DE19818044A1 - Verwendung von Vitamin-PP-Verbindungen - Google Patents
Verwendung von Vitamin-PP-VerbindungenInfo
- Publication number
- DE19818044A1 DE19818044A1 DE19818044A DE19818044A DE19818044A1 DE 19818044 A1 DE19818044 A1 DE 19818044A1 DE 19818044 A DE19818044 A DE 19818044A DE 19818044 A DE19818044 A DE 19818044A DE 19818044 A1 DE19818044 A1 DE 19818044A1
- Authority
- DE
- Germany
- Prior art keywords
- pyridin
- butyl
- acrylamide
- piperidin
- piperazin
- Prior art date
- 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.)
- Ceased
Links
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical class NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 title claims abstract description 189
- 230000003327 cancerostatic effect Effects 0.000 title claims abstract description 91
- 230000000694 effects Effects 0.000 title claims abstract description 72
- 239000003018 immunosuppressive agent Substances 0.000 title claims abstract description 20
- 239000011570 nicotinamide Substances 0.000 title claims description 80
- 235000005152 nicotinamide Nutrition 0.000 title claims description 79
- 229960003966 nicotinamide Drugs 0.000 title claims description 71
- 229940125721 immunosuppressive agent Drugs 0.000 title abstract 7
- 230000003472 neutralizing effect Effects 0.000 title abstract 3
- 150000003222 pyridines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims abstract description 50
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 41
- 235000019160 vitamin B3 Nutrition 0.000 claims abstract description 35
- 239000011708 vitamin B3 Substances 0.000 claims abstract description 35
- 238000002512 chemotherapy Methods 0.000 claims abstract description 22
- 239000000824 cytostatic agent Substances 0.000 claims abstract description 13
- 239000000969 carrier Substances 0.000 claims abstract description 12
- 230000001085 cytostatic effect Effects 0.000 claims abstract description 12
- 238000001959 radiotherapy Methods 0.000 claims abstract description 11
- 230000001154 acute effect Effects 0.000 claims abstract description 10
- 150000001408 amides Chemical class 0.000 claims abstract description 10
- 230000009471 action Effects 0.000 claims abstract description 9
- 230000001506 immunosuppresive effect Effects 0.000 claims abstract description 9
- 230000001028 anti-proliverative effect Effects 0.000 claims abstract description 6
- 206010027476 Metastases Diseases 0.000 claims abstract description 4
- 230000001120 cytoprotective effect Effects 0.000 claims abstract description 4
- 230000009401 metastasis Effects 0.000 claims abstract description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 3
- 230000008105 immune reaction Effects 0.000 claims abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 24
- -1 pyridyl alkene Chemical class 0.000 claims description 286
- 239000000126 substance Substances 0.000 claims description 94
- 239000003814 drug Substances 0.000 claims description 82
- 229940079593 drug Drugs 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 239000000243 solution Substances 0.000 claims description 50
- 239000002246 antineoplastic agent Substances 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 239000004480 active ingredient Substances 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 32
- 239000000843 powder Substances 0.000 claims description 31
- 150000003839 salts Chemical group 0.000 claims description 30
- 239000003826 tablet Substances 0.000 claims description 30
- 229960003512 nicotinic acid Drugs 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 229920006395 saturated elastomer Polymers 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 19
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 239000008101 lactose Substances 0.000 claims description 18
- 239000003380 propellant Substances 0.000 claims description 18
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 239000000725 suspension Substances 0.000 claims description 17
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 230000001225 therapeutic effect Effects 0.000 claims description 15
