JP2006514917A5 - - Google Patents
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- Publication number
- JP2006514917A5 JP2006514917A5 JP2004520071A JP2004520071A JP2006514917A5 JP 2006514917 A5 JP2006514917 A5 JP 2006514917A5 JP 2004520071 A JP2004520071 A JP 2004520071A JP 2004520071 A JP2004520071 A JP 2004520071A JP 2006514917 A5 JP2006514917 A5 JP 2006514917A5
- Authority
- JP
- Japan
- Prior art keywords
- quinoline
- amino
- diethylamino
- butylamino
- carboxy
- 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.)
- Pending
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- 239000000203 mixture Substances 0.000 claims 21
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 12
- 230000002093 peripheral effect Effects 0.000 claims 8
- -1 4-ethyl- (2-hydroxyethyl) -amino-1-methylbutylamino Quinoline Chemical compound 0.000 claims 6
- 239000002671 adjuvant Substances 0.000 claims 6
- 239000003112 inhibitor Substances 0.000 claims 6
- 239000004480 active ingredient Substances 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 230000004060 metabolic process Effects 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 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 4
- 208000018737 Parkinson disease Diseases 0.000 claims 4
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 claims 3
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 claims 2
- ITPDYQOUSLNIHG-UHFFFAOYSA-N Amiodarone hydrochloride Chemical compound [Cl-].CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCC[NH+](CC)CC)C(I)=C1 ITPDYQOUSLNIHG-UHFFFAOYSA-N 0.000 claims 2
- 102000004328 Cytochrome P-450 CYP3A Human genes 0.000 claims 2
- 108010081668 Cytochrome P-450 CYP3A Proteins 0.000 claims 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims 2
- 229960005260 amiodarone Drugs 0.000 claims 2
- 150000003943 catecholamines Chemical class 0.000 claims 2
- 229960003677 chloroquine Drugs 0.000 claims 2
- 229960001380 cimetidine Drugs 0.000 claims 2
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 claims 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 claims 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims 2
- 239000003623 enhancer Substances 0.000 claims 2
- 239000002532 enzyme inhibitor Substances 0.000 claims 2
- 239000000938 histamine H1 antagonist Substances 0.000 claims 2
- XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 claims 2
- 229960004171 hydroxychloroquine Drugs 0.000 claims 2
- 229960003248 mifepristone Drugs 0.000 claims 2
- VKHAHZOOUSRJNA-GCNJZUOMSA-N mifepristone Chemical compound C1([C@@H]2C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]3CC[C@@]([C@]3(C2)C)(O)C#CC)=CC=C(N(C)C)C=C1 VKHAHZOOUSRJNA-GCNJZUOMSA-N 0.000 claims 2
- LSGISLMKNCXXNS-UHFFFAOYSA-N n-(7-chloroquinolin-4-yl)-n',n'-diethylbutane-1,4-diamine Chemical compound ClC1=CC=C2C(NCCCCN(CC)CC)=CC=NC2=C1 LSGISLMKNCXXNS-UHFFFAOYSA-N 0.000 claims 2
- 210000002569 neuron Anatomy 0.000 claims 2
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims 1
- 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 1
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims 1
- JXYWFNAQESKDNC-BTJKTKAUSA-N (z)-4-hydroxy-4-oxobut-2-enoate;2-[(4-methoxyphenyl)methyl-pyridin-2-ylamino]ethyl-dimethylazanium Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 JXYWFNAQESKDNC-BTJKTKAUSA-N 0.000 claims 1
- YQDKVTYBHKVETH-UHFFFAOYSA-N 1-(3,4-dihydro-2h-quinolin-1-yl)butan-1-one Chemical compound C1=CC=C2N(C(=O)CCC)CCCC2=C1 YQDKVTYBHKVETH-UHFFFAOYSA-N 0.000 claims 1
- RRWLNRQGJSQRAF-UHFFFAOYSA-N 1-(3,4-dihydro-2h-quinolin-1-yl)ethanone Chemical compound C1=CC=C2N(C(=O)C)CCCC2=C1 RRWLNRQGJSQRAF-UHFFFAOYSA-N 0.000 claims 1
- OTKWDNCXANVGKB-UHFFFAOYSA-N 1-n,1-n-diethyl-4-n-(7-fluoroquinolin-4-yl)pentane-1,4-diamine Chemical compound FC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 OTKWDNCXANVGKB-UHFFFAOYSA-N 0.000 claims 1
- VHKXUUQMMLOHCT-UHFFFAOYSA-N 2-[(2-chloroquinolin-4-yl)amino]-5-(diethylamino)pentanoic acid Chemical compound ClC1=NC2=CC=CC=C2C(=C1)NC(CCCN(CC)CC)C(=O)O VHKXUUQMMLOHCT-UHFFFAOYSA-N 0.000 claims 1
- VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 claims 1
- HLYKPDXXIDMNHY-UHFFFAOYSA-N 2-[(7-chloroquinolin-4-yl)amino]-5-(diethylamino)-2-methylpentanoic acid Chemical compound ClC1=CC=C2C(NC(C)(CCCN(CC)CC)C(O)=O)=CC=NC2=C1 HLYKPDXXIDMNHY-UHFFFAOYSA-N 0.000 claims 1
- CRCWPKGKPRVXAP-UHFFFAOYSA-N 2-[4-[(7-chloroquinolin-4-yl)amino]pentyl-ethylamino]ethanol;phosphoric acid Chemical compound OP(O)(O)=O.OP(O)(O)=O.ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 CRCWPKGKPRVXAP-UHFFFAOYSA-N 0.000 claims 1
- USCWUEAEIGDJQJ-UHFFFAOYSA-N 2-[amino(quinolin-4-yl)amino]-3-(2-hydroxyethyl)-2-methylheptanoic acid Chemical compound C1=CC=C2C(N(N)C(C)(C(CCO)CCCC)C(O)=O)=CC=NC2=C1 USCWUEAEIGDJQJ-UHFFFAOYSA-N 0.000 claims 1
- JIPMJMODMIWJKN-UHFFFAOYSA-N 2-[amino-(7-chloroquinolin-4-yl)amino]-5-ethyl-7-hydroxyheptanoic acid Chemical compound ClC1=CC=C2C(N(N)C(CCC(CCO)CC)C(O)=O)=CC=NC2=C1 JIPMJMODMIWJKN-UHFFFAOYSA-N 0.000 claims 1
- TUDGWCRLCIOVOJ-UHFFFAOYSA-N 2-[amino-(7-fluoroquinolin-4-yl)amino]-5-ethyl-7-hydroxyheptanoic acid Chemical compound FC1=CC=C2C(N(N)C(CCC(CCO)CC)C(O)=O)=CC=NC2=C1 TUDGWCRLCIOVOJ-UHFFFAOYSA-N 0.000 claims 1
- FSFQHUDTQQRPRF-UHFFFAOYSA-N 2-[amino-(7-hydroxyquinolin-4-yl)amino]-3-(2-hydroxyethyl)-2-methylheptanoic acid Chemical compound OC1=CC=C2C(N(N)C(C)(C(CCO)CCCC)C(O)=O)=CC=NC2=C1 FSFQHUDTQQRPRF-UHFFFAOYSA-N 0.000 claims 1
- NXFRLHZIDSABNT-UHFFFAOYSA-N 2-[amino-(7-hydroxyquinolin-4-yl)amino]-5-ethyl-7-hydroxyheptanoic acid Chemical compound OC1=CC=C2C(N(N)C(CCC(CCO)CC)C(O)=O)=CC=NC2=C1 NXFRLHZIDSABNT-UHFFFAOYSA-N 0.000 claims 1
- RPZDJWSZVSCQDU-UHFFFAOYSA-N 3,4-dihydro-2h-quinoline-1-carbaldehyde Chemical compound C1=CC=C2N(C=O)CCCC2=C1 RPZDJWSZVSCQDU-UHFFFAOYSA-N 0.000 claims 1
- HXQVDILZYYOGIA-UHFFFAOYSA-N 3-[amino-(7-fluoroquinolin-4-yl)amino]-3-methyloctan-1-ol Chemical compound FC1=CC=C2C(N(N)C(C)(CCO)CCCCC)=CC=NC2=C1 HXQVDILZYYOGIA-UHFFFAOYSA-N 0.000 claims 1
- QHILAOKBLSXUFN-UHFFFAOYSA-N 4-[4-(diethylamino)butylamino]quinolin-7-ol Chemical compound OC1=CC=C2C(NCCCCN(CC)CC)=CC=NC2=C1 QHILAOKBLSXUFN-UHFFFAOYSA-N 0.000 claims 1
- XFYNSXDIWDIXCT-UHFFFAOYSA-N 4-[amino-(1-hydroxy-3-methyloctan-3-yl)amino]quinolin-7-ol 3-[amino(quinolin-4-yl)amino]-3-methyloctan-1-ol Chemical compound C1=CC=C2C(N(N)C(C)(CCO)CCCCC)=CC=NC2=C1.OC1=CC=C2C(N(N)C(C)(CCO)CCCCC)=CC=NC2=C1 XFYNSXDIWDIXCT-UHFFFAOYSA-N 0.000 claims 1
- UMRGTKNUIHCPNA-UHFFFAOYSA-N 4-[amino-(4-ethyl-6-hydroxyhexyl)amino]quinolin-7-ol Chemical compound OC1=CC=C2C(N(N)CCCC(CCO)CC)=CC=NC2=C1 UMRGTKNUIHCPNA-UHFFFAOYSA-N 0.000 claims 1
- AEUAEICGCMSYCQ-UHFFFAOYSA-N 4-n-(7-chloroquinolin-1-ium-4-yl)-1-n,1-n-diethylpentane-1,4-diamine;dihydrogen phosphate Chemical compound OP(O)(O)=O.ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 AEUAEICGCMSYCQ-UHFFFAOYSA-N 0.000 claims 1
- CVHAOXMRXFUHLJ-UHFFFAOYSA-N 5-(diethylamino)-2-(quinolin-4-ylamino)pentanoic acid Chemical compound C1=CC=C2C(NC(CCCN(CC)CC)C(O)=O)=CC=NC2=C1 CVHAOXMRXFUHLJ-UHFFFAOYSA-N 0.000 claims 1
- PRSVYKDLQBBGOB-UHFFFAOYSA-N 5-(diethylamino)-2-[(7-hydroxyquinolin-4-yl)amino]-2-methylpentanoic acid Chemical compound OC1=CC=C2C(NC(C)(CCCN(CC)CC)C(O)=O)=CC=NC2=C1 PRSVYKDLQBBGOB-UHFFFAOYSA-N 0.000 claims 1
- CPNKXOBXSJTMAY-UHFFFAOYSA-N 6-[amino(quinolin-4-yl)amino]-3-ethylhexan-1-ol Chemical compound C1=CC=C2C(N(N)CCCC(CCO)CC)=CC=NC2=C1 CPNKXOBXSJTMAY-UHFFFAOYSA-N 0.000 claims 1
- TYVAPQROTCCTGR-UHFFFAOYSA-N 6-[amino-(7-fluoroquinolin-4-yl)amino]-3-ethylhexan-1-ol Chemical compound FC1=CC=C2C(N(N)CCCC(CCO)CC)=CC=NC2=C1 TYVAPQROTCCTGR-UHFFFAOYSA-N 0.000 claims 1
- 206010003694 Atrophy Diseases 0.000 claims 1
- QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 claims 1
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 claims 1
- DBAKFASWICGISY-BTJKTKAUSA-N Chlorpheniramine maleate Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 DBAKFASWICGISY-BTJKTKAUSA-N 0.000 claims 1
- GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 claims 1
- 108010001237 Cytochrome P-450 CYP2D6 Proteins 0.000 claims 1
- 108010052832 Cytochromes Proteins 0.000 claims 1
- 102000018832 Cytochromes Human genes 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
- OCJYIGYOJCODJL-UHFFFAOYSA-N Meclizine Chemical compound CC1=CC=CC(CN2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=C1 OCJYIGYOJCODJL-UHFFFAOYSA-N 0.000 claims 1
- HBNPJJILLOYFJU-VMPREFPWSA-N Mibefradil Chemical compound C1CC2=CC(F)=CC=C2[C@H](C(C)C)[C@@]1(OC(=O)COC)CCN(C)CCCC1=NC2=CC=CC=C2N1 HBNPJJILLOYFJU-VMPREFPWSA-N 0.000 claims 1
- 208000009668 Neurobehavioral Manifestations Diseases 0.000 claims 1
- 201000005625 Neuroleptic malignant syndrome Diseases 0.000 claims 1
- YYVFXSYQSOZCOQ-UHFFFAOYSA-N Oxyquinoline sulfate Chemical compound [O-]S([O-])(=O)=O.C1=C[NH+]=C2C(O)=CC=CC2=C1.C1=C[NH+]=C2C(O)=CC=CC2=C1 YYVFXSYQSOZCOQ-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims 1
- UFLGIAIHIAPJJC-UHFFFAOYSA-N Tripelennamine Chemical compound C=1C=CC=NC=1N(CCN(C)C)CC1=CC=CC=C1 UFLGIAIHIAPJJC-UHFFFAOYSA-N 0.000 claims 1
