DK142362B - Analogifremgangsmåde til fremstilling af benzamidderivater eller salte deraf. - Google Patents
Analogifremgangsmåde til fremstilling af benzamidderivater eller salte deraf. Download PDFInfo
- Publication number
- DK142362B DK142362B DK440376AA DK440376A DK142362B DK 142362 B DK142362 B DK 142362B DK 440376A A DK440376A A DK 440376AA DK 440376 A DK440376 A DK 440376A DK 142362 B DK142362 B DK 142362B
- Authority
- DK
- Denmark
- Prior art keywords
- compounds
- formula
- pyrrolidinyl
- chloro
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 20
- 150000003839 salts Chemical class 0.000 title description 6
- 150000003936 benzamides Chemical class 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 description 41
- -1 e.g. Chemical group 0.000 description 30
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 19
- 239000005711 Benzoic acid Substances 0.000 description 16
- 235000010233 benzoic acid Nutrition 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 230000000561 anti-psychotic effect Effects 0.000 description 11
- 238000007429 general method Methods 0.000 description 11
- 241000700159 Rattus Species 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000012442 inert solvent Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- HBVNLKQGRZPGRP-UHFFFAOYSA-N 1-benzylpyrrolidin-3-amine Chemical compound C1C(N)CCN1CC1=CC=CC=C1 HBVNLKQGRZPGRP-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 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 7
- 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 7
- 229960001076 chlorpromazine Drugs 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 229960004046 apomorphine Drugs 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 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 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 239000003874 central nervous system depressant Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- LEHPVQYYMXMDNK-UHFFFAOYSA-N n-(1-benzylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-(methylamino)benzamide Chemical compound C1=C(Cl)C(NC)=CC(OC)=C1C(=O)NC1CN(CC=2C=CC=CC=2)CC1 LEHPVQYYMXMDNK-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 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 2
- KBFVIAZXAFQHPG-UHFFFAOYSA-N 4-amino-5-chloro-n-(1-cyclohexylpyrrolidin-3-yl)-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NC1CN(C2CCCCC2)CC1 KBFVIAZXAFQHPG-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- TXQYEKWBKCPUAT-UHFFFAOYSA-N 5-chloro-4-(dimethylamino)-n-[1-[(4-fluorophenyl)methyl]pyrrolidin-3-yl]-2-methoxybenzamide Chemical compound COC1=CC(N(C)C)=C(Cl)C=C1C(=O)NC1CN(CC=2C=CC(F)=CC=2)CC1 TXQYEKWBKCPUAT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 206010022998 Irritability Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000005910 alkyl carbonate group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 230000003474 anti-emetic effect Effects 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- SQAHDOLPHCQADA-UHFFFAOYSA-N n-(1-benzylpyrrolidin-3-yl)-3,4,5-trimethoxybenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NC2CN(CC=3C=CC=CC=3)CC2)=C1 SQAHDOLPHCQADA-UHFFFAOYSA-N 0.000 description 2
- KMYLBLPBNZMPMC-UHFFFAOYSA-N n-(1-benzylpyrrolidin-3-yl)-5-chloro-4-(dimethylamino)-2-methoxybenzamide Chemical compound COC1=CC(N(C)C)=C(Cl)C=C1C(=O)NC1CN(CC=2C=CC=CC=2)CC1 KMYLBLPBNZMPMC-UHFFFAOYSA-N 0.000 description 2
- IDAGXMLQUPNCAT-UHFFFAOYSA-N n-(1-cyclohexylpyrrolidin-3-yl)-4-(dimethylamino)benzamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)NC1CN(C2CCCCC2)CC1 IDAGXMLQUPNCAT-UHFFFAOYSA-N 0.000 description 2
- MBWDQFNYVZIVDI-UHFFFAOYSA-N n-(1-cyclohexylpyrrolidin-3-yl)-n-methyl-4-(methylamino)benzamide Chemical compound C1=CC(NC)=CC=C1C(=O)N(C)C1CN(C2CCCCC2)CC1 MBWDQFNYVZIVDI-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229960004940 sulpiride Drugs 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XQBNUZCWBALDMP-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]pyrrolidin-3-amine Chemical compound C1C(N)CCN1CC1=CC=C(F)C=C1 XQBNUZCWBALDMP-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- YUJYEGDMJZHLMY-UHFFFAOYSA-N 2-chloro-1,3,2-benzodioxaphosphole Chemical compound C1=CC=C2OP(Cl)OC2=C1 YUJYEGDMJZHLMY-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- UDKMDJLVIVEUBU-UHFFFAOYSA-N 5-chloro-4-(diethylamino)-2-methoxybenzoic acid Chemical compound CCN(CC)C1=CC(OC)=C(C(O)=O)C=C1Cl UDKMDJLVIVEUBU-UHFFFAOYSA-N 0.000 description 1
- NRLNGYGXFOGMEE-UHFFFAOYSA-N 5-chloro-4-(dimethylamino)-2-ethoxybenzoic acid Chemical compound CCOC1=CC(N(C)C)=C(Cl)C=C1C(O)=O NRLNGYGXFOGMEE-UHFFFAOYSA-N 0.000 description 1
- WBGSOLZWWUVDHU-UHFFFAOYSA-N 5-chloro-4-[ethyl(methyl)amino]-2-methoxybenzoic acid Chemical compound CCN(C)C1=CC(OC)=C(C(O)=O)C=C1Cl WBGSOLZWWUVDHU-UHFFFAOYSA-N 0.000 description 1
- GYTGBGZDXLDZED-UHFFFAOYSA-N 5-chloro-n-[1-[(4-chlorophenyl)methyl]pyrrolidin-3-yl]-4-(dimethylamino)-2-methoxybenzamide Chemical compound COC1=CC(N(C)C)=C(Cl)C=C1C(=O)NC1CN(CC=2C=CC(Cl)=CC=2)CC1 GYTGBGZDXLDZED-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 229940005529 antipsychotics Drugs 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- XFEIRVZQVUQECX-UHFFFAOYSA-N bromo ethyl carbonate Chemical compound CCOC(=O)OBr XFEIRVZQVUQECX-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- TXHWYSOQHNMOOU-UHFFFAOYSA-N chloro(diethoxy)phosphane Chemical compound CCOP(Cl)OCC TXHWYSOQHNMOOU-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- PVCINRPAXRJLEP-UHFFFAOYSA-N dichloro(ethoxy)phosphane Chemical compound CCOP(Cl)Cl PVCINRPAXRJLEP-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- WZXDBTFCVFAYSX-UHFFFAOYSA-N n-(1-benzylpyrrolidin-3-yl)-5-chloro-4-(diethylamino)-2-methoxybenzamide Chemical compound C1=C(Cl)C(N(CC)CC)=CC(OC)=C1C(=O)NC1CN(CC=2C=CC=CC=2)CC1 WZXDBTFCVFAYSX-UHFFFAOYSA-N 0.000 description 1
- REZWCTUGHYMXPA-UHFFFAOYSA-N n-(1-benzylpyrrolidin-3-yl)-5-chloro-4-[ethyl(methyl)amino]-2-methoxybenzamide Chemical compound C1=C(Cl)C(N(C)CC)=CC(OC)=C1C(=O)NC1CN(CC=2C=CC=CC=2)CC1 REZWCTUGHYMXPA-UHFFFAOYSA-N 0.000 description 1
- OZTAUSLSCHWPKD-UHFFFAOYSA-N n-(1-benzylpyrrolidin-3-yl)-n-phenylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N(C=1C=CC=CC=1)C(C1)CCN1CC1=CC=CC=C1 OZTAUSLSCHWPKD-UHFFFAOYSA-N 0.000 description 1
- ZWAYJCONKUNJLA-UHFFFAOYSA-N n-(1-benzylpyrrolidin-3-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C1)CCN1CC1=CC=CC=C1 ZWAYJCONKUNJLA-UHFFFAOYSA-N 0.000 description 1
- GCXCUXOCGSIMRB-UHFFFAOYSA-N n-(1-cyclohexylpyrrolidin-3-yl)-4-(dimethylamino)-n-methylbenzamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N(C)C1CN(C2CCCCC2)CC1 GCXCUXOCGSIMRB-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/402—1-aryl substituted, e.g. piretanide
-
- 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
- C07D207/10—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 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
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1166276 | 1976-03-23 | ||
| GB11662/76A GB1520584A (en) | 1975-04-02 | 1976-03-23 | 2 - alkoxy - 5 substituted benzamide derivatives and their use in pharmaceutical compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK440376A DK440376A (ja) | 1977-09-24 |
| DK142362B true DK142362B (da) | 1980-10-20 |
| DK142362C DK142362C (ja) | 1981-03-23 |
Family
ID=9990381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK440376AA DK142362B (da) | 1976-03-23 | 1976-09-30 | Analogifremgangsmåde til fremstilling af benzamidderivater eller salte deraf. |
Country Status (4)
| Country | Link |
|---|---|
| CA (1) | CA1064042A (ja) |
| DK (1) | DK142362B (ja) |
| ES (1) | ES451953A1 (ja) |
| SE (1) | SE416647B (ja) |
-
1976
- 1976-09-21 CA CA261,709A patent/CA1064042A/en not_active Expired
- 1976-09-29 ES ES451953A patent/ES451953A1/es not_active Expired
- 1976-09-30 DK DK440376AA patent/DK142362B/da unknown
- 1976-10-01 SE SE7610906A patent/SE416647B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE416647B (sv) | 1981-01-26 |
| SE7610906L (sv) | 1977-09-24 |
| DK142362C (ja) | 1981-03-23 |
| CA1064042A (en) | 1979-10-09 |
| ES451953A1 (es) | 1977-10-16 |
| DK440376A (ja) | 1977-09-24 |
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