JP2006518761A5 - - Google Patents
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- Publication number
- JP2006518761A5 JP2006518761A5 JP2006503842A JP2006503842A JP2006518761A5 JP 2006518761 A5 JP2006518761 A5 JP 2006518761A5 JP 2006503842 A JP2006503842 A JP 2006503842A JP 2006503842 A JP2006503842 A JP 2006503842A JP 2006518761 A5 JP2006518761 A5 JP 2006518761A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- agent
- present
- nicotine
- sublingual
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 description 100
- -1 fatty acid ester Chemical class 0.000 description 98
- 239000003814 drug Substances 0.000 description 92
- 229940079593 drug Drugs 0.000 description 90
- 241000894007 species Species 0.000 description 75
- 150000001408 amides Chemical class 0.000 description 68
- 238000000034 method Methods 0.000 description 63
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 58
- 229960002715 nicotine Drugs 0.000 description 58
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 58
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 57
- 239000003795 chemical substances by application Substances 0.000 description 52
- 238000009472 formulation Methods 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- 239000002253 acid Substances 0.000 description 48
- 238000012384 transportation and delivery Methods 0.000 description 48
- 239000006190 sub-lingual tablet Substances 0.000 description 47
- 239000002904 solvent Substances 0.000 description 46
- 239000003826 tablet Substances 0.000 description 44
- 239000000546 pharmaceutical excipient Substances 0.000 description 41
- 239000006189 buccal tablet Substances 0.000 description 39
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 36
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 150000001412 amines Chemical class 0.000 description 32
- 239000002552 dosage form Substances 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
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- 238000004519 manufacturing process Methods 0.000 description 26
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 24
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 24
- 239000005642 Oleic acid Substances 0.000 description 24
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 24
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 24
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 23
- 239000000843 powder Substances 0.000 description 23
- 230000008569 process Effects 0.000 description 22
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 20
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 20
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 20
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 20
- 229930195725 Mannitol Natural products 0.000 description 19
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 19
- 239000011888 foil Substances 0.000 description 19
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 19
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- CWXVMYDJJNKKQC-UHFFFAOYSA-N [ClH]1N=CC=CC=C1 Chemical compound [ClH]1N=CC=CC=C1 CWXVMYDJJNKKQC-UHFFFAOYSA-N 0.000 description 18
- 238000000465 moulding Methods 0.000 description 18
- 239000012453 solvate Substances 0.000 description 18
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 17
- 229930182837 (R)-adrenaline Natural products 0.000 description 17
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 17
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 17
- 229960005139 epinephrine Drugs 0.000 description 17
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 17
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 17
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 17
- OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 description 16
- 238000004090 dissolution Methods 0.000 description 16
- 238000004108 freeze drying Methods 0.000 description 16
- 239000008194 pharmaceutical composition Substances 0.000 description 16
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 15
- 235000014113 dietary fatty acids Nutrition 0.000 description 15
- 239000007884 disintegrant Substances 0.000 description 15
- 239000000194 fatty acid Substances 0.000 description 15
- 229930195729 fatty acid Natural products 0.000 description 15
- 238000004806 packaging method and process Methods 0.000 description 15
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 15
- 230000000391 smoking effect Effects 0.000 description 15
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 14
- 125000000524 functional group Chemical group 0.000 description 14
- 239000000314 lubricant Substances 0.000 description 14
- 150000004665 fatty acids Chemical class 0.000 description 13
- 210000004877 mucosa Anatomy 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 12
- 229960002428 fentanyl Drugs 0.000 description 12
- IVLVTNPOHDFFCJ-UHFFFAOYSA-N fentanyl citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 IVLVTNPOHDFFCJ-UHFFFAOYSA-N 0.000 description 12
- 229960004063 propylene glycol Drugs 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000007921 spray Substances 0.000 description 12
- 239000002202 Polyethylene glycol Substances 0.000 description 11
- 239000002250 absorbent Substances 0.000 description 11
- 230000002745 absorbent Effects 0.000 description 11
- 229940062527 alendronate Drugs 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 238000002156 mixing Methods 0.000 description 11
- 229920001223 polyethylene glycol Polymers 0.000 description 11
- 235000021357 Behenic acid Nutrition 0.000 description 10
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 10
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 10
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 10
- 239000005639 Lauric acid Substances 0.000 description 10
- 235000021353 Lignoceric acid Nutrition 0.000 description 10
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 10
- 235000021314 Palmitic acid Nutrition 0.000 description 10
- DLRVVLDZNNYCBX-UHFFFAOYSA-N Polydextrose Polymers OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(O)O1 DLRVVLDZNNYCBX-UHFFFAOYSA-N 0.000 description 10
- 235000021355 Stearic acid Nutrition 0.000 description 10
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 10
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 10
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- 230000000295 complement effect Effects 0.000 description 10
- 239000003085 diluting agent Substances 0.000 description 10
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical group CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 10
- 235000011187 glycerol Nutrition 0.000 description 10
- 239000001087 glyceryl triacetate Substances 0.000 description 10
- 235000013773 glyceryl triacetate Nutrition 0.000 description 10
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- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 10
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 10
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- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 10
- 235000013769 triethyl citrate Nutrition 0.000 description 10
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- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 9
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2004
- 2004-02-24 CN CN2004800106000A patent/CN1777411B/zh not_active Expired - Lifetime
- 2004-02-24 MX MXPA05008918A patent/MXPA05008918A/es active IP Right Grant
- 2004-02-24 CA CA2516816A patent/CA2516816C/en not_active Expired - Lifetime
- 2004-02-24 ES ES04714139T patent/ES2414084T3/es not_active Expired - Lifetime
- 2004-02-24 JP JP2006503842A patent/JP5475215B2/ja not_active Expired - Fee Related
- 2004-02-24 RU RU2005130013/15A patent/RU2342953C2/ru active
- 2004-02-24 EP EP04714139.5A patent/EP1599186B1/en not_active Expired - Lifetime
- 2004-02-24 KR KR1020057015592A patent/KR101170844B1/ko not_active Expired - Fee Related
- 2004-02-24 US US10/545,774 patent/US8992974B2/en active Active
- 2004-02-24 EP EP10182094A patent/EP2316418A3/en not_active Withdrawn
- 2004-02-24 KR KR1020127014734A patent/KR20120066688A/ko not_active Withdrawn
- 2004-02-24 EP EP10182127A patent/EP2343045A3/en not_active Withdrawn
- 2004-02-24 WO PCT/US2004/005490 patent/WO2004075877A1/en not_active Ceased
- 2004-02-24 DK DK04714139.5T patent/DK1599186T3/da active
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2005
- 2005-08-09 IL IL170174A patent/IL170174A/en active IP Right Grant
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2011
- 2011-01-12 JP JP2011004397A patent/JP2011074086A/ja active Pending
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2015
- 2015-02-27 US US14/634,693 patent/US20150174116A1/en not_active Abandoned
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2021
- 2021-05-03 US US17/246,852 patent/US20210251977A1/en not_active Abandoned
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