DE3800256A1 - Bioadhaesive suppositorienmassen - Google Patents
Bioadhaesive suppositorienmassenInfo
- Publication number
- DE3800256A1 DE3800256A1 DE3800256A DE3800256A DE3800256A1 DE 3800256 A1 DE3800256 A1 DE 3800256A1 DE 3800256 A DE3800256 A DE 3800256A DE 3800256 A DE3800256 A DE 3800256A DE 3800256 A1 DE3800256 A1 DE 3800256A1
- Authority
- DE
- Germany
- Prior art keywords
- suppository
- cellulose
- water
- weight
- drug
- 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.)
- Ceased
Links
- 239000000829 suppository Substances 0.000 title claims abstract description 110
- 239000000203 mixture Substances 0.000 claims abstract description 67
- 239000003814 drug Substances 0.000 claims abstract description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000002511 suppository base Substances 0.000 claims abstract description 42
- 239000001768 carboxy methyl cellulose Substances 0.000 claims abstract description 22
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims abstract description 18
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims abstract description 18
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims abstract description 18
- 229920001477 hydrophilic polymer Polymers 0.000 claims abstract description 17
- 239000000227 bioadhesive Substances 0.000 claims abstract description 10
- 229920002125 Sokalan® Polymers 0.000 claims abstract description 9
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 3
- 229940079593 drug Drugs 0.000 claims description 47
- 239000000416 hydrocolloid Substances 0.000 claims description 41
- 229960000988 nystatin Drugs 0.000 claims description 27
- VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 claims description 27
- 229940121375 antifungal agent Drugs 0.000 claims description 26
- 238000002844 melting Methods 0.000 claims description 23
- 239000000839 emulsion Substances 0.000 claims description 22
- 229920001577 copolymer Polymers 0.000 claims description 19
- 229920002678 cellulose Polymers 0.000 claims description 17
- 239000001913 cellulose Substances 0.000 claims description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 15
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 claims description 15
- 229960004022 clotrimazole Drugs 0.000 claims description 15
- 229920001223 polyethylene glycol Polymers 0.000 claims description 14
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 13
- 229920001519 homopolymer Polymers 0.000 claims description 13
- 239000000155 melt Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- -1 alkali metal salt Chemical class 0.000 claims description 12
- 230000000843 anti-fungal effect Effects 0.000 claims description 12
- 229920003086 cellulose ether Polymers 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 230000008018 melting Effects 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 11
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 11
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 11
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 230000003472 neutralizing effect Effects 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- 239000003242 anti bacterial agent Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- 239000004094 surface-active agent Substances 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 9
- 239000002202 Polyethylene glycol Substances 0.000 claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 8
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 8
- 125000001033 ether group Chemical group 0.000 claims description 8
- 239000000194 fatty acid Substances 0.000 claims description 8
- 229930195729 fatty acid Natural products 0.000 claims description 8
- 239000003346 palm kernel oil Substances 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 230000008023 solidification Effects 0.000 claims description 7
- 238000007711 solidification Methods 0.000 claims description 7
- 239000003381 stabilizer Substances 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims description 6
- 230000036760 body temperature Effects 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- 239000004584 polyacrylic acid Substances 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 229940124597 therapeutic agent Drugs 0.000 claims description 6
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 claims description 5
- 229930182566 Gentamicin Natural products 0.000 claims description 5
- BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 239000000032 diagnostic agent Substances 0.000 claims description 5
- 229940039227 diagnostic agent Drugs 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229960002509 miconazole Drugs 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- LEZWWPYKPKIXLL-UHFFFAOYSA-N 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound C1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 LEZWWPYKPKIXLL-UHFFFAOYSA-N 0.000 claims description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 4
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 4
- 108010010803 Gelatin Proteins 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 239000005639 Lauric acid Substances 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 235000021355 Stearic acid Nutrition 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 229960002537 betamethasone Drugs 0.000 claims description 4
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 claims description 4
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 4
- 229920003064 carboxyethyl cellulose Polymers 0.000 claims description 4
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 4
- 235000019864 coconut oil Nutrition 0.000 claims description 4
- 239000003240 coconut oil Substances 0.000 claims description 4
- 229960003913 econazole Drugs 0.000 claims description 4
- 239000008273 gelatin Substances 0.000 claims description 4
- 229920000159 gelatin Polymers 0.000 claims description 4
- 235000019322 gelatine Nutrition 0.000 claims description 4
- 235000011852 gelatine desserts Nutrition 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
- 229920003063 hydroxymethyl cellulose Polymers 0.000 claims description 4
- 229940031574 hydroxymethyl cellulose Drugs 0.000 claims description 4
- 238000001727 in vivo Methods 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 4
- 210000004379 membrane Anatomy 0.000 claims description 4
- 239000012528 membrane Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 4
- 235000019865 palm kernel oil Nutrition 0.000 claims description 4
- 239000001814 pectin Substances 0.000 claims description 4
- 235000010987 pectin Nutrition 0.000 claims description 4
- 229920001277 pectin Polymers 0.000 claims description 4
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 claims description 4
- 210000000664 rectum Anatomy 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000008117 stearic acid Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 150000003626 triacylglycerols Chemical class 0.000 claims description 4
- 210000001215 vagina Anatomy 0.000 claims description 4
- 235000013311 vegetables Nutrition 0.000 claims description 4
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 claims description 3
- NLJVXZFCYKWXLH-DXTIXLATSA-N 3-[(3r,6s,9s,12s,15s,17s,20s,22r,25s,28s)-20-(2-amino-2-oxoethyl)-9-(3-aminopropyl)-3,22,25-tribenzyl-15-[(4-hydroxyphenyl)methyl]-6-(2-methylpropyl)-2,5,8,11,14,18,21,24,27-nonaoxo-12-propan-2-yl-1,4,7,10,13,16,19,23,26-nonazabicyclo[26.3.0]hentriacontan Chemical compound C([C@H]1C(=O)N[C@H](C(=O)N[C@@H](CCCN)C(=O)N[C@H](C(N[C@H](CC=2C=CC=CC=2)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(O)=O)N1)=O)CC(C)C)C(C)C)C1=CC=C(O)C=C1 NLJVXZFCYKWXLH-DXTIXLATSA-N 0.000 claims description 3
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 claims description 3
- 108010026389 Gramicidin Proteins 0.000 claims description 3
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 claims description 3
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 claims description 3
- 229930193140 Neomycin Natural products 0.000 claims description 3
- 108010021006 Tyrothricin Proteins 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 229960004905 gramicidin Drugs 0.000 claims description 3
- ZWCXYZRRTRDGQE-SORVKSEFSA-N gramicidina Chemical compound C1=CC=C2C(C[C@H](NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@H](NC(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](NC=O)C(C)C)CC(C)C)C(=O)NCCO)=CNC2=C1 ZWCXYZRRTRDGQE-SORVKSEFSA-N 0.000 claims description 3
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 claims description 3
- 229960002867 griseofulvin Drugs 0.000 claims description 3
