CN102260290A - Quinolinone compounds, and application thereof in preparing antipsychotic drugs - Google Patents
Quinolinone compounds, and application thereof in preparing antipsychotic drugs Download PDFInfo
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- CN102260290A CN102260290A CN2010101812639A CN201010181263A CN102260290A CN 102260290 A CN102260290 A CN 102260290A CN 2010101812639 A CN2010101812639 A CN 2010101812639A CN 201010181263 A CN201010181263 A CN 201010181263A CN 102260290 A CN102260290 A CN 102260290A
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- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title abstract 5
- 239000000164 antipsychotic agent Substances 0.000 title 1
- 239000003814 drug Substances 0.000 claims abstract description 9
- 208000024891 symptom Diseases 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- -1 C12 secondary amine Chemical class 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 208000028017 Psychotic disease Diseases 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005322 morpholin-1-yl group Chemical group 0.000 claims description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 101150063022 CHRD gene Proteins 0.000 claims description 2
- 101100274355 Danio rerio chd gene Proteins 0.000 claims description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 208000024732 dysthymic disease Diseases 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- 230000007547 defect Effects 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract description 10
- 239000004031 partial agonist Substances 0.000 abstract description 6
- 230000003042 antagnostic effect Effects 0.000 abstract description 3
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 abstract description 2
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 abstract description 2
- 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 abstract description 2
- 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 abstract description 2
- 208000019901 Anxiety disease Diseases 0.000 abstract description 2
- 230000036506 anxiety Effects 0.000 abstract description 2
- 102000004980 Dopamine D2 Receptors Human genes 0.000 abstract 1
- 108090001111 Dopamine D2 Receptors Proteins 0.000 abstract 1
- 230000007278 cognition impairment Effects 0.000 abstract 1
- 108020003175 receptors Proteins 0.000 abstract 1
- 102000005962 receptors Human genes 0.000 abstract 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 3
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 2
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 2
- 208000028698 Cognitive impairment Diseases 0.000 description 2
- 101150049660 DRD2 gene Proteins 0.000 description 2
- CTENFNNZBMHDDG-UHFFFAOYSA-N Dopamine hydrochloride Chemical compound Cl.NCCC1=CC=C(O)C(O)=C1 CTENFNNZBMHDDG-UHFFFAOYSA-N 0.000 description 2
- 108050004812 Dopamine receptor Proteins 0.000 description 2
- 102000015554 Dopamine receptor Human genes 0.000 description 2
- 208000027776 Extrapyramidal disease Diseases 0.000 description 2
- 230000008484 agonism Effects 0.000 description 2
- 208000010877 cognitive disease Diseases 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 102000003946 Prolactin Human genes 0.000 description 1
- 108010057464 Prolactin Proteins 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 102000030621 adenylate cyclase Human genes 0.000 description 1
- 108060000200 adenylate cyclase Proteins 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 230000002197 limbic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229940097325 prolactin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention relates to quinolinone compounds which can be a partial agonist for dopamine D2 receptor and also a partial agonist for 5-hydroxytryptamine (5-HT) receptor. The quinolinone compounds have a partial agitating action on 5-HT1A receptor, and have an antagonistic action on 5-HT2A. Therefore, the quinolinone compounds or medicine composition containing the quinolinone compounds can be used for improving anxiety, depression, cognitive deficit and negative symptoms.
Description
Technical field
The present invention relates to quinoline quinoline ketone compounds and they in the preparation psychosis medicine purposes in the dysthymia disorders medicine particularly.
Background technology
Dopamine HCL is present in maincenter and peripheral tissues widely as the 3rd acacatechin amine neurotransmitter, and is synthesized at the different sites of maincenter and peripheral tissues.Dopamine Receptors can be divided into D1 and two families of D2; Wherein D1 family comprises D1 and two hypotypes of D5, but its activated adenyl cyclase; D2 family comprises D2, D3 and three hypotypes of D4.Dopamine Receptors plays a major role in the effect of intermediary's antipsychotic drug.At the D2 acceptor, D2 acceptor branch agonist centering limbic brain path can produce functional antagonistic action, can effectively improve the positive symptom that schizophrenia causes because of the D2 over-activity; Centering cortex path can produce functional agonism, improves the caused negative symptoms of D2 hypofunction, cognitive impairment; To the nigrostriatum path, partial agonist is blocked the nigrostriatum path fully unlike antagonist, seldom causes The extrapyramidal symptoms (EPS); To tubercle funnel path,, cause that seldom prolactin level raises because of it is not the activity of blocking tubercle funnel path Dopamine HCL fully.
Serotonin is very high at cerebral cortex and nerve synapse intensive amount, is to regulate neururgic a kind of important substance, and it can have different pharmacological actions by activating different 5-HT receptor subtypes.
Summary of the invention
Technical problem to be solved by this invention provide a kind of quinoline the quinoline ketone compounds, it can be used as the optionally partial agonist of target 5-hydroxytryptamine receptor, d2 dopamine receptor.
For solving above technical problem, the present invention takes following technical scheme:
Compound with general formula (I):
In the formula (I):
R
01, R
02, R
03, R
04, R
05, R
06, R
07, R
08, R
09, be hydrogen or deuterium independently;
R
NFor being selected from a kind of in the following groups:
H、OH、CH
2Ra、OCH
2Ra、COR
c、CHRdRi、(CH
2)nRj、
And
Wherein:
Ra represents H; C1～C5 alkyl; C1～C8 alkyl that one or more fluorine atoms replace; Phenyl, it is perhaps replaced by one or more groups that are selected from fluorine, chlorine, bromine, C1～C6 alkoxyl group, C1～C6 sulfydryl, C1～C6 amido for not replacing; Perhaps pyridyl, it is perhaps replaced by one or more groups that are selected from fluorine, chlorine, bromine, C1～C6 alkoxyl group, C1～C6 sulfydryl, C1～C6 amido for replacing;
R
cExpression H, CH
2Ra, OCH
2Ra, C2～C12 secondary amine, CHRd (NHRe), NReCHRd (COORg), 2-furyl, 1-connection hexahydropyridine base or 1-morpholinyl;
Rd is H or C1～C6 alkyl;
Re is H, CH
2Rf, C1～C7 carbonyl or C1～C7 ester group;
Rg represents H or CH
2Rf;
Rf represents C1～C5 alkyl; C1～C8 alkyl that one or more fluorine atoms replace; Phenyl, it is perhaps replaced by one or more groups that are selected from fluorine, chlorine, bromine, C1～C6 alkoxyl group, C1～C6 sulfydryl, C1～C6 amido for not replacing; Perhaps Rf represents pyridyl, and it is perhaps replaced by one or more groups that are selected from fluorine, chlorine, bromine, C1～C6 alkoxyl group, C1～C6 sulfydryl, C1～C6 amido for not replacing;
Ri represents NReCHRd (COORg), OCOCHRd (NHRe) or OCOORg;
Rj represents 2-furyl, 1-connection hexahydropyridine base or 1-morpholinyl;
N is the integer between 1～6, and Y represents C1～C6 alkyl.
According to the present invention, n is preferably 2 or 3.
According to the present invention, representational compound has the compound of formula II, formula III, formula IV, formula (V), formula VI, formula (VII) and formula (VIII) expression.
According to the present invention, described pharmacologically acceptable salt includes but not limited to hydrochloride, phosphoric acid salt, vitriol, acetate, maleate, benzene sulfonate, toluenesulfonate, fumarate, tartrate etc.
Because the enforcement of above technical scheme, the present invention compared with prior art has following advantage:
The quinoline that the present invention relates to the quinoline ketone compounds be partial agonist at d2 dopamine receptor, simultaneously, its still be serotonin (5-HT) acceptor and partial agonist, the 5-HT1A acceptor is had the part agonism, 5-HT2A is had antagonistic action.Therefore, the present invention or comprise pharmaceutical composition of the present invention and can be used for improving schizoid anxiety, depression, cognitive impairment and negative symptoms.
Embodiment
The present invention will be further described in detail below in conjunction with specific embodiment, but the present invention is not limited to following examples.
