NZ591394A - Anti-cancer drugs and uses relating thereto for metastatic malignant melanoma and other cancers - Google Patents
Anti-cancer drugs and uses relating thereto for metastatic malignant melanoma and other cancersInfo
- Publication number
- NZ591394A NZ591394A NZ591394A NZ59139409A NZ591394A NZ 591394 A NZ591394 A NZ 591394A NZ 591394 A NZ591394 A NZ 591394A NZ 59139409 A NZ59139409 A NZ 59139409A NZ 591394 A NZ591394 A NZ 591394A
- Authority
- NZ
- New Zealand
- Prior art keywords
- diazenyl
- dimethylamino
- carboxamide
- thiophene
- triazin
- Prior art date
Links
- 206010028980 Neoplasm Diseases 0.000 title abstract 3
- 239000002246 antineoplastic agent Substances 0.000 title abstract 2
- 206010027480 Metastatic malignant melanoma Diseases 0.000 title 1
- 229940041181 antineoplastic drug Drugs 0.000 title 1
- 208000021039 metastatic melanoma Diseases 0.000 title 1
- -1 COSH Chemical group 0.000 abstract 3
- BRKSHTFZKOTZGD-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)thiophene-2-carboxylic acid Chemical compound CN(C)N=NC=1C=CSC=1C(O)=O BRKSHTFZKOTZGD-UHFFFAOYSA-N 0.000 abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 2
- 201000011510 cancer Diseases 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical class CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 abstract 1
- XCNVKXHFBYRXOX-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)-4-methoxythiophene-2,5-dicarboxamide Chemical compound COC1=C(C(N)=O)SC(C(N)=O)=C1N=NN(C)C XCNVKXHFBYRXOX-UHFFFAOYSA-N 0.000 abstract 1
- BGWLAAMXLGLLOX-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)-5-nitrothiophene-2-carboxamide Chemical compound CN(C)N=NC=1C=C([N+]([O-])=O)SC=1C(N)=O BGWLAAMXLGLLOX-UHFFFAOYSA-N 0.000 abstract 1
- IHXVULHYZAGNOQ-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)-5-nitrothiophene-2-carboxylic acid Chemical compound CN(C)N=NC=1C=C([N+]([O-])=O)SC=1C(O)=O IHXVULHYZAGNOQ-UHFFFAOYSA-N 0.000 abstract 1
- JODOHQOKFYCSLT-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)-5-phenylthiophene-2-carboxamide Chemical compound S1C(C(N)=O)=C(N=NN(C)C)C=C1C1=CC=CC=C1 JODOHQOKFYCSLT-UHFFFAOYSA-N 0.000 abstract 1
- FFIINGQLYOWBQU-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)-5-phenylthiophene-2-carboxylic acid Chemical compound S1C(C(O)=O)=C(N=NN(C)C)C=C1C1=CC=CC=C1 FFIINGQLYOWBQU-UHFFFAOYSA-N 0.000 abstract 1
- SRONACWOWHDIFG-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)-n-(2-hydroxyethyl)thiophene-2-carboxamide Chemical compound CN(C)N=NC=1C=CSC=1C(=O)NCCO SRONACWOWHDIFG-UHFFFAOYSA-N 0.000 abstract 1
- AFBXRCSQERBLCD-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)-n-methylthiophene-2-carboxamide Chemical compound CNC(=O)C=1SC=CC=1N=NN(C)C AFBXRCSQERBLCD-UHFFFAOYSA-N 0.000 abstract 1
- JEKTZIPLXIBRFH-UHFFFAOYSA-N 3-(dimethylaminodiazenyl)thiophene-2-carboxamide Chemical compound CN(C)N=NC=1C=CSC=1C(N)=O JEKTZIPLXIBRFH-UHFFFAOYSA-N 0.000 abstract 1
- GBBZWFPJGBPQDG-UHFFFAOYSA-N 3-methyl-6-nitrothieno[2,3-d]triazin-4-one Chemical compound O=C1N(C)N=NC2=C1C=C([N+]([O-])=O)S2 GBBZWFPJGBPQDG-UHFFFAOYSA-N 0.000 abstract 1
- LBSBADCUEOPGFV-UHFFFAOYSA-N 3-methyl-6-phenylthieno[3,2-d]triazin-4-one Chemical compound S1C=2C(=O)N(C)N=NC=2C=C1C1=CC=CC=C1 LBSBADCUEOPGFV-UHFFFAOYSA-N 0.000 abstract 1
