SK282357B6 - Aminoguanidínkarboxyláty a ich použitie - Google Patents

Aminoguanidínkarboxyláty a ich použitie Download PDF

Info

Publication number: SK282357B6
Authority: SK; Slovakia
Prior art keywords: aminoiminomethyl; acid; acetic acid; hydrazine; mmol
Prior art date: 1994-11-23

Application number

SK640-97A

Other languages

English (en)

Slovak (sk)

Other versions

SK64097A3 (en

Inventor

Scott D. Larsen

Valerie A. Vaillancourt

Paul D. May

Steven P. Tanis

John A. Tucker

Martin D. Meglasson

Heinrich J. Schostarez

Original Assignee

Pharmacia And Upjohn Company

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.)

1994-11-23

Filing date

1995-11-13

Publication date

2002-01-07

1995-06-07 Priority claimed from US08/484,547 external-priority patent/US5994577A/en

1995-11-13 Application filed by Pharmacia And Upjohn Company filed Critical Pharmacia And Upjohn Company

1997-11-05 Publication of SK64097A3 publication Critical patent/SK64097A3/sk

2002-01-07 Publication of SK282357B6 publication Critical patent/SK282357B6/sk

Links

-1 Aminoguanidine carboxylates Chemical class 0.000 title claims description 23
150000001875 compounds Chemical class 0.000 claims abstract description 75
238000011282 treatment Methods 0.000 claims abstract description 20
206010012601 diabetes mellitus Diseases 0.000 claims description 60
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 34
239000004471 Glycine Substances 0.000 claims description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
208000008589 Obesity Diseases 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 12
235000020824 obesity Nutrition 0.000 claims description 12
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 11
FQQQSNAVVZSYMB-UHFFFAOYSA-N 1,1-diaminoguanidine Chemical compound NN(N)C(N)=N FQQQSNAVVZSYMB-UHFFFAOYSA-N 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
ISDMMAMTIMFUKA-UHFFFAOYSA-N 2-(dihydrazinylmethylideneamino)acetic acid Chemical compound NNC(NN)=NCC(O)=O ISDMMAMTIMFUKA-UHFFFAOYSA-N 0.000 claims description 6
230000001419 dependent effect Effects 0.000 claims description 6
229940125396 insulin Drugs 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
102000004877 Insulin Human genes 0.000 claims description 5
108090001061 Insulin Proteins 0.000 claims description 5
229960003767 alanine Drugs 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 3
150000004682 monohydrates Chemical class 0.000 claims description 3
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
SZLPXEIPKKJLGV-UWTATZPHSA-N (2r)-2-(dihydrazinylmethylideneamino)propanoic acid Chemical compound OC(=O)[C@@H](C)N=C(NN)NN SZLPXEIPKKJLGV-UWTATZPHSA-N 0.000 claims description 2
RQFYXICWQNFXJQ-BYPYZUCNSA-N (2s)-2-(dihydrazinylmethylideneamino)-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)N=C(NN)NN RQFYXICWQNFXJQ-BYPYZUCNSA-N 0.000 claims description 2
PLCWUGVOZVCBPA-UHFFFAOYSA-N 3-(dihydrazinylmethylideneamino)propanoic acid Chemical compound NNC(NN)=NCCC(O)=O PLCWUGVOZVCBPA-UHFFFAOYSA-N 0.000 claims description 2
CKWZZMQMHKAGKV-UHFFFAOYSA-N 3-(hydrazinylmethylamino)propanoic acid Chemical compound N(N)CNCCC(=O)O CKWZZMQMHKAGKV-UHFFFAOYSA-N 0.000 claims description 2
150000007857 hydrazones Chemical class 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
230000002265 prevention Effects 0.000 claims description 2
OTKZQCSZPYXWCJ-UHFFFAOYSA-N acetic acid;n,n'-diaminomethanimidamide Chemical compound CC(O)=O.NN\C=N\N OTKZQCSZPYXWCJ-UHFFFAOYSA-N 0.000 claims 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
SLEMVTMJWXHEBP-KPKJPENVSA-N (2e)-2-(diaminomethylidenehydrazinylidene)octanoic acid Chemical compound CCCCCC\C(C(O)=O)=N/N=C(N)N SLEMVTMJWXHEBP-KPKJPENVSA-N 0.000 claims 1
BUFICAGIEQZREO-UHFFFAOYSA-N 2-[(2-aminohydrazinyl)methylideneamino]acetic acid Chemical compound NNN=CNCC(O)=O BUFICAGIEQZREO-UHFFFAOYSA-N 0.000 claims 1
HRLLBWIAWUMBRH-UHFFFAOYSA-N 2-[amino(carbamohydrazonoyl)amino]acetic acid Chemical compound NNC(=N)N(N)CC(O)=O HRLLBWIAWUMBRH-UHFFFAOYSA-N 0.000 claims 1
VJEGYCPVNVCNSX-UHFFFAOYSA-N NN=CNN=C(C(=O)O)CC1=CC=CC=C1 Chemical compound NN=CNN=C(C(=O)O)CC1=CC=CC=C1 VJEGYCPVNVCNSX-UHFFFAOYSA-N 0.000 claims 1
WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 claims 1
LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 claims 1
229910000096 monohydride Inorganic materials 0.000 claims 1
208000001072 type 2 diabetes mellitus Diseases 0.000 abstract description 26
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 58
239000008103 glucose Substances 0.000 description 58
239000007787 solid Substances 0.000 description 47
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
239000000203 mixture Substances 0.000 description 43
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 42
241000699670 Mus sp. Species 0.000 description 42
210000004369 blood Anatomy 0.000 description 38
239000008280 blood Substances 0.000 description 38
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 30
230000013595 glycosylation Effects 0.000 description 24
238000006206 glycosylation reaction Methods 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 22
229960003105 metformin Drugs 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
102000004169 proteins and genes Human genes 0.000 description 20
108090000623 proteins and genes Proteins 0.000 description 20
239000002904 solvent Substances 0.000 description 17
230000002255 enzymatic effect Effects 0.000 description 16
238000002844 melting Methods 0.000 description 15
230000008018 melting Effects 0.000 description 15
230000037396 body weight Effects 0.000 description 14
230000000694 effects Effects 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
241000700159 Rattus Species 0.000 description 11
239000003921 oil Substances 0.000 description 11
239000000725 suspension Substances 0.000 description 11
206010067584 Type 1 diabetes mellitus Diseases 0.000 description 10
238000001914 filtration Methods 0.000 description 10
230000004580 weight loss Effects 0.000 description 10
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
230000009467 reduction Effects 0.000 description 9
238000012360 testing method Methods 0.000 description 9
208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 8
208000002705 Glucose Intolerance Diseases 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
201000001421 hyperglycemia Diseases 0.000 description 7
238000000034 method Methods 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
239000000843 powder Substances 0.000 description 7
241001465754 Metazoa Species 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
239000012043 crude product Substances 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
201000009104 prediabetes syndrome Diseases 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
229910014033 C-OH Inorganic materials 0.000 description 5
229910014570 C—OH Inorganic materials 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 5
229940079593 drug Drugs 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
125000001841 imino group Chemical group [H]N=* 0.000 description 5
238000000338 in vitro Methods 0.000 description 5
238000010992 reflux Methods 0.000 description 5
AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 5
238000003756 stirring Methods 0.000 description 5
102000009027 Albumins Human genes 0.000 description 4
108010088751 Albumins Proteins 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
241000283984 Rodentia Species 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
HIMXGTXNXJYFGB-UHFFFAOYSA-N alloxan Chemical compound O=C1NC(=O)C(=O)C(=O)N1 HIMXGTXNXJYFGB-UHFFFAOYSA-N 0.000 description 4
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
201000010099 disease Diseases 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 4
235000019260 propionic acid Nutrition 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
229940126062 Compound A Drugs 0.000 description 3
208000002249 Diabetes Complications Diseases 0.000 description 3
206010012655 Diabetic complications Diseases 0.000 description 3
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
102000008100 Human Serum Albumin Human genes 0.000 description 3
108091006905 Human Serum Albumin Proteins 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
XQZZSJQCHLCCCU-UHFFFAOYSA-N acetic acid;n'-amino-n-hydrazinylmethanimidamide Chemical compound CC(O)=O.NNN\C=N\N XQZZSJQCHLCCCU-UHFFFAOYSA-N 0.000 description 3
GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 3
238000000540 analysis of variance Methods 0.000 description 3
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
230000008859 change Effects 0.000 description 3
230000001684 chronic effect Effects 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
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239000012990 dithiocarbamate Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
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230000004190 glucose uptake Effects 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 3
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
239000000047 product Substances 0.000 description 3
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FBWUQOCZUAQETQ-UHFFFAOYSA-N 2-(2-methanehydrazonoylhydrazinyl)acetic acid Chemical compound N\N=C\NNCC(O)=O FBWUQOCZUAQETQ-UHFFFAOYSA-N 0.000 description 2
KHZVLGLEHBZEPO-UHFFFAOYSA-N 2-hydrazinyl-3-phenylpropanoic acid Chemical compound NNC(C(O)=O)CC1=CC=CC=C1 KHZVLGLEHBZEPO-UHFFFAOYSA-N 0.000 description 2
KMXXSJLYVJEBHI-UHFFFAOYSA-N 3-guanidinopropanoic acid Chemical compound NC(=[NH2+])NCCC([O-])=O KMXXSJLYVJEBHI-UHFFFAOYSA-N 0.000 description 2
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones

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

SK640-97A 1994-11-23 1995-11-13 Aminoguanidínkarboxyláty a ich použitie SK282357B6 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US34427494A	1994-11-23	1994-11-23
US08/484,547 US5994577A (en)	1994-11-23	1995-06-07	Aminoguanidine carboxylates for the treatment of non-insulin-dependent diabetes mellitus
PCT/US1995/014126 WO1996016031A1 (en)	1994-11-23	1995-11-13	Aminoguanidine carboxylates for the treatment of non-insulin-dependent diabetes mellitus

Publications (2)

Publication Number	Publication Date
SK64097A3 SK64097A3 (en)	1997-11-05
SK282357B6 true SK282357B6 (sk)	2002-01-07

Family

ID=26993832

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK640-97A SK282357B6 (sk)	1994-11-23	1995-11-13	Aminoguanidínkarboxyláty a ich použitie

Country Status (24)

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US (2)	US6166080A (es)
EP (1)	EP0793646B1 (es)
JP (1)	JPH10509455A (es)
CN (2)	CN1097580C (es)
AT (1)	ATE205188T1 (es)
AU (1)	AU705893B2 (es)
BR (1)	BR9509741A (es)
CA (1)	CA2202265A1 (es)
CZ (1)	CZ288597B6 (es)
DE (2)	DE793646T1 (es)
DK (1)	DK0793646T3 (es)
EE (1)	EE03392B1 (es)
ES (1)	ES2163531T3 (es)
FI (1)	FI972185A0 (es)
GE (1)	GEP20002026B (es)
HU (1)	HUT77133A (es)
MX (1)	MX9703807A (es)
NO (1)	NO308992B1 (es)
NZ (1)	NZ297604A (es)
PL (1)	PL184614B1 (es)
PT (1)	PT793646E (es)
RU (1)	RU2162462C2 (es)
SK (1)	SK282357B6 (es)
WO (1)	WO1996016031A1 (es)

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EP0957909A1 (en) *	1997-02-13	1999-11-24	Smithkline Beecham Plc	Use of nitric oxid synthase inhibitors for the treatment of diabetes
SE9702457D0 (sv) *	1997-06-26	1997-06-26	Pharmacia & Upjohn Ab	Screening
US6001578A (en) *	1997-06-26	1999-12-14	Pharmacia & Upjohn Ab	Methods of screening for modulators of uncoupling protein-2 (UCP-2) as potential treatments for obesity
US6288124B1 (en)	1998-05-22	2001-09-11	Rima Kaddurah-Daouk	Methods of inhibiting undesirable cell growth using an aminoguanidine compound
US6169115B1 (en)	1998-05-22	2001-01-02	Rima Kaddurah-Daouk	Use of aminoguanidine analogs for the treatment of diseases of the nervous system
US6815421B1 (en) *	2001-03-22	2004-11-09	Osteopharm Inc.	Polypeptides for use in ameliorating effects of aging in mammals
WO2009133152A1 (en) *	2008-04-29	2009-11-05	Becton, Dickinson And Company	Method and system for measuring a sample to determine the presence of and optionally treat a pathologic condition
BRPI0822909B8 (pt) *	2008-06-26	2021-05-25	Laboratorios Silanes S A De C V	sal de glicinato de metformina para o controle da glicose sanguínea
GB201300435D0 (en) *	2013-01-10	2013-02-27	Medical Res Council	Benzylideneguanidine Derivatives and Therapeutic Use for the Treatment of Protein Misfolding Diseases
WO2016171038A1 (ja) *	2015-04-23	2016-10-27	三菱瓦斯化学株式会社	ガス発生剤、及びそれを用いた発泡体の製造方法
US20170056352A1 (en) *	2015-08-25	2017-03-02	Rgenix, Inc.	PHARMACEUTICALLY ACCEPTABLE SALTS OF beta-GUANIDINOPROPIONIC ACID WITH IMPROVED PROPERTIES AND USES THEREOF
WO2018160178A1 (en)	2017-03-01	2018-09-07	Rgenix, Inc.	Pharmaceutically acceptable salts of b-guanidinopropionic acid with improved properties and uses thereof
WO2021119316A1 (en)	2019-12-11	2021-06-17	Rgenix, Inc.	Methods of treating cancer

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JPS54128523A (en)	1978-03-29	1979-10-05	Nippon Carbide Ind Co Ltd	3-guanidinoamino propionic acid and its preparation
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US5272165A (en) *	1984-03-19	1993-12-21	The Rockefeller University	2-alkylidene-aminoguanidines and methods of use therefor
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1995
- 1995-11-08 PT PT95939672T patent/PT793646E/pt unknown
- 1995-11-08 DE DE0793646T patent/DE793646T1/de active Pending
- 1995-11-13 CN CN95196384A patent/CN1097580C/zh not_active Expired - Fee Related
- 1995-11-13 MX MX9703807A patent/MX9703807A/es unknown
- 1995-11-13 US US08/952,717 patent/US6166080A/en not_active Expired - Fee Related
- 1995-11-13 ES ES95939672T patent/ES2163531T3/es not_active Expired - Lifetime
- 1995-11-13 GE GEAP19953797A patent/GEP20002026B/en unknown
- 1995-11-13 BR BR9509741A patent/BR9509741A/pt not_active Application Discontinuation
- 1995-11-13 AU AU42796/96A patent/AU705893B2/en not_active Ceased
- 1995-11-13 DK DK95939672T patent/DK0793646T3/da active
- 1995-11-13 DE DE69522580T patent/DE69522580T2/de not_active Expired - Fee Related
- 1995-11-13 PL PL95320361A patent/PL184614B1/pl unknown
- 1995-11-13 HU HU9701701A patent/HUT77133A/hu unknown
- 1995-11-13 WO PCT/US1995/014126 patent/WO1996016031A1/en active IP Right Grant
- 1995-11-13 CZ CZ19971369A patent/CZ288597B6/cs not_active IP Right Cessation
- 1995-11-13 JP JP8516882A patent/JPH10509455A/ja not_active Ceased
- 1995-11-13 CA CA002202265A patent/CA2202265A1/en not_active Abandoned
- 1995-11-13 RU RU97110081/04A patent/RU2162462C2/ru not_active IP Right Cessation
- 1995-11-13 SK SK640-97A patent/SK282357B6/sk unknown
- 1995-11-13 EE EE9700094A patent/EE03392B1/xx not_active IP Right Cessation
- 1995-11-13 AT AT95939672T patent/ATE205188T1/de not_active IP Right Cessation
- 1995-11-13 EP EP95939672A patent/EP0793646B1/en not_active Expired - Lifetime
- 1995-11-13 NZ NZ297604A patent/NZ297604A/en unknown
1997
- 1997-05-22 NO NO972346A patent/NO308992B1/no unknown
- 1997-05-22 FI FI972185A patent/FI972185A0/fi unknown
1999
- 1999-11-08 US US09/435,717 patent/US6329545B1/en not_active Expired - Fee Related
2002
- 2002-04-10 CN CN02106295A patent/CN1377642A/zh active Pending

Also Published As

Publication number	Publication date
ATE205188T1 (de)	2001-09-15
US6329545B1 (en)	2001-12-11
CN1377642A (zh)	2002-11-06
NO308992B1 (no)	2000-11-27
SK64097A3 (en)	1997-11-05
BR9509741A (pt)	1997-10-21
ES2163531T3 (es)	2002-02-01
CZ136997A3 (cs)	1998-02-18
RU2162462C2 (ru)	2001-01-27
JPH10509455A (ja)	1998-09-14
MX9703807A (es)	1997-08-30
EP0793646B1 (en)	2001-09-05
PL320361A1 (en)	1997-09-29
CN1164226A (zh)	1997-11-05
FI972185A (fi)	1997-05-22
PL184614B1 (pl)	2002-11-29
DK0793646T3 (da)	2001-12-17
NO972346D0 (no)	1997-05-22
GEP20002026B (en)	2000-04-10
EP0793646A1 (en)	1997-09-10
EE9700094A (et)	1997-10-15
DE69522580D1 (de)	2001-10-11
NO972346L (no)	1997-07-23
CN1097580C (zh)	2003-01-01
FI972185A0 (fi)	1997-05-22
EE03392B1 (et)	2001-04-16
US6166080A (en)	2000-12-26
NZ297604A (en)	2000-07-28
AU4279696A (en)	1996-06-17
HUT77133A (hu)	1998-03-02
AU705893B2 (en)	1999-06-03
CA2202265A1 (en)	1996-05-30
DE793646T1 (de)	1999-12-30
PT793646E (pt)	2002-03-28
CZ288597B6 (cs)	2001-07-11
DE69522580T2 (de)	2002-10-10
WO1996016031A1 (en)	1996-05-30

Publication	Publication Date	Title
SK282357B6 (sk)	2002-01-07	Aminoguanidínkarboxyláty a ich použitie
AU664710B2 (en)	1995-11-30	A method for treatment of metabolic disorders
DE69227512T2 (de)	1999-04-08	N6-(hydrazinoiminomethyl)lysin und verfahren zur hemmung der stickstoffbildung im körper
MXPA97003807A (es)	1997-08-01	Carboxilatos de aminoguanidina para el tratamiento de la diabetes mellitus no dependiente de la insulina
US5994577A (en)	1999-11-30	Aminoguanidine carboxylates for the treatment of non-insulin-dependent diabetes mellitus
EP0680469A1 (de)	1995-11-08	Aminosäurederivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
EP2260022B1 (de)	2017-01-04	Substituierte cyclohexyldiamine
CA2478599A1 (en)	2003-09-18	Salts of nateglinide
CA3020393A1 (en)	2017-10-19	Chiral peptides
US20020082448A1 (en)	2002-06-27	Aminoguanidine carboxylates for the treatment of non-insulin-dependent diabetes mellitus
US6177453B1 (en)	2001-01-23	Aminoguanidine carboxylate lactams for the treatment of non-insulin-dependent diabetes mellitus
US4206231A (en)	1980-06-03	Hypoglycaemically active 2-alkyl- or -alkenyl-hydrazono propionic acid derivatives
WO2010078867A1 (de)	2010-07-15	Verfahren zur verbesserten bioaktivierung von arzneistoffen
US20030225087A1 (en)	2003-12-04	N-alkyl-N-phenylhydroxylamine compounds containing metal chelating groups, their preparation and their therapeutic uses
WO2000042001A1 (en)	2000-07-20	((aminoiminomethyl) amino) alkanecarboxamides and their applications in therapy
JPH08208481A (ja)	1996-08-13	脳障害治療剤
WO2006134963A1 (ja)	2006-12-21	オキサルル酸誘導体を含有する線維性疾患用剤