JP2003500350A5 - - Google Patents
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- Publication number
- JP2003500350A5 JP2003500350A5 JP2000619408A JP2000619408A JP2003500350A5 JP 2003500350 A5 JP2003500350 A5 JP 2003500350A5 JP 2000619408 A JP2000619408 A JP 2000619408A JP 2000619408 A JP2000619408 A JP 2000619408A JP 2003500350 A5 JP2003500350 A5 JP 2003500350A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- tetrahydroisoquinoline
- salt
- compound
- tetrahydroisoquinolinyl
- 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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- 150000001875 compounds Chemical class 0.000 description 54
- 150000003839 salts Chemical class 0.000 description 49
- 239000002253 acid Substances 0.000 description 48
- 150000002148 esters Chemical class 0.000 description 48
- 102000036770 Islet Amyloid Polypeptide Human genes 0.000 description 28
- 108010041872 Islet Amyloid Polypeptide Proteins 0.000 description 28
- PLOPBXQQPZYQFA-AXPWDRQUSA-N amlintide Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H]1NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CCCCN)CSSC1)[C@@H](C)O)C(C)C)C1=CC=CC=C1 PLOPBXQQPZYQFA-AXPWDRQUSA-N 0.000 description 28
- 208000037259 Amyloid Plaque Diseases 0.000 description 24
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 23
- 201000010099 disease Diseases 0.000 description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 22
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 20
- 239000008194 pharmaceutical composition Substances 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- -1 1,2,3,4-tetrahydroisoquinolyl Chemical group 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 239000003814 drug Substances 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- YYTAYINRPUJPNH-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1NCCC2=CC(OC)=CC=C21 YYTAYINRPUJPNH-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 4
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
- BPSLFSXCUJYFIR-UHFFFAOYSA-N 7-methoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1CNCC2=CC(OC)=CC=C21 BPSLFSXCUJYFIR-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- KKCYVQMWTVIFFX-LJIZCISZSA-N (2r,3s,4r,5r,6s)-2-(hydroxymethyl)-6-(7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-yl)oxane-3,4,5-triol Chemical compound COC1=CC=2CNCCC=2C=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O KKCYVQMWTVIFFX-LJIZCISZSA-N 0.000 description 2
- LZXHHNKULPHARO-UHFFFAOYSA-M (3,4-dichlorophenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].C1=C(Cl)C(Cl)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LZXHHNKULPHARO-UHFFFAOYSA-M 0.000 description 2
- BWKMGYQJPOAASG-VIFPVBQESA-N (3s)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid Chemical compound C1=CC=C2CN[C@H](C(=O)O)CC2=C1 BWKMGYQJPOAASG-VIFPVBQESA-N 0.000 description 2
- YZGSLLPFIVQGHO-UHFFFAOYSA-N 1,2,3,4-tetrahydrobenzo[g]isoquinoline Chemical compound C1=CC=C2C=C(CNCC3)C3=CC2=C1 YZGSLLPFIVQGHO-UHFFFAOYSA-N 0.000 description 2
- ATFPYFJVFQYJPT-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-1-ylphosphonic acid Chemical compound C1=CC=C2C(P(O)(=O)O)NCCC2=C1 ATFPYFJVFQYJPT-UHFFFAOYSA-N 0.000 description 2
- CQNSOIKACZHLHP-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-2-ium-7-carboxylate Chemical compound C1CNCC2=CC(C(=O)O)=CC=C21 CQNSOIKACZHLHP-UHFFFAOYSA-N 0.000 description 2
- SAAFIVJVSQVSSW-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-6-amine Chemical compound C1NCCC2=CC(N)=CC=C21 SAAFIVJVSQVSSW-UHFFFAOYSA-N 0.000 description 2
- VMEDBFRQSKKEEQ-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-7-amine Chemical compound C1CNCC2=CC(N)=CC=C21 VMEDBFRQSKKEEQ-UHFFFAOYSA-N 0.000 description 2
- RADQTHXRZJGDQI-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-7-ol Chemical compound C1CNCC2=CC(O)=CC=C21 RADQTHXRZJGDQI-UHFFFAOYSA-N 0.000 description 2
- RAUHFTOXJZRVIJ-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-7-ylmethanol Chemical compound C1CNCC2=CC(CO)=CC=C21 RAUHFTOXJZRVIJ-UHFFFAOYSA-N 0.000 description 2
- RRFVBQIHYMTPIX-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline-5-sulfonic acid Chemical compound C1NCCC2=C1C=CC=C2S(=O)(=O)O RRFVBQIHYMTPIX-UHFFFAOYSA-N 0.000 description 2
- RKWNQODBLXZUES-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline-6-carbonitrile Chemical compound C1NCCC2=CC(C#N)=CC=C21 RKWNQODBLXZUES-UHFFFAOYSA-N 0.000 description 2
- LJFNUFCUPDECPC-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline-7-carbonitrile Chemical compound C1CNCC2=CC(C#N)=CC=C21 LJFNUFCUPDECPC-UHFFFAOYSA-N 0.000 description 2
- DBBJBGPWKFVBDD-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline-8-sulfonic acid Chemical compound C1CNCC2=C1C=CC=C2S(=O)(=O)O DBBJBGPWKFVBDD-UHFFFAOYSA-N 0.000 description 2
- UXYRXGFUANQKTA-UHFFFAOYSA-N 1,2-oxazole-3-carboxylic acid Chemical compound OC(=O)C=1C=CON=1 UXYRXGFUANQKTA-UHFFFAOYSA-N 0.000 description 2
- MIIQJAUWHSUTIT-UHFFFAOYSA-N 1,2-oxazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=NO1 MIIQJAUWHSUTIT-UHFFFAOYSA-N 0.000 description 2
- KKJBHMRJVQULAV-UHFFFAOYSA-N 1-(1,2,3,4-tetrahydroisoquinolin-7-yl)ethanone Chemical compound C1CNCC2=CC(C(=O)C)=CC=C21 KKJBHMRJVQULAV-UHFFFAOYSA-N 0.000 description 2
