AR062405A1 - ISOINDOL DERIVATIVES - Google Patents
ISOINDOL DERIVATIVESInfo
- Publication number
- AR062405A1 AR062405A1 ARP070103649A ARP070103649A AR062405A1 AR 062405 A1 AR062405 A1 AR 062405A1 AR P070103649 A ARP070103649 A AR P070103649A AR P070103649 A ARP070103649 A AR P070103649A AR 062405 A1 AR062405 A1 AR 062405A1
- Authority
- AR
- Argentina
- Prior art keywords
- substituted
- alkyl
- taken together
- independently selected
- hydrogen
- Prior art date
Links
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical class C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 229910052799 carbon Inorganic materials 0.000 abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- 125000004043 oxo group Chemical group O=* 0.000 abstract 7
- 229910052760 oxygen Inorganic materials 0.000 abstract 7
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 6
- 150000002431 hydrogen Chemical group 0.000 abstract 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 6
- 229910052757 nitrogen Inorganic materials 0.000 abstract 6
- 229910052717 sulfur Inorganic materials 0.000 abstract 6
- 239000001301 oxygen Substances 0.000 abstract 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 150000001721 carbon Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000001153 fluoro group Chemical group F* 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical group 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 125000005415 substituted alkoxy group Chemical group 0.000 abstract 3
- 125000004434 sulfur atom Chemical group 0.000 abstract 3
- 125000004011 3 membered carbocyclic group Chemical group 0.000 abstract 2
- 125000001845 4 membered carbocyclic group Chemical group 0.000 abstract 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 abstract 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- MJYFVDNMTKLGTH-UHFFFAOYSA-N 4-bromo-6-(3,4-dichlorophenyl)sulfanyl-1-[[4-(dimethylcarbamoyl)phenyl]methyl]indole-2-carboxylic acid Chemical compound BrC1=C2C=C(N(C2=CC(=C1)SC1=CC(=C(C=C1)Cl)Cl)CC1=CC=C(C=C1)C(N(C)C)=O)C(=O)O MJYFVDNMTKLGTH-UHFFFAOYSA-N 0.000 abstract 1
- 208000020925 Bipolar disease Diseases 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 201000000980 schizophrenia Diseases 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- 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
- C07D209/96—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Procedimiento para preparar estos compuestos, a composiciones farmacéuticas que contienen uno o más de estos compuestos o sus sales, y a su uso para el tratamiento de la esquizofrenia, trastorno bipolar, u otros trastornos del sistema nervioso central. Reivindicacion 1: Un compuesto de formula (1), o una sal farmacéuticamente aceptable del mismo, en el que: R1 se selecciona de hidrogeno, -C(=O)CH3, alquilo, alquilo sustituido o -C(=O)CH3 sustituido con uno, dos o tres átomos de fluor; R2 y R3 se seleccionan independientemente de hidrogeno, alquilo, o alquilo sustituido; o R2 y R3 tomados juntos forman un grupo oxo; o R2 y R3 tomados junto con el átomo de carbono al que están unidos forman un anillo carbocíclico de 3, 4 o 5 miembros en el que uno de los átomos de carbono de anillo distinto de aquel al que están unidos R2 y R3 puede estar opcionalmente sustituido por un átomo de nitrogeno, oxígeno o azufre; siempre que cuando R4 y R5 tomados juntos forman un grupo oxo, R2 y R3 tomados juntos no forman un grupo oxo; R4 y R5 se seleccionan independientemente de hidrogeno, alquilo, o alquilo sustituido; o R4 y R5 tomados juntos forman un grupo oxo; o R4 y R5 tomados junto con el átomo de carbono al que están unidos forman un anillo carbocíclico de 3, 4 o 5 miembros en el que uno de los átomos de carbono de anillo distinto de aquel al que están unidos R4 y R5 puede estar opcionalmente sustituido por un átomo de nitrogeno, oxigeno o azufre; siempre que cuando R2 y R3 tomados juntos forman un grupo oxo, R4 y R5 tomados juntos no forman un grupo oxo; R6, R7 y R8 se seleccionan independientemente de hidrogeno, halogeno, ciano, alquilo, alquilo sustituido, alcoxilo o alcoxilo sustituido; R9 y R10 se seleccionan independientemente de hidrogeno, alquilo o alquilo sustituido; Z se selecciona de carbono, oxígeno o NR1; n es un numero entero y es 2, 3, 4 o 5; m es un numero entero y es 0, 1, 2, 3, o 4; D se selecciona de N, C o CH; siempre que cuando D es N, cada átomo de carbono unido a D está unido mediante un enlace sencillo; G es un grupo seleccionado de la formula (2), la formula (3) o la formula (4) siguientes; J y K se seleccionan independientemente de S, O, N, C o CH; L, M, V y W se seleccionan independientemente de N, C o CH; el anillo AA es un anillo carbocíclico saturado o insaturado de 5, 6 o 7 miembros, en el que uno, dos o tres de los átomos de carbono del anillo AA que no están compartidos con el anillo que contiene J y K o L y M pueden estar sustituidos, opcional e independientemente, por un átomo de nitrogeno, oxigeno o azufre; R11, R12, R13, R16, R17, R18 y R19 se seleccionan independientemente de hidrogeno, halogeno, -C(=O)CH3, alquilo, alquilo sustituido, alcoxilo, alcoxilo sustituido, arilo, arilo sustituido, ariloxilo, ariloxilo sustituido, grupo hidroxilo, N(R1)2 en el que ambos R1 en N(R1)2 pueden ser iguales o diferentes, o -C(=O)CH3 sustituido con uno, dos o tres átomos de fluor; siempre que cuando J es O o S, entonces R18 está ausente, y además siempre que cuando K es O o S, entonces R19 está ausente; R14 y R15 se seleccionan independientemente de hidrogeno, halogeno, ciano, oxo, hidroxilo, -C(=O)CH3, alquilo, alquilo sustituido, hidroxilo, alcoxilo, alcoxilo sustituido o -C(=O)CH3 sustituido con uno, dos o tres átomos de fluor, o N(R1)2 en el que ambos R1 en N(R1)2 pueden ser iguales o diferentes, y ----- representa un enlace sencillo o un doble enlace.Procedure for preparing these compounds, pharmaceutical compositions containing one or more of these compounds or their salts, and their use for the treatment of schizophrenia, bipolar disorder, or other disorders of the central nervous system. Claim 1: A compound of formula (1), or a pharmaceutically acceptable salt thereof, wherein: R1 is selected from hydrogen, -C (= O) CH3, alkyl, substituted alkyl or -C (= O) CH3 substituted with one, two or three fluorine atoms; R2 and R3 are independently selected from hydrogen, alkyl, or substituted alkyl; or R2 and R3 taken together form an oxo group; or R2 and R3 taken together with the carbon atom to which they are attached form a 3, 4 or 5 membered carbocyclic ring in which one of the ring carbon atoms other than that to which R2 and R3 are attached may optionally be substituted by a nitrogen, oxygen or sulfur atom; provided that when R4 and R5 taken together form an oxo group, R2 and R3 taken together do not form an oxo group; R4 and R5 are independently selected from hydrogen, alkyl, or substituted alkyl; or R4 and R5 taken together form an oxo group; or R4 and R5 taken together with the carbon atom to which they are attached form a 3, 4 or 5-membered carbocyclic ring in which one of the ring carbon atoms other than that to which R4 and R5 are attached may optionally be substituted by a nitrogen, oxygen or sulfur atom; provided that when R2 and R3 taken together form an oxo group, R4 and R5 taken together do not form an oxo group; R6, R7 and R8 are independently selected from hydrogen, halogen, cyano, alkyl, substituted alkyl, alkoxy or substituted alkoxy; R9 and R10 are independently selected from hydrogen, alkyl or substituted alkyl; Z is selected from carbon, oxygen or NR1; n is an integer and is 2, 3, 4 or 5; m is an integer and is 0, 1, 2, 3, or 4; D is selected from N, C or CH; provided that when D is N, each carbon atom attached to D is linked by a single bond; G is a group selected