LU87304A1 - Nouveaux derives d'ureylene triamino-2,4,6 pyrimidine oxyde-3,leur preparation et leur utilisation en cosmetique et dermopharmacie - Google Patents

Nouveaux derives d'ureylene triamino-2,4,6 pyrimidine oxyde-3,leur preparation et leur utilisation en cosmetique et dermopharmacie Download PDF

Info

Publication number: LU87304A1
Authority: LU; Luxembourg
Prior art keywords: formula; amino; group; denote; compounds
Prior art date: 1988-07-29

Application number

LU87304A

Other languages

English (en)

French (fr)

Inventor

Maignan Jean

Lang Gerard

Original Assignee

Oreal

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.)

1988-07-29

Filing date

1988-07-29

Publication date

1990-02-07

1988-07-29 Application filed by Oreal filed Critical Oreal

1988-07-29 Priority to LU87304A priority Critical patent/LU87304A1/fr

1989-07-12 Priority to DE68917660T priority patent/DE68917660T2/de

1989-07-12 Priority to AT89402001T priority patent/ATE110370T1/de

1989-07-12 Priority to ES89402001T priority patent/ES2058572T3/es

1989-07-12 Priority to EP89402001A priority patent/EP0353123B1/de

1989-07-27 Priority to JP1192824A priority patent/JPH0278667A/ja

1989-07-31 Priority to CA000607056A priority patent/CA1334850C/fr

1990-02-07 Publication of LU87304A1 publication Critical patent/LU87304A1/fr

Links

238000002360 preparation method Methods 0.000 title claims description 23
239000002537 cosmetic Substances 0.000 title claims description 12
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title claims description 9
150000001875 compounds Chemical class 0.000 claims abstract description 48
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 17
125000000217 alkyl group Chemical group 0.000 claims abstract description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 7
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
125000003118 aryl group Chemical group 0.000 claims abstract description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 36
-1 nitro, hydroxyl Chemical group 0.000 claims description 26
150000001412 amines Chemical class 0.000 claims description 14
238000000034 method Methods 0.000 claims description 13
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
239000000243 solution Substances 0.000 claims description 9
201000004384 Alopecia Diseases 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
239000006210 lotion Substances 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
239000000499 gel Substances 0.000 claims description 6
201000004624 Dermatitis Diseases 0.000 claims description 5
208000004631 alopecia areata Diseases 0.000 claims description 5
208000024963 hair loss Diseases 0.000 claims description 5
230000003676 hair loss Effects 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
210000004761 scalp Anatomy 0.000 claims description 5
230000000699 topical effect Effects 0.000 claims description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
239000002674 ointment Substances 0.000 claims description 4
239000000843 powder Substances 0.000 claims description 4
230000003659 hair regrowth Effects 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
239000003880 polar aprotic solvent Substances 0.000 claims description 3
239000003755 preservative agent Substances 0.000 claims description 3
230000003637 steroidlike Effects 0.000 claims description 3
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
239000003963 antioxidant agent Substances 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
235000021466 carotenoid Nutrition 0.000 claims description 2
150000001747 carotenoids Chemical class 0.000 claims description 2
239000006071 cream Substances 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
239000003995 emulsifying agent Substances 0.000 claims description 2
239000000839 emulsion Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
230000003204 osmotic effect Effects 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
230000001737 promoting effect Effects 0.000 claims description 2
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
230000001105 regulatory effect Effects 0.000 claims description 2
239000002453 shampoo Substances 0.000 claims description 2
239000000344 soap Substances 0.000 claims description 2
239000007921 spray Substances 0.000 claims description 2
239000003381 stabilizer Substances 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
239000002260 anti-inflammatory agent Substances 0.000 claims 1
229940121363 anti-inflammatory agent Drugs 0.000 claims 1
239000007900 aqueous suspension Substances 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000000392 cycloalkenyl group Chemical group 0.000 claims 1
230000000887 hydrating effect Effects 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000001984 thiazolidinyl group Chemical group 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
235000013877 carbamide Nutrition 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 18
239000004202 carbamide Substances 0.000 description 17
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
235000019441 ethanol Nutrition 0.000 description 13
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
239000000725 suspension Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
229910001868 water Inorganic materials 0.000 description 11
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
239000013078 crystal Substances 0.000 description 9
238000004458 analytical method Methods 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
CLAHOZSYMRNIPY-UHFFFAOYSA-N 2-hydroxyethylurea Chemical compound NC(=O)NCCO CLAHOZSYMRNIPY-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
0 CCCC(C(C)(C)C)*1=CCC=CC1 Chemical compound CCCC(C(C)(C)C)*1=CCC=CC1 0.000 description 6
238000001816 cooling Methods 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000007858 starting material Substances 0.000 description 6
IWJFGRNIFIABLP-UHFFFAOYSA-N 2,3-dihydroxypropylurea Chemical compound NC(=O)NCC(O)CO IWJFGRNIFIABLP-UHFFFAOYSA-N 0.000 description 5
239000007787 solid Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
150000002513 isocyanates Chemical class 0.000 description 4
JTTIOYHBNXDJOD-UHFFFAOYSA-N 2,4,6-triaminopyrimidine Chemical compound NC1=CC(N)=NC(N)=N1 JTTIOYHBNXDJOD-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
231100000360 alopecia Toxicity 0.000 description 3
238000010586 diagram Methods 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000012258 stirred mixture Substances 0.000 description 3
150000003672 ureas Chemical class 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000013543 active substance Substances 0.000 description 2
OENHQHLEOONYIE-UKMVMLAPSA-N beta-Carotene Chemical compound CC=1CCCC(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)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 2
229940031098 ethanolamine Drugs 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
XMKLTEGSALONPH-UHFFFAOYSA-N 1,2,4,5-tetrazinane-3,6-dione Chemical class O=C1NNC(=O)NN1 XMKLTEGSALONPH-UHFFFAOYSA-N 0.000 description 1
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
UASSNOUWVBVUSX-UHFFFAOYSA-N 1-ethyl-1-(2-hydroxyethyl)urea Chemical compound CCN(C(N)=O)CCO UASSNOUWVBVUSX-UHFFFAOYSA-N 0.000 description 1
IHBLBMDDUQOYLA-UHFFFAOYSA-N 1-octadecyl-3-[4-[[4-(octadecylcarbamoylamino)phenyl]methyl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCCCCCCCCCCCCCCCCC)=CC=C1CC1=CC=C(NC(=O)NCCCCCCCCCCCCCCCCCC)C=C1 IHBLBMDDUQOYLA-UHFFFAOYSA-N 0.000 description 1
PNCWHIAZZSDHPU-UHFFFAOYSA-N 2-benzylsulfanylethanamine Chemical compound NCCSCC1=CC=CC=C1 PNCWHIAZZSDHPU-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
229920003091 Methocel™ Polymers 0.000 description 1
ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
GBFLZEXEOZUWRN-VKHMYHEASA-N S-carboxymethyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CSCC(O)=O GBFLZEXEOZUWRN-VKHMYHEASA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
239000000654 additive Substances 0.000 description 1
SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical compound C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 1
235000013734 beta-carotene Nutrition 0.000 description 1
239000011648 beta-carotene Substances 0.000 description 1
229960002747 betacarotene Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
150000001925 cycloalkenes Chemical group 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
229960002311 dithranol Drugs 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940031575 hydroxyethyl urea Drugs 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
229960003632 minoxidil Drugs 0.000 description 1
230000003020 moisturizing effect Effects 0.000 description 1
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 description 1
230000035515 penetration Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
229960002036 phenytoin Drugs 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229930002330 retinoic acid Natural products 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000002294 steroidal antiinflammatory agent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229960001295 tocopherol Drugs 0.000 description 1
239000011732 tocopherol Substances 0.000 description 1
229960001727 tretinoin Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Dermatology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cosmetics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

LU87304A 1988-07-29 1988-07-29 Nouveaux derives d'ureylene triamino-2,4,6 pyrimidine oxyde-3,leur preparation et leur utilisation en cosmetique et dermopharmacie LU87304A1 (fr)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
LU87304A LU87304A1 (fr)	1988-07-29	1988-07-29	Nouveaux derives d'ureylene triamino-2,4,6 pyrimidine oxyde-3,leur preparation et leur utilisation en cosmetique et dermopharmacie
DE68917660T DE68917660T2 (de)	1988-07-29	1989-07-12	Harnstoffhaltige 2,4,6-Triaminopyrimidin-3-oxid-Derivate, deren Herstellung und deren Verwendung für Kosmetika und Hautpharmazie.
AT89402001T ATE110370T1 (de)	1988-07-29	1989-07-12	Harnstoffhaltige 2,4,6-triaminopyrimidin-3-oxid- derivate, deren herstellung und deren verwendung für kosmetika und hautpharmazie.
ES89402001T ES2058572T3 (es)	1988-07-29	1989-07-12	Nuevos derivados de ureileno-2,4,6-triamino-pirimidina-3-oxido, su preparacion y su empleo en cosmetica y dermofarmacia.
EP89402001A EP0353123B1 (de)	1988-07-29	1989-07-12	Harnstoffhaltige 2,4,6-Triaminopyrimidin-3-oxid-Derivate, deren Herstellung und deren Verwendung für Kosmetika und Hautpharmazie
JP1192824A JPH0278667A (ja)	1988-07-29	1989-07-27	新規ユリレン２，４，６―トリアミノピリミジン３―オキサイド誘導体、その製造法及び化粧料及び皮膚薬剤における使用
CA000607056A CA1334850C (fr)	1988-07-29	1989-07-31	Derives d'ureylene triamino-2,4,6 pyrimidine oxyde-3, leur preparation et leur utilisation en cosmetique et dermopharmacie

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU87304		1988-07-29
LU87304A LU87304A1 (fr)	1988-07-29	1988-07-29	Nouveaux derives d'ureylene triamino-2,4,6 pyrimidine oxyde-3,leur preparation et leur utilisation en cosmetique et dermopharmacie

Publications (1)

Publication Number	Publication Date
LU87304A1 true LU87304A1 (fr)	1990-02-07

Family

ID=19731082

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU87304A LU87304A1 (fr)	1988-07-29	1988-07-29	Nouveaux derives d'ureylene triamino-2,4,6 pyrimidine oxyde-3,leur preparation et leur utilisation en cosmetique et dermopharmacie

Country Status (7)

Country	Link
EP (1)	EP0353123B1 (de)
JP (1)	JPH0278667A (de)
AT (1)	ATE110370T1 (de)
CA (1)	CA1334850C (de)
DE (1)	DE68917660T2 (de)
ES (1)	ES2058572T3 (de)
LU (1)	LU87304A1 (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6159950A (en) *	1998-10-16	2000-12-12	Cornell Research Foundation, Inc.	Method of modulating hair growth
FR2791671B1 (fr)	1999-04-01	2001-05-11	Oreal	Nouveaux composes derives d'esters d'acide benzoique, composition les comprenant et utilisation
ES2774911T3 (es)	2002-06-21	2020-07-23	Oreal	Utilización de la taurina o derivados para el tratamiento de la alopecia
FR2920309B1 (fr)	2007-08-28	2010-05-28	Galderma Res & Dev	Utilisation de travoprost pour traiter la chute des cheveux
FR2953722B1 (fr)	2009-12-16	2012-03-09	Expanscience Lab	Composition comprenant au moins un sucre en c7 pour le traitement de l'alopecie, pour le traitement cosmetique des phaneres, et pour le soin des cheveux, cils ou ongles
WO2015085373A1 (en)	2013-12-12	2015-06-18	Cellmid Limited	Method of treatment of alopecia with monoterpenoids
AU2017275657B2 (en)	2016-06-02	2021-08-19	Novartis Ag	Potassium channel modulators
UA123810C2 (uk)	2017-01-23	2021-06-02	Цадент Терапеутікс, Інк.	Модулятори калієвих каналів
MX2021004647A (es)	2018-10-22	2021-08-16	Novartis Ag	Formas cristalinas de moduladores de los canales de potasio.
EP3895686B1 (de)	2020-04-14	2025-04-09	Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V.	Natürliche zusammensetzung zur stimulierung des haarwuchses und zur vorbeugung und behandlung von haarausfall
EP3895685A1 (de)	2020-04-14	2021-10-20	Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V.	Natürliche zusammensetzung zur haarwachstumsstimulation und haarverlustverhinderung und behandlung ohne konservierungsmittel

