NO312101B1 - Fremgangsmåte for syntese av substituerte sulfoksider, og slike produktforbindelser - Google Patents

Fremgangsmåte for syntese av substituerte sulfoksider, og slike produktforbindelser Download PDF

Info

Publication number: NO312101B1
Authority: NO; Norway
Prior art keywords: chiral; alkyl; hydrogen; mmol; alkoxy
Prior art date: 1994-07-15

Application number

NO19970153A

Other languages

English (en)

Norwegian (no)

Other versions

NO970153L (no

NO970153D0 (no

Inventor

Erik Magnus Larsson

Urban Jan Stenhede

Henrik Soerensen

Per Oskar Sverker Von Unge

Hanna Kristina Cotton

Original Assignee

Astrazeneca 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

1997-01-14

Publication date

2002-03-18

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=NO312101(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1997-01-14 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

1997-01-14 Publication of NO970153L publication Critical patent/NO970153L/no

1997-01-14 Publication of NO970153D0 publication Critical patent/NO970153D0/no

2002-03-18 Publication of NO312101B1 publication Critical patent/NO312101B1/no

Links

238000000034 method Methods 0.000 title claims description 87
150000003462 sulfoxides Chemical class 0.000 title claims description 73
150000001875 compounds Chemical class 0.000 title claims description 71
230000015572 biosynthetic process Effects 0.000 title claims description 12
238000003786 synthesis reaction Methods 0.000 title claims description 11
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 84
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 62
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 60
238000007254 oxidation reaction Methods 0.000 claims description 51
230000003647 oxidation Effects 0.000 claims description 49
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 41
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 39
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 35
239000010936 titanium Substances 0.000 claims description 33
239000000047 product Substances 0.000 claims description 32
229910052719 titanium Inorganic materials 0.000 claims description 32
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical group CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 30
229910052739 hydrogen Inorganic materials 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 30
125000003545 alkoxy group Chemical group 0.000 claims description 25
150000002431 hydrogen Chemical group 0.000 claims description 25
238000002360 preparation method Methods 0.000 claims description 25
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 23
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 description 22
-1 sulfoxide compound Chemical class 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical group 0.000 claims description 20
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 claims description 15
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 15
125000001424 substituent group Chemical group 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 13
239000003960 organic solvent Substances 0.000 claims description 12
239000012043 crude product Substances 0.000 claims description 10
238000002425 crystallisation Methods 0.000 claims description 10
230000008025 crystallization Effects 0.000 claims description 10
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims description 8
239000003446 ligand Substances 0.000 claims description 8
239000007800 oxidant agent Substances 0.000 claims description 8
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000006165 cyclic alkyl group Chemical group 0.000 claims description 5
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
125000004663 dialkyl amino group Chemical group 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
125000004438 haloalkoxy group Chemical group 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000002971 oxazolyl group Chemical group 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000002071 phenylalkoxy group Chemical group 0.000 claims description 5
125000003884 phenylalkyl group Chemical group 0.000 claims description 5
125000004950 trifluoroalkyl group Chemical group 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
150000002009 diols Chemical class 0.000 claims description 4
YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 3
150000007530 organic bases Chemical class 0.000 claims description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
150000004703 alkoxides Chemical class 0.000 claims description 2
159000000011 group IA salts Chemical class 0.000 claims description 2
235000002906 tartaric acid Nutrition 0.000 claims description 2
239000011975 tartaric acid Substances 0.000 claims description 2
KKKDZZRICRFGSD-UHFFFAOYSA-N 1-benzylimidazole Chemical compound C1=CN=CN1CC1=CC=CC=C1 KKKDZZRICRFGSD-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 description 106
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 79
239000000243 solution Substances 0.000 description 63
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
230000003287 optical effect Effects 0.000 description 51
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
238000011914 asymmetric synthesis Methods 0.000 description 32
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
150000003457 sulfones Chemical class 0.000 description 23
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 21
230000014759 maintenance of location Effects 0.000 description 20
238000003756 stirring Methods 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
XURCIPRUUASYLR-UHFFFAOYSA-N Omeprazole sulfide Chemical compound N=1C2=CC(OC)=CC=C2NC=1SCC1=NC=C(C)C(OC)=C1C XURCIPRUUASYLR-UHFFFAOYSA-N 0.000 description 17
238000004458 analytical method Methods 0.000 description 17
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 15
235000011114 ammonium hydroxide Nutrition 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
238000001704 evaporation Methods 0.000 description 13
230000008020 evaporation Effects 0.000 description 13
239000010410 layer Substances 0.000 description 13
239000002244 precipitate Substances 0.000 description 12
150000003568 thioethers Chemical class 0.000 description 12
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 description 11
239000003480 eluent Substances 0.000 description 11
235000019439 ethyl acetate Nutrition 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
238000001914 filtration Methods 0.000 description 11
239000002904 solvent Substances 0.000 description 11
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 11
239000000463 material Substances 0.000 description 10
RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical compound CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
239000013078 crystal Substances 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
229910052717 sulfur Inorganic materials 0.000 description 9
125000004434 sulfur atom Chemical group 0.000 description 9
238000010626 work up procedure Methods 0.000 description 9
238000000605 extraction Methods 0.000 description 8
238000004519 manufacturing process Methods 0.000 description 8
229960000381 omeprazole Drugs 0.000 description 7
238000000926 separation method Methods 0.000 description 7
POQMHHDKXWTFHB-UHFFFAOYSA-N 1-[5-[(4,5-diphenyl-1h-imidazol-2-yl)sulfinyl]pentyl]-3,5-dimethylpyrazole Chemical compound N1=C(C)C=C(C)N1CCCCCS(=O)C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 POQMHHDKXWTFHB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
238000003818 flash chromatography Methods 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
HVAJOLFRLWQQQL-UHFFFAOYSA-N 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1h-benzimidazole;sodium Chemical compound [Na].N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C HVAJOLFRLWQQQL-UHFFFAOYSA-N 0.000 description 5
OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
KTXVWWXXGRAFKB-UHFFFAOYSA-N 2-[[4-(cyclopropylmethoxy)pyridin-2-yl]methylsulfanyl]-6-fluoro-1h-benzimidazole Chemical compound N=1C2=CC(F)=CC=C2NC=1SCC(N=CC=1)=CC=1OCC1CC1 KTXVWWXXGRAFKB-UHFFFAOYSA-N 0.000 description 4
DIUOJMLXZJHNDR-UHFFFAOYSA-N 2-[[4-(cyclopropylmethoxy)pyridin-2-yl]methylsulfinyl]-6-fluoro-1h-benzimidazole Chemical compound N=1C2=CC(F)=CC=C2NC=1S(=O)CC(N=CC=1)=CC=1OCC1CC1 DIUOJMLXZJHNDR-UHFFFAOYSA-N 0.000 description 4
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
GFDHSPQGYGSEBJ-UHFFFAOYSA-N methyl 2-[(3,4-dimethoxypyridin-2-yl)methylsulfanyl]-6-methyl-1h-benzimidazole-5-carboxylate Chemical compound N1C=2C=C(C)C(C(=O)OC)=CC=2N=C1SCC1=NC=CC(OC)=C1OC GFDHSPQGYGSEBJ-UHFFFAOYSA-N 0.000 description 4
RFJGNWGMCBFYTP-UHFFFAOYSA-N methyl 2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-6-methyl-1h-benzimidazole-5-carboxylate Chemical compound N1C=2C=C(C)C(C(=O)OC)=CC=2N=C1S(=O)CC1=NC=CC(OC)=C1OC RFJGNWGMCBFYTP-UHFFFAOYSA-N 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
150000003608 titanium Chemical class 0.000 description 4
UUPITLNVYVCTFW-UHFFFAOYSA-N 1-[5-[(4,5-diphenyl-1h-imidazol-2-yl)sulfanyl]pentyl]-3,5-dimethylpyrazole Chemical compound N1=C(C)C=C(C)N1CCCCCSC1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 UUPITLNVYVCTFW-UHFFFAOYSA-N 0.000 description 3
PSIREIZGKQBEEO-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfinylmethyl)-n-methyl-n-(2-methylpropyl)aniline Chemical compound CC(C)CN(C)C1=CC=CC=C1CS(=O)C1=NC2=CC=CC=C2N1 PSIREIZGKQBEEO-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
IQPSEEYGBUAQFF-UHFFFAOYSA-N Pantoprazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
125000001174 sulfone group Chemical group 0.000 description 3
JSSNZRRZJATBLR-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfanylmethyl)-n-methyl-n-(2-methylpropyl)aniline Chemical compound CC(C)CN(C)C1=CC=CC=C1CSC1=NC2=CC=CC=C2N1 JSSNZRRZJATBLR-UHFFFAOYSA-N 0.000 description 2
BSXAHDOWMOSVAP-UHFFFAOYSA-N 2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfanyl]-1h-benzimidazole Chemical compound COCCCOC1=CC=NC(CSC=2NC3=CC=CC=C3N=2)=C1C BSXAHDOWMOSVAP-UHFFFAOYSA-N 0.000 description 2
UKILEIRWOYBGEJ-UHFFFAOYSA-N 6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfanyl]-1h-benzimidazole Chemical compound COC1=CC=NC(CSC=2NC3=CC(OC(F)F)=CC=C3N=2)=C1OC UKILEIRWOYBGEJ-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical class [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
230000007613 environmental effect Effects 0.000 description 2
238000002386 leaching Methods 0.000 description 2
229910000069 nitrogen hydride Inorganic materials 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000012064 sodium phosphate buffer Substances 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
125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
JXOSPTBRSOYXGC-UHFFFAOYSA-N 1-Chloro-4-iodobutane Chemical compound ClCCCCI JXOSPTBRSOYXGC-UHFFFAOYSA-N 0.000 description 1
VCMADTQZCBWKAB-UHFFFAOYSA-N 1-benzylsulfanyl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1SCC1=CC=CC=C1 VCMADTQZCBWKAB-UHFFFAOYSA-N 0.000 description 1
PQZKJXSQHLOQRF-UHFFFAOYSA-N 1-chloro-5-(5-chloropentylsulfinyl)pentane Chemical class ClCCCCCS(=O)CCCCCCl PQZKJXSQHLOQRF-UHFFFAOYSA-N 0.000 description 1
HFOVHZUQZANCPI-UHFFFAOYSA-N 1-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfanyl]benzimidazole Chemical compound COC1=C(C)C=NC(CSC=2N(C3=CC=CC=C3N=2)OC)=C1C HFOVHZUQZANCPI-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
UCUIRNGEPTXZBS-UHFFFAOYSA-N 2-[(4-cyclopropyl-3-methoxypyridin-2-yl)methylsulfinyl]-6-fluoro-1h-benzimidazole Chemical compound COC1=C(CS(=O)C=2NC3=CC=C(F)C=C3N=2)N=CC=C1C1CC1 UCUIRNGEPTXZBS-UHFFFAOYSA-N 0.000 description 1
CCHLMSUZHFPSFC-UHFFFAOYSA-N 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfanyl]-1h-benzimidazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CSC1=NC2=CC=CC=C2N1 CCHLMSUZHFPSFC-UHFFFAOYSA-N 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
102000057234 Acyl transferases Human genes 0.000 description 1
108700016155 Acyl transferases Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000003699 antiulcer agent Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000004296 chiral HPLC Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000027119 gastric acid secretion Effects 0.000 description 1
239000000499 gel Substances 0.000 description 1
230000014509 gene expression Effects 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229960003174 lansoprazole Drugs 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
229950007395 leminoprazole Drugs 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
VHILIAIEEYLJNA-UHFFFAOYSA-N methyl p-tolyl sulfide Chemical compound CSC1=CC=C(C)C=C1 VHILIAIEEYLJNA-UHFFFAOYSA-N 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 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
229960005019 pantoprazole Drugs 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
238000001556 precipitation Methods 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
229920006395 saturated elastomer Polymers 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
RRFCKCAQHRITRG-UHFFFAOYSA-N sodium;5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazol-3-ide;hydrate Chemical compound O.[Na+].N=1C2=CC(OC)=CC=C2[N-]C=1S(=O)CC1=NC=C(C)C(OC)=C1C RRFCKCAQHRITRG-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000003335 steric effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO19970153A 1994-07-15 1997-01-14 Fremgangsmåte for syntese av substituerte sulfoksider, og slike produktforbindelser NO312101B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE9402510A SE504459C2 (sv)	1994-07-15	1994-07-15	Förfarande för framställning av substituerade sulfoxider
PCT/SE1995/000818 WO1996002535A1 (fr)	1994-07-15	1995-07-03	Procede de synthese de sulfoxydes substitues

Publications (3)

Publication Number	Publication Date
NO970153L NO970153L (no)	1997-01-14
NO970153D0 NO970153D0 (no)	1997-01-14
NO312101B1 true NO312101B1 (no)	2002-03-18

Family

ID=20394753

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19970153A NO312101B1 (no)	1994-07-15	1997-01-14	Fremgangsmåte for syntese av substituerte sulfoksider, og slike produktforbindelser

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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CZ6497A3 (en)	1997-06-11
EP0773940B2 (fr)	2010-11-17
PL318165A1 (en)	1997-05-26
EP0773940B1 (fr)	2003-06-04
NO970153L (no)	1997-01-14
ATE242233T1 (de)	2003-06-15
AR003443A1 (es)	1998-08-05
TR199500861A2 (tr)	1996-06-21
SK284059B6 (sk)	2004-09-08
BR9508292A (pt)	1997-12-23
TNSN95081A1 (fr)	1996-02-06
YU49475B (sh)	2006-05-25
CA2193994C (fr)	2005-05-03
RU2157806C2 (ru)	2000-10-20
CN1070489C (zh)	2001-09-05
MY113180A (en)	2001-12-31
HUT76642A (en)	1997-10-28
AU688074B2 (en)	1998-03-05
HRP950401B1 (en)	2004-04-30
WO1996002535A1 (fr)	1996-02-01
SI0773940T2 (sl)	2011-02-28
NZ289959A (en)	1998-01-26
US5948789A (en)	1999-09-07
SI0773940T1 (en)	2004-02-29
FI970102A0 (fi)	1997-01-10
YU47695A (sh)	1998-07-10
SK4897A3 (en)	1997-08-06
IL114477A0 (en)	1995-11-27
SE9402510D0 (sv)	1994-07-15
DZ1911A1 (fr)	2002-02-17
HU226361B1 (en)	2008-09-29
SE504459C2 (sv)	1997-02-17
DE69530987T3 (de)	2011-07-07
WO1996002535A8 (fr)	1999-12-23
KR100356252B1 (ko)	2002-11-18
IS4406A (is)	1996-12-27
DE69530987D1 (de)	2003-07-10
NO970153D0 (no)	1997-01-14
DE69530987T2 (de)	2004-05-19
EP0773940A1 (fr)	1997-05-21
JP3795917B2 (ja)	2006-07-12
CN1157614A (zh)	1997-08-20
ES2199998T3 (es)	2004-03-01
DK0773940T4 (da)	2011-02-07
MA23611A1 (fr)	1996-04-01
HK1008331A1 (en)	1999-05-07
UA47409C2 (uk)	2002-07-15
FI970102L (fi)	1997-01-10
ES2199998T5 (es)	2011-03-16
ZA955724B (en)	1996-01-15
TW372971B (en)	1999-11-01
PL186342B1 (pl)	2003-12-31
DK0773940T3 (da)	2003-09-15
CA2193994A1 (fr)	1996-02-01
KR970704731A (ko)	1997-09-06
MX9700358A (es)	1997-04-30
SA95160294B1 (ar)	2006-07-31
JPH10504290A (ja)	1998-04-28
PT773940E (pt)	2003-10-31
IL114477A (en)	2001-07-24
IS1772B (is)	2001-06-01
HRP950401A2 (en)	1997-10-31
SE9402510L (sv)	1996-01-16
FI117830B (fi)	2007-03-15
EE03354B1 (et)	2001-02-15
CZ297987B6 (cs)	2007-05-16
EG24534A (en)	2009-08-30
FI117672B (fi)	2007-01-15
AU2994895A (en)	1996-02-16

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Publication	Publication Date	Title
NO312101B1 (no)	2002-03-18	Fremgangsmåte for syntese av substituerte sulfoksider, og slike produktforbindelser
EP0836601B1 (fr)	2008-12-24	Procede de purification optique pour derives de benzimidazole enrichis par enantiomorphe
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
MXPA98000160A (en)	1998-10-15	A process for the optic purification of derivatives of benzimidazol enriquecidos enantiomericame