JP2009502809A5 - - Google Patents
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- Publication number
- JP2009502809A5 JP2009502809A5 JP2008523041A JP2008523041A JP2009502809A5 JP 2009502809 A5 JP2009502809 A5 JP 2009502809A5 JP 2008523041 A JP2008523041 A JP 2008523041A JP 2008523041 A JP2008523041 A JP 2008523041A JP 2009502809 A5 JP2009502809 A5 JP 2009502809A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- dihydro
- hydrogen
- alkynyl
- alkenyl
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims 79
- 239000001257 hydrogen Substances 0.000 claims 79
- 125000000217 alkyl group Chemical group 0.000 claims 68
- -1 tetracycline compound Chemical class 0.000 claims 64
- 150000002431 hydrogen Chemical group 0.000 claims 57
- 125000003342 alkenyl group Chemical group 0.000 claims 52
- 125000000304 alkynyl group Chemical group 0.000 claims 51
- 125000003118 aryl group Chemical group 0.000 claims 46
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 44
- 125000003710 aryl alkyl group Chemical group 0.000 claims 43
- 125000003545 alkoxy group Chemical group 0.000 claims 33
- 125000004414 alkyl thio group Chemical group 0.000 claims 32
- 125000000623 heterocyclic group Chemical group 0.000 claims 32
- 229960002180 Tetracycline Drugs 0.000 claims 30
- 239000004098 Tetracycline Substances 0.000 claims 30
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 30
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 30
- 235000019364 tetracycline Nutrition 0.000 claims 30
- 229910052736 halogen Inorganic materials 0.000 claims 27
- 150000002367 halogens Chemical class 0.000 claims 27
- 125000003282 alkyl amino group Chemical group 0.000 claims 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 22
- 150000003573 thiols Chemical class 0.000 claims 22
- 239000000651 prodrug Substances 0.000 claims 21
- 229940002612 prodrugs Drugs 0.000 claims 21
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 15
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 15
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 15
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims 15
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 15
- 125000002252 acyl group Chemical group 0.000 claims 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 14
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 12
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 12
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims 11
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2H-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 claims 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 10
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 10
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims 9
- 125000004103 aminoalkyl group Chemical group 0.000 claims 9
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 9
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 9
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 8
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- OFVLGDICTFRJMM-WESIUVDSSA-N Tetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O OFVLGDICTFRJMM-WESIUVDSSA-N 0.000 claims 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 6
- 125000004442 acylamino group Chemical group 0.000 claims 6
- 125000005089 alkenylaminocarbonyl group Chemical group 0.000 claims 6
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 6
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims 6
- 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims 6
- 125000005095 alkynylaminocarbonyl group Chemical group 0.000 claims 6
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims 6
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims 6
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 6
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- 150000007942 carboxylates Chemical class 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 239000010452 phosphate Substances 0.000 claims 6
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- JWPMHRXIIOEZRU-UHFFFAOYSA-N 2,5-dihydro-1,2,4-thiadiazole Chemical compound C1NC=NS1 JWPMHRXIIOEZRU-UHFFFAOYSA-N 0.000 claims 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims 5
- 125000004946 alkenylalkyl group Chemical group 0.000 claims 5
- 125000005038 alkynylalkyl group Chemical group 0.000 claims 5
- 150000001408 amides Chemical class 0.000 claims 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 5
- 125000003435 aroyl group Chemical group 0.000 claims 5
- 125000001589 carboacyl group Chemical group 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 5
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims 5
- NJRWNWYFPOFDFN-UHFFFAOYSA-L phosphonate(2-) Chemical compound [O-][P]([O-])=O NJRWNWYFPOFDFN-UHFFFAOYSA-L 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000011780 sodium chloride Substances 0.000 claims 5
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 4
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims 3
- 125000005103 alkyl silyl group Chemical group 0.000 claims 3
- 150000001356 alkyl thiols Chemical class 0.000 claims 3
- 125000001769 aryl amino group Chemical group 0.000 claims 3
- 125000005104 aryl silyl group Chemical group 0.000 claims 3
- 125000005110 aryl thio group Chemical group 0.000 claims 3
- 150000001504 aryl thiols Chemical class 0.000 claims 3
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 3
- 201000006417 multiple sclerosis Diseases 0.000 claims 3
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 3
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims 2
- JRLFRFTXXMZSND-UHFFFAOYSA-N 1,2,4-triazoline Chemical compound C1NNC=N1 JRLFRFTXXMZSND-UHFFFAOYSA-N 0.000 claims 2
- USSYLANTAAUELR-UHFFFAOYSA-N 1,2-dihydro-1,2,4-triazine Chemical compound N1NC=NC=C1 USSYLANTAAUELR-UHFFFAOYSA-N 0.000 claims 2
- RMQOXNXLVICLNK-UHFFFAOYSA-N 1,4-dihydro-1,3,5-triazine Chemical compound C1NC=NC=N1 RMQOXNXLVICLNK-UHFFFAOYSA-N 0.000 claims 2
- PNJBXRVMRQIFKK-UHFFFAOYSA-N 1,4-dihydrotriazine Chemical compound C1C=CNN=N1 PNJBXRVMRQIFKK-UHFFFAOYSA-N 0.000 claims 2
- CQHHFSBXAPCQFG-UHFFFAOYSA-N 2,3-dihydro-1,2,4-oxadiazole Chemical compound C1NOC=N1 CQHHFSBXAPCQFG-UHFFFAOYSA-N 0.000 claims 2
- ALBVNKOEWADZPF-UHFFFAOYSA-N 2,3-dihydro-1,2,4-thiadiazole Chemical compound C1NSC=N1 ALBVNKOEWADZPF-UHFFFAOYSA-N 0.000 claims 2
- HBJUQLMVCIEESP-UHFFFAOYSA-N 2,5-dihydro-1,2,4-oxadiazole Chemical compound C1NC=NO1 HBJUQLMVCIEESP-UHFFFAOYSA-N 0.000 claims 2
- IIATVLXXAYLQIZ-UHFFFAOYSA-N 2,5-dihydro-1,2,4-triazine Chemical compound C1C=NNC=N1 IIATVLXXAYLQIZ-UHFFFAOYSA-N 0.000 claims 2
- KWIVRAVCZJXOQC-UHFFFAOYSA-N 3H-oxathiazole Chemical compound N1SOC=C1 KWIVRAVCZJXOQC-UHFFFAOYSA-N 0.000 claims 2
- RLDJTWKQIMTLEN-UHFFFAOYSA-N 5,6-dihydro-1,4,2-dioxazine Chemical compound C1CON=CO1 RLDJTWKQIMTLEN-UHFFFAOYSA-N 0.000 claims 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N Pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000002458 infectious Effects 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
- 229960001663 sulfanilamide Drugs 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- MKVBVTOSWPBSNC-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,2,4-triazine Chemical compound C1NNC=CN1 MKVBVTOSWPBSNC-UHFFFAOYSA-N 0.000 claims 1
- FUIQANIDAMJELP-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,3,5-triazine Chemical compound C1NCN=CN1 FUIQANIDAMJELP-UHFFFAOYSA-N 0.000 claims 1
- OQJVXNHMUWQQEW-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrazine Chemical compound C1CNC=CN1 OQJVXNHMUWQQEW-UHFFFAOYSA-N 0.000 claims 1
- JQIZHNLEFQMDCQ-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridazine Chemical compound C1CC=CNN1 JQIZHNLEFQMDCQ-UHFFFAOYSA-N 0.000 claims 1
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims 1
- JZTKNVMVUVSGJF-UHFFFAOYSA-N 1,2,3,5-oxatriazole Chemical compound C=1N=NON=1 JZTKNVMVUVSGJF-UHFFFAOYSA-N 0.000 claims 1
- XLEDBLKSWOYHES-UHFFFAOYSA-N 1,2,3,5-thiatriazole Chemical compound C=1N=NSN=1 XLEDBLKSWOYHES-UHFFFAOYSA-N 0.000 claims 1
- LVEKWSMAGKNFCF-UHFFFAOYSA-N 1,2,3,6-tetrahydro-1,2,4-triazine Chemical compound C1NNCN=C1 LVEKWSMAGKNFCF-UHFFFAOYSA-N 0.000 claims 1
- IOLQWFQLCNMKAZ-UHFFFAOYSA-N 1,2,3,6-tetrahydropyrazine Chemical compound C1CN=CCN1 IOLQWFQLCNMKAZ-UHFFFAOYSA-N 0.000 claims 1
- WNSPCCWAAVHWIM-UHFFFAOYSA-N 1,2,3,6-tetrahydropyridazine Chemical compound C1NNCC=C1 WNSPCCWAAVHWIM-UHFFFAOYSA-N 0.000 claims 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- GBLQGXFTPLQBTA-UHFFFAOYSA-N 1,2,3-triazoline Chemical compound C1CN=NN1 GBLQGXFTPLQBTA-UHFFFAOYSA-N 0.000 claims 1
- BLWJJPNXUDWVCG-UHFFFAOYSA-N 1,2,4-oxadiazolidine Chemical compound C1NCON1 BLWJJPNXUDWVCG-UHFFFAOYSA-N 0.000 claims 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims 1
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims 1
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims 1
- WNBQDDAKLKODPH-UHFFFAOYSA-N 1,2,4-triazolidine Chemical compound C1NCNN1 WNBQDDAKLKODPH-UHFFFAOYSA-N 0.000 claims 1
- OYEHFRMFJLFNSD-UHFFFAOYSA-N 1,2,5,6-tetrahydro-1,2,4-triazine Chemical compound C1CN=CNN1 OYEHFRMFJLFNSD-UHFFFAOYSA-N 0.000 claims 1
- OHFXUPDPPRJZES-UHFFFAOYSA-N 1,2,5,6-tetrahydropyrimidine Chemical compound C1CC=NCN1 OHFXUPDPPRJZES-UHFFFAOYSA-N 0.000 claims 1
- QYMGRIFMUQCAJW-UHFFFAOYSA-N 1,2-dihydropyrazine Chemical compound C1NC=CN=C1 QYMGRIFMUQCAJW-UHFFFAOYSA-N 0.000 claims 1
- BKWQKVJYXODDAC-UHFFFAOYSA-N 1,2-dihydropyridazine Chemical compound N1NC=CC=C1 BKWQKVJYXODDAC-UHFFFAOYSA-N 0.000 claims 1
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 claims 1
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 claims 1
- NTSJGNVMDZAPJE-UHFFFAOYSA-N 1,2-dihydrotriazine Chemical compound N1NN=CC=C1 NTSJGNVMDZAPJE-UHFFFAOYSA-N 0.000 claims 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 1
- SKLDBJVFTOQKHE-UHFFFAOYSA-N 1,3,4-oxadiazolidine Chemical compound C1NNCO1 SKLDBJVFTOQKHE-UHFFFAOYSA-N 0.000 claims 1
- NWEFQXYVAUNGNI-UHFFFAOYSA-N 1,3,4-oxathiazolidine Chemical compound C1NSCO1 NWEFQXYVAUNGNI-UHFFFAOYSA-N 0.000 claims 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims 1
- BRQBVEHLEITSPT-UHFFFAOYSA-N 1,3,4-thiadiazolidine Chemical compound C1NNCS1 BRQBVEHLEITSPT-UHFFFAOYSA-N 0.000 claims 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-Triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims 1
- UKOMUVPFRFPHDS-UHFFFAOYSA-N 1,4,2-dioxazine Chemical compound O1C=CON=C1 UKOMUVPFRFPHDS-UHFFFAOYSA-N 0.000 claims 1
- DDGWEFMIIOIMEF-UHFFFAOYSA-N 1,4,2-dithiazine Chemical compound S1C=CSN=C1 DDGWEFMIIOIMEF-UHFFFAOYSA-N 0.000 claims 1
- FMYSHKHSQFXYRS-UHFFFAOYSA-N 1,4,2-oxathiazine Chemical compound O1C=CSC=N1 FMYSHKHSQFXYRS-UHFFFAOYSA-N 0.000 claims 1
- GWOPJRXEMFYVQP-UHFFFAOYSA-N 1,4,2-oxathiazolidine Chemical compound C1NOCS1 GWOPJRXEMFYVQP-UHFFFAOYSA-N 0.000 claims 1
- BGMLUCPALPKNOV-UHFFFAOYSA-N 1,4,5,6-tetrahydropyridazine Chemical compound C1CNN=CC1 BGMLUCPALPKNOV-UHFFFAOYSA-N 0.000 claims 1
- VBXZSFNZVNDOPB-UHFFFAOYSA-N 1,4,5,6-tetrahydropyrimidine Chemical compound C1CNC=NC1 VBXZSFNZVNDOPB-UHFFFAOYSA-N 0.000 claims 1
- XYNBEQAWBCGIMD-UHFFFAOYSA-N 1,4-dihydropyrazine Chemical compound N1C=CNC=C1 XYNBEQAWBCGIMD-UHFFFAOYSA-N 0.000 claims 1
- HZVGMPJZVYBYEK-UHFFFAOYSA-N 1,4-dihydropyridazine Chemical compound C1C=CNN=C1 HZVGMPJZVYBYEK-UHFFFAOYSA-N 0.000 claims 1
- OKGNMRKOGWTADH-UHFFFAOYSA-N 1,4-dihydropyrimidine Chemical compound C1C=CNC=N1 OKGNMRKOGWTADH-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- LOZWAPSEEHRYPG-UHFFFAOYSA-N 1,4-dithiane Chemical compound C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 claims 1
- AKAIWNDBVZJOAJ-UHFFFAOYSA-N 1,4-dithiine Chemical compound S1C=CSC=C1 AKAIWNDBVZJOAJ-UHFFFAOYSA-N 0.000 claims 1
- JBYHSSAVUBIJMK-UHFFFAOYSA-N 1,4-oxathiane Chemical compound C1CSCCO1 JBYHSSAVUBIJMK-UHFFFAOYSA-N 0.000 claims 1
- CPRVXMQHLPTWLY-UHFFFAOYSA-N 1,4-oxathiine Chemical compound O1C=CSC=C1 CPRVXMQHLPTWLY-UHFFFAOYSA-N 0.000 claims 1
- YYSJNACCWYRKMK-UHFFFAOYSA-N 1,5-didehydro-2,4-dihydroimidazol-1-ium-3-ide Chemical compound C1[N-]C[N+]#C1 YYSJNACCWYRKMK-UHFFFAOYSA-N 0.000 claims 1
- QFXRFFKVJYBGLQ-UHFFFAOYSA-N 1,6-dihydro-1,2,4-triazine Chemical compound C1NN=CN=C1 QFXRFFKVJYBGLQ-UHFFFAOYSA-N 0.000 claims 1
- ZEFGUWRQFNTGGX-UHFFFAOYSA-N 1,6-dihydropyridazine Chemical compound C1NN=CC=C1 ZEFGUWRQFNTGGX-UHFFFAOYSA-N 0.000 claims 1