- QHSYXMARPLFYEN-UHFFFAOYSA-N 1-amino-6-hydroxyhexane-1-sulfonic acid Chemical compound OCCCCCC(S(=O)(=O)O)N QHSYXMARPLFYEN-UHFFFAOYSA-N 0.000 description 2
- MHRYARQMWNEHBN-UHFFFAOYSA-N 2-(1,2,3,4-tetrahydroisoquinolin-7-ylsulfonyl)aniline Chemical compound NC1=CC=CC=C1S(=O)(=O)C1=CC=C(CCNC2)C2=C1 MHRYARQMWNEHBN-UHFFFAOYSA-N 0.000 description 2
- NTWSYFLHXNIBJU-UHFFFAOYSA-N 2-(3,4-dihydro-1h-isoquinolin-2-yl)-2-oxoethanesulfonic acid Chemical compound C1=CC=C2CN(C(=O)CS(=O)(=O)O)CCC2=C1 NTWSYFLHXNIBJU-UHFFFAOYSA-N 0.000 description 2
- XWDMLZXQYCEXHG-UHFFFAOYSA-N 2-(3,4-dihydro-1h-isoquinolin-2-ylmethyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1CN1CC2=CC=CC=C2CC1 XWDMLZXQYCEXHG-UHFFFAOYSA-N 0.000 description 2
- IDUQEQWLYKWVQJ-UHFFFAOYSA-N 2-(3,4-dihydro-1h-isoquinoline-2-carbonyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C(=O)N1CC2=CC=CC=C2CC1 IDUQEQWLYKWVQJ-UHFFFAOYSA-N 0.000 description 2
- VFCWGXGWQPTGNQ-UHFFFAOYSA-N 2-ethyl-3,4-dihydro-1h-isoquinoline Chemical compound C1=CC=C2CN(CC)CCC2=C1 VFCWGXGWQPTGNQ-UHFFFAOYSA-N 0.000 description 2
- SIVMAKNQXUEGIS-UHFFFAOYSA-N 2-hydroxyethylsulfamic acid Chemical compound OCCNS(O)(=O)=O SIVMAKNQXUEGIS-UHFFFAOYSA-N 0.000 description 2
- IPZNMGRUBGFDDE-UHFFFAOYSA-N 2-hydroxypropane-1,3-disulfonic acid Chemical compound OS(=O)(=O)CC(O)CS(O)(=O)=O IPZNMGRUBGFDDE-UHFFFAOYSA-N 0.000 description 2
- ZTGTXQJFHLHMSM-UHFFFAOYSA-N 2-hydroxypropylsulfamic acid Chemical compound OC(CNS(O)(=O)=O)C ZTGTXQJFHLHMSM-UHFFFAOYSA-N 0.000 description 2
- CCIQJYJAIYBYEU-UHFFFAOYSA-N 2-propyl-3,4-dihydro-1h-isoquinoline Chemical compound C1=CC=C2CN(CCC)CCC2=C1 CCIQJYJAIYBYEU-UHFFFAOYSA-N 0.000 description 2
- RGTUKZPKWZAIAF-UHFFFAOYSA-N 3-(1,3-dihydroisoindol-2-yl)propane-1-sulfonic acid Chemical compound C1=CC=C2CN(CCCS(=O)(=O)O)CC2=C1 RGTUKZPKWZAIAF-UHFFFAOYSA-N 0.000 description 2
- FLWPEYJUZRLMOU-UHFFFAOYSA-N 3-(2,3-dihydroindol-1-yl)propane-1-sulfonic acid Chemical compound C1=CC=C2N(CCCS(=O)(=O)O)CCC2=C1 FLWPEYJUZRLMOU-UHFFFAOYSA-N 0.000 description 2
- SCAXLHTZHMCKKP-UHFFFAOYSA-N 3-(4h-pyridin-1-yl)propane-1-sulfonic acid;sodium Chemical compound [Na].OS(=O)(=O)CCCN1C=CCC=C1 SCAXLHTZHMCKKP-UHFFFAOYSA-N 0.000 description 2
- DVLFYONBTKHTER-UHFFFAOYSA-N 3-(N-morpholino)propanesulfonic acid Chemical compound OS(=O)(=O)CCCN1CCOCC1 DVLFYONBTKHTER-UHFFFAOYSA-N 0.000 description 2
- GYJNVSAUBGJVLV-UHFFFAOYSA-N 3-(dimethylazaniumyl)propane-1-sulfonate Chemical compound CN(C)CCCS(O)(=O)=O GYJNVSAUBGJVLV-UHFFFAOYSA-N 0.000 description 2
- SNKZJIOFVMKAOJ-UHFFFAOYSA-N 3-Amino-1-propanesulfonic acid Natural products NCCCS(O)(=O)=O SNKZJIOFVMKAOJ-UHFFFAOYSA-N 0.000 description 2
- BZVKOCJZTCLEMW-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropane-1-sulfonate Chemical compound NCC(O)CS(O)(=O)=O BZVKOCJZTCLEMW-UHFFFAOYSA-N 0.000 description 2
- QIKMDZAUHYRRQV-UHFFFAOYSA-N 3-hydroxypropane-1-sulfonic acid;sulfuric acid Chemical compound OS(O)(=O)=O.OCCCS(O)(=O)=O QIKMDZAUHYRRQV-UHFFFAOYSA-N 0.000 description 2
- REEBJQTUIJTGAL-UHFFFAOYSA-N 3-pyridin-1-ium-1-ylpropane-1-sulfonate Chemical compound [O-]S(=O)(=O)CCC[N+]1=CC=CC=C1 REEBJQTUIJTGAL-UHFFFAOYSA-N 0.000 description 2
- OURSFPZPOXNNKX-UHFFFAOYSA-N 3-sulfopropanoic acid Chemical compound OC(=O)CCS(O)(=O)=O OURSFPZPOXNNKX-UHFFFAOYSA-N 0.000 description 2
- XRUIERQCHYNNEP-UHFFFAOYSA-N 4-chloro-n-methyl-2-(1,2,3,4-tetrahydroisoquinolin-1-yl)aniline Chemical compound CNC1=CC=C(Cl)C=C1C1C2=CC=CC=C2CCN1 XRUIERQCHYNNEP-UHFFFAOYSA-N 0.000 description 2
- ORQDJGSWJKNUKH-UHFFFAOYSA-N 4-sulfobutanoic acid Chemical compound OC(=O)CCCS(O)(=O)=O ORQDJGSWJKNUKH-UHFFFAOYSA-N 0.000 description 2
- OWMVLLARHUUNMY-UHFFFAOYSA-N 5-(3,4-dihydro-1h-isoquinolin-2-ylmethyl)-1,2-oxazol-3-one Chemical compound O1N=C(O)C=C1CN1CC2=CC=CC=C2CC1 OWMVLLARHUUNMY-UHFFFAOYSA-N 0.000 description 2
- JRQUJWZBBVDOQE-UHFFFAOYSA-N 5-[(6-methoxy-3,4-dihydro-1h-isoquinolin-2-yl)methyl]-1,2-oxazol-3-one Chemical compound C1CC2=CC(OC)=CC=C2CN1CC1=CC(O)=NO1 JRQUJWZBBVDOQE-UHFFFAOYSA-N 0.000 description 2
- OBYMZHCNAHRSDH-UHFFFAOYSA-N 6-methoxy-2-propyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CC=C2CN(CCC)CCC2=C1 OBYMZHCNAHRSDH-UHFFFAOYSA-N 0.000 description 2
- ZYOMQQCBYBAJAT-UHFFFAOYSA-N 7-(2h-tetrazol-5-yl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C2CNCCC2=CC=C1C1=NN=NN1 ZYOMQQCBYBAJAT-UHFFFAOYSA-N 0.000 description 2
- NGQHLYGRTFVUEM-UHFFFAOYSA-N 7-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1CNCC2=CC(C(F)(F)F)=CC=C21 NGQHLYGRTFVUEM-UHFFFAOYSA-N 0.000 description 2
- VMBKQHVXRMDVNK-UHFFFAOYSA-N 7-benzyl-1,2,3,4-tetrahydroisoquinoline Chemical compound C=1C=C2CCNCC2=CC=1CC1=CC=CC=C1 VMBKQHVXRMDVNK-UHFFFAOYSA-N 0.000 description 2
- FCTMZZUXBMQAER-UHFFFAOYSA-N 7-methyl-1,2,3,4-tetrahydroisoquinoline Chemical compound C1CNCC2=CC(C)=CC=C21 FCTMZZUXBMQAER-UHFFFAOYSA-N 0.000 description 2
- XXVAZHMAHYNQBC-UHFFFAOYSA-N 7-methylsulfanyl-1,2,3,4-tetrahydroisoquinoline Chemical compound C1CNCC2=CC(SC)=CC=C21 XXVAZHMAHYNQBC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PJWWRFATQTVXHA-UHFFFAOYSA-N Cyclohexylaminopropanesulfonic acid Chemical compound OS(=O)(=O)CCCNC1CCCCC1 PJWWRFATQTVXHA-UHFFFAOYSA-N 0.000 description 2
- CEIXWJHURKEBMQ-UHFFFAOYSA-N Heliamine Chemical compound C1CNCC2=C1C=C(OC)C(OC)=C2 CEIXWJHURKEBMQ-UHFFFAOYSA-N 0.000 description 2
- WRWOASJVVAVJHL-UHFFFAOYSA-N [2-(6-methoxy-3,4-dihydro-1h-isoquinolin-2-yl)-2-oxoethyl]phosphonic acid Chemical compound C1N(C(=O)CP(O)(O)=O)CCC2=CC(OC)=CC=C21 WRWOASJVVAVJHL-UHFFFAOYSA-N 0.000 description 2
- 229960003767 alanine Drugs 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KHWCYOOXWWVZOY-UHFFFAOYSA-N bis(2-hydroxyethyl)sulfamic acid;sulfo hydrogen sulfate Chemical compound OS(=O)(=O)OS(O)(=O)=O.OCCN(S(O)(=O)=O)CCO KHWCYOOXWWVZOY-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- XVOYSCVBGLVSOL-UHFFFAOYSA-N cysteic acid Chemical compound OC(=O)C(N)CS(O)(=O)=O XVOYSCVBGLVSOL-UHFFFAOYSA-N 0.000 description 2
- WSYUEVRAMDSJKL-UHFFFAOYSA-N ethanolamine-o-sulfate Chemical compound NCCOS(O)(=O)=O WSYUEVRAMDSJKL-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- UNNFEYPNQVSVJX-UHFFFAOYSA-N pentane-3-sulfonic acid Chemical compound CCC(CC)S(O)(=O)=O UNNFEYPNQVSVJX-UHFFFAOYSA-N 0.000 description 2
- 229960005190 phenylalanine Drugs 0.000 description 2
- HNDXKIMMSFCCFW-UHFFFAOYSA-N propane-2-sulphonic acid Chemical compound CC(C)S(O)(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- MQEDXLHIUBFSML-UHFFFAOYSA-M sodium;3-aminopropyl sulfate Chemical compound [Na+].NCCCOS([O-])(=O)=O MQEDXLHIUBFSML-UHFFFAOYSA-M 0.000 description 2
- MWEMXEWFLIDTSJ-UHFFFAOYSA-M sodium;3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCN1CCOCC1 MWEMXEWFLIDTSJ-UHFFFAOYSA-M 0.000 description 2
- GEDBQJUJNQVBHE-UHFFFAOYSA-M sodium;4-hydroxybutane-1-sulfonate Chemical compound [Na+].OCCCCS([O-])(=O)=O GEDBQJUJNQVBHE-UHFFFAOYSA-M 0.000 description 2
- KQFAFFYKLIBKDE-UHFFFAOYSA-M sodium;ethanesulfonate Chemical compound [Na+].CCS([O-])(=O)=O KQFAFFYKLIBKDE-UHFFFAOYSA-M 0.000 description 2
- ROBLTDOHDSGGDT-UHFFFAOYSA-M sodium;pentane-1-sulfonate Chemical compound [Na+].CCCCCS([O-])(=O)=O ROBLTDOHDSGGDT-UHFFFAOYSA-M 0.000 description 2
- NPAWNPCNZAPTKA-UHFFFAOYSA-M sodium;propane-1-sulfonate Chemical compound [Na+].CCCS([O-])(=O)=O NPAWNPCNZAPTKA-UHFFFAOYSA-M 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 229960003080 taurine Drugs 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 0 *C(C(C(*)(F)F)(F)F)(F)F Chemical compound *C(C(C(*)(F)F)(F)F)(F)F 0.000 description 1
- LZXQFYUUMWVPQK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-1-amine Chemical compound C1=CC=C2C(N)NCCC2=C1 LZXQFYUUMWVPQK-UHFFFAOYSA-N 0.000 description 1
- BRPFEQDYPUVJAP-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-7-ylmethanamine Chemical compound C1CNCC2=CC(CN)=CC=C21 BRPFEQDYPUVJAP-UHFFFAOYSA-N 0.000 description 1
- JIIYMCJTNBTCMR-UHFFFAOYSA-N CC(C(C(O)=O)(F)F)(C(C(O)=O)(F)F)C(F)(F)F Chemical compound CC(C(C(O)=O)(F)F)(C(C(O)=O)(F)F)C(F)(F)F JIIYMCJTNBTCMR-UHFFFAOYSA-N 0.000 description 1
- FOXFUGCJJRDBNG-UHFFFAOYSA-N Cc(c1c2cccn1)ccc2Cl Chemical compound Cc(c1c2cccn1)ccc2Cl FOXFUGCJJRDBNG-UHFFFAOYSA-N 0.000 description 1
- BUJJZEQSBUFPMZ-UHFFFAOYSA-N OS(Cc(cc(c1c2cccn1)Br)c2Br)(=O)=O Chemical compound OS(Cc(cc(c1c2cccn1)Br)c2Br)(=O)=O BUJJZEQSBUFPMZ-UHFFFAOYSA-N 0.000 description 1
- HVFGFAAYRDAYDB-UHFFFAOYSA-N OS(NC1=CCCCC1)(=O)=O Chemical compound OS(NC1=CCCCC1)(=O)=O HVFGFAAYRDAYDB-UHFFFAOYSA-N 0.000 description 1
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- ABXZOXDTHTTZJW-UHFFFAOYSA-N norlaudanosoline Chemical compound C1=C(O)C(O)=CC=C1CC1C2=CC(O)=C(O)C=C2CCN1 ABXZOXDTHTTZJW-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13554599P | 1999-05-24 | 1999-05-24 | |
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| PCT/CA2000/000607 WO2000071101A2 (en) | 1999-05-24 | 2000-05-24 | Methods and compounds for inhibiting amyloid deposits |
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| NZ (3) | NZ541238A (https=) |
| WO (1) | WO2000071101A2 (https=) |
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-
2000
- 2000-05-23 US US09/576,677 patent/US6562836B1/en not_active Expired - Fee Related
- 2000-05-24 HK HK03100829.4A patent/HK1050133A1/zh unknown
- 2000-05-24 MX MXPA01011989A patent/MXPA01011989A/es not_active Application Discontinuation
- 2000-05-24 CN CNB008107203A patent/CN100435785C/zh not_active Expired - Fee Related
- 2000-05-24 JP JP2000619408A patent/JP2003500350A/ja active Pending
- 2000-05-24 DE DE60044365T patent/DE60044365D1/de not_active Expired - Lifetime
- 2000-05-24 CA CA002684016A patent/CA2684016A1/en not_active Abandoned
- 2000-05-24 IL IL14668100A patent/IL146681A0/xx active IP Right Grant
- 2000-05-24 NZ NZ541238A patent/NZ541238A/en not_active IP Right Cessation
- 2000-05-24 NZ NZ566739A patent/NZ566739A/en not_active IP Right Cessation
- 2000-05-24 AT AT00930923T patent/ATE466571T1/de not_active IP Right Cessation
- 2000-05-24 NZ NZ552354A patent/NZ552354A/en not_active IP Right Cessation
- 2000-05-24 EP EP00930923A patent/EP1227803B1/en not_active Expired - Lifetime
- 2000-05-24 CA CA002373093A patent/CA2373093C/en not_active Expired - Fee Related
- 2000-05-24 WO PCT/CA2000/000607 patent/WO2000071101A2/en not_active Ceased
- 2000-05-24 AU AU49050/00A patent/AU4905000A/en not_active Abandoned
-
2001
- 2001-11-22 IL IL146681A patent/IL146681A/en not_active IP Right Cessation
-
2003
- 2003-05-02 US US10/429,198 patent/US7393875B2/en not_active Expired - Fee Related
-
2007
- 2007-01-03 IL IL180523A patent/IL180523A0/en unknown
-
2008
- 2008-05-22 US US12/125,842 patent/US7786174B2/en not_active Expired - Fee Related
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