GB1505085A - 6,11-dihydrodibenzo - thiepin - 11 - ones methods of preparation compositions and uses thereof - Google Patents
6,11-dihydrodibenzo - thiepin - 11 - ones methods of preparation compositions and uses thereofInfo
- Publication number
- GB1505085A GB1505085A GB1783/76A GB178376A GB1505085A GB 1505085 A GB1505085 A GB 1505085A GB 1783/76 A GB1783/76 A GB 1783/76A GB 178376 A GB178376 A GB 178376A GB 1505085 A GB1505085 A GB 1505085A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- thiepin
- alkyl
- salt
- free acid
- Prior art date
- 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
Links
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/12—[b,e]-condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Abstract
1505085 6,11-Dihydro-dibenzo[b,e]thiepin- 11-ones SYNTEX (USA) Inc 16 Jan 1976 [18 Feb 1975 30 June 1975 21 Nov 1975 (2)] 01783/76 Heading C2C Novel compounds I in which R is H, C 1-12 alkyl or a salt-forming group and R<SP>11</SP> is H or Me are prepared by (a) reacting 3 - diazoacetyl - 6,11 - dihydrodibenzo[b,e]thiepin - 11 - one with silver benzoate in the presence of a C 1-12 alkanol to form a compound I [R = C 1-12 alkyl ; R<SP>11</SP> = H] (b) α-methylating a compound I [R = C 1-12 alkyl; R<SP>11</SP> = H] to form a compound I (R = C 1-12 alkyl; R<SP>11</SP> = Me) or (c) hydrolysing an ester or converting a salt into the free acid, esterifying a free acid or converting one ester into another by transesterification, converting a salt into another salt by metathesis or salifying a free acid. Compound I (R = H, R<SP>11</SP> = Me] is resolved into optical isomers and the lisomers thereof is racemised to the dl form. Nitroterephthalic acid is esterified to form the isopropyl ester which is reacted in the presence of NaH with benzyl mercaptan to form diisopropyl benzylthioterephthalate which is hydrolysed to the free acid and converted to the acid chloride; cyclization of the acid chloride leads to 6,11-dihydro-11-oxo-dibenzo[b,e]thiepin- 3-carbonyl chloride which is reacted with CH 2 N 2 or CH 3 CH 2 N 2 to form the 3-diazoacetyl or 3-(α- diazopropionyl) compound. Compounds I [R<SP>11</SP> = H and d and dl compounds where R<SP>11</SP> = Me] have anti-inflammatory analgesic, anti-pyretic, platelet aggregation inhibiting, fibrinolytic and smooth-muscle releasing activity; they form with an excipient a pharmaceutical composition which may be administered orally, parenterally, rectally, topically or vaginally.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55031675A | 1975-02-18 | 1975-02-18 | |
| US59172575A | 1975-06-30 | 1975-06-30 | |
| US05/634,086 US4000308A (en) | 1975-02-18 | 1975-11-21 | 6,11-Dihydrodibenzo-thiepin-11-ones, compositions and uses thereof |
| US05/634,085 US4000288A (en) | 1975-02-18 | 1975-11-21 | 6,11-dihydrodibenzo-thiepin-11-ones, compositions and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1505085A true GB1505085A (en) | 1978-03-22 |
Family
ID=27504746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1783/76A Expired GB1505085A (en) | 1975-02-18 | 1976-01-16 | 6,11-dihydrodibenzo - thiepin - 11 - ones methods of preparation compositions and uses thereof |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS51143688A (en) |
| AR (1) | AR216050A1 (en) |
| AT (1) | AT352731B (en) |
| AU (1) | AU500501B2 (en) |
| BE (1) | BE838637A (en) |
| DE (1) | DE2606312A1 (en) |
| DK (1) | DK67676A (en) |
| ES (2) | ES459400A1 (en) |
