SK284059B6 - Spôsob prípravy substituovaných sulfoxidov - Google Patents

Spôsob prípravy substituovaných sulfoxidov Download PDF

Info

Publication number: SK284059B6
Authority: SK; Slovakia
Prior art keywords: mmol; het; chiral; sulfoxide; titanium
Prior art date: 1994-07-15

Application number

SK48-97A

Other languages

English (en)

Slovak (sk)

Other versions

SK4897A3 (en

Inventor

Erik Magnus Larsson

Urban Jan Stenhede

Henrik S�RENSEN

Unge Per Oskar Sverker Von

Hanna Kristina Cotton

Original Assignee

Astra Aktiebolag

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

1995-07-03

Publication date

2004-09-08

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=SK284059(B6) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1995-07-03 Application filed by Astra Aktiebolag filed Critical Astra Aktiebolag

1997-08-06 Publication of SK4897A3 publication Critical patent/SK4897A3/sk

2004-09-08 Publication of SK284059B6 publication Critical patent/SK284059B6/sk

Links

238000000034 method Methods 0.000 title claims abstract description 86
230000015572 biosynthetic process Effects 0.000 title abstract description 8
238000003786 synthesis reaction Methods 0.000 title abstract description 8
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 59
238000007254 oxidation reaction Methods 0.000 claims abstract description 52
230000003647 oxidation Effects 0.000 claims abstract description 50
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 20
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 90
150000003462 sulfoxides Chemical class 0.000 claims description 85
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 48
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 39
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 37
239000010936 titanium Substances 0.000 claims description 35
229910052719 titanium Inorganic materials 0.000 claims description 33
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239000000047 product Substances 0.000 claims description 29
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 28
239000002585 base Substances 0.000 claims description 28
-1 sulfoxide compound Chemical class 0.000 claims description 28
238000002360 preparation method Methods 0.000 claims description 22
YSAVZVORKRDODB-PHDIDXHHSA-N diethyl (2r,3r)-2,3-dihydroxybutanedioate Chemical group CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC YSAVZVORKRDODB-PHDIDXHHSA-N 0.000 claims description 21
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230000035484 reaction time Effects 0.000 claims description 13
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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 13
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150000003568 thioethers Chemical class 0.000 description 13
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 12
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238000002425 crystallisation Methods 0.000 description 9
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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238000002474 experimental method Methods 0.000 description 5
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ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-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
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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 3
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GDVPKQONYOBALE-UHFFFAOYSA-N C1(=CC=CC=C1)C=1N=C(NC=1C1=CC=CC=C1)CSCC=1NC(=C(N=1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C=1N=C(NC=1C1=CC=CC=C1)CSCC=1NC(=C(N=1)C1=CC=CC=C1)C1=CC=CC=C1 GDVPKQONYOBALE-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
YSAVZVORKRDODB-UHFFFAOYSA-N Diethyl tartrate Chemical compound CCOC(=O)C(O)C(O)C(=O)OCC YSAVZVORKRDODB-UHFFFAOYSA-N 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 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
GELXFVQAWNTGPQ-UHFFFAOYSA-N [N].C1=CNC=N1 Chemical group [N].C1=CNC=N1 GELXFVQAWNTGPQ-UHFFFAOYSA-N 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
150000001409 amidines Chemical class 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
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000008021 deposition Effects 0.000 description 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000003821 enantio-separation Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 description 1
SIXIIKVOZAGHPV-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=C[CH]C2=N1 SIXIIKVOZAGHPV-UHFFFAOYSA-N 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
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
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229940063517 omeprazole sodium Drugs 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229960005019 pantoprazole Drugs 0.000 description 1
IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
230000005588 protonation Effects 0.000 description 1
239000013014 purified material Substances 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
230000028327 secretion Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 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
230000003335 steric effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
150000003899 tartaric acid esters Chemical class 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
238000005406 washing Methods 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)

SK48-97A 1994-07-15 1995-07-03 Spôsob prípravy substituovaných sulfoxidov SK284059B6 (sk)

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 (2)

Publication Number	Publication Date
SK4897A3 SK4897A3 (en)	1997-08-06
SK284059B6 true SK284059B6 (sk)	2004-09-08

Family

ID=20394753

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK48-97A SK284059B6 (sk)	1994-07-15	1995-07-03	Spôsob prípravy substituovaných sulfoxidov

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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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
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
SE504459C2 (sv)	1997-02-17
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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Publication	Publication Date	Title
SK284059B6 (sk)	2004-09-08	Spôsob prípravy substituovaných sulfoxidov
CA2226184C (fr)	2008-08-05	Procede de purification optique pour derives de benzimidazole enrichis par enantiomorphe
US7452998B2 (en)	2008-11-18	Process for preparing optically pure active compounds
CA2507889C (fr)	2012-02-07	Procede de preparation de (s)-pantoprazole
HK1008331B (en)	2003-11-21	Process for synthesis of substituted sulphoxides
MXPA98000160A (en)	1998-10-15	A process for the optic purification of derivatives of benzimidazol enriquecidos enantiomericame
HK1010193B (en)	2009-04-17	A process for the optical purification of enantiomerically enriched benzimidazole derivatives