MXPA02010325A - Derivados de oxadiazol los cuales tienen efectos anticancer. - Google Patents
Derivados de oxadiazol los cuales tienen efectos anticancer.Info
- Publication number
- MXPA02010325A MXPA02010325A MXPA02010325A MXPA02010325A MXPA02010325A MX PA02010325 A MXPA02010325 A MX PA02010325A MX PA02010325 A MXPA02010325 A MX PA02010325A MX PA02010325 A MXPA02010325 A MX PA02010325A MX PA02010325 A MXPA02010325 A MX PA02010325A
- Authority
- MX
- Mexico
- Prior art keywords
- optionally substituted
- compound
- lower alkyl
- hydrogen
- pharmaceutically acceptable
- Prior art date
Links
- 230000001093 anti-cancer Effects 0.000 title description 2
- 150000004866 oxadiazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 229940002612 prodrug Drugs 0.000 claims abstract description 19
- 239000000651 prodrug Substances 0.000 claims abstract description 19
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000012453 solvate Substances 0.000 claims abstract description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 239000004480 active ingredient Substances 0.000 claims abstract description 7
- 125000000732 arylene group Chemical group 0.000 claims abstract description 7
- 230000002265 prevention Effects 0.000 claims abstract 2
- -1 2,5-thiophene-diyl Chemical group 0.000 claims description 113
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 201000011510 cancer Diseases 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 206010027476 Metastases Diseases 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 230000009401 metastasis Effects 0.000 claims description 4
- 125000006302 indol-3-yl methyl group Chemical group [H]N1C([H])=C(C2=C([H])C([H])=C([H])C([H])=C12)C([H])([H])* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 37
- 239000011541 reaction mixture Substances 0.000 description 27
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- 238000000034 method Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
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- 108010000684 Matrix Metalloproteinases Proteins 0.000 description 13
- 229910052736 halogen Inorganic materials 0.000 description 12
- 150000002367 halogens Chemical class 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
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- 238000004458 analytical method Methods 0.000 description 11
- 239000012267 brine Substances 0.000 description 11
- 230000002401 inhibitory effect Effects 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- 238000002425 crystallisation Methods 0.000 description 10
- 230000008025 crystallization Effects 0.000 description 10
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
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- 210000004027 cell Anatomy 0.000 description 8
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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- 239000008101 lactose Substances 0.000 description 7
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 description 6
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical class C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
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- 229920002261 Corn starch Polymers 0.000 description 5
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- 102100030412 Matrix metalloproteinase-9 Human genes 0.000 description 5
- 125000004423 acyloxy group Chemical group 0.000 description 5
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 229920003114 HPC-L Polymers 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
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- 125000002252 acyl group Chemical group 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- 238000012360 testing method Methods 0.000 description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4245—Oxadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000120234 | 2000-04-21 | ||
| PCT/JP2001/003214 WO2001083463A1 (en) | 2000-04-21 | 2001-04-16 | Oxadiazole derivatives having anticancer effects |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA02010325A true MXPA02010325A (es) | 2003-04-25 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA02010325A MXPA02010325A (es) | 2000-04-21 | 2001-04-16 | Derivados de oxadiazol los cuales tienen efectos anticancer. |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US6720343B2 (enExample) |
| EP (1) | EP1277744A4 (enExample) |
| JP (1) | JP3974781B2 (enExample) |
| KR (1) | KR100542780B1 (enExample) |
| CN (1) | CN1199956C (enExample) |
| AU (2) | AU2001246916B2 (enExample) |
| BR (1) | BR0110211A (enExample) |
| CA (1) | CA2406685C (enExample) |
| HU (1) | HUP0300619A3 (enExample) |
| MX (1) | MXPA02010325A (enExample) |
| NO (1) | NO324868B1 (enExample) |
| PL (1) | PL203161B1 (enExample) |