| FI (1) | FI760273A (en) |
| FR (1) | FR2301245A1 (en) |
| GB (1) | GB1505085A (en) |
| IL (1) | IL48807A0 (en) |
| NL (1) | NL7600899A (en) |
| NO (1) | NO760297L (en) |
| PT (1) | PT64692B (en) |
| SE (1) | SE7601754L (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006051477A3 (en) * | 2004-11-10 | 2006-08-03 | Nicholas Piramal India Ltd | Fused tricyclic compounds as inhibitors of tumor necrosis factor-alpha |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4130654A (en) * | 1978-01-30 | 1978-12-19 | Syntex (U.S.A.) Inc. | Novel 4-(8X-6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-yl)-4-oxobutyric acids, methods of preparation, compositions and uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK467274A (en) * | 1973-09-13 | 1975-05-12 | Sandoz Ag |
-
1976
- 1976-01-08 IL IL48807A patent/IL48807A0/en unknown
- 1976-01-14 PT PT64692A patent/PT64692B/en unknown
- 1976-01-16 GB GB1783/76A patent/GB1505085A/en not_active Expired
- 1976-01-29 NL NL7600899A patent/NL7600899A/en not_active Application Discontinuation
- 1976-01-30 NO NO760297A patent/NO760297L/no unknown
- 1976-01-30 AU AU10686/76A patent/AU500501B2/en not_active Expired
- 1976-02-04 AR AR262140A patent/AR216050A1/en active
- 1976-02-05 FI FI760273A patent/FI760273A/fi not_active Application Discontinuation
- 1976-02-17 BE BE164382A patent/BE838637A/en unknown
- 1976-02-17 FR FR7604353A patent/FR2301245A1/en active Granted
- 1976-02-17 SE SE7601754A patent/SE7601754L/en unknown
- 1976-02-17 DE DE19762606312 patent/DE2606312A1/en active Pending
- 1976-02-17 JP JP51016446A patent/JPS51143688A/en active Pending
- 1976-02-18 DK DK67676*#A patent/DK67676A/en unknown
- 1976-02-18 AT AT115976A patent/AT352731B/en not_active IP Right Cessation
-
1977
- 1977-06-01 ES ES459400A patent/ES459400A1/en not_active Expired
- 1977-06-01 ES ES459401A patent/ES459401A1/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006051477A3 (en) * | 2004-11-10 | 2006-08-03 | Nicholas Piramal India Ltd | Fused tricyclic compounds as inhibitors of tumor necrosis factor-alpha |
| US7834052B2 (en) | 2004-11-10 | 2010-11-16 | Piramal Life Sciences Limited | Fused tricyclic compounds as inhibitors of tumor necrosis factor-alpha |
| US7964631B2 (en) | 2004-11-10 | 2011-06-21 | Piramal Life Sciences Limited | Fused tricyclic compounds as inhibitors of tumor necrosis factor-α |
| AU2005303410B2 (en) * | 2004-11-10 | 2011-12-15 | Piramal Enterprises Limited | Fused tricyclic compounds as inhibitors of tumor necrosis factor-alpha |
| US8163730B2 (en) | 2004-11-10 | 2012-04-24 | Piramal Life Sciences Limited | Fused tricyclic compounds as inhibitors of tumor necrosis factor-alpha |
Also Published As
| Publication number | Publication date |
|---|---|
| FI760273A (en) | 1976-08-19 |
| AU500501B2 (en) | 1979-05-24 |
| JPS51143688A (en) | 1976-12-10 |
| IL48807A0 (en) | 1976-03-31 |
| DE2606312A1 (en) | 1976-08-26 |
| AT352731B (en) | 1979-10-10 |
| ES459400A1 (en) | 1978-08-16 |
| ATA115976A (en) | 1979-03-15 |
| AR216050A1 (en) | 1979-11-30 |
| ES459401A1 (en) | 1979-06-16 |
| NL7600899A (en) | 1976-08-20 |
| NO760297L (en) | 1976-08-19 |
| BE838637A (en) | 1976-08-17 |
| SE7601754L (en) | 1976-10-25 |
| DK67676A (en) | 1976-08-19 |
| FR2301245A1 (en) | 1976-09-17 |
| PT64692B (en) | 1978-01-04 |
| FR2301245B1 (en) | 1979-07-20 |
| PT64692A (en) | 1976-02-01 |
| AU1068676A (en) | 1977-08-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |