DE2306075A1 - Injizierbare oelige peptidpraeparate und verfahren zu ihrer herstellung - Google Patents
Injizierbare oelige peptidpraeparate und verfahren zu ihrer herstellungInfo
- Publication number
- DE2306075A1 DE2306075A1 DE2306075A DE2306075A DE2306075A1 DE 2306075 A1 DE2306075 A1 DE 2306075A1 DE 2306075 A DE2306075 A DE 2306075A DE 2306075 A DE2306075 A DE 2306075A DE 2306075 A1 DE2306075 A1 DE 2306075A1
- Authority
- DE
- Germany
- Prior art keywords
- preparations
- peptide
- contain
- peptides
- gel
- 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.)
- Pending
Links
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- 238000002360 preparation method Methods 0.000 title claims description 67
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- 150000001413 amino acids Chemical class 0.000 claims description 40
- -1 fatty acid aluminum salt Chemical class 0.000 claims description 38
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 36
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- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- BZQFBWGGLXLEPQ-REOHCLBHSA-N phosphoserine Chemical compound OC(=O)[C@@H](N)COP(O)(O)=O BZQFBWGGLXLEPQ-REOHCLBHSA-N 0.000 description 1
- 229920001308 poly(aminoacid) Polymers 0.000 description 1
- 229920002643 polyglutamic acid Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940048914 protamine Drugs 0.000 description 1
- XNSAINXGIQZQOO-SRVKXCTJSA-N protirelin Chemical compound NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H]1NC(=O)CC1)CC1=CN=CN1 XNSAINXGIQZQOO-SRVKXCTJSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 108010068072 salmon calcitonin Proteins 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 230000001748 thyrotropin Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/33—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
- A61K38/35—Corticotropin [ACTH]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/145—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic compounds
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dermatology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH229972A CH574247A5 (en) | 1972-02-17 | 1972-02-17 | Oily, injectable peptide/aluminium alkanoate compsns - - with prolonged duration of activity |
| CH1782972 | 1972-12-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2306075A1 true DE2306075A1 (de) | 1973-08-23 |
Family
ID=25690055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2306075A Pending DE2306075A1 (de) | 1972-02-17 | 1973-02-08 | Injizierbare oelige peptidpraeparate und verfahren zu ihrer herstellung |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3869549A (https=) |
| JP (1) | JPS4892516A (https=) |
| AR (1) | AR197116A1 (https=) |
| AT (1) | AT335615B (https=) |
| AU (1) | AU472655B2 (https=) |
| BE (1) | BE795516A (https=) |
| CS (1) | CS172967B2 (https=) |
| DD (1) | DD102584A5 (https=) |
| DE (1) | DE2306075A1 (https=) |
| DK (1) | DK134098B (https=) |
| ES (1) | ES411655A1 (https=) |
| FR (1) | FR2181734B1 (https=) |
| GB (1) | GB1418408A (https=) |
| IE (1) | IE37151B1 (https=) |
| IL (1) | IL41416A (https=) |
| NL (1) | NL7300953A (https=) |
| PL (1) | PL90318B1 (https=) |
| SE (1) | SE7600435L (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2205307A1 (en) * | 1972-11-04 | 1974-05-31 | Hoechst Ag | Luteal hormone-releasing hormone prepns - for treatment of hypothalamus insufficiency by intranasal admin. |
| FR2205308A1 (en) * | 1972-11-04 | 1974-05-31 | Hoechst Ag | Luteal hormone-releasing hormone prepns - for treatment of hypothalamus insufficiency by intranasal admin. |
| EP0177478A3 (en) * | 1984-10-04 | 1987-04-01 | Monsanto Company | Prolonged release by biologically active polypeptides |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS528375B2 (https=) * | 1973-07-02 | 1977-03-09 | ||
| GB1575343A (en) * | 1977-05-10 | 1980-09-17 | Ici Ltd | Method for preparing liposome compositions containing biologically active compounds |
| JPS55118415A (en) * | 1979-02-28 | 1980-09-11 | Pii Papahadojiyopo Dometoriosu | Method of encapsulating biologically active substance in lipoid cell |
| US4770874A (en) * | 1983-08-22 | 1988-09-13 | Syntex (U.S.A.) Inc. | Polyoxypropylene-polyoxyethylene block polymer based adjuvants |
| US4933179A (en) * | 1983-08-22 | 1990-06-12 | Syntex (U.S.A.) Inc. | Feline leukemia virus antigen vaccines |
| US4772466A (en) * | 1983-08-22 | 1988-09-20 | Syntex (U.S.A.) Inc. | Vaccines comprising polyoxypropylene-polyoxyethylene block polymer based adjuvants |
| US4606918A (en) * | 1983-08-22 | 1986-08-19 | Syntex (U.S.A.) Inc. | Polyoxypropylene-polyoxyethylene block polymer based adjuvants |
| US5086041A (en) * | 1984-10-04 | 1992-02-04 | Monsanto Company | Methods of using prolonged release somatotropin compositions |
| US5411951A (en) * | 1984-10-04 | 1995-05-02 | Monsanto Company | Prolonged release of biologically active somatotropin |
| US5474980A (en) * | 1984-10-04 | 1995-12-12 | Monsanto Company | Prolonged release of biologically active somatotropins |
| DE3502099A1 (de) * | 1985-01-23 | 1986-08-07 | Dieter Prof. Dr. Dr. 5883 Kierspe Aderhold | Therapeutisches, peptid- und/oder aminosaeurehaltiges mittel |
| US4804742A (en) * | 1985-06-06 | 1989-02-14 | Rorer Pharmaceutical Corporation | Amide analogs of calcitonin |
| US4650854A (en) * | 1985-06-06 | 1987-03-17 | Usv Pharmaceutical Corporation | Amide analogs of calcitonin |
| US4775659A (en) * | 1985-08-19 | 1988-10-04 | Eli Lilly And Company | Injectable semi-solid formulations |
| CA1285874C (en) * | 1985-08-23 | 1991-07-09 | Thomas Harry Ferguson | Injectable sustained release formulation |
| US5554372A (en) * | 1986-09-22 | 1996-09-10 | Emory University | Methods and vaccines comprising surface-active copolymers |
| US5179079A (en) * | 1986-12-16 | 1993-01-12 | Novo Nordisk A/S | Nasal formulation and intranasal administration therewith |
| US5635161A (en) * | 1995-06-07 | 1997-06-03 | Abbott Laboratories | Aerosol drug formulations containing vegetable oils |
| KR19990071255A (ko) | 1998-02-28 | 1999-09-15 | 성재갑 | 소마토트로핀과 비타민의 합제 조성물 |
| US7919109B2 (en) | 1999-02-08 | 2011-04-05 | Intarcia Therapeutics, Inc. | Stable non-aqueous single phase viscous vehicles and formulations utilizing such vehicles |
| US7258869B1 (en) * | 1999-02-08 | 2007-08-21 | Alza Corporation | Stable non-aqueous single phase viscous vehicles and formulations utilizing such vehicle |
| US7731947B2 (en) | 2003-11-17 | 2010-06-08 | Intarcia Therapeutics, Inc. | Composition and dosage form comprising an interferon particle formulation and suspending vehicle |
| CA2563533C (en) * | 2004-04-15 | 2013-10-01 | Shmuel A. Ben-Sasson | Compositions capable of facilitating penetration across a biological barrier |
| WO2006083761A2 (en) | 2005-02-03 | 2006-08-10 | Alza Corporation | Solvent/polymer solutions as suspension vehicles |
| US11246913B2 (en) | 2005-02-03 | 2022-02-15 | Intarcia Therapeutics, Inc. | Suspension formulation comprising an insulinotropic peptide |
| GB0511269D0 (en) * | 2005-06-02 | 2005-07-13 | Creative Peptides Sweden Ab | Sustained release preparation of pro-insulin C-peptide |
| KR101106510B1 (ko) | 2006-05-30 | 2012-01-20 | 인타르시아 세라퓨틱스 인코포레이티드 | 투피스, 내부채널 삼투압 전달 시스템 유동 조절기 |
| EP2359808B1 (en) | 2006-08-09 | 2013-05-22 | Intarcia Therapeutics, Inc | Osmotic delivery systems and piston assemblies |
| WO2008133908A2 (en) | 2007-04-23 | 2008-11-06 | Intarcia Therapeutics, Inc. | Suspension formulations of insulinotropic peptides and uses thereof |
| CA2691531C (en) | 2007-06-22 | 2016-11-01 | Board Of Regents,The University Of Texas System | Formation of stable submicron peptide or protein particles by thin film freezing |
| CA2726861C (en) | 2008-02-13 | 2014-05-27 | Intarcia Therapeutics, Inc. | Devices, formulations, and methods for delivery of multiple beneficial agents |
| KR101814186B1 (ko) | 2008-09-17 | 2018-03-14 | 키아스마 인코포레이티드 | 약제학적 조성물 및 연관된 투여방법 |
| EP2376522A4 (en) | 2008-11-16 | 2013-12-25 | Univ Texas | LOW VISCOSIS HIGHLY CONCENTRATED SUSPENSIONS |
| RU2547990C2 (ru) | 2009-09-28 | 2015-04-10 | Интарсия Терапьютикс, Инк. | Быстрое достижение и/или прекращение существенной стабильной доставки лекарственного средства |
| US20120208755A1 (en) | 2011-02-16 | 2012-08-16 | Intarcia Therapeutics, Inc. | Compositions, Devices and Methods of Use Thereof for the Treatment of Cancers |
| US9956164B2 (en) | 2014-04-16 | 2018-05-01 | Veyx-Pharma Gmbh | Veterinary pharmaceutical composition and use thereof |
| US9889085B1 (en) | 2014-09-30 | 2018-02-13 | Intarcia Therapeutics, Inc. | Therapeutic methods for the treatment of diabetes and related conditions for patients with high baseline HbA1c |
| WO2016126830A1 (en) | 2015-02-03 | 2016-08-11 | Chiasma Inc. | Method of treating diseases |
| RU2730996C2 (ru) | 2015-06-03 | 2020-08-26 | Интарсия Терапьютикс, Инк. | Системы установки и извлечения имплантата |
| CL2016000217A1 (es) * | 2016-01-27 | 2016-07-01 | Farmacologia En Aquacultura Veterinaria Fav S A | Nueva composición veterinaria inyectable para la sincronización del desove en peces |
| KR102574993B1 (ko) | 2016-05-16 | 2023-09-06 | 인타르시아 세라퓨틱스 인코포레이티드 | 글루카곤-수용체 선택적 폴리펩티드 및 이들의 이용 방법 |
| USD860451S1 (en) | 2016-06-02 | 2019-09-17 | Intarcia Therapeutics, Inc. | Implant removal tool |
| USD840030S1 (en) | 2016-06-02 | 2019-02-05 | Intarcia Therapeutics, Inc. | Implant placement guide |
| JP7286542B2 (ja) | 2017-01-03 | 2023-06-05 | インターシア セラピューティクス，インコーポレイティド | Ｇｌｐ－１受容体アゴニストの持続的投与及び薬物の同時投与を含む方法 |
| US11141457B1 (en) | 2020-12-28 | 2021-10-12 | Amryt Endo, Inc. | Oral octreotide therapy and contraceptive methods |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE950676C (de) * | 1948-01-06 | 1956-10-11 | Bristol Lab Inc | Verfahren zur Herstellung eines injizierbaren Arzneimittels |
| DE920148C (de) * | 1951-03-31 | 1954-11-15 | Nyegaard & Co As | Verfahren zur Herstellung von Adrenocorticotrophin-Praeparaten mit verlaengerter Wirkungsdauer |
| US2944940A (en) * | 1956-01-16 | 1960-07-12 | Armour & Co | Adrenocorticotrophin and zinc composition |
| US2945783A (en) * | 1957-06-20 | 1960-07-19 | Reheis Company Inc | Aluminum protein antacid and process of making |
-
0
- BE BE795516D patent/BE795516A/xx unknown
-
1973
- 1973-01-23 NL NL7300953A patent/NL7300953A/xx unknown
- 1973-01-29 IE IE135/73A patent/IE37151B1/xx unknown
- 1973-01-29 IL IL41416A patent/IL41416A/en unknown
- 1973-02-05 US US329519A patent/US3869549A/en not_active Expired - Lifetime
- 1973-02-08 DE DE2306075A patent/DE2306075A1/de active Pending
- 1973-02-14 AR AR246593A patent/AR197116A1/es active
- 1973-02-15 CS CS1106A patent/CS172967B2/cs unknown
- 1973-02-15 FR FR7305303A patent/FR2181734B1/fr not_active Expired
- 1973-02-15 PL PL1973160769A patent/PL90318B1/pl unknown
- 1973-02-15 ES ES411655A patent/ES411655A1/es not_active Expired
- 1973-02-15 AU AU52189/73A patent/AU472655B2/en not_active Expired
- 1973-02-16 AT AT140873A patent/AT335615B/de not_active IP Right Cessation
- 1973-02-16 DK DK86073AA patent/DK134098B/da unknown
- 1973-02-16 DD DD168904A patent/DD102584A5/xx unknown
- 1973-02-16 GB GB773573A patent/GB1418408A/en not_active Expired
- 1973-02-17 JP JP48018908A patent/JPS4892516A/ja active Pending
-
1976
- 1976-01-16 SE SE7600435A patent/SE7600435L/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2205307A1 (en) * | 1972-11-04 | 1974-05-31 | Hoechst Ag | Luteal hormone-releasing hormone prepns - for treatment of hypothalamus insufficiency by intranasal admin. |
| FR2205308A1 (en) * | 1972-11-04 | 1974-05-31 | Hoechst Ag | Luteal hormone-releasing hormone prepns - for treatment of hypothalamus insufficiency by intranasal admin. |
| EP0177478A3 (en) * | 1984-10-04 | 1987-04-01 | Monsanto Company | Prolonged release by biologically active polypeptides |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2181734B1 (https=) | 1975-10-10 |
| AU5218973A (en) | 1974-08-15 |
| IE37151B1 (en) | 1977-05-11 |
| DK134098B (da) | 1976-09-13 |
| GB1418408A (en) | 1975-12-17 |
| DD102584A5 (https=) | 1973-12-20 |
| IL41416A0 (en) | 1973-03-30 |
| AT335615B (de) | 1977-03-25 |
| SE7600435L (sv) | 1976-01-16 |
| ES411655A1 (es) | 1976-09-01 |
| IL41416A (en) | 1976-03-31 |
| US3869549A (en) | 1975-03-04 |
| PL90318B1 (https=) | 1977-01-31 |
| FR2181734A1 (https=) | 1973-12-07 |
| IE37151L (en) | 1973-08-17 |
| NL7300953A (https=) | 1973-08-21 |
| JPS4892516A (https=) | 1973-11-30 |
| CS172967B2 (https=) | 1977-01-28 |
| BE795516A (fr) | 1973-08-16 |
| DK134098C (https=) | 1977-02-21 |
| AU472655B2 (en) | 1976-06-03 |
| ATA140873A (de) | 1976-07-15 |
| AR197116A1 (es) | 1974-03-15 |
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