CH662273A5 - Composition pharmaceutique. - Google Patents

Composition pharmaceutique. Download PDF

Info

Publication number: CH662273A5
Authority: CH; Switzerland
Prior art keywords: levamisole; dimethylisosorbide; glycofurol; salt; composition according
Prior art date: 1983-11-21

Application number

CH5562/84A

Other languages

English (en)

French (fr)

Inventor

Maria Rosina Clark

Andrew Lewis

Original Assignee

May & Baker Ltd

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.)

1983-11-21

Filing date

1984-11-21

Publication date

1987-09-30

1984-11-21 Application filed by May & Baker Ltd filed Critical May & Baker Ltd

1987-09-30 Publication of CH662273A5 publication Critical patent/CH662273A5/fr

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 15
229960001614 levamisole Drugs 0.000 claims description 50
239000000203 mixture Substances 0.000 claims description 50
SGKGVABHDAQAJO-UHFFFAOYSA-N nitroxynil Chemical class OC1=C(I)C=C(C#N)C=C1[N+]([O-])=O SGKGVABHDAQAJO-UHFFFAOYSA-N 0.000 claims description 36
HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 claims description 32
MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 claims description 31
CTPDSKVQLSDPLC-UHFFFAOYSA-N 2-(oxolan-2-ylmethoxy)ethanol Chemical compound OCCOCC1CCCO1 CTPDSKVQLSDPLC-UHFFFAOYSA-N 0.000 claims description 30
239000002904 solvent Substances 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
238000007911 parenteral administration Methods 0.000 claims description 14
239000006184 cosolvent Substances 0.000 claims description 9
238000004090 dissolution Methods 0.000 claims description 5
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 4
230000002500 effect on skin Effects 0.000 claims description 3
238000005507 spraying Methods 0.000 claims description 3
229930188620 butyrolactone Natural products 0.000 claims description 2
-1 levamisole nitroxynil salt Chemical class 0.000 description 23
239000000243 solution Substances 0.000 description 19
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 15
241001465754 Metazoa Species 0.000 description 12
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 8
239000003085 diluting agent Substances 0.000 description 7
238000009472 formulation Methods 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
241000244206 Nematoda Species 0.000 description 6
238000000034 method Methods 0.000 description 6
239000008174 sterile solution Substances 0.000 description 6
230000000721 bacterilogical effect Effects 0.000 description 5
235000019445 benzyl alcohol Nutrition 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
241000869417 Trematodes Species 0.000 description 4
244000045947 parasite Species 0.000 description 4
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000654 additive Substances 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
239000008298 dragée Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
150000002334 glycols Chemical class 0.000 description 3
244000000013 helminth Species 0.000 description 3
230000000968 intestinal effect Effects 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
229920001451 polypropylene glycol Polymers 0.000 description 3
239000004540 pour-on Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
IKXCHOUDIPZROZ-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(ethylamino)hexane-1,2,3,4,5-pentol Chemical class CCNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO IKXCHOUDIPZROZ-LXGUWJNJSA-N 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
241000931178 Bunostomum Species 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
241000283707 Capra Species 0.000 description 2
241001126268 Cooperia Species 0.000 description 2
241001147667 Dictyocaulus Species 0.000 description 2
241000283086 Equidae Species 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
241000243974 Haemonchus contortus Species 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
241001494479 Pecora Species 0.000 description 2
239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 2
230000000694 effects Effects 0.000 description 2
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229960003194 meglumine Drugs 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
239000012266 salt solution Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 2
SDOFMBGMRVAJNF-SLPGGIOYSA-N (2r,3r,4r,5s)-6-aminohexane-1,2,3,4,5-pentol Chemical compound NC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO SDOFMBGMRVAJNF-SLPGGIOYSA-N 0.000 description 1
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
241000322475 Bovicola Species 0.000 description 1
241000931177 Bunostomum trigonocephalum Species 0.000 description 1
241000893172 Chabertia Species 0.000 description 1
241000893174 Chabertia ovina Species 0.000 description 1
241000204939 Fasciola gigantica Species 0.000 description 1
241000242711 Fasciola hepatica Species 0.000 description 1
108010034145 Helminth Proteins Proteins 0.000 description 1
208000006968 Helminthiasis Diseases 0.000 description 1
LAZPBGZRMVRFKY-HNCPQSOCSA-N Levamisole hydrochloride Chemical compound Cl.C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 LAZPBGZRMVRFKY-HNCPQSOCSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
RZCHTMXTKQHYDT-UHFFFAOYSA-N N-Lactoyl ethanolamine Chemical compound CC(O)C(=O)NCCO RZCHTMXTKQHYDT-UHFFFAOYSA-N 0.000 description 1
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
241001137882 Nematodirus Species 0.000 description 1
241000243795 Ostertagia Species 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
241000319489 Phora Species 0.000 description 1
241000282887 Suidae Species 0.000 description 1
241000243797 Trichostrongylus Species 0.000 description 1
241000122945 Trichostrongylus axei Species 0.000 description 1
241001489151 Trichuris Species 0.000 description 1
241000344768 Trichuris ovis Species 0.000 description 1
241000534450 Viviparus Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000000507 anthelmentic effect Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007859 condensation product Chemical class 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
229940113088 dimethylacetamide Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229940116333 ethyl lactate Drugs 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013373 food additive Nutrition 0.000 description 1
239000002778 food additive Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
UFBBWLWUIISIPW-UHFFFAOYSA-N imidazo[2,1-b][1,3]thiazole Chemical compound C1=CSC2=NC=CN21 UFBBWLWUIISIPW-UHFFFAOYSA-N 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229960003734 levamisole hydrochloride Drugs 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 1
UWEYRJFJVCLAGH-UHFFFAOYSA-N perfluorodecalin Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C21F UWEYRJFJVCLAGH-UHFFFAOYSA-N 0.000 description 1
239000008063 pharmaceutical solvent Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
239000007921 spray Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000003826 tablet Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- 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
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
- 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
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Tropical Medicine & Parasitology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CH5562/84A 1983-11-21 1984-11-21 Composition pharmaceutique. CH662273A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB838331037A GB8331037D0 (en)	1983-11-21	1983-11-21	Compositions of matter

