PL95790B1 - Sposob wytwarzania nowych amidowych pochodnych nonapetydow - Google Patents
Sposob wytwarzania nowych amidowych pochodnych nonapetydow Download PDFInfo
- Publication number
- PL95790B1 PL95790B1 PL1973162210A PL16221073A PL95790B1 PL 95790 B1 PL95790 B1 PL 95790B1 PL 1973162210 A PL1973162210 A PL 1973162210A PL 16221073 A PL16221073 A PL 16221073A PL 95790 B1 PL95790 B1 PL 95790B1
- Authority
- PL
- Poland
- Prior art keywords
- pro
- ser
- trp
- arg
- pir
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001408 amides Chemical class 0.000 claims abstract 7
- 238000000034 method Methods 0.000 claims 19
- 125000003440 L-leucyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 claims 8
- 125000003798 L-tyrosyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 8
- -1 L-norleucyl Chemical group 0.000 claims 7
- 125000002435 L-phenylalanyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 238000009833 condensation Methods 0.000 claims 5
- 230000005494 condensation Effects 0.000 claims 5
- 125000000524 functional group Chemical group 0.000 claims 4
- 150000001413 amino acids Chemical class 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000002061 L-isoleucyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])[C@](C([H])([H])[H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- 230000004913 activation Effects 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 239000004615 ingredient Substances 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- ZGKXAUIVGIBISK-SZMVWBNQSA-N Glu-His-Trp Chemical compound N[C@@H](CCC(O)=O)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(O)=O ZGKXAUIVGIBISK-SZMVWBNQSA-N 0.000 claims 1
- 125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/23—Luteinising hormone-releasing hormone [LHRH]; Related peptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/13—Luteinizing hormone-releasing hormone; related peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Endocrinology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Claims (12)
1. Zastrzezenia patentowe 1. Sposób wytwarzania nowyck amidowych po¬ chodnych nonapeptydów o wzorze L-piroglutamyl- -L-histydyl -L -tryptofil -L-seryl-At -glicyl-A2-L- -arginil-L-Prolil-Y- (wzór 1), w którym At oznacza L-tyrozyl, A2 oznacza L-leucyl, a Y ozna¬ cza grupe o wzorze -NHR, w którym R oznacza prosty lub rozgaleziony rodnik alkilowy, o 1—3 atomach wegla, ewentualnie podstawiony grupa wodorotlenowa lub Y oznacza grupe pirolidynowa, oraz farmaceutycznie dopuszczalnych soli tych zwiazków, znamienny tym, ze skladnik A, którym jest H-Pir/Glu-OH, H-/PhVGlu-His-OH, H-/Hr/ /Glu-His-Trip-OH, Hn/Pir/Gflu-His-Tng-Ser-OIH, H- -/Pir-ZGlu-His-Trp-Ser-Ai-OH, H-/Pir/Glu-His- -/Pir-ZGlu-His-Trp-Ser-Ai-OH, H-/Pir/Glu-His- -Trp-Ser-Ai-Gli-OH, H-ZPir/Glu-Has-Trp-Ser-Ai- -Gli-A2-OH, H-ZPiir/Glu^His-Trp-Ser-A^li-Aj- -Arg-OH albo H^/Pir/Glu-His-Trp-Ser-Ai-Gli-Ag- -Arg-Pro-OH, w którym Ai i A^ maja wyzej poda¬ ne znaczenia poddaje sie kondensacji ze skladni¬ kiem B, którym jest H-His-Trp-Ser-Ai-Gli-Ag-Arg- -Pro-Y, H-Trp-Ser-Ai-Gli-Aj-Arg-Pro-Y, H-Ser- -Ai-Gli-Aa-Arg-Pro-Y, H-Aj-Gli-Aj-Arg-Pro-Y, H- -Gli-A2-Arg-Pro-Y, H-Ag-Arg-Pro-Y, H-Arg-Pro-95790 24 -Y, H-Pro-Y albo H-Y, w których Alf A2 i Y ma¬ ja wyzej podane znaczenie, przy czym suma ami¬ nokwasów skladników A i B sklada sie na amido¬ wa pochodna nonapeptydu o powyzszym wzorze, i grupy funkcyjne skladników wyjsciowych A i B moga byc ewentualnie chronione, a po kondensacji poddaje sie je ewentualnie odszczepieniu.
