CH653324A5 - Derives aromatiques d'acide acetique substitue en alpha par un groupe sulfo et leur procede de fabrication. - Google Patents

Derives aromatiques d'acide acetique substitue en alpha par un groupe sulfo et leur procede de fabrication. Download PDF

Info

Publication number: CH653324A5
Authority: CH; Switzerland
Prior art keywords: acid; alkaline; hydroxy; racemic; phenyl
Prior art date: 1980-05-08

Application number

CH5482A

Other languages

English (en)

French (fr)

Inventor

Alain Schouteeten

Yani Christidis

Original Assignee

Hoechst France

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.)

1980-05-08

Filing date

1981-04-10

Publication date

1985-12-31

1981-04-10 Application filed by Hoechst France filed Critical Hoechst France

1985-12-31 Publication of CH653324A5 publication Critical patent/CH653324A5/fr

Links

QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims description 9
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 title claims description 5
238000004519 manufacturing process Methods 0.000 title claims 2
239000002253 acid Substances 0.000 claims description 35
229910001868 water Inorganic materials 0.000 claims description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
238000000034 method Methods 0.000 claims description 23
-1 amine salt Chemical class 0.000 claims description 17
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
150000001768 cations Chemical class 0.000 claims description 12
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
150000003868 ammonium compounds Chemical class 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 8
239000007864 aqueous solution Substances 0.000 claims description 8
YHXHKYRQLYQUIH-UHFFFAOYSA-N 4-hydroxymandelic acid Chemical compound OC(=O)C(O)C1=CC=C(O)C=C1 YHXHKYRQLYQUIH-UHFFFAOYSA-N 0.000 claims description 7
ATPBHLAWGXOMOR-UHFFFAOYSA-N 2-hydroxy-2-(4-hydroxyphenyl)acetic acid;hydrate Chemical compound O.OC(=O)C(O)C1=CC=C(O)C=C1 ATPBHLAWGXOMOR-UHFFFAOYSA-N 0.000 claims description 6
239000002585 base Substances 0.000 claims description 5
230000007935 neutral effect Effects 0.000 claims description 5
YTXVNJRADGDCMO-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-2-sulfoacetic acid Chemical compound OC(=O)C(S(O)(=O)=O)C1=CC=C(O)C=C1 YTXVNJRADGDCMO-UHFFFAOYSA-N 0.000 claims description 4
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
WBZKQQHYRPRKNJ-UHFFFAOYSA-N disulfurous acid Chemical compound OS(=O)S(O)(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-N 0.000 claims description 4
235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims description 3
235000010262 sodium metabisulphite Nutrition 0.000 claims description 3
235000010265 sodium sulphite Nutrition 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
229940001584 sodium metabisulfite Drugs 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
159000000011 group IA salts Chemical class 0.000 claims 2
150000003863 ammonium salts Chemical class 0.000 claims 1
ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 claims 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims 1
UPUJGSUSGASQJV-UHFFFAOYSA-J tetrasodium;disulfite Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S([O-])=O.[O-]S([O-])=O UPUJGSUSGASQJV-UHFFFAOYSA-J 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000000243 solution Substances 0.000 description 18
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 12
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 12
238000009835 boiling Methods 0.000 description 10
239000012429 reaction media Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
239000012299 nitrogen atmosphere Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 6
239000008188 pellet Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
235000010269 sulphur dioxide Nutrition 0.000 description 6
229940101006 anhydrous sodium sulfite Drugs 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
239000013078 crystal Substances 0.000 description 5
238000004452 microanalysis Methods 0.000 description 5
150000004682 monohydrates Chemical class 0.000 description 5
150000007513 acids Chemical class 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000011707 mineral Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
HGBGABMSTHQFNJ-UHFFFAOYSA-N 1,4-dioxane;sulfur trioxide Chemical compound O=S(=O)=O.C1COCCO1 HGBGABMSTHQFNJ-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
150000004677 hydrates Chemical class 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229920003053 polystyrene-divinylbenzene Polymers 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
238000010583 slow cooling Methods 0.000 description 2
229940001482 sodium sulfite Drugs 0.000 description 2
239000002904 solvent Substances 0.000 description 2
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
WAKFRZBXTKUFIW-UHFFFAOYSA-N 2-bromo-2-phenylacetic acid Chemical compound OC(=O)C(Br)C1=CC=CC=C1 WAKFRZBXTKUFIW-UHFFFAOYSA-N 0.000 description 1
JQRBBVRBGGXTLZ-UHFFFAOYSA-N 2-methoxyethanol Chemical compound COCCO.COCCO JQRBBVRBGGXTLZ-UHFFFAOYSA-N 0.000 description 1
229930186147 Cephalosporin Natural products 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
238000001632 acidimetric titration Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000002386 leaching Methods 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
238000007614 solvation Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH5482A 1980-05-08 1981-04-10 Derives aromatiques d'acide acetique substitue en alpha par un groupe sulfo et leur procede de fabrication. CH653324A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8010265A FR2482094A1 (fr)	1980-05-08	1980-05-08	Derives aromatiques d'acide acetique substitue en a par un groupe sulfo et leur procede de fabrication

Publications (1)

Publication Number	Publication Date
CH653324A5 true CH653324A5 (fr)	1985-12-31

Family

ID=9241746

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH5482A CH653324A5 (fr)	1980-05-08	1981-04-10	Derives aromatiques d'acide acetique substitue en alpha par un groupe sulfo et leur procede de fabrication.

Country Status (5)

Country	Link
JP (1)	JPS57501283A (da)
CH (1)	CH653324A5 (da)
DK (1)	DK159773C (da)
FR (1)	FR2482094A1 (da)
WO (1)	WO1981003171A1 (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN103787929B (zh) *	2014-03-03	2015-04-15	济南盛弘医药科技有限公司	一种d,l-磺苯乙酸的拆分方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1310642A (en) *	1970-11-09	1973-03-21	Pfizer	Alpha-sulfo-and alpha-sulfoalkylacylcephalosporins
JPS5285143A (en) *	1976-01-05	1977-07-15	Takeda Chem Ind Ltd	Antimicrobial agents and method of preparing same

1980
- 1980-05-08 FR FR8010265A patent/FR2482094A1/fr active Granted
1981
- 1981-04-10 CH CH5482A patent/CH653324A5/fr not_active IP Right Cessation
- 1981-04-10 JP JP56501248A patent/JPS57501283A/ja active Pending
- 1981-04-10 WO PCT/FR1981/000048 patent/WO1981003171A1/fr not_active Ceased
1982
- 1982-01-07 DK DK002582A patent/DK159773C/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS57501283A (da)	1982-07-22
FR2482094A1 (fr)	1981-11-13
WO1981003171A1 (fr)	1981-11-12
DK159773C (da)	1991-04-22
DK2582A (da)	1982-01-07
FR2482094B1 (da)	1985-03-08
DK159773B (da)	1990-12-03

Legal Events

Date	Code	Title	Description
1994-12-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
JPS5935381B2 (ja)	1984-08-28	（＋）−および（−）−６−メトキシ−α−メチル−２−ナフタレン酢酸の分割法
IL188600A (en)	2011-12-29	Process for the preparation of azomaprazole
FR2601005A1 (fr)	1988-01-08	Procede de preparation d'esters alkyliques de l'acide cyano-2 tetrachlorobenzoique
FR2793490A1 (fr)	2000-11-17	Procede de preparation du (1r,2s,4r)-(-)-2-[(2'-{n,n- dimethylamino}-ethoxy)]-2-[phenyl]-1,7,7-tri-[methyl]- bicyclo[2.2.1]-heptane et ses sels d'addition d'acide pharmaceutiquement acceptables
CH653324A5 (fr)	1985-12-31	Derives aromatiques d'acide acetique substitue en alpha par un groupe sulfo et leur procede de fabrication.
FR2571366A1 (fr)	1986-04-11	Procede de preparation de la l-carnitine et de ses sels
FR2686876A1 (fr)	1993-08-06	Procede de preparation d'acides arylacetiques et de leurs sels de metaux alcalins.
JP4397990B2 (ja)	2010-01-13	３−アルキルフラバノノール誘導体の精製法
EP0221815B1 (fr)	1989-08-02	Procédé pour la fabrication d'acides alkanoiques
EP0627403B1 (fr)	1996-12-18	Procédé de préparation d'acides hydroxyphénylacétiques
FR2577222A1 (fr)	1986-08-14	Procede pour la preparation de l'acide 1-(3-mercapto-25-methylpropionyl)-pyrrolidine-(25)-carboxylique
EP0124407B1 (fr)	1989-08-23	Procédé de préparation d'acides alkanoiques
EP0132201A2 (fr)	1985-01-23	Procédé de préparation du phénylpyruvate de sodium monohydraté cristallisé
KR20020091078A (ko)	2002-12-05	α-(2-4-디술포페닐)-Ｎ-ｔｅｒｔ-부틸니트론 및 제약상허용되는 그의 염의 신규 제조 방법
RU2741389C1 (ru)	2021-01-25	Способ получения промежуточного соединения для синтеза лекарственного средства
JP3523661B2 (ja)	2004-04-26	２−アルキル−４−ハロゲノ−５−ホルミルイミダゾールの精製方法
BE897708A (fr)	1984-03-08	Procede de preparation de 2-benzothiazole-sulfenamides a empechement sterique
KR100503267B1 (ko)	2005-07-22	2-아세틸옥시-4-트리플루오로메틸 벤조산의 제조 방법
EP0258117A1 (fr)	1988-03-02	Procédé de préparation de diamino-2,4 benzyl-5 pyrimidines
JPH0588700B2 (da)	1993-12-24
CN121378289A (zh)	2026-01-23	用于制备生物素中间体的方法
JP3738470B2 (ja)	2006-01-25	光学活性１−（ジクロロ置換フェニル）エチルアミン類の製造方法
EP0627402B1 (fr)	1998-04-08	Procédé d'obtention d'acides hydroxyphénylacétiques
JP2576598B2 (ja)	1997-01-29	光学活性１−メチル−３−フェニルプロピルアミンの製法
JPH11228532A (ja)	1999-08-24	光学活性２−アセチルチオメチル−３−フェニルプロピオン酸の製造方法