AU596806B2 - Creation of Inventions and Patents with Artificial Intelligence

AU596806B2 – Injectable semi-solid formulations
– Google Patents

AU596806B2 – Injectable semi-solid formulations
– Google Patents
Injectable semi-solid formulations

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Publication number
AU596806B2

AU596806B2
AU61199/86A
AU6119986A
AU596806B2
AU 596806 B2
AU596806 B2
AU 596806B2
AU 61199/86 A
AU61199/86 A
AU 61199/86A
AU 6119986 A
AU6119986 A
AU 6119986A
AU 596806 B2
AU596806 B2
AU 596806B2
Authority
AU
Australia
Prior art keywords
formulation
weight
gelucire
release
modifying agent
Prior art date
1985-08-19
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.)

Ceased

Application number
AU61199/86A
Other versions

AU6119986A
(en

Inventor
Roger Garrick Harrison
Arvind Lavji Thakkar
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eli Lilly and Co

Original Assignee
Eli Lilly and Co
Priority date (The priority date 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 date listed.)
1985-08-19
Filing date
1986-08-15
Publication date
1990-05-17

1986-08-15
Application filed by Eli Lilly and Co
filed
Critical
Eli Lilly and Co

1987-02-26
Publication of AU6119986A
publication
Critical
patent/AU6119986A/en

1990-05-17
Application granted
granted
Critical

1990-05-17
Publication of AU596806B2
publication
Critical
patent/AU596806B2/en

2006-08-15
Anticipated expiration
legal-status
Critical

Status
Ceased
legal-status
Critical
Current

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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

