LU81636A1 - Procede perfectionne de preparation d'hydroxymethyl-4(5)alkyl inferieur-5(4)imidazoles et de leurs sels d'addition d'acide - Google Patents

Procede perfectionne de preparation d'hydroxymethyl-4(5)alkyl inferieur-5(4)imidazoles et de leurs sels d'addition d'acide Download PDF

Info

Publication number: LU81636A1
Authority: LU; Luxembourg
Prior art keywords: base; lower alkyl; formula; formaldehyde; formulas
Prior art date: 1978-08-30

Application number

LU81636A

Other languages

English (en)

French (fr)

Inventor

Brierre Y Hubert

Original Assignee

Delalande Sa

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.)

1978-08-30

Filing date

1979-08-28

Publication date

1981-03-24

1979-08-28 Application filed by Delalande Sa filed Critical Delalande Sa

1981-03-24 Publication of LU81636A1 publication Critical patent/LU81636A1/fr

Links

238000000034 method Methods 0.000 title claims description 21
150000003839 salts Chemical class 0.000 title claims description 14
230000008569 process Effects 0.000 title claims description 11
239000002253 acid Substances 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 6
150000002460 imidazoles Chemical class 0.000 title description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 29
150000001875 compounds Chemical class 0.000 claims description 20
239000002585 base Substances 0.000 claims description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
150000003512 tertiary amines Chemical class 0.000 claims description 6
229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
239000011707 mineral Substances 0.000 claims description 5
235000010755 mineral Nutrition 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
241000283986 Lepus Species 0.000 claims description 3
230000009471 action Effects 0.000 claims description 3
229940072033 potash Drugs 0.000 claims description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
235000015320 potassium carbonate Nutrition 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
235000019441 ethanol Nutrition 0.000 claims 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
229930040373 Paraformaldehyde Natural products 0.000 description 7
229920002866 paraformaldehyde Polymers 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
238000001632 acidimetric titration Methods 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
229940075930 picrate Drugs 0.000 description 3
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
PZVRSDBLMSXDCX-UHFFFAOYSA-N 1,3-benzodioxolyl-n-methylpentanamine Chemical compound CCCC(NC)CC1=CC=C2OCOC2=C1 PZVRSDBLMSXDCX-UHFFFAOYSA-N 0.000 description 2
230000006872 improvement Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
244000292604 Salvia columbariae Species 0.000 description 1
235000012377 Salvia columbariae var. columbariae Nutrition 0.000 description 1
235000001498 Salvia hispanica Nutrition 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
239000003699 antiulcer agent Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
235000014167 chia Nutrition 0.000 description 1
AQIXAKUUQRKLND-UHFFFAOYSA-N cimetidine Chemical compound N#C/N=C(/NC)NCCSCC=1N=CNC=1C AQIXAKUUQRKLND-UHFFFAOYSA-N 0.000 description 1
229960001380 cimetidine Drugs 0.000 description 1
239000002131 composite material Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
239000010931 gold Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
OTVAEFIXJLOWRX-NXEZZACHSA-N thiamphenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl)C=C1 OTVAEFIXJLOWRX-NXEZZACHSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

LU81636A 1978-08-30 1979-08-28 Procede perfectionne de preparation d'hydroxymethyl-4(5)alkyl inferieur-5(4)imidazoles et de leurs sels d'addition d'acide LU81636A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7825051A FR2434807A1 (fr)	1978-08-30	1978-08-30	Procede perfectionne de preparation d'hydroxymethyl-4(5) alkyl inferieur-5 (4)-imidazoles et de leurs sels d'addition d'acide
FR7825051		1978-08-30

Publications (1)

Publication Number	Publication Date
LU81636A1 true LU81636A1 (fr)	1981-03-24

Family

ID=9212212

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU81636A LU81636A1 (fr)	1978-08-30	1979-08-28	Procede perfectionne de preparation d'hydroxymethyl-4(5)alkyl inferieur-5(4)imidazoles et de leurs sels d'addition d'acide

Country Status (13)

Country	Link
US (1)	US4275216A (de)
JP (1)	JPS5535075A (de)
AT (1)	AT373245B (de)
BE (1)	BE878490A (de)
DE (1)	DE2934925A1 (de)
FR (1)	FR2434807A1 (de)
GB (1)	GB2029414B (de)
IL (1)	IL58130A (de)
IT (1)	IT1122746B (de)
LU (1)	LU81636A1 (de)
NL (1)	NL7906109A (de)
SE (1)	SE7907188L (de)
YU (1)	YU204279A (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2908212A1 (de) *	1979-03-02	1980-09-11	Basf Ag	Verfahren zur herstellung von 5-hydroxymethylimidazolen
IL75063A (en) *	1985-05-01	1989-03-31	Teva Pharma	Preparation of 4(5)-hydroxymethyl-5(4)-methylimidazole
DE3534083A1 (de) *	1985-09-25	1987-04-02	Basf Ag	Verfahren zur herstellung von hydroximethylimidazolen
US6107490A (en) *	1995-12-13	2000-08-22	Brantford Chemicals Inc.	Process for the manufacture of 4-methyl-5-hydroxymethyl-imidazole

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4104473A (en) *	1976-04-23	1978-08-01	Shikoku Chemicals Corporation	Novel imidazole compounds and process for preparations thereof
ES477086A1 (es) *	1978-04-07	1979-12-16	Eprova Ag	Procedimiento para la preparacion de 4-metil-5-hidroximetil-imidazol.

1978
- 1978-08-30 FR FR7825051A patent/FR2434807A1/fr active Granted
1979
- 1979-07-31 US US06/062,501 patent/US4275216A/en not_active Expired - Lifetime
- 1979-08-09 NL NL7906109A patent/NL7906109A/nl not_active Application Discontinuation
- 1979-08-09 IT IT25028/79A patent/IT1122746B/it active
- 1979-08-21 YU YU02042/79A patent/YU204279A/xx unknown
- 1979-08-23 AT AT0566479A patent/AT373245B/de not_active IP Right Cessation
- 1979-08-28 JP JP10961479A patent/JPS5535075A/ja active Pending
- 1979-08-28 IL IL58130A patent/IL58130A/xx unknown
- 1979-08-28 LU LU81636A patent/LU81636A1/fr unknown
- 1979-08-29 GB GB7929945A patent/GB2029414B/en not_active Expired
- 1979-08-29 DE DE19792934925 patent/DE2934925A1/de not_active Withdrawn
- 1979-08-29 SE SE7907188A patent/SE7907188L/xx not_active Application Discontinuation
- 1979-08-29 BE BE0/196929A patent/BE878490A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
GB2029414A (en)	1980-03-19
BE878490A (fr)	1980-02-29
GB2029414B (en)	1983-01-12
YU204279A (en)	1983-01-21
IT1122746B (it)	1986-04-23
FR2434807B1 (de)	1981-03-06
IL58130A0 (en)	1979-12-30
US4275216A (en)	1981-06-23
DE2934925A1 (de)	1980-03-13
IT7925028A0 (it)	1979-08-09
AT373245B (de)	1983-12-27
FR2434807A1 (fr)	1980-03-28
JPS5535075A (en)	1980-03-11
SE7907188L (sv)	1980-03-01
ATA566479A (de)	1983-05-15
IL58130A (en)	1983-09-30
NL7906109A (nl)	1980-03-04

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