CA2245693C - Nail growth-promoting formulations - Google Patents

Nail growth-promoting formulations Download PDF

Info

Publication number: CA2245693C
Authority: CA; Canada
Prior art keywords: nail; compound; composition; action; alkyl
Prior art date: 1996-02-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CA002245693A

Other languages

English (en)

French (fr)

Other versions

CA2245693A1 (en

Inventor

Manfred Bohn

Karl Theodor Kraemer

Horst Ulbricht

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanofi Aventis Deutschland GmbH

Original Assignee

Aventis Pharma Deutschland GmbH

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.)

1996-02-06

Filing date

1997-01-23

Publication date

2004-11-02

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=7784609&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2245693(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1997-01-23 Application filed by Aventis Pharma Deutschland GmbH filed Critical Aventis Pharma Deutschland GmbH

1997-08-14 Publication of CA2245693A1 publication Critical patent/CA2245693A1/en

2004-11-02 Application granted granted Critical

2004-11-02 Publication of CA2245693C publication Critical patent/CA2245693C/en

2017-01-23 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims description 48
238000009472 formulation Methods 0.000 title description 25
239000002966 varnish Substances 0.000 claims abstract description 41
150000001875 compounds Chemical class 0.000 claims abstract description 40
238000011282 treatment Methods 0.000 claims abstract description 35
239000003795 chemical substances by application Substances 0.000 claims abstract description 17
230000000304 vasodilatating effect Effects 0.000 claims abstract description 11
230000009548 growth disturbance Effects 0.000 claims abstract description 5
230000001857 anti-mycotic effect Effects 0.000 claims description 19
239000002543 antimycotic Substances 0.000 claims description 18
-1 diisapropylamine Chemical compound 0.000 claims description 13
230000000699 topical effect Effects 0.000 claims description 12
229920001577 copolymer Polymers 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
230000009471 action Effects 0.000 claims description 8
230000036562 nail growth Effects 0.000 claims description 8
230000008569 process Effects 0.000 claims description 7
SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 claims description 5
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical group CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 5
239000000654 additive Substances 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
229960001722 verapamil Drugs 0.000 claims description 5
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
ZIMGGGWCDYVHOY-UHFFFAOYSA-N 3-hydroxy-2-imino-6-(1-piperidinyl)-4-pyrimidinamine Chemical compound N=C1N(O)C(N)=CC(N2CCCCC2)=N1 ZIMGGGWCDYVHOY-UHFFFAOYSA-N 0.000 claims description 4
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
239000000020 Nitrocellulose Substances 0.000 claims description 4
FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
SCKYRAXSEDYPSA-UHFFFAOYSA-N ciclopirox Chemical group ON1C(=O)C=C(C)C=C1C1CCCCC1 SCKYRAXSEDYPSA-UHFFFAOYSA-N 0.000 claims description 4
