KR830005232A - 2β-클로로메틸-2α-메틸페남-3α-카르복실산 술폰, 염 또는 그의 에스테르의 제조방법 - Google Patents
2β-클로로메틸-2α-메틸페남-3α-카르복실산 술폰, 염 또는 그의 에스테르의 제조방법 Download PDFInfo
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- KR830005232A KR830005232A KR1019810000176A KR810000176A KR830005232A KR 830005232 A KR830005232 A KR 830005232A KR 1019810000176 A KR1019810000176 A KR 1019810000176A KR 810000176 A KR810000176 A KR 810000176A KR 830005232 A KR830005232 A KR 830005232A
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- South Korea
- Prior art keywords
- ester
- acid
- compound
- hydrogen
- benzyl
- Prior art date
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- 150000002148 esters Chemical class 0.000 title claims 16
- 238000000034 method Methods 0.000 title claims 13
- 150000003839 salts Chemical class 0.000 title claims 9
- -1 acetoxymethyl Chemical group 0.000 claims 18
- 239000002253 acid Substances 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 239000004480 active ingredient Substances 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims 6
- 239000002132 β-lactam antibiotic Substances 0.000 claims 6
- 229940124586 β-lactam antibiotics Drugs 0.000 claims 6
- 150000007513 acids Chemical class 0.000 claims 5
- 230000003115 biocidal effect Effects 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 239000003242 anti bacterial agent Substances 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 150000004965 peroxy acids Chemical class 0.000 claims 3
- 239000000243 solution Substances 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 241000894006 Bacteria Species 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- 108090000204 Dipeptidase 1 Proteins 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims 2
- 229960000723 ampicillin Drugs 0.000 claims 2
- 102000006635 beta-lactamase Human genes 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims 2
- 150000002978 peroxides Chemical class 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 241001494479 Pecora Species 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 150000002696 manganese Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 150000004967 organic peroxy acids Chemical class 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
Classifications
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/04—Preparation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/28—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with modified 2-carboxyl group
- C07D499/32—Esters
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/28—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with modified 2-carboxyl group
- C07D499/34—Thio-acid; Esters thereof
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- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/28—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with modified 2-carboxyl group
- C07D499/34—Thio-acid; Esters thereof
- C07D499/36—O-esters
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
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- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
- C07D499/66—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms with alicyclic rings as additional substituents on the carbon chain
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- C07—ORGANIC CHEMISTRY
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- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
- C07D499/68—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms with aromatic rings as additional substituents on the carbon chain
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- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
- C07D499/70—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms with hetero rings as additional substituents on the carbon chain
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- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/86—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with only atoms other than nitrogen atoms directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
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- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/87—Compounds being unsubstituted in position 3 or with substituents other than only two methyl radicals attached in position 3, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
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- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/897—Compounds with substituents other than a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, directly attached in position 2
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- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (32)
- 다음 구조식을 갖는 산 또는 언급한 산의 약학적으로 받아들여질 수 있는 염 또는 언급한 산의 물리학적으로 가수분해될 수 있는 에스테르.
- 펜아실, 아세톡시메틸, 피발오일옥시메틸, α-아세톡시에틸, α-아세톡시벤질, α-피발오일옥시에틸, 3-프타리딜, 5-인다닐, 메톡시메틸, 벤조일옥시메틸, α-에틸부티릴옥시메틸, 프로피오닐옥시메틸, 발레틸옥시메틸, 이소부티릴옥시메틸, 6-[(R)-2-아미노-2-페닐아세트아미도]-3,3-디메틸-7-옥소-4-티아-1-아자비사이클로[3,2,0]-헵탄-2-카르보닐옥시메틸 또는 6-[(R)-2-아미노-2-p-하이드록시페닐 아세트아미도]-3,3-디메틸-7-옥소-4-티아-1-아자비사이클로[3,2,0]-헵탄-2-카르보닐옥시메틸의 구성그룹으로부터 선택된 청구범위 1의 에스테르.
- 6-[(R)-2-아미노-2-페닐아세트아미도]-3,3-디메틸-7-옥소-4-티아-1-아자비사이클로[3,2,0] 헵탄-2-카르보닐메틸인 청구범위 2의 에스테르.
- 6-[(R)-2-아미노-2-p-하이드록시페닐 아세트아미도]-3,3-디메틸-7-옥소-4-티아-1-아자비사이클로[3,2,0] 헵탄-2-카르보닐메틸인 청구범위 2의 에스테르.
- 다음 구조식의 에스테르상기 식에서,R은또는상기에서 R1은 수소 또는 하이드록시이고 R2는 수소, 하이드록시, 메틸, 메톡시 또는 클로로이다.
- a) 다음 구조식을 갖는 에스테르를 촉매적으로 수첨시킨 후상기 식에서 R1은 벤질 또는 치환된 벤질b) 수첨화시킨 생성물을 산화시켜 언급한 원하는 산 또는 이들의 염을 생성한 후, 만약 원한다면c) 언급한 산 또는 이들의 염을 에스테르화시켜 언급한 산의 쉽게 가수분해될 수 있는 에스테르를 생성하는 것으로 구성되는 청구범위 1-4에서 청구된 화합물의 제조방법.
- 수첨을 팔람듐 촉매로 수행하는 청구범위 6에 따른 공정.
- 산화를 알카리금속과 망간염 또는 유기과산으로 수행하는 청구범위 6에 따른 공정.
- KMnO4, H2O2또는 과산화물 또는 과산으로 다음 구조식을 갖는 에스테르를 산화시켜다음 구조식을 갖는 에스테르 설폭사이드를 생성하고 그후(b) 언급한 에스테르를 설폭사이드를 산에서 금속과 예를 들면 빙초산에서 아연과 반응시켜 언급한 산 또는 염을 생성한 후, 만약 원한다면,(c) 언급한 산 또는 이들의 염을 에스테르화시켜 언급한 산의 쉽게 가수분해될 수 있는 에스테르를 생성하는 단계로 구성되는 청구범위 1-4에서 청구된 화합물의 제조방법.
- 다음 구조식을 갖는 화합물 용액의 산으로 처리하는 것으로 구성되는 청구범위 5에서 청구된 화합물의 제조방법.상기 식에서R은또는상기에서 R4는 수소 또는 하이드록시이고 R5는 수소, 하이드록시, 메틸, 메톡시 또는 클로로이고 R1은 알킬, 아르알킬 또는 아릴, R2는 수소, 알킬, 아르알킬 또는 아릴이고 R3는 알킬, 아르알킬, 아릴, 알콕시, 아르알콕시 또는 아릴옥시 또는상기에서R4와 R5는 수소, 알킬, 아르알킬 또는 아릴 또는 질소와 함께 취해질 때 피페리디노, 또는 모르포리노이고 산과 언급한 처리는 상온에서 유기용매 또는 수성에서 또는 부분적으로 수성용액에서 수행된다.
- R1이 메틸, R2가 수소이고, R3가 메톡시, 에톡시 또는 메틸인 청구범위 10의 공정.
- 반응이 아세톤 또는 클로로포름에서 수행하는 청구범위 10의 공정.
- 반응을 pH가 1 내지 5 사이에서 수행하는 청구범위 10-12의 공정.
- 활성성분으로서 유리산 또는 담체 또는 희석제 존재하에 청구범위 1에서 청구된 화합물의 약학적으로 받아들여질 수 있는 염을 투여하는 것으로 구성되는 β-락타메이스 생성 박테리아에 대해 β-락탐 항생작용의 효과를 강화시키기 위한 약학적 조성물.
- 청구범위 2-5의 어느 하나에서 청구된 활성성분 에스테르로서 구성되는 항생제 조성물.
- 유리산 또는 담체 또는 희석제 존재하에 β-락탐 항생제와 혼합물인 청구범위 1 산의 약학적으로 받아들여질 수 있는 염을 저해하는 활성성분 β-락타메이스로서 구성되는 항생제 조성물.
- β-락탐 항생제가 세포라니드, 아목실린 또는 암피실린인 청구범위 16의 조성물.
- 활성성분의 비가 1:5 내지 5:1인 청구범위 16과 17의 조성물.
- 활성성분의 비가 1:1인 청구범위 16과 17의 조성물.
- 유리산 또는 청구범위 1에서 청구된 화합물의 약학적으로 받아들여질 수 있는 염을 투여하는 것으로 구성되는 β-락타케이스 생성 박테리아에 대해 β-락탐 항생효과를 강화시키는 방법.
- 청구범위 2-5의 어느 하나에서 청구된 항생적으로 효과적인 양에스테르를 투여하는 것으로 구성되는 감염성 질병 치료방법.
- 유리산 또는 β-락탐 항생제와 청구범위 1에서 청구된 산의 약학적으로 받아들여질 수 있는 염의 항생적으로 효과적인 양을 함께 투여하는 것으로 구성되는 감염성 질병 치료방법.
- β-락탐 항생제가 세포라니드, 암피실린 또는 아목실린인 청구범위 22의 방법.
- 투여된 활성성분의 비가 1:5 내지 5:1인 청구범위 22 또는 23의 방법.
- 활성성분의 비가 1:1인 청구범위 22 또는 23의 방법.
- 다음 구조식을 갖는 에스테르.상기에서 R은 벤질 또는 p-니트로벤질.
- 다음 구조식을 갖는 에스테르.상기에서 R은 벤질, p-니트로벤질 또는 β, β, β-트리클로로에틸.
- R이 β, β, β-트리클로로에틸인 청구범위 27의 에스테르.
- 다음 구조식을 갖는 에스테르.
- 다음 구조식을 갖는 화합물을 3급아민과 산클로라이드의 등몰량 존재하에 불활성 유기용매에서 반응이 거의 완결될때까지 가열하는 것으로 구성되는 청구범위 26에서 청구된 화합물의 제조방법.상기 식에서 R은 벤질 또는 치환된 벤질.
- 과산의 사용에 의해 상온에서 다음 구조식을 갖는 화합물의 용액을 불활성 용매에서 산화시키는 것으로 구성되는 청구범위 27과 28에서 청구된 화합물의 제조방법.상기 식에서 R은 벤질 또는 치환된 벤질.
- KMnO4, H2O2와 같은 산화제 또는 과산화물 또는 과산의 사용에 의해 상온에서 다음 구조식을 갖는 화합물의 용액을 불활성 용매에서 산화시키는 것으로 구성되는 청구범위 29에서 청구된 화합물의 제조 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019840004326A KR850001066B1 (ko) | 1980-01-21 | 1984-07-21 | 2β-클로로메틸-2α-메틸페남-3α-카르복실산술폰, 2염 또는 그의 에스테르의 제조방법 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11389480A | 1980-01-21 | 1980-01-21 | |
US113894 | 1980-01-21 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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KR1019840004326A Division KR850001066B1 (ko) | 1980-01-21 | 1984-07-21 | 2β-클로로메틸-2α-메틸페남-3α-카르복실산술폰, 2염 또는 그의 에스테르의 제조방법 |
Publications (2)
Publication Number | Publication Date |
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KR830005232A true KR830005232A (ko) | 1983-08-03 |
KR840002214B1 KR840002214B1 (ko) | 1984-12-03 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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KR1019810000176A KR840002214B1 (ko) | 1980-01-21 | 1981-01-21 | 2β-클로로메틸-2α-메틸페남-3α-카르복실산 술폰, 염 또는 그의 에스테르의 제조방법 |
Country Status (16)
Country | Link |
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JP (1) | JPS56104886A (ko) |
KR (1) | KR840002214B1 (ko) |
AT (1) | AT371469B (ko) |
AU (2) | AU539768B2 (ko) |
BE (1) | BE887173A (ko) |
ES (3) | ES498717A0 (ko) |
FI (1) | FI67553C (ko) |
FR (2) | FR2482103A1 (ko) |
GR (1) | GR73512B (ko) |
IE (1) | IE51078B1 (ko) |
LU (1) | LU83071A1 (ko) |
NZ (1) | NZ196055A (ko) |
PH (1) | PH18955A (ko) |