- 238000003780 insertion Methods 0.000 claims description 3
- 230000037431 insertion Effects 0.000 claims description 3
- 229960004125 ketoconazole Drugs 0.000 claims description 3
- 229960004927 neomycin Drugs 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 229960003281 tyrothricin Drugs 0.000 claims description 3
- PROQIPRRNZUXQM-UHFFFAOYSA-N (16alpha,17betaOH)-Estra-1,3,5(10)-triene-3,16,17-triol Natural products OC1=CC=C2C3CCC(C)(C(C(O)C4)O)C4C3CCC2=C1 PROQIPRRNZUXQM-UHFFFAOYSA-N 0.000 claims description 2
- MINDHVHHQZYEEK-UHFFFAOYSA-N (E)-(2S,3R,4R,5S)-5-[(2S,3S,4S,5S)-2,3-epoxy-5-hydroxy-4-methylhexyl]tetrahydro-3,4-dihydroxy-(beta)-methyl-2H-pyran-2-crotonic acid ester with 9-hydroxynonanoic acid Natural products CC(O)C(C)C1OC1CC1C(O)C(O)C(CC(C)=CC(=O)OCCCCCCCCC(O)=O)OC1 MINDHVHHQZYEEK-UHFFFAOYSA-N 0.000 claims description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- IQXJCCZJOIKIAD-UHFFFAOYSA-N 1-(2-methoxyethoxy)hexadecane Chemical compound CCCCCCCCCCCCCCCCOCCOC IQXJCCZJOIKIAD-UHFFFAOYSA-N 0.000 claims description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 claims description 2
- QXHHHPZILQDDPS-UHFFFAOYSA-N 1-{2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound S1C=CC(COC(CN2C=NC=C2)C=2C(=CC(Cl)=CC=2)Cl)=C1Cl QXHHHPZILQDDPS-UHFFFAOYSA-N 0.000 claims description 2
- MTPJEFOSTIKRSS-UHFFFAOYSA-N 3-(dimethylamino)propanenitrile Chemical compound CN(C)CCC#N MTPJEFOSTIKRSS-UHFFFAOYSA-N 0.000 claims description 2
- PJJGZPJJTHBVMX-UHFFFAOYSA-N 5,7-Dihydroxyisoflavone Chemical compound C=1C(O)=CC(O)=C(C2=O)C=1OC=C2C1=CC=CC=C1 PJJGZPJJTHBVMX-UHFFFAOYSA-N 0.000 claims description 2
- 244000301344 Acacia baileyana Species 0.000 claims description 2
- 229920002126 Acrylic acid copolymer Polymers 0.000 claims description 2
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 2
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- 241000222122 Candida albicans Species 0.000 claims description 2
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 2
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- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 claims description 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 2
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- 229920001615 Tragacanth Polymers 0.000 claims description 2
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- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 2
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- 235000010407 ammonium alginate Nutrition 0.000 claims description 2
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- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
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- 239000007864 aqueous solution Substances 0.000 claims description 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
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- 229950009789 cetomacrogol 1000 Drugs 0.000 claims description 2
- 229940117583 cocamine Drugs 0.000 claims description 2
- 229940110456 cocoa butter Drugs 0.000 claims description 2
- 235000019868 cocoa butter Nutrition 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 230000003111 delayed effect Effects 0.000 claims description 2
- 229960003957 dexamethasone Drugs 0.000 claims description 2
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims description 2
- 229940043276 diisopropanolamine Drugs 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
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- 239000000975 dye Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 229960003276 erythromycin Drugs 0.000 claims description 2
- PROQIPRRNZUXQM-ZXXIGWHRSA-N estriol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)C4)O)[C@@H]4[C@@H]3CCC2=C1 PROQIPRRNZUXQM-ZXXIGWHRSA-N 0.000 claims description 2
- 229960001348 estriol Drugs 0.000 claims description 2
- LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 claims description 2
- 229960004369 flufenamic acid Drugs 0.000 claims description 2
- 229960002949 fluorouracil Drugs 0.000 claims description 2
- 239000000499 gel Substances 0.000 claims description 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 2
- 235000010417 guar gum Nutrition 0.000 claims description 2
- 239000000665 guar gum Substances 0.000 claims description 2
- 229960002154 guar gum Drugs 0.000 claims description 2
- 229960000890 hydrocortisone Drugs 0.000 claims description 2
- 239000008172 hydrogenated vegetable oil Substances 0.000 claims description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 2
- CYWFCPPBTWOZSF-UHFFFAOYSA-N ibufenac Chemical compound CC(C)CC1=CC=C(CC(O)=O)C=C1 CYWFCPPBTWOZSF-UHFFFAOYSA-N 0.000 claims description 2
- 229950009183 ibufenac Drugs 0.000 claims description 2
- 229960001680 ibuprofen Drugs 0.000 claims description 2
- 229960004716 idoxuridine Drugs 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 230000007774 longterm Effects 0.000 claims description 2
- 229960003464 mefenamic acid Drugs 0.000 claims description 2
- DJGAAPFSPWAYTJ-UHFFFAOYSA-M metamizole sodium Chemical compound [Na+].O=C1C(N(CS([O-])(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 DJGAAPFSPWAYTJ-UHFFFAOYSA-M 0.000 claims description 2
- 229920000609 methyl cellulose Polymers 0.000 claims description 2
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims description 2
- 239000001923 methylcellulose Substances 0.000 claims description 2
- 235000010981 methylcellulose Nutrition 0.000 claims description 2
- 229960000282 metronidazole Drugs 0.000 claims description 2
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 210000002200 mouth mucosa Anatomy 0.000 claims description 2
- 229960003128 mupirocin Drugs 0.000 claims description 2
- 229930187697 mupirocin Natural products 0.000 claims description 2
- DDHVILIIHBIMQU-YJGQQKNPSA-L mupirocin calcium hydrate Chemical compound O.O.[Ca+2].C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@@H]1[C@@H](O)[C@@H](O)[C@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)OC1.C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@@H]1[C@@H](O)[C@@H](O)[C@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)OC1 DDHVILIIHBIMQU-YJGQQKNPSA-L 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 229920000847 nonoxynol Polymers 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 235000019198 oils Nutrition 0.000 claims description 2
- 230000003204 osmotic effect Effects 0.000 claims description 2
- 229960005489 paracetamol Drugs 0.000 claims description 2
- 229960000292 pectin Drugs 0.000 claims description 2
- 229960003893 phenacetin Drugs 0.000 claims description 2
- 229960002895 phenylbutazone Drugs 0.000 claims description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 claims description 2
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 claims description 2
- 229940068918 polyethylene glycol 400 Drugs 0.000 claims description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 229940068968 polysorbate 80 Drugs 0.000 claims description 2
- 229920000053 polysorbate 80 Polymers 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 2
- 159000000001 potassium salts Chemical class 0.000 claims description 2
- 229960005205 prednisolone Drugs 0.000 claims description 2
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[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 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 2
- 229960004618 prednisone Drugs 0.000 claims description 2
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 2
- 229960000329 ribavirin Drugs 0.000 claims description 2
- 210000003296 saliva Anatomy 0.000 claims description 2
- 235000010413 sodium alginate Nutrition 0.000 claims description 2
- 239000000661 sodium alginate Substances 0.000 claims description 2
- 229940005550 sodium alginate Drugs 0.000 claims description 2
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- RMLUKZWYIKEASN-UHFFFAOYSA-M sodium;2-amino-9-(2-hydroxyethoxymethyl)purin-6-olate Chemical compound [Na+].O=C1[N-]C(N)=NC2=C1N=CN2COCCO RMLUKZWYIKEASN-UHFFFAOYSA-M 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 150000003431 steroids Chemical class 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 229960004214 tioconazole Drugs 0.000 claims description 2
- 235000010487 tragacanth Nutrition 0.000 claims description 2
- 239000000196 tragacanth Substances 0.000 claims description 2
- 229940116362 tragacanth Drugs 0.000 claims description 2
- 229960005294 triamcinolone Drugs 0.000 claims description 2
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 claims description 2
- 229920003169 water-soluble polymer Polymers 0.000 claims description 2
