CN1048240C - 制备7－取代－9－取代氨基－6－去甲基－6－去氧四环素的方法 - Google Patents

制备7－取代－9－取代氨基－6－去甲基－6－去氧四环素的方法 Download PDF

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Publication number: CN1048240C
Authority: CN; China
Prior art keywords: alkyl; amino; group; ring; branched
Prior art date: 1991-10-04
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.): Expired - Lifetime

Application number

CN92112130A

Other languages

English (en)

Chinese (zh)

Other versions

CN1072172A (zh

Inventor

J·J·赫拉夫卡

苏费恩

Y·格卢兹曼

V·J·李

A·A·罗斯

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

Priority date (The priority date 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 date listed.)

1991-10-04

Filing date

1992-10-03

Publication date

2000-01-12

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=25092264&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CN1048240(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1992-10-03 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1993-05-19 Publication of CN1072172A publication Critical patent/CN1072172A/zh

2000-01-12 Application granted granted Critical

2000-01-12 Publication of CN1048240C publication Critical patent/CN1048240C/zh

2007-10-03 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

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125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 69
150000001875 compounds Chemical class 0.000 claims abstract description 34
238000000034 method Methods 0.000 claims abstract description 11
-1 monosubstituted amino Chemical group 0.000 claims description 696
229910052760 oxygen Inorganic materials 0.000 claims description 446
229910052717 sulfur Inorganic materials 0.000 claims description 408
229910052711 selenium Inorganic materials 0.000 claims description 394
125000005842 heteroatom Chemical group 0.000 claims description 271
125000003118 aryl group Chemical group 0.000 claims description 181
229910052739 hydrogen Inorganic materials 0.000 claims description 177
239000001257 hydrogen Substances 0.000 claims description 176
229920006395 saturated elastomer Chemical group 0.000 claims description 171
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 157
125000001424 substituent group Chemical group 0.000 claims description 153
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 140
229910052736 halogen Inorganic materials 0.000 claims description 135
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 129
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 127
125000004093 cyano group Chemical group *C#N 0.000 claims description 125
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 120
125000005605 benzo group Chemical group 0.000 claims description 118
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 117
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 114
125000000217 alkyl group Chemical group 0.000 claims description 109
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 109
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 106
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 102
125000005843 halogen group Chemical group 0.000 claims description 87
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 83
125000003710 aryl alkyl group Chemical group 0.000 claims description 79
150000002367 halogens Chemical class 0.000 claims description 79
125000000623 heterocyclic group Chemical group 0.000 claims description 77
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 77
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 75
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 73
125000004344 phenylpropyl group Chemical group 0.000 claims description 72
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 71
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
238000006467 substitution reaction Methods 0.000 claims description 49
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 46
239000001301 oxygen Substances 0.000 claims description 46
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 44
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 40
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 33
125000002252 acyl group Chemical group 0.000 claims description 30
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 29
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 27
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
229910052740 iodine Inorganic materials 0.000 claims description 24
239000011630 iodine Substances 0.000 claims description 24
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 23
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 23
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 21
125000002757 morpholinyl group Chemical group 0.000 claims description 20
125000003435 aroyl group Chemical group 0.000 claims description 17
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
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 description 16
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 15
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 14
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 14
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 13
125000003282 alkyl amino group Chemical group 0.000 claims description 13
125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 12
239000000460 chlorine Substances 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 12
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
QWCKQJZIFLGMSD-UHFFFAOYSA-N 2-Aminobutanoic acid Natural products CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
230000003287 optical effect Effects 0.000 claims description 10
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 9
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 9
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 9
125000004423 acyloxy group Chemical group 0.000 claims description 8
229920002554 vinyl polymer Polymers 0.000 claims description 8
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 7
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
QPNJHVDIRZNKOX-LURJTMIESA-N ethyl (2s)-pyrrolidine-2-carboxylate Chemical compound CCOC(=O)[C@@H]1CCCN1 QPNJHVDIRZNKOX-LURJTMIESA-N 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
125000005918 1,2-dimethylbutyl group Chemical group 0.000 claims description 6
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 6
QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims description 6
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 6
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 6
150000004696 coordination complex Chemical class 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
238000002360 preparation method Methods 0.000 claims description 6
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 6
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 5
125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
125000006628 propoxycarbonylamino group Chemical group 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 2
125000003396 thiol group Chemical class [H]S* 0.000 claims 14
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 8
125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims 8
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 8
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 8
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims 6
125000005252 haloacyl group Chemical group 0.000 claims 6
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 6
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 4
125000005916 2-methylpentyl group Chemical group 0.000 claims 4
QWCKQJZIFLGMSD-GSVOUGTGSA-N D-alpha-aminobutyric acid Chemical compound CC[C@@H](N)C(O)=O QWCKQJZIFLGMSD-GSVOUGTGSA-N 0.000 claims 4
239000004471 Glycine Substances 0.000 claims 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
239000002253 acid Substances 0.000 claims 4
125000004659 aryl alkyl thio group Chemical group 0.000 claims 4
125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 4
USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 claims 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
150000001335 aliphatic alkanes Chemical class 0.000 claims 3
125000003277 amino group Chemical group 0.000 claims 3
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
125000005110 aryl thio group Chemical group 0.000 claims 2
238000006243 chemical reaction Methods 0.000 claims 2
239000000039 congener Substances 0.000 claims 2
125000004706 n-propylthio group Chemical group C(CC)S* 0.000 claims 2
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 2
150000003254 radicals Chemical group 0.000 claims 2
239000011593 sulfur Substances 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
UXTFKIJKRJJXNV-UHFFFAOYSA-N 1-$l^{1}-oxidanylethanone Chemical compound CC([O])=O UXTFKIJKRJJXNV-UHFFFAOYSA-N 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
150000001266 acyl halides Chemical class 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
230000002140 halogenating effect Effects 0.000 claims 1
229910017053 inorganic salt Inorganic materials 0.000 claims 1
150000002576 ketones Chemical class 0.000 claims 1
239000002184 metal Chemical class 0.000 claims 1
229910001960 metal nitrate Inorganic materials 0.000 claims 1
229910017604 nitric acid Inorganic materials 0.000 claims 1
150000003141 primary amines Chemical class 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
125000006633 tert-butoxycarbonylamino group Chemical group 0.000 claims 1
239000004098 Tetracycline Substances 0.000 abstract description 30
235000019364 tetracycline Nutrition 0.000 abstract description 30
150000003522 tetracyclines Chemical class 0.000 abstract description 23
229940040944 tetracyclines Drugs 0.000 abstract description 9
239000000543 intermediate Substances 0.000 abstract description 4
230000000694 effects Effects 0.000 abstract description 3
238000001228 spectrum Methods 0.000 abstract 1
239000002585 base Substances 0.000 description 313
239000011669 selenium Substances 0.000 description 252
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 159
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 123
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 106
229910052757 nitrogen Inorganic materials 0.000 description 86
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 82
238000009740 moulding (composite fabrication) Methods 0.000 description 74
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 56
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 54
125000003545 alkoxy group Chemical group 0.000 description 47
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 47
125000001544 thienyl group Chemical group 0.000 description 46
239000005864 Sulphur Substances 0.000 description 42
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 41
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 41
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 41
125000002541 furyl group Chemical group 0.000 description 41
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 41
BLRHMMGNCXNXJL-UHFFFAOYSA-N 1-methylindole Chemical compound C1=CC=C2N(C)C=CC2=C1 BLRHMMGNCXNXJL-UHFFFAOYSA-N 0.000 description 40
125000005958 tetrahydrothienyl group Chemical group 0.000 description 40
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 37
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 36
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 36
125000003226 pyrazolyl group Chemical group 0.000 description 36
125000000335 thiazolyl group Chemical group 0.000 description 36
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 35
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 35
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 35
125000002971 oxazolyl group Chemical group 0.000 description 35
125000003373 pyrazinyl group Chemical group 0.000 description 34
125000002098 pyridazinyl group Chemical group 0.000 description 34
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 26
229960002180 tetracycline Drugs 0.000 description 21
229930101283 tetracycline Natural products 0.000 description 21
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 18
125000005999 2-bromoethyl group Chemical group 0.000 description 18
ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
125000005997 bromomethyl group Chemical group 0.000 description 18
NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 18
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 18
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 17
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 17
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 17
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 17
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 15
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 14
150000003573 thiols Chemical class 0.000 description 14
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 13
125000003368 amide group Chemical group 0.000 description 13
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 10
235000002639 sodium chloride Nutrition 0.000 description 10
125000006526 (C1-C2) alkyl group Chemical group 0.000 description 8
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 8
241000894006 Bacteria Species 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
239000005977 Ethylene Substances 0.000 description 7
230000001580 bacterial effect Effects 0.000 description 7
108090000623 proteins and genes Proteins 0.000 description 7
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 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
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
230000000844 anti-bacterial effect Effects 0.000 description 6
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 6
230000003115 biocidal effect Effects 0.000 description 6
150000002460 imidazoles Chemical class 0.000 description 6
229960004023 minocycline Drugs 0.000 description 6
125000005976 1-phenylethyloxy group Chemical group 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
125000000524 functional group Chemical group 0.000 description 5
150000003053 piperidines Chemical class 0.000 description 5
235000018102 proteins Nutrition 0.000 description 5
102000004169 proteins and genes Human genes 0.000 description 5
150000003235 pyrrolidines Chemical class 0.000 description 5
210000003705 ribosome Anatomy 0.000 description 5
IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 5
125000006583 (C1-C3) haloalkyl group Chemical group 0.000 description 4
206010059866 Drug resistance Diseases 0.000 description 4
125000006637 cyclobutyl carbonyl group Chemical group 0.000 description 4
125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 4
125000006638 cyclopentyl carbonyl group Chemical group 0.000 description 4
125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 4
239000003814 drug Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
230000007246 mechanism Effects 0.000 description 4
IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 description 4
125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 4
241001597008 Nomeidae Species 0.000 description 3
239000004100 Oxytetracycline Substances 0.000 description 3
241000191940 Staphylococcus Species 0.000 description 3
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
229960000625 oxytetracycline Drugs 0.000 description 3
235000019366 oxytetracycline Nutrition 0.000 description 3
125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
DHPRQBPJLMKORJ-XRNKAMNCSA-N (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O DHPRQBPJLMKORJ-XRNKAMNCSA-N 0.000 description 2
QOOQLKSEGVNYLA-UHFFFAOYSA-N 1-$l^{1}-oxidanylbutane Chemical compound CCCC[O] QOOQLKSEGVNYLA-UHFFFAOYSA-N 0.000 description 2
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
208000035473 Communicable disease Diseases 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
241000194017 Streptococcus Species 0.000 description 2
102000004377 Thiopurine S-methyltransferases Human genes 0.000 description 2
108090000958 Thiopurine S-methyltransferases Proteins 0.000 description 2
125000005336 allyloxy group Chemical group 0.000 description 2
CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 description 2
229960004475 chlortetracycline Drugs 0.000 description 2
235000019365 chlortetracycline Nutrition 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
238000000855 fermentation Methods 0.000 description 2
230000004151 fermentation Effects 0.000 description 2
125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
125000004193 piperazinyl group Chemical group 0.000 description 2
101150015970 tetM gene Proteins 0.000 description 2
229940072172 tetracycline antibiotic Drugs 0.000 description 2
CSUGQXMRKOKBFI-UHFFFAOYSA-N 1-methylindazole Chemical compound C1=CC=C2N(C)N=CC2=C1 CSUGQXMRKOKBFI-UHFFFAOYSA-N 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
241000607534 Aeromonas Species 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
241000589876 Campylobacter Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000790917 Dioxys <bee> Species 0.000 description 1
241000588921 Enterobacteriaceae Species 0.000 description 1
GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 1
241000207202 Gardnerella Species 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
241000204031 Mycoplasma Species 0.000 description 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
125000000033 alkoxyamino group Chemical group 0.000 description 1
125000000266 alpha-aminoacyl group Chemical group 0.000 description 1
125000002393 azetidinyl group Chemical group 0.000 description 1
125000004069 aziridinyl group Chemical group 0.000 description 1
244000285940 beete Species 0.000 description 1
239000003139 biocide Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
235000011222 chang cao shi Nutrition 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
125000006317 cyclopropyl amino group Chemical group 0.000 description 1
230000001086 cytosolic effect Effects 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
238000011049 filling Methods 0.000 description 1
150000003948 formamides Chemical class 0.000 description 1
239000002955 immunomodulating agent Substances 0.000 description 1
229940121354 immunomodulator Drugs 0.000 description 1
230000002584 immunomodulator Effects 0.000 description 1
230000001976 improved effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000007154 intracellular accumulation Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
244000005700 microbiome Species 0.000 description 1
MENOBBYDZHOWLE-UHFFFAOYSA-N morpholine-2,3-dione Chemical class O=C1NCCOC1=O MENOBBYDZHOWLE-UHFFFAOYSA-N 0.000 description 1
229950003587 nitrocycline Drugs 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000003748 selenium group Chemical group *[Se]* 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
101150045159 tetB gene Proteins 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000004385 trihaloalkyl group Chemical group 0.000 description 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
- 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)

CN92112130A 1991-10-04 1992-10-03 制备7－取代－9－取代氨基－6－去甲基－6－去氧四环素的方法 Expired - Lifetime CN1048240C (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US77157691A	1991-10-04	1991-10-04
US771,576		1991-10-04

Publications (2)

Publication Number	Publication Date
CN1072172A CN1072172A (zh)	1993-05-19
CN1048240C true CN1048240C (zh)	2000-01-12

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CN92112130A Expired - Lifetime CN1048240C (zh)	1991-10-04	1992-10-03	制备7－取代－9－取代氨基－6－去甲基－6－去氧四环素的方法

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Country	Link
EP (1)	EP0536515B1 (2)
JP (1)	JP3186863B2 (2)
KR (1)	KR100269072B1 (2)
CN (1)	CN1048240C (2)
AT (1)	ATE211128T1 (2)
AU (1)	AU654049B2 (2)
BR (1)	BR1100853A (2)
CA (1)	CA2079692C (2)
CL (1)	CL2004001623A1 (2)
CZ (2)	CZ309397A3 (2)
DE (4)	DE122006000058I2 (2)
DK (1)	DK0536515T3 (2)
ES (1)	ES2168254T3 (2)
FI (1)	FI114911B (2)
HU (2)	HU219973B (2)
IL (3)	IL103320A (2)
LU (1)	LU91279I2 (2)
MX (1)	MX9205532A (2)
NL (1)	NL300244I1 (2)
NO (3)	NO301472B1 (2)
NZ (1)	NZ244585A (2)
PL (4)	PL172282B1 (2)
PT (1)	PT536515E (2)
SG (1)	SG52361A1 (2)
SK (2)	SK284826B6 (2)
TW (1)	TW275616B (2)
ZA (1)	ZA927607B (2)

Families Citing this family (39)

* Cited by examiner, † Cited by third party
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

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3579579A (en) *	1968-04-18	1971-05-18	American Cyanamid Co	Substituted 7- and/or 9-amino-6-demethyl-6-deoxytetracyclines

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3338963A (en) *	1960-10-28	1967-08-29	American Cyanamid Co	Tetracycline compounds

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1996
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2017
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Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3579579A (en) *	1968-04-18	1971-05-18	American Cyanamid Co	Substituted 7- and/or 9-amino-6-demethyl-6-deoxytetracyclines