229920001220 nitrocellulos Polymers 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
229920000642 polymer Polymers 0.000 claims description 4
HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims description 3
229960002509 miconazole Drugs 0.000 claims description 3
150000002780 morpholines Chemical class 0.000 claims description 3
239000000049 pigment Substances 0.000 claims description 3
OIQJEQLSYJSNDS-UHFFFAOYSA-N piroctone Chemical compound CC(C)(C)CC(C)CC1=CC(C)=CC(=O)N1O OIQJEQLSYJSNDS-UHFFFAOYSA-N 0.000 claims description 3
239000004014 plasticizer Substances 0.000 claims description 3
229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 3
229960003401 ramipril Drugs 0.000 claims description 3
DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 claims description 3
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 2
HMJIYCCIJYRONP-UHFFFAOYSA-N (+-)-Isradipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12 HMJIYCCIJYRONP-UHFFFAOYSA-N 0.000 claims description 2
XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 claims description 2
BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
MPIPASJGOJYODL-SFHVURJKSA-N (R)-isoconazole Chemical compound ClC1=CC(Cl)=CC=C1[C@@H](OCC=1C(=CC=CC=1Cl)Cl)CN1C=NC=C1 MPIPASJGOJYODL-SFHVURJKSA-N 0.000 claims description 2
PVHUJELLJLJGLN-INIZCTEOSA-N (S)-nitrendipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 PVHUJELLJLJGLN-INIZCTEOSA-N 0.000 claims description 2
ZCJYUTQZBAIHBS-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-{[4-(phenylsulfanyl)benzyl]oxy}ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=1C=CC(SC=2C=CC=CC=2)=CC=1)CN1C=NC=C1 ZCJYUTQZBAIHBS-UHFFFAOYSA-N 0.000 claims description 2
OCAPBUJLXMYKEJ-UHFFFAOYSA-N 1-[biphenyl-4-yl(phenyl)methyl]imidazole Chemical compound C1=NC=CN1C(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OCAPBUJLXMYKEJ-UHFFFAOYSA-N 0.000 claims description 2
LEZWWPYKPKIXLL-UHFFFAOYSA-N 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound C1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 LEZWWPYKPKIXLL-UHFFFAOYSA-N 0.000 claims description 2
QXHHHPZILQDDPS-UHFFFAOYSA-N 1-{2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound S1C=CC(COC(CN2C=NC=C2)C=2C(=CC(Cl)=CC=2)Cl)=C1Cl QXHHHPZILQDDPS-UHFFFAOYSA-N 0.000 claims description 2
NMKSAYKQLCHXDK-UHFFFAOYSA-N 3,3-diphenyl-N-(1-phenylethyl)-1-propanamine Chemical compound C=1C=CC=CC=1C(C)NCCC(C=1C=CC=CC=1)C1=CC=CC=C1 NMKSAYKQLCHXDK-UHFFFAOYSA-N 0.000 claims description 2
LBSRZVRITCRLIU-UHFFFAOYSA-N 3-o-ethyl 5-o-(2-piperidin-1-ylethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCN2CCCCC2)C1C1=CC=CC([N+]([O-])=O)=C1 LBSRZVRITCRLIU-UHFFFAOYSA-N 0.000 claims description 2
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
BCIGYDKZWDEHCO-UHFFFAOYSA-N 4-piperidin-1-ylpyridine-2,6-diamine Chemical compound NC1=NC(N)=CC(N2CCCCC2)=C1 BCIGYDKZWDEHCO-UHFFFAOYSA-N 0.000 claims description 2
RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 claims description 2
UDYUIWXQUBNDHC-UHFFFAOYSA-N 6-[[4-(4-chlorophenoxy)phenoxy]methyl]-1-hydroxy-4-methylpyridin-2-one Chemical compound ON1C(=O)C=C(C)C=C1COC(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 UDYUIWXQUBNDHC-UHFFFAOYSA-N 0.000 claims description 2
QSXXLDDWVCEBFP-UHFFFAOYSA-N 7-(ethoxymethyl)-1-(5-hydroxy-5-methylhexyl)-3-methylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCCC(C)(C)O)C(=O)C2=C1N=CN2COCC QSXXLDDWVCEBFP-UHFFFAOYSA-N 0.000 claims description 2
QOYHHIBFXOOADH-UHFFFAOYSA-N 8-[4,4-bis(4-fluorophenyl)butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 QOYHHIBFXOOADH-UHFFFAOYSA-N 0.000 claims description 2
YKRDKMNLBVQSOH-UHFFFAOYSA-N CCCCOC1=NC(N)=[N+]([O-])C(N)=N1 Chemical compound CCCCOC1=NC(N)=[N+]([O-])C(N)=N1 YKRDKMNLBVQSOH-UHFFFAOYSA-N 0.000 claims description 2
WHPAGCJNPTUGGD-UHFFFAOYSA-N Croconazole Chemical compound ClC1=CC=CC(COC=2C(=CC=CC=2)C(=C)N2C=NC=C2)=C1 WHPAGCJNPTUGGD-UHFFFAOYSA-N 0.000 claims description 2
IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 claims description 2
XQLWNAFCTODIRK-UHFFFAOYSA-N Gallopamil Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC(OC)=C(OC)C(OC)=C1 XQLWNAFCTODIRK-UHFFFAOYSA-N 0.000 claims description 2
UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 claims description 2
239000004166 Lanolin Substances 0.000 claims description 2
108010007859 Lisinopril Proteins 0.000 claims description 2
DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 claims description 2
ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 claims description 2
YSEXMKHXIOCEJA-FVFQAYNVSA-N Nicergoline Chemical compound C([C@@H]1C[C@]2([C@H](N(C)C1)CC=1C3=C2C=CC=C3N(C)C=1)OC)OC(=O)C1=CN=CC(Br)=C1 YSEXMKHXIOCEJA-FVFQAYNVSA-N 0.000 claims description 2
FAIIFDPAEUKBEP-UHFFFAOYSA-N Nilvadipine Chemical compound COC(=O)C1=C(C#N)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 FAIIFDPAEUKBEP-UHFFFAOYSA-N 0.000 claims description 2
CANCCLAKQQHLNK-LSDHHAIUSA-N O-[[(1R,8S)-4-tricyclo[6.2.1.02,7]undeca-2(7),3,5-trienyl]] N-methyl-N-(3-methylphenyl)carbamothioate Chemical compound CN(C(=S)Oc1ccc2[C@H]3CC[C@H](C3)c2c1)c1cccc(C)c1 CANCCLAKQQHLNK-LSDHHAIUSA-N 0.000 claims description 2
BYPFEZZEUUWMEJ-UHFFFAOYSA-N Pentoxifylline Chemical compound O=C1N(CCCCC(=O)C)C(=O)N(C)C2=C1N(C)C=N2 BYPFEZZEUUWMEJ-UHFFFAOYSA-N 0.000 claims description 2
RBQOQRRFDPXAGN-UHFFFAOYSA-N Propentofylline Chemical compound CN1C(=O)N(CCCCC(C)=O)C(=O)C2=C1N=CN2CCC RBQOQRRFDPXAGN-UHFFFAOYSA-N 0.000 claims description 2
VXFJYXUZANRPDJ-WTNASJBWSA-N Trandopril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 VXFJYXUZANRPDJ-WTNASJBWSA-N 0.000 claims description 2
TYVWBCMQECJNSK-UHFFFAOYSA-N [2-methyl-3-(2-methylprop-2-enoyloxy)butan-2-yl]azanium;chloride Chemical compound [Cl-].CC([NH3+])(C)C(C)OC(=O)C(C)=C TYVWBCMQECJNSK-UHFFFAOYSA-N 0.000 claims description 2
MFAIKGYHWQMVDE-UHFFFAOYSA-N [OH-].NC1[NH+]=C(C=C(N1OS(=O)(=O)O)N)OCCCC Chemical compound [OH-].NC1[NH+]=C(C=C(N1OS(=O)(=O)O)N)OCCCC MFAIKGYHWQMVDE-UHFFFAOYSA-N 0.000 claims description 2
229960000528 amlodipine Drugs 0.000 claims description 2
HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 claims description 2
125000004069 aziridinyl group Chemical group 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
229960002206 bifonazole Drugs 0.000 claims description 2
229960000830 captopril Drugs 0.000 claims description 2
FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 claims description 2
229960003749 ciclopirox Drugs 0.000 claims description 2
229960004022 clotrimazole Drugs 0.000 claims description 2
VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 claims description 2
229960002042 croconazole Drugs 0.000 claims description 2
229960004042 diazoxide Drugs 0.000 claims description 2
VQKLRVZQQYVIJW-UHFFFAOYSA-N dihydralazine Chemical compound C1=CC=C2C(NN)=NN=C(NN)C2=C1 VQKLRVZQQYVIJW-UHFFFAOYSA-N 0.000 claims description 2
229960002877 dihydralazine Drugs 0.000 claims description 2
HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 claims description 2
229960004166 diltiazem Drugs 0.000 claims description 2
229960003913 econazole Drugs 0.000 claims description 2
229960003580 felodipine Drugs 0.000 claims description 2
229960002602 fendiline Drugs 0.000 claims description 2
229960001274 fenticonazole Drugs 0.000 claims description 2
229960000326 flunarizine Drugs 0.000 claims description 2
SMANXXCATUTDDT-QPJJXVBHSA-N flunarizine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)N1CCN(C\C=C\C=2C=CC=CC=2)CC1 SMANXXCATUTDDT-QPJJXVBHSA-N 0.000 claims description 2
229960003532 fluspirilene Drugs 0.000 claims description 2
229960002490 fosinopril Drugs 0.000 claims description 2
229960000457 gallopamil Drugs 0.000 claims description 2
229960002867 griseofulvin Drugs 0.000 claims description 2
DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 claims description 2
229960004849 isoconazole Drugs 0.000 claims description 2
229960004427 isradipine Drugs 0.000 claims description 2
229960004125 ketoconazole Drugs 0.000 claims description 2
229940039717 lanolin Drugs 0.000 claims description 2
235000019388 lanolin Nutrition 0.000 claims description 2
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RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 claims description 2
VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
229960004313 naftifine Drugs 0.000 claims description 2
OZGNYLLQHRPOBR-DHZHZOJOSA-N naftifine Chemical compound C=1C=CC2=CC=CC=C2C=1CN(C)C\C=C\C1=CC=CC=C1 OZGNYLLQHRPOBR-DHZHZOJOSA-N 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
229960001783 nicardipine Drugs 0.000 claims description 2
229960003642 nicergoline Drugs 0.000 claims description 2
HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 claims description 2
229960001597 nifedipine Drugs 0.000 claims description 2
229960005366 nilvadipine Drugs 0.000 claims description 2
229960000227 nisoldipine Drugs 0.000 claims description 2
229960005425 nitrendipine Drugs 0.000 claims description 2
229960003483 oxiconazole Drugs 0.000 claims description 2
QRJJEGAJXVEBNE-MOHJPFBDSA-N oxiconazole Chemical compound ClC1=CC(Cl)=CC=C1CO\N=C(C=1C(=CC(Cl)=CC=1)Cl)\CN1C=NC=C1 QRJJEGAJXVEBNE-MOHJPFBDSA-N 0.000 claims description 2
229960001476 pentoxifylline Drugs 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
229950001046 piroctone Drugs 0.000 claims description 2
229960002934 propentofylline Drugs 0.000 claims description 2
239000011814 protection agent Substances 0.000 claims description 2
229960001455 quinapril Drugs 0.000 claims description 2
JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 claims description 2
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YVUQSNJEYSNKRX-UHFFFAOYSA-N pimozide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC(N2C(NC3=CC=CC=C32)=O)CC1 YVUQSNJEYSNKRX-UHFFFAOYSA-N 0.000 description 1
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Classifications

- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q3/00—Manicure or pedicure preparations
- A61Q3/02—Nail coatings

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Birds (AREA)
Dermatology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Cosmetics (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicines Containing Plant Substances (AREA)
Finger-Pressure Massage (AREA)

CA002245693A 1996-02-06 1997-01-23 Nail growth-promoting formulations Expired - Lifetime CA2245693C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19604190A DE19604190A1 (de)	1996-02-06	1996-02-06	Nagelwachstumsfördernde Zubereitungen
DE19604190.2		1996-02-06
PCT/EP1997/000311 WO1997028790A1 (de)	1996-02-06	1997-01-23	Nagelwachstumsfördernde zubereitungen

Publications (2)

Publication Number	Publication Date
CA2245693A1 CA2245693A1 (en)	1997-08-14
CA2245693C true CA2245693C (en)	2004-11-02

Family

ID=7784609

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002245693A Expired - Lifetime CA2245693C (en)	1996-02-06	1997-01-23	Nail growth-promoting formulations

Country Status (28)

Country	Link
US (1)	US6007798A (2)
EP (1)	EP0879052B1 (2)
JP (1)	JP4119480B2 (2)
KR (1)	KR100457849B1 (2)
CN (1)	CN1239157C (2)
AT (1)	ATE198155T1 (2)
AU (1)	AU706531B2 (2)
BG (1)	BG63485B1 (2)
BR (1)	BR9707353A (2)
CA (1)	CA2245693C (2)
CZ (1)	CZ290231B6 (2)
DE (2)	DE19604190A1 (2)
DK (1)	DK0879052T3 (2)
ES (1)	ES2154021T3 (2)
GR (1)	GR3035085T3 (2)
HU (1)	HU228521B1 (2)
IL (2)	IL125536A0 (2)
NO (1)	NO320443B1 (2)
NZ (1)	NZ326362A (2)
OA (1)	OA10829A (2)
PL (1)	PL186876B1 (2)
PT (1)	PT879052E (2)
RU (1)	RU2178289C2 (2)
TR (1)	TR199801475T2 (2)
TW (1)	TW493989B (2)
UA (1)	UA57015C2 (2)
WO (1)	WO1997028790A1 (2)
ZA (1)	ZA97930B (2)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8697753B1 (en)	2013-02-07	2014-04-15	Polichem Sa	Method of treating onychomycosis

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6231875B1 (en) *	1998-03-31	2001-05-15	Johnson & Johnson Consumer Companies, Inc.	Acidified composition for topical treatment of nail and skin conditions
US6143794A (en) *	1998-04-17	2000-11-07	Bertek Pharmaceuticals, Inc.	Topical formulations for the treatment of nail fungal diseases
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1996
- 1996-02-06 DE DE19604190A patent/DE19604190A1/de not_active Withdrawn
1997
- 1997-01-23 BR BR9707353A patent/BR9707353A/pt active IP Right Grant
- 1997-01-23 US US08/930,562 patent/US6007798A/en not_active Expired - Lifetime
- 1997-01-23 IL IL12553697A patent/IL125536A0/xx unknown
- 1997-01-23 ES ES97901078T patent/ES2154021T3/es not_active Expired - Lifetime
- 1997-01-23 JP JP52809597A patent/JP4119480B2/ja not_active Expired - Lifetime
- 1997-01-23 DK DK97901078T patent/DK0879052T3/da active
- 1997-01-23 NZ NZ326362A patent/NZ326362A/xx not_active IP Right Cessation
- 1997-01-23 TR TR1998/01475T patent/TR199801475T2/xx unknown
- 1997-01-23 EP EP97901078A patent/EP0879052B1/de not_active Expired - Lifetime
- 1997-01-23 AT AT97901078T patent/ATE198155T1/de active
- 1997-01-23 WO PCT/EP1997/000311 patent/WO1997028790A1/de not_active Ceased
- 1997-01-23 UA UA98094694A patent/UA57015C2/uk unknown
- 1997-01-23 CN CNB971920826A patent/CN1239157C/zh not_active Expired - Lifetime
- 1997-01-23 RU RU98116789/14A patent/RU2178289C2/ru active
- 1997-01-23 CA CA002245693A patent/CA2245693C/en not_active Expired - Lifetime
- 1997-01-23 PT PT97901078T patent/PT879052E/pt unknown
- 1997-01-23 DE DE59702786T patent/DE59702786D1/de not_active Expired - Lifetime
- 1997-01-23 CZ CZ19982439A patent/CZ290231B6/cs not_active IP Right Cessation
- 1997-01-23 KR KR10-1998-0706023A patent/KR100457849B1/ko not_active Expired - Lifetime
- 1997-01-23 PL PL97328397A patent/PL186876B1/pl unknown
- 1997-01-23 HU HU9900654A patent/HU228521B1/hu unknown
- 1997-01-23 AU AU14447/97A patent/AU706531B2/en not_active Expired
- 1997-02-04 TW TW086101258A patent/TW493989B/zh not_active IP Right Cessation
- 1997-02-05 ZA ZA9700930A patent/ZA97930B/xx unknown
1998
- 1998-07-15 BG BG102636A patent/BG63485B1/bg unknown
- 1998-07-27 IL IL12553698A patent/IL125536A/en not_active IP Right Cessation
- 1998-08-05 NO NO19983598A patent/NO320443B1/no not_active IP Right Cessation
- 1998-08-06 OA OA9800134A patent/OA10829A/fr unknown
2000
- 2000-12-15 GR GR20000402773T patent/GR3035085T3/el unknown