- 239000001993 wax Chemical class 0.000 claims description 2
- 235000010493 xanthan gum Nutrition 0.000 claims description 2
- 239000000230 xanthan gum Substances 0.000 claims description 2
- 229920001285 xanthan gum Polymers 0.000 claims description 2
- 229940082509 xanthan gum Drugs 0.000 claims description 2
- 239000003429 antifungal agent Substances 0.000 claims 5
- 239000004615 ingredient Substances 0.000 claims 4
- 239000007937 lozenge Substances 0.000 claims 2
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 claims 1
- 201000007096 Vulvovaginal Candidiasis Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 230000001464 adherent effect Effects 0.000 claims 1
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims 1
- 229960003942 amphotericin b Drugs 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 239000003183 carcinogenic agent Substances 0.000 claims 1
- 238000013270 controlled release Methods 0.000 claims 1
- 230000000887 hydrating effect Effects 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 239000006194 liquid suspension Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract 2
- 239000006216 vaginal suppository Substances 0.000 abstract 1
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 235000010603 pastilles Nutrition 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229960001338 colchicine Drugs 0.000 description 1
- 239000000599 controlled substance Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
- 229960003081 probenecid Drugs 0.000 description 1
- 239000000934 spermatocidal agent Substances 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
- A61K9/0034—Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants
Landscapes
- Health & Medical Sciences (AREA)
- Gynecology & Obstetrics (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US131587A | 1987-01-08 | 1987-01-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3800256A1 true DE3800256A1 (de) | 1988-07-21 |
Family
ID=21695411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3800256A Ceased DE3800256A1 (de) | 1987-01-08 | 1988-01-07 | Bioadhaesive suppositorienmassen |
Country Status (12)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990007325A1 (en) * | 1988-12-30 | 1990-07-12 | Edko Trading And Representation Company Limited | A pessary containing antibacterial drugs |
| WO1994010977A1 (en) * | 1992-11-16 | 1994-05-26 | Leonidov Nikolai B | Anti-microbial and interferon-inducing pharmaceutical compound |
| US5510387A (en) * | 1992-11-16 | 1996-04-23 | Nikolai Borisovich Leonidov | Antimicrobial interferon-inducing medicament |
| DE19756314A1 (de) * | 1997-12-12 | 1999-06-24 | Roland Prof Dr Bodmeier | Zubereitung mit verlängerter Verweildauer am Applikationsort |
| SG91242A1 (en) * | 1993-07-28 | 2002-09-17 | Johnson & Johnson Consumer | A spermicidal anti-viral lubricant composition and method of using same |
| WO2022091016A1 (en) * | 2020-10-29 | 2022-05-05 | Exeltis Pharma México S.A. De C.V. | Pharmaceutical composition suitable for vaginal administration in the form of ovules and use thereof |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4999342A (en) * | 1988-08-16 | 1991-03-12 | Ortho Pharmaceutical Corporation | Long lasting contraceptive suppository composition and methods of use |
| GR1000603B (el) * | 1989-08-16 | 1992-08-26 | Ortho Pharma Corp | Μακρας διαρκειας αντισυλληπτικη συνθεσις υποθετου και μεθοδοι χρησεως. |
| JPH0692317B2 (ja) * | 1990-08-06 | 1994-11-16 | 龍也 橋岡 | 肛門用外用薬剤 |
| IT1251114B (it) * | 1991-07-26 | 1995-05-04 | Farcon Ag | Forme farmaceutiche antivirali per applicazione vaginale |
| WO1993007884A1 (en) * | 1991-10-25 | 1993-04-29 | Senju Pharmaceutical Co., Ltd. | External preparation for treating hemorrhoidal diseases |
| US5354558A (en) * | 1992-09-10 | 1994-10-11 | Mcneil-Pcc, Inc. | Bioerodible contraceptive suppository |
| RU2139707C1 (ru) * | 1996-12-24 | 1999-10-20 | ОАО Нижегородский химико-фармацевтический завод | Суппозитории, обладающие противогрибковым действием (варианты) |
| ES2237298B1 (es) | 2003-07-16 | 2006-11-01 | Italfarmaco, S.A. | Formulaciones mucoadhesivas semisolidas. |
| US7456207B2 (en) * | 2003-09-25 | 2008-11-25 | Teva Pharmaceuticals Usa, Inc. | Vaginal pharmaceutical compositions and methods for preparing them |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1916084A1 (de) * | 1968-03-28 | 1969-10-16 | Kyowa Hakko Kogyo Kk | Suppositorien mit Wasser als Vehiculm |
