JP2000501100A - ２―チオキソ―イミダゾリジン―４―オン誘導体およびｈｄｌコレステロール濃度を上昇させるためのそれらの使用 - Google Patents

２―チオキソ―イミダゾリジン―４―オン誘導体およびｈｄｌコレステロール濃度を上昇させるためのそれらの使用

Info

Publication number: JP2000501100A
Authority: JP; Japan
Prior art keywords: thioxo; ethyl; alkyl; carbons; imidazolidin
Prior art date: 1995-11-28
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.): Pending

Application number

JP9520724A

Other languages

English (en)

Japanese (ja)

Inventor

エロクダー，ハッサン・マーモウド

チャイ，シー―ヤール

スルコウスキー，セオドア・シルベスター

ストライク，ドナルド・ピーター

Original Assignee

アメリカン・ホーム・プロダクツ・コーポレイション

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.)

1995-11-28

Filing date

1996-11-25

Publication date

2000-02-02

1995-11-28 Priority claimed from US08/563,325 external-priority patent/US5554607A/en

1996-11-25 Application filed by アメリカン・ホーム・プロダクツ・コーポレイション filed Critical アメリカン・ホーム・プロダクツ・コーポレイション

2000-02-02 Publication of JP2000501100A publication Critical patent/JP2000501100A/ja

Status Pending legal-status Critical Current

Links

HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 title claims abstract description 56
UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical class O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 title description 11
150000001875 compounds Chemical class 0.000 claims abstract description 189
125000000217 alkyl group Chemical group 0.000 claims abstract description 83
238000000034 method Methods 0.000 claims abstract description 59
125000003342 alkenyl group Chemical group 0.000 claims abstract description 23
125000000304 alkynyl group Chemical group 0.000 claims abstract description 18
125000001424 substituent group Chemical group 0.000 claims abstract description 18
125000003118 aryl group Chemical group 0.000 claims abstract description 16
125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
241000124008 Mammalia Species 0.000 claims abstract description 10
229920001774 Perfluoroether Chemical group 0.000 claims abstract description 10
210000004369 blood Anatomy 0.000 claims abstract description 8
239000008280 blood Substances 0.000 claims abstract description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 7
229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims abstract description 5
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 3
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
-1 perfluoro Chemical group 0.000 claims description 101
125000004432 carbon atom Chemical group C* 0.000 claims description 42
229910052739 hydrogen Inorganic materials 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 33
238000010992 reflux Methods 0.000 claims description 22
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 17
150000002431 hydrogen Chemical class 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
235000012000 cholesterol Nutrition 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 12
125000003258 trimethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 11
238000011282 treatment Methods 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000000383 tetramethylene group Chemical class [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 7
239000003610 charcoal Substances 0.000 claims description 6
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
XZJRRJZOWDPGQM-UHFFFAOYSA-N 3-(2-chloro-6-methylphenyl)-1-ethyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=C(C)C=CC=C1Cl XZJRRJZOWDPGQM-UHFFFAOYSA-N 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
AKFPRRUTXZFADG-UHFFFAOYSA-N 1-butyl-3-(4-fluorophenyl)-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CCCC)CC(=O)N1C1=CC=C(F)C=C1 AKFPRRUTXZFADG-UHFFFAOYSA-N 0.000 claims description 4
XRMBERGIRQWHDP-UHFFFAOYSA-N 1-ethyl-3-(4-fluorophenyl)-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=CC=C(F)C=C1 XRMBERGIRQWHDP-UHFFFAOYSA-N 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
VRVHDAPELYNQEP-UHFFFAOYSA-N 3-(2,6-dimethylphenyl)-1-propan-2-yl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(C(C)C)CC(=O)N1C1=C(C)C=CC=C1C VRVHDAPELYNQEP-UHFFFAOYSA-N 0.000 claims description 4
125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
IQJZOQXJKAUESC-UHFFFAOYSA-N 1-ethyl-3-(2-ethylphenyl)-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=CC=CC=C1CC IQJZOQXJKAUESC-UHFFFAOYSA-N 0.000 claims description 3
RVNFWEHUVLBXEY-UHFFFAOYSA-N 1-ethyl-3-(2-methylphenyl)-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=CC=CC=C1C RVNFWEHUVLBXEY-UHFFFAOYSA-N 0.000 claims description 3
UXFMOSJANJUHKK-UHFFFAOYSA-N 1-ethyl-3-(2-methylpropyl)-2-sulfanylideneimidazolidin-4-one Chemical compound CCN1CC(=O)N(CC(C)C)C1=S UXFMOSJANJUHKK-UHFFFAOYSA-N 0.000 claims description 3
OAMMTFNJZIGSDM-UHFFFAOYSA-N 1-ethyl-3-(2-propan-2-ylphenyl)-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=CC=CC=C1C(C)C OAMMTFNJZIGSDM-UHFFFAOYSA-N 0.000 claims description 3
JUVVAQAITFIESN-UHFFFAOYSA-N 1-methyl-3-(2-propan-2-ylphenyl)-2-sulfanylideneimidazolidin-4-one Chemical compound CC(C)C1=CC=CC=C1N1C(=S)N(C)CC1=O JUVVAQAITFIESN-UHFFFAOYSA-N 0.000 claims description 3
GRQDHYSORYMGNF-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-1-ethyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=CC=C(Cl)C=C1Cl GRQDHYSORYMGNF-UHFFFAOYSA-N 0.000 claims description 3
SCCNLEIQXKBXQE-UHFFFAOYSA-N 3-(2,6-dimethylphenyl)-1-ethyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=C(C)C=CC=C1C SCCNLEIQXKBXQE-UHFFFAOYSA-N 0.000 claims description 3
LYMYDEGHCJPIGY-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-ethyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=CC=CC=C1Cl LYMYDEGHCJPIGY-UHFFFAOYSA-N 0.000 claims description 3
YWNIIMXOOLURSG-UHFFFAOYSA-N 3-(3-chloro-2-methylphenyl)-1-methyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(C)CC(=O)N1C1=CC=CC(Cl)=C1C YWNIIMXOOLURSG-UHFFFAOYSA-N 0.000 claims description 3
CGRGLUVBRXZOBE-UHFFFAOYSA-N 3-(4-chloro-2-methylphenyl)-1-methyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(C)CC(=O)N1C1=CC=C(Cl)C=C1C CGRGLUVBRXZOBE-UHFFFAOYSA-N 0.000 claims description 3
VIUZPNQTARUJED-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-1-methyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(C)CC(=O)N1C1=CC=C(C(C)(C)C)C=C1 VIUZPNQTARUJED-UHFFFAOYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000006663 (C1-C6) perfluoroalkyl group Chemical group 0.000 claims description 2
LOYBBTWIKKIMSB-UHFFFAOYSA-N 1-ethyl-2-sulfanylidene-3-(2,4,5-trimethylphenyl)imidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=CC(C)=C(C)C=C1C LOYBBTWIKKIMSB-UHFFFAOYSA-N 0.000 claims description 2
