PL172282B1 - S p o só b w ytw arzania now ych 7-po dstaw io nyc h-9-po d s taw ionych-am ino-6- dem etylo-6-deoksytetracyklin PL PL PL PL PL PL PL PL - Google Patents
S p o só b w ytw arzania now ych 7-po dstaw io nyc h-9-po d s taw ionych-am ino-6- dem etylo-6-deoksytetracyklin PL PL PL PL PL PL PL PLInfo
- Publication number
- PL172282B1 PL172282B1 PL92310717A PL31071792A PL172282B1 PL 172282 B1 PL172282 B1 PL 172282B1 PL 92310717 A PL92310717 A PL 92310717A PL 31071792 A PL31071792 A PL 31071792A PL 172282 B1 PL172282 B1 PL 172282B1
- Authority
- PL
- Poland
- Prior art keywords
- group
- formula
- alkyl
- methylpropyl
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- -1 dimethylamino, diethylamino, ethyl Chemical group 0.000 claims abstract description 652
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 123
- 239000001257 hydrogen Substances 0.000 claims abstract description 122
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 111
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 104
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 103
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 103
- 125000001424 substituent group Chemical group 0.000 claims abstract description 98
- 150000002367 halogens Chemical group 0.000 claims abstract description 95
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 85
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 75
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 67
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 63
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 62
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 57
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 55
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 46
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 42
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims abstract description 30
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 30
- 125000003277 amino group Chemical group 0.000 claims abstract description 30
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 28
- 125000002252 acyl group Chemical group 0.000 claims abstract description 20
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 16
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 125000004889 1-methylethylamino group Chemical group CC(C)N* 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 218
- 229910052717 sulfur Inorganic materials 0.000 claims description 206
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 190
- 125000005842 heteroatom Chemical group 0.000 claims description 172
- 229910052711 selenium Inorganic materials 0.000 claims description 164
- 125000000217 alkyl group Chemical group 0.000 claims description 129
- 125000003118 aryl group Chemical group 0.000 claims description 122
- 229920006395 saturated elastomer Polymers 0.000 claims description 98
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 77
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 68
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 53
- 125000000623 heterocyclic group Chemical group 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 27
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims description 26
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 20
- 125000003282 alkyl amino group Chemical group 0.000 claims description 20
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 17
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 16
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 15
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 15
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- 125000003435 aroyl group Chemical group 0.000 claims description 12
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 10
- 229910052751 metal Chemical class 0.000 claims description 10
- 239000002184 metal Chemical class 0.000 claims description 10
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 10
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 150000001412 amines Chemical group 0.000 claims description 9
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 9
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 8
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 7
- 229960002449 glycine Drugs 0.000 claims description 7
- 235000013905 glycine and its sodium salt Nutrition 0.000 claims description 7
- 125000005252 haloacyl group Chemical group 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 5
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 5
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 5
- QPNJHVDIRZNKOX-LURJTMIESA-N ethyl (2s)-pyrrolidine-2-carboxylate Chemical compound CCOC(=O)[C@@H]1CCCN1 QPNJHVDIRZNKOX-LURJTMIESA-N 0.000 claims description 5
- 235000013930 proline Nutrition 0.000 claims description 5
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 claims description 5
- QWCKQJZIFLGMSD-UHFFFAOYSA-N 2-Aminobutanoic acid Natural products CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 4
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 4
- 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 4
- 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 4
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 claims description 3
- 125000005916 2-methylpentyl group Chemical group 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- QWCKQJZIFLGMSD-GSVOUGTGSA-N D-alpha-aminobutyric acid Chemical compound CC[C@@H](N)C(O)=O QWCKQJZIFLGMSD-GSVOUGTGSA-N 0.000 claims description 3
- 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 3
- 230000008569 process Effects 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 claims description 2
- 150000003148 prolines Chemical class 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract description 6
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 abstract description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 2
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 abstract 1
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 abstract 1
- 125000004385 trihaloalkyl group Chemical group 0.000 abstract 1
- 239000011669 selenium Substances 0.000 description 160
- 238000006467 substitution reaction Methods 0.000 description 88
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 85
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 56
- 125000004076 pyridyl group Chemical group 0.000 description 53
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 46
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 39
- 125000004344 phenylpropyl group Chemical group 0.000 description 38
- 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 description 36
- 125000000168 pyrrolyl group Chemical group 0.000 description 36
- 239000004098 Tetracycline Substances 0.000 description 35
- 125000001041 indolyl group Chemical group 0.000 description 35
- 235000019364 tetracycline Nutrition 0.000 description 35
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 34
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 33
- 125000001544 thienyl group Chemical group 0.000 description 33
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 31
- 125000002541 furyl group Chemical group 0.000 description 31
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 31
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 30
- 125000003373 pyrazinyl group Chemical group 0.000 description 30
- 125000000714 pyrimidinyl group Chemical group 0.000 description 30
- 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 description 29
- 125000002098 pyridazinyl group Chemical group 0.000 description 29
- 229960002180 tetracycline Drugs 0.000 description 29
- 229930101283 tetracycline Natural products 0.000 description 29
- 150000003522 tetracyclines Chemical class 0.000 description 29
- 125000002971 oxazolyl group Chemical group 0.000 description 28
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 27
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 27
- 125000002883 imidazolyl group Chemical group 0.000 description 27
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 description 27
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 25
- 125000000335 thiazolyl group Chemical group 0.000 description 25
- 125000003226 pyrazolyl group Chemical group 0.000 description 24
- DHIVBEZCBBHIPZ-UHFFFAOYSA-N 1-aminoimidazolidin-2-one Chemical compound NN1CCNC1=O DHIVBEZCBBHIPZ-UHFFFAOYSA-N 0.000 description 22
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 16
- 239000000460 chlorine Chemical group 0.000 description 15
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 15
- 125000005999 2-bromoethyl group Chemical group 0.000 description 14
- 241000589877 Campylobacter coli Species 0.000 description 14
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 14
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 13
- 125000003710 aryl alkyl group Chemical group 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 12
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 11
- 125000005336 allyloxy group Chemical group 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
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 11
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 11
- 230000014616 translation Effects 0.000 description 11
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 9
- 241000894006 Bacteria Species 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- 241000588724 Escherichia coli Species 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000003115 biocidal effect Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000000338 in vitro Methods 0.000 description 7
- 101150015970 tetM gene Proteins 0.000 description 7
- 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
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000003242 anti bacterial agent Substances 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
- 230000000694 effects Effects 0.000 description 6
- 229960004023 minocycline Drugs 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229940040944 tetracyclines Drugs 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 230000000845 anti-microbial effect Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000013519 translation Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229940088710 antibiotic agent Drugs 0.000 description 4
- 230000001580 bacterial effect Effects 0.000 description 4
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- QQBPIHBUCMDKFG-UHFFFAOYSA-N phenazopyridine hydrochloride Chemical group Cl.NC1=NC(N)=CC=C1N=NC1=CC=CC=C1 QQBPIHBUCMDKFG-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
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- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- KDOLGICVVPEEHO-UHFFFAOYSA-N pyrrolidine-3-carbaldehyde Chemical compound O=CC1CCNC1 KDOLGICVVPEEHO-UHFFFAOYSA-N 0.000 description 1
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- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 101150045159 tetB gene Proteins 0.000 description 1
- 229940072172 tetracycline antibiotic Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- PTMFUWGXPRYYMC-UHFFFAOYSA-N triethylazanium;formate Chemical compound OC=O.CCN(CC)CC PTMFUWGXPRYYMC-UHFFFAOYSA-N 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 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)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (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)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrrole Compounds (AREA)
- Furan Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
- Saccharide Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Moulding By Coating Moulds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (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 |
|---|---|
| PL172282B1 true PL172282B1 (pl) | 1997-08-29 |
Family
ID=25092264
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL92310717A PL172282B1 (pl) | 1991-10-04 | 1992-10-02 | S p o só b w ytw arzania now ych 7-po dstaw io nyc h-9-po d s taw ionych-am ino-6- dem etylo-6-deoksytetracyklin PL PL PL PL PL PL PL PL |
| PL92310719A PL176333B1 (pl) | 1991-10-04 | 1992-10-02 | Sposób wytwarzania nowych 7-podstawionych-9-podstawionych-amino-6-demetylo-6-deoksytetracyklin |
| PL92310718A PL175957B1 (pl) | 1991-10-04 | 1992-10-02 | Sposób wytwarzania nowych 7-podstawionych-9-podstawionych-amino-6-demetylo-6-deoksytetracyklin |
| PL92296143A PL173311B1 (pl) | 1991-10-04 | 1992-10-02 | Nowy sposób wytwarzania nowych 7-podstawionych-9-podstawionych-amino-6-demetylo-6-deoksytetracyklin |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL92310719A PL176333B1 (pl) | 1991-10-04 | 1992-10-02 | Sposób wytwarzania nowych 7-podstawionych-9-podstawionych-amino-6-demetylo-6-deoksytetracyklin |
| PL92310718A PL175957B1 (pl) | 1991-10-04 | 1992-10-02 | Sposób wytwarzania nowych 7-podstawionych-9-podstawionych-amino-6-demetylo-6-deoksytetracyklin |
| PL92296143A PL173311B1 (pl) | 1991-10-04 | 1992-10-02 | Nowy sposób wytwarzania nowych 7-podstawionych-9-podstawionych-amino-6-demetylo-6-deoksytetracyklin |
Country Status (27)
Families Citing this family (39)
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| US5420272A (en) * | 1992-08-13 | 1995-05-30 | American Cyanamid Company | 7-(substituted)-8-(substituted)-9-](substituted glycyl)amido]-6-demethyl-6-deoxytetracyclines |
| 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 |
| 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 |
| JP5093953B2 (ja) | 1999-09-14 | 2012-12-12 | トラスティーズ オブ タフツ カレッジ | 遷移金属を用いた化学反応による置換テトラサイクリンの調製方法 |
| US6818634B2 (en) | 2000-03-31 | 2004-11-16 | Paratek Pharmaceuticals, Inc. | 7-and 9-carbamate, urea, thiourea, thiocarbamate, and heteroaryl-amino substituted tetracycline compounds |
| WO2001087824A2 (en) * | 2000-05-15 | 2001-11-22 | 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 |
| 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 |
| 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 |
| AU2002250331A1 (en) | 2001-03-13 | 2002-09-24 | Paratek Pharmaceuticals, Inc. | 7-pyrollyl tetracycline compounds and methods of use thereof |
| EP2298732A1 (en) | 2001-03-13 | 2011-03-23 | Paratek Pharmaceuticals, Inc. | 7,9-Substituted tetracycline compounds |
| JP2004529927A (ja) * | 2001-04-24 | 2004-09-30 | パラテック ファーマシューティカルズ， インク． | マラリアの治療のための置換されたテトラサイクリン化合物 |
| WO2003005971A2 (en) | 2001-07-13 | 2003-01-23 | Paratek Pharmaceuticals, Inc. | Tetracycline compounds having target therapeutic activities |
| AU2002365120A1 (en) | 2001-08-02 | 2003-07-15 | Paratek Pharmaceuticals, Inc. | Medicaments |
| EP2311798A1 (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 |
| EP2295404A3 (en) | 2003-07-09 | 2011-05-11 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| UA83266C2 (en) * | 2003-12-08 | 2008-06-25 | Уайет | Oxazole derivatives of tetracyclines |
| CA2892332C (en) | 2004-05-21 | 2017-03-21 | President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
| 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 |
| US8518912B2 (en) | 2007-11-29 | 2013-08-27 | Actelion Pharmaceuticals Ltd. | Phosphonic acid derivates and their use as P2Y12 receptor antagonists |
| 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 |
| TW202332671A (zh) | 2008-05-19 | 2023-08-16 | 美商Ｐｒｔｋ Ｓｐｖ２公司 | 四環素化合物之甲苯磺酸鹽及同素異形體 |
| PT2323972E (pt) * | 2008-08-08 | 2013-10-09 | Tetraphase Pharmaceuticals Inc | Compostos de tetraciclina substituídos com c7-flúor |
| US9073829B2 (en) | 2009-04-30 | 2015-07-07 | President And Fellows Of Harvard College | Synthesis of tetracyclines and intermediates thereto |
| US9315451B2 (en) | 2009-05-08 | 2016-04-19 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
| IN2012DN02502A (cg-RX-API-DMAC10.html) | 2009-08-28 | 2015-08-28 | Tetraphase Pharmaceuticals Inc | |
| JP6025712B2 (ja) | 2010-05-12 | 2016-11-16 | レンペックス・ファーマシューティカルズ・インコーポレイテッド | テトラサイクリン組成物 |
| WO2013013504A1 (zh) * | 2011-07-26 | 2013-01-31 | 山东亨利医药科技有限责任公司 | 替加环素衍生物 |
| LT2890673T (lt) | 2012-08-31 | 2019-04-10 | Tetraphase Pharmaceuticals, Inc. | Tetraciklino junginiai |
| EP3068370A2 (en) | 2013-11-12 | 2016-09-21 | Galenicum Health S.L. | Stable pharmaceutical compositions |
| ES2978198T3 (es) | 2016-10-19 | 2024-09-06 | Tetraphase Pharmaceuticals Inc | Formas cristalinas de eravaciclina |
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| 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 |
-
1992
- 1992-08-21 PT PT92114281T patent/PT536515E/pt unknown
- 1992-08-21 DE DE200612000058 patent/DE122006000058I2/de active Active
- 1992-08-21 AT AT92114281T patent/ATE211128T1/de active
- 1992-08-21 DE DE69232302T patent/DE69232302T4/de not_active Expired - Lifetime
- 1992-08-21 DE DE69232302A patent/DE69232302D1/de not_active Expired - Lifetime
- 1992-08-21 EP EP92114281A patent/EP0536515B1/en not_active Expired - Lifetime
- 1992-08-21 DE DE1992632302 patent/DE122006000058I1/de active Pending
- 1992-08-21 DK DK92114281T patent/DK0536515T3/da active
- 1992-08-21 ES ES92114281T patent/ES2168254T3/es not_active Expired - Lifetime
- 1992-08-21 SG SG1996003437A patent/SG52361A1/en unknown
- 1992-08-27 TW TW081106768A patent/TW275616B/zh not_active IP Right Cessation
- 1992-09-29 MX MX9205532A patent/MX9205532A/es unknown
- 1992-09-30 CZ CZ973093A patent/CZ309397A3/cs not_active IP Right Cessation
- 1992-09-30 SK SK2984-92A patent/SK280837B6/sk not_active IP Right Cessation
- 1992-09-30 HU HU9203110A patent/HU219973B/hu unknown
- 1992-09-30 SK SK1149-99A patent/SK284826B6/sk not_active IP Right Cessation
- 1992-09-30 CZ CS922984A patent/CZ284159B6/cs not_active IP Right Cessation
- 1992-10-01 NZ NZ244585A patent/NZ244585A/en not_active IP Right Cessation
- 1992-10-01 IL IL10332092A patent/IL103320A/en not_active IP Right Cessation
- 1992-10-01 IL IL11959092A patent/IL119590A/xx not_active IP Right Cessation
- 1992-10-02 FI FI924454A patent/FI114911B/fi active Protection Beyond IP Right Term
- 1992-10-02 KR KR1019920018122A patent/KR100269072B1/ko not_active Expired - Lifetime
- 1992-10-02 PL PL92310717A patent/PL172282B1/pl unknown
- 1992-10-02 PL PL92310719A patent/PL176333B1/pl unknown
- 1992-10-02 ZA ZA927607A patent/ZA927607B/xx unknown
- 1992-10-02 PL PL92310718A patent/PL175957B1/pl unknown
- 1992-10-02 PL PL92296143A patent/PL173311B1/pl unknown
- 1992-10-02 NO NO923857A patent/NO301472B1/no not_active IP Right Cessation
- 1992-10-02 CA CA002079692A patent/CA2079692C/en not_active Expired - Lifetime
- 1992-10-02 AU AU26183/92A patent/AU654049B2/en not_active Expired
- 1992-10-03 CN CN92112130A patent/CN1048240C/zh not_active Expired - Lifetime
- 1992-10-05 JP JP28811492A patent/JP3186863B2/ja not_active Expired - Lifetime
-
1995
- 1995-04-28 HU HU95P/P00116P patent/HU211172A9/hu active Protection Beyond IP Right Term
-
1996
- 1996-11-10 IL IL11959096A patent/IL119590A0/xx unknown
-
1997
- 1997-05-12 BR BR1100853-9A patent/BR1100853A/pt active IP Right Grant
-
2004
- 2004-06-25 CL CL200401623A patent/CL2004001623A1/es unknown
-
2006
- 2006-10-11 LU LU91279C patent/LU91279I2/fr unknown
- 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
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