SE504459C2 - Förfarande för framställning av substituerade sulfoxider - Google Patents

Förfarande för framställning av substituerade sulfoxider

Info

Publication number: SE504459C2
Authority: SE; Sweden
Prior art keywords: process according; methoxy; benzimidazole; mmol; methyl
Prior art date: 1994-07-15

Application number

SE9402510A

Other languages

English (en)

Swedish (sv)

Other versions

SE9402510D0 (sv

SE9402510L (sv

Inventor

Magnus Larsson

Henrik Soerensen

Urban Stenhede

Unge Sverker Von

Original Assignee

Astra Ab

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.)

1994-07-15

Filing date

1994-07-15

Publication date

1997-02-17

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=20394753&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SE504459(C2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1994-07-15 Publication of SE9402510D0 publication Critical patent/SE9402510D0/xx

1994-07-15 Priority to SE9402510A priority Critical patent/SE504459C2/sv

1994-07-15 Application filed by Astra Ab filed Critical Astra Ab

1995-07-03 Priority to RU97102162/04A priority patent/RU2157806C2/ru

1995-07-03 Priority to AT95926068T priority patent/ATE242233T1/de

1995-07-03 Priority to CA002193994A priority patent/CA2193994C/fr

1995-07-03 Priority to PT95926068T priority patent/PT773940E/pt

1995-07-03 Priority to EE9700006A priority patent/EE03354B1/xx

1995-07-03 Priority to HK98109230.4A priority patent/HK1008331B/en

1995-07-03 Priority to KR1019970700221A priority patent/KR100356252B1/ko

1995-07-03 Priority to EP95926068A priority patent/EP0773940B2/fr

1995-07-03 Priority to BR9508292A priority patent/BR9508292A/pt

1995-07-03 Priority to US08/492,087 priority patent/US5948789A/en

1995-07-03 Priority to UA97020638A priority patent/UA47409C2/uk

1995-07-03 Priority to DK95926068.8T priority patent/DK0773940T4/da

1995-07-03 Priority to PCT/SE1995/000818 priority patent/WO1996002535A1/fr

1995-07-03 Priority to MX9700358D priority patent/MX9700358A/es

1995-07-03 Priority to ES95926068T priority patent/ES2199998T5/es

1995-07-03 Priority to DE69530987T priority patent/DE69530987T3/de

1995-07-03 Priority to SI9530676T priority patent/SI0773940T2/sl

1995-07-03 Priority to SK48-97A priority patent/SK284059B6/sk

1995-07-03 Priority to JP50493896A priority patent/JP3795917B2/ja

1995-07-03 Priority to AU29948/95A priority patent/AU688074B2/en

1995-07-04 Priority to TW084106875A priority patent/TW372971B/zh

1995-07-05 Priority to NZ289959A priority patent/NZ289959A/en

1995-07-05 Priority to CZ0006497A priority patent/CZ297987B6/cs

1995-07-05 Priority to PL95318165A priority patent/PL186342B1/pl

1995-07-05 Priority to CN95194956.XA priority patent/CN1070489C/zh

1995-07-05 Priority to HU9700108A priority patent/HU226361B1/hu

1995-07-06 Priority to IL11447795A priority patent/IL114477A/en

1995-07-10 Priority to ZA955724A priority patent/ZA955724B/xx

1995-07-10 Priority to MA23950A priority patent/MA23611A1/fr

1995-07-11 Priority to EG57195A priority patent/EG24534A/xx

1995-07-11 Priority to DZ950088A priority patent/DZ1911A1/fr

1995-07-12 Priority to HR950401A priority patent/HRP950401B1/xx

1995-07-13 Priority to TNTNSN95081A priority patent/TNSN95081A1/fr

1995-07-14 Priority to TR95/00861A priority patent/TR199500861A2/xx

1995-07-14 Priority to YU47695A priority patent/YU49475B/sh

1995-07-14 Priority to MYPI95001998A priority patent/MY113180A/en

1995-10-07 Priority to SA95160294A priority patent/SA95160294B1/ar

1996-01-16 Publication of SE9402510L publication Critical patent/SE9402510L/xx

1996-06-28 Priority to ARP960103398A priority patent/AR003443A1/es

1996-12-27 Priority to IS4406A priority patent/IS1772B/is

1997-01-10 Priority to FI970102A priority patent/FI117672B/fi

1997-01-10 Priority to FI970102D priority patent/FI117830B/fi

1997-01-14 Priority to NO19970153A priority patent/NO312101B1/no

1997-02-17 Publication of SE504459C2 publication Critical patent/SE504459C2/sv

Links

238000000034 method Methods 0.000 title claims abstract description 48
150000003462 sulfoxides Chemical class 0.000 title claims description 37
238000002360 preparation method Methods 0.000 title description 3
238000007254 oxidation reaction Methods 0.000 claims abstract description 29
230000003647 oxidation Effects 0.000 claims abstract description 25
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 7
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 6
230000015572 biosynthetic process Effects 0.000 claims abstract description 5
238000003786 synthesis reaction Methods 0.000 claims abstract description 4
159000000011 group IA salts Chemical class 0.000 claims abstract 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 17
-1 4-methoxy-3,5-dimethyl-2-pyridinyl Chemical group 0.000 claims description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 12
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 10
YSAVZVORKRDODB-PHDIDXHHSA-N diethyl (2r,3r)-2,3-dihydroxybutanedioate Chemical compound CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC YSAVZVORKRDODB-PHDIDXHHSA-N 0.000 claims description 10
239000000047 product Substances 0.000 claims description 10
238000002425 crystallisation Methods 0.000 claims description 9
230000008025 crystallization Effects 0.000 claims description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 7
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
235000011114 ammonium hydroxide Nutrition 0.000 claims description 6
239000012043 crude product Substances 0.000 claims description 5
239000003446 ligand Substances 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
239000007800 oxidant agent Substances 0.000 claims description 5
238000010626 work up procedure Methods 0.000 claims description 5
150000007530 organic bases Chemical class 0.000 claims description 4
150000003608 titanium Chemical class 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
YSAVZVORKRDODB-WDSKDSINSA-N diethyl tartrate Chemical compound CCOC(=O)[C@@H](O)[C@H](O)C(=O)OCC YSAVZVORKRDODB-WDSKDSINSA-N 0.000 claims description 3
150000007529 inorganic bases Chemical class 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims 5
239000001257 hydrogen Substances 0.000 claims 5
125000000217 alkyl group Chemical group 0.000 claims 4
229910052736 halogen Inorganic materials 0.000 claims 4
150000002367 halogens Chemical group 0.000 claims 4
150000002431 hydrogen Chemical class 0.000 claims 4
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 4
125000003545 alkoxy group Chemical group 0.000 claims 3
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
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 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 claims 1
125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
125000005206 alkoxycarbonyloxymethyl group Chemical group 0.000 claims 1
125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
125000002947 alkylene group Chemical group 0.000 claims 1
125000003710 aryl alkyl group Chemical group 0.000 claims 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
125000005265 dialkylamine group Chemical group 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
125000004438 haloalkoxy group Chemical group 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
125000002971 oxazolyl group Chemical group 0.000 claims 1
125000002071 phenylalkoxy group Chemical group 0.000 claims 1
125000003884 phenylalkyl group Chemical group 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract description 4
SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 abstract description 3
229960000381 omeprazole Drugs 0.000 abstract description 3
HBDKFZNDMVLSHM-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfinyl)-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1S(=O)CC1=CC=CC=N1 HBDKFZNDMVLSHM-UHFFFAOYSA-N 0.000 abstract 1
239000003814 drug Substances 0.000 abstract 1
239000000203 mixture Substances 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
238000007792 addition Methods 0.000 description 20
239000000243 solution Substances 0.000 description 17
239000002585 base Substances 0.000 description 12
125000000446 sulfanediyl group Chemical group *S* 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
150000001875 compounds Chemical class 0.000 description 9
238000004296 chiral HPLC Methods 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
238000011914 asymmetric synthesis Methods 0.000 description 7
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
238000002474 experimental method Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
150000003457 sulfones Chemical class 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
125000004434 sulfur atom Chemical group 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000010936 titanium Substances 0.000 description 4
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 3
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical class [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
238000000746 purification Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
229910052719 titanium Inorganic materials 0.000 description 2
JXOSPTBRSOYXGC-UHFFFAOYSA-N 1-Chloro-4-iodobutane Chemical compound ClCCCCI JXOSPTBRSOYXGC-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
AIABEETXTKSDLE-UHFFFAOYSA-J 2,3-dihydroxybutanedioate;titanium(4+) Chemical compound [Ti+4].[O-]C(=O)C(O)C(O)C([O-])=O.[O-]C(=O)C(O)C(O)C([O-])=O AIABEETXTKSDLE-UHFFFAOYSA-J 0.000 description 1
GMTAWLUJHGIUPU-UHFFFAOYSA-N 4,5-diphenyl-1,3-dihydroimidazole-2-thione Chemical compound N1C(S)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 GMTAWLUJHGIUPU-UHFFFAOYSA-N 0.000 description 1
241000272814 Anser sp. Species 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical group COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
102000001494 Sterol O-Acyltransferase Human genes 0.000 description 1
108010054082 Sterol O-acyltransferase Proteins 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
125000005002 aryl methyl group Chemical group 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
MRIZMKJLUDDMHF-UHFFFAOYSA-N cumene;hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC=C1 MRIZMKJLUDDMHF-UHFFFAOYSA-N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000011978 dissolution method Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 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
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
230000005588 protonation Effects 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000012958 reprocessing Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000003335 steric effect Effects 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/28—Sulfur atoms
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
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SE9402510A 1994-07-15 1994-07-15 Förfarande för framställning av substituerade sulfoxider SE504459C2 (sv)