2. Sposób wytwarzania nowych amidowych po¬ chodnych nonapeptydów o wzorze L-piroglutamyl- -L-histydyl-L -tryptofil-L -Seryl-Ai-Glicyl-Aa-L-ar- ginyl-L-prolil-Y (wzór 1), w którym At oznacza L- -fenyloalanyl, A2 oznacza L-leucyl, L-izoleucyl, L- -norleucyl, L-waMl, L-norfalil, L-metionyl lub L-fe- ryloalanyl, a Y oznacza grupe o wzorze -NHR, w którym R oznacza prosty lub rozgaleziony rodnik alkilowy o 1—3 atomach wegla, ewentualnie pod¬ stawiony grupa wodorotlenowa lub Y-oznacza gru¬ pe pdroiidynowa oraz farmaceutycznie dopuszczal¬ nych soli tych zwiaizków, znamienny tym, ze skla¬ dnik A, którym jest H-^TPir/Glu-OH, H-/Pir/Glu- -His~OH, H-/Pir/Glu-His-Trp-OH, H-^Pir/Glu-His- -Trp-Seron, H-^PirZ-Glu-His-Trp-Ser-Aj-OH, H- -/Pir/Ghi-His-Trp-Ser-A^GM-OH, H-/Pir/Glu-His- -Trp-Ser-A^Gli-Aa-OH, H-/Pir/Glu-His-Trp-Ser- -Ai-Gli-Ag-Arg-OH, albo H^/Pir/Olu-Hds-Trp-Ser- -At-GM-Ag-Arg-Pro-OH, w których Ax i A2 maja wyzej podane znaczenie poddaje sie kondensacji ze skladnikiem B, którym jest H-His-Trp-Ser-At-Gli- -A2-Arg-Pro-Y, H-Trp-Ser-At-GM-Aa-Arg-Pro-Y, H-Ser-Ai-Gli-Aa-Arg-Pro-Y, H-A^Gli-A2-Arg-Pro- -Y, H-Gli-A2-Arg-Pro-Y, H-A2-Arg-Pro-Y, H-Arg- -Pro-Y, H-Pro-Y, albo H-Y, w których Ai, A2 i Y maja wyzej podane znaczenie, przy czym suma aminokwasów skladników A i B sklada sie na ami¬ dowa pochodna nonatpeipttydu o poiwyzlszyim wzorze i grupy funkcyjne skladników wyjsciowych A i B moga byc ewentualnie obronione, a po kondeosatoji podaje sie je ewentualnie odszczepieniu.
3. , Sposób wytwarzania nowych amidowych po¬ chodnych nonapeptydów o wzorze L-piroglutamyl- -Lnhistydyl-L -tryptofil-L -Seryl-A1-glicyl-A2-L-ar- ginyl-L-prolil-Y7 w którym A, oznacza L-tyrozyl, A2 — oznacza L-izoleucyl, L-norleucyl, L-walil, L- -norwalil, L-metionyl lub L-fenyloalanyl, a Y ozna¬ cza grupe o wzorze -NHR, w którym R oznacza prosty lub rozgaleziony rodnik alkilowy o 1—3 atomach wegla, ewentualnie podstawiony grupa wodorotlenowa, lub Y oznacza grupe pirolidynowa oraz farmaceutycznie dopuszczalnych soli tych zwiazków, znamienny tym, ze skladnik A, którym jest H-/Pir/Glu-OH, H-/Pir/Glu-His-OH, H-/Pir/ /Glu-His-Trp-OH, H^Pir/Glu-His-Trp-Ser-OH, H-yPk/Glu-His-Trp-Ser-Ai-OH, H-iTir/Giu-His- -Trp-Ser-A^Gli-OH, H^Pir/Glu-His-Trp-Ser-A!- -Gli-A2-OH, H^Pir/Glu-Has-Trij-Ser-Ai-GM-Ajj- wAng-OH sUho H-ZPri/^Gau-His-Trp-Setr-Ai-Gli- -A2-Arg-Pro-OH, w których At i A2 maja wyzej 5 podane znaczenie, poddaje sie kondensacji ze skla¬ dnikiem B, którym jest H-His-Trp-Ser-Ai-Gli-Aa- -Arg-Pro-Y, H-Trp-Ser-AinGM-Ajj-Arg-Pro-Y, H- -Ser-Ai-Glli-Az-Arg-Pro-Y, H-A^Gli-Ag-Arg-Pro-Y, H-Gli-A2-Arg-Pro-Y, H-A2-Arg-PrO-Y, H-Arg-Pro- 10 -Y, H-Pro-Y albo H-Y, w których Al9 A2 i Y maja wyzej podane znaczenie, przy czym su¬ ma aminokwasów skladników A i B sklada sie na amidowa pochodna nonapeptydu o powyzszym wzorze i grupy funkcyjne skladników wyjsciowych 15 A i B moga byc ewentualnie chronione, a po kon¬ densacji poddaje sie je ewentualnie odszczepie¬ niu.
4. Sposób wedlug zastrz. 1, znamienny tym, ze poddaje sie kondensacji skladniki A i B, w któ- 20 rych Ax oznacza L-tyrozyl, A2 oznacza L-leucyl, a Y oznacza grupe -NH-CH2-CH3.
5. Sposób wedlug zastrz. 1, znamienny tym, ze poddaje sie kondensacji skladniki A i B, w których Ax oznacza L-ltyirozyl, A2 oznacza L-leucyl, a Y ozma- 25 cza grupe -NH-CH2-CH2-OH.
6. Sposób wedlug zastrz. 1, znamienny tym, ze poddaje sie kondensacji skladniki A i B, w któ¬ rych AL oznacza L-tyrozyl, A2 oznacza L-leucyl, a Y oznacza grupe -NH-CH3. 30
7. Sposób wedlug zastrz. 1, znamienny tym, ze poddaje sie kondensacji skladniki A i B, w któ¬ rych Aj oznacza L-tyrozyl, A2 oznacza L-leucyl, a Y oznacza grupe o wzorze -NH-^CH^-OHa.
8. Sposób wedlug zastrz. 1, znamienny tym, ze 35 poddaje sie kondensacji skladniki A i B, w któ¬ rych At oznacza L-tyrozyl, A2 oznacza L-leucyl, a Y oznacza grupe -NH-CH-ZCH/a.
9. Sposób wedlug zasitrz. 2, znamienny tym, ze poddaje sie kondensacji skladniki A i B, w któ- 40 rych Ax oznacza L-fenyloalanyl, A2 oznacza L-leu¬ cyl, a Y oznacza grupe -NH-CH2-CH3.
10. Sposób wedlug zastrz. 2, znamienny tym, ze poddaje sie kondensacji skladniki A i B, w któ¬ rych At oznacza L-fenyloalanyl, A2 oznacza L-leu- 45 cyl, a Y oznacza grupe -NH-CH2-CH3.
