GB1456514A - Substituted dialkyl 2-oxopropylphosphonates - Google Patents
Substituted dialkyl 2-oxopropylphosphonatesInfo
- Publication number
- GB1456514A GB1456514A GB2285876A GB2285876A GB1456514A GB 1456514 A GB1456514 A GB 1456514A GB 2285876 A GB2285876 A GB 2285876A GB 2285876 A GB2285876 A GB 2285876A GB 1456514 A GB1456514 A GB 1456514A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxopropylphosphonates
- nov
- alkyl
- substituted dialkyl
- formula
- 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
Links
- DVSHXLWNRCEDCW-UHFFFAOYSA-N 2-oxopropylphosphonic acid Chemical class CC(=O)CP(O)(O)=O DVSHXLWNRCEDCW-UHFFFAOYSA-N 0.000 title 1
- -1 trifluoromethylphenyl Chemical group 0.000 abstract 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 abstract 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 abstract 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 abstract 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 abstract 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005059 halophenyl group Chemical group 0.000 abstract 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical class CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- 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
- C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
-
- 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
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/40—Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6524—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having four or more nitrogen atoms as the only ring hetero atoms
Abstract
1456514 Phosphonates PFIZER Inc 7 Nov 1973 [8 Nov 1972] 22858/76 Divided out of 1456512 Heading C2P Novel phosphonates of the formula wherein Ar is phenyl, halophenyl, trifluoromethylphenyl, biphenylyl, C 1-6 alkylphenyl, C 1-6 alkoxyphenyl, 3,4 - dimethoxyphenyl, 3,4,5 - trimethoxyphenyl, 3,4 - methylenedioxyphenyl, or 1- or 2-naphthyl; R is C 1-6 alkyl; and m and n are 0 to 3 with the proviso that the sum of m and n does not exceed 3 are prepared by reacting esters of the formula wherein R<SP>1</SP> is C 1-6 alkyl, with the appropriate dialkyl methylphosphonates.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30481372A | 1972-11-08 | 1972-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1456514A true GB1456514A (en) | 1976-11-24 |
Family
ID=23178133
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2285876A Expired GB1456514A (en) | 1972-11-08 | 1973-11-07 | Substituted dialkyl 2-oxopropylphosphonates |
| GB2395076A Expired GB1456513A (en) | 1972-11-08 | 1973-11-07 | Derivatives of cyclopentaneacetic acid |
| GB5175873A Expired GB1456512A (en) | 1972-11-08 | 1973-11-07 | Substituted 16,17,18,19,20-pentanorprostaglandins |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2395076A Expired GB1456513A (en) | 1972-11-08 | 1973-11-07 | Derivatives of cyclopentaneacetic acid |
| GB5175873A Expired GB1456512A (en) | 1972-11-08 | 1973-11-07 | Substituted 16,17,18,19,20-pentanorprostaglandins |
Country Status (29)
| Country | Link |
|---|---|
| JP (3) | JPS5416491B2 (en) |
| AR (3) | AR200585A1 (en) |
| AT (3) | AT367034B (en) |
| AU (1) | AU470375B2 (en) |
| BE (1) | BE806995A (en) |
| CA (3) | CA1085831A (en) |
| CH (1) | CH597176A5 (en) |
| CS (3) | CS182793B2 (en) |
| DD (4) | DD118856A5 (en) |
| DE (1) | DE2355540C2 (en) |
| DK (1) | DK144247C (en) |
| ES (3) | ES420325A1 (en) |
| FI (1) | FI60389C (en) |
| FR (3) | FR2205335B1 (en) |
| GB (3) | GB1456514A (en) |
| HK (3) | HK28079A (en) |
| HU (3) | HU172703B (en) |
| IE (1) | IE39537B1 (en) |
| IL (1) | IL43589A (en) |
| IN (1) | IN139384B (en) |
| KE (3) | KE2932A (en) |
| MY (3) | MY7900246A (en) |
| NL (1) | NL164273C (en) |
| NO (3) | NO147836C (en) |
| PH (3) | PH13272A (en) |
| SE (4) | SE448992B (en) |
| SU (4) | SU584766A3 (en) |
| YU (3) | YU39715B (en) |
| ZA (1) | ZA738554B (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6894175B1 (en) | 1999-08-04 | 2005-05-17 | The Procter & Gamble Company | 2-Decarboxy-2-phosphinico prostaglandin derivatives and methods for their preparation and use |
