NZ244585A - 9-substituted-amino tetracycline derivatives and pharmaceutical compositions - Google Patents
9-substituted-amino tetracycline derivatives and pharmaceutical compositionsInfo
- Publication number
- NZ244585A NZ244585A NZ244585A NZ24458592A NZ244585A NZ 244585 A NZ244585 A NZ 244585A NZ 244585 A NZ244585 A NZ 244585A NZ 24458592 A NZ24458592 A NZ 24458592A NZ 244585 A NZ244585 A NZ 244585A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkyl
- group
- amino
- branched
- heteroatoms
- Prior art date
Links
- 239000004098 Tetracycline Substances 0.000 title abstract description 26
- 235000019364 tetracycline Nutrition 0.000 title abstract description 25
- 229960002180 tetracycline Drugs 0.000 title description 18
- 229930101283 tetracycline Natural products 0.000 title description 18
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 115
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 14
- -1 monosubstituted amino Chemical group 0.000 claims description 765
- 125000005842 heteroatom Chemical group 0.000 claims description 593
- 229910052717 sulfur Inorganic materials 0.000 claims description 563
- 125000000217 alkyl group Chemical group 0.000 claims description 520
- 229910052711 selenium Inorganic materials 0.000 claims description 510
- 125000003118 aryl group Chemical group 0.000 claims description 367
- 229920006395 saturated elastomer Chemical group 0.000 claims description 261
- 125000005843 halogen group Chemical group 0.000 claims description 248
- 229910052739 hydrogen Inorganic materials 0.000 claims description 247
- 239000001257 hydrogen Substances 0.000 claims description 246
- 238000006467 substitution reaction Methods 0.000 claims description 224
- 125000005605 benzo group Chemical group 0.000 claims description 181
- 125000003282 alkyl amino group Chemical group 0.000 claims description 177
- 125000003545 alkoxy group Chemical group 0.000 claims description 172
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 160
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 152
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 146
- 125000000623 heterocyclic group Chemical group 0.000 claims description 124
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 122
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 121
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 118
- 229910052760 oxygen Inorganic materials 0.000 claims description 115
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 109
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 106
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 106
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 101
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 94
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 94
- 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 description 93
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 93
- 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 description 92
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 90
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 90
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 89
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 60
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 52
- 125000003435 aroyl group Chemical group 0.000 claims description 45
- 229910052705 radium Inorganic materials 0.000 claims description 44
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 39
- 125000002252 acyl group Chemical group 0.000 claims description 37
- 125000002757 morpholinyl group Chemical group 0.000 claims description 36
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 33
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 31
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 25
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 24
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 24
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 23
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 23
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 23
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 21
- 125000005252 haloacyl group Chemical group 0.000 claims description 21
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 21
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 21
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 20
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 19
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- PINRUEQFGKWBTO-UHFFFAOYSA-N 3-methyl-5-phenyl-1,3-oxazolidin-2-imine Chemical compound O1C(=N)N(C)CC1C1=CC=CC=C1 PINRUEQFGKWBTO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 16
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- 125000004423 acyloxy group Chemical group 0.000 claims description 12
- 229920002554 vinyl polymer Polymers 0.000 claims description 12
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 11
- 229910052751 metal Chemical class 0.000 claims description 11
- 239000002184 metal Chemical class 0.000 claims description 11
- 125000006628 propoxycarbonylamino group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 6
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 6
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 6
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 claims description 6
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 claims description 5
- 125000005916 2-methylpentyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052706 scandium Inorganic materials 0.000 claims description 5
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 229910052720 vanadium Inorganic materials 0.000 claims description 5
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 claims description 3
- 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 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000005333 aroyloxy group Chemical group 0.000 claims 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 9
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 9
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 4
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 3
- 230000003287 optical effect Effects 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 2
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims 2
- 229960002449 glycine Drugs 0.000 claims 2
- 235000013905 glycine and its sodium salt Nutrition 0.000 claims 2
- 125000004385 trihaloalkyl 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
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- SILPHZBZVUMAJT-UHFFFAOYSA-N CN(C)C1C(=C(C(C2(C(=C3C(C4=C(C(=CC=C4CC3CC12)NC(C1=CC=C(C=C1)OC)=O)O)=O)O)O)=O)C(=O)N)O Chemical compound CN(C)C1C(=C(C(C2(C(=C3C(C4=C(C(=CC=C4CC3CC12)NC(C1=CC=C(C=C1)OC)=O)O)=O)O)O)=O)C(=O)N)O SILPHZBZVUMAJT-UHFFFAOYSA-N 0.000 claims 1
- DNUMBBYLGLXBTJ-UHFFFAOYSA-N Cl.C1C2CC3=CC=CC(O)=C3C(=O)C2=C(O)C2(O)C1CC(O)=C(C(=O)N)C2=O Chemical compound Cl.C1C2CC3=CC=CC(O)=C3C(=O)C2=C(O)C2(O)C1CC(O)=C(C(=O)N)C2=O DNUMBBYLGLXBTJ-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 240000007594 Oryza sativa Species 0.000 claims 1
- 235000007164 Oryza sativa Nutrition 0.000 claims 1
- 150000001266 acyl halides Chemical class 0.000 claims 1
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims 1
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 claims 1
- 125000006311 cyclobutyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical class O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 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
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229920002114 octoxynol-9 Polymers 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 235000009566 rice Nutrition 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003461 sulfonyl halides Chemical class 0.000 claims 1
- 125000004149 thio group Chemical group *S* 0.000 claims 1
- 150000003522 tetracyclines Chemical class 0.000 abstract description 18
- 229940040944 tetracyclines Drugs 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 5
- 239000000543 intermediate Substances 0.000 abstract description 4
- 238000001228 spectrum Methods 0.000 abstract description 2
- 125000004076 pyridyl group Chemical group 0.000 description 48
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 27
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 27
- 125000001041 indolyl group Chemical group 0.000 description 27
- 125000000168 pyrrolyl group Chemical group 0.000 description 27
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 27
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 27
- 125000001544 thienyl group Chemical group 0.000 description 27
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 26
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 25
- 125000002541 furyl group Chemical group 0.000 description 25
- DHIVBEZCBBHIPZ-UHFFFAOYSA-N 1-aminoimidazolidin-2-one Chemical compound NN1CCNC1=O DHIVBEZCBBHIPZ-UHFFFAOYSA-N 0.000 description 24
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 24
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 24
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 24
- 125000002883 imidazolyl group Chemical group 0.000 description 24
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 24
- 125000003373 pyrazinyl group Chemical group 0.000 description 24
- 125000003226 pyrazolyl group Chemical group 0.000 description 24
- 125000002098 pyridazinyl group Chemical group 0.000 description 24
- 125000000335 thiazolyl group Chemical group 0.000 description 24
- 125000002971 oxazolyl group Chemical group 0.000 description 23
- 125000000714 pyrimidinyl group Chemical group 0.000 description 23
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 21
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 14