PT (1) | PT72373B (ko) |
YU (5) | YU44195B (ko) |
ZA (1) | ZA81306B (ko) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4406887A (en) * | 1981-10-13 | 1983-09-27 | Bristol-Myers Company | Method for treating resistant bacteria including anaerobes |
JPS58185589A (ja) * | 1982-04-23 | 1983-10-29 | Taiho Yakuhin Kogyo Kk | ペニシリン誘導体 |
US4496484A (en) * | 1983-04-22 | 1985-01-29 | Taiho Pharmaceutical Company, Limited | Penicillin derivatives |
DE3752124T2 (de) * | 1986-01-17 | 1998-03-26 | Beecham Group Plc | Verfahren zur Herstellung von Penem Derivaten und Zwischenprodukte zu dieser Herstellung |
JP2603082B2 (ja) * | 1987-09-07 | 1997-04-23 | 大塚化学株式会社 | ペニシラン酸誘導体の製造法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US4241050A (en) * | 1978-09-01 | 1980-12-23 | Pfizer Inc. | Penam 1,1-dioxides as beta-lactamase inhibitors |
IE49881B1 (en) * | 1979-02-13 | 1986-01-08 | Leo Pharm Prod Ltd | B-lactam intermediates |
-
1981
- 1981-01-16 ZA ZA00810306A patent/ZA81306B/xx unknown
- 1981-01-16 FI FI810121A patent/FI67553C/fi not_active IP Right Cessation
- 1981-01-19 PH PH25094A patent/PH18955A/en unknown
- 1981-01-20 PT PT72373A patent/PT72373B/pt not_active IP Right Cessation
- 1981-01-20 FR FR8100970A patent/FR2482103A1/fr active Granted
- 1981-01-20 NZ NZ196055A patent/NZ196055A/en unknown
- 1981-01-20 IE IE102/81A patent/IE51078B1/en not_active IP Right Cessation
- 1981-01-20 YU YU144/81A patent/YU44195B/xx unknown
- 1981-01-21 GR GR63929A patent/GR73512B/el unknown
- 1981-01-21 ES ES498717A patent/ES498717A0/es active Granted
- 1981-01-21 AU AU66514/81A patent/AU539768B2/en not_active Ceased
- 1981-01-21 LU LU83071A patent/LU83071A1/fr unknown
- 1981-01-21 AT AT0023381A patent/AT371469B/de not_active IP Right Cessation
- 1981-01-21 BE BE0/203552A patent/BE887173A/fr not_active IP Right Cessation
- 1981-01-21 JP JP653681A patent/JPS56104886A/ja active Granted
- 1981-01-21 KR KR1019810000176A patent/KR840002214B1/ko active
- 1981-07-30 FR FR8114863A patent/FR2491071A1/fr active Granted
- 1981-12-24 ES ES508346A patent/ES508346A0/es active Granted
- 1981-12-24 ES ES508347A patent/ES508347A0/es active Granted
-
1983
- 1983-04-22 YU YU923/83A patent/YU45557B/xx unknown
- 1983-04-22 YU YU922/83A patent/YU45556B/xx unknown
- 1983-04-22 YU YU924/83A patent/YU44740B/xx unknown
- 1983-10-31 YU YU02175/83A patent/YU217583A/xx unknown
-
1984
- 1984-08-10 AU AU31833/84A patent/AU558708B2/en not_active Ceased
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