FI61032C - Foerfarande foer framstaellning av terapeutiskt anvaendbara peptidylfosfonsyror - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara peptidylfosfonsyror Download PDFInfo
- Publication number
- FI61032C FI61032C FI760084A FI760084A FI61032C FI 61032 C FI61032 C FI 61032C FI 760084 A FI760084 A FI 760084A FI 760084 A FI760084 A FI 760084A FI 61032 C FI61032 C FI 61032C
- Authority
- FI
- Finland
- Prior art keywords
- acid
- alanyl
- benzyloxycarbonyl
- water
- amino
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 64
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 30
- BHAYDBSYOBONRV-IUYQGCFVSA-N alafosfalin Chemical compound C[C@H](N)C(=O)N[C@@H](C)P(O)(O)=O BHAYDBSYOBONRV-IUYQGCFVSA-N 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 125000006239 protecting group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 174
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 134
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 108
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 90
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 85
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
- 239000000203 mixture Substances 0.000 description 62
- 239000000243 solution Substances 0.000 description 56
- 239000007858 starting material Substances 0.000 description 55
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
- 239000012467 final product Substances 0.000 description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 229960000583 acetic acid Drugs 0.000 description 38
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 38
- 238000004519 manufacturing process Methods 0.000 description 35
- 239000007787 solid Substances 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 239000012362 glacial acetic acid Substances 0.000 description 26
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 150000003939 benzylamines Chemical class 0.000 description 24
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 24
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 22
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 20
- -1 aminobutyl Chemical group 0.000 description 19
- TYRGLVWXHJRKMT-QMMMGPOBSA-N n-benzyloxycarbonyl-l-serine-betalactone Chemical compound OC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1 TYRGLVWXHJRKMT-QMMMGPOBSA-N 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 15
- 238000001953 recrystallisation Methods 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VSCIMFFPYDZRDE-VKHMYHEASA-N [[(2s)-2-aminopropanoyl]amino]methylphosphonic acid Chemical compound C[C@H](N)C(=O)NCP(O)(O)=O VSCIMFFPYDZRDE-VKHMYHEASA-N 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000003729 cation exchange resin Substances 0.000 description 11
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 11
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 10
- 108090000765 processed proteins & peptides Proteins 0.000 description 10
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 9
- 239000000908 ammonium hydroxide Substances 0.000 description 9
- 230000003115 biocidal effect Effects 0.000 description 9
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
- JXCIHSTVVBWUIM-UHFFFAOYSA-N C(C1=CC=CC=C1)N.C(C)P(O)(O)=O Chemical compound C(C1=CC=CC=C1)N.C(C)P(O)(O)=O JXCIHSTVVBWUIM-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- NEFMGVGBPHIVRK-VIFPVBQESA-N [[(2s)-2-amino-3-phenylpropanoyl]amino]methylphosphonic acid Chemical compound OP(=O)(O)CNC(=O)[C@@H](N)CC1=CC=CC=C1 NEFMGVGBPHIVRK-VIFPVBQESA-N 0.000 description 8
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 8
- FNAUIPGNLGDWRB-UHFFFAOYSA-N dimethoxyphosphorylmethanamine;hydrochloride Chemical compound Cl.COP(=O)(CN)OC FNAUIPGNLGDWRB-UHFFFAOYSA-N 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 7
