NZ537204A - Oral pharmaceutical forms of liquid drugs having improved bioavailability - Google Patents
Oral pharmaceutical forms of liquid drugs having improved bioavailabilityInfo
- Publication number
- NZ537204A NZ537204A NZ537204A NZ53720403A NZ537204A NZ 537204 A NZ537204 A NZ 537204A NZ 537204 A NZ537204 A NZ 537204A NZ 53720403 A NZ53720403 A NZ 53720403A NZ 537204 A NZ537204 A NZ 537204A
- Authority
- NZ
- New Zealand
- Prior art keywords
- nitrooxy
- acid
- ester
- ono
- methyl
- Prior art date
Links
- 239000007788 liquid Substances 0.000 title claims abstract description 22
- 229940079593 drug Drugs 0.000 title description 14
- 239000003814 drug Substances 0.000 title description 14
- 239000000203 mixture Substances 0.000 claims abstract description 46
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 34
- 239000004094 surface-active agent Substances 0.000 claims abstract description 34
- 239000004480 active ingredient Substances 0.000 claims abstract description 23
- 238000010521 absorption reaction Methods 0.000 claims abstract description 20
- 239000007787 solid Substances 0.000 claims abstract description 19
- 239000003623 enhancer Substances 0.000 claims abstract description 13
- 239000012736 aqueous medium Substances 0.000 claims abstract description 7
- 239000007764 o/w emulsion Substances 0.000 claims abstract description 6
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims abstract description 5
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims abstract description 5
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims abstract description 3
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000006 Nitroglycerin Substances 0.000 claims abstract description 3
- MAFMQEKGGFWBAB-UHFFFAOYSA-N benzonatate Chemical compound CCCCNC1=CC=C(C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC)C=C1 MAFMQEKGGFWBAB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229960003789 benzonatate Drugs 0.000 claims abstract description 3
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229960001214 clofibrate Drugs 0.000 claims abstract description 3
- 229960003711 glyceryl trinitrate Drugs 0.000 claims abstract description 3
- 229960002715 nicotine Drugs 0.000 claims abstract description 3
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229960000604 valproic acid Drugs 0.000 claims abstract description 3
- 239000011782 vitamin Substances 0.000 claims abstract description 3
- 229940088594 vitamin Drugs 0.000 claims abstract description 3
- 229930003231 vitamin Natural products 0.000 claims abstract description 3
- 235000013343 vitamin Nutrition 0.000 claims abstract description 3
- ZCKAMNXUHHNZLN-UHFFFAOYSA-N Chlorphentermine Chemical compound CC(C)(N)CC1=CC=C(Cl)C=C1 ZCKAMNXUHHNZLN-UHFFFAOYSA-N 0.000 claims abstract 2
- 229950007046 chlorphentermine Drugs 0.000 claims abstract 2
- -1 (nitrooxy)propyl Chemical group 0.000 claims description 51
- 239000002253 acid Substances 0.000 claims description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 19
- 229960001259 diclofenac Drugs 0.000 claims description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 13
- DLWSRGHNJVLJAH-UHFFFAOYSA-N nitroflurbiprofen Chemical compound FC1=CC(C(C(=O)OCCCCO[N+]([O-])=O)C)=CC=C1C1=CC=CC=C1 DLWSRGHNJVLJAH-UHFFFAOYSA-N 0.000 claims description 10
- 239000002775 capsule Substances 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 235000019441 ethanol Nutrition 0.000 claims description 8
- 239000000454 talc Substances 0.000 claims description 8
- 229910052623 talc Inorganic materials 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- AKFJWRDCWYYTIG-ZDUSSCGKSA-N naproxcinod Chemical compound C1=C([C@H](C)C(=O)OCCCCO[N+]([O-])=O)C=CC2=CC(OC)=CC=C21 AKFJWRDCWYYTIG-ZDUSSCGKSA-N 0.000 claims description 5
- 229920000136 polysorbate Polymers 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 4
- 229920002472 Starch Polymers 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 239000013060 biological fluid Substances 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 229940068965 polysorbates Drugs 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000344 soap Substances 0.000 claims description 4
- 235000019698 starch Nutrition 0.000 claims description 4
- CQVHWLHWUZRTQC-UHFFFAOYSA-N 4-nitrooxybutyl 2-[2-(2,6-dichloroanilino)phenyl]acetate Chemical compound [O-][N+](=O)OCCCCOC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl CQVHWLHWUZRTQC-UHFFFAOYSA-N 0.000 claims description 3
- KDVWFHDTQGOBHM-UHFFFAOYSA-N [2-methyl-3-(nitrooxymethyl)phenyl] 2-acetyloxybenzoate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)OC1=CC=CC(CO[N+]([O-])=O)=C1C KDVWFHDTQGOBHM-UHFFFAOYSA-N 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 235000000346 sugar Nutrition 0.000 claims description 3
- 150000008163 sugars Chemical class 0.000 claims description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 2
- JJLKXBIUMBGNNY-UHFFFAOYSA-N 2-(4-phenylphenyl)acetamide Chemical compound C1=CC(CC(=O)N)=CC=C1C1=CC=CC=C1 JJLKXBIUMBGNNY-UHFFFAOYSA-N 0.000 claims description 2
- BTVWZWFKMIUSGS-UHFFFAOYSA-N 2-methylpropane-1,2-diol Chemical compound CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 claims description 2
- ZETOHPSSBWBMED-UHFFFAOYSA-N 4-nitrooxybutanoic acid Chemical compound OC(=O)CCCO[N+]([O-])=O ZETOHPSSBWBMED-UHFFFAOYSA-N 0.000 claims description 2
- 239000005995 Aluminium silicate Substances 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
- 229920000858 Cyclodextrin Polymers 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- 229910021502 aluminium hydroxide Inorganic materials 0.000 claims description 2
- 235000012211 aluminium silicate Nutrition 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 239000003945 anionic surfactant Substances 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 239000000440 bentonite Substances 0.000 claims description 2
- 229910000278 bentonite Inorganic materials 0.000 claims description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical group O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 2
- 229960000686 benzalkonium chloride Drugs 0.000 claims description 2
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 2
- 239000003613 bile acid Chemical class 0.000 claims description 2
- 239000003093 cationic surfactant Substances 0.000 claims description 2
- 239000001913 cellulose Chemical class 0.000 claims description 2
- 229920002678 cellulose Chemical class 0.000 claims description 2
- 229960002798 cetrimide Drugs 0.000 claims description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 2
- 235000018417 cysteine Nutrition 0.000 claims description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 2
- GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 claims description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 229940035429 isobutyl alcohol Drugs 0.000 claims description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- 239000000391 magnesium silicate Substances 0.000 claims description 2
- 229940099273 magnesium trisilicate Drugs 0.000 claims description 2
- 229910000386 magnesium trisilicate Inorganic materials 0.000 claims description 2
