GB1436893A - Tetrahydrocarbazole derivatives and process for their manufa cture - Google Patents
Tetrahydrocarbazole derivatives and process for their manufa ctureInfo
- Publication number
- GB1436893A GB1436893A GB2279573A GB2279573A GB1436893A GB 1436893 A GB1436893 A GB 1436893A GB 2279573 A GB2279573 A GB 2279573A GB 2279573 A GB2279573 A GB 2279573A GB 1436893 A GB1436893 A GB 1436893A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- compounds
- esters
- conh
- cyclohexanone
- 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
- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- -1 aminomethyl compound Chemical class 0.000 abstract 1
- 238000005915 ammonolysis reaction Methods 0.000 abstract 1
- 230000000843 anti-fungal effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 229940121375 antifungal agent Drugs 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- CANSWZHFWLNCPV-UHFFFAOYSA-N ethyl 3-bromo-5-methyl-2-oxocyclohexane-1-carboxylate Chemical compound C(C)OC(=O)C1C(C(CC(C1)C)Br)=O CANSWZHFWLNCPV-UHFFFAOYSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722226703 DE2226703A1 (de) | 1972-05-25 | 1972-05-25 | Neue tetrahydrocarbazolderivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1436893A true GB1436893A (en) | 1976-05-26 |
Family
ID=5846530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2279573A Expired GB1436893A (en) | 1972-05-25 | 1973-05-14 | Tetrahydrocarbazole derivatives and process for their manufa cture |
Country Status (12)
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005033112A3 (en) * | 2003-10-02 | 2005-06-09 | Salmedix Inc | Substituted indole derivatives |
| US7105560B1 (en) | 1999-07-23 | 2006-09-12 | The Regents Of The University Of California | Use of etodolac in the treatment of multiple myeloma |
| US7105561B2 (en) | 1999-07-23 | 2006-09-12 | The Regents Of The University Of California | Use of etodolac for the treatment of prostate cancer |
| US7122570B2 (en) * | 2001-12-14 | 2006-10-17 | Zentaris Ag | Tetrahydrocarbazol derivatives as ligands for G-protein-coupled receptors (GPCR) |
| US7129262B2 (en) | 1999-07-23 | 2006-10-31 | The Regents Of The University Of California | Indole compounds useful for the treatment of cancer |
| US7151100B1 (en) | 1999-07-23 | 2006-12-19 | The Regents Of The University Of California | Indole compounds useful for the treatment of cancer |
| US7211599B2 (en) | 2002-09-19 | 2007-05-01 | The Regents Of The University Of California | Use of etodolac to treat hyperplasia |
| EP1793817A4 (en) * | 2004-09-13 | 2008-04-02 | Elixir Pharmaceuticals Inc | METHODS OF TREATING A DISEASE |
| US7361680B2 (en) | 1999-07-23 | 2008-04-22 | The Regents Of The University Of California | Indole compounds useful for the treatment of cancer |
| WO2010011316A1 (en) * | 2008-07-23 | 2010-01-28 | Arena Pharmaceuticals, Inc. | SUBSTITUTED 1,2,3,4- TETRAHYDROCYCLOPENTA[b]INDOL-3-YL) ACETIC ACID DERIVATIVES USEFUL IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISORDERS |
| EP1677794A4 (en) * | 2003-09-12 | 2010-05-19 | Elixir Pharmaceuticals Inc | METHODS OF TREATING DISORDERS |
| US8415484B2 (en) | 2008-08-27 | 2013-04-09 | Arena Pharmaceuticals, Inc. | Substituted tricyclic acid derivatives as S1P1 receptor agonists useful in the treatment of autoimmune and inflammatory disorders |
| US8853419B2 (en) | 2010-01-27 | 2014-10-07 | Arena Pharmaceuticals, Inc. | Processes for the preparation of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof |
| US9085581B2 (en) | 2010-03-03 | 2015-07-21 | Arena Pharmaceuticals, Inc. | Processes for the preparation of S1P1 receptor modulators and crystalline forms thereof |
| US10301262B2 (en) | 2015-06-22 | 2019-05-28 | Arena Pharmaceuticals, Inc. | Crystalline L-arginine salt of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta [b]indol-3-yl)acetic acid(Compund1) for use in SIPI receptor-associated disorders |
| US11007175B2 (en) | 2015-01-06 | 2021-05-18 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| CN114634442A (zh) * | 2022-04-02 | 2022-06-17 | 内蒙古民族大学 | 一种四氢咔唑酮化合物的制备方法 |
| US11478448B2 (en) | 2017-02-16 | 2022-10-25 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of inflammatory bowel disease with extra-intestinal manifestations |
| US11534424B2 (en) | 2017-02-16 | 2022-12-27 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| US11555015B2 (en) | 2018-09-06 | 2023-01-17 | Arena Pharmaceuticals, Inc. | Compounds useful in the treatment of autoimmune and inflammatory disorders |
| US12156866B2 (en) | 2018-06-06 | 2024-12-03 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4235903A (en) * | 1979-08-06 | 1980-11-25 | American Home Products Corporation | 1-Hydroxyalkanamine tetrahydrocarbazoles and cyclopent[b]indoles, compositions and method of use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH586678A5 (enrdf_load_stackoverflow) * | 1970-05-25 | 1977-04-15 | Hoffmann La Roche | |
| ZA715217B (en) * | 1970-08-20 | 1972-04-26 | Org Nv | Anti-inflammatory preparations |
-
1972
- 1972-05-25 DE DE19722226703 patent/DE2226703A1/de active Pending
-
1973
- 1973-04-17 DD DD17023273A patent/DD106170A5/xx unknown
- 1973-05-14 GB GB2279573A patent/GB1436893A/en not_active Expired
- 1973-05-16 CS CS350973A patent/CS179416B2/cs unknown
- 1973-05-17 CH CH707473A patent/CH582144A5/xx not_active IP Right Cessation
- 1973-05-23 AT AT449173A patent/AT323155B/de not_active IP Right Cessation
- 1973-05-24 AU AU56078/73A patent/AU5607873A/en not_active Expired
- 1973-05-25 BE BE131549A patent/BE800066A/xx unknown
- 1973-05-25 JP JP5848173A patent/JPS4941367A/ja active Pending
- 1973-05-25 FR FR7319087A patent/FR2185414B1/fr not_active Expired
- 1973-05-25 CA CA172,234A patent/CA1005062A/en not_active Expired
- 1973-05-25 NL NL7307313A patent/NL7307313A/xx not_active Application Discontinuation
Cited By (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7361680B2 (en) | 1999-07-23 | 2008-04-22 | The Regents Of The University Of California | Indole compounds useful for the treatment of cancer |
| US7105560B1 (en) | 1999-07-23 | 2006-09-12 | The Regents Of The University Of California | Use of etodolac in the treatment of multiple myeloma |
| US7105561B2 (en) | 1999-07-23 | 2006-09-12 | The Regents Of The University Of California | Use of etodolac for the treatment of prostate cancer |
| US7129262B2 (en) | 1999-07-23 | 2006-10-31 | The Regents Of The University Of California | Indole compounds useful for the treatment of cancer |
| US7151100B1 (en) | 1999-07-23 | 2006-12-19 | The Regents Of The University Of California | Indole compounds useful for the treatment of cancer |
| US7189752B2 (en) | 1999-07-23 | 2007-03-13 | Carson Dennis A | Use of etodolac for the treatment of chronic lymphocytic leukemia |
| US7122570B2 (en) * | 2001-12-14 | 2006-10-17 | Zentaris Ag | Tetrahydrocarbazol derivatives as ligands for G-protein-coupled receptors (GPCR) |
