DK166499B1 - Fremgangsmaade til fremstilling af thienoimidazolderivater - Google Patents

Fremgangsmaade til fremstilling af thienoimidazolderivater Download PDF

Info

Publication number: DK166499B1
Authority: DK; Denmark
Prior art keywords: sub; formula; sup; preparation; descarboxybiotin
Prior art date: 1985-03-14

Application number

DK115686A

Other languages

Danish (da)

English (en)

Other versions

DK115686A (da

DK115686D0 (da

Inventor

Gordon Dwight Gruetzmacher

Robert Alfred Volkmann

Original Assignee

Pfizer

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.)

1985-03-14

Filing date

1986-03-13

Publication date

1993-06-01

1986-03-13 Application filed by Pfizer filed Critical Pfizer

1986-03-13 Publication of DK115686D0 publication Critical patent/DK115686D0/da

1986-09-15 Publication of DK115686A publication Critical patent/DK115686A/da

1993-06-01 Application granted granted Critical

1993-06-01 Publication of DK166499B1 publication Critical patent/DK166499B1/da

Links

238000000034 method Methods 0.000 title claims abstract description 28
238000002360 preparation method Methods 0.000 title claims abstract description 17
150000001875 compounds Chemical class 0.000 claims abstract description 16
239000004593 Epoxy Substances 0.000 claims abstract description 8
JCZAVVUIFWZMQI-UHFFFAOYSA-N 1h-thieno[2,3-d]imidazole Chemical class N1C=NC2=C1C=CS2 JCZAVVUIFWZMQI-UHFFFAOYSA-N 0.000 claims abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 9
229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 abstract description 15
125000000217 alkyl group Chemical group 0.000 abstract description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
239000000543 intermediate Substances 0.000 description 9
229960002685 biotin Drugs 0.000 description 8
239000011616 biotin Substances 0.000 description 8
235000020958 biotin Nutrition 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 3
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229910015900 BF3 Inorganic materials 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
229940068840 d-biotin Drugs 0.000 description 2
239000007789 gas Substances 0.000 description 2
FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 2
229940088594 vitamin Drugs 0.000 description 2
239000011782 vitamin Substances 0.000 description 2
229930003231 vitamin Natural products 0.000 description 2
235000013343 vitamin Nutrition 0.000 description 2
150000003722 vitamin derivatives Chemical class 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
ZEPXAFZTJPAGHT-UHFFFAOYSA-N 2-bromoheptanal Chemical compound CCCCCC(Br)C=O ZEPXAFZTJPAGHT-UHFFFAOYSA-N 0.000 description 1
QRZPCAMSVQQRGQ-UHFFFAOYSA-N 3,5-dihydroimidazo[1,5-c][1,3]thiazole Chemical compound C1=NCN2CSC=C21 QRZPCAMSVQQRGQ-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000282461 Canis lupus Species 0.000 description 1
241000186216 Corynebacterium Species 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
239000012448 Lithium borohydride Substances 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
241000222068 Sporobolomyces <Sporidiobolaceae> Species 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
239000012267 brine Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
-1 bromine heptanal Chemical compound 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
UWRRAHYBHTWXAQ-UHFFFAOYSA-N ethyl 2-isothiocyanatoacetate;lithium Chemical compound [Li].CCOC(=O)CN=C=S UWRRAHYBHTWXAQ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
244000005700 microbiome Species 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Chemical group 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000010959 steel Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
231100000925 very toxic Toxicity 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Nutrition Science (AREA)
Hematology (AREA)
Obesity (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Diabetes (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DK115686A 1985-03-14 1986-03-13 Fremgangsmaade til fremstilling af thienoimidazolderivater DK166499B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/711,682 US4670564A (en)	1985-03-14	1985-03-14	Preparation of thieno-imidazole derivatives
US71168285		1985-03-14

Publications (3)

Publication Number	Publication Date
DK115686D0 DK115686D0 (da)	1986-03-13
DK115686A DK115686A (da)	1986-09-15
DK166499B1 true DK166499B1 (da)	1993-06-01

Family

ID=24859083

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK115686A DK166499B1 (da)	1985-03-14	1986-03-13	Fremgangsmaade til fremstilling af thienoimidazolderivater

Country Status (9)