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EP0042669A3 (de) *	1980-06-23	1982-03-24	The Upjohn Company	In Tierfutter verwendbare Verbindungen und Zusammensetzungen
WO1986000616A1 (en) *	1984-07-13	1986-01-30	Gail Sansone Bazzano	Substituted pyrimidine oxides useful for hair growth promotion
LU86958A1 (fr) *	1987-07-31	1989-03-08	Oreal	Sels d'acide thiamorpholinone carboxylique et de derives de diamino-2,4 pyrimidine,leur utilisation en cosmetique et pharmacie
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1988
- 1988-07-29 LU LU87304A patent/LU87304A1/fr unknown
1989
- 1989-07-12 EP EP89402001A patent/EP0353123B1/de not_active Expired - Lifetime
- 1989-07-12 AT AT89402001T patent/ATE110370T1/de not_active IP Right Cessation
- 1989-07-12 DE DE68917660T patent/DE68917660T2/de not_active Expired - Fee Related
- 1989-07-12 ES ES89402001T patent/ES2058572T3/es not_active Expired - Lifetime
- 1989-07-27 JP JP1192824A patent/JPH0278667A/ja active Pending
- 1989-07-31 CA CA000607056A patent/CA1334850C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE68917660D1 (de)	1994-09-29
EP0353123A1 (de)	1990-01-31
DE68917660T2 (de)	1995-01-12
ATE110370T1 (de)	1994-09-15
CA1334850C (fr)	1995-03-21
ES2058572T3 (es)	1994-11-01
JPH0278667A (ja)	1990-03-19
EP0353123B1 (de)	1994-08-24

Publication	Publication Date	Title
EP0356271B1 (de)	1995-04-05	2,4-Diamino-pyrimidin-3-oxid-Derivate und deren Verwendung bei der Behandlung und zur Verhütung von Haarfall
EP0420707B1 (de)	1993-12-15	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
EP0522964B1 (de)	2000-10-04	Zusammenstellungen, um den Haarausfall zu hemmen und um Haarwuchs zu induzieren und zu stimulieren auf Basis von 2,4-Diamino-pyrimidin-3-Oxydderivaten
EP0459890B1 (de)	1994-01-05	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
EP0408442B1 (de)	1994-08-31	Halogenierte Pyrimidin-3-oxid-Derivate, deren Verwendung für die Behandlung und die Verhütung von Haarausfall und für die Wachstumsförderung von Haaren
EP0540629A1 (de)	1993-05-12	Verwendung von pyrimidin-3-oxydderivaten zur verhütung von haarausfall und deren anwendung in topischen zusammensetzungen.
EP0353123B1 (de)	1994-08-24	Harnstoffhaltige 2,4,6-Triaminopyrimidin-3-oxid-Derivate, deren Herstellung und deren Verwendung für Kosmetika und Hautpharmazie
EP0303871B1 (de)	1992-12-09	Oxadiazol-pyrimidinone, ihre Herstellung und ihre kosmetische und dermopharmazeutische Verwendung
CA2110273C (fr)	2002-02-12	Composes derives de benzimidazole, leur procede de preparation et leur utilisation dans les domaines therapeutique et cosmetique
EP0209770A1 (de)	1987-01-28	Eicosatriynester und Amide und deren Verwendung in der Pharmazie und Kosmetik
EP0342115B1 (de)	1992-09-09	Sulfurierte Eicosanoide und deren Verwendung in Arzneimitteln und Kosmetika
EP0290020B1 (de)	1992-04-08	Quaternäre Ammonium-Retinoate, ihre Verwendung in der Kosmetik und Dermopharmazie
EP0179697A1 (de)	1986-04-30	Vitamin A-säure Derivate, Verfahren zu ihrer Herstellung und pharmazeutische und kosmetische Präparate die sie enthalten
CA1314884C (fr)	1993-03-23	Sels d'acide thiamorpholinone carboxylique et de derives de diamino-2,4 pyrimidine, leur utilisation en cosmetique et pharmacie
FR2677247A1 (fr)	1992-12-11	Composition pour freiner la chute des cheveux et pour induire et stimuler leur croissance, a base de derives de pyridine-1 oxyde.
EP0279954A2 (de)	1988-08-31	Eicosattraynsäureamide, ihre Verwendung in der Arzneimittelkunde und Kosmetika, ihre Herstellung und Verfahren zur Herstellung von Eicosattraynsäure
CA2285886C (fr)	2002-01-01	Compositions destinees a etre utilisees pour freiner la chute des cheveux et pour induire et stimuler leur croissance, contenant des oxadiazolopyrimidines
EP0487698A1 (de)	1992-06-03	2,4-diamino-1,3,5-triazinderivate und ihre anwendung für die behandlung und die verhütung des haarausfalls
EP0427625B1 (de)	1995-01-04	Interne Salze des 2,4-Diamino-6-alkoxy-3-sulphooxypyrmidium-Hydroxids und ihre Verwendung für die Behandlung und die Verhütung des Haarausfalls
FR2657609A1 (fr)	1991-08-02	Nouveaux derives de pyrimidine oxyde-3 halogenes, leur utilisation pour le traitement et la prevention de la chute des cheveux et pour stimuler leur repousse.