JP4705782B2 - 肥満の処置のためのプロスタグランジン化合物 - Google Patents
肥満の処置のためのプロスタグランジン化合物 Download PDFInfo
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- JP4705782B2 JP4705782B2 JP2004546433A JP2004546433A JP4705782B2 JP 4705782 B2 JP4705782 B2 JP 4705782B2 JP 2004546433 A JP2004546433 A JP 2004546433A JP 2004546433 A JP2004546433 A JP 2004546433A JP 4705782 B2 JP4705782 B2 JP 4705782B2
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- Prior art keywords
- alkyl
- prostaglandin
- compound
- hydroxy
- halogen
- 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.)
- Expired - Fee Related
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- -1 Prostaglandin compounds Chemical class 0.000 title claims abstract description 52
- 208000008589 Obesity Diseases 0.000 title claims abstract description 26
- 235000020824 obesity Nutrition 0.000 title claims abstract description 26
- 238000011282 treatment Methods 0.000 title claims description 10
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000004043 oxo group Chemical group O=* 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004423 acyloxy group Chemical group 0.000 claims description 12
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 12
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
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- 239000011593 sulfur Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
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- 150000001875 compounds Chemical class 0.000 abstract description 41
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- 238000012360 testing method Methods 0.000 description 18
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- 125000001424 substituent group Chemical group 0.000 description 13
- 229940079593 drug Drugs 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
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- 125000005843 halogen group Chemical group 0.000 description 8
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- 229910052731 fluorine Inorganic materials 0.000 description 5
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- 230000002496 gastric effect Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical compound CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- 125000002619 bicyclic group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 125000005842 heteroatom Chemical group 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 1
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- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
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- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
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- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- 125000004193 piperazinyl group Chemical group 0.000 description 1
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- 150000003053 piperidines Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 235000010409 propane-1,2-diol alginate Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 1
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- 235000020357 syrup Nutrition 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
-
- 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
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
- A61K31/5575—Eicosanoids, e.g. leukotrienes or prostaglandins having a cyclopentane, e.g. prostaglandin E2, prostaglandin F2-alpha
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Description
下付1:13,14−不飽和−15−OH
下付2:5,6−および13,14−ジ不飽和−15−OH
下付3:5,6−、13,14−および17,18−トリ不飽和−15−OH。
本発明は哺乳類対象における肥満の処置方法に関し、該方法は有効量のプロスタグランジン化合物をかかる処置を必要とする対象に投与することを含む。
本発明のPG化合物の命名に際しては、前記式(A)に示したプロスタン酸の番号を用いる。
Aは、−CH3または−CH2OH、−COCH2OH、−COOHまたはそれらの官能性誘導体;
Bは、単結合、−CH2−CH2−、−CH=CH−、−C≡C−、−CH2−CH2−CH2−、−CH=CH−CH2−、−CH2−CH=CH−、−C≡C−CH2−または−CH2−C≡C−;
Zは
(ここでR4およびR5は、水素、ヒドロキシ、ハロゲン、低級アルキル、低級アルコキシまたはヒドロキシ(低級)アルキルであり、ただし、R4およびR5が同時にヒドロキシおよび低級アルコキシであることはない);
R1は、非置換またはハロゲン、アルキル、ヒドロキシ、オキソ、アリールまたは複素環基で置換された飽和または不飽和二価低〜中級脂肪族炭化水素残基であり、脂肪族炭化水素における少なくとも1の炭素原子は任意に酸素、窒素または硫黄によって置換されていてもよい;そして、
Raは、非置換またはハロゲン、オキソ、ヒドロキシ、低級アルコキシ、低級アルカノイルオキシ、シクロ(低級)アルキル、シクロ(低級)アルキルオキシ、アリール、アリールオキシ、複素環基または複素環オキシ基で置換された飽和または不飽和の低〜中級脂肪族炭化水素残基;低級アルコキシ;低級アルカノイルオキシ;シクロ(低級)アルキル;シクロ(低級)アルキルオキシ;アリール;アリールオキシ;複素環基;複素環オキシ基]。
Aは、−CH3、または−CH2OH、−COCH2OH、−COOHまたはそれらの官能性誘導体;
Bは、単結合、−CH2−CH2−、−CH=CH−、−C≡C−、−CH2−CH2−CH2−、−CH=CH−CH2−、−CH2−CH=CH−、−C≡C−CH2−または−CH2−C≡C−;
Zは
(ここでR4およびR5は、水素、ヒドロキシ、ハロゲン、低級アルキル、低級アルコキシまたはヒドロキシ(低級)アルキルであり、ただし、R4およびR5が同時にヒドロキシおよび低級アルコキシであることはない)
X1およびX2は、水素、低級アルキルまたはハロゲン;
R1は、非置換またはハロゲン、アルキル、ヒドロキシ、オキソ、アリールまたは複素環で置換された、二価の飽和または不飽和の低〜中級の脂肪族炭化水素残基であり、脂肪族炭化水素における少なくとも1の炭素原子は任意に酸素、窒素または硫黄によって置換されていてもよい;
R2は、単結合または低級アルキレン;そして、
R3は、低級アルキル、低級アルコキシ、低級アルカノイルオキシ、シクロ(低級)アルキル、シクロ(低級)アルキルオキシ、アリール、アリールオキシ、複素環基または複素環オキシ基]。
−CH2−CH2−CH2−CH2−CH2−CH2−、
−CH2−CH=CH−CH2−CH2−CH2−、
−CH2−CH2−CH2−CH2−CH=CH−、
−CH2−C≡C−CH2−CH2−CH2−、
−CH2−CH2−CH2−CH2−O−CH2−、
−CH2−CH=CH−CH2−O−CH2−、
−CH2−C≡C−CH2−O−CH2−、
−CH2−CH2−CH2−CH2−CH2−CH2−CH2−、
−CH2−CH=CH−CH2−CH2−CH2−CH2−、
−CH2−CH2−CH2−CH2−CH2−CH=CH−、
−CH2−C≡C−CH2−CH2−CH2−CH2−、
−CH2−CH2−CH2−CH2−CH2−CH(CH3)−CH2−、
−CH2−CH2−CH2−CH2−CH(CH3)−CH2−、
−CH2−CH2−CH2−CH2−CH2−CH2−CH2−CH2−、
−CH2−CH=CH−CH2−CH2−CH2−CH2−CH2−、
−CH2−CH2−CH2−CH2−CH2−CH2−CH=CH−、
−CH2−C≡C−CH2−CH2−CH2−CH2−CH2−、および、
−CH2−CH2−CH2−CH2−CH2−CH2−CH(CH3)−CH2−。
X1’およびX2’は、水素、低級アルキルまたはハロゲン;
Yは、
R1は、非置換またはハロゲン、アルキル、ヒドロキシ、オキソ、アリールまたは複素環で置換された、二価の飽和または不飽和の低〜中級の脂肪族炭化水素残基;そして、脂肪族炭化水素における少なくとも1つの炭素原子は酸素、窒素または硫黄で置換されていてもよい、
R2’は、非置換またはハロゲン、オキソ、ヒドロキシ、低級アルコキシ、低級アルカノイルオキシ、シクロ(低級)アルキル、シクロ(低級)アルキルオキシ、アリール、アリールオキシ、複素環基または複素環オキシ基で置換された飽和または不飽和の低〜中級の脂肪族炭化水素残基;低級アルコキシ;低級アルカノイルオキシ;シクロ(低級)アルキル;シクロ(低級)アルキルオキシ;アリール;アリールオキシ;複素環基;複素環オキシ基;
R3’は、水素、低級アルキル、シクロ(低級)アルキル、アリールまたは複素環基]。
Claims (15)
- 活性成分として下記一般式(II)によって示されるプロスタグランジン化合物を含有する、肥満の処置用組成物:
Aは、−CH3、または−CH2OH、−COCH2OH、−COOHまたはそれらの官能性誘導体;
Bは、単結合、−CH2−CH2−、−CH=CH−、−C≡C−、−CH2−CH2−CH2−、−CH=CH−CH2−、−CH2−CH=CH−、−C≡C−CH2−または−CH2−C≡C−;
Zは
(ここでR4およびR5は、水素、ヒドロキシ、ハロゲン、低級アルキル、低級アルコキシまたはヒドロキシ(低級)アルキルであり、ただし、R4およびR5が同時にヒドロキシおよび低級アルコキシであることはない)
X1およびX2は、水素、低級アルキルまたはハロゲン;
R1は、非置換またはハロゲン、アルキル、ヒドロキシ、オキソ、アリールまたは複素環で置換された、二価の飽和または不飽和の低〜中級の脂肪族炭化水素残基であり、脂肪族炭化水素における少なくとも1の炭素原子は任意に酸素、窒素または硫黄によって置換されていてもよい;
R2は、単結合または低級アルキレン;そして、
R3は、低級アルキル、低級アルコキシ、低級アルカノイルオキシ、シクロ(低級)アルキル、シクロ(低級)アルキルオキシ、アリール、アリールオキシ、複素環基または複素環オキシ基、
但し、ZはC=Oである、および/またはX1およびX2の少なくとも一方はハロゲンである]。 - 該プロスタグランジン化合物が16−モノまたはジハロゲン−プロスタグランジン化合物である請求項1に記載の組成物。
- 該プロスタグランジン化合物が13,14−ジヒドロ−16−モノまたはジハロゲン−プロスタグランジン化合物である請求項1に記載の組成物。
- 該プロスタグランジン化合物が13,14−ジヒドロ−15−ケト−16−モノまたはジハロゲン−プロスタグランジン化合物である請求項1に記載の組成物。
- 該プロスタグランジン化合物が13,14−ジヒドロ−16−モノまたはジフルオロ−プロスタグランジン化合物である請求項1に記載の組成物。
- 該プロスタグランジン化合物が13,14−ジヒドロ−15−ケト−16−モノまたはジフルオロ−プロスタグランジン化合物である請求項1に記載の組成物。
- 該プロスタグランジン化合物が13,14−ジヒドロ−16−モノまたはジハロゲン−プロスタグランジンE化合物である請求項1に記載の組成物。
- 該プロスタグランジン化合物が13,14−ジヒドロ−15−ケト−16−モノまたはジハロゲン−プロスタグランジンE化合物である請求項1に記載の組成物。
- 該プロスタグランジン化合物が13,14−ジヒドロ−16,16−ジフルオロ−プロスタグランジンE1化合物である請求項1に記載の組成物。
- 該プロスタグランジン化合物が、式(II)においてLがオキソ、Mが水素またはヒドロキシ、X1およびX2がいずれもフルオロである請求項1に記載の組成物。
- 該プロスタグランジン化合物が13,14−ジヒドロ−15−ケト−16,16−ジフルオロ−プロスタグランジンE1化合物または13,14−ジヒドロ−15−ケト−16,16−ジフルオロ−18−メチル−プロスタグランジンE1化合物である請求項1に記載の組成物。
- 該プロスタグランジン化合物が13,14−ジヒドロ−15−ケト−16,16−ジフルオロ−プロスタグランジンE1または13,14−ジヒドロ−15−ケト−16,16−ジフルオロ−18−メチル−プロスタグランジンE1である請求項1に記載の組成物。
- 1日当たり1〜4回の全身投与または1日当たり0.01〜100μg/kgの量の連続投与のための請求項1〜12いずれかに記載の組成物。
- 投与が1日当たり0.1〜10μg/kgの量である請求項13に記載の組成物。
- 肥満の処置薬の製造のための、式(II)で示されるプロスタグランジン化合物の使用:
Aは、−CH3、または−CH2OH、−COCH2OH、−COOHまたはそれらの官能性誘導体;
Bは、単結合、−CH2−CH2−、−CH=CH−、−C≡C−、−CH2−CH2−CH2−、−CH=CH−CH2−、−CH2−CH=CH−、−C≡C−CH2−または−CH2−C≡C−;
Zは
(ここでR4およびR5は、水素、ヒドロキシ、ハロゲン、低級アルキル、低級アルコキシまたはヒドロキシ(低級)アルキルであり、ただし、R4およびR5が同時にヒドロキシおよび低級アルコキシであることはない)
X1およびX2は、水素、低級アルキルまたはハロゲン;
R1は、非置換またはハロゲン、アルキル、ヒドロキシ、オキソ、アリールまたは複素環で置換された、二価の飽和または不飽和の低〜中級の脂肪族炭化水素残基であり、脂肪族炭化水素における少なくとも1の炭素原子は任意に酸素、窒素または硫黄によって置換されていてもよい;
R2は、単結合または低級アルキレン;そして、
R3は、低級アルキル、低級アルコキシ、低級アルカノイルオキシ、シクロ(低級)アルキル、シクロ(低級)アルキルオキシ、アリール、アリールオキシ、複素環基または複素環オキシ基、
但し、ZはC=Oである、および/またはX1およびX2の少なくとも一方はハロゲンである]。
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DK (1) | DK1562604T3 (ja) |
ES (1) | ES2379652T3 (ja) |
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US8337891B2 (en) | 2003-07-03 | 2012-12-25 | Sucampo Ag | Enteric coated composition comprising prostaglandin analogs as chloride channel opener |
CA2681668C (en) | 2006-03-23 | 2014-04-01 | Michael S. Singer | Compositions comprising prostaglandin f2-alpha analogs and methods for reducing body fat |
ES2579990T3 (es) | 2011-01-19 | 2016-08-18 | Terakine Therapeutics, Inc. | Métodos y composiciones para tratar el síndrome metabólico |
US8426471B1 (en) | 2011-12-19 | 2013-04-23 | Topokine Therapeutics, Inc. | Methods and compositions for reducing body fat and adipocytes |
US8778981B2 (en) | 2012-11-21 | 2014-07-15 | Topokine Therapeutics, Inc. | Methods and compositions for locally increasing body fat |
WO2014159679A1 (en) | 2013-03-12 | 2014-10-02 | The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Methods for using lubiprostone to absorb fluid from the subretinal space |
BR112015025915A8 (pt) | 2013-04-12 | 2020-01-14 | Allergan Inc | uso de composto para redução de gordura e composições |
NO2753788T3 (ja) | 2013-05-10 | 2018-06-16 | ||
US9820993B2 (en) | 2013-05-15 | 2017-11-21 | Topokine Therapeutics, Inc. | Methods and compositions for topical delivery of prostaglandins to subcutaneous fat |
WO2015200425A1 (en) | 2014-06-27 | 2015-12-30 | Topokine Therapeutics, Inc. | Topical dosage regimen |
US11452703B2 (en) | 2020-05-21 | 2022-09-27 | Peregrine Ophthalmic PTE LTD. | Methods and compositions for reducing adipocyte numbers |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03163024A (ja) * | 1989-07-27 | 1991-07-15 | Ueno Seiyaku Oyo Kenkyusho:Kk | 高脂質血症処置・血中脂質成分低下剤 |
JPH11504331A (ja) * | 1995-04-25 | 1999-04-20 | ザ ソールク インスチチュート フォア バイオロジカル スタディズ | ペルオキシソーム増殖因子によって活性化されるレセプター−γの選択的モジュレーター、およびその使用法 |
WO1999053927A1 (en) * | 1998-04-17 | 1999-10-28 | Trustees Of Tufts College | Methods for treating and preventing insulin resistance and related disorders |
Family Cites Families (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US388919A (en) * | 1888-09-04 | Benjamin scables | ||
US3888919A (en) * | 1971-03-11 | 1975-06-10 | Upjohn Co | 11,15 dimethyl pge' 1 'and pgf' 1' |
CA1322749C (en) * | 1987-01-28 | 1993-10-05 | Ryuzo Ueno | Prostaglandins of the d series, and tranquilizers and soporifics containing the same |
US5166174A (en) * | 1987-01-28 | 1992-11-24 | K.K. Ueno Seiyaku Oyo Kenkyujo | Prostaglandins E and anti-ulcers containing same |
US5221763A (en) * | 1987-04-30 | 1993-06-22 | R-Tech Ueno, Ltd. | Prostaglandins of the F series |
US5317032A (en) * | 1987-10-02 | 1994-05-31 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Prostaglandin cathartic |
JP2597629B2 (ja) | 1988-02-26 | 1997-04-09 | 株式会社 上野製薬応用研究所 | 13,14−ジヒドロ−15−ケトプロスタグランジン類の安定化 |
NZ226198A (en) | 1988-09-15 | 1991-05-28 | Ueno Seiyaku Oyo Kenkyujo Kk | Fervescence (temperature raising) composition comprising 15-keto-pge |
NZ226199A (en) | 1988-09-15 | 1991-05-28 | Ueno Seiyaku Oyo Kenkyujo Kk | 13,14-dihydro-15-keto-pgf derivatives and pharmaceutical compositions |
EP0410646B1 (en) | 1989-07-27 | 1994-03-02 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Treatment of hyperlipidemia with 15-keto-prostaglandin compounds |
US5234954A (en) * | 1989-07-27 | 1993-08-10 | K.K. Ueno Seiyaku Oyo Kenkyujo | Treatment of hyperlipidemia with 15-keto-prostaglandin compounds |
TW224942B (ja) * | 1990-04-04 | 1994-06-11 | Adka Ueno Kk | |
CA2150287C (en) * | 1994-06-03 | 2004-08-10 | Ryuji Ueno | Agent for treating hepato-biliary diseases |
EP0857718B1 (en) * | 1996-06-10 | 2002-08-14 | Sucampo AG | Endothelin antagonist |
JP2000157260A (ja) | 1998-11-26 | 2000-06-13 | Toyobo Co Ltd | 初代前駆脂肪細胞の分化誘導方法及びその分化用培地 |
JP4332316B2 (ja) * | 1999-10-15 | 2009-09-16 | スキャンポ・アーゲー | 二環式化合物組成物およびその安定化方法 |
US6414016B1 (en) * | 2000-09-05 | 2002-07-02 | Sucampo, A.G. | Anti-constipation composition |
TWI302100B (en) * | 2001-05-02 | 2008-10-21 | Sucampo Ag | Composition for treating drug-induced constipation |
KR100867295B1 (ko) * | 2001-05-18 | 2008-11-06 | 수캄포 아게 | 하제 조성물 |
BR0212233A (pt) * | 2001-08-31 | 2004-10-05 | Sucampo Ag | Abridor de canal de cloreto |
AR037524A1 (es) * | 2001-11-14 | 2004-11-17 | Sucampo Ag | Unidad de dosificacion que comprende un analogo de prostaglandina para el tratamiento de la constipacion |
TWI263505B (en) * | 2001-11-19 | 2006-10-11 | Sucampo Ag | Pharmaceutical composition comprising a C1C-2 channel opener |
AU2003292556B2 (en) * | 2002-12-27 | 2009-09-10 | Sucampo Ag | Derivatives of prostaglandins for treating abdominal discomfort |
US8337891B2 (en) * | 2003-07-03 | 2012-12-25 | Sucampo Ag | Enteric coated composition comprising prostaglandin analogs as chloride channel opener |
TWI387454B (zh) * | 2004-09-02 | 2013-03-01 | Sucampo Ag | 治療胃腸道疾病之方法及組成物 |
US20060281818A1 (en) * | 2005-03-21 | 2006-12-14 | Sucampo Ag, North Carolina State University | Method for treating mucosal disorders |
EP1871380B1 (en) * | 2005-04-12 | 2011-10-19 | Sucampo AG | Combined use of prostaglandin compound and proton pump inhibitor for the treatment of gastrointestinal disorders |
-
2003
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03163024A (ja) * | 1989-07-27 | 1991-07-15 | Ueno Seiyaku Oyo Kenkyusho:Kk | 高脂質血症処置・血中脂質成分低下剤 |
JPH11504331A (ja) * | 1995-04-25 | 1999-04-20 | ザ ソールク インスチチュート フォア バイオロジカル スタディズ | ペルオキシソーム増殖因子によって活性化されるレセプター−γの選択的モジュレーター、およびその使用法 |
WO1999053927A1 (en) * | 1998-04-17 | 1999-10-28 | Trustees Of Tufts College | Methods for treating and preventing insulin resistance and related disorders |
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US20050261373A1 (en) | 2005-11-24 |
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AU2003274735A1 (en) | 2004-05-13 |
WO2004037268A1 (en) | 2004-05-06 |
CA2502439A1 (en) | 2004-05-06 |
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US8114911B2 (en) | 2012-02-14 |
EP1562604A1 (en) | 2005-08-17 |
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