ATE42278T1 - Verfahren zur herstellung von cis-5-fluor-2methyl-1-(4-methylthiobenzyliden)-indenyl-3essigs|ure. - Google Patents
Verfahren zur herstellung von cis-5-fluor-2methyl-1-(4-methylthiobenzyliden)-indenyl-3essigs|ure.Info
- Publication number
- ATE42278T1 ATE42278T1 AT86108310T AT86108310T ATE42278T1 AT E42278 T1 ATE42278 T1 AT E42278T1 AT 86108310 T AT86108310 T AT 86108310T AT 86108310 T AT86108310 T AT 86108310T AT E42278 T1 ATE42278 T1 AT E42278T1
- Authority
- AT
- Austria
- Prior art keywords
- fluoro
- methylthiobenzylidene
- cis
- preparation
- phase
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- QDDPPRDVFIJASZ-UHFFFAOYSA-N 2-(6-fluoro-2-methyl-3h-inden-1-yl)acetic acid Chemical compound FC1=CC=C2CC(C)=C(CC(O)=O)C2=C1 QDDPPRDVFIJASZ-UHFFFAOYSA-N 0.000 abstract 1
- PIMQQGJMDMAZGT-UHFFFAOYSA-N 4-methylthiobenzaldehyde Chemical compound CC1=CC=C(C=S)C=C1 PIMQQGJMDMAZGT-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000012071 phase Substances 0.000 abstract 1
- 239000003444 phase transfer catalyst Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 239000007790 solid phase Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21215/85A IT1190371B (it) | 1985-06-19 | 1985-06-19 | Processo per la preparazione dell'acido cis-5-fluoro-2-metil-1-(4-metiltiobenziliden)-indenil-3-acetico |
| EP86108310A EP0206241B1 (de) | 1985-06-19 | 1986-06-18 | Verfahren zur Herstellung von cis-5-Fluor-2-methyl-1-(4-methylthiobenzyliden)-indenyl-3-essigsäure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE42278T1 true ATE42278T1 (de) | 1989-05-15 |
Family
ID=11178502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT86108310T ATE42278T1 (de) | 1985-06-19 | 1986-06-18 | Verfahren zur herstellung von cis-5-fluor-2methyl-1-(4-methylthiobenzyliden)-indenyl-3essigs|ure. |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4748271A (de) |
| EP (1) | EP0206241B1 (de) |
| JP (1) | JPH0733368B2 (de) |
| AT (1) | ATE42278T1 (de) |
| DE (1) | DE3662882D1 (de) |
| IT (1) | IT1190371B (de) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3623944A1 (de) * | 1986-07-16 | 1988-02-11 | Thomae Gmbh Dr K | Neue benzolsulfonamido-indanylverbindungen, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| JPH0662547B2 (ja) * | 1989-01-10 | 1994-08-17 | 田辺製薬株式会社 | グリシン誘導体 |
| US5093356A (en) * | 1990-01-16 | 1992-03-03 | Merck Frosst Canada, Inc. | Indenyl hydroxamic acids and hydroxy ureas as inhibitors of 5-lipoxygenase |
| EP0612244B1 (de) * | 1991-11-05 | 2001-09-19 | Smithkline Beecham Corporation | Endothelin-rezeptor-antagonisten |
| US5817693A (en) | 1991-11-05 | 1998-10-06 | Cousins; Russell Donovan | Endothelin receptor antagonists |
| US5654007A (en) * | 1995-06-07 | 1997-08-05 | Inhale Therapeutic Systems | Methods and system for processing dispersible fine powders |
| US6121321A (en) * | 1996-06-13 | 2000-09-19 | Cell Pathways, Inc. | Substituted methoxy benzylidene indenyl acetic and propionic acids for treating patients with precancerous lesions |
| US6063818A (en) * | 1996-06-13 | 2000-05-16 | Cell Pathways Inc. | Substituted benzylidene indenyl formamides, acetamides and propionamides |
| US5965619A (en) * | 1996-06-13 | 1999-10-12 | Cell Pathways Inc. | Method for treating patients having precancerous lesions with substituted indene derivatives |
| US5998477A (en) * | 1996-06-13 | 1999-12-07 | Cell Pathways Inc. | Substituted methoxy benzylidene indenyl-acetic and propionic acids for treating patients with precancerous lesions |
| US5948779A (en) * | 1997-12-12 | 1999-09-07 | Cell Pathways, Inc. | Substituted condensation products of n-benzyl-3-indenyl acetamides with heterocyclic aldehydes |
| US6028116A (en) * | 1998-04-03 | 2000-02-22 | Cell Pathways, Inc. | Substituted condensation products of 1H-indenyl-hydroxyalkanes with aldehydes for neoplasia |
| IT1315233B1 (it) * | 1999-10-04 | 2003-02-03 | Zambon Spa | Processo per la preparazione dell'acido cis 5-fluoro -2-metil-1-/p-(metiltio) benziliden/inden-3-acetico. |
| CN111233706A (zh) * | 2020-01-19 | 2020-06-05 | 安徽峆一药业股份有限公司 | 一种舒林酸的绿色合成方法 |
| CN117326991B (zh) * | 2022-06-23 | 2025-11-21 | 宁波大红鹰药业股份有限公司 | 一种工业化生产舒林酸的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3692651A (en) * | 1970-05-01 | 1972-09-19 | Meyer Sletzinger | Process for preparing cis 5-fluoro-2-methyl - 1 - (p-methylsulfinylbenzylidene)-3-indenyl acetic acid |
| US3647858A (en) * | 1970-05-01 | 1972-03-07 | Merck & Co Inc | Process for preparing 1-benzylidene-3-indenyl acetic acids |
| US3654349A (en) * | 1970-05-01 | 1972-04-04 | Merck & Co Inc | Substituted indenyl acetic acids |
| US3766259A (en) * | 1970-05-01 | 1973-10-16 | Merck & Co Inc | Preparation of 1-aryl-3-indenyl acetic acids |
| US3932498A (en) * | 1971-01-21 | 1976-01-13 | Merck & Co., Inc. | 3-Indenyl-γ-(ketobutyric)-acid compounds |
| US3998875A (en) * | 1974-10-02 | 1976-12-21 | Merck & Co., Inc. | Process of preparing 5-fluoro-2-methyl-1-(paramethylsulfinylbenzylidene)-indenyl-3-acetic acid |
-
1985
- 1985-06-19 IT IT21215/85A patent/IT1190371B/it active
-
1986
- 1986-06-17 US US06/875,405 patent/US4748271A/en not_active Expired - Lifetime
- 1986-06-18 AT AT86108310T patent/ATE42278T1/de not_active IP Right Cessation
- 1986-06-18 EP EP86108310A patent/EP0206241B1/de not_active Expired
- 1986-06-18 DE DE8686108310T patent/DE3662882D1/de not_active Expired
- 1986-06-19 JP JP61143992A patent/JPH0733368B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0206241A1 (de) | 1986-12-30 |
| EP0206241B1 (de) | 1989-04-19 |
| JPH0733368B2 (ja) | 1995-04-12 |
| JPS6258A (ja) | 1987-01-06 |
| DE3662882D1 (en) | 1989-05-24 |
| US4748271A (en) | 1988-05-31 |
| IT8521215A0 (it) | 1985-06-19 |
| IT1190371B (it) | 1988-02-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| UEP | Publication of translation of european patent specification | ||
| REN | Ceased due to non-payment of the annual fee |