AU2001264891A1 - Cyclopentane derivatives as therapeutic agents - Google Patents
Cyclopentane derivatives as therapeutic agentsInfo
- Publication number
- AU2001264891A1 AU2001264891A1 AU2001264891A AU6489101A AU2001264891A1 AU 2001264891 A1 AU2001264891 A1 AU 2001264891A1 AU 2001264891 A AU2001264891 A AU 2001264891A AU 6489101 A AU6489101 A AU 6489101A AU 2001264891 A1 AU2001264891 A1 AU 2001264891A1
- Authority
- AU
- Australia
- Prior art keywords
- enyl
- hydroxy
- pent
- oct
- cyclopentyl
- 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.)
- Abandoned
Links
- 125000001511 cyclopentyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 title description 41
- 239000003814 drug Substances 0.000 title description 5
- 229940124597 therapeutic agent Drugs 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 144
- 238000000034 method Methods 0.000 claims description 56
- -1 dibromothienyl Chemical group 0.000 claims description 51
- 208000010412 Glaucoma Diseases 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 206010030043 Ocular hypertension Diseases 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- WAYUEXIIMXHCIK-CJMQDTFBSA-N C([C@H](OC)\C=C\[C@@H]1[C@H]([C@@H](O)C[C@H]1O)C\C=C/CCCC(CO)OC(=O)C=1C=CC=CC=1)CC1=CC=C(Br)S1 Chemical compound C([C@H](OC)\C=C\[C@@H]1[C@H]([C@@H](O)C[C@H]1O)C\C=C/CCCC(CO)OC(=O)C=1C=CC=CC=1)CC1=CC=C(Br)S1 WAYUEXIIMXHCIK-CJMQDTFBSA-N 0.000 claims description 4
- VAHKAXJARGEQCO-IOZWXPRTSA-N CC(=O)OCC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](OC(C)=O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=C(Cl)S1 Chemical compound CC(=O)OCC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](OC(C)=O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=C(Cl)S1 VAHKAXJARGEQCO-IOZWXPRTSA-N 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000002997 ophthalmic solution Substances 0.000 claims description 4
- FPEZOGILBZHFOO-ZIPLXWHSSA-N (z)-8-[(1r,2r,3r,5s)-2-[(e,3s)-5-(4-chloro-5-methylthiophen-2-yl)-3-hydroxypent-1-enyl]-3,5-dihydroxycyclopentyl]-1-hydroxyoct-6-en-2-one Chemical compound ClC1=C(C)SC(CC[C@H](O)\C=C\[C@@H]2[C@H]([C@@H](O)C[C@H]2O)C\C=C/CCCC(=O)CO)=C1 FPEZOGILBZHFOO-ZIPLXWHSSA-N 0.000 claims description 3
- MTCLODTZCFEIMD-PQPXSEEMSA-N (z)-8-[(1r,2r,3r,5s)-2-[(e,3s)-5-(5-bromothiophen-2-yl)-3-hydroxypent-1-enyl]-3,5-dihydroxycyclopentyl]-1-hydroxyoct-6-en-2-one Chemical compound OCC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=C(Br)S1 MTCLODTZCFEIMD-PQPXSEEMSA-N 0.000 claims description 3
- ALDWZWZZHYRGHP-GWPWBHHYSA-N (z)-8-[(1r,2r,3r,5s)-2-[(e,3s)-5-(5-bromothiophen-2-yl)-3-methoxypent-1-enyl]-3,5-dihydroxycyclopentyl]-1-hydroxyoct-6-en-2-one Chemical compound C([C@H](OC)\C=C\[C@@H]1[C@H]([C@@H](O)C[C@H]1O)C\C=C/CCCC(=O)CO)CC1=CC=C(Br)S1 ALDWZWZZHYRGHP-GWPWBHHYSA-N 0.000 claims description 3
- PRPNXAFTPGQINW-PQPXSEEMSA-N (z)-8-[(1r,2r,3r,5s)-2-[(e,3s)-5-(5-chlorothiophen-2-yl)-3-hydroxypent-1-enyl]-3,5-dihydroxycyclopentyl]-1-hydroxyoct-6-en-2-one Chemical compound OCC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=C(Cl)S1 PRPNXAFTPGQINW-PQPXSEEMSA-N 0.000 claims description 3
- GBUBKLGNYVDUFB-QMNWUTKHSA-N (z)-8-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(e,3s)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-1-hydroxyoct-6-en-2-one Chemical compound OCC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=CC=C1 GBUBKLGNYVDUFB-QMNWUTKHSA-N 0.000 claims description 3
- TVXDUAIHUCNEHD-RAPUABRKSA-N [(z)-8-[(1r,2r,3r,5s)-2-[(e,3s)-5-(5-chlorothiophen-2-yl)-3-hydroxypent-1-enyl]-3,5-dihydroxycyclopentyl]-2-oxooct-6-enyl] acetate Chemical compound CC(=O)OCC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=C(Cl)S1 TVXDUAIHUCNEHD-RAPUABRKSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000001631 hypertensive effect Effects 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 229940054534 ophthalmic solution Drugs 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- HFLHGXCTQRUHCG-NEOWASLHSA-N (1r,3s,4r,5r)-4-[(z)-7,8-dihydroxyoct-2-enyl]-5-[(e,3s)-3-hydroxy-5-(5-methylthiophen-2-yl)pent-1-enyl]cyclopentane-1,3-diol Chemical compound S1C(C)=CC=C1CC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)CO)[C@@H](O)C[C@H]1O HFLHGXCTQRUHCG-NEOWASLHSA-N 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 230000003832 immune regulation Effects 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims 2
- VNTDVZNCXNTXKS-FFLKAMFBSA-N (1r,3s,4r,5r)-4-[(z)-7,8-dihydroxyoct-2-enyl]-5-[(e,3s)-3-hydroxyoct-1-enyl]cyclopentane-1,3-diol Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)CO VNTDVZNCXNTXKS-FFLKAMFBSA-N 0.000 claims 1
- NIVJTWJVCFIDQF-IHHPBAKNSA-N (1s,3r,4r,5r)-4-[(e,3r)-5-(5-chlorothiophen-2-yl)-3-hydroxypent-1-enyl]-5-[(z)-7,8-dihydroxyoct-2-enyl]cyclopentane-1,3-diol Chemical compound OCC(O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@H](O)CCC1=CC=C(Cl)S1 NIVJTWJVCFIDQF-IHHPBAKNSA-N 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 206010021639 Incontinence Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 230000004097 bone metabolism Effects 0.000 claims 1
- 208000010643 digestive system disease Diseases 0.000 claims 1
- 230000035558 fertility Effects 0.000 claims 1
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 1
- 230000003463 hyperproliferative effect Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 230000008085 renal dysfunction Effects 0.000 claims 1
- 230000035939 shock Effects 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- 239000000203 mixture Substances 0.000 description 40
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 34
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
- 150000002148 esters Chemical class 0.000 description 28
- 235000019439 ethyl acetate Nutrition 0.000 description 28
- 238000003818 flash chromatography Methods 0.000 description 24
- 229920006395 saturated elastomer Polymers 0.000 description 23
- 239000000741 silica gel Substances 0.000 description 23
- 229910002027 silica gel Inorganic materials 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000007832 Na2SO4 Substances 0.000 description 22
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
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- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 1
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- 208000018769 loss of vision Diseases 0.000 description 1
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- 239000000463 material Substances 0.000 description 1
- JFJDNPRDELNSRT-NSCUHMNNSA-N methyl (e)-3-(2,5-dibromothiophen-3-yl)prop-2-enoate Chemical compound COC(=O)\C=C\C=1C=C(Br)SC=1Br JFJDNPRDELNSRT-NSCUHMNNSA-N 0.000 description 1
- GHCZBEQXSRLFSP-UHFFFAOYSA-N methyl 3-(2,5-dibromothiophen-3-yl)propanoate Chemical compound COC(=O)CCC=1C=C(Br)SC=1Br GHCZBEQXSRLFSP-UHFFFAOYSA-N 0.000 description 1
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- HWWVAHCWJLGKLW-UHFFFAOYSA-N n,n-dimethylhydroxylamine;hydron;chloride Chemical compound Cl.CN(C)O HWWVAHCWJLGKLW-UHFFFAOYSA-N 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 229940066842 petrolatum Drugs 0.000 description 1
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- 229940096826 phenylmercuric acetate Drugs 0.000 description 1
- PDTFCHSETJBPTR-UHFFFAOYSA-N phenylmercuric nitrate Chemical compound [O-][N+](=O)O[Hg]C1=CC=CC=C1 PDTFCHSETJBPTR-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
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- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
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- PXGPLTODNUVGFL-YNNPMVKQSA-N prostaglandin F2alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O PXGPLTODNUVGFL-YNNPMVKQSA-N 0.000 description 1
- PXGPLTODNUVGFL-JZFBHDEDSA-N prostaglandin F2beta Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H](O)[C@@H]1C\C=C/CCCC(O)=O PXGPLTODNUVGFL-JZFBHDEDSA-N 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
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- 239000012266 salt solution Substances 0.000 description 1
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- 210000002460 smooth muscle Anatomy 0.000 description 1
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- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 229940001474 sodium thiosulfate Drugs 0.000 description 1
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- 239000007901 soft capsule Substances 0.000 description 1
- 210000005070 sphincter Anatomy 0.000 description 1
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- 238000007920 subcutaneous administration Methods 0.000 description 1
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- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
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- 235000010487 tragacanth Nutrition 0.000 description 1
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- 230000008733 trauma Effects 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
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- 239000003871 white petrolatum Substances 0.000 description 1
- 239000011995 wilkinson's catalyst Substances 0.000 description 1
- UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 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
- C07D333/28—Halogen atoms
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0016—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing only hydroxy, etherified or esterified hydroxy groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/665,791 US6248783B1 (en) | 2000-09-20 | 2000-09-20 | Cyclopentane 1-hydroxy alkyl or alkenyl-2-one or 2-hydroxy derivatives as therapeutic agents |
| US09665791 | 2000-09-20 | ||
| PCT/US2001/016770 WO2002024639A1 (fr) | 2000-09-20 | 2001-05-23 | Dérivés de cyclopentane utilisés comme agents thérapeutiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2001264891A1 true AU2001264891A1 (en) | 2002-04-02 |
Family
ID=24671590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001264891A Abandoned AU2001264891A1 (en) | 2000-09-20 | 2001-05-23 | Cyclopentane derivatives as therapeutic agents |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US6248783B1 (fr) |
| EP (1) | EP1318979A1 (fr) |
| JP (1) | JP2004511446A (fr) |
| AR (1) | AR029940A1 (fr) |
| AU (1) | AU2001264891A1 (fr) |
| CA (1) | CA2433157A1 (fr) |
| WO (1) | WO2002024639A1 (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2259010T3 (es) * | 2001-10-26 | 2006-09-16 | Allergan, Inc. | Analogos de omega-cicloalquil-17-heteroaril-prostaglandina e2 como agonistas del receptor ep2. |
| KR20050039733A (ko) * | 2001-11-05 | 2005-04-29 | 알러간, 인코포레이티드 | ＥＰ₂-수용체 작용제로서의 ω-시클로알킬 17-헤테로아릴프로스타글란딘 Ｅ₂유사체 |
| US7179820B2 (en) * | 2003-06-06 | 2007-02-20 | Allergan, Inc. | Piperidinyl prostaglandin E analogs |
| JP2005511607A (ja) * | 2003-07-10 | 2005-04-28 | アラーガン、インコーポレイテッド | ＥＰ２受容体作動剤としてのω−シクロアルキル１７−ヘテロアリールプロスタグランジンＥ２類似体 |
| US20070232660A1 (en) * | 2006-04-04 | 2007-10-04 | Allergan, Inc. | Therapeutic and delivery methods of prostaglandin ep4 agonists |
| US20110293549A1 (en) | 2009-02-03 | 2011-12-01 | Athena Cosmetics, Inc. | Composition, method and kit for enhancing hair |
| CN102757459B (zh) * | 2011-04-29 | 2016-01-27 | 上海源力生物技术有限公司 | 用于合成前列腺素类药物的中间体及其制备方法 |
| EP3235810A1 (fr) * | 2016-04-19 | 2017-10-25 | Gentec, S.A. | Procédé pour la préparation de bimatoprost |
| CA3132572A1 (fr) | 2019-03-27 | 2020-10-01 | Kyowa Pharma Chemical Co., Ltd. | Procede de production de prostaglandine |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1148149A (fr) * | 1977-12-08 | 1983-06-14 | Allan Wissner | Activite des prostaglandines |
| US4994274A (en) | 1989-07-27 | 1991-02-19 | Allergan, Inc. | Intraocular pressure reducing 11,15-diacyl prostaglandins and method of using |
| US5034413A (en) | 1989-07-27 | 1991-07-23 | Allergan, Inc. | Intraocular pressure reducing 9,11-diacyl prostaglandins |
| CA2021316C (fr) | 1989-07-27 | 2000-10-24 | Ming Fai Chan | 11-acyl prostaglandines reductrices de la pression intraoculaire |
| US5028624A (en) | 1989-07-27 | 1991-07-02 | Allergan, Inc. | Intraocular pressure reducing 9,15-diacyl prostaglandins |
| EP0825980B1 (fr) * | 1995-05-18 | 2001-07-04 | Allergan Sales, Inc. | Utilisation de derives d'acide cyclopentane heptan(ene)oique, 2-heteroarylalkenyle en tant qu'agents therapeutiques pour le traitement de l'hypertension oculaire |
| US5741810A (en) * | 1996-02-29 | 1998-04-21 | Allergan | Cyclopentane heptan(ene)oic acid, 2- heteroarylalkenyl derivatives as therapeutic agents |
-
2000
- 2000-09-20 US US09/665,791 patent/US6248783B1/en not_active Expired - Fee Related
-
2001
- 2001-05-08 US US09/850,834 patent/US6307092B1/en not_active Expired - Lifetime
- 2001-05-23 AU AU2001264891A patent/AU2001264891A1/en not_active Abandoned
- 2001-05-23 WO PCT/US2001/016770 patent/WO2002024639A1/fr not_active Application Discontinuation
- 2001-05-23 EP EP01939364A patent/EP1318979A1/fr not_active Withdrawn
- 2001-05-23 JP JP2002529052A patent/JP2004511446A/ja active Pending
- 2001-05-23 CA CA002433157A patent/CA2433157A1/fr not_active Abandoned
- 2001-06-11 AR ARP010102760A patent/AR029940A1/es unknown
- 2001-07-26 US US09/915,908 patent/US6359181B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004511446A (ja) | 2004-04-15 |
| US6359181B1 (en) | 2002-03-19 |
| WO2002024639A1 (fr) | 2002-03-28 |
| US6307092B1 (en) | 2001-10-23 |
| EP1318979A1 (fr) | 2003-06-18 |
| CA2433157A1 (fr) | 2002-03-28 |
| US6248783B1 (en) | 2001-06-19 |
| AR029940A1 (es) | 2003-07-23 |
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