JP6836017B2

JP6836017B2 - 皮膚外用組成物

皮膚外用組成物 Download PDF

Info

Publication number: JP6836017B2
Authority: JP; Japan
Prior art keywords: acid; ether; mass; polyoxypropylene; polyoxyethylene
Prior art date: 2019-02-01
Legal status : Ceased

Application number

JP2020520078A

Other languages

English (en)

Japanese (ja)

Other versions

JPWO2020158908A1 (ja

Inventor

愛桝本

幸恵藤田

景子升田

未知瑠黒木

Current Assignee

Rohto Pharmaceutical Co Ltd

Original Assignee

Rohto Pharmaceutical Co Ltd

Priority date

2019-02-01

Filing date

2020-01-31

Publication date

2021-02-24

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=71841050&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=JP6836017(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2020-01-31 Application filed by Rohto Pharmaceutical Co Ltd filed Critical Rohto Pharmaceutical Co Ltd

2021-02-18 Publication of JPWO2020158908A1 publication Critical patent/JPWO2020158908A1/ja

2021-02-24 Application granted granted Critical

2021-02-24 Publication of JP6836017B2 publication Critical patent/JP6836017B2/ja

Status Ceased legal-status Critical Current

2040-01-31 Anticipated expiration legal-status Critical

Links

239000000203 mixture Substances 0.000 title claims description 150
230000000699 topical effect Effects 0.000 title 1
-1 alkyl glucoside Chemical class 0.000 claims description 305
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 106
229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims description 88
239000002253 acid Substances 0.000 claims description 45
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 42
229920001451 polypropylene glycol Polymers 0.000 claims description 42
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 39
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 36
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 33
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 30
229930182478 glucoside Natural products 0.000 claims description 30
HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 claims description 28
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 26
229920001577 copolymer Polymers 0.000 claims description 24
235000005152 nicotinamide Nutrition 0.000 claims description 21
239000011570 nicotinamide Substances 0.000 claims description 21
HOVAGTYPODGVJG-UVSYOFPXSA-N (3s,5r)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol Chemical compound COC1OC(CO)[C@@H](O)C(O)[C@H]1O HOVAGTYPODGVJG-UVSYOFPXSA-N 0.000 claims description 20
GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 20
229960003966 nicotinamide Drugs 0.000 claims description 20
HOVAGTYPODGVJG-UHFFFAOYSA-N methyl beta-galactoside Natural products COC1OC(CO)C(O)C(O)C1O HOVAGTYPODGVJG-UHFFFAOYSA-N 0.000 claims description 19
239000001509 sodium citrate Substances 0.000 claims description 19
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 17
239000004615 ingredient Substances 0.000 claims description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims description 16
150000005215 alkyl ethers Chemical class 0.000 claims description 15
235000014113 dietary fatty acids Nutrition 0.000 claims description 15
150000002148 esters Chemical class 0.000 claims description 15
239000000194 fatty acid Substances 0.000 claims description 15
229930195729 fatty acid Natural products 0.000 claims description 15
239000003755 preservative agent Substances 0.000 claims description 15
239000005711 Benzoic acid Substances 0.000 claims description 14
235000010233 benzoic acid Nutrition 0.000 claims description 14
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 claims description 14
235000011187 glycerol Nutrition 0.000 claims description 14
230000002335 preservative effect Effects 0.000 claims description 13
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
WMNULTDOANGXRT-UHFFFAOYSA-N bis(2-ethylhexyl) butanedioate Chemical compound CCCCC(CC)COC(=O)CCC(=O)OCC(CC)CCCC WMNULTDOANGXRT-UHFFFAOYSA-N 0.000 claims description 9
239000004386 Erythritol Substances 0.000 claims description 8
UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 8
229930006000 Sucrose Natural products 0.000 claims description 8
CEBAWORGZDCFQS-UHFFFAOYSA-N butylcarbamic acid 1-iodoprop-1-yne Chemical compound C(#CC)I.C(CCC)NC(O)=O CEBAWORGZDCFQS-UHFFFAOYSA-N 0.000 claims description 8
229940105984 diethylhexyl succinate Drugs 0.000 claims description 8
229940105990 diglycerin Drugs 0.000 claims description 8
UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 8
229940009714 erythritol Drugs 0.000 claims description 8
235000019414 erythritol Nutrition 0.000 claims description 8
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 8
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 8
239000006210 lotion Substances 0.000 claims description 8
235000010199 sorbic acid Nutrition 0.000 claims description 8
239000004334 sorbic acid Substances 0.000 claims description 8
229940075582 sorbic acid Drugs 0.000 claims description 8
239000005720 sucrose Substances 0.000 claims description 8
HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims description 7
IJALWSVNUBBQRA-UHFFFAOYSA-N 4-Isopropyl-3-methylphenol Chemical compound CC(C)C1=CC=C(O)C=C1C IJALWSVNUBBQRA-UHFFFAOYSA-N 0.000 claims description 7
SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 claims description 7
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 7
HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 claims description 7
HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 claims description 7
SWQUTKGVXGTROS-UHFFFAOYSA-N bis(2-ethoxyethyl) butanedioate Chemical compound CCOCCOC(=O)CCC(=O)OCCOCC SWQUTKGVXGTROS-UHFFFAOYSA-N 0.000 claims description 7
229960004926 chlorobutanol Drugs 0.000 claims description 7
229940119676 diethoxyethyl succinate Drugs 0.000 claims description 7
CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 claims description 7
229960000367 inositol Drugs 0.000 claims description 7
NFIDBGJMFKNGGQ-UHFFFAOYSA-N isopropylmethylphenol Natural products CC(C)CC1=CC=CC=C1O NFIDBGJMFKNGGQ-UHFFFAOYSA-N 0.000 claims description 7
RGUVUPQQFXCJFC-UHFFFAOYSA-N n-hydroxyoctanamide Chemical compound CCCCCCCC(=O)NO RGUVUPQQFXCJFC-UHFFFAOYSA-N 0.000 claims description 7
CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims description 7
XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 6
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 6
239000004359 castor oil Substances 0.000 claims description 6
235000019438 castor oil Nutrition 0.000 claims description 6
PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 claims description 6
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 description 6
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
239000000811 xylitol Substances 0.000 claims description 6
235000010447 xylitol Nutrition 0.000 claims description 6
229960002675 xylitol Drugs 0.000 claims description 6
NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 5
229940071120 dehydroacetate Drugs 0.000 claims description 5
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 5
229920001223 polyethylene glycol Polymers 0.000 claims description 5
WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 claims description 4
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 4
YMTZCQOAGFRQHV-UHFFFAOYSA-N 3-methyl-4,5-dihydro-1,2-thiazole Chemical compound CC1=NSCC1 YMTZCQOAGFRQHV-UHFFFAOYSA-N 0.000 claims description 4
150000001733 carboxylic acid esters Chemical class 0.000 claims description 4
150000004665 fatty acids Chemical class 0.000 claims description 4
BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 claims description 4
229940041616 menthol Drugs 0.000 claims description 4
229940075554 sorbate Drugs 0.000 claims description 4
PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
JEBFVOLFMLUKLF-IFPLVEIFSA-N Astaxanthin Natural products CC(=C/C=C/C(=C/C=C/C1=C(C)C(=O)C(O)CC1(C)C)/C)C=CC=C(/C)C=CC=C(/C)C=CC2=C(C)C(=O)C(O)CC2(C)C JEBFVOLFMLUKLF-IFPLVEIFSA-N 0.000 claims description 3
239000004287 Dehydroacetic acid Substances 0.000 claims description 3
229920002125 Sokalan® Polymers 0.000 claims description 3
235000013793 astaxanthin Nutrition 0.000 claims description 3
MQZIGYBFDRPAKN-ZWAPEEGVSA-N astaxanthin Chemical compound C([C@H](O)C(=O)C=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C(=O)[C@@H](O)CC1(C)C MQZIGYBFDRPAKN-ZWAPEEGVSA-N 0.000 claims description 3
229940022405 astaxanthin Drugs 0.000 claims description 3
239000001168 astaxanthin Substances 0.000 claims description 3
229940050390 benzoate Drugs 0.000 claims description 3
229960004365 benzoic acid Drugs 0.000 claims description 3
229960003237 betaine Drugs 0.000 claims description 3
235000019258 dehydroacetic acid Nutrition 0.000 claims description 3
229940061632 dehydroacetic acid Drugs 0.000 claims description 3
150000008131 glucosides Chemical class 0.000 claims description 3
229920001285 xanthan gum Polymers 0.000 claims description 3
235000010493 xanthan gum Nutrition 0.000 claims description 3
239000000230 xanthan gum Substances 0.000 claims description 3
229940082509 xanthan gum Drugs 0.000 claims description 3
PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
HXQDXOBJMWXQFR-UHFFFAOYSA-N CCCCNC(OC#CC)=O.I Chemical compound CCCCNC(OC#CC)=O.I HXQDXOBJMWXQFR-UHFFFAOYSA-N 0.000 claims description 2
229960000271 arbutin Drugs 0.000 claims description 2
235000019864 coconut oil Nutrition 0.000 claims description 2
239000003240 coconut oil Substances 0.000 claims description 2
239000003205 fragrance Substances 0.000 claims description 2
JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 claims description 2
BJRNKVDFDLYUGJ-UHFFFAOYSA-N p-hydroxyphenyl beta-D-alloside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-UHFFFAOYSA-N 0.000 claims description 2
229940032094 squalane Drugs 0.000 claims description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
150000004676 glycans Chemical class 0.000 claims 3
229920001282 polysaccharide Polymers 0.000 claims 3
239000005017 polysaccharide Substances 0.000 claims 3
239000008213 purified water Substances 0.000 claims 3
229940058015 1,3-butylene glycol Drugs 0.000 claims 2
JNAYPSWVMNJOPQ-UHFFFAOYSA-N 2,3-bis(16-methylheptadecanoyloxy)propyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC(C)C)COC(=O)CCCCCCCCCCCCCCC(C)C JNAYPSWVMNJOPQ-UHFFFAOYSA-N 0.000 claims 2
241000233866 Fungi Species 0.000 claims 2
235000019437 butane-1,3-diol Nutrition 0.000 claims 2
HNRMPXKDFBEGFZ-UHFFFAOYSA-N ethyl trimethyl methane Natural products CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 claims 2
NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims 1
QYPPJABKJHAVHS-UHFFFAOYSA-N Agmatine Natural products NCCCCNC(N)=N QYPPJABKJHAVHS-UHFFFAOYSA-N 0.000 claims 1
241000588986 Alcaligenes Species 0.000 claims 1
FVCMOHDQNLUHBT-UHFFFAOYSA-N C(CCC)N(C(=O)I)C#CC Chemical compound C(CCC)N(C(=O)I)C#CC FVCMOHDQNLUHBT-UHFFFAOYSA-N 0.000 claims 1
ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 claims 1
OEWBEINAQKIQLZ-CMRBMDBWSA-N [(2s)-2-[(2r)-3,4-bis(2-hexyldecanoyloxy)-5-oxo-2h-furan-2-yl]-2-(2-hexyldecanoyloxy)ethyl] 2-hexyldecanoate Chemical compound CCCCCCCCC(CCCCCC)C(=O)OC[C@H](OC(=O)C(CCCCCC)CCCCCCCC)[C@H]1OC(=O)C(OC(=O)C(CCCCCC)CCCCCCCC)=C1OC(=O)C(CCCCCC)CCCCCCCC OEWBEINAQKIQLZ-CMRBMDBWSA-N 0.000 claims 1
QYPPJABKJHAVHS-UHFFFAOYSA-P agmatinium(2+) Chemical compound NC(=[NH2+])NCCCC[NH3+] QYPPJABKJHAVHS-UHFFFAOYSA-P 0.000 claims 1
229960001631 carbomer Drugs 0.000 claims 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims 1
229920001748 polybutylene Polymers 0.000 claims 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 154
239000000284 extract Substances 0.000 description 101
235000010323 ascorbic acid Nutrition 0.000 description 93
239000011668 ascorbic acid Substances 0.000 description 93
229960005070 ascorbic acid Drugs 0.000 description 93
125000004432 carbon atom Chemical group C* 0.000 description 46
150000007524 organic acids Chemical class 0.000 description 35
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 35
125000002947 alkylene group Chemical group 0.000 description 34
230000000694 effects Effects 0.000 description 30
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 30
229960000401 tranexamic acid Drugs 0.000 description 29
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 description 28
GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 27
229910019142 PO4 Inorganic materials 0.000 description 25
235000021317 phosphate Nutrition 0.000 description 25
239000010452 phosphate Substances 0.000 description 24
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 22
239000011734 sodium Substances 0.000 description 22
239000006096 absorbing agent Substances 0.000 description 21
229920002674 hyaluronan Polymers 0.000 description 21
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JJOJFIHJIRWASH-UHFFFAOYSA-N Eicosanedioic acid Natural products OC(=O)CCCCCCCCCCCCCCCCCCC(O)=O JJOJFIHJIRWASH-UHFFFAOYSA-N 0.000 description 20
239000003921 oil Substances 0.000 description 19
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229910052708 sodium Inorganic materials 0.000 description 19
229940083542 sodium Drugs 0.000 description 19
235000015424 sodium Nutrition 0.000 description 19
KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 18
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 description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 18
238000001556 precipitation Methods 0.000 description 18
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