Also Published As

Publication number	Publication date
CL2004001623A1 (es)	2005-06-03
NO2006015I2 (no)	2011-03-14
KR930007894A (ko)	1993-05-20
IL119590A0 (en)	1997-02-18
IL119590A (en)	1999-03-12
ATE211128T1 (de)	2002-01-15
PL173311B1 (pl)	1998-02-27
SK298492A3 (en)	1995-03-08
LU91279I2 (fr)	2006-12-11
NO301472B1 (no)	1997-11-03
NL300244I2 (nl)	2007-01-02
ZA927607B (en)	1993-04-13
AU2618392A (en)	1993-04-08
ES2168254T3 (es)	2002-06-16
PL176333B1 (pl)	1999-05-31
NL300244I1 (nl)	2007-01-02
HUT63145A (en)	1993-07-28
SK284826B6 (sk)	2005-12-01
PT536515E (pt)	2002-05-31
HU9203110D0 (en)	1992-12-28
NO2017037I1 (no)	2017-08-01
HU211172A9 (en)	1995-11-28
EP0536515B1 (en)	2001-12-19
CZ284209B6 (cs)	1998-09-16
JPH05255219A (ja)	1993-10-05
KR100269072B1 (ko)	2000-10-16
JP3186863B2 (ja)	2001-07-11
CA2079692C (en)	2004-06-08
SG52361A1 (en)	1998-09-28
DE69232302T2 (de)	2002-08-14
NO2006015I1 (no)	2006-11-27
PL175957B1 (pl)	1999-03-31
PL296143A1 (en)	1993-05-31
DK0536515T3 (da)	2002-04-08
DE69232302T4 (de)	2003-02-13
NO923857L (no)	1993-04-05
IL103320A (en)	1998-12-06
AU654049B2 (en)	1994-10-20
NO2017037I2 (no)	2017-08-01
SK280837B6 (sk)	2000-08-14
SK114999A3 (en)	2000-07-11
MX9205532A (es)	1993-04-01
NO923857D0 (no)	1992-10-02
CZ298492A3 (en)	1993-05-12
HK1011348A1 (en)	1999-07-09
PL172282B1 (pl)	1997-08-29
FI924454L (fi)	1993-04-05
DE122006000058I1 (de)	2007-01-18
CZ284159B6 (cs)	1998-08-12
CA2079692A1 (en)	1993-04-05
IL103320A0 (en)	1993-03-15
BR1100853A (pt)	1999-12-07
DE122006000058I2 (de)	2007-09-13
CN1072172A (zh)	1993-05-19
NZ244585A (en)	1995-07-26
DE69232302D1 (de)	2002-01-31
FI924454A0 (fi)	1992-10-02
EP0536515A1 (en)	1993-04-14
TW275616B (2)	1996-05-11
HU219973B (hu)	2001-10-28
CZ309397A3 (cs)	1998-09-16
FI114911B (fi)	2005-01-31

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Date	Code	Title	Description
1993-05-19	C06	Publication
1993-05-19	PB01	Publication
1995-02-15	C10	Entry into substantive examination
1995-02-15	SE01	Entry into force of request for substantive examination
2000-01-12	C14	Grant of patent or utility model
2000-01-12	GR01	Patent grant
2002-06-12	C15	Extension of patent right duration from 15 to 20 years for appl. with date before 31.12.1992 and still valid on 11.12.2001 (patent law change 1993)
2002-06-12	OR01	Other related matters
2004-03-31	C56	Change in the name or address of the patentee	Owner name: WYETH(AMERICAN HOME PRODUCTS) HOLDING CO., LTD. Free format text: FORMER NAME OR ADDRESS: AMERICAN CYANAMID COMPANY
2004-03-31	CP01	Change in the name or title of a patent holder	Patentee after: Wyeth Holding Corp. Patentee before: American Cyanamid Co.
2012-11-14	C17	Cessation of patent right
2012-11-14	CX01	Expiry of patent term	Expiration termination date: 20121008 Granted publication date: 20000112

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