- MPZVKKVKDAMAKY-UHFFFAOYSA-N 3-methylthieno[2,3-d]triazin-4-one Chemical compound O=C1N(C)N=NC2=C1C=CS2 MPZVKKVKDAMAKY-UHFFFAOYSA-N 0.000 abstract 1
- LFITZROYUAUXCO-UHFFFAOYSA-N 4-(dimethylaminodiazenyl)thiophene-3-carboxamide Chemical compound CN(C)N=NC1=CSC=C1C(N)=O LFITZROYUAUXCO-UHFFFAOYSA-N 0.000 abstract 1
- JIXFBKMQZSOWLN-UHFFFAOYSA-N 4-bromo-3-(dimethylaminodiazenyl)thiophene-2-carboxamide Chemical compound CN(C)N=NC=1C(Br)=CSC=1C(N)=O JIXFBKMQZSOWLN-UHFFFAOYSA-N 0.000 abstract 1
- VNDSXZWEYBFGHD-UHFFFAOYSA-N 6-amino-3-methylthieno[2,3-d]triazin-4-one Chemical compound O=C1N(C)N=NC2=C1C=C(N)S2 VNDSXZWEYBFGHD-UHFFFAOYSA-N 0.000 abstract 1
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 abstract 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 abstract 1
- 229910006074 SO2NH2 Inorganic materials 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 230000010261 cell growth Effects 0.000 abstract 1
- 230000022534 cell killing Effects 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 229940127089 cytotoxic agent Drugs 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 abstract 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 abstract 1
- FRBXIGJRDSLZSX-UHFFFAOYSA-N n-(2-aminoethyl)-3-(dimethylaminodiazenyl)thiophene-2-carboxamide Chemical compound CN(C)N=NC=1C=CSC=1C(=O)NCCN FRBXIGJRDSLZSX-UHFFFAOYSA-N 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 229930192474 thiophene Natural products 0.000 abstract 1
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 abstract 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D333/40—Thiophene-2-carboxylic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN2230CH2008 | 2008-09-15 | ||
| PCT/IN2009/000504 WO2010029577A2 (en) | 2008-09-15 | 2009-09-14 | Anti-cancer drugs and uses relating thereto for metastatic malignant melanoma and other cancers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ591394A true NZ591394A (en) | 2013-03-28 |
Family
ID=41565903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ591394A NZ591394A (en) | 2008-09-15 | 2009-09-14 | Anti-cancer drugs and uses relating thereto for metastatic malignant melanoma and other cancers |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8258119B2 (https=) |
| EP (1) | EP2324006B1 (https=) |
| JP (1) | JP2012502900A (https=) |
| KR (1) | KR20110063537A (https=) |
| CN (1) | CN102149703B (https=) |
| AU (1) | AU2009290365B2 (https=) |
| BR (1) | BRPI0913485A2 (https=) |
| CA (1) | CA2736732A1 (https=) |
| IL (1) | IL211366A0 (https=) |
| NZ (1) | NZ591394A (https=) |
| WO (1) | WO2010029577A2 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2424351B1 (en) * | 2009-04-27 | 2015-10-21 | Kasina Laila Innova Pharmaceuticals Private Ltd. | Anti-cancer drugs, and uses relating for malignant melanoma and other cancers |
| NO2686520T3 (https=) | 2011-06-06 | 2018-03-17 | ||
| WO2012170439A1 (en) * | 2011-06-06 | 2012-12-13 | The Ohio State University | Methods for stabilizing hypoxia inducible factor-2 alpha as a method for treating cancer |
| JP2016521747A (ja) | 2013-06-13 | 2016-07-25 | アケビア セラピューティクス インコーポレイテッドＡｋｅｂｉａ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｉｎｃ． | 貧血治療のための組成物及び方法 |
| US9593095B2 (en) | 2013-06-14 | 2017-03-14 | Duke University | Methods for the treatment of bacterial infections |
