DK174169B1 - Guanidinsalte af amino- -lactamsyrer og fremgangsmåde til fremstilling deraf - Google Patents

Guanidinsalte af amino- -lactamsyrer og fremgangsmåde til fremstilling deraf Download PDF

Info

Publication number: DK174169B1
Authority: DK; Denmark
Prior art keywords: formula; salt; acid; methyl; amino
Prior art date: 1983-05-26

Application number

DK198402557A

Other languages

Danish (da)

English (en)

Other versions

DK255784D0 (da

DK255784A (da

Inventor

Juan Cabre Castellvi

Antonio Luis Palomo Coll

Alberto Palomo Coll

Original Assignee

Biochemie Sa

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.)

1983-05-26

Filing date

1984-05-24

Publication date

2002-08-12

1984-05-24 Application filed by Biochemie Sa filed Critical Biochemie Sa

1984-05-24 Publication of DK255784D0 publication Critical patent/DK255784D0/da

1984-11-27 Publication of DK255784A publication Critical patent/DK255784A/da

2002-08-12 Application granted granted Critical

2002-08-12 Publication of DK174169B1 publication Critical patent/DK174169B1/da

Links

239000002253 acid Substances 0.000 title claims abstract description 93
238000002360 preparation method Methods 0.000 title claims abstract description 19
238000000034 method Methods 0.000 title claims abstract description 12
150000007513 acids Chemical class 0.000 title claims description 18
150000002357 guanidines Chemical class 0.000 title claims description 6
150000003839 salts Chemical class 0.000 claims abstract description 121
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 39
-1 ethoxyl group Chemical group 0.000 claims abstract description 35
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
125000004429 atom Chemical group 0.000 claims abstract description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
125000003118 aryl group Chemical group 0.000 claims abstract description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
229910052799 carbon Inorganic materials 0.000 claims abstract description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims abstract description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 3
239000001301 oxygen Substances 0.000 claims abstract description 3
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VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims abstract description 3
125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 163
150000001875 compounds Chemical class 0.000 claims description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
239000000203 mixture Substances 0.000 claims description 41
239000002904 solvent Substances 0.000 claims description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 8
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 5
150000001408 amides Chemical class 0.000 claims description 5
DVZXTQGTLXFVRQ-UHFFFAOYSA-N 1-benzyl-1,2,3,3-tetramethylguanidine Chemical compound CN=C(N(C)C)N(C)CC1=CC=CC=C1 DVZXTQGTLXFVRQ-UHFFFAOYSA-N 0.000 claims description 3
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
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125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
KYDCMCVBKYYQCI-JLOHTSLTSA-N (6r)-7-amino-8-oxo-3-(phenylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)N)CC=1CSC1=CC=CC=C1 KYDCMCVBKYYQCI-JLOHTSLTSA-N 0.000 claims 1
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FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 1
150000003457 sulfones Chemical class 0.000 claims 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 1
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239000005864 Sulphur Substances 0.000 abstract 1
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125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
150000002431 hydrogen Chemical group 0.000 abstract 1
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 abstract 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
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150000003852 triazoles Chemical class 0.000 abstract 1
239000000243 solution Substances 0.000 description 97
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
238000003756 stirring Methods 0.000 description 18
238000001556 precipitation Methods 0.000 description 14
239000002244 precipitate Substances 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
238000001704 evaporation Methods 0.000 description 10
230000008020 evaporation Effects 0.000 description 10
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 10
150000003952 β-lactams Chemical class 0.000 description 10
240000007817 Olea europaea Species 0.000 description 9
239000000047 product Substances 0.000 description 8
ISNICOKBNZOJQG-UHFFFAOYSA-N 1,1,2,3,3-pentamethylguanidine Chemical compound CN=C(N(C)C)N(C)C ISNICOKBNZOJQG-UHFFFAOYSA-N 0.000 description 7
239000007787 solid Substances 0.000 description 7
LJNQGWIMQCKPSH-UHFFFAOYSA-N 2-ethyl-1,1,3,3-tetramethylguanidine Chemical compound CCN=C(N(C)C)N(C)C LJNQGWIMQCKPSH-UHFFFAOYSA-N 0.000 description 6
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
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125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 4
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JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 3
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238000004452 microanalysis Methods 0.000 description 3
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HJSGHKMSDOLGJJ-IOJJLOCKSA-N (6r)-7-amino-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)C(N)[C@H]2SC1 HJSGHKMSDOLGJJ-IOJJLOCKSA-N 0.000 description 2
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229910052698 phosphorus Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
NTRMGKGYFRQRJL-UHFFFAOYSA-N (3-amino-2-oxoazetidin-1-yl)phosphonic acid Chemical compound NC1CN(P(O)(O)=O)C1=O NTRMGKGYFRQRJL-UHFFFAOYSA-N 0.000 description 1
RFTNRDGDQJYFAM-OMNKOJBGSA-N (6R)-7-amino-3-[(2-methoxyacetyl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC1[C@@H]2N(C(=C(CS2)CSC(=O)COC)C(=O)O)C1=O RFTNRDGDQJYFAM-OMNKOJBGSA-N 0.000 description 1
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238000005160 1H NMR spectroscopy Methods 0.000 description 1
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239000004927 clay Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
ZFDIRQKJPRINOQ-UHFFFAOYSA-N ethyl but-2-enoate Chemical group CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000003956 methylamines Chemical class 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
KINULKKPVJYRON-PVNXHVEDSA-N n-[(e)-[10-[(e)-(4,5-dihydro-1h-imidazol-2-ylhydrazinylidene)methyl]anthracen-9-yl]methylideneamino]-4,5-dihydro-1h-imidazol-2-amine;hydron;dichloride Chemical compound Cl.Cl.N1CCN=C1N\N=C\C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1\C=N\NC1=NCCN1 KINULKKPVJYRON-PVNXHVEDSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
210000000287 oocyte Anatomy 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical compound P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
229940108461 rennet Drugs 0.000 description 1
108010058314 rennet Proteins 0.000 description 1
XOVSRHHCHKUFKM-UHFFFAOYSA-N s-methylthiohydroxylamine Chemical compound CSN XOVSRHHCHKUFKM-UHFFFAOYSA-N 0.000 description 1
238000010517 secondary reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229960004257 sulfaguanidine Drugs 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000002132 β-lactam antibiotic Substances 0.000 description 1
229940124586 β-lactam antibiotics Drugs 0.000 description 1
150000003953 γ-lactams Chemical class 0.000 description 1
150000003955 ε-lactams Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- 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
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/02—Preparation
- C07D477/06—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
- C07D477/08—Modification of a carboxyl group directly attached in position 2, e.g. esterification
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/568—Four-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Molecular Biology (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Cephalosporin Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DK198402557A 1983-05-26 1984-05-24 Guanidinsalte af amino- -lactamsyrer og fremgangsmåde til fremstilling deraf DK174169B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ES522728		1983-05-26
ES522728A ES8505362A1 (es)	1983-05-26	1983-05-26	"sales de acidos amino-beta-lactamicos, para su aplicacion a la obtencion de n-acil derivados de los mismos, y procedimiento para la obtencion de dichas sales"

Publications (3)

Publication Number	Publication Date
DK255784D0 DK255784D0 (da)	1984-05-24
DK255784A DK255784A (da)	1984-11-27
DK174169B1 true DK174169B1 (da)	2002-08-12

Family

ID=8485785

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK198402557A DK174169B1 (da)	1983-05-26	1984-05-24	Guanidinsalte af amino- -lactamsyrer og fremgangsmåde til fremstilling deraf

Country Status (8)

Country	Link
US (1)	US4659814A (ja)
EP (1)	EP0127541B1 (ja)
JP (2)	JPH07108896B2 (ja)
AT (1)	ATE55134T1 (ja)
CA (1)	CA1278568C (ja)
DE (1)	DE3482853D1 (ja)
DK (1)	DK174169B1 (ja)
ES (1)	ES8505362A1 (ja)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT400717B (de) *	1993-07-30	1996-03-25	Biochemie Gmbh	Neue guanidin- und amidinsalze von 7-amino-3- hydroxymethyl-3-cephem-4-carbonsäure
US5908929A (en) *	1996-12-05	1999-06-01	Vitara Chemicals Limited	Process for the manufacture of the antibiotic 7-(D-α-amino-α-phenylacetamido)-3-methyl-3-cephem-4-carboxylic acid (cephalexin) and pharmaceutically acceptable salts thereof
AT411996B (de)	2000-09-11	2004-08-26	Sandoz Ag	Verfahren zur herstellung von cefuroxim in der form seines n-butylammoniumsalzes
GB0118764D0 (en)	2001-08-01	2001-09-26	Biochemie Gmbh	Organic compounds
EP1363345A3 (en) *	2002-05-09	2005-04-27	Wilson Greatbatch Technologies, Inc.	Guanidine derivatives as cations for ambient temperature molten salts in electrochemical power sources
US7214825B2 (en)	2003-10-17	2007-05-08	Honeywell International Inc.	O-(3-chloropropenyl) hydroxylamine free base
CN102977122A (zh) *	2012-10-08	2013-03-20	江苏德峰药业有限公司	一种头孢替唑酸的制备方法
CN110317215A (zh) *	2019-07-26	2019-10-11	伊犁川宁生物技术有限公司	一种降低d-7-aca中do-7-aca杂质含量的方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2865913A (en) *	1957-04-29	1958-12-23	Monsanto Canada Ltd	Arylsulfonyl derivatives of bicyclic guanidines
EP0048953B1 (en) *	1980-09-29	1988-03-09	E.R. Squibb & Sons, Inc.	Beta-lactam antibiotics
DK165118C (da) *	1980-11-22	1993-03-01	Gema Sa	Fremgangsmaade til fremstilling af oploesninger af 7-aminocephalosporansyrer

1983
- 1983-05-26 ES ES522728A patent/ES8505362A1/es not_active Expired
1984
- 1984-05-15 CA CA000454356A patent/CA1278568C/en not_active Expired - Lifetime
- 1984-05-18 US US06/612,053 patent/US4659814A/en not_active Expired - Lifetime
- 1984-05-24 AT AT84401077T patent/ATE55134T1/de not_active IP Right Cessation
- 1984-05-24 DE DE8484401077T patent/DE3482853D1/de not_active Expired - Lifetime
- 1984-05-24 DK DK198402557A patent/DK174169B1/da not_active IP Right Cessation
- 1984-05-24 EP EP84401077A patent/EP0127541B1/en not_active Expired - Lifetime
- 1984-05-25 JP JP10629584A patent/JPH07108896B2/ja not_active Expired - Lifetime
1995
- 1995-05-15 JP JP7115868A patent/JP2708724B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
EP0127541B1 (en)	1990-08-01
DK255784D0 (da)	1984-05-24
JPS6034945A (ja)	1985-02-22
CA1278568C (en)	1991-01-02
DE3482853D1 (de)	1990-09-06
JPH07108896B2 (ja)	1995-11-22
EP0127541A2 (en)	1984-12-05
EP0127541A3 (en)	1985-11-06
JPH09110870A (ja)	1997-04-28
DK255784A (da)	1984-11-27
US4659814A (en)	1987-04-21
ES522728A0 (es)	1985-06-01
ES8505362A1 (es)	1985-06-01
JP2708724B2 (ja)	1998-02-04
ATE55134T1 (de)	1990-08-15

Legal Events

Date	Code	Title	Description
2002-08-12	B1	Patent granted (law 1993)
2004-06-14	PUP	Patent expired

Publication	Publication Date	Title
CA1272713A (en)	1990-08-14	Carboxyalkenamidocephalosporins
KR20030078882A (ko)	2003-10-08	티아졸릴 아세트산의 신규 티오에스테르 유도체 및세팔로스포린 화합물의 제조에서 그의 용도
CN103254213A (zh)	2013-08-21	类美登素酯的制备方法及用于所述方法的组合物
NO844006L (no)	1985-04-09	Cefalosporinderivater og fremgangsmaate til deres fremstilling
EP0264091B1 (en)	1992-02-05	3-propenylcephem derivative, preparation thereof, chemical intermediates therein, pharmaceutical composition and use
AU731265B2 (en)	2001-03-29	A process for the selective preparation of z-isomers of a 3-(2-substituted vinyl-)-cephalosporin
US5202315A (en)	1993-04-13	Cephalosporin compounds
EP0127541B1 (en)	1990-08-01	Salts of amino-beta-lactamic acids and process for the preparation thereof
DK163584B (da)	1992-03-16	7-amino-3-propenylcephalosporinsyrederivater samt fremgangsmaade til fremstilling deraf
SE458607B (sv)	1989-04-17	1-metyltetrazol-5-yl-(4-etyl-2,3-dioxopierazin-1-yl)-karbonyltiolat och tetrazolo-(1,5-b)pyridazin-6-yl-(4-etyl-2,3-dioxopiperazin-l-yl) karbonyltiolat
IE50176B1 (en)	1986-03-05	Process for the production of phenylglycyl chloride hydrochlorides
KR880001775B1 (ko)	1988-09-15	3위치가 티오메틸 헤테로 고리기에 의해 치환된 세팔로스포린 유도체의 제조방법
US3799924A (en)	1974-03-26	Ester cleavage process
EP0640608A1 (en)	1995-03-01	Intermediates in the synthesis of cephalosporins
SE446188B (sv)	1986-08-18	7-/2,3-dioxo-1-piperzinkarboxamido/-cefalosporinderivat
EP0045717B1 (en)	1985-09-25	New cephalosporin derivatives, their production and their use
CA1056812A (en)	1979-06-19	7a-methoxycephalosporin compounds
NO752202L (ja)	1975-12-23
IE49368B1 (en)	1985-09-18	Cephalosporin derivatives
LATTRELL et al.	1988	SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS IN THE CEFPIROME SERIES II. ANALOGUES OF CEFPIROME WITH DIFFERENT 7-HETEROARYLACETAMIDO AND 3'-AMMONIUM SUBSTITUENTS
GB2195334A (en)	1988-04-07	1-Methanesulfonyloxy-6-trifluoromethyl-1H-benzotriazole and its use in preparing cephalosporin derivatives
US4159373A (en)	1979-06-26	7-Acyl-3-(sulfonic acid and sulfamoyl substituted tetrazolyl thiomethyl) cephalosporins
KR0129567B1 (ko)	1998-04-09	반응성 유기산 유도체로부터 세팔로스포린 화합물의 제조방법
EP0000285A1 (en)	1979-01-10	7-Acylamino-3-((3-(carboxymethyl) thio-1 H-1,2,4-triazol-5-yl) thiomethyl)-3-cephem-4-carboxylic acid derivatives, processes for their preparation and compositions containing them
KR790001175B1 (ko)	1979-09-10	7-아미노 세팔로스포란산 및 그 유도체의 에스테르의 제조방법