SU556724A3 - Способ получени 6- -дезокситетрациклинов - Google Patents

Способ получени 6- -дезокситетрациклинов

Info

Publication number: SU556724A3
Authority: SU; USSR - Soviet Union
Prior art keywords: deoxy; hydrogen; mixture; methanol; hours
Prior art date: 1973-06-08

Application number

SU2002077A

Other languages

English (en)

Russian (ru)

Inventor

Мотт Бреннан Томас

Фаубл Герман

Original Assignee

Пфайзер Инк (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.)

1973-06-08

Filing date

1974-02-15

Publication date

1977-04-30

1974-02-15 Application filed by Пфайзер Инк (Фирма) filed Critical Пфайзер Инк (Фирма)

1977-04-30 Application granted granted Critical

1977-04-30 Publication of SU556724A3 publication Critical patent/SU556724A3/ru

Links

238000000034 method Methods 0.000 title claims 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
238000004458 analytical method Methods 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
239000012299 nitrogen atmosphere Substances 0.000 claims description 10
239000011541 reaction mixture Substances 0.000 claims description 10
238000002474 experimental method Methods 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
239000000047 product Substances 0.000 claims description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
239000003054 catalyst Substances 0.000 claims description 7
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
239000004100 Oxytetracycline Substances 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
229960000625 oxytetracycline Drugs 0.000 claims description 5
WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
238000007872 degassing Methods 0.000 claims description 3
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
229910052703 rhodium Inorganic materials 0.000 claims description 3
239000010948 rhodium Substances 0.000 claims description 3
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 3
239000007787 solid Substances 0.000 claims description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
239000000706 filtrate Substances 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims 6
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims 4
238000005984 hydrogenation reaction Methods 0.000 claims 3
125000000217 alkyl group Chemical group 0.000 claims 2
229910001507 metal halide Inorganic materials 0.000 claims 2
150000005309 metal halides Chemical class 0.000 claims 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
238000001816 cooling Methods 0.000 claims 1
-1 dialkylamino radical Chemical group 0.000 claims 1
238000001914 filtration Methods 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 claims 1
229910052700 potassium Inorganic materials 0.000 claims 1
239000011591 potassium Substances 0.000 claims 1
239000002244 precipitate Substances 0.000 claims 1
238000002360 preparation method Methods 0.000 claims 1
150000003254 radicals Chemical class 0.000 claims 1
QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 claims 1
MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical class OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 claims 1
239000002904 solvent Substances 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
238000002211 ultraviolet spectrum Methods 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 3
238000011084 recovery Methods 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229960004368 oxytetracycline hydrochloride Drugs 0.000 description 2
BDDWSAASCFBVBK-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 BDDWSAASCFBVBK-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical class OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 1
241000191368 Chlorobi Species 0.000 description 1
YRUGGBDNPPOYBZ-UHFFFAOYSA-N [Cl].[Rh].C=C.C=C Chemical class [Cl].[Rh].C=C.C=C YRUGGBDNPPOYBZ-UHFFFAOYSA-N 0.000 description 1
229910001508 alkali metal halide Inorganic materials 0.000 description 1
150000008045 alkali metal halides Chemical class 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000000539 dimer Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000003446 ligand Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
238000005070 sampling Methods 0.000 description 1
239000012265 solid product Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
IQKSLJOIKWOGIZ-UHFFFAOYSA-N tris(4-chlorophenyl)phosphane Chemical compound C1=CC(Cl)=CC=C1P(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 IQKSLJOIKWOGIZ-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SU2002077A 1973-06-08 1974-02-15 Способ получени 6- -дезокситетрациклинов SU556724A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US36806073A	1973-06-08	1973-06-08

Publications (1)

Publication Number	Publication Date
SU556724A3 true SU556724A3 (ru)	1977-04-30

Family

ID=23449714

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU2002077A SU556724A3 (ru)	1973-06-08	1974-02-15	Способ получени 6- -дезокситетрациклинов

Country Status (3)

Country	Link
CS (1)	CS200465B2 (cs)
PL (1)	PL98239B1 (cs)
SU (1)	SU556724A3 (cs)

1974
- 1974-02-06 CS CS82674A patent/CS200465B2/cs unknown
- 1974-02-15 SU SU2002077A patent/SU556724A3/ru active
- 1974-03-07 PL PL16934574A patent/PL98239B1/pl unknown

Also Published As

Publication number	Publication date
CS200465B2 (cs)	1980-09-15
PL98239B1 (pl)	1978-04-29

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