BRPI0311318B1 - inibidores de peptídeo desformilase - Google Patents
inibidores de peptídeo desformilase Download PDFInfo
- Publication number
- BRPI0311318B1 BRPI0311318B1 BRPI0311318A BR0311318A BRPI0311318B1 BR PI0311318 B1 BRPI0311318 B1 BR PI0311318B1 BR PI0311318 A BRPI0311318 A BR PI0311318A BR 0311318 A BR0311318 A BR 0311318A BR PI0311318 B1 BRPI0311318 B1 BR PI0311318B1
- Authority
- BR
- Brazil
- Prior art keywords
- hydrazino
- carbonyl
- hydroxy
- heptyl
- formamide
- Prior art date
Links
- 239000000081 peptide deformylase inhibitor Substances 0.000 title abstract description 3
- -1 anthracyl Chemical group 0.000 claims description 633
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 379
- 150000001875 compounds Chemical class 0.000 claims description 95
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 70
- 125000003118 aryl group Chemical group 0.000 claims description 48
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 125000000623 heterocyclic group Chemical group 0.000 claims description 42
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 28
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 12
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 9
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 9
- 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 7
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000003435 aroyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- DZBLYGRCIPVSMB-GFCCVEGCSA-N n-[(2r)-2-[(1,2,4-benzotriazin-3-ylamino)carbamoyl]-5-methylhexyl]-n-hydroxyformamide Chemical compound C1=CC=CC2=NC(NNC(=O)[C@@H](CN(O)C=O)CCC(C)C)=NN=C21 DZBLYGRCIPVSMB-GFCCVEGCSA-N 0.000 claims description 3
- AZNDRDPWPRUQHE-GICMACPYSA-N n-[(2r)-2-[(2,3-dihydro-1,4-benzodioxin-3-ylmethylamino)carbamoyl]heptyl]-n-hydroxyformamide Chemical compound C1=CC=C2OC(CNNC(=O)[C@@H](CN(O)C=O)CCCCC)COC2=C1 AZNDRDPWPRUQHE-GICMACPYSA-N 0.000 claims description 3
- YJSYWZANKKGKCB-GFCCVEGCSA-N n-[(2r)-2-[[[4-(azetidin-1-yl)-5-fluoropyrimidin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=C(F)C(N2CCC2)=N1 YJSYWZANKKGKCB-GFCCVEGCSA-N 0.000 claims description 3
- ZRHNIWZZSZABNE-CYBMUJFWSA-N n-[(2r)-3-[amino(1,2,4-benzotriazin-3-yl)amino]-2-(cyclopentylmethyl)-3-oxopropyl]-n-hydroxyformamide Chemical compound C([C@@H](C(=O)N(N)C=1N=C2C=CC=CC2=NN=1)CN(O)C=O)C1CCCC1 ZRHNIWZZSZABNE-CYBMUJFWSA-N 0.000 claims description 3
- OVCZJZNDTLDKAN-GFCCVEGCSA-N n-hydroxy-n-[(2r)-2-[(pyridin-2-ylamino)carbamoyl]heptyl]formamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=CC=CC=N1 OVCZJZNDTLDKAN-GFCCVEGCSA-N 0.000 claims description 3
- CDRYLMLPLOHUEB-QGZVFWFLSA-N n-hydroxy-n-[(2r)-2-[[[4-[3-(hydroxymethyl)phenyl]pyrimidin-2-yl]amino]carbamoyl]heptyl]formamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=CC(C=2C=C(CO)C=CC=2)=N1 CDRYLMLPLOHUEB-QGZVFWFLSA-N 0.000 claims description 3
- BEXVLEHESXXHBX-QGZVFWFLSA-N n-hydroxy-n-[(2r)-2-[[[4-[4-(hydroxymethyl)phenyl]pyrimidin-2-yl]amino]carbamoyl]heptyl]formamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=CC(C=2C=CC(CO)=CC=2)=N1 BEXVLEHESXXHBX-QGZVFWFLSA-N 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 3
- PEOVTXAOQZOBEY-UHFFFAOYSA-N 4-ethylpiperazin-2-one Chemical compound CCN1CCNC(=O)C1 PEOVTXAOQZOBEY-UHFFFAOYSA-N 0.000 claims description 2
- IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical compound ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- OFFPHYGBAWHERG-GFCCVEGCSA-N n-[(2r)-2-(cyclopentylmethyl)-3-[2-[4-(cyclopropylamino)-5-fluoropyrimidin-2-yl]hydrazinyl]-3-oxopropyl]-n-hydroxyformamide Chemical compound C([C@H](CN(O)C=O)C(=O)NNC=1N=C(NC2CC2)C(F)=CN=1)C1CCCC1 OFFPHYGBAWHERG-GFCCVEGCSA-N 0.000 claims description 2
- XLGGVXQFZPZGAW-CYBMUJFWSA-N n-[(2r)-2-(cyclopentylmethyl)-3-[2-[4-[2-hydroxyethyl(methyl)amino]-6-(trifluoromethyl)pyrimidin-2-yl]hydrazinyl]-3-oxopropyl]-n-hydroxyformamide Chemical compound OCCN(C)C1=CC(C(F)(F)F)=NC(NNC(=O)[C@H](CC2CCCC2)CN(O)C=O)=N1 XLGGVXQFZPZGAW-CYBMUJFWSA-N 0.000 claims description 2
- SRSKFTCUAYHENW-CQSZACIVSA-N n-[(2r)-2-[(4-cyanoanilino)carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=CC=C(C#N)C=C1 SRSKFTCUAYHENW-CQSZACIVSA-N 0.000 claims description 2
- FOUPLBYRROPGNC-CYBMUJFWSA-N n-[(2r)-2-[(6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-ylamino)carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=C2CCCC2=N1 FOUPLBYRROPGNC-CYBMUJFWSA-N 0.000 claims description 2
- OOMCXCRFNXIWBP-LLVKDONJSA-N n-[(2r)-2-[[(2,5-dimethyl-4-nitropyrazol-3-yl)amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=C([N+]([O-])=O)C(C)=NN1C OOMCXCRFNXIWBP-LLVKDONJSA-N 0.000 claims description 2
- XSNGGEMEHMJSRL-CYBMUJFWSA-N n-[(2r)-2-[[(3,6-dimethylpyrazin-2-yl)amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC(C)=CN=C1C XSNGGEMEHMJSRL-CYBMUJFWSA-N 0.000 claims description 2
- MAZFXKMROMQPPI-QGZVFWFLSA-N n-[(2r)-2-[[[1-(1,3-benzodioxole-5-carbonyl)piperidin-4-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound C1CC(NNC(=O)[C@@H](CN(O)C=O)CCCCC)CCN1C(=O)C1=CC=C(OCO2)C2=C1 MAZFXKMROMQPPI-QGZVFWFLSA-N 0.000 claims description 2
- RFJZGPYTNXBHSP-GOSISDBHSA-N n-[(2r)-2-[[[1-(1-benzofuran-2-carbonyl)piperidin-4-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound C1CC(NNC(=O)[C@@H](CN(O)C=O)CCCCC)CCN1C(=O)C1=CC2=CC=CC=C2O1 RFJZGPYTNXBHSP-GOSISDBHSA-N 0.000 claims description 2
- DWPXQXDDSWDZSG-OAHLLOKOSA-N n-[(2r)-2-[[[1-(2,3-dichlorobenzoyl)piperidin-4-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound C1CC(NNC(=O)[C@@H](CN(O)C=O)CCCCC)CCN1C(=O)C1=CC=CC(Cl)=C1Cl DWPXQXDDSWDZSG-OAHLLOKOSA-N 0.000 claims description 2
- NBRCRSAAEBUMBR-MRXNPFEDSA-N n-[(2r)-2-[[[1-(3,4-dichlorobenzoyl)piperidin-4-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound C1CC(NNC(=O)[C@@H](CN(O)C=O)CCCCC)CCN1C(=O)C1=CC=C(Cl)C(Cl)=C1 NBRCRSAAEBUMBR-MRXNPFEDSA-N 0.000 claims description 2
- QWOLFLYGRYJPOI-CQSZACIVSA-N n-[(2r)-2-[[[4-(3,5-dimethyl-1,2-oxazol-4-yl)pyrimidin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=CC(C2=C(ON=C2C)C)=N1 QWOLFLYGRYJPOI-CQSZACIVSA-N 0.000 claims description 2
- QVJBMXJEHHMRLY-QGZVFWFLSA-N n-[(2r)-2-[[[4-ethyl-6-(4-propylpiperazin-1-yl)-1,3,5-triazin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC(CC)=NC(N2CCN(CCC)CC2)=N1 QVJBMXJEHHMRLY-QGZVFWFLSA-N 0.000 claims description 2
- OPJDXCQXVJYWRT-GFCCVEGCSA-N n-[(2r)-2-[[[5,6-dimethyl-2-(trifluoromethyl)pyrimidin-4-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC(C(F)(F)F)=NC(C)=C1C OPJDXCQXVJYWRT-GFCCVEGCSA-N 0.000 claims description 2
- COVLCIQERKYPDR-MRXNPFEDSA-N n-[(2r)-2-[[[5-(dimethylamino)-4-pyridin-3-ylpyrimidin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=C(N(C)C)C(C=2C=NC=CC=2)=N1 COVLCIQERKYPDR-MRXNPFEDSA-N 0.000 claims description 2
- UEHCAOSBCIVDFW-SNVBAGLBSA-N n-[(2r)-2-[[[5-cyano-4-(trifluoromethyl)pyrimidin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=C(C#N)C(C(F)(F)F)=N1 UEHCAOSBCIVDFW-SNVBAGLBSA-N 0.000 claims description 2
- COCSRUUWASAPGN-HNNXBMFYSA-N n-[(2r)-2-cycloheptyl-3-[2-(4-methylpyridin-2-yl)hydrazinyl]-3-oxopropyl]-n-hydroxyformamide Chemical compound CC1=CC=NC(NNC(=O)[C@@H](CN(O)C=O)C2CCCCCC2)=C1 COCSRUUWASAPGN-HNNXBMFYSA-N 0.000 claims description 2
- XDFAXJGAPJGTKV-ZDUSSCGKSA-N n-[(2r)-2-cyclopentyl-3-[2-(4-methylpyridin-2-yl)hydrazinyl]-3-oxopropyl]-n-hydroxyformamide Chemical compound CC1=CC=NC(NNC(=O)[C@@H](CN(O)C=O)C2CCCC2)=C1 XDFAXJGAPJGTKV-ZDUSSCGKSA-N 0.000 claims description 2
- WWNXKADOEADIQS-GFCCVEGCSA-N n-[(2r)-3-[2-[4-ethyl-6-[ethyl(methyl)amino]-1,3,5-triazin-2-yl]hydrazinyl]-3-oxo-2-(thiophen-2-ylmethyl)propyl]-n-hydroxyformamide Chemical compound CCN(C)C1=NC(CC)=NC(NNC(=O)[C@@H](CN(O)C=O)CC=2SC=CC=2)=N1 WWNXKADOEADIQS-GFCCVEGCSA-N 0.000 claims description 2
- SVJPISQELXNZSI-SECBINFHSA-N n-[(2r)-4,4-dimethyl-2-[[[4-(trifluoromethyl)pyrimidin-2-yl]amino]carbamoyl]pentyl]-n-hydroxyformamide Chemical compound O=CN(O)C[C@@H](CC(C)(C)C)C(=O)NNC1=NC=CC(C(F)(F)F)=N1 SVJPISQELXNZSI-SECBINFHSA-N 0.000 claims description 2
- HBUUEGUKIOLBDF-LLVKDONJSA-N n-[(2r)-4-ethyl-2-[[[4-(trifluoromethyl)pyrimidin-2-yl]amino]carbamoyl]hexyl]-n-hydroxyformamide Chemical compound CCC(CC)C[C@H](CN(O)C=O)C(=O)NNC1=NC=CC(C(F)(F)F)=N1 HBUUEGUKIOLBDF-LLVKDONJSA-N 0.000 claims description 2
- KHGNNRRDJARNJI-LLVKDONJSA-N n-hydroxy-n-[(2r)-2-[(1-methylcyclopentyl)methyl]-3-oxo-3-[2-[4-(trifluoromethyl)pyrimidin-2-yl]hydrazinyl]propyl]formamide Chemical compound C([C@H](CN(O)C=O)C(=O)NNC=1N=C(C=CN=1)C(F)(F)F)C1(C)CCCC1 KHGNNRRDJARNJI-LLVKDONJSA-N 0.000 claims description 2
- ILRSBWLNRQYMMH-CYBMUJFWSA-N n-hydroxy-n-[(2r)-2-[(3-methoxyanilino)carbamoyl]heptyl]formamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=CC=CC(OC)=C1 ILRSBWLNRQYMMH-CYBMUJFWSA-N 0.000 claims description 2
- NJAFJMATRYDQQG-OAHLLOKOSA-N n-hydroxy-n-[(2r)-2-[(isoquinolin-1-ylamino)carbamoyl]heptyl]formamide Chemical compound C1=CC=C2C(NNC(=O)[C@@H](CN(O)C=O)CCCCC)=NC=CC2=C1 NJAFJMATRYDQQG-OAHLLOKOSA-N 0.000 claims description 2
- BVWCULIIVOUKGF-GFCCVEGCSA-N n-hydroxy-n-[(2r)-2-[(pyridin-3-ylamino)carbamoyl]heptyl]formamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=CC=CN=C1 BVWCULIIVOUKGF-GFCCVEGCSA-N 0.000 claims description 2
- GTDKFMTYXQPHTN-CYBMUJFWSA-N n-hydroxy-n-[(2r)-2-[[(4-methylpyridin-2-yl)amino]carbamoyl]heptyl]formamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=CC(C)=CC=N1 GTDKFMTYXQPHTN-CYBMUJFWSA-N 0.000 claims description 2
- AVJYOBOPIOFGBO-GFCCVEGCSA-N n-hydroxy-n-[(2r)-2-[[(4-methylpyrimidin-2-yl)amino]carbamoyl]-4-thiophen-2-ylbutyl]formamide Chemical compound CC1=CC=NC(NNC(=O)[C@H](CCC=2SC=CC=2)CN(O)C=O)=N1 AVJYOBOPIOFGBO-GFCCVEGCSA-N 0.000 claims description 2
- NURINNKXUSFBFB-GFCCVEGCSA-N n-hydroxy-n-[(2r)-2-[[(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]carbamoyl]heptyl]formamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=CC(C)=NC2=NC=NN12 NURINNKXUSFBFB-GFCCVEGCSA-N 0.000 claims description 2
- RCDFEXFTXNVZQO-CYBMUJFWSA-N n-hydroxy-n-[(2r)-2-[[(6-methylpyridin-2-yl)amino]carbamoyl]heptyl]formamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=CC=CC(C)=N1 RCDFEXFTXNVZQO-CYBMUJFWSA-N 0.000 claims description 2
- DKVOTYNJAWMLFA-CQSZACIVSA-N n-hydroxy-n-[(2r)-2-[[(6-morpholin-4-ylpyrimidin-4-yl)amino]carbamoyl]heptyl]formamide Chemical compound C1=NC(NNC(=O)[C@@H](CN(O)C=O)CCCCC)=CC(N2CCOCC2)=N1 DKVOTYNJAWMLFA-CQSZACIVSA-N 0.000 claims description 2
- HYMXBKALYKRAIZ-CYBMUJFWSA-N n-hydroxy-n-[(2r)-2-[[(7-methyl-1,2,4-benzotriazin-3-yl)amino]carbamoyl]heptyl]formamide Chemical compound C1=C(C)C=CC2=NC(NNC(=O)[C@@H](CN(O)C=O)CCCCC)=NN=C21 HYMXBKALYKRAIZ-CYBMUJFWSA-N 0.000 claims description 2
- XGCHEWHTRVHSQB-GOSISDBHSA-N n-hydroxy-n-[(2r)-2-[[[1-(7-methoxy-1-benzofuran-2-carbonyl)piperidin-4-yl]amino]carbamoyl]heptyl]formamide Chemical compound C1CC(NNC(=O)[C@@H](CN(O)C=O)CCCCC)CCN1C(=O)C1=CC2=CC=CC(OC)=C2O1 XGCHEWHTRVHSQB-GOSISDBHSA-N 0.000 claims description 2
- PYGDVHDFBLCASS-OAHLLOKOSA-N n-hydroxy-n-[(2r)-2-[[[4-(2,3,4-trimethoxyphenyl)pyrimidin-2-yl]amino]carbamoyl]heptyl]formamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=CC(C=2C(=C(OC)C(OC)=CC=2)OC)=N1 PYGDVHDFBLCASS-OAHLLOKOSA-N 0.000 claims description 2
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- OBUSYDJFUJXEIH-OAHLLOKOSA-N n-hydroxy-n-[(2r)-2-[[[4-[2-methoxyethyl(methyl)amino]-6-propan-2-yl-1,3,5-triazin-2-yl]amino]carbamoyl]heptyl]formamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC(C(C)C)=NC(N(C)CCOC)=N1 OBUSYDJFUJXEIH-OAHLLOKOSA-N 0.000 claims description 2
- IDGPJZWFNGBYCT-LLVKDONJSA-N n-hydroxy-n-[(2r)-2-[[[5-(2-hydroxyethylamino)-4-(trifluoromethyl)pyrimidin-2-yl]amino]carbamoyl]heptyl]formamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=C(NCCO)C(C(F)(F)F)=N1 IDGPJZWFNGBYCT-LLVKDONJSA-N 0.000 claims description 2
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- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
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- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
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- CJWIFKOGFPBVTP-UHFFFAOYSA-N tert-butyl n-(1,3-benzodioxol-5-yl)-n-(methylamino)carbamate Chemical compound CC(C)(C)OC(=O)N(NC)C1=CC=C2OCOC2=C1 CJWIFKOGFPBVTP-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
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- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
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- RNGOYRMJHFBTRJ-SECBINFHSA-N 2-[2-[(2r)-2-[[formyl(hydroxy)amino]methyl]heptanoyl]hydrazinyl]-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=C(C(O)=O)C(C(F)(F)F)=N1 RNGOYRMJHFBTRJ-SECBINFHSA-N 0.000 claims 3
- MYXAGMGSGIGXED-UHFFFAOYSA-N (sulfonylamino)carbamic acid Chemical group OC(=O)NN=S(=O)=O MYXAGMGSGIGXED-UHFFFAOYSA-N 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- XPFRTICCNRDEAK-UHFFFAOYSA-N 1,2-dihydro-4h-pyrrolo[3,2,1-ij]quinolin-4-one Chemical compound O=C1C=CC2=CC=CC3=C2N1CC3 XPFRTICCNRDEAK-UHFFFAOYSA-N 0.000 claims 1
- GHGZGDGWFWIAQM-UHFFFAOYSA-N 1,3,4-trimethylpyrazole Chemical compound CC1=CN(C)N=C1C GHGZGDGWFWIAQM-UHFFFAOYSA-N 0.000 claims 1
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- LKIMDXQLHFCXQF-UHFFFAOYSA-N 3-methoxy-1h-pyridin-2-one Chemical compound COC1=CC=CN=C1O LKIMDXQLHFCXQF-UHFFFAOYSA-N 0.000 claims 1
- FYQXZVNMKXBILY-FWJOYPJLSA-N N-[(2R)-2-[[(1-amino-4-cyclopropyl-6-ethyl-2H-1,3,5-triazin-2-yl)amino]carbamoyl]heptyl]-N-hydroxyformamide Chemical compound C1(CC1)C1=NC(N(C(=N1)CC)N)NNC(=O)[C@@H](CN(C=O)O)CCCCC FYQXZVNMKXBILY-FWJOYPJLSA-N 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
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- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
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- AYIWSTLTXWJTQZ-CYBMUJFWSA-N n-[(2r)-2-(cyclohexylmethyl)-3-[2-[4-(cyclopropylamino)-5-fluoropyrimidin-2-yl]hydrazinyl]-3-oxopropyl]-n-hydroxyformamide Chemical compound C([C@H](CN(O)C=O)C(=O)NNC=1N=C(NC2CC2)C(F)=CN=1)C1CCCCC1 AYIWSTLTXWJTQZ-CYBMUJFWSA-N 0.000 claims 1
- ISSNZGLFMLXQRA-CYBMUJFWSA-N n-[(2r)-2-(cyclopentylmethyl)-3-[2-(7-methoxy-1,2,4-benzotriazin-3-yl)hydrazinyl]-3-oxopropyl]-n-hydroxyformamide Chemical compound C([C@@H](C(=O)NNC1=NC2=CC=C(C=C2N=N1)OC)CN(O)C=O)C1CCCC1 ISSNZGLFMLXQRA-CYBMUJFWSA-N 0.000 claims 1
- MPBPDJCWFDTIHJ-CYBMUJFWSA-N n-[(2r)-2-(cyclopentylmethyl)-3-[2-[4-(cyclopropylamino)-6-ethyl-1,3,5-triazin-2-yl]hydrazinyl]-3-oxopropyl]-n-hydroxyformamide Chemical compound C([C@@H](C(=O)NNC=1N=C(N=C(NC2CC2)N=1)CC)CN(O)C=O)C1CCCC1 MPBPDJCWFDTIHJ-CYBMUJFWSA-N 0.000 claims 1
- BEMHYQLUQKUGDU-CYBMUJFWSA-N n-[(2r)-2-(cyclopentylmethyl)-3-[2-[4-(dimethylamino)-6-ethyl-1,3,5-triazin-2-yl]hydrazinyl]-3-oxopropyl]-n-hydroxyformamide Chemical compound CN(C)C1=NC(CC)=NC(NNC(=O)[C@H](CC2CCCC2)CN(O)C=O)=N1 BEMHYQLUQKUGDU-CYBMUJFWSA-N 0.000 claims 1
- AQYFZTUHVKJKIC-CQSZACIVSA-N n-[(2r)-2-(cyclopentylmethyl)-3-[2-[4-morpholin-4-yl-6-(trifluoromethyl)pyrimidin-2-yl]hydrazinyl]-3-oxopropyl]-n-hydroxyformamide Chemical compound C([C@H](CN(O)C=O)C(=O)NNC=1N=C(C=C(N=1)N1CCOCC1)C(F)(F)F)C1CCCC1 AQYFZTUHVKJKIC-CQSZACIVSA-N 0.000 claims 1
- JHRMNLVJENVSDP-CYBMUJFWSA-N n-[(2r)-2-[(1,2,4-benzotriazin-3-ylamino)carbamoyl]octyl]-n-hydroxyformamide Chemical compound C1=CC=CC2=NC(NNC(=O)[C@@H](CN(O)C=O)CCCCCC)=NN=C21 JHRMNLVJENVSDP-CYBMUJFWSA-N 0.000 claims 1
- ARJAJAOHVFMCKN-GFCCVEGCSA-N n-[(2r)-2-[(cyclopropylmethylamino)carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNCC1CC1 ARJAJAOHVFMCKN-GFCCVEGCSA-N 0.000 claims 1
- HKZUXNOXQYBGOZ-LJQANCHMSA-N n-[(2r)-2-[[(1-benzylpiperidin-4-yl)amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound C1CC(NNC(=O)[C@@H](CN(O)C=O)CCCCC)CCN1CC1=CC=CC=C1 HKZUXNOXQYBGOZ-LJQANCHMSA-N 0.000 claims 1
- UTIVMHKBRNSQCT-MRXNPFEDSA-N n-[(2r)-2-[[(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound N=1C(NNC(=O)[C@@H](CN(O)C=O)CCCCC)=NC(N2CCOCC2)=NC=1N1CCOCC1 UTIVMHKBRNSQCT-MRXNPFEDSA-N 0.000 claims 1
- VJAIJJWXVJWGAQ-LLVKDONJSA-N n-[(2r)-2-[[(4-amino-6-propan-2-yl-1,3,5-triazin-2-yl)amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC(N)=NC(C(C)C)=N1 VJAIJJWXVJWGAQ-LLVKDONJSA-N 0.000 claims 1
- XLFYYHDNDUQYFF-OAHLLOKOSA-N n-[(2r)-2-[[(4-ethyl-6-morpholin-4-ylpyrimidin-2-yl)amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC(CC)=CC(N2CCOCC2)=N1 XLFYYHDNDUQYFF-OAHLLOKOSA-N 0.000 claims 1
- UAIJTYBEXHOQIW-SNVBAGLBSA-N n-[(2r)-2-[[(5-fluoro-4-methoxypyrimidin-2-yl)amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=C(F)C(OC)=N1 UAIJTYBEXHOQIW-SNVBAGLBSA-N 0.000 claims 1
- NLAZNKSZDVJKQH-CYBMUJFWSA-N n-[(2r)-2-[[(6-ethoxypyridin-2-yl)amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=CC=CC(OCC)=N1 NLAZNKSZDVJKQH-CYBMUJFWSA-N 0.000 claims 1
- YYEZNNBRJRJESP-GFCCVEGCSA-N n-[(2r)-2-[[(7-fluoro-1,2,4-benzotriazin-3-yl)amino]carbamoyl]-6-methylheptyl]-n-hydroxyformamide Chemical compound C1=C(F)C=CC2=NC(NNC(=O)[C@@H](CN(O)C=O)CCCC(C)C)=NN=C21 YYEZNNBRJRJESP-GFCCVEGCSA-N 0.000 claims 1
- LDMXIEOPKDMRRD-OAHLLOKOSA-N n-[(2r)-2-[[[4-(2,6-dimethoxyphenyl)pyrimidin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=CC(C=2C(=CC=CC=2OC)OC)=N1 LDMXIEOPKDMRRD-OAHLLOKOSA-N 0.000 claims 1
- JQMNTVJSWFHFLX-MRXNPFEDSA-N n-[(2r)-2-[[[4-(4-ethylpiperazin-1-yl)-6-(trifluoromethyl)pyrimidin-2-yl]amino]carbamoyl]-6-methylheptyl]-n-hydroxyformamide Chemical compound C1CN(CC)CCN1C1=CC(C(F)(F)F)=NC(NNC(=O)[C@H](CCCC(C)C)CN(O)C=O)=N1 JQMNTVJSWFHFLX-MRXNPFEDSA-N 0.000 claims 1
- MVKJQIWDQGSVCH-LLVKDONJSA-N n-[(2r)-2-[[[4-(cyclopropylamino)-5-fluoropyrimidin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=C(F)C(NC2CC2)=N1 MVKJQIWDQGSVCH-LLVKDONJSA-N 0.000 claims 1
- QVXSJLFTGBKTCG-CYBMUJFWSA-N n-[(2r)-2-[[[4-(cyclopropylamino)-6-methylpyrimidin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC(C)=CC(NC2CC2)=N1 QVXSJLFTGBKTCG-CYBMUJFWSA-N 0.000 claims 1
- IROJOJJEQFWWMF-CQSZACIVSA-N n-[(2r)-2-[[[4-(diethylamino)-6-methyl-1,3,5-triazin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC(C)=NC(N(CC)CC)=N1 IROJOJJEQFWWMF-CQSZACIVSA-N 0.000 claims 1
- SJEUZEAMZOLVQF-CQSZACIVSA-N n-[(2r)-2-[[[4-(dimethylamino)-6-morpholin-4-yl-1,3,5-triazin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC(N(C)C)=NC(N2CCOCC2)=N1 SJEUZEAMZOLVQF-CQSZACIVSA-N 0.000 claims 1
- XSKLFVLGRYSZJC-CQSZACIVSA-N n-[(2r)-2-[[[4-(dimethylamino)quinazolin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound C1=CC=CC2=NC(NNC(=O)[C@@H](CN(O)C=O)CCCCC)=NC(N(C)C)=C21 XSKLFVLGRYSZJC-CQSZACIVSA-N 0.000 claims 1
- JPPJZUCFCLSWSJ-CYBMUJFWSA-N n-[(2r)-2-[[[4-(furan-2-yl)pyrimidin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=CC(C=2OC=CC=2)=N1 JPPJZUCFCLSWSJ-CYBMUJFWSA-N 0.000 claims 1
- ATOGACDVWRWBEV-CYBMUJFWSA-N n-[(2r)-2-[[[4-(furan-3-yl)pyrimidin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=CC(C2=COC=C2)=N1 ATOGACDVWRWBEV-CYBMUJFWSA-N 0.000 claims 1
- KGSNZIPPIFPXKN-OAHLLOKOSA-N n-[(2r)-2-[[[4-[2-(dimethylamino)ethyl-methylamino]-6-ethyl-1,3,5-triazin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC(CC)=NC(N(C)CCN(C)C)=N1 KGSNZIPPIFPXKN-OAHLLOKOSA-N 0.000 claims 1
- YFGIAXXOLQFQPG-CYBMUJFWSA-N n-[(2r)-2-[[[4-[ethyl(methyl)amino]-6-methyl-1,3,5-triazin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC(C)=NC(N(C)CC)=N1 YFGIAXXOLQFQPG-CYBMUJFWSA-N 0.000 claims 1
- NYEANNRGSKXJBP-QGZVFWFLSA-N n-[(2r)-2-[[[4-ethyl-6-(4-propan-2-ylpiperazin-1-yl)-1,3,5-triazin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC(CC)=NC(N2CCN(CC2)C(C)C)=N1 NYEANNRGSKXJBP-QGZVFWFLSA-N 0.000 claims 1
- ZQMOWEGQAILJAL-ZIAGYGMSSA-N n-[(2r)-2-[[[4-ethyl-6-[(3r)-3-hydroxypyrrolidin-1-yl]-1,3,5-triazin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC(CC)=NC(N2C[C@H](O)CC2)=N1 ZQMOWEGQAILJAL-ZIAGYGMSSA-N 0.000 claims 1