A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue

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

Description

FORM 10 596806 SPRUSON FERGUSON COMMONWEALTH OF AUSTRALIA PATENTS ACT 1952 COMPLETE SPECIFICATION
(ORIGINAL)
FOR OFFICE USE: Class Int. Class Complete Specification Lodged:
J
0 0 0 0 000000 o 0 000-fit 0 4 0 04 00 0 0000 0 0 0 Accepted: Published: Priority: Related Art: f Ii X) r U p1 0 0 00 *0 0 Name of Applicant: Address of Applicant: Actual Inventor(s): Address for SEcvice: ELI LILLY AND COMPANY Lilly Corporate Center, Indianapolis, Indiana 46285, United States of America ARVIND LAVJI THAKKAR and ROGER GARRICK HARRISON Spruson Ferguson, Patent Attorneys, Level 33 St Martins Tower, 31 Market Street, Sydney, New South Wales, 2000, Australia 0 0* 00 0 000 0 0,4,100 0 0 Complete Specification for the invention entitled: “INJECTABLE SEMI-SOLID FORMULATIONS” The following statement is a full description of this invention, including the best method of performing it kniown to us SBR:eah 39F l -1- INJECTABLE SEMI-SOLID FORMULATIONS The present invention provides a slow release injectable pharmaceutical or veterinary formulation comprising from 0.01% to 5.0% by weight of a pharmaceutically or veterinary active peptide or protein derived by recombinant DNA technology, or a modified form thereof, from 60.0% to 94.99% by weight of an oil and from 5.0% to 35.0% by weight of a suitable glyceride release-modifying agent which is a non-waxy substance having a melting point greater than that of the body temperature of the animal to which a formulation of the invention is administered, or o approximately 37 0
C.
%0°’o0l Figures 1 and 2 illustrate the cumulative weight gain changes of certain formulations of the present invention containing methionyl-HGH in So comparison to various control formulations. The formulations for which data is provided are described in detail in the Examples. In the Figures, S.O. means sesame oil and the numerical values represent the type of Gelucire glyceride derivative tested. For example, 37/02 in Figure 2 represents Gelucire 37/02. Further details will be made clear in the discussion below.
The quantities of ingredients employed in a formulation of the o\O invention are set forth as percentages of the total weight of the formulation. Those skilled in the art will recognize that the concentration ranges for the ingredients of the formulations are i approximations, and that minor variations to these ranges will provide useful formulations contemplated within the scope of the present invention.
The formulations of the present invention are semi-solid injectable matrices containing an active KK:5963W 2 peptide or protein derived by recombinant DNA technology, an oil and a suitable glyceride release-modifying agent. These nonaqueous formulations provide sustained release of the desired active peptide or protein derived by recombinant DNA technology by formation of a viscous, semi-solid depot at the site of intramuscular injection. Once injected, these hydrophobic formulations are believed to erode slowly upon contact with aqueous biological fluid. By varying the hydrophobicity of a formulation of the invention, the release rate of the particular active peptide or protein derived by recombinant DNA technology may be varied as well. In the formulations of the invention, hydrophobicity is varied with a suitable glyceride release-modifying agent.
The term “suitable glyceride release-modifying agent” means a compound, or mixture of compounds, having a combined lipophilic and hydrophobic effect which is miscible in oil and which contains an ester of glycerol and one or more fatty acids. The glyceride release-modifying o agent employed herein will be a non-waxy substance and will have a melting point greater than that of the body temperature of the animal to which a formulation of the invention is administered, or approximately 370C.
S° Preferably, the glyceride release modifying agent will have a melting point 20 in the range of about 50 0 C to about 750C.
0 o’o The release-modifying agents employed herein are amphiphiles in which the molecule or ion contains both hydrophilic and lipophilic portions.
These agents can be defined by a numerical value based on the Hydrophile- Lipophile Balance system, called the HLB system. The HLB scale is a oo g5 numerical scale, extending o 0 00 00000 00 0 TMR/720v
~IIL~Y
X-6758 -3from 0 to approximately 50, where lower numbers denote more lipophilic and hydrophobic substances, and higher numbers denote more hydrophilic and lipophobic substances. The affinity of a compound for water, or for oily substances, is determined and its HLB value is assigned experimentally. Tables of such values have been published and formulation chemists will be familiar with them. The total HLB value of the present composition may be calculated from the individual HLB’s of its various components. The HLB of the present composition will be in the range of about 1 to about 10, more particularly from about 1 to The preferred glyceride release-modifying agents for use in the present invention are sold under 15 the trademark Gelucire by Gattefosse Corporation, Hawthorne, New York. Gelucires are available with a variety of HLB values and melting points. The preferred glyceride derivative from this series is Gelucire 64/02, meaning that the substance has a melting point in the range around 64 0 C and an HLB value of about 2. Other preferred substances from this class include Gelucire 54/02 and Gelucire 50/02. A detailed discussion of the properties of Gelucire products is presented by C. Doelker et al. in “Incorporation of Liquid, Deliquescent, and Unstable Active Ingredients Into o Excipients for Hard Gelatin Capsules”, Proceedings of the 3rd International Conference on Pharmaceutical Technology (Paris), 73-82 (1983). The glyceride releasemodifying agent employed in a formulation of the invention will be present at a concentration in the range of 1 1 i, 1~1 ~rl~-~U -4 a 5.0% to abeae 35.0% by weight of the total formulation, more preferably from about 10.0% to about 25.0% by weight of the total formulation.