11. : Sjposófo wedlug zastriz. 3, znamienny tym, ze poddaje sie kondensacji skladniki A i B, w któ¬ rych Aj ozniacza L-tyrozyl, A2 oznacza L-norleucyl, a Y oznacza grupe -NH-CH2CH3, 50
12. Sposób wedlug zastriz. 3, znamienny tym, ze poddaje sie kondensacji skladniki A i B, w któ¬ rych Ai oznacza L-tyrozyl, A2 oznacza L-metionyl, a Y oznacza grupe -NH-CH2CH3.95790 H-(Pir)Glu-His-Trp-Ser-ArGLL-OH+DCC+HONBI (skladnik (A)) aktywacja Z H-(Pir)GLu7His-Trp-Ser-ArGlL)-ONBI+H-A2-Arq-Pro-y zaktywowany skladnik (A)) (skladnik (B) z chroniona v V ^ grupa, funkcyjna] utworzenie wiazania peptydowego H-(Pir)GLa-His-Trp-Ser-A,-GLL|-A2-Arg-Pro-y usuniecie grupy ochronnej H-(Pir)Glu-His-Trp-Ser-ArGli-A2-Arg-Pro-Y , , . . Schemat \ Wzór 1 H-(Pir)Glu-His-Trp-Ser-ArGlL-OH+H-A2-Arg-Pro-y (skladnik (A) ) (skladnik (B) z chroniona \ \ // xqrupq funkcyjna, + DCOHONBI ' ® aktywacja (Z) utworzenie wiazania peptydowego Z H-(Pir)Glu-His-Trp-Ser-ArGly-A2-Arg-Pro-y usuniecie grupLj ochronnej H-(Pir) GLu-His-Trp-Ser- Ai- GL -A2-Arg-Pro-Y Schemat Z95790 HN \ -NHCH,CH,CH,CHCOOH / I H2N NH2 Wzór la H o% A /Co- Wzor 2 Drukarnia Narodowa Zaklad Nr 6, zam. 1024/77 Cena 45 zl PL PL
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4268672A JPS5324423B2 (pl) | 1972-04-29 | 1972-04-29 | |
| JP11845272A JPS5324424B2 (pl) | 1972-11-24 | 1972-11-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL95790B1 true PL95790B1 (pl) | 1977-11-30 |
Family
ID=26382407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973162210A PL95790B1 (pl) | 1972-04-29 | 1973-04-28 | Sposob wytwarzania nowych amidowych pochodnych nonapetydow |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3853837A (pl) |
| AT (1) | AT333988B (pl) |
| AU (1) | AU453931B2 (pl) |
| CA (1) | CA1005815A (pl) |
| CH (1) | CH580065A5 (pl) |
| CS (1) | CS188162B2 (pl) |
| DE (2) | DE2366379C2 (pl) |
| DK (1) | DK147851C (pl) |
| ES (1) | ES414197A1 (pl) |
| FI (1) | FI56676C (pl) |
| FR (1) | FR2183021B1 (pl) |
| GB (1) | GB1403642A (pl) |
| HU (1) | HU168696B (pl) |
| NL (2) | NL176856C (pl) |
| NO (1) | NO139560C (pl) |
| PL (1) | PL95790B1 (pl) |
| SE (1) | SE397520B (pl) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931138A (en) * | 1973-03-13 | 1976-01-06 | Abbott Laboratories | N-carbobenzoxy-pyroglutamyl-histidine |
| CS180644B2 (en) * | 1973-09-29 | 1978-01-31 | Takeda Chemical Industries Ltd | Process for preparing nonapeptides |
| GB1532211A (en) * | 1974-10-25 | 1978-11-15 | Wellcome Found | Lh-rh peptide analogues |
| US4338305A (en) * | 1975-03-24 | 1982-07-06 | American Home Products Corporation | Use of LRH and LRH agonists |
| AU497512B2 (en) * | 1975-04-15 | 1978-12-14 | Ici Australia Limited | Nona and deca-peptides |
| US4034082A (en) * | 1976-03-01 | 1977-07-05 | Abbott Laboratories | Method to prevent reproduction in warm-blooded female animals with nonapeptides |
| DE2905502C2 (de) * | 1979-02-14 | 1982-07-15 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von LH-RH bzw. LH-RH-Analoga und Pyroglutamyl-N↑i↑m↑-dinitrophenyl-histidin |
| DE3020941A1 (de) * | 1980-06-03 | 1981-12-17 | Hoechst Ag, 6000 Frankfurt | Nonapeptid, verfahren zu seiner herstellung, dieses enthaltendes mittel und seine verwendung |
| US4675189A (en) * | 1980-11-18 | 1987-06-23 | Syntex (U.S.A.) Inc. | Microencapsulation of water soluble active polypeptides |