- DWKUKQRKVCMOLP-UHFFFAOYSA-N 1-piperideine Chemical compound C1CCN=CC1 DWKUKQRKVCMOLP-UHFFFAOYSA-N 0.000 claims 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims 1
- HGYGEJZLUZEDIH-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1,2,4-triazine Chemical compound C1NCC=NN1 HGYGEJZLUZEDIH-UHFFFAOYSA-N 0.000 claims 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-Dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims 1
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 claims 1
- GRYYTSJXIFGRAL-UHFFFAOYSA-N 2,3-dihydro-1,2,4-triazine Chemical compound C1NN=CC=N1 GRYYTSJXIFGRAL-UHFFFAOYSA-N 0.000 claims 1
- FJRPOHLDJUJARI-UHFFFAOYSA-N 2,3-dihydro-1,2-oxazole Chemical compound C1NOC=C1 FJRPOHLDJUJARI-UHFFFAOYSA-N 0.000 claims 1
- YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 claims 1
- RZQQXRVPPOOCQR-UHFFFAOYSA-N 2,3-dihydro-1,3,4-oxadiazole Chemical compound C1NN=CO1 RZQQXRVPPOOCQR-UHFFFAOYSA-N 0.000 claims 1
- VKRGLHLCUMMXHA-UHFFFAOYSA-N 2,3-dihydro-1,3,4-thiadiazole Chemical compound C1NN=CS1 VKRGLHLCUMMXHA-UHFFFAOYSA-N 0.000 claims 1
- OYJGEOAXBALSMM-UHFFFAOYSA-N 2,3-dihydro-1,3-thiazole Chemical compound C1NC=CS1 OYJGEOAXBALSMM-UHFFFAOYSA-N 0.000 claims 1
- AXYMXGSRCWCVIK-UHFFFAOYSA-N 2,3-dihydro-1,4,2-dioxazine Chemical compound C1NOC=CO1 AXYMXGSRCWCVIK-UHFFFAOYSA-N 0.000 claims 1
- RTQGSDHQFAONPG-UHFFFAOYSA-N 2,3-dihydro-1,4,3-oxathiazine Chemical compound C1NSC=CO1 RTQGSDHQFAONPG-UHFFFAOYSA-N 0.000 claims 1
- LWTIGYSPAXKMDG-UHFFFAOYSA-N 2,3-dihydro-1H-imidazole Chemical compound C1NC=CN1 LWTIGYSPAXKMDG-UHFFFAOYSA-N 0.000 claims 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1H-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims 1
- WUCWFMVYIKMAPG-UHFFFAOYSA-N 2,3-dihydropyrazine Chemical compound C1CN=CC=N1 WUCWFMVYIKMAPG-UHFFFAOYSA-N 0.000 claims 1
- NZHIIDNOLFOHSG-UHFFFAOYSA-N 2,3-dihydropyridine Chemical compound C1CN=CC=C1 NZHIIDNOLFOHSG-UHFFFAOYSA-N 0.000 claims 1
- OFJBYLCQNJHFMI-UHFFFAOYSA-N 2,5-dihydro-1,2-oxazole Chemical compound C1ONC=C1 OFJBYLCQNJHFMI-UHFFFAOYSA-N 0.000 claims 1
- UPUWMQZUXFAUCJ-UHFFFAOYSA-N 2,5-dihydro-1,2-thiazole Chemical compound C1SNC=C1 UPUWMQZUXFAUCJ-UHFFFAOYSA-N 0.000 claims 1
- JLPUISACQXFVRC-UHFFFAOYSA-N 2,5-dihydro-1,3-thiazole Chemical compound C1SCN=C1 JLPUISACQXFVRC-UHFFFAOYSA-N 0.000 claims 1
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1H-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 claims 1
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-
2006
- 2006-07-21 US US11/490,867 patent/US20070093455A1/en not_active Abandoned
- 2006-07-21 CA CA002616224A patent/CA2616224A1/en not_active Abandoned
- 2006-07-21 WO PCT/US2006/028676 patent/WO2007014154A2/en active Application Filing
- 2006-07-21 JP JP2008523041A patent/JP2009502809A/ja active Pending
- 2006-07-21 AU AU2006272698A patent/AU2006272698B2/en not_active Ceased
- 2006-07-21 EP EP06788310A patent/EP1910273A2/en not_active Withdrawn
-
2008
- 2008-01-15 IL IL188794A patent/IL188794A/en not_active IP Right Cessation
-
2012
- 2012-01-03 IL IL217350A patent/IL217350A0/en unknown
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