CA2506238C - Composes derives de chroman et leurs formulations pour utilisation a des fins therapeutiques - Google Patents

Composes derives de chroman et leurs formulations pour utilisation a des fins therapeutiques Download PDF

Info

Publication number: CA2506238C
Authority: CA; Canada
Prior art keywords: hydrogen; compound; alkyl; hmc; compounds
Prior art date: 2004-09-21
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.): Expired - Fee Related

Application number

CA 2506238

Other languages

English (en)

Other versions

CA2506238A1 (fr

Inventor

Andrew Heaton

Alan Husband

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mei Pharma Inc

Original Assignee

Mei Pharma 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.)

2004-09-21

Filing date

2005-05-03

Publication date

2014-04-01

2004-10-29 Priority claimed from JP2004315009A external-priority patent/JP4976649B2/ja

2004-11-05 Priority claimed from AU2004906363A external-priority patent/AU2004906363A0/en

2005-05-03 Application filed by Mei Pharma Inc filed Critical Mei Pharma Inc

2006-03-21 Publication of CA2506238A1 publication Critical patent/CA2506238A1/fr

2014-04-01 Application granted granted Critical

2014-04-01 Publication of CA2506238C publication Critical patent/CA2506238C/fr

2025-05-03 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 216
239000000203 mixture Substances 0.000 title abstract description 53
238000002560 therapeutic procedure Methods 0.000 title abstract description 9
238000009472 formulation Methods 0.000 title description 21
VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 title description 2
239000001257 hydrogen Substances 0.000 claims abstract description 101
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 101
206010028980 Neoplasm Diseases 0.000 claims abstract description 89
125000000217 alkyl group Chemical group 0.000 claims abstract description 48
201000011510 cancer Diseases 0.000 claims abstract description 42
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 37
238000011282 treatment Methods 0.000 claims abstract description 35
150000003839 salts Chemical class 0.000 claims abstract description 30
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 28
125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
238000000034 method Methods 0.000 claims abstract description 20
125000003118 aryl group Chemical group 0.000 claims abstract description 15
230000008569 process Effects 0.000 claims abstract description 11
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims abstract description 5
125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 13
125000001475 halogen functional group Chemical group 0.000 claims abstract 6
ZZUBHVMHNVYXRR-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-2h-chromen-7-ol Chemical compound C1=CC(O)=CC=C1C1=CC2=CC=C(O)C=C2OC1 ZZUBHVMHNVYXRR-UHFFFAOYSA-N 0.000 claims description 92
201000001441 melanoma Diseases 0.000 claims description 45
239000003814 drug Substances 0.000 claims description 28
239000003795 chemical substances by application Substances 0.000 claims description 25
229960004316 cisplatin Drugs 0.000 claims description 25
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 22
LLVWVIIOKIWERJ-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-7-ol Chemical compound C1CCOC2=CC(O)=CC=C21 LLVWVIIOKIWERJ-UHFFFAOYSA-N 0.000 claims description 16
229960001592 paclitaxel Drugs 0.000 claims description 16
229930012538 Paclitaxel Natural products 0.000 claims description 15
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 15
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 7
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125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
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ALZDHGLVGZETNR-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-4-(3-methoxyphenyl)-3,4-dihydro-2h-chromen-7-ol Chemical compound COC1=CC=CC(C2C3=CC=C(O)C=C3OCC2C=2C=CC(O)=CC=2)=C1 ALZDHGLVGZETNR-UHFFFAOYSA-N 0.000 claims 2
KQCJZAUNKSGEFM-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-4-(4-methoxyphenyl)-3,4-dihydro-2h-chromen-7-ol Chemical compound C1=CC(OC)=CC=C1C1C2=CC=C(O)C=C2OCC1C1=CC=C(O)C=C1 KQCJZAUNKSGEFM-UHFFFAOYSA-N 0.000 claims 2
VXHSDGZMRLGSEJ-UHFFFAOYSA-N 3,4-bis(4-hydroxyphenyl)-3,4-dihydro-2h-chromen-7-ol Chemical compound C1=CC(O)=CC=C1C1C(C=2C=CC(O)=CC=2)C2=CC=C(O)C=C2OC1 VXHSDGZMRLGSEJ-UHFFFAOYSA-N 0.000 claims 1
SXMHBZFCCRGHQA-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-4-(4-methoxyphenyl)-3,4-dihydro-2h-chromen-7-ol Chemical compound C1=CC(OC)=CC=C1C1C2=CC=C(O)C=C2OCC1C1=CC=C(OC)C(OC)=C1 SXMHBZFCCRGHQA-UHFFFAOYSA-N 0.000 claims 1
RQXXIQGPZCPNBN-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-4-(3-methoxyphenyl)-3,4-dihydro-2h-chromen-7-ol Chemical compound COC1=CC=CC(C2C3=CC=C(O)C=C3OCC2C=2C=C(O)C=CC=2)=C1 RQXXIQGPZCPNBN-UHFFFAOYSA-N 0.000 claims 1
FPBSRNSXKZBHRK-UHFFFAOYSA-N 3-(4-bromophenyl)-4-(4-methoxyphenyl)-3,4-dihydro-2h-chromen-7-ol Chemical compound C1=CC(OC)=CC=C1C1C2=CC=C(O)C=C2OCC1C1=CC=C(Br)C=C1 FPBSRNSXKZBHRK-UHFFFAOYSA-N 0.000 claims 1
NALARBCJDJUJAW-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-4-(4-methylphenyl)-3,4-dihydro-2h-chromen-7-ol Chemical compound C1=CC(C)=CC=C1C1C2=CC=C(O)C=C2OCC1C1=CC=C(O)C=C1 NALARBCJDJUJAW-UHFFFAOYSA-N 0.000 claims 1
RYXXGDBORUOCLC-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-4-(4-phenoxyphenyl)-3,4-dihydro-2h-chromen-7-ol Chemical compound C1=CC(O)=CC=C1C1C(C=2C=CC(OC=3C=CC=CC=3)=CC=2)C2=CC=C(O)C=C2OC1 RYXXGDBORUOCLC-UHFFFAOYSA-N 0.000 claims 1
FDMOAYIDJXKXDX-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-4-phenyl-3,4-dihydro-2h-chromen-7-ol Chemical compound C1=CC(O)=CC=C1C1C(C=2C=CC=CC=2)C2=CC=C(O)C=C2OC1 FDMOAYIDJXKXDX-UHFFFAOYSA-N 0.000 claims 1
IKCGZGMUGBLRNA-UHFFFAOYSA-N 4-(2-hydroxyphenyl)-3-(4-hydroxyphenyl)-3,4-dihydro-2h-chromen-7-ol Chemical compound C1=CC(O)=CC=C1C1C(C=2C(=CC=CC=2)O)C2=CC=C(O)C=C2OC1 IKCGZGMUGBLRNA-UHFFFAOYSA-N 0.000 claims 1
NYPDDQKXFGEDBJ-UHFFFAOYSA-N 4-(3-aminophenyl)-3-(4-hydroxyphenyl)-3,4-dihydro-2h-chromen-7-ol Chemical compound NC1=CC=CC(C2C3=CC=C(O)C=C3OCC2C=2C=CC(O)=CC=2)=C1 NYPDDQKXFGEDBJ-UHFFFAOYSA-N 0.000 claims 1
RPBNDQQITRYOCU-UHFFFAOYSA-N 4-(4-hydroxy-2,6-dimethoxyphenyl)-3-(4-hydroxyphenyl)-3,4-dihydro-2h-chromen-7-ol Chemical compound COC1=CC(O)=CC(OC)=C1C1C2=CC=C(O)C=C2OCC1C1=CC=C(O)C=C1 RPBNDQQITRYOCU-UHFFFAOYSA-N 0.000 claims 1
125000002252 acyl group Chemical group 0.000 abstract description 8
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150000002431 hydrogen Chemical group 0.000 description 43
230000000694 effects Effects 0.000 description 29
125000002887 hydroxy group Chemical group [H]O* 0.000 description 29
-1 hydroxy, methoxy, ethoxy, propoxy, isopropoxy Chemical group 0.000 description 26
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230000001988 toxicity Effects 0.000 description 24
231100000419 toxicity Toxicity 0.000 description 24
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
230000006907 apoptotic process Effects 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
229920000858 Cyclodextrin Polymers 0.000 description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 20
238000004458 analytical method Methods 0.000 description 19
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
238000007912 intraperitoneal administration Methods 0.000 description 16
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PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
208000016261 weight loss Diseases 0.000 description 1
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Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA 2506238 2004-09-21 2005-05-03 Composes derives de chroman et leurs formulations pour utilisation a des fins therapeutiques Expired - Fee Related CA2506238C (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US61129904P	2004-09-21	2004-09-21
US60/611,299		2004-09-21
JP2004315009A JP4976649B2 (ja)	2004-09-21	2004-10-29	化合物
JP2004-315009		2004-10-29
AU2004/906,363		2004-11-05
AU2004906363A AU2004906363A0 (en)		2004-11-05	Compounds

