ZA200509019B - Substituted 3-alkyl and 3-alkenyl azetidine derivatives - Google Patents
Substituted 3-alkyl and 3-alkenyl azetidine derivatives Download PDFInfo
- Publication number
- ZA200509019B ZA200509019B ZA200509019A ZA200509019A ZA200509019B ZA 200509019 B ZA200509019 B ZA 200509019B ZA 200509019 A ZA200509019 A ZA 200509019A ZA 200509019 A ZA200509019 A ZA 200509019A ZA 200509019 B ZA200509019 B ZA 200509019B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- azetidin
- chlorophenyl
- difluorophenyl
- fluoro
- Prior art date
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- -1 (2) pyridyl Chemical group 0.000 claims description 92
- 125000001424 substituent group Chemical group 0.000 claims description 79
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 76
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 42
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 36
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 12
- 235000014632 disordered eating Nutrition 0.000 claims description 12
- 150000001721 carbon Chemical group 0.000 claims description 11
- 208000030814 Eating disease Diseases 0.000 claims description 10
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 10
- 208000008589 Obesity Diseases 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 235000020824 obesity Nutrition 0.000 claims description 10
- 230000037406 food intake Effects 0.000 claims description 9
- 235000012631 food intake Nutrition 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
- ILFIRBGRMCGNOO-UHFFFAOYSA-N 1,1-bis($l^{1}-oxidanyl)ethene Chemical group [O]C([O])=C ILFIRBGRMCGNOO-UHFFFAOYSA-N 0.000 claims description 8
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 6
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
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- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 139
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 20
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 16
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 claims 10
- 125000000068 chlorophenyl group Chemical group 0.000 claims 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims 2
- 208000010235 Food Addiction Diseases 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 206010027175 memory impairment Diseases 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
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- LOVPHSMOAVXQIH-UHFFFAOYSA-N (4-nitrophenyl) hydrogen carbonate Chemical compound OC(=O)OC1=CC=C([N+]([O-])=O)C=C1 LOVPHSMOAVXQIH-UHFFFAOYSA-N 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- NGTREPAVXJWHRY-UHFFFAOYSA-N 1-(1-methylimidazol-4-yl)propan-2-ol Chemical compound CC(O)CC1=CN(C)C=N1 NGTREPAVXJWHRY-UHFFFAOYSA-N 0.000 claims 1
- ZHRXBRLKJALMRK-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-yl]-1-(3-fluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C=CC(F)=CC=1C(C(C)(O)C)C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 ZHRXBRLKJALMRK-UHFFFAOYSA-N 0.000 claims 1
- JRWFXJMIFMVHEY-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-1-(3-fluorophenyl)-2-methylpropan-2-ol Chemical compound C=1C=CC(F)=CC=1C(C(C)(O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 JRWFXJMIFMVHEY-UHFFFAOYSA-N 0.000 claims 1
- JWBGEFWLKHNGHR-UHFFFAOYSA-N 1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-2-methyl-1-[3-(trifluoromethyl)phenyl]propan-2-ol Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(C(C)(O)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 JWBGEFWLKHNGHR-UHFFFAOYSA-N 0.000 claims 1
- QTVMNDFLTGOAED-UHFFFAOYSA-N 1-benzhydryl-3-[1-(3,5-difluorophenyl)-2-methylprop-1-enyl]azetidine Chemical compound C=1C(F)=CC(F)=CC=1C(=C(C)C)C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 QTVMNDFLTGOAED-UHFFFAOYSA-N 0.000 claims 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims 1