from the formula (2), the formula (3) or the following formula (4); J and K are independently selected from S, O, N, C or CH; L, M, V and W are independently selected from N, C or CH; the AA ring is a saturated, unsaturated carbocyclic ring of 5, 6 or 7 members, in which one, two or three of the carbon atoms of the AA ring that are not shared with the ring containing J and K or L and M they may be substituted, optionally and independently, by a nitrogen, oxygen or sulfur atom; R11, R12, R13, R16, R17, R18 and R19 are independently selected from hydrogen, halogen, -C (= O) CH3, alkyl, substituted alkyl, alkoxy, substituted alkoxy, aryl, substituted aryl, aryloxy, substituted aryloxy, group hydroxyl, N (R1) 2 in which both R1 in N (R1) 2 may be the same or different, or -C (= O) CH3 substituted with one, two or three fluorine atoms; whenever when J is O or S, then R18 is absent, and also whenever when K is O or S, then R19 is absent; R14 and R15 are independently selected from hydrogen, halogen, cyano, oxo, hydroxyl, -C (= O) CH3, alkyl, substituted alkyl, hydroxyl, alkoxy, substituted alkoxy or -C (= O) CH3 substituted with one, two or three fluorine atoms, or N (R1) 2 in which both R1 in N (R1) 2 can be the same or different, and ----- represents a single bond or a double bond.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82276706P | 2006-08-18 | 2006-08-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR062405A1 true AR062405A1 (en) | 2008-11-05 |
Family
ID=38740296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP070103649A AR062405A1 (en) | 2006-08-18 | 2007-08-16 | ISOINDOL DERIVATIVES |
Country Status (2)
| Country | Link |
|---|---|
| AR (1) | AR062405A1 (en) |
| WO (1) | WO2008020306A2 (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20110016891A (en) * | 2008-05-09 | 2011-02-18 | 에모리 유니버시티 | Nmda receptor antagonists for the treatment of neuropsychiatric disorders |
| JP5656364B2 (en) * | 2009-04-20 | 2015-01-21 | 株式会社トクヤマ | Method for producing naphthopyran derivatives |
| US9156822B2 (en) | 2010-07-02 | 2015-10-13 | The University Of North Carolina At Chapel Hill | Functionally selective ligands of dopamine D2 receptors |
| GB201101959D0 (en) | 2011-02-04 | 2011-03-23 | Univ Nottingham | Novel ether linked compoundsand improved treatments for cardiac and cardiovascular disease |
| WO2012159662A1 (en) * | 2011-05-24 | 2012-11-29 | Universita' Degli Studi Di Bari | New 1-arylpiperazinic ligands of 5-ht7 receptor and use thereof |
| CA2890009C (en) * | 2012-11-08 | 2017-11-28 | Pfizer Inc. | Heteroaromatic compounds and their use as dopamine d1 ligands |
| JP6440625B2 (en) | 2012-11-14 | 2018-12-19 | ザ・ジョンズ・ホプキンス・ユニバーシティー | Methods and compositions for treating schizophrenia |
| MA41169A (en) * | 2014-12-17 | 2017-10-24 | Acraf | WIDE-SPECTRUM ANTIBACTERIAL COMPOUNDS |
| CN105153013B (en) * | 2015-09-16 | 2017-12-29 | 苏州昊帆生物科技有限公司 | The synthetic method of the ketone of 6 bromine isoindoline 1 |
| CN106749219A (en) * | 2015-11-20 | 2017-05-31 | 江苏恩华药业股份有限公司 | A kind of lactam derivative and its application |
| CN105859732B (en) * | 2016-04-11 | 2018-04-06 | 浙江海正药业股份有限公司 | The technique for preparing AD 35 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2551346A1 (en) * | 2003-12-31 | 2005-07-21 | Warner-Lambert Company Llc | N-substituted piperidine and piperazine derivatives |
| TWI329641B (en) * | 2005-08-31 | 2010-09-01 | Otsuka Pharma Co Ltd | (benzo[b]thiophen-4-yl)piperazine compounds, pharmaceutical compositions comprising the same, uses of the same and processes for preparing the same |
-
2007
- 2007-08-15 WO PCT/IB2007/002469 patent/WO2008020306A2/en active Application Filing
- 2007-08-16 AR ARP070103649A patent/AR062405A1/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008020306A2 (en) | 2008-02-21 |
| WO2008020306A3 (en) | 2008-11-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |