SU574145A3 - Способ получени производных тетрациклина - Google Patents

Способ получени производных тетрациклина

Info

Publication number: SU574145A3
Authority: SU; USSR - Soviet Union
Prior art keywords: demethyl; butyl; tert; methyl; solution
Prior art date: 1972-09-18

Application number

SU7301957942A

Other languages

English (en)

Russian (ru)

Inventor

Бернарди Луиджи

Коллонна Винченцо

Ди Кастиглионе Роберто

Маси Паоло

Original Assignee

Сочиета Фармасьютичи Италиа С.П.А. (Фирма)

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.)

1972-09-18

Filing date

1973-09-17

Publication date

1977-09-25

1973-09-17 Application filed by Сочиета Фармасьютичи Италиа С.П.А. (Фирма) filed Critical Сочиета Фармасьютичи Италиа С.П.А. (Фирма)

1977-09-25 Application granted granted Critical

1977-09-25 Publication of SU574145A3 publication Critical patent/SU574145A3/ru

Links

239000004098 Tetracycline Substances 0.000 title claims description 6
229960002180 tetracycline Drugs 0.000 title claims description 6
235000019364 tetracycline Nutrition 0.000 title claims description 6
229930101283 tetracycline Natural products 0.000 title claims description 6
238000000034 method Methods 0.000 title claims description 5
150000003522 tetracyclines Chemical class 0.000 title claims description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 93
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
239000000243 solution Substances 0.000 claims description 31
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
-1 trifluoroacetamidomethyl Chemical group 0.000 claims description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 20
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 17
229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 16
239000003208 petroleum Substances 0.000 claims description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 12
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
229910052938 sodium sulfate Inorganic materials 0.000 claims description 11
235000011152 sodium sulphate Nutrition 0.000 claims description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 8
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
239000003610 charcoal Substances 0.000 claims description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 6
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 4
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
239000007864 aqueous solution Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
239000012074 organic phase Substances 0.000 claims description 3
229910052763 palladium Inorganic materials 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 2
239000008098 formaldehyde solution Substances 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
229910052697 platinum Inorganic materials 0.000 claims description 2
125000006239 protecting group Chemical group 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
VIZVGXOLAURPQI-UHFFFAOYSA-N 2,2,2-trichloro-n-(chloromethyl)acetamide Chemical compound ClCNC(=O)C(Cl)(Cl)Cl VIZVGXOLAURPQI-UHFFFAOYSA-N 0.000 claims 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 2
229910000041 hydrogen chloride Inorganic materials 0.000 claims 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 claims 1
WXBWKMLIVXELSF-UHFFFAOYSA-N 2,2,2-trifluoro-n,n-dimethylacetamide Chemical compound CN(C)C(=O)C(F)(F)F WXBWKMLIVXELSF-UHFFFAOYSA-N 0.000 claims 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
125000004423 acyloxy group Chemical group 0.000 claims 1
150000001345 alkine derivatives Chemical class 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
238000006243 chemical reaction Methods 0.000 claims 1
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
239000012452 mother liquor Substances 0.000 claims 1
229910052700 potassium Inorganic materials 0.000 claims 1
239000011591 potassium Substances 0.000 claims 1
150000005376 secondary alkyl halides Chemical class 0.000 claims 1
101150008563 spir gene Proteins 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
238000006467 substitution reaction Methods 0.000 claims 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 10
239000000284 extract Substances 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 6
229940098779 methanesulfonic acid Drugs 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
VFTOHJFKIJLYKN-UHFFFAOYSA-N 7-nitro-9h-fluoren-2-ol Chemical group [O-][N+](=O)C1=CC=C2C3=CC=C(O)C=C3CC2=C1 VFTOHJFKIJLYKN-UHFFFAOYSA-N 0.000 description 3
239000004100 Oxytetracycline Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
229960000625 oxytetracycline Drugs 0.000 description 3
239000004323 potassium nitrate Substances 0.000 description 3
235000010333 potassium nitrate Nutrition 0.000 description 3
MTCQOMXDZUULRV-ADOAZJKMSA-N (4s,4as,5ar,12ar)-4-(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=CC=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 MTCQOMXDZUULRV-ADOAZJKMSA-N 0.000 description 2
SWWQQSDRUYSMAR-UHFFFAOYSA-N 1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol;hydrochloride Chemical group Cl.C1=CC(O)=CC=C1CC1C2=CC(O)=C(O)C=C2CCN1 SWWQQSDRUYSMAR-UHFFFAOYSA-N 0.000 description 2
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
235000019366 oxytetracycline Nutrition 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
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 2
239000002023 wood Substances 0.000 description 2
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 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
229910019020 PtO2 Inorganic materials 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
241001413693 Tetrastes Species 0.000 description 1
241001122767 Theaceae Species 0.000 description 1
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
QRTXZGIQTYDABO-UHFFFAOYSA-N carbanolate Chemical compound CNC(=O)OC1=CC(C)=C(C)C=C1Cl QRTXZGIQTYDABO-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
QSPOJWMZYOMAEI-UHFFFAOYSA-N ethyl n-[(ethoxycarbonylamino)methyl]carbamate Chemical compound CCOC(=O)NCNC(=O)OCC QSPOJWMZYOMAEI-UHFFFAOYSA-N 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000010410 layer Substances 0.000 description 1
DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 1
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
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 1
239000002304 perfume Substances 0.000 description 1
OSUYWXKKGWZOJT-UHFFFAOYSA-N prop-1-en-2-yl n,n-diethylcarbamate Chemical compound CCN(CC)C(=O)OC(C)=C OSUYWXKKGWZOJT-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Inorganic materials [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 1
238000003756 stirring Methods 0.000 description 1
PCZXEAAHGUQDNV-XBNKRBCZSA-N tetrahymanol Natural products CC1(C)CC[C@]2(C)CC[C@]3(C)[C@H]4CC[C@H]5[C@@H](CC[C@H](O)C5(C)C)[C@]4(C)CC[C@@]3(C)[C@@H]2C1 PCZXEAAHGUQDNV-XBNKRBCZSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU7301957942A 1972-09-18 1973-09-17 Способ получени производных тетрациклина SU574145A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT2932872		1972-09-18