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- YPIOMNBXBMTSEN-UHFFFAOYSA-N 3-[1-(1-benzhydrylazetidin-3-yl)-2-fluoro-2-methylpropyl]-5-fluorobenzonitrile Chemical compound C=1C(F)=CC(C#N)=CC=1C(C(C)(F)C)C(C1)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 YPIOMNBXBMTSEN-UHFFFAOYSA-N 0.000 claims 1
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- XCQWICIJSZORFF-UHFFFAOYSA-N [1-[1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene]-1-(3,5-difluorophenyl)propan-2-yl] n,n-dimethylcarbamate Chemical compound C=1C(F)=CC(F)=CC=1C(C(OC(=O)N(C)C)C)=C(C1)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 XCQWICIJSZORFF-UHFFFAOYSA-N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
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- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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- 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
- C07D401/02—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 two hetero rings
- C07D401/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
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- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
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- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
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| US47785003P | 2003-06-11 | 2003-06-11 |
Publications (1)
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| ZA200509019B true ZA200509019B (en) | 2006-11-29 |
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| ZA200509019A ZA200509019B (en) | 2003-06-11 | 2005-11-08 | Substituted 3-alkyl and 3-alkenyl azetidine derivatives |
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| NZ534757A (en) | 2002-03-12 | 2006-07-28 | Merck & Co Inc | Substituted amides |
| CA2494091C (en) | 2002-08-02 | 2011-02-01 | Richard B. Toupence | Substituted furo [2,3-b| pyridine derivatives |
| EP1575901B1 (en) | 2002-12-19 | 2012-10-10 | Merck Sharp & Dohme Corp. | Substituted amides |
| CN1802351A (zh) | 2003-06-11 | 2006-07-12 | 麦克公司 | 被取代的3－烷基和3－链烯基氮杂环丁烷衍生物 |
| WO2005044785A1 (en) | 2003-10-30 | 2005-05-19 | Merck & Co., Inc. | Aralkyl amines as cannabinoid receptor modulators |
| WO2006119260A2 (en) * | 2005-05-02 | 2006-11-09 | Merck & Co., Inc. | Combination of dipeptidyl peptidase-iv inhibitor and a cannabinoid cb1 receptor antagonist for the treatment of diabetes and obesity |
| KR20080048502A (ko) | 2005-09-29 | 2008-06-02 | 머크 앤드 캄파니 인코포레이티드 | 멜라노코르틴-4 수용체 조절제로서의 아실화스피로피페리딘 유도체 |
| AR058199A1 (es) * | 2005-11-28 | 2008-01-23 | Merck & Co Inc | Derivados de 3- alquilazetidina sustituidos con heterociclos |
| US7906652B2 (en) * | 2005-11-28 | 2011-03-15 | Merck Sharp & Dohme Corp. | Heterocycle-substituted 3-alkyl azetidine derivatives |
| PE20071092A1 (es) * | 2005-12-08 | 2007-12-10 | Aventis Pharma Inc | Composicion farmaceutica que comprende un antagonista de cb1 y un agente antisicotico |
| AU2007221366B2 (en) | 2006-02-22 | 2012-08-23 | Msd Italia S.R.L. | Oxyntomodulin derivatives |
| EP2061767B1 (de) | 2006-08-08 | 2014-12-17 | Sanofi | Arylaminoaryl-alkyl-substituierte Imidazolidin-2,4-dione, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Arzneimittel und ihre Verwendung |
| AU2007300627B2 (en) | 2006-09-22 | 2012-02-16 | Merck Sharp & Dohme Corp. | Method of treatment using fatty acid synthesis inhibitors |
| WO2008118141A2 (en) * | 2006-10-17 | 2008-10-02 | Acadia Pharmaceuticals Inc. | Use of cannabinoid modulating compounds in combination with other therapeutic compounds for adjunctive therapy |
| US7999107B2 (en) | 2007-01-31 | 2011-08-16 | Merck Sharp & Dohme Corp. | Substituted pyrano[2,3-B]pyridine derivatives as cannabinoid-1 receptor modulators |
| JP5319518B2 (ja) | 2007-04-02 | 2013-10-16 | Ｍｓｄ株式会社 | インドールジオン誘導体 |
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| AU2008317482A1 (en) * | 2007-10-24 | 2009-04-30 | Merck Sharp & Dohme Corp. | Synthesis and crystalline forms of CB-1 antagonist/inverse agonist |
| EP2095814A1 (de) * | 2008-02-26 | 2009-09-02 | Wolfgang J. Kox | Medikamentengestützter Nikotinentzug |
| US8470841B2 (en) | 2008-07-09 | 2013-06-25 | Sanofi | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
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| EP2348857B1 (en) | 2008-10-22 | 2016-02-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| EP2350010B1 (en) | 2008-10-30 | 2014-03-26 | Merck Sharp & Dohme Corp. | Isonicotinamide orexin receptor antagonists |
| AU2009309037A1 (en) | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| WO2010144664A1 (en) | 2009-06-12 | 2010-12-16 | Schering Corporation | Thiophenes as glucagon receptor antagonists, compositions, and methods for their use |
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| US8895596B2 (en) | 2010-02-25 | 2014-11-25 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| EP3159331A1 (en) | 2010-05-05 | 2017-04-26 | Infinity Pharmaceuticals, Inc. | Tetrazolones as inhibitors of fatty acid synthase |
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| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| MY159058A (en) | 2011-02-25 | 2016-12-15 | Merck Sharp & Dohme | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agent |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120051A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8901114B2 (en) | 2011-03-08 | 2014-12-02 | Sanofi | Oxathiazine derivatives substituted with carbocycles or heterocycles, method for producing same, drugs containing said compounds, and use thereof |
| EP2683705B1 (de) | 2011-03-08 | 2015-04-22 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683703B1 (de) | 2011-03-08 | 2015-05-27 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
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| US8846666B2 (en) | 2011-03-08 | 2014-09-30 | Sanofi | Oxathiazine derivatives which are substituted with benzyl or heteromethylene groups, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
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| EP2880028B1 (en) | 2012-08-02 | 2020-09-30 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
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| US11098029B2 (en) | 2019-02-13 | 2021-08-24 | Merck Sharp & Dohme Corp. | 5-alkyl pyrrolidine orexin receptor agonists |
| EP4010314B1 (en) | 2019-08-08 | 2024-02-28 | Merck Sharp & Dohme LLC | Heteroaryl pyrrolidine and piperidine orexin receptor agonists |
| CN116249697A (zh) | 2020-08-18 | 2023-06-09 | 默沙东有限责任公司 | 二环庚烷吡咯烷食欲素受体激动剂 |
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| AU2001241927A1 (en) | 2000-02-28 | 2001-09-12 | Scios Inc. | Inhibitors of p38-alpha kinase |
| US6355631B1 (en) * | 2000-03-03 | 2002-03-12 | Aventis Pharma S.A. | Pharmaceutical compositions containing azetidine derivatives, novel azetidine derivatives and their preparation |
| US6479479B2 (en) * | 2000-03-03 | 2002-11-12 | Aventis Pharma S.A. | Azetidine derivatives, their preparation and pharmaceutical compositions containing them |
| FR2805818B1 (fr) | 2000-03-03 | 2002-04-26 | Aventis Pharma Sa | Derives d'azetidine, leur preparation et les compositions pharmaceutiques les contenant |
| FR2805810B1 (fr) | 2000-03-03 | 2002-04-26 | Aventis Pharma Sa | Compositions pharmaceutiques contenant des derives de 3- amino-azetidine, les nouveaux derives et leur preparation |
| FR2805817B1 (fr) * | 2000-03-03 | 2002-04-26 | Aventis Pharma Sa | Compositions pharmaceutiques contenant des derives d'azetidine, les nouveaux derives d'azetidine et leur preparation |
| GB0019006D0 (en) | 2000-08-04 | 2000-09-20 | Astrazeneca Ab | Novel compounds |
| FR2814678B1 (fr) | 2000-10-04 | 2002-12-20 | Aventis Pharma Sa | Association d'un antagoniste du recepteur cb1 et de sibutramine, les compositions pharmaceutiques les contenant et leur utilisation pour la traitement de l'obesite |
| GB0117387D0 (en) | 2001-07-17 | 2001-09-05 | Novartis Ag | Organic compounds |
| FR2829028B1 (fr) | 2001-08-29 | 2004-12-17 | Aventis Pharma Sa | Association d'un antagoniste du recepteur cb1 et d'un produit qui active la neurotransmission dopaminergique dans le cerveau, les compositions pharmaceutiques les contenant et leur utilisation pour le traitement de la maladie de |
| FR2829027A1 (fr) | 2001-08-29 | 2003-03-07 | Aventis Pharma Sa | Association avec un antagoniste du recepteur cb1, les compositions pharmaceutiques les contenant et leur utilisation pour le traitement de la maladie de parkinson |
| JP4660199B2 (ja) | 2002-12-23 | 2011-03-30 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 置換１−ピペリジン−４−イル−４−アゼチジン−３−イル−ピペラジン誘導体およびそれらのニューロキニン拮抗薬としての使用 |
| US20070173486A1 (en) | 2003-05-01 | 2007-07-26 | Vernalis Research Limited | Azetidinecarboxamide derivatives and their use in the treatment of cb1 receptor mediated disordrs |
| EA010583B1 (ru) | 2003-05-01 | 2008-10-30 | Вернэлис Рисёч Лимитед | Производные азетидинкарбоксамида и их применение при лечении нарушений, опосредованных св1 рецепторами |
| CN1802351A (zh) | 2003-06-11 | 2006-07-12 | 麦克公司 | 被取代的3－烷基和3－链烯基氮杂环丁烷衍生物 |
| BRPI0507801A (pt) | 2004-02-17 | 2007-07-10 | Esteve Labor Dr | compostos de azetidina substituìda, processo para a preparação de compostos de azetidina substituìda, medicamento e uso de pelo menos um composto de azetidina substituìda |
| US7906652B2 (en) * | 2005-11-28 | 2011-03-15 | Merck Sharp & Dohme Corp. | Heterocycle-substituted 3-alkyl azetidine derivatives |
-
2004
- 2004-06-09 CN CNA2004800160109A patent/CN1802351A/zh active Pending
- 2004-06-09 US US10/557,246 patent/US7485732B2/en not_active Expired - Fee Related
- 2004-06-09 NZ NZ543451A patent/NZ543451A/en unknown
- 2004-06-09 CA CA002527933A patent/CA2527933C/en not_active Expired - Fee Related
- 2004-06-09 UA UAA200600239A patent/UA83230C2/ru unknown
- 2004-06-09 RU RU2006100298/04A patent/RU2006100298A/ru not_active Application Discontinuation
- 2004-06-09 BR BRPI0411131-1A patent/BRPI0411131A/pt not_active IP Right Cessation
- 2004-06-09 AU AU2004252109A patent/AU2004252109B2/en not_active Ceased
- 2004-06-09 WO PCT/US2004/018348 patent/WO2005000809A1/en not_active Ceased
- 2004-06-09 JP JP2006533655A patent/JP3939744B2/ja not_active Expired - Fee Related
- 2004-06-09 MX MXPA05013583A patent/MXPA05013583A/es unknown
- 2004-06-09 EP EP04776404A patent/EP1636181A1/en not_active Withdrawn
- 2004-06-09 KR KR1020057023696A patent/KR20060019587A/ko not_active Ceased
-
2005
- 2005-11-08 ZA ZA200509019A patent/ZA200509019B/en unknown
- 2005-11-24 IS IS8146A patent/IS8146A/is unknown
- 2005-12-05 MA MA28634A patent/MA27847A1/fr unknown
- 2005-12-05 CO CO05123378A patent/CO5650244A2/es not_active Application Discontinuation
- 2005-12-06 IL IL172417A patent/IL172417A0/en unknown
- 2005-12-08 EC EC2005006207A patent/ECSP056207A/es unknown
-
2006
- 2006-01-10 NO NO20060141A patent/NO20060141L/no not_active Application Discontinuation
-
2007
- 2007-02-13 JP JP2007031781A patent/JP2007186518A/ja active Pending
-
2008
- 2008-10-21 US US12/288,518 patent/US7906503B2/en not_active Expired - Fee Related
-
2011
- 2011-03-11 JP JP2011053759A patent/JP2011144196A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005000809A1 (en) | 2005-01-06 |
| KR20060019587A (ko) | 2006-03-03 |
| US20090069284A1 (en) | 2009-03-12 |
| CA2527933A1 (en) | 2005-01-06 |
| UA83230C2 (ru) | 2008-06-25 |
| NO20060141L (no) | 2006-03-13 |
| CN1802351A (zh) | 2006-07-12 |
| US20060293299A1 (en) | 2006-12-28 |
| JP2007186518A (ja) | 2007-07-26 |
| ECSP056207A (es) | 2006-04-19 |
| JP3939744B2 (ja) | 2007-07-04 |
| RU2006100298A (ru) | 2006-05-10 |
| MA27847A1 (fr) | 2006-04-03 |
| BRPI0411131A (pt) | 2006-07-18 |
| JP2007500246A (ja) | 2007-01-11 |
| NZ543451A (en) | 2008-08-29 |
| EP1636181A1 (en) | 2006-03-22 |
| AU2004252109B2 (en) | 2010-04-08 |
| CO5650244A2 (es) | 2006-06-30 |
| US7485732B2 (en) | 2009-02-03 |
| US7906503B2 (en) | 2011-03-15 |
| AU2004252109A1 (en) | 2005-01-06 |
| CA2527933C (en) | 2009-08-11 |
| JP2011144196A (ja) | 2011-07-28 |
| IL172417A0 (en) | 2006-04-10 |
| MXPA05013583A (es) | 2006-03-09 |
| IS8146A (is) | 2005-11-24 |
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