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
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)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (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 (40)
| 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 |
| ZA918168B (en) | 1990-10-16 | 1993-04-14 | Takeda Chemical Industries Ltd | Prolonged release preparation and polymers thereof. |
| 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 |
| DE69316101T2 (de) | 1992-08-07 | 1998-10-22 | Takeda Chemical Industries Ltd | Herstellung von Mikrokapseln, die wasserlösliche Arzneimittel enthalten |
| DE69508985T2 (de) * | 1994-02-21 | 1999-08-19 | Takeda Chemical Industries Ltd | Polyester Matrix für eine pharmazeutische Zusammensetzung mit verzögerter Freigabe |
| 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 |
| US7833543B2 (en) * | 1995-06-07 | 2010-11-16 | Durect Corporation | High viscosity liquid controlled delivery system and medical or surgical device |
| US6413536B1 (en) | 1995-06-07 | 2002-07-02 | Southern Biosystems, Inc. | High viscosity liquid controlled delivery system and medical or surgical device |
| CA2192773C (en) | 1995-12-15 | 2008-09-23 | Hiroaki Okada | Production of sustained-release preparation for injection |
| CA2192782C (en) | 1995-12-15 | 2008-10-14 | Nobuyuki Takechi | Production of microspheres |
| US5908400A (en) * | 1996-06-20 | 1999-06-01 | Hisamitsu Pharmaceutical Co., Inc. | Device structure for iontophoresis |
| US6051558A (en) * | 1997-05-28 | 2000-04-18 | Southern Biosystems, Inc. | Compositions suitable for controlled release of the hormone GnRH and its analogs |
| US20060025328A1 (en) * | 1997-05-28 | 2006-02-02 | Burns Patrick J | 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 |
| AU2003299659A1 (en) * | 2002-12-13 | 2004-07-09 | Durect Corporation | Oral drug delivery system comprising high viscosity liquid carrier materials |
| JP5285275B2 (ja) | 2004-09-17 | 2013-09-11 | デュレクト コーポレーション | 制御されたデリバリーシステム |
| US20070027105A1 (en) | 2005-07-26 | 2007-02-01 | Alza Corporation | Peroxide removal from drug delivery vehicle |
| AU2007325918B2 (en) | 2006-11-03 | 2013-10-17 | Durect Corporation | Transdermal delivery systems comprising bupivacaine |
| JP2011506318A (ja) | 2007-12-06 | 2011-03-03 | デュレクト コーポレーション | 経口医薬製剤 |
| US20100260844A1 (en) | 2008-11-03 | 2010-10-14 | Scicinski Jan J | Oral pharmaceutical dosage forms |
| CA2905131A1 (en) | 2013-03-15 | 2014-09-18 | Durect Corporation | Compositions with a rheological modifier to reduce dissolution variability |
| KR20220140711A (ko) | 2020-01-13 | 2022-10-18 | 듀렉트 코퍼레이션 | 불순물이 감소된 지속 방출 약물 전달 시스템 및 관련 방법 |
-
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 FR FR7315044A patent/FR2183021B1/fr 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
- 1973-04-26 DE DE2366379A patent/DE2366379C2/de not_active Expired
- 1973-04-26 DE DE2321174A patent/DE2321174C2/de not_active Expired
- 1973-04-26 SE SE7305905A patent/SE397520B/xx unknown
- 1973-04-27 AT AT377173A patent/AT333988B/de not_active IP Right Cessation
- 1973-04-27 CA CA169,683A patent/CA1005815A/en not_active Expired
- 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 CH CH606673A patent/CH580065A5/xx not_active IP Right Cessation
- 1973-04-27 FI FI1375/73A patent/FI56676C/fi active
- 1973-04-28 PL PL1973162210A patent/PL95790B1/pl unknown
- 1973-04-28 HU HUTA1249A patent/HU168696B/hu unknown
- 1973-04-28 ES ES414197A patent/ES414197A1/es not_active Expired
- 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 |
|---|---|
| AU453931B2 (en) | 1974-10-17 |
| AU5467673A (en) | 1974-10-17 |
| DK147851B (da) | 1984-12-24 |
| NL930004I1 (nl) | 1993-04-01 |
| GB1403642A (en) | 1975-08-28 |
| US3853837A (en) | 1974-12-10 |
| ATA377173A (de) | 1976-04-15 |
| FR2183021A1 (pl) | 1973-12-14 |
| FI56676C (fi) | 1980-03-10 |
| FR2183021B1 (pl) | 1976-04-09 |
| HU168696B (pl) | 1976-06-28 |
| DE2366379C2 (de) | 1985-01-17 |
| AT333988B (de) | 1976-12-27 |
| ES414197A1 (es) | 1976-05-01 |
| DK147851C (da) | 1986-03-10 |
| FI56676B (fi) | 1979-11-30 |
| CH580065A5 (pl) | 1976-09-30 |
| CS188162B2 (en) | 1979-02-28 |
| DE2321174A1 (de) | 1973-11-08 |
| NO139560C (no) | 1979-04-04 |
| NL176856C (nl) | 1985-06-17 |
| NL7305995A (pl) | 1973-10-31 |
| NO139560B (no) | 1978-12-27 |
| SE397520B (sv) | 1977-11-07 |
| DE2321174C2 (de) | 1982-04-15 |
| CA1005815A (en) | 1977-02-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PL95790B1 (pl) | Sposob wytwarzania nowych amidowych pochodnych nonapetydow | |
| ID29632A (id) | Pembuatan bentuk-bentuk dosis larutan bening berair dengan asam-asam empedu | |
| TR199901968T2 (xx) | Sabit s�v� interferon form�lleri. | |
| FI84836C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara (2-metyl-tiazolidin-4-karbonyl) aminosyra. | |
| EP0781781A3 (en) | Camptothecin derivatives | |
| EP0394989A3 (en) | Peptide compounds, process for preparation thereof and pharmaceutical composition comprising the same | |
| ES2172780T3 (es) | Derivados de acido fenilpropanoico sustituidos en para como antagonistas de integrina. | |
| SE8302130L (sv) | Farmakologiskt aktiva bifosfonater, forfarande for deras framstellning och farmaceutiska kompositioner innehallande desamma | |
| HU9401323D0 (en) | New aminoacid derivates, process for producing the same and pharmaceutical compositions containing these compounds | |
| HU913331D0 (en) | Peptides and process for their production | |
| CA2182244A1 (en) | Camptothecin derivatives | |
| BG100946A (en) | New amino acid derivatives, method for their preparation and pharmaceutical compositions containing them | |
| CA2281049A1 (en) | Water-soluble pharmaceutical composition in an ionic complex and the use thereof | |
| IE821846L (en) | Carbamimidoyl-1-carbadethiapen-2-em-3 carboxylic acid | |
| KR870700067A (ko) | 피리도(2,3-d)-피리미딘 유도체 | |
| GB1279895A (en) | O-acyl-lysergols and process for preparing them | |
| ES506284A0 (es) | Un procedimiento para la preparacion de acidos 1, carbadestiapen-2-em-3-carboxililos 2- y 6- sustituidos. | |
| IT1244501B (it) | Derivati amminoacilici e oligopeptidici dell'allopurinolo dotati di attivita' immunostimolante e composizioni farmaceutiche che li contengono | |
| ZA839615B (en) | Dialkyl-amino-alkoxy derivatives,process for their preparation and pharmaceutical compositions containing them | |
| GB1415471A (en) | Phenylethylamine derivatives | |
| PL143712B1 (en) | Method of obtaining novel salts - derivatives of oxazephorine | |
| EP0309971A3 (en) | New spergualin-related compound and pharmaceutical composition | |
| ATE78816T1 (de) | N-substituierte 3,4-dihydropyrimidinderivate, verfahren zu deren herstellung und diese enthaltende zusammenstellung fuer die behandlung von anordnungen eines kardiovascularen systems. | |
| KR830007684A (ko) | 세펨 화합물, 이것의 제조방법 및 제약학적 조성물 | |
| KR950014130A (ko) | 글루코사민 유도체, 그의 제조방법 및 그의 합성 중간체 |