CA2883014A1 - Derivatives of 1-(substituted sulfonyl)-2-aminoimidazoline as antitumor and antiproliferative agents - Google Patents
Derivatives of 1-(substituted sulfonyl)-2-aminoimidazoline as antitumor and antiproliferative agents Download PDFInfo
- Publication number
- CA2883014A1 CA2883014A1 CA2883014A CA2883014A CA2883014A1 CA 2883014 A1 CA2883014 A1 CA 2883014A1 CA 2883014 A CA2883014 A CA 2883014A CA 2883014 A CA2883014 A CA 2883014A CA 2883014 A1 CA2883014 A1 CA 2883014A1
- Authority
- CA
- Canada
- Prior art keywords
- imidazol
- dihydro
- amine
- sulfonyl
- indoline
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- -1 1-(substituted sulfonyl)-2-aminoimidazoline Chemical class 0.000 title claims description 32
- 230000000259 anti-tumor effect Effects 0.000 title description 4
- 230000001028 anti-proliverative effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- 238000000034 method Methods 0.000 claims abstract description 20
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
- 201000011510 cancer Diseases 0.000 claims abstract description 8
- 201000010099 disease Diseases 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000000651 prodrug Substances 0.000 claims description 21
- 229940002612 prodrug Drugs 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 229910052717 sulfur Chemical group 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 239000011593 sulfur Chemical group 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 210000004027 cell Anatomy 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000012453 solvate Substances 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000002246 antineoplastic agent Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 201000005962 mycosis fungoides Diseases 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 2
- 201000005569 Gout Diseases 0.000 claims description 2
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims description 2
- 208000017604 Hodgkin disease Diseases 0.000 claims description 2
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims description 2
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 208000030289 Lymphoproliferative disease Diseases 0.000 claims description 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 208000009359 Sezary Syndrome Diseases 0.000 claims description 2
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- 230000001154 acute effect Effects 0.000 claims description 2
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- 230000000172 allergic effect Effects 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 210000000988 bone and bone Anatomy 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
- 210000000481 breast Anatomy 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 2
- 230000002496 gastric effect Effects 0.000 claims description 2
