HRP20050687A2 - Tri(ciclo) substituted amide compounds - Google Patents
Tri(ciclo) substituted amide compounds Download PDFInfo
- Publication number
- HRP20050687A2 HRP20050687A2 HR20050687A HRP20050687A HRP20050687A2 HR P20050687 A2 HRP20050687 A2 HR P20050687A2 HR 20050687 A HR20050687 A HR 20050687A HR P20050687 A HRP20050687 A HR P20050687A HR P20050687 A2 HRP20050687 A2 HR P20050687A2
- Authority
- HR
- Croatia
- Prior art keywords
- tetrahydropyran
- thiazol
- acrylamide
- ylpropionamide
- propionamide
- Prior art date
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- -1 amide compounds Chemical class 0.000 title claims description 105
- 150000001875 compounds Chemical class 0.000 claims abstract description 220
- 150000003839 salts Chemical class 0.000 claims abstract description 85
- 238000011282 treatment Methods 0.000 claims abstract description 19
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 15
- 201000001421 hyperglycemia Diseases 0.000 claims abstract description 15
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 10
- 230000000069 prophylactic effect Effects 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 117
- 238000000034 method Methods 0.000 claims description 87
- 239000001257 hydrogen Substances 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 26
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 150000001408 amides Chemical class 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 10
- 238000009833 condensation Methods 0.000 claims description 9
- 230000005494 condensation Effects 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- 230000004913 activation Effects 0.000 claims description 7
- 239000003472 antidiabetic agent Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- HMJAUNHXYJKDGD-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CCOCC1 HMJAUNHXYJKDGD-UHFFFAOYSA-N 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- NIDLAMGLZQRQLJ-HXUWFJFHSA-N (2r)-2-(4-cyclobutylsulfonylphenyl)-3-(oxan-4-yl)-n-pyrazin-2-ylpropanamide Chemical compound O=C([C@H](CC1CCOCC1)C=1C=CC(=CC=1)S(=O)(=O)C1CCC1)NC1=CN=CC=N1 NIDLAMGLZQRQLJ-HXUWFJFHSA-N 0.000 claims description 5
- DWIPGNHOTXSYBW-GOSISDBHSA-N (2r)-2-(4-cyclobutylsulfonylphenyl)-n-(5-fluoro-1,3-thiazol-2-yl)-3-(oxan-4-yl)propanamide Chemical compound S1C(F)=CN=C1NC(=O)[C@@H](C=1C=CC(=CC=1)S(=O)(=O)C1CCC1)CC1CCOCC1 DWIPGNHOTXSYBW-GOSISDBHSA-N 0.000 claims description 5
- DQIITKNITDKAJZ-LJQANCHMSA-N (2r)-2-(4-cyclopropylsulfonylphenyl)-3-(oxan-4-yl)-n-pyrazin-2-ylpropanamide Chemical compound O=C([C@H](CC1CCOCC1)C=1C=CC(=CC=1)S(=O)(=O)C1CC1)NC1=CN=CC=N1 DQIITKNITDKAJZ-LJQANCHMSA-N 0.000 claims description 5
- DBMFNEZMJWKKPU-QGZVFWFLSA-N (2r)-2-(4-cyclopropylsulfonylphenyl)-n-(5-fluoro-1,3-thiazol-2-yl)-3-(oxan-4-yl)propanamide Chemical compound S1C(F)=CN=C1NC(=O)[C@@H](C=1C=CC(=CC=1)S(=O)(=O)C1CC1)CC1CCOCC1 DBMFNEZMJWKKPU-QGZVFWFLSA-N 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- MNNGVQPWHYBWLL-LFIBNONCSA-N (e)-2-(4-cyclopropylsulfonylphenyl)-3-(oxan-4-yl)prop-2-enoic acid Chemical compound C=1C=C(S(=O)(=O)C2CC2)C=CC=1/C(C(=O)O)=C\C1CCOCC1 MNNGVQPWHYBWLL-LFIBNONCSA-N 0.000 claims description 4
- QYBGDJMLOIMBAO-XNTDXEJSSA-N (e)-n-(5-fluoro-1,3-thiazol-2-yl)-2-(4-methylsulfonylphenyl)-3-(oxan-4-yl)prop-2-enamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC(F)=CN=1)=C/C1CCOCC1 QYBGDJMLOIMBAO-XNTDXEJSSA-N 0.000 claims description 4
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 4
- 101100533877 Hypocrea jecorina (strain QM6a) sor8 gene Proteins 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 230000001747 exhibiting effect Effects 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 3
