LU87308A1 - Nouveaux derives de diamino-2,4 pyrimidine oxyde-3 et leur utilisation pour le traitement et la prevention de la chute des cheveux - Google Patents

Nouveaux derives de diamino-2,4 pyrimidine oxyde-3 et leur utilisation pour le traitement et la prevention de la chute des cheveux Download PDF

Info

Publication number: LU87308A1
Authority: LU; Luxembourg
Prior art keywords: agents; composition; compound; composition according; diamino
Prior art date: 1988-08-01

Application number

LU87308A

Other languages

English (en)

French (fr)

Inventor

Hocquaux Michel

Dumats Jacqueline

Gaetani Quinto

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.)

1988-08-01

Filing date

1988-08-01

Publication date

1990-03-13

1988-08-01 Application filed by Oreal filed Critical Oreal

1988-08-01 Priority to LU87308A priority Critical patent/LU87308A1/fr

1989-07-12 Priority to EP89402002A priority patent/EP0356271B1/de

1989-07-12 Priority to AT89402002T priority patent/ATE120738T1/de

1989-07-12 Priority to DE68922044T priority patent/DE68922044T2/de

1989-07-12 Priority to ES89402002T priority patent/ES2070186T3/es

1989-07-28 Priority to JP1194437A priority patent/JP2669903B2/ja

1989-07-31 Priority to US07/387,590 priority patent/US4973474A/en

1989-08-01 Priority to CA000607180A priority patent/CA1340445C/fr

1990-03-13 Publication of LU87308A1 publication Critical patent/LU87308A1/fr

Links

201000004384 Alopecia Diseases 0.000 title claims abstract description 15
208000024963 hair loss Diseases 0.000 title claims abstract description 11
230000003676 hair loss Effects 0.000 title claims abstract description 11
230000002265 prevention Effects 0.000 title abstract description 5
YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 28
125000003118 aryl group Chemical group 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
239000001257 hydrogen Substances 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 47
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 13
-1 2-ethylhexyl Chemical group 0.000 claims description 12
239000002537 cosmetic Substances 0.000 claims description 11
239000003795 chemical substances by application Substances 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 6
239000000499 gel Substances 0.000 claims description 5
239000006210 lotion Substances 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
210000004761 scalp Anatomy 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
230000000699 topical effect Effects 0.000 claims description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
239000000839 emulsion Substances 0.000 claims description 4
230000003659 hair regrowth Effects 0.000 claims description 4
239000002674 ointment Substances 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
239000002562 thickening agent Substances 0.000 claims description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
239000000443 aerosol Substances 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
239000003963 antioxidant agent Substances 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
239000003995 emulsifying agent Substances 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000006260 foam Substances 0.000 claims description 2
125000006038 hexenyl group Chemical group 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 2
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 2
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
230000003204 osmotic effect Effects 0.000 claims description 2
239000000843 powder Substances 0.000 claims description 2
239000003755 preservative agent Substances 0.000 claims description 2
230000001737 promoting effect Effects 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
239000002294 steroidal antiinflammatory agent Substances 0.000 claims description 2
230000003637 steroidlike Effects 0.000 claims description 2
229940098465 tincture Drugs 0.000 claims description 2
125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims 2
MMTAQMVXGXVICH-UHFFFAOYSA-N 6-ethoxypyrimidine-2,4-diamine Chemical group CCOC1=CC(N)=NC(N)=N1 MMTAQMVXGXVICH-UHFFFAOYSA-N 0.000 claims 1
150000005215 alkyl ethers Chemical class 0.000 claims 1
239000007900 aqueous suspension Substances 0.000 claims 1
239000003349 gelling agent Substances 0.000 claims 1
230000003020 moisturizing effect Effects 0.000 claims 1
230000008719 thickening Effects 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 abstract 2
SGHQFNHCCOBUKB-UHFFFAOYSA-N NC1=CC=NC(N)=[N+]1[O-] Chemical class NC1=CC=NC(N)=[N+]1[O-] SGHQFNHCCOBUKB-UHFFFAOYSA-N 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
235000019441 ethanol Nutrition 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
201000004624 Dermatitis Diseases 0.000 description 4
231100000360 alopecia Toxicity 0.000 description 4
QJIUMVUZDYPQRT-UHFFFAOYSA-N 6-chloro-2,4-pyrimidinediamine Chemical compound NC1=CC(Cl)=NC(N)=N1 QJIUMVUZDYPQRT-UHFFFAOYSA-N 0.000 description 3
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 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
208000004631 alopecia areata Diseases 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
230000004936 stimulating effect Effects 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000013543 active substance Substances 0.000 description 2
230000003276 anti-hypertensive effect Effects 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
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000001863 hydroxypropyl cellulose Substances 0.000 description 2
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
229940071676 hydroxypropylcellulose Drugs 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
229960003632 minoxidil Drugs 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
HQWAEQCLIWVOMF-UHFFFAOYSA-M 1,3-dioxolan-4-ylmethyl(trimethyl)azanium;iodide Chemical compound [I-].C[N+](C)(C)CC1COCO1 HQWAEQCLIWVOMF-UHFFFAOYSA-M 0.000 description 1
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
PNCWHIAZZSDHPU-UHFFFAOYSA-N 2-benzylsulfanylethanamine Chemical compound NCCSCC1=CC=CC=C1 PNCWHIAZZSDHPU-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-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
HMRUEKSBELJHMN-UHFFFAOYSA-N CC[N]1(C=C1)C(C)=N Chemical compound CC[N]1(C=C1)C(C)=N HMRUEKSBELJHMN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
229920003091 Methocel™ Polymers 0.000 description 1
239000007832 Na2SO4 Substances 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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
229920002305 Schizophyllan Polymers 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000001476 alcoholic effect Effects 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
238000004458 analytical method Methods 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
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
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
239000004202 carbamide Substances 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 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
238000000921 elemental analysis Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
230000003779 hair growth Effects 0.000 description 1
230000000887 hydrating effect Effects 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229950005431 oxapropanium iodide Drugs 0.000 description 1
230000035515 penetration Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229960002036 phenytoin Drugs 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229930002330 retinoic acid Natural products 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
238000011699 spontaneously hypertensive rat Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
SLYPOVJCSQHITR-UHFFFAOYSA-N tioxolone Chemical compound OC1=CC=C2SC(=O)OC2=C1 SLYPOVJCSQHITR-UHFFFAOYSA-N 0.000 description 1
229960003070 tioxolone Drugs 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
239000000230 xanthan gum Substances 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
235000010493 xanthan gum Nutrition 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
- C07D239/48—Two nitrogen atoms
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
- 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
- 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)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Dermatology (AREA)
Birds (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cosmetics (AREA)
Indole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

LU87308A 1988-08-01 1988-08-01 Nouveaux derives de diamino-2,4 pyrimidine oxyde-3 et leur utilisation pour le traitement et la prevention de la chute des cheveux LU87308A1 (fr)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
LU87308A LU87308A1 (fr)	1988-08-01	1988-08-01	Nouveaux derives de diamino-2,4 pyrimidine oxyde-3 et leur utilisation pour le traitement et la prevention de la chute des cheveux
EP89402002A EP0356271B1 (de)	1988-08-01	1989-07-12	2,4-Diamino-pyrimidin-3-oxid-Derivate und deren Verwendung bei der Behandlung und zur Verhütung von Haarfall
AT89402002T ATE120738T1 (de)	1988-08-01	1989-07-12	2,4-diamino-pyrimidin-3-oxid-derivate und deren verwendung bei der behandlung und zur verhütung von haarfall.
DE68922044T DE68922044T2 (de)	1988-08-01	1989-07-12	2,4-Diamino-pyrimidin-3-oxid-Derivate und deren Verwendung bei der Behandlung und zur Verhütung von Haarfall.
ES89402002T ES2070186T3 (es)	1988-08-01	1989-07-12	Nuevos derivados de 2,4-diamino-pirimidina-3-oxido y su utilizacion en la prevencion de la caida de los cabellos.
JP1194437A JP2669903B2 (ja)	1988-08-01	1989-07-28	新規な２・４―ジアミノピリミジン３―オキシド誘導体およびそれを含む組成物
US07/387,590 US4973474A (en)	1988-08-01	1989-07-31	2,4-diaminopyrimidine 3-oxide derivatives and their use for the treatment and prevention of hair loss
CA000607180A CA1340445C (fr)	1988-08-01	1989-08-01	Derives de diamino-2,4 pyrimidine oxyde-3 et leur utilisation pour le traitement et la prevention de la chute des cheveux

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU87308		1988-08-01
LU87308A LU87308A1 (fr)	1988-08-01	1988-08-01	Nouveaux derives de diamino-2,4 pyrimidine oxyde-3 et leur utilisation pour le traitement et la prevention de la chute des cheveux

Publications (1)

Publication Number	Publication Date
LU87308A1 true LU87308A1 (fr)	1990-03-13

Family

ID=19731083

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU87308A LU87308A1 (fr)	1988-08-01	1988-08-01	Nouveaux derives de diamino-2,4 pyrimidine oxyde-3 et leur utilisation pour le traitement et la prevention de la chute des cheveux

Country Status (8)

Country	Link
US (1)	US4973474A (de)
EP (1)	EP0356271B1 (de)
JP (1)	JP2669903B2 (de)
AT (1)	ATE120738T1 (de)
CA (1)	CA1340445C (de)
DE (1)	DE68922044T2 (de)
ES (1)	ES2070186T3 (de)
LU (1)	LU87308A1 (de)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR920700023A (ko) *	1989-06-12	1992-02-19	원본미기재	양모제
EP0408442B1 (de) *	1989-07-12	1994-08-31	L'oreal	Halogenierte Pyrimidin-3-oxid-Derivate, deren Verwendung für die Behandlung und die Verhütung von Haarausfall und für die Wachstumsförderung von Haaren
FR2662607B1 (fr) *	1990-05-30	1992-08-28	Oreal	Composition destinee a etre utilisee pour freiner la chute des cheveux et pour induire et stimuler leur croissance, contenant des derives d'alkyl-2 amino-4 (ou dialkyl-2-4) pyrimidine oxyde-3 .
FR2663327B1 (fr) *	1990-06-19	1992-09-25	Oreal	Nouveaux derives de diamino-2,4 triazine-1,3,5 et leur utilisation pour le traitement et la prevention de la chute des cheveux.
LU87766A1 (fr) *	1990-07-20	1992-03-11	Oreal	Utilisation de derives de pyrimidine 3-oxyde pour freiner la chute des cheveux et compositions topiques mises en oeuvre
US5043162A (en) *	1990-09-05	1991-08-27	Trager Seymour F	Hair growth promoter
US5143650A (en) *	1990-11-13	1992-09-01	Aster, Inc.	Electrophoretic coatable sealant compositions comprising polyvinyl chloride and furnace carbon black
FR2671082B1 (fr) *	1990-12-28	1993-04-16	Oreal	Agent a plusieurs composants ou kit de preparation de la forme sulfo-conjuguee de composes pyrimidino- ou triazino-n-oxyde et procede de mise en óoeuvre.
FR2678929A1 (fr) *	1991-07-11	1993-01-15	Oreal	Compositions pour freiner la chute des cheveux et pour induire et stimuler leur croissance a base de derives de 2,4-diamino pyrimidine 3-oxyde, nouveaux derives 2,4-diamino pyrimidine 3-oxyde.
US5451407A (en) *	1993-06-21	1995-09-19	Alza Corporation	Reduction or prevention of skin irritation or sensitization during transdermal administration of a irritating or sensitizing drug
FR2711060B1 (fr) *	1993-10-13	1995-11-17	Oreal	Procédé pour modifier la pousse des poils et/ou des cheveux et compositions utilisables à cet effet.
FR2732597B1 (fr) *	1995-04-05	1997-05-16	Oreal	Utilisation dans une composition en tant qu'activateur et/ou stabilisateur de cyclooxygenase d'au moins un derive de pyrimidine substitue en 6
US6159950A (en) *	1998-10-16	2000-12-12	Cornell Research Foundation, Inc.	Method of modulating hair growth
FR2785802B1 (fr) *	1998-11-12	2002-10-31	Oreal	2-amino, 4-alkylamino pyrimidine 3-oxydes comme anti-inflammatoires
FR2791671B1 (fr)	1999-04-01	2001-05-11	Oreal	Nouveaux composes derives d'esters d'acide benzoique, composition les comprenant et utilisation
SE0104421D0 (sv) *	2001-12-21	2001-12-21	Ponsus Pharma Ab	New composition
US9138408B2 (en)	2002-06-21	2015-09-22	L'oreal	Use of taurine for treating alopecia
US7326717B2 (en) *	2003-05-06	2008-02-05	L'oreal	Pyrimidine n-oxide compounds for stimulating the growth of keratin fibers and/or reducing loss thereof
US20060193804A1 (en) *	2005-02-24	2006-08-31	L'oreal	Haircare use of cyclic amine derivatives
DE102007015282B4 (de) *	2007-03-29	2017-10-05	Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V.	Viskositätsregulator, Verfahren zu dessen Herstellung und dessen Verwendung
FR2920309B1 (fr)	2007-08-28	2010-05-28	Galderma Res & Dev	Utilisation de travoprost pour traiter la chute des cheveux
US8551463B2 (en)	2007-10-22	2013-10-08	Living Proof, Inc.	Hair care compositions and methods of treating hair
FR2949052B1 (fr)	2009-08-13	2015-03-27	Oreal	Procede de traitement cosmetique du cuir chevelu.
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
DK2838533T3 (da)	2012-04-16	2017-11-27	Univ Case Western Reserve	Sammensætninger og fremgangsmåder til at modulere 15-pgdh-aktivitet
AU2014342811B2 (en)	2013-10-15	2019-01-03	Board Of Regents Of The University Of Texas System	Compositions and methods of modulating short-chain dehydrogenase activity
AU2014361754B2 (en)	2013-12-12	2020-04-30	Cellmid Limited	Method of treatment of alopecia with monoterpenoids
WO2016090373A1 (en)	2014-12-05	2016-06-09	Case Western Reserve University	Compositions and methods of modulating s-nitrosylation
EP3548035A4 (de)	2016-11-30	2020-07-22	Case Western Reserve University	Kombinationen von 15-pgdh-inhibitoren mit corticosteroiden und/oder tnf-inhibitoren und verwendungen davon
JP2020514323A (ja)	2017-02-06	2020-05-21	ケースウエスタンリザーブユニバーシティ	短鎖デヒドロゲナーゼ活性を調節する組成物と方法
KR102921276B1 (ko)	2018-11-21	2026-02-03	케이스 웨스턴 리저브 유니버시티	단쇄 데히드로게나아제 활성을 조절하는 조성물 및 방법
FR3106058B1 (fr) *	2020-01-09	2022-01-07	Oreal	Procédé de traitement cosmétique
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
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
AU2021275122A1 (en)	2020-05-20	2022-12-15	Board Of Regents Of The University Of Texas System	Compositions and methods of modulating short-chain dehydrogenase activity