| US4659696A (en) * | 1982-04-30 | 1987-04-21 | Takeda Chemical Industries, Ltd. | Pharmaceutical composition and its nasal or vaginal use |
| HU193607B (en) * | 1985-07-18 | 1987-11-30 | Innofinance Altalanos Innovaci | Process for production of sexual products applyable for natural or artificial insemination for mammates |
| US4897268A (en) * | 1987-08-03 | 1990-01-30 | Southern Research Institute | Drug delivery system and method of making the same |
| US5068221A (en) * | 1989-05-09 | 1991-11-26 | Mathias John R | Treatment of motility disorders with a gnrh analog |
| JP2653255B2 (ja) | 1990-02-13 | 1997-09-17 | 武田薬品工業株式会社 | 長期徐放型マイクロカプセル |
| CA2050425A1 (en) | 1990-09-03 | 1992-03-04 | Yoshiaki Uda | Pharmaceutical composition and its mucous use |
| NZ240214A (en) | 1990-10-16 | 1993-02-25 | Takeda Chemical Industries Ltd | Polymer compositions comprising a polylactic acid and a copolymer of glycolic acid and a hydroxycarboxylic acid; use as carrier for prolonged release pharmaceutical compositions of water soluble drugs |
| US5434136A (en) * | 1990-12-14 | 1995-07-18 | Mathias; John R. | Treatment of motility disorders with a GNRH analog |
| US5518730A (en) * | 1992-06-03 | 1996-05-21 | Fuisz Technologies Ltd. | Biodegradable controlled release flash flow melt-spun delivery system |
| ATE161716T1 (de) | 1992-08-07 | 1998-01-15 | Takeda Chemical Industries Ltd | Herstellung von mikrokapseln, die wasserlösliche arzneimittel enthalten |
| CA2143044C (en) * | 1994-02-21 | 2005-04-12 | Yasutaka Igari | Matrix for sustained-release preparation |
| US6117455A (en) * | 1994-09-30 | 2000-09-12 | Takeda Chemical Industries, Ltd. | Sustained-release microcapsule of amorphous water-soluble pharmaceutical active agent |
| US5837281A (en) | 1995-03-17 | 1998-11-17 | Takeda Chemical Industries, Ltd. | Stabilized interface for iontophoresis |
| US6413536B1 (en) | 1995-06-07 | 2002-07-02 | Southern Biosystems, Inc. | High viscosity liquid controlled delivery system and medical or surgical device |
| US7833543B2 (en) * | 1995-06-07 | 2010-11-16 | Durect Corporation | High viscosity liquid controlled delivery system and medical or surgical device |
| CA2192782C (en) | 1995-12-15 | 2008-10-14 | Nobuyuki Takechi | Production of microspheres |
| CA2192773C (en) | 1995-12-15 | 2008-09-23 | Hiroaki Okada | Production of sustained-release preparation for injection |
| CN1095681C (zh) * | 1996-06-20 | 2002-12-11 | 久光制药株式会社 | 一种用于离子电渗疗法的装置结构 |
| US20060025328A1 (en) * | 1997-05-28 | 2006-02-02 | Burns Patrick J | Compositions suitable for controlled release of the hormone GnRH and its analogs |
| US6051558A (en) * | 1997-05-28 | 2000-04-18 | Southern Biosystems, Inc. | Compositions suitable for controlled release of the hormone GnRH and its analogs |
| EP0882736A1 (en) * | 1997-06-02 | 1998-12-09 | Laboratoire Theramex S.A. | LH-RH peptide analogues, their uses and pharmaceutical compositions containing them |
| JP4414517B2 (ja) | 1999-09-01 | 2010-02-10 | 久光製薬株式会社 | イオントフォレーシス用デバイス構造体 |
| US20040001889A1 (en) | 2002-06-25 | 2004-01-01 | Guohua Chen | Short duration depot formulations |
| CN101797221B (zh) * | 2002-12-13 | 2013-06-12 | 杜雷科特公司 | 包含高粘度液体载体材料的口服递药系统 |
| HUE032040T2 (en) | 2004-09-17 | 2017-09-28 | Durect Corp | Saib-containing (sucrose acetate-isobutyrate) sustained-release local anesthetic composition |