| DE112014006766T5 (de) * | 2014-06-27 | 2017-04-27 | Ecole Polytechnique Federale De Lausanne (Epfl) Epfl-Tto | Herstellung und medizinische Verwendung von Triazenen |
| US10150734B2 (en) | 2015-01-23 | 2018-12-11 | Akebia Therapeutics, Inc. | Solid forms of 2-(5-(3-fluorophenyl)-3-hydroxypicolinamido)acetic acid, compositions, and uses thereof |
| US11324734B2 (en) | 2015-04-01 | 2022-05-10 | Akebia Therapeutics, Inc. | Compositions and methods for treating anemia |
| AU2016265922B2 (en) | 2015-05-18 | 2021-05-20 | Syn-Nat Products Enterprise LLC | A pharmaceutical co-crystal and use thereof |
| BR112017027277A2 (pt) * | 2015-06-19 | 2018-09-04 | Syn Nat Products Entpr Llc | ?método para o tratamento ou prevenção de uma doença e métodos para matar uma célula? |
| BR112017027285A2 (pt) | 2015-06-19 | 2018-09-11 | Syn Nat Products Entpr Llc | ?cocristal, composição farmacêutica e método para o tratamento de uma doença? |
| US10428099B2 (en) | 2015-06-25 | 2019-10-01 | Syn-Nat Products Enterprise LLC | Pharmaceutical co-crystal composition and use thereof |
| US11713298B2 (en) | 2018-05-09 | 2023-08-01 | Akebia Therapeutics, Inc. | Process for preparing 2-[[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino]acetic acid |
| WO2021117767A1 (ja) | 2019-12-10 | 2021-06-17 | 田辺三菱製薬株式会社 | 含窒素ヘテロアリールカルボキサミド酢酸誘導体の製造方法 |
| KR102648781B1 (ko) | 2021-11-09 | 2024-03-19 | 국립공주대학교 산학협력단 | 항암 활성을 갖는 인데노피라졸론 유도체 화합물, 그의 제조방법 및 그의 용도 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1020641B (de) | 1955-10-15 | 1957-12-12 | Basf Ag | Verfahren zur Herstellung von Derivaten der 3-Oxythiophen-2-carbonsaeure |
| CA968347A (en) * | 1968-09-09 | 1975-05-27 | John F. Gerster | Substituted pyrazoles and process |
-
2009
- 2009-09-14 KR KR1020117008490A patent/KR20110063537A/ko not_active Ceased
- 2009-09-14 JP JP2011526634A patent/JP2012502900A/ja active Pending
- 2009-09-14 NZ NZ591394A patent/NZ591394A/xx not_active IP Right Cessation
- 2009-09-14 CN CN200980135652.3A patent/CN102149703B/zh not_active Expired - Fee Related
- 2009-09-14 BR BRPI0913485A patent/BRPI0913485A2/pt not_active IP Right Cessation
- 2009-09-14 AU AU2009290365A patent/AU2009290365B2/en not_active Ceased
- 2009-09-14 EP EP09760623.0A patent/EP2324006B1/en not_active Not-in-force
- 2009-09-14 WO PCT/IN2009/000504 patent/WO2010029577A2/en not_active Ceased
- 2009-09-14 CA CA2736732A patent/CA2736732A1/en not_active Abandoned
- 2009-09-15 US US12/559,811 patent/US8258119B2/en not_active Expired - Fee Related
-
2011
- 2011-02-23 IL IL211366A patent/IL211366A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN102149703A (zh) | 2011-08-10 |
| US20100068178A1 (en) | 2010-03-18 |
| EP2324006A2 (en) | 2011-05-25 |
| WO2010029577A3 (en) | 2010-05-06 |
| AU2009290365A1 (en) | 2010-03-18 |
| WO2010029577A2 (en) | 2010-03-18 |
| JP2012502900A (ja) | 2012-02-02 |
| BRPI0913485A2 (pt) | 2016-06-07 |
| KR20110063537A (ko) | 2011-06-10 |
| US8258119B2 (en) | 2012-09-04 |
| EP2324006B1 (en) | 2014-08-13 |
| IL211366A0 (en) | 2011-04-28 |
| CN102149703B (zh) | 2014-09-10 |
| CA2736732A1 (en) | 2010-03-18 |
| AU2009290365B2 (en) | 2014-08-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 3 YEARS UNTIL 14 SEP 2016 BY BALDWINS INTELLECTUAL PROPERTY Effective date: 20130930 |
|
| LAPS | Patent lapsed |