CA1140132A - Procede de preparation de nouveaux benzamides - Google Patents
Procede de preparation de nouveaux benzamidesInfo
- Publication number
- CA1140132A CA1140132A CA000260488A CA260488A CA1140132A CA 1140132 A CA1140132 A CA 1140132A CA 000260488 A CA000260488 A CA 000260488A CA 260488 A CA260488 A CA 260488A CA 1140132 A CA1140132 A CA 1140132A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- product
- oxo
- acid
- dihydro
- Prior art date
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 14
- 229940054066 benzamide antipsychotics Drugs 0.000 title claims abstract description 9
- 150000003936 benzamides Chemical class 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 239000000460 chlorine Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000011737 fluorine Chemical group 0.000 claims abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Chemical group 0.000 claims abstract description 3
- 150000007513 acids Chemical class 0.000 claims abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 11
- 239000011707 mineral Substances 0.000 claims description 11
- -1 atom hydrogen Chemical class 0.000 claims description 8
- VNDHYTGVCGVETQ-UHFFFAOYSA-N 4-fluorobenzamide Chemical compound NC(=O)C1=CC=C(F)C=C1 VNDHYTGVCGVETQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- 150000001768 cations Chemical class 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 claims 1
- DVRGLLCBTUAOBC-UHFFFAOYSA-N 4-fluoro-n-[2-[4-(2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]ethyl]benzamide Chemical compound OC1=NC2=CC=CC=C2N1C(CC1)CCN1CCNC(=O)C1=CC=C(F)C=C1 DVRGLLCBTUAOBC-UHFFFAOYSA-N 0.000 claims 1
- DRMQIEHSDJCGNT-UHFFFAOYSA-N 4-fluorobenzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=C(F)C=C1 DRMQIEHSDJCGNT-UHFFFAOYSA-N 0.000 claims 1
- 241001331845 Equus asinus x caballus Species 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 230000035943 smell Effects 0.000 claims 1
- 230000003474 anti-emetic effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 25
- 241001465754 Metazoa Species 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229960004046 apomorphine Drugs 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
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 210000004916 vomit Anatomy 0.000 description 4
- 230000008673 vomiting Effects 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 231100000111 LD50 Toxicity 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000000506 psychotropic effect Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- SKYZYDSNJIOXRL-BTQNPOSSSA-N (6ar)-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol;hydrochloride Chemical compound Cl.C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 SKYZYDSNJIOXRL-BTQNPOSSSA-N 0.000 description 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- PYHRZPFZZDCOPH-QXGOIDDHSA-N (S)-amphetamine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C[C@H](N)CC1=CC=CC=C1.C[C@H](N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-QXGOIDDHSA-N 0.000 description 1
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- DSPHFASHOJAOKN-UHFFFAOYSA-N 1-[(7-oxobenzo[a]phenalen-2-yl)amino]anthracene-9,10-dione Chemical compound C1=CC2=CC(NC3=C4C(=O)C5=CC=CC=C5C(C4=CC=C3)=O)=CC(C=3C(=CC=CC=3)C3=O)=C2C3=C1 DSPHFASHOJAOKN-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-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
- KGGHWIKBOIQEAJ-UHFFFAOYSA-N 2-fluorobenzamide Chemical compound NC(=O)C1=CC=CC=C1F KGGHWIKBOIQEAJ-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 206010063409 Acarodermatitis Diseases 0.000 description 1
- 241000579579 Acidea Species 0.000 description 1
- 241000272814 Anser sp. Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000283074 Equus asinus Species 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 241000755093 Gaidropsarus vulgaris Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 1
- 241001302187 Moina Species 0.000 description 1
- 241000699729 Muridae Species 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 208000037656 Respiratory Sounds Diseases 0.000 description 1
- 241000447727 Scabies Species 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 229960003990 apomorphine hydrochloride Drugs 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229940028332 halog Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 206010037833 rales Diseases 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 208000005687 scabies Diseases 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7527311A FR2322599A1 (fr) | 1975-09-05 | 1975-09-05 | Nouveaux benzamides et leurs sels, procede de preparation et application a titre de medicaments de ces nouveaux produits |
| FR75-27311 | 1975-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1140132A true CA1140132A (fr) | 1983-01-25 |
Family
ID=9159670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000260488A Expired CA1140132A (fr) | 1975-09-05 | 1976-09-03 | Procede de preparation de nouveaux benzamides |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5233680A (cs) |
| AT (1) | AT352725B (cs) |
| BE (1) | BE845817A (cs) |
| CA (1) | CA1140132A (cs) |
| CH (1) | CH614440A5 (cs) |
| DE (1) | DE2638705A1 (cs) |
| DK (1) | DK142236B (cs) |
| ES (1) | ES451197A1 (cs) |
| FR (1) | FR2322599A1 (cs) |
| GB (1) | GB1556502A (cs) |
| IE (1) | IE44293B1 (cs) |
| LU (1) | LU75724A1 (cs) |
| NL (1) | NL7609821A (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19952146A1 (de) * | 1999-10-29 | 2001-06-07 | Boehringer Ingelheim Pharma | Arylalkane, Arylalkene und Aryl-azaalkane, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
-
1975
- 1975-09-05 FR FR7527311A patent/FR2322599A1/fr active Granted
-
1976
- 1976-08-27 DE DE19762638705 patent/DE2638705A1/de not_active Withdrawn
- 1976-09-03 JP JP10510076A patent/JPS5233680A/ja active Pending
- 1976-09-03 CH CH1121676A patent/CH614440A5/xx not_active IP Right Cessation
- 1976-09-03 BE BE170318A patent/BE845817A/xx unknown
- 1976-09-03 LU LU75724A patent/LU75724A1/xx unknown
- 1976-09-03 DK DK398176A patent/DK142236B/da not_active IP Right Cessation
- 1976-09-03 CA CA000260488A patent/CA1140132A/fr not_active Expired
- 1976-09-03 ES ES451197A patent/ES451197A1/es not_active Expired
- 1976-09-03 NL NL7609821A patent/NL7609821A/xx not_active Application Discontinuation
- 1976-09-06 GB GB3680276A patent/GB1556502A/en not_active Expired
- 1976-09-06 AT AT659076A patent/AT352725B/de not_active IP Right Cessation
- 1976-09-06 IE IE198276A patent/IE44293B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7609821A (nl) | 1977-03-08 |
| FR2322599A1 (fr) | 1977-04-01 |
| DK398176A (cs) | 1977-03-06 |
| DK142236B (da) | 1980-09-29 |
| FR2322599B1 (cs) | 1979-09-14 |
| IE44293L (en) | 1977-03-05 |
| DE2638705A1 (de) | 1977-03-17 |
| IE44293B1 (en) | 1981-10-07 |
| ATA659076A (de) | 1979-03-15 |
| DK142236C (cs) | 1981-02-23 |
| CH614440A5 (en) | 1979-11-30 |
| JPS5233680A (en) | 1977-03-14 |
| AT352725B (de) | 1979-10-10 |
| GB1556502A (en) | 1979-11-28 |
| ES451197A1 (es) | 1977-11-16 |
| BE845817A (fr) | 1977-03-03 |
| LU75724A1 (cs) | 1977-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |