SK12802003A3 - Derivát biguanidu, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje - Google Patents

Derivát biguanidu, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje Download PDF

Info

Publication number: SK12802003A3
Authority: SK; Slovakia
Prior art keywords: formula; nitrogen atom; diabetes; biguanide derivative; composition
Prior art date: 2001-03-21

Application number

SK1280-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Grard Moinet

Daniel Cravo

Original Assignee

Merck Patent Gmbh

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.)

2001-03-21

Filing date

2002-03-20

Publication date

2004-02-03

2002-03-20 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2004-02-03 Publication of SK12802003A3 publication Critical patent/SK12802003A3/sk

Links

150000004283 biguanides Chemical class 0.000 title claims abstract description 16
239000008194 pharmaceutical composition Substances 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims abstract description 36
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 29
201000001421 hyperglycemia Diseases 0.000 claims abstract description 12
230000007170 pathology Effects 0.000 claims abstract description 5
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 35
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 claims description 25
239000008103 glucose Substances 0.000 claims description 25
102000004877 Insulin Human genes 0.000 claims description 18
108090001061 Insulin Proteins 0.000 claims description 18
229940125396 insulin Drugs 0.000 claims description 18
229910052757 nitrogen Inorganic materials 0.000 claims description 18
125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
125000004122 cyclic group Chemical group 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
210000003205 muscle Anatomy 0.000 claims description 9
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
238000001179 sorption measurement Methods 0.000 claims description 9
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 8
239000004480 active ingredient Substances 0.000 claims description 8
125000002883 imidazolyl group Chemical group 0.000 claims description 8
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 8
125000001041 indolyl group Chemical group 0.000 claims description 8
125000004193 piperazinyl group Chemical group 0.000 claims description 8
125000005936 piperidyl group Chemical group 0.000 claims description 8
125000003226 pyrazolyl group Chemical group 0.000 claims description 8
125000000168 pyrrolyl group Chemical group 0.000 claims description 8
238000000034 method Methods 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
230000001939 inductive effect Effects 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
239000012453 solvate Substances 0.000 claims description 3
BTQDMKCLZXPABT-UHFFFAOYSA-N 2-[(dimethylhydrazinylidene)methyl]pyrrolidine-1-carboximidamide;hydrochloride Chemical compound Cl.CN(C)N=CC1CCCN1C(N)=N BTQDMKCLZXPABT-UHFFFAOYSA-N 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
230000002708 enhancing effect Effects 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
230000006698 induction Effects 0.000 claims 1
241000700159 Rattus Species 0.000 description 16
XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 11
229960003105 metformin Drugs 0.000 description 11
239000008280 blood Substances 0.000 description 10
210000004369 blood Anatomy 0.000 description 10
208000001072 type 2 diabetes mellitus Diseases 0.000 description 8
229940123208 Biguanide Drugs 0.000 description 7
239000002253 acid Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
239000003826 tablet Substances 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
239000003472 antidiabetic agent Substances 0.000 description 6
-1 bactericidal Substances 0.000 description 6
239000002775 capsule Substances 0.000 description 6
206010022489 Insulin Resistance Diseases 0.000 description 5
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 5
206010067584 Type 1 diabetes mellitus Diseases 0.000 description 5
239000007924 injection Substances 0.000 description 5
238000002347 injection Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
230000003178 anti-diabetic effect Effects 0.000 description 4
229940125708 antidiabetic agent Drugs 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
235000005911 diet Nutrition 0.000 description 4
230000037213 diet Effects 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
230000000694 effects Effects 0.000 description 4
235000013305 food Nutrition 0.000 description 4
230000002093 peripheral effect Effects 0.000 description 4
210000001519 tissue Anatomy 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
201000010099 disease Diseases 0.000 description 3
239000012154 double-distilled water Substances 0.000 description 3
210000004185 liver Anatomy 0.000 description 3
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000829 suppository Substances 0.000 description 3
102000003746 Insulin Receptor Human genes 0.000 description 2
108010001127 Insulin Receptor Proteins 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
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
101100321409 Rattus norvegicus Zdhhc23 gene Proteins 0.000 description 2
YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 description 2
230000033228 biological regulation Effects 0.000 description 2
229960004111 buformin Drugs 0.000 description 2
XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229940110456 cocoa butter Drugs 0.000 description 2
235000019868 cocoa butter Nutrition 0.000 description 2
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
230000004064 dysfunction Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
230000002068 genetic effect Effects 0.000 description 2
229940088597 hormone Drugs 0.000 description 2
239000005556 hormone Substances 0.000 description 2
230000003914 insulin secretion Effects 0.000 description 2
210000004153 islets of langerhan Anatomy 0.000 description 2
208000006443 lactic acidosis Diseases 0.000 description 2
239000008101 lactose Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000012423 maintenance Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
210000000496 pancreas Anatomy 0.000 description 2
229960001412 pentobarbital Drugs 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
230000037081 physical activity Effects 0.000 description 2
HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
229920001592 potato starch Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 1
BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 description 1
OOSZCNKVJAVHJI-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]piperazine Chemical compound C1=CC(F)=CC=C1CN1CCNCC1 OOSZCNKVJAVHJI-UHFFFAOYSA-N 0.000 description 1
LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical class CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
VLZKFOUNRQWHQU-UHFFFAOYSA-N 2-[(dimethylhydrazinylidene)methyl]pyrrolidine-1-carboximidamide Chemical compound CN(C)N=CC1CCCN1C(N)=N VLZKFOUNRQWHQU-UHFFFAOYSA-N 0.000 description 1
TUYAIZHPVZJKIN-UHFFFAOYSA-N 2-cyano-1,1-dimethylguanidine Chemical compound CN(C)C(N)=NC#N TUYAIZHPVZJKIN-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
208000023275 Autoimmune disease Diseases 0.000 description 1
XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
206010010071 Coma Diseases 0.000 description 1
208000018035 Dental disease Diseases 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
208000034826 Genetic Predisposition to Disease Diseases 0.000 description 1
102000051325 Glucagon Human genes 0.000 description 1
108060003199 Glucagon Proteins 0.000 description 1
208000002705 Glucose Intolerance Diseases 0.000 description 1
206010018429 Glucose tolerance impaired Diseases 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
229920002527 Glycogen Polymers 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
208000007976 Ketosis Diseases 0.000 description 1
206010054805 Macroangiopathy Diseases 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
208000017442 Retinal disease Diseases 0.000 description 1
206010038923 Retinopathy Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
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 1
206010043417 Therapeutic response unexpected Diseases 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 description 1
229960002632 acarbose Drugs 0.000 description 1
XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
210000000577 adipose tissue Anatomy 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
239000003888 alpha glucosidase inhibitor Substances 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000078 anti-malarial effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
238000006065 biodegradation reaction Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000019259 carbohydrate homeostasis Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000001364 causal effect Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
230000006378 damage Effects 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
230000029087 digestion Effects 0.000 description 1
208000016097 disease of metabolism Diseases 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000499 gel Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
229960000346 gliclazide Drugs 0.000 description 1
MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 1
229960004666 glucagon Drugs 0.000 description 1
230000004110 gluconeogenesis Effects 0.000 description 1
230000009229 glucose formation Effects 0.000 description 1
230000004190 glucose uptake Effects 0.000 description 1
229940096919 glycogen Drugs 0.000 description 1
230000036541 health Effects 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229940126904 hypoglycaemic agent Drugs 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
230000004140 ketosis Effects 0.000 description 1
208000017169 kidney disease Diseases 0.000 description 1
230000003520 lipogenic effect Effects 0.000 description 1
210000003141 lower extremity Anatomy 0.000 description 1
GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
239000004137 magnesium phosphate Substances 0.000 description 1
229960002261 magnesium phosphate Drugs 0.000 description 1
229910000157 magnesium phosphate Inorganic materials 0.000 description 1
235000010994 magnesium phosphates Nutrition 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
208000030159 metabolic disease Diseases 0.000 description 1
206010062198 microangiopathy Diseases 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
229960000698 nateglinide Drugs 0.000 description 1
OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 description 1
201000001119 neuropathy Diseases 0.000 description 1
230000007823 neuropathy Effects 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
229940127017 oral antidiabetic Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000008520 organization Effects 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
208000033808 peripheral neuropathy Diseases 0.000 description 1
229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229960003243 phenformin Drugs 0.000 description 1
ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
229960005095 pioglitazone Drugs 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
230000000291 postprandial effect Effects 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
229960004586 rosiglitazone Drugs 0.000 description 1
230000000276 sedentary effect Effects 0.000 description 1
231100000489 sensitizer Toxicity 0.000 description 1
229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
230000003820 β-cell dysfunction Effects 0.000 description 1

Classifications

- 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
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Hematology (AREA)
Obesity (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Indole Compounds (AREA)
Pyrrole Compounds (AREA)
Lubricants (AREA)

SK1280-2003A 2001-03-21 2002-03-20 Derivát biguanidu, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje SK12802003A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR0103846A FR2822464B1 (fr)	2001-03-21	2001-03-21	Derives biguanides et leurs applications en therapeutique
PCT/EP2002/003119 WO2002074740A1 (fr)	2001-03-21	2002-03-20	Derives de biguanide

Publications (1)

Publication Number	Publication Date
SK12802003A3 true SK12802003A3 (sk)	2004-02-03

Family

ID=8861407

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1280-2003A SK12802003A3 (sk)	2001-03-21	2002-03-20	Derivát biguanidu, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje

Country Status (21)

Country	Link
US (1)	US7285681B2 (fr)
EP (1)	EP1370525B1 (fr)
JP (1)	JP4418157B2 (fr)
KR (1)	KR20030085558A (fr)
CN (1)	CN1228325C (fr)
AT (1)	ATE449066T1 (fr)
AU (1)	AU2002308178B2 (fr)
BR (1)	BR0208131A (fr)
CA (1)	CA2441309C (fr)
CZ (1)	CZ20032766A3 (fr)
DE (1)	DE60234424D1 (fr)
ES (1)	ES2336771T3 (fr)
FR (1)	FR2822464B1 (fr)
HU (1)	HUP0303593A3 (fr)
MX (1)	MXPA03008404A (fr)
NO (1)	NO20034171D0 (fr)
PL (1)	PL362528A1 (fr)
RU (1)	RU2276136C2 (fr)
SK (1)	SK12802003A3 (fr)
WO (1)	WO2002074740A1 (fr)
ZA (1)	ZA200308146B (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101417988B (zh) *	2007-10-24	2011-04-27	山东轩竹医药科技有限公司	双胍哌嗪类二肽酰肽酶ⅳ抑制剂
KR101041428B1 (ko) *	2008-10-13	2011-06-14	한국화학연구원	Ｎ1-2-티오펜-2-일에틸-ｎ2-치환된 바이구아나이드 유도체,이의 제조방법 및 이를 유효성분으로 함유하는 약학 조성물
WO2010103040A1 (fr)	2009-03-10	2010-09-16	INSERM (Institut National de la Santé et de la Recherche Médicale)	Activateurs de protéine kinases activées par le 5'-adénosine monophosphate (ampk), destinés au traitement de l'hypertension pulmonaire
KR101136045B1 (ko) *	2009-11-16	2012-04-18	한국화학연구원	Ｎ1-(펜에틸)-ｎ2-치환된 바이구아나이드 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 약학 조성물
NL1037643C2 (en) *	2010-01-22	2011-07-25	Karel Paul Bouter	Nutritional product comprising a biguanide.
KR101324283B1 (ko) *	2010-04-27	2013-11-01	한올바이오파마주식회사	바이구아나이드 화합물의 신규 염, 그의 제조방법, 그를 포함하는 약제학적 조성물
WO2013188452A1 (fr) *	2012-06-11	2013-12-19	The Regents Of The University Of California	Composés et procédés de traitement du cancer
KR102216701B1 (ko)	2014-11-20	2021-02-18	이뮤노메트테라퓨틱스 인코포레이티드	바이구아나이드 화합물 및 이의 용도
KR102364358B1 (ko)	2015-04-30	2022-02-17	이뮤노메트테라퓨틱스 인코포레이티드	구아니딘 화합물 및 이의 용도
CN105125689B (zh) *	2015-09-21	2018-01-19	株洲千金药业股份有限公司	一种含有妇科千金片药渣的足浴粉及其制备方法
US10344002B2 (en)	2016-09-26	2019-07-09	Nusirt Sciences, Inc.	Compositions and methods for treating metabolic disorders
CN113354561B (zh) *	2021-04-17	2023-03-28	中山大学	双胍衍生物及其应用与制剂

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB852584A (en) *	1956-05-31	1960-10-26	Us Vitamin Corp	Biguanide compositions
US2937173A (en) *	1959-05-06	1960-05-17	Us Vitamin Pharm Corp	Indolino and tetrahydroquinolino triazines
DE2009743A1 (de) *	1970-03-03	1971-09-16	Farbenfabriken Bayer Ag, 5090 Leverkusen	Substituierte Biguanide mit antihyperglykämischer Wirkung
US3879541A (en)	1970-03-03	1975-04-22	Bayer Ag	Antihyperglycemic methods and compositions
US3960949A (en)	1971-04-02	1976-06-01	Schering Aktiengesellschaft	1,2-Biguanides
EP0034002A3 (fr) *	1980-01-22	1981-09-23	Beecham Group Plc	Dérivés de carboxamidine
JPS6141367A (ja) *	1984-08-02	1986-02-27	三菱瓦斯化学株式会社	繊維または繊維製品の過酸化水素による漂白法
FR2696740B1 (fr) *	1992-10-13	1994-12-30	Dospharma Sa	Dérivés prodrogués de la diméthylbiguanide et applications comme médicaments.

2001
- 2001-03-21 FR FR0103846A patent/FR2822464B1/fr not_active Expired - Fee Related
2002
- 2002-03-20 EP EP02753575A patent/EP1370525B1/fr not_active Expired - Lifetime
- 2002-03-20 BR BR0208131-8A patent/BR0208131A/pt not_active IP Right Cessation
- 2002-03-20 RU RU2003130070/04A patent/RU2276136C2/ru not_active IP Right Cessation
- 2002-03-20 PL PL02362528A patent/PL362528A1/xx unknown
- 2002-03-20 DE DE60234424T patent/DE60234424D1/de not_active Expired - Lifetime
- 2002-03-20 AT AT02753575T patent/ATE449066T1/de not_active IP Right Cessation
- 2002-03-20 SK SK1280-2003A patent/SK12802003A3/sk unknown
- 2002-03-20 AU AU2002308178A patent/AU2002308178B2/en not_active Ceased
- 2002-03-20 WO PCT/EP2002/003119 patent/WO2002074740A1/fr not_active Ceased
- 2002-03-20 CZ CZ20032766A patent/CZ20032766A3/cs unknown
- 2002-03-20 HU HU0303593A patent/HUP0303593A3/hu unknown
- 2002-03-20 CA CA2441309A patent/CA2441309C/fr not_active Expired - Fee Related
- 2002-03-20 KR KR10-2003-7012150A patent/KR20030085558A/ko not_active Ceased
- 2002-03-20 ES ES02753575T patent/ES2336771T3/es not_active Expired - Lifetime
- 2002-03-20 JP JP2002573749A patent/JP4418157B2/ja not_active Expired - Fee Related
- 2002-03-20 CN CNB02806254XA patent/CN1228325C/zh not_active Expired - Fee Related
- 2002-03-20 MX MXPA03008404A patent/MXPA03008404A/es not_active Application Discontinuation
- 2002-03-20 US US10/472,229 patent/US7285681B2/en not_active Expired - Fee Related
2003
- 2003-09-19 NO NO20034171A patent/NO20034171D0/no not_active Application Discontinuation
- 2003-10-20 ZA ZA200308146A patent/ZA200308146B/en unknown

Also Published As

Publication number	Publication date
EP1370525A1 (fr)	2003-12-17
NO20034171L (no)	2003-09-19
BR0208131A (pt)	2004-03-02
US20040092495A1 (en)	2004-05-13
JP4418157B2 (ja)	2010-02-17
ZA200308146B (en)	2005-01-20
RU2003130070A (ru)	2005-04-10
RU2276136C2 (ru)	2006-05-10
HK1062172A1 (en)	2004-10-21
JP2004523580A (ja)	2004-08-05
ES2336771T3 (es)	2010-04-16
FR2822464A1 (fr)	2002-09-27
HUP0303593A2 (hu)	2004-03-01
CA2441309A1 (fr)	2002-09-26
FR2822464B1 (fr)	2004-08-06
CA2441309C (fr)	2010-06-15
HUP0303593A3 (en)	2007-03-28
CN1496347A (zh)	2004-05-12
US7285681B2 (en)	2007-10-23
CN1228325C (zh)	2005-11-23
ATE449066T1 (de)	2009-12-15
PL362528A1 (en)	2004-11-02
MXPA03008404A (es)	2004-01-29
EP1370525B1 (fr)	2009-11-18
NO20034171D0 (no)	2003-09-19
KR20030085558A (ko)	2003-11-05
AU2002308178B2 (en)	2007-03-01
DE60234424D1 (en)	2009-12-31
WO2002074740A1 (fr)	2002-09-26
CZ20032766A3 (cs)	2004-01-14

Legal Events

Date	Code	Title	Description
2010-11-08	FB9A	Suspension of patent application procedure

Publication	Publication Date	Title
DE2951675C2 (de)	1982-07-01	Guanidinothiazolverbindungen, Verfahren zu deren Herstellung und Arzneimittelzubereitungen
ES2267715T3 (es)	2007-03-16	Derivados aminados de dihidro-1,3,5-triazina utiles en el tratamiento de patologias asociadas al sindrome de resistencia a la insulina.
EP0937459A2 (fr)	1999-08-25	Compositions pharmaceutiques pour traiter les troubles cérébraux de nature ischémique
US6737436B1 (en)	2004-05-18	Pyrrole derivatives as phosphodiesterase VII inhibitors
EP1452526A1 (fr)	2004-09-01	Compose indolique, et utilisation a des fins therapeutiques
SK12802003A3 (sk)	2004-02-03	Derivát biguanidu, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje
DE10163992A1 (de)	2003-07-03	4-Aryl-chinazoline
CZ289449B6 (cs)	2002-01-16	3-[4-(4-(4-Kyanfenyl)-1-piperazinyl)butyl]-5-kyanindol, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje
AU2002308178A1 (en)	2003-03-27	Biguanide derivatives
CN1318428C (zh)	2007-05-30	噻吩并吡啶取代的乙酰肼衍生物
WO2004002477A1 (fr)	2004-01-08	Derives de 2-(phenyl)-2h-pyrazol-3-acide carboxylique-n-4-(thioxo-heterocyclyl)-phenyl-amide, derives d'imino-heterocyclyle correspondants et composes derives servant d'inhibiteurs des facteurs de coagulation xa et/ou viia dans le traitement de thromboses
DE10161767A1 (de)	2003-06-26	2-Guanidino-4-heterocyclyl-chinazoline
WO2003101984A1 (fr)	2003-12-11	Thiophenes substitues, procedes de fabrication, utilisation en tant que medicament ou agent diagnostique et medicament contenant ces thiophenes
US4624956A (en)	1986-11-25	Ulcer and gastric secretion inhibiting 4,5,6,7-tetrahydrothiazole[5,4-c]pyridine derivatives
EP1664058B1 (fr)	2007-11-14	Thienoimidazoles substitues, procede de production, utilisation comme medicament ou produit de diagnostic et medicaments contenant ces composes
KR100630291B1 (ko)	2006-09-29	((아미노이미노메틸)아미노)알칸카르복스아미드 및 이의치료법에서의 용도
US3928341A (en)	1975-12-23	N-Aminoalkyl-4-anilino pyridines
CS220336B2 (en)	1983-03-25	Method of producing new guanidine derivatives
JPS6042792B2 (ja)	1985-09-25	ピリドキシン誘導体及びその製法並びに医薬組成物
HK40082298B (en)	2023-07-28	Triazine derivatives
CZ20011785A3 (cs)	2001-10-17	Pouľití benzoylguanidinů pro oąetřování diabetes mellitus nezávislého na inzulínu
KR840002432B1 (ko)	1984-12-27	아미노프로판올 유도체의 제조방법
HK1050529B (en)	2006-09-29	Dihydro-1,3,5-triazine amine derivatives and their therapeutic uses
JPH0459725A (ja)	1992-02-26	抗アレルギー剤
KR20080003600A (ko)	2008-01-08	피롤로피리미디논 유도체의 말리에이트 염 및 이의제조방법