TW200823188A - Certain chemical entities, compositions, and methods - Google Patents

Certain chemical entities, compositions, and methods Download PDF

Info

Publication number: TW200823188A
Authority: TW; Taiwan
Prior art keywords: group; ethyl; optionally substituted; amino; methyl
Prior art date: 2006-08-01

Application number

TW096128145A

Other languages

English (en)

Chinese (zh)

Inventor

Xiangping Qian

Jeffrey T Finer

Pu-Ping Lu

Chihyan Grace Chuang

Bradley P Morgan

Morgans, Jr

Original Assignee

Cytokinetics Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2006-08-01

Filing date

2007-08-01

Publication date

2008-06-01

2007-08-01 Application filed by Cytokinetics Inc filed Critical Cytokinetics Inc

2008-06-01 Publication of TW200823188A publication Critical patent/TW200823188A/zh

Links

238000000034 method Methods 0.000 title claims abstract description 12
239000000203 mixture Substances 0.000 title claims description 8
150000005829 chemical entities Chemical class 0.000 title abstract description 5
102000003505 Myosin Human genes 0.000 claims abstract description 37
108060008487 Myosin Proteins 0.000 claims abstract description 37
210000003205 muscle Anatomy 0.000 claims abstract description 17
201000010099 disease Diseases 0.000 claims abstract description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
210000002460 smooth muscle Anatomy 0.000 claims abstract description 14
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
-1 nitro, sulfonyl Chemical group 0.000 claims description 1388
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 864
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 611
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 377
125000000217 alkyl group Chemical group 0.000 claims description 244
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 183
239000000126 substance Substances 0.000 claims description 177
229910052739 hydrogen Inorganic materials 0.000 claims description 164
239000001257 hydrogen Substances 0.000 claims description 163
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 148
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 123
125000003396 thiol group Chemical group [H]S* 0.000 claims description 122
125000001072 heteroaryl group Chemical group 0.000 claims description 116
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 101
150000001875 compounds Chemical class 0.000 claims description 100
150000001412 amines Chemical class 0.000 claims description 89
125000000547 substituted alkyl group Chemical group 0.000 claims description 89
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 83
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 82
125000003277 amino group Chemical group 0.000 claims description 80
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 74
125000004093 cyano group Chemical group *C#N 0.000 claims description 68
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 68
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 67
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 58
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 56
125000003118 aryl group Chemical group 0.000 claims description 56
125000004076 pyridyl group Chemical group 0.000 claims description 55
125000003107 substituted aryl group Chemical group 0.000 claims description 55
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 48
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 44
125000005843 halogen group Chemical group 0.000 claims description 42
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 37
125000005415 substituted alkoxy group Chemical group 0.000 claims description 37
125000001424 substituent group Chemical group 0.000 claims description 35
125000000753 cycloalkyl group Chemical group 0.000 claims description 34
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 32
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 30
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 29
229910052799 carbon Inorganic materials 0.000 claims description 29
229910052757 nitrogen Inorganic materials 0.000 claims description 28
125000005017 substituted alkenyl group Chemical group 0.000 claims description 28
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 28
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 26
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 26
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical group C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 25
239000007789 gas Substances 0.000 claims description 25
150000001540 azides Chemical class 0.000 claims description 24
125000003342 alkenyl group Chemical group 0.000 claims description 23
125000004104 aryloxy group Chemical group 0.000 claims description 23
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 23
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical group OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 22
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 22
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 22
125000001207 fluorophenyl group Chemical group 0.000 claims description 20
150000002923 oximes Chemical class 0.000 claims description 20
125000003282 alkyl amino group Chemical group 0.000 claims description 19
125000001041 indolyl group Chemical group 0.000 claims description 19
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 19
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
229910052760 oxygen Inorganic materials 0.000 claims description 18
239000001301 oxygen Substances 0.000 claims description 18
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 18
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 16
125000000623 heterocyclic group Chemical group 0.000 claims description 16
YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 15
125000001309 chloro group Chemical group Cl* 0.000 claims description 15
125000001153 fluoro group Chemical group F* 0.000 claims description 15
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 14
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 13
125000001769 aryl amino group Chemical group 0.000 claims description 13
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 13
125000005842 heteroatom Chemical group 0.000 claims description 13
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 13
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 12
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 12
125000004426 substituted alkynyl group Chemical group 0.000 claims description 12
150000001335 aliphatic alkanes Chemical class 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
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 11
125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 11
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 9
VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical class N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 claims description 9
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 9
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 9
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 8
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 8
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 claims description 8
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
125000001246 bromo group Chemical group Br* 0.000 claims description 8
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 7
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 claims description 7
229930192474 thiophene Natural products 0.000 claims description 7
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 6
229910052786 argon Inorganic materials 0.000 claims description 6
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 6
125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 6
239000002689 soil Substances 0.000 claims description 6
238000006467 substitution reaction Methods 0.000 claims description 6
125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims description 5
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 5
KFCUPNHUPHDVJC-UHFFFAOYSA-N bromine azide Chemical compound BrN=[N+]=[N-] KFCUPNHUPHDVJC-UHFFFAOYSA-N 0.000 claims description 5
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
125000006308 propyl amino group Chemical group 0.000 claims description 5
229910052707 ruthenium Inorganic materials 0.000 claims description 5
208000024891 symptom Diseases 0.000 claims description 5
RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 claims description 5
150000003573 thiols Chemical class 0.000 claims description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 4
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 claims description 4
125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
230000000007 visual effect Effects 0.000 claims description 4
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
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 3
241000124008 Mammalia Species 0.000 claims description 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 3
125000006630 butoxycarbonylamino group Chemical group 0.000 claims description 3
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000004212 difluorophenyl group Chemical group 0.000 claims description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
125000004475 heteroaralkyl group Chemical group 0.000 claims description 3
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
241000894007 species Species 0.000 claims description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
VEKIYFGCEAJDDT-UHFFFAOYSA-N 2-pyridin-3-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1 VEKIYFGCEAJDDT-UHFFFAOYSA-N 0.000 claims description 2
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
KJTRXVXWSSPHRV-UHFFFAOYSA-N 4-benzoyl-5-methyl-2-phenyl-1h-pyrazol-3-one Chemical compound O=C1C(C(=O)C=2C=CC=CC=2)=C(C)NN1C1=CC=CC=C1 KJTRXVXWSSPHRV-UHFFFAOYSA-N 0.000 claims description 2
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
239000004472 Lysine Substances 0.000 claims description 2
239000005864 Sulphur Substances 0.000 claims description 2
125000005577 anthracene group Chemical group 0.000 claims description 2
239000012298 atmosphere Substances 0.000 claims description 2
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims description 2
229960005286 carbaryl Drugs 0.000 claims description 2
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical group C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 2
CUPOOAWTRIURFT-UHFFFAOYSA-N thiophene-2-carbonitrile Chemical compound N#CC1=CC=CS1 CUPOOAWTRIURFT-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 33
239000004305 biphenyl Substances 0.000 claims 8
208000006673 asthma Diseases 0.000 claims 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 3
208000030090 Acute Disease Diseases 0.000 claims 2
206010069632 Bladder dysfunction Diseases 0.000 claims 2
208000017667 Chronic Disease Diseases 0.000 claims 2
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
206010010904 Convulsion Diseases 0.000 claims 2
208000010412 Glaucoma Diseases 0.000 claims 2
206010020772 Hypertension Diseases 0.000 claims 2
208000006011 Stroke Diseases 0.000 claims 2
208000032851 Subarachnoid Hemorrhage Diseases 0.000 claims 2
206010046543 Urinary incontinence Diseases 0.000 claims 2
230000002159 abnormal effect Effects 0.000 claims 2
230000001154 acute effect Effects 0.000 claims 2
230000003435 bronchoconstrictive effect Effects 0.000 claims 2
230000036461 convulsion Effects 0.000 claims 2
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
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238000012360 testing method Methods 0.000 description 1
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Substances [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
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238000012549 training Methods 0.000 description 1
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Classifications

- 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
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- 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
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
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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
- C07D405/14—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 three or more hetero rings
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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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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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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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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TW096128145A 2006-08-01 2007-08-01 Certain chemical entities, compositions, and methods TW200823188A (en)

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US83490406P	2006-08-01	2006-08-01
US83490106P	2006-08-01	2006-08-01
US83501006P	2006-08-01	2006-08-01
US83490306P	2006-08-01	2006-08-01
US83518306P	2006-08-01	2006-08-01
US83523606P	2006-08-02	2006-08-02

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US20230023124A1 (en) *	2019-11-06	2023-01-26	Remedy Plan, Inc.	Cancer treatments targeting cancer stem cells
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WO2008016643A2 (en)	2008-02-07
AR062176A1 (es)	2008-10-22
PE20080432A1 (es)	2008-05-29

Publication	Publication Date	Title
TW200823188A (en)	2008-06-01	Certain chemical entities, compositions, and methods
AU2003261807B9 (en)	2007-02-15	Azaarene derivatives
DK2718266T3 (en)	2016-06-13	PYRIDIN-2-AMIDES USED AS CB2 AGONISTS
CA3010847C (en)	2025-09-23	METHODS AND COMPOUNDS FOR RESTORING THE FUNCTION OF THE MUTANT P53
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AU2010289353B2 (en)	2016-12-08	Compounds as tyrosine kinase modulators
AU2007272972B2 (en)	2011-12-01	Triazolyl pyridyl benzenesulfonamides as CCR2 or CCR9 modulators for the treatment of atherosclerosis
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CA2315117C (en)	2011-03-15	Heterocyclic ether and thioether compounds useful in controlling chemical synaptic transmission
TW200306180A (en)	2003-11-16	New compounds
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TW200804379A (en)	2008-01-16	PI-3 kinase inhibitors and methods of their use
TW200307678A (en)	2003-12-16	Substituted pyridines having antiangiogenic activity
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TW200524901A (en)	2005-08-01	6-membered heteroaryl compounds for the treatment of neurodegenerative disorders
WO2006015159A2 (en)	2006-02-09	Potassium channel inhibitors
JP2023518831A (ja)	2023-05-08	変異ｌｒｒｋ２タンパク質分解の選択的モジュレーター及び関連する使用方法
EA021464B1 (ru)	2015-06-30	Производные индол-пиридона, обладающие ингибиторной активностью в отношении киназы 1, содержащая их фармацевтическая композиция и их применение
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TW201038554A (en)	2010-11-01	Nicotinamide derivatives, their preparation and their therapeutic application