JP2006514956A - バソプレッシンアゴニストとしてのピロロ［２，１−ｃ］［１，４］ベンゾジアゼピン - Google Patents
バソプレッシンアゴニストとしてのピロロ［２，１−ｃ］［１，４］ベンゾジアゼピン Download PDFInfo
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- JP2006514956A JP2006514956A JP2004565510A JP2004565510A JP2006514956A JP 2006514956 A JP2006514956 A JP 2006514956A JP 2004565510 A JP2004565510 A JP 2004565510A JP 2004565510 A JP2004565510 A JP 2004565510A JP 2006514956 A JP2006514956 A JP 2006514956A
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- alkylene
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- 229940083335 Vasopressin agonist Drugs 0.000 title description 6
- MSNVESLISHTIRS-UHFFFAOYSA-N 9h-pyrrolo[2,1-c][1,4]benzodiazepine Chemical compound N1=C2C=CC=CC2=CN2CC=CC2=C1 MSNVESLISHTIRS-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 208000008967 Enuresis Diseases 0.000 claims abstract description 7
- 208000005346 nocturnal enuresis Diseases 0.000 claims abstract description 5
- -1 monofluoroalkyl Chemical group 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 6
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 6
- VKIODPSRTWIKKR-UHFFFAOYSA-N [2-chloro-4-[3-(hydroxymethyl)pyrazol-1-yl]phenyl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound N1=C(CO)C=CN1C(C=C1Cl)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 VKIODPSRTWIKKR-UHFFFAOYSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 206010046543 Urinary incontinence Diseases 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 206010029446 nocturia Diseases 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 27
- 239000002934 diuretic Substances 0.000 abstract description 5
- 230000000422 nocturnal effect Effects 0.000 abstract description 5
- 230000001882 diuretic effect Effects 0.000 abstract description 4
- 208000024891 symptom Diseases 0.000 abstract 1
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 description 31
- 108010004977 Vasopressins Proteins 0.000 description 30
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 description 29
- 102000002852 Vasopressins Human genes 0.000 description 29
- 125000003636 chemical group Chemical group 0.000 description 29
- 125000004432 carbon atom Chemical group C* 0.000 description 27
- 229960003726 vasopressin Drugs 0.000 description 27
- 241001465754 Metazoa Species 0.000 description 19
- 150000002430 hydrocarbons Chemical group 0.000 description 18
- 238000012360 testing method Methods 0.000 description 15
- 239000000126 substance Substances 0.000 description 13
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- 102000005962 receptors Human genes 0.000 description 12
- 210000002700 urine Anatomy 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000546 pharmaceutical excipient Substances 0.000 description 9
- 229930195734 saturated hydrocarbon Natural products 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229940116211 Vasopressin antagonist Drugs 0.000 description 8
- 108090000765 processed proteins & peptides Proteins 0.000 description 8
- 239000003038 vasopressin antagonist Substances 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 239000003792 electrolyte Substances 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- 241000282414 Homo sapiens Species 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000002148 esters Chemical group 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 230000003204 osmotic effect Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 4
- 125000005110 aryl thio group Chemical group 0.000 description 4
- 125000005164 aryl thioalkyl group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000003336 oxytocin antagonist Substances 0.000 description 4
- 229940121361 oxytocin antagonists Drugs 0.000 description 4
- 239000000651 prodrug Substances 0.000 description 4
- 229940002612 prodrug Drugs 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- NFLWUMRGJYTJIN-PNIOQBSNSA-N desmopressin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSCCC(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](CCCNC(N)=N)C(=O)NCC(N)=O)=O)CCC(=O)N)C1=CC=CC=C1 NFLWUMRGJYTJIN-PNIOQBSNSA-N 0.000 description 3
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- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
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- 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
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- 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
- A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/320,761 US7138393B2 (en) | 1998-07-24 | 2002-12-16 | Biologically active vasopressin agonist metabolites |
| PCT/US2003/039897 WO2004060894A1 (en) | 2002-12-16 | 2003-12-16 | Pyrrolo`2,1-c!`1,4! benzodiazepines as vasopressin agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006514956A true JP2006514956A (ja) | 2006-05-18 |
| JP2006514956A5 JP2006514956A5 (https=) | 2008-03-27 |
Family
ID=32710746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004565510A Pending JP2006514956A (ja) | 2002-12-16 | 2003-12-16 | バソプレッシンアゴニストとしてのピロロ［２，１−ｃ］［１，４］ベンゾジアゼピン |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7138393B2 (https=) |
| EP (1) | EP1572694B1 (https=) |
| JP (1) | JP2006514956A (https=) |
| CN (1) | CN1745083A (https=) |
| AR (1) | AR042467A1 (https=) |
| AT (1) | ATE410428T1 (https=) |
| AU (1) | AU2003297127A1 (https=) |
| BR (1) | BR0317383A (https=) |
| CA (1) | CA2508764A1 (https=) |
| DE (1) | DE60324018D1 (https=) |
| DK (1) | DK1572694T3 (https=) |
| ES (1) | ES2312859T3 (https=) |
| MX (1) | MXPA05006241A (https=) |
| TW (1) | TW200413355A (https=) |
| WO (1) | WO2004060894A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0210397D0 (en) | 2002-05-07 | 2002-06-12 | Ferring Bv | Pharmaceutical formulations |
| AU2008283929B2 (en) | 2007-08-06 | 2013-10-10 | Serenity Pharmaceuticals, Llc | Methods and devices for desmopressin drug delivery |
| US20100286045A1 (en) | 2008-05-21 | 2010-11-11 | Bjarke Mirner Klein | Methods comprising desmopressin |
| PL2712622T3 (pl) * | 2008-05-21 | 2017-01-31 | Ferring B.V. | Ulegająca rozpadowi w ustach desmopresyna do zwiększania początkowego okresu snu niezakłócanego przez nokturię |
| US11963995B2 (en) | 2008-05-21 | 2024-04-23 | Ferring B.V. | Methods comprising desmopressin |
| RU2510397C2 (ru) | 2008-11-18 | 2014-03-27 | Ф. Хоффманн-Ля Рош Аг | Алкилциклогексиловые эфиры дигидротетраазабензоазуленов |
| US9532959B2 (en) | 2010-07-08 | 2017-01-03 | Wellesley Pharmaceuticals, Llc | Pharmaceutical formulation for reducing frequency of urination and method of use thereof |
| US10010514B2 (en) | 2010-07-08 | 2018-07-03 | Wellesley Pharmaceuticals, Llc | Pharmaceutical formulation for reducing frequency of urination and method of use thereof |
| US10278925B2 (en) | 2012-01-04 | 2019-05-07 | Wellesley Pharmaceuticals, Llc | Delayed-release formulations, methods of making and use thereof |
| KR20190049928A (ko) * | 2012-01-04 | 2019-05-09 | 웰즐리 파마슈티컬스 엘엘씨 | 배뇨 빈도를 감소시키기 위한 서방형 제제 및 이의 사용 방법 |
| MY173582A (en) * | 2012-01-04 | 2020-02-04 | Wellesley Pharmaceuticals Llc | Extended-release formulation for reducing the frequency of urination and method of use thereof |
| US10105330B2 (en) | 2012-01-04 | 2018-10-23 | Wellesley Pharmaceuticals, Llc | Extended, delayed and immediate release formulation method of manufacturing and use thereof |
| US10105328B2 (en) | 2014-06-06 | 2018-10-23 | Wellesley Pharmaceuticals, Llc | Composition for reducing frequency of urination, method of making and use thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999006409A1 (en) * | 1997-07-30 | 1999-02-11 | American Home Products Corporation | Tricyclic vasopressin agonists |
| WO2001022969A2 (en) * | 1999-09-27 | 2001-04-05 | American Cynamid Company | Vasopressin agonist formulation and process |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1251767B (de) * | 1964-02-28 | 1968-04-18 | Dr Karl Thomae Gesellschaft mit beschrankter Haftung Biberach/Riß | Verfahren zur Herstellung von neuen m 6 Stellung substituierten 5 6 Dihydro-5oxo HH pyrido[2,3-b] [l,5]benzodiazepinen |
| US4680298A (en) | 1983-05-31 | 1987-07-14 | Schering Corporation | Tricyclic anti-allergy and use as anti-inflammatory agents |
| US4766108A (en) * | 1986-12-04 | 1988-08-23 | Smith Kline Beckman Corporation | Tyr-Arg-vasopressin antagonists |
| US5055448A (en) * | 1987-06-25 | 1991-10-08 | Medical College Of Ohio | Linear derivatives of arginine vasopressin antagonists |
| US4839355A (en) | 1987-09-09 | 1989-06-13 | Sterling Drug Inc. | Tricyclic-pyridinylquinoline compounds, their preparation and use |
| US5070187A (en) * | 1989-11-03 | 1991-12-03 | Trustees Of Boston University | Pharmacologically effective antagonists of arginine-vasopressin |
| CA2048003A1 (en) | 1990-08-21 | 1992-02-22 | Serge Burner | Tricyclic pyridone derivatives |
| US5516774A (en) * | 1993-07-29 | 1996-05-14 | American Cyanamid Company | Tricyclic diazepine vasopressin antagonists and oxytocin antagonists |
| US5512563A (en) * | 1993-07-29 | 1996-04-30 | American Cyanamid Company | Tricyclic benzazepine vasopressin antagonists |
| US5420270A (en) * | 1993-10-07 | 1995-05-30 | G. D. Searle & Co. | Aryl substituted dibenzoxazepine compounds, pharmaceutical compositions and methods of use |
| ES2284741T3 (es) | 1994-06-15 | 2007-11-16 | Otsuka Pharmaceutical Company, Limited | Derivados de benzoheterociclicos utilizados como moduladores de vasoprsinao de oxitocina. |
| JPH0881460A (ja) | 1994-09-08 | 1996-03-26 | Yamanouchi Pharmaceut Co Ltd | 新規なテトラヒドロベンゾジアゼピン誘導体又はその塩 |
| US5536718A (en) * | 1995-01-17 | 1996-07-16 | American Cyanamid Company | Tricyclic benzazepine vasopressin antagonists |
| US5521173A (en) * | 1995-01-17 | 1996-05-28 | American Home Products Corporation | Tricyclic benzazepine vasopressin antagonists |
| AR002459A1 (es) | 1995-01-17 | 1998-03-25 | American Cyanamid Co | Antagonistas de vasopresina de benzacepina triciclicos, una composicion farmaceutica que los contiene, un metodo para tratar enfermedades y unprocedimiento para su preparacion. |
| TW359669B (en) | 1995-12-15 | 1999-06-01 | Otsuka Pharma Co Ltd | Benzazepine derivatives |
| US5880122A (en) * | 1996-11-01 | 1999-03-09 | American Home Products Corporation | 3-Carboxamide derivatives of 5H-pyrrolo 2,1-c! 1,4!-benzodiazepines |
| AU727654B2 (en) | 1997-06-13 | 2000-12-21 | Yamanouchi Pharmaceutical Co., Ltd. | Tricyclic pyrazole derivative |
| US6194407B1 (en) * | 1997-07-30 | 2001-02-27 | American Home Products Corporation | Tricyclic pyrido vasopressin agonists |
| WO2000046228A2 (en) | 1999-02-04 | 2000-08-10 | American Home Products Corporation | Pyrrolobenzodiazepine carboxyamide vasopressin agonists |
| US6297234B1 (en) | 1999-02-04 | 2001-10-02 | American Home Products Corporation | Arylthiophene vasopressin agonists |
| EA200200415A1 (ru) | 1999-09-27 | 2002-10-31 | Американ Цианамид Компани | Композиция фармацевтического носителя |
| GB0000079D0 (en) | 2000-01-05 | 2000-02-23 | Ferring Bv | Novel antidiuretic agents |
| GB0015601D0 (en) | 2000-06-26 | 2000-08-16 | Ferring Bv | Novel antidiuretic agents |
-
2002
- 2002-12-16 US US10/320,761 patent/US7138393B2/en not_active Expired - Fee Related
-
2003
- 2003-12-09 TW TW092134683A patent/TW200413355A/zh unknown
- 2003-12-15 AR ARP030104629A patent/AR042467A1/es not_active Application Discontinuation
- 2003-12-16 WO PCT/US2003/039897 patent/WO2004060894A1/en not_active Ceased
- 2003-12-16 JP JP2004565510A patent/JP2006514956A/ja active Pending
- 2003-12-16 BR BR0317383-6A patent/BR0317383A/pt not_active IP Right Cessation
- 2003-12-16 DE DE60324018T patent/DE60324018D1/de not_active Expired - Lifetime
- 2003-12-16 MX MXPA05006241A patent/MXPA05006241A/es active IP Right Grant
- 2003-12-16 EP EP03814820A patent/EP1572694B1/en not_active Expired - Lifetime
- 2003-12-16 ES ES03814820T patent/ES2312859T3/es not_active Expired - Lifetime
- 2003-12-16 AT AT03814820T patent/ATE410428T1/de not_active IP Right Cessation
- 2003-12-16 CN CNA2003801095935A patent/CN1745083A/zh active Pending
- 2003-12-16 CA CA002508764A patent/CA2508764A1/en not_active Abandoned
- 2003-12-16 AU AU2003297127A patent/AU2003297127A1/en not_active Withdrawn
- 2003-12-16 DK DK03814820T patent/DK1572694T3/da active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999006409A1 (en) * | 1997-07-30 | 1999-02-11 | American Home Products Corporation | Tricyclic vasopressin agonists |
| WO2001022969A2 (en) * | 1999-09-27 | 2001-04-05 | American Cynamid Company | Vasopressin agonist formulation and process |
Also Published As
| Publication number | Publication date |
|---|---|
| US20030134845A1 (en) | 2003-07-17 |
| WO2004060894A1 (en) | 2004-07-22 |
| ES2312859T3 (es) | 2009-03-01 |
| CA2508764A1 (en) | 2004-07-22 |
| EP1572694A1 (en) | 2005-09-14 |
| AU2003297127A1 (en) | 2004-07-29 |
| DE60324018D1 (de) | 2008-11-20 |
| US7138393B2 (en) | 2006-11-21 |
| DK1572694T3 (da) | 2009-02-02 |
| BR0317383A (pt) | 2005-11-16 |
| AR042467A1 (es) | 2005-06-22 |
| CN1745083A (zh) | 2006-03-08 |
| ATE410428T1 (de) | 2008-10-15 |
| MXPA05006241A (es) | 2005-08-19 |
| TW200413355A (en) | 2004-08-01 |
| EP1572694B1 (en) | 2008-10-08 |
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