An oil to act as a vehicle for injection will be present in the composition of the present invention. Suitable oils for parenteral administration of biologically active substances are well known to formulation chemists. These oils will preferably be of vegetable origin so that they may be biodegraded readily. The oil ideally will provide little or no muscular irritation upon injection. Further, these oils should be liquid at room temperature, and should be of the type that do not become rapidly rancid when stored. The oils typically will be esters of unsaturated fatty acids. Exemplary oil vehicles for use in the present compositions include corn oil, cottonseed oil, peanut oil, sesame oil, ethyl oleate, and the like, including other oil vehicles which would not interfere with the therapeutic efficacy of the biologically active o ingredient included In the composition of the invention. The oil vehicle .o employed herein will be present in a range of abet 60.0% by weight to aote 94.99% by weight of the total formulation, more preferably from about 75.0% to about 90.0% by weight.
20 A variety of pharmaceutically or veterinary active peptides or o, o proteins may be employed in the formulations of the invention. These active peptides or proteins are of the type which can be used as injectables, and which will be comprised of one or more amino acid fragments derived by recombinant DNA technology. Examples of these active peptides or proteins derived by recombinant DNA technology include growth hormones such as, human growth hormone (HGH), or modified growth hormones, I especially methionyl-HGH; insulin; insulin-like growth factors 1 and 2; o bovine growth hormone (BGH); growth hormone releasing factor; glucagon; i proinsulin; interleukin 1, 2 and 3; colony stimulating factor; tissue activator of plasminogen; thrombomodulin; lipomodulin; skeletal growth factor; erythropoetin; interferons; factor VIIIc; atrial naturetic factor; and related proteins, polypeptides or modified forms thereof. A “modified form” of the active peptide or protein derived by recombinant DNA technology is an active agent modified in some respect, such as by adding, deleting or changing one or more amino acids but which retains in similar, greater or somewhat lesser degree the basic biological activity of the natural form of the peptide or protein. The active peptide or protein will be present in the formulation in a range of about 0.01% by weight to about by weight of the formulation, or as otherwise required to provide the desired rate of release of active peptide or protein derived by recombinant DNA technology to the animal subject.
The present composition also may contain one or more antioxidants in order to provide stability to the formulation and to prevent the oxidation of the active peptide or protein and of the other components used. These antioxidants will be of the type known for use in oil-based pharmaceutical or veterinary compositions. Suitable antioxIi1ants may include a-tocopherol, ascorbyl palmitate, BHT and other like substances suitable for use in nonaqueous, oil based formulations. The quantity of antioxidant employed will be dictated by the amount 00 0 0 (H o TMR/720v X-6758 -6of other ingredients present in the formulation, and the particular antioxidant, but will typically be in the range of about 0.01% by weight to about 10.0% by weight of the total formulation.
One or more preservatives also may be present to protect against the growth of potentially harmful microorganisms. Typical preservatives may include hexyl resorcinol and phenyl mercuric benzoate. These preservatives should be present at an adequate concentration in the composition so as to prevent the multiplication of microorganisms inadvertently introduced into the composition while withdrawing the composition from its container with a hypodermic needle and syringe.
Generally, the preservatives will be present at a con- 15 centration in.the range of about 0.05% by weight to about 1.0% by weight of the total formulation.
i f As noted, the composition of the invention, once injected into an animal, will form a depot at the site of injection and slowly release the active ag*nt over time. Compositions of the invention having an HLB in the desired range are believed to function by partitioning of the active4age from the depot into the surrounding biological fluid. iowever, the present formulations are not limited by any mode of operation and this explanation is provided only as a possible mechanism of action.
The formulations of the invention may be prepared by procedures generally known to formulation chemists. Typically, a matrix, consisting of an oil and a suitable glyceride release-modifying agent, is pept’ c_ o cb r\ !7 j
I-
-I4′ X-6758 -7prepared by adding the glyceride release-moCifying agent to the hot oil, that is, at a temperature in the iange of about 50 0 C to about 150 0 C, and stirring until a clear solution is obtained. The homogeneous mixture then is cooled rapidly with stirring. If necessary, any preservatives and antioxidants then are added. Finally, the active4age-t is blended into the matrix at a temperature that would not adversely effect its stability.
The resulting mixture is then suitable for administration to the mammal in need of treatment with a composition of the invention.
As an additional aspect of the invention, therefore, there is provided a method for the treatment of a warm-blooded animal in need of treatment which 15 comprises administering to said animal a formulation as defined above.
B
aeo o c a o The following non-limiting Examples are provided to further illustrate specific formulations of the present invention, and methods for their preparation.
Example 1 0 *0 A glass vial was charged with 4.91520 g of a matrix containing 4.17792 g of sesame oil and 0.73728 g of Gelucire 46/07. A small stirring bar was added to the vial and the contents of the vial were stirred at a temperature of about 65 0 C until homogeneous. The vial was placed in a cold water bath and the mixture was stirred for about 20 minutes. The stirring bar was removed from the matrix and 0.05209 g of biosynthetically derived methionyl-HGH was added to provide a con- I c”l X-6758 -8centration of methionyl-HGH in the formulation of about 0.998 mg per 0.1 ml of formulation. The resulting formulation of the invention was stored in a refrigerator until needed for further study.
Following the general procedure of Example 1, additional formulations of the invention were prepared.
These formulations are set forth below.
Example 2 A glass vial was charged with 4.92723 g of a matrix containing 4.18815 g of sesame oil and 0.73908 g of Gelucire 48/09, and 0.05389 g of methionyl-HGH, and formulated as described in Example 1 to provide methionyl-HGH at a concentration of about 1.004 mg for each 0.1 ml of formulation.
Example 3 Following the general procedure of Example 1, 4.92582 g of a matrix containing 4.18695 g of sesame oil and 0.73887 g of Gelucire 50/02 and was combined with o o 0.0557 g of methionyl-HGH to provide a formulation of the invention having a concentration of methionyl-HGH of 1.004 mg for each 0.1 ml of formulation.
40 Example 4 o 0 Following the general procedure of Example 1, 4.65124 g of a matrix containing 3.95355 g of sesame
_I
X-6758 -9oil and 0.69769 g of Gelucire 54/02 was combined with 0.05018 g of methionyl-HGH to provide a formulation of the invention having a concentration of methionyl-HGH of 0.990 mg for each 0.1 ml of formulation.
Example Following the general procedure of Example 1, 4.91816 g of matrix containing 4.18044 g of sesame oil and 0.73772 g of Gelucire 62/05 was combined with 0.05359 g of methionyl-HGH to provide a formulation of the invention having a concentration of methionyl-HGH of 1.000 mg for each 0.1 ml of formulation.
Example 6 Following the general procedure of Example 1, 4.89041 g of matrix containing 4.15685 g of sesame oil and 0.73356 g of Gelucire 64/02 was combined with 0.05272 g of methionyl-HGH to provide a formulation of the invention having a concentration of methionyl-HGH of 1.004 mg for each 0.1 ml of formulation.
Example 7 o Following the general procedure of Example 1, 5.069 g of matrix containing 4.30865 g of sesame oil o and 0.76035 g of Gelucire 37/02 was combined with 0.05589 g of methionyl-HGH to provide a formulation of the invention having a concentration of methionyl-HGH of 1.002 mg for each 0.1 ml of formulation.
X-6758 Example 8 Following the general procedure of Example 1, 5.052 g of a matrix containing 4.2942 g of sesame oil and 0.7578 g of Gelucire 37/06 was combined with 0.05585 g of methionyl-HGH to provide a formulation of the invention having a concentration of methionyl-HGH of 1.004 mg for each 0.1 ml of formulation.
Example 9 Following the general procedure of Example 1, 5.078 g of matrix containing 4.3163 g of sesame oil and 0.7617 g of Gelucire 53/10 was combined with 0.05707 g of methionyl-HGH to provide a formulation of the invention having a concentration of methionyl-HGH of 1.006 mg for each 0.1 ml of formulation.
A sesame oil control formulation was prepared by combining 5.00842 g of sesame oil and 0.05414 g of methionyl-HGH to provide a concentration of 0.992 mg of methionyl-HGH per 0.1 ml of formulation.
SThe following procedure was employed to determine the sustained release activity of compositions of the invention.
o ,o Seven female Sprague Dawley hypophysectomized 44 day old rats were administered a single intramuscular injection of 0.1 ml of a specified formulation.
Individual body weights were recorded just prior to administration and at 3, 7, 10 and 14 days after administration.
i X-6758 -11- The data obtained by the above described experiment indicates the body weight increase observed with various formulations of the invention containing methionyl-HGH and is set forth below in Table I. In the Table, column 1 provides the Example Number of the formulation tested; column 2, the days after administration; column 3, the body weight increase in grams from the weight of the rat on day 0; and column 4, the standard deviation (SD) for the body weight change based on seven trials.
Table I Body Weight Increase Observed with Formulations S 15 Containing Methionyl-HGH Example No. Days After Body Weight of Formulation Administration Increase SD 1 3 5 o’ 7 5 2.6 5 3.6 14 5 2 3 5 7 6 1.1 7 1.3 14 7 3 3 12 7 15 2.8 14 2.6 14 13 2.9 0 0 35 4 3 11 4.6 0 7 18 19 4.4 14 21 i I i 1~1 X-6758 -12- Table I continued Example No.
of Formulation 6 Days After Administration 3 7 14 Body Weight Increase (g) 9 9 9 10
SD
2.8 5.1 5.3 1.7 1.6 3.4 3.1 7 8 9 Sesame Oil Control 1.8 2.1 2.2 2.1 1.2 1.1 1.1 1.8 2.7 2.4 3.4 0.8 1.1 1.7 2.4 oe o o.,J 0 0 X-6758 -13- Figures 1 and 2 illustrate the cumulative weight change of various formulations of methionyl -HGH following intramuscular injection. The data in these Figures is that which is presented in Table I as previously described. As can be noted from the Figures, in general, those formulations of the invention which contain Gelucire glyceride derivatives having higher melting points and lower HLB values gave preferred cumulative weight gain increases.
i C o