- RRONHWAVOYADJL-HNNXBMFYSA-N (2s)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 RRONHWAVOYADJL-HNNXBMFYSA-N 0.000 description 6
- 241000588724 Escherichia coli Species 0.000 description 6
- 229940024606 amino acid Drugs 0.000 description 6
- 235000001014 amino acid Nutrition 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
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- 239000002244 precipitate Substances 0.000 description 6
- UIQSKEDQPSEGAU-UWTATZPHSA-N (R)-(1-aminoethyl)phosphonic acid Chemical compound C[C@H](N)P(O)(O)=O UIQSKEDQPSEGAU-UWTATZPHSA-N 0.000 description 5
- DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-N 0.000 description 5
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- USPFMEKVPDBMCG-LBPRGKRZSA-M N-benzyloxycarbonyl-L-leucinate Chemical compound CC(C)C[C@@H](C([O-])=O)NC(=O)OCC1=CC=CC=C1 USPFMEKVPDBMCG-LBPRGKRZSA-M 0.000 description 5
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- PJHFHKYWTILCKG-HMFOOQLRSA-N [(3S)-3-amino-1-[[(2S)-2-aminopropanoyl]amino]-2-oxobutyl]phosphonic acid Chemical compound N[C@@H](C)C(=O)C(NC([C@@H](N)C)=O)P(O)(O)=O PJHFHKYWTILCKG-HMFOOQLRSA-N 0.000 description 5
- XCOFKTFCRZLZIV-LURJTMIESA-N [[(2s)-2-amino-4-methylpentanoyl]amino]methylphosphonic acid Chemical compound CC(C)C[C@H](N)C(=O)NCP(O)(O)=O XCOFKTFCRZLZIV-LURJTMIESA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
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- 229910052757 nitrogen Inorganic materials 0.000 description 5
- FPLBAYCRDXIGAY-JEDNCBNOSA-N (2s)-2-amino-n-(dimethoxyphosphorylmethyl)propanamide;hydrochloride Chemical compound Cl.COP(=O)(OC)CNC(=O)[C@H](C)N FPLBAYCRDXIGAY-JEDNCBNOSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
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- 150000008064 anhydrides Chemical class 0.000 description 4
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- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 3
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- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 description 3
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- AAABTHNNTXZLHU-RITPCOANSA-N [(1r)-1-[[(2s)-2-amino-3-methylbutanoyl]amino]ethyl]phosphonic acid Chemical compound CC(C)[C@H](N)C(=O)N[C@@H](C)P(O)(O)=O AAABTHNNTXZLHU-RITPCOANSA-N 0.000 description 3
- FCWXRYNRJSCDIN-SCZZXKLOSA-N [(1r)-1-[[(2s)-2-amino-3-phenylpropanoyl]amino]ethyl]phosphonic acid Chemical compound OP(=O)(O)[C@H](C)NC(=O)[C@@H](N)CC1=CC=CC=C1 FCWXRYNRJSCDIN-SCZZXKLOSA-N 0.000 description 3
- BPOGEECQMYCWJL-RQJHMYQMSA-N [(1r)-1-[[(2s)-2-amino-4-methylpentanoyl]amino]ethyl]phosphonic acid Chemical compound CC(C)C[C@H](N)C(=O)N[C@@H](C)P(O)(O)=O BPOGEECQMYCWJL-RQJHMYQMSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/10—Alpha-amino-carboxylic acids
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- 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
- A61K31/66—Phosphorus compounds
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- 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
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- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Biophysics (AREA)
- Polymers & Plastics (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB341775 | 1975-01-27 | ||
| GB3417/75A GB1533239A (en) | 1975-01-27 | 1975-01-27 | Peptide derivatives of phosphonic and phosphinic acids |
| GB4778775 | 1975-11-20 | ||
| GB4778775 | 1975-11-20 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI760084A FI760084A (nl) | 1976-07-28 |
| FI61032B FI61032B (fi) | 1982-01-29 |
| FI61032C true FI61032C (fi) | 1982-05-10 |
Family
ID=26238285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI760084A FI61032C (fi) | 1975-01-27 | 1976-01-15 | Foerfarande foer framstaellning av terapeutiskt anvaendbara peptidylfosfonsyror |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4016148A (nl) |
| JP (1) | JPS598278B2 (nl) |
| AR (1) | AR218850A1 (nl) |
| AT (1) | AT359217B (nl) |
| AU (1) | AU502919B2 (nl) |
| BR (1) | BR7600449A (nl) |
| CA (1) | CA1065857A (nl) |
| CH (2) | CH624965A5 (nl) |
| DD (1) | DD123756A5 (nl) |
| DE (1) | DE2602193C2 (nl) |
| DK (1) | DK143755C (nl) |
| DO (1) | DOP1976002544A (nl) |
| ES (1) | ES444622A1 (nl) |
| FI (1) | FI61032C (nl) |
| FR (1) | FR2298335A1 (nl) |
| GR (1) | GR58609B (nl) |
| HU (1) | HU176800B (nl) |
| IE (1) | IE42466B1 (nl) |
| IL (1) | IL48835A (nl) |
| LU (1) | LU74249A1 (nl) |
| NL (1) | NL177021C (nl) |
| NO (1) | NO146429C (nl) |
| PH (1) | PH16560A (nl) |
| PL (1) | PL99096B1 (nl) |
| PT (1) | PT64743B (nl) |
| SE (2) | SE424328B (nl) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1577232A (en) * | 1976-05-14 | 1980-10-22 | Roche Products Ltd | Peptide derivatives of phosphonic and phosphinic acids |
| FR2351125A1 (fr) * | 1976-05-14 | 1977-12-09 | Hoffmann La Roche | Derives peptidiques et procede pour leur preparation |
| GB1585076A (en) * | 1976-07-13 | 1981-02-25 | Roche Products Ltd | Peptides of phosphonic and phosphinic acids |
| IT1081511B (it) * | 1976-07-13 | 1985-05-21 | Hoffmann La Roche | Derivati di peptidi e loro preparazione |
| GB1585275A (en) * | 1976-07-21 | 1981-02-25 | Roche Products Ltd | Peptide derivatives of phosphonic and phosphinic acids |
| US4179464A (en) * | 1977-11-14 | 1979-12-18 | Schultz Robert J | Preparation of N-(phosphonoacetyl)-L-aspartic acid |
| EP0002039A1 (en) * | 1977-11-19 | 1979-05-30 | Ciba-Geigy Ag | Phosphonous acid derivatives, processes for their preparation and their use in combating microorganisms |
| CA1108125A (en) * | 1977-12-23 | 1981-09-01 | Frank R. Atherton | Olgiopeptide derivatives of phosphonic acid |
| US4178306A (en) * | 1978-08-10 | 1979-12-11 | Parsons Jack L | Preparation of N-(phosphonoacetyl)-L-aspartic acid |
| US4154759A (en) * | 1978-08-10 | 1979-05-15 | Henryk Dubicki | Preparation of N-(phosphonoacetyl)-L-aspartic acid |
| US4331591A (en) * | 1978-10-05 | 1982-05-25 | Ciba-Geigy Corporation | Chemical process for the production of α-aminophosphonic acids and peptide derivatives |
| DE2966111D1 (en) * | 1978-10-05 | 1983-10-06 | Ciba Geigy Ag | Process for influencing plant growth |
| EP0026867A1 (de) * | 1979-09-28 | 1981-04-15 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Peptidylphosphonsäuren, deren Herstellung und Verwendung und sie enthaltende pharmazeutische Präparate |
| JPS5831992A (ja) * | 1981-08-19 | 1983-02-24 | Kyowa Hakko Kogyo Co Ltd | 新規生理活性物質ｋ−４およびその製造法 |
| JPS5885897A (ja) * | 1981-11-17 | 1983-05-23 | Kyowa Hakko Kogyo Co Ltd | 光学活性な１−アミノ−２−（４−ヒドロキシフエニル）エチルホスホン酸およびその誘導体 |
| JPS57156498A (en) * | 1981-03-20 | 1982-09-27 | Kyowa Hakko Kogyo Co Ltd | Novel physiologically active substance k-26 |
| EP0103867B1 (en) * | 1982-09-17 | 1986-12-17 | Kyowa Hakko Kogyo Co., Ltd. | Phosphorus-containing peptide derivative |
| US4463092A (en) * | 1982-09-27 | 1984-07-31 | Eli Lilly And Company | Process for production antibiotic A53868 |
| US4482488A (en) * | 1982-09-27 | 1984-11-13 | Eli Lilly And Company | Antibiotic A53868 and process for production thereof |
| PT77368A (en) * | 1982-09-27 | 1983-10-01 | Lilly Co Eli | Improved process for preparing immunomodulating agents or rela-ting there to |
| DE3669512D1 (de) | 1985-06-11 | 1990-04-19 | Ciba Geigy Ag | Mikrobizide mittel. |
| FR2584077B1 (fr) * | 1985-06-28 | 1988-07-08 | Irceba | L-di ou tripeptides possedant une activite biologique utilisable en medecine humaine et veterinaire, procede pour leur obtention et medicament en contenant |
| GB8726714D0 (en) * | 1987-11-14 | 1987-12-16 | Beecham Group Plc | Compounds |
| WO1989007940A1 (en) * | 1988-03-03 | 1989-09-08 | E.R. Squibb & Sons, Inc. | 1,2-hydroxy phosphonates and derivatives thereof |
| AU3964489A (en) * | 1988-07-08 | 1990-02-05 | Smithkline Beckman Corporation | Retroviral protease binding peptides |
| US5468732A (en) * | 1989-02-16 | 1995-11-21 | Pfizer Inc. | Phosphorus containing renin inhibitors |
| WO1990009172A1 (en) * | 1989-02-16 | 1990-08-23 | Pfizer Inc. | Phosphorus containing renin inhibitors |
| US5321153A (en) * | 1992-06-15 | 1994-06-14 | Monsanto Company | Process for making chiral alpha-amino phosphonates selected novel chiral alpha-amino phosphonates |
| US5473092A (en) * | 1992-11-20 | 1995-12-05 | Monsanto Company | Synthesis of optically-active phosphono analogs of succinates |
| GB0022556D0 (en) * | 2000-09-14 | 2000-11-01 | Oxoid Ltd | Improvements in or relating to selective agents for biological cultures |
| EP1325024B1 (en) * | 2000-09-18 | 2011-04-20 | The Newcastle upon Tyne Hospitals National Health Service Trust | Selective growth media |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3893992A (en) * | 1970-11-19 | 1975-07-08 | Rohm & Haas | N-acylated peptides of amino aromatic sulfonic acids and their derivatives |
| GB1445087A (en) * | 1972-11-08 | 1976-08-04 | Ici Ltd | Preparing n-phosphonomethylglycine and nitrile intermediates therefor |
| US3954860A (en) * | 1973-08-06 | 1976-05-04 | Monsanto Company | Phosphorous compounds |
| US3969398A (en) * | 1974-05-01 | 1976-07-13 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
-
1976
- 1976-01-14 IL IL48835A patent/IL48835A/xx unknown
- 1976-01-15 FI FI760084A patent/FI61032C/fi not_active IP Right Cessation
- 1976-01-15 DO DO1976002544A patent/DOP1976002544A/es unknown
- 1976-01-16 PH PH17981A patent/PH16560A/en unknown
- 1976-01-16 AU AU10354/76A patent/AU502919B2/en not_active Expired
- 1976-01-19 CH CH57576A patent/CH624965A5/de not_active IP Right Cessation
- 1976-01-19 US US05/650,336 patent/US4016148A/en not_active Expired - Lifetime
- 1976-01-20 JP JP51004684A patent/JPS598278B2/ja not_active Expired
- 1976-01-20 NL NLAANVRAGE7600539,A patent/NL177021C/nl not_active IP Right Cessation
- 1976-01-21 HU HU76HO1873A patent/HU176800B/hu unknown
- 1976-01-21 DE DE2602193A patent/DE2602193C2/de not_active Expired
- 1976-01-23 DD DD190930A patent/DD123756A5/xx unknown
- 1976-01-23 SE SE7600731A patent/SE424328B/xx unknown
- 1976-01-26 ES ES444622A patent/ES444622A1/es not_active Expired
- 1976-01-26 IE IE143/76A patent/IE42466B1/en unknown
- 1976-01-26 CA CA244,191A patent/CA1065857A/en not_active Expired
- 1976-01-26 DK DK29576A patent/DK143755C/da not_active IP Right Cessation
- 1976-01-26 LU LU74249A patent/LU74249A1/xx unknown
- 1976-01-26 PL PL1976186818A patent/PL99096B1/pl unknown
- 1976-01-26 PT PT64743A patent/PT64743B/pt unknown
- 1976-01-26 NO NO760231A patent/NO146429C/no unknown
- 1976-01-26 GR GR49862A patent/GR58609B/el unknown
- 1976-01-26 BR BR7600449A patent/BR7600449A/pt unknown
- 1976-01-26 FR FR7601973A patent/FR2298335A1/fr active Granted
- 1976-01-26 AT AT49276A patent/AT359217B/de not_active IP Right Cessation
- 1976-01-27 AR AR262030A patent/AR218850A1/es active
-
1977
- 1977-09-07 SE SE7710045A patent/SE7710045L/xx unknown
-
1979
- 1979-09-18 CH CH841979A patent/CH623829A5/de not_active IP Right Cessation
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: F. HOFFMANN-LA ROCHE & CO. |