Priority Applications (43)

Application Number	Priority Date	Filing Date	Title
SE9402510A SE504459C2 (sv)	1994-07-15	1994-07-15	Förfarande för framställning av substituerade sulfoxider
JP50493896A JP3795917B2 (ja)	1994-07-15	1995-07-03	置換スルホキシドの合成法
AU29948/95A AU688074B2 (en)	1994-07-15	1995-07-03	Process for synthesis of substituted sulphoxides
BR9508292A BR9508292A (pt)	1994-07-15	1995-07-03	Processos para a sintese enãncio-seletiva de um composto,(-)-5-metóxi-2[[(4-metóxi-3,5-dimetil-2-piridinil) metil]sulfinil]-1h-benzimidazol,(+)-5-fluoro-2-(((4-ciclopropilmetóxi-2-piridinil) metil) sulfinil)-1h-benzimidazol,(-)-5-fluoro-2-(((4-ciclopropilmetóxi-2-piridinil) metil) sulfinil)-1h-benzimidazol,(-)-5-fluoro-2-(((4-ciclopropilmetóxi-2-piridinil) metil) sulfinil)-1h-benzimidazol,(-)-5-carbometóxi-6-metil-2-[[(3,4-dimetóxi-2-piridinil) metil] sulfinil]-1h-benzimidazol,(+)-5-carbometóxi-6-metil-2-[[(3,4-dimetóxi-2-piridinil) metil] sulfinil]-1h benzimidazol composto e uso dos compostos
DK95926068.8T DK0773940T4 (da)	1994-07-15	1995-07-03	Fremgangsmåde til syntese af substituerede sulfoxider
CA002193994A CA2193994C (fr)	1994-07-15	1995-07-03	Procede de synthese de sulfoxydes substitues
PT95926068T PT773940E (pt)	1994-07-15	1995-07-03	Processo de sintese de sulfoxidos substituidos
EE9700006A EE03354B1 (et)	1994-07-15	1995-07-03	Asendatud sulfoksiidide sünteesi protsess
HK98109230.4A HK1008331B (en)	1994-07-15	1995-07-03	Process for synthesis of substituted sulphoxides
KR1019970700221A KR100356252B1 (ko)	1994-07-15	1995-07-03	치환술폭시드의합성방법
EP95926068A EP0773940B2 (fr)	1994-07-15	1995-07-03	Procede de synthese de sulfoxydes substitues
RU97102162/04A RU2157806C2 (ru)	1994-07-15	1995-07-03	Способы синтеза замещенных сульфоксидов
US08/492,087 US5948789A (en)	1994-07-15	1995-07-03	Process for synthesis of substituted sulphoxides
UA97020638A UA47409C2 (uk)	1994-07-15	1995-07-03	Спосіб синтезу заміщених сульфоксидів (варіанти) та сульфоксид
AT95926068T ATE242233T1 (de)	1994-07-15	1995-07-03	Verfahren zur herstellung von substituierten sulfoxiden
PCT/SE1995/000818 WO1996002535A1 (fr)	1994-07-15	1995-07-03	Procede de synthese de sulfoxydes substitues
MX9700358D MX9700358A (es)	1994-07-15	1995-07-03	Proceso par a la sintesis de sulfoxidos substituidos.
ES95926068T ES2199998T5 (es)	1994-07-15	1995-07-03	Procedimiento para la síntesis de sulfóxidos sustituidos.
DE69530987T DE69530987T3 (de)	1994-07-15	1995-07-03	Verfahren zur herstellung von substituierten sulfoxiden
SI9530676T SI0773940T2 (sl)	1994-07-15	1995-07-03	Postopek za sintezo substituiranih sulfoksidov
SK48-97A SK284059B6 (sk)	1994-07-15	1995-07-03	Spôsob prípravy substituovaných sulfoxidov
TW084106875A TW372971B (en)	1994-07-15	1995-07-04	Process for synthesis of substituted sulphoxides
CN95194956.XA CN1070489C (zh)	1994-07-15	1995-07-05	取代的亚砜类化合物的合成方法
NZ289959A NZ289959A (en)	1994-07-15	1995-07-05	Process for enantioselective synthesis of substituted 2-[(2-pyridinyl(or phenyl)methyl)sulphinyl]-1h-[benzimidazole (or thienoimidazole)] (including omeprazole) and other structurally related suphoxides and salts thereof
CZ0006497A CZ297987B6 (cs)	1994-07-15	1995-07-05	Zpusob prípravy substituovaných sulfoxidu
HU9700108A HU226361B1 (en)	1994-07-15	1995-07-05	Process for synthesis of substituted sulphoxides
PL95318165A PL186342B1 (pl)	1994-07-15	1995-07-05	Sposób enancjoselektywnej syntezy związku sulfotlenkowego
IL11447795A IL114477A (en)	1994-07-15	1995-07-06	Process for enantioselective synthesis of substituted sulfoxides, single enantiomers obtained by the process and their use for the preparation of medicaments
ZA955724A ZA955724B (en)	1994-07-15	1995-07-10	Process for synthesis of substituted sulphoxides
MA23950A MA23611A1 (fr)	1994-07-15	1995-07-10	Procede pour la synthese de sulfoxydes substitues
EG57195A EG24534A (en)	1994-07-15	1995-07-11	Process for synthesis of substituted sulfoxides
DZ950088A DZ1911A1 (fr)	1994-07-15	1995-07-11	Procédé pour la synthèse de sulfoxydes substitues.
HR950401A HRP950401B1 (en)	1994-07-15	1995-07-12	Process for synthesis of substituted sulphoxides
TNTNSN95081A TNSN95081A1 (fr)	1994-07-15	1995-07-13	Procede pour la synthese de sulfoxydes substitues
MYPI95001998A MY113180A (en)	1994-07-15	1995-07-14	Process for synthesis of substituted sulfoxides
TR95/00861A TR199500861A2 (tr)	1994-07-15	1995-07-14	Ikame edilmis sulfoksidlerin sentezi icin proses.
YU47695A YU49475B (sh)	1994-07-15	1995-07-14	Postupak za sintezu supstituisanih sulfoksida
SA95160294A SA95160294B1 (ar)	1994-07-15	1995-10-07	عملية لتحضير synthesisمركبات سلفوكسيد مستبدلة substituted sulphoxide
ARP960103398A AR003443A1 (es)	1994-07-15	1996-06-28	Procedimiento para la purificacion optica de preparaciones enantiomericamente enriquecidas de compuestos derivados de 2-sulfinil-bencimidazol
IS4406A IS1772B (is)	1994-07-15	1996-12-27	Aðferð við myndun útskiptra súlfoxíða
FI970102A FI117672B (fi)	1994-07-15	1997-01-10	Menetelmä substituoitujen sulfoksidien syntetisoimiseksi
FI970102D FI117830B (fi)	1994-07-15	1997-01-10	Menetelmä substituoitujen sulfoksidien syntetisoimiseksi
NO19970153A NO312101B1 (no)	1994-07-15	1997-01-14	Fremgangsmåte for syntese av substituerte sulfoksider, og slike produktforbindelser

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE9402510A SE504459C2 (sv)	1994-07-15	1994-07-15	Förfarande för framställning av substituerade sulfoxider

Publications (3)

Publication Number	Publication Date
SE9402510D0 SE9402510D0 (sv)	1994-07-15
SE9402510L SE9402510L (sv)	1996-01-16
SE504459C2 true SE504459C2 (sv)	1997-02-17

Family

ID=20394753

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE9402510A SE504459C2 (sv)	1994-07-15	1994-07-15	Förfarande för framställning av substituerade sulfoxider

Country Status (41)

Country	Link
US (1)	US5948789A (fr)
EP (1)	EP0773940B2 (fr)
JP (1)	JP3795917B2 (fr)
KR (1)	KR100356252B1 (fr)
CN (1)	CN1070489C (fr)
AR (1)	AR003443A1 (fr)
AT (1)	ATE242233T1 (fr)
AU (1)	AU688074B2 (fr)
BR (1)	BR9508292A (fr)
CA (1)	CA2193994C (fr)
CZ (1)	CZ297987B6 (fr)
DE (1)	DE69530987T3 (fr)
DK (1)	DK0773940T4 (fr)
DZ (1)	DZ1911A1 (fr)
EE (1)	EE03354B1 (fr)
EG (1)	EG24534A (fr)
ES (1)	ES2199998T5 (fr)
FI (2)	FI117672B (fr)
HR (1)	HRP950401B1 (fr)
HU (1)	HU226361B1 (fr)
IL (1)	IL114477A (fr)
IS (1)	IS1772B (fr)
MA (1)	MA23611A1 (fr)
MX (1)	MX9700358A (fr)
MY (1)	MY113180A (fr)
NO (1)	NO312101B1 (fr)
NZ (1)	NZ289959A (fr)
PL (1)	PL186342B1 (fr)
PT (1)	PT773940E (fr)
RU (1)	RU2157806C2 (fr)
SA (1)	SA95160294B1 (fr)
SE (1)	SE504459C2 (fr)
SI (1)	SI0773940T2 (fr)
SK (1)	SK284059B6 (fr)
TN (1)	TNSN95081A1 (fr)
TR (1)	TR199500861A2 (fr)
TW (1)	TW372971B (fr)
UA (1)	UA47409C2 (fr)
WO (1)	WO1996002535A1 (fr)
YU (1)	YU49475B (fr)
ZA (1)	ZA955724B (fr)

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1994
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Publication number	Publication date
IL114477A0 (en)	1995-11-27
SA95160294B1 (ar)	2006-07-31
NO312101B1 (no)	2002-03-18
ATE242233T1 (de)	2003-06-15
KR970704731A (ko)	1997-09-06
CA2193994C (fr)	2005-05-03
JPH10504290A (ja)	1998-04-28
EP0773940B2 (fr)	2010-11-17
UA47409C2 (uk)	2002-07-15
SI0773940T1 (en)	2004-02-29
IS1772B (is)	2001-06-01
EP0773940A1 (fr)	1997-05-21
AU688074B2 (en)	1998-03-05
FI117672B (fi)	2007-01-15
AR003443A1 (es)	1998-08-05
MA23611A1 (fr)	1996-04-01
SK284059B6 (sk)	2004-09-08
CA2193994A1 (fr)	1996-02-01
WO1996002535A1 (fr)	1996-02-01
TR199500861A2 (tr)	1996-06-21
MX9700358A (es)	1997-04-30
SK4897A3 (en)	1997-08-06
CZ297987B6 (cs)	2007-05-16
DE69530987D1 (de)	2003-07-10
CZ6497A3 (en)	1997-06-11
CN1157614A (zh)	1997-08-20
NO970153L (no)	1997-01-14
FI970102L (fi)	1997-01-10
DZ1911A1 (fr)	2002-02-17
EG24534A (en)	2009-08-30
DK0773940T3 (da)	2003-09-15
DE69530987T2 (de)	2004-05-19
JP3795917B2 (ja)	2006-07-12
DK0773940T4 (da)	2011-02-07
IS4406A (is)	1996-12-27
SI0773940T2 (sl)	2011-02-28
EP0773940B1 (fr)	2003-06-04
KR100356252B1 (ko)	2002-11-18
FI117830B (fi)	2007-03-15
YU49475B (sh)	2006-05-25
BR9508292A (pt)	1997-12-23
YU47695A (sh)	1998-07-10
PL318165A1 (en)	1997-05-26
HK1008331A1 (en)	1999-05-07
ZA955724B (en)	1996-01-15
FI970102A0 (fi)	1997-01-10
SE9402510D0 (sv)	1994-07-15
NZ289959A (en)	1998-01-26
US5948789A (en)	1999-09-07
ES2199998T5 (es)	2011-03-16
HUT76642A (en)	1997-10-28
PT773940E (pt)	2003-10-31
SE9402510L (sv)	1996-01-16
IL114477A (en)	2001-07-24
MY113180A (en)	2001-12-31
AU2994895A (en)	1996-02-16
DE69530987T3 (de)	2011-07-07
HRP950401B1 (en)	2004-04-30
RU2157806C2 (ru)	2000-10-20
TW372971B (en)	1999-11-01
PL186342B1 (pl)	2003-12-31
HRP950401A2 (en)	1997-10-31
TNSN95081A1 (fr)	1996-02-06
EE03354B1 (et)	2001-02-15
CN1070489C (zh)	2001-09-05
NO970153D0 (no)	1997-01-14
HU226361B1 (en)	2008-09-29
WO1996002535A8 (fr)	1999-12-23
ES2199998T3 (es)	2004-03-01

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2014-09-23	NUG	Patent has lapsed

Publication	Publication Date	Title
SE504459C2 (sv)	1997-02-17	Förfarande för framställning av substituerade sulfoxider
EP0836601B1 (fr)	2008-12-24	Procede de purification optique pour derives de benzimidazole enrichis par enantiomorphe
EP1293507B1 (fr)	2007-11-28	Procede de production d'un cristal
US7928241B2 (en)	2011-04-19	Stereoselective synthesis of benzimidazole sulfoxides
WO2003089408A2 (fr)	2003-10-30	Pyridinylmethyl-sulphinyl-benzimidazole substitue optiquement actif et sels
RU2211218C2 (ru)	2003-08-27	Способ получения омепразола
WO2010095144A2 (fr)	2010-08-26	Procédé de préparation d'inhibiteurs de pompe à protons
WO2007088559A1 (fr)	2007-08-09	Procédé de production de sulphoxydes substitués
EP2106397B1 (fr)	2011-11-16	Procédé de préparation d'ésoméprazole pur sur le plan énantiomère
US7557217B2 (en)	2009-07-07	Process for production of benzimidazole derivative salt precipitate
WO2007066202A1 (fr)	2007-06-14	Procede de fabrication de 2-(2-pyridylmethyl)-sulfinyl-1h-benzimidazoles
HK1008331B (en)	2003-11-21	Process for synthesis of substituted sulphoxides
HK1010193B (en)	2009-04-17	A process for the optical purification of enantiomerically enriched benzimidazole derivatives