FR2338043A1 - Antidepressant 4-aryl-piperidines and salts - some having local anaesthetic and antiarrhythmic activity - Google Patents
Antidepressant 4-aryl-piperidines and salts - some having local anaesthetic and antiarrhythmic activityInfo
- Publication number
- FR2338043A1 FR2338043A1 FR7600727A FR7600727A FR2338043A1 FR 2338043 A1 FR2338043 A1 FR 2338043A1 FR 7600727 A FR7600727 A FR 7600727A FR 7600727 A FR7600727 A FR 7600727A FR 2338043 A1 FR2338043 A1 FR 2338043A1
- Authority
- FR
- France
- Prior art keywords
- opt
- substd
- aryl
- halo
- alkyl
- 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.)
- Granted
Links
- 230000003444 anaesthetic effect Effects 0.000 title abstract 2
- 230000003288 anthiarrhythmic effect Effects 0.000 title abstract 2
- 230000001430 anti-depressive effect Effects 0.000 title abstract 2
- 239000000935 antidepressant agent Substances 0.000 title abstract 2
- 229940005513 antidepressants Drugs 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 230000000694 effects Effects 0.000 abstract 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 abstract 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 230000001078 anti-cholinergic effect Effects 0.000 abstract 1
- 230000001387 anti-histamine Effects 0.000 abstract 1
- -1 anticholinergic Substances 0.000 abstract 1
- 239000000739 antihistaminic agent Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000000812 cholinergic antagonist Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical group O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 230000002048 spasmolytic effect Effects 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D211/56—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/64—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having an aryl radical as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
4-Aryl-amino-hydroxypiperidines of formula (I) are new together with their acid-addn. salts (where R' is H,alkyl, alkenyl, alkynyl, aralkyl, acyl, 2-6C alkylamino opt. substd. by one or two alkyls or opt. substd. by alkylene to complete a satd. N-heterocycle; a gp. where R7 and R8 are H, phenyl opt. substd. by halo, or alkyl; or R7 + R8 and the attached N-atom form a 6 or 7-membered heterocyclic ring opt. contg. an O-atom; n is 1, 2, 3 or 4; a gp. -(CH2)n. CO2H; a gp. where X is H or halo; one of R2 and R3 is CN, free NH2 or a radical derived from it; the other is a free or protected OH; or R2 is where R3 is free or protected OH; or R2 + R3 and the attached C atoms form an oxazepin ring; Ar is aryl opt. substd. by one or more alkyl, alkoxy, halo or CF3). One subgp. has antidepressant activity, another gp. has local anaesthetic and antiarrhythmic activity. Other activities in the gp. include antihistamine, anticholinergic, spasmolytic, and diuretic activity.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7600727A FR2338043A1 (en) | 1976-01-13 | 1976-01-13 | Antidepressant 4-aryl-piperidines and salts - some having local anaesthetic and antiarrhythmic activity |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7600727A FR2338043A1 (en) | 1976-01-13 | 1976-01-13 | Antidepressant 4-aryl-piperidines and salts - some having local anaesthetic and antiarrhythmic activity |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2338043A1 true FR2338043A1 (en) | 1977-08-12 |
FR2338043B1 FR2338043B1 (en) | 1978-11-03 |
Family
ID=9167862
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR7600727A Granted FR2338043A1 (en) | 1976-01-13 | 1976-01-13 | Antidepressant 4-aryl-piperidines and salts - some having local anaesthetic and antiarrhythmic activity |
Country Status (1)
Country | Link |
---|---|
FR (1) | FR2338043A1 (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0965588A1 (en) * | 1998-06-18 | 1999-12-22 | Hoechst Marion Roussel | Process for the preparation of 4-phenyl-1,2,3,6-tetrahydropyridine derivatives and intermediates used in this process |
US7129228B2 (en) | 1999-05-25 | 2006-10-31 | Sepracor Inc. | Heterocyclic analgesic compounds and methods of use thereof |
US7361666B2 (en) * | 1999-05-25 | 2008-04-22 | Sepracor, Inc. | Heterocyclic analgesic compounds and methods of use thereof |