| USRE43372E1 (en) | 1999-03-05 | 2012-05-08 | Duke University | C16 unsaturated FP-selective prostaglandins analogs |
| US8541466B2 (en) | 2000-03-31 | 2013-09-24 | Duke University | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
| US8618086B2 (en) | 2000-03-31 | 2013-12-31 | Duke University | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
| US8623918B2 (en) | 2008-10-29 | 2014-01-07 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| US8722739B2 (en) | 2008-10-29 | 2014-05-13 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| US9346837B2 (en) | 2000-03-31 | 2016-05-24 | Duke University | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3929862A (en) * | 1974-01-08 | 1975-12-30 | Upjohn Co | Substituted tolylesters of PGF{HD 2{B {60 |
| GB1506816A (en) * | 1975-03-31 | 1978-04-12 | Upjohn Co | Prostaglandins |
| US3986764A (en) * | 1975-03-31 | 1976-10-19 | Gte Automatic Electric Laboratories Incorporated | Panel for supporting a pair of elongated mating connectors and selectively locking them together |
| ES449162A1 (en) * | 1975-06-23 | 1977-12-16 | Syntex Inc | 16-Phenoxy and 16-substituted phenoxy-prostatrienoic acid derivatives |
| GB1516414A (en) * | 1975-08-22 | 1978-07-05 | Ici Ltd | Prostane derivatives |
| SE7809008L (en) * | 1977-12-12 | 1979-06-13 | Upjohn Co | USE OF PROSTAGLAND TYPE AMIDES TO CONTROL OR REGULATE THE REPRODUCTION CYCLE IN INDIVIDUALS OF MAMMALS |
| IN150279B (en) * | 1978-01-16 | 1982-09-04 | Pfizer | |
| DE69809268T2 (en) * | 1997-09-09 | 2003-08-28 | Procter & Gamble | AROMATIC C16-C20 SUBSTITUTED TETRAHYDRO PROSTAGLANDINS AND THEIR USE AS PROSTAGLANDIN F AGONISTS |
| JP2002329615A (en) * | 2001-05-02 | 2002-11-15 | Ohira Denshi Kk | Toroidal coil |
| US6476064B1 (en) * | 2001-06-13 | 2002-11-05 | Allergan, Inc. | Cyclopentane heptan(ene) acyl sulfonamide, 2-alkyl or 2-arylalkyl, or 2-heteroarylalkenyl derivatives as therapeutic agents |
| WO2006047466A2 (en) | 2004-10-21 | 2006-05-04 | Duke University | Ophthamological drugs |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1324737A (en) * | 1970-11-02 | 1973-07-25 | Upjohn Co | Prostaglandins and the preparation thereof |
| IE37602B1 (en) * | 1971-05-11 | 1977-08-31 | Ici Ltd | Cyclopentane derivatives |
-
1972
- 1972-11-07 DD DD182498*A patent/DD118856A5/xx unknown
-
1973
- 1973-10-29 SE SE7314686A patent/SE448992B/en unknown
- 1973-11-07 JP JP12527273A patent/JPS5416491B2/ja not_active Expired
- 1973-11-07 CH CH1563973A patent/CH597176A5/xx not_active IP Right Cessation
- 1973-11-07 GB GB2285876A patent/GB1456514A/en not_active Expired
- 1973-11-07 YU YU2880/73A patent/YU39715B/en unknown
- 1973-11-07 DK DK601073A patent/DK144247C/en not_active IP Right Cessation
- 1973-11-07 IE IE2002/73A patent/IE39537B1/en unknown
- 1973-11-07 IL IL43589A patent/IL43589A/en unknown
- 1973-11-07 NL NL7315263.A patent/NL164273C/en not_active IP Right Cessation
- 1973-11-07 NO NO4288/73A patent/NO147836C/en unknown
- 1973-11-07 DD DD182497*A patent/DD117233A5/xx unknown
- 1973-11-07 PH PH15191A patent/PH13272A/en unknown
- 1973-11-07 AU AU62247/73A patent/AU470375B2/en not_active Expired
- 1973-11-07 DD DD174504A patent/DD109212A5/xx unknown
- 1973-11-07 ES ES420325A patent/ES420325A1/en not_active Expired
- 1973-11-07 IN IN2448/CAL/73A patent/IN139384B/en unknown
- 1973-11-07 GB GB2395076A patent/GB1456513A/en not_active Expired
- 1973-11-07 AT AT0936973A patent/AT367034B/en not_active IP Right Cessation
- 1973-11-07 FR FR7339544A patent/FR2205335B1/fr not_active Expired
- 1973-11-07 DD DD182499*A patent/DD119411A5/xx unknown
- 1973-11-07 AR AR250885A patent/AR200585A1/en active
- 1973-11-07 DE DE2355540A patent/DE2355540C2/en not_active Expired
- 1973-11-07 ZA ZA738554A patent/ZA738554B/en unknown
- 1973-11-07 CA CA185,274A patent/CA1085831A/en not_active Expired
- 1973-11-07 GB GB5175873A patent/GB1456512A/en not_active Expired
- 1973-11-07 FI FI3443/73A patent/FI60389C/en active
- 1973-11-07 BE BE1005485A patent/BE806995A/en not_active IP Right Cessation
- 1973-11-08 CS CS7500006065A patent/CS182793B2/en unknown
- 1973-11-08 CS CS7300007669A patent/CS182791B2/en unknown
- 1973-11-08 HU HU72PI00000399A patent/HU172703B/en unknown
- 1973-11-08 HU HU73PI451A patent/HU173507B/en unknown
- 1973-11-08 CS CS7500006066A patent/CS182794B2/en unknown
- 1973-11-08 HU HU73PI00000452A patent/HU171819B/en unknown
- 1973-11-11 SU SU7301971722A patent/SU584766A3/en active
-
1974
- 1974-06-06 AR AR254090A patent/AR202931A1/en active
- 1974-06-06 AR AR254091A patent/AR199966A1/en active
- 1974-09-26 NO NO743493A patent/NO148998C/en unknown
- 1974-12-18 ES ES433046A patent/ES433046A1/en not_active Expired
- 1974-12-18 ES ES433047A patent/ES433047A1/en not_active Expired
-
1975
- 1975-02-18 NO NO750535A patent/NO149139C/en unknown
- 1975-02-18 SU SU752106791A patent/SU667141A3/en active
- 1975-02-19 SU SU752106125A patent/SU893130A3/en active
- 1975-07-24 PH PH17410A patent/PH13110A/en unknown
- 1975-07-24 PH PH17409A patent/PH13325A/en unknown
- 1975-08-22 FR FR7526059A patent/FR2279729A1/en active Granted
- 1975-08-22 FR FR7526060A patent/FR2283146A1/en active Granted
-
1976
- 1976-07-23 AT AT544576A patent/AT360672B/en not_active IP Right Cessation
- 1976-07-23 AT AT544676A patent/AT353285B/en active
- 1976-10-15 JP JP51123737A patent/JPS5253841A/en active Pending
- 1976-10-15 JP JP51123738A patent/JPS5257147A/en active Pending
-
1977
- 1977-01-24 SE SE7700716A patent/SE445111B/en not_active IP Right Cessation
- 1977-01-24 SE SE7700718A patent/SE431756B/en not_active IP Right Cessation
- 1977-01-24 SE SE7700717A patent/SE436278B/en not_active IP Right Cessation
- 1977-07-11 CA CA341,897A patent/CA1088930A/en not_active Expired
- 1977-07-11 CA CA341,898A patent/CA1088931A/en not_active Expired
-
1978
- 1978-07-27 SU SU782629453A patent/SU745362A3/en active
-
1979
- 1979-03-15 KE KE2932A patent/KE2932A/en unknown
- 1979-03-15 KE KE2931A patent/KE2931A/en unknown
- 1979-03-15 KE KE2930A patent/KE2930A/en unknown
- 1979-05-03 HK HK280/79A patent/HK28079A/en unknown
- 1979-05-03 HK HK281/79A patent/HK28179A/en unknown
- 1979-05-03 HK HK279/79A patent/HK27979A/en unknown
- 1979-12-30 MY MY246/79A patent/MY7900246A/en unknown
- 1979-12-30 MY MY243/79A patent/MY7900243A/en unknown
- 1979-12-30 MY MY245/79A patent/MY7900245A/en unknown
-
1980
- 1980-10-23 YU YU2707/80A patent/YU36975B/en unknown
- 1980-10-23 YU YU2706/80A patent/YU37316B/en unknown
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE43372E1 (en) | 1999-03-05 | 2012-05-08 | Duke University | C16 unsaturated FP-selective prostaglandins analogs |
| US6894175B1 (en) | 1999-08-04 | 2005-05-17 | The Procter & Gamble Company | 2-Decarboxy-2-phosphinico prostaglandin derivatives and methods for their preparation and use |
| US7074942B2 (en) | 1999-08-04 | 2006-07-11 | The Procter & Gamble Company | 2-decarboxy-2-phosphinico prostaglandin derivatives and methods for their preparation and use |
| US7115659B2 (en) | 1999-08-04 | 2006-10-03 | The Procter & Gamble Company | Method of treating a condition by administering a prostaglandin derivative |
| US8541466B2 (en) | 2000-03-31 | 2013-09-24 | Duke University | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
| US8618086B2 (en) | 2000-03-31 | 2013-12-31 | Duke University | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
| US8906962B2 (en) | 2000-03-31 | 2014-12-09 | Duke University | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
| US9346837B2 (en) | 2000-03-31 | 2016-05-24 | Duke University | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
| US9579270B2 (en) | 2000-03-31 | 2017-02-28 | Duke University | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
| US9675539B2 (en) | 2000-03-31 | 2017-06-13 | Duke University | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
| US8623918B2 (en) | 2008-10-29 | 2014-01-07 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| US8722739B2 (en) | 2008-10-29 | 2014-05-13 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19921107 |