ES288785A1 - Un procedimiento para preparar pirrolo (1,2-a) indoles 6,7-disustituídos - Google Patents
Un procedimiento para preparar pirrolo (1,2-a) indoles 6,7-disustituídosInfo
- Publication number
- ES288785A1 ES288785A1 ES288785A ES288785A ES288785A1 ES 288785 A1 ES288785 A1 ES 288785A1 ES 288785 A ES288785 A ES 288785A ES 288785 A ES288785 A ES 288785A ES 288785 A1 ES288785 A1 ES 288785A1
- Authority
- ES
- Spain
- Prior art keywords
- indole
- pyrrolo
- ester
- product
- amide
- 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
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title 1
- 150000002475 indoles Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical class C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 abstract 6
- 150000001408 amides Chemical class 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- -1 6,7-disubstituted pyrrolo [1,2-a] indoles Chemical class 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 150000002825 nitriles Chemical class 0.000 abstract 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 2
- 150000002081 enamines Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- BXDCKLKMCFTCCM-UHFFFAOYSA-N 1H-pyrrolo[1,2-a]indol-3-ol Chemical compound C1(=CCN2C1=CC=1C=CC=CC2=1)O BXDCKLKMCFTCCM-UHFFFAOYSA-N 0.000 abstract 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
- 125000001041 indolyl group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000002560 nitrile group Chemical group 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US200649A US3206470A (en) | 1962-06-07 | 1962-06-07 | Novel pyrrolo[1, 2-alpha]indoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES288785A1 true ES288785A1 (es) | 1963-11-16 |
Family
ID=22742594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES288785A Expired ES288785A1 (es) | 1962-06-07 | 1963-06-06 | Un procedimiento para preparar pirrolo (1,2-a) indoles 6,7-disustituídos |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3206470A (enExample) |
| AT (1) | AT250951B (enExample) |
| BE (1) | BE633281A (enExample) |
| BR (1) | BR6349521D0 (enExample) |
| DE (1) | DE1445422A1 (enExample) |
| ES (1) | ES288785A1 (enExample) |
| GB (1) | GB1033253A (enExample) |
| NL (1) | NL293572A (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4089969A (en) * | 1976-07-14 | 1978-05-16 | Syntex (U.S.A.) Inc. | 5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid derivatives and process for the production thereof |
| US4097579A (en) * | 1977-03-31 | 1978-06-27 | Syntex (U.S.A.) Inc. | 5-(2-Pyrroyl)-1,2-dihydro-3H-pyrrolo 1,2-a!pyrrole-1-carboxylic acid derivatives and process for the production thereof |
| US4134894A (en) * | 1978-05-04 | 1979-01-16 | Warner-Lambert Company | Pyrrolo[1,2-a]indole compounds |
| US4778812A (en) * | 1987-06-12 | 1988-10-18 | American Home Products Corporation | 2,3-dihydro-9-methyl-1H-pyrrolo[1,2-a]indol-1-amines and derivatives thereof |
| AU2003214462A1 (en) | 2002-04-03 | 2003-10-13 | Astrazeneca Ab | Indole derivatives having anti-angiogenetic activity |
| 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 |
| EP2342205B1 (en) | 2008-08-27 | 2016-04-20 | Arena Pharmaceuticals, Inc. | Substituted tricyclic acid derivatives as s1p1 receptor agonists useful in the treatment of autoimmune and inflammatory disorders |
| EP4148045A1 (en) | 2010-01-27 | 2023-03-15 | Arena Pharmaceuticals, Inc. | Intermediate compounds 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 |
| ES2558087T3 (es) * | 2010-03-03 | 2016-02-01 | Arena Pharmaceuticals, Inc. | Procesos para la preparación de moduladores del receptor S1P1 y formas cristalinas de los mismos |
| AU2016205361C1 (en) | 2015-01-06 | 2021-04-08 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| CA3002551A1 (en) | 2015-06-22 | 2016-12-29 | 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(com pound 1)for use in s1p1 receptor-associated disorders |
| CA3053418A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| WO2018151834A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of inflammatory bowel disease with extra-intestinal manifestations |
| CA3102136A1 (en) | 2018-06-06 | 2019-12-12 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
| CN119751336A (zh) | 2018-09-06 | 2025-04-04 | 艾尼纳制药公司 | 可用于治疗自身免疫性病症和炎性病症的化合物 |
| CN110878099B (zh) * | 2019-11-25 | 2021-11-30 | 五邑大学 | 一种吡咯[1,2,α]吲哚生物碱衍生物的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2707187A (en) * | 1952-07-14 | 1955-04-26 | Upjohn Co | Chemical process |
-
0
- NL NL293572D patent/NL293572A/xx unknown
-
1962
- 1962-06-07 US US200649A patent/US3206470A/en not_active Expired - Lifetime
-
1963
- 1963-05-23 GB GB20589/63A patent/GB1033253A/en not_active Expired
- 1963-05-31 BR BR149521/63A patent/BR6349521D0/pt unknown
- 1963-06-05 BE BE633281A patent/BE633281A/fr unknown
- 1963-06-06 DE DE19631445422 patent/DE1445422A1/de active Pending
- 1963-06-06 AT AT457663A patent/AT250951B/de active
- 1963-06-06 ES ES288785A patent/ES288785A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3206470A (en) | 1965-09-14 |
| BE633281A (fr) | 1963-12-05 |
| DE1445422A1 (de) | 1969-04-10 |
| BR6349521D0 (pt) | 1973-07-03 |
| AT250951B (de) | 1966-12-12 |
| GB1033253A (en) | 1966-06-22 |
| NL293572A (enExample) |
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