EA019167B1 - Соединения, ингибирующие активность семикарбазид-чувствительной аминооксидазы - Google Patents
Соединения, ингибирующие активность семикарбазид-чувствительной аминооксидазы Download PDFInfo
- Publication number
- EA019167B1 EA019167B1 EA201100391A EA201100391A EA019167B1 EA 019167 B1 EA019167 B1 EA 019167B1 EA 201100391 A EA201100391 A EA 201100391A EA 201100391 A EA201100391 A EA 201100391A EA 019167 B1 EA019167 B1 EA 019167B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- imidazo
- isopropyl
- tetrahydro
- carboxylate
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 75
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- 125000000217 alkyl group Chemical group 0.000 claims description 50
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- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 claims description 5
- WEEUMIAFJMZQBT-UHFFFAOYSA-N (2-chloro-2,2-difluoroethyl) 4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate Chemical compound CC(C)C1N(C(=O)OCC(F)(F)Cl)CCC2=C1N=CN2 WEEUMIAFJMZQBT-UHFFFAOYSA-N 0.000 claims description 4
- XGYVJPDCZHHEDT-UHFFFAOYSA-N 2-(4-chlorophenoxy)ethyl 4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate Chemical compound C1CC=2NC=NC=2C(C(C)C)N1C(=O)OCCOC1=CC=C(Cl)C=C1 XGYVJPDCZHHEDT-UHFFFAOYSA-N 0.000 claims description 4
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- ZEUJFDJOZZUINU-UHFFFAOYSA-N COC(=O)N1CCC2=C(N=CN2)C1C(C)C Chemical compound COC(=O)N1CCC2=C(N=CN2)C1C(C)C ZEUJFDJOZZUINU-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 238000011321 prophylaxis Methods 0.000 claims description 4
- OMDOZAXSWPRNOK-UHFFFAOYSA-N pyridin-4-ylmethyl 4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate Chemical compound C1CC=2NC=NC=2C(C(C)C)N1C(=O)OCC1=CC=NC=C1 OMDOZAXSWPRNOK-UHFFFAOYSA-N 0.000 claims description 4
- UJHBPTGXXAVMQB-UHFFFAOYSA-N (4-chlorophenyl)methyl 4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate Chemical compound C1CC=2NC=NC=2C(C(C)C)N1C(=O)OCC1=CC=C(Cl)C=C1 UJHBPTGXXAVMQB-UHFFFAOYSA-N 0.000 claims description 3
- BNWCNSHBXPGXIS-UHFFFAOYSA-N 1,3-thiazol-2-ylmethyl 4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate Chemical compound C1CC=2NC=NC=2C(C(C)C)N1C(=O)OCC1=NC=CS1 BNWCNSHBXPGXIS-UHFFFAOYSA-N 0.000 claims description 3
- VKNCAJJASMWUGD-UHFFFAOYSA-N 2-phenoxyethyl 4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate Chemical compound C1CC=2NC=NC=2C(C(C)C)N1C(=O)OCCOC1=CC=CC=C1 VKNCAJJASMWUGD-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
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- BJLVVNQWHJZXSZ-UHFFFAOYSA-N pyrazin-2-ylmethyl 4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate Chemical compound C1CC=2NC=NC=2C(C(C)C)N1C(=O)OCC1=CN=CC=N1 BJLVVNQWHJZXSZ-UHFFFAOYSA-N 0.000 claims description 3
- HPOQKUXMZZNIDG-UHFFFAOYSA-N pyridin-2-ylmethyl 4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate Chemical compound C1CC=2NC=NC=2C(C(C)C)N1C(=O)OCC1=CC=CC=N1 HPOQKUXMZZNIDG-UHFFFAOYSA-N 0.000 claims description 3
- BRLXXVFUSZYJNB-UHFFFAOYSA-N pyridin-3-ylmethyl 4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate Chemical compound C1CC=2NC=NC=2C(C(C)C)N1C(=O)OCC1=CC=CN=C1 BRLXXVFUSZYJNB-UHFFFAOYSA-N 0.000 claims description 3
- HQYLBAHHQXRLJN-UHFFFAOYSA-N (3-chlorophenyl)methyl 4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate Chemical compound C1CC=2NC=NC=2C(C(C)C)N1C(=O)OCC1=CC=CC(Cl)=C1 HQYLBAHHQXRLJN-UHFFFAOYSA-N 0.000 claims description 2
- BZLMDWBBPQZXJD-UHFFFAOYSA-N (5-methyl-1,2-oxazol-3-yl)methyl 4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate Chemical compound C1CC=2NC=NC=2C(C(C)C)N1C(=O)OCC=1C=C(C)ON=1 BZLMDWBBPQZXJD-UHFFFAOYSA-N 0.000 claims description 2
- PJBJKGROWVXEJW-UHFFFAOYSA-N 2,2,2-trichloroethyl 4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate Chemical compound CC(C)C1N(C(=O)OCC(Cl)(Cl)Cl)CCC2=C1N=CN2 PJBJKGROWVXEJW-UHFFFAOYSA-N 0.000 claims description 2
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- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 2
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- HRVFDWZOZHBSJM-UHFFFAOYSA-N oxetan-2-ylmethyl 4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate Chemical compound C1CC=2NC=NC=2C(C(C)C)N1C(=O)OCC1CCO1 HRVFDWZOZHBSJM-UHFFFAOYSA-N 0.000 claims description 2
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- XYKAPZXCAKKASW-UHFFFAOYSA-N 2-(dimethylamino)ethyl 4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate Chemical compound CC(C)C1N(C(=O)OCCN(C)C)CCC2=C1N=CN2 XYKAPZXCAKKASW-UHFFFAOYSA-N 0.000 claims 1
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- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
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- 235000020357 syrup Nutrition 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 206010043207 temporal arteritis Diseases 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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- 210000002700 urine Anatomy 0.000 description 1
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Classifications
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- 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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- 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
- A61K31/435—Heterocyclic 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
- A61K31/4353—Heterocyclic 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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic 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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Immunology (AREA)
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- Pulmonology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Transplantation (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Gastroenterology & Hepatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0801979 | 2008-09-16 | ||
| US10673408P | 2008-10-20 | 2008-10-20 | |
| PCT/EP2009/062011 WO2010031789A1 (en) | 2008-09-16 | 2009-09-16 | New compounds i |
Publications (2)
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| EA201100391A1 EA201100391A1 (ru) | 2011-10-31 |
| EA019167B1 true EA019167B1 (ru) | 2014-01-30 |
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| US (7) | US8263616B2 (OSRAM) |
| EP (1) | EP2334672B1 (OSRAM) |
| JP (1) | JP5539989B2 (OSRAM) |
| CN (1) | CN102232073B (OSRAM) |
| AU (1) | AU2009294660B2 (OSRAM) |
| BR (1) | BRPI0918602B8 (OSRAM) |
| CA (1) | CA2737527C (OSRAM) |
| DK (1) | DK2334672T3 (OSRAM) |
| EA (1) | EA019167B1 (OSRAM) |
| ES (1) | ES2440279T3 (OSRAM) |
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| NZ (1) | NZ592238A (OSRAM) |
| PL (1) | PL2334672T3 (OSRAM) |
| PT (1) | PT2334672E (OSRAM) |
| WO (1) | WO2010031789A1 (OSRAM) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2334672E (pt) | 2008-09-16 | 2014-01-02 | Proximagen Ltd | Compostos novos i |
| UA112154C2 (uk) | 2009-09-08 | 2016-08-10 | Біоті Терапіс Корп. | Застосування повністю людського анти-vap-1-антитіла для лікування фіброзних станів |
| GB201004311D0 (en) | 2010-03-15 | 2010-04-28 | Proximagen Ltd | New enzyme inhibitor compounds |
| CN102311396B (zh) * | 2010-07-05 | 2015-01-07 | 暨南大学 | 一种吡嗪类衍生物和其制备方法及在制药中的应用 |
| FI20115234A0 (fi) | 2011-03-08 | 2011-03-08 | Biotie Therapies Corp | Uusia pyridatsinoni- ja pyridoniyhdisteitä |
| US9150574B2 (en) | 2011-09-14 | 2015-10-06 | Proximagen Limited | Enzyme inhibitor compounds |
| GB201304526D0 (en) | 2013-03-13 | 2013-04-24 | Proximagen Ltd | New compounds |
| GB201304527D0 (en) | 2013-03-13 | 2013-04-24 | Proximagen Ltd | New compounds |
| US20160113893A1 (en) | 2013-06-12 | 2016-04-28 | Proximagen Limited | New therapeutic uses of enzyme inhibitors |
| WO2015189534A1 (en) | 2014-06-12 | 2015-12-17 | Proximagen Limited | Vap-1 inhibitors for treating muscular dystrophy |
| GB201416444D0 (en) * | 2014-09-17 | 2014-10-29 | Proximagen Ltd | New compounds |
| GB201416446D0 (en) * | 2014-09-17 | 2014-10-29 | Proximagen Ltd | New enzyme inhibitor compounds |
| WO2016139909A1 (ja) | 2015-03-02 | 2016-09-09 | 日本電気株式会社 | 復号装置、受信機器、送信機器、送受信システム、復号方法、および復号用プログラムが記憶された記憶媒体 |
| GB201507048D0 (en) * | 2015-04-24 | 2015-06-10 | Proximagen Ltd | Treatment of pain |
| GB201507036D0 (en) * | 2015-04-24 | 2015-06-10 | Proximagen Ltd | Crystalline enzyme inhibitor compound |
| GB201507031D0 (en) * | 2015-04-24 | 2015-06-10 | Proximagen Ltd | New pharmaceutical salt forms |
| GB201513115D0 (en) * | 2015-07-24 | 2015-09-09 | Proximagen Ltd | New therapeutic compound and use in therapy |
| EP3377493B1 (en) | 2015-11-20 | 2020-04-08 | Forma Therapeutics, Inc. | Purinones as ubiquitin-specific protease 1 inhibitors |
| CA3007768A1 (en) * | 2015-12-07 | 2017-06-15 | Benevolentai Cambridge Limited | Vap-1 inhibitors for treating pain |
| GB201618029D0 (en) | 2016-10-25 | 2016-12-07 | Proximagen Ltd | New process |
| US20220073525A1 (en) * | 2018-12-28 | 2022-03-10 | Forma Therapeutics, Inc. | Compositions for inhibiting ubiquitin specific protease 1 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002038153A1 (en) * | 2000-11-09 | 2002-05-16 | Biovitrum Ab | New use of 4, 5, 6, 7-tetrahydroimidazo-[4,5-c]pyridine derivatives |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4141899A (en) * | 1976-01-07 | 1979-02-27 | Societa' Farmaceutici Italia S.P.A. | 4,5,6,7-Tetrahydroimidazo-[4,5-c]-pyridine derivatives |
| JPS5285191A (en) * | 1976-01-07 | 1977-07-15 | Farmaceutici Italia | Novel 4*5*6*77tetrahydroimidazoo *4*55c*pyridine derivative process for preparing same and medicine having antiiulcer antiisecretion and antiicolline activities containing same |
| IT1098015B (it) * | 1978-08-07 | 1985-08-31 | Farmaceutici Italia | Nuovi 4,5,6,7,-tetraidroimidazo-aperta par.quadrata 4,5-c chiusa par.quadrata-piridin-derivati |
| US6908926B1 (en) | 1999-04-16 | 2005-06-21 | Novo Nordