AR095674A2 - PERIPHERALLY SELECTIVE DOPAMINE-B-HYDROXYLASE INHIBITORS AND METHOD FOR PREPARATION - Google Patents
PERIPHERALLY SELECTIVE DOPAMINE-B-HYDROXYLASE INHIBITORS AND METHOD FOR PREPARATIONInfo
- Publication number
- AR095674A2 AR095674A2 ARP140101283A ARP140101283A AR095674A2 AR 095674 A2 AR095674 A2 AR 095674A2 AR P140101283 A ARP140101283 A AR P140101283A AR P140101283 A ARP140101283 A AR P140101283A AR 095674 A2 AR095674 A2 AR 095674A2
- Authority
- AR
- Argentina
- Prior art keywords
- group
- preparation
- alkyl
- halogen
- term
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 108700006189 dopamine beta hydroxylase deficiency Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- -1 hydroxy, nitro, amino Chemical group 0.000 abstract 3
- 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 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- XESORRKVRNORPM-SSDOTTSWSA-N (3r)-6,8-difluoro-3,4-dihydro-2h-chromen-3-amine Chemical compound C1=C(F)C=C2C[C@@H](N)COC2=C1F XESORRKVRNORPM-SSDOTTSWSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 206010007558 Cardiac failure chronic Diseases 0.000 abstract 1
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 206010020772 Hypertension Diseases 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000005544 phthalimido group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 125000004665 trialkylsilyl group Chemical group 0.000 abstract 1
Classifications
-
- 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
- C07D487/22—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 four or more hetero rings
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
-
- 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
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/409—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having four such rings, e.g. porphine derivatives, bilirubin, biliverdine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Se describen compuestos de fórmula (1) y un método para su preparación, donde R¹, R² y R³ son iguales o diferentes y significan hidrógenos, halógenos, grupo alquilo, alquiloxi, hidroxi, nitro, amino, alquilcarbonilamino, alquilamino o dialquilamino; R⁴ significa hidrógeno, grupo alquilo o alquilarilo; X significa CH₂, átomo de oxígeno o átomo de azufre; n es 1, 2 ó 3, con la condición de que cuando n es 1, X no es CH₂; y los enantiómeros (R) y (S) individuales o mezclas de enantiómeros y sus sales farmacéuticamente aceptables; donde el término alquilo significa cadenas de hidrocarburos, rectas o ramificadas que contienen entre uno y seis átomos de carbono, opcionalmente sustituidas con grupos arilo, alcoxi, halógeno, alcoxicarbonilo o hidroxicarbonilo; el término arilo significa un grupo fenilo o naftilo, opcionalmente sustituido con un grupo alquiloxi, halógeno o nitro; el término halógeno significa flúor, cloro, bromo o yodo. Los compuestos tienen propiedades farmacéuticas potencialmente valiosas para el tratamiento de trastornos cardiovasculares tales como la hipertensión y la insuficiencia cardíaca crónica. También se describe, una composición farmacéutica, su uso para la preparación de medicamentos, procesos e intermediarios. Reivindicación 11: Un compuesto de fórmula (2), donde n significa 3, R⁵ significa un grupo protector hidroxilo; y R⁴ y R⁶ tomados en forma conjunta representan un grupo ftalimido, donde el grupo protector hidroxilo es un grupo trialquilsililo, trifenilsililo, fenildialquilsililo