GB1472342A - Derivatives of 2-2-pyridylcarbonyl-indole - Google Patents
Derivatives of 2-2-pyridylcarbonyl-indoleInfo
- Publication number
- GB1472342A GB1472342A GB299475A GB299475A GB1472342A GB 1472342 A GB1472342 A GB 1472342A GB 299475 A GB299475 A GB 299475A GB 299475 A GB299475 A GB 299475A GB 1472342 A GB1472342 A GB 1472342A
- Authority
- GB
- United Kingdom
- Prior art keywords
- indole
- prepared
- derivatives
- substituted
- picolyl
- 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
- INXMOYLZSTUBBF-UHFFFAOYSA-N 1h-indol-2-yl(pyridin-2-yl)methanone Chemical class C=1C2=CC=CC=C2NC=1C(=O)C1=CC=CC=N1 INXMOYLZSTUBBF-UHFFFAOYSA-N 0.000 title 1
- ANVQGHPFUNSAPE-UHFFFAOYSA-N 2-(pyridin-2-ylmethyl)-1h-indole Chemical class C=1C2=CC=CC=C2NC=1CC1=CC=CC=N1 ANVQGHPFUNSAPE-UHFFFAOYSA-N 0.000 abstract 2
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 abstract 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 abstract 2
- -1 picolinoyl Chemical group 0.000 abstract 2
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 abstract 1
- PBDCXDMFBSWHPU-UHFFFAOYSA-N C1=CC=C2NC([Li])=CC2=C1 Chemical compound C1=CC=C2NC([Li])=CC2=C1 PBDCXDMFBSWHPU-UHFFFAOYSA-N 0.000 abstract 1
- COHLMUXFVGVBKX-UHFFFAOYSA-N [Li]C1=CC=CC=N1 Chemical compound [Li]C1=CC=CC=N1 COHLMUXFVGVBKX-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000003146 anticoagulant agent Substances 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 239000003527 fibrinolytic agent Substances 0.000 abstract 1
- 230000003480 fibrinolytic effect Effects 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 230000002537 thrombolytic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1472342 Derivatives of 2-(2-picolyl)indole CIBA-GEIGY AG 23 Jan 1975 [25 Jan 1974] 2994/75 Heading C2C The invention comprises indoles-and their salts-which are substituted (a) in the 1-position by aliphatic hydrocarbyl (possibly aryl-substituted), and (b) in the 2-position by (possibly C 1-7 -alkyl substituted) picolinoyl or alphahydroxypicolyl, and optionally (c) in other ring positions. In examples, these compounds are prepared by (1) reducing the ketones to carbinols, or the reverse oxidation process, (2) converting substituent methoxy groups to OH, or (3) reacting together either (i) a 2-lithioindole with 2-formylpyridine or 2-picolinic acid, or (ii) a 2-lithiopyridine with the corresponding indole- 2-carboxylic acid (which reagents are themselves prepared by hydrolysis of the methyl or ethyl esters). The acids may react in the form of their Li salts. Starting materials otherwise prepared have the formula 2,5-MeNH(Cl)C 6 H 3 X, where X is CONHNH 2 , CONHNHO 2 SC 6 H 4 Me(-p) or CHO. Therapeutic compositions having fibrinolytic, thrombolytic and platelet aggregation inhibitive activity, comprise the above 2-(2-picolyl)indole derivatives, and may be administered orally or parenterally.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH104774 | 1974-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1472342A true GB1472342A (en) | 1977-05-04 |
Family
ID=4201215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB299475A Expired GB1472342A (en) | 1974-01-25 | 1975-01-23 | Derivatives of 2-2-pyridylcarbonyl-indole |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS50106969A (en) |
