1993-05-06 | 2003-02-11 | Research Corporation Technologies, Inc. | Compounds for cancer imaging and therapy |
| US5911970A (en) * | 1993-05-06 | 1999-06-15 | Research Corporation Technologies, Inc. | Methods for cancer imaging and therapy using benzamine compounds |
| EP0650372A4 (en) * | 1993-05-06 | 1996-07-03 | Christy S John | COMPOUNDS FOR CANCER VISUALIZATION AND THERAPY. |
| DK72693D0 (da) * | 1993-06-18 | 1993-06-18 | Lundbeck & Co As H | Compounds |
| DE19531464A1 (de) * | 1995-08-26 | 1997-02-27 | Merck Patent Gmbh | N-Methyl-N-[(1S-)-1-phenyl-2-((3S)-3-hydroxypyrrolidin 1-yl-)-ethyl]-2,2-diphenyl-acetamid |
| KR20080055111A (ko) | 2006-12-14 | 2008-06-19 | 제일모직주식회사 | 컬러필터용 안료분산액 조성물 및 이를 이용하여 제조된컬러 촬상 소자용 컬러필터 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3342826A (en) * | 1964-01-13 | 1967-09-19 | Ile De France | Heterocyclic aminoalkyl benzamides |
| BE695272A (en]) * | 1967-03-09 | 1967-09-11 | ||
| CH507938A (fr) * | 1968-08-01 | 1971-05-31 | Ile De France | Procédé de préparation de benzamides hétérocycliques |
| US3793030A (en) * | 1971-09-02 | 1974-02-19 | Ricoh Kk | Process for producing diazotype light-sensitive material |
| US3914418A (en) * | 1971-09-02 | 1975-10-21 | Merck & Co Inc | Methods of controlling liver fluke infections |
| US3862139A (en) * | 1972-06-23 | 1975-01-21 | Delmar Chem | Heterocyclic benzamide compounds |
| IT1070992B (it) * | 1973-12-21 | 1985-04-02 | Italfarmaco Spa | Processo per la preparazione della i etil 2 2 metossi 5 sulfamoil benzamidometil pirrolidina |
| FR2294698A1 (fr) * | 1974-12-18 | 1976-07-16 | Synthelabo | Nouveaux derives des methoxy-2 benzamides substitues, leurs sels, leur preparation et les medicaments qui en renferment |
| SE412908B (sv) * | 1974-12-18 | 1980-03-24 | Synthelabo | Forfarande for framstellning av terapeutiskt aktiva 2-metoxibensamider innehallande en pyrrolidin- eller en piperidinrest |
| US4029678A (en) * | 1975-12-08 | 1977-06-14 | Hoffmann-La Roche Inc. | Asymmetric synthesis |
| JPS5319447A (en) * | 1976-08-07 | 1978-02-22 | Igeta Seikou Kk | Manufacture of endless wire rope |
| NZ186175A (en) * | 1977-01-27 | 1980-03-05 | Shionogi & Co | Meta-sulphonamidobenzamide derivatives |
| FR2440946A2 (fr) * | 1978-01-20 | 1980-06-06 | Ile De France | Nouveaux benzamides heterocycliques substitues, leurs procedes de preparation et leur application comme modificateurs du comportement |
| SE411118B (sv) * | 1978-03-23 | 1979-12-03 | Astra Laekemedel Ab | Ett forfarande for framstellning av 2,6-dialkoxibensamider med terapentiska egenskaper |
| FR2438650A1 (fr) * | 1978-10-11 | 1980-05-09 | Ile De France | N-(1-methyl 2-pyrrolidinyl methyl) 2,3-dimethoxy 5-methylsulfamoyl benzamide et ses derives, leurs methodes de preparation et leur application dans le traitement des troubles du bas appareil urinaire |
| IT1141095B (it) * | 1980-11-27 | 1986-10-01 | Ravizza Spa | Processo di risoluzione della sulpiride racema |
| SE8101536L (sv) * | 1981-03-11 | 1982-09-12 | Astra Laekemedel Ab | Bensamid-derivat |
| JPH0331704A (ja) * | 1989-06-29 | 1991-02-12 | Matsushita Electric Ind Co Ltd | 位置合わせ装置 |
-
1982
- 1982-09-09 SE SE8205135A patent/SE8205135D0/xx unknown
-
1983
- 1983-08-18 DE DE8383850215T patent/DE3378761D1/de not_active Expired
- 1983-08-18 AT AT83850215T patent/ATE39482T1/de active
- 1983-08-18 EP EP83850215A patent/EP0117384B1/en not_active Expired
