SK50142006A3 - Spôsob odstraňovania trifenylmetánovej ochrannej skupiny - Google Patents

Spôsob odstraňovania trifenylmetánovej ochrannej skupiny Download PDF

Info

Publication number: SK50142006A3
Authority: SK; Slovakia
Prior art keywords: formula; process according; biphenyl; methyl; tetrazol
Prior art date: 2003-08-27

Application number

SK5014-2006A

Other languages

English (en)

Slovak (sk)

Inventor

Stanislav R�Dl

Jan Stach

Ond�Ej Klec�N

Original Assignee

Zentiva, A. S.

Priority date (The priority date 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 date listed.)

2003-08-27

Filing date

2004-08-26

Publication date

2006-05-04

2003-08-27 Priority claimed from CZ20032319A external-priority patent/CZ297016B6/cs

2004-06-16 Priority claimed from CZ20040733A external-priority patent/CZ298329B6/cs

2004-08-26 Application filed by Zentiva, A. S. filed Critical Zentiva, A. S.

2006-05-04 Publication of SK50142006A3 publication Critical patent/SK50142006A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 54
AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 title claims abstract description 6
239000002083 C09CA01 - Losartan Substances 0.000 claims abstract description 21
229960004773 losartan Drugs 0.000 claims abstract description 21
YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical class O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 claims abstract description 19
239000004072 C09CA03 - Valsartan Chemical class 0.000 claims abstract description 17
229960004699 valsartan Drugs 0.000 claims abstract description 17
239000002947 C09CA04 - Irbesartan Chemical class 0.000 claims abstract description 14
229960002198 irbesartan Drugs 0.000 claims abstract description 14
GHOSNRCGJFBJIB-UHFFFAOYSA-N Candesartan cilexetil Chemical class C=12N(CC=3C=CC(=CC=3)C=3C(=CC=CC=3)C3=NNN=N3)C(OCC)=NC2=CC=CC=1C(=O)OC(C)OC(=O)OC1CCCCC1 GHOSNRCGJFBJIB-UHFFFAOYSA-N 0.000 claims abstract description 10
229960004349 candesartan cilexetil Drugs 0.000 claims abstract description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
238000003797 solvolysis reaction Methods 0.000 claims abstract description 4
125000003118 aryl group Chemical group 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
150000002367 halogens Chemical class 0.000 claims abstract description 3
229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical class CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 claims abstract 4
230000007935 neutral effect Effects 0.000 claims abstract 2
238000002360 preparation method Methods 0.000 claims abstract 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 129
-1 1-triphenylmethyl-5- (4'-substituted methyl-1,1-biphenyl- 2-yl) -1H-tetrazoles Chemical class 0.000 claims description 46
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 41
230000008569 process Effects 0.000 claims description 34
239000000203 mixture Substances 0.000 claims description 31
IRMNIXXVOOMKKP-UHFFFAOYSA-N [methoxy(diphenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC)C1=CC=CC=C1 IRMNIXXVOOMKKP-UHFFFAOYSA-N 0.000 claims description 30
239000002904 solvent Substances 0.000 claims description 26
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 25
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 21
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 15
238000002425 crystallisation Methods 0.000 claims description 13
230000008025 crystallization Effects 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 12
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 12
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 11
238000001816 cooling Methods 0.000 claims description 10
229910000027 potassium carbonate Inorganic materials 0.000 claims description 9
235000011181 potassium carbonates Nutrition 0.000 claims description 9
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical class [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 claims description 8
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 7
239000011736 potassium bicarbonate Substances 0.000 claims description 7
235000015497 potassium bicarbonate Nutrition 0.000 claims description 7
229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 5
NDTNRUYCXAKMPU-UHFFFAOYSA-N 2-butyl-3-[[4-[2-(2-trityltetrazol-5-yl)phenyl]phenyl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C2=NN(N=N2)C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C(CCCC)=NC21CCCC2 NDTNRUYCXAKMPU-UHFFFAOYSA-N 0.000 claims description 5
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 5
229960004295 valine Drugs 0.000 claims description 5
150000001298 alcohols Chemical class 0.000 claims description 4
VXKKFWDUSKMRNO-LJAQVGFWSA-N benzyl (2s)-3-methyl-2-[pentanoyl-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]amino]butanoate Chemical compound CCCCC(=O)N([C@@H](C(C)C)C(=O)OCC=1C=CC=CC=1)CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 VXKKFWDUSKMRNO-LJAQVGFWSA-N 0.000 claims description 4
150000001733 carboxylic acid esters Chemical class 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
VBMKOTRJWPIKMG-UHFFFAOYSA-N 2-ethoxy-3-[[4-[2-(1-trityltetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid Chemical compound CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 VBMKOTRJWPIKMG-UHFFFAOYSA-N 0.000 claims description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
150000001983 dialkylethers Chemical class 0.000 claims description 3
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 3
229940011051 isopropyl acetate Drugs 0.000 claims description 3
GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 3
239000012452 mother liquor Substances 0.000 claims description 3
IPEZQBALWLNRGH-UHFFFAOYSA-N 2-butyl-3-[[4-[2-(1-trityltetrazol-5-yl)phenyl]phenyl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2N(N=NN=2)C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C(CCCC)=NC21CCCC2 IPEZQBALWLNRGH-UHFFFAOYSA-N 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
ZKJNVODQIYQUNQ-UHFFFAOYSA-N [2-butyl-5-chloro-3-[[4-[2-(1-trityltetrazol-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2N(N=NN=2)C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 ZKJNVODQIYQUNQ-UHFFFAOYSA-N 0.000 claims description 2
238000001914 filtration Methods 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
235000011118 potassium hydroxide Nutrition 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims 4
229950006523 cilexetil Drugs 0.000 claims 2
VTDCYOLLYVAJSY-UHFFFAOYSA-N cyclohexyl propan-2-yl carbonate Chemical compound CC(C)OC(=O)OC1CCCCC1 VTDCYOLLYVAJSY-UHFFFAOYSA-N 0.000 claims 2
HQCWKLWGCQAUOU-FAIXQHPJSA-N (2s)-3-methyl-2-[pentanoyl-[[4-[2-(2-trityltetrazol-5-yl)phenyl]phenyl]methyl]amino]butanoic acid Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)N=N1 HQCWKLWGCQAUOU-FAIXQHPJSA-N 0.000 claims 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
VVQNAFBGAWCMLU-UHFFFAOYSA-N 1h-benzimidazole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1N=CN2 VVQNAFBGAWCMLU-UHFFFAOYSA-N 0.000 claims 1
150000001450 anions Chemical class 0.000 claims 1
238000006264 debenzylation reaction Methods 0.000 claims 1
238000001704 evaporation Methods 0.000 claims 1
230000008020 evaporation Effects 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 claims 1
ACWBQPMHZXGDFX-QFIPXVFZSA-N valsartan Chemical class C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 0.000 abstract description 21
239000003814 drug Substances 0.000 abstract description 6
229940079593 drug Drugs 0.000 abstract description 4
KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 abstract description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 abstract description 2
125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
125000003545 alkoxy group Chemical group 0.000 abstract 1
125000004849 alkoxymethyl group Chemical group 0.000 abstract 1
125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
159000000001 potassium salts Chemical class 0.000 abstract 1
239000013078 crystal Substances 0.000 description 22
PSIFNNKUMBGKDQ-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2NN=NN=2)C=C1 PSIFNNKUMBGKDQ-UHFFFAOYSA-N 0.000 description 20
239000000047 product Substances 0.000 description 14
238000010992 reflux Methods 0.000 description 11
239000000725 suspension Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000000706 filtrate Substances 0.000 description 8
230000008859 change Effects 0.000 description 7
238000006642 detritylation reaction Methods 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
QQPGGBNMTNDKEY-UHFFFAOYSA-N [2-butyl-5-chloro-3-[[4-[2-(2-trityltetrazol-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=NN(N=N2)C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 QQPGGBNMTNDKEY-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ZTMXJAXHRVRFRZ-UHFFFAOYSA-N [2-butyl-5-chloro-3-[4-[2-(1-trityltetrazol-5-yl)phenyl]phenyl]imidazol-4-yl]methanol Chemical compound CCCCC1=NC(Cl)=C(CO)N1C1=CC=C(C=2C(=CC=CC=2)C=2N(N=NN=2)C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 ZTMXJAXHRVRFRZ-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
230000008901 benefit Effects 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
238000010899 nucleation Methods 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
150000003138 primary alcohols Chemical class 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
AICIYIDUYNFPRY-UHFFFAOYSA-N 1,3-dihydro-2H-imidazol-2-one Chemical compound O=C1NC=CN1 AICIYIDUYNFPRY-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
229940123413 Angiotensin II antagonist Drugs 0.000 description 1
238000007171 acid catalysis Methods 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
239000002333 angiotensin II receptor antagonist Substances 0.000 description 1
229940127282 angiotensin receptor antagonist Drugs 0.000 description 1
239000012296 anti-solvent Substances 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
150000001924 cycloalkanes Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000002542 deteriorative effect Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical group 0.000 description 1
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 1
QDYTUZCWBJRHKK-UHFFFAOYSA-N imidazole-4-methanol Chemical compound OCC1=CNC=N1 QDYTUZCWBJRHKK-UHFFFAOYSA-N 0.000 description 1
230000006872 improvement Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Encapsulation Of And Coatings For Semiconductor Or Solid State Devices (AREA)
Dicing (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Manufacture Of Electron Tubes, Discharge Lamp Vessels, Lead-In Wires, And The Like (AREA)
Peptides Or Proteins (AREA)