- BUUMCCCRRFQHMB-DEDYPNTBSA-N (e)-2-(4-cyclopropylsulfonylphenyl)-n-(5-fluoropyridin-2-yl)-3-(oxan-4-yl)prop-2-enamide Chemical compound N1=CC(F)=CC=C1NC(=O)C(\C=1C=CC(=CC=1)S(=O)(=O)C1CC1)=C\C1CCOCC1 BUUMCCCRRFQHMB-DEDYPNTBSA-N 0.000 claims description 3
- INXMLFBJZKIDHL-GXDHUFHOSA-N (e)-2-(4-methylsulfonylphenyl)-3-(oxan-4-yl)prop-2-enoic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(\C(O)=O)=C/C1CCOCC1 INXMLFBJZKIDHL-GXDHUFHOSA-N 0.000 claims description 3
- ZOKRSUIVATZNNQ-XNTDXEJSSA-N (e)-n-(5-chloro-1,3-thiazol-2-yl)-2-(4-methylsulfonylphenyl)-3-(thian-4-yl)prop-2-enamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC(Cl)=CN=1)=C/C1CCSCC1 ZOKRSUIVATZNNQ-XNTDXEJSSA-N 0.000 claims description 3
- BVDIPOMNZVHUHS-UHFFFAOYSA-N 2-(3-amino-4-methylsulfonylphenyl)-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=C(N)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CCOCC1 BVDIPOMNZVHUHS-UHFFFAOYSA-N 0.000 claims description 3
- FDDGTVMRLFSINT-UHFFFAOYSA-N 2-(3-fluoro-4-methylsulfonylphenyl)-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=C(F)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CCOCC1 FDDGTVMRLFSINT-UHFFFAOYSA-N 0.000 claims description 3
- UAHDKOITUXMTEL-UHFFFAOYSA-N 2-(4-cyclobutylsulfonylphenyl)-3-(oxan-4-yl)propanoic acid Chemical compound C=1C=C(S(=O)(=O)C2CCC2)C=CC=1C(C(=O)O)CC1CCOCC1 UAHDKOITUXMTEL-UHFFFAOYSA-N 0.000 claims description 3
- IMDSBCGXPMSCCM-UHFFFAOYSA-N 2-(4-cyclopropylsulfonylphenyl)-3-(oxan-4-yl)propanoic acid Chemical compound C=1C=C(S(=O)(=O)C2CC2)C=CC=1C(C(=O)O)CC1CCOCC1 IMDSBCGXPMSCCM-UHFFFAOYSA-N 0.000 claims description 3
- BCWQXFMJAUSUJF-UHFFFAOYSA-N 2-[4-(ethylsulfamoyl)phenyl]-3-(oxan-4-yl)propanoic acid Chemical compound C1=CC(S(=O)(=O)NCC)=CC=C1C(C(O)=O)CC1CCOCC1 BCWQXFMJAUSUJF-UHFFFAOYSA-N 0.000 claims description 3
- GUSSDECQXMLCNC-UHFFFAOYSA-N 2-[4-(methoxymethylsulfanyl)phenyl]-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=CC(SCOC)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CCOCC1 GUSSDECQXMLCNC-UHFFFAOYSA-N 0.000 claims description 3
- JAVVGKVAMOAKJY-UHFFFAOYSA-N 3-(oxan-4-yl)-2-(4-pyridin-3-ylsulfanylphenyl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(SC=2C=NC=CC=2)=CC=1)C(=O)NC1=NC=CS1 JAVVGKVAMOAKJY-UHFFFAOYSA-N 0.000 claims description 3
- OKCSLRBGVVZWTM-UHFFFAOYSA-N 3-(oxan-4-yl)-2-[4-(2-oxopropylsulfonyl)phenyl]-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=CC(S(=O)(=O)CC(=O)C)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CCOCC1 OKCSLRBGVVZWTM-UHFFFAOYSA-N 0.000 claims description 3
- XRSUYPNWCZILLT-UHFFFAOYSA-N 3-(oxan-4-yl)-2-[4-(oxan-4-ylmethylsulfanyl)phenyl]-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(SCC2CCOCC2)=CC=1)C(=O)NC1=NC=CS1 XRSUYPNWCZILLT-UHFFFAOYSA-N 0.000 claims description 3
- HUUPNPWVDMNTAH-UHFFFAOYSA-N 5-fluoro-1,3-thiazol-2-amine Chemical group NC1=NC=C(F)S1 HUUPNPWVDMNTAH-UHFFFAOYSA-N 0.000 claims description 3
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 3
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- PMMYDURMMJDGHR-UHFFFAOYSA-N n-(5-chloro-1,3-thiazol-2-yl)-3-(oxan-4-yl)-2-(4-piperazin-1-ylsulfonylphenyl)propanamide Chemical compound S1C(Cl)=CN=C1NC(=O)C(C=1C=CC(=CC=1)S(=O)(=O)N1CCNCC1)CC1CCOCC1 PMMYDURMMJDGHR-UHFFFAOYSA-N 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- UAHDKOITUXMTEL-QGZVFWFLSA-N (2r)-2-(4-cyclobutylsulfonylphenyl)-3-(oxan-4-yl)propanoic acid Chemical compound C([C@@H](C(=O)O)C=1C=CC(=CC=1)S(=O)(=O)C1CCC1)C1CCOCC1 UAHDKOITUXMTEL-QGZVFWFLSA-N 0.000 claims description 2
- IMDSBCGXPMSCCM-MRXNPFEDSA-N (2r)-2-(4-cyclopropylsulfonylphenyl)-3-(oxan-4-yl)propanoic acid Chemical compound C([C@@H](C(=O)O)C=1C=CC(=CC=1)S(=O)(=O)C1CC1)C1CCOCC1 IMDSBCGXPMSCCM-MRXNPFEDSA-N 0.000 claims description 2