- GXDALQBWZGODGZ-UHFFFAOYSA-N astemizole Chemical compound C1=CC(OC)=CC=C1CCN1CCC(NC=2N(C3=CC=CC=C3N=2)CC=2C=CC(F)=CC=2)CC1 GXDALQBWZGODGZ-UHFFFAOYSA-N 0.000 claims 1
- 230000037444 atrophy Effects 0.000 claims 1
- 229960000725 brompheniramine Drugs 0.000 claims 1
- ZDIGNSYAACHWNL-UHFFFAOYSA-N brompheniramine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Br)C=C1 ZDIGNSYAACHWNL-UHFFFAOYSA-N 0.000 claims 1
- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 claims 1
- 239000001354 calcium citrate Substances 0.000 claims 1
- 229960004256 calcium citrate Drugs 0.000 claims 1
- 239000004227 calcium gluconate Substances 0.000 claims 1
- 229960004494 calcium gluconate Drugs 0.000 claims 1
- 235000013927 calcium gluconate Nutrition 0.000 claims 1
- MKJXYGKVIBWPFZ-UHFFFAOYSA-L calcium lactate Chemical compound [Ca+2].CC(O)C([O-])=O.CC(O)C([O-])=O MKJXYGKVIBWPFZ-UHFFFAOYSA-L 0.000 claims 1
- 239000001527 calcium lactate Substances 0.000 claims 1
- 229960002401 calcium lactate Drugs 0.000 claims 1
- 235000011086 calcium lactate Nutrition 0.000 claims 1
- 239000001506 calcium phosphate Substances 0.000 claims 1
- 229910000389 calcium phosphate Inorganic materials 0.000 claims 1
- 229960001714 calcium phosphate Drugs 0.000 claims 1
- 235000011010 calcium phosphates Nutrition 0.000 claims 1
- NEEHYRZPVYRGPP-UHFFFAOYSA-L calcium;2,3,4,5,6-pentahydroxyhexanoate Chemical compound [Ca+2].OCC(O)C(O)C(O)C(O)C([O-])=O.OCC(O)C(O)C(O)C(O)C([O-])=O NEEHYRZPVYRGPP-UHFFFAOYSA-L 0.000 claims 1
- 229960000428 carbinoxamine Drugs 0.000 claims 1
- OJFSXZCBGQGRNV-UHFFFAOYSA-N carbinoxamine Chemical compound C=1C=CC=NC=1C(OCCN(C)C)C1=CC=C(Cl)C=C1 OJFSXZCBGQGRNV-UHFFFAOYSA-N 0.000 claims 1
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims 1
- 229960000590 celecoxib Drugs 0.000 claims 1
- 230000004098 cellular respiration Effects 0.000 claims 1
- 229960004342 cetirizine hydrochloride Drugs 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229960002328 chloroquine phosphate Drugs 0.000 claims 1
- SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 claims 1
- 229960003291 chlorphenamine Drugs 0.000 claims 1
- 229940046978 chlorpheniramine maleate Drugs 0.000 claims 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims 1
- 229960003405 ciprofloxacin Drugs 0.000 claims 1
- 229960002626 clarithromycin Drugs 0.000 claims 1
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 claims 1
- 229960002881 clemastine Drugs 0.000 claims 1
- YNNUSGIPVFPVBX-NHCUHLMSSA-N clemastine Chemical compound CN1CCC[C@@H]1CCO[C@@](C)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 YNNUSGIPVFPVBX-NHCUHLMSSA-N 0.000 claims 1
- 229960004606 clomipramine Drugs 0.000 claims 1
- 229960005319 delavirdine Drugs 0.000 claims 1
- 239000003405 delayed action preparation Substances 0.000 claims 1
- 229940116901 diethyldithiocarbamate Drugs 0.000 claims 1
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 229960004166 diltiazem Drugs 0.000 claims 1
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/192,414 US20020198231A1 (en) | 1999-07-13 | 2002-07-09 | Compositions and methods for the treatment of Parkinson's disease |