- 235000019793 magnesium trisilicate Nutrition 0.000 claims description 2
- 239000002736 nonionic surfactant Substances 0.000 claims description 2
- 229920000847 nonoxynol Polymers 0.000 claims description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims description 2
- 229960001180 norfloxacin Drugs 0.000 claims description 2
- 150000003904 phospholipids Chemical class 0.000 claims description 2
- 229920001223 polyethylene glycol Chemical class 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 229940114930 potassium stearate Drugs 0.000 claims description 2
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000004760 silicates Chemical class 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- SYQXAKPJCDYTQH-UHFFFAOYSA-N 2-(2-nitrooxyethoxy)ethyl 2-[2-(2,6-dichloroanilino)phenyl]acetate Chemical compound [O-][N+](=O)OCCOCCOC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl SYQXAKPJCDYTQH-UHFFFAOYSA-N 0.000 claims 1
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 claims 1
- USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- USGQHOIUUJSIPV-UHFFFAOYSA-N 3-nitrooxypropyl 2-[2-(2,6-dichloroanilino)phenyl]acetate Chemical compound [O-][N+](=O)OCCCOC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl USGQHOIUUJSIPV-UHFFFAOYSA-N 0.000 claims 1
- FCVFMTUVUDZCPJ-UHFFFAOYSA-N 3-nitrooxypropyl 5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound [O-][N+](=O)OCCCOC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 FCVFMTUVUDZCPJ-UHFFFAOYSA-N 0.000 claims 1
- XTSNDAAUQJBEGO-UHFFFAOYSA-N 4-nitrooxybutyl 1,3-thiazolidine-4-carboxylate Chemical compound [O-][N+](=O)OCCCCOC(=O)C1CSCN1 XTSNDAAUQJBEGO-UHFFFAOYSA-N 0.000 claims 1
- YIIBICVDALWFPD-UHFFFAOYSA-N 4-nitrooxybutyl 2-acetyloxybenzoate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)OCCCCO[N+]([O-])=O YIIBICVDALWFPD-UHFFFAOYSA-N 0.000 claims 1
- BRYLPYVVKWRBSW-UHFFFAOYSA-N 4-nitrooxybutyl 5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound [O-][N+](=O)OCCCCOC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BRYLPYVVKWRBSW-UHFFFAOYSA-N 0.000 claims 1
- KRFWHCBIUKYSDG-UHFFFAOYSA-N 6-nitrooxyhexyl 5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound [O-][N+](=O)OCCCCCCOC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 KRFWHCBIUKYSDG-UHFFFAOYSA-N 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Chemical class 0.000 claims 1
- SGZDZWGUDOSVHP-UHFFFAOYSA-N [4-(nitrooxymethyl)phenyl]methyl 5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound C1=CC(CO[N+](=O)[O-])=CC=C1COC(=O)C1C2=CC=C(C(=O)C=3C=CC=CC=3)N2CC1 SGZDZWGUDOSVHP-UHFFFAOYSA-N 0.000 claims 1
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- OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
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- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
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Landscapes
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- Organic Chemistry (AREA)
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- Pain & Pain Management (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2002MI001392A ITMI20021392A1 (it) | 2002-06-25 | 2002-06-25 | Forme farmaceutiche per la somministrazione orale di farmaci liquidi a temperatura ambiente dotate di migliore biodisponibilita' |
| PCT/EP2003/006496 WO2004000273A1 (en) | 2002-06-25 | 2003-06-20 | Oral pharmaceutical forms of liquid drugs having improved bioavailability |
Publications (1)
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| NZ537204A true NZ537204A (en) | 2006-07-28 |
