DE102008052618A1 - Tricyclische Aldehyde und C,H-acide Verbindungen - Google Patents

Tricyclische Aldehyde und C,H-acide Verbindungen Download PDF

Info

Publication number: DE102008052618A1
Authority: DE; Germany
Prior art keywords: group; hydroxy; amino; alkyl; acid
Prior art date: 2008-10-21
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

DE200810052618

Other languages

German (de)

English (en)

Inventor

Wibke Dr. Gross

Doris Dr. Oberkobusch

Ralph Nemitz

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.)

Henkel AG and Co KGaA

Original Assignee

Henkel AG and Co KGaA

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.)

2008-10-21

Filing date

2008-10-21

Publication date

2010-04-22

2008-10-21 Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA

2008-10-21 Priority to DE200810052618 priority Critical patent/DE102008052618A1/de

2009-09-21 Priority to PCT/EP2009/062216 priority patent/WO2010046190A2/fr

2010-04-22 Publication of DE102008052618A1 publication Critical patent/DE102008052618A1/de

Status Withdrawn legal-status Critical Current

Links

229910052799 carbon Inorganic materials 0.000 title claims abstract description 52
150000001299 aldehydes Chemical class 0.000 title claims description 14
150000001875 compounds Chemical class 0.000 claims abstract description 147
239000003795 chemical substances by application Substances 0.000 claims abstract description 76
239000000835 fiber Substances 0.000 claims abstract description 43
238000004043 dyeing Methods 0.000 claims abstract description 42
210000004209 hair Anatomy 0.000 claims abstract description 34
102000011782 Keratins Human genes 0.000 claims abstract description 28
108010076876 Keratins Proteins 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 27
-1 nitro, amino Chemical group 0.000 claims description 166
150000003839 salts Chemical class 0.000 claims description 88
239000000203 mixture Substances 0.000 claims description 56
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
125000004432 carbon atom Chemical group C* 0.000 claims description 44
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 42
150000003254 radicals Chemical class 0.000 claims description 41
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
125000000217 alkyl group Chemical group 0.000 claims description 31
125000005843 halogen group Chemical group 0.000 claims description 31
125000003118 aryl group Chemical group 0.000 claims description 29
125000003277 amino group Chemical group 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 24
125000001072 heteroaryl group Chemical group 0.000 claims description 23
239000003086 colorant Substances 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 20
230000008569 process Effects 0.000 claims description 18
230000001590 oxidative effect Effects 0.000 claims description 17
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 16
150000001728 carbonyl compounds Chemical class 0.000 claims description 16
125000003107 substituted aryl group Chemical group 0.000 claims description 15
125000001424 substituent group Chemical group 0.000 claims description 13
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
125000000623 heterocyclic group Chemical group 0.000 claims description 11
UIKMKSOLPGMDOI-UHFFFAOYSA-N 4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-triene-7-carbaldehyde Chemical compound C1COC2=CC(C=O)=CC3=C2N1CCC3 UIKMKSOLPGMDOI-UHFFFAOYSA-N 0.000 claims description 10
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
238000002156 mixing Methods 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
PYVBGEUEQLAGGN-UHFFFAOYSA-N 2,3,6-trihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1O PYVBGEUEQLAGGN-UHFFFAOYSA-N 0.000 claims description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 6
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
239000002453 shampoo Substances 0.000 claims description 5
125000004149 thio group Chemical group *S* 0.000 claims description 5
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
APHLYZNGFCQHCT-UHFFFAOYSA-N 2,3,6-trimethoxybenzaldehyde Chemical compound COC1=CC=C(OC)C(C=O)=C1OC APHLYZNGFCQHCT-UHFFFAOYSA-N 0.000 claims description 4
IXWOUPGDGMCKGT-UHFFFAOYSA-N 2,3-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1O IXWOUPGDGMCKGT-UHFFFAOYSA-N 0.000 claims description 4
JIVGSHFYXPRRSZ-UHFFFAOYSA-N 2,3-dimethoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1OC JIVGSHFYXPRRSZ-UHFFFAOYSA-N 0.000 claims description 4
WNCNWLVQSHZVKV-UHFFFAOYSA-N 2,4,5-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(C=O)C=C1O WNCNWLVQSHZVKV-UHFFFAOYSA-N 0.000 claims description 4
BTQAJGSMXCDDAJ-UHFFFAOYSA-N 2,4,6-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(C=O)C(O)=C1 BTQAJGSMXCDDAJ-UHFFFAOYSA-N 0.000 claims description 4
CRBZVDLXAIFERF-UHFFFAOYSA-N 2,4,6-trimethoxybenzaldehyde Chemical compound COC1=CC(OC)=C(C=O)C(OC)=C1 CRBZVDLXAIFERF-UHFFFAOYSA-N 0.000 claims description 4
LJFQTUKKYWDRAT-UHFFFAOYSA-N 2,4-dihydroxy-6-methylbenzaldehyde Chemical compound CC1=CC(O)=CC(O)=C1C=O LJFQTUKKYWDRAT-UHFFFAOYSA-N 0.000 claims description 4
IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 claims description 4
LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 claims description 4
CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-UHFFFAOYSA-N 0.000 claims description 4
WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 claims description 4
PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 claims description 4
RGZHEOWNTDJLAQ-UHFFFAOYSA-N 3,4,5-trihydroxybenzaldehyde Chemical compound OC1=CC(C=O)=CC(O)=C1O RGZHEOWNTDJLAQ-UHFFFAOYSA-N 0.000 claims description 4
OSYMDNUEVGSSKZ-UHFFFAOYSA-N 3,4-dihydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C(O)=CC=C1C=O OSYMDNUEVGSSKZ-UHFFFAOYSA-N 0.000 claims description 4
IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 claims description 4
VFZRZRDOXPRTSC-UHFFFAOYSA-N 3,5-Dimethoxybenzaldehyde Chemical compound COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 claims description 4
SXRHGLQCOLNZPT-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzaldehyde Chemical compound OC1=C(Br)C=C(C=O)C=C1Br SXRHGLQCOLNZPT-UHFFFAOYSA-N 0.000 claims description 4
GVSGSHGXUXLQNS-UHFFFAOYSA-N 3-bromo-4,5-dihydroxybenzaldehyde Chemical compound OC1=CC(C=O)=CC(Br)=C1O GVSGSHGXUXLQNS-UHFFFAOYSA-N 0.000 claims description 4
UOTMHAOCAJROQF-UHFFFAOYSA-N 3-bromo-4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1Br UOTMHAOCAJROQF-UHFFFAOYSA-N 0.000 claims description 4
IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 claims description 4
WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 claims description 4
GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 claims description 4
BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims description 4
YMWYSWXWDNMUIX-UHFFFAOYSA-N 4-hydroxy-2,3-dimethoxybenzaldehyde Chemical compound COC1=C(O)C=CC(C=O)=C1OC YMWYSWXWDNMUIX-UHFFFAOYSA-N 0.000 claims description 4
WBIZZNFQJPOKDK-UHFFFAOYSA-N 4-hydroxy-2-methoxybenzaldehyde Chemical compound COC1=CC(O)=CC=C1C=O WBIZZNFQJPOKDK-UHFFFAOYSA-N 0.000 claims description 4
UYGBSRJODQHNLQ-UHFFFAOYSA-N 4-hydroxy-3,5-dimethylbenzaldehyde Chemical compound CC1=CC(C=O)=CC(C)=C1O UYGBSRJODQHNLQ-UHFFFAOYSA-N 0.000 claims description 4
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims description 4
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 4
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 4
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 4
WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 claims description 4
CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 claims description 4
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 claims description 4
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 4
SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 claims description 4
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 4
COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 claims description 4
DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 claims description 4
WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 claims description 4
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 3
BWOVACANEIVHST-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)acetonitrile Chemical compound C1=CC=C2NC(CC#N)=NC2=C1 BWOVACANEIVHST-UHFFFAOYSA-N 0.000 claims description 3
KCWXFIYBVUTOGD-UHFFFAOYSA-N 4-nitro-1,3-benzodioxole-5-carbaldehyde Chemical compound C1=C(C=O)C([N+](=O)[O-])=C2OCOC2=C1 KCWXFIYBVUTOGD-UHFFFAOYSA-N 0.000 claims description 3
YEYPSUQQZNDKDE-UHFFFAOYSA-N 5-bromo-2-hydroxy-3-nitrobenzaldehyde Chemical compound OC1=C(C=O)C=C(Br)C=C1[N+]([O-])=O YEYPSUQQZNDKDE-UHFFFAOYSA-N 0.000 claims description 3
ZEHYRTJBFMZHCY-UHFFFAOYSA-N 5-nitrovanillin Chemical compound COC1=CC(C=O)=CC([N+]([O-])=O)=C1O ZEHYRTJBFMZHCY-UHFFFAOYSA-N 0.000 claims description 3
JEUPZZWOWIMJMH-UHFFFAOYSA-N 6-hydroxy-3,6-dinitrocyclohexa-2,4-diene-1-carbaldehyde Chemical compound [O-][N+](=O)C1(O)C=CC([N+]([O-])=O)=CC1C=O JEUPZZWOWIMJMH-UHFFFAOYSA-N 0.000 claims description 3
NRZWECORTTWSEF-UHFFFAOYSA-N 6-nitro-1,3-benzodioxole-5-carbaldehyde Chemical compound C1=C(C=O)C([N+](=O)[O-])=CC2=C1OCO2 NRZWECORTTWSEF-UHFFFAOYSA-N 0.000 claims description 3
239000004475 Arginine Substances 0.000 claims description 3
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 3
229940117916 cinnamic aldehyde Drugs 0.000 claims description 3
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
150000002390 heteroarenes Chemical class 0.000 claims description 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 claims description 2
JKTVNBZTQKQRSH-DUXPYHPUSA-N (e)-3-(3-nitrophenyl)prop-2-enal Chemical compound [O-][N+](=O)C1=CC=CC(\C=C\C=O)=C1 JKTVNBZTQKQRSH-DUXPYHPUSA-N 0.000 claims description 2
ALGQVMMYDWQDEC-OWOJBTEDSA-N (e)-3-(4-nitrophenyl)prop-2-enal Chemical compound [O-][N+](=O)C1=CC=C(\C=C\C=O)C=C1 ALGQVMMYDWQDEC-OWOJBTEDSA-N 0.000 claims description 2
FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 2
CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims description 2
KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims description 2
OFFWGCOIQGEEGE-UHFFFAOYSA-N 1,3,4,6-tetramethyl-4H-pyrimidin-2-one Chemical class CC1C=C(C)N(C)C(=O)N1C OFFWGCOIQGEEGE-UHFFFAOYSA-N 0.000 claims description 2
MINUAUZUQLUNHT-UHFFFAOYSA-N 1,3,4,6-tetramethyl-4H-pyrimidine-2-thione Chemical compound CC1C=C(C)N(C)C(=S)N1C MINUAUZUQLUNHT-UHFFFAOYSA-N 0.000 claims description 2
WAYDNYGUKUTTCL-UHFFFAOYSA-N 1,3,4-trimethyl-4h-pyrimidin-2-one Chemical class CC1C=CN(C)C(=O)N1C WAYDNYGUKUTTCL-UHFFFAOYSA-N 0.000 claims description 2
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 2
DTBUSCFWSNZSGL-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3,4,6-trimethyl-4h-pyrimidin-2-one Chemical compound CC1C=C(C)N(CCO)C(=O)N1C DTBUSCFWSNZSGL-UHFFFAOYSA-N 0.000 claims description 2
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 2
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 2
TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 2
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 2
CRPNQSVBEWWHIJ-UHFFFAOYSA-N 2,3,4-trihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1O CRPNQSVBEWWHIJ-UHFFFAOYSA-N 0.000 claims description 2
UCTUXUGXIFRVGX-UHFFFAOYSA-N 2,3,4-trimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1OC UCTUXUGXIFRVGX-UHFFFAOYSA-N 0.000 claims description 2
HUTITODAYBWJRG-UHFFFAOYSA-N 2,3,5-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(O)C(C=O)=C1 HUTITODAYBWJRG-UHFFFAOYSA-N 0.000 claims description 2
NSEBBFDHPSOJLT-UHFFFAOYSA-N 2,3,5-trimethoxybenzaldehyde Chemical compound COC1=CC(OC)=C(OC)C(C=O)=C1 NSEBBFDHPSOJLT-UHFFFAOYSA-N 0.000 claims description 2
VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims description 2
IAJBQAYHSQIQRE-UHFFFAOYSA-N 2,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(OC)=C(C=O)C=C1OC IAJBQAYHSQIQRE-UHFFFAOYSA-N 0.000 claims description 2
HOFPWODHZJNTBF-UHFFFAOYSA-N 2,4-dihydroxy-3-methoxybenzaldehyde Chemical compound COC1=C(O)C=CC(C=O)=C1O HOFPWODHZJNTBF-UHFFFAOYSA-N 0.000 claims description 2
AOPMHYFEQDBXPZ-UHFFFAOYSA-N 2,4-dihydroxy-3-methylbenzaldehyde Chemical compound CC1=C(O)C=CC(C=O)=C1O AOPMHYFEQDBXPZ-UHFFFAOYSA-N 0.000 claims description 2
ZFZAFNQYRZGWNK-UHFFFAOYSA-N 2,4-dihydroxy-5-methoxybenzaldehyde Chemical compound COC1=CC(C=O)=C(O)C=C1O ZFZAFNQYRZGWNK-UHFFFAOYSA-N 0.000 claims description 2
JATWPRIBCRVOHC-UHFFFAOYSA-N 2,4-dihydroxy-5-methylbenzaldehyde Chemical compound CC1=CC(C=O)=C(O)C=C1O JATWPRIBCRVOHC-UHFFFAOYSA-N 0.000 claims description 2
MFYFZAYWFVCZES-UHFFFAOYSA-N 2,4-dihydroxynaphthalene-1-carbaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC(O)=C21 MFYFZAYWFVCZES-UHFFFAOYSA-N 0.000 claims description 2
NNQTVZVNHYJOKQ-UHFFFAOYSA-N 2,4-dimethoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=CC2=C(C=O)C(OC)=CC(OC)=C21 NNQTVZVNHYJOKQ-UHFFFAOYSA-N 0.000 claims description 2
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NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
229960001763 zinc sulfate Drugs 0.000 description 1
229910000368 zinc sulfate Inorganic materials 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
239000001841 zingiber officinale Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
- 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
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair

Landscapes

Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Birds (AREA)
Epidemiology (AREA)
Cosmetics (AREA)

DE200810052618 2008-10-21 2008-10-21 Tricyclische Aldehyde und C,H-acide Verbindungen Withdrawn DE102008052618A1 (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
DE200810052618 DE102008052618A1 (de)	2008-10-21	2008-10-21	Tricyclische Aldehyde und C,H-acide Verbindungen
PCT/EP2009/062216 WO2010046190A2 (fr)	2008-10-21	2009-09-21	Aldéhydes tricycliques et composés acides c,h

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE200810052618 DE102008052618A1 (de)	2008-10-21	2008-10-21	Tricyclische Aldehyde und C,H-acide Verbindungen

Publications (1)

Publication Number	Publication Date
DE102008052618A1 true DE102008052618A1 (de)	2010-04-22

Family

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Application Number	Title	Priority Date	Filing Date
DE200810052618 Withdrawn DE102008052618A1 (de)	2008-10-21	2008-10-21	Tricyclische Aldehyde und C,H-acide Verbindungen

Country Status (2)

Country	Link
DE (1)	DE102008052618A1 (fr)
WO (1)	WO2010046190A2 (fr)

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EP2970282B1 (fr)	2013-03-15	2019-08-21	Incyte Holdings Corporation	Hétérocycles tricycliques en tant qu'inhibiteurs de protéine bet
ES2635560T3 (es)	2013-07-08	2017-10-04	Incyte Holdings Corporation	Heterociclos tricíclicos como inhibidores de la proteína NET
US9315501B2 (en)	2013-11-26	2016-04-19	Incyte Corporation	Bicyclic heterocycles as BET protein inhibitors
US9399640B2 (en)	2013-11-26	2016-07-26	Incyte Corporation	Substituted pyrrolo[2,3-c]pyridines and pyrazolo[3,4-c]pyridines as BET protein inhibitors
US9309246B2 (en)	2013-12-19	2016-04-12	Incyte Corporation	Tricyclic heterocycles as BET protein inhibitors
PL3674302T3 (pl)	2014-04-23	2023-07-24	Incyte Holdings Corporation	1H-pirolo[2,3-c]pirydyn-7(6H)-ony i pirazolo[3,4-c]pirydyn-7(6H)-ony jako inhibitory białek BET
TWI712603B (zh)	2014-09-15	2020-12-11	美商英塞特公司	作為ｂｅｔ蛋白抑制劑之三環雜環
AR106520A1 (es)	2015-10-29	2018-01-24	Incyte Corp	Forma sólida amorfa de un inhibidor de proteína bet
HRP20230466T1 (hr)	2016-06-20	2023-07-21	Incyte Corporation	Kristalni čvrsti oblici bet inhibitora
US11833155B2 (en)	2020-06-03	2023-12-05	Incyte Corporation	Combination therapy for treatment of myeloproliferative neoplasms

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EP0998908A2 (fr)	1998-11-04	2000-05-10	L'oreal	Composition tinctoriale contenant un colorant direct cationique et une pyrazolo-(1,5-a)-pyrimidine à titre de base d'oxydation, et procédés de teinture
WO2004022016A1 (fr)	2002-09-05	2004-03-18	Henkel Kommanditgesellschaft Auf Aktien	Produits pour la teinture de fibres keratiniques
WO2006119819A1 (fr)	2005-05-12	2006-11-16	Henkel Kommanditgesellschaft Auf Aktien	Agent pour colorer des fibres à base de kératine
EP1778176A2 (fr)	2004-06-12	2007-05-02	Henkel Kommanditgesellschaft auf Aktien	Produits pour colorer des fibres contenant de la keratine
EP1789014A1 (fr)	2004-09-14	2007-05-30	Henkel Kommanditgesellschaft Auf Aktien	Substances servant a teindre des fibres keratiniques
WO2007079802A1 (fr)	2005-12-23	2007-07-19	Henkel Ag & Co. Kgaa	Agent de coloration de fibres keratiniques
WO2008074578A2 (fr)	2006-12-18	2008-06-26	Henkel Ag & Co. Kgaa	Agent de coloration de fibres kératiniques

2008
- 2008-10-21 DE DE200810052618 patent/DE102008052618A1/de not_active Withdrawn
2009
- 2009-09-21 WO PCT/EP2009/062216 patent/WO2010046190A2/fr not_active Ceased

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WO2004022016A1 (fr)	2002-09-05	2004-03-18	Henkel Kommanditgesellschaft Auf Aktien	Produits pour la teinture de fibres keratiniques
EP1534227A1 (fr)	2002-09-05	2005-06-01	Henkel Kommanditgesellschaft auf Aktien	Produits pour la teinture de fibres keratiniques
EP1778176A2 (fr)	2004-06-12	2007-05-02	Henkel Kommanditgesellschaft auf Aktien	Produits pour colorer des fibres contenant de la keratine
EP1789014A1 (fr)	2004-09-14	2007-05-30	Henkel Kommanditgesellschaft Auf Aktien	Substances servant a teindre des fibres keratiniques
WO2006119819A1 (fr)	2005-05-12	2006-11-16	Henkel Kommanditgesellschaft Auf Aktien	Agent pour colorer des fibres à base de kératine
WO2007079802A1 (fr)	2005-12-23	2007-07-19	Henkel Ag & Co. Kgaa	Agent de coloration de fibres keratiniques
WO2008074578A2 (fr)	2006-12-18	2008-06-26	Henkel Ag & Co. Kgaa	Agent de coloration de fibres kératiniques