o alquildifenilsililo. Reivindicación 13: (R)-6,8-diflúor-3,4-dihidro-2H-1-benzopiran-3-amina.Compounds of formula (1) and a method for their preparation are described, wherein R¹, R² and R³ are the same or different and mean hydrogens, halogens, alkyl, alkyloxy, hydroxy, nitro, amino, alkylcarbonylamino, alkylamino or dialkylamino groups; R⁴ means hydrogen, alkyl or alkylaryl group; X means CH₂, oxygen atom or sulfur atom; n is 1, 2 or 3, with the proviso that when n is 1, X is not CH₂; and the individual (R) and (S) enantiomers or mixtures of enantiomers and their pharmaceutically acceptable salts; where the term "alkyl" means straight or branched hydrocarbon chains containing between one and six carbon atoms, optionally substituted with aryl, alkoxy, halogen, alkoxycarbonyl or hydroxycarbonyl groups; the term "aryl" means a phenyl or naphthyl group, optionally substituted with an alkyloxy, halogen or nitro group; The term halogen means fluorine, chlorine, bromine or iodine. The compounds have potentially valuable pharmaceutical properties for the treatment of cardiovascular disorders such as hypertension and chronic heart failure. Also described is a pharmaceutical composition, its use for the preparation of medicines, processes and intermediaries. Claim 11: A compound of formula (2), wherein n means 3, R⁵ means a hydroxyl protecting group; and R⁴ and R⁶ taken together represent a phthalimido group, where the hydroxyl protecting group is a trialkylsilyl, triphenylsilyl, phenyldialkylsilyl or alkyldiphenylsilyl group. Claim 13: (R) -6,8-difluoro-3,4-dihydro-2H-1-benzopyran-3-amine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0223719A GB2393958A (en) | 2002-10-11 | 2002-10-11 | Peripherally-selective imidazole inhibitors of dopamine-beta-hydroxylase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR095674A2 true AR095674A2 (en) | 2015-11-04 |
Family
ID=9945777
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP030103711A AR041589A1 (en) | 2002-10-11 | 2003-10-10 | PERIPHERALLY SELECTIVE DOPAMINE-BETA-HYDROXYLASE INHIBITORS AND METHOD FOR PREPARATION |
| ARP140101283A AR095674A2 (en) | 2002-10-11 | 2014-03-18 | PERIPHERALLY SELECTIVE DOPAMINE-B-HYDROXYLASE INHIBITORS AND METHOD FOR PREPARATION |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP030103711A AR041589A1 (en) | 2002-10-11 | 2003-10-10 | PERIPHERALLY SELECTIVE DOPAMINE-BETA-HYDROXYLASE INHIBITORS AND METHOD FOR PREPARATION |
Country Status (11)
| Country | Link |
|---|---|
| KR (1) | KR101350741B1 (en) |
| CN (1) | CN100393715C (en) |
| AR (2) | AR041589A1 (en) |
| AT (5) | ATE500248T1 (en) |
| CY (2) | CY1108452T1 (en) |
| DE (4) | DE60336275D1 (en) |
| DK (2) | DK1908760T3 (en) |
| ES (5) | ES2309279T3 (en) |
| GB (2) | GB2393958A (en) |
| HK (1) | HK1116188A1 (en) |
| SI (2) | SI1408038T1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0708818D0 (en) * | 2007-05-08 | 2007-06-13 | Portela & Ca Sa | Compounds |
| WO2012087174A2 (en) * | 2010-12-22 | 2012-06-28 | BIAL - PORTELA & Cª., S.A. | Crystalline forms and processes for their preparation |
| GB201316410D0 (en) * | 2013-09-13 | 2013-10-30 | Bial Portela & Ca Sa | Processes for preparing peripherally-selective inhibitors of dopamine-?-hydroxylase and intermediates for use therein |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL82401A0 (en) * | 1986-05-06 | 1987-11-30 | Merrell Dow Pharma | Dopamine beta hydroxy-lase inhibiting imidazole derivatives and pharmaceutical compositions containing them |
| US4868210A (en) | 1988-03-30 | 1989-09-19 | Warner-Lambert Company | Antihyperlipidemic and antiatherosclerotic compounds and compositions |
| MX9605145A (en) * | 1994-04-26 | 1997-12-31 | Syntex Inc | Benzocycloalkylazolethione derivatives. |
-
2002
- 2002-10-11 GB GB0223719A patent/GB2393958A/en not_active Withdrawn
- 2002-10-18 GB GB0224306A patent/GB2394223B/en not_active Expired - Lifetime
-
2003
- 2003-10-10 KR KR1020127005102A patent/KR101350741B1/en active IP Right Grant
- 2003-10-10 AT AT07076122T patent/ATE500248T1/en not_active IP Right Cessation
- 2003-10-10 SI SI200331309T patent/SI1408038T1/en unknown
- 2003-10-10 DK DK07076125.9T patent/DK1908760T3/en active
- 2003-10-10 DK DK03256420T patent/DK1408038T3/en active
- 2003-10-10 CN CNB2003801059426A patent/CN100393715C/en not_active Expired - Fee Related
- 2003-10-10 AT AT07076125T patent/ATE505465T1/en active
- 2003-10-10 ES ES03256420T patent/ES2309279T3/en not_active Expired - Lifetime
- 2003-10-10 DE DE60336275T patent/DE60336275D1/en not_active Expired - Lifetime
- 2003-10-10 ES ES07076122T patent/ES2361938T3/en not_active Expired - Lifetime
- 2003-10-10 DE DE60336276T patent/DE60336276D1/en not_active Expired - Lifetime
- 2003-10-10 ES ES07076124T patent/ES2361939T3/en not_active Expired - Lifetime
- 2003-10-10 DE DE60322642T patent/DE60322642D1/en not_active Expired - Lifetime
- 2003-10-10 DE DE60336772T patent/DE60336772D1/en not_active Expired - Lifetime
- 2003-10-10 ES ES07076125T patent/ES2364919T3/en not_active Expired - Lifetime
- 2003-10-10 AR ARP030103711A patent/AR041589A1/en active IP Right Grant
- 2003-10-10 AT AT03256420T patent/ATE403652T1/en active
- 2003-10-10 SI SI200331986T patent/SI1908760T1/en unknown
- 2003-10-10 AT AT07076123T patent/ATE550335T1/en active
- 2003-10-10 ES ES07076123T patent/ES2384118T3/en not_active Expired - Lifetime
- 2003-10-10 AT AT07076124T patent/ATE500247T1/en not_active IP Right Cessation
-
2008
- 2008-10-09 HK HK08111214.9A patent/HK1116188A1/en not_active IP Right Cessation
- 2008-10-24 CY CY20081101204T patent/CY1108452T1/en unknown
-
2011
- 2011-07-01 CY CY20111100639T patent/CY1112457T1/en unknown
-
2014
- 2014-03-18 AR ARP140101283A patent/AR095674A2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB2393958A (en) | 2004-04-14 |
| ATE550335T1 (en) | 2012-04-15 |
| ATE505465T1 (en) | 2011-04-15 |
| DK1408038T3 (en) | 2008-11-24 |
| GB0224306D0 (en) | 2002-11-27 |
| CN1726211A (en) | 2006-01-25 |
| GB2394223B (en) | 2007-05-16 |
| DE60336276D1 (en) | 2011-04-14 |
| ES2309279T3 (en) | 2008-12-16 |
| GB2394223A (en) | 2004-04-21 |
| HK1116188A1 (en) | 2008-12-19 |
| ATE403652T1 (en) | 2008-08-15 |
| SI1908760T1 (en) | 2011-05-31 |
| ATE500247T1 (en) | 2011-03-15 |
| CY1108452T1 (en) | 2014-04-09 |
| KR101350741B1 (en) | 2014-01-10 |
| SI1408038T1 (en) | 2008-10-31 |
| AR041589A1 (en) | 2005-05-26 |
| CN100393715C (en) | 2008-06-11 |
| DE60336275D1 (en) | 2011-04-14 |
| CY1112457T1 (en) | 2015-12-09 |
| ATE500248T1 (en) | 2011-03-15 |
| DK1908760T3 (en) | 2011-07-25 |
| ES2361938T3 (en) | 2011-06-24 |
| DE60322642D1 (en) | 2008-09-18 |
| ES2364919T3 (en) | 2011-09-16 |
| GB0223719D0 (en) | 2002-11-20 |
| DE60336772D1 (en) | 2011-05-26 |
| ES2361939T3 (en) | 2011-06-24 |
| KR20120038014A (en) | 2012-04-20 |
| ES2384118T3 (en) | 2012-06-29 |
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