UWFGYMNXGVIRTG-UHFFFAOYSA-N 1-ethyl-3-(2-phenylethyl)-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1CCC1=CC=CC=C1 UWFGYMNXGVIRTG-UHFFFAOYSA-N 0.000 claims description 2
XTUZZKAVPZIIHE-UHFFFAOYSA-N 1-ethyl-3-[(4-fluorophenyl)methyl]-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1CC1=CC=C(F)C=C1 XTUZZKAVPZIIHE-UHFFFAOYSA-N 0.000 claims description 2
CFEZFGNJDGXEEK-UHFFFAOYSA-N 1-ethyl-3-naphthalen-2-yl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=CC=C(C=CC=C2)C2=C1 CFEZFGNJDGXEEK-UHFFFAOYSA-N 0.000 claims description 2
JFJCZWPKTPPYLX-UHFFFAOYSA-N 1-methyl-3-pyridin-3-yl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(C)CC(=O)N1C1=CC=CN=C1 JFJCZWPKTPPYLX-UHFFFAOYSA-N 0.000 claims description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
LNAMMQSFHJHFPF-UHFFFAOYSA-N 3-(2,3-dihydro-1h-inden-5-yl)-1-methyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(C)CC(=O)N1C1=CC=C(CCC2)C2=C1 LNAMMQSFHJHFPF-UHFFFAOYSA-N 0.000 claims description 2
MNZYSOFDUISXTE-UHFFFAOYSA-N 3-(2,4-dimethylphenyl)-1-ethyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=CC=C(C)C=C1C MNZYSOFDUISXTE-UHFFFAOYSA-N 0.000 claims description 2
POFQOUVDEVIYTO-UHFFFAOYSA-N 3-(2,5-dimethylphenyl)-1-ethyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=CC(C)=CC=C1C POFQOUVDEVIYTO-UHFFFAOYSA-N 0.000 claims description 2
SKEFZYSSPRAHLA-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-1-ethyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=C(Cl)C=CC=C1Cl SKEFZYSSPRAHLA-UHFFFAOYSA-N 0.000 claims description 2
KKQMIMGLLQIIJM-UHFFFAOYSA-N 3-(2-chloro-6-methylphenyl)-1-methyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(C)CC(=O)N1C1=C(C)C=CC=C1Cl KKQMIMGLLQIIJM-UHFFFAOYSA-N 0.000 claims description 2
KFYLJQOXOLFXFZ-UHFFFAOYSA-N 3-(2-ethyl-6-methylphenyl)-1-methyl-2-sulfanylideneimidazolidin-4-one Chemical compound CCC1=CC=CC(C)=C1N1C(=S)N(C)CC1=O KFYLJQOXOLFXFZ-UHFFFAOYSA-N 0.000 claims description 2
FHFTWKDDJGZVIF-UHFFFAOYSA-N 3-(2-ethylphenyl)-1-methyl-2-sulfanylideneimidazolidin-4-one Chemical compound CCC1=CC=CC=C1N1C(=S)N(C)CC1=O FHFTWKDDJGZVIF-UHFFFAOYSA-N 0.000 claims description 2
JUISGPCLIBCEMN-UHFFFAOYSA-N 3-(3-chloro-4-methylphenyl)-1-methyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(C)CC(=O)N1C1=CC=C(C)C(Cl)=C1 JUISGPCLIBCEMN-UHFFFAOYSA-N 0.000 claims description 2
OOCSJDWFSDSUBT-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-propan-2-yl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(C(C)C)CC(=O)N1C1=CC=C(F)C=C1 OOCSJDWFSDSUBT-UHFFFAOYSA-N 0.000 claims description 2
FKVLPQQMNPAKDQ-UHFFFAOYSA-N 3-(5-chloro-2-methylphenyl)-1-methyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(C)CC(=O)N1C1=CC(Cl)=CC=C1C FKVLPQQMNPAKDQ-UHFFFAOYSA-N 0.000 claims description 2
JXZCLPIMYFOZOX-UHFFFAOYSA-N 3-[2,6-di(propan-2-yl)phenyl]-1-ethyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=C(C(C)C)C=CC=C1C(C)C JXZCLPIMYFOZOX-UHFFFAOYSA-N 0.000 claims description 2
DETIHMBQBXRGGS-UHFFFAOYSA-N 3-[2,6-di(propan-2-yl)phenyl]-1-methyl-2-sulfanylideneimidazolidin-4-one Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N1C(=S)N(C)CC1=O DETIHMBQBXRGGS-UHFFFAOYSA-N 0.000 claims description 2
RXPWCQQEIWMTSR-UHFFFAOYSA-N 3-benzhydryl-1-methyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(C)CC(=O)N1C(C=1C=CC=CC=1)C1=CC=CC=C1 RXPWCQQEIWMTSR-UHFFFAOYSA-N 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
238000006467 substitution reaction Methods 0.000 claims description 2
230000003312 cholesterol blood level Effects 0.000 claims 3
WFOZHXDSZIJLFK-UHFFFAOYSA-N 3-(5-chloro-2-methylphenyl)-1-ethyl-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=CC(Cl)=CC=C1C WFOZHXDSZIJLFK-UHFFFAOYSA-N 0.000 claims 2
SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims 1
ARIWWEFHSLVCII-UHFFFAOYSA-N 1-ethyl-3-(2-ethyl-4-methylphenyl)-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CC)CC(=O)N1C1=CC=C(C)C=C1CC ARIWWEFHSLVCII-UHFFFAOYSA-N 0.000 claims 1
LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000003709 fluoroalkyl group Chemical group 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 abstract description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 195
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 90
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 81
239000007787 solid Substances 0.000 description 81
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 56
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
238000002425 crystallisation Methods 0.000 description 40
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
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YPIGGYHFMKJNKV-UHFFFAOYSA-N N-ethylglycine Chemical compound CC[NH2+]CC([O-])=O YPIGGYHFMKJNKV-UHFFFAOYSA-N 0.000 description 20
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239000007788 liquid Substances 0.000 description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
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BNDZNKDOPHTAFQ-UHFFFAOYSA-N ethyl 2-(prop-2-ynylamino)acetate Chemical compound CCOC(=O)CNCC#C BNDZNKDOPHTAFQ-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
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IZJDOKYDEWTZSO-UHFFFAOYSA-N phenethyl isothiocyanate Chemical compound S=C=NCCC1=CC=CC=C1 IZJDOKYDEWTZSO-UHFFFAOYSA-N 0.000 description 1
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Classifications

