LT3309B - Process for the preparation of aminoalkylguanidines - Google Patents
Process for the preparation of aminoalkylguanidines Download PDFInfo
- Publication number
- LT3309B LT3309B LTIP1940A LTIP1940A LT3309B LT 3309 B LT3309 B LT 3309B LT IP1940 A LTIP1940 A LT IP1940A LT IP1940 A LTIP1940 A LT IP1940A LT 3309 B LT3309 B LT 3309B
- Authority
- LT
- Lithuania
- Prior art keywords
- group
- linear
- benzyl
- guanidine
- benzyloxycarbonyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 24
- 150000004985 diamines Chemical class 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 107
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 23
- -1 Aminoalkyl guanidines Chemical class 0.000 claims description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 20
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 8
- 239000008096 xylene Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- RMFQGQYZMYQGGW-UHFFFAOYSA-N benzyl n-[n'-(2-aminoethyl)carbamimidoyl]carbamate Chemical compound NCCNC(=N)NC(=O)OCC1=CC=CC=C1 RMFQGQYZMYQGGW-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 3
- AAMQEHJYBWSPBR-UHFFFAOYSA-N benzyl n-[n'-(12-aminododecyl)carbamimidoyl]carbamate Chemical compound NCCCCCCCCCCCCNC(=N)NC(=O)OCC1=CC=CC=C1 AAMQEHJYBWSPBR-UHFFFAOYSA-N 0.000 claims description 3
- NJNOSOZIVRRKCT-UHFFFAOYSA-N benzyl n-[n'-(5-aminopentyl)carbamimidoyl]carbamate Chemical compound NCCCCCNC(=N)NC(=O)OCC1=CC=CC=C1 NJNOSOZIVRRKCT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- XJXVUQKEFCGFNA-UHFFFAOYSA-N tert-butyl N-[amino-(3,5-dimethyl-1H-pyrazol-4-yl)methylidene]carbamate Chemical compound CC1=NNC(C)=C1C(=N)NC(=O)OC(C)(C)C XJXVUQKEFCGFNA-UHFFFAOYSA-N 0.000 claims description 3
- IMLCWHLPMKBUSP-UHFFFAOYSA-N tert-butyl n-[n'-(3-aminopropyl)carbamimidoyl]carbamate Chemical compound CC(C)(C)OC(=O)NC(=N)NCCCN IMLCWHLPMKBUSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000002015 acyclic group Chemical group 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- ZFQZEWXWVVMRFB-UHFFFAOYSA-N benzyl N-[amino-(3,5-dimethyl-1H-pyrazol-4-yl)methylidene]carbamate Chemical compound CC1=NNC(C)=C1C(=N)NC(=O)OCC1=CC=CC=C1 ZFQZEWXWVVMRFB-UHFFFAOYSA-N 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 2
- 241000272525 Anas platyrhynchos Species 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 8
- 125000003277 amino group Chemical group 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 abstract description 2
- 125000006239 protecting group Chemical group 0.000 description 24
- 238000001914 filtration Methods 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 14
- 239000013078 crystal Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- 108090000765 processed proteins & peptides Proteins 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QYPPJABKJHAVHS-UHFFFAOYSA-N agmatine Chemical compound NCCCCNC(N)=N QYPPJABKJHAVHS-UHFFFAOYSA-N 0.000 description 6
- IXDJJDXZZPHUAY-UHFFFAOYSA-N benzyl n-[n'-(3-aminopropyl)carbamimidoyl]carbamate Chemical compound NCCCNC(=N)NC(=O)OCC1=CC=CC=C1 IXDJJDXZZPHUAY-UHFFFAOYSA-N 0.000 description 6
- DLEXEXIDPYXCNP-UHFFFAOYSA-N benzyl n-[n'-(4-aminobutyl)carbamimidoyl]carbamate Chemical compound NCCCCNC(=N)NC(=O)OCC1=CC=CC=C1 DLEXEXIDPYXCNP-UHFFFAOYSA-N 0.000 description 6
- MLYVUDZUFYUWHE-UHFFFAOYSA-N benzyl (nz)-n-[amino(methoxy)methylidene]carbamate Chemical compound COC(N)=NC(=O)OCC1=CC=CC=C1 MLYVUDZUFYUWHE-UHFFFAOYSA-N 0.000 description 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 5
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 125000003944 tolyl group Chemical group 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001483 arginine derivatives Chemical class 0.000 description 3
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 150000002357 guanidines Chemical class 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- ZHNUXJSPYNQQHV-UHFFFAOYSA-N benzyl (nz)-n-[amino(methylsulfanyl)methylidene]carbamate Chemical compound CSC(=N)NC(=O)OCC1=CC=CC=C1 ZHNUXJSPYNQQHV-UHFFFAOYSA-N 0.000 description 2
- UIUCNCJSSLVZLY-UHFFFAOYSA-N benzyl n-[n'-(8-aminooctyl)carbamimidoyl]carbamate Chemical compound NCCCCCCCCNC(=N)NC(=O)OCC1=CC=CC=C1 UIUCNCJSSLVZLY-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- KWCPQPFOPUCWPH-UHFFFAOYSA-N 1-(oxomethylidene)guanidine Chemical compound NC(=N)N=C=O KWCPQPFOPUCWPH-UHFFFAOYSA-N 0.000 description 1
- WRGLZNWEJGKYHH-UHFFFAOYSA-N 2-(3-aminopropyl)guanidine Chemical compound NCCCNC(N)=N WRGLZNWEJGKYHH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- BMXFPSYOCKSSBE-UHFFFAOYSA-N guanidine Chemical compound NC(N)=N.NC(N)=N BMXFPSYOCKSSBE-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
- 229950008754 pyricarbate Drugs 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
-
- 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
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE19939301912A SE9301912D0 (sv) | 1993-06-03 | 1993-06-03 | Process for the production of aminoalkylguandines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP1940A LTIP1940A (en) | 1994-12-27 |
| LT3309B true LT3309B (en) | 1995-06-26 |
Family
ID=20390162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP1940A LT3309B (en) | 1993-06-03 | 1994-05-18 | Process for the preparation of aminoalkylguanidines |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5659071A (is) |
| EP (1) | EP0701550B1 (is) |
| JP (1) | JP3662925B2 (is) |
| CN (1) | CN1124956A (is) |
| AT (1) | ATE178316T1 (is) |
| AU (1) | AU674970B2 (is) |
| BR (1) | BR9406713A (is) |
| CA (1) | CA2162920C (is) |
| CZ (1) | CZ320095A3 (is) |
| DE (1) | DE69417554T2 (is) |
| DK (1) | DK0701550T3 (is) |
| EE (1) | EE9400348A (is) |
| ES (1) | ES2131688T3 (is) |
| FI (1) | FI120093B (is) |
| GR (1) | GR3030501T3 (is) |
| HR (1) | HRP940317A2 (is) |
| HU (1) | HUT74293A (is) |
| IL (1) | IL109683A0 (is) |
| IS (1) | IS4165A (is) |
| LT (1) | LT3309B (is) |
| NO (1) | NO305514B1 (is) |
| NZ (1) | NZ267192A (is) |
| PL (1) | PL311760A1 (is) |
| SE (1) | SE9301912D0 (is) |
| SK (1) | SK151895A3 (is) |
| WO (1) | WO1994029269A1 (is) |
| YU (1) | YU33594A (is) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5610308A (en) * | 1995-05-18 | 1997-03-11 | Bristol-Myers Squibb Company | Process for preparing intermediates for thrombin inhibitors |
| CA2239908A1 (en) * | 1995-12-09 | 1997-06-19 | Boehringer Mannheim Gmbh | 3-aminoethyl-n-amidino-2,5-dihydropyrrole derivatives having arginine mimetic properties |
| US7129233B2 (en) | 2000-12-01 | 2006-10-31 | Astrazeneca Ab | Mandelic acid derivatives and their use as thrombin inhibitors |
| AR035216A1 (es) * | 2000-12-01 | 2004-05-05 | Astrazeneca Ab | Derivados de acido mandelico ,derivados farmaceuticamente aceptables, uso de estos derivados para la fabricacion de medicamentos, metodos de tratamiento ,procesos para la preparacion de estos derivados, y compuestos intermediarios |