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- 238000009472 formulation Methods 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 239000000839 emulsion Substances 0.000 claims description 12
- 239000002674 ointment Substances 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 150000001204 N-oxides Chemical class 0.000 claims description 11
- 239000000443 aerosol Substances 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
- 229960003444 immunosuppressant agent Drugs 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
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- 230000009467 reduction Effects 0.000 claims description 10
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 229930195725 Mannitol Natural products 0.000 claims description 9
- 125000004423 acyloxy group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 239000002775 capsule Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000000594 mannitol Substances 0.000 claims description 9
- 235000010355 mannitol Nutrition 0.000 claims description 9
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 8
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 230000008030 elimination Effects 0.000 claims description 8
- 238000003379 elimination reaction Methods 0.000 claims description 8
- 239000007943 implant Substances 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
- 239000008298 dragée Substances 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 239000000600 sorbitol Substances 0.000 claims description 7
- 235000010356 sorbitol Nutrition 0.000 claims description 7
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 6
- 239000008103 glucose Substances 0.000 claims description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 239000007921 spray Substances 0.000 claims description 6
- 230000009885 systemic effect Effects 0.000 claims description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 238000001727 in vivo Methods 0.000 claims description 5
- 238000001802 infusion Methods 0.000 claims description 5
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 5
- 229940071648 metered dose inhaler Drugs 0.000 claims description 5
- JBSPSVYVYTWQNL-UHFFFAOYSA-N n-[4-(1-benzhydrylpiperidin-4-yl)butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCC(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 JBSPSVYVYTWQNL-UHFFFAOYSA-N 0.000 claims description 5
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 239000001273 butane Substances 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 4
- 238000013270 controlled release Methods 0.000 claims description 4
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- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
- 239000007938 effervescent tablet Substances 0.000 claims description 4
- UKACHOXRXFQJFN-UHFFFAOYSA-N heptafluoropropane Chemical compound FC(F)C(F)(F)C(F)(F)F UKACHOXRXFQJFN-UHFFFAOYSA-N 0.000 claims description 4
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 claims description 4
- VZGLEQAAAJNIAH-UHFFFAOYSA-N n-[4-(1-benzhydrylpiperidin-4-yl)butyl]-3-pyridin-3-ylpropanamide Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC1CCCCNC(=O)CCC1=CC=CN=C1 VZGLEQAAAJNIAH-UHFFFAOYSA-N 0.000 claims description 4
- ABNUGIPWBGEPAS-UHFFFAOYSA-N n-[4-(1-benzhydrylpiperidin-4-yl)butyl]-5-pyridin-3-ylpenta-2,4-dienamide Chemical compound C=1C=CN=CC=1C=CC=CC(=O)NCCCCC(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 ABNUGIPWBGEPAS-UHFFFAOYSA-N 0.000 claims description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 239000002243 precursor Substances 0.000 claims description 4
- 239000001294 propane Substances 0.000 claims description 4
- 125000004761 (C2-C7) alkylaminocarbonyl group Chemical group 0.000 claims description 3
- 125000004763 (C3-C13) dialkylaminocarbonyl group Chemical group 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
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- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 230000027455 binding Effects 0.000 claims description 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 230000002496 gastric effect Effects 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 3
- 238000009117 preventive therapy Methods 0.000 claims description 3
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 claims description 3
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- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 3
- 229960002675 xylitol Drugs 0.000 claims description 3
- CUCDLJSFYHNNJV-VQTJNVASSA-N (1r,2r)-2-phenyl-n-[4-(3-pyridin-3-ylprop-2-enoylamino)butyl]cyclopropane-1-carboxamide Chemical compound C1([C@@H]2C[C@H]2C(=O)NCCCCNC(=O)C=CC=2C=NC=CC=2)=CC=CC=C1 CUCDLJSFYHNNJV-VQTJNVASSA-N 0.000 claims description 2
- 125000004754 (C2-C12) dialkylamino group Chemical group 0.000 claims description 2
- SQHKJSPPFSVNDF-UHFFFAOYSA-N 1,2,2,3-tetrakis(hydroxymethyl)cyclohexan-1-ol Chemical compound OCC1CCCC(O)(CO)C1(CO)CO SQHKJSPPFSVNDF-UHFFFAOYSA-N 0.000 claims description 2
- COMRSYCVLKBODY-UHFFFAOYSA-N 3-pyridin-3-yl-n-[4-[4-(1,2,3,4-tetrahydronaphthalen-1-yl)piperazin-1-yl]butyl]prop-2-enamide Chemical compound C1CN(C2C3=CC=CC=C3CCC2)CCN1CCCCNC(=O)C=CC1=CC=CN=C1 COMRSYCVLKBODY-UHFFFAOYSA-N 0.000 claims description 2
- PZYHBBYPOVMRAY-UHFFFAOYSA-N 3-pyridin-3-yl-n-[4-[4-(5,6,7,8-tetrahydronaphthalen-1-yl)piperazin-1-yl]butyl]prop-2-enamide Chemical compound C1CN(C=2C=3CCCCC=3C=CC=2)CCN1CCCCNC(=O)C=CC1=CC=CN=C1 PZYHBBYPOVMRAY-UHFFFAOYSA-N 0.000 claims description 2
- ABZAKAHITMFTMC-UHFFFAOYSA-N 3-pyridin-3-yl-n-[4-[4-(5h-thieno[2,3-c][2]benzothiepin-10-ylidene)piperidin-1-yl]butyl]propanamide Chemical compound C1CC(=C2C3=CC=CC=C3CSC=3SC=CC=32)CCN1CCCCNC(=O)CCC1=CC=CN=C1 ABZAKAHITMFTMC-UHFFFAOYSA-N 0.000 claims description 2
- RUOPWDVFAXCKCF-UHFFFAOYSA-N 4-[4-[4-(3-pyridin-3-ylprop-2-enoylamino)butyl]piperazine-1-carbonyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)N1CCN(CCCCNC(=O)C=CC=2C=NC=CC=2)CC1 RUOPWDVFAXCKCF-UHFFFAOYSA-N 0.000 claims description 2
- LMSDNEUOCUNNFM-UHFFFAOYSA-N 4-[phenyl-[4-[4-(3-pyridin-3-ylprop-2-enoylamino)butyl]piperazin-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C=1C=CC=CC=1)N1CCN(CCCCNC(=O)C=CC=2C=NC=CC=2)CC1 LMSDNEUOCUNNFM-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
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- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 claims description 2
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- DWVHXGDHRMZZJF-UHFFFAOYSA-N N-[4-[4-[bis(4-fluorophenyl)methyl]piperazin-1-yl]but-2-ynyl]-3-pyridin-3-ylprop-2-enamide Chemical compound FC1=CC=C(C=C1)C(N1CCN(CC1)CC#CCNC(C=CC=1C=NC=CC=1)=O)C1=CC=C(C=C1)F DWVHXGDHRMZZJF-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
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- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 2
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- 239000000865 liniment Substances 0.000 claims description 2
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- 125000000335 thiazolyl group Chemical group 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
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- FEZBIKUBAYAZIU-UHFFFAOYSA-N trimethobenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NCC=2C=CC(OCCN(C)C)=CC=2)=C1 FEZBIKUBAYAZIU-UHFFFAOYSA-N 0.000 description 1
- 229960004161 trimethobenzamide Drugs 0.000 description 1
- 229960001099 trimetrexate Drugs 0.000 description 1
- NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
-
- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Toxicology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19818044A DE19818044A1 (de) | 1998-04-22 | 1998-04-22 | Verwendung von Vitamin-PP-Verbindungen |
| DK99922119T DK1079832T3 (da) | 1998-04-22 | 1999-04-21 | Anvendelse af vitamin-PP-forbindelser |
| PCT/EP1999/002686 WO1999053920A1 (en) | 1998-04-22 | 1999-04-21 | Use of vitamin pp compounds |
| DE69928660T DE69928660T2 (de) | 1998-04-22 | 1999-04-21 | Verwendung von vitamin-pp-verbindungen |
| JP2000544324A JP4607319B2 (ja) | 1998-04-22 | 1999-04-21 | ビタミンｐｐ化合物の使用 |
| ES99922119T ES2253890T3 (es) | 1998-04-22 | 1999-04-21 | Uso de compuestos de vitamina pp. |
| EP99922119A EP1079832B1 (en) | 1998-04-22 | 1999-04-21 | Use of vitamin pp compounds |
| AT99922119T ATE311186T1 (de) | 1998-04-22 | 1999-04-21 | Verwendung von vitamin pp verbindungen |
| AU39282/99A AU3928299A (en) | 1998-04-22 | 1999-04-21 | Use of vitamin pp compounds |
| US12/779,698 US20100227896A1 (en) | 1998-04-22 | 2010-05-13 | Use of vitamin pp compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19818044A DE19818044A1 (de) | 1998-04-22 | 1998-04-22 | Verwendung von Vitamin-PP-Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19818044A1 true DE19818044A1 (de) | 1999-10-28 |
Family
ID=7865483
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19818044A Ceased DE19818044A1 (de) | 1998-04-22 | 1998-04-22 | Verwendung von Vitamin-PP-Verbindungen |
| DE69928660T Expired - Lifetime DE69928660T2 (de) | 1998-04-22 | 1999-04-21 | Verwendung von vitamin-pp-verbindungen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69928660T Expired - Lifetime DE69928660T2 (de) | 1998-04-22 | 1999-04-21 | Verwendung von vitamin-pp-verbindungen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20100227896A1 (https=) |
| EP (1) | EP1079832B1 (https=) |
| JP (1) | JP4607319B2 (https=) |
| AT (1) | ATE311186T1 (https=) |
| AU (1) | AU3928299A (https=) |
| DE (2) | DE19818044A1 (https=) |
| DK (1) | DK1079832T3 (https=) |
| ES (1) | ES2253890T3 (https=) |
| WO (1) | WO1999053920A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000007580A3 (en) * | 1998-08-03 | 2000-05-18 | Gene Kutato Kft N | Pharmaceutical compositions against autoimmune diseases |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0104240D0 (en) | 2001-02-21 | 2001-04-11 | Clariant Int Ltd | Copolymer composition having pigment like properties |
| EP1348434A1 (en) * | 2002-03-27 | 2003-10-01 | Fujisawa Deutschland GmbH | Use of pyridyl amides as inhibitors of angiogenesis |
| US8067457B2 (en) | 2005-11-01 | 2011-11-29 | Millennium Pharmaceuticals, Inc. | Compounds useful as antagonists of CCR2 |
| WO2007053499A2 (en) | 2005-11-01 | 2007-05-10 | Millennium Pharmaceuticals, Inc. | Compounds useful as antagonists of ccr2 |
| WO2009072004A2 (en) * | 2007-09-26 | 2009-06-11 | Gemin X Pharmaceuticals Canada, Inc. | Compositions and methods for effecting nad+ levels using a nicotinamide phosphoribosyl transferase inhibitor |
| EP2213288A1 (en) * | 2009-01-30 | 2010-08-04 | Karl Welte | NAMPT and vitamin B3 for treating or preventing diseases |
| CA2768338A1 (en) | 2009-07-17 | 2011-01-20 | Topotarget A/S | Method for predicting the utility of administering nicotinic acid or a precursor or prodrug thereof to reduce the severity of side-effects of cancer treatment with nicotinamide phosphoribosyltransferase inhibitors |
| US8912184B1 (en) | 2010-03-01 | 2014-12-16 | Alzheimer's Institute Of America, Inc. | Therapeutic and diagnostic methods |
| US8791045B2 (en) | 2011-11-09 | 2014-07-29 | Kimberly-Clark Worldwide, Inc. | Non-tacky wetness indicator composition for application on a polymeric substrate |
| US9889222B2 (en) | 2011-11-09 | 2018-02-13 | Kimberly-Clark Worldwide, Inc. | Aqueous medium-sensitive coating compositions for triggered release of active ingredients and visual indication for wetness |
| US9585826B2 (en) | 2012-11-07 | 2017-03-07 | Kimberly-Clark Worldwide, Inc. | Triggerable compositions for two-stage, controlled release of active chemistry |
| HK1215579A1 (zh) | 2012-11-29 | 2016-09-02 | Karyopharm Therapeutics, Inc. | 被取代的2，3-二氫苯並呋喃基化合物和其用途 |
| DK3016946T3 (da) | 2013-07-03 | 2023-01-09 | Karyopharm Therapeutics Inc | Substituerede benzofuranyl- og benzoxazolylforbindelser og anvendelser deraf |
| US9994558B2 (en) | 2013-09-20 | 2018-06-12 | Karyopharm Therapeutics Inc. | Multicyclic compounds and methods of using same |
| US9119780B2 (en) | 2013-10-30 | 2015-09-01 | Kimberly-Clark Worldwide, Inc. | Triggerable compositions for two-stage, controlled release of proactive chemistry |
| WO2017031323A1 (en) | 2015-08-18 | 2017-02-23 | Karyopharm Therapeutics Inc. | (s,e)-3-(6-aminopyridin-3-yl)-n-((5-(4-(3-fluoro-3-methylpyrrolidine-1-carbonyl)phenyl)-7-(4-fluorophenyl)benzofuran-2-yl)methyl)acrylamide for the treatment of cancer |