- XUEODDKAAFNJMZ-CQSZACIVSA-N n-[(2r)-2-[[[4-ethyl-6-[2-methoxyethyl(methyl)amino]-1,3,5-triazin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC(CC)=NC(N(C)CCOC)=N1 XUEODDKAAFNJMZ-CQSZACIVSA-N 0.000 claims 1
- RSVRCTVUKOCPBW-CYBMUJFWSA-N n-[(2r)-2-[[[4-ethyl-6-[ethyl(methyl)amino]-1,3,5-triazin-2-yl]amino]carbamoyl]-4-thiophen-2-ylbutyl]-n-hydroxyformamide Chemical compound CCN(C)C1=NC(CC)=NC(NNC(=O)[C@H](CCC=2SC=CC=2)CN(O)C=O)=N1 RSVRCTVUKOCPBW-CYBMUJFWSA-N 0.000 claims 1
- LPSANBPSZKHGNL-OAHLLOKOSA-N n-[(2r)-2-[[[5-(4,6-dimethoxypyrimidin-2-yl)pyridin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound C1=NC(NNC(=O)[C@@H](CN(O)C=O)CCCCC)=CC=C1C1=NC(OC)=CC(OC)=N1 LPSANBPSZKHGNL-OAHLLOKOSA-N 0.000 claims 1
- GTHQOCGJODKMSU-CYBMUJFWSA-N n-[(2r)-2-[[[5-(dimethylamino)-4-methylpyrimidin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=C(N(C)C)C(C)=N1 GTHQOCGJODKMSU-CYBMUJFWSA-N 0.000 claims 1
- KEEUHIIGWUZXTL-MRXNPFEDSA-N n-[(2r)-2-[[[5-(dimethylamino)-4-pyridin-4-ylpyrimidin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=C(N(C)C)C(C=2C=CN=CC=2)=N1 KEEUHIIGWUZXTL-MRXNPFEDSA-N 0.000 claims 1
- JUCJUWDORMKREE-GFCCVEGCSA-N n-[(2r)-2-[[[5-[ethyl(methyl)amino]-4-fluoropyrimidin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=C(N(C)CC)C(F)=N1 JUCJUWDORMKREE-GFCCVEGCSA-N 0.000 claims 1
- TVHGVWWSNPMXKV-LLVKDONJSA-N n-[(2r)-2-[[[6-(dimethylamino)-7h-purin-2-yl]amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC(N(C)C)=C2N=CNC2=N1 TVHGVWWSNPMXKV-LLVKDONJSA-N 0.000 claims 1
- BZGNBJXPMIZTRK-ZDUSSCGKSA-N n-[(2r)-2-cyclopentyl-3-[2-(7-methyl-1,2,4-benzotriazin-3-yl)hydrazinyl]-3-oxopropyl]-n-hydroxyformamide Chemical compound C1([C@H](CN(O)C=O)C(=O)NNC2=NC3=CC=C(C=C3N=N2)C)CCCC1 BZGNBJXPMIZTRK-ZDUSSCGKSA-N 0.000 claims 1
- RJWTUPRZOZUNKF-CYBMUJFWSA-N n-[(2r)-3-[2-[4-(azetidin-1-yl)-5-fluoropyrimidin-2-yl]hydrazinyl]-2-(cyclopentylmethyl)-3-oxopropyl]-n-hydroxyformamide Chemical compound C([C@H](CN(O)C=O)C(=O)NNC=1N=C(C(F)=CN=1)N1CCC1)C1CCCC1 RJWTUPRZOZUNKF-CYBMUJFWSA-N 0.000 claims 1
- VOQAZUZDAUOBDA-RUXDESIVSA-N n-[(2r)-3-[2-[4-(dimethylamino)-6-ethyl-1,3,5-triazin-2-yl]hydrazinyl]-2-(4-methylcyclohexyl)-3-oxopropyl]-n-hydroxyformamide Chemical compound CN(C)C1=NC(CC)=NC(NNC(=O)[C@@H](CN(O)C=O)C2CCC(C)CC2)=N1 VOQAZUZDAUOBDA-RUXDESIVSA-N 0.000 claims 1
- JNLJWEMVNPLIKD-JXQTWKCFSA-N n-[(2r)-3-[2-[4-(dimethylamino)-6-ethyl-1,3,5-triazin-2-yl]hydrazinyl]-2-[(2-methylcyclopentyl)methyl]-3-oxopropyl]-n-hydroxyformamide Chemical compound CN(C)C1=NC(CC)=NC(NNC(=O)[C@H](CC2C(CCC2)C)CN(O)C=O)=N1 JNLJWEMVNPLIKD-JXQTWKCFSA-N 0.000 claims 1
- PYOIISJJRHCGIM-CQSZACIVSA-N n-[(2r)-4,4-dimethyl-2-[[(4-methylpyridin-2-yl)amino]carbamoyl]heptyl]-n-hydroxyformamide Chemical compound CCCC(C)(C)C[C@H](CN(O)C=O)C(=O)NNC1=CC(C)=CC=N1 PYOIISJJRHCGIM-CQSZACIVSA-N 0.000 claims 1
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- NOVKNPSYCOUSKF-CYBMUJFWSA-N n-[(2r)-4,4-dimethyl-2-[[(5-methyl-1,2,4-benzotriazin-3-yl)amino]carbamoyl]hexyl]-n-hydroxyformamide Chemical compound C1=CC=C(C)C2=NC(NNC(=O)[C@@H](CN(O)C=O)CC(C)(C)CC)=NN=C21 NOVKNPSYCOUSKF-CYBMUJFWSA-N 0.000 claims 1
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- DCHIUDIKUZNWNW-SNVBAGLBSA-N n-hydroxy-n-[(2r)-2-[[[6-(trifluoromethyl)pyridazin-3-yl]amino]carbamoyl]heptyl]formamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=CC=C(C(F)(F)F)N=N1 DCHIUDIKUZNWNW-SNVBAGLBSA-N 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WCGLOPIBARBWKT-GFCCVEGCSA-N n-tert-butyl-2-[2-[(2r)-2-[[formyl(hydroxy)amino]methyl]heptanoyl]hydrazinyl]-4-(trifluoromethyl)pyrimidine-5-carboxamide Chemical compound CCCCC[C@H](CN(O)C=O)C(=O)NNC1=NC=C(C(=O)NC(C)(C)C)C(C(F)(F)F)=N1 WCGLOPIBARBWKT-GFCCVEGCSA-N 0.000 description 1
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 230000003647 oxidation Effects 0.000 description 1
