JPWO2019229249A5 - - Google Patents
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- JPWO2019229249A5 JPWO2019229249A5 JP2020567039A JP2020567039A JPWO2019229249A5 JP WO2019229249 A5 JPWO2019229249 A5 JP WO2019229249A5 JP 2020567039 A JP2020567039 A JP 2020567039A JP 2020567039 A JP2020567039 A JP 2020567039A JP WO2019229249 A5 JPWO2019229249 A5 JP WO2019229249A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- preparation
- nicotine
- weight
- pharmaceutical preparation
- 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
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- 239000002253 acid Substances 0.000 claims 20
- 238000002360 preparation method Methods 0.000 claims 18
- 239000000825 pharmaceutical preparation Substances 0.000 claims 14
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 9
- 229960002715 nicotine Drugs 0.000 claims 9
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 9
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims 8
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims 8
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 claims 8
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 claims 8
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 7
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 7
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 7
- 239000005642 Oleic acid Substances 0.000 claims 7
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims 7
- 150000002148 esters Chemical class 0.000 claims 7
- 229930195729 fatty acid Natural products 0.000 claims 7
- 239000000194 fatty acid Substances 0.000 claims 7
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 7
- 239000007788 liquid Substances 0.000 claims 7
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 7
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 6
- 150000004665 fatty acids Chemical class 0.000 claims 6
- 239000000796 flavoring agent Substances 0.000 claims 6
- 235000013355 food flavoring agent Nutrition 0.000 claims 6
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 6
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 235000013162 Cocos nucifera Nutrition 0.000 claims 5
- 244000060011 Cocos nucifera Species 0.000 claims 5
- 229920001223 polyethylene glycol Polymers 0.000 claims 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 claims 4
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 4
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 claims 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 4
- 150000007513 acids Chemical class 0.000 claims 4
- GJWSUKYXUMVMGX-UHFFFAOYSA-N citronellic acid Chemical compound OC(=O)CC(C)CCC=C(C)C GJWSUKYXUMVMGX-UHFFFAOYSA-N 0.000 claims 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 4
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims 4
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 claims 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 4
- -1 polyoxyethylene Polymers 0.000 claims 4
- 239000003784 tall oil Substances 0.000 claims 4
- 229960003080 taurine Drugs 0.000 claims 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 4
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 claims 3
- 235000021355 Stearic acid Nutrition 0.000 claims 3
- 235000011054 acetic acid Nutrition 0.000 claims 3
- 229960000583 acetic acid Drugs 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 239000004310 lactic acid Substances 0.000 claims 3
- 235000014655 lactic acid Nutrition 0.000 claims 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 3
- 235000019260 propionic acid Nutrition 0.000 claims 3
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 claims 2
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 claims 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims 2
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims 2
- FYEHYMARPSSOBO-UHFFFAOYSA-N Aurin Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)=C1C=CC(=O)C=C1 FYEHYMARPSSOBO-UHFFFAOYSA-N 0.000 claims 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims 2
- 229930008398 Citronellate Natural products 0.000 claims 2
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 claims 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 2
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 claims 2
- 239000005643 Pelargonic acid Substances 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- 229920002696 Polyoxyl 40 castor oil Polymers 0.000 claims 2
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims 2
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims 2
- 238000012387 aerosolization Methods 0.000 claims 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 2
- 235000010323 ascorbic acid Nutrition 0.000 claims 2
- 229960005070 ascorbic acid Drugs 0.000 claims 2
- 239000011668 ascorbic acid Substances 0.000 claims 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims 2
- UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 2
- 239000004359 castor oil Substances 0.000 claims 2
- 235000019438 castor oil Nutrition 0.000 claims 2
- 229930016911 cinnamic acid Natural products 0.000 claims 2
- 235000013985 cinnamic acid Nutrition 0.000 claims 2
- 239000003571 electronic cigarette Substances 0.000 claims 2
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims 2
- 229960000304 folic acid Drugs 0.000 claims 2
- 235000019152 folic acid Nutrition 0.000 claims 2
- 239000011724 folic acid Substances 0.000 claims 2
- 235000003599 food sweetener Nutrition 0.000 claims 2
- 239000001530 fumaric acid Substances 0.000 claims 2
- 229960002598 fumaric acid Drugs 0.000 claims 2
- 235000011087 fumaric acid Nutrition 0.000 claims 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims 2
- 235000011187 glycerol Nutrition 0.000 claims 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 2
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 claims 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 2
- 229940040102 levulinic acid Drugs 0.000 claims 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 2
- 239000011976 maleic acid Substances 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 claims 2
- 239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 claims 2
- 229920001451 polypropylene glycol Polymers 0.000 claims 2
- 229920000136 polysorbate Polymers 0.000 claims 2
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- 239000004334 sorbic acid Substances 0.000 claims 2
- 235000010199 sorbic acid Nutrition 0.000 claims 2
- 229940075582 sorbic acid Drugs 0.000 claims 2
- 239000003765 sweetening agent Substances 0.000 claims 2
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims 2
- 229940116269 uric acid Drugs 0.000 claims 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims 1
- MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 claims 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
- LPMBTLLQQJBUOO-KTKRTIGZSA-N (z)-n,n-bis(2-hydroxyethyl)octadec-9-enamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(CCO)CCO LPMBTLLQQJBUOO-KTKRTIGZSA-N 0.000 claims 1
- 229940015975 1,2-hexanediol Drugs 0.000 claims 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims 1
- NYKRTKYIPKOPLK-UHFFFAOYSA-N 1-bromo-2-dichlorophosphoryloxyethane Chemical compound ClP(Cl)(=O)OCCBr NYKRTKYIPKOPLK-UHFFFAOYSA-N 0.000 claims 1
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Polymers CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 claims 1
- LDQYRCPDQDZUOY-UHFFFAOYSA-N 2-(2-dodecoxyethoxy)propan-1-ol Chemical compound CCCCCCCCCCCCOCCOC(C)CO LDQYRCPDQDZUOY-UHFFFAOYSA-N 0.000 claims 1
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 claims 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 claims 1
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| EP18175640.4 | 2018-06-01 | ||
| PCT/EP2019/064212 WO2019229249A1 (en) | 2018-06-01 | 2019-05-31 | Nicotine formulation |
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| GB201817865D0 (en) * | 2018-11-01 | 2018-12-19 | Nicoventures Trading Ltd | Aerosolisable formulation |
| GB201817868D0 (en) * | 2018-11-01 | 2018-12-19 | Nicoventures Trading Ltd | Aerosolised formulation |
| GB201817867D0 (en) * | 2018-11-01 | 2018-12-19 | Nicoventures Trading Ltd | Aerosolisable formulation |
| GB201817859D0 (en) * | 2018-11-01 | 2018-12-19 | Nicoventures Trading Ltd | Aerosolisable formulation |
| GB201817863D0 (en) * | 2018-11-01 | 2018-12-19 | Nicoventures Trading Ltd | Aerosolisable formulation |
| GB201817860D0 (en) | 2018-11-01 | 2018-12-19 | Nicoventures Trading Ltd | Aerosolised formulation |
| BR112021010222A2 (pt) * | 2018-12-31 | 2021-08-24 | Philip Morris Products S.A. | Formulação de nicotina líquida compreendendo solventes imiscíveis em água |
| PL3905908T3 (pl) | 2019-06-20 | 2025-03-24 | Shaheen Innovations Holding Limited | Ultradźwiękowe urządzenie rozpylające do użytku osobistego |
| FR3102041B1 (fr) * | 2019-10-22 | 2025-02-14 | Aroma Sens | Edulcorant pour liquides de cigarette électronique |
| US12233207B2 (en) | 2019-12-15 | 2025-02-25 | Shaheen Innovations Holding Limited | Mist inhaler devices |
| US11730193B2 (en) | 2019-12-15 | 2023-08-22 | Shaheen Innovations Holding Limited | Hookah device |
| ES3014051T3 (en) | 2019-12-15 | 2025-04-16 | Shaheen Innovations Holding Ltd | Mist inhaler devices |
| US11666713B2 (en) | 2019-12-15 | 2023-06-06 | Shaheen Innovations Holding Limited | Mist inhaler devices |
| JP7583061B2 (ja) | 2019-12-15 | 2024-11-13 | シャヒーン イノベーションズ ホールディング リミテッド | 超音波ミスト吸入器 |
| US12213516B2 (en) | 2019-12-15 | 2025-02-04 | Shaheen Innovations Holding Limited | Ultrasonic mist inhaler |
| US12121056B2 (en) | 2019-12-15 | 2024-10-22 | Shaheen Innovations Holding Limited | Hookah device |
| PL4292632T3 (pl) | 2019-12-15 | 2025-11-24 | Shaheen Innovations Holding Limited | Ultradźwiękowy inhalator mgiełki |
| US11589610B2 (en) | 2019-12-15 | 2023-02-28 | Shaheen Innovations Holding Limited | Nicotine delivery device having a mist generator device and a driver device |
| US11911559B2 (en) | 2019-12-15 | 2024-02-27 | Shaheen Innovations Holding Limited | Ultrasonic mist inhaler |
| US11944120B2 (en) | 2019-12-15 | 2024-04-02 | Shaheen Innovations Holding Limited | Ultrasonic mist inhaler with capillary retainer |
| US12201144B2 (en) | 2019-12-15 | 2025-01-21 | Shaheen Innovations Holding Limited | Hookah device |
| US11730191B2 (en) | 2019-12-15 | 2023-08-22 | Shaheen Innovations Holding Limited | Hookah device |
| US12538944B2 (en) | 2019-12-15 | 2026-02-03 | Shaheen Innovations Holding Limited | Nicotine delivery device with identification arrangement |
| BR112022011449A2 (pt) * | 2019-12-18 | 2022-08-30 | Philip Morris Products Sa | Formulação para uso em um sistema gerador de aerossol |
| JP7609561B2 (ja) * | 2020-02-05 | 2025-01-07 | 日本たばこ産業株式会社 | 液体加熱式の加熱型香味吸引器用の液体組成物 |
| IL296737A (en) | 2020-03-27 | 2022-11-01 | Mcneil Ab | A cartridge with nicotine |
| MA57567B1 (fr) * | 2020-04-06 | 2022-09-30 | Shaheen Innovations Holding Ltd | Dispositifs d'inhalateur de brouillard |
| CN111802686A (zh) * | 2020-07-27 | 2020-10-23 | 湖北中烟工业有限责任公司 | 含脂肪酸、植物油的雾化剂以及加热不燃烧卷烟 |
| CN111855866A (zh) * | 2020-08-25 | 2020-10-30 | 甘肃烟草工业有限责任公司 | 一种快速测定烟用添加剂中甲醛的方法 |
| IL303786B2 (en) * | 2020-12-15 | 2024-07-01 | Shaheen Innovations Holding Ltd | Mist inhaler devices |
| CN114947174A (zh) * | 2021-02-25 | 2022-08-30 | 深圳市合元科技有限公司 | 气溶胶形成基质以及气溶胶生成系统 |
| CN113197330A (zh) * | 2021-04-28 | 2021-08-03 | 深圳市博睿生物科技有限公司 | 一种电子烟新型甜味剂及制备方法及应用 |
| IL283002A (en) * | 2021-05-06 | 2022-12-01 | Nicogen Ltd | Nicotine formulations and aerosols |
| CN113912585B (zh) * | 2021-11-09 | 2023-02-24 | 深圳萨特瓦生物科技有限公司 | 复合尼古丁盐及其制备方法与应用、电子烟油及电子烟 |
| US20230188901A1 (en) | 2021-12-15 | 2023-06-15 | Shaheen Innovations Holding Limited | Apparatus for transmitting ultrasonic waves |
| CN116326810B (zh) * | 2021-12-22 | 2026-03-17 | 深圳市富淼生物科技有限公司 | 水基雾化剂、指定用途水基雾化物、雾化弹以及雾化装置 |
| CN114886145A (zh) * | 2022-06-10 | 2022-08-12 | 广州市维城生物科技有限公司 | 一种水基烟碱电子烟雾化液及其制备方法 |
| KR20240012197A (ko) * | 2022-07-20 | 2024-01-29 | 주식회사 케이티앤지 | 표면파 아토마이저에 사용하기 위한 액상형 흡입제형, 이를 포함하는 카트리지 및 에어로졸 생성장치 |
| KR102872477B1 (ko) * | 2022-08-10 | 2025-10-20 | 주식회사 케이티앤지 | 니코틴 흡입성 조성물 및 이를 포함하는 에어로졸 발생 장치 및 시스템 |
| CN116019250B (zh) * | 2022-12-22 | 2025-02-14 | 东莞市吉纯生物技术有限公司 | 基于酸性电解水的雾化液、制备方法和酸性电解水制备方法 |
| WO2024138377A1 (zh) * | 2022-12-27 | 2024-07-04 | 思摩尔国际控股有限公司 | 一种雾化液、雾化器及电子雾化装置 |
| WO2024161313A1 (en) * | 2023-01-31 | 2024-08-08 | Rai Strategic Holdings, Inc. | Stabilized aerosol precursor formulations |
| CN118787123A (zh) * | 2023-04-14 | 2024-10-18 | 思摩尔国际控股有限公司 | 一种水基电子烟雾化制剂及其制备方法和应用 |
| PL446676A1 (pl) * | 2023-11-08 | 2025-05-12 | Dmitrii Shesternenko | Kompozycja liquidu do e-papierosa oraz e-papieros zawierający taką kompozycję |
| FR3159394A1 (fr) * | 2024-02-19 | 2025-08-22 | Swm Holdco Luxembourg | Feuille de papier comprenant un extrait de plante et de la nicotine stabilisée |
| CN117898466B (zh) * | 2024-02-29 | 2024-09-24 | 深圳市艾斯摩迪斯科技有限公司 | 一种复合尼古丁盐的制备方法及其应用 |
| CN120923467A (zh) * | 2025-07-31 | 2025-11-11 | 深圳曼华生物科技有限公司 | 尼古丁盐的制备方法、检测方法、制备的尼古丁盐及应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8301659D0 (en) * | 1983-01-21 | 1983-02-23 | Leo Ab | Smoking substitutes |
| GB2133691B (en) * | 1983-01-21 | 1986-05-21 | Leo Ab | Smoking substitutes for nasal administration |
| CA2231968A1 (en) * | 1998-03-11 | 1999-09-11 | Smoke-Stop, A Partnership Consisting Of Art Slutsky | Method of producing a nicotine medicament |
| US7767698B2 (en) * | 2002-06-03 | 2010-08-03 | Mcneil Ab | Formulation and use thereof |
| SE0201669D0 (sv) | 2002-06-03 | 2002-06-03 | Pharmacia Ab | New formulation and use thereof |
| GB0712308D0 (en) * | 2007-06-25 | 2007-08-01 | Kind Group Ltd | An inhalable composition |
| WO2014182736A1 (en) * | 2013-05-06 | 2014-11-13 | Ploom, Inc. | Nicotine salt formulations for aerosol devices and methods thereof |
| CN110367592B (zh) * | 2013-07-19 | 2022-12-02 | 奥驰亚客户服务有限责任公司 | 电子吸烟器具的液体气溶胶制剂 |
| DE102015117811A1 (de) * | 2015-10-20 | 2017-04-20 | Chv Pharma Gmbh & Co. Kg | Inhalator sowie wirkstoffhaltige Zubereitung für einen Inhalator |
| EP3574902A1 (en) * | 2018-06-01 | 2019-12-04 | Yatzz Limited | Nicotine formulation and mode of delivery |
-
2018
- 2018-06-01 EP EP18175640.4A patent/EP3574902A1/en not_active Withdrawn
-
2019
- 2019-05-31 WO PCT/EP2019/064212 patent/WO2019229249A1/en not_active Ceased
- 2019-05-31 BR BR112020024088-5A patent/BR112020024088B1/pt active IP Right Grant
- 2019-05-31 EP EP21174043.6A patent/EP3909581A1/en active Pending
- 2019-05-31 MA MA50205A patent/MA50205B1/fr unknown
- 2019-05-31 ES ES19727687T patent/ES2883799T3/es active Active
- 2019-05-31 MA MA054714A patent/MA54714A/fr unknown
- 2019-05-31 JP JP2020567039A patent/JP7224375B2/ja active Active
- 2019-05-31 EP EP19727687.6A patent/EP3684362B1/en active Active
- 2019-05-31 MX MX2020012810A patent/MX390509B/es unknown
- 2019-05-31 AU AU2019276357A patent/AU2019276357B2/en active Active
- 2019-05-31 SG SG11202011761XA patent/SG11202011761XA/en unknown
- 2019-05-31 CN CN201980034986.5A patent/CN112218637A/zh active Pending
- 2019-05-31 US US17/057,700 patent/US11833145B2/en active Active
- 2019-05-31 PL PL19727687T patent/PL3684362T3/pl unknown
-
2020
- 2020-12-10 ZA ZA2020/07717A patent/ZA202007717B/en unknown
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2023
- 2023-05-08 AU AU2023202855A patent/AU2023202855B2/en active Active
- 2023-10-26 US US18/495,012 patent/US20240050424A1/en not_active Abandoned
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