- BCWQXFMJAUSUJF-OAHLLOKOSA-N (2r)-2-[4-(ethylsulfamoyl)phenyl]-3-(oxan-4-yl)propanoic acid Chemical compound C1=CC(S(=O)(=O)NCC)=CC=C1[C@H](C(O)=O)CC1CCOCC1 BCWQXFMJAUSUJF-OAHLLOKOSA-N 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- GXVGHWZNUFYRSW-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-n-(5-fluoro-1,3-thiazol-2-yl)-3-(oxan-4-yl)propanamide Chemical compound S1C(F)=CN=C1NC(=O)C(C=1C=C(Cl)C(Cl)=CC=1)CC1CCOCC1 GXVGHWZNUFYRSW-UHFFFAOYSA-N 0.000 claims description 2
- FHGVMYOILIXKJQ-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CCOCC1 FHGVMYOILIXKJQ-UHFFFAOYSA-N 0.000 claims description 2
- CVZAVSHUQGUQMQ-UHFFFAOYSA-N 2-(3-chloro-4-methylsulfonylphenyl)-n-(5-fluoro-1,3-thiazol-2-yl)-3-(oxan-4-yl)propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1C(C(=O)NC=1SC(F)=CN=1)CC1CCOCC1 CVZAVSHUQGUQMQ-UHFFFAOYSA-N 0.000 claims description 2
- NFBYFHVUKFKSNZ-UHFFFAOYSA-N 2-(3-fluoro-4-methylsulfanylphenyl)-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=C(F)C(SC)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CCOCC1 NFBYFHVUKFKSNZ-UHFFFAOYSA-N 0.000 claims description 2
- CDDVTCOOFCKRPF-UHFFFAOYSA-N 2-(4-cyclopropylsulfonylphenyl)-n-(5-formyl-1,3-thiazol-2-yl)-3-(oxan-4-yl)propanamide Chemical compound S1C(C=O)=CN=C1NC(=O)C(C=1C=CC(=CC=1)S(=O)(=O)C1CC1)CC1CCOCC1 CDDVTCOOFCKRPF-UHFFFAOYSA-N 0.000 claims description 2
- DQKIMAIVKMWANO-UHFFFAOYSA-N 2-(4-methylsulfanyl-3-nitrophenyl)-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=C([N+]([O-])=O)C(SC)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CCOCC1 DQKIMAIVKMWANO-UHFFFAOYSA-N 0.000 claims description 2
- TYLADYPAZCBXPE-UHFFFAOYSA-N 2-(4-morpholin-4-ylsulfonylphenyl)-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)N1CCOCC1)C(=O)NC1=NC=CS1 TYLADYPAZCBXPE-UHFFFAOYSA-N 0.000 claims description 2
- SGRSALQZAPHSAM-UHFFFAOYSA-N 3-(oxan-4-yl)-2-[4-(oxan-4-ylmethylsulfonyl)phenyl]-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)CC1CCOCC1)C(=O)NC1=NC=CS1 SGRSALQZAPHSAM-UHFFFAOYSA-N 0.000 claims description 2
- DOCFYJACCBDKEG-UHFFFAOYSA-N 3-(oxan-4-yl)-2-[4-(oxetan-3-ylsulfonyl)phenyl]-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)C1COC1)C(=O)NC1=NC=CS1 DOCFYJACCBDKEG-UHFFFAOYSA-N 0.000 claims description 2
- 101100134927 Gallus gallus COR8 gene Proteins 0.000 claims description 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 229940125708 antidiabetic agent Drugs 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- UKRSGIMTXRJUHR-UHFFFAOYSA-N n-(5-bromo-1,3-thiazol-2-yl)-2-(4-methylsulfonylphenyl)-3-(oxan-4-yl)propanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=O)NC=1SC(Br)=CN=1)CC1CCOCC1 UKRSGIMTXRJUHR-UHFFFAOYSA-N 0.000 claims description 2
- RQTGSHWPCRNTKL-UHFFFAOYSA-N n-ethyl-4-[3-(oxan-4-yl)-1-oxo-1-(1,3-thiazol-2-ylamino)propan-2-yl]benzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CCOCC1 RQTGSHWPCRNTKL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- GJQQHYNZZYZIKE-UHFFFAOYSA-N n-(1,3-thiazol-2-yl)prop-2-enamide Chemical compound C=CC(=O)NC1=NC=CS1 GJQQHYNZZYZIKE-UHFFFAOYSA-N 0.000 claims 11
- OGNHGQOTYHQMQC-UHFFFAOYSA-N 2-(1,3-thiazol-2-yl)propanamide Chemical compound NC(=O)C(C)C1=NC=CS1 OGNHGQOTYHQMQC-UHFFFAOYSA-N 0.000 claims 8
- HFGHLEDHAXUTTP-GZTJUZNOSA-N (e)-2-(4-cyclopropylsulfonylphenyl)-n-(5-fluoro-1,3-thiazol-2-yl)-3-(oxan-4-yl)prop-2-enamide Chemical compound S1C(F)=CN=C1NC(=O)C(\C=1C=CC(=CC=1)S(=O)(=O)C1CC1)=C\C1CCOCC1 HFGHLEDHAXUTTP-GZTJUZNOSA-N 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- WZDVMMXSSQLTNJ-LJQANCHMSA-N (2r)-2-(4-cyclobutylsulfonylphenyl)-3-(oxan-4-yl)-n-(1,2-oxazol-3-yl)propanamide Chemical compound O=C([C@H](CC1CCOCC1)C=1C=CC(=CC=1)S(=O)(=O)C1CCC1)NC=1C=CON=1 WZDVMMXSSQLTNJ-LJQANCHMSA-N 0.000 claims 2
- BPXNPIJGKLIHBF-HXUWFJFHSA-N (2r)-2-(4-cyclobutylsulfonylphenyl)-3-(oxan-4-yl)-n-pyrimidin-4-ylpropanamide Chemical compound O=C([C@H](CC1CCOCC1)C=1C=CC(=CC=1)S(=O)(=O)C1CCC1)NC1=CC=NC=N1 BPXNPIJGKLIHBF-HXUWFJFHSA-N 0.000 claims 2
