ZA200205180B - Condensed azepines as vasopressin agonists. - Google Patents
Condensed azepines as vasopressin agonists. Download PDFInfo
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- ZA200205180B ZA200205180B ZA200205180A ZA200205180A ZA200205180B ZA 200205180 B ZA200205180 B ZA 200205180B ZA 200205180 A ZA200205180 A ZA 200205180A ZA 200205180 A ZA200205180 A ZA 200205180A ZA 200205180 B ZA200205180 B ZA 200205180B
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- ZA
- South Africa
- Prior art keywords
- pharmaceutically acceptable
- acceptable salt
- compound according
- methyl
- proline
- Prior art date
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- 150000001538 azepines Chemical class 0.000 title claims description 4
- 229940083335 Vasopressin agonist Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 208000004880 Polyuria Diseases 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 208000008967 Enuresis Diseases 0.000 claims description 3
- 208000003450 Neurogenic Diabetes Insipidus Diseases 0.000 claims description 3
- 206010046543 Urinary incontinence Diseases 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 208000028235 central diabetes insipidus Diseases 0.000 claims description 3
- 201000010064 diabetes insipidus Diseases 0.000 claims description 3
- 208000031169 hemorrhagic disease Diseases 0.000 claims description 3
- 201000005119 neurohypophyseal diabetes insipidus Diseases 0.000 claims description 3
- 206010029446 nocturia Diseases 0.000 claims description 3
- 208000005346 nocturnal enuresis Diseases 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- RUOLFWZIFNQQGH-DEOSSOPVSA-N (2s)-2-n,2-n-dimethyl-1-n-[[2-methyl-4-(2,3,4,5-tetrahydro-1-benzazepine-1-carbonyl)phenyl]methyl]pyrrolidine-1,2-dicarboxamide Chemical compound CN(C)C(=O)[C@@H]1CCCN1C(=O)NCC1=CC=C(C(=O)N2C3=CC=CC=C3CCCC2)C=C1C RUOLFWZIFNQQGH-DEOSSOPVSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 239000012634 fragment Substances 0.000 description 16
- 108010004977 Vasopressins Proteins 0.000 description 11
- 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 11
- 239000001257 hydrogen Substances 0.000 description 11
- 102000002852 Vasopressins Human genes 0.000 description 10
- 229960003726 vasopressin Drugs 0.000 description 10
- 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 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 108010000437 Deamino Arginine Vasopressin Proteins 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- NFLWUMRGJYTJIN-NXBWRCJVSA-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-NXBWRCJVSA-N 0.000 description 7
- 229960004281 desmopressin Drugs 0.000 description 7
- -1 hydroxymethylene Chemical group 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000000556 agonist Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- 230000002686 anti-diuretic effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 3
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 102000004136 Vasopressin Receptors Human genes 0.000 description 2
- 108090000643 Vasopressin Receptors Proteins 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000001631 hypertensive effect Effects 0.000 description 2
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- 150000002829 nitrogen Chemical class 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000000813 peptide hormone Substances 0.000 description 2
- 239000000018 receptor agonist Substances 0.000 description 2
- 229940044601 receptor agonist Drugs 0.000 description 2
- AWOLMGJLKPNBDY-NOZRDPDXSA-N (2s,4r)-4-methoxy-2-n,2-n-dimethyl-1-n-[[2-methyl-4-(2,3,4,5-tetrahydro-1-benzazepine-1-carbonyl)phenyl]methyl]pyrrolidine-1,2-dicarboxamide Chemical compound C1[C@H](OC)C[C@@H](C(=O)N(C)C)N1C(=O)NCC1=CC=C(C(=O)N2C3=CC=CC=C3CCCC2)C=C1C AWOLMGJLKPNBDY-NOZRDPDXSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- WQADWIOXOXRPLN-AZXPZELESA-N 1,3-dithiane Chemical group C1CS[13CH2]SC1 WQADWIOXOXRPLN-AZXPZELESA-N 0.000 description 1
- IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-SCSAIBSYSA-N D-arginine Chemical compound OC(=O)[C@H](N)CCCNC(N)=N ODKSFYDXXFIFQN-SCSAIBSYSA-N 0.000 description 1
- 201000003542 Factor VIII deficiency 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 125000002785 azepinyl group Chemical group 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- QGCXDVIAGVEYLT-UHFFFAOYSA-N n-benzylpyrrolidine-1-carboxamide Chemical class C1CCCN1C(=O)NCC1=CC=CC=C1 QGCXDVIAGVEYLT-UHFFFAOYSA-N 0.000 description 1
- 229940127264 non-peptide agonist Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 210000001883 posterior pituitary gland Anatomy 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 108010047303 von Willebrand Factor Proteins 0.000 description 1
- 102100036537 von Willebrand factor Human genes 0.000 description 1
- 229960001134 von willebrand factor Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
-
- 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
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- 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
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- 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)
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- Hematology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0000079.4A GB0000079D0 (en) | 2000-01-05 | 2000-01-05 | Novel antidiuretic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200205180B true ZA200205180B (en) | 2004-02-05 |
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| Application Number | Title | Priority Date | Filing Date |
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| ZA200205180A ZA200205180B (en) | 2000-01-05 | 2002-06-27 | Condensed azepines as vasopressin agonists. |
Country Status (34)
| Country | Link |
|---|---|
| US (3) | US7074781B2 (ja) |
| EP (1) | EP1248784B1 (ja) |
| JP (2) | JP3869723B2 (ja) |
| KR (1) | KR100605466B1 (ja) |
| CN (1) | CN1183129C (ja) |
| AR (1) | AR035327A1 (ja) |
| AT (1) | ATE366730T1 (ja) |
| AU (1) | AU777538B2 (ja) |
| BR (1) | BR0107414B1 (ja) |
| CA (1) | CA2396277C (ja) |
| CY (1) | CY1108034T1 (ja) |
| CZ (1) | CZ303444B6 (ja) |
| DE (1) | DE60129298T2 (ja) |
| DK (1) | DK1248784T3 (ja) |
| EE (1) | EE200200367A (ja) |
| ES (1) | ES2288923T3 (ja) |
| GB (1) | GB0000079D0 (ja) |
| HK (1) | HK1046910B (ja) |
| HR (1) | HRP20020481B1 (ja) |
| HU (1) | HU229937B1 (ja) |
| IL (1) | IL149528A0 (ja) |
| MX (1) | MXPA02006546A (ja) |
| MY (1) | MY140467A (ja) |
| NO (1) | NO322571B1 (ja) |
| NZ (1) | NZ518803A (ja) |
| PL (1) | PL211341B1 (ja) |
| PT (1) | PT1248784E (ja) |
| RU (1) | RU2259367C2 (ja) |
| SI (1) | SI1248784T1 (ja) |
| SK (1) | SK287005B6 (ja) |
| UA (1) | UA73152C2 (ja) |
| UY (1) | UY26521A1 (ja) |
| WO (1) | WO2001049682A1 (ja) |
| ZA (1) | ZA200205180B (ja) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7138393B2 (en) | 1998-07-24 | 2006-11-21 | Wyeth | Biologically active vasopressin agonist metabolites |
| GB0000079D0 (en) * | 2000-01-05 | 2000-02-23 | Ferring Bv | Novel antidiuretic agents |
| SI1268418T1 (sl) * | 2000-03-27 | 2006-10-31 | Applied Research Systems | Farmacevtsko aktivni pirolidinski derivati kot bax-inhibitorji |
| DE60120940T2 (de) * | 2000-03-27 | 2007-01-25 | Applied Research Systems Ars Holding N.V. | Pyrrolidin-derivate verwendbar als bax-inhibitoren |
| GB0015601D0 (en) | 2000-06-26 | 2000-08-16 | Ferring Bv | Novel antidiuretic agents |
| GB0115515D0 (en) * | 2001-06-25 | 2001-08-15 | Ferring Bv | Oxytocin agonisys |
| GB0210397D0 (en) * | 2002-05-07 | 2002-06-12 | Ferring Bv | Pharmaceutical formulations |
| DK1619185T3 (da) | 2003-04-28 | 2011-07-18 | Astellas Pharma Inc | 4,4-difluor-1,2,3,4-tetrahydro-5H-1-benzazepinderivat eller salt deraf |
| DK1530967T3 (da) * | 2003-11-13 | 2006-07-03 | Ferring Bv | Blisterpakning og dertil hörende fast dosisform |
| EP1813603A1 (en) * | 2004-11-17 | 2007-08-01 | Kissei Pharmaceutical Co., Ltd. | Aromatic amide derivatives, medicinal compositions containing the same, medical uses of both |
| EP1867639A1 (en) * | 2005-03-25 | 2007-12-19 | Kissei Pharmaceutical Co., Ltd. | Urea derivative, medicinal composition containing the same, and medicinal use of these |
| WO2007052517A1 (ja) * | 2005-10-31 | 2007-05-10 | Sumitomo Chemical Company, Limited | ヒドロキシ－２－ピロリジンカルボキシアミド化合物の製法 |
| JP5220611B2 (ja) * | 2006-09-25 | 2013-06-26 | キッセイ薬品工業株式会社 | １，４−ベンゾジアゼピン誘導体、それを含有する医薬組成物およびそれらの医薬用途 |
| WO2008141081A1 (en) * | 2007-05-10 | 2008-11-20 | Amr Technology, Inc. | Aryl- and heteroaryl-substituted tetrahydrobenzo-1,4-diazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| 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 |
| US11963995B2 (en) | 2008-05-21 | 2024-04-23 | Ferring B.V. | Methods comprising desmopressin |
| EP2712622B1 (en) * | 2008-05-21 | 2016-07-13 | Ferring B.V. | Orodispersible desmopressin for increasing initial period of sleep undisturbed by nocturia |
| GB201005623D0 (en) * | 2010-04-01 | 2010-05-19 | Vantia Ltd | New polymorph |
| GB201105537D0 (en) | 2011-03-31 | 2011-05-18 | Vantia Ltd | New process |
| WO2020154581A1 (en) | 2019-01-24 | 2020-07-30 | Assia Chemical Industries Ltd | Solid state forms of fedovapagon-salicyclic acid co-crystal |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3960886A (en) | 1968-07-03 | 1976-06-01 | Sterling Drug Inc. | Substituted N-arylanilines |
| CA1047490A (en) | 1973-04-18 | 1979-01-30 | Friedrich Karrer | Ethers |
| CH599752A5 (ja) | 1973-04-18 | 1978-05-31 | Ciba Geigy Ag | |
| DE2355454A1 (de) | 1973-11-07 | 1976-10-07 | Paul Geisslinger | Lochmaschine |
| EP0186817B1 (en) | 1984-12-10 | 1989-08-02 | Nissan Chemical Industries Ltd. | 3(2h)pyridazinone, process for its preparation and anti-allergic agent containing it |
| ES2089033T3 (es) | 1989-10-20 | 1996-10-01 | Otsuka Pharma Co Ltd | Compuestos benzoheterociclicos. |
| US5753677A (en) | 1989-10-20 | 1998-05-19 | Otsuka Pharmaceutical Co., Ltd. | Benzoheterocyclic compounds |
| CA2066104C (en) | 1991-04-19 | 2003-05-27 | Hidenori Ogawa | Benzazepine derivatives as vasopressin antagonists |
| JPH05320135A (ja) * | 1992-05-19 | 1993-12-03 | Yamanouchi Pharmaceut Co Ltd | テトラヒドロベンズアゼピン誘導体 |
| AU657431B2 (en) | 1992-08-20 | 1995-03-09 | Otsuka Pharmaceutical Co., Ltd. | Benzoheterocyclic compounds as oxytocin and vasopressin antagonists |
| TW270927B (ja) * | 1992-10-16 | 1996-02-21 | Otsuka Pharma Co Ltd | |
| WO1994012476A1 (en) * | 1992-11-25 | 1994-06-09 | Yamanouchi Pharmaceutical Co., Ltd. | Benzanilide derivative |
| AU6219994A (en) * | 1993-03-11 | 1994-09-26 | Yamanouchi Pharmaceutical Co., Ltd. | Compound with vasopressin antagonism |
| GB9307527D0 (en) | 1993-04-13 | 1993-06-02 | Fujisawa Pharmaceutical Co | New venzamide derivatives,processes for the preparation thereof and pharmaceutical composition comprising the same |
| US5843952A (en) | 1993-07-29 | 1998-12-01 | American Cyanamid Company | Tricyclic benzazepine vasopressin antagonists |
| US5968930A (en) | 1993-07-29 | 1999-10-19 | American Cyanamid Company | Tricyclic diazepine vasopressin antagonists and oxytocin antagonists |
| US5516774A (en) | 1993-07-29 | 1996-05-14 | American Cyanamid Company | Tricyclic diazepine vasopressin antagonists and oxytocin antagonists |
| US5760031A (en) | 1993-07-29 | 1998-06-02 | American Cyanamid Company | Tricyclic benzazepine vasopressin antagonists |
| FI1215U1 (fi) * | 1993-12-03 | 1994-02-21 | Valmet Paper Machinery Inc | Anlaeggning i samband med styrningen av en vira |
| AU690980B2 (en) * | 1994-05-06 | 1998-05-07 | Koninklijke Philips Electronics N.V. | Microwave transmission system |
| ES2199251T3 (es) | 1994-06-15 | 2004-02-16 | Otsuka Pharmaceutical Company, Limited | Derivados benzoheterociclicos utilizables como moduladores de vasopresina o de oxitocina. |
| JP2926335B2 (ja) * | 1997-06-13 | 1999-07-28 | 大塚製薬株式会社 | 医薬組成物 |
| DE69826677T2 (de) * | 1997-07-30 | 2005-02-10 | Wyeth | Trizyclische Vasopressin-Agonisten |
| JP4338305B2 (ja) * | 1997-07-30 | 2009-10-07 | ワイス | 三環系バソプレシンアゴニスト |
| EP1119568B1 (en) | 1998-10-09 | 2004-02-18 | Janssen Pharmaceutica N.V. | 4,5-dihydro-isoxazole derivatives and their pharmaceutical use |
| GB2355454A (en) | 1999-10-20 | 2001-04-25 | Ferring Bv | Antidiuretic agents |
| 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 |
| DE10033337A1 (de) | 2000-07-08 | 2002-01-17 | Boehringer Ingelheim Pharma | Biphenylcarbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
| GB0120051D0 (en) | 2001-08-16 | 2001-10-10 | Ferring Bv | Oxytocin agonists |
| GB0224557D0 (en) | 2002-10-22 | 2002-11-27 | Glaxo Group Ltd | Novel compounds |
| EP1449844A1 (en) | 2003-02-14 | 2004-08-25 | Ferring B.V. | benzamide derivatives as oxytocin agonists and vasopressin antagonists |
| EP1627876A1 (en) | 2004-08-20 | 2006-02-22 | Ferring B.V. | Heterocyclic condensed compounds useful as antidiuretic agents |
| US7341963B2 (en) * | 2005-05-17 | 2008-03-11 | Milliken & Company | Non-woven material with barrier skin |
-
2000
- 2000-01-05 GB GBGB0000079.4A patent/GB0000079D0/en not_active Ceased
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2001
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- 2001-01-04 WO PCT/GB2001/000023 patent/WO2001049682A1/en active IP Right Grant
- 2001-01-04 PT PT01900169T patent/PT1248784E/pt unknown
- 2001-01-04 AU AU23846/01A patent/AU777538B2/en not_active Ceased
- 2001-01-04 DK DK01900169T patent/DK1248784T3/da active
- 2001-01-04 MY MYPI20010027A patent/MY140467A/en unknown
- 2001-01-04 PL PL355808A patent/PL211341B1/pl unknown
- 2001-01-04 US US10/130,749 patent/US7074781B2/en not_active Expired - Lifetime
- 2001-01-04 NZ NZ518803A patent/NZ518803A/xx not_active IP Right Cessation
- 2001-01-04 CN CNB018031323A patent/CN1183129C/zh not_active Expired - Fee Related
- 2001-01-04 AT AT01900169T patent/ATE366730T1/de active
- 2001-01-04 HU HU0203917A patent/HU229937B1/hu not_active IP Right Cessation
- 2001-01-04 BR BRPI0107414-8A patent/BR0107414B1/pt not_active IP Right Cessation
- 2001-01-04 KR KR1020027006382A patent/KR100605466B1/ko active IP Right Grant
- 2001-01-04 EE EEP200200367A patent/EE200200367A/xx unknown
- 2001-01-04 JP JP2001550222A patent/JP3869723B2/ja not_active Expired - Fee Related
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- 2001-01-04 UY UY26521A patent/UY26521A1/es not_active IP Right Cessation
- 2001-01-04 DE DE60129298T patent/DE60129298T2/de not_active Expired - Lifetime
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- 2001-01-04 ES ES01900169T patent/ES2288923T3/es not_active Expired - Lifetime
- 2001-01-04 IL IL14952801A patent/IL149528A0/xx active IP Right Grant
- 2001-01-04 CZ CZ20022305A patent/CZ303444B6/cs not_active IP Right Cessation
- 2001-01-04 AR ARP010100035A patent/AR035327A1/es active IP Right Grant
- 2001-01-04 EP EP01900169A patent/EP1248784B1/en not_active Expired - Lifetime
- 2001-01-04 MX MXPA02006546A patent/MXPA02006546A/es active IP Right Grant
- 2001-01-04 SI SI200130766T patent/SI1248784T1/sl unknown
- 2001-04-01 UA UA2002075517A patent/UA73152C2/uk unknown
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2002
- 2002-05-31 HR HR20020481A patent/HRP20020481B1/xx not_active IP Right Cessation
- 2002-06-27 NO NO20023137A patent/NO322571B1/no not_active IP Right Cessation
- 2002-06-27 ZA ZA200205180A patent/ZA200205180B/en unknown
- 2002-11-26 HK HK02108525.5A patent/HK1046910B/zh not_active IP Right Cessation
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2005
- 2005-12-20 JP JP2005366100A patent/JP3813629B2/ja not_active Expired - Fee Related
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- 2008-06-23 US US12/213,651 patent/US20080261951A1/en not_active Abandoned
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