- 210000003128 head Anatomy 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 150000002466 imines Chemical group 0.000 claims description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- 210000003734 kidney Anatomy 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 210000004072 lung Anatomy 0.000 claims description 2
- 206010025135 lupus erythematosus Diseases 0.000 claims description 2
- 210000004698 lymphocyte Anatomy 0.000 claims description 2
- 230000000527 lymphocytic effect Effects 0.000 claims description 2
- 230000003211 malignant effect Effects 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 210000003739 neck Anatomy 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 230000002611 ovarian Effects 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 230000035755 proliferation Effects 0.000 claims description 2
- 210000002307 prostate Anatomy 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 210000003491 skin Anatomy 0.000 claims description 2
- 230000009885 systemic effect Effects 0.000 claims description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
- 210000001685 thyroid gland Anatomy 0.000 claims description 2
- 238000002054 transplantation Methods 0.000 claims description 2
- 210000003932 urinary bladder Anatomy 0.000 claims description 2
- 230000002792 vascular Effects 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 230000003463 hyperproliferative effect Effects 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 2
- IADPVLGMDGPWFG-VXNXSFHZSA-N (4-aminophenyl)-[5-[[(4s)-2-amino-4-phenyl-4,5-dihydroimidazol-1-yl]sulfonyl]-2-methyl-2,3-dihydroindol-1-yl]methanone Chemical compound CC1CC2=CC(S(=O)(=O)N3C(=N[C@H](C3)C=3C=CC=CC=3)N)=CC=C2N1C(=O)C1=CC=C(N)C=C1 IADPVLGMDGPWFG-VXNXSFHZSA-N 0.000 claims 1
- OVGGXWUHMJTVPN-CQSZACIVSA-N (4s)-1-(benzenesulfonyl)-4-phenyl-4,5-dihydroimidazol-2-amine Chemical compound C([C@@H](N=C1N)C=2C=CC=CC=2)N1S(=O)(=O)C1=CC=CC=C1 OVGGXWUHMJTVPN-CQSZACIVSA-N 0.000 claims 1
- CDHDIKKTNXMKQA-INIZCTEOSA-N (4s)-1-[[1-(1-methylpyrrol-2-yl)-2,3-dihydroindol-5-yl]sulfonyl]-4-pyrimidin-2-yl-4,5-dihydroimidazol-2-amine Chemical compound CN1C=CC=C1N1C2=CC=C(S(=O)(=O)N3C(=N[C@@H](C3)C=3N=CC=CN=3)N)C=C2CC1 CDHDIKKTNXMKQA-INIZCTEOSA-N 0.000 claims 1
- GVMWXQJWLRLUMX-LJQANCHMSA-N (4s)-4-(2,4-difluorophenyl)-1-[[1-(1-methylpyrrol-2-yl)-2,3-dihydroindol-5-yl]sulfonyl]-4,5-dihydroimidazol-2-amine Chemical compound CN1C=CC=C1N1C2=CC=C(S(=O)(=O)N3C(=N[C@H](C3)C=3C(=CC(F)=CC=3)F)N)C=C2CC1 GVMWXQJWLRLUMX-LJQANCHMSA-N 0.000 claims 1
- DPMHLPZQJQWLED-LJQANCHMSA-N (4s)-4-(2-chlorophenyl)-1-[[1-(1-methylpyrrol-2-yl)-2,3-dihydroindol-5-yl]sulfonyl]-4,5-dihydroimidazol-2-amine Chemical compound CN1C=CC=C1N1C2=CC=C(S(=O)(=O)N3C(=N[C@H](C3)C=3C(=CC=CC=3)Cl)N)C=C2CC1 DPMHLPZQJQWLED-LJQANCHMSA-N 0.000 claims 1
- PTYODDDSCBYIRD-HXUWFJFHSA-N (4s)-4-(2-methylphenyl)-1-[[1-(1-methylpyrrol-2-yl)-2,3-dihydroindol-5-yl]sulfonyl]-4,5-dihydroimidazol-2-amine Chemical compound CC1=CC=CC=C1[C@@H]1N=C(N)N(S(=O)(=O)C=2C=C3CCN(C3=CC=2)C=2N(C=CC=2)C)C1 PTYODDDSCBYIRD-HXUWFJFHSA-N 0.000 claims 1
