DE2136067C3 - 3-Fluor-D-alanin, 3-Fluor-D-alanin-2-d, deren Salze und diese Verbindungen enthaltende Arzneimittel - Google Patents
3-Fluor-D-alanin, 3-Fluor-D-alanin-2-d, deren Salze und diese Verbindungen enthaltende ArzneimittelInfo
- Publication number
- DE2136067C3 DE2136067C3 DE2136067A DE2136067A DE2136067C3 DE 2136067 C3 DE2136067 C3 DE 2136067C3 DE 2136067 A DE2136067 A DE 2136067A DE 2136067 A DE2136067 A DE 2136067A DE 2136067 C3 DE2136067 C3 DE 2136067C3
- Authority
- DE
- Germany
- Prior art keywords
- alanine
- fluoro
- antibacterial
- salts
- effectiveness
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- UYTSRQMXRROFPU-UWTATZPHSA-N (2s)-2-amino-3-fluoropropanoic acid Chemical compound FC[C@@H](N)C(O)=O UYTSRQMXRROFPU-UWTATZPHSA-N 0.000 title claims description 26
- 150000001875 compounds Chemical class 0.000 title claims description 10
- UYTSRQMXRROFPU-LIIDHCAMSA-N (2s)-2-amino-2-deuterio-3-fluoropropanoic acid Chemical compound FC[C@](N)([2H])C(O)=O UYTSRQMXRROFPU-LIIDHCAMSA-N 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 title claims 7
- 229940126601 medicinal product Drugs 0.000 title 1
- UYTSRQMXRROFPU-REOHCLBHSA-N (2r)-2-amino-3-fluoropropanoic acid Chemical compound FC[C@H](N)C(O)=O UYTSRQMXRROFPU-REOHCLBHSA-N 0.000 claims description 10
- 230000000844 anti-bacterial effect Effects 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims description 8
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims description 8
- 241001465754 Metazoa Species 0.000 claims description 6
- 239000002775 capsule Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 238000000338 in vitro Methods 0.000 claims description 5
- 238000001727 in vivo Methods 0.000 claims description 5
- 241000588724 Escherichia coli Species 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 241000607142 Salmonella Species 0.000 claims description 3
- 241000191967 Staphylococcus aureus Species 0.000 claims description 3
- 239000003242 anti bacterial agent Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 claims description 3
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 2
- 241000194017 Streptococcus Species 0.000 claims description 2
- 241000193996 Streptococcus pyogenes Species 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 244000052616 bacterial pathogen Species 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 231100000518 lethal Toxicity 0.000 claims description 2
- 230000001665 lethal effect Effects 0.000 claims description 2
- 244000052769 pathogen Species 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 6
- 230000003287 optical effect Effects 0.000 claims 3
- UYTSRQMXRROFPU-UHFFFAOYSA-N 2-azaniumyl-3-fluoropropanoate Chemical compound FCC(N)C(O)=O UYTSRQMXRROFPU-UHFFFAOYSA-N 0.000 claims 2
- 102000004674 D-amino-acid oxidase Human genes 0.000 claims 2
- 108010003989 D-amino-acid oxidase Proteins 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- 150000008541 D-alanines Chemical class 0.000 claims 1
- 241000588722 Escherichia Species 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 1
- 241000588748 Klebsiella Species 0.000 claims 1
- 241000186359 Mycobacterium Species 0.000 claims 1
- 241000606860 Pasteurella Species 0.000 claims 1
- 206010034133 Pathogen resistance Diseases 0.000 claims 1
- 241000588769 Proteus <enterobacteria> Species 0.000 claims 1
- 241000588770 Proteus mirabilis Species 0.000 claims 1
- 241000588767 Proteus vulgaris Species 0.000 claims 1
- 241000589516 Pseudomonas Species 0.000 claims 1
- 241000700159 Rattus Species 0.000 claims 1
- 241000607720 Serratia Species 0.000 claims 1
- 241000191940 Staphylococcus Species 0.000 claims 1
- 229910000831 Steel Inorganic materials 0.000 claims 1
- 241000607598 Vibrio Species 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001294 alanine derivatives Chemical class 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 230000036765 blood level Effects 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000015556 catabolic process Effects 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 230000001627 detrimental effect Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000003682 fluorination reaction Methods 0.000 claims 1
- 239000003979 granulating agent Substances 0.000 claims 1
- 230000035876 healing Effects 0.000 claims 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000005865 ionizing radiation Effects 0.000 claims 1
- 239000006193 liquid solution Substances 0.000 claims 1
- 239000006194 liquid suspension Substances 0.000 claims 1
- 230000004060 metabolic process Effects 0.000 claims 1
- 230000037323 metabolic rate Effects 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 239000003755 preservative agent Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 229940007042 proteus vulgaris Drugs 0.000 claims 1
- 239000010959 steel Substances 0.000 claims 1
- 238000010998 test method Methods 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 238000011287 therapeutic dose Methods 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 238000005303 weighing Methods 0.000 claims 1
- 241000699670 Mus sp. Species 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 5
- 229960003767 alanine Drugs 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- QNAYBMKLOCPYGJ-LIIDHCAMSA-N (2r)-2-amino-2-deuteriopropanoic acid Chemical compound [2H][C@](C)(N)C(O)=O QNAYBMKLOCPYGJ-LIIDHCAMSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 239000004098 Tetracycline Substances 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 229960005091 chloramphenicol Drugs 0.000 description 2
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 229960002180 tetracycline Drugs 0.000 description 2
- 229930101283 tetracycline Natural products 0.000 description 2
- 235000019364 tetracycline Nutrition 0.000 description 2
- 150000003522 tetracyclines Chemical class 0.000 description 2
- 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 1
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 108010041525 Alanine racemase Proteins 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-N 0.000 description 1
- DYDCUQKUCUHJBH-UHFFFAOYSA-N D-Cycloserine Natural products NC1CONC1=O DYDCUQKUCUHJBH-UHFFFAOYSA-N 0.000 description 1
- 125000000030 D-alanine group Chemical group [H]N([H])[C@](C([H])([H])[H])(C(=O)[*])[H] 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 102000003929 Transaminases Human genes 0.000 description 1
- 108090000340 Transaminases Proteins 0.000 description 1
- 206010066901 Treatment failure Diseases 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 108010003977 aminoacylase I Proteins 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 244000144980 herd Species 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- VSQYNPJPULBZKU-UHFFFAOYSA-N mercury xenon Chemical compound [Xe].[Hg] VSQYNPJPULBZKU-UHFFFAOYSA-N 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
Classifications
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/385—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing halogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
- C07C53/21—Acids containing three or more carbon atoms containing fluorine
-
- 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
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/38—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6064570A | 1970-08-03 | 1970-08-03 | |
| US14981471A | 1971-06-03 | 1971-06-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2136067A1 DE2136067A1 (de) | 1972-02-10 |
| DE2136067B2 DE2136067B2 (de) | 1980-01-17 |
| DE2136067C3 true DE2136067C3 (de) | 1980-09-11 |
Family
ID=26740157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2136067A Expired DE2136067C3 (de) | 1970-08-03 | 1971-07-19 | 3-Fluor-D-alanin, 3-Fluor-D-alanin-2-d, deren Salze und diese Verbindungen enthaltende Arzneimittel |
Country Status (13)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ211490A (en) * | 1984-03-23 | 1988-10-28 | Commw Scient Ind Res Org | Deuterated compounds and arthropodicidal compositions |
| JP2009531315A (ja) * | 2006-03-16 | 2009-09-03 | バーテックス ファーマシューティカルズ インコーポレイテッド | 重水素化ｃ型肝炎プロテアーゼインヒビター |
| RU2465264C2 (ru) * | 2006-03-16 | 2012-10-27 | Вертекс Фармасьютикалз Инкорпорейтед | Дейтерированные ингибиторы протеазы гепатита с |
| US20070244334A1 (en) * | 2006-03-16 | 2007-10-18 | Tanoury Gerald J | Processes and intermediates for preparing steric compounds |
-
1971
- 1971-07-19 NL NLAANVRAGE7109947,A patent/NL174248C/xx not_active IP Right Cessation
- 1971-07-19 DE DE2136067A patent/DE2136067C3/de not_active Expired
- 1971-07-20 AU AU31464/71A patent/AU468229B2/en not_active Expired
- 1971-07-21 CA CA118,804A patent/CA956646A/en not_active Expired
- 1971-07-22 IT IT51834/71A patent/IT1061753B/it active
- 1971-07-26 GB GB3488671A patent/GB1367674A/en not_active Expired
- 1971-08-03 CH CH1140771A patent/CH563961A5/xx not_active IP Right Cessation
- 1971-08-03 IL IL37429A patent/IL37429A/xx unknown
- 1971-08-03 BE BE770888A patent/BE770888A/xx not_active IP Right Cessation
- 1971-08-03 JP JP5802771A patent/JPS565217B1/ja active Pending
- 1971-08-03 IE IE984/71A patent/IE35489B1/xx unknown
- 1971-08-03 FR FR7128394A patent/FR2101198B1/fr not_active Expired
-
1979
- 1979-12-20 HK HK863/79A patent/HK86379A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2101198B1 (enrdf_load_stackoverflow) | 1975-08-01 |
| JPS565217B1 (enrdf_load_stackoverflow) | 1981-02-04 |
| BE770888A (fr) | 1972-02-03 |
| NL174248C (nl) | 1984-05-16 |
| HK86379A (en) | 1979-12-28 |
| IE35489L (en) | 1972-02-03 |
| CH563961A5 (enrdf_load_stackoverflow) | 1975-07-15 |
| AU3146471A (en) | 1973-01-25 |
| IE35489B1 (en) | 1976-03-03 |
| IL37429A (en) | 1975-05-22 |
| FR2101198A1 (enrdf_load_stackoverflow) | 1972-03-31 |
| AU468229B2 (en) | 1976-01-08 |
| NL7109947A (enrdf_load_stackoverflow) | 1972-02-07 |
| DE2136067B2 (de) | 1980-01-17 |
| IL37429A0 (en) | 1971-11-29 |
| DE2136067A1 (de) | 1972-02-10 |
| IT1061753B (it) | 1983-04-30 |
| CA956646A (en) | 1974-10-22 |
| GB1367674A (en) | 1974-09-18 |
| NL174248B (nl) | 1983-12-16 |
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