Cited By (3)

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US8697753B1 (en)	2013-02-07	2014-04-15	Polichem Sa	Method of treating onychomycosis
US9107877B2 (en)	2013-02-07	2015-08-18	Polichem Sa	Method of treating onychomycosis
US10172811B2 (en)	2013-02-07	2019-01-08	Polichem Sa	Topical antifungal composition for treating onychomycosis

Also Published As

Publication number	Publication date
EP0879052A1 (de)	1998-11-25
BG102636A (en)	1999-02-26
CN1239157C (zh)	2006-02-01
CZ290231B6 (cs)	2002-06-12
AU1444797A (en)	1997-08-28
PL328397A1 (en)	1999-01-18
EP0879052B1 (de)	2000-12-20
HU228521B1 (en)	2013-03-28
US6007798A (en)	1999-12-28
NO983598D0 (no)	1998-08-05
JP4119480B2 (ja)	2008-07-16
TW493989B (en)	2002-07-11
NZ326362A (en)	1999-01-28
CN1210460A (zh)	1999-03-10
JP2000504674A (ja)	2000-04-18
DK0879052T3 (da)	2001-02-19
HUP9900654A3 (en)	2001-11-28
ZA97930B (en)	1997-08-06
TR199801475T2 (xx)	1998-10-21
ATE198155T1 (de)	2001-01-15
DE19604190A1 (de)	1997-08-07
IL125536A (en)	2001-10-31
HK1018398A1 (en)	1999-12-24
PT879052E (pt)	2001-04-30
KR100457849B1 (ko)	2005-07-08
OA10829A (fr)	2003-01-29
CA2245693A1 (en)	1997-08-14
UA57015C2 (uk)	2003-06-16
BG63485B1 (bg)	2002-03-29
DE59702786D1 (de)	2001-01-25
NO320443B1 (no)	2005-12-05
GR3035085T3 (en)	2001-03-30
IL125536A0 (en)	1999-03-12
ES2154021T3 (es)	2001-03-16
WO1997028790A1 (de)	1997-08-14
KR19990082294A (ko)	1999-11-25
PL186876B1 (pl)	2004-03-31
RU2178289C2 (ru)	2002-01-20
AU706531B2 (en)	1999-06-17
BR9707353A (pt)	1999-07-20
NO983598L (no)	1998-10-02
CZ243998A3 (cs)	1998-11-11
HUP9900654A1 (hu)	1999-07-28

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2017-03-27	MKEX	Expiry	Effective date: 20170123

Publication	Publication Date	Title
CA2245693C (en)	2004-11-02	Nail growth-promoting formulations
US4957730A (en)	1990-09-18	Antimycotic nail varnish
US6162420A (en)	2000-12-19	Use of glyceryl triacetate for treating onychomycoses
US20030012749A1 (en)	2003-01-16	Preparations for the non-traumatic excision of a nail
JP5162064B2 (ja)	2013-03-13	抗アンドロゲン作用を有する物質を局所適用するための処方物
ES2242027T3 (es)	2005-11-01	Preparacion para eleminar material queratinoso anormal.
ES2857949T3 (es)	2021-09-29	Laca de uñas queratolítica de color
KR20160123549A (ko)	2016-10-26	모발 강화용 화장료 조성물
HK1018398B (en)	2006-07-07	Nail frowth-promoting formulations