IL111791A - Crystalline, polymorphic forms of (sss) -n- (1-[2-carboxy -3- (n<2>-mesyllysysylamino) propyl] -1- cyclopentylcarbonyl) tyrosine, their preparation and pharmaceutical compositions comprising them - Google Patents
Crystalline, polymorphic forms of (sss) -n- (1-[2-carboxy -3- (n<2>-mesyllysysylamino) propyl] -1- cyclopentylcarbonyl) tyrosine, their preparation and pharmaceutical compositions comprising themInfo
- Publication number
- IL111791A IL111791A IL11179194A IL11179194A IL111791A IL 111791 A IL111791 A IL 111791A IL 11179194 A IL11179194 A IL 11179194A IL 11179194 A IL11179194 A IL 11179194A IL 111791 A IL111791 A IL 111791A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- formula
- nujol
- polymorphic form
- hydrated
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 49
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 15
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 title description 14
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 title description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 132
- 238000010521 absorption reaction Methods 0.000 claims abstract description 13
- 238000002329 infrared spectrum Methods 0.000 claims abstract description 13
- 239000000243 solution Substances 0.000 claims description 76
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 63
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 48
- 239000003054 catalyst Substances 0.000 claims description 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 26
- 125000006239 protecting group Chemical group 0.000 claims description 23
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- 230000008569 process Effects 0.000 claims description 17
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- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 16
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 15
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- 239000002904 solvent Substances 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 102000003729 Neprilysin Human genes 0.000 claims description 10
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- 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 claims description 3
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- 239000000496 cardiotonic agent Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
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- KMKLIOQYUUPLMA-UHFFFAOYSA-N chloromethyl prop-2-enoate Chemical compound ClCOC(=O)C=C KMKLIOQYUUPLMA-UHFFFAOYSA-N 0.000 description 1
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- 238000006731 degradation reaction Methods 0.000 description 1
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- 208000035475 disorder Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 1
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- 238000011067 equilibration Methods 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
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- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 108010016268 hippuryl-histidyl-leucine Proteins 0.000 description 1
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- 230000036543 hypotension Effects 0.000 description 1
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- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
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- 230000036584 pressor response Effects 0.000 description 1
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- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- SVBJTBWVTZLHIZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)prop-2-enoate Chemical compound CC(C)(C)OC(=O)C(=C)CO SVBJTBWVTZLHIZ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C311/06—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (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)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Vascular Medicine (AREA)
- Reproductive Health (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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)
- Peptides Or Proteins (AREA)
- Steroid Compounds (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL12883594A IL128835A (en) | 1993-12-04 | 1994-11-28 | Intermediates for the preparation of crystalline, polymorphic (sss) -n- (1-[2-carboxy-3-(n<2>-mesyllysylamino)propyl]-1-cyclopentylcarbonyl) tyrosine |
| IL12883599A IL128835A0 (en) | 1993-12-04 | 1999-03-04 | Intermediates for the preparation of crystalline polymorphic (SSS)-N-(1-(2-carboxy-3-(N2-mesyllysylamino)propyl)-1-cyclopentylcarbonyl) tyrosine and their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939324931A GB9324931D0 (en) | 1993-12-04 | 1993-12-04 | Glutaramide derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL111791A0 IL111791A0 (en) | 1995-01-24 |
| IL111791A true IL111791A (en) | 2002-09-12 |
Family
ID=10746163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL11179194A IL111791A (en) | 1993-12-04 | 1994-11-28 | Crystalline, polymorphic forms of (sss) -n- (1-[2-carboxy -3- (n<2>-mesyllysysylamino) propyl] -1- cyclopentylcarbonyl) tyrosine, their preparation and pharmaceutical compositions comprising them |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6180665B1 (de) |
| EP (1) | EP0731787B1 (de) |
| JP (1) | JP2701988B2 (de) |
| KR (1) | KR100203314B1 (de) |
| CN (1) | CN1068586C (de) |
| AT (1) | ATE175664T1 (de) |
| CA (1) | CA2178085C (de) |
| CZ (1) | CZ296428B6 (de) |
| DE (1) | DE69416003T2 (de) |
| DK (1) | DK0731787T3 (de) |
| EG (1) | EG20562A (de) |
| ES (1) | ES2128031T3 (de) |
| FI (1) | FI120305B (de) |
| GB (1) | GB9324931D0 (de) |
| GR (1) | GR3029590T3 (de) |
| HU (1) | HU225959B1 (de) |
| IL (1) | IL111791A (de) |
| MY (1) | MY115430A (de) |
| NO (1) | NO306714B1 (de) |
| NZ (1) | NZ276087A (de) |
| PE (1) | PE9296A1 (de) |
| PL (1) | PL178559B1 (de) |
| RU (1) | RU2131869C1 (de) |
| TW (2) | TW434210B (de) |
| WO (1) | WO1995015308A1 (de) |
| ZA (1) | ZA949595B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2001287405A1 (en) | 2000-08-29 | 2002-03-13 | Riverside Forest Products Limited | Collapsible bin |
| FR2824477B1 (fr) * | 2001-05-09 | 2005-09-09 | Ethypharm Lab Prod Ethiques | Granules enrobes a base d'inhibiteur de l'enzyme de conversion de l'anfiotensine, leur procede de preparation et comprimes orodispersibles contenant les granules enrobes |
| US6975515B2 (en) | 2001-08-15 | 2005-12-13 | Agilent Technologies, Inc. | Electrical module |
| CN102285916B (zh) * | 2003-02-12 | 2015-02-25 | 日产化学工业株式会社 | 匹伐他汀钙的晶形 |
| WO2005123702A1 (en) * | 2004-06-15 | 2005-12-29 | Pfizer Limited | Neutral endopeptidase inhibitor polymorph |
| CN109350736A (zh) * | 2018-09-20 | 2019-02-19 | 南通大学 | 防治运动病、梅尼埃病的药物及心房钠尿肽的医药用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8820844D0 (en) * | 1988-09-05 | 1988-10-05 | Pfizer Ltd | Therapeutic agents |
| US5208236A (en) | 1992-09-23 | 1993-05-04 | Schering Corporation | N-(acylaminomethyl)glutaryl amino acids and use |
-
1993
- 1993-12-04 GB GB939324931A patent/GB9324931D0/en active Pending
-
1994
- 1994-11-07 TW TW083110283A patent/TW434210B/zh not_active IP Right Cessation
- 1994-11-07 TW TW089110999A patent/TW534901B/zh not_active IP Right Cessation
- 1994-11-09 DE DE69416003T patent/DE69416003T2/de not_active Expired - Lifetime
- 1994-11-09 WO PCT/EP1994/003750 patent/WO1995015308A1/en not_active Ceased
- 1994-11-09 DK DK95900719T patent/DK0731787T3/da active
- 1994-11-09 CN CN94194942A patent/CN1068586C/zh not_active Expired - Fee Related
- 1994-11-09 EP EP95900719A patent/EP0731787B1/de not_active Expired - Lifetime
- 1994-11-09 US US08/648,001 patent/US6180665B1/en not_active Expired - Fee Related
- 1994-11-09 AT AT95900719T patent/ATE175664T1/de not_active IP Right Cessation
- 1994-11-09 JP JP7515356A patent/JP2701988B2/ja not_active Expired - Fee Related
- 1994-11-09 KR KR1019960702912A patent/KR100203314B1/ko not_active Expired - Fee Related
- 1994-11-09 CA CA002178085A patent/CA2178085C/en not_active Expired - Fee Related
- 1994-11-09 CZ CZ0160496A patent/CZ296428B6/cs not_active IP Right Cessation
- 1994-11-09 RU RU96115251A patent/RU2131869C1/ru not_active IP Right Cessation
- 1994-11-09 ES ES95900719T patent/ES2128031T3/es not_active Expired - Lifetime
- 1994-11-09 NZ NZ276087A patent/NZ276087A/en not_active IP Right Cessation
- 1994-11-09 PL PL94314794A patent/PL178559B1/pl not_active IP Right Cessation
- 1994-11-09 HU HU9601506A patent/HU225959B1/hu not_active IP Right Cessation
- 1994-11-28 IL IL11179194A patent/IL111791A/en not_active IP Right Cessation
- 1994-11-28 PE PE1994255868A patent/PE9296A1/es not_active Application Discontinuation
- 1994-11-29 MY MYPI94003169A patent/MY115430A/en unknown
- 1994-12-01 EG EG75294A patent/EG20562A/xx active
- 1994-12-02 ZA ZA949595A patent/ZA949595B/xx unknown
-
1996
- 1996-06-03 FI FI962322A patent/FI120305B/fi not_active IP Right Cessation
- 1996-06-04 NO NO962294A patent/NO306714B1/no not_active IP Right Cessation
-
1999
- 1999-03-05 GR GR990400677T patent/GR3029590T3/el unknown
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Legal Events
| Date | Code | Title | Description |
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| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |