SK151895A3 - Process for production of aminoalkylguanides - Google Patents

Process for production of aminoalkylguanides Download PDF

Info

Publication number: SK151895A3
Authority: SK; Slovakia
Prior art keywords: group; linear; benzyl; branched; alkyl group
Prior art date: 1993-06-03

Application number

SK1518-95A

Other languages

English (en)

Slovak (sk)

Inventor

Jan-Erik Nystrom

Hans F Sjobom

Original Assignee

Astra Ab

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.)

1993-06-03

Filing date

1994-06-01

Publication date

1996-04-03

1994-06-01 Application filed by Astra Ab filed Critical Astra Ab

1996-04-03 Publication of SK151895A3 publication Critical patent/SK151895A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 47
238000004519 manufacturing process Methods 0.000 title claims abstract 3
150000001875 compounds Chemical class 0.000 claims abstract description 15
150000004985 diamines 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 105
239000011541 reaction mixture Substances 0.000 claims description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 19
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 17
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
239000003795 chemical substances by application Substances 0.000 claims description 14
-1 alkylbenzene Chemical class 0.000 claims description 10
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
239000002904 solvent Substances 0.000 claims description 8
239000008096 xylene Substances 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
239000004215 Carbon black (E152) Substances 0.000 claims description 4
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 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
125000003226 pyrazolyl group Chemical group 0.000 claims description 4
150000004996 alkyl benzenes Chemical class 0.000 claims description 3
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 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
125000004122 cyclic group Chemical group 0.000 claims description 3
150000002357 guanidines Chemical class 0.000 claims description 3
150000002430 hydrocarbons Chemical class 0.000 claims description 3
238000001556 precipitation Methods 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000002015 acyclic group Chemical group 0.000 claims 1
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 abstract description 8
125000003277 amino group Chemical group 0.000 abstract description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 3
239000003153 chemical reaction reagent Substances 0.000 abstract description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 24
125000006239 protecting group Chemical group 0.000 description 21
238000001914 filtration Methods 0.000 description 19
239000000047 product Substances 0.000 description 19
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 15
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 12
239000000203 mixture Substances 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
238000002360 preparation method Methods 0.000 description 9
238000005406 washing Methods 0.000 description 9
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 8
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 8
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 8
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 7
239000004475 Arginine Substances 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
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 6
125000003944 tolyl group Chemical group 0.000 description 6
108090000765 processed proteins & peptides Proteins 0.000 description 5
UDYGTYSIHGJFPB-UHFFFAOYSA-N NCCCCN(C(=N)N)C(=O)OCC1=CC=CC=C1 Chemical compound NCCCCN(C(=N)N)C(=O)OCC1=CC=CC=C1 UDYGTYSIHGJFPB-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 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
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 description 3
GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
238000003756 stirring Methods 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
WDKXVZMFXWQVFH-UHFFFAOYSA-N NCCCN(C(=N)N)C(=O)OCC1=CC=CC=C1 Chemical compound NCCCN(C(=N)N)C(=O)OCC1=CC=CC=C1 WDKXVZMFXWQVFH-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
239000005700 Putrescine Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001483 arginine derivatives Chemical class 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
KQHMSHHGVIRSTA-UHFFFAOYSA-N benzyl n-[n'-(3-aminopropyl)carbamimidoyl]carbamate;dihydrochloride Chemical compound Cl.Cl.NCCCNC(=N)NC(=O)OCC1=CC=CC=C1 KQHMSHHGVIRSTA-UHFFFAOYSA-N 0.000 description 2
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 2
VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000010596 desymmetrization reaction Methods 0.000 description 2
QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000000376 reactant Substances 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
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 2
WRGLZNWEJGKYHH-UHFFFAOYSA-N 2-(3-aminopropyl)guanidine Chemical compound NCCCNC(N)=N WRGLZNWEJGKYHH-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
LHZHYALHRDISND-UHFFFAOYSA-O [amino-(3,5-dimethylpyrazol-3-yl)methylidene]azanium;nitrate Chemical compound [O-][N+]([O-])=O.CC1=CC(C)(C(N)=[NH2+])N=N1 LHZHYALHRDISND-UHFFFAOYSA-O 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
125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 description 1
KKYALIQGNUBCNB-UHFFFAOYSA-N benzyl (methylcarbamoylamino) carbonate Chemical compound C(C1=CC=CC=C1)OC(=O)ON=C(NC)O KKYALIQGNUBCNB-UHFFFAOYSA-N 0.000 description 1
DCQAIGHVRXHOSL-UHFFFAOYSA-N benzyl [carbamoyl(ethyl)amino] carbonate Chemical compound C(C1=CC=CC=C1)OC(=O)ON(C(O)=N)CC DCQAIGHVRXHOSL-UHFFFAOYSA-N 0.000 description 1
NTNCPJNFWSCLEB-UHFFFAOYSA-N benzyl [carbamoyl(methyl)amino] carbonate Chemical compound C(C1=CC=CC=C1)OC(=O)ON(C(O)=N)C NTNCPJNFWSCLEB-UHFFFAOYSA-N 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
230000000903 blocking effect Effects 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
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 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
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
238000004090 dissolution 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
239000001257 hydrogen Substances 0.000 description 1
238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
238000001953 recrystallisation Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
UMOZLQVSOVNSCA-UHFFFAOYSA-N tert-butyl n-(diaminomethylidene)carbamate Chemical compound CC(C)(C)OC(=O)NC(N)=N UMOZLQVSOVNSCA-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000005292 vacuum distillation 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)

SK1518-95A 1993-06-03 1994-06-01 Process for production of aminoalkylguanides SK151895A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE19939301912A SE9301912D0 (sv)	1993-06-03	1993-06-03	Process for the production of aminoalkylguandines
PCT/SE1994/000517 WO1994029269A1 (en)	1993-06-03	1994-06-01	Process for the production of aminoalkylguanidines

Publications (1)

Publication Number	Publication Date
SK151895A3 true SK151895A3 (en)	1996-04-03

Family

ID=20390162

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1518-95A SK151895A3 (en)	1993-06-03	1994-06-01	Process for production of aminoalkylguanides

Country Status (27)

Country	Link
US (1)	US5659071A (cs)
EP (1)	EP0701550B1 (cs)
JP (1)	JP3662925B2 (cs)
CN (1)	CN1124956A (cs)
AT (1)	ATE178316T1 (cs)
AU (1)	AU674970B2 (cs)
BR (1)	BR9406713A (cs)
CA (1)	CA2162920C (cs)
CZ (1)	CZ320095A3 (cs)
DE (1)	DE69417554T2 (cs)
DK (1)	DK0701550T3 (cs)
EE (1)	EE9400348A (cs)
ES (1)	ES2131688T3 (cs)
FI (1)	FI120093B (cs)
GR (1)	GR3030501T3 (cs)
HR (1)	HRP940317A2 (cs)
HU (1)	HUT74293A (cs)
IL (1)	IL109683A0 (cs)
IS (1)	IS4165A (cs)
LT (1)	LT3309B (cs)
NO (1)	NO305514B1 (cs)
NZ (1)	NZ267192A (cs)
PL (1)	PL311760A1 (cs)
SE (1)	SE9301912D0 (cs)
SK (1)	SK151895A3 (cs)
WO (1)	WO1994029269A1 (cs)
YU (1)	YU33594A (cs)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1997021725A1 (en) *	1995-12-09	1997-06-19	Boehringer Mannheim Gmbh	3-aminoethyl-n-amidino-2,5-dihydropyrrole derivatives having arginine mimetic properties
US5610308A (en) *	1995-05-18	1997-03-11	Bristol-Myers Squibb Company	Process for preparing intermediates for 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
US7129233B2 (en) *	2000-12-01	2006-10-31	Astrazeneca Ab	Mandelic acid derivatives and their use as thrombin inhibitors
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
SE0201661D0 (sv)	2002-05-31	2002-05-31	Astrazeneca Ab	New salts
SE0201659D0 (sv)	2002-05-31	2002-05-31	Astrazeneca Ab	Modified release pharmaceutical formulation
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
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1993
- 1993-06-03 SE SE19939301912A patent/SE9301912D0/xx unknown
1994
- 1994-05-11 IS IS4165A patent/IS4165A/is unknown
- 1994-05-18 LT LTIP1940A patent/LT3309B/lt not_active IP Right Cessation
- 1994-05-19 IL IL10968394A patent/IL109683A0/xx unknown
- 1994-05-23 HR HR9301912-3A patent/HRP940317A2/xx not_active Application Discontinuation
- 1994-06-01 WO PCT/SE1994/000517 patent/WO1994029269A1/en not_active Ceased
- 1994-06-01 DE DE69417554T patent/DE69417554T2/de not_active Expired - Lifetime
- 1994-06-01 DK DK94917867T patent/DK0701550T3/da active
- 1994-06-01 US US08/244,924 patent/US5659071A/en not_active Expired - Lifetime
- 1994-06-01 CA CA002162920A patent/CA2162920C/en not_active Expired - Fee Related
- 1994-06-01 BR BR9406713A patent/BR9406713A/pt not_active Application Discontinuation
- 1994-06-01 AU AU69404/94A patent/AU674970B2/en not_active Ceased
- 1994-06-01 NZ NZ267192A patent/NZ267192A/en not_active IP Right Cessation
- 1994-06-01 EP EP94917867A patent/EP0701550B1/en not_active Expired - Lifetime
- 1994-06-01 ES ES94917867T patent/ES2131688T3/es not_active Expired - Lifetime
- 1994-06-01 AT AT94917867T patent/ATE178316T1/de active
- 1994-06-01 PL PL94311760A patent/PL311760A1/xx unknown
- 1994-06-01 HU HU9503444A patent/HUT74293A/hu unknown
- 1994-06-01 SK SK1518-95A patent/SK151895A3/sk unknown
- 1994-06-01 CZ CZ953200A patent/CZ320095A3/cs unknown
- 1994-06-01 CN CN94192325A patent/CN1124956A/zh active Pending
- 1994-06-01 JP JP50165295A patent/JP3662925B2/ja not_active Expired - Fee Related
- 1994-06-03 YU YU33594A patent/YU33594A/sh unknown
- 1994-11-17 EE EE9400348A patent/EE9400348A/xx unknown
1995
- 1995-11-28 NO NO954835A patent/NO305514B1/no not_active IP Right Cessation
- 1995-12-01 FI FI955800A patent/FI120093B/fi not_active IP Right Cessation
1999
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Also Published As

Publication number	Publication date
YU33594A (sh)	1997-05-28
FI955800A0 (fi)	1995-12-01
NO954835L (no)	1995-11-28
US5659071A (en)	1997-08-19
IS4165A (is)	1994-12-04
CA2162920C (en)	2005-08-09
NO305514B1 (no)	1999-06-14
ES2131688T3 (es)	1999-08-01
EE9400348A (et)	1996-04-15
HRP940317A2 (en)	1996-10-31
EP0701550A1 (en)	1996-03-20
CA2162920A1 (en)	1994-12-22
SE9301912D0 (sv)	1993-06-03
DK0701550T3 (da)	1999-10-11
LTIP1940A (en)	1994-12-27
NZ267192A (en)	1997-03-24
CN1124956A (zh)	1996-06-19
ATE178316T1 (de)	1999-04-15
EP0701550B1 (en)	1999-03-31
CZ320095A3 (en)	1996-07-17
JP3662925B2 (ja)	2005-06-22
FI955800L (fi)	1995-12-01
DE69417554T2 (de)	1999-09-02
WO1994029269A1 (en)	1994-12-22
JPH08511016A (ja)	1996-11-19
AU6940494A (en)	1995-01-03
FI120093B (fi)	2009-06-30
IL109683A0 (en)	1994-08-26
PL311760A1 (en)	1996-03-18
BR9406713A (pt)	1996-03-19
NO954835D0 (no)	1995-11-28
LT3309B (en)	1995-06-26
GR3030501T3 (en)	1999-10-29
HUT74293A (en)	1996-11-28
AU674970B2 (en)	1997-01-16
HU9503444D0 (en)	1996-01-29
DE69417554D1 (de)	1999-05-06

Publication	Publication Date	Title
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CZ20031715A3 (cs)	2003-11-12	Nové deriváty N- (fenylsulfonyl)glycinu a jejich terapeutické použití
US5498724A (en)	1996-03-12	Pyrazoleamidine compounds
US6576786B2 (en)	2003-06-10	Process for preparing substituted cyclopentane derivatives and novel crystalline structures thereof
JP4135809B2 (ja)	2008-08-20	薬学的に活性な化合物の中間体としてのヒダントイン誘導体
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US5856579A (en)	1999-01-05	Adduct salts of novel substituted benzylamines and a process for optically resolving them
US2543345A (en)	1951-02-27	Method of preparing glutamic acid amides
US4587337A (en)	1986-05-06	Process for the preparation of 2-amino-s-triazines
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US6258976B1 (en)	2001-07-10	Process for the preparation of polyamines and polyamine derivatives
US4335247A (en)	1982-06-15	Novel nitrosourea derivatives and process for their production
US4837332A (en)	1989-06-06	Process for blocking amino acids with the tertiary-alkoxycarbonyl group
US5010196A (en)	1991-04-23	Acylated hexahydropyrimidines
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US5112996A (en)	1992-05-12	Method for alkylating guanidino groups
Popaj et al.	2001	Synthetic Analogues of Naturally Occurring Spider Toxins: Synthesis of 2‐(Hydroxyphenyl) propanamides of Spermidine and Spermine
SK283372B6 (sk)	2003-06-03	Zlúčeniny zo skupiny 15-deoxyspergualínových analógov, spôsob ich prípravy, medziprodukty tohto spôsobu, terapeutický prostriedok a použitie
US5962722A (en)	1999-10-05	α-hydrazino acid derivatives and method for making same
MXPA01012048A (es)	2002-05-06	Sales de cis-(4- (3-ciclopentiloxi- 4-metoxifenil) ciclohexan- 1-carboxilato).