SK5014-2006A 2003-08-27 2004-08-26 Spôsob odstraňovania trifenylmetánovej ochrannej skupiny SK50142006A3 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CZ20032319A CZ297016B6 (cs)	2003-08-27	2003-08-27	Zpusob odstranování trifenylmethanové chránicí skupiny z 1-trityl-5-(4'-subst. aminomethyl-1,1' -bifenyl-2-yl)-1H-tetrazolu a zpusob výroby draselné soli losartanu, irbesartanu a valsartanu s jeho pouzitím
CZ20040733A CZ298329B6 (cs)	2004-06-16	2004-06-16	Zpusob výroby 1-(cyklohexyloxykarbonyloxy)ethyl-2-ethoxy-1-[[2´-(1H-tetrazol-5-yl)bifenyl-4-yl]methyl]benzimidazol-7-karboxylátu (candesartan cilexetilu)
PCT/CZ2004/000051 WO2005021535A2 (en)	2003-08-27	2004-08-26	A method of removing the triphenylmethane protecting group

Publications (1)

Publication Number	Publication Date
SK50142006A3 true SK50142006A3 (sk)	2006-05-04

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Application Number	Title	Priority Date	Filing Date
SK5014-2006A SK50142006A3 (sk)	2003-08-27	2004-08-26	Spôsob odstraňovania trifenylmetánovej ochrannej skupiny

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US (1)	US20060287537A1 (de)
EP (1)	EP1658281B1 (de)
AT (1)	ATE482950T1 (de)
CA (1)	CA2536781A1 (de)
DE (1)	DE602004029373D1 (de)
EA (1)	EA011507B1 (de)
ES (1)	ES2348300T3 (de)
HR (1)	HRP20060119A2 (de)
PL (2)	PL1658281T3 (de)
PT (1)	PT1658281E (de)
RS (1)	RS20060125A (de)
SK (1)	SK50142006A3 (de)
WO (1)	WO2005021535A2 (de)

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SI22127A (sl)	2005-10-07	2007-04-30	Krka, Tovarna Zdravil, D.D., Novo Mesto	Postopek za pripravo kandesartan cileksetila
CZ299902B6 (cs) *	2005-10-27	2008-12-29	Zentiva, A. S	Zpusob odstranování trifenylmethanové chránicí skupiny u prekurzoru antihypertenzních léciv
WO2008018843A1 (en) *	2006-08-08	2008-02-14	Ulkar Kimya Sanayi Ve Ticaret As	Process for producing useful salts form of biphenyl-tetrazole compounds
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US11327065B1 (en) *	2021-08-27	2022-05-10	Jubilant Generics Limited	Preparation of angiotensin receptor blockers or pharmaceutically acceptable salts thereof
CN116606282A (zh) *	2023-05-17	2023-08-18	杭州新曦科技有限公司	用于制备氯沙坦钾及其相关中间体的方法

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2004
- 2004-08-26 US US10/569,428 patent/US20060287537A1/en not_active Abandoned
- 2004-08-26 ES ES04762303T patent/ES2348300T3/es not_active Expired - Lifetime
- 2004-08-26 HR HR20060119A patent/HRP20060119A2/hr not_active Application Discontinuation
- 2004-08-26 RS YUP-2006/0125A patent/RS20060125A/sr unknown
- 2004-08-26 CA CA002536781A patent/CA2536781A1/en not_active Abandoned
- 2004-08-26 PL PL04762303T patent/PL1658281T3/pl unknown
- 2004-08-26 EP EP04762303A patent/EP1658281B1/de not_active Expired - Lifetime
- 2004-08-26 SK SK5014-2006A patent/SK50142006A3/sk unknown
- 2004-08-26 AT AT04762303T patent/ATE482950T1/de not_active IP Right Cessation
- 2004-08-26 WO PCT/CZ2004/000051 patent/WO2005021535A2/en not_active Ceased
- 2004-08-26 EA EA200600079A patent/EA011507B1/ru not_active IP Right Cessation
- 2004-08-26 PL PL379886A patent/PL379886A1/pl not_active Application Discontinuation
- 2004-08-26 PT PT04762303T patent/PT1658281E/pt unknown
- 2004-08-26 DE DE602004029373T patent/DE602004029373D1/de not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2536781A1 (en)	2005-03-10
US20060287537A1 (en)	2006-12-21
EA011507B1 (ru)	2009-04-28
EA200600079A1 (ru)	2006-08-25
ATE482950T1 (de)	2010-10-15
HRP20060119A2 (en)	2006-05-31
RS20060125A (sr)	2008-06-05
PL379886A1 (pl)	2006-11-27
EP1658281B1 (de)	2010-09-29
WO2005021535A3 (en)	2005-06-09
DE602004029373D1 (de)	2010-11-11
EP1658281A2 (de)	2006-05-24
ES2348300T3 (es)	2010-12-02
PT1658281E (pt)	2010-10-12
WO2005021535A2 (en)	2005-03-10
PL1658281T3 (pl)	2010-12-31

Legal Events

Date	Code	Title	Description
2012-09-03	FB9A	Suspension of patent application procedure

Publication	Publication Date	Title
SK50142006A3 (sk)	2006-05-04	Spôsob odstraňovania trifenylmetánovej ochrannej skupiny
CA2036304C (en)	2001-04-17	Pyrimidinedione derivatives, their production and use
CA2562597A1 (en)	2005-11-24	Preparation of candesartan cilexetil in high purity
CZ2005679A3 (cs)	2007-05-09	Zpusob odstranování trifenylmethanové chránící skupiny u prekursoru antihypertensních léciv
WO2005051929A1 (en)	2005-06-09	Conversion of aromatic nitriles into tetrazoles
BG107478A (bg)	2004-01-30	Метод за кристализация на лозартан калий
SK286740B6 (sk)	2009-04-06	Spôsob syntézy draselnej soli losartanu
EP1474417B1 (de)	2006-03-22	Verfahren zur herstellung von losartan und losartan-kaliumsalz
CA2555294A1 (en)	2005-08-25	Candesartan cilexetil polymorphs
CA2515138A1 (en)	2004-08-26	Synthesis of 2-butyl-3-(2'-(1-trityl-1h-tetrazol-5-yl)biphenyl-4-yl)-1,3-diazaspirol[4,4]-non-ene-4-one
CZ297016B6 (cs)	2006-08-16	Zpusob odstranování trifenylmethanové chránicí skupiny z 1-trityl-5-(4'-subst. aminomethyl-1,1' -bifenyl-2-yl)-1H-tetrazolu a zpusob výroby draselné soli losartanu, irbesartanu a valsartanu s jeho pouzitím
US20080214637A1 (en)	2008-09-04	Process for the Synthesis of Tetrazoles
CN103304543A (zh)	2013-09-18	一种坎地沙坦酯的制备方法
JP3032844B2 (ja)	2000-04-17	ピリミジンジオン誘導体
ES2264641B1 (es)	2008-03-01	Procedimiento para la obtencion de derivados de bencimidazol y sus intermedios.
KR101009404B1 (ko)	2011-01-19	(에스)-엔-(1-카르복시-2-메틸-프로-1-필)-엔-펜타노일-엔-[2'-(1에이취-테트라졸-5-일)비페닐-4-일-메틸]아민화합물의 고순도 제조방법
CZ298329B6 (cs)	2007-08-29	Zpusob výroby 1-(cyklohexyloxykarbonyloxy)ethyl-2-ethoxy-1-[[2´-(1H-tetrazol-5-yl)bifenyl-4-yl]methyl]benzimidazol-7-karboxylátu (candesartan cilexetilu)
CZ299265B6 (cs)	2008-05-28	Zpusob výroby 1-(cyklohexyloxykarbonyloxy)ethyl-2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)bifenyl-4-yl]methyl]benzimidazol-7-karboxylátu (candesartan cilexetilu)
SE505562C2 (sv)	1997-09-15	Karboximetylidencykloheptimidazolderivat, förfarande för deras framställning och terapeutiska medel innehållande dessa föreningar
KR101009383B1 (ko)	2011-01-19	고순도의2-부틸-3-[[2'-(1에이취-테트라졸-5-일)[1,1'-비페닐]-4-일]메틸]-1,3-디아자스피로[4.4]논-1-엔-4-온 화합물의제조방법
KR20100110438A (ko)	2010-10-13	올메살탄의 신규한 에스테르 화합물, 이의 중간체, 이의 제조방법 및 이를 포함하는 조성물
Young &Co	0	EUROPEAN PATENT SPECIFICATION
CZ302240B6 (cs)	2011-01-05	Zpusob odstranování trifenylmethanové chránicí skupiny u prekursoru antihypertensiv majících labilní, metabolicky odbouratelnou skupinu
WO2008041957A1 (en)	2008-04-10	Method for producing pure crystalline form of 2-n-butyl-3-((2-(1h-tetrazole-5-yl) (1,1'-biphenyl)-4-methyl)-1,3-diazapspiro (4,4') non -1- en-4-one
EP1634880A2 (de)	2006-03-15	Verfahren zur Herstellung von Losartan und Kaliumlosartan