SK14732000A3 - C11-oximylová a hydroxylamínová prostaglandínová zlúčenina a jej použitie - Google Patents
C11-oximylová a hydroxylamínová prostaglandínová zlúčenina a jej použitie Download PDFInfo
- Publication number
- SK14732000A3 SK14732000A3 SK1473-2000A SK14732000A SK14732000A3 SK 14732000 A3 SK14732000 A3 SK 14732000A3 SK 14732000 A SK14732000 A SK 14732000A SK 14732000 A3 SK14732000 A3 SK 14732000A3
- Authority
- SK
- Slovakia
- Prior art keywords
- monocyclic
- ring
- oximyl
- formula
- hydroxylamine
- Prior art date
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- -1 hydroxylamino prostaglandins Chemical class 0.000 title claims description 29
- 239000003814 drug Substances 0.000 title claims 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 title description 17
- 208000020084 Bone disease Diseases 0.000 claims abstract description 11
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 150000001408 amides Chemical class 0.000 claims abstract description 4
- 230000003287 optical effect Effects 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims abstract description 3
- 150000003949 imides Chemical class 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 20
- 125000002950 monocyclic group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 208000001132 Osteoporosis Diseases 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 150000003536 tetrazoles Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 111
- 239000000203 mixture Substances 0.000 abstract description 30
- 150000003180 prostaglandins Chemical class 0.000 abstract description 21
- 238000000034 method Methods 0.000 abstract description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 3
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- 125000001424 substituent group Chemical group 0.000 description 21
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- 125000001188 haloalkyl group Chemical group 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
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- 239000012298 atmosphere Substances 0.000 description 6
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- 150000002367 halogens Chemical class 0.000 description 6
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- 238000012360 testing method Methods 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- DZUXGQBLFALXCR-UHFFFAOYSA-N (+)-(9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprost-13-en-1-oic acid Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CCCCCCC(O)=O DZUXGQBLFALXCR-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
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- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
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- 230000004410 intraocular pressure Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- 125000006413 ring segment Chemical group 0.000 description 4
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- 125000001544 thienyl group Chemical group 0.000 description 4
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- 150000001412 amines Chemical class 0.000 description 3
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 208000005368 osteomalacia Diseases 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 208000001685 postmenopausal osteoporosis Diseases 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
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000004648 relaxation of smooth muscle Effects 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- JGWFUSVYECJQDT-UHFFFAOYSA-N trimethyl(2-trimethylsilyloxyethoxy)silane Chemical compound C[Si](C)(C)OCCO[Si](C)(C)C JGWFUSVYECJQDT-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
- C07C239/18—Hydroxylamino compounds or their ethers or esters having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- 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
- C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8007598P | 1998-03-31 | 1998-03-31 | |
| PCT/IB1999/000478 WO1999050241A1 (fr) | 1998-03-31 | 1999-03-22 | Prostaglandines c11 oxymyl et hydroxylamino utilisees comme medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK14732000A3 true SK14732000A3 (sk) | 2001-04-09 |
Family
ID=22155104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1473-2000A SK14732000A3 (sk) | 1998-03-31 | 1999-03-22 | C11-oximylová a hydroxylamínová prostaglandínová zlúčenina a jej použitie |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6410780B1 (fr) |
| EP (1) | EP1082299B1 (fr) |
| JP (1) | JP2002509915A (fr) |
| KR (1) | KR20010042286A (fr) |
| CN (1) | CN1295560A (fr) |
| AR (1) | AR020063A1 (fr) |
| AT (1) | ATE270272T1 (fr) |
| AU (1) | AU749796B2 (fr) |
| BR (1) | BR9909267A (fr) |
| CA (1) | CA2324343C (fr) |
| DE (1) | DE69918433T2 (fr) |
| ES (1) | ES2223180T3 (fr) |
| HU (1) | HUP0102789A2 (fr) |
| ID (1) | ID26699A (fr) |
| IL (1) | IL138446A0 (fr) |
| NO (1) | NO20004904L (fr) |
| NZ (1) | NZ506853A (fr) |
| PE (1) | PE20000350A1 (fr) |
| PL (1) | PL343113A1 (fr) |
| SK (1) | SK14732000A3 (fr) |
| TR (1) | TR200002808T2 (fr) |
| WO (1) | WO1999050241A1 (fr) |
| ZA (1) | ZA992393B (fr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ513825A (en) | 1999-03-05 | 2001-09-28 | Procter & Gamble | C 16 unsaturated FP-selective prostaglandins analogs |
| US20020146439A1 (en) * | 2000-03-31 | 2002-10-10 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using oximyl and hydroxylamino prostaglandins |
| US20020172693A1 (en) * | 2000-03-31 | 2002-11-21 | Delong Michell Anthony | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
| US20020037914A1 (en) | 2000-03-31 | 2002-03-28 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
| US20020013294A1 (en) | 2000-03-31 | 2002-01-31 | Delong Mitchell Anthony | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
| US20060135609A1 (en) | 2004-10-21 | 2006-06-22 | Duke University | Ophthamological drugs |
| US20070254920A1 (en) * | 2006-04-26 | 2007-11-01 | Aerie Pharmaceuticals, Inc. | Prodrug derivatives of acids using alcohols with homotopic hydroxy groups and methods for their preparation and use |
| US8722739B2 (en) | 2008-10-29 | 2014-05-13 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| US8623918B2 (en) * | 2008-10-29 | 2014-01-07 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| US20110293549A1 (en) | 2009-02-03 | 2011-12-01 | Athena Cosmetics, Inc. | Composition, method and kit for enhancing hair |
| CN102101835B (zh) * | 2009-12-16 | 2015-07-22 | 武汉启瑞药业有限公司 | 前列腺素衍生物及其中间体的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3776938A (en) | 1958-05-28 | 1973-12-04 | S Bergstrom | Dihydro-pge1 |
| US3636120A (en) * | 1967-10-09 | 1972-01-18 | Upjohn Co | Prostaglandin e primary alcohols |
| US4011262A (en) | 1972-07-13 | 1977-03-08 | Pfizer Inc. | 13,14-Dihydro-15-substituted-ω-pentanorprostaglandins of the two series |
| US4024179A (en) | 1972-11-08 | 1977-05-17 | Pfizer Inc. | Substituted ω-pentanorprostaglandins |
| DE2460990A1 (de) | 1974-12-21 | 1976-07-01 | Hoechst Ag | Neue prostaglandin-analoga und verfahren zu ihrer herstellung |
| GB1507211A (en) | 1975-02-14 | 1978-04-12 | Ono Pharmaceutical Co | Prostaglandin analogues |
| JPH0222226A (ja) * | 1988-07-12 | 1990-01-25 | Ono Pharmaceut Co Ltd | Ｐｇｄ類似化合物を有効成分として含有する骨疾患治療剤 |
| JP2721414B2 (ja) | 1988-09-06 | 1998-03-04 | フアーマシア・アンド・アツプジヨン・アー・ベー | 縁内障または眼圧亢進の治療のためのプロスタグランジン誘導体 |
-
1999
- 1999-03-22 ID IDW20002225A patent/ID26699A/id unknown
- 1999-03-22 CA CA002324343A patent/CA2324343C/fr not_active Expired - Fee Related
- 1999-03-22 WO PCT/IB1999/000478 patent/WO1999050241A1/fr active IP Right Grant
- 1999-03-22 AT AT99942610T patent/ATE270272T1/de not_active IP Right Cessation
- 1999-03-22 CN CN99804645A patent/CN1295560A/zh active Pending
- 1999-03-22 HU HU0102789A patent/HUP0102789A2/hu unknown
- 1999-03-22 TR TR2000/02808T patent/TR200002808T2/xx unknown
- 1999-03-22 ES ES99942610T patent/ES2223180T3/es not_active Expired - Lifetime
- 1999-03-22 US US09/647,381 patent/US6410780B1/en not_active Expired - Fee Related
- 1999-03-22 NZ NZ506853A patent/NZ506853A/xx unknown
- 1999-03-22 PL PL99343113A patent/PL343113A1/xx unknown
- 1999-03-22 BR BR9909267-0A patent/BR9909267A/pt not_active IP Right Cessation
- 1999-03-22 AU AU32701/99A patent/AU749796B2/en not_active Ceased
- 1999-03-22 JP JP2000541146A patent/JP2002509915A/ja not_active Withdrawn
- 1999-03-22 DE DE69918433T patent/DE69918433T2/de not_active Expired - Fee Related
- 1999-03-22 EP EP99942610A patent/EP1082299B1/fr not_active Expired - Lifetime
- 1999-03-22 KR KR1020007010829A patent/KR20010042286A/ko not_active Application Discontinuation
- 1999-03-22 IL IL13844699A patent/IL138446A0/xx unknown
- 1999-03-22 SK SK1473-2000A patent/SK14732000A3/sk unknown
- 1999-03-29 ZA ZA9902393A patent/ZA992393B/xx unknown
- 1999-03-30 AR ARP990101444A patent/AR020063A1/es unknown
- 1999-03-30 PE PE1999000252A patent/PE20000350A1/es not_active Application Discontinuation
-
2000
- 2000-09-29 NO NO20004904A patent/NO20004904L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA992393B (en) | 1999-09-03 |
| EP1082299A1 (fr) | 2001-03-14 |
| KR20010042286A (ko) | 2001-05-25 |
| TR200002808T2 (tr) | 2001-01-22 |
| PE20000350A1 (es) | 2000-06-22 |
| NO20004904D0 (no) | 2000-09-29 |
| ID26699A (id) | 2001-02-01 |
| PL343113A1 (en) | 2001-07-30 |
| ATE270272T1 (de) | 2004-07-15 |
| ES2223180T3 (es) | 2005-02-16 |
| WO1999050241A1 (fr) | 1999-10-07 |
| CA2324343C (fr) | 2005-05-31 |
| NO20004904L (no) | 2000-11-29 |
| JP2002509915A (ja) | 2002-04-02 |
| EP1082299B1 (fr) | 2004-06-30 |
| AR020063A1 (es) | 2002-04-10 |
| CN1295560A (zh) | 2001-05-16 |
| CA2324343A1 (fr) | 1999-10-07 |
| AU749796B2 (en) | 2002-07-04 |
| IL138446A0 (en) | 2001-10-31 |
| HUP0102789A2 (hu) | 2001-12-28 |
| US6410780B1 (en) | 2002-06-25 |
| AU3270199A (en) | 1999-10-18 |
| DE69918433D1 (de) | 2004-08-05 |
| DE69918433T2 (de) | 2005-09-01 |
| BR9909267A (pt) | 2000-11-21 |
| NZ506853A (en) | 2002-09-27 |
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