- ZUWSRHRGHHWFPG-HXUWFJFHSA-N (2r)-2-(4-cyclobutylsulfonylphenyl)-n-(1-methylpyrazol-3-yl)-3-(oxan-4-yl)propanamide Chemical compound CN1C=CC(NC(=O)[C@H](CC2CCOCC2)C=2C=CC(=CC=2)S(=O)(=O)C2CCC2)=N1 ZUWSRHRGHHWFPG-HXUWFJFHSA-N 0.000 claims 2
- REZAQEOMRWZPEJ-QGZVFWFLSA-N (2r)-2-(4-cyclopropylsulfonylphenyl)-3-(oxan-4-yl)-n-(1,2,4-thiadiazol-5-yl)propanamide Chemical compound O=C([C@H](CC1CCOCC1)C=1C=CC(=CC=1)S(=O)(=O)C1CC1)NC1=NC=NS1 REZAQEOMRWZPEJ-QGZVFWFLSA-N 0.000 claims 2
- XXQUXRVEFJGEPM-GOSISDBHSA-N (2r)-2-(4-cyclopropylsulfonylphenyl)-n-(3-methyl-1,2,4-thiadiazol-5-yl)-3-(oxan-4-yl)propanamide Chemical compound CC1=NSC(NC(=O)[C@H](CC2CCOCC2)C=2C=CC(=CC=2)S(=O)(=O)C2CC2)=N1 XXQUXRVEFJGEPM-GOSISDBHSA-N 0.000 claims 2
- UXSQKWUEYZCYMX-GOSISDBHSA-N (2r)-2-[4-(ethylsulfamoyl)phenyl]-3-(oxan-4-yl)-n-pyrazin-2-ylpropanamide Chemical compound C1=CC(S(=O)(=O)NCC)=CC=C1[C@H](C(=O)NC=1N=CC=NC=1)CC1CCOCC1 UXSQKWUEYZCYMX-GOSISDBHSA-N 0.000 claims 2
- BAMQXRCGGLVHNQ-LJQANCHMSA-N (2r)-2-[4-(ethylsulfamoyl)phenyl]-3-(oxan-4-yl)-n-pyridin-2-ylpropanamide Chemical compound C1=CC(S(=O)(=O)NCC)=CC=C1[C@H](C(=O)NC=1N=CC=CC=1)CC1CCOCC1 BAMQXRCGGLVHNQ-LJQANCHMSA-N 0.000 claims 2
- XFOFEZSUWFRWHI-GOSISDBHSA-N (2r)-2-[4-(ethylsulfamoyl)phenyl]-3-(oxan-4-yl)-n-pyrimidin-4-ylpropanamide Chemical compound C1=CC(S(=O)(=O)NCC)=CC=C1[C@H](C(=O)NC=1N=CN=CC=1)CC1CCOCC1 XFOFEZSUWFRWHI-GOSISDBHSA-N 0.000 claims 2
- VXRCLIPPCBRTJM-GOSISDBHSA-N (2r)-2-[4-(ethylsulfamoyl)phenyl]-n-(1-methylpyrazol-3-yl)-3-(oxan-4-yl)propanamide Chemical compound C1=CC(S(=O)(=O)NCC)=CC=C1[C@H](C(=O)NC1=NN(C)C=C1)CC1CCOCC1 VXRCLIPPCBRTJM-GOSISDBHSA-N 0.000 claims 2
- LQZQXINXHUUTEV-QGZVFWFLSA-N (2r)-2-[4-(ethylsulfamoyl)phenyl]-n-(3-methyl-1,2,4-thiadiazol-5-yl)-3-(oxan-4-yl)propanamide Chemical compound C1=CC(S(=O)(=O)NCC)=CC=C1[C@H](C(=O)NC=1SN=C(C)N=1)CC1CCOCC1 LQZQXINXHUUTEV-QGZVFWFLSA-N 0.000 claims 2
- VMOWTQMIQLQNHR-GOSISDBHSA-N (2r)-2-[4-(ethylsulfamoyl)phenyl]-n-(6-methoxypyrimidin-4-yl)-3-(oxan-4-yl)propanamide Chemical compound C1=CC(S(=O)(=O)NCC)=CC=C1[C@H](C(=O)NC=1N=CN=C(OC)C=1)CC1CCOCC1 VMOWTQMIQLQNHR-GOSISDBHSA-N 0.000 claims 2
- YMJKYTOZNSBULD-QGOAFFKASA-N (e)-2-(4-ethylsulfonylphenyl)-3-(oxan-4-yl)-n-pyrimidin-4-ylprop-2-enamide Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1C(\C(=O)NC=1N=CN=CC=1)=C/C1CCOCC1 YMJKYTOZNSBULD-QGOAFFKASA-N 0.000 claims 2
- CAUIQZMSJLZRDB-XNTDXEJSSA-N (e)-n-(5-bromo-1,3-thiazol-2-yl)-2-(4-methylsulfonylphenyl)-3-(oxan-4-yl)prop-2-enamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC(Br)=CN=1)=C/C1CCOCC1 CAUIQZMSJLZRDB-XNTDXEJSSA-N 0.000 claims 2
- XZJCBYGJKKADFU-GZTJUZNOSA-N (e)-n-(5-chloro-1,3-thiazol-2-yl)-2-(4-cyclopropylsulfinylphenyl)-3-(oxan-4-yl)prop-2-enamide Chemical compound S1C(Cl)=CN=C1NC(=O)C(\C=1C=CC(=CC=1)S(=O)C1CC1)=C\C1CCOCC1 XZJCBYGJKKADFU-GZTJUZNOSA-N 0.000 claims 2
- IWFIHTHSDUIGSP-XNTDXEJSSA-N (e)-n-(5-chloro-1,3-thiazol-2-yl)-2-(4-methylsulfanylphenyl)-3-(oxan-4-yl)prop-2-enamide Chemical compound C1=CC(SC)=CC=C1C(\C(=O)NC=1SC(Cl)=CN=1)=C/C1CCOCC1 IWFIHTHSDUIGSP-XNTDXEJSSA-N 0.000 claims 2
- IWONKESQUNTQFN-XNTDXEJSSA-N (e)-n-(5-chloro-1,3-thiazol-2-yl)-2-(4-methylsulfinylphenyl)-3-(thian-4-yl)prop-2-enamide Chemical compound C1=CC(S(=O)C)=CC=C1C(\C(=O)NC=1SC(Cl)=CN=1)=C/C1CCSCC1 IWONKESQUNTQFN-XNTDXEJSSA-N 0.000 claims 2
- PWTXOSVKVNVJJK-XNTDXEJSSA-N (e)-n-(5-chloro-1,3-thiazol-2-yl)-2-(4-methylsulfonylphenyl)-3-(oxan-4-yl)prop-2-enamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC(Cl)=CN=1)=C/C1CCOCC1 PWTXOSVKVNVJJK-XNTDXEJSSA-N 0.000 claims 2
- JXOYSGUHHCUWRC-NTEUORMPSA-N (e)-n-(5-chloro-1,3-thiazol-2-yl)-2-(4-nitrophenyl)-3-(oxan-4-yl)prop-2-enamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(\C(=O)NC=1SC(Cl)=CN=1)=C/C1CCOCC1 JXOYSGUHHCUWRC-NTEUORMPSA-N 0.000 claims 2
- SLNHJGGMIWLPSD-UHFFFAOYSA-N 2-(4-cyclobutylsulfonylphenyl)-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)C1CCC1)C(=O)NC1=NC=CS1 SLNHJGGMIWLPSD-UHFFFAOYSA-N 0.000 claims 2
- REZAQEOMRWZPEJ-UHFFFAOYSA-N 2-(4-cyclopropylsulfonylphenyl)-3-(oxan-4-yl)-n-(1,2,4-thiadiazol-5-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)C1CC1)C(=O)NC1=NC=NS1 REZAQEOMRWZPEJ-UHFFFAOYSA-N 0.000 claims 2
- VYLRVLPTTGJPMN-UHFFFAOYSA-N 2-(4-imidazol-1-ylsulfonylphenyl)-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)N1C=NC=C1)C(=O)NC1=NC=CS1 VYLRVLPTTGJPMN-UHFFFAOYSA-N 0.000 claims 2
- PJXJCNQJHGXCDE-UHFFFAOYSA-N 2-[4-(1,3-dioxolan-2-ylmethylsulfonyl)phenyl]-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)CC1OCCO1)C(=O)NC1=NC=CS1 PJXJCNQJHGXCDE-UHFFFAOYSA-N 0.000 claims 2
- KEFRRBHRUFXXAD-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(C(CC2CCOCC2)C(=O)NC=2SC=CN=2)C=C1 KEFRRBHRUFXXAD-UHFFFAOYSA-N 0.000 claims 2
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- JKRCQEKRSDZPOH-UHFFFAOYSA-N 2-[4-(cyclopropylmethylsulfamoyl)phenyl]-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)NCC1CC1)C(=O)NC1=NC=CS1 JKRCQEKRSDZPOH-UHFFFAOYSA-N 0.000 claims 2
- ATZDKIUTEGSRCR-UHFFFAOYSA-N 2-[4-(cyclopropylmethylsulfonyl)phenyl]-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)CC1CC1)C(=O)NC1=NC=CS1 ATZDKIUTEGSRCR-UHFFFAOYSA-N 0.000 claims 2
- LLAWDJRAYDVHRO-UHFFFAOYSA-N 2-[4-(cyclopropylsulfamoyl)phenyl]-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)NC1CC1)C(=O)NC1=NC=CS1 LLAWDJRAYDVHRO-UHFFFAOYSA-N 0.000 claims 2
- VLBRSHOHSRUCDN-UHFFFAOYSA-N 2-[4-(ethylsulfamoyl)phenyl]-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=CC(S(=O)(=O)NCC)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CCOCC1 VLBRSHOHSRUCDN-UHFFFAOYSA-N 0.000 claims 2
- GCIDOAHMBFCACF-UHFFFAOYSA-N 2-[4-(methoxymethylsulfonyl)phenyl]-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=CC(S(=O)(=O)COC)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CCOCC1 GCIDOAHMBFCACF-UHFFFAOYSA-N 0.000 claims 2
- XVDBWOBWURIKDJ-UHFFFAOYSA-N 2-[4-(methylsulfamoyl)phenyl]-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CCOCC1 XVDBWOBWURIKDJ-UHFFFAOYSA-N 0.000 claims 2
- HYSINOPDLMFMLN-UHFFFAOYSA-N 2-[4-[(4-methyl-1,4-diazepan-1-yl)sulfonyl]phenyl]-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1CN(C)CCCN1S(=O)(=O)C1=CC=C(C(CC2CCOCC2)C(=O)NC=2SC=CN=2)C=C1 HYSINOPDLMFMLN-UHFFFAOYSA-N 0.000 claims 2
- NNEKRCSAASOGBL-IJXZTRCJSA-N 2-[4-[[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]sulfonyl]phenyl]-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2S(=O)(=O)C(C=C1)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CCOCC1 NNEKRCSAASOGBL-IJXZTRCJSA-N 0.000 claims 2
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- VOABPSXEVMBGJS-UHFFFAOYSA-N 3-(oxan-4-yl)-2-[4-(oxan-4-ylsulfonyl)phenyl]-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)C1CCOCC1)C(=O)NC1=NC=CS1 VOABPSXEVMBGJS-UHFFFAOYSA-N 0.000 claims 2
- GPNIHLYUXVYYMU-UHFFFAOYSA-N 3-(oxan-4-yl)-2-[4-(pyridin-2-ylmethylsulfamoyl)phenyl]-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)NCC=1N=CC=CC=1)C(=O)NC1=NC=CS1 GPNIHLYUXVYYMU-UHFFFAOYSA-N 0.000 claims 2
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- UQELQAOGACYKKG-MRTLOADZSA-N 3-(oxan-4-yl)-2-[4-[(3r)-oxolan-3-yl]sulfonylphenyl]-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)[C@H]1COCC1)C(=O)NC1=NC=CS1 UQELQAOGACYKKG-MRTLOADZSA-N 0.000 claims 2
- UQELQAOGACYKKG-OYKVQYDMSA-N 3-(oxan-4-yl)-2-[4-[(3s)-oxolan-3-yl]sulfonylphenyl]-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)[C@@H]1COCC1)C(=O)NC1=NC=CS1 UQELQAOGACYKKG-OYKVQYDMSA-N 0.000 claims 2