US10265310B2 (en) * | 2016-09-21 | 2019-04-23 | Grünenthal GmbH | 6-membered cyclic amines or lactames substituted with urea and phenyl |
US10562925B2 (en) | 2015-05-18 | 2020-02-18 | Tolero Pharmaceuticals, Inc. | Alvocidib prodrugs having increased bioavailability |
US10568887B2 (en) | 2015-08-03 | 2020-02-25 | Tolero Pharmaceuticals, Inc. | Combination therapies for treatment of cancer |
US10624880B2 (en) | 2015-04-20 | 2020-04-21 | Tolero Pharmaceuticals, Inc. | Predicting response to alvocidib by mitochondrial profiling |
US11034710B2 (en) | 2018-12-04 | 2021-06-15 | Sumitomo Dainippon Pharma Oncology, Inc. | CDK9 inhibitors and polymorphs thereof for use as agents for treatment of cancer |
US11279694B2 (en) | 2016-11-18 | 2022-03-22 | Sumitomo Dainippon Pharma Oncology, Inc. | Alvocidib prodrugs and their use as protein kinase inhibitors |
US11497756B2 (en) | 2017-09-12 | 2022-11-15 | Sumitomo Pharma Oncology, Inc. | Treatment regimen for cancers that are insensitive to BCL-2 inhibitors using the MCL-1 inhibitor alvocidib |
US11793802B2 (en) | 2019-03-20 | 2023-10-24 | Sumitomo Pharma Oncology, Inc. | Treatment of acute myeloid leukemia (AML) with venetoclax failure |
-
1976
- 1976-01-13 FR FR7600727A patent/FR2338043A1/en active Granted
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0965588A1 (en) * | 1998-06-18 | 1999-12-22 | Hoechst Marion Roussel | Process for the preparation of 4-phenyl-1,2,3,6-tetrahydropyridine derivatives and intermediates used in this process |
FR2780056A1 (en) * | 1998-06-18 | 1999-12-24 | Hoechst Marion Roussel Inc | NEW PROCESS FOR PREPARATION OF 4-PHENYL-1-2 3,6-TETRAHYDROPYRIDINE DERIVATIVES AND THE INTERMEDIATE PRODUCTS USED |
US6136981A (en) * | 1998-06-18 | 2000-10-24 | Hoechst Marion Roussel | Preparation of 4-phenyl-1,2,3,6-tetrahydropyridines |
US7129228B2 (en) | 1999-05-25 | 2006-10-31 | Sepracor Inc. | Heterocyclic analgesic compounds and methods of use thereof |
US7361666B2 (en) * | 1999-05-25 | 2008-04-22 | Sepracor, Inc. | Heterocyclic analgesic compounds and methods of use thereof |
US10624880B2 (en) | 2015-04-20 | 2020-04-21 | Tolero Pharmaceuticals, Inc. | Predicting response to alvocidib by mitochondrial profiling |
US10562925B2 (en) | 2015-05-18 | 2020-02-18 | Tolero Pharmaceuticals, Inc. | Alvocidib prodrugs having increased bioavailability |
US12338261B2 (en) | 2015-05-18 | 2025-06-24 | Sumitomo Pharma Oncology, Inc. | Alvocidib prodrugs having increased bioavailability |
US10568887B2 (en) | 2015-08-03 | 2020-02-25 | Tolero Pharmaceuticals, Inc. | Combination therapies for treatment of cancer |
US10682356B2 (en) | 2015-08-03 | 2020-06-16 | Tolero Pharmaceuticals, Inc. | Combination therapies for treatment of cancer |
US10835537B2 (en) | 2015-08-03 | 2020-11-17 | Sumitomo Dainippon Pharma Oncology, Inc. | Combination therapies for treatment of cancer |
US10265310B2 (en) * | 2016-09-21 | 2019-04-23 | Grünenthal GmbH | 6-membered cyclic amines or lactames substituted with urea and phenyl |
US11279694B2 (en) | 2016-11-18 | 2022-03-22 | Sumitomo Dainippon Pharma Oncology, Inc. | Alvocidib prodrugs and their use as protein kinase inhibitors |
US11497756B2 (en) | 2017-09-12 | 2022-11-15 | Sumitomo Pharma Oncology, Inc. | Treatment regimen for cancers that are insensitive to BCL-2 inhibitors using the MCL-1 inhibitor alvocidib |
US11034710B2 (en) | 2018-12-04 | 2021-06-15 | Sumitomo Dainippon Pharma Oncology, Inc. | CDK9 inhibitors and polymorphs thereof for use as agents for treatment of cancer |
US11530231B2 (en) | 2018-12-04 | 2022-12-20 | Sumitomo Pharma Oncology, Inc. | CDK9 inhibitors and polymorphs thereof for use as agents for treatment of cancer |
US12077554B2 (en) | 2018-12-04 | 2024-09-03 | Sumitomo Pharma Oncology, Inc. | CDK9 inhibitors and polymorphs thereof for use as agents for treatment of cancer |
US11793802B2 (en) | 2019-03-20 | 2023-10-24 | Sumitomo Pharma Oncology, Inc. | Treatment of acute myeloid leukemia (AML) with venetoclax failure |
Also Published As
Publication number | Publication date |
---|---|
FR2338043B1 (en) | 1978-11-03 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
ST | Notification of lapse |