Embodiment 1
The compound that present embodiment provides a kind of formula II to represent:
Embodiment 2
The compound that present embodiment provides a kind of formula III to represent:
Embodiment 3
The compound that present embodiment provides a kind of formula IV to represent:
Embodiment 4
Present embodiment provides the compound of a kind of formula (V) expression:
Embodiment 5
The compound that present embodiment provides a kind of formula VI to represent:
Embodiment 6
Present embodiment provides the compound of a kind of formula (VII) expression:
Embodiment 7
Present embodiment provides the compound of a kind of formula (VIII) expression:
Claims (5)
1. the compound and the pharmacologically acceptable salt thereof that have general formula (I):
In the formula (I):
R
01, R
02, R
03, R
04, R
05, R
06, R
07, R
08, R
09, be hydrogen or deuterium independently;
R
NFor being selected from a kind of in the following groups:
H、OH、CH
2Ra、OCH
2Ra、CORc、CHRdRi、(CH
2)nRj、
Wherein:
Ra represents H; C1～C5 alkyl; C1～C8 alkyl that one or more fluorine atoms replace; Phenyl, it is perhaps replaced by one or more groups that are selected from fluorine, chlorine, bromine, C1～C6 alkoxyl group, C1～C6 sulfydryl, C1～C6 amido for not replacing; Perhaps pyridyl, it is perhaps replaced by one or more groups that are selected from fluorine, chlorine, bromine, C1～C6 alkoxyl group, C1～C6 sulfydryl, C1～C6 amido for replacing;
Rc represents H, CH
2Ra, OCH
2Ra, C2～C12 secondary amine, CHRd (NHRe), NReCHRd (COORg), 2-furyl, 1-connection hexahydropyridine base or 1-morpholinyl;
Rd is H or C 1～C6 alkyl;
Re is H, CH
2Rf, C1～C7 carbonyl or C1～C7 ester group;
Rg represents H or CH
2Rf;
Rf represents C1～C5 alkyl; C1～C8 alkyl that one or more fluorine atoms replace; Phenyl, it is perhaps replaced by one or more groups that are selected from fluorine, chlorine, bromine, C1～C6 alkoxyl group, C1～C6 sulfydryl, C1～C6 amido for not replacing; Perhaps Rf represents pyridyl, and it is perhaps replaced by one or more groups that are selected from fluorine, chlorine, bromine, C1～C6 alkoxyl group, C1～C6 sulfydryl, C1～C6 amido for not replacing;
Ri represents NReCHRd (COORg), OCOCHRd (NHRe) or OCOORg;
Rj represents 2-furyl, 1-connection hexahydropyridine base or 1-morpholinyl;
N is the integer between 1～6, and Y represents C1～C6 alkyl.
2. compound according to claim 1 and pharmacologically acceptable salt thereof is characterized in that: described n is 2 or 3.
3. compound according to claim 1 and pharmacologically acceptable salt thereof is characterized in that: described compound is a kind of in the compound of formula II, formula III, formula IV, formula V, formula VI, formula (VII) and formula (VIII) expression.
4. but described compound of claim 1 and drug salts thereof the purposes in preparation psychosis medicine.
5. purposes according to claim 4 is characterized in that: described psychosis medicine is for improving the medicine of dysthymia disorders, schizophrenia positive symptom, negative symptoms, anxiety-depression, cognitive defect.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010101812639A CN102260290A (en) | 2010-05-25 | 2010-05-25 | Quinolinone compounds, and application thereof in preparing antipsychotic drugs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010101812639A CN102260290A (en) | 2010-05-25 | 2010-05-25 | Quinolinone compounds, and application thereof in preparing antipsychotic drugs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102260290A true CN102260290A (en) | 2011-11-30 |
Family
ID=45007150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010101812639A Pending CN102260290A (en) | 2010-05-25 | 2010-05-25 | Quinolinone compounds, and application thereof in preparing antipsychotic drugs |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102260290A (en) |
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| US10112903B2 (en) | 2009-06-25 | 2018-10-30 | Alkermes Pharma Ireland Limited | Heterocyclic compounds for the treatment of neurological and psychological disorders |
| US10175257B2 (en) | 2012-08-21 | 2019-01-08 | Janssen Pharmaceutica Nv | Antibodies to aripiprazole and use thereof |
| US10379105B2 (en) | 2012-08-21 | 2019-08-13 | Janssen Pharmaceutica Nv | Antibodies to aripiprazole haptens and use thereof |
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| CN113181183A (en) * | 2021-05-20 | 2021-07-30 | 桂林医学院 | Application of cabergoline in preparing medicine composition for treating anxiety disorder |
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2010
- 2010-05-25 CN CN2010101812639A patent/CN102260290A/en active Pending
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| WO2014031584A1 (en) * | 2012-08-21 | 2014-02-27 | Janssen Pharmaceutica Nv | Haptens of aripiprazole and their use in immunoassays |
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| CN104822660A (en) * | 2012-08-21 | 2015-08-05 | 詹森药业有限公司 | Aripiprazole hapten and its application in immunoassay |
| US11105793B2 (en) | 2012-08-21 | 2021-08-31 | Janssen Pharmaceutica Nv | Antibodies to aripiprazole haptens and use thereof |
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| JP2015527363A (en) * | 2012-08-21 | 2015-09-17 | ヤンセン ファーマシューティカ エヌ．ベー． | Aripiprazole haptens and their use in immunoassays |
| US11273158B2 (en) | 2018-03-05 | 2022-03-15 | Alkermes Pharma Ireland Limited | Aripiprazole dosing strategy |
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| CN113181183A (en) * | 2021-05-20 | 2021-07-30 | 桂林医学院 | Application of cabergoline in preparing medicine composition for treating anxiety disorder |
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Application publication date: 20111130 |