AU2014252281A1 - 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
- AU2014252281A1 AU2014252281A1 AU2014252281A AU2014252281A AU2014252281A1 AU 2014252281 A1 AU2014252281 A1 AU 2014252281A1 AU 2014252281 A AU2014252281 A AU 2014252281A AU 2014252281 A AU2014252281 A AU 2014252281A AU 2014252281 A1 AU2014252281 A1 AU 2014252281A1
- Authority
- AU
- Australia
- 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
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- -1 1-(substituted sulfonyl)-2-aminoimidazoline Chemical class 0.000 title claims description 63
- 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 85
- 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
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000000651 prodrug Substances 0.000 claims description 20
- 229940002612 prodrug Drugs 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 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
- 229910052717 sulfur Chemical group 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000011593 sulfur Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Chemical group 0.000 claims description 7
- 239000012453 solvate 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 241000124008 Mammalia Species 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
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
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- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
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- 230000003211 malignant effect Effects 0.000 claims description 2
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- 201000005962 mycosis fungoides Diseases 0.000 claims description 2
- 210000003739 neck Anatomy 0.000 claims description 2
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- 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
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- DEPDDPLQZYCHOH-UHFFFAOYSA-N 1h-imidazol-2-amine Chemical compound NC1=NC=CN1 DEPDDPLQZYCHOH-UHFFFAOYSA-N 0.000 claims 10
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 230000003463 hyperproliferative effect Effects 0.000 claims 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 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 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
- 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
- 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
- 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
- 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
- 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
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 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
- 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
- GXYHEMLILDXGMN-GOSISDBHSA-N 5-[[(4s)-2-amino-4-(4-fluorophenyl)-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=C(F)C=C1 GXYHEMLILDXGMN-GOSISDBHSA-N 0.000 claims 1
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- CQJFCNQWIMTADR-LJQANCHMSA-N 5-[[(4s)-2-amino-4-phenyl-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=C1 CQJFCNQWIMTADR-LJQANCHMSA-N 0.000 claims 1
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Classifications
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Oncology (AREA)
- Rheumatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (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 |
|---|---|
| AU2014252281A1 true AU2014252281A1 (en) | 2015-04-02 |
Family
ID=51662842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2014252281A Abandoned AU2014252281A1 (en) | 2013-04-10 | 2014-03-27 | Derivatives of 1-(substituted sulfonyl)-2-aminoimidazoline as antitumor and antiproliferative agents |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US9095575B2 (https=) |
| EP (1) | EP2875017A1 (https=) |
| JP (1) | JP2015535239A (https=) |
| CN (1) | CN104619697A (https=) |
| AU (1) | AU2014252281A1 (https=) |
| CA (1) | CA2883014A1 (https=) |
| IN (1) | IN2015KN00569A (https=) |
| PL (1) | PL231063B1 (https=) |
| WO (1) | WO2014167446A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201617630D0 (en) | 2016-10-18 | 2016-11-30 | Cellcentric Ltd | Pharmaceutical compounds |
| GB201806320D0 (en) | 2018-04-18 | 2018-05-30 | Cellcentric Ltd | Process |
| WO2021072487A1 (en) | 2019-10-15 | 2021-04-22 | TroBio Therapeutics Pty Ltd | Sulfonamide compounds and the use thereof in the treatment of cancer |
| AU2021331624A1 (en) * | 2020-08-31 | 2023-05-04 | Visus Therapeutics, Inc. | Compounds and formulations for treating ophthalmic diseases |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS97860B5 (https=) * | 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 |
| CN1079096C (zh) | 1996-08-22 | 2002-02-13 | 同和药品工业株式会社 | 用作抗肿瘤剂的芳磺酰基咪唑啉酮衍生物 |
| US6184242B1 (en) | 1997-09-04 | 2001-02-06 | Syntex Usa (Llc) | 2-(substituted-phenyl)amino-imidazoline derivatives |
| AU2002363655A1 (en) | 2001-11-14 | 2003-05-26 | Novartis Ag | Non-peptide somatostatin receptor ligands |
| SI1864976T1 (sl) * | 2005-03-31 | 2012-12-31 | Astellas Pharma Inc. | Propan-1,3-dionski derivat ali njegova sol |
-
2013
- 2013-04-10 PL PL403491A patent/PL231063B1/pl unknown
-
2014
- 2014-03-27 WO PCT/IB2014/060200 patent/WO2014167446A1/en not_active Ceased
- 2014-03-27 AU AU2014252281A patent/AU2014252281A1/en not_active Abandoned
- 2014-03-27 CA CA2883014A patent/CA2883014A1/en not_active Abandoned
- 2014-03-27 JP JP2015538627A patent/JP2015535239A/ja active Pending
- 2014-03-27 CN CN201480002363.7A patent/CN104619697A/zh active Pending
- 2014-03-27 IN IN569KON2015 patent/IN2015KN00569A/en unknown
- 2014-03-27 EP EP14719203.3A patent/EP2875017A1/en not_active Withdrawn
- 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 |
|---|---|
| IN2015KN00569A (https=) | 2015-07-17 |
| JP2015535239A (ja) | 2015-12-10 |
| PL231063B1 (pl) | 2019-01-31 |
| WO2014167446A1 (en) | 2014-10-16 |
| US8981114B2 (en) | 2015-03-17 |
| CN104619697A (zh) | 2015-05-13 |
| EP2875017A1 (en) | 2015-05-27 |
| US9095575B2 (en) | 2015-08-04 |
| PL403491A1 (pl) | 2014-10-13 |
| US20140309240A1 (en) | 2014-10-16 |
| CA2883014A1 (en) | 2014-10-16 |
| US20140309259A1 (en) | 2014-10-16 |
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