- 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
- 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
- A61K31/4164—1,3-Diazoles
- A61K31/4166—1,3-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
- 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
- A61K31/4164—1,3-Diazoles
- A61K31/4174—Arylalkylimidazoles, e.g. oxymetazolin, naphazoline, miconazole
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Epidemiology (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

JP9520724A 1995-11-28 1996-11-25 ２―チオキソ―イミダゾリジン―４―オン誘導体およびｈｄｌコレステロール濃度を上昇させるためのそれらの使用 Pending JP2000501100A (ja)

Applications Claiming Priority (13)

Application Number	Priority Date	Filing Date	Title
US766695P	1995-11-28	1995-11-28
US765895P	1995-11-28	1995-11-28
US766595P	1995-11-28	1995-11-28
US765495P	1995-11-28	1995-11-28
US766195P	1995-11-28	1995-11-28
US60/007,665		1995-11-28
US08/563,325		1995-11-28
US60/007,654		1995-11-28
US60/007,661		1995-11-28
US60/007,666		1995-11-28
US08/563,325 US5554607A (en)	1995-11-28	1995-11-28	Use of 2-thioxo-imidazolin-4-one derivatives in the treatment of atherosclerosis
US60/007,658		1995-11-28
PCT/US1996/019164 WO1997019932A1 (en)	1995-11-28	1996-11-25	2-thioxo-imidazolidin-4-one derivatives and their use for increasing hdl cholesterol concentration

Publications (1)

Publication Number	Publication Date
JP2000501100A true JP2000501100A (ja)	2000-02-02

Family

ID=27555583

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP9520724A Pending JP2000501100A (ja)	1995-11-28	1996-11-25	２―チオキソ―イミダゾリジン―４―オン誘導体およびｈｄｌコレステロール濃度を上昇させるためのそれらの使用

Country Status (5)

Country	Link
EP (1)	EP0876355A1 (de)
JP (1)	JP2000501100A (de)
AU (1)	AU1127697A (de)
CA (1)	CA2238762A1 (de)
WO (1)	WO1997019932A1 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6455566B1 (en)	1997-09-03	2002-09-24	Wyeth	Substituted 1-aryl-3-heteroaryl-thioureas (or isothioureas) as antiatherosclerotic agents
TW415942B (en) *	1997-09-03	2000-12-21	American Home Prod	Novel substituted 1-aryl-3-heteroaryl-thioureas and substituted 1-aryl-3-heteroaryl-isothioureas as antiatherosclerotic agents
EP1112072A2 (de) *	1998-08-31	2001-07-04	Sentron Medical, Inc.	Methimazole derivate und tautomerische cyclische thione zur behandlung von autoimmunkrankheiten
US20040235877A1 (en)	2001-09-14	2004-11-25	Natsuki Ishizuka	Novel use of tricyclic compound
FR2845384B1 (fr) *	2002-10-04	2004-12-31	Fournier Lab Sa	Composes derives de la 2-thiohydantoine et leur utilisation en therapeutique
WO2004031160A2 (fr) *	2002-10-04	2004-04-15	Laboratoires Fournier S.A.	Composes derives de la 2-thiohydantoïne et leur utilisation pour le traitement du diabete
FR2845385B1 (fr) *	2002-10-04	2004-12-31	Fournier Lab Sa	Composes derives de la 2-thiohydantoine et leur utilisation en therapeutique