| AT (1) | ATA53175A (en) |
| AU (1) | AU7756375A (en) |
| BE (1) | BE824742A (en) |
| DE (1) | DE2501468A1 (en) |
| DK (1) | DK3375A (en) |
| ES (1) | ES434079A1 (en) |
| FR (1) | FR2258853B1 (en) |
| GB (1) | GB1472342A (en) |
| IE (1) | IE40368B1 (en) |
| IL (1) | IL46505A0 (en) |
| NL (1) | NL7500535A (en) |
| SE (1) | SE7500262L (en) |
| ZA (1) | ZA75522B (en) |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001082909A3 (en) * | 2000-04-28 | 2002-03-14 | Asta Medica Ag | 2-acyl indol derivatives and their use as anti-tumour agents |
| DE10152306A1 (en) * | 2001-10-26 | 2003-07-24 | Asta Medica Ag | 2-acylindole derivatives with new therapeutically valuable properties |
| US8680108B2 (en) | 2009-12-18 | 2014-03-25 | Incyte Corporation | Substituted fused aryl and heteroaryl derivatives as PI3K inhibitors |
| US8759359B2 (en) | 2009-12-18 | 2014-06-24 | Incyte Corporation | Substituted heteroaryl fused derivatives as PI3K inhibitors |
| US8940752B2 (en) | 2009-06-29 | 2015-01-27 | Incyte Corporation | Pyrimidinones as PI3K inhibitors |
| US9062055B2 (en) | 2010-06-21 | 2015-06-23 | Incyte Corporation | Fused pyrrole derivatives as PI3K inhibitors |
| US9096600B2 (en) | 2010-12-20 | 2015-08-04 | Incyte Corporation | N-(1-(substituted-phenyl)ethyl)-9H-purin-6-amines as PI3K inhibitors |
| US9108984B2 (en) | 2011-03-14 | 2015-08-18 | Incyte Corporation | Substituted diamino-pyrimidine and diamino-pyridine derivatives as PI3K inhibitors |
| US9126948B2 (en) | 2011-03-25 | 2015-09-08 | Incyte Holdings Corporation | Pyrimidine-4,6-diamine derivatives as PI3K inhibitors |
| US9193721B2 (en) | 2010-04-14 | 2015-11-24 | Incyte Holdings Corporation | Fused derivatives as PI3Kδ inhibitors |
| US9199982B2 (en) | 2011-09-02 | 2015-12-01 | Incyte Holdings Corporation | Heterocyclylamines as PI3K inhibitors |
| US9309251B2 (en) | 2012-04-02 | 2016-04-12 | Incyte Holdings Corporation | Bicyclic azaheterocyclobenzylamines as PI3K inhibitors |
| US9732097B2 (en) | 2015-05-11 | 2017-08-15 | Incyte Corporation | Process for the synthesis of a phosphoinositide 3-kinase inhibitor |
| US9988401B2 (en) | 2015-05-11 | 2018-06-05 | Incyte Corporation | Crystalline forms of a PI3K inhibitor |
| US10077277B2 (en) | 2014-06-11 | 2018-09-18 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors |
| US10336759B2 (en) | 2015-02-27 | 2019-07-02 | Incyte Corporation | Salts and processes of preparing a PI3K inhibitor |
| US12226418B2 (en) | 2018-06-01 | 2025-02-18 | Incyte Corporation | Dosing regimen for the treatment of PI3K related disorders |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4999186A (en) * | 1986-06-27 | 1991-03-12 | The Procter & Gamble Company | Novel sunscreen agents, sunscreen compositions and methods for preventing sunburn |
| JP2010540641A (en) * | 2007-10-05 | 2010-12-24 | アミラ ファーマシューティカルス，インコーポレーテッド | 5-Lipoxygenase activating protein (FLAP) inhibitor |
-
1975
- 1975-01-08 DK DK3375*BA patent/DK3375A/da unknown
- 1975-01-10 SE SE7500262A patent/SE7500262L/xx unknown
- 1975-01-16 DE DE19752501468 patent/DE2501468A1/en active Pending
- 1975-01-16 NL NL7500535A patent/NL7500535A/en unknown
- 1975-01-23 ES ES434079A patent/ES434079A1/en not_active Expired
- 1975-01-23 GB GB299475A patent/GB1472342A/en not_active Expired
- 1975-01-23 AU AU77563/75A patent/AU7756375A/en not_active Expired
- 1975-01-23 FR FR7502129A patent/FR2258853B1/fr not_active Expired
- 1975-01-24 ZA ZA00750522A patent/ZA75522B/en unknown
- 1975-01-24 IL IL46505A patent/IL46505A0/en unknown
- 1975-01-24 IE IE137/75A patent/IE40368B1/en unknown
- 1975-01-24 BE BE152675A patent/BE824742A/en unknown
- 1975-01-24 AT AT53175A patent/ATA53175A/en not_active IP Right Cessation
- 1975-01-25 JP JP50010179A patent/JPS50106969A/ja active Pending
Cited By (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001082909A3 (en) * | 2000-04-28 | 2002-03-14 | Asta Medica Ag | 2-acyl indol derivatives and their use as anti-tumour agents |
| DE10152306A1 (en) * | 2001-10-26 | 2003-07-24 | Asta Medica Ag | 2-acylindole derivatives with new therapeutically valuable properties |
| DE10152306A8 (en) | 2001-10-26 | 2004-07-08 | Asta Medica Onkologie Gmbh & Co. Kg | 2-acylindole derivatives with new therapeutically valuable properties |
| US9975907B2 (en) | 2009-06-29 | 2018-05-22 | Incyte Holdings Corporation | Pyrimidinones as PI3K inhibitors |
| US10829502B2 (en) | 2009-06-29 | 2020-11-10 | Incyte Corporation | Pyrimidinones as PI3K inhibitors |
| US8940752B2 (en) | 2009-06-29 | 2015-01-27 | Incyte Corporation | Pyrimidinones as PI3K inhibitors |
| US11401280B2 (en) | 2009-06-29 | 2022-08-02 | Incyte Holdings Corporation | Pyrimidinones as PI3K inhibitors |
| US9434746B2 (en) | 2009-06-29 | 2016-09-06 | Incyte Corporation | Pyrimidinones as PI3K inhibitors |
| US10428087B2 (en) | 2009-06-29 | 2019-10-01 | Incyte Corporation | Pyrimidinones as PI3K inhibitors |
| US8680108B2 (en) | 2009-12-18 | 2014-03-25 | Incyte Corporation | Substituted fused aryl and heteroaryl derivatives as PI3K inhibitors |
| US8759359B2 (en) | 2009-12-18 | 2014-06-24 | Incyte Corporation | Substituted heteroaryl fused derivatives as PI3K inhibitors |
| US9403847B2 (en) | 2009-12-18 | 2016-08-02 | Incyte Holdings Corporation | Substituted heteroaryl fused derivatives as P13K inhibitors |
| US9193721B2 (en) | 2010-04-14 | 2015-11-24 | Incyte Holdings Corporation | Fused derivatives as PI3Kδ inhibitors |
| US9062055B2 (en) | 2010-06-21 | 2015-06-23 | Incyte Corporation | Fused pyrrole derivatives as PI3K inhibitors |
| US9815839B2 (en) | 2010-12-20 | 2017-11-14 | Incyte Corporation | N-(1-(substituted-phenyl)ethyl)-9H-purin-6-amines as PI3K inhibitors |
| US9527848B2 (en) | 2010-12-20 | 2016-12-27 | Incyte Holdings Corporation | N-(1-(substituted-phenyl)ethyl)-9H-purin-6-amines as PI3K inhibitors |
| US9096600B2 (en) | 2010-12-20 | 2015-08-04 | Incyte Corporation | N-(1-(substituted-phenyl)ethyl)-9H-purin-6-amines as PI3K inhibitors |
| US9108984B2 (en) | 2011-03-14 | 2015-08-18 | Incyte Corporation | Substituted diamino-pyrimidine and diamino-pyridine derivatives as PI3K inhibitors |
| US9126948B2 (en) | 2011-03-25 | 2015-09-08 | Incyte Holdings Corporation | Pyrimidine-4,6-diamine derivatives as PI3K inhibitors |
| US9707233B2 (en) | 2011-09-02 | 2017-07-18 | Incyte Holdings Corporation | Heterocyclylamines as PI3K inhibitors |
| US11819505B2 (en) | 2011-09-02 | 2023-11-21 | Incyte Corporation | Heterocyclylamines as PI3K inhibitors |
| US10376513B2 (en) | 2011-09-02 | 2019-08-13 | Incyte Holdings Corporation | Heterocyclylamines as PI3K inhibitors |
| US11433071B2 (en) | 2011-09-02 | 2022-09-06 | Incyte Corporation | Heterocyclylamines as PI3K inhibitors |
| US9730939B2 (en) | 2011-09-02 | 2017-08-15 | Incyte Holdings Corporation | Heterocyclylamines as PI3K inhibitors |
| US10092570B2 (en) | 2011-09-02 | 2018-10-09 | Incyte Holdings Corporation | Heterocyclylamines as PI3K inhibitors |
| US12201636B2 (en) | 2011-09-02 | 2025-01-21 | Incyte Corporation | Heterocyclylamines as PI3K inhibitors |
| US10646492B2 (en) | 2011-09-02 | 2020-05-12 | Incyte Corporation | Heterocyclylamines as PI3K inhibitors |
| US9199982B2 (en) | 2011-09-02 | 2015-12-01 | Incyte Holdings Corporation | Heterocyclylamines as PI3K inhibitors |
| US9944646B2 (en) | 2012-04-02 | 2018-04-17 | Incyte Holdings Corporation | Bicyclic azaheterocyclobenzylamines as PI3K inhibitors |
| US10259818B2 (en) | 2012-04-02 | 2019-04-16 | Incyte Corporation | Bicyclic azaheterocyclobenzylamines as PI3K inhibitors |
| US9309251B2 (en) | 2012-04-02 | 2016-04-12 | Incyte Holdings Corporation | Bicyclic azaheterocyclobenzylamines as PI3K inhibitors |
| US11999751B2 (en) | 2014-06-11 | 2024-06-04 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors |
| US11130767B2 (en) | 2014-06-11 | 2021-09-28 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors |
| US10077277B2 (en) | 2014-06-11 | 2018-09-18 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors |
| US10479803B2 (en) | 2014-06-11 | 2019-11-19 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors |
| US11084822B2 (en) | 2015-02-27 | 2021-08-10 | Incyte Corporation | Salts and processes of preparing a PI3K inhibitor |
| US10336759B2 (en) | 2015-02-27 | 2019-07-02 | Incyte Corporation | Salts and processes of preparing a PI3K inhibitor |
| US12024522B2 (en) | 2015-02-27 | 2024-07-02 | Incyte Corporation | Salts and processes of preparing a PI3K inhibitor |
| US10125150B2 (en) | 2015-05-11 | 2018-11-13 | Incyte Corporation | Crystalline forms of a PI3K inhibitor |
| US9988401B2 (en) | 2015-05-11 | 2018-06-05 | Incyte Corporation | Crystalline forms of a PI3K inhibitor |
| US9732097B2 (en) | 2015-05-11 | 2017-08-15 | Incyte Corporation | Process for the synthesis of a phosphoinositide 3-kinase inhibitor |
| US12226418B2 (en) | 2018-06-01 | 2025-02-18 | Incyte Corporation | Dosing regimen for the treatment of PI3K related disorders |
Also Published As
| Publication number | Publication date |
|---|---|
| IL46505A0 (en) | 1975-04-25 |
| SE7500262L (en) | 1975-07-28 |
| ZA75522B (en) | 1976-01-28 |
| NL7500535A (en) | 1975-07-29 |
| FR2258853A1 (en) | 1975-08-22 |
| JPS50106969A (en) | 1975-08-22 |
| IE40368B1 (en) | 1979-05-09 |
| BE824742A (en) | 1975-07-24 |
| DK3375A (en) | 1975-09-15 |
| ES434079A1 (en) | 1977-03-01 |
| ATA53175A (en) | 1977-08-15 |
| DE2501468A1 (en) | 1975-07-31 |
| AU7756375A (en) | 1976-07-29 |
| FR2258853B1 (en) | 1978-06-30 |
| IE40368L (en) | 1975-07-25 |
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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 |