CA1152103A - Procede de purification et d'obtention d'itanoxone de qualite pharmaceutique - Google Patents

Procede de purification et d'obtention d'itanoxone de qualite pharmaceutique

Info

Publication number: CA1152103A
Authority: CA; Canada
Prior art keywords: itanoxone; water; solution; carried out; residual organic
Prior art date: 1979-10-01
Legal status (The legal status 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 status listed.): Expired

Application number

CA000361311A

Other languages

English (en)

French (fr)

Inventor

Henri Cousse

Pierre Hascoet

Gilbert Mouzin

Jean-Pierre Rieu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pierre Fabre SA

Original Assignee

Pierre Fabre 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.)

1979-10-01

Filing date

1980-10-01

Publication date

1983-08-16

1980-10-01 Application filed by Pierre Fabre SA filed Critical Pierre Fabre SA

1983-08-16 Application granted granted Critical

1983-08-16 Publication of CA1152103A publication Critical patent/CA1152103A/fr

Status Expired legal-status Critical Current

Links

HJWLWNLAIBFKDO-UHFFFAOYSA-N 4-[4-(2-chlorophenyl)phenyl]-2-methylidene-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CC(=C)C(=O)O)=CC=C1C1=CC=CC=C1Cl HJWLWNLAIBFKDO-UHFFFAOYSA-N 0.000 title claims abstract description 15
229950008966 itanoxone Drugs 0.000 title claims abstract description 14
230000001225 therapeutic effect Effects 0.000 title abstract description 3
238000000746 purification Methods 0.000 title description 2
238000002360 preparation method Methods 0.000 title 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 22
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 7
238000001914 filtration Methods 0.000 claims abstract description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 5
239000002253 acid Substances 0.000 claims abstract description 5
239000007810 chemical reaction solvent Substances 0.000 claims abstract description 5
239000003960 organic solvent Substances 0.000 claims abstract description 5
238000002425 crystallisation Methods 0.000 claims abstract description 4
230000008025 crystallization Effects 0.000 claims abstract description 4
WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 claims abstract description 4
238000001953 recrystallisation Methods 0.000 claims abstract description 4
230000010933 acylation Effects 0.000 claims abstract description 3
238000005917 acylation reaction Methods 0.000 claims abstract description 3
230000008030 elimination Effects 0.000 claims abstract description 3
238000003379 elimination reaction Methods 0.000 claims abstract description 3
238000004519 manufacturing process Methods 0.000 claims abstract description 3
239000000243 solution Substances 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
LAXBNTIAOJWAOP-UHFFFAOYSA-N 2-chlorobiphenyl Chemical group ClC1=CC=CC=C1C1=CC=CC=C1 LAXBNTIAOJWAOP-UHFFFAOYSA-N 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 2
238000005406 washing Methods 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims 2
239000011707 mineral Substances 0.000 claims 2
239000007864 aqueous solution Substances 0.000 claims 1
239000002585 base Substances 0.000 claims 1
238000004090 dissolution Methods 0.000 claims 1
150000007530 organic bases Chemical class 0.000 claims 1
235000021178 picnic Nutrition 0.000 claims 1
OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 abstract description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 abstract description 3
150000001875 compounds Chemical class 0.000 abstract description 3
125000001309 chloro group Chemical group Cl* 0.000 abstract description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
239000002904 solvent Substances 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
229940022682 acetone Drugs 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
125000000896 monocarboxylic acid group Chemical group 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
241000238876 Acari Species 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
238000007792 addition Methods 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000005012 migration Effects 0.000 description 2
238000013508 migration Methods 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
KFCLOPRWEZEAJG-UHFFFAOYSA-N 1,3-diazete Chemical compound C1=NC=N1 KFCLOPRWEZEAJG-UHFFFAOYSA-N 0.000 description 1
101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
102000011759 adducin Human genes 0.000 description 1
108010076723 adducin Proteins 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000012159 carrier gas Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000007547 defect Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000499 gel Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000008693 nausea Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
-1 oxo-4, 2-methylene Chemical group 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000009967 tasteless effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Crystallography & Structural Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000361311A 1979-10-01 1980-10-01 Procede de purification et d'obtention d'itanoxone de qualite pharmaceutique Expired CA1152103A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR79.245.82		1979-10-01
FR7924582A FR2466450A1 (fr)	1979-10-01	1979-10-01	Procede industriel de purification et d'obtention d'itanoxone de qualite pharmaceutique

Publications (1)

Publication Number	Publication Date
CA1152103A true CA1152103A (fr)	1983-08-16

Family

ID=9230249

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000361311A Expired CA1152103A (fr)	1979-10-01	1980-10-01	Procede de purification et d'obtention d'itanoxone de qualite pharmaceutique

Country Status (10)

Country	Link
AR (1)	AR225056A1 (da)
AU (1)	AU535964B2 (da)
CA (1)	CA1152103A (da)
DK (1)	DK412880A (da)
FR (1)	FR2466450A1 (da)
HU (1)	HU179386B (da)
IT (1)	IT8068420A0 (da)
NL (1)	NL8004622A (da)
SE (1)	SE8006785L (da)
ZA (1)	ZA805678B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3800989A1 (de) *	1988-01-15	1989-07-27	Hoechst Ag	Verfahren zur reinigung von 2-hydroxy-naphthalin-6-carbonsaeure
DE19850695A1 (de) *	1998-11-04	2000-05-11	Bayer Ag	Verfahren zur technischen Herstellung von 4'-Chlor-alpha-methylen-gamma-oxo-(1.1'-biphenyl)-4'-butansäure

1979
- 1979-10-01 FR FR7924582A patent/FR2466450A1/fr active Granted
1980
- 1980-08-14 NL NL8004622A patent/NL8004622A/nl not_active Application Discontinuation
- 1980-09-05 HU HU80802185A patent/HU179386B/hu unknown
- 1980-09-15 ZA ZA00805678A patent/ZA805678B/xx unknown
- 1980-09-15 IT IT8068420A patent/IT8068420A0/it unknown
- 1980-09-26 AU AU62755/80A patent/AU535964B2/en not_active Ceased
- 1980-09-29 AR AR282693A patent/AR225056A1/es active
- 1980-09-29 SE SE8006785A patent/SE8006785L/xx not_active Application Discontinuation
- 1980-09-30 DK DK412880A patent/DK412880A/da not_active Application Discontinuation
- 1980-10-01 CA CA000361311A patent/CA1152103A/fr not_active Expired

Also Published As

Publication number	Publication date
AR225056A1 (es)	1982-02-15
HU179386B (en)	1982-10-28
SE8006785L (sv)	1981-04-02
IT8068420A0 (it)	1980-09-15
AU6275580A (en)	1981-04-09
FR2466450A1 (fr)	1981-04-10
FR2466450B1 (da)	1983-06-24
AU535964B2 (en)	1984-04-12
DK412880A (da)	1981-04-02
NL8004622A (nl)	1981-04-03
ZA805678B (en)	1981-09-30

Legal Events

Date	Code	Title	Description
2000-08-16	MKEX	Expiry

Publication	Publication Date	Title
BE1008403A4 (fr)	1996-05-07	Procede de cristallisation d'iopamidol.
EP0001534B1 (fr)	1981-08-12	Nouveaux dérivés du pyrrole, leur procédé de préparation et leurs applications en thérapeutique
EP0377381A1 (fr)	1990-07-11	Procédé de préparation du phényl-1 diéthylaminocarbonyl-1 phtalimidométhyl-2 cyclopropane Z
JPH08133999A (ja)	1996-05-28	ゲラニルゲラニオ−ルの製造方法
FR2510109A1 (fr)	1983-01-28	Acide 7-alcoxycarbonyl-6,8-dimethyl-1-phtalazone-4-a-hydroxyacetique et son procede de preparation
EP2173701A1 (fr)	2010-04-14	Procede de preparation du fenofibrate
FR2466450A1 (fr)	1981-04-10	Procede industriel de purification et d'obtention d'itanoxone de qualite pharmaceutique
CA1298839C (fr)	1992-04-14	Procede de preparation de l'acide (pyridyl-3)-3 1h,3h- pyrrolo [1,2-c] thiazolecarboxylique-7 dextrogyre
US4264500A (en)	1981-04-28	Process of making 6-chloro-α-methyl-carbazole-2-acetic acid
RU2106344C1 (ru)	1998-03-10	Способ получения 1-фенил-2,3-диметил-4-йодпиразолона-5(йодантипирина) (варианты)
JP2001002621A (ja)	2001-01-09	ポリプレニル系化合物の精製方法
FR2663024A1 (fr)	1991-12-13	Procede de preparation d'acide (2-hydroxyphenyl) acetique.
BE858864A (fr)	1978-01-16	Nouveaux esters d'acides phenyl- et pyridine-3-carboxylique et procede permettant leur preparation
FI74949C (fi)	1988-04-11	Framstaellningsfoerfarande foer 6-klor- -metyl-karbazol-2-aettiksyra. lisaeys patenttiin 71130 - tillaegg till patent 71130
FR2470127A1 (fr)	1981-05-29	Thienyl-2-glycolate de sodium racemique cristallise, son procede de preparation et son application a la fabrication de l'acide thienyl-2 acetique
FR2547726A1 (fr)	1984-12-28	Acide 2-(4-biphenylyl)-4-hexenoique et ses derives ayant une activite anti-inflammatoire
KR840000766B1 (ko)	1984-06-08	비스모라노린 유도체의 제조방법
JPS61103853A (ja)	1986-05-22	２―フェニルプロピオン酸エステル類の光学分割法
FR2460930A2 (fr)	1981-01-30	Nouveau procede de preparation de derives de 4-amino 5-alkylsulfonyl ortho-anisamides et nouveaux derives de 4-nitro 5-alkylsulfonyl ortho-anisamides utiles comme intermediaires de synthese
BE901069A (fr)	1985-03-15	Procede de synthese d'acide ursodesoxycholique conjugue avec la taurine et produit ainsi obtenu.
BE864692A (fr)	1978-07-03	Derives de chalcone, leur procede de preparation et leur application en therapeutique
FR2460922A1 (fr)	1981-01-30	Nouveaux acides 2-methoxy-4-nitro-5-alkylsulfonyl benzoiques, leur procedes de preparation et leur utilisation comme intermediaires de synthese de medicaments
CH623048A5 (en)	1981-05-15	Process for the preparation of 2,3-dichloro-4-(2-thenoyl)phenoxyacetic acid
CH618174A5 (da)	1980-07-15
CH327724A (fr)	1958-02-15	Procédé de dédoublement de la Dl-proline