DD239787A5

DD239787A5 - Verfahren zur herstellung neuer benzamide

Verfahren zur herstellung neuer benzamide Download PDF

Info

Publication number: DD239787A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; compound; cyano; salt; chloro
Prior art date: 1984-11-23

Application number

DD85283145A

Other languages

German (de)

English (en)

Inventor

Angelo Storni

Serge F Bischoff

Georg Von Sprecher

Original Assignee

Ciba-Geigy Ag,Ch

Priority date

1984-11-23

Filing date

1985-11-22

Publication date

1986-10-08

1985-11-22 Application filed by Ciba-Geigy Ag,Ch filed Critical Ciba-Geigy Ag,Ch

1986-10-08 Publication of DD239787A5 publication Critical patent/DD239787A5/de

Links

229940054066 benzamide antipsychotics Drugs 0.000 title claims abstract description 8
150000003936 benzamides Chemical class 0.000 title claims abstract description 8
238000004519 manufacturing process Methods 0.000 title description 3
150000003839 salts Chemical class 0.000 claims abstract description 79
238000000034 method Methods 0.000 claims abstract description 44
125000000217 alkyl group Chemical group 0.000 claims abstract description 28
229910052736 halogen Inorganic materials 0.000 claims abstract description 20
150000002367 halogens Chemical class 0.000 claims abstract description 20
230000008569 process Effects 0.000 claims abstract description 19
238000002360 preparation method Methods 0.000 claims abstract description 17
125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
150000001875 compounds Chemical class 0.000 claims description 90
-1 hydroxyiminomethyl Chemical group 0.000 claims description 60
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
239000000825 pharmaceutical preparation Substances 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
238000006467 substitution reaction Methods 0.000 claims description 6
239000012024 dehydrating agents‎ Substances 0.000 claims description 5
239000000969 carrier Substances 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 3
VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
239000003814 drug Substances 0.000 abstract description 5
230000009471 action Effects 0.000 abstract description 4
239000000935 antidepressant agent Substances 0.000 abstract description 4
229940005513 antidepressants Drugs 0.000 abstract description 4
230000000144 pharmacologic effect Effects 0.000 abstract description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
239000002253 acid Substances 0.000 description 24
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
239000004480 active ingredient Substances 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000007858 starting material Substances 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
150000007513 acids Chemical class 0.000 description 13
239000000203 mixture Substances 0.000 description 12
238000003756 stirring Methods 0.000 description 12
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 11
239000002585 base Substances 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
150000008064 anhydrides Chemical class 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
239000000454 talc Substances 0.000 description 9
229910052623 talc Inorganic materials 0.000 description 9
235000012222 talc Nutrition 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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 8
229920002472 Starch Polymers 0.000 description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
238000001816 cooling Methods 0.000 description 8
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
239000008101 lactose Substances 0.000 description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
239000002775 capsule Substances 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
229910052801 chlorine Inorganic materials 0.000 description 7
238000002955 isolation Methods 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
235000019698 starch Nutrition 0.000 description 7
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
238000011065 in-situ storage Methods 0.000 description 6
235000019359 magnesium stearate Nutrition 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
229920001567 vinyl ester resin Polymers 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
108010010803 Gelatin Proteins 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
229960003638 dopamine Drugs 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000008273 gelatin Substances 0.000 description 5
229920000159 gelatin Polymers 0.000 description 5
229940014259 gelatin Drugs 0.000 description 5
235000019322 gelatine Nutrition 0.000 description 5
235000011852 gelatine desserts Nutrition 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
239000008107 starch Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
KBYZFTMBSZCYGM-UHFFFAOYSA-N 4-chloro-5-cyano-2-methoxybenzoic acid Chemical compound COC1=CC(Cl)=C(C#N)C=C1C(O)=O KBYZFTMBSZCYGM-UHFFFAOYSA-N 0.000 description 4
MEVZDNOEBFXULG-UHFFFAOYSA-N 4-chloro-5-cyano-n-[2-(diethylamino)ethyl]-2-hydroxybenzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(C#N)=C(Cl)C=C1O MEVZDNOEBFXULG-UHFFFAOYSA-N 0.000 description 4
JEMKCYHUYUPGFN-UHFFFAOYSA-N 4-chloro-5-cyano-n-[2-(diethylamino)ethyl]-2-methoxybenzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(C#N)=C(Cl)C=C1OC JEMKCYHUYUPGFN-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000001335 aliphatic alkanes Chemical class 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
229910052802 copper Inorganic materials 0.000 description 4
239000010949 copper Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
229920001592 potato starch Polymers 0.000 description 4
238000000746 purification Methods 0.000 description 4
150000003460 sulfonic acids Chemical class 0.000 description 4
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
XHLNSTLZBINQRM-UHFFFAOYSA-N 4-chloro-5-cyano-2-methoxy-n-[2-(propan-2-ylamino)butyl]benzamide Chemical compound CC(C)NC(CC)CNC(=O)C1=CC(C#N)=C(Cl)C=C1OC XHLNSTLZBINQRM-UHFFFAOYSA-N 0.000 description 3
WCEAGVVYFJUQTR-UHFFFAOYSA-N 5-chloro-4-cyano-n-[2-(diethylamino)ethyl]-2-methoxybenzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(C#N)C=C1OC WCEAGVVYFJUQTR-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
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 3
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WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
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241000700159 Rattus Species 0.000 description 3
235000021355 Stearic acid Nutrition 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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229910052783 alkali metal Inorganic materials 0.000 description 3
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230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
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ABFPKTQEQNICFT-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Cl ABFPKTQEQNICFT-UHFFFAOYSA-M 0.000 description 2
XGQLCPWGEGYXAT-UHFFFAOYSA-N 4-chloro-5-cyano-2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC(C#N)=C(Cl)C=C1O XGQLCPWGEGYXAT-UHFFFAOYSA-N 0.000 description 2
ODDRCWUZEVGMLP-UHFFFAOYSA-N 4-chloro-5-cyano-2-methoxy-n-[2-(propylamino)ethyl]benzamide Chemical compound CCCNCCNC(=O)C1=CC(C#N)=C(Cl)C=C1OC ODDRCWUZEVGMLP-UHFFFAOYSA-N 0.000 description 2
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HCRQHOBMIVYWBP-UHFFFAOYSA-N 4-chloro-5-cyano-n-[2-(diethylamino)ethyl]-2-propan-2-yloxybenzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(C#N)=C(Cl)C=C1OC(C)C HCRQHOBMIVYWBP-UHFFFAOYSA-N 0.000 description 2
ZSPQIFUIWDTCCQ-UHFFFAOYSA-N 4-chloro-5-cyano-n-[2-(ethylamino)ethyl]-2-methoxybenzamide;hydrochloride Chemical compound Cl.CCNCCNC(=O)C1=CC(C#N)=C(Cl)C=C1OC ZSPQIFUIWDTCCQ-UHFFFAOYSA-N 0.000 description 2
YNHPKXYNKACSSS-UHFFFAOYSA-N 4-chloro-5-cyano-n-[2-[di(propan-2-yl)amino]ethyl]-2-methoxybenzamide Chemical compound COC1=CC(Cl)=C(C#N)C=C1C(=O)NCCN(C(C)C)C(C)C YNHPKXYNKACSSS-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
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239000011230 binding agent Substances 0.000 description 2
PPQNDCSTOHZQEH-UHFFFAOYSA-N bis(benzotriazol-1-yl) carbonate Chemical compound N1=NC2=CC=CC=C2N1OC(=O)ON1C2=CC=CC=C2N=N1 PPQNDCSTOHZQEH-UHFFFAOYSA-N 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
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