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR956150A (de) *		1950-01-26
BE550650A (de) *	1955-08-30
IL66242A0 (en) *	1981-07-23	1982-11-30	Erba Farmitalia	N-imidazolyl derivatives of 1,2,3,4-tetrahydro-naphthalene,indan and 2-substituted-1-chroman,their preparation and pharmaceutical compositions containing them
JPH0629943B2 (ja) *	1983-10-31	1994-04-20	富士写真フイルム株式会社	画像形成方法
JPH01187543A (ja) *	1988-01-21	1989-07-26	Mitsubishi Paper Mills Ltd	写真用分光増感色素
FR2694290B1 (fr) *	1992-07-08	1994-09-02	Roussel Uclaf	Nouvelles phénylimidazolidines éventuellement substituées, leur procédé de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant.
US5554607A (en) *	1995-11-28	1996-09-10	American Home Products Corporation	Use of 2-thioxo-imidazolin-4-one derivatives in the treatment of atherosclerosis

1996
- 1996-11-25 WO PCT/US1996/019164 patent/WO1997019932A1/en not_active Ceased
- 1996-11-25 CA CA002238762A patent/CA2238762A1/en not_active Abandoned
- 1996-11-25 EP EP96942118A patent/EP0876355A1/de not_active Withdrawn
- 1996-11-25 JP JP9520724A patent/JP2000501100A/ja active Pending
- 1996-11-25 AU AU11276/97A patent/AU1127697A/en not_active Abandoned

Also Published As

Publication number	Publication date
CA2238762A1 (en)	1997-06-05
EP0876355A1 (de)	1998-11-11
WO1997019932A1 (en)	1997-06-05
AU1127697A (en)	1997-06-19

Publication	Publication Date	Title
DE69418243T2 (de)	1999-09-30	N-Heteroaryl-N'-Phenylharnstoffderivate, ihre Herstellung und Verwendung
US5554607A (en)	1996-09-10	Use of 2-thioxo-imidazolin-4-one derivatives in the treatment of atherosclerosis
JP2000514401A (ja)	2000-10-31	２―（置換スルファニル）―３，５―ジヒドロ―イミダゾール―４―オン誘導体
KR20050121681A (ko)	2005-12-27	면역조절 헤테로고리 화합물
JPH11513993A (ja)	1999-11-30	プロトン・ポンプ・インヒビター
HU201015B (en)	1990-09-28	Process for producing pyridine derivatives
JPS59206356A (ja)	1984-11-22	新規５−アシル−２−（１ｈ）−ピリジノン類
EP0876355A1 (de)	1998-11-11	2-thioxo-imidazolidin-4-eins derivate und ihre verwendung zur erhöhung der hdl-cholesterolkonzentration
JP2000507926A (ja)	2000-06-27	２―チオキソテトラヒドロピリミジン―４―オン誘導体
US5599829A (en)	1997-02-04	2-(substituted sulfanyl)-3,5-dihydro-imidazol-4-one derivatives for increasing HDL cholesterol levels
JPH0764844B2 (ja)	1995-07-12	ピリダジノピロロイソキノリン誘導体
US5861517A (en)	1999-01-19	2-thioxo-imidazolidin-4-one derivatives
US5877324A (en)	1999-03-02	2-(substituted sulfanyl)-3,5-dihydro-imidazol-4-one derivatives
US5821372A (en)	1998-10-13	2-thioxo-imidazolidin-4-one derivatives
US7135492B2 (en)	2006-11-14	1,3-disubstituted-2- thioxo-imidazolidine-4,5-dione derivatives useful in the treatment of atherosclerosis
US4255573A (en)	1981-03-10	Imidazoindole derivatives and pharmaceutical compositions comprising imidazoindole derivatives
JPH0374661B2 (de)	1991-11-27
PT89749B (pt)	1994-03-31	Processo para a preparacao de alcanoil- e aroil-oxazolonas com accao tonicardiaca
JPH0892248A (ja)	1996-04-09	インドリノン誘導体
US6562814B2 (en)	2003-05-13	3-thioxo-[1,2,4]-oxadiazinan-5-one derivatives
JPH06172365A (ja)	1994-06-21	１０−チアイソアロキサジン誘導体およびその用途
HU187338B (en)	1985-12-28	Process for the preperation of indole-acitic-acid
JP2001503769A (ja)	2001-03-21	抗アテローム性動脈硬化症薬としての置換テトラヒドロ―１，３，５―トリアジン―２［１ｈ］―チオン
US6472430B2 (en)	2002-10-29	Amino thioxomethyl amino oxyacetic acid derivatives
US6448255B1 (en)	2002-09-10	Imidazo-isoquinolin-5-one derivatives, pyrimido-isoquinolin-6-one derivatives and imidazo-naphthyridin-5-one derivatives