| US10858347B2 (en) | 2015-12-31 | 2020-12-08 | Karyopharm Therapeutics Inc. | Multicyclic compounds and uses thereof |
| RU2651047C1 (ru) * | 2017-05-04 | 2018-04-18 | Общество С Ограниченной Ответственностью "Научно-Технологическая Фармацевтическая Фирма "Полисан" | Лекарственная композиция цитопротекторного действия и способ ее получения |
| WO2019153007A2 (en) * | 2018-02-05 | 2019-08-08 | The Boaro Of Trustees Of The University Of Illinois | Nicotinamide phosphoribosyltransferase inhibitors and methods for use of the same |
| CN115177594B (zh) * | 2022-07-04 | 2023-08-15 | 武汉大学中南医院 | 一种阿昔替尼药物制剂及其制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3148115A (en) * | 1958-12-08 | 1964-09-08 | Horner Frank W Ltd | Potentiation of tumor-growth inhibition from deoxypyridoxine, testosterone, or 6-mercaptopurine, by 6-aminonicotinamide |
| JPH04103538A (ja) * | 1990-08-24 | 1992-04-06 | Ajinomoto Co Inc | 制癌剤副作用抑制剤 |
| US5547927A (en) * | 1993-05-28 | 1996-08-20 | Abbott Laboratories | Enteral nutritional product for patients undergoing radiation therapy and/or chemotherapy |
| FI970588A7 (fi) * | 1994-08-12 | 1997-04-11 | Wellstat Therapeutics Corp | Menetelmät verenmyrkytyksen tai tulehdussairauksien hoitamiseksi oksipuriininukleosideillä |
| JPH0881371A (ja) * | 1994-09-09 | 1996-03-26 | Suntory Ltd | 造血機能亢進剤 |
| EP0800829B2 (en) * | 1994-12-29 | 2012-07-25 | Chugai Seiyaku Kabushiki Kaisha | Use of a pm-1 antibody or of a mh 166 antibody for enhancing the anti-tumor effect of cisplatin or carboplatin |
| JP3119430B2 (ja) * | 1995-07-25 | 2000-12-18 | 大鵬薬品工業株式会社 | 水酸基ラジカル消去剤 |
| JP2860637B2 (ja) * | 1995-12-11 | 1999-02-24 | 末綱 陽子 | 新規なペプチドおよび活性化酸素阻害剤 |
| JP3836203B2 (ja) * | 1995-12-20 | 2006-10-25 | 日本臓器製薬株式会社 | 活性酸素・フリーラジカル消去剤 |
| DE19624668A1 (de) * | 1996-06-20 | 1998-02-19 | Klinge Co Chem Pharm Fab | Verwendung von Pyridylalkan-, Pyridylalken- bzw. Pyridylalkinsäureamiden |
| DE19624704A1 (de) * | 1996-06-20 | 1998-01-08 | Klinge Co Chem Pharm Fab | Neue Pyridylalkansäureamide |
| US6451816B1 (en) * | 1997-06-20 | 2002-09-17 | Klinge Pharma Gmbh | Use of pyridyl alkane, pyridyl alkene and/or pyridyl alkine acid amides in the treatment of tumors or for immunosuppression |
| DE19624659A1 (de) * | 1996-06-20 | 1998-01-08 | Klinge Co Chem Pharm Fab | Neue Pyridylalken- und Pyridylalkinsäureamide |
| JPH1036260A (ja) * | 1996-07-18 | 1998-02-10 | Mitsui Norin Kk | 抗ガン剤の効力増強方法 |
| JPH1045594A (ja) * | 1996-07-30 | 1998-02-17 | Mitsubishi Gas Chem Co Inc | 活性酸素消去剤 |
-
1998
- 1998-04-22 DE DE19818044A patent/DE19818044A1/de not_active Ceased
-
1999
- 1999-04-21 WO PCT/EP1999/002686 patent/WO1999053920A1/en not_active Ceased
- 1999-04-21 AT AT99922119T patent/ATE311186T1/de active
- 1999-04-21 DK DK99922119T patent/DK1079832T3/da active
- 1999-04-21 EP EP99922119A patent/EP1079832B1/en not_active Expired - Lifetime
- 1999-04-21 AU AU39282/99A patent/AU3928299A/en not_active Abandoned
- 1999-04-21 JP JP2000544324A patent/JP4607319B2/ja not_active Expired - Fee Related
- 1999-04-21 DE DE69928660T patent/DE69928660T2/de not_active Expired - Lifetime
- 1999-04-21 ES ES99922119T patent/ES2253890T3/es not_active Expired - Lifetime
-
2010
- 2010-05-13 US US12/779,698 patent/US20100227896A1/en not_active Abandoned
Non-Patent Citations (3)
| Title |
|---|
| Chem. Abstr.115:150041w * |
| Chem. Abstr.124:173015r * |
| Rote Liste 1997, Nr.86013 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000007580A3 (en) * | 1998-08-03 | 2000-05-18 | Gene Kutato Kft N | Pharmaceutical compositions against autoimmune diseases |
Also Published As
| Publication number | Publication date |
|---|---|
| DK1079832T3 (da) | 2006-04-03 |
| AU3928299A (en) | 1999-11-08 |
| ATE311186T1 (de) | 2005-12-15 |
| WO1999053920A1 (en) | 1999-10-28 |
| US20100227896A1 (en) | 2010-09-09 |
| DE69928660T2 (de) | 2006-09-14 |
| JP4607319B2 (ja) | 2011-01-05 |
| ES2253890T3 (es) | 2006-06-01 |
| EP1079832B1 (en) | 2005-11-30 |
| JP2002512190A (ja) | 2002-04-23 |
| EP1079832A1 (en) | 2001-03-07 |
| DE69928660D1 (de) | 2006-01-05 |
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