| US20070027105A1 (en) | 2005-07-26 | 2007-02-01 | Alza Corporation | Peroxide removal from drug delivery vehicle |
| US8337883B2 (en) | 2006-11-03 | 2012-12-25 | Durect Corporation | Transdermal delivery systems |
| AU2008335809A1 (en) | 2007-12-06 | 2009-06-18 | Durect Corporation | Methods useful for the treatment of pain, arthritic conditions, or inflammation associated with a chronic condition |
| US20100260844A1 (en) | 2008-11-03 | 2010-10-14 | Scicinski Jan J | Oral pharmaceutical dosage forms |
| WO2014144975A1 (en) | 2013-03-15 | 2014-09-18 | Durect Corporation | Compositions with a rheological modifier to reduce dissolution variability |
| CA3028450A1 (en) | 2016-07-06 | 2018-01-11 | Durect Corporation | Oral dosage form with drug composition, barrier layer and drug layer |
| WO2021146215A1 (en) | 2020-01-13 | 2021-07-22 | Durect Corporation | Sustained release drug delivery systems with reduced impurities and related methods |
| JP2024503402A (ja) | 2021-01-12 | 2024-01-25 | デュレクト コーポレーション | 徐放性薬物送達システム及び関連の方法 |
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1973
- 1973-04-10 NO NO1481/73A patent/NO139560C/no unknown
- 1973-04-18 AU AU54676/73A patent/AU453931B2/en not_active Expired
- 1973-04-25 US US00354381A patent/US3853837A/en not_active Expired - Lifetime
- 1973-04-25 DK DK225073A patent/DK147851C/da not_active IP Right Cessation
- 1973-04-25 FR FR7315044A patent/FR2183021B1/fr not_active Expired
- 1973-04-26 DE DE2366379A patent/DE2366379C2/de not_active Expired
- 1973-04-26 SE SE7305905A patent/SE397520B/xx unknown
- 1973-04-26 DE DE2321174A patent/DE2321174C2/de not_active Expired
- 1973-04-27 AT AT377173A patent/AT333988B/de not_active IP Right Cessation
- 1973-04-27 FI FI1375/73A patent/FI56676C/fi active
- 1973-04-27 CS CS733045A patent/CS188162B2/cs unknown
- 1973-04-27 NL NLAANVRAGE7305995,A patent/NL176856C/xx active Protection Beyond IP Right Term
- 1973-04-27 CA CA169,683A patent/CA1005815A/en not_active Expired
- 1973-04-27 CH CH606673A patent/CH580065A5/xx not_active IP Right Cessation
- 1973-04-28 ES ES414197A patent/ES414197A1/es not_active Expired
- 1973-04-28 PL PL1973162210A patent/PL95790B1/pl unknown
- 1973-04-28 HU HUTA1249A patent/HU168696B/hu unknown
- 1973-04-30 GB GB2042773A patent/GB1403642A/en not_active Expired
-
1993
- 1993-02-04 NL NL930004C patent/NL930004I1/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU5467673A (en) | 1974-10-17 |
| FR2183021B1 (pl) | 1976-04-09 |
| HU168696B (pl) | 1976-06-28 |
| ES414197A1 (es) | 1976-05-01 |
| NO139560B (no) | 1978-12-27 |
| DE2321174A1 (de) | 1973-11-08 |
| DE2321174C2 (de) | 1982-04-15 |
| DK147851C (da) | 1986-03-10 |
| GB1403642A (en) | 1975-08-28 |
| US3853837A (en) | 1974-12-10 |
| DE2366379C2 (de) | 1985-01-17 |
| FI56676B (fi) | 1979-11-30 |
| DK147851B (da) | 1984-12-24 |
| NL176856C (nl) | 1985-06-17 |
| FR2183021A1 (pl) | 1973-12-14 |
| ATA377173A (de) | 1976-04-15 |
| AT333988B (de) | 1976-12-27 |
| CH580065A5 (pl) | 1976-09-30 |
| CA1005815A (en) | 1977-02-22 |
| NL930004I1 (nl) | 1993-04-01 |
| AU453931B2 (en) | 1974-10-17 |
| NO139560C (no) | 1979-04-04 |
| NL7305995A (pl) | 1973-10-31 |
| SE397520B (sv) | 1977-11-07 |
| CS188162B2 (en) | 1979-02-28 |
| FI56676C (fi) | 1980-03-10 |
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