TW201102065A

TW201102065A - Heterocyclic urea derivatives and methods of use thereof

Heterocyclic urea derivatives and methods of use thereof Download PDF

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Publication number: TW201102065A
Authority: TW; Taiwan
Prior art keywords: group; alkyl; compound; amine; ethyl
Prior art date: 2009-05-29

Application number

TW099117083A

Other languages

English (en)

Chinese (zh)

Inventor

Allison Choy

Brian Sherer

Olga Ouiroga

Neil Bifulco

Original Assignee

Astrazeneca Ab

Priority date

2009-05-29

Filing date

2010-05-27

Publication date

2011-01-16

2010-05-27 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2011-01-16 Publication of TW201102065A publication Critical patent/TW201102065A/zh

Links

238000000034 method Methods 0.000 title claims abstract description 90
-1 Heterocyclic urea derivatives Chemical class 0.000 title claims description 185
150000001875 compounds Chemical class 0.000 claims abstract description 259
208000035143 Bacterial infection Diseases 0.000 claims abstract description 145
208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 145
150000003839 salts Chemical class 0.000 claims abstract description 98
238000011282 treatment Methods 0.000 claims abstract description 39
239000003814 drug Substances 0.000 claims abstract description 23
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
208000015181 infectious disease Diseases 0.000 claims description 248
125000000217 alkyl group Chemical group 0.000 claims description 140
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 77
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 64
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 60
125000000623 heterocyclic group Chemical group 0.000 claims description 59
241001465754 Metazoa Species 0.000 claims description 53
229910052757 nitrogen Inorganic materials 0.000 claims description 45
150000001412 amines Chemical class 0.000 claims description 41
125000003545 alkoxy group Chemical group 0.000 claims description 38
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 36
QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 31
125000003277 amino group Chemical group 0.000 claims description 26
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 26
229910052799 carbon Inorganic materials 0.000 claims description 25
206010035664 Pneumonia Diseases 0.000 claims description 24
241000894006 Bacteria Species 0.000 claims description 23
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 22
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
241000191967 Staphylococcus aureus Species 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 20
238000004519 manufacturing process Methods 0.000 claims description 20
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
230000002401 inhibitory effect Effects 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 18
230000000844 anti-bacterial effect Effects 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
208000019206 urinary tract infection Diseases 0.000 claims description 17
108010041052 DNA Topoisomerase IV Proteins 0.000 claims description 16
239000007789 gas Substances 0.000 claims description 15
230000001580 bacterial effect Effects 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 14
229910052760 oxygen Inorganic materials 0.000 claims description 14
239000001301 oxygen Substances 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims description 13
241000193998 Streptococcus pneumoniae Species 0.000 claims description 13
108010059993 Vancomycin Proteins 0.000 claims description 13
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
125000004429 atom Chemical group 0.000 claims description 13
125000002837 carbocyclic group Chemical group 0.000 claims description 13
239000003795 chemical substances by application Substances 0.000 claims description 13
229940031000 streptococcus pneumoniae Drugs 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 claims description 13
229960003165 vancomycin Drugs 0.000 claims description 13
MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 claims description 13
229930182555 Penicillin Natural products 0.000 claims description 12
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 12
206010040047 Sepsis Diseases 0.000 claims description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
229940049954 penicillin Drugs 0.000 claims description 12
208000002633 Febrile Neutropenia Diseases 0.000 claims description 11
RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims description 11
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 11
229940079593 drug Drugs 0.000 claims description 11
206010014665 endocarditis Diseases 0.000 claims description 11
229960003085 meticillin Drugs 0.000 claims description 11
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
239000000546 pharmaceutical excipient Substances 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 11
239000011593 sulfur Substances 0.000 claims description 11
125000003396 thiol group Chemical group [H]S* 0.000 claims description 11
206010031252 Osteomyelitis Diseases 0.000 claims description 10
241000191963 Staphylococcus epidermidis Species 0.000 claims description 10
125000000304 alkynyl group Chemical group 0.000 claims description 10
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
206010006451 bronchitis Diseases 0.000 claims description 9
208000022760 infectious otitis media Diseases 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
230000001225 therapeutic effect Effects 0.000 claims description 9
206010001076 Acute sinusitis Diseases 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
108020000946 Bacterial DNA Proteins 0.000 claims description 7
208000008745 Healthcare-Associated Pneumonia Diseases 0.000 claims description 7
150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 7
125000004452 carbocyclyl group Chemical group 0.000 claims description 7
125000002757 morpholinyl group Chemical group 0.000 claims description 7
229910052707 ruthenium Inorganic materials 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000003386 piperidinyl group Chemical group 0.000 claims description 6
108090000769 Isomerases Proteins 0.000 claims description 5
102000004195 Isomerases Human genes 0.000 claims description 5
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 5
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
125000001589 carboacyl group Chemical group 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 5
125000004193 piperazinyl group Chemical group 0.000 claims description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
150000001721 carbon Chemical group 0.000 claims description 4
MYPYJXKWCTUITO-KIIOPKALSA-N chembl3301825 Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)C(O)[C@H](C)O1 MYPYJXKWCTUITO-KIIOPKALSA-N 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000000524 functional group Chemical group 0.000 claims description 3
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
238000006467 substitution reaction Methods 0.000 claims description 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 claims description 2
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 2
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
230000000069 prophylactic effect Effects 0.000 claims description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims 2
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 1
PFJOTFSIBVZGPK-UHFFFAOYSA-N 1-ethyl-2-methylhydrazine Chemical compound CCNNC PFJOTFSIBVZGPK-UHFFFAOYSA-N 0.000 claims 1
MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical group CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 claims 1
208000004145 Endometritis Diseases 0.000 claims 1
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229910002651 NO3 Inorganic materials 0.000 claims 1
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241000239226 Scorpiones Species 0.000 claims 1
NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 claims 1
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150000004056 anthraquinones Chemical class 0.000 claims 1
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims 1
229960005286 carbaryl Drugs 0.000 claims 1
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
WIKWUBHEBLFWHH-UHFFFAOYSA-N ethyl 2-propylpentanoate Chemical compound CCCC(CCC)C(=O)OCC WIKWUBHEBLFWHH-UHFFFAOYSA-N 0.000 claims 1
125000005842 heteroatom Chemical group 0.000 claims 1
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NIWKXCIWWOTLKA-UHFFFAOYSA-N methylsulfonylsulfonylsulfonylmethane Chemical group CS(=O)(=O)S(=O)(=O)S(C)(=O)=O NIWKXCIWWOTLKA-UHFFFAOYSA-N 0.000 claims 1
NCXUBWUMCXIMHK-UHFFFAOYSA-N n,n-diethyl-2-piperidin-1-ylethanamine Chemical compound CCN(CC)CCN1CCCCC1 NCXUBWUMCXIMHK-UHFFFAOYSA-N 0.000 claims 1
238000010883 osseointegration Methods 0.000 claims 1
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HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical group CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 11
230000008569 process Effects 0.000 abstract description 11
239000000543 intermediate Substances 0.000 description 331
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 241
239000007858 starting material Substances 0.000 description 117
238000005481 NMR spectroscopy Methods 0.000 description 109
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
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