NZ200641A - Pharmaceutical compositions containing(+)and(-)enantiomers of indacrinone - Google Patents
Pharmaceutical compositions containing(+)and(-)enantiomers of indacrinoneInfo
- Publication number
- NZ200641A NZ200641A NZ200641A NZ20064182A NZ200641A NZ 200641 A NZ200641 A NZ 200641A NZ 200641 A NZ200641 A NZ 200641A NZ 20064182 A NZ20064182 A NZ 20064182A NZ 200641 A NZ200641 A NZ 200641A
- Authority
- NZ
- New Zealand
- Prior art keywords
- enantiomer
- indacrinone
- proline
- weight
- phenylpropyl
- Prior art date
Links
- PRKWVSHZYDOZLP-UHFFFAOYSA-N 2-[(6,7-dichloro-2-methyl-1-oxo-2-phenyl-3h-inden-5-yl)oxy]acetic acid Chemical compound C1C2=CC(OCC(O)=O)=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=CC=C1 PRKWVSHZYDOZLP-UHFFFAOYSA-N 0.000 title claims description 66
- 229950009607 indacrinone Drugs 0.000 title claims description 42
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 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 title description 17
- XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 claims description 25
- 229960002576 amiloride Drugs 0.000 claims description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- 206010020772 Hypertension Diseases 0.000 claims description 8
- 206010030113 Oedema Diseases 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 150000002688 maleic acid derivatives Chemical class 0.000 claims description 7
- RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 claims description 6
- 229920000881 Modified starch Polymers 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 4
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 4
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 3
- -1 carboxy-3-phenylpropyl Chemical group 0.000 claims description 3
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000000314 lubricant Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 29
- 230000003424 uricosuric effect Effects 0.000 description 22
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 19
- 229940116269 uric acid Drugs 0.000 description 19
- 239000002934 diuretic Substances 0.000 description 15
- 230000009103 reabsorption Effects 0.000 description 12
- 201000001431 Hyperuricemia Diseases 0.000 description 10
- 230000001882 diuretic effect Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- 210000005239 tubule Anatomy 0.000 description 8
- 229940030606 diuretics Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000005541 ACE inhibitor Substances 0.000 description 6
- 229940097420 Diuretic Drugs 0.000 description 6
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- 229960000356 tienilic acid Drugs 0.000 description 6
- AGHANLSBXUWXTB-UHFFFAOYSA-N tienilic acid Chemical compound ClC1=C(Cl)C(OCC(=O)O)=CC=C1C(=O)C1=CC=CS1 AGHANLSBXUWXTB-UHFFFAOYSA-N 0.000 description 6
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 230000029142 excretion Effects 0.000 description 5
- 229960002003 hydrochlorothiazide Drugs 0.000 description 5
- 230000003389 potentiating effect Effects 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 210000003722 extracellular fluid Anatomy 0.000 description 4
- 239000002833 natriuretic agent Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 230000032258 transport Effects 0.000 description 4
- PRKWVSHZYDOZLP-GOSISDBHSA-N 2-[[(2r)-6,7-dichloro-2-methyl-1-oxo-2-phenyl-3h-inden-5-yl]oxy]acetic acid Chemical compound C1([C@@]2(C(C3=C(Cl)C(Cl)=C(OCC(O)=O)C=C3C2)=O)C)=CC=CC=C1 PRKWVSHZYDOZLP-GOSISDBHSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 230000001452 natriuretic effect Effects 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 210000000512 proximal kidney tubule Anatomy 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 208000019025 Hypokalemia Diseases 0.000 description 2
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 2
- 208000017169 kidney disease Diseases 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- WNBSDCKJFDZMHT-UHFFFAOYSA-N n-(diaminomethylidene)pyrazine-2-carboxamide Chemical compound NC(N)=NC(=O)C1=CN=CC=N1 WNBSDCKJFDZMHT-UHFFFAOYSA-N 0.000 description 2
- 208000024896 potassium deficiency disease Diseases 0.000 description 2
- 229910001414 potassium ion Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000000894 saliuretic effect Effects 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 230000007723 transport mechanism Effects 0.000 description 2
- PRKWVSHZYDOZLP-SFHVURJKSA-N 2-[[(2s)-6,7-dichloro-2-methyl-1-oxo-2-phenyl-3h-inden-5-yl]oxy]acetic acid Chemical compound C1([C@]2(C(C3=C(Cl)C(Cl)=C(OCC(O)=O)C=C3C2)=O)C)=CC=CC=C1 PRKWVSHZYDOZLP-SFHVURJKSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- ALLLEKJCUDAZJR-UHFFFAOYSA-N 6,7-dichloro-5-(thiophene-2-carbonyl)-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound ClC=1C(Cl)=C2OC(C(=O)O)CC2=CC=1C(=O)C1=CC=CS1 ALLLEKJCUDAZJR-UHFFFAOYSA-N 0.000 description 1
- 208000009304 Acute Kidney Injury Diseases 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 206010071200 Carbohydrate intolerance Diseases 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000000059 Dyspnea Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010019851 Hepatotoxicity Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010050394 Hyperkaliuria Diseases 0.000 description 1
- 206010021131 Hypouricaemia Diseases 0.000 description 1
- 206010021137 Hypovolaemia Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000000913 Kidney Calculi Diseases 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000010428 Muscle Weakness Diseases 0.000 description 1
- 206010028372 Muscular weakness Diseases 0.000 description 1
- 206010029148 Nephrolithiasis Diseases 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- 206010030124 Oedema peripheral Diseases 0.000 description 1
- 206010031123 Orthopnoea Diseases 0.000 description 1
- 208000002151 Pleural effusion Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 229940122767 Potassium sparing diuretic Drugs 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 206010037423 Pulmonary oedema Diseases 0.000 description 1
- 208000033626 Renal failure acute Diseases 0.000 description 1
- 229940116731 Uricosuric agent Drugs 0.000 description 1
- 208000006568 Urinary Bladder Calculi Diseases 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 201000011040 acute kidney failure Diseases 0.000 description 1
- 208000012998 acute renal failure Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001668 ameliorated effect Effects 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 230000002457 bidirectional effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical class OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 229940000406 drug candidate Drugs 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000003777 experimental drug Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- 230000007686 hepatotoxicity Effects 0.000 description 1
- 231100000304 hepatotoxicity Toxicity 0.000 description 1
- 229940097243 high-ceiling diuretic Drugs 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 230000036230 kaliuresis Effects 0.000 description 1
- 230000002077 kaliuretic effect Effects 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 208000009928 nephrosis Diseases 0.000 description 1
- 231100001027 nephrosis Toxicity 0.000 description 1
- 208000012144 orthopnea Diseases 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 239000003286 potassium sparing diuretic agent Substances 0.000 description 1
- 229940097241 potassium-sparing diuretic Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
- 229960003081 probenecid Drugs 0.000 description 1
- 229960002429 proline Drugs 0.000 description 1
- 208000005333 pulmonary edema Diseases 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000031 sodium potassium chloride symporter inhibitor Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000003383 uricosuric agent Substances 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 239000003981 vehicle Substances 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Gastroenterology & Hepatology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ212310A NZ212310A (en) | 1982-05-17 | 1982-05-17 | Pharmaceutical compositions containing(+)and(-)enantiomers of indacrinone and amiloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28236081A | 1981-07-13 | 1981-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ200641A true NZ200641A (en) | 1985-12-13 |
Family
ID=23081158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ200641A NZ200641A (en) | 1981-07-13 | 1982-05-17 | Pharmaceutical compositions containing(+)and(-)enantiomers of indacrinone |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0069846A1 (enExample) |
| JP (2) | JPS5810516A (enExample) |
| AU (1) | AU548904B2 (enExample) |
| CA (1) | CA1179603A (enExample) |
| DK (1) | DK223582A (enExample) |
| GR (1) | GR78032B (enExample) |
| NZ (1) | NZ200641A (enExample) |
| PT (1) | PT74955B (enExample) |
| ZA (1) | ZA823538B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1531221A (en) * | 1974-09-02 | 1978-11-08 | Smith Kline French Lab | Process for preparing guanidine derivatives |
| US4693996A (en) * | 1985-12-23 | 1987-09-15 | Warner-Lambert Company | Method of treating heart failure and medicaments therefor |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7412823A (nl) * | 1973-10-11 | 1975-04-15 | Merck & Co Inc | Werkwijze voor het bereiden van diuretisch ame preparaten en de door toepassing an verkregen voorwerpen. |
| PL98342B1 (pl) * | 1974-07-30 | 1978-04-29 | Sposob wytwarzania kwasu 1-keto-2-arylo-/lub tienylo/-2-podstawionego-indanyloksy-/lub tio/-5-alkanokarboksylowego | |
| US4087542A (en) * | 1975-07-09 | 1978-05-02 | Merck & Co., Inc. | 2,3-Dihydro-6,7-disubstituted-5-acyl benzofuran-2-carboxylic acids |
-
1982
- 1982-05-17 NZ NZ200641A patent/NZ200641A/en unknown
- 1982-05-18 DK DK223582A patent/DK223582A/da not_active Application Discontinuation
- 1982-05-19 AU AU83854/82A patent/AU548904B2/en not_active Ceased
- 1982-05-19 EP EP82104393A patent/EP0069846A1/en not_active Withdrawn
- 1982-05-21 ZA ZA823538A patent/ZA823538B/xx unknown
- 1982-05-25 PT PT74955A patent/PT74955B/pt unknown
- 1982-05-28 GR GR68288A patent/GR78032B/el unknown
- 1982-06-28 JP JP57110074A patent/JPS5810516A/ja active Pending
- 1982-07-09 CA CA000406976A patent/CA1179603A/en not_active Expired
-
1983
- 1983-07-01 JP JP58118372A patent/JPS5946220A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU548904B2 (en) | 1986-01-09 |
| PT74955B (en) | 1985-05-16 |
| PT74955A (en) | 1982-06-01 |
| DK223582A (da) | 1983-01-14 |
| CA1179603A (en) | 1984-12-18 |
| JPS5946220A (ja) | 1984-03-15 |
| JPS5810516A (ja) | 1983-01-21 |
| ZA823538B (en) | 1983-12-28 |
| GR78032B (enExample) | 1984-09-26 |
| AU8385482A (en) | 1983-01-20 |
| EP0069846A1 (en) | 1983-01-19 |
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