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- 230000020477 pH reduction Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
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- 150000003230 pyrimidines Chemical class 0.000 description 1
- YNZAFFFENDLJQG-UHFFFAOYSA-N pyrrol-1-amine Chemical compound NN1C=CC=C1 YNZAFFFENDLJQG-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
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- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
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- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- IOPZBVFVFPPDSC-UHFFFAOYSA-N tert-butyl n-(1,3-dioxoisoindol-2-yl)carbamate Chemical compound C1=CC=C2C(=O)N(NC(=O)OC(C)(C)C)C(=O)C2=C1 IOPZBVFVFPPDSC-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
- C07C23/18—Polycyclic halogenated hydrocarbons
- C07C23/20—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic
- C07C23/27—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic with a bicyclo ring system containing seven carbon atoms
- C07C23/28—Saturated bicyclo ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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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
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/10—Hydrazines
- C07C243/22—Hydrazines having nitrogen atoms of hydrazine groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
- C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D213/60—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 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
- C07D237/20—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
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- C—CHEMISTRY; METALLURGY
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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms
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- C07D253/10—Condensed 1,2,4-triazines; Hydrogenated condensed 1,2,4-triazines
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- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
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| US38445702P | 2002-05-31 | 2002-05-31 | |
| PCT/US2003/017054 WO2003101442A1 (en) | 2002-05-31 | 2003-05-30 | Peptide deformylase inhibitors |
Publications (2)
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| BR0311318A BR0311318A (pt) | 2005-02-22 |
| BRPI0311318B1 true BRPI0311318B1 (pt) | 2016-05-10 |
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| BRPI0311318A BRPI0311318B1 (pt) | 2002-05-31 | 2003-05-30 | inibidores de peptídeo desformilase |
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| GB0229673D0 (en) * | 2002-12-19 | 2003-01-29 | British Biotech Pharm | Antibacterial agents |
| WO2005005456A2 (en) * | 2003-07-08 | 2005-01-20 | Glaxo Group Limited | Peptide deformylase inhibitors |
| JP2007502825A (ja) * | 2003-08-15 | 2007-02-15 | スミスクライン・ビーチャム・コーポレイション | ペプチドデホルミラーゼ阻害剤 |
| AR050858A1 (es) * | 2004-09-07 | 2006-11-29 | Glaxo Group Ltd | Compuesto de heteroaril-nitrilo sustituido, su uso para la fabricacion de un medicamento, composicion farmaceutica que lo comprende y procedimiento para la preparacion del mismo |
| US20080161249A1 (en) * | 2004-11-17 | 2008-07-03 | Smithkline Beecham Corporation | Use of Novel Antibacterial Compounds |
| DE102005019181A1 (de) | 2005-04-25 | 2006-10-26 | Novartis Ag | Peptid-Deformylase (PDF) Inhibitoren 1 |
| WO2006114261A1 (en) * | 2005-04-25 | 2006-11-02 | Novartis Ag | Imidazo(1,2-a)pyridine derivatives useful as peptide deformylase (pdf) inhibitors |
| WO2007067904A2 (en) * | 2005-12-06 | 2007-06-14 | Smithkline Beecham Corporation | Peptide deformylase inhibitors |
| WO2007067906A2 (en) * | 2005-12-09 | 2007-06-14 | Smithkline Beecham Corporation | Peptide deformylase inhibitors |
| EP1918284A1 (en) * | 2006-10-30 | 2008-05-07 | Glaxo Group | Hydrazinopyrimidines as cysteine protease inhibitors |