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- DOTNXOZFPLAGNY-GOSISDBHSA-N (2r)-2-(4-cyclopropylsulfonylphenyl)-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound O=C([C@H](CC1CCOCC1)C=1C=CC(=CC=1)S(=O)(=O)C1CC1)NC1=NC=CS1 DOTNXOZFPLAGNY-GOSISDBHSA-N 0.000 claims 1
- CILQAVQRGKBESP-HXUWFJFHSA-N (2r)-2-(4-cyclopropylsulfonylphenyl)-n-(5-fluoropyridin-2-yl)-3-(oxan-4-yl)propanamide Chemical compound N1=CC(F)=CC=C1NC(=O)[C@@H](C=1C=CC(=CC=1)S(=O)(=O)C1CC1)CC1CCOCC1 CILQAVQRGKBESP-HXUWFJFHSA-N 0.000 claims 1
- JIKOFDJUFCPMRR-OAHLLOKOSA-N (2r)-n-(5-chloro-1,3-thiazol-2-yl)-2-(4-methylsulfonylphenyl)-3-(oxan-4-yl)propanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1SC(Cl)=CN=1)CC1CCOCC1 JIKOFDJUFCPMRR-OAHLLOKOSA-N 0.000 claims 1
- IERGAZGAANLJJZ-OAHLLOKOSA-N (2r)-n-(5-fluoro-1,3-thiazol-2-yl)-2-(4-methylsulfonylphenyl)-3-(oxan-4-yl)propanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1SC(F)=CN=1)CC1CCOCC1 IERGAZGAANLJJZ-OAHLLOKOSA-N 0.000 claims 1
- MFXVKZCXRYWRCI-GOSISDBHSA-N (2r)-n-(5-fluoropyridin-2-yl)-2-(4-methylsulfonylphenyl)-3-(oxan-4-yl)propanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC=1N=CC(F)=CC=1)CC1CCOCC1 MFXVKZCXRYWRCI-GOSISDBHSA-N 0.000 claims 1
- GMIDEGNGAWBEPP-OQLLNIDSSA-N (e)-2-(4-bromophenyl)-3-(furan-2-yl)-n-(5-methyl-1,3-thiazol-2-yl)prop-2-enamide Chemical compound S1C(C)=CN=C1NC(=O)C(\C=1C=CC(Br)=CC=1)=C\C1=CC=CO1 GMIDEGNGAWBEPP-OQLLNIDSSA-N 0.000 claims 1
- RFAJVDOTBIPOJX-RVDMUPIBSA-N (e)-2-(4-ethylsulfonylphenyl)-3-(oxan-4-yl)prop-2-enoic acid Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1C(\C(O)=O)=C/C1CCOCC1 RFAJVDOTBIPOJX-RVDMUPIBSA-N 0.000 claims 1
- TXNZVVSGEICVLV-MHWRWJLKSA-N (e)-3-(furan-2-yl)-2-(4-methoxyphenyl)-n-(5-methyl-1,3-thiazol-2-yl)prop-2-enamide Chemical compound C1=CC(OC)=CC=C1C(\C(=O)NC=1SC(C)=CN=1)=C/C1=CC=CO1 TXNZVVSGEICVLV-MHWRWJLKSA-N 0.000 claims 1
- GZLORFGQDOGCAA-FOWTUZBSSA-N (e)-3-(oxan-4-yl)-2-(4-propylsulfonylphenyl)prop-2-enoic acid Chemical compound C1=CC(S(=O)(=O)CCC)=CC=C1C(\C(O)=O)=C/C1CCOCC1 GZLORFGQDOGCAA-FOWTUZBSSA-N 0.000 claims 1
- ZHVMEASEGQJUNT-GZTJUZNOSA-N (e)-3-(thian-4-yl)-n-(1,3-thiazol-2-yl)-2-[4-(1,2,4-triazol-1-yl)phenyl]prop-2-enamide Chemical compound C1CSCCC1/C=C(\C=1C=CC(=CC=1)N1N=CN=C1)C(=O)NC1=NC=CS1 ZHVMEASEGQJUNT-GZTJUZNOSA-N 0.000 claims 1
- YKJKMEAMHKAJKF-MHWRWJLKSA-N (e)-n-(5-chloro-1,3-thiazol-2-yl)-2-(4-cyanophenyl)-3-phenylprop-2-enamide Chemical compound S1C(Cl)=CN=C1NC(=O)C(\C=1C=CC(=CC=1)C#N)=C\C1=CC=CC=C1 YKJKMEAMHKAJKF-MHWRWJLKSA-N 0.000 claims 1
- ZDLBJHWDWABECS-LFIBNONCSA-N (e)-n-(5-chloro-4-methyl-1,3-thiazol-2-yl)-2-(4-methylsulfonylphenyl)-3-(thian-4-yl)prop-2-enamide Chemical compound S1C(Cl)=C(C)N=C1NC(=O)C(\C=1C=CC(=CC=1)S(C)(=O)=O)=C\C1CCSCC1 ZDLBJHWDWABECS-LFIBNONCSA-N 0.000 claims 1
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- YBQQVSWTMHNSQB-UHFFFAOYSA-N 2-(3-fluoro-4-methylsulfinylphenyl)-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1=C(F)C(S(=O)C)=CC=C1C(C(=O)NC=1SC=CN=1)CC1CCOCC1 YBQQVSWTMHNSQB-UHFFFAOYSA-N 0.000 claims 1
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- KELUOWBFLOEYIN-UHFFFAOYSA-N 2-(3-methylsulfonylphenyl)-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound CS(=O)(=O)C1=CC=CC(C(CC2CCOCC2)C(=O)NC=2SC=CN=2)=C1 KELUOWBFLOEYIN-UHFFFAOYSA-N 0.000 claims 1
- DQIITKNITDKAJZ-UHFFFAOYSA-N 2-(4-cyclopropylsulfonylphenyl)-3-(oxan-4-yl)-n-pyrazin-2-ylpropanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)C1CC1)C(=O)NC1=CN=CC=N1 DQIITKNITDKAJZ-UHFFFAOYSA-N 0.000 claims 1
- XXQUXRVEFJGEPM-UHFFFAOYSA-N 2-(4-cyclopropylsulfonylphenyl)-n-(3-methyl-1,2,4-thiadiazol-5-yl)-3-(oxan-4-yl)propanamide Chemical compound CC1=NSC(NC(=O)C(CC2CCOCC2)C=2C=CC(=CC=2)S(=O)(=O)C2CC2)=N1 XXQUXRVEFJGEPM-UHFFFAOYSA-N 0.000 claims 1
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- PZSHPLYDZZAPSV-UHFFFAOYSA-N 2-(4-ethylsulfonylphenyl)-n-(3-methyl-1,2,4-thiadiazol-5-yl)-3-(oxan-4-yl)propanamide Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1C(C(=O)NC=1SN=C(C)N=1)CC1CCOCC1 PZSHPLYDZZAPSV-UHFFFAOYSA-N 0.000 claims 1
- SMSKOXZUNGMFPW-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-3-(oxan-4-yl)-n-pyrazin-2-ylpropanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CC=NC=1)CC1CCOCC1 SMSKOXZUNGMFPW-UHFFFAOYSA-N 0.000 claims 1
- OMQGHWIRIGBPOL-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-3-(oxan-4-yl)-n-pyrimidin-4-ylpropanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=O)NC=1N=CN=CC=1)CC1CCOCC1 OMQGHWIRIGBPOL-UHFFFAOYSA-N 0.000 claims 1
- BDABPUQLRHDWNV-UHFFFAOYSA-N 2-[4-(1,2,4-oxadiazol-3-ylmethylsulfonyl)phenyl]-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)CC1=NOC=N1)C(=O)NC1=NC=CS1 BDABPUQLRHDWNV-UHFFFAOYSA-N 0.000 claims 1
- HXGGIKMNFTVTKL-UHFFFAOYSA-N 2-[4-(2-aminoethylsulfamoyl)phenyl]-n-(5-chloro-1,3-thiazol-2-yl)-3-(oxan-4-yl)propanamide Chemical compound C1=CC(S(=O)(=O)NCCN)=CC=C1C(C(=O)NC=1SC(Cl)=CN=1)CC1CCOCC1 HXGGIKMNFTVTKL-UHFFFAOYSA-N 0.000 claims 1
- SWEWOJLLUPCTMO-UHFFFAOYSA-N 2-[4-(cyanomethylsulfonyl)phenyl]-3-(oxan-4-yl)-n-(1,3-thiazol-2-yl)propanamide Chemical compound C1COCCC1CC(C=1C=CC(=CC=1)S(=O)(=O)CC#N)C(=O)NC1=NC=CS1 SWEWOJLLUPCTMO-UHFFFAOYSA-N 0.000 claims 1
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- UXSQKWUEYZCYMX-UHFFFAOYSA-N 2-[4-(ethylsulfamoyl)phenyl]-3-(oxan-4-yl)-n-pyrazin-2-ylpropanamide Chemical compound C1=CC(S(=O)(=O)NCC)=CC=C1C(C(=O)NC=1N=CC=NC=1)CC1CCOCC1 UXSQKWUEYZCYMX-UHFFFAOYSA-N 0.000 claims 1
- XFOFEZSUWFRWHI-UHFFFAOYSA-N 2-[4-(ethylsulfamoyl)phenyl]-3-(oxan-4-yl)-n-pyrimidin-4-ylpropanamide Chemical compound C1=CC(S(=O)(=O)NCC)=CC=C1C(C(=O)NC=1N=CN=CC=1)CC1CCOCC1 XFOFEZSUWFRWHI-UHFFFAOYSA-N 0.000 claims 1
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-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
- 150000003212 purines Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 229960004586 rosiglitazone Drugs 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
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
- 229960004425 sibutramine Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- DHHKPEUQJIEKOA-UHFFFAOYSA-N tert-butyl 2-[6-(nitromethyl)-6-bicyclo[3.2.0]hept-3-enyl]acetate Chemical compound C1C=CC2C(CC(=O)OC(C)(C)C)(C[N+]([O-])=O)CC21 DHHKPEUQJIEKOA-UHFFFAOYSA-N 0.000 description 1
- GSFHMVIECSQBLV-UHFFFAOYSA-N tert-butyl 4-[4-[1-[(5-chloro-1,3-thiazol-2-yl)amino]-3-(oxan-4-yl)-1-oxopropan-2-yl]phenyl]sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1S(=O)(=O)C1=CC=C(C(CC2CCOCC2)C(=O)NC=2SC(Cl)=CN=2)C=C1 GSFHMVIECSQBLV-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 description 1
- NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JWCVYQRPINPYQJ-UHFFFAOYSA-N thiepane Chemical compound C1CCCSCC1 JWCVYQRPINPYQJ-UHFFFAOYSA-N 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- AMIGYDGSJCJWSD-UHFFFAOYSA-N thiocane Chemical compound C1CCCSCCC1 AMIGYDGSJCJWSD-UHFFFAOYSA-N 0.000 description 1
- 229960002277 tolazamide Drugs 0.000 description 1
- OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
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- A61P3/00—Drugs for disorders of the metabolism
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
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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
- C07D213/24—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 with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- 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
- C07D309/04—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- 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
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/28—Halogen atoms
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- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
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- 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
- C07D405/10—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 aromatic rings
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- 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
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- C07D405/12—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 chain containing hetero atoms as chain links
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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US44668303P | 2003-02-11 | 2003-02-11 | |
US49443403P | 2003-08-11 | 2003-08-11 | |
US51280003P | 2003-10-20 | 2003-10-20 | |
PCT/US2004/003968 WO2004072031A2 (en) | 2003-02-11 | 2004-02-10 | Phenylacetamides and their use as glucokinase modulators |
Publications (1)
Publication Number | Publication Date |
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HRP20050687A2 true HRP20050687A2 (en) | 2006-02-28 |
Family
ID=32872762
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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HR20050687A HRP20050687A2 (en) | 2003-02-11 | 2005-08-01 | Tri(ciclo) substituted amide compounds |
Country Status (26)
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US (2) | US7214681B2 (es) |
EP (2) | EP2168962A3 (es) |
JP (1) | JP4757188B2 (es) |
KR (1) | KR101120916B1 (es) |
AR (1) | AR043157A1 (es) |
AT (1) | ATE391718T1 (es) |
AU (1) | AU2004212500B2 (es) |
BR (1) | BRPI0407139A (es) |
CA (1) | CA2515670A1 (es) |
CY (1) | CY1110254T1 (es) |
DE (1) | DE602004012969T2 (es) |
DK (1) | DK1594867T3 (es) |
EA (1) | EA012700B1 (es) |
ES (1) | ES2303628T3 (es) |
HR (1) | HRP20050687A2 (es) |
IL (1) | IL169954A (es) |
MA (1) | MA27708A1 (es) |
MX (1) | MXPA05008406A (es) |
MY (1) | MY145590A (es) |
NO (1) | NO20053742L (es) |
NZ (1) | NZ541759A (es) |
PL (1) | PL378117A1 (es) |
PT (1) | PT1594867E (es) |
SI (1) | SI1594867T1 (es) |
TW (1) | TWI314553B (es) |
WO (1) | WO2004072031A2 (es) |
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GB0226931D0 (en) | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
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-
2004
- 2004-02-03 PL PL378117A patent/PL378117A1/pl not_active Application Discontinuation
- 2004-02-10 DE DE602004012969T patent/DE602004012969T2/de not_active Expired - Lifetime
- 2004-02-10 AT AT04707845T patent/ATE391718T1/de active
- 2004-02-10 ES ES04707845T patent/ES2303628T3/es not_active Expired - Lifetime
- 2004-02-10 JP JP2006503482A patent/JP4757188B2/ja not_active Expired - Fee Related
- 2004-02-10 WO PCT/US2004/003968 patent/WO2004072031A2/en active Application Filing
- 2004-02-10 AU AU2004212500A patent/AU2004212500B2/en not_active Ceased
- 2004-02-10 US US10/776,584 patent/US7214681B2/en not_active Expired - Fee Related
- 2004-02-10 NZ NZ541759A patent/NZ541759A/en not_active IP Right Cessation
- 2004-02-10 BR BR0407139-5A patent/BRPI0407139A/pt not_active Application Discontinuation
- 2004-02-10 EA EA200501095A patent/EA012700B1/ru not_active IP Right Cessation
- 2004-02-10 EP EP08150303A patent/EP2168962A3/en not_active Withdrawn
- 2004-02-10 SI SI200430768T patent/SI1594867T1/sl unknown
- 2004-02-10 EP EP04707845A patent/EP1594867B1/en not_active Expired - Lifetime
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- 2004-02-10 KR KR1020057014855A patent/KR101120916B1/ko not_active IP Right Cessation
- 2004-02-10 CA CA002515670A patent/CA2515670A1/en not_active Abandoned
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