| DE3529397A1 (de) * | 1984-08-17 | 1986-02-27 | E.R. Squibb & Sons, Inc., Princeton, N.J. | Fungizide zusammensetzung mit verlaengerter wirkungsdauer |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1593261A (en) * | 1976-07-23 | 1981-07-15 | Inveresk Res Int | Controlled release suppository |
| JPS5625109A (en) * | 1979-08-07 | 1981-03-10 | Dia Seiyaku:Kk | Gelled drug for rectal infusion |
| FR2542616B1 (fr) * | 1983-03-17 | 1987-07-31 | Unilever Nv | Composition pour le traitement des muqueuses a base d'un antibiotique et d'un hydrocolloide formateur de gel |
| NL8500724A (nl) * | 1985-03-13 | 1986-10-01 | Univ Groningen | Inrichtingen voor geregelde afgifte van werkzame stoffen, alsmede werkwijze ter vervaardiging daarvan. |
| US4699776A (en) * | 1985-06-28 | 1987-10-13 | R. P. Scherer Corporation | Suppositories containing analgesics, antipyretics or anti-inflammatory agents |
| GB8520664D0 (en) * | 1985-08-17 | 1985-09-25 | Euro Celtique Sa | Suppository |
-
1987
- 1987-11-26 NZ NZ222698A patent/NZ222698A/xx unknown
- 1987-12-02 ZA ZA879060A patent/ZA879060B/xx unknown
- 1987-12-08 NL NL8702956A patent/NL8702956A/nl not_active Application Discontinuation
- 1987-12-17 CH CH4933/87A patent/CH674463A5/fr not_active IP Right Cessation
- 1987-12-17 AU AU82644/87A patent/AU614069B2/en not_active Ceased
-
1988
- 1988-01-04 GB GB08800044A patent/GB2199495A/en active Pending
- 1988-01-07 BE BE8800012A patent/BE1000266A5/fr not_active IP Right Cessation
- 1988-01-07 DE DE3800256A patent/DE3800256A1/de not_active Ceased
- 1988-01-07 IT IT8819014A patent/IT1215667B/it active
- 1988-01-07 SE SE8800025A patent/SE8800025L/ not_active Application Discontinuation
- 1988-01-08 FR FR888800147A patent/FR2609391B1/fr not_active Expired - Fee Related
- 1988-01-08 JP JP63003032A patent/JPS63174923A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1916084A1 (de) * | 1968-03-28 | 1969-10-16 | Kyowa Hakko Kogyo Kk | Suppositorien mit Wasser als Vehiculm |
| DE3529397A1 (de) * | 1984-08-17 | 1986-02-27 | E.R. Squibb & Sons, Inc., Princeton, N.J. | Fungizide zusammensetzung mit verlaengerter wirkungsdauer |
Non-Patent Citations (1)
| Title |
|---|
| NORO: Chem. and Pharm. Bull., Vol. 30, (1982), S. 2900-2905 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990007325A1 (en) * | 1988-12-30 | 1990-07-12 | Edko Trading And Representation Company Limited | A pessary containing antibacterial drugs |
| WO1994010977A1 (en) * | 1992-11-16 | 1994-05-26 | Leonidov Nikolai B | Anti-microbial and interferon-inducing pharmaceutical compound |
| US5510387A (en) * | 1992-11-16 | 1996-04-23 | Nikolai Borisovich Leonidov | Antimicrobial interferon-inducing medicament |
| SG91242A1 (en) * | 1993-07-28 | 2002-09-17 | Johnson & Johnson Consumer | A spermicidal anti-viral lubricant composition and method of using same |
| DE19756314A1 (de) * | 1997-12-12 | 1999-06-24 | Roland Prof Dr Bodmeier | Zubereitung mit verlängerter Verweildauer am Applikationsort |
| DE19756314C2 (de) * | 1997-12-12 | 2000-06-29 | Roland Bodmeier | Zubereitung mit verlängerter Verweildauer am Applikationsort |
| WO2022091016A1 (en) * | 2020-10-29 | 2022-05-05 | Exeltis Pharma México S.A. De C.V. | Pharmaceutical composition suitable for vaginal administration in the form of ovules and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2199495A (en) | 1988-07-13 |
| CH674463A5 (enrdf_load_stackoverflow) | 1990-06-15 |
| SE8800025L (sv) | 1988-07-09 |
| BE1000266A5 (fr) | 1988-09-27 |
| FR2609391B1 (fr) | 1991-02-15 |
| IT8819014A0 (it) | 1988-01-07 |
| ZA879060B (en) | 1988-05-26 |
| NL8702956A (nl) | 1988-08-01 |
| FR2609391A1 (fr) | 1988-07-15 |
| GB8800044D0 (en) | 1988-02-10 |
| AU8264487A (en) | 1988-07-14 |
| SE8800025D0 (sv) | 1988-01-07 |
| NZ222698A (en) | 1990-02-26 |
| AU614069B2 (en) | 1991-08-22 |
| JPS63174923A (ja) | 1988-07-19 |
| IT1215667B (it) | 1990-02-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: VOSSIUS, V., DIPL.-CHEM. DR.RER.NAT. TAUCHNER, P., |
|
| 8128 | New person/name/address of the agent |
Representative=s name: TAUCHNER, P., DIPL.-CHEM. DR.RER.NAT. HEUNEMANN, D |
|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |