CA2066945C - Oral, cutaneous and intravaginal pharmaceutical compositions in the form of foam - Google Patents
Oral, cutaneous and intravaginal pharmaceutical compositions in the form of foam Download PDFInfo
- Publication number
- CA2066945C CA2066945C CA 2066945 CA2066945A CA2066945C CA 2066945 C CA2066945 C CA 2066945C CA 2066945 CA2066945 CA 2066945 CA 2066945 A CA2066945 A CA 2066945A CA 2066945 C CA2066945 C CA 2066945C
- Authority
- CA
- Canada
- Prior art keywords
- composition according
- foam
- active ingredient
- salt
- composition
- 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.)
- Expired - Lifetime
Links
- 239000006260 foam Substances 0.000 title claims abstract description 25
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 41
- 239000004480 active ingredient Substances 0.000 claims abstract description 22
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 239000004094 surface-active agent Substances 0.000 claims abstract description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims abstract description 3
- 239000002671 adjuvant Substances 0.000 claims abstract description 3
- 230000007935 neutral effect Effects 0.000 claims abstract description 3
- NKDJNEGDJVXHKM-UHFFFAOYSA-N n,2-dimethyl-4,5,6,7-tetrahydroindazol-3-amine Chemical group C1CCCC2=NN(C)C(NC)=C21 NKDJNEGDJVXHKM-UHFFFAOYSA-N 0.000 claims description 10
- 229950006500 tetridamine Drugs 0.000 claims description 10
- MBRHNTMUYWQHMR-UHFFFAOYSA-N 2-aminoethanol;6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one Chemical group NCCO.ON1C(=O)C=C(C)C=C1C1CCCCC1 MBRHNTMUYWQHMR-UHFFFAOYSA-N 0.000 claims description 9
- 229960004375 ciclopirox olamine Drugs 0.000 claims description 9
- UUTKICFRNVKFRG-WDSKDSINSA-N (4R)-3-[oxo-[(2S)-5-oxo-2-pyrrolidinyl]methyl]-4-thiazolidinecarboxylic acid Chemical compound OC(=O)[C@@H]1CSCN1C(=O)[C@H]1NC(=O)CC1 UUTKICFRNVKFRG-WDSKDSINSA-N 0.000 claims description 8
- 229960001163 pidotimod Drugs 0.000 claims description 8
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003380 propellant Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- OMDMTHRBGUBUCO-IUCAKERBSA-N (1s,5s)-5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-en-1-ol Chemical compound CC1=CC[C@H](C(C)(C)O)C[C@@H]1O OMDMTHRBGUBUCO-IUCAKERBSA-N 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 4
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzydamine Chemical compound C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 4
- 239000011782 vitamin Substances 0.000 claims description 4
- 229940024606 amino acid Drugs 0.000 claims description 3
- 230000001857 anti-mycotic effect Effects 0.000 claims description 3
- 239000002543 antimycotic Substances 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- 229940088594 vitamin Drugs 0.000 claims description 3
- 229930003231 vitamin Natural products 0.000 claims description 3
- 235000013343 vitamin Nutrition 0.000 claims description 3
- JJVXHDTWVIPRBZ-VKHMYHEASA-N (2r)-2-[carboxy(methyl)amino]-3-sulfanylpropanoic acid Chemical compound OC(=O)N(C)[C@@H](CS)C(O)=O JJVXHDTWVIPRBZ-VKHMYHEASA-N 0.000 claims description 2
- 244000098338 Triticum aestivum Species 0.000 claims description 2
- 230000001741 anti-phlogistic effect Effects 0.000 claims description 2
- 229960000333 benzydamine Drugs 0.000 claims description 2
- 239000003246 corticosteroid Substances 0.000 claims description 2
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 2
- 229960001259 diclofenac Drugs 0.000 claims description 2
- 229960000890 hydrocortisone Drugs 0.000 claims description 2
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims description 2
- 229960000991 ketoprofen Drugs 0.000 claims description 2
- 230000001569 mucosecretolytic effect Effects 0.000 claims description 2
- 150000003904 phospholipids Chemical class 0.000 claims description 2
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims description 2
- 229960002702 piroxicam Drugs 0.000 claims description 2
- 229920001983 poloxamer Polymers 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 229960000230 sobrerol Drugs 0.000 claims description 2
- OMDMTHRBGUBUCO-UHFFFAOYSA-N trans-sobrerol Natural products CC1=CCC(C(C)(C)O)CC1O OMDMTHRBGUBUCO-UHFFFAOYSA-N 0.000 claims description 2
- 230000029663 wound healing Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 8
- HWIMWAMLHNOMRW-UHFFFAOYSA-N 3-(cyclopropylmethyl)-7h-purine-2,6-dione Chemical compound O=C1NC(=O)C=2NC=NC=2N1CC1CC1 HWIMWAMLHNOMRW-UHFFFAOYSA-N 0.000 claims 1
- 229920000858 Cyclodextrin Polymers 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229960001334 corticosteroids Drugs 0.000 claims 1
- 229940097362 cyclodextrins Drugs 0.000 claims 1
- 230000002519 immonomodulatory effect Effects 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 5
- 239000011877 solvent mixture Substances 0.000 abstract description 2
- 241000700159 Rattus Species 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 10
- 229940042130 topical foam Drugs 0.000 description 7
- 239000006264 topical foam Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 235000010418 carrageenan Nutrition 0.000 description 5
- 229920001525 carrageenan Polymers 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 230000036407 pain Effects 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- 229940044952 vaginal foam Drugs 0.000 description 4
- 239000000259 vaginal foam Substances 0.000 description 4
- 241000222122 Candida albicans Species 0.000 description 3
- 229940095731 candida albicans Drugs 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- 229940042127 oral foam Drugs 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 206010046914 Vaginal infection Diseases 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000002500 effect on skin Effects 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- KRCMKUNIILUXPF-UHFFFAOYSA-N methyl 4-hydroxybenzoate;sodium Chemical compound [Na].COC(=O)C1=CC=C(O)C=C1 KRCMKUNIILUXPF-UHFFFAOYSA-N 0.000 description 2
- 229950004864 olamine Drugs 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 235000010268 sodium methyl p-hydroxybenzoate Nutrition 0.000 description 2
- 239000004290 sodium methyl p-hydroxybenzoate Substances 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 230000009747 swallowing Effects 0.000 description 2
- 229960001312 tiaprofenic acid Drugs 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 231100000820 toxicity test Toxicity 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 229960000281 trometamol Drugs 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- GUHPRPJDBZHYCJ-SECBINFHSA-N (2s)-2-(5-benzoylthiophen-2-yl)propanoic acid Chemical compound S1C([C@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CC=C1 GUHPRPJDBZHYCJ-SECBINFHSA-N 0.000 description 1
- WBQNUTJPYOXRCC-BTJKTKAUSA-N (z)-but-2-enedioic acid;n,2-dimethyl-4,5,6,7-tetrahydroindazol-3-amine Chemical compound OC(=O)\C=C/C(O)=O.C1CCCC2=NN(C)C(NC)=C21 WBQNUTJPYOXRCC-BTJKTKAUSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- KWTQSFXGGICVPE-UHFFFAOYSA-N 2-amino-5-(diaminomethylideneamino)pentanoic acid;hydron;chloride Chemical compound Cl.OC(=O)C(N)CCCN=C(N)N KWTQSFXGGICVPE-UHFFFAOYSA-N 0.000 description 1
- WIGIZIANZCJQQY-UHFFFAOYSA-N 4-ethyl-3-methyl-N-[2-[4-[[[(4-methylcyclohexyl)amino]-oxomethyl]sulfamoyl]phenyl]ethyl]-5-oxo-2H-pyrrole-1-carboxamide Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCC(C)CC2)C=C1 WIGIZIANZCJQQY-UHFFFAOYSA-N 0.000 description 1
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000206575 Chondrus crispus Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000006159 Sabouraud's agar Substances 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229950006137 dexfosfoserine Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229960005309 estradiol Drugs 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 208000024386 fungal infectious disease Diseases 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000001524 infective effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000012009 microbiological test Methods 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 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
- USRGIUJOYOXOQJ-GBXIJSLDSA-N phosphothreonine Chemical compound OP(=O)(O)O[C@H](C)[C@H](N)C(O)=O USRGIUJOYOXOQJ-GBXIJSLDSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012449 sabouraud dextrose agar Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000011493 spray foam Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- GUHPRPJDBZHYCJ-UHFFFAOYSA-N tiaprofenic acid Chemical compound S1C(C(C(O)=O)C)=CC=C1C(=O)C1=CC=CC=C1 GUHPRPJDBZHYCJ-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229940100613 topical solution Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- -1 trimethylacetyl Chemical group 0.000 description 1
- 238000011121 vaginal smear Methods 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI91A001149 | 1991-04-24 | ||
| ITMI911149A IT1247529B (it) | 1991-04-24 | 1991-04-24 | Composizioni farmaceutiche in forma di schiuma per somministrazione intravaginale, cutanea e orale |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2066945A1 CA2066945A1 (en) | 1992-10-25 |
| CA2066945C true CA2066945C (en) | 2004-06-22 |
Family
ID=11359784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2066945 Expired - Lifetime CA2066945C (en) | 1991-04-24 | 1992-04-23 | Oral, cutaneous and intravaginal pharmaceutical compositions in the form of foam |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | ATE140623T1 (de) |
| CA (1) | CA2066945C (de) |
| CZ (1) | CZ283238B6 (de) |
| DE (2) | DE510561T1 (de) |
| RU (1) | RU2093146C1 (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2289360C2 (ru) * | 2004-05-26 | 2006-12-20 | Государственное научное учреждение Северо-Кавказский зональный научно-исследовательский ветеринарный институт Российской академии сельскохозяйственных наук | Способ профилактики и лечения заболеваний полостных органов животных лекарственными веществами, вводимыми с пеной |
-
1992
- 1992-04-21 AT AT92106739T patent/ATE140623T1/de active
- 1992-04-21 DE DE1992106739 patent/DE510561T1/de active Pending
- 1992-04-21 DE DE1992612371 patent/DE69212371T2/de not_active Expired - Lifetime
- 1992-04-23 CZ CS921239A patent/CZ283238B6/cs unknown
- 1992-04-23 CA CA 2066945 patent/CA2066945C/en not_active Expired - Lifetime
- 1992-04-23 RU SU5011762 patent/RU2093146C1/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| DE69212371D1 (de) | 1996-08-29 |
| CZ283238B6 (cs) | 1998-02-18 |
| DE69212371T2 (de) | 1997-01-16 |
| ATE140623T1 (de) | 1996-08-15 |
| CA2066945A1 (en) | 1992-10-25 |
| DE510561T1 (de) | 1993-04-08 |
| CS123992A3 (en) | 1992-11-18 |
| RU2093146C1 (ru) | 1997-10-20 |
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