TWI507410B - 新穎磷酸二酯酶抑制劑 - Google Patents

新穎磷酸二酯酶抑制劑 Download PDF

Info

Publication number
TWI507410B
TWI507410B TW100122303A TW100122303A TWI507410B TW I507410 B TWI507410 B TW I507410B TW 100122303 A TW100122303 A TW 100122303A TW 100122303 A TW100122303 A TW 100122303A TW I507410 B TWI507410 B TW I507410B
Authority
TW
Taiwan
Prior art keywords
compound
spiro
difluoromethoxy
dichloro
oxo
Prior art date
Application number
TW100122303A
Other languages
English (en)
Chinese (zh)
Other versions
TW201206940A (en
Inventor
Simon Feldbaek Nielsen
Original Assignee
Leo Pharma As
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Leo Pharma As filed Critical Leo Pharma As
Publication of TW201206940A publication Critical patent/TW201206940A/zh
Application granted granted Critical
Publication of TWI507410B publication Critical patent/TWI507410B/zh

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02Heterocyclic 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
    • C07D495/10Spiro-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/443Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4433Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with oxygen as a ring hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4436Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0053Mouth and digestive tract, i.e. intraoral and peroral administration
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/02Nasal agents, e.g. decongestants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/06Antiasthmatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/12Drugs for disorders of the urinary system of the kidneys
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/02Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/04Antipruritics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/06Antipsoriatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/14Drugs for dermatological disorders for baldness or alopecia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/08Antiallergic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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
    • C07D405/06Heterocyclic 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 linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D493/00Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10Spiro-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Immunology (AREA)
  • Pulmonology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Diabetes (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Psychiatry (AREA)
  • Physiology (AREA)
  • Nutrition Science (AREA)
  • Endocrinology (AREA)
  • Vascular Medicine (AREA)
  • Emergency Medicine (AREA)
  • Otolaryngology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Hospice & Palliative Care (AREA)
TW100122303A 2010-06-24 2011-06-24 新穎磷酸二酯酶抑制劑 TWI507410B (zh)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US35820910P 2010-06-24 2010-06-24

Publications (2)

Publication Number Publication Date
TW201206940A TW201206940A (en) 2012-02-16
TWI507410B true TWI507410B (zh) 2015-11-11

Family

ID=44351701

Family Applications (1)

Application Number Title Priority Date Filing Date
TW100122303A TWI507410B (zh) 2010-06-24 2011-06-24 新穎磷酸二酯酶抑制劑

Country Status (29)

Country Link
US (3) US8980905B2 (enExample)
EP (2) EP3070091B1 (enExample)
JP (2) JP6174997B2 (enExample)
KR (1) KR101864578B1 (enExample)
CN (1) CN102958937B (enExample)
AU (1) AU2011269429B2 (enExample)
BR (1) BR112012032813B1 (enExample)
CA (1) CA2802895C (enExample)
CY (2) CY1117862T1 (enExample)
DK (2) DK3070091T3 (enExample)
ES (2) ES2733092T3 (enExample)
HR (2) HRP20160919T1 (enExample)
HU (2) HUE030081T2 (enExample)
IL (1) IL223329A (enExample)
LT (2) LT3070091T (enExample)
MX (1) MX2012014131A (enExample)
MY (1) MY157481A (enExample)
NZ (1) NZ603895A (enExample)
PL (2) PL2585469T3 (enExample)
PT (2) PT3070091T (enExample)
RS (2) RS58945B1 (enExample)
RU (1) RU2583787C2 (enExample)
SG (1) SG186140A1 (enExample)
SI (2) SI3070091T1 (enExample)
TR (1) TR201909709T4 (enExample)
TW (1) TWI507410B (enExample)
UA (1) UA109140C2 (enExample)
WO (1) WO2011160632A1 (enExample)
ZA (1) ZA201209031B (enExample)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9855285B2 (en) * 2012-11-30 2018-01-02 Leo Pharma A/S Method of inhibiting the expression of IL-22 in activated T-cells
CA2953284A1 (en) * 2014-06-23 2015-12-30 Leo Pharma A/S Methods for the preparation of 1,3-benzodioxole heterocyclic compounds
WO2017089347A1 (en) 2015-11-25 2017-06-01 Inserm (Institut National De La Sante Et De La Recherche Medicale) Methods and pharmaceutical compositions for the treatment of braf inhibitor resistant melanomas
CA3007432A1 (en) * 2015-12-18 2017-06-22 Leo Pharma A/S Methods for the preparation of 1,3-benzodioxole heterocyclic compounds
WO2018234299A1 (en) * 2017-06-20 2018-12-27 Leo Pharma A/S Methods for the preparation of 1,3-benzodioxole heterocyclic compounds
CN111727191B (zh) 2017-12-15 2024-01-05 联合疗法公司 取代的氮杂环丁烷二氢噻吩并吡啶类化合物及其作为磷酸二酯酶抑制剂的用途
US11919912B2 (en) 2018-05-21 2024-03-05 Constellation Pharmaceuticals, Inc. Modulators of methyl modifying enzymes, compositions and uses thereof
IL284815B2 (en) * 2019-01-15 2025-10-01 Union Therapeutics As Modified-release tablet formulations containing phosphodiesterase inhibitors
EP4003343A1 (en) * 2019-07-24 2022-06-01 Constellation Pharmaceuticals, Inc. Ezh2 inhibition in combination therapies for the treatment of cancers
CN112552276B (zh) * 2019-09-25 2023-03-21 中国科学院上海药物研究所 苯并氧杂卓-5-酮类化合物及其制备方法和用途
AU2022245186A1 (en) 2021-03-22 2023-10-05 UNION therapeutics A/S Treatment of hidradenitis suppurativa with orismilast
GB202205715D0 (en) 2022-04-19 2022-06-01 Union Therapeutics As Treatment of neutrophilic dermatoses
GB202306662D0 (en) 2023-05-05 2023-06-21 Union Therapeutics As Dosage regimen
GB202306663D0 (en) 2023-05-05 2023-06-21 Union Therapeutics As Combination therapy

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008104175A2 (en) * 2007-02-28 2008-09-04 Leo Pharma A/S Novel phosphodiesterase inhibitors

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100331255B1 (ko) 1993-07-02 2002-10-25 빅굴덴 롬베르그 케미쉐 화부리크 게엠베하 플루오로알콕시-치환된벤즈아미드및시클릭뉴클레오티드포스포디에스테라아제억제제로서의그의용도
GB9507297D0 (en) 1995-04-07 1995-05-31 Rh Ne Poulenc Rorer Limited New composition of matter
AU705690B2 (en) 1995-05-19 1999-05-27 Kyowa Hakko Kogyo Co. Ltd. Oxygen-containing heterocyclic compounds
CA2252537A1 (en) * 1996-05-20 1997-11-27 Darwin Discovery Limited Benzofuran carboxamides and their therapeutic use
WO1998022455A1 (en) 1996-11-19 1998-05-28 Kyowa Hakko Kogyo Co., Ltd. Oxygenic heterocyclic compounds
JP2005060375A (ja) * 2003-07-28 2005-03-10 Kyowa Hakko Kogyo Co Ltd 含酸素複素環化合物
DE10360792A1 (de) 2003-12-23 2005-07-28 Grünenthal GmbH Spirocyclische Cyclohexan-Derivate
EA014956B1 (ru) * 2004-12-17 2011-04-29 ГЛЕНМАРК ФАРМАСЬЮТИКАЛС Эс.Эй. Гетероциклические соединения, применяемые для лечения воспалительных и аллергических нарушений
UA98639C2 (en) * 2007-02-28 2012-06-11 Лео Фарма А/С Phosphodiesterase inhibitors
PT2794603T (pt) * 2011-12-21 2016-07-26 Leo Pharma As [1,2,4] triazolopiridinas e seu uso como inibidores de fosfodiesterase

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008104175A2 (en) * 2007-02-28 2008-09-04 Leo Pharma A/S Novel phosphodiesterase inhibitors

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Kevin et al, Annual Review of Pharmacology and Toxicology, 2001, 41(1), p443-470 *

Also Published As

Publication number Publication date
HRP20160919T1 (hr) 2016-10-07
DK3070091T3 (da) 2019-07-08
EP3070091B1 (en) 2019-04-17
EP3070091A1 (en) 2016-09-21
ES2584055T3 (es) 2016-09-23
HUE044301T2 (hu) 2019-10-28
IL223329A0 (en) 2013-02-03
NZ603895A (en) 2014-10-31
RU2583787C2 (ru) 2016-05-10
MY157481A (en) 2016-06-15
UA109140C2 (uk) 2015-07-27
DK2585469T3 (en) 2016-08-29
RU2013103079A (ru) 2014-07-27
RS55104B1 (sr) 2016-12-30
SI3070091T1 (sl) 2019-08-30
BR112012032813A2 (pt) 2016-11-08
IL223329A (en) 2017-01-31
HK1182699A1 (zh) 2013-12-06
HUE030081T2 (en) 2017-04-28
ES2733092T3 (es) 2019-11-27
HRP20191136T1 (hr) 2019-09-20
WO2011160632A1 (en) 2011-12-29
CN102958937B (zh) 2016-03-30
LT3070091T (lt) 2019-07-25
RS58945B1 (sr) 2019-08-30
US20150111915A1 (en) 2015-04-23
US8980905B2 (en) 2015-03-17
CY1122201T1 (el) 2020-11-25
CY1117862T1 (el) 2017-05-17
AU2011269429B2 (en) 2015-07-09
EP2585469B1 (en) 2016-05-25
BR112012032813B1 (pt) 2022-02-01
US9637499B2 (en) 2017-05-02
JP2016164168A (ja) 2016-09-08
TR201909709T4 (tr) 2019-07-22
TW201206940A (en) 2012-02-16
KR101864578B1 (ko) 2018-06-07
LT2585469T (lt) 2016-10-10
ZA201209031B (en) 2014-02-26
CA2802895A1 (en) 2011-12-29
SG186140A1 (en) 2013-01-30
US20130123291A1 (en) 2013-05-16
PT2585469T (pt) 2016-08-29
PT3070091T (pt) 2019-07-22
JP2013529602A (ja) 2013-07-22
KR20130038341A (ko) 2013-04-17
EP2585469A1 (en) 2013-05-01
PL3070091T3 (pl) 2019-09-30
US20160022657A1 (en) 2016-01-28
MX2012014131A (es) 2013-01-29
CA2802895C (en) 2019-05-21
SI2585469T1 (sl) 2016-11-30
PL2585469T3 (pl) 2017-07-31
AU2011269429A1 (en) 2012-12-20
CN102958937A (zh) 2013-03-06
JP6174997B2 (ja) 2017-08-02
US9273064B2 (en) 2016-03-01

Similar Documents

Publication Publication Date Title
TWI507410B (zh) 新穎磷酸二酯酶抑制劑
KR101571654B1 (ko) 신규한 포스포디에스테라제 억제제
KR20210107046A (ko) 거대고리 화합물 및 질환 치료에서 이들의 용도
KR20230122083A (ko) 약제학적 활성 화합물로서 칸나비노이드 유도체 및이의 제조 방법
CN101631792B (zh) 新的磷酸二酯酶抑制剂
US20240239766A1 (en) 3-amino piperidyl sodium channel inhibitors
TWI432439B (zh) 新穎磷酸二酯酶抑制劑
HK1182699B (en) Benzodioxole or benzodioxepine heterocyclic compounds phosphodiesterase inhibitors