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| NZ537204A NZ537204A (en) | 2002-06-25 | 2003-06-20 | Oral pharmaceutical forms of liquid drugs having improved bioavailability |
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| JP (1) | JP2005530835A (https=) |
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| CA (1) | CA2491152A1 (https=) |
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| DK (1) | DK1526839T3 (https=) |
| ES (1) | ES2285182T3 (https=) |
| HK (1) | HK1080364B (https=) |
| IL (1) | IL165601A0 (https=) |
| IT (1) | ITMI20021392A1 (https=) |
| MX (1) | MXPA04012852A (https=) |
| NO (1) | NO20050347L (https=) |
| NZ (1) | NZ537204A (https=) |
| PL (1) | PL206599B1 (https=) |
| PT (1) | PT1526839E (https=) |
| RU (1) | RU2323003C2 (https=) |
| SI (1) | SI1526839T1 (https=) |
| WO (1) | WO2004000273A1 (https=) |
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| IT1303671B1 (it) * | 1998-07-28 | 2001-02-23 | Nicox Sa | Sali dell'acido nitrico con farmaci attivi nel trattamento dipatologie del sistema respiratorio |
| US20030148818A1 (en) * | 2002-01-18 | 2003-08-07 | Myrhum Mark C. | Golf club woods with wood club head having a selectable center of gravity and a selectable shaft |
| SE0200895D0 (sv) * | 2002-03-22 | 2002-03-22 | Astrazeneca Ab | New pharmaceutical composition |
| WO2003103602A2 (en) | 2002-06-11 | 2003-12-18 | Nitromed, Inc. | Nitrosated and/or nitrosylated cyclooxygenase-2 selective inhibitors, compositions and methods of use |
| CA2491127A1 (en) | 2002-07-03 | 2004-01-15 | Nitromed, Inc. | Nitrosated nonsteroidal antiinflammatory compounds, compositions and methods of use |
| ES2285233T3 (es) | 2002-12-20 | 2007-11-16 | Niconovum Ab | Un material en particulas que contiene nicotina y celulosa microcristalina fisicamente y quimicamente estable. |
| FR2873923B1 (fr) * | 2004-08-05 | 2007-01-12 | Gattefosse Holding Sa | Particule solide anhydre contenant une composition lipidique liquide et composition pharmaceutique contenant lesdites particules |
| WO2006085217A2 (en) * | 2005-02-08 | 2006-08-17 | Pfizer Products Inc. | Solid adsorbates of hydrophobic drugs |
| PL1879466T5 (pl) * | 2005-03-04 | 2016-07-29 | Dsm Ip Assets Bv | Spożywcza cząsteczkowa kompozycja lipidowa |
| US20080260816A1 (en) * | 2005-09-16 | 2008-10-23 | Bengt Herslof | Particulate Lipid Pharmaceutical Composition |
| US20080293781A1 (en) | 2005-11-23 | 2008-11-27 | Alberto Gasco | Salicylic Acid Derivatives |
| EP2786749A1 (en) * | 2006-02-03 | 2014-10-08 | Nicox S.A. | Use of nitrooxyderivative of drug for the treatment of muscular dystrophies |
| US9402809B2 (en) | 2006-03-16 | 2016-08-02 | Niconovum Usa, Inc. | Snuff composition |
| MX2009011493A (es) * | 2007-04-25 | 2009-11-09 | Teva Pharma | Complejo de excipiente farmaceutico. |
| WO2009149053A2 (en) * | 2008-06-02 | 2009-12-10 | Dr. Reddy's Laboratories Ltd. | Naproxcinod process and solid dispersion |
| US9474303B2 (en) | 2011-09-22 | 2016-10-25 | R.J. Reynolds Tobacco Company | Translucent smokeless tobacco product |
| US20130078307A1 (en) | 2011-09-22 | 2013-03-28 | Niconovum Usa, Inc. | Nicotine-containing pharmaceutical composition |
| US9629392B2 (en) | 2011-09-22 | 2017-04-25 | R.J. Reynolds Tobacco Company | Translucent smokeless tobacco product |
| US9084439B2 (en) | 2011-09-22 | 2015-07-21 | R.J. Reynolds Tobacco Company | Translucent smokeless tobacco product |
| US9763928B2 (en) | 2012-02-10 | 2017-09-19 | Niconovum Usa, Inc. | Multi-layer nicotine-containing pharmaceutical composition |
| US9044035B2 (en) | 2012-04-17 | 2015-06-02 | R.J. Reynolds Tobacco Company | Remelted ingestible products |
| ES2821528T3 (es) | 2012-11-14 | 2021-04-26 | Grace W R & Co | Composiciones que contienen un material biológicamente activo y un óxido inorgánico no ordenado |
| CN102964250A (zh) * | 2012-11-19 | 2013-03-13 | 吉林大学 | 氟比洛芬丁香酚酯药用化合物及其制剂和制备方法 |
| US9180104B2 (en) | 2013-03-13 | 2015-11-10 | Tris Pharma, Inc. | Benzonatate modified release solid tablets and capsules |
| CN105188677A (zh) | 2013-03-13 | 2015-12-23 | 特瑞斯制药股份有限公司 | 苯佐那酯调释固体片剂和胶囊剂 |
| EP4072516A1 (en) | 2019-12-09 | 2022-10-19 | Nicoventures Trading Limited | Oral product comprising a cannabinoid |
| US11617744B2 (en) | 2019-12-09 | 2023-04-04 | Nico Ventures Trading Limited | Moist oral compositions |
| US11969502B2 (en) | 2019-12-09 | 2024-04-30 | Nicoventures Trading Limited | Oral products |
| US11793230B2 (en) | 2019-12-09 | 2023-10-24 | Nicoventures Trading Limited | Oral products with improved binding of active ingredients |
| US12433321B2 (en) | 2019-12-09 | 2025-10-07 | Nicoventures Trading Limited | Oral composition with beet material |
| US12310959B2 (en) | 2019-12-09 | 2025-05-27 | Nicoventures Trading Limited | Oral compositions with reduced water content |
| US12439952B2 (en) | 2019-12-09 | 2025-10-14 | Nicoventures Trading Limited | Moist oral compositions |
| US12520867B2 (en) | 2019-12-09 | 2026-01-13 | Nicoventures Trading Limited | Buffered oral compositions |
| US12439949B2 (en) | 2019-12-09 | 2025-10-14 | Nicoventures Trading Limited | Oral compositions with reduced water activity |
| US11826462B2 (en) | 2019-12-09 | 2023-11-28 | Nicoventures Trading Limited | Oral product with sustained flavor release |
| MX2022007085A (es) * | 2019-12-09 | 2022-08-19 | Nicoventures Trading Ltd | Nanoemulsion para uso oral. |
| US11872231B2 (en) | 2019-12-09 | 2024-01-16 | Nicoventures Trading Limited | Moist oral product comprising an active ingredient |
| MX2023015529A (es) | 2021-06-25 | 2024-03-05 | Nicoventures Trading Ltd | Productos orales y metodo de fabricacion. |
| IL312564A (en) | 2021-11-05 | 2024-07-01 | Cinclus Pharma Holding Ab Publ | Polymorphs of the hydrochloride salt of linfarezan glurate |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5266615A (en) * | 1975-11-29 | 1977-06-02 | Sawai Seiyaku Kk | Manufacturing of solidified oily liquid substance |
| JPS56169622A (en) * | 1980-06-03 | 1981-12-26 | Kissei Pharmaceut Co Ltd | Method of making solid preparation from oily substance |
| JPS58213073A (ja) * | 1982-06-07 | 1983-12-10 | Masatoshi Yamada | 油状物質の固形化法 |
| US6054136A (en) * | 1993-09-30 | 2000-04-25 | Gattefosse S.A. | Orally administrable composition capable of providing enhanced bioavailability when ingested |
| US5968542A (en) * | 1995-06-07 | 1999-10-19 | Southern Biosystems, Inc. | High viscosity liquid controlled delivery system as a device |
| BRPI9810945B8 (pt) * | 1997-06-27 | 2021-05-25 | Abraxis Bioscience Inc | formulações de agentes farmacológicos, métodos para sua preparação e métodos para uso das mesmas |
| JP2000016934A (ja) * | 1998-06-30 | 2000-01-18 | Eisai Co Ltd | テプレノンを含有した錠剤 |
| EP2127642A3 (en) * | 1998-08-13 | 2010-02-24 | Cima Labs, Inc. | Microemulsions as solid dosage forms for oral administration |
| EP1140027B1 (en) * | 1998-12-23 | 2005-10-12 | Alza Corporation | Dosage forms comprising porous particles |
| US6294192B1 (en) * | 1999-02-26 | 2001-09-25 | Lipocine, Inc. | Triglyceride-free compositions and methods for improved delivery of hydrophobic therapeutic agents |
| IT1311924B1 (it) * | 1999-04-13 | 2002-03-20 | Nicox Sa | Composti farmaceutici. |