- 1983-08-24 ZA ZA836280A patent/ZA836280B/xx unknown
- 1983-09-01 CS CS836362A patent/CS239943B2/cs unknown
- 1983-09-05 PH PH29491A patent/PH18900A/en unknown
- 1983-09-06 DK DK403883A patent/DK157846C/da not_active IP Right Cessation
- 1983-09-06 IE IE2094/83A patent/IE55907B1/en not_active IP Right Cessation
- 1983-09-07 FI FI833206A patent/FI78905C/fi not_active IP Right Cessation
- 1983-09-07 DD DD83254597A patent/DD211552A5/de not_active IP Right Cessation
- 1983-09-07 IL IL69682A patent/IL69682A/xx unknown
- 1983-09-07 PL PL1983243670A patent/PL139342B1/pl unknown
- 1983-09-08 ES ES525488A patent/ES8501748A1/es not_active Expired
- 1983-09-08 NO NO833219A patent/NO161853C/no unknown
- 1983-09-08 HU HU833144A patent/HU189745B/hu not_active IP Right Cessation
- 1983-09-08 GB GB08324080A patent/GB2126585B/en not_active Expired
- 1983-09-08 NZ NZ205527A patent/NZ205527A/en unknown
- 1983-09-08 JP JP58164275A patent/JPS5967260A/ja active Granted
- 1983-09-08 CA CA000436275A patent/CA1207776A/en not_active Expired
- 1983-09-08 PT PT77310A patent/PT77310B/pt not_active IP Right Cessation
- 1983-09-08 SU SU833643500A patent/SU1342412A3/ru active
- 1983-09-08 BG BG062309A patent/BG37992A3/xx unknown
- 1983-09-09 GR GR72413A patent/GR79666B/el unknown
- 1983-09-09 RO RO112024A patent/RO86674B/ro unknown
- 1983-09-09 KR KR1019830004251A patent/KR900008316B1/ko not_active Expired
-
1987
- 1987-12-30 MY MY304/87A patent/MY8700304A/xx unknown
-
1988
- 1988-01-27 US US07/148,104 patent/US4937260A/en not_active Expired - Fee Related
-
1989
- 1989-02-16 HK HK145/89A patent/HK14589A/xx unknown
- 1989-07-21 CY CY1461A patent/CY1461A/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7598271B1 (en) | Crystalline paroxetine methane sulfonate | |
| CS239943B2 (en) | Processing of benzoamide derivatives | |
| CZ416291A3 (en) | Derivatives of cis, endo-2-azabicyclo-(3.3.0)-octane-3-carboxylic acid, process of their preparation, compounds in which said derivatives are contained and their use | |
| DE69332718T2 (de) | Enantiomere von carbazolderivaten als 5-ht1-ähnliche agonisten | |
| SU1261561A3 (ru) | Способ получени производных бензамида,их солей или их оптических изомеров | |
| US4232037A (en) | 2,6-Dialkoxybenzamides, intermediates, pharamaceutical compositions and methods for treatment of psychotic disorders | |
| DE69803445T2 (de) | 5-hydroxymethyl-2-aminotetraline als cardiovasculäre mittel | |
| US4465692A (en) | Selective D-2 dopamine receptor agonist | |
| EP0115714A1 (fr) | Composition pharmaceutique à action psychotrope dopanimergique | |
| Zelle et al. | Synthesis and pharmacological characterization of ABT-200: A putative novel antidepressant combining potent α-2 antagonism with moderate NE uptake inhibition | |
| KR20210124976A (ko) | 볼리난세린의 중수소화 형태 및 유도체 | |
| US4285942A (en) | Cyclododecanone oximes | |
| US5583142A (en) | Analgesic and nootropic drugs | |
| JPH05105627A (ja) | 腸機能性疾患の治療に用いられる新規な医薬組成物と、その調整方法と、治療用医薬の調製方法 | |
| KR20010014294A (ko) | (Ｓ) 2-메틸아미노-2-페닐-ｎ-부틸3,4,5-트리메톡시벤조에이트 및 만성 통증을 치료하기위한 그의 용도 | |
| US4990534A (en) | Aralkyl esters and processes for their preparation | |
| CS266314B2 (cs) | Způsob výroby benzamidových derivátů | |
| CA1109484A (en) | 2,6-dialkoxybenzamides, intermediates, pharmaceutical compositions and methods for treatment of psychotic disorders | |
| JPS625417B2 (en]) | ||
| NL8002417A (nl) | Alfa-halogeenmethylaminozuurderivaten. |