AU654049B2 - Novel 7-substituted-9-(substituted amino)-6-demethyl-6-deoxytetracyclines - Google Patents
Novel 7-substituted-9-(substituted amino)-6-demethyl-6-deoxytetracyclines Download PDFInfo
- Publication number
- AU654049B2 AU654049B2 AU26183/92A AU2618392A AU654049B2 AU 654049 B2 AU654049 B2 AU 654049B2 AU 26183/92 A AU26183/92 A AU 26183/92A AU 2618392 A AU2618392 A AU 2618392A AU 654049 B2 AU654049 B2 AU 654049B2
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- Australia
- Prior art keywords
- alkyl
- amino
- group
- branched
- straight
- 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.)
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- 238000000034 method Methods 0.000 claims abstract description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 154
- 150000001875 compounds Chemical class 0.000 claims abstract 24
- 239000004098 Tetracycline Substances 0.000 claims abstract 2
- 230000000694 effects Effects 0.000 claims abstract 2
- 239000000543 intermediate Substances 0.000 claims abstract 2
- 238000001228 spectrum Methods 0.000 claims abstract 2
- 235000019364 tetracycline Nutrition 0.000 claims abstract 2
- 150000003522 tetracyclines Chemical class 0.000 claims abstract 2
- 229940040944 tetracyclines Drugs 0.000 claims abstract 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims 419
- -1 monosubstituted amino Chemical group 0.000 claims 409
- 229910052717 sulfur Inorganic materials 0.000 claims 358
- 229910052711 selenium Inorganic materials 0.000 claims 321
- 125000003118 aryl group Chemical group 0.000 claims 264
- 229920006395 saturated elastomer Chemical group 0.000 claims 190
- 229910052739 hydrogen Inorganic materials 0.000 claims 176
- 239000001257 hydrogen Substances 0.000 claims 176
- 125000005843 halogen group Chemical group 0.000 claims 174
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 154
- 238000006467 substitution reaction Methods 0.000 claims 153
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 149
- 125000005605 benzo group Chemical group 0.000 claims 138
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 128
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 125
- 125000004093 cyano group Chemical group *C#N 0.000 claims 121
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 115
- 125000000217 alkyl group Chemical group 0.000 claims 115
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 115
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 113
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 109
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 101
- 229910052760 oxygen Inorganic materials 0.000 claims 100
- 125000000623 heterocyclic group Chemical group 0.000 claims 88
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 84
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 80
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 79
- 125000003710 aryl alkyl group Chemical group 0.000 claims 75
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 75
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 68
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 63
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 59
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 55
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 54
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 54
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 51
- 125000004344 phenylpropyl group Chemical group 0.000 claims 45
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 42
- 125000003435 aroyl group Chemical group 0.000 claims 41
- 125000003282 alkyl amino group Chemical group 0.000 claims 40
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 38
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 31
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 30
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 28
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 28
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 27
- 125000002252 acyl group Chemical group 0.000 claims 27
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 25
- 125000002757 morpholinyl group Chemical group 0.000 claims 25
- 125000003545 alkoxy group Chemical group 0.000 claims 24
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 23
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 23
- 229910052736 halogen Inorganic materials 0.000 claims 21
- 150000002367 halogens Chemical class 0.000 claims 21
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 20
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims 20
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 19
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 19
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims 19
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 18
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 16
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 15
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 15
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 15
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 14
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 14
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 13
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 12
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 12
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 12
- 125000005252 haloacyl group Chemical group 0.000 claims 12
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 12
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 12
- 125000004429 atom Chemical group 0.000 claims 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 11
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 10
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 10
- 125000004423 acyloxy group Chemical group 0.000 claims 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 10
- 239000000039 congener Substances 0.000 claims 10
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 10
- 239000002184 metal Chemical class 0.000 claims 10
- 230000003287 optical effect Effects 0.000 claims 10
- 239000001301 oxygen Substances 0.000 claims 10
- ONIBWKKTOPOVIA-UHFFFAOYSA-M prolinate Chemical compound [O-]C(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-M 0.000 claims 10
- 125000006628 propoxycarbonylamino group Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 239000011593 sulfur Substances 0.000 claims 10
- 229920002554 vinyl polymer Polymers 0.000 claims 10
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 9
- 229960002449 glycine Drugs 0.000 claims 9
- 235000013905 glycine and its sodium salt Nutrition 0.000 claims 9
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 8
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 claims 8
- 239000002253 acid Substances 0.000 claims 7
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 7
- 150000002431 hydrogen Chemical group 0.000 claims 7
- 229910052740 iodine Inorganic materials 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims 6
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 5
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 239000011737 fluorine Substances 0.000 claims 5
- 229940060037 fluorine Drugs 0.000 claims 5
- 235000019000 fluorine Nutrition 0.000 claims 5
- 239000011630 iodine Substances 0.000 claims 5
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 claims 4
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims 4
- 125000005916 2-methylpentyl group Chemical group 0.000 claims 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 229940124277 aminobutyric acid Drugs 0.000 claims 3
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 3
- IVFLPPKNEWVNFG-UHFFFAOYSA-N tetracene-1-carboxamide Chemical compound C1=CC=C2C=C(C=C3C(C(=O)N)=CC=CC3=C3)C3=CC2=C1 IVFLPPKNEWVNFG-UHFFFAOYSA-N 0.000 claims 3
- 241001465754 Metazoa Species 0.000 claims 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 2
- 125000003943 azolyl group Chemical group 0.000 claims 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 2
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 claims 2
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 claims 2
- DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000002981 3-(trifluoromethyl)benzoyl group Chemical group FC(C=1C=C(C(=O)*)C=CC1)(F)F 0.000 claims 1
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims 1
- 241000208140 Acer Species 0.000 claims 1
- 101150058765 BACE1 gene Proteins 0.000 claims 1
- XDVCLKFLRAWGIT-UHFFFAOYSA-N C1C2CC3=CC=CC(O)=C3C(=O)C2=C(O)C2(O)C1C(N(C)C)C(O)=C(C(N)=O)C2=O Chemical compound C1C2CC3=CC=CC(O)=C3C(=O)C2=C(O)C2(O)C1C(N(C)C)C(O)=C(C(N)=O)C2=O XDVCLKFLRAWGIT-UHFFFAOYSA-N 0.000 claims 1
- 125000006414 CCl Chemical group ClC* 0.000 claims 1
- 101100300757 Caenorhabditis elegans rab-3 gene Proteins 0.000 claims 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- 241000820057 Ithone Species 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 208000013840 Non-involuting congenital hemangioma Diseases 0.000 claims 1
- RFSXUZYKRDCQTD-UHFFFAOYSA-N S(=O)(=O)(O)O.COC(N)=O Chemical compound S(=O)(=O)(O)O.COC(N)=O RFSXUZYKRDCQTD-UHFFFAOYSA-N 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 150000001266 acyl halides Chemical class 0.000 claims 1
- 125000005336 allyloxy group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 235000015278 beef Nutrition 0.000 claims 1
- HDWIHXWEUNVBIY-UHFFFAOYSA-N bendroflumethiazidum Chemical group C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2CC1=CC=CC=C1 HDWIHXWEUNVBIY-UHFFFAOYSA-N 0.000 claims 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000006309 butyl amino group Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 101150113965 carH gene Proteins 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000004695 complexes Chemical class 0.000 claims 1
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- DBPFRRFGLYGEJI-UHFFFAOYSA-N ethyl glyoxylate Chemical compound CCOC(=O)C=O DBPFRRFGLYGEJI-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 229910001960 metal nitrate Inorganic materials 0.000 claims 1
- 125000006626 methoxycarbonylamino group Chemical group 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 claims 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims 1
- 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- OCAAZRFBJBEVPS-UHFFFAOYSA-N prop-2-enyl carbamate Chemical compound NC(=O)OCC=C OCAAZRFBJBEVPS-UHFFFAOYSA-N 0.000 claims 1
- 125000006308 propyl amino group Chemical group 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- 150000003461 sulfonyl halides Chemical class 0.000 claims 1
- ZGRCCSGEDQBOMU-UHFFFAOYSA-N sulfuric acid tetracene-2-carboxamide Chemical compound S(=O)(=O)(O)O.C1=C(C=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)C(=O)N ZGRCCSGEDQBOMU-UHFFFAOYSA-N 0.000 claims 1
- ARGOFCSACXCMNN-UHFFFAOYSA-N tetracene-2-carboxamide Chemical compound C1=CC=CC2=CC3=CC4=CC(C(=O)N)=CC=C4C=C3C=C21 ARGOFCSACXCMNN-UHFFFAOYSA-N 0.000 claims 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
- C07C237/26—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton of a ring being part of a condensed ring system formed by at least four rings, e.g. tetracycline
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/16—Amides, e.g. hydroxamic acids
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
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- C—CHEMISTRY; METALLURGY
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
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- C—CHEMISTRY; METALLURGY
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C—CHEMISTRY; METALLURGY
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/44—Naphthacenes; Hydrogenated naphthacenes
- C07C2603/46—1,4,4a,5,5a,6,11,12a- Octahydronaphthacenes, e.g. tetracyclines
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- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
- Pyrrole Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Moulding By Coating Moulds (AREA)
- Hydrogenated Pyridines (AREA)
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- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (2)
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| US77157691A | 1991-10-04 | 1991-10-04 | |
| US771576 | 1991-10-04 |
Publications (2)
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| AU2618392A AU2618392A (en) | 1993-04-08 |
| AU654049B2 true AU654049B2 (en) | 1994-10-20 |
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| AU26183/92A Expired AU654049B2 (en) | 1991-10-04 | 1992-10-02 | Novel 7-substituted-9-(substituted amino)-6-demethyl-6-deoxytetracyclines |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU674690B2 (en) * | 1992-08-13 | 1997-01-09 | Wyeth Holdings Corporation | 7-(substituted)-9-{(substituted glycyl)amido}-6-demethyl-6- deoxytetracyclines |
| AU674689B2 (en) * | 1992-08-13 | 1997-01-09 | Wyeth Holdings Corporation | Novel method of producing 7-(substituted)-9-{(substituted glycyl)amido}-6-demethyl-6-deoxytetracyclines |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5420272A (en) * | 1992-08-13 | 1995-05-30 | American Cyanamid Company | 7-(substituted)-8-(substituted)-9-](substituted glycyl)amido]-6-demethyl-6-deoxytetracyclines |
| WO1995022529A1 (en) * | 1994-02-17 | 1995-08-24 | Pfizer Inc. | 9-(substituted amino)-alpha-6-deoxy-5-oxy tetracycline derivatives, their preparation and their use as antibiotics |
| EA016099B1 (ru) | 1999-09-14 | 2012-02-28 | Трастис Оф Тафтс Коллидж | Замещенный аналог тетрациклина (варианты) и способ получения замещенного аналога тетрациклина |
| US8106225B2 (en) | 1999-09-14 | 2012-01-31 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
| IL151971A0 (en) * | 2000-03-31 | 2003-04-10 | Tufts College | 7-and 9-carbamate, urea, thiourea, thiocarbabamate, and heteroaryl-amino substituted tetracycline compounds |
| EP2308863A1 (en) * | 2000-05-15 | 2011-04-13 | Paratek Pharmaceuticals, Inc. | 7-substituted fused ring tetracycline compounds |
| EA013908B1 (ru) * | 2000-07-07 | 2010-08-30 | Трастис Оф Тафтс Коллидж | Замещенные соединения миноциклина (варианты), фармацевтическая композиция и способ лечения чувствительного к тетрациклину состояния млекопитающего |
| US7094806B2 (en) | 2000-07-07 | 2006-08-22 | Trustees Of Tufts College | 7, 8 and 9-substituted tetracycline compounds |
| EA201000388A1 (ru) | 2001-03-13 | 2010-10-29 | Пэрэтек Фамэсьютикэлс, Инк. | Замещенные соединения тетрациклина (варианты), фармацевтическая композиция и способ лечения чувствительного к тетрациклину состояния субъекта |
| US7553828B2 (en) | 2001-03-13 | 2009-06-30 | Paratek Pharmaceuticals, Inc. | 9-aminomethyl substituted minocycline compounds |
| WO2002072506A2 (en) | 2001-03-13 | 2002-09-19 | Paratek Pharmaceuticals, Inc. | 7-pyrollyl tetracycline compounds and methods of use thereof |
| EP1241160A1 (en) | 2001-03-13 | 2002-09-18 | Glaxo Group Limited | Tetracycline derivatives and their use as antibiotic agents |
| EP2186793A1 (en) * | 2001-04-24 | 2010-05-19 | Paratek Pharmaceuticals, Inc. | Substituted Tetracycline Compounds |
| US20040063674A1 (en) | 2001-07-13 | 2004-04-01 | Levy Stuart B. | Tetracycline compounds having target therapeutic activities |
| WO2003055441A2 (en) | 2001-08-02 | 2003-07-10 | Paratek Pharmaceuticals, Inc. | Medicaments |
| AU2003235759A1 (en) | 2002-01-08 | 2003-07-24 | Paratek Pharmaceuticals, Inc. | 4-dedimethylamino tetracycline compounds |
| EP1482926A4 (en) * | 2002-03-08 | 2006-04-12 | Paratek Pharm Innc | AMINO METHYL SUBSTITUTED TETRACYCLINE COMPOUNDS |
| EP2319828A3 (en) | 2003-07-09 | 2011-07-06 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| UA83266C2 (en) * | 2003-12-08 | 2008-06-25 | Уайет | Oxazole derivatives of tetracyclines |
| PL1753713T3 (pl) | 2004-05-21 | 2017-02-28 | President And Fellows Of Harvard College | Synteza tetracyklin oraz ich analogów |
| PA8652001A1 (es) | 2004-11-05 | 2006-10-13 | Wyeth Corp | Metabolitos glucuronidos de tigeciclina y epimeros de los mismos |
| AR057649A1 (es) | 2005-05-27 | 2007-12-12 | Wyeth Corp | Formas solidas cristalinas de tigeciclina y metodos para preparar las mismas |
| AU2006285043A1 (en) * | 2005-08-31 | 2007-03-08 | Wyeth | 9-aminocarbonylsubstituted derivatives of glycylcyclines |
| AU2007249695A1 (en) | 2006-05-15 | 2007-11-22 | Paratek Pharmaceuticals, Inc. | Methods of regulating expression of genes or of gene products using substituted tetracycline compounds |
| CN101868469B (zh) | 2007-11-29 | 2014-04-02 | 埃科特莱茵药品有限公司 | 膦酸衍生物及其作为p2y12受体拮抗剂 |
| PT2271348T (pt) | 2008-03-28 | 2018-04-16 | Paratek Pharm Innc | Formulação de comprimido oral de composto de tetraciclina |
| ITMI20080807A1 (it) | 2008-05-05 | 2009-11-06 | Antibioticos Spa | Procedimento per la preparazione di tigeciclina in forma amorfa |
| TW202021946A (zh) | 2008-05-19 | 2020-06-16 | 美商派洛泰克藥物股份有限公司 | 四環素化合物之甲苯磺酸鹽及同素異形體 |
| MX358961B (es) * | 2008-08-08 | 2018-09-10 | Tetraphase Pharmaceuticals Inc Star | Compuestos de tetraciclina sustituidos con fluor en c7. |
| EP2424834B1 (en) | 2009-04-30 | 2018-07-11 | President and Fellows of Harvard College | Synthesis of tetracyclines and intermediates thereof |
| ES2627772T3 (es) | 2009-05-08 | 2017-07-31 | Tetraphase Pharmaceuticals, Inc. | Compuestos de tetraciclina |
| CN105622496B (zh) | 2009-08-28 | 2019-03-05 | 四相制药公司 | 四环素类化合物 |
| ES2715551T3 (es) | 2010-05-12 | 2019-06-04 | The Medicines Company San Diego Llc | Composiciones de tetraciclina |
| CN103635456B (zh) * | 2011-07-26 | 2016-03-09 | 山东亨利医药科技有限责任公司 | 替加环素衍生物 |
| SG10201801703RA (en) | 2012-08-31 | 2018-04-27 | Tetraphase Pharmaceuticals Inc | Tetracycline compounds |
| EP3068370A2 (en) | 2013-11-12 | 2016-09-21 | Galenicum Health S.L. | Stable pharmaceutical compositions |
| MA46567A (fr) | 2016-10-19 | 2019-08-28 | Tetraphase Pharmaceuticals Inc | Formes cristallines de l'éravacycline |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3338963A (en) * | 1960-10-28 | 1967-08-29 | American Cyanamid Co | Tetracycline compounds |
| US3579579A (en) * | 1968-04-18 | 1971-05-18 | American Cyanamid Co | Substituted 7- and/or 9-amino-6-demethyl-6-deoxytetracyclines |
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1992
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1996
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1997
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2004
- 2004-06-25 CL CL200401623A patent/CL2004001623A1/es unknown
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2006
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- 2006-10-23 NL NL300244C patent/NL300244I2/nl unknown
- 2006-11-15 NO NO2006015C patent/NO2006015I2/no unknown
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2017
- 2017-08-01 NO NO2017037C patent/NO2017037I2/no unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3338963A (en) * | 1960-10-28 | 1967-08-29 | American Cyanamid Co | Tetracycline compounds |
| US3579579A (en) * | 1968-04-18 | 1971-05-18 | American Cyanamid Co | Substituted 7- and/or 9-amino-6-demethyl-6-deoxytetracyclines |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU674690B2 (en) * | 1992-08-13 | 1997-01-09 | Wyeth Holdings Corporation | 7-(substituted)-9-{(substituted glycyl)amido}-6-demethyl-6- deoxytetracyclines |
| AU674689B2 (en) * | 1992-08-13 | 1997-01-09 | Wyeth Holdings Corporation | Novel method of producing 7-(substituted)-9-{(substituted glycyl)amido}-6-demethyl-6-deoxytetracyclines |
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