Publications (1)

Publication Number	Publication Date
SU574145A3 true SU574145A3 (ru)	1977-09-25

Family

ID=11226772

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU7301957942A SU574145A3 (ru)	1972-09-18	1973-09-17	Способ получени производных тетрациклина

Country Status (14)

Country	Link
US (1)	US3901942A (2)
JP (1)	JPS5741458B2 (2)
AT (1)	AT328613B (2)
BE (1)	BE804913A (2)
CA (1)	CA999855A (2)
DE (1)	DE2346535C3 (2)
ES (1)	ES418809A1 (2)
FR (1)	FR2208885B1 (2)
GB (1)	GB1413347A (2)
HU (1)	HU167850B (2)
IE (1)	IE38820B1 (2)
NL (1)	NL158172B (2)
SU (1)	SU574145A3 (2)
ZA (1)	ZA737317B (2)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2577331C2 (ru) *	2007-02-23	2016-03-20	Ховионе Сциентиа Лимитед	Кристаллическое основание миноциклина и способы его получения

Families Citing this family (35)

* Cited by examiner, † Cited by third party
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DE2437487A1 (de) *	1974-08-03	1976-02-19	Merck Patent Gmbh	7-methoxy-6-thia-tetracycline und verfahren zu ihrer herstellung
AU578068B2 (en) *	1984-03-08	1988-10-13	Nippon Zoki Pharmaceutical Co., Ltd.	Hydantoin derivatives and pharmaceutical compositions containing them
JPH0737433B2 (ja) *	1987-06-11	1995-04-26	協和醗酵工業株式会社	７−アミノ−６−デメチル−６−デオキシテトラサイクリンの製造法
US4837030A (en) *	1987-10-06	1989-06-06	American Cyanamid Company	Novel controlled release formulations of tetracycline compounds
JPH01116549U (2) *	1988-01-29	1989-08-07
US5494903A (en)	1991-10-04	1996-02-27	American Cyanamid Company	7-substituted-9-substituted amino-6-demethyl-6-deoxytetracyclines
US5281628A (en) *	1991-10-04	1994-01-25	American Cyanamid Company	9-amino-7-(substituted)-6-demethyl-6-deoxytetracyclines
USRE40183E1 (en)	1991-10-04	2008-03-25	Wyeth Holdings Corporation	7-Substituted-9-substituted amino-6-demethyl-6-deoxytetracyclines
US5675030A (en) *	1994-11-16	1997-10-07	American Cyanamid Company	Method for selective extracting a 7-(hydrogen or substituted amino)-9- (substituted glycyl) amido!-6-demethyl-6-deoxytetracycline compound
WO1999037306A1 (en) *	1998-01-23	1999-07-29	Trustees Of Tufts College	Pharmaceutically active compounds and methods of use thereof
EA016099B1 (ru) *	1999-09-14	2012-02-28	Трастис Оф Тафтс Коллидж	Замещенный аналог тетрациклина (варианты) и способ получения замещенного аналога тетрациклина
US8106225B2 (en) *	1999-09-14	2012-01-31	Trustees Of Tufts College	Methods of preparing substituted tetracyclines with transition metal-based chemistries
US20020132798A1 (en)	2000-06-16	2002-09-19	Nelson Mark L.	7-phenyl-substituted tetracycline compounds
AU2001268475A1 (en) *	2000-06-16	2002-01-02	Trustees Of Tufts College	7-phenyl-substituted tetracycline compounds
US20040224927A1 (en)	2000-06-16	2004-11-11	Trustees Of Tufts College	7-N-substituted phenyl tetracycline compounds
US7094806B2 (en) *	2000-07-07	2006-08-22	Trustees Of Tufts College	7, 8 and 9-substituted tetracycline compounds
EA009175B1 (ru) *	2000-07-07	2007-12-28	Трастис Оф Тафтс Коллидж	Замещенные соединения миноциклина, фармацевтическая композиция и способ лечения чувствительного к тетрациклину состояния млекопитающего
IL153672A0 (en) *	2000-07-07	2003-07-06	Tufts College	7-substituted tetracycline compounds
WO2002072506A2 (en) *	2001-03-13	2002-09-19	Paratek Pharmaceuticals, Inc.	7-pyrollyl tetracycline compounds and methods of use thereof
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1973
- 1973-09-13 NL NL7312648.A patent/NL158172B/xx unknown
- 1973-09-13 CA CA181,034A patent/CA999855A/en not_active Expired
- 1973-09-14 IE IE1645/73A patent/IE38820B1/xx unknown
- 1973-09-14 JP JP48104458A patent/JPS5741458B2/ja not_active Expired
- 1973-09-14 ZA ZA737317A patent/ZA737317B/xx unknown
- 1973-09-14 FR FR7333067A patent/FR2208885B1/fr not_active Expired
- 1973-09-15 DE DE2346535A patent/DE2346535C3/de not_active Expired
- 1973-09-17 SU SU7301957942A patent/SU574145A3/ru active
- 1973-09-17 AT AT799673A patent/AT328613B/de not_active IP Right Cessation
- 1973-09-17 HU HUSO1098A patent/HU167850B/hu unknown
- 1973-09-17 GB GB4356473A patent/GB1413347A/en not_active Expired
- 1973-09-17 BE BE135695A patent/BE804913A/xx unknown
- 1973-09-17 US US397691A patent/US3901942A/en not_active Expired - Lifetime
- 1973-09-17 ES ES418809A patent/ES418809A1/es not_active Expired