| US7211599B2 (en) | 2002-09-19 | 2007-05-01 | The Regents Of The University Of California | Use of etodolac to treat hyperplasia |
| US8486990B2 (en) | 2003-09-12 | 2013-07-16 | Elixir Pharmaceuticals, Inc. | SirT inhibitors that bind to NAD |
| EP1677794A4 (en) * | 2003-09-12 | 2010-05-19 | Elixir Pharmaceuticals Inc | METHODS OF TREATING DISORDERS |
| US7314886B2 (en) | 2003-10-02 | 2008-01-01 | Cephalon, Inc. | Tetrahydropyrano-indole derivatives |
| WO2005033113A3 (en) * | 2003-10-02 | 2005-06-30 | Salmedix Inc | Indole derivatives |
| US7446122B2 (en) | 2003-10-02 | 2008-11-04 | Cephalon, Inc. | Substituted indole derivatives |
| WO2005033112A3 (en) * | 2003-10-02 | 2005-06-09 | Salmedix Inc | Substituted indole derivatives |
| EP1793817A4 (en) * | 2004-09-13 | 2008-04-02 | Elixir Pharmaceuticals Inc | METHODS OF TREATING A DISEASE |
| CN102164891B (zh) * | 2008-07-23 | 2014-09-03 | 艾尼纳制药公司 | 可用于治疗自身免疫性疾病和炎性疾病的经取代的1,2,3,4-四氢环戊并[b]吲哚-3-基乙酸衍生物 |
| US9522133B2 (en) | 2008-07-23 | 2016-12-20 | Arena Pharmaceuticals, Inc. | Substituted 1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid derivatives useful in the treatment of autoimmune and inflammatory disorders |
| US8580841B2 (en) | 2008-07-23 | 2013-11-12 | Arena Pharmaceuticals, Inc. | Substituted 1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid derivatives useful in the treatment of autoimmune and inflammatory disorders |
| EA019252B1 (ru) * | 2008-07-23 | 2014-02-28 | Арена Фармасьютикалз, Инк. | ЗАМЕЩЕННЫЕ ПРОИЗВОДНЫЕ (1,2,3,4-ТЕТРАГИДРОЦИКЛОПЕНТА[b]ИНДОЛ-3-ИЛ)УКСУСНОЙ КИСЛОТЫ, ПРИМЕНИМЫЕ В ЛЕЧЕНИИ АУТОИММУННЫХ И ВОСПАЛИТЕЛЬНЫХ РАССТРОЙСТВ |
| CN104311472B9 (zh) * | 2008-07-23 | 2020-03-17 | 艾尼纳制药公司 | 经取代的1,2,3,4-四氢环戊并[b]吲哚-3-基乙酸衍生物 |
| CN104311472B (zh) * | 2008-07-23 | 2019-12-31 | 艾尼纳制药公司 | 经取代的1,2,3,4-四氢环戊并[b]吲哚-3-基乙酸衍生物 |
| CN104311472A (zh) * | 2008-07-23 | 2015-01-28 | 艾尼纳制药公司 | 经取代的1,2,3,4-四氢环戊并[b]吲哚-3-基乙酸衍生物 |
| WO2010011316A1 (en) * | 2008-07-23 | 2010-01-28 | Arena Pharmaceuticals, Inc. | SUBSTITUTED 1,2,3,4- TETRAHYDROCYCLOPENTA[b]INDOL-3-YL) ACETIC ACID DERIVATIVES USEFUL IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISORDERS |
| JP2016029067A (ja) * | 2008-07-23 | 2016-03-03 | アリーナ ファーマシューティカルズ， インコーポレイテッド | 自己免疫障害および炎症性障害の処置において有用な置換型１，２，３，４−テトラヒドロシクロペンタ［ｂ］インドル−３−イル）酢酸誘導体 |
| US9126932B2 (en) | 2008-07-23 | 2015-09-08 | Arena Pharmaceuticals, Inc. | Substituted 1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid derivatives useful in the treatment of autoimmune and inflammatory disorders |
| US9108969B2 (en) | 2008-08-27 | 2015-08-18 | Arena Pharmaceuticals, Inc. | Substituted tricyclic acid derivatives as S1P1 receptor agonists useful in the treatment of autoimmune and inflammatory disorders |
| US8415484B2 (en) | 2008-08-27 | 2013-04-09 | Arena Pharmaceuticals, Inc. | Substituted tricyclic acid derivatives as S1P1 receptor agonists useful in the treatment of autoimmune and inflammatory disorders |
| US9175320B2 (en) | 2010-01-27 | 2015-11-03 | Arena Pharmaceuticals, Inc. | Processes for the preparation of (R)-2-(7-4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[B]indol-3-yl)acetic acid and salts thereof |
| US9447041B2 (en) | 2010-01-27 | 2016-09-20 | Arena Pharmaceuticals, Inc. | Processes for the preparation of (R)-2-(7-4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[B]indol-3-yl)acetic acid and salts thereof |
