ZA200601146B - Piperazone with OR-substituted phenyl group and their use as Gly T1 inhibitors - Google Patents

Piperazone with OR-substituted phenyl group and their use as Gly T1 inhibitors Download PDF

Info

Publication number: ZA200601146B
Authority: ZA; South Africa
Prior art keywords: phenyl; piperazin; methanesulfonyl; fluoro; methanone
Prior art date: 2003-08-11

Application number

ZA200601146A

Other languages

English (en)

Inventor

Jolidon Synese

Nettekoven Matthias Heinrich

Pinard Emmanuel

Narquizian Robert

Norcross Roger David

Stalder Henri

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

2003-08-11

Filing date

2006-02-08

Publication date

2007-05-30

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=34130061&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ZA200601146(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2006-02-08 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2007-05-30 Publication of ZA200601146B publication Critical patent/ZA200601146B/en

Links

125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 20
239000003112 inhibitor Substances 0.000 title description 5
IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 title 1
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 104
150000001875 compounds Chemical class 0.000 claims description 80
229910052736 halogen Inorganic materials 0.000 claims description 46
150000002367 halogens Chemical group 0.000 claims description 46
-1 bicyclo[2.2.1]heptyl Chemical group 0.000 claims description 32
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 17
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
125000001072 heteroaryl group Chemical group 0.000 claims description 14
201000000980 schizophrenia Diseases 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 11
229910052792 caesium Inorganic materials 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
208000028017 Psychotic disease Diseases 0.000 claims description 7
201000010099 disease Diseases 0.000 claims description 7
208000035475 disorder Diseases 0.000 claims description 7
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
238000011282 treatment Methods 0.000 claims description 6
206010012289 Dementia Diseases 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
239000005864 Sulphur Substances 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
230000001771 impaired effect Effects 0.000 claims description 5
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 4
208000024827 Alzheimer disease Diseases 0.000 claims description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
230000019771 cognition Effects 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 3
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
230000003213 activating effect Effects 0.000 claims description 3
230000006735 deficit Effects 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
125000003107 substituted aryl group Chemical group 0.000 claims description 3
CLPDPJIINMSDAG-UHFFFAOYSA-N 4-[4-(2-cyclopentyloxy-5-methylsulfonylbenzoyl)piperazin-1-yl]-2-fluorobenzonitrile Chemical compound C1CN(C=2C=C(F)C(C#N)=CC=2)CCN1C(=O)C1=CC(S(=O)(=O)C)=CC=C1OC1CCCC1 CLPDPJIINMSDAG-UHFFFAOYSA-N 0.000 claims description 2
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 2
239000012317 TBTU Substances 0.000 claims description 2
HXWMJBQWXCYJSG-UHFFFAOYSA-N [4-(4-chloro-2-nitrophenyl)piperazin-1-yl]-[4-(dimethylamino)-2-methoxy-5-nitrophenyl]methanone Chemical compound COC1=CC(N(C)C)=C([N+]([O-])=O)C=C1C(=O)N1CCN(C=2C(=CC(Cl)=CC=2)[N+]([O-])=O)CC1 HXWMJBQWXCYJSG-UHFFFAOYSA-N 0.000 claims description 2
CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 2
229910000024 caesium carbonate Inorganic materials 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 2
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
235000013350 formula milk Nutrition 0.000 claims 36
229960005141 piperazine Drugs 0.000 claims 14
150000002431 hydrogen Chemical class 0.000 claims 3
102100028644 Tenascin-R Human genes 0.000 claims 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
239000000126 substance Substances 0.000 claims 2
229940124530 sulfonamide Drugs 0.000 claims 2
150000003456 sulfonamides Chemical class 0.000 claims 2
108010020387 tenascin R Proteins 0.000 claims 2
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
FDAUGFSWIZUKGM-UHFFFAOYSA-N 1-[4-[4-[2-(cyclobutylmethoxy)-5-methylsulfonylbenzoyl]piperazin-1-yl]-3-fluorophenyl]ethanone Chemical compound FC1=CC(C(=O)C)=CC=C1N1CCN(C(=O)C=2C(=CC=C(C=2)S(C)(=O)=O)OCC2CCC2)CC1 FDAUGFSWIZUKGM-UHFFFAOYSA-N 0.000 claims 1
WBYYGBHFXXFGOM-UHFFFAOYSA-N 1-[4-[4-[2-(cyclopropylmethoxy)-5-methylsulfonylbenzoyl]piperazin-1-yl]-3-fluorophenyl]ethanone Chemical compound FC1=CC(C(=O)C)=CC=C1N1CCN(C(=O)C=2C(=CC=C(C=2)S(C)(=O)=O)OCC2CC2)CC1 WBYYGBHFXXFGOM-UHFFFAOYSA-N 0.000 claims 1
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
JESFTAIITPRUSJ-UHFFFAOYSA-N 2,5-difluoro-4-[4-[2-(2-methylpropoxy)-5-methylsulfonylbenzoyl]piperazin-1-yl]benzonitrile Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CCN(C=2C(=CC(=C(F)C=2)C#N)F)CC1 JESFTAIITPRUSJ-UHFFFAOYSA-N 0.000 claims 1
GQBGEESEVXRXFR-UHFFFAOYSA-N 2,6-difluoro-4-[4-[2-(2-methylpropoxy)-5-methylsulfonylbenzoyl]piperazin-1-yl]benzonitrile Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CCN(C=2C=C(F)C(C#N)=C(F)C=2)CC1 GQBGEESEVXRXFR-UHFFFAOYSA-N 0.000 claims 1
GQFVRYSQXIQEKC-UHFFFAOYSA-N 2-fluoro-4-[4-[2-(2-methylpropoxy)-5-methylsulfonylbenzoyl]piperazin-1-yl]benzonitrile Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CCN(C=2C=C(F)C(C#N)=CC=2)CC1 GQFVRYSQXIQEKC-UHFFFAOYSA-N 0.000 claims 1
KSKJRPDLQBDCAY-UHFFFAOYSA-N 3,5-difluoro-4-[4-[2-(2-methylpropoxy)-5-methylsulfonylbenzoyl]piperazin-1-yl]benzonitrile Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CCN(C=2C(=CC(=CC=2F)C#N)F)CC1 KSKJRPDLQBDCAY-UHFFFAOYSA-N 0.000 claims 1
IIKQERNGSZVMCA-UHFFFAOYSA-N 3-[4-(3-chlorophenyl)piperazine-1-carbonyl]-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(=O)N1CCN(C=2C=C(Cl)C=CC=2)CC1 IIKQERNGSZVMCA-UHFFFAOYSA-N 0.000 claims 1
HXKGYJNCJMXXEE-UHFFFAOYSA-N 3-[4-(4-acetyl-2-fluorophenyl)piperazine-1-carbonyl]-4-(2,2-dimethylpropoxy)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCC(C)(C)C)C(C(=O)N2CCN(CC2)C=2C(=CC(=CC=2)C(C)=O)F)=C1 HXKGYJNCJMXXEE-UHFFFAOYSA-N 0.000 claims 1
FALWCSBJGDGRBX-UHFFFAOYSA-N 3-[4-(4-cyano-2-fluorophenyl)piperazine-1-carbonyl]-4-(2,2-dimethylpropoxy)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCC(C)(C)C)C(C(=O)N2CCN(CC2)C=2C(=CC(=CC=2)C#N)F)=C1 FALWCSBJGDGRBX-UHFFFAOYSA-N 0.000 claims 1
GTMJJECWFSYTLY-UHFFFAOYSA-N 3-[4-(4-cyano-2-fluorophenyl)piperazine-1-carbonyl]-n-methyl-4-(2,2,2-trifluoroethoxy)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCC(F)(F)F)C(C(=O)N2CCN(CC2)C=2C(=CC(=CC=2)C#N)F)=C1 GTMJJECWFSYTLY-UHFFFAOYSA-N 0.000 claims 1
MDILCRFEKWGLDH-UHFFFAOYSA-N 3-fluoro-4-[4-[2-(2-methylpropoxy)-5-methylsulfonylbenzoyl]piperazin-1-yl]benzonitrile Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CCN(C=2C(=CC(=CC=2)C#N)F)CC1 MDILCRFEKWGLDH-UHFFFAOYSA-N 0.000 claims 1
PGMNFQXFRLOYOT-UHFFFAOYSA-N 4-(cyclobutylmethoxy)-n-methyl-3-[4-[4-(trifluoromethyl)phenyl]piperazine-1-carbonyl]benzenesulfonamide Chemical compound C1CN(C=2C=CC(=CC=2)C(F)(F)F)CCN1C(=O)C1=CC(S(=O)(=O)NC)=CC=C1OCC1CCC1 PGMNFQXFRLOYOT-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
229940123355 Glycine uptake inhibitor Drugs 0.000 claims 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
241000009298 Trigla lyra Species 0.000 claims 1
RQKPLLFVBWOACY-UHFFFAOYSA-N [4-(2-fluoro-4-methylsulfonylphenyl)piperazin-1-yl]-[2-(2-methylpropoxy)-5-methylsulfonylphenyl]methanone Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CCN(C=2C(=CC(=CC=2)S(C)(=O)=O)F)CC1 RQKPLLFVBWOACY-UHFFFAOYSA-N 0.000 claims 1
UAEWYJBPCXZRGM-UHFFFAOYSA-N [4-(3-amino-4-nitrophenyl)-2-methylpiperazin-1-yl]-[4-(dimethylamino)-2-methoxy-5-nitrophenyl]methanone Chemical compound COC1=CC(N(C)C)=C([N+]([O-])=O)C=C1C(=O)N1C(C)CN(C=2C=C(N)C(=CC=2)[N+]([O-])=O)CC1 UAEWYJBPCXZRGM-UHFFFAOYSA-N 0.000 claims 1
BTDNOUMJPYHXLL-UHFFFAOYSA-N [4-[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-(5-methylsulfonyl-2-propan-2-yloxyphenyl)methanone Chemical compound CC(C)OC1=CC=C(S(C)(=O)=O)C=C1C(=O)N1CCN(C=2C(=CC(=CN=2)C(F)(F)F)F)CC1 BTDNOUMJPYHXLL-UHFFFAOYSA-N 0.000 claims 1
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125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
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MOFQYSNJEBSGRH-UHFFFAOYSA-N n-methyl-4-(2,2,2-trifluoroethoxy)-3-[4-[4-(trifluoromethyl)phenyl]piperazine-1-carbonyl]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(OCC(F)(F)F)C(C(=O)N2CCN(CC2)C=2C=CC(=CC=2)C(F)(F)F)=C1 MOFQYSNJEBSGRH-UHFFFAOYSA-N 0.000 claims 1
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229910052700 potassium Inorganic materials 0.000 claims 1
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108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 description 17
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WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 6
229930195712 glutamate Natural products 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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Classifications

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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
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- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen 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
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen 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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers

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Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
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ZA200601146A 2003-08-11 2006-02-08 Piperazone with OR-substituted phenyl group and their use as Gly T1 inhibitors ZA200601146B (en)

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JP (1)	JP4252598B2 (de)
KR (1)	KR100774622B1 (de)
CN (1)	CN1867554B (de)
AR (1)	AR045360A1 (de)
AT (1)	ATE382611T1 (de)
AU (1)	AU2004263306B2 (de)
BR (1)	BRPI0413497B8 (de)
CA (1)	CA2534675C (de)
CO (1)	CO5650253A2 (de)
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CY (1)	CY1108616T1 (de)
DE (1)	DE602004011076T2 (de)
DK (1)	DK1656361T3 (de)
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SI (1)	SI1656361T1 (de)
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UA (1)	UA85194C2 (de)
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US20050119251A1 (en) *	2001-12-21	2005-06-02	Jian-Min Fu	Nicotinamide derivatives and their use as therapeutic agents
UA85194C2 (ru)	2003-08-11	2009-01-12	Ф.Хоффманн-Ля Рош Аг	Пиперазины с or-замещенной фенильной группой и их применение как ингибиторов glyt 1
ATE374610T1 (de) *	2003-09-09	2007-10-15	Hoffmann La Roche	1-(2-amino-benzoyl)-piperazin-derivate als glycin-aufnahmehemmer zur behandlung von psychosen
AU2004269892B2 (en) *	2003-09-09	2010-03-11	F. Hoffmann-La Roche Ag	1-benzoyl-piperazine derivatives as glycine uptake inhibitors for the treatment of psychoses
JP4958786B2 (ja)	2004-09-20	2012-06-20	ゼノン・ファーマシューティカルズ・インコーポレイテッド	複素環誘導体および治療薬としてのそれらの使用
MX2007003327A (es)	2004-09-20	2007-06-05	Xenon Pharmaceuticals Inc	Derivados heterociclicos, y su uso como mediadores de estearoil-coa desaturasa.
US20080167321A1 (en) *	2004-09-20	2008-07-10	Xenon Pharmaceuticals Inc.	Pyridine Derivatives For Inhibiting Human Stearoyl-Coa-Desaturase
MX2007003319A (es)	2004-09-20	2007-06-05	Xenon Pharmaceuticals Inc	Derivados heterociclicos y su uso como agentes terapeuticos.
US7547698B2 (en) *	2004-09-20	2009-06-16	Xenon Pharmaceuticals Inc.	Bicyclic heterocyclic derivatives and their use as inhibitors of stearoyl-coadesaturase (SCD)
EP2289510A1 (de)	2004-09-20	2011-03-02	Xenon Pharmaceuticals Inc.	Heterozyklische Derivate zur Behandlung von durch Stearoyl-Coa-Desaturase-Enzyme verursachten Krankheiten
MX2007003332A (es)	2004-09-20	2007-06-05	Xenon Pharmaceuticals Inc	Derivados heterociclicos y su uso como inhibidores de estearoil-coa-desaturasa.
EP1799667B1 (de)	2004-09-20	2013-03-20	Xenon Pharmaceuticals Inc.	Heterozyklische derivate und ihre verwendung als therapeutische wirkstoffe
EP2269610A3 (de)	2004-09-20	2011-03-09	Xenon Pharmaceuticals Inc.	Heterozyklische Derivate und ihre Verwendung als Stearoyl-Coa-Desaturase-Inhibitoren
RU2395502C2 (ru) *	2004-12-09	2010-07-27	Ф.Хоффманн-Ля Рош Аг	Производные фенил-пиперазин метанона
DE602005019465D1 (de) *	2004-12-15	2010-04-01	Hoffmann La Roche	Bi- und trizyklische substituierte phenyl-methanone als inhibitoren von glycin-i (glyt-1)-transportern zur behandlung der alzheimer-krankheit
US7485637B2 (en) *	2005-01-04	2009-02-03	Hoffmann-La Roche Inc.	Benzoyl-tetrahydropiperidine derivatives
CA2593453A1 (en) *	2005-01-06	2006-07-13	F. Hoffmann-La Roche Ag	Sulfanyl substituted phenyl methanones as glycine transporter 1 (glyt-1) inhibitors for the treatment of neurological and neuropsychiatric disorders
AU2005324024B2 (en)	2005-01-07	2011-02-17	F. Hoffmann-La Roche Ag	[4-(Heteroaryl) piperazin-1-yl]-(2,5-substituted -phenyl)methanone derivatives as glycine transporter 1 (GlyT-1) inhibitors for the treatment of neurological and neuropsychiatric disorders
JP2008527016A (ja) *	2005-01-18	2008-07-24	エフ．ホフマン−ラロシュアーゲー	神経及び神経精神病の疾患の治療のためのグリシントランスポーター１（ＧｌｙＴ−１）阻害剤としての２，５−二置換フェニルメタノン誘導体
KR100915472B1 (ko) *	2005-01-26	2009-09-03	에프. 호프만-라 로슈 아게	페닐 메탄온 유도체 및 그의 글라이신 트랜스포터 1억제제로서의 용도
UA91536C2 (uk) *	2005-02-07	2010-08-10	Ф. Хоффманн-Ля Рош Аг	Гетероциклічні заміщені фенілметанони як інгібітори переносника гліцину 1
GB0505085D0 (en) *	2005-03-11	2005-04-20	Glaxo Group Ltd	Compounds
GB0505086D0 (en) *	2005-03-11	2005-04-20	Glaxo Group Ltd	Compounds
GB0505084D0 (en) *	2005-03-11	2005-04-20	Glaxo Group Ltd	Compounds
BRPI0611187A2 (pt)	2005-06-03	2010-08-24	Xenon Pharmaceuticals Inc	derivados aminotiazàis como inibidores da estearoil-coa desaturase humana
WO2007006650A2 (en) *	2005-07-08	2007-01-18	F. Hoffmann-La Roche Ag	Asymmetric reduction of 1,1,1-trifluoroacetone
GB0523853D0 (en) *	2005-11-24	2006-01-04	3M Innovative Properties Co	Fluorinated surfactants for use in making a fluoropolymer
CA2636929A1 (en) *	2005-12-21	2007-07-12	Decode Genetics, Ehf	Biaryl nitrogen heterocycle inhibitors of lta4h for treating inflammation
WO2007134457A1 (en) *	2006-05-22	2007-11-29	Merck Frosst Canada Ltd.	Cyclic amine derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase
ES2406085T3 (es)	2006-06-22	2013-06-05	F. Hoffmann-La Roche Ag	Derivados de fenil-metanona sustituida y su empleo como inhibidores de receptores de GlyT1 y GlyT2
SG172685A1 (en)	2006-06-28	2011-07-28	Amgen Inc	Glycine transporter-1 inhibitors
ES2411713T3 (es)	2006-07-27	2013-07-08	F. Hoffmann-La Roche Ag	Hidrogenación asimétrica de 1,1,1-trifluoroacetona
KR101364353B1 (ko) *	2006-11-30	2014-02-18	다우 아그로사이언시즈 엘엘씨	2-치환된-5-(1-알킬티오)알킬피리딘의 제조 방법
NZ577502A (en) *	2006-12-28	2012-02-24	Hoffmann La Roche	Crystalline forms glyt1
WO2008107334A2 (en) *	2007-03-05	2008-09-12	F. Hoffmann-La Roche Ag	Process for the synthesis of glyt-1 inhibitors
WO2008148840A1 (en)	2007-06-08	2008-12-11	Janssen Pharmaceutica N.V.	Piperidine/piperazine derivatives
JO2972B1 (en)	2007-06-08	2016-03-15	جانسين فارماسوتيكا ان. في	Piperidine / piperazine derivatives
AU2008258560C1 (en) *	2007-06-08	2014-04-10	Janssen Pharmaceutica N.V.	Piperidine/piperazine derivatives
PE20090362A1 (es) *	2007-06-08	2009-04-04	Janssen Pharmaceutica Nv	Derivados de piperidina/piperazina como moduladores de dgat
EP2178842A2 (de)	2007-08-22	2010-04-28	Abbott GmbH & Co. KG	4-benzylaminochinoline, pharmazeutische zusammensetzungen, die diese enthalten, und ihre verwendung
ES2397764T3 (es)	2008-04-01	2013-03-11	Abbott Gmbh & Co. Kg	Tetrahidroisoquinolinas, composiciones farmacéuticas que las contienen, y su uso en terapia
PE20140572A1 (es)	2008-06-05	2014-05-16	Janssen Pharmaceutica Nv	Combinaciones de drogas que comprenden un inhibidor de dgat y un agonista de ppar
JP2012501344A (ja) *	2008-08-29	2012-01-19	トレヴェンティスコーポレイション	アミロイド症を治療する組成物及び方法
US20160283652A1 (en)	2008-08-29	2016-09-29	Treventis Corporation	Methods for identifying inhibitors of amyloid protein aggregation
CA2739869C (en)	2008-11-04	2016-09-27	F. Hoffmann-La Roche Ag	Radiolabelled inhibitors of the glycine 1 transporter
CN101759665B (zh) *	2008-12-23	2012-03-28	江苏恩华药业股份有限公司	取代苯基哌嗪芳烷醇衍生物及其在制备镇痛药物中的应用
AR075442A1 (es)	2009-02-16	2011-03-30	Abbott Gmbh & Co Kg	Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia
TW201038569A (en)	2009-02-16	2010-11-01	Abbott Gmbh & Co Kg	Heterocyclic compounds, pharmaceutical compositions containing them, and their use in therapy
WO2011002067A1 (ja) *	2009-07-02	2011-01-06	武田薬品工業株式会社	複素環化合物およびその用途
US20120035156A1 (en) *	2010-08-09	2012-02-09	Daniela Alberati	Combination of glyt1 compound with antipsychotics
US8877794B2 (en)	2010-08-13	2014-11-04	Abbott Laboratories	Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy
US8846743B2 (en)	2010-08-13	2014-09-30	Abbott Laboratories	Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy
US9045459B2 (en)	2010-08-13	2015-06-02	AbbVie Deutschland GmbH & Co. KG	Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy
US8883839B2 (en)	2010-08-13	2014-11-11	Abbott Laboratories	Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy
US9051280B2 (en)	2010-08-13	2015-06-09	AbbVie Deutschland GmbH & Co. KG	Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy
WO2012027495A1 (en)	2010-08-27	2012-03-01	University Of The Pacific	Piperazinylpyrimidine analogues as protein kinase inhibitors
US9309200B2 (en)	2011-05-12	2016-04-12	AbbVie Deutschland GmbH & Co. KG	Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy
JP2014521682A (ja)	2011-08-05	2014-08-28	アッヴィ・ドイチュラント・ゲー・エム・ベー・ハー・ウント・コー・カー・ゲー	アミノクロマン、アミノチオクロマンおよびアミノ−１，２，３，４−テトラヒドロキノリン誘導体、これらを含有する医薬組成物、ならびに治療におけるこれらの使用
EP2780328A1 (de)	2011-11-18	2014-09-24	Abbvie Deutschland GmbH & Co. KG	N-substituierte aminobenzocyclohepten-, aminotetralin-, aminoindan- und phenylalkylaminderivate, diese enthaltende pharmazeutische zusammensetzungen und ihre therapeutische verwendung
US9365512B2 (en)	2012-02-13	2016-06-14	AbbVie Deutschland GmbH & Co. KG	Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy
US9656955B2 (en)	2013-03-15	2017-05-23	Abbvie Inc.	Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy
US9650334B2 (en)	2013-03-15	2017-05-16	Abbvie Inc.	Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy
WO2014163156A1 (ja)	2013-04-04	2014-10-09	味の素株式会社	脱保護方法
WO2014192865A1 (ja) *	2013-05-30	2014-12-04	大日本住友製薬株式会社	フェニルピペラジン誘導体
KR101472916B1 (ko) *	2013-06-27	2014-12-16	한국과학기술연구원	모르폴린 또는 피페라진 화합물, 및 도네페질을 포함하는 인지 장애 관련 질병의 예방 또는 치료용 약학적 조성물
MX2016004936A (es)	2013-10-17	2016-12-20	Abbvie Deutschland	Derivados de aminocromano, aminotiocromano y amino-1,2,3,4-tetrahi droquinilina, composiciones farmaceuticas que los contienen, y su uso en terapia.
WO2015055771A1 (en)	2013-10-17	2015-04-23	AbbVie Deutschland GmbH & Co. KG	Aminotetraline and aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy
CN104628679B (zh) *	2013-11-08	2018-02-09	江苏恩华药业股份有限公司	Bitopertin的合成方法及其中间体
WO2015082367A1 (en) *	2013-12-03	2015-06-11	F. Hoffmann-La Roche Ag	Pharmaceutical composition
RU2577039C2 (ru) *	2014-02-28	2016-03-10	Закрытое Акционерное Общество "Вертекс"	Вещество, обладающее сочетанной антиагрегантной, антикоагулянтной и вазодилаторной активностью, и способ получения n, n'-замещенных пиперазинов
EP3134406A1 (de)	2014-04-24	2017-03-01	Dart Neuroscience (Cayman) Ltd	Substituierte 2,4,5,6-tetrahydropyrrolo [ 3,4-c ] pyrazol-und 4,5,6,7-tetrahydro-2 h-pyrazolo [ 4,3-c ] pyridinverbindungen als glyt1-inhibitoren
SG11201608397UA (en) *	2014-04-30	2016-11-29	Hoffmann La Roche	Glyt1 inhibitors for use in the treatment of hematological disorders
US9550754B2 (en)	2014-09-11	2017-01-24	AbbVie Deutschland GmbH & Co. KG	4,5-dihydropyrazole derivatives, pharmaceutical compositions containing them, and their use in therapy
US10040759B2 (en)	2014-11-05	2018-08-07	Dart Neuroscience (Cayman) Ltd.	Substituted azetidinyl compounds as GlyT1 inhibitors
CN105712952B (zh) *	2014-12-22	2021-03-26	上海翰森生物医药科技有限公司	2-取代氧基-5-甲砜基苯基哌嗪酰胺类似物及其制备方法和用途
CN105017098A (zh) *	2015-07-17	2015-11-04	大连奇凯医药科技有限公司	烷氧基类苯磺酰胺及其衍生物的制备工艺
CN106397312B (zh) *	2015-07-31	2020-03-24	广东东阳光药业有限公司	一种制备glyt-1抑制剂的方法
JP7359783B2 (ja)	2018-06-05	2023-10-11	クリネティックスファーマシューティカルズ，インク．	メラノコルチンサブタイプ－２受容体（ｍｃ２ｒ）アンタゴニストおよびその使用
JP7657792B2 (ja)	2019-11-07	2025-04-07	クリネティックスファーマシューティカルズ，インク．	メラノコルチンサブタイプ－２受容体（ｍｃ２ｒ）アンタゴニストおよびその使用
PT4077307T (pt)	2019-12-18	2025-06-03	Crinetics Pharmaceuticals Inc	Antagonistas do recetor de subtipo 2 da melanocortina (mc2r) à base de piperidina gem-dissubstituída e suas utilizações
JP7651574B2 (ja)	2019-12-23	2025-03-26	クリネティックスファーマシューティカルズ，インク．	スピロ環式ピペリジンメラノコルチンサブタイプ－２受容体（ｍｃ２ｒ）アンタゴニストおよびその使用
EP4087570A4 (de)	2020-01-09	2024-04-03	Disc Medicine, Inc.	Verfahren zur behandlung von erythropoetischer protoporphyrie, x-verknüpfter protoporphyrie oder kongenitaler erythropoetischer porphyrie mit glycintransportinhibitoren
CN117567449A (zh)	2020-10-13	2024-02-20	勃林格殷格翰国际有限公司	再加工方法
IL305952A (en)	2021-03-19	2023-11-01	Crinetics Pharmaceuticals Inc	Melanocortin subtype 2 receptor (MC2R) antagonist for disease treatment

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5018112A (en) *	1982-10-18	1991-05-21	Conoco Inc.	Method for hydrocarbon reservoir identification
IT1176613B (it) *	1984-08-14	1987-08-18	Ravizza Spa	Derivati piperazinici farmacologicamente attivi e processo per la loro preparazione
JPH0651625B2 (ja) *	1986-12-29	1994-07-06	株式会社大塚製薬工場	高脂質血症治療剤
CN1291984A (zh) *	1998-03-06	2001-04-18	詹森药业有限公司	甘氨酸传输抑制剂
GB0021419D0 (en) *	2000-08-31	2000-10-18	Oxford Glycosciences Uk Ltd	Compounds
DE10112040A1 (de)	2001-03-14	2002-10-02	Aventis Pharma Gmbh	Verbessertes Verfahren zur Herstellung von Sulfonylcarboxamidderivaten
BR0215202A (pt) *	2001-12-20	2004-10-13	Osi Pharm Inc	Compostos antagonistas seletivos a2b de pirimidina, sua sìntese e uso
UA85194C2 (ru)	2003-08-11	2009-01-12	Ф.Хоффманн-Ля Рош Аг	Пиперазины с or-замещенной фенильной группой и их применение как ингибиторов glyt 1

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TWI289556B (en)	2007-11-11
MEP27708A (en)	2010-06-10
CO5650253A2 (es)	2006-06-30
EP1656361B1 (de)	2008-01-02
DK1656361T3 (da)	2008-05-05
US20050209241A1 (en)	2005-09-22
AU2004263306A1 (en)	2005-02-17
US7319099B2 (en)	2008-01-15
KR100774622B1 (ko)	2007-11-08
BRPI0413497B1 (pt)	2017-12-19
DE602004011076D1 (de)	2008-02-14
HK1098147A1 (en)	2007-07-13
AR045360A1 (es)	2005-10-26
JP4252598B2 (ja)	2009-04-08
JP2007501820A (ja)	2007-02-01
AU2004263306A2 (en)	2005-02-17
DE602004011076T2 (de)	2009-01-02
ME00116B (me)	2010-10-10
BRPI0413497B8 (pt)	2021-05-25
RS53252B (sr)	2014-08-29
NZ544820A (en)	2009-02-28
AU2004263306B2 (en)	2010-04-22
ATE382611T1 (de)	2008-01-15
NO20060541L (no)	2006-03-08
KR20060037434A (ko)	2006-05-03
TNSN06042A1 (en)	2007-10-03
IL173274A (en)	2012-06-28
ECSP066358A (es)	2006-08-30
BRPI0413497A (pt)	2006-10-17
HRP20080137T3 (en)	2008-06-30
CA2534675C (en)	2013-07-23
SI1656361T1 (sl)	2008-04-30
EA009986B1 (ru)	2008-04-28
EA200600336A1 (ru)	2006-08-25
US7605163B2 (en)	2009-10-20
CA2534675A1 (en)	2005-02-17
TW200524883A (en)	2005-08-01
CN1867554B (zh)	2011-07-06
MA27995A1 (fr)	2006-07-03
EP1656361A1 (de)	2006-05-17
WO2005014563A1 (en)	2005-02-17
IL173274A0 (en)	2006-06-11
EG26404A (en)	2013-10-21
NO332263B1 (no)	2012-08-13
CY1108616T1 (el)	2014-04-09
MXPA06001665A (es)	2006-04-28
ES2297458T3 (es)	2008-05-01
PL1656361T3 (pl)	2008-06-30
RS20060076A (sr)	2008-08-07
MY145356A (en)	2012-01-31
CN1867554A (zh)	2006-11-22
US20080119486A1 (en)	2008-05-22
PT1656361E (pt)	2008-03-05
UA85194C2 (ru)	2009-01-12
CR8193A (es)	2006-10-06

Publication	Publication Date	Title
ZA200601990B (en)	2007-05-30	1-(2-Amino-benzol)-piperazine derivatives as glycine uptake inhibitors for the treatment of psychoses
CA2538135C (en)	2015-01-27	1-benzoyl-piperazine derivatives as glycine uptake inhibitors for the treatment of psychoses
EP1656361B1 (de)	2008-01-02	Piperazin mit or-substituierter phenylgruppe und deren verwendung als glyt1-inhibitoren
US20080287455A1 (en)	2008-11-20	Sulfanyl substituted phenyl methanones
EP1828154B1 (de)	2009-04-29	Phenylpiperazin-methanon-derivate
EP1836168B1 (de)	2009-02-25	Benzoyltetrahydropyridine als glyt-1-inhibitoren
HK1100483B (en)	2010-04-16	1-benzoyl-piperazine derivatives as glycine uptake inhibitors for the treatment of psychoses