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Also Published As

Publication number	Publication date
ZA737317B (en)	1974-09-25
US3901942A (en)	1975-08-26
DE2346535B2 (de)	1980-09-11
DE2346535C3 (de)	1981-05-21
BE804913A (fr)	1974-03-18
FR2208885A1 (2)	1974-06-28
CA999855A (en)	1976-11-16
IE38820B1 (en)	1978-06-07
ATA799673A (de)	1975-06-15
NL158172B (nl)	1978-10-16
DE2346535A1 (de)	1974-04-11
GB1413347A (en)	1975-11-12
AT328613B (de)	1976-03-25
JPS4969653A (2)	1974-07-05
IE38820L (en)	1974-03-18
ES418809A1 (es)	1976-03-16
NL7312648A (2)	1974-03-20
JPS5741458B2 (2)	1982-09-03
FR2208885B1 (2)	1977-05-20
AU6033373A (en)	1975-03-20
HU167850B (2)	1975-12-25

Publication	Publication Date	Title
SU574145A3 (ru)	1977-09-25	Способ получени производных тетрациклина
SU1077566A3 (ru)	1984-02-29	Способ получени производных пиридоксина или их солей с кислотами
US2936308A (en)	1960-05-10	Novel reductones and methods of making them
SU1356960A3 (ru)	1987-11-30	Способ получени производных пиридазина
US2734904A (en)	1956-02-14	Xcxnhxc-nh
Knaak et al.	1966	Metabolism of 2-Methyl-2-(methylthio) propionaldehyde O-(Methylcarbamoyl) oxime in Rat
SU628822A3 (ru)	1978-10-15	Способ получени хлоргидрата 4 -эпи-6 оксиадриамицина
US2185220A (en)	1940-01-02	Medicinal agent
SU564805A3 (ru)	1977-07-05	Способ получени производных -(3,3-дифенилпропил)пропилендиамина или их солей
US2883394A (en)	1959-04-21	New indole derivatives
US3665037A (en)	1972-05-23	4-methylcylohexylhydroxy amine
US2725399A (en)	1955-11-29	Tertiary dialkylamino propanols
US3467710A (en)	1969-09-16	Beta-(4- or 5-phenyl-1-naphthalene) ethylamines
US3886195A (en)	1975-05-27	1-Trifluoromethylphenyl-2-cyanoalkylamine propane
US2878254A (en)	1959-03-17	N, n'-alkylene-bis-(3-hydroxypiperidine) compounds and preparation thereof
US2916498A (en)	1959-12-08	J-aryl-j-alkyl-z-pyrrolidones
Ross	1959	The tumour growth inhibitory activity of some sulphur mustard gas derivatives
US3417100A (en)	1968-12-17	8,(9)-dehydro-6-thiaestrone-3-methyl ether
CN115385777B (zh)	2023-12-22	一种基于硼氢化钠还原生成的醇的纯化方法
Holly et al.	1952	Carcinolytic Compounds. III. 9-(1'-Glycityl)-isoalloxazines
US2748120A (en)	1956-05-29	2-amino-6-aryl-5, 6-dihydro-4-hydroxy-pyrimidines
Takahashi et al.	1958	Syntheses of Analgesics. XVII. Antipyrine Derivatives.(4)
Cambanis et al.	1969	Potential anticancer agents. V. Aromatic nitrogen mustards related to 3-[N, N-bis (2-chloroethyl) amino]-4-methylbenzoic acid
CA1116631A (en)	1982-01-19	Phenoxy alcoylamides
NO137498B (no)	1977-11-28	Mellomprodukt for fremstilling av lokalanestetisk virksomt 2-(n-n-propyl-tert.-amylamino)-2`, 6`-acetoxylidid

SU574145A3 - Способ получени производных тетрациклина - Google Patents

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