ME02193B - Derivati imidazola kao inhibitori enzima pde10a - Google Patents
Derivati imidazola kao inhibitori enzima pde10aInfo
- Publication number
- ME02193B ME02193B MEP-2015-130A MEP13015A ME02193B ME 02193 B ME02193 B ME 02193B ME P13015 A MEP13015 A ME P13015A ME 02193 B ME02193 B ME 02193B
- Authority
- ME
- Montenegro
- Prior art keywords
- group
- compound
- ethyl
- triazolo
- imidazo
- Prior art date
Links
- 239000002532 enzyme inhibitor Substances 0.000 title 1
- 150000002460 imidazoles Chemical class 0.000 title 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims 4
- 239000003176 neuroleptic agent Substances 0.000 claims 4
- 208000020016 psychiatric disease Diseases 0.000 claims 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 230000000626 neurodegenerative effect Effects 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- -1 tetrahydropyran-4-yl-methyl Chemical group 0.000 claims 2
- UXSSEAFAQUPALG-UHFFFAOYSA-N 2-[2-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)ethenyl]-5h-imidazo[2,1-a]isoindole Chemical compound C1=CC=C2C3=NC(C=CC=4N=C5C(C)=NC=C(N5N=4)C)=CN3CC2=C1 UXSSEAFAQUPALG-UHFFFAOYSA-N 0.000 claims 1
- KCEGJZKYKCTWDC-UHFFFAOYSA-N 2-[2-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)ethyl]-5h-imidazo[2,1-a]isoindole Chemical compound C1=CC=C2C3=NC(CCC4=NN5C(C)=CC=C(C5=N4)C)=CN3CC2=C1 KCEGJZKYKCTWDC-UHFFFAOYSA-N 0.000 claims 1
- GXEQKJXPCPLDJR-UHFFFAOYSA-N 2-[2-(5-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)ethyl]-5h-imidazo[2,1-a]isoindole Chemical compound C1=CC=C2C3=NC(CCC=4N=C5C=CC=C(N5N=4)C)=CN3CC2=C1 GXEQKJXPCPLDJR-UHFFFAOYSA-N 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- OVGBICIMKVMTBR-UHFFFAOYSA-N 5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine Chemical compound CC1=CN=C(C)C2=NC=NN12 OVGBICIMKVMTBR-UHFFFAOYSA-N 0.000 claims 1
- OONLJFQZTUPWQV-UHFFFAOYSA-N 5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC1=CC=C(C)N2N=CN=C12 OONLJFQZTUPWQV-UHFFFAOYSA-N 0.000 claims 1
- HRUGYRNGCHJAHA-UHFFFAOYSA-N 5-methyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC1=CC=CC2=NC=NN12 HRUGYRNGCHJAHA-UHFFFAOYSA-N 0.000 claims 1
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 208000024254 Delusional disease Diseases 0.000 claims 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 229960004372 aripiprazole Drugs 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229960004170 clozapine Drugs 0.000 claims 1
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 208000026725 cyclothymic disease Diseases 0.000 claims 1
- 229910052805 deuterium Inorganic materials 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229960003878 haloperidol Drugs 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 150000002537 isoquinolines Chemical class 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229960005017 olanzapine Drugs 0.000 claims 1
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims 1
- 229950009875 osanetant Drugs 0.000 claims 1
- DZOJBGLFWINFBF-UMSFTDKQSA-N osanetant Chemical compound C([C@](C1)(CCCN2CCC(CC2)(N(C(C)=O)C)C=2C=CC=CC=2)C=2C=C(Cl)C(Cl)=CC=2)CCN1C(=O)C1=CC=CC=C1 DZOJBGLFWINFBF-UMSFTDKQSA-N 0.000 claims 1
- 208000002851 paranoid schizophrenia Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229960004431 quetiapine Drugs 0.000 claims 1
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 claims 1
- 229960001534 risperidone Drugs 0.000 claims 1
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims 1
- 208000022610 schizoaffective disease Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 230000000698 schizophrenic effect Effects 0.000 claims 1
- 229960000652 sertindole Drugs 0.000 claims 1
- GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 claims 1
- 229960000607 ziprasidone Drugs 0.000 claims 1
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
-
- 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
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Claims (12)
1. Jedinjenje strukture Iu kojojn je 0 ili 1, X je CH; R1 i R2 su svaki nezavisno odabrani iz grupe koju čine H; C1-C6 alkil; C1-C6 alkil(C3-C8)cikloalkil; C1-C6 hidroksialkil; C1-C6 alkoksi; CH2CN; CH2C(O)NH2; C1-C6 arilalkil; i C1-C6 alkil-heterocikloalkil; halogen; i hidroksi;R3 i R4 su svaki nezavisno odabrani iz grupe koju čine H, OH, F, CH3 i OCH3;L je veznik odabran iz grupe koju čine -CH2-CH2-, -CH = CH-, -CH2-S-, i -S-CH2-; iHET je heteroaromatična grupa odabrana iz grupe koju čine [1,2,4]triazol[1,5-a]pirazin, [1,2,4]triazol[1,5-a]piridin i [1,2,4]triazol[1,5-a]pirimidin,HET grupa može biti supstituisana sa do tri supstituenta R5, R6 i R7 pojedinačno izabrana od grupe koju čine H, CH3, i OCH3;i njegovi tautomeri i farmaceutski prihvatljive adicione soli sa kiselinama, i njegovi polimorfni oblici.
2. Jedinjenje prema zahtevu 1 u kojem je n = 0.
3. Jedinjenje prema zahtevu 1 u kojem a) C1-C6 alkil je odabran iz grupe koju čine metil, etil, 1-propil, 2-propil, izobutil; b) C1-C6 alkil(C3-C8)cikloalkil je ciklopropilmetil; c) C1-C6 hidroksialkil je hidroksietil d) C1-C6 alkoksi je izabran iz grupe koju čine metoksi i etoksi e) C1-C6 arilalkil je izabran iz grupe koju čine benzil i 4-hlorobenzil f) C1-C6 alkil-heterocikloalkil je odabran iz grupe koju čine tetrahidropiran-4-il-metil i 2-morfolin-4-il-etil g) halogen je F.
4. Jedinjenje prema zahtevu 3 u kojem je HET izabrana iz grupe koju čine 5,8-dimetil-[1,2,4]triazol[1,5-a]pirazin; 5,8-dimetil-[1,2,4]triazol[1,5-a]piridin, 5-metil-[1,2,4]triazol[1,5-a]piridin, i (5-metil-[1,2,4]triazol[1,5-a]pirazin-8-il)-metanol.
5. Jedinjenje prema zahtevu 1, gde su R1 i R2 nezavisno izabrani iz grupe koju čine H, OH, F, CH3 i OCH3.
6. Jedinjenje prema zahtevu 1 u kojem su jedan ili više atoma vodonika jedinjenja zamenjeni deuterijumom.
7. Jedinjenje prema zahtevu 1, u kojem je jedinjenje izabrano iz grupe koju čine 2-[2-(5,8-dimetil-[1,2,4]triazol[1,5-a]pirazin-2-il)-etil]-5H-imidazo[2,1-a]izoindol; 2-[2-(5,8-dimetil-[1,2,4]triazol[1,5-a]piridin-2-il)-etil]-5H-imidazo[2,1-a]izoindol; 2-[2-(5-metil-[1,2,4]triazol[1,5-a]piridin-2-il)-etil]-5H-imidazo[2,1-a]izoindol; 2-[2-(5,8-dimetil-[1,2,4]triazol[1,5-a]pirazin-2-il)-vinil]-5H-imidazo[2,1-a]izoindol; {2-[2-(5H-imidazo[2,1-a]izoindol-2-il)-etil]-5-metil-[1,2,4]triazol[1,5-a]pirazin-8-il} metanol; i 2-[2-(5,8-dimetil-[1,2,4]triazol[1,5-a]pirazin-2-il)-etil]-7-fluoro-5H-imidazo[2,1-a]izoindol, 2-[2-(5,8-dimetil-[1,2,4]triazol[1,5-a]pirazin-2-il)-etil]-5,6-dihidro-imidazo[2, 1-a]izokvinolini njihove farmaceutski prihvatljive adicione soli sa kiselinama.
8. Jedinjenje prema bilo kom od zahteva 1 do 7 kao lek.
9. Jedinjenje prema bilo kom od zahteva 1 do 8 za primenu u tretiranju neurodegenerativnih ili psihijatrijskih poremećaja, samo ili u kombinaciji sa jednim ili više neuroleptičnim agensima.
10. Jedinjenje prema zahtevu 9 za primenu u tretiranju neurodegenerativnih ili psihijatrijskih poremećaja, u kombinaciji sa jednim ili više neuroleptičnim agensima, pri čemu je neuroleptični agens odabran iz grupe koja se sastoji od grupe koja sadrži sertindol, olanzapin, risperidon, kvetiapin, aripiprazol, haloperidol, klozapin, ziprasidon i osanetant.
11. Jedinjenje prema zahtevu 9 za primenu u tretiranju neurodegenerativnih ili psihijatrijskih poremećaja, u kombinaciji sa jednim ili više neuroleptičnim agensima, gde je neurodegenerativni poremećaj Hantingtonova bolest, a psihijatrijski poremećaj je odabran iz grupe koju čine šizofrenija, poremećaj šizofrenog oblika; šizoafektivni poremećaj; poremećaj zablude; bipolarni poremećaj, i ciklotimični poremećaj.
12. Farmaceutska kompozicija koja obuhvata terapeutski efikasnu količinu jedinjenja prema bilo kom od zahteva 1 do 8, i jedan ili više farmaceutski prihvatljivih nosača, razblaživača i ekscipijenata.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41535610P | 2010-11-19 | 2010-11-19 | |
| DKPA201001045 | 2010-11-19 | ||
| PCT/DK2011/000136 WO2012065612A1 (en) | 2010-11-19 | 2011-11-18 | Imidazole derivatives as pde10a enzyme inhibitors |
| EP11793325.9A EP2640731B9 (en) | 2010-11-19 | 2011-11-18 | Imidazole derivatives as pde10a enzyme inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ME02193B true ME02193B (me) | 2016-02-20 |
Family
ID=45217102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2015-130A ME02193B (me) | 2010-11-19 | 2011-11-18 | Derivati imidazola kao inhibitori enzima pde10a |
Country Status (32)
| Country | Link |
|---|---|
| EP (1) | EP2640731B9 (me) |
| JP (1) | JP5937608B2 (me) |
| KR (1) | KR101916487B1 (me) |
| CN (1) | CN103328487B (me) |
| AP (1) | AP3342A (me) |
| AR (1) | AR083926A1 (me) |
| AU (1) | AU2011331607B2 (me) |
| BR (1) | BR112013012378A2 (me) |
| CA (1) | CA2817663C (me) |
| CR (1) | CR20130226A (me) |
| DK (1) | DK2640731T3 (me) |
| EA (1) | EA027082B1 (me) |
| EC (1) | ECSP13012698A (me) |
| ES (1) | ES2547090T3 (me) |
| GE (1) | GEP20156346B (me) |
| GT (1) | GT201300130A (me) |
| HU (1) | HUE025596T2 (me) |
| JO (1) | JO3089B1 (me) |
| ME (1) | ME02193B (me) |
| MY (1) | MY163327A (me) |
| NZ (1) | NZ610353A (me) |
| PE (1) | PE20141534A1 (me) |
| PH (1) | PH12013500968A1 (me) |
| PL (1) | PL2640731T3 (me) |
| PT (1) | PT2640731E (me) |
| RS (1) | RS54210B1 (me) |
| SG (1) | SG190282A1 (me) |
| SI (1) | SI2640731T1 (me) |
| TW (1) | TWI541245B (me) |
| UA (1) | UA112065C2 (me) |
| WO (1) | WO2012065612A1 (me) |
| ZA (1) | ZA201303607B (me) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8552045B2 (en) | 2010-11-19 | 2013-10-08 | H. Lundbeck A/S | Tricyclic imidazole compounds as PDE10 inhibitors |
| CN107141309A (zh) * | 2011-01-11 | 2017-09-08 | 桑诺维恩药品公司 | 杂芳基化合物及其使用方法 |
| WO2013045607A1 (en) * | 2011-09-30 | 2013-04-04 | H. Lundbeck A/S | Quinazoline linked heteroaromatic tricycle derivatives as pde10a enzyme inhibitors |
| WO2013107856A1 (en) * | 2012-01-20 | 2013-07-25 | H. Lundbeck A/S | Imidazole derivatives as pde10a enzyme inhibitors |
| KR20150021120A (ko) | 2012-06-19 | 2015-02-27 | 선오비온 파마슈티컬스 인코포레이티드 | 헤테로아릴 화합물 및 이의 이용 방법 |
| CN103435617B (zh) * | 2013-08-22 | 2016-04-27 | 南京华安药业有限公司 | 一种6,7-二氢-5H-吡咯并[1,2-a]咪唑-2-甲醛的合成方法 |
| JO3627B1 (ar) | 2015-04-30 | 2020-08-27 | H Lundbeck As | إيميدازو بيرازينونات على هيئة مثبطات pde1 |
| TWI729109B (zh) | 2016-04-12 | 2021-06-01 | 丹麥商Ｈ 朗德貝克公司 | 作爲PDE1抑制劑的1,5-二氫-4H-吡唑并[3,4-d]嘧啶-4-酮和1,5-二氫-4H-吡唑并[4,3-c]吡啶-4-酮 |
| EP3529250B1 (en) | 2016-10-18 | 2023-12-06 | H. Lundbeck A/S | Imidazopyrazinones, pyrazolopyrimidinones and pyrazolopyridinones as pde1 inhibitors |
| BR112018013084A2 (pt) | 2016-10-28 | 2018-12-11 | H Lundbeck As | tratamentos de combinação compreendendo a administração de imidazopirazinonas |
| SG11201903770UA (en) | 2016-10-28 | 2019-05-30 | H Lundbeck As | Combination treatments comprising imidazopyrazinones for the treatment of psychiatric and/or cognitive disorders |
| TW202031250A (zh) | 2018-11-06 | 2020-09-01 | 丹麥商Ｈ 朗德貝克公司 | 用於治療負性症狀和認知損傷之pde10a抑制劑 |
| CN109776527A (zh) * | 2019-02-21 | 2019-05-21 | 药雅科技(上海)有限公司 | 一种5-溴-7-氮杂吲哚的合成方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8307865D0 (en) | 1983-03-22 | 1983-04-27 | Fujisawa Pharmaceutical Co | Benzimidazole derivatives |
| US5571775A (en) | 1994-07-11 | 1996-11-05 | Dowelanco | N-aryl[1,2,4]triazolo[1,5-a]pyridine-2-sulfonamide herbicides |
| IL149106A0 (en) | 2001-04-20 | 2002-11-10 | Pfizer Prod Inc | Therapeutic use of selective pde10 inhibitors |
| US20030032579A1 (en) | 2001-04-20 | 2003-02-13 | Pfizer Inc. | Therapeutic use of selective PDE10 inhibitors |
| CA2530114A1 (en) | 2003-06-30 | 2005-01-13 | Altana Pharma Ag | Pyrrolo-dihydroisoquinoline derivatives as pde10 inhibitors |
| KR20060030483A (ko) | 2003-06-30 | 2006-04-10 | 알타나 파마 아게 | Ｐｄｅ10 억제제로서 피롤로디히드로이소퀴놀린 |
| WO2005012485A2 (en) | 2003-07-31 | 2005-02-10 | Bayer Pharmaceuticals Corporation | Methods for treating diabetes and related disorders using pde10a inhibitors |
| JP2007523152A (ja) | 2004-02-18 | 2007-08-16 | ファイザー・プロダクツ・インク | キナゾリンおよびイソキノリンのテトラヒドロイソキノリニル誘導体 |
| EP1755611A1 (en) | 2004-06-07 | 2007-02-28 | Pfizer Products Inc. | Phosphodiesterase 10 inhibition as treatment for obesity-related and metabolic syndrome-related conditions |
| US20060019975A1 (en) | 2004-07-23 | 2006-01-26 | Pfizer Inc | Novel piperidyl derivatives of quinazoline and isoquinoline |
| AU2005282721A1 (en) | 2004-09-03 | 2006-03-16 | Memory Pharmaceuticals Corporation | 4-substituted 4, 6-dialkoxy-cinnoline derivatives as phospodiesterase 10 inhibitors for the treatment of psychiatric or neurological syndroms |
| WO2010145668A1 (en) * | 2009-06-19 | 2010-12-23 | H. Lundbeck A/S | Novel phenylimidazole derivative as pde10a enzyme inhibitor |
| US8133897B2 (en) | 2008-06-20 | 2012-03-13 | H. Lundbeck A/S | Phenylimidazole derivatives as PDE10A enzyme inhibitors |
| TWI501965B (zh) | 2008-06-20 | 2015-10-01 | Lundbeck & Co As H | 作為ｐｄｅ１０ａ酵素抑制劑之新穎苯基咪唑衍生物 |
| TW201200516A (en) * | 2009-12-17 | 2012-01-01 | Lundbeck & Co As H | Phenylimidazole derivatives comprising an ethynylene linker as PDE10A enzyme inhibitors |
| TWI485151B (zh) * | 2009-12-17 | 2015-05-21 | Lundbeck & Co As H | 作為ｐｄｅ１０ａ酵素抑制劑之雜芳香族苯基咪唑衍生物 |
| TWI481607B (zh) * | 2009-12-17 | 2015-04-21 | Lundbeck & Co As H | 作為ｐｄｅ１０ａ酵素抑制劑的２－芳基咪唑衍生物 |
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