| EP2028182A1 (en) * | 2007-08-21 | 2009-02-25 | Glaxo Group Limited | Cysteine protease inhibitors |
| UA108596C2 (xx) | 2007-11-09 | 2015-05-25 | Інгібітори пептиддеформілази | |
| DE102010044131A1 (de) * | 2010-11-18 | 2012-05-24 | Bayer Schering Pharma Aktiengesellschaft | Substituiertes Natrium-1H-pyrazol-5-olat |
| JP5959537B2 (ja) | 2011-01-28 | 2016-08-02 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 置換ピリジニル−ピリミジン及び医薬としてのその使用 |
| AR085698A1 (es) * | 2011-03-09 | 2013-10-23 | Glaxosmithkline Llc | Inhibidores de la peptido desformilasa |
| AU2013258107B2 (en) * | 2012-05-08 | 2017-06-22 | Bayer Pharma Aktiengesellschaft | Method for the preparation of triazole compounds |
| WO2014141181A1 (en) | 2013-03-15 | 2014-09-18 | Glaxosmithkline Intellectual Property No 2 Limited | Process for preparing peptide deformylase inhibitors |
| CN110452224B (zh) * | 2019-08-30 | 2022-06-03 | 西南大学 | 嘧啶唑醇类化合物及其制备方法和应用 |
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| GB9223904D0 (en) * | 1992-11-13 | 1993-01-06 | British Bio Technology | Inhibition of cytokine production |
| US6013792A (en) * | 1993-08-05 | 2000-01-11 | Syntex (U.S.A.), Inc. | Matrix metalloprotease inhibitors |
| US6037472A (en) * | 1993-11-04 | 2000-03-14 | Syntex (U.S.A.) Inc. | Matrix metalloprotease inhibitors |
| WO1995032944A1 (en) * | 1994-05-28 | 1995-12-07 | British Biotech Pharmaceuticals Limited | Succinyl hydroxamic acid, n-formyl-n-hydroxy amino carboxylic acid and succinic acid amide derivatives as metalloprotease inhibitors |
| US6235787B1 (en) * | 1997-06-30 | 2001-05-22 | Hoffmann-La Roche Inc. | Hydrazine derivatives |
| NZ505675A (en) * | 1998-02-07 | 2002-11-26 | British Biotech Pharm | N-alkylamide substituted hydroxamic acid derivatives are used as antibacterial agents |
| US6239151B1 (en) * | 1998-06-26 | 2001-05-29 | Hoffmann-La Roche Inc. | Compounds as inhibitor of tumor necrosis factor alpha release |
| GB9827805D0 (en) | 1998-12-16 | 1999-02-10 | British Biotech Pharm | Antibacterial agents |
| JP2002534512A (ja) | 1999-01-15 | 2002-10-15 | ノボ ノルディスク アクティーゼルスカブ | 非ペプチドglp−1アゴニスト |
| WO2000061134A1 (en) * | 1999-04-09 | 2000-10-19 | British Biotech Pharmaceuticals Limited | Antimicrobial agents |
| CA2379061C (en) * | 1999-08-10 | 2008-12-09 | British Biotech Pharmaceuticals Limited | Antibacterial agents |
| EP1210330B1 (en) * | 1999-08-10 | 2005-04-20 | Vernalis (Oxford) Ltd | Antibacterial agents |
| AR028075A1 (es) * | 2000-05-05 | 2003-04-23 | Smithkline Beecham Corp | Inhibidores de la peptido-desformilasa |
| DE10040783A1 (de) | 2000-08-21 | 2002-03-07 | Merck Patent Gmbh | AZA-Aminosäurederivate (Faktor X¶a¶-Inhibitoren 15) |
| EP1339400B1 (en) * | 2000-11-23 | 2005-06-29 | Vernalis (Oxford) Ltd | N-formyl hydroxylamine derivatives as inhibitors of bacterial polypeptide deformylase for treating microbial infections |
| AR032920A1 (es) * | 2001-03-01 | 2003-12-03 | Smithkline Beecham Corp | Compuestos inhibidores de las peptido-deformilasas y medios para tratar infecciones bacterianas utilizando dichos inhibidores |
| WO2004052919A2 (en) | 2002-12-11 | 2004-06-24 | Smithkline Beecham Corporation | Peptide deformylase inhibitors |
| WO2005005456A2 (en) | 2003-07-08 | 2005-01-20 | Glaxo Group Limited | Peptide deformylase inhibitors |
| JP2007502825A (ja) | 2003-08-15 | 2007-02-15 | スミスクライン・ビーチャム・コーポレイション | ペプチドデホルミラーゼ阻害剤 |
| US20080161249A1 (en) | 2004-11-17 | 2008-07-03 | Smithkline Beecham Corporation | Use of Novel Antibacterial Compounds |
| UA108596C2 (xx) | 2007-11-09 | 2015-05-25 | Інгібітори пептиддеформілази |
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- 2003-05-29 PE PE2003000518A patent/PE20040528A1/es not_active Application Discontinuation
- 2003-05-30 KR KR1020047019400A patent/KR101032823B1/ko not_active Expired - Fee Related
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