Publications (2)

Publication Number	Publication Date
CA2506238A1 CA2506238A1 (fr)	2006-03-21
CA2506238C true CA2506238C (fr)	2014-04-01

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ID=36096935

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2506238 Expired - Fee Related CA2506238C (fr)	2004-09-21	2005-05-03	Composes derives de chroman et leurs formulations pour utilisation a des fins therapeutiques

Country Status (1)

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CA (1)	CA2506238C (fr)

2005
- 2005-05-03 CA CA 2506238 patent/CA2506238C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2506238A1 (fr)	2006-03-21

Publication	Publication Date	Title
US8461361B2 (en)	2013-06-11	Chroman derivatives, medicaments and use in therapy
US9381186B2 (en)	2016-07-05	Substituted chroman derivatives, medicaments and use in therapy
JP5816868B2 (ja)	2015-11-18	化合物
EP1809618B1 (fr)	2013-07-17	Dérivés de chromane, médicaments et utilisation à des fins thérapeutiques
CA2506238C (fr)	2014-04-01	Composes derives de chroman et leurs formulations pour utilisation a des fins therapeutiques
AU2005201855B2 (en)	2012-03-29	Chroman derived compounds and formulations thereof for use in therapy
JP4913056B2 (ja)	2012-04-11	置換クロマン誘導体、医薬品、および治療における使用
ES2431045T3 (es)	2013-11-22	Derivados de cromano, medicamentos y uso terapéutico
IL182042A (en)	2012-03-29	Chroman derivatives, medicaments and use in therapy
HK1112617B (en)	2013-04-26	Chroman derivatives, medicaments and use in therapy
HK1108685A1 (en)	2008-05-16	Substituted chroman derivatives, medicaments and use in therapy
HK1108685B (en)	2013-02-08	Substituted chroman derivatives, medicaments and use in therapy

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Date	Code	Title	Description
2010-02-03	EEER	Examination request
2018-06-14	MKLA	Lapsed	Effective date: 20180503