| RU (1) | RU2275371C2 (enExample) |
| TW (1) | TWI294877B (enExample) |
| WO (1) | WO2001083463A1 (enExample) |
| ZA (1) | ZA200208307B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030105144A1 (en) | 2001-04-17 | 2003-06-05 | Ping Gao | Stabilized oral pharmaceutical composition |
| US7825146B2 (en) | 2003-07-30 | 2010-11-02 | Shionogi & Co., Ltd. | Sulfonamide derivative having isoxazole ring |
| WO2006047195A2 (en) * | 2004-10-22 | 2006-05-04 | Merck & Co., Inc. | 2-(aryl)azacyclylmethyl carboxylates, sulfonates, phosphonates, phosphinates and heterocycles as s1p receptor agonists |
| US7576222B2 (en) | 2004-12-28 | 2009-08-18 | Wyeth | Alkynyl-containing tryptophan derivative inhibitors of TACE/matrix metalloproteinase |
| GB0601744D0 (en) * | 2006-01-27 | 2006-03-08 | Novartis Ag | Organic compounds |
| KR20090007792A (ko) * | 2006-05-09 | 2009-01-20 | 화이자 프로덕츠 인크. | 시클로알킬아미노산 유도체 및 이들의 제약 조성물 |
| KR100783585B1 (ko) | 2006-08-22 | 2007-12-07 | 한국생명공학연구원 | 스탯의 활성을 저해하는 옥사다이아졸 우레아 화합물을 유효성분으로 함유하는 암의 예방 또는 치료제 |
| ES2748599T3 (es) | 2007-08-27 | 2020-03-17 | Dart Neuroscience Cayman Ltd | Compuestos terapéuticos de isoxazol |
| BRPI0820868A2 (pt) * | 2007-12-10 | 2019-09-24 | Actelion Pharmaceuticals Ltd | composto de tiofeno fórmula(i), composição farmacêutica contendo o mesmo e uso deste para a prevenção ou tratamento de doenças ou disturbíos associados a um sistema imune ativado |
| AR077969A1 (es) | 2009-08-31 | 2011-10-05 | Abbott Healthcare Products Bv | Derivados de (tio)morfolina comomoduladores de s1p |
| RU2415845C1 (ru) * | 2009-10-14 | 2011-04-10 | Государственное образовательное учреждение высшего профессионального образования "Астраханский государственный университет" (АГУ) | Сульфонные производные 2-нитро-2-(3-арил-1,2,4-оксадиазол-5-ил)этана, обладающие противолепрозной и противотуберкулезной активностью |
| TW201206893A (en) | 2010-07-09 | 2012-02-16 | Abbott Healthcare Products Bv | Bisaryl (thio) morpholine derivatives as S1P modulators |
| TW201643169A (zh) | 2010-07-09 | 2016-12-16 | 艾伯維股份有限公司 | 作為s1p調節劑的螺-哌啶衍生物 |
| TWI522361B (zh) | 2010-07-09 | 2016-02-21 | 艾伯維公司 | 作為s1p調節劑的稠合雜環衍生物 |
| CN103450167A (zh) * | 2012-05-28 | 2013-12-18 | 南京大学 | 一类含1,3,4-噁二唑和吡嗪环的酰腙类衍生物及其制备方法与用途 |
| US10710994B2 (en) * | 2018-03-19 | 2020-07-14 | Genentech, Inc. | Oxadiazole transient receptor potential channel inhibitors |
| JP2022553802A (ja) | 2019-10-31 | 2022-12-26 | エスケープ・バイオ・インコーポレイテッド | Ｓ１ｐ受容体モジュレーターの固体形態 |
| CN113264899B (zh) * | 2021-04-09 | 2022-06-14 | 台州学院 | 一种1，3，5-噁二嗪类化合物及其制备和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0003851A3 (en) | 1997-07-22 | 2002-10-28 | Shionogi & Co | Pharmaceutical composition for the treatment or prevention of glomerulopathy |
| AU5647099A (en) * | 1998-09-11 | 2000-04-03 | Shionogi & Co., Ltd. | Remedal or preventive agent for congestive heart failure |
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- 2001-04-16 MX MXPA02010325A patent/MXPA02010325A/es active IP Right Grant
- 2001-04-16 EP EP01919938A patent/EP1277744A4/en not_active Withdrawn
- 2001-04-16 BR BR0110211-7A patent/BR0110211A/pt not_active IP Right Cessation
- 2001-04-16 KR KR1020027013969A patent/KR100542780B1/ko not_active Expired - Fee Related
- 2001-04-16 CN CNB018112404A patent/CN1199956C/zh not_active Expired - Fee Related
- 2001-04-16 RU RU2002130247/04A patent/RU2275371C2/ru not_active IP Right Cessation
- 2001-04-16 US US10/257,917 patent/US6720343B2/en not_active Expired - Fee Related
- 2001-04-16 WO PCT/JP2001/003214 patent/WO2001083463A1/ja not_active Ceased
- 2001-04-16 HU HU0300619A patent/HUP0300619A3/hu unknown
- 2001-04-16 AU AU2001246916A patent/AU2001246916B2/en not_active Ceased
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- 2001-04-16 JP JP2001580892A patent/JP3974781B2/ja not_active Expired - Fee Related
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| US20030203940A1 (en) | 2003-10-30 |
| CN1199956C (zh) | 2005-05-04 |
| AU2001246916B2 (en) | 2004-10-07 |
| RU2275371C2 (ru) | 2006-04-27 |
| US6720343B2 (en) | 2004-04-13 |
| TWI294877B (enExample) | 2008-03-21 |
| KR20030019357A (ko) | 2003-03-06 |
| CA2406685C (en) | 2006-10-31 |
| WO2001083463A1 (en) | 2001-11-08 |
| PL359415A1 (en) | 2004-08-23 |
| EP1277744A1 (en) | 2003-01-22 |
| CN1436179A (zh) | 2003-08-13 |
| NO20025035L (no) | 2002-12-19 |
| PL203161B1 (pl) | 2009-08-31 |
| KR100542780B1 (ko) | 2006-01-11 |
| BR0110211A (pt) | 2003-06-03 |
| HUP0300619A2 (hu) | 2003-07-28 |
| NO20025035D0 (no) | 2002-10-18 |
| US20040122066A1 (en) | 2004-06-24 |
| AU4691601A (en) | 2001-11-12 |
| EP1277744A4 (en) | 2007-07-11 |
| JP3974781B2 (ja) | 2007-09-12 |
| CA2406685A1 (en) | 2002-10-17 |
| HUP0300619A3 (en) | 2006-02-28 |
| NO324868B1 (no) | 2007-12-17 |
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