Publications (1)

Publication Number	Publication Date
CH662273A5 true CH662273A5 (fr)	1987-09-30

Family

ID=10552109

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH5562/84A CH662273A5 (fr)	1983-11-21	1984-11-21	Composition pharmaceutique.

Country Status (15)

Country	Link
JP (1)	JPS60123419A (it)
AU (1)	AU3564984A (it)
BE (1)	BE901095A (it)
CA (1)	CA1236402A (it)
CH (1)	CH662273A5 (it)
DE (1)	DE3442402A1 (it)
DK (1)	DK548884A (it)
ES (1)	ES8600933A1 (it)
FR (1)	FR2555047B1 (it)
GB (2)	GB8331037D0 (it)
HU (1)	HU196307B (it)
IT (1)	IT1177262B (it)
NL (1)	NL8403528A (it)
NZ (1)	NZ210247A (it)
ZA (1)	ZA849008B (it)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0147883A3 (en) *	1983-12-21	1986-12-30	Janssen Pharmaceutica N.V.	Aqueous non-aggressive anthelmintic pour-on formulations
AU5733986A (en) *	1985-05-13	1986-11-20	Syntex (U.S.A.) Inc.	Anthelmintic compositions comprising a benzimidazole derivative and the fasciolicide rafoxanide
IT1223343B (it) *	1987-11-03	1990-09-19	Also Lab Sas	Formulazioni farmaceutiche per somministrazione transdermica
BRPI0506279B1 (pt)	2005-12-16	2018-01-09	Npa - Núcleo De Pesquisas Aplicadas Ltda	Composição sinergística de antihelmínticos e endectocidas
CN100500648C (zh) *	2006-12-29	2009-06-17	浙江工业大学	一种硝碘酚腈的合成方法
BRPI0904365A2 (pt) *	2009-11-05	2011-11-16	Ouro Fino Participacoes E Empreendimentos S A	associações farmacêuticas, composições farmacêuticas, medicamento e método para o tratamento de animais
WO2012089623A1 (en) *	2010-12-27	2012-07-05	Intervet International B.V.	Topical localized isoxazoline formulation comprising glycofurol

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4082881A (en) *	1976-12-23	1978-04-04	E. R. Squibb & Sons, Inc.	Topical and other type pharmaceutical formulations containing isosorbide carrier
AU527154B2 (en) *	1978-12-15	1983-02-17	Pitman-Moore Australia Limited	Composition and process
EP0052962B1 (en) *	1980-11-20	1984-05-09	Beecham Group Plc	Pharmaceutical compositions containing two beta-lactam derivatives
NZ202422A (en) *	1981-11-25	1985-02-28	Ici Australia Ltd	D, l-and l-2,3,5,6-tetrahydro-6-phenylimidazo(2,1-b)thiazolium 4-cyano-2-iodo-6-nitrophenoxide and veterinary compositions

1983
- 1983-11-21 GB GB838331037A patent/GB8331037D0/en active Pending
1984
- 1984-11-19 NZ NZ210247A patent/NZ210247A/en unknown
- 1984-11-19 DK DK548884A patent/DK548884A/da not_active Application Discontinuation
- 1984-11-19 ZA ZA849008A patent/ZA849008B/xx unknown
- 1984-11-19 AU AU35649/84A patent/AU3564984A/en not_active Abandoned
- 1984-11-19 JP JP59242550A patent/JPS60123419A/ja active Pending
- 1984-11-20 BE BE0/214033A patent/BE901095A/fr not_active IP Right Cessation
- 1984-11-20 CA CA000468249A patent/CA1236402A/en not_active Expired
- 1984-11-20 DE DE19843442402 patent/DE3442402A1/de not_active Withdrawn
- 1984-11-20 HU HU844307A patent/HU196307B/hu unknown
- 1984-11-20 NL NL8403528A patent/NL8403528A/nl not_active Application Discontinuation
- 1984-11-20 FR FR8417647A patent/FR2555047B1/fr not_active Expired
- 1984-11-20 GB GB08429264A patent/GB2150024B/en not_active Expired
- 1984-11-20 IT IT23660/84A patent/IT1177262B/it active
- 1984-11-21 CH CH5562/84A patent/CH662273A5/fr not_active IP Right Cessation
- 1984-11-21 ES ES537825A patent/ES8600933A1/es not_active Expired

Also Published As

Publication number	Publication date
FR2555047B1 (fr)	1987-04-17
DK548884D0 (da)	1984-11-19
AU3564984A (en)	1985-05-30
DK548884A (da)	1985-05-22
DE3442402A1 (de)	1985-05-30
ES537825A0 (es)	1985-10-16
ES8600933A1 (es)	1985-10-16
IT8423660A0 (it)	1984-11-20
GB2150024A (en)	1985-06-26
CA1236402A (en)	1988-05-10
HUT35955A (en)	1985-08-28
JPS60123419A (ja)	1985-07-02
BE901095A (fr)	1985-05-20
GB2150024B (en)	1987-02-04
NZ210247A (en)	1988-01-08
GB8331037D0 (en)	1983-12-29
GB8429264D0 (en)	1984-12-27
FR2555047A1 (fr)	1985-05-24
NL8403528A (nl)	1985-06-17
ZA849008B (en)	1985-07-31
IT8423660A1 (it)	1986-05-20
HU196307B (en)	1988-11-28
IT1177262B (it)	1987-08-26

Legal Events

Date	Code	Title	Description
1989-07-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0078785B1 (fr)	1985-04-03	Sels d'acide valproîque, leur préparation et leur utilisation
WO1998007423A1 (fr)	1998-02-26	Procede de lutte contre les myiases des cheptels bovins et ovins et compositions pour la mise en oeuvre de ce procede
FR2670487A1 (fr)	1992-06-19	Nouveau sel de 3-[2-dimethylamino)ethyl-]-n-methyl-1h-indole-5-methanesulfonamide, sa preparation et son utilisation comme medicament.
NZ237086A (en)	1993-07-27	Veterinary anthelminitic drench compositions containing praziquantel and at least one other anthelmintic compound; method of treatment
OA10678A (fr)	2002-11-20	Nouvelles formulations liquides stables à base de paracétamol et leur mode de préparation
FR2851164A1 (fr)	2004-08-20	Formulation liquide injectable de paracetamol
CH662273A5 (fr)	1987-09-30	Composition pharmaceutique.
LU86484A1 (fr)	1986-12-02	Sels de furosemide
CH644015A5 (fr)	1984-07-13	Solution aqueuse injectable a base d'oxytetracycline.
FR2511598A1 (fr)	1983-02-25	Produit pharmaceutique contenant une substance activant la circulation sanguine, en combinaison avec un concentrat de dialyse de sang de veau deproteine
FR2609631A1 (fr)	1988-07-22	Compositions liquides stables a base de bithionol
FR2516923A1 (fr)	1983-05-27	Nouveaux sels organiques du tetramisole et compositions pharmaceutiques les contenant
EP0209462A1 (fr)	1987-01-21	Composition liquide, stable, anthelmintique et fongicide, â base de bithionol sulfoxyde
MC1485A1 (fr)	1983-09-12	Procede de preparation de solutions aqueuses de sulfonamides potentialises
EP0575481B1 (fr)	1996-05-29	Nouvelles compositions liquides a base de derives de la piperidine substitues en 1,4
FR2722988A1 (fr)	1996-02-02	Composition pharmaceutique pour abaisser la pression sanguine et son procede de preparation
MC1372A1 (fr)	1982-01-19	Preparations pharmaceutiques
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