| US47974803P | 2003-06-19 | 2003-06-19 | |
| PCT/US2003/021463 WO2004004660A2 (en) | 2002-07-09 | 2003-07-09 | Compositions and methods for the treatment of parkinson’s disease and tardive dyskinesias |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006514917A JP2006514917A (ja) | 2006-05-18 |
| JP2006514917A5 true JP2006514917A5 (https=) | 2006-08-17 |
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| JP2004520071A Pending JP2006514917A (ja) | 2002-07-09 | 2003-07-09 | パーキンソン病および遅発性ジスキネジーの処置のための組成物および方法 |
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| EP (1) | EP1581167A4 (https=) |
| JP (1) | JP2006514917A (https=) |
| AU (1) | AU2003248893A1 (https=) |
| CA (1) | CA2531810A1 (https=) |
| WO (1) | WO2004004660A2 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007067714A2 (en) | 2005-12-08 | 2007-06-14 | The Mclean Hospital Corporation | Treatment of sequelae of psychiatric disorders |
| RU2008135762A (ru) * | 2006-02-16 | 2010-03-27 | Де МакЛин Хоспитал Корпорейшн (US) | Способы и композиции для лечения болезни паркинсона |
| AU2010256541B2 (en) * | 2009-06-03 | 2016-03-10 | Marquette University | Modulation of KCNQ potassium channel activity for treatment of psychiatric disorders and the symptoms thereof |
| CN103180297A (zh) * | 2009-12-11 | 2013-06-26 | 基因密码公司 | 使用gdnf家族配体(gfl)模拟剂或ret信号传导通路活化剂促进神经细胞存活的方法 |
| CN113354581B (zh) * | 2020-03-06 | 2023-06-20 | 华南理工大学 | 手性氯喹及其磷酸盐的制备方法及其应用 |
| CN113527201A (zh) * | 2020-04-14 | 2021-10-22 | 瀚海新拓(杭州)生物医药有限公司 | 光学活性氯喹和羟氯喹及其类似物、其制备方法、组合物和用途 |
| WO2025213007A1 (en) * | 2024-04-04 | 2025-10-09 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | S-hydroxychloroquine, optionally with tauroursodeoxycholic acid and/or 3,3'-diindolylmethane, for treating and/or preventing neurological disorders |
| CN119924299B (zh) * | 2025-04-08 | 2025-06-06 | 内蒙古农业大学 | 羊精子内源铁死亡抑制蛋白保护剂及保护方法与应用 |
Family Cites Families (4)
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| US5430039A (en) * | 1990-09-28 | 1995-07-04 | Cephalon, Inc. | Treatment of neurological disorders |
| US5496836A (en) * | 1994-05-05 | 1996-03-05 | Mount Sinai School Of Medicine Of The City University Of New York | Use of famotidine and related compounds in the treatment of movement disorders |
| DE4428199A1 (de) * | 1994-08-09 | 1996-02-15 | Univ Ludwigs Albert | Verwendung von Flunitrazepam und/oder Chloroquin zur Behandlung von Spätdyskinesien |
| ATE431141T1 (de) * | 1999-07-13 | 2009-05-15 | Alpha Res Group Llc | Zusammensetzungen und verfahren zur behandlung der parkinson-krankheit |
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- 2003-07-09 WO PCT/US2003/021463 patent/WO2004004660A2/en not_active Ceased
- 2003-07-09 EP EP03763398A patent/EP1581167A4/en not_active Withdrawn
- 2003-07-09 CA CA002531810A patent/CA2531810A1/en not_active Abandoned
- 2003-07-09 AU AU2003248893A patent/AU2003248893A1/en not_active Abandoned
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