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 11
- 125000005999 2-bromoethyl group Chemical group 0.000 description 11
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 11
- 125000005997 bromomethyl group Chemical group 0.000 description 11
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 11
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 11
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 11
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 11
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 11
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 9
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 8
- 125000005336 allyloxy group Chemical group 0.000 description 8
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- FFTVPQUHLQBXQZ-KVUCHLLUSA-N (4s,4as,5ar,12ar)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O FFTVPQUHLQBXQZ-KVUCHLLUSA-N 0.000 description 6
- 125000005975 2-phenylethyloxy group Chemical group 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- 229960004023 minocycline Drugs 0.000 description 6
- 230000003115 biocidal effect Effects 0.000 description 5
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 5
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 210000003705 ribosome Anatomy 0.000 description 4
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- 241000191940 Staphylococcus Species 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000006637 cyclobutyl carbonyl group Chemical group 0.000 description 3
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 description 3
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 125000003386 piperidinyl group Chemical group 0.000 description 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 3
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- 125000001241 2-phenylethylthio group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])S* 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 208000035473 Communicable disease Diseases 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 2
- 241000194017 Streptococcus Species 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000039 congener Substances 0.000 description 2
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 2
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- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- XHCNINMOALIGKM-UHFFFAOYSA-N 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetrazacyclotetradecane Chemical compound CC1CC(C)(C)NCCNC(C)CC(C)(C)NCCN1 XHCNINMOALIGKM-UHFFFAOYSA-N 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- 241000192125 Firmicutes Species 0.000 description 1
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- 239000012954 diazonium Substances 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 1
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Furan Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Moulding By Coating Moulds (AREA)
- Saccharide Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77157691A | 1991-10-04 | 1991-10-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ244585A true NZ244585A (en) | 1995-07-26 |
Family
ID=25092264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ244585A NZ244585A (en) | 1991-10-04 | 1992-10-01 | 9-substituted-amino tetracycline derivatives and pharmaceutical compositions |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP0536515B1 (enExample) |
| JP (1) | JP3186863B2 (enExample) |
| KR (1) | KR100269072B1 (enExample) |
| CN (1) | CN1048240C (enExample) |
| AT (1) | ATE211128T1 (enExample) |
| AU (1) | AU654049B2 (enExample) |
| BR (1) | BR1100853A (enExample) |
| CA (1) | CA2079692C (enExample) |
| CL (1) | CL2004001623A1 (enExample) |
| CZ (2) | CZ309397A3 (enExample) |
| DE (4) | DE122006000058I2 (enExample) |
| DK (1) | DK0536515T3 (enExample) |
| ES (1) | ES2168254T3 (enExample) |
| FI (1) | FI114911B (enExample) |
| HU (2) | HU219973B (enExample) |
| IL (3) | IL103320A (enExample) |
| LU (1) | LU91279I2 (enExample) |
| MX (1) | MX9205532A (enExample) |
| NL (1) | NL300244I1 (enExample) |
| NO (3) | NO301472B1 (enExample) |
| NZ (1) | NZ244585A (enExample) |
| PL (4) | PL172282B1 (enExample) |
| PT (1) | PT536515E (enExample) |
| SG (1) | SG52361A1 (enExample) |
| SK (2) | SK284826B6 (enExample) |
| TW (1) | TW275616B (enExample) |
| ZA (1) | ZA927607B (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5284963A (en) * | 1992-08-13 | 1994-02-08 | American Cyanamid Company | Method of producing 7-(substituted)-9-[(substituted glycyl)-amidol]-6-demethyl-6-deoxytetra-cyclines |
| US5328902A (en) * | 1992-08-13 | 1994-07-12 | American Cyanamid Co. | 7-(substituted)-9-[(substituted glycyl)amido]-6-demethyl-6-deoxytetracyclines |
| 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 |
| US8106225B2 (en) | 1999-09-14 | 2012-01-31 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
| CZ301835B6 (cs) | 1999-09-14 | 2010-07-07 | Trustees Of Tufts College | Zpusob prípravy 7-, 9- nebo 13- substituované tetracyklinové slouceniny, reaktivní tetracyklinový chemický komplex a tetracyklinová sloucenina substituovaná v poloze 7 nebo 9 |
| ATE365710T1 (de) | 2000-03-31 | 2007-07-15 | Tufts College | 7- und 9-carbamat, harnstoff, thioharnstoff, thiocarbamat und heteroaryl-amino substituierte tetracyclinverbindungen |
| AU2001259701A1 (en) * | 2000-05-15 | 2001-11-26 | Paratek Pharmaceuticals, Inc | 7-substituted fused ring tetracycline compounds |
| US7094806B2 (en) | 2000-07-07 | 2006-08-22 | Trustees Of Tufts College | 7, 8 and 9-substituted tetracycline compounds |
| CZ2003344A3 (cs) * | 2000-07-07 | 2003-05-14 | Trustees Of Tufts College | 9-Substituované minocyklinové sloučeniny |
| AU2002250331A1 (en) | 2001-03-13 | 2002-09-24 | Paratek Pharmaceuticals, Inc. | 7-pyrollyl tetracycline compounds and methods of use thereof |
| WO2002072532A1 (en) | 2001-03-13 | 2002-09-19 | Paratek Pharmaceuticals, Inc. | 7, 9-substituted tetracycline compounds |
| US7553828B2 (en) | 2001-03-13 | 2009-06-30 | Paratek Pharmaceuticals, Inc. | 9-aminomethyl substituted minocycline compounds |
| EP1241160A1 (en) | 2001-03-13 | 2002-09-18 | Glaxo Group Limited | Tetracycline derivatives and their use as antibiotic agents |
| EP1399414B1 (en) * | 2001-04-24 | 2010-01-13 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for the treatment of malaria |
| EP1408987B1 (en) | 2001-07-13 | 2013-04-10 | Paratek Pharmaceuticals, Inc. | Tetracycline compounds having target therapeutic activities |
| WO2003055441A2 (en) | 2001-08-02 | 2003-07-10 | Paratek Pharmaceuticals, Inc. | Medicaments |
| EP2311797A1 (en) | 2002-01-08 | 2011-04-20 | Paratek Pharmaceuticals, Inc. | 4-dedimethylamino tetracycline compounds |
| JP2005526754A (ja) * | 2002-03-08 | 2005-09-08 | パラテック ファーマシューティカルズ インコーポレイテッド | アミノメチル置換されたテトラサイクリン化合物 |
| WO2005009943A2 (en) | 2003-07-09 | 2005-02-03 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| UA83266C2 (en) * | 2003-12-08 | 2008-06-25 | Уайет | Oxazole derivatives of tetracyclines |
| KR101171408B1 (ko) | 2004-05-21 | 2012-08-08 | 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 | 테트라사이클린 및 이의 유사체의 합성 |
| US7534766B2 (en) | 2004-11-05 | 2009-05-19 | Wyeth | Glucuronide metabolites and epimers thereof of tigecycline |
| AR057649A1 (es) | 2005-05-27 | 2007-12-12 | Wyeth Corp | Formas solidas cristalinas de tigeciclina y metodos para preparar las mismas |
| JP2009507793A (ja) * | 2005-08-31 | 2009-02-26 | ワイス | グリシルサイクリンの９−アミノカルボニル置換誘導体 |
| WO2007133797A2 (en) | 2006-05-15 | 2007-11-22 | Paratek Pharmaceuticals, Inc. | Methods of regulating expression of genes or of gene products using substituted tetracycline compounds |
| RU2483072C2 (ru) | 2007-11-29 | 2013-05-27 | Актелион Фармасьютиклз Лтд | Производные фосфоновой кислоты и их применение в качестве антагонистов рецептора p2y12 |
| 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 |
| TWI585071B (zh) | 2008-05-19 | 2017-06-01 | 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 |
| HUE026562T2 (hu) * | 2008-08-08 | 2016-06-28 | Tetraphase Pharmaceuticals Inc | C7-fluor-helyettesített tetraciklin vegyületek |
| WO2010126607A2 (en) | 2009-04-30 | 2010-11-04 | President And Fellows Of Harvard College | Synthesis of tetracyclines and intermediates thereto |
| CN102459153A (zh) | 2009-05-08 | 2012-05-16 | 四相制药公司 | 四环素类化合物 |
| EP2470500B1 (en) | 2009-08-28 | 2017-10-04 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
| MX347919B (es) | 2010-05-12 | 2017-05-17 | Rempex Pharmaceuticals Inc * | 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 |
| TR201902057T4 (tr) | 2012-08-31 | 2019-03-21 | Tetraphase Pharmaceuticals Inc | Tetrasiklin bileşikleri. |
| WO2015071299A2 (en) | 2013-11-12 | 2015-05-21 | Galenicum Health S.L. | Stable pharmaceutical compositions |
| MA46567A (fr) | 2016-10-19 | 2019-08-28 | Tetraphase Pharmaceuticals Inc | Formes cristallines de l'éravacycline |
Family Cites Families (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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- 1992-10-02 PL PL92310718A patent/PL175957B1/pl unknown
- 1992-10-02 PL PL92296143A patent/PL173311B1/pl unknown
- 1992-10-02 AU AU26183/92A patent/AU654049B2/en not_active Expired
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1995
- 1995-04-28 HU HU95P/P00116P patent/HU211172A9/hu active Protection Beyond IP Right Term
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1996
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1997
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2004
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2006
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2017
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