| US6793934B1 (en) * | 1999-12-08 | 2004-09-21 | Shire Laboratories, Inc. | Solid oral dosage form |
| SE0000773D0 (sv) * | 2000-03-08 | 2000-03-08 | Astrazeneca Ab | New formulation |
| SE0000774D0 (sv) * | 2000-03-08 | 2000-03-08 | Astrazeneca Ab | New formulation |
| SE0200895D0 (sv) * | 2002-03-22 | 2002-03-22 | Astrazeneca Ab | New pharmaceutical composition |
-
2002
- 2002-06-25 IT IT2002MI001392A patent/ITMI20021392A1/it unknown
-
2003
- 2003-06-20 CN CNB038151812A patent/CN1319518C/zh not_active Expired - Fee Related
- 2003-06-20 CA CA002491152A patent/CA2491152A1/en not_active Abandoned
- 2003-06-20 DE DE60312523T patent/DE60312523T2/de not_active Expired - Lifetime
- 2003-06-20 AU AU2003246564A patent/AU2003246564B2/en not_active Ceased
- 2003-06-20 NZ NZ537204A patent/NZ537204A/en not_active IP Right Cessation
- 2003-06-20 PT PT03760660T patent/PT1526839E/pt unknown
- 2003-06-20 MX MXPA04012852A patent/MXPA04012852A/es active IP Right Grant
- 2003-06-20 PL PL374388A patent/PL206599B1/pl not_active IP Right Cessation
- 2003-06-20 AT AT03760660T patent/ATE356612T1/de not_active IP Right Cessation
- 2003-06-20 EP EP03760660A patent/EP1526839B1/en not_active Expired - Lifetime
- 2003-06-20 IL IL16560103A patent/IL165601A0/xx not_active IP Right Cessation
- 2003-06-20 RU RU2004138554/15A patent/RU2323003C2/ru not_active IP Right Cessation
- 2003-06-20 WO PCT/EP2003/006496 patent/WO2004000273A1/en not_active Ceased
- 2003-06-20 ES ES03760660T patent/ES2285182T3/es not_active Expired - Lifetime
- 2003-06-20 DK DK03760660T patent/DK1526839T3/da active
- 2003-06-20 HK HK06100214.4A patent/HK1080364B/zh not_active IP Right Cessation
- 2003-06-20 KR KR1020047021307A patent/KR20060076136A/ko not_active Ceased
- 2003-06-20 JP JP2004514802A patent/JP2005530835A/ja active Pending
- 2003-06-20 SI SI200330822T patent/SI1526839T1/sl unknown
- 2003-06-20 US US10/515,621 patent/US20060171969A1/en not_active Abandoned
-
2004
- 2004-12-14 ZA ZA200410109A patent/ZA200410109B/xx unknown
-
2005
- 2005-01-21 NO NO20050347A patent/NO20050347L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004000273A1 (en) | 2003-12-31 |
| HK1080364A1 (en) | 2006-04-28 |
| ATE356612T1 (de) | 2007-04-15 |
| MXPA04012852A (es) | 2005-06-08 |
| RU2323003C2 (ru) | 2008-04-27 |
| EP1526839B1 (en) | 2007-03-14 |
| JP2005530835A (ja) | 2005-10-13 |
| ITMI20021392A1 (it) | 2003-12-29 |
| KR20060076136A (ko) | 2006-07-04 |
| PL206599B1 (pl) | 2010-08-31 |
| SI1526839T1 (sl) | 2007-08-31 |
| EP1526839A1 (en) | 2005-05-04 |
| PL374388A1 (en) | 2005-10-17 |
| CN1665486A (zh) | 2005-09-07 |
| HK1080364B (zh) | 2008-02-01 |
| US20060171969A1 (en) | 2006-08-03 |
| NO20050347L (no) | 2005-01-21 |
| ITMI20021392A0 (it) | 2002-06-25 |
| AU2003246564B2 (en) | 2008-06-12 |
| IL165601A0 (en) | 2006-01-15 |
| CN1319518C (zh) | 2007-06-06 |
| PT1526839E (pt) | 2007-06-06 |
| RU2004138554A (ru) | 2005-08-27 |
| ES2285182T3 (es) | 2007-11-16 |
| CA2491152A1 (en) | 2003-12-31 |
| DE60312523D1 (de) | 2007-04-26 |
| AU2003246564A1 (en) | 2004-01-06 |
| DE60312523T2 (de) | 2008-01-10 |
| ZA200410109B (en) | 2005-09-02 |
| DK1526839T3 (da) | 2007-05-21 |
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Legal Events
| Date | Code | Title | Description |
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| S23 | Proceedings under section 23: mention of inventor as such in patent |
Inventor name: CRISTINA MACELLONI Inventor name: GIANCARLO SANTUS Inventor name: PIERO DEL SOLDATO |
|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) | ||
| LAPS | Patent lapsed |