Claims (6)

1. A slow release injectable pharmaceutical or veterinary formulation comprising from 0.01% to 5.0% by weight of a pharmaceutically or veterinary active peptide or protein derived by recombinant DNA technology, or a modified form thereof, from 60.0% to 94.99% by weight of an oil and from 5.0% to 35.0% by weight of a suitable glyceride release-modifying agent which is a non-waxy substance having a melting point greater than that of the body temperature of the animal to which a formulation of the invention is administered, or approximately 37 0 C.

2. A formulation as claimed in Claim 1 in which the pharmaceutically or veterinary active peptide or protein derived by recombinant DNA technology is a growth hormone, or modified form thereof.

3. A formulation as claimed in Claim 2 which comprises as an active peptide or protein derived by recombinant DNA technology human growth hormone, bovine growth hormone or methionyl human growth hormone.

4. A formulation as claimed in any one of Claims 1 to 3 which has an HLB value in the range of about 1 to about A formulation as claimed in Claim 4 in which the glyceride release-modifying agent has a melting point in the range of about 50 0 C to 22 about oO”oo 6. A formulation as claimed in Claim 5 in which the suitable glyceride release-modifying agent is present at a concentration in the °oo range of about 10.0% to about 25.0% by weight.

7. A formulation as claimed in Claim 6 in which the glyceride release-modifying agent is Gelucire 64/02, Gelucire 54/02 or Gelucire 50/02. I i 8. A method for the treatment of a warm-blooded animal in need of treatment which comprises administering to said animal a formulation as S claimed in any one of Claims 1 to 7. KK:5963W X-6758-(0)

9. A slow release injectable pharmaceutical or veterinary formulation substantially as hereinbefore described with reference to any one of the Examples. DATED this FOURTEENTH day of AUGUST 1986 ELI LILLY AND COMPANY Patent Attorneys for the Applicant SPRUSON FERGUSON nar c g 43 a; 4 3

AU61199/86A
1985-08-19
1986-08-15
Injectable semi-solid formulations

Ceased

AU596806B2
(en)

Applications Claiming Priority (2)

Application Number
Priority Date
Filing Date
Title

US06/766,725

US4775659A
(en)

1985-08-19
1985-08-19
Injectable semi-solid formulations

US766725

1985-08-19

Publications (2)

Publication Number
Publication Date

AU6119986A

AU6119986A
(en)

1987-02-26

AU596806B2
true

AU596806B2
(en)

1990-05-17

Family
ID=25077329
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

AU61199/86A
Ceased

AU596806B2
(en)

1985-08-19
1986-08-15
Injectable semi-solid formulations

Country Status (12)

Country
Link

US
(1)

US4775659A
(en)

EP
(1)

EP0213851B1
(en)

JP
(1)

JPH0710781B2
(en)

AU
(1)

AU596806B2
(en)

CA
(1)

CA1269933A
(en)

DE
(1)

DE3684386D1
(en)

DK
(1)

DK386986A
(en)

IE
(1)

IE59130B1
(en)

IL
(1)

IL79683A
(en)

NZ
(1)

NZ217176A
(en)

PH
(1)

PH23476A
(en)

ZA
(1)

ZA866025B
(en)

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Assignee
Title

ZA866218B
(en)

1985-08-23
1988-03-30
Lilly Co Eli
Injectable sustained release formulation

CA1257199A
(en)

1986-05-20
1989-07-11
Paul Y. Wang
Preparation containing bioactive macromolecular substance for multi-months release in vivo

GB8725427D0
(en)

1987-10-30
1987-12-02
Lilly Industries Ltd
Somatotropin formulations

US5179080A
(en)

1989-08-31
1993-01-12
Clinical Homecare, Corp.
Formulations containing growth hormone and nutritional supplements, and methods of treating malnutrition in chronic lung disease

AU652022B2
(en)

1991-02-12
1994-08-11
C.R. Bard Inc.
Injectable medical device

YU87892A
(en)

1991-10-01
1995-12-04
Eli Lilly And Company Lilly Corporate Center

INJECTIBLE LONG TERM RELEASE FORMULATIONS AND PROCEDURES FOR THEIR OBTAINING AND USE

US5629008A
(en)

1992-06-02
1997-05-13
C.R. Bard, Inc.
Method and device for long-term delivery of drugs

SE9202128D0
(en)

1992-07-09
1992-07-09
Astra Ab

PRECIPITATION OF ONE OR MORE ACTIVE COMPOUNDS IN SITU

US5559110A
(en)

1994-03-09
1996-09-24
The Dupont Merck Pharmaceutical Company
Pharmaceutical formulations of cyclic urea type compounds

ZA9711731B
(en)

1996-12-31
1998-07-01
Monsanto Co
Aqueous glycerol formulations of somatotropin

KR19990071255A
(en)

1998-02-28
1999-09-15
성재갑

Combination composition of somatotropin and vitamin

US10220093B2
(en)

2013-02-28
2019-03-05
Mira Pharma Corporation
Long-acting semi-solid lipid formulations

WO2014134586A2
(en)

2013-02-28
2014-09-04
Mira Pharma Corporation
Injectable long-acting local anesthetic semi-solid formulations and its compostions

BR102013008990A2
(en)

2013-04-12
2014-12-30
Ouro Fino Participacoes E Empreendimentos S A

PHARMACEUTICAL COMPOSITIONS UNDERSTANDING KISSPEPTIN OR ITS DERIVATIVES

US10561606B2
(en)

2017-12-06
2020-02-18
Mira Pharma Corporation
Injectable long-acting local anesthetic semi-solid gel formulations

US11426418B2
(en)

2017-12-06
2022-08-30
Mira Pharma Corporation
Injectable long-acting semi-solid gel formulations

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Process of making a fluid oil-beeswax vehicle for the parenteral administration of drugs

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1985

1985-08-19
US
US06/766,725
patent/US4775659A/en
not_active
Expired – Lifetime

1986

1986-08-11
CA
CA000515666A
patent/CA1269933A/en
not_active
Expired – Lifetime

1986-08-11
IL
IL79683A
patent/IL79683A/en
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IP Right Cessation

1986-08-11
ZA
ZA866025A
patent/ZA866025B/en
unknown

1986-08-12
NZ
NZ217176A
patent/NZ217176A/en
unknown

1986-08-14
PH
PH34137A
patent/PH23476A/en
unknown

1986-08-14
DE
DE8686306282T
patent/DE3684386D1/en
not_active
Expired – Lifetime

1986-08-14
DK
DK386986A
patent/DK386986A/en
not_active
Application Discontinuation

1986-08-14
EP
EP86306282A
patent/EP0213851B1/en
not_active
Expired – Lifetime

1986-08-15
AU
AU61199/86A
patent/AU596806B2/en
not_active
Ceased

1986-08-18
IE
IE221286A
patent/IE59130B1/en
not_active
IP Right Cessation

1986-08-18
JP
JP61193866A
patent/JPH0710781B2/en
not_active
Expired – Lifetime

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(en)

1978-03-07
1979-09-12
Sandoz Ltd
Compositions comprising mono-cyclic peptides

EP0140255A2
(en)

1983-10-14
1985-05-08
Sumitomo Pharmaceuticals Company, Limited
Sustained-release injections

Also Published As

Publication number
Publication date

ZA866025B
(en)

1988-04-27

AU6119986A
(en)

1987-02-26

IE862212L
(en)

1987-02-19

CA1269933A
(en)

1990-06-05

EP0213851A2
(en)

1987-03-11

IL79683A
(en)

1990-11-05

DK386986A
(en)

1987-02-20

US4775659A
(en)

1988-10-04

JPH0710781B2
(en)

1995-02-08

PH23476A
(en)

1989-08-07

IL79683A0
(en)

1986-11-30

DK386986D0
(en)

1986-08-14

EP0213851A3
(en)

1987-09-02

JPS6245538A
(en)

1987-02-27

NZ217176A
(en)

1989-06-28

IE59130B1
(en)

1994-01-12

EP0213851B1
(en)

1992-03-18

DE3684386D1
(en)

1992-04-23

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