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0187854A4 (de) *	1984-07-13	1987-01-22	Gail S Bazzano	Substituierte pyrimidinoxide, einsetzbar zur haarwachsanregung.

1988
- 1988-08-01 LU LU87308A patent/LU87308A1/fr unknown
1989
- 1989-07-12 ES ES89402002T patent/ES2070186T3/es not_active Expired - Lifetime
- 1989-07-12 DE DE68922044T patent/DE68922044T2/de not_active Expired - Fee Related
- 1989-07-12 EP EP89402002A patent/EP0356271B1/de not_active Expired - Lifetime
- 1989-07-12 AT AT89402002T patent/ATE120738T1/de not_active IP Right Cessation
- 1989-07-28 JP JP1194437A patent/JP2669903B2/ja not_active Expired - Fee Related
- 1989-07-31 US US07/387,590 patent/US4973474A/en not_active Expired - Lifetime
- 1989-08-01 CA CA000607180A patent/CA1340445C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE68922044D1 (de)	1995-05-11
DE68922044T2 (de)	1995-08-03
ATE120738T1 (de)	1995-04-15
CA1340445C (fr)	1999-03-16
JPH0278666A (ja)	1990-03-19
EP0356271A1 (de)	1990-02-28
US4973474A (en)	1990-11-27
ES2070186T3 (es)	1995-06-01
EP0356271B1 (de)	1995-04-05
JP2669903B2 (ja)	1997-10-29

Publication	Publication Date	Title
LU87308A1 (fr)	1990-03-13	Nouveaux derives de diamino-2,4 pyrimidine oxyde-3 et leur utilisation pour le traitement et la prevention de la chute des cheveux
EP0540629B1 (de)	1994-05-04	Verwendung von pyrimidin-3-oxydderivaten zur verhütung von haarausfall und deren anwendung in topischen zusammensetzungen
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
CA1299572C (fr)	1992-04-28	Salicylates lipophiles d'ammoniums quaternaires, leur utilisation en cosmetique et en dermopharmacie
EP0519819B1 (de)	1995-07-19	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
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
EP0916652B1 (de)	2001-10-31	Neue N-Aryl-2-hydroxy-alkylamide
EP0353123B1 (de)	1994-08-24	Harnstoffhaltige 2,4,6-Triaminopyrimidin-3-oxid-Derivate, deren Herstellung und deren Verwendung für Kosmetika und Hautpharmazie
CA2273989C (fr)	2003-10-21	Nouveaux derives d'histidine, procede de preparation et leur utilisation comme agents anti-radicaux libres
EP0336813B1 (de)	1992-10-07	Assoziat bestehend aus Pyrimidin-Derivaten und Harnstoff- und/oder Allantoin-Derivaten zum Induzieren und Stimulieren des Haarwuchses und zum Vermindern des Haarausfalles
EP0304649B1 (de)	1991-03-20	Salze von 6-Piperidino-2,4-diaminopyrimidin-3-oxyd und von Derivaten der Thiamorpholin-3-on-5-carbonsäure und deren Verwendung in kosmetischen Stoffen und als Heilmittel
WO1992021317A1 (fr)	1992-12-10	Composition pour freiner la chute des cheveux et pour induire et stimuler leur croissance, a base de derives de pyridine 1-oxyde
EP0915857B1 (de)	2002-07-17	Verbindungen aus der gruppe der 3-aryl-2,4-dioxo-oxazolidine und ihre verwendung in der kosmetik und pharmazie
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
CA2087591C (fr)	2006-05-23	Utilisation de derives de pyrimidine 3-oxyde pour freiner la chute des cheveux et compositions topiques mises en oeuvre
CA2064910A1 (fr)	1991-12-20	Derives de diamino-2,4 triazine 1,3,5 et leur utilisation pour le traitement et la prevention de la chute des cheveux
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
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.