CH678810A5 - - Google Patents

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Publication number: CH678810A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; group; compound; substituted; hair
Prior art date: 1988-02-18

Application number

CH563/89A

Other languages

German (de)

English (en)

Inventor

Hajime Aoyama

Satoshi Ono

Osamu Oohashi

Hirokazu Narita

Shuntaro Takano

Original Assignee

Toyama Chemical Co Ltd

Priority date (The priority date 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 date listed.)

1988-02-18

Filing date

1989-02-17

Publication date

1991-11-15

1989-01-27 Priority claimed from JP1813489A external-priority patent/JP2819415B2/ja

1989-01-27 Priority claimed from JP1813589A external-priority patent/JP2787695B2/ja

1989-02-02 Priority claimed from JP1022560A external-priority patent/JP2787696B2/ja

1989-02-17 Application filed by Toyama Chemical Co Ltd filed Critical Toyama Chemical Co Ltd

1991-11-15 Publication of CH678810A5 publication Critical patent/CH678810A5/de

Links

125000004432 carbon atom Chemical group C* 0.000 claims description 123
150000001875 compounds Chemical class 0.000 claims description 97
-1 Alkyisuifonyl Chemical group 0.000 claims description 87
238000000034 method Methods 0.000 claims description 49
150000003839 salts Chemical class 0.000 claims description 37
125000004423 acyloxy group Chemical group 0.000 claims description 33
125000002015 acyclic group Chemical group 0.000 claims description 28
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
230000003779 hair growth Effects 0.000 claims description 26
125000001931 aliphatic group Chemical group 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 25
125000004414 alkyl thio group Chemical group 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 13
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
125000002252 acyl group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000001189 phytyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
239000004480 active ingredient Substances 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
125000003282 alkyl amino group Chemical group 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
239000006210 lotion Substances 0.000 claims description 7
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 6
125000005530 alkylenedioxy group Chemical group 0.000 claims description 6
125000004663 dialkyl amino group Chemical group 0.000 claims description 6
HJMZWDOOERQMND-ILWBRPEASA-N (e,7r,11r)-1-methoxy-3,7,11,15-tetramethylhexadec-2-ene Chemical compound COC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C HJMZWDOOERQMND-ILWBRPEASA-N 0.000 claims description 4
239000006071 cream Substances 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
230000000699 topical effect Effects 0.000 claims description 4
241000124008 Mammalia Species 0.000 claims description 3
229950010765 pivalate Drugs 0.000 claims description 3
239000000443 aerosol Substances 0.000 claims description 2
BOABYHFMEHVUTD-HEHNFIMWSA-N ethyl (e)-3,7,11,15-tetramethylhexadec-2-enoate Chemical compound CCOC(=O)\C=C(/C)CCCC(C)CCCC(C)CCCC(C)C BOABYHFMEHVUTD-HEHNFIMWSA-N 0.000 claims description 2
239000008266 hair spray Substances 0.000 claims description 2
235000015110 jellies Nutrition 0.000 claims description 2
239000000843 powder Substances 0.000 claims description 2
230000001256 tonic effect Effects 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 4
125000000623 heterocyclic group Chemical group 0.000 claims 4
239000003937 drug carrier Substances 0.000 claims 2
KUAAWKXICOBVGC-MRIFWDATSA-N C(C)(C)(C)OC\C=C(/C)\CCC[C@H](C)CCC[C@H](C)CCCC(C)C Chemical compound C(C)(C)(C)OC\C=C(/C)\CCC[C@H](C)CCC[C@H](C)CCCC(C)C KUAAWKXICOBVGC-MRIFWDATSA-N 0.000 claims 1
238000010960 commercial process Methods 0.000 claims 1
239000008274 jelly Substances 0.000 claims 1
239000002674 ointment Substances 0.000 claims 1
239000000243 solution Substances 0.000 description 50
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
239000002904 solvent Substances 0.000 description 41
238000006243 chemical reaction Methods 0.000 description 39
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
239000000203 mixture Substances 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
238000004821 distillation Methods 0.000 description 19
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
230000000694 effects Effects 0.000 description 14
235000017557 sodium bicarbonate Nutrition 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
235000019441 ethanol Nutrition 0.000 description 12
238000004440 column chromatography Methods 0.000 description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
239000003480 eluent Substances 0.000 description 10
239000008213 purified water Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 description 8
HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 description 8
BOTWFXYSPFMFNR-OALUTQOASA-N all-rac-phytol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)=CCO BOTWFXYSPFMFNR-OALUTQOASA-N 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
239000012085 test solution Substances 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
230000002411 adverse Effects 0.000 description 6
239000000284 extract Substances 0.000 description 6
239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
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 5
241000699666 Mus <mouse, genus> Species 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
239000012948 isocyanate Substances 0.000 description 5
239000000787 lecithin Substances 0.000 description 5
235000010445 lecithin Nutrition 0.000 description 5
229940067606 lecithin Drugs 0.000 description 5
229940057995 liquid paraffin Drugs 0.000 description 5
239000011591 potassium Substances 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 4
ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 4
239000012359 Methanesulfonyl chloride Substances 0.000 description 4
150000008065 acid anhydrides Chemical class 0.000 description 4
FUWUEFKEXZQKKA-UHFFFAOYSA-N beta-thujaplicin Chemical compound CC(C)C=1C=CC=C(O)C(=O)C=1 FUWUEFKEXZQKKA-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
150000007530 organic bases Chemical class 0.000 description 4
239000007800 oxidant agent Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
229940079889 pyrrolidonecarboxylic acid Drugs 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
235000013871 bee wax Nutrition 0.000 description 3
239000012166 beeswax Substances 0.000 description 3
239000004359 castor oil Substances 0.000 description 3
235000019438 castor oil Nutrition 0.000 description 3
REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 3
239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
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 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000004006 olive oil Substances 0.000 description 3
235000008390 olive oil Nutrition 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
235000019333 sodium laurylsulphate Nutrition 0.000 description 3
150000003462 sulfoxides Chemical class 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 2
QSKPZDMBULYMDQ-UHFFFAOYSA-N 2,3-dihydroxypropyl pentadecanoate Chemical compound CCCCCCCCCCCCCCC(=O)OCC(O)CO QSKPZDMBULYMDQ-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 2
208000001840 Dandruff Diseases 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
229940124091 Keratolytic Drugs 0.000 description 2
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
229930003427 Vitamin E Natural products 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
TUFYVOCKVJOUIR-UHFFFAOYSA-N alpha-Thujaplicin Natural products CC(C)C=1C=CC=CC(=O)C=1O TUFYVOCKVJOUIR-UHFFFAOYSA-N 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
229940121363 anti-inflammatory agent Drugs 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
229960000541 cetyl alcohol Drugs 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000002826 coolant Substances 0.000 description 2
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
229930182833 estradiol Natural products 0.000 description 2
229960005309 estradiol Drugs 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 2
FOYKKGHVWRFIBD-UHFFFAOYSA-N gamma-tocopherol acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 FOYKKGHVWRFIBD-UHFFFAOYSA-N 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
229940088597 hormone Drugs 0.000 description 2
239000005556 hormone Substances 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
230000001530 keratinolytic effect Effects 0.000 description 2
239000003410 keratolytic agent Substances 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
229930182817 methionine Natural products 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
235000001968 nicotinic acid Nutrition 0.000 description 2
239000011664 nicotinic acid Substances 0.000 description 2
SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
239000002304 perfume Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/673—Vitamin B group
- A61K8/675—Vitamin B3 or vitamin B3 active, e.g. nicotinamide, nicotinic acid, nicotinyl aldehyde
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Birds (AREA)
Epidemiology (AREA)
Emergency Medicine (AREA)
Dermatology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cosmetics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH563/89A 1988-02-18 1989-02-17 CH678810A5 (2)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
JP3396888		1988-02-18
JP13682488		1988-06-03
JP1813489A JP2819415B2 (ja)	1988-06-03	1989-01-27	養毛剤
JP1813589A JP2787695B2 (ja)	1989-01-27	1989-01-27	養毛剤
JP1022560A JP2787696B2 (ja)	1988-02-18	1989-02-02	発毛促進剤

Publications (1)

Publication Number	Publication Date
CH678810A5 true CH678810A5 (2)	1991-11-15

Family

ID=27519995

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH563/89A CH678810A5 (2)	1988-02-18	1989-02-17

Country Status (11)

Country	Link
US (1)	US5236950A (2)
KR (1)	KR910004583B1 (2)
AU (1)	AU619247B2 (2)
BE (1)	BE1004398A4 (2)
CA (1)	CA1339196C (2)
CH (1)	CH678810A5 (2)
DE (1)	DE3904751C2 (2)
FR (1)	FR2627384B1 (2)
GB (1)	GB2216003B (2)
NL (1)	NL8900396A (2)
SE (1)	SE8900567A0 (2)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2787695B2 (ja)	1989-01-27	1998-08-20	富山化学工業株式会社	養毛剤
CH683426A5 (de) *	1993-08-24	1994-03-15	Marigen Sa	Biotenside Lösungsvermittler für Pharmazeutika und Kosmetika.
EP0752465A1 (en) *	1995-06-01	1997-01-08	The Procter & Gamble Company	Betaine esters for delivery of alcohols
WO1997009039A2 (en) *	1995-09-08	1997-03-13	The Government Of The United States Of America, Represented By The Secretary Of The Department Of Health And Human Services	Composition comprising vitamin f
US5776443A (en) *	1996-03-18	1998-07-07	Chesebrough-Pond's Usa Co., Division Of Conopco, Inc.	Hair care compositions
US6177067B1 (en)	1996-08-09	2001-01-23	Shiseido Company, Ltd.	Hair revitalizing tonic composition containing a 2,2-dimethylpropanediol compound and use thereof
EP0823251A3 (en) *	1996-08-09	2000-02-09	Shiseido Company Limited	Hair revitalizing tonic composition containing a 2,2-dimethylpropanediol compound and use thereof
US6050990A (en) *	1996-12-05	2000-04-18	Thermolase Corporation	Methods and devices for inhibiting hair growth and related skin treatments
US5945441A (en) *	1997-06-04	1999-08-31	Gpi Nil Holdings, Inc.	Pyrrolidine carboxylate hair revitalizing agents
US6110450A (en) *	1998-09-15	2000-08-29	Helene Curtis, Inc.	Hair care compositions comprising ceramide
WO2000032179A2 (en)	1998-12-01	2000-06-08	University Of Kentucky Research Foundation	Use of nicotonic acid derivatives for the treatment of dna damage in skin cells
JP2002179549A (ja) *	2000-12-12	2002-06-26	Kishohin Kagaku Kaiho Kenkyusho:Kk	皮膚外用剤
CN1809330B (zh) *	2003-06-17	2010-10-13	Dsmip资产公司	含有植烷酸或其衍生物的局部用制剂
WO2008106091A1 (en) *	2007-02-26	2008-09-04	Yeda Research And Development Co. Ltd.	Use of long-chain alcohol derivatives for the treatment of alopecia areata
US20170172869A1 (en)	2015-12-17	2017-06-22	Sidiram S. Ragoonath	Hair Growth Product
FR3110427B1 (fr) *	2020-05-20	2023-07-14	Laboratoires Eriger	Conjugué terpenique de couplage
CN120603812A (zh) *	2023-01-27	2025-09-05	株式会社萩原农场生产研究所	癌细胞增殖抑制组合物和加工食品

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Publication number	Priority date	Publication date	Assignee	Title
GB780801A (en) *	1953-01-22	1957-08-07	Dehydag Gmbh	Improvements in and relating to cosmetic preparations, soap, deodorants and preparations for repelling insects
FR1190002A (fr) *	1956-10-18	1959-10-08	Wickhen Products	Procédé et composition pour augmenter la porosité à la vapeur d'eau des matières grasses notamment en cosmétologie
GB923400A (en) *	1960-09-07	1963-04-10	Hoffmann La Roche	Aliphatic triols, a process for their manufacture and cosmetic preparations containing same
NL278987A (2) *	1961-06-26
DE1467955A1 (de) *	1964-05-12	1969-02-06	Hugo Janistyn	Kosmetische Zubereitung von Phytol und/oder Phytolderivaten
JPS5327771B2 (2) *	1972-11-06	1978-08-10
US4192953A (en) *	1975-11-18	1980-03-11	Sankyo Company Limited	Polyprenyl derivatives
US4059641A (en) *	1975-11-18	1977-11-22	Sankyo Company Limited	Polyprenyl derivatives
US4260551A (en) *	1975-11-18	1981-04-07	Sankyo Company Limited	Polyprenyl derivatives
US4139619A (en) *	1976-05-24	1979-02-13	The Upjohn Company	6-Amino-4-(substituted amino)-1,2-dihydro-1-hydroxy-2-iminopyrimidine, topical compositions and process for hair growth
US4596812A (en) *	1976-05-24	1986-06-24	The Upjohn Company	Methods and solutions for treating male pattern alopecia
DE2812978C2 (de) *	1978-03-23	1984-09-20	Nisshin Flour Milling Co., Ltd.,, Tokio / Tokyo	Antimagengeschwürmittel
US4738801A (en) *	1978-03-23	1988-04-19	Nisshin Flour Milling Co., Ltd.	Antiulcer compounds
JPS5731615A (en) *	1980-07-31	1982-02-20	Eisai Co Ltd	Remedy for skin disease with keratinization
DE3201511A1 (de) *	1982-01-20	1983-07-28	Henkel Kgaa	Sebosuppressive kosmetische mittel, welche laengerkettige alkanole und antioxidantien enthalten
JPS5973516A (ja) *	1982-10-21	1984-04-25	Eisai Co Ltd	抗炎症剤
JPS604113A (ja) *	1983-06-21	1985-01-10	Lion Corp	養毛剤
JPS61207321A (ja) *	1985-03-13	1986-09-13	Asama Kasei Kk	養毛料
JPS61282310A (ja) *	1985-06-07	1986-12-12	Shionogi & Co Ltd	毛髪化粧料
DE3711841A1 (de) *	1987-04-08	1988-10-27	Henkel Kgaa	Haarregenerierende zubereitungen
DE3738405A1 (de) *	1987-11-12	1989-05-24	Henkel Kgaa	Sebosuppressive zubereitungen
DE3738406A1 (de) *	1987-11-12	1989-05-24	Henkel Kgaa	Sebosuppressive topische zubereitungen

1989
- 1989-02-14 GB GB8903335A patent/GB2216003B/en not_active Expired - Lifetime
- 1989-02-15 AU AU29953/89A patent/AU619247B2/en not_active Ceased
- 1989-02-16 DE DE3904751A patent/DE3904751C2/de not_active Expired - Fee Related
- 1989-02-16 CA CA000591244A patent/CA1339196C/en not_active Expired - Fee Related
- 1989-02-17 US US07/311,945 patent/US5236950A/en not_active Expired - Fee Related
- 1989-02-17 NL NL8900396A patent/NL8900396A/nl unknown
- 1989-02-17 SE SE8900567A patent/SE8900567A0/sv not_active Application Discontinuation
- 1989-02-17 CH CH563/89A patent/CH678810A5/de not_active IP Right Cessation
- 1989-02-17 FR FR8902101A patent/FR2627384B1/fr not_active Expired - Fee Related
- 1989-02-17 BE BE8900164A patent/BE1004398A4/fr not_active IP Right Cessation
- 1989-02-18 KR KR1019890001898A patent/KR910004583B1/ko not_active Expired

Also Published As

Publication number	Publication date
AU619247B2 (en)	1992-01-23
KR890012623A (ko)	1989-09-18
AU2995389A (en)	1989-08-24
SE8900567D0 (sv)	1989-02-17
KR910004583B1 (ko)	1991-07-06
US5236950A (en)	1993-08-17
DE3904751A1 (de)	1989-08-24
SE8900567A0 (sv)	1989-08-19
GB2216003B (en)	1992-06-10
CA1339196C (en)	1997-08-05
DE3904751C2 (de)	1998-03-26
BE1004398A4 (fr)	1992-11-17
GB8903335D0 (en)	1989-04-05
FR2627384A1 (fr)	1989-08-25
NL8900396A (nl)	1989-09-18
GB2216003A (en)	1989-10-04
FR2627384B1 (fr)	1993-10-29

Legal Events

Date	Code	Title	Description
1999-10-15	PL	Patent ceased

Publication	Publication Date	Title
DE69203545T2 (de)	1996-01-11	2,4,6-Triaminopyrimidin-N-Oxidderivate enthaltende Zusammensetzungen zur Verwendung beim Vermindern des Haarausfalles sowie zum Auslösen und Anregen des Haarwuchses und neue 2,4,6-Triaminopyrimidin-N-Oxidderivate.
DE69317044T2 (de)	1998-06-10	Mittel zur regulierung vom hautfettigkeitsgrad
DE69005248T2 (de)	1994-04-14	2-Aminopyrimidin-3-oxid-Derivate enthaltende Zusammensetzungen zur Verwendung zum Vermindern des Haarausfalles und zum Induzieren und Stimulieren des Haarwuchses und neue von 2-Aminopyrimidin-3-oxid abgeleitete Verbindungen.
DE3533308C2 (de)	1996-09-26	Aromatische, heterocyclische Derivate und ihre Verwendung auf dem pharmazeutischen und kosmetischen Gebiet
DE69231488T2 (de)	2001-02-08	Zusammenstellungen, um den Haarausfall zu hemmen und um Haarwuchs zu induzieren und zu stimulieren auf Basis von 2,4-Diamino-pyrimidin-3-Oxydderivaten
DE69100919T2 (de)	1994-05-05	Mittel zur Verwendung zum Verlangsamen des Haarausfalls sowie zum Auslösen und Anregen ihres Wachstums, die 2-Alkyl-4-amino(bzw. 2,4-Dialkyl)pyrimidin-3-oxidderivate enthalten sowie neue 2-Alkyl-4-aminopyrimidin-3-oxidderivate.
DE3904751C2 (de)	1998-03-26	Verwendung von Derivaten höherer Alkohole zur Haarwiederherstellung
DE69502130T2 (de)	1998-08-13	Polyenderivate, diese enthaltende pharmazeutische und kosmetische Zusammensetzungen und ihre Verwendung
DE60003021T2 (de)	2004-04-01	Benzoesäureesterderivate, diese enthaltende zusammenstellungen und deren anwendung
DE3780091T2 (de)	1993-02-11	Behandlung von pilzinfektionen.
US5132106A (en)	1992-07-21	Halogenated pyrimidine 3-oxide derivatives, their use for the treatment and prevention of hair loss and for stimulating its regrowth
DE3415413C2 (2)	1992-07-16
DE69513484T2 (de)	2000-03-16	Neue, von Dibenzofuran abgeleitete Verbindungen und pharmazeutische und kosmetische Zusammensetzungen, die sie enthalten.
DE60010925T2 (de)	2005-06-16	Vitamin d - analoga
DE3707245C2 (de)	1995-11-23	2,3,4,4a-Tetrahydro-4a,10,10-trimethyl - 1H-3, 9b - methandibenzofuranderivate, Verfahren zur Herstellung dieser Verbindungen und pharmazeutische und kosmetische Mittel, die diese Verbindungen enthalten
DE2850483C2 (2)	1987-07-09
EP0100827A1 (en)	1984-02-22	Pharmaceutical composition containing an aliphatic aminosulphonic acid
DE3855520T2 (de)	1997-02-06	Methode zur Verbesserung des Schlafes
DE69806465T2 (de)	2003-02-27	Eine heteroethynylen-brücke enthaltende bi-aromatische verbindungen und diese enthaltende pharmazeutische und kosmetische zusammensetzungen
DE69704213T2 (de)	2001-06-21	Bioaromatische dibenzofuranderivate und verwendung in der human- oder tiermedizin und in der kosmetik
DE3882722T2 (de)	1993-12-02	Gelöste Zusammensetzung von [Benzo-1,2,4-thiadiazin]-1,1-dioxid für die Haarkeimung und zur Förderung des Haarwachstums.
EP0906911A1 (de)	1999-04-07	Sulfonamid-substituierte Chromane (K+Kanal-Blocker), Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen
EP0913396A2 (de)	1999-05-06	Sulfonamid-substituierte Benzopyranderivate, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen
DE68915094T2 (de)	1994-12-08	Benzofuranverbindungen, Verfahren zu ihrer Herstellung, diese enthaltende pharmazeutische und kosmetische Zusammenstellungen und Verwendung dieser Zusammenstellungen.
CA2132528C (en)	2004-06-08	Agent for use as an anti-irritant