NZ237249A - Veterinary compositions of 3-guanidinopropionic acid - Google Patents
Veterinary compositions of 3-guanidinopropionic acidInfo
- Publication number
- NZ237249A NZ237249A NZ237249A NZ23724991A NZ237249A NZ 237249 A NZ237249 A NZ 237249A NZ 237249 A NZ237249 A NZ 237249A NZ 23724991 A NZ23724991 A NZ 23724991A NZ 237249 A NZ237249 A NZ 237249A
- Authority
- NZ
- New Zealand
- Prior art keywords
- gpa
- mice
- insulin
- glucose
- see
- Prior art date
Links
- KMXXSJLYVJEBHI-UHFFFAOYSA-N 3-guanidinopropanoic acid Chemical group NC(=[NH2+])NCCC([O-])=O KMXXSJLYVJEBHI-UHFFFAOYSA-N 0.000 title claims abstract description 76
- 239000000203 mixture Substances 0.000 title description 11
- 238000000034 method Methods 0.000 claims abstract description 9
- 241001465754 Metazoa Species 0.000 claims description 16
- 230000003247 decreasing effect Effects 0.000 claims description 14
- 230000007423 decrease Effects 0.000 claims description 10
- 210000003205 muscle Anatomy 0.000 claims description 10
- 230000037213 diet Effects 0.000 claims description 6
- 235000005911 diet Nutrition 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 238000013268 sustained release Methods 0.000 claims description 4
- 239000012730 sustained-release form Substances 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 239000008183 oral pharmaceutical preparation Substances 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 abstract description 7
- 238000007910 systemic administration Methods 0.000 abstract description 2
- 241000699670 Mus sp. Species 0.000 description 39
- 239000008103 glucose Substances 0.000 description 39
- 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 37
- 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 description 30
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 24
- 206010012601 diabetes mellitus Diseases 0.000 description 20
- 210000004369 blood Anatomy 0.000 description 16
- 239000008280 blood Substances 0.000 description 16
- 230000037396 body weight Effects 0.000 description 16
- 102000004877 Insulin Human genes 0.000 description 15
- 108090001061 Insulin Proteins 0.000 description 15
- 229940125396 insulin Drugs 0.000 description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
- 206010022489 Insulin Resistance Diseases 0.000 description 12
- 208000008589 Obesity Diseases 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 201000001421 hyperglycemia Diseases 0.000 description 12
- 235000020824 obesity Nutrition 0.000 description 12
- 201000010099 disease Diseases 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 10
- 201000001320 Atherosclerosis Diseases 0.000 description 9
- 108010041872 Islet Amyloid Polypeptide Proteins 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 206010020772 Hypertension Diseases 0.000 description 8
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- 206010060378 Hyperinsulinaemia Diseases 0.000 description 7
- 102000036770 Islet Amyloid Polypeptide Human genes 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 230000035877 hyperamylinemia Effects 0.000 description 7
- 230000003451 hyperinsulinaemic effect Effects 0.000 description 7
- 201000008980 hyperinsulinism Diseases 0.000 description 7
- 208000002705 Glucose Intolerance Diseases 0.000 description 6
- 241000282412 Homo Species 0.000 description 6
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- 241000283984 Rodentia Species 0.000 description 6
- 230000009286 beneficial effect Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 241000282693 Cercopithecidae Species 0.000 description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 5
- 208000013016 Hypoglycemia Diseases 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 230000002218 hypoglycaemic effect Effects 0.000 description 5
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- 150000002632 lipids Chemical class 0.000 description 5
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- 210000002966 serum Anatomy 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- YHVFECVVGNXFKO-UHFFFAOYSA-N 4-guanidinobutanamide Chemical compound NC(=O)CCCNC(N)=N YHVFECVVGNXFKO-UHFFFAOYSA-N 0.000 description 4
- 230000003914 insulin secretion Effects 0.000 description 4
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 4
- 229960003105 metformin Drugs 0.000 description 4
- 210000002027 skeletal muscle Anatomy 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 241000251468 Actinopterygii Species 0.000 description 3
- 239000004475 Arginine Substances 0.000 description 3
- 229920002527 Glycogen Polymers 0.000 description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 3
- 108090001030 Lipoproteins Proteins 0.000 description 3
- 102000004895 Lipoproteins Human genes 0.000 description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 3
- 244000309466 calf Species 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 238000002405 diagnostic procedure Methods 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229940096919 glycogen Drugs 0.000 description 3
- 230000003345 hyperglycaemic effect Effects 0.000 description 3
- 244000144977 poultry Species 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 2
- 208000002249 Diabetes Complications Diseases 0.000 description 2
- 206010012655 Diabetic complications Diseases 0.000 description 2
- 206010018429 Glucose tolerance impaired Diseases 0.000 description 2
- 102100027670 Islet amyloid polypeptide Human genes 0.000 description 2
- 102000007330 LDL Lipoproteins Human genes 0.000 description 2
- 108010007622 LDL Lipoproteins Proteins 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- 208000001280 Prediabetic State Diseases 0.000 description 2
- 210000000577 adipose tissue Anatomy 0.000 description 2
- HIMXGTXNXJYFGB-UHFFFAOYSA-N alloxan Chemical compound O=C1NC(=O)C(=O)C(=O)N1 HIMXGTXNXJYFGB-UHFFFAOYSA-N 0.000 description 2
- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 2
- PLOPBXQQPZYQFA-AXPWDRQUSA-N amlintide Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H]1NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CCCCN)CSSC1)[C@@H](C)O)C(C)C)C1=CC=CC=C1 PLOPBXQQPZYQFA-AXPWDRQUSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000003178 anti-diabetic effect Effects 0.000 description 2
- 229940125708 antidiabetic agent Drugs 0.000 description 2
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- 229940098164 augmentin Drugs 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000001364 causal effect Effects 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 208000029078 coronary artery disease Diseases 0.000 description 2
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 201000010063 epididymitis Diseases 0.000 description 2
- 210000002468 fat body Anatomy 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 238000007446 glucose tolerance test Methods 0.000 description 2
- 230000013595 glycosylation Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000003127 radioimmunoassay Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 230000009469 supplementation Effects 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- AOFUBOWZWQFQJU-SNOJBQEQSA-N (2r,3s,4s,5r)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol;(2s,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O.OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O AOFUBOWZWQFQJU-SNOJBQEQSA-N 0.000 description 1
- -1 3-GPA compound Chemical class 0.000 description 1
- 102100031126 6-phosphogluconolactonase Human genes 0.000 description 1
- 108010029731 6-phosphogluconolactonase Proteins 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000031295 Animal disease Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010009192 Circulatory collapse Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 208000004930 Fatty Liver Diseases 0.000 description 1
- 102000005915 GABA Receptors Human genes 0.000 description 1
- 108010005551 GABA Receptors Proteins 0.000 description 1
- 229940121931 Gluconeogenesis inhibitor Drugs 0.000 description 1
- 108010018962 Glucosephosphate Dehydrogenase Proteins 0.000 description 1
- 206010018473 Glycosuria Diseases 0.000 description 1
- 108010023302 HDL Cholesterol Proteins 0.000 description 1
- 206010019708 Hepatic steatosis Diseases 0.000 description 1
- 102000005548 Hexokinase Human genes 0.000 description 1
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- 206010021143 Hypoxia Diseases 0.000 description 1
- 206010022562 Intermittent claudication Diseases 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 241000282560 Macaca mulatta Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 208000010428 Muscle Weakness Diseases 0.000 description 1
- 206010049565 Muscle fatigue Diseases 0.000 description 1
- 206010028372 Muscular weakness Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 208000000474 Poliomyelitis Diseases 0.000 description 1
- 208000017442 Retinal disease Diseases 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
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- 230000032683 aging Effects 0.000 description 1
- 230000002058 anti-hyperglycaemic effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 210000000476 body water Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 208000024980 claudication Diseases 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 229960003624 creatine Drugs 0.000 description 1
- 239000006046 creatine Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 208000010706 fatty liver disease Diseases 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- TUHVEAJXIMEOSA-UHFFFAOYSA-N gamma-guanidinobutyric acid Natural products NC(=[NH2+])NCCCC([O-])=O TUHVEAJXIMEOSA-UHFFFAOYSA-N 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 208000004104 gestational diabetes Diseases 0.000 description 1
- 230000004110 gluconeogenesis Effects 0.000 description 1
- 230000004153 glucose metabolism Effects 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000000910 hyperinsulinemic effect Effects 0.000 description 1
- 208000020346 hyperlipoproteinemia Diseases 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000006362 insulin response pathway Effects 0.000 description 1
- 206010022498 insulinoma Diseases 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 230000013190 lipid storage Effects 0.000 description 1
- 210000005228 liver tissue Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 230000005996 muscular dysfunction Effects 0.000 description 1
- 201000006938 muscular dystrophy Diseases 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001019 normoglycemic effect Effects 0.000 description 1
- 238000013116 obese mouse model Methods 0.000 description 1
- 229940100691 oral capsule Drugs 0.000 description 1
- 229940096978 oral tablet Drugs 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 208000021255 pancreatic insulinoma Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 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
- 229960003243 phenformin Drugs 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 230000000291 postprandial effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000011808 rodent model Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 206010040560 shock Diseases 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 231100000240 steatosis hepatitis Toxicity 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- APIBROGXENTUGB-ZUQRMPMESA-M triphenyl-[(e)-3-phenylprop-2-enyl]phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C\C=C\C1=CC=CC=C1 APIBROGXENTUGB-ZUQRMPMESA-M 0.000 description 1
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48661590A | 1990-02-28 | 1990-02-28 | |
| PCT/US1991/000334 WO1991012799A1 (en) | 1990-02-28 | 1991-01-22 | Use of 3-guanidinopropionic acid in the treatment and prevention of metabolic disorders |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ237249A true NZ237249A (en) | 1994-09-27 |
Family
ID=26782896
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ237249A NZ237249A (en) | 1990-02-28 | 1991-02-27 | Veterinary compositions of 3-guanidinopropionic acid |
| NZ245541A NZ245541A (en) | 1990-02-28 | 1991-02-27 | Oral pharmaceutical composition containing 3-guanidinopropionic acid |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ245541A NZ245541A (en) | 1990-02-28 | 1991-02-27 | Oral pharmaceutical composition containing 3-guanidinopropionic acid |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US5132324A (enExample) |
| EP (2) | EP0713699A2 (enExample) |
| JP (2) | JPH0825875B2 (enExample) |
| KR (1) | KR100190257B1 (enExample) |
| AT (1) | ATE141505T1 (enExample) |
| AU (2) | AU7316591A (enExample) |
| CA (1) | CA2073873C (enExample) |
| DE (1) | DE69121561T2 (enExample) |
| DK (1) | DK0517820T3 (enExample) |
| ES (1) | ES2090317T3 (enExample) |
| GR (1) | GR3021424T3 (enExample) |
| NZ (2) | NZ237249A (enExample) |
| WO (2) | WO1991012799A1 (enExample) |
| ZA (1) | ZA911496B (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5356913A (en) * | 1990-02-09 | 1994-10-18 | The Upjohn Company | Use of insulin sensitizing agents to treat hypertension |
| US6008253A (en) * | 1991-08-26 | 1999-12-28 | The Upjohn Company | Use of 3-guanidinopropionic acid to increase endurance, stamina and exercise capacity in a mammal |
| DK0601001T3 (da) * | 1991-08-26 | 1997-10-20 | Upjohn Co | Flydende næringsmiddelprodukt indeholdende 3-guanidinopropionsyre. |
| WO1993003714A2 (en) * | 1991-08-27 | 1993-03-04 | The Upjohn Company | Method for treatment of metabolic disorders |
| AU6950294A (en) * | 1993-05-14 | 1994-12-12 | Amira, Inc. | Treating body parts susceptible to ischemia using creatine analogs |
| US5808246A (en) * | 1995-09-25 | 1998-09-15 | Otis Elevator Company | Triac drive for three-phase line-powered linear induction motor elevator door operator |
| JPH11513671A (ja) * | 1995-10-11 | 1999-11-24 | アヴィセナ グループ，インク． | 糖代謝異常の治療のためのクレアチン類似体の利用 |
| ES2292176T3 (es) * | 1995-12-22 | 2008-03-01 | Smithkline Beecham Plc | Aminoguanidina para tratar la niddm. |
| US20040122096A1 (en) * | 1996-06-03 | 2004-06-24 | Hoechst Aktiengesellschaft | Use of inhibitors of the cellular Na+/H+ exchanger (NHE) for preparing a medicament for normalizing serum lipids |
| DE19622222A1 (de) * | 1996-06-03 | 1997-12-04 | Hoechst Ag | Verwendung von Inhibitoren des zellulären Na·+·/H·+·-Exchangers (NHE) zur Herstellung eines Medikament zur Normalisierung der Serumlipide |
| WO1998035667A1 (en) * | 1997-02-13 | 1998-08-20 | Smithkline Beecham Plc | Use of nitric oxid synthase inhibitors for the treatment of diabetes |
| US7910548B2 (en) * | 1997-06-06 | 2011-03-22 | Amylin Pharmaceuticals, Inc. | Methods for treating obesity |
| CN1150034C (zh) | 1998-08-24 | 2004-05-19 | 黑川清 | 羰基压力改善剂和腹膜透析液 |
| US7014307B2 (en) * | 1998-11-09 | 2006-03-21 | Silverbrook Research Pty Ltd | Printing unit for an image recordal and generation apparatus |
| US20050027005A1 (en) * | 2003-08-02 | 2005-02-03 | Matthias Boldt | Nutrient compositions and methods for sustenance and promotion of positive metabolic energy levels in a targeted manner |
| US8506934B2 (en) | 2005-04-29 | 2013-08-13 | Robert I. Henkin | Methods for detection of biological substances |
| WO2006119292A2 (en) * | 2005-04-29 | 2006-11-09 | Henkin, Robert | Methods for detection of biological substances |
| JP4777225B2 (ja) * | 2006-12-04 | 2011-09-21 | キヤノン株式会社 | 吐出用液体及び吐出方法 |
| WO2008095136A2 (en) | 2007-01-31 | 2008-08-07 | Henkin Robert I | Methods for detection of biological substances |
| US8580801B2 (en) | 2008-07-23 | 2013-11-12 | Robert I. Henkin | Phosphodiesterase inhibitor treatment |
| WO2012138214A1 (en) * | 2011-04-08 | 2012-10-11 | Brewster Lizzy Maritza | Beta-guanidinopropionic acid for the treatment of hypertension |
| CN106233141B (zh) | 2014-02-18 | 2018-08-21 | 罗伯特·I·汉金 | 用于诊断和治疗味觉或嗅觉的损失和/或失真的方法和组合物 |
| CN105963250A (zh) * | 2016-06-21 | 2016-09-28 | 俞力 | 一种口服葡萄糖溶液及其制备方法 |
| AU2020402994A1 (en) * | 2019-12-11 | 2022-06-23 | Inspirna, Inc. | Methods of treating cancer |
| KR102615692B1 (ko) * | 2021-10-13 | 2023-12-19 | 주식회사 휴엔켐 | 베타-구아니디노프로피온산을 포함하는 간섬유화 예방 또는 치료용 조성물 |
| KR102822799B1 (ko) | 2022-11-09 | 2025-06-20 | 충남대학교산학협력단 | 베타-구아니디노프로피온산을 포함하는 장내 미생물 개선용 조성물 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA891509A (en) * | 1972-01-25 | Beecham Group Limited | Esters and amides of guanidine aliphatic acids | |
| GB1153424A (en) * | 1965-04-15 | 1969-05-29 | Horlicks Ltd | Pharmaceutical Compositions |
| GB1195199A (en) * | 1966-11-25 | 1970-06-17 | Horlicks Pharmaceuticals Ltd | Improvements in Compositions comprising Insulin. |
| GB1195200A (en) * | 1967-02-07 | 1970-06-17 | Horlicks Pharmaceuticals Ltd | Pharmaceutical Compositions. |
| US3843798A (en) * | 1973-03-12 | 1974-10-22 | Stanley Drug Products Inc | Methods and compositions for inducing resistance to bacterial infections |
| GB1552179A (en) * | 1976-11-02 | 1979-09-12 | Beecham Group Ltd | Pharmaceutical compositions for treating hyperglycaemia |
| DK0601001T3 (da) * | 1991-08-26 | 1997-10-20 | Upjohn Co | Flydende næringsmiddelprodukt indeholdende 3-guanidinopropionsyre. |
-
1991
- 1991-01-22 WO PCT/US1991/000334 patent/WO1991012799A1/en not_active Ceased
- 1991-01-22 AU AU73165/91A patent/AU7316591A/en not_active Abandoned
- 1991-02-27 DK DK91905921.2T patent/DK0517820T3/da active
- 1991-02-27 DE DE69121561T patent/DE69121561T2/de not_active Expired - Fee Related
- 1991-02-27 KR KR1019920702067A patent/KR100190257B1/ko not_active Expired - Fee Related
- 1991-02-27 AT AT91905921T patent/ATE141505T1/de not_active IP Right Cessation
- 1991-02-27 AU AU74850/91A patent/AU645076B2/en not_active Ceased
- 1991-02-27 WO PCT/US1991/001109 patent/WO1991012800A1/en not_active Ceased
- 1991-02-27 NZ NZ237249A patent/NZ237249A/en unknown
- 1991-02-27 EP EP95117214A patent/EP0713699A2/en not_active Ceased
- 1991-02-27 EP EP91905921A patent/EP0517820B1/en not_active Expired - Lifetime
- 1991-02-27 JP JP3505980A patent/JPH0825875B2/ja not_active Expired - Lifetime
- 1991-02-27 NZ NZ245541A patent/NZ245541A/en unknown
- 1991-02-27 ES ES91905921T patent/ES2090317T3/es not_active Expired - Lifetime
- 1991-02-27 CA CA002073873A patent/CA2073873C/en not_active Expired - Fee Related
- 1991-02-28 ZA ZA911496A patent/ZA911496B/xx unknown
- 1991-06-10 US US07/712,862 patent/US5132324A/en not_active Expired - Fee Related
- 1991-08-14 US US07/780,432 patent/US5134164A/en not_active Expired - Fee Related
-
1995
- 1995-07-14 JP JP7178546A patent/JP2637712B2/ja not_active Expired - Lifetime
-
1996
- 1996-10-23 GR GR960402796T patent/GR3021424T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU7485091A (en) | 1991-09-18 |
| NZ245541A (en) | 1997-05-26 |
| ATE141505T1 (de) | 1996-09-15 |
| ZA911496B (en) | 1991-12-24 |
| EP0517820A1 (en) | 1992-12-16 |
| DE69121561D1 (de) | 1996-09-26 |
| JP2637712B2 (ja) | 1997-08-06 |
| AU645076B2 (en) | 1994-01-06 |
| JPH0825875B2 (ja) | 1996-03-13 |
| AU7316591A (en) | 1991-09-18 |
| JPH0820534A (ja) | 1996-01-23 |
| EP0713699A2 (en) | 1996-05-29 |
| EP0517820B1 (en) | 1996-08-21 |
| CA2073873C (en) | 1996-10-29 |
| WO1991012800A1 (en) | 1991-09-05 |
| JPH05505189A (ja) | 1993-08-05 |
| WO1991012799A1 (en) | 1991-09-05 |
| KR100190257B1 (ko) | 1999-06-01 |
| GR3021424T3 (en) | 1997-01-31 |
| CA2073873A1 (en) | 1991-08-29 |
| US5132324A (en) | 1992-07-21 |
| ES2090317T3 (es) | 1996-10-16 |
| EP0713699A3 (enExample) | 1996-07-10 |
| DK0517820T3 (da) | 1997-06-09 |
| US5134164A (en) | 1992-07-28 |
| DE69121561T2 (de) | 1997-01-30 |
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