CA2440238C - Novel amines as histamine-3 receptor ligands and their therapeutic applications - Google Patents
Novel amines as histamine-3 receptor ligands and their therapeutic applications Download PDFInfo
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- CA2440238C CA2440238C CA2440238A CA2440238A CA2440238C CA 2440238 C CA2440238 C CA 2440238C CA 2440238 A CA2440238 A CA 2440238A CA 2440238 A CA2440238 A CA 2440238A CA 2440238 C CA2440238 C CA 2440238C
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- CA
- Canada
- Prior art keywords
- ethyl
- benzofuran
- methyl
- pyrrolidinyl
- pyrrolidin
- 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.)
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- 239000003446 ligand Substances 0.000 title abstract description 8
- 150000001412 amines Chemical class 0.000 title description 22
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 412
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
- 208000035475 disorder Diseases 0.000 claims abstract description 13
- 241000124008 Mammalia Species 0.000 claims abstract description 7
- 230000001668 ameliorated effect Effects 0.000 claims abstract description 5
- 238000011282 treatment Methods 0.000 claims abstract description 5
- -1 imadazolyl Chemical group 0.000 claims description 1311
- 125000000217 alkyl group Chemical group 0.000 claims description 186
- 125000000623 heterocyclic group Chemical group 0.000 claims description 177
- 229910052739 hydrogen Inorganic materials 0.000 claims description 154
- 239000001257 hydrogen Substances 0.000 claims description 153
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 119
- 229910052757 nitrogen Inorganic materials 0.000 claims description 112
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 107
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 100
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 99
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 95
- 229910052736 halogen Inorganic materials 0.000 claims description 76
- 150000002367 halogens Chemical group 0.000 claims description 76
- 125000003545 alkoxy group Chemical group 0.000 claims description 75
- 125000001188 haloalkyl group Chemical group 0.000 claims description 73
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 72
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 71
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 71
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 62
- 125000004414 alkyl thio group Chemical group 0.000 claims description 62
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 60
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 58
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 58
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 58
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 57
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 56
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 56
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 56
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 56
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 56
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 56
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 55
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 54
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 52
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 51
- 125000004076 pyridyl group Chemical group 0.000 claims description 49
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 49
- 125000002393 azetidinyl group Chemical group 0.000 claims description 47
- 125000002757 morpholinyl group Chemical group 0.000 claims description 47
- 125000004193 piperazinyl group Chemical group 0.000 claims description 47
- 125000003386 piperidinyl group Chemical group 0.000 claims description 47
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000003725 azepanyl group Chemical group 0.000 claims description 42
- 125000003342 alkenyl group Chemical group 0.000 claims description 40
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 30
- 125000000304 alkynyl group Chemical group 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000002947 alkylene group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 21
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 18
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 14
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 12
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 5
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- MLKLMMHXAFOMLR-UJONTBEJSA-N 4-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2,3-dihydro-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1OC2=CC=C(C=3C=CC(=CC=3)C#N)C=C2C1 MLKLMMHXAFOMLR-UJONTBEJSA-N 0.000 claims description 4
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- KPNUCNMZTCZSCQ-CYBMUJFWSA-N 3,5-dimethyl-4-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1,2-oxazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C3=C(ON=C3C)C)=CC=C2O1 KPNUCNMZTCZSCQ-CYBMUJFWSA-N 0.000 claims description 3
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- PLRBHSSVBVBIBD-MRXNPFEDSA-N 1-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzimidazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N3C4=CC=CC=C4N=C3)=CC=C2O1 PLRBHSSVBVBIBD-MRXNPFEDSA-N 0.000 claims description 2
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- 229910052799 carbon Inorganic materials 0.000 claims description 2
- BGHFRTUKSRZCQR-CYBMUJFWSA-N cyclopropyl-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C3CC3)=CC=C2O1 BGHFRTUKSRZCQR-CYBMUJFWSA-N 0.000 claims description 2
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
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- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
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- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
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- 239000011347 resin Substances 0.000 description 1
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- 208000023504 respiratory system disease Diseases 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
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- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
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- 230000005062 synaptic transmission Effects 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
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- C07D491/10—Spiro-condensed systems
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pulmonology (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Otolaryngology (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Communicable Diseases (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Addiction (AREA)
- Obesity (AREA)
- Oncology (AREA)
- Anesthesiology (AREA)
- Urology & Nephrology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/810,648 US20020177589A1 (en) | 2001-03-16 | 2001-03-16 | Novel amines as histamine-3 receptor ligands and their therapeutic applications |
| US09/810,648 | 2001-03-16 | ||
| US10/044,495 | 2002-01-11 | ||
| US10/044,495 US20020183309A1 (en) | 2001-03-16 | 2002-01-11 | Novel amines as histamine-3 receptor ligands and their therapeutic applications |
| US10/081,207 | 2002-02-25 | ||
| US10/081,207 US6969730B2 (en) | 2001-03-16 | 2002-02-25 | Amines as histamine-3 receptor ligands and their therapeutic applications |
| PCT/US2002/007107 WO2002074758A2 (en) | 2001-03-16 | 2002-03-11 | Novel amines as histamine-3 receptor ligands and their therapeutic applications |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2440238A1 CA2440238A1 (en) | 2002-09-26 |
| CA2440238C true CA2440238C (en) | 2011-09-13 |
Family
ID=27366495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2440238A Expired - Fee Related CA2440238C (en) | 2001-03-16 | 2002-03-11 | Novel amines as histamine-3 receptor ligands and their therapeutic applications |