Country	Link
US (1)	US4670564A (de)
EP (1)	EP0194846B1 (de)
JP (2)	JPH0686456B2 (de)
AT (1)	ATE63310T1 (de)
AU (1)	AU557395B2 (de)
CA (1)	CA1270254A (de)
DE (1)	DE3679091D1 (de)
DK (1)	DK166499B1 (de)
IE (1)	IE58456B1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU580042B2 (en) *	1984-03-22	1988-12-22	Bresatec Limited	Non-radioactive biological probes
US8993039B2 (en)	2006-01-25	2015-03-31	Tate & Lyle Ingredients Americas Llc	Fiber-containing carbohydrate composition
CN104987342B (zh) *	2015-06-30	2017-03-15	江西科技师范大学	天然产物(+)‑生物素的全合成方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2489236A (en) *	1947-07-24	1949-11-22	Hoffmann La Roche	Synthesis of biotin and related compounds
US2489235A (en) *	1947-07-24	1949-11-22	Hoffmann La Roche	Synthesis of biotin
US3393129A (en) *	1964-12-23	1968-07-16	Takeda Chemical Industries Ltd	Method for producing d-biotin
US4029647A (en) *	1973-12-03	1977-06-14	Hoffmann-La Roche Inc.	Synthesis of biotin
US4062868A (en) *	1977-02-23	1977-12-13	Hoffmann-La Roche Inc.	Synthesis of biotin
US4468516A (en) *	1982-05-17	1984-08-28	Pfizer Inc.	Process for the preparation of biotin
CA1192947A (en) *	1982-10-28	1985-09-03	General Motors Corporation	Low silhouette venting system for electric storage battery

1985
- 1985-03-14 US US06/711,682 patent/US4670564A/en not_active Expired - Fee Related
1986
- 1986-03-11 AT AT86301718T patent/ATE63310T1/de not_active IP Right Cessation
- 1986-03-11 EP EP86301718A patent/EP0194846B1/de not_active Expired - Lifetime
- 1986-03-11 DE DE8686301718T patent/DE3679091D1/de not_active Expired - Lifetime
- 1986-03-12 CA CA000503855A patent/CA1270254A/en not_active Expired - Lifetime
- 1986-03-13 AU AU54685/86A patent/AU557395B2/en not_active Ceased
- 1986-03-13 DK DK115686A patent/DK166499B1/da not_active IP Right Cessation
- 1986-03-13 IE IE66986A patent/IE58456B1/en not_active IP Right Cessation
- 1986-03-14 JP JP61056767A patent/JPH0686456B2/ja not_active Expired - Lifetime
1993
- 1993-10-27 JP JP5269016A patent/JPH0759585B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DK115686A (da)	1986-09-15
US4670564A (en)	1987-06-02
IE860669L (en)	1986-09-14
EP0194846A3 (en)	1988-01-07
EP0194846A2 (de)	1986-09-17
IE58456B1 (en)	1993-09-22
DE3679091D1 (de)	1991-06-13
ATE63310T1 (de)	1991-05-15
AU557395B2 (en)	1986-12-18
AU5468586A (en)	1986-09-18
JPS61233687A (ja)	1986-10-17
JPH0686456B2 (ja)	1994-11-02
JPH06293771A (ja)	1994-10-21
JPH0759585B2 (ja)	1995-06-28
EP0194846B1 (de)	1991-05-08
DK115686D0 (da)	1986-03-13
CA1270254A (en)	1990-06-12

Legal Events

Date	Code	Title	Description
1993-06-01	B1	Patent granted (law 1993)
1999-10-18	PBP	Patent lapsed

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DK166499B1 (da)	1993-06-01	Fremgangsmaade til fremstilling af thienoimidazolderivater
RU2007402C1 (ru)	1994-02-15	Способ получения производных 2-азабицикло(2,2,1)гепт-5-ен-2-уксусной кислоты
CN116925023B (zh)	2025-11-21	2-全氟烷基-4h-吡喃-4-酮衍生物的改进合成方法
EP0112939B1 (de)	1986-09-17	Pentacycloundecan Derivate, Verfahren zu ihrer Herstellung, und diese enthaltende pharmazeutische Zusammensetzungen
US8080663B2 (en)	2011-12-20	Process for the preparation of 2-methylspiro(1,3-oxathiolane-5,3′)quiniclidine
US4292431A (en)	1981-09-29	Process for the production of hydroxymethylimidazoles
US4424356A (en)	1984-01-03	Process for the preparation of 5,6,7,7a-tetrahydro-4H-thieno- 3,2,-c!pyridin-2-one
SK20192000A3 (sk)	2001-08-06	Soli n-terc-butylhydroxylamínu
SU618045A3 (ru)	1978-07-30	Способ получени производных тиено (2,3-с) пиридина или их солей
US3845076A (en)	1974-10-29	Method of preparing aldehydes
Lowell Jr et al.	1966	The Stereochemistry of Δ2-Thiazoline Formation from Episulfides
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KR100203233B1 (ko)	1999-06-15	아스타크산틴의 제조방법
US3359290A (en)	1967-12-19	Production of omega-aminoketo-carboxylic acids
EP0058070A2 (de)	1982-08-18	Verfahren zur Herstellung von Pirbuterol
ES3033407T3 (en)	2025-08-04	Method for the preparation of alkyl-4-oxo-tetrahydrofuran-2-carboxylate
KR20000018793A (ko)	2000-04-06	1,2-벤즈이소티아졸린-3-온의 제조방법
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US5073538A (en)	1991-12-17	Cycloalkylidene derivatives and fragrance composition
SE502722C2 (sv)	1995-12-18	Förfarande för framställning av N,N-disubstituerade mandelsyraamider
SU620210A3 (ru)	1978-08-15	Способ получени 2,4,5-триметилтиено (3,2- ) морфана или его солей
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