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Also Published As

Publication number	Publication date
WO2010046190A3 (fr)	2011-04-14
WO2010046190A2 (fr)	2010-04-29

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DE102008022710A1 (de)	2009-11-12	Aufhellmittel mit kationischen Acylpyridiniumderivaten, Co-Bleichaktivatoren und Wasserstoffperoxid
DE102008024030A1 (de)	2009-11-19	Aufhellmittel mit kationischen 3,4-Dihydroisochinoliniumderivaten, speziellen Alkanolaminen und Wasserstoffperoxid
DE102008046433A1 (de)	2010-03-11	Aufhellmittel mit 2-Acylpyridinium-Derivaten
DE102008052618A1 (de)	2010-04-22	Tricyclische Aldehyde und C,H-acide Verbindungen
EP2192957A1 (fr)	2010-06-09	Agent éclaircissant contenant des dérivés cationiques de 3,4-dihydroisoquinoléinium et du peroxyde d'hydrogène
DE102010030434A1 (de)	2011-04-07	Kationische Direktzieher mit Dimethyl[(2-oxo-1,3-dioxolan-4-yl)methyl]-ammonium-Gruppierung und Mittel zum Färben von keratinhaltigen Fasern
EP2014275A2 (fr)	2009-01-14	Kit de préparation de formulations stables au stockage
DE102008044714A1 (de)	2010-03-04	Kationische Dihydroisochinolinium-Derivate als Bleichaktivatoren
DE102008036535A1 (de)	2010-02-11	Coloration mit kationisierbaren Polymer
DE102008046883A1 (de)	2010-03-18	Haarbehandlungsmittel mit Spirulina-Extrakt
DE102008061861A1 (de)	2010-06-17	Pflegende Haarfarbe
DE102008046882A1 (de)	2010-03-18	Haarbehandlungsmittel mit Chitosan Succinamid
DE102009001039A1 (de)	2009-12-03	Kationische Direktzieher und Mittel zum Färben von keratinhaltigen Fasern
DE102008018132A1 (de)	2009-10-15	Kationische Direktzieher und Mittel zum Färben von keratinhaltigen Fasern
WO2009019048A2 (fr)	2009-02-12	Teinture pour cheveux
DE102008034845A1 (de)	2010-02-04	Färbemittel mit Wirkstoffkomplex, enthaltend Thiolactat, zur Verringerung der Haarstrukturschädigung
DE102010031243A1 (de)	2011-06-01	Polycyclische Cumarinderivate mit kationischer Ladung und Mittel zum Färben von keratinhaltigen Fasern
EP1944010B1 (fr)	2015-03-11	Matériau d'éclaircissement et/ou de coloration à dérivé(s) d'acide(s) d'acryle(s)
DE102008056811A1 (de)	2009-09-17	Neue Oxidationsfarbstoffvorprodukte
DE102008061342A1 (de)	2010-06-17	Haarfarbe mit Kakaobutter
DE102008061860A1 (de)	2010-06-17	Pflegende Haarfarbe
DE102009001687A1 (de)	2010-01-14	Kationische Direktzieher und Mittel zum Färben von keratinhaltigen Fasern
DE102007018380A1 (de)	2008-10-30	Kationische Direktzieher und Mittel zum Färben von keratinhaltigen Fasern
DE102008061863A1 (de)	2010-04-29	Verfahren zur Kaschierung grauer Haare

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Date	Code	Title	Description
2012-08-16	R119	Application deemed withdrawn, or ip right lapsed, due to non-payment of renewal fee	Effective date: 20120501