- DJVIVJQELZKJDB-LJQANCHMSA-N (4s)-4-(3,5-dichlorophenyl)-1-[[1-(1-methylpyrrol-2-yl)-2,3-dihydroindol-5-yl]sulfonyl]-4,5-dihydroimidazol-2-amine Chemical compound CN1C=CC=C1N1C2=CC=C(S(=O)(=O)N3C(=N[C@H](C3)C=3C=C(Cl)C=C(Cl)C=3)N)C=C2CC1 DJVIVJQELZKJDB-LJQANCHMSA-N 0.000 claims 1
- VQBSIXRMBMROOB-LJQANCHMSA-N (4s)-4-(3-chlorophenyl)-1-[[1-(1-methylpyrrol-2-yl)-2,3-dihydroindol-5-yl]sulfonyl]-4,5-dihydroimidazol-2-amine Chemical compound CN1C=CC=C1N1C2=CC=C(S(=O)(=O)N3C(=N[C@H](C3)C=3C=C(Cl)C=CC=3)N)C=C2CC1 VQBSIXRMBMROOB-LJQANCHMSA-N 0.000 claims 1
- FXTADSFGWAYWSA-HXUWFJFHSA-N (4s)-4-(3-methylphenyl)-1-[[1-(1-methylpyrrol-2-yl)-2,3-dihydroindol-5-yl]sulfonyl]-4,5-dihydroimidazol-2-amine Chemical compound CC1=CC=CC([C@@H]2N=C(N)N(C2)S(=O)(=O)C=2C=C3CCN(C3=CC=2)C=2N(C=CC=2)C)=C1 FXTADSFGWAYWSA-HXUWFJFHSA-N 0.000 claims 1
- QTDCTWNXNYSWQL-LJQANCHMSA-N (4s)-4-(4-chlorophenyl)-1-[[1-(1-methylpyrrol-2-yl)-2,3-dihydroindol-5-yl]sulfonyl]-4,5-dihydroimidazol-2-amine Chemical compound CN1C=CC=C1N1C2=CC=C(S(=O)(=O)N3C(=N[C@H](C3)C=3C=CC(Cl)=CC=3)N)C=C2CC1 QTDCTWNXNYSWQL-LJQANCHMSA-N 0.000 claims 1
- XOZIFMKKJOCZMU-LJQANCHMSA-N (4s)-4-(4-fluorophenyl)-1-[[1-(1-methylpyrrol-2-yl)-2,3-dihydroindol-5-yl]sulfonyl]-4,5-dihydroimidazol-2-amine Chemical compound CN1C=CC=C1N1C2=CC=C(S(=O)(=O)N3C(=N[C@H](C3)C=3C=CC(F)=CC=3)N)C=C2CC1 XOZIFMKKJOCZMU-LJQANCHMSA-N 0.000 claims 1
- WEUFIWOXBKYUQC-HXUWFJFHSA-N (4s)-4-(4-methoxyphenyl)-1-[[1-(1-methylpyrrol-2-yl)-2,3-dihydroindol-5-yl]sulfonyl]-4,5-dihydroimidazol-2-amine Chemical compound C1=CC(OC)=CC=C1[C@@H]1N=C(N)N(S(=O)(=O)C=2C=C3CCN(C3=CC=2)C=2N(C=CC=2)C)C1 WEUFIWOXBKYUQC-HXUWFJFHSA-N 0.000 claims 1
- ZCSLLBPPYUSVBS-LBPRGKRZSA-N (4s)-4-methyl-1-[[1-(1-methylpyrrol-2-yl)-2,3-dihydroindol-5-yl]sulfonyl]-4,5-dihydroimidazol-2-amine Chemical compound NC1=N[C@@H](C)CN1S(=O)(=O)C1=CC=C(N(CC2)C=3N(C=CC=3)C)C2=C1 ZCSLLBPPYUSVBS-LBPRGKRZSA-N 0.000 claims 1
- LIGJMUDWIGAHRT-UHFFFAOYSA-N 1-(benzenesulfonyl)-4,5-dihydroimidazol-2-amine Chemical compound NC1=NCCN1S(=O)(=O)C1=CC=CC=C1 LIGJMUDWIGAHRT-UHFFFAOYSA-N 0.000 claims 1
- TVAZKEKTUDFUND-QGZVFWFLSA-N 1-[4-[[(4s)-2-amino-4-phenyl-4,5-dihydroimidazol-1-yl]sulfonyl]phenyl]pyrrolidin-2-one Chemical compound C([C@@H](N=C1N)C=2C=CC=CC=2)N1S(=O)(=O)C(C=C1)=CC=C1N1CCCC1=O TVAZKEKTUDFUND-QGZVFWFLSA-N 0.000 claims 1
- RAQDCKZZWDYZSV-MRXNPFEDSA-N 1-[4-[[(4s)-2-amino-4-phenyl-4,5-dihydroimidazol-1-yl]sulfonyl]phenyl]pyrrolidine-2,5-dione Chemical compound C([C@@H](N=C1N)C=2C=CC=CC=2)N1S(=O)(=O)C(C=C1)=CC=C1N1C(=O)CCC1=O RAQDCKZZWDYZSV-MRXNPFEDSA-N 0.000 claims 1
- OBBGBOGVKOACEJ-SFHVURJKSA-N 1-[5-[[(4R)-2-amino-4-phenyl-4,5-dihydroimidazol-1-yl]sulfonyl]-2,3-dihydroindol-1-yl]butan-1-one Chemical compound CCCC(=O)N1CCc2cc(ccc12)S(=O)(=O)N1C[C@H](N=C1N)c1ccccc1 OBBGBOGVKOACEJ-SFHVURJKSA-N 0.000 claims 1
- USTQRFUIGKSECC-GOSISDBHSA-N 1-[5-[[(4s)-2-amino-4-phenyl-4,5-dihydroimidazol-1-yl]sulfonyl]-2,3-dihydroindol-1-yl]-2-methylpropan-1-one Chemical compound C1([C@H]2CN(C(=N2)N)S(=O)(=O)C=2C=C3CCN(C3=CC=2)C(=O)C(C)C)=CC=CC=C1 USTQRFUIGKSECC-GOSISDBHSA-N 0.000 claims 1
- VYJGUOKAXILVOU-JOCHJYFZSA-N 1-[5-[[(4s)-2-amino-4-phenyl-4,5-dihydroimidazol-1-yl]sulfonyl]-2,3-dihydroindol-1-yl]-2-phenylethanone Chemical compound C([C@@H](N=C1N)C=2C=CC=CC=2)N1S(=O)(=O)C(C=C1CC2)=CC=C1N2C(=O)CC1=CC=CC=C1 VYJGUOKAXILVOU-JOCHJYFZSA-N 0.000 claims 1
- GAKUPVRBLIDIEY-HXUWFJFHSA-N 1-[5-[[(4s)-2-amino-4-phenyl-4,5-dihydroimidazol-1-yl]sulfonyl]-2,3-dihydroindol-1-yl]-2-thiophen-2-ylethanone Chemical compound C([C@@H](N=C1N)C=2C=CC=CC=2)N1S(=O)(=O)C(C=C1CC2)=CC=C1N2C(=O)CC1=CC=CS1 GAKUPVRBLIDIEY-HXUWFJFHSA-N 0.000 claims 1
- OBBGBOGVKOACEJ-GOSISDBHSA-N 1-[5-[[(4s)-2-amino-4-phenyl-4,5-dihydroimidazol-1-yl]sulfonyl]-2,3-dihydroindol-1-yl]butan-1-one Chemical compound C1([C@H]2CN(C(=N2)N)S(=O)(=O)C=2C=C3CCN(C3=CC=2)C(=O)CCC)=CC=CC=C1 OBBGBOGVKOACEJ-GOSISDBHSA-N 0.000 claims 1
- MJPNZGVFSLTIQK-QGZVFWFLSA-N 1-[5-[[(4s)-2-amino-4-phenyl-4,5-dihydroimidazol-1-yl]sulfonyl]-2,3-dihydroindol-1-yl]ethanone Chemical compound C1([C@H]2CN(C(=N2)N)S(=O)(=O)C=2C=C3CCN(C3=CC=2)C(=O)C)=CC=CC=C1 MJPNZGVFSLTIQK-QGZVFWFLSA-N 0.000 claims 1
- XAWNYPYZHDREIC-QGZVFWFLSA-N 1-[5-[[(4s)-2-amino-4-phenyl-4,5-dihydroimidazol-1-yl]sulfonyl]-2,3-dihydroindol-1-yl]propan-1-one Chemical compound C1([C@H]2CN(C(=N2)N)S(=O)(=O)C=2C=C3CCN(C3=CC=2)C(=O)CC)=CC=CC=C1 XAWNYPYZHDREIC-QGZVFWFLSA-N 0.000 claims 1
- SFLKKYDVEBSIEL-GOSISDBHSA-N 1-[5-[[(4s)-2-amino-4-phenyl-4,5-dihydroimidazol-1-yl]sulfonyl]-3,4-dihydro-2h-quinolin-1-yl]butan-1-one Chemical compound C1([C@H]2CN(C(=N2)N)S(=O)(=O)C2=CC=CC3=C2CCCN3C(=O)CCC)=CC=CC=C1 SFLKKYDVEBSIEL-GOSISDBHSA-N 0.000 claims 1
- QIBNDGVFJTVQTB-UHFFFAOYSA-N 5-[(2-amino-4,5-dihydroimidazol-1-yl)sulfonyl]-n-(2-aminoethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C=1C=C2N(C(=O)NCCN)CCC2=CC=1S(=O)(=O)N1CCN=C1N QIBNDGVFJTVQTB-UHFFFAOYSA-N 0.000 claims 1
- BHIVMCNTTBOCJX-UHFFFAOYSA-N 5-[(2-amino-4,5-dihydroimidazol-1-yl)sulfonyl]-n-butyl-2,3-dihydroindole-1-carboxamide Chemical compound C=1C=C2N(C(=O)NCCCC)CCC2=CC=1S(=O)(=O)N1CCN=C1N BHIVMCNTTBOCJX-UHFFFAOYSA-N 0.000 claims 1
- FDKZNVHPOVPPRX-LJQANCHMSA-N 5-[[(4s)-2-amino-4-(2-chlorophenyl)-4,5-dihydroimidazol-1-yl]sulfonyl]-n-butyl-2,3-dihydroindole-1-carboxamide Chemical compound C1([C@H]2CN(C(=N2)N)S(=O)(=O)C=2C=C3CCN(C3=CC=2)C(=O)NCCCC)=CC=CC=C1Cl FDKZNVHPOVPPRX-LJQANCHMSA-N 0.000 claims 1
- BDKWGOPFDMUVRM-GOSISDBHSA-N 5-[[(4s)-2-amino-4-(2-chlorophenyl)-4,5-dihydroimidazol-1-yl]sulfonyl]-n-propyl-2,3-dihydroindole-1-carboxamide Chemical compound C1([C@H]2CN(C(=N2)N)S(=O)(=O)C=2C=C3CCN(C3=CC=2)C(=O)NCCC)=CC=CC=C1Cl BDKWGOPFDMUVRM-GOSISDBHSA-N 0.000 claims 1
- DJBHDYVFBCJJBY-HXUWFJFHSA-N 5-[[(4s)-2-amino-4-(2-methylphenyl)-4,5-dihydroimidazol-1-yl]sulfonyl]-n-(2,2-dimethylpropyl)-2,3-dihydroindole-1-carboxamide Chemical compound CC1=CC=CC=C1[C@@H]1N=C(N)N(S(=O)(=O)C=2C=C3CCN(C3=CC=2)C(=O)NCC(C)(C)C)C1 DJBHDYVFBCJJBY-HXUWFJFHSA-N 0.000 claims 1
