JP2017513887A5 - - Google Patents
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- JP2017513887A5 JP2017513887A5 JP2016564057A JP2016564057A JP2017513887A5 JP 2017513887 A5 JP2017513887 A5 JP 2017513887A5 JP 2016564057 A JP2016564057 A JP 2016564057A JP 2016564057 A JP2016564057 A JP 2016564057A JP 2017513887 A5 JP2017513887 A5 JP 2017513887A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- haloalkyl
- alkoxy
- group
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 170
- 125000003545 alkoxy group Chemical group 0.000 claims 44
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 43
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 41
- 125000004093 cyano group Chemical group *C#N 0.000 claims 40
- 229910052736 halogen Inorganic materials 0.000 claims 38
- 150000002367 halogens Chemical class 0.000 claims 38
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 34
- 150000003839 salts Chemical class 0.000 claims 34
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 28
- 125000003118 aryl group Chemical group 0.000 claims 28
- -1 2 -cyclopropyl Chemical group 0.000 claims 27
- 229910052799 carbon Inorganic materials 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 23
- 208000010877 cognitive disease Diseases 0.000 claims 21
- 125000001424 substituent group Chemical group 0.000 claims 19
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 16
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 15
- 208000028698 Cognitive impairment Diseases 0.000 claims 14
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 13
- 125000001188 haloalkyl group Chemical group 0.000 claims 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 201000000980 schizophrenia Diseases 0.000 claims 9
- 208000011117 substance-related disease Diseases 0.000 claims 9
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 208000024827 Alzheimer disease Diseases 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 208000005793 Restless legs syndrome Diseases 0.000 claims 6
- 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 claims 6
- 230000001684 chronic effect Effects 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 208000024714 major depressive disease Diseases 0.000 claims 6
- 208000027061 mild cognitive impairment Diseases 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- YSEAGKXERZRQSR-UHFFFAOYSA-N CC1=C(C(=NC=N1)C#N)C1=C(C=C(C=C1)OC=1N=CC=C2C1SC=C2)C Chemical compound CC1=C(C(=NC=N1)C#N)C1=C(C=C(C=C1)OC=1N=CC=C2C1SC=C2)C YSEAGKXERZRQSR-UHFFFAOYSA-N 0.000 claims 4
- KKNLJIKADMZRDL-UHFFFAOYSA-N CN1C(NC(C(=C1C1=C(C=C(C=C1)OC=1C2=C(N=CN1)C=CS2)C)C)=O)=O Chemical compound CN1C(NC(C(=C1C1=C(C=C(C=C1)OC=1C2=C(N=CN1)C=CS2)C)C)=O)=O KKNLJIKADMZRDL-UHFFFAOYSA-N 0.000 claims 4
- 206010012289 Dementia Diseases 0.000 claims 4
- 201000001880 Sexual dysfunction Diseases 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000006413 ring segment Chemical group 0.000 claims 4
- 231100000872 sexual dysfunction Toxicity 0.000 claims 4
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 3
- 206010065040 AIDS dementia complex Diseases 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 3
- 208000020925 Bipolar disease Diseases 0.000 claims 3
- 208000032841 Bulimia Diseases 0.000 claims 3
- 206010006550 Bulimia nervosa Diseases 0.000 claims 3
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims 3
- 206010013654 Drug abuse Diseases 0.000 claims 3
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 3
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 3
- 208000023105 Huntington disease Diseases 0.000 claims 3
- 206010024264 Lethargy Diseases 0.000 claims 3
- 208000009829 Lewy Body Disease Diseases 0.000 claims 3
- 201000002832 Lewy body dementia Diseases 0.000 claims 3
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- 206010034158 Pathological gambling Diseases 0.000 claims 3
- 201000009916 Postpartum depression Diseases 0.000 claims 3
- 206010039966 Senile dementia Diseases 0.000 claims 3
- 206010040108 Serotonin syndrome Diseases 0.000 claims 3
- 206010041250 Social phobia Diseases 0.000 claims 3
- 206010041349 Somnolence Diseases 0.000 claims 3
- 208000000323 Tourette Syndrome Diseases 0.000 claims 3
- 208000016620 Tourette disease Diseases 0.000 claims 3
- 239000005557 antagonist Substances 0.000 claims 3
- 230000036506 anxiety Effects 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 208000029560 autism spectrum disease Diseases 0.000 claims 3
- 230000001149 cognitive effect Effects 0.000 claims 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- 206010013663 drug dependence Diseases 0.000 claims 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 3
- 206010025482 malaise Diseases 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 208000022821 personality disease Diseases 0.000 claims 3
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 3
- 230000000698 schizophrenic effect Effects 0.000 claims 3
- 208000012672 seasonal affective disease Diseases 0.000 claims 3
- 208000019116 sleep disease Diseases 0.000 claims 3
- 201000009032 substance abuse Diseases 0.000 claims 3
- 231100000736 substance abuse Toxicity 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- 238000002560 therapeutic procedure Methods 0.000 claims 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 2
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- ZDCVIKLPOZFEOR-UHFFFAOYSA-N CC1=NC=NC(=C1C1=C(C#N)C=C(C=C1)OC=1N=CC=C2C1SC=C2)C Chemical compound CC1=NC=NC(=C1C1=C(C#N)C=C(C=C1)OC=1N=CC=C2C1SC=C2)C ZDCVIKLPOZFEOR-UHFFFAOYSA-N 0.000 claims 2
- LENPHRQYTMJQRF-UHFFFAOYSA-N ClC=1C=C(OC=2C3=C(N=CN2)C=CS3)C=CC1C=1C(=NC=NC1C)C Chemical compound ClC=1C=C(OC=2C3=C(N=CN2)C=CS3)C=CC1C=1C(=NC=NC1C)C LENPHRQYTMJQRF-UHFFFAOYSA-N 0.000 claims 2
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 2
- 201000004810 Vascular dementia Diseases 0.000 claims 2
- 230000007000 age related cognitive decline Effects 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 238000002651 drug therapy Methods 0.000 claims 2
- 230000002996 emotional effect Effects 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 201000001881 impotence Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims 2
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 1
- AXLAIAASHKOILK-UHFFFAOYSA-N 1,5-dimethyl-6-(2-methyl-4-thieno[2,3-c]pyridin-7-yloxyphenyl)pyrazin-2-one Chemical compound CN1C(C=NC(=C1C1=C(C=C(C=C1)OC=1N=CC=C2C1SC=C2)C)C)=O AXLAIAASHKOILK-UHFFFAOYSA-N 0.000 claims 1
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 1
- PUYOAVGNCWPANW-UHFFFAOYSA-N 2-methylpropyl 4-aminobenzoate Chemical compound CC(C)COC(=O)C1=CC=C(N)C=C1 PUYOAVGNCWPANW-UHFFFAOYSA-N 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- BSJATJKAHSPIPP-UHFFFAOYSA-N CC1=NC=NC(=C1C1=C(C=C(OC2=NC=CC3=C2SC=N3)C=C1)C)C Chemical compound CC1=NC=NC(=C1C1=C(C=C(OC2=NC=CC3=C2SC=N3)C=C1)C)C BSJATJKAHSPIPP-UHFFFAOYSA-N 0.000 claims 1
- XWQYZFQKYDPKJA-UHFFFAOYSA-N CC1=NC=NC(=C1C1=C(C=C(OC=2N=CC=C3C2OC=C3)C=C1)C)C Chemical compound CC1=NC=NC(=C1C1=C(C=C(OC=2N=CC=C3C2OC=C3)C=C1)C)C XWQYZFQKYDPKJA-UHFFFAOYSA-N 0.000 claims 1
- YYUPYYFUYVOUHE-UHFFFAOYSA-N CC1=NC=NC(=C1C1=C(C=C(OC=2N=CC=C3C2SC=C3)C=C1)C)C Chemical compound CC1=NC=NC(=C1C1=C(C=C(OC=2N=CC=C3C2SC=C3)C=C1)C)C YYUPYYFUYVOUHE-UHFFFAOYSA-N 0.000 claims 1
- GYXIMCNXDBRESN-UHFFFAOYSA-N CC=1C(NN=C(C1C1=C(C=C(C=C1)OC1=NC=CC2=C1SC=N2)C)C)=O Chemical compound CC=1C(NN=C(C1C1=C(C=C(C=C1)OC1=NC=CC2=C1SC=N2)C)C)=O GYXIMCNXDBRESN-UHFFFAOYSA-N 0.000 claims 1
- JJDMRILUIZQVDS-UHFFFAOYSA-N CC=1C(NN=C(C1C1=C(C=C(C=C1)OC=1N=CC=C2C1SN=C2)C)C)=O Chemical compound CC=1C(NN=C(C1C1=C(C=C(C=C1)OC=1N=CC=C2C1SN=C2)C)C)=O JJDMRILUIZQVDS-UHFFFAOYSA-N 0.000 claims 1
- YMMZJZWKLWMPLI-UHFFFAOYSA-N CC=1C(NN=C(C1C1=CC=C(C=C1)OC1=NC=CC2=C1SC=N2)C)=O Chemical compound CC=1C(NN=C(C1C1=CC=C(C=C1)OC1=NC=CC2=C1SC=N2)C)=O YMMZJZWKLWMPLI-UHFFFAOYSA-N 0.000 claims 1
- SXKRKDRCMOQQSU-UHFFFAOYSA-N CC=1C(NN=C(C1C1=CC=C(C=C1)OC=1C2=C(N=CN1)C=CS2)C)=O Chemical compound CC=1C(NN=C(C1C1=CC=C(C=C1)OC=1C2=C(N=CN1)C=CS2)C)=O SXKRKDRCMOQQSU-UHFFFAOYSA-N 0.000 claims 1
- RCXHRNVSCIHDCF-UHFFFAOYSA-N CN1C(C=NC(=C1C1=C(C=C(C=C1)OC=1C2=C(N=CN1)C=CS2)C)C)=O Chemical compound CN1C(C=NC(=C1C1=C(C=C(C=C1)OC=1C2=C(N=CN1)C=CS2)C)C)=O RCXHRNVSCIHDCF-UHFFFAOYSA-N 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- ICKLWCYUCOGXMF-UHFFFAOYSA-N ClC=1C=C(OC=2N=CC=C3C2SC=C3)C=CC1C=1C(=NC=NC1C)C Chemical compound ClC=1C=C(OC=2N=CC=C3C2SC=C3)C=CC1C=1C(=NC=NC1C)C ICKLWCYUCOGXMF-UHFFFAOYSA-N 0.000 claims 1
- 208000012661 Dyskinesia Diseases 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010021036 Hyponatraemia Diseases 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000007950 Ocular Hypotension Diseases 0.000 claims 1
- 206010030113 Oedema Diseases 0.000 claims 1
- 208000001647 Renal Insufficiency Diseases 0.000 claims 1
- 206010038540 Renal tubular necrosis Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000005873 benzo[d]thiazolyl group Chemical group 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 230000006999 cognitive decline Effects 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000008451 emotion Effects 0.000 claims 1
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 201000001421 hyperglycemia Diseases 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 201000006370 kidney failure Diseases 0.000 claims 1
- 201000003631 narcolepsy Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 230000002980 postoperative effect Effects 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 0 *c1c(*)c(*)c(*)c(*)c1* Chemical compound *c1c(*)c(*)c(*)c(*)c1* 0.000 description 3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461984070P | 2014-04-25 | 2014-04-25 | |
| US61/984,070 | 2014-04-25 | ||
| PCT/IB2015/052594 WO2015162515A1 (en) | 2014-04-25 | 2015-04-09 | Heteroaromatic compounds and their use as dopamine d1 ligands |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017513887A JP2017513887A (ja) | 2017-06-01 |
| JP2017513887A5 true JP2017513887A5 (enExample) | 2017-07-13 |
| JP6190076B2 JP6190076B2 (ja) | 2017-08-30 |
Family
ID=53002687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016564057A Expired - Fee Related JP6190076B2 (ja) | 2014-04-25 | 2015-04-09 | 複素芳香族化合物およびそのドーパミンｄ１リガンドとしての使用 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US9688698B2 (enExample) |
| EP (1) | EP3134087B1 (enExample) |
| JP (1) | JP6190076B2 (enExample) |
| KR (1) | KR20160142401A (enExample) |
| CN (1) | CN106232118A (enExample) |
| AP (1) | AP2016009464A0 (enExample) |
| AU (1) | AU2015249496A1 (enExample) |
| BR (1) | BR112016023623A2 (enExample) |
| CA (1) | CA2946471C (enExample) |
| CL (1) | CL2016002678A1 (enExample) |
| CR (1) | CR20160493A (enExample) |
| CU (1) | CU20160155A7 (enExample) |
| DO (1) | DOP2016000290A (enExample) |
| EA (1) | EA201691831A1 (enExample) |
| EC (1) | ECSP16090804A (enExample) |
| IL (1) | IL247849A0 (enExample) |
| MD (1) | MD20160112A2 (enExample) |
| MX (1) | MX2016013968A (enExample) |
| NI (1) | NI201600160A (enExample) |
| PE (1) | PE20170008A1 (enExample) |
| PH (1) | PH12016501863A1 (enExample) |
| SG (1) | SG11201607990QA (enExample) |
| SV (1) | SV2016005306A (enExample) |
| TN (1) | TN2016000452A1 (enExample) |
| TW (1) | TWI553011B (enExample) |
| WO (1) | WO2015162515A1 (enExample) |
| ZA (1) | ZA201606716B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3134404A1 (en) | 2014-04-25 | 2017-03-01 | Pfizer Inc. | Heteroaromatic compounds and their use as dopamine d1 ligands |
| US9868744B2 (en) | 2014-04-25 | 2018-01-16 | Pfizer Inc. | Heteroaromatic compounds and their use as dopamine D1 ligands |
| WO2015166370A1 (en) | 2014-04-28 | 2015-11-05 | Pfizer Inc. | Heteroaromatic compounds and their use as dopamine d1 ligands |
| EP3137469B1 (en) | 2014-04-28 | 2019-10-09 | Pfizer Inc | Heterocyclic compounds and their use as dopamine d1 ligands |
| MX385576B (es) * | 2016-11-02 | 2025-03-18 | Janssen Pharmaceutica Nv | Derivados de [1,2,4]triazol[1,5-a]pirimidina como inhibidores de pde2 |
| BR112019008604A2 (pt) | 2016-11-02 | 2019-07-09 | Janssen Pharmaceutica Nv | compostos de [1,2,4]triazolo[1,5-a]pirimidina como inibidores de pde2 |
| AR116635A1 (es) | 2018-10-15 | 2021-05-26 | Servier Lab | Proceso para la síntesis de derivados de piperazinil-etoxi-bromofenilo y su aplicación en la producción de compuestos que los contienen |
| WO2020087031A1 (en) | 2018-10-26 | 2020-04-30 | The Research Foundation For The State University Of New York | Combination serotonin specific reuptake inhibitor and serotonin 1a receptor partial agonist for reducing l-dopa-induced dyskinesia |
| CN117126176A (zh) * | 2023-08-21 | 2023-11-28 | 常州大学 | 一种噻吩并嘧啶类化合物及其作为多巴胺d2受体别构拮抗剂的应用 |
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| US5681941A (en) | 1990-01-11 | 1997-10-28 | Isis Pharmaceuticals, Inc. | Substituted purines and oligonucleotide cross-linking |
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| AU651337B2 (en) | 1990-03-30 | 1994-07-21 | Dowelanco | Thienopyrimidine derivatives |
| US5322847A (en) | 1992-11-05 | 1994-06-21 | Pfizer Inc. | Azabenzimidazoles in the treatment of asthma, arthritis and related diseases |
| GB9518953D0 (en) | 1995-09-15 | 1995-11-15 | Pfizer Ltd | Pharmaceutical formulations |
| AR004010A1 (es) | 1995-10-11 | 1998-09-30 | Glaxo Group Ltd | Compuestos heterociclicos |
| ZA971896B (en) | 1996-03-26 | 1998-09-07 | Du Pont Merck Pharma | Aryloxy-and arythio-fused pyridines and pyrimidines and derivatives |
| WO2000035298A1 (en) | 1996-11-27 | 2000-06-22 | Wm. Wrigley Jr. Company | Chewing gum containing medicament active agents |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| US6232320B1 (en) | 1998-06-04 | 2001-05-15 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory compounds |
| US6995171B2 (en) | 2001-06-21 | 2006-02-07 | Agouron Pharmaceuticals, Inc. | Bicyclic pyrimidine and pyrimidine derivatives useful as anticancer agents |
| US20030187026A1 (en) | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
| JP2005527511A (ja) | 2002-03-01 | 2005-09-15 | ファイザー インコーポレイテッド | 抗血管形成剤として有用なチエノピリジンのインドリル−尿素誘導体およびその使用法 |
| US20050284101A1 (en) * | 2004-06-24 | 2005-12-29 | Brandes Donald J | Method and apparatus for assembling strong, lightweight thermal panel and insulated building structure |
| US20050165029A1 (en) | 2004-01-13 | 2005-07-28 | Ambit Biosciences Corporation | Pyrrolopyrimidine derivatives and analogs and their use in the treatment and prevention of diseases |
| CA2566158A1 (en) * | 2004-05-14 | 2005-11-24 | Abbott Laboratories | Kinase inhibitors as therapeutic agents |
| MXPA06013996A (es) | 2004-06-02 | 2007-02-08 | Takeda Pharmaceutical | Compuesto heterociclico fusionado. |
| EP1773826A4 (en) | 2004-07-02 | 2009-06-03 | Exelixis Inc | MODULATORS OF C-MET AND THEIR METHOD OF USE |
| GB0502573D0 (en) | 2005-02-08 | 2005-03-16 | Topotarget As | Therapeutic compounds |
| CA2607021C (en) | 2005-05-05 | 2013-10-29 | Ardea Biosciences, Inc. | Diaryl-purines, -azapurines and -deazapurines as non-nucleoside reverse transcriptase inhibitors for treatment of hiv |
| BRPI0610322B8 (pt) | 2005-05-20 | 2021-05-25 | Methylgene Inc | inibidores de sinalização de receptor de vegf e de receptor de hgf e composição farmacêutica |
| EP1746096A1 (en) * | 2005-07-15 | 2007-01-24 | 4Sc Ag | 2-Arylbenzothiazole analogues and uses thereof in the treatment of cancer |
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2015
- 2015-04-09 MD MDA20160112A patent/MD20160112A2/ro not_active Application Discontinuation
- 2015-04-09 CA CA2946471A patent/CA2946471C/en not_active Expired - Fee Related
- 2015-04-09 AP AP2016009464A patent/AP2016009464A0/en unknown
- 2015-04-09 PE PE2016002125A patent/PE20170008A1/es not_active Application Discontinuation
- 2015-04-09 WO PCT/IB2015/052594 patent/WO2015162515A1/en not_active Ceased
- 2015-04-09 MX MX2016013968A patent/MX2016013968A/es unknown
- 2015-04-09 BR BR112016023623A patent/BR112016023623A2/pt not_active IP Right Cessation
- 2015-04-09 AU AU2015249496A patent/AU2015249496A1/en not_active Abandoned
- 2015-04-09 CR CR20160493A patent/CR20160493A/es unknown
- 2015-04-09 CN CN201580020992.7A patent/CN106232118A/zh active Pending
- 2015-04-09 EP EP15718387.2A patent/EP3134087B1/en active Active
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- 2015-04-09 EA EA201691831A patent/EA201691831A1/ru unknown
- 2015-04-09 KR KR1020167032876A patent/KR20160142401A/ko not_active Withdrawn
- 2015-04-22 TW TW104112873A patent/TWI553011B/zh not_active IP Right Cessation
- 2015-04-23 US US14/694,039 patent/US9688698B2/en active Active
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