| FR2822463B1 (fr) | 2001-03-21 | 2004-07-30 | Lipha | Derives bicycliques de guanidines et leurs applications en therapeutique |
| AR034517A1 (es) * | 2001-06-21 | 2004-02-25 | Astrazeneca Ab | Formulacion farmaceutica |
| SE0201659D0 (sv) * | 2002-05-31 | 2002-05-31 | Astrazeneca Ab | Modified release pharmaceutical formulation |
| SE0201661D0 (sv) | 2002-05-31 | 2002-05-31 | Astrazeneca Ab | New salts |
| US7781424B2 (en) * | 2003-05-27 | 2010-08-24 | Astrazeneca Ab | Modified release pharmaceutical formulation |
| US7524354B2 (en) * | 2005-07-07 | 2009-04-28 | Research Foundation Of State University Of New York | Controlled synthesis of highly monodispersed gold nanoparticles |
| EP2043767B1 (en) | 2006-07-14 | 2020-03-25 | Wisconsin Alumni Research Foundation | Adsorptive membranes for trapping viruses |
| TW200827336A (en) | 2006-12-06 | 2008-07-01 | Astrazeneca Ab | New crystalline forms |
| US20090061000A1 (en) * | 2007-08-31 | 2009-03-05 | Astrazeneca Ab | Pharmaceutical formulation use 030 |
| JP6006634B2 (ja) * | 2011-12-28 | 2016-10-12 | 東和薬品株式会社 | イソウレア化合物を用いるエピナスチンの製造方法 |
| JP6484220B2 (ja) * | 2014-03-28 | 2019-03-13 | 株式会社カネカ | トリ−カルボベンゾキシ−アルギニンの製造方法 |
| US12098118B2 (en) | 2018-11-07 | 2024-09-24 | Regents Of The University Of Minnesota | Analgesic and anti-addictive compositions for treatment of chronic pain and opioid addiction |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4346078A (en) | 1979-06-12 | 1982-08-24 | Richter Gedeon Vegyeszeti Gyar Rt. | Novel anticoagulant agmatine derivatives and process for the preparation thereof |
| US4387049A (en) | 1982-02-22 | 1983-06-07 | Smithkline Beckman Corporation | Adamantyl containing peptides |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE463576C (de) * | 1924-08-06 | 1928-07-31 | Schering Kahlbaum Akt Ges | Verfahren zur Darstellung von Aminoguanidinen oder deren Salzen |
| FR2294699A1 (fr) * | 1974-12-19 | 1976-07-16 | Bottu | Nouveaux derives du pyrazole et compositions pharmaceutiques les renfermant |
| DE3222342A1 (de) * | 1982-06-14 | 1983-12-15 | Hoechst Ag, 6230 Frankfurt | 6-aryl-1,2,4-triazolo (4,3-b) pyridazin-3-carbaminate, ihre herstellung und sie enthaltende arzneimittel |
| US4914189A (en) * | 1987-02-05 | 1990-04-03 | The Adminstrators Of The Tulane Educational Fund | Synthetic GHRH analogs |
| DE69209293T3 (de) * | 1991-07-03 | 1999-12-02 | E.I. Du Pont De Nemours And Co., Wilmington | Azeotrope und azeotropartige zusammensetzungen von pentafluorethan und propan oder isobuthan |
| US5498724A (en) * | 1994-06-28 | 1996-03-12 | Aktiebolaget Astra | Pyrazoleamidine compounds |
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1993
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4346078A (en) | 1979-06-12 | 1982-08-24 | Richter Gedeon Vegyeszeti Gyar Rt. | Novel anticoagulant agmatine derivatives and process for the preparation thereof |
| US4387049A (en) | 1982-02-22 | 1983-06-07 | Smithkline Beckman Corporation | Adamantyl containing peptides |
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| Title |
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| HOUBEN-WEYL: "Methoden der Organischen Chemie", pages: 506 |
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