Country Status (7)
| Country | Link |
|---|---|
| EP (2) | EP1370546A2 (enExample) |
| JP (1) | JP4612990B2 (enExample) |
| AR (1) | AR035783A1 (enExample) |
| BR (1) | BR0205829A (enExample) |
| CA (1) | CA2440238C (enExample) |
| MX (1) | MXPA03008319A (enExample) |
| WO (1) | WO2002074758A2 (enExample) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7314937B2 (en) | 2002-03-21 | 2008-01-01 | Eli Lilly And Company | Non-imidazole aryl alkylamines compounds as histamine H3 receptor antagonists, preparation and therapeutic uses |
| US6822101B2 (en) | 2002-09-16 | 2004-11-23 | Abbott Laboratories | Process for preparing amine-substituted benzofurans |
| JP4820094B2 (ja) * | 2002-11-12 | 2011-11-24 | アボット・ラボラトリーズ | ヒスタミン−3受容体リガンドとしての2環式置換アミン |
| US7153889B2 (en) | 2002-11-12 | 2006-12-26 | Abbott Laboratories | Bicyclic-substituted amines as histamine-3 receptor ligands |
| US7244852B2 (en) | 2003-02-27 | 2007-07-17 | Abbott Laboratories | Process for preparing 2-methylpyrrolidine and specific enantiomers thereof |
| TW201018661A (en) | 2003-03-14 | 2010-05-16 | Ono Pharmaceutical Co | Heterocyclic rinf having nitrogen atom derivatives and medicament containing the derivatives as active ingredient |
| EP1611902A4 (en) * | 2003-04-03 | 2006-04-12 | Kyowa Hakko Kogyo Kk | MEANS FOR THE PREVENTION AND / OR TREATMENT OF NEUROPATHIC PAIN |
| US7094790B2 (en) | 2003-05-07 | 2006-08-22 | Abbott Laboratories | Fused bicyclic-substituted amines as histamine-3 receptor ligands |
| US20040224952A1 (en) * | 2003-05-07 | 2004-11-11 | Cowart Marlon D. | Fused bicyclic-substituted amines as histamine-3 receptor ligands |
| CA2524787A1 (en) * | 2003-05-07 | 2004-11-25 | Abbott Laboratories | Fused bicyclic-substituted amines as histamine-3 receptor ligands |
| JP2007510629A (ja) * | 2003-10-22 | 2007-04-26 | イーライ リリー アンド カンパニー | 新規mch受容体アンタゴニスト |
| US7435837B2 (en) | 2003-10-24 | 2008-10-14 | Wyeth | Dihydrobenzofuranyl alkanamine derivatives and methods for using same |
| SE0303480D0 (sv) * | 2003-12-19 | 2003-12-19 | Biovitrum Ab | Benzofuranes |
| CN1934094A (zh) * | 2004-03-05 | 2007-03-21 | 万有制药株式会社 | 二芳基取代杂环5元环衍生物 |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| US7145005B2 (en) | 2004-05-12 | 2006-12-05 | Abbott Laboratories | 2-(6-{2-[(2R)-2-Methyl-1-pyrrolidin-1-yl]-ethyl}-2-naphthalen-2-yl)-2H-pyridazin-3-one salts and their preparation |
| US7098222B2 (en) | 2004-05-12 | 2006-08-29 | Abbott Laboratories | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| US20050256309A1 (en) * | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Tri-and bi-cyclic heteroaryl histamine-3 receptor ligands |
| US7205316B2 (en) | 2004-05-12 | 2007-04-17 | Abbott Laboratories | Tri- and bi-cyclic heteroaryl histamine-3 receptor ligands |
| US20050256118A1 (en) * | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| DE102004030099A1 (de) * | 2004-06-22 | 2006-01-12 | Grünenthal GmbH | Gesättigte und ungesättigte 3-Pyridyl-benzocycloalkylmethyl-amine als Serotonin- und/oder Noradrenalin-Reuptake-Hemmer und/oder µ-Opioidrezeptor-Modulatoren |
| TWI400232B (zh) | 2004-09-13 | 2013-07-01 | Ono Pharmaceutical Co | 含氮雜環衍生物及以該含氮雜環衍生物為有效成分之藥劑 |
| US7553964B2 (en) | 2005-06-03 | 2009-06-30 | Abbott Laboratories | Cyclobutyl amine derivatives |
| AU2007225836A1 (en) | 2006-03-10 | 2007-09-20 | Ono Pharmaceutical Co., Ltd. | Nitrogenated heterocyclic derivative, and pharmaceutical agent comprising the derivative as active ingredient |
| US20080015193A1 (en) * | 2006-06-20 | 2008-01-17 | Mendoza Jose S | Certain azoles exhibiting ATP-utilizing enzyme inhibitory activity, compositions, and uses thereof |
| US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| MX2008016343A (es) | 2006-06-23 | 2009-01-19 | Abbott Lab | Derivados ciclopropil amina como moduladores del receptro de histamina h3. |
| CN101855211B (zh) | 2007-11-13 | 2013-06-12 | 大正制药株式会社 | 苯基吡唑衍生物 |