| US11149292B2 (en) | 2010-01-27 | 2021-10-19 | Arena Pharmaceuticals, Inc. | Processes for the preparation of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[B]indol-3-yl)acetic acid and salts thereof |
| US11674163B2 (en) | 2010-01-27 | 2023-06-13 | Arena Pharmaceuticals, Inc. | Processes for the preparation of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof |
| US8853419B2 (en) | 2010-01-27 | 2014-10-07 | Arena Pharmaceuticals, Inc. | Processes for the preparation of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof |
| US9085581B2 (en) | 2010-03-03 | 2015-07-21 | Arena Pharmaceuticals, Inc. | Processes for the preparation of S1P1 receptor modulators and crystalline forms thereof |
| US11896578B2 (en) | 2015-01-06 | 2024-02-13 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| US11007175B2 (en) | 2015-01-06 | 2021-05-18 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| US11091435B2 (en) | 2015-06-22 | 2021-08-17 | Arena Pharmaceuticals, Inc. | Crystalline L-arginine salt of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3, 4-tetrahydrocyclo-penta [b]indol-3-yl)acetic acid(compound1) for use in S1P1 receptor-associated disorders |
| US10676435B2 (en) | 2015-06-22 | 2020-06-09 | Arena Pharmaceuticals, Inc. | Crystalline L-arginine salt of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta [b]indol-3-yl)acetic acid(Compound 1) for use in SIPI receptor-associated disorders |
| US10301262B2 (en) | 2015-06-22 | 2019-05-28 | Arena Pharmaceuticals, Inc. | Crystalline L-arginine salt of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta [b]indol-3-yl)acetic acid(Compund1) for use in SIPI receptor-associated disorders |
| US11884626B2 (en) | 2015-06-22 | 2024-01-30 | Arena Pharmaceuticals, Inc. | Crystalline L-arginine salt of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta [b]indol-3-yl)acetic acid(Compound1) for use in S1P1 receptor-associated disorders |
| US11478448B2 (en) | 2017-02-16 | 2022-10-25 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of inflammatory bowel disease with extra-intestinal manifestations |
| US11534424B2 (en) | 2017-02-16 | 2022-12-27 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| US12097182B2 (en) | 2017-02-16 | 2024-09-24 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of inflammatory bowel disease with extra-intestinal manifestations |
| US12156866B2 (en) | 2018-06-06 | 2024-12-03 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| US11555015B2 (en) | 2018-09-06 | 2023-01-17 | Arena Pharmaceuticals, Inc. | Compounds useful in the treatment of autoimmune and inflammatory disorders |
| CN114634442B (zh) * | 2022-04-02 | 2023-10-13 | 内蒙古民族大学 | 一种四氢咔唑酮化合物的制备方法 |
| CN114634442A (zh) * | 2022-04-02 | 2022-06-17 | 内蒙古民族大学 | 一种四氢咔唑酮化合物的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU5607873A (en) | 1974-11-28 |
| BE800066A (fr) | 1973-11-26 |
| DD106170A5 (enrdf_load_stackoverflow) | 1974-06-05 |
| CH582144A5 (enrdf_load_stackoverflow) | 1976-11-30 |
| AT323155B (de) | 1975-06-25 |
| JPS4941367A (enrdf_load_stackoverflow) | 1974-04-18 |
| CS179416B2 (en) | 1977-10-31 |
| NL7307313A (enrdf_load_stackoverflow) | 1973-11-27 |
| FR2185414A1 (enrdf_load_stackoverflow) | 1974-01-04 |
| CA1005062A (en) | 1977-02-08 |
| FR2185414B1 (enrdf_load_stackoverflow) | 1976-08-13 |
| DE2226703A1 (de) | 1973-12-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |