CA2673435A1 - Succinate salt of 2-((4-(1-methyl-4-(pyridin-4-yl)-1h-pyrazol-3-yl) phenoxy)methyl)quinoline - Google Patents
Succinate salt of 2-((4-(1-methyl-4-(pyridin-4-yl)-1h-pyrazol-3-yl) phenoxy)methyl)quinoline Download PDFInfo
- Publication number
- CA2673435A1 CA2673435A1 CA002673435A CA2673435A CA2673435A1 CA 2673435 A1 CA2673435 A1 CA 2673435A1 CA 002673435 A CA002673435 A CA 002673435A CA 2673435 A CA2673435 A CA 2673435A CA 2673435 A1 CA2673435 A1 CA 2673435A1
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- CA
- Canada
- Prior art keywords
- disorder
- salt
- dementia
- delusional
- succinate salt
- 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
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- 150000003890 succinate salts Chemical class 0.000 title claims abstract 12
- AZEXWHKOMMASPA-UHFFFAOYSA-N 2-{[4-(1-methyl-4-pyridin-4-yl-1h-pyrazol-3-yl)phenoxy]methyl}quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(C)C=C1C1=CC=NC=C1 AZEXWHKOMMASPA-UHFFFAOYSA-N 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 3
- 239000003937 drug carrier Substances 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims 12
- 208000028017 Psychotic disease Diseases 0.000 claims 9
- 206010012289 Dementia Diseases 0.000 claims 7
- 208000024254 Delusional disease Diseases 0.000 claims 6
- 230000004770 neurodegeneration Effects 0.000 claims 6
- 208000002851 paranoid schizophrenia Diseases 0.000 claims 6
- 208000020401 Depressive disease Diseases 0.000 claims 5
- 208000011963 Substance-induced psychotic disease Diseases 0.000 claims 5
- 231100000393 Substance-induced psychotic disorder Toxicity 0.000 claims 5
- 208000019901 Anxiety disease Diseases 0.000 claims 4
- 208000019022 Mood disease Diseases 0.000 claims 4
- 208000016285 Movement disease Diseases 0.000 claims 4
- 201000002545 drug psychosis Diseases 0.000 claims 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims 4
- 206010013663 drug dependence Diseases 0.000 claims 3
- 208000024714 major depressive disease Diseases 0.000 claims 3
- 230000036651 mood Effects 0.000 claims 3
- 238000000634 powder X-ray diffraction Methods 0.000 claims 3
- 208000011117 substance-related disease Diseases 0.000 claims 3
- 206010065040 AIDS dementia complex Diseases 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000005314 Multi-Infarct Dementia Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 201000004810 Vascular dementia Diseases 0.000 claims 2
- 206010007776 catatonia Diseases 0.000 claims 2
- 230000002490 cerebral effect Effects 0.000 claims 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
- 229910052802 copper Inorganic materials 0.000 claims 2
- 239000010949 copper Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 208000022821 personality disease Diseases 0.000 claims 2
- 230000005855 radiation Effects 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 230000008733 trauma Effects 0.000 claims 2
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
- 208000031091 Amnestic disease Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 206010012218 Delirium Diseases 0.000 claims 1
- 206010049669 Dyscalculia Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 208000013016 Hypoglycemia Diseases 0.000 claims 1
- 208000020358 Learning disease Diseases 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000036626 Mental retardation Diseases 0.000 claims 1
- 208000001089 Multiple system atrophy Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 101710138657 Neurotoxin Proteins 0.000 claims 1
- 206010070606 Post stroke depression Diseases 0.000 claims 1
- 208000027030 Premenstrual dysphoric disease Diseases 0.000 claims 1
- 208000022372 Reading disease Diseases 0.000 claims 1
- 208000020186 Schizophreniform disease Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 230000007000 age related cognitive decline Effects 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 229940025084 amphetamine Drugs 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- 208000022257 bipolar II disease Diseases 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 229960003920 cocaine Drugs 0.000 claims 1
- 208000026725 cyclothymic disease Diseases 0.000 claims 1
- 230000003001 depressive effect Effects 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 206010058319 dysgraphia Diseases 0.000 claims 1
- 206010013932 dyslexia Diseases 0.000 claims 1
- 208000024732 dysthymic disease Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 208000028329 epileptic seizure Diseases 0.000 claims 1
- 239000000380 hallucinogen Substances 0.000 claims 1
- 230000002218 hypoglycaemic effect Effects 0.000 claims 1
- 230000001505 hypomanic effect Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 238000007917 intracranial administration Methods 0.000 claims 1
- 201000003723 learning disability Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 240000004308 marijuana Species 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 239000002581 neurotoxin Substances 0.000 claims 1
- 231100000618 neurotoxin Toxicity 0.000 claims 1
- 229940005483 opioid analgesics Drugs 0.000 claims 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims 1
- 229950010883 phencyclidine Drugs 0.000 claims 1
- 231100000572 poisoning Toxicity 0.000 claims 1
- 230000000607 poisoning effect Effects 0.000 claims 1
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 1
- 208000022610 schizoaffective disease Diseases 0.000 claims 1
- 238000001179 sorption measurement Methods 0.000 claims 1
- 241000124008 Mammalia Species 0.000 abstract 2
- 210000003169 central nervous system Anatomy 0.000 abstract 2
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
- C07D401/14—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 three or more hetero rings
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present invention relates to a succinate salt of 2-((4-(1-methyl-4- (pyridin-4-yl)-1 H-pyrazol-3-yl)phenoxy)methyl)quinoline, and to a method for treating disorders of the Central Nervous System (CNS) and other disorders in a mammal, including a human, by administering to the mammal the succinate salt. It also relates to pharmaceutical compositions containing a pharmaceutically acceptable carrier and the succinate salt.
Claims (14)
1. A succinate salt of Formula I:
2. The salt according to claim 1, wherein the salt has characteristic X-ray powder diffraction peaks as measured with copper radiation of 2-Theta ~
0.1 °
of 15.8, 21.0 and 26.6.
0.1 °
of 15.8, 21.0 and 26.6.
3. The salt according to claim 1, wherein the salt has characteristic X-ray powder diffraction peaks as measured with copper radiation of 2-Theta ~
0.1 °
of 15.8, 16.7, 21.0, 24.2 and 26.6.
0.1 °
of 15.8, 16.7, 21.0, 24.2 and 26.6.
4. The salt according to claim 1, wherein the salt has the characteristic X-ray powder diffraction pattern of FIG. 1.
5. The salt according to claim 1, 2, 3 or 4, wherein the salt has a melting onset temperature of 184 ~ 3°C.
6. The salt according to claim 1, 2, 3, 4 or 5, wherein the salt increases in weight by less than 0.5% at 90 ~ 2% relative humidity in an isothermal (25.1 ~ 0.1 °C) moisture sorption test conducted from approximately 1%
to 90%
(~2%) humidity.
to 90%
(~2%) humidity.
7. The salt according to claim 1, 2, 3, 4, 5 or 6, wherein the salt is anhydrous.
8. A pharmaceutical composition comprising a succinate salt as defined in claim 1, 2, 3, 4, 5, 6 or 7, and a pharmaceutically acceptable carrier.
9. The pharmaceutical composition according to claim 8 wherein the succinate salt is crystalline.
10. A pharmaceutical composition for use in the treatment of a psychotic disorder, delusional disorder or drug induced psychosis; anxiety disorder, movement disorder, mood disorder, neurodegenerative disorder or drug addiction, comprising an amount of a succinate salt as defined in claim 1, 2, 3, 4, 5, 6 or 7 effective in treating said disorder or condition, and a pharmaceutically acceptable carrier.
11. Use of an effective amount of a succinate salt as defined in claim 1, 2, 3, 4, 5, 6 or 7 for the treatment of a psychotic disorder, delusional disorder or drug induced psychosis; anxiety disorder, movement disorder, mood disorder, or neurodegenerative disorder.
12. Use of an effective amount of a succinate salt as defined in claim 1, 2, 3, 4, 5, 6 or 7 for the treatment of dementia, Alzheimer's disease, multi-infarct dementia, alcoholic dementia or other drug-related dementia, dementia associated with intracranial tumors or cerebral trauma, dementia associated with Huntington's disease or Parkinson's disease, or AIDS-related dementia; delirium; amnestic disorder; post-traumatic stress disorder; mental retardation; a learning disorder, reading disorder, mathematics disorder, or a disorder of written expression;
attention-deficit/hyperactivity disorder; age-related cognitive decline, major depressive episode of the mild, moderate or severe type; a manic or mixed mood episode; a hypomanic mood episode; a depressive episode with atypical features;
a depressive episode with melancholic features; a depressive episode with catatonic features; a mood episode with postpartum onset; post-stroke depression; major depressive disorder; dysthymic disorder; minor depressive disorder; premenstrual dysphoric disorder; post-psychotic depressive disorder of schizophrenia; a major depressive disorder superimposed on a psychotic disorder comprising a delusional disorder or schizophrenia; a bipolar disorder comprising bipolar I disorder, bipolar II disorder, cyclothymic disorder, Parkinson's disease;
Huntington's disease; dementia, Alzheimer's disease, multi-infarct dementia, AIDS-related dementia, Fronto temperal Dementia; neurodegeneration associated with cerebral trauma; neurodegeneration associated with stroke;
neurodegeneration associated with cerebral infarct; hypoglycemia-induced neurodegeneration; neurodegeneration associated with epileptic seizure;
neurodegeneration associated with neurotoxin poisoning; multi-system atrophy, paranoid, disorganized, catatonic, undifferentiated or residual type;
schizophreniform disorder; schizoaffective disorder of the delusional type or the depressive type; delusional disorder; substance-induced psychotic disorder, psychosis induced by alcohol, amphetamine, cannabis, cocaine, hallucinogens, inhalants, opioids, or phencyclidine; personality disorder of the paranoid type; or personality disorder of the schizoid type.
attention-deficit/hyperactivity disorder; age-related cognitive decline, major depressive episode of the mild, moderate or severe type; a manic or mixed mood episode; a hypomanic mood episode; a depressive episode with atypical features;
a depressive episode with melancholic features; a depressive episode with catatonic features; a mood episode with postpartum onset; post-stroke depression; major depressive disorder; dysthymic disorder; minor depressive disorder; premenstrual dysphoric disorder; post-psychotic depressive disorder of schizophrenia; a major depressive disorder superimposed on a psychotic disorder comprising a delusional disorder or schizophrenia; a bipolar disorder comprising bipolar I disorder, bipolar II disorder, cyclothymic disorder, Parkinson's disease;
Huntington's disease; dementia, Alzheimer's disease, multi-infarct dementia, AIDS-related dementia, Fronto temperal Dementia; neurodegeneration associated with cerebral trauma; neurodegeneration associated with stroke;
neurodegeneration associated with cerebral infarct; hypoglycemia-induced neurodegeneration; neurodegeneration associated with epileptic seizure;
neurodegeneration associated with neurotoxin poisoning; multi-system atrophy, paranoid, disorganized, catatonic, undifferentiated or residual type;
schizophreniform disorder; schizoaffective disorder of the delusional type or the depressive type; delusional disorder; substance-induced psychotic disorder, psychosis induced by alcohol, amphetamine, cannabis, cocaine, hallucinogens, inhalants, opioids, or phencyclidine; personality disorder of the paranoid type; or personality disorder of the schizoid type.
13. Use of an amount of the succinate salt as defined in claim 1, 2, 3, 4, 5, 6 or 7 effective in inhibiting PDE10 for the treatment of a psychotic disorder, delusional disorder or drug induced psychosis; anxiety disorder, movement disorder, mood disorder, neurodegenerative disorder or drug addiction.
14. Use of a succinate salt as defined in claim 1, 2, 3, 4, 5, 6 or 7 in the manufacture of a medicament for the treatment of a psychotic disorder, delusional disorder or drug induced psychosis; anxiety disorder, movement disorder, mood disorder, neurodegenerative disorder or drug addiction.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87126006P | 2006-12-21 | 2006-12-21 | |
| US60/871,260 | 2006-12-21 | ||
| PCT/IB2007/003819 WO2008084299A1 (en) | 2006-12-21 | 2007-12-03 | Succinate salt of 2-((4-(1-methyl-4-(pyridin-4-yl)-1h-pyrazol-3-yl) phenoxy)methyl)quinoline |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2673435A1 true CA2673435A1 (en) | 2008-07-17 |
| CA2673435C CA2673435C (en) | 2012-10-09 |
Family
ID=39321475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2673435A Expired - Fee Related CA2673435C (en) | 2006-12-21 | 2007-12-03 | Succinate salt of 2-((4-(1-methyl-4-(pyridin-4-yl)-1h-pyrazol-3-yl) phenoxy)methyl)quinoline |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US8283471B2 (en) |
| EP (1) | EP2125786B1 (en) |
| JP (1) | JP5254602B2 (en) |
| KR (2) | KR20090092338A (en) |
| CN (1) | CN101611029B (en) |
| AR (1) | AR064417A1 (en) |
| AT (1) | ATE502028T1 (en) |
| AU (1) | AU2007343135B2 (en) |
| BR (1) | BRPI0720936A2 (en) |
| CA (1) | CA2673435C (en) |
| CY (1) | CY1111919T1 (en) |
| DE (1) | DE602007013294D1 (en) |
| DK (1) | DK2125786T3 (en) |
| ES (1) | ES2360014T3 (en) |
| HK (1) | HK1134670A1 (en) |
| IL (1) | IL199389A (en) |
| MX (1) | MX2009006528A (en) |
| NZ (1) | NZ577716A (en) |
| PL (1) | PL2125786T3 (en) |
| PT (1) | PT2125786E (en) |
| RU (1) | RU2430918C2 (en) |
| SI (1) | SI2125786T1 (en) |
| TW (1) | TWI359660B (en) |
| WO (1) | WO2008084299A1 (en) |
| ZA (1) | ZA200904230B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010033045A1 (en) * | 2008-09-16 | 2010-03-25 | Igor Anatolievich Pomytkin | Compositions and methods for prevention or treatment of beta amyloid deposition |
| TWI396689B (en) | 2008-11-14 | 2013-05-21 | Amgen Inc | Pyrazine derivatives as phosphodiesterase 10 inhibitors |
| US20120214842A1 (en) * | 2011-02-18 | 2012-08-23 | Exonhit Therapeutics Sa | Methods for treating diseases of the retina |
| JPWO2014142322A1 (en) | 2013-03-15 | 2017-02-16 | 第一三共株式会社 | Benzothiophene derivatives |
| US10039764B2 (en) | 2013-07-12 | 2018-08-07 | University Of South Alabama | Treatment and diagnosis of cancer and precancerous conditions using PDE10A inhibitors and methods to measure PDE10A expression |
| KR102233916B1 (en) * | 2019-05-28 | 2021-03-30 | 주식회사 엘지생활건강 | Composition for Skin Moisturizing, Improving Skin Wrinkle and Elasticity comprising PQ1 Succinic Acid |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5795909A (en) * | 1996-05-22 | 1998-08-18 | Neuromedica, Inc. | DHA-pharmaceutical agent conjugates of taxanes |
| CA2436668C (en) * | 2001-02-12 | 2009-05-26 | Wyeth | Novel succinate salt of o-desmethyl-venlafaxine |
| ES2258652T3 (en) * | 2001-11-29 | 2006-09-01 | Pfizer Products Inc. | SUCCINATE SALTS OF 5,8,14-TRIAZATETRACICLO (10.3.1.02,11.04,9) -HEXADECA-2 (11), 3,5,7,9-PENTAENE AND PHARMACEUTICAL COMPOSITIONS OF THE SAME. |
| KR20040065259A (en) * | 2001-12-12 | 2004-07-21 | 화이자 프로덕츠 인크. | Salt Forms of E-2-Methoxy-N-(3-(4-(3-Methyl-Pyridin-3-yloxy)-Phenylamino)-Quinazolin-6-yl)-Allyl)-Acetamide, Its Preparation and Its Use against Cancer |
| AU2004265021B2 (en) * | 2003-08-18 | 2010-05-27 | H. Lundbeck A/S | Succinate and malonate salt of trans-4-(IR,3S)-6-chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine and the use as a medicament |
| EP1841757B1 (en) * | 2005-01-07 | 2010-06-30 | Pfizer Products Incorporated | Heteroaromatic quinoline compounds and their use as pde10 inhibitors |
| US20060166057A1 (en) | 2005-01-21 | 2006-07-27 | Cabot Corporation | Method of making nanoparticulates and use of the nanoparticulates to make products using a flame reactor |
| BRPI0619962A2 (en) * | 2005-12-16 | 2011-10-25 | Wyeth Corp | lyophilized compositions of a triazolopyrimidine compound |
-
2007
- 2007-12-03 WO PCT/IB2007/003819 patent/WO2008084299A1/en active Application Filing
- 2007-12-03 DK DK07858987.6T patent/DK2125786T3/en active
- 2007-12-03 AT AT07858987T patent/ATE502028T1/en active
- 2007-12-03 CA CA2673435A patent/CA2673435C/en not_active Expired - Fee Related
- 2007-12-03 KR KR1020097015193A patent/KR20090092338A/en not_active Application Discontinuation
- 2007-12-03 DE DE602007013294T patent/DE602007013294D1/en active Active
- 2007-12-03 PT PT07858987T patent/PT2125786E/en unknown
- 2007-12-03 NZ NZ577716A patent/NZ577716A/en not_active IP Right Cessation
- 2007-12-03 MX MX2009006528A patent/MX2009006528A/en active IP Right Grant
- 2007-12-03 US US12/515,612 patent/US8283471B2/en not_active Expired - Fee Related
- 2007-12-03 EP EP07858987A patent/EP2125786B1/en not_active Not-in-force
- 2007-12-03 BR BRPI0720936-3A patent/BRPI0720936A2/en not_active IP Right Cessation
- 2007-12-03 AU AU2007343135A patent/AU2007343135B2/en not_active Ceased
- 2007-12-03 PL PL07858987T patent/PL2125786T3/en unknown
- 2007-12-03 RU RU2009123347/04A patent/RU2430918C2/en not_active IP Right Cessation
- 2007-12-03 CN CN200780051566.5A patent/CN101611029B/en not_active Expired - Fee Related
- 2007-12-03 ES ES07858987T patent/ES2360014T3/en active Active
- 2007-12-03 KR KR1020127009903A patent/KR20120043775A/en not_active Application Discontinuation
- 2007-12-03 SI SI200730561T patent/SI2125786T1/en unknown
- 2007-12-18 AR ARP070105692A patent/AR064417A1/en not_active Application Discontinuation
- 2007-12-19 JP JP2007327323A patent/JP5254602B2/en not_active Expired - Fee Related
- 2007-12-20 TW TW096148920A patent/TWI359660B/en not_active IP Right Cessation
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2009
- 2009-06-16 IL IL199389A patent/IL199389A/en active IP Right Review Request
- 2009-06-17 ZA ZA200904230A patent/ZA200904230B/en unknown
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2010
- 2010-02-10 HK HK10101480.3A patent/HK1134670A1/en not_active IP Right Cessation
-
2011
- 2011-05-17 CY CY20111100481T patent/CY1111919T1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2360014T3 (en) | 2011-05-31 |
| EP2125786A1 (en) | 2009-12-02 |
| JP5254602B2 (en) | 2013-08-07 |
| US8283471B2 (en) | 2012-10-09 |
| HK1134670A1 (en) | 2010-05-07 |
| JP2008208114A (en) | 2008-09-11 |
| PT2125786E (en) | 2011-04-21 |
| KR20090092338A (en) | 2009-08-31 |
| AR064417A1 (en) | 2009-04-01 |
| RU2430918C2 (en) | 2011-10-10 |
| AU2007343135B2 (en) | 2013-03-21 |
| PL2125786T3 (en) | 2011-07-29 |
| ATE502028T1 (en) | 2011-04-15 |
| TWI359660B (en) | 2012-03-11 |
| IL199389A (en) | 2014-01-30 |
| MX2009006528A (en) | 2009-06-26 |
| ZA200904230B (en) | 2010-04-28 |
| RU2009123347A (en) | 2011-01-27 |
| TW200833337A (en) | 2008-08-16 |
| EP2125786B1 (en) | 2011-03-16 |
| CY1111919T1 (en) | 2015-11-04 |
| BRPI0720936A2 (en) | 2014-03-11 |
| DE602007013294D1 (en) | 2011-04-28 |
| US20100063089A1 (en) | 2010-03-11 |
| KR20120043775A (en) | 2012-05-04 |
| DK2125786T3 (en) | 2011-05-09 |
| CA2673435C (en) | 2012-10-09 |
| CN101611029B (en) | 2014-09-10 |
| WO2008084299A1 (en) | 2008-07-17 |
| AU2007343135A1 (en) | 2008-07-17 |
| SI2125786T1 (en) | 2011-05-31 |
| NZ577716A (en) | 2012-10-26 |
| CN101611029A (en) | 2009-12-23 |
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| MKLA | Lapsed |
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