- DGDYCCKRIMWCNM-OAQYLSRUSA-N 5-[[(4s)-2-amino-4-(2-methylphenyl)-4,5-dihydroimidazol-1-yl]sulfonyl]-n-(2-cyclopropylethyl)-2,3-dihydroindole-1-carboxamide Chemical compound CC1=CC=CC=C1[C@@H]1N=C(N)N(S(=O)(=O)C=2C=C3CCN(C3=CC=2)C(=O)NCCC2CC2)C1 DGDYCCKRIMWCNM-OAQYLSRUSA-N 0.000 claims 1
- QZMIQEMGFARKOV-HXUWFJFHSA-N 5-[[(4s)-2-amino-4-(2-methylphenyl)-4,5-dihydroimidazol-1-yl]sulfonyl]-n-(2-methylpropyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1([C@H]2CN(C(=N2)N)S(=O)(=O)C=2C=C3CCN(C3=CC=2)C(=O)NCC(C)C)=CC=CC=C1C QZMIQEMGFARKOV-HXUWFJFHSA-N 0.000 claims 1
- HNFBPJBALIVLIN-HXUWFJFHSA-N 5-[[(4s)-2-amino-4-(2-methylphenyl)-4,5-dihydroimidazol-1-yl]sulfonyl]-n-(cyclopropylmethyl)-2,3-dihydroindole-1-carboxamide Chemical compound CC1=CC=CC=C1[C@@H]1N=C(N)N(S(=O)(=O)C=2C=C3CCN(C3=CC=2)C(=O)NCC2CC2)C1 HNFBPJBALIVLIN-HXUWFJFHSA-N 0.000 claims 1
- PRJWWCIVNQMCRO-HXUWFJFHSA-N 5-[[(4s)-2-amino-4-(2-methylphenyl)-4,5-dihydroimidazol-1-yl]sulfonyl]-n-butyl-2,3-dihydroindole-1-carboxamide Chemical compound C1([C@H]2CN(C(=N2)N)S(=O)(=O)C=2C=C3CCN(C3=CC=2)C(=O)NCCCC)=CC=CC=C1C PRJWWCIVNQMCRO-HXUWFJFHSA-N 0.000 claims 1
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Classifications
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
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- C07C247/00—Compounds containing azido groups
- C07C247/02—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton
- C07C247/04—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being saturated
- C07C247/06—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being saturated and containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
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- C07—ORGANIC CHEMISTRY
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Transplantation (AREA)
- Rheumatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361810276P | 2013-04-10 | 2013-04-10 | |
| PLPL403491 | 2013-04-10 | ||
| US61/810,276 | 2013-04-10 | ||
| PL403491A PL231063B1 (pl) | 2013-04-10 | 2013-04-10 | Pochodne 1-(podstawionej sulfonylo)-2-aminoimidazoliny jako środki przeciwnowotworowe |
| PCT/IB2014/060200 WO2014167446A1 (en) | 2013-04-10 | 2014-03-27 | Derivatives of 1-(substituted sulfonyl)-2-aminoimidazoline as antitumor and antiproliferative agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2883014A1 true CA2883014A1 (en) | 2014-10-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2883014A Abandoned CA2883014A1 (en) | 2013-04-10 | 2014-03-27 | Derivatives of 1-(substituted sulfonyl)-2-aminoimidazoline as antitumor and antiproliferative agents |
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| Country | Link |
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| US (2) | US9095575B2 (enExample) |
| EP (1) | EP2875017A1 (enExample) |
| JP (1) | JP2015535239A (enExample) |
| CN (1) | CN104619697A (enExample) |
| AU (1) | AU2014252281A1 (enExample) |
| CA (1) | CA2883014A1 (enExample) |
| IN (1) | IN2015KN00569A (enExample) |
| PL (1) | PL231063B1 (enExample) |
| WO (1) | WO2014167446A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB201617630D0 (en) | 2016-10-18 | 2016-11-30 | Cellcentric Ltd | Pharmaceutical compounds |
| GB201806320D0 (en) | 2018-04-18 | 2018-05-30 | Cellcentric Ltd | Process |
| US12528792B2 (en) | 2019-10-15 | 2026-01-20 | TroBio Therapeutics Pty Ltd | Sulfonamide compounds and the use thereof in the treatment of cancer |
| CN116194448A (zh) | 2020-08-31 | 2023-05-30 | 视点医疗股份有限公司 | 用于治疗眼科疾病的化合物和制剂 |
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| CS97860B5 (enExample) * | 1959-09-04 | 1960-12-15 | ||
| US3538085A (en) | 1966-03-24 | 1970-11-03 | Geigy Chem Corp | 1-phenylsulfonyl-2-imino-imidazolidines and hexahydropyrimidines |
| CH470397A (de) | 1966-03-24 | 1969-03-31 | Geigy Ag J R | Verfahren zur Herstellung neuer Derivate des Sulfanilamids |
| AU6578090A (en) | 1989-11-06 | 1991-05-09 | Warner-Lambert Company | Acat inhibitors |
| CA2263353C (en) | 1996-08-22 | 2002-04-23 | Dong Wha Pharm. Ind. Co., Ltd. | Arylsulfonylimidazolone derivatives as an antitumor agent |
| US6184242B1 (en) | 1997-09-04 | 2001-02-06 | Syntex Usa (Llc) | 2-(substituted-phenyl)amino-imidazoline derivatives |
| US20040019092A1 (en) | 2001-11-14 | 2004-01-29 | Daniel Berney | Non-peptide somatostatin receptor ligands |
| SI1864976T1 (sl) * | 2005-03-31 | 2012-12-31 | Astellas Pharma Inc. | Propan-1,3-dionski derivat ali njegova sol |
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2014
- 2014-03-27 CN CN201480002363.7A patent/CN104619697A/zh active Pending
- 2014-03-27 IN IN569KON2015 patent/IN2015KN00569A/en unknown
- 2014-03-27 JP JP2015538627A patent/JP2015535239A/ja active Pending
- 2014-03-27 CA CA2883014A patent/CA2883014A1/en not_active Abandoned
- 2014-03-27 AU AU2014252281A patent/AU2014252281A1/en not_active Abandoned
- 2014-03-27 EP EP14719203.3A patent/EP2875017A1/en not_active Withdrawn
- 2014-03-27 WO PCT/IB2014/060200 patent/WO2014167446A1/en not_active Ceased
- 2014-04-09 US US14/249,226 patent/US9095575B2/en not_active Expired - Fee Related
- 2014-06-17 US US14/307,272 patent/US8981114B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PL231063B1 (pl) | 2019-01-31 |
| CN104619697A (zh) | 2015-05-13 |
| EP2875017A1 (en) | 2015-05-27 |
| IN2015KN00569A (enExample) | 2015-07-17 |
| WO2014167446A1 (en) | 2014-10-16 |
| US8981114B2 (en) | 2015-03-17 |
| US9095575B2 (en) | 2015-08-04 |
| JP2015535239A (ja) | 2015-12-10 |
| AU2014252281A1 (en) | 2015-04-02 |
| US20140309259A1 (en) | 2014-10-16 |
| PL403491A1 (pl) | 2014-10-13 |
| US20140309240A1 (en) | 2014-10-16 |
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| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20150224 |
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| FZDE | Discontinued |
Effective date: 20170510 |