| US8383657B2 (en) | 2007-12-21 | 2013-02-26 | Abbott Laboratories | Thiazolylidine urea and amide derivatives and methods of use thereof |
| AU2009304598B2 (en) | 2008-10-17 | 2015-01-29 | Akaal Pharma Pty Ltd | S1P receptors modulators and their use thereof |
| CA2739901A1 (en) | 2008-10-17 | 2010-04-22 | Akaal Pharma Pty Ltd | S1p receptors modulators |
| US9186353B2 (en) | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
| JP2012082186A (ja) * | 2010-09-15 | 2012-04-26 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
| GB201113538D0 (en) | 2011-08-04 | 2011-09-21 | Karobio Ab | Novel estrogen receptor ligands |
| ES2886914T3 (es) * | 2013-01-09 | 2021-12-21 | Arena Pharm Inc | Acido (R)-3-(4'-(2-(2-metilpirrolidin-1-il)etil)-bifenil-4-il)propanoico como moduladores del receptor de histamina H3 para el tratamiento de trastornos cognitivos |
| US9796673B2 (en) * | 2014-12-22 | 2017-10-24 | Teva Pharmaceuticals International Gmbh | L-tartrate salt of pridopidine |
| CN109456292B (zh) * | 2018-10-23 | 2022-06-10 | 中山大学 | 一种海洋真菌来源的香豆素类化合物及其制备方法与应用 |
| EP4251148A1 (en) | 2020-11-27 | 2023-10-04 | Richter Gedeon Nyrt. | Histamine h3 receptor antagonists/inverse agonists for the treatment of autism spectrum disorder |
| CN114805261B (zh) * | 2021-01-18 | 2023-03-21 | 沈阳药科大学 | 苯并呋喃类lsd1抑制剂及其制备方法 |
| CN115385885A (zh) * | 2022-05-05 | 2022-11-25 | 深圳海创生物科技有限公司 | 一种蓝莓多酚、组合物及其在制备具有降血脂和/或减肥作用的药物或食品中的应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4237144A (en) * | 1979-06-21 | 1980-12-02 | Merck & Co., Inc. | 2,3-Dihydro-2,6,7-trisubstituted-5-acylbenzofurans |
| IL101785A0 (en) * | 1991-05-10 | 1992-12-30 | Fujisawa Pharmaceutical Co | Urea derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same |
| US5436246A (en) * | 1992-09-17 | 1995-07-25 | Merrell Dow Pharmaceuticals Inc. | Serotonin receptor agents |
| JP2759257B2 (ja) * | 1993-09-28 | 1998-05-28 | 大塚製薬株式会社 | 糖尿病治療剤 |
| JPH07173158A (ja) * | 1993-12-17 | 1995-07-11 | Taiho Yakuhin Kogyo Kk | チアゾリジンジオン誘導体又はその塩 |
| US5585492A (en) * | 1994-10-11 | 1996-12-17 | G. D. Searle & Co. | LTA4 Hydrolase inhibitors |
| US6130187A (en) * | 1996-02-09 | 2000-10-10 | Kumiai Chemical Industry Co., Ltd. | Benzofuran-7-yl uracil derivatives and herbicides |
| US6077812A (en) * | 1997-02-26 | 2000-06-20 | Fmc Corporation | Cycloimido-substituted benzofused heterocyclic herbicides |
| WO1998052946A1 (en) * | 1997-12-02 | 1998-11-26 | Dr. Reddy's Research Foundation | Azolidinediones useful for the treatment of diabetes, dyslipidemia and hypertension |
| EP0978512A1 (en) | 1998-07-29 | 2000-02-09 | Societe Civile Bioprojet | Non-imidazole aryloxy (or arylthio) alkylamines as histamine H3-receptor antagonists and their therapeutic applications |
| EP0982300A3 (en) * | 1998-07-29 | 2000-03-08 | Societe Civile Bioprojet | Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications |
| WO2002010156A1 (en) * | 2000-07-29 | 2002-02-07 | Arpida Ag | Benzofuran derivatives and their use as antibacterial agents |
-
2002
- 2002-03-11 BR BR0205829-4A patent/BR0205829A/pt not_active IP Right Cessation
- 2002-03-11 EP EP02715079A patent/EP1370546A2/en not_active Withdrawn
- 2002-03-11 WO PCT/US2002/007107 patent/WO2002074758A2/en not_active Ceased
- 2002-03-11 MX MXPA03008319A patent/MXPA03008319A/es active IP Right Grant
- 2002-03-11 CA CA2440238A patent/CA2440238C/en not_active Expired - Fee Related
- 2002-03-11 JP JP2002573767A patent/JP4612990B2/ja not_active Expired - Fee Related
- 2002-03-11 EP EP10180385A patent/EP2258694A1/en not_active Withdrawn
- 2002-03-15 AR ARP020100947A patent/AR035783A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR035783A1 (es) | 2004-07-14 |
| EP1370546A2 (en) | 2003-12-17 |
| MXPA03008319A (es) | 2003-12-11 |
| WO2002074758A2 (en) | 2002-09-26 |
| JP2005500986A (ja) | 2005-01-13 |
| JP4612990B2 (ja) | 2011-01-12 |
| CA2440238A1 (en) | 2002-09-26 |
| WO2002074758A3 (en) | 2003-03-20 |
| EP2258694A1 (en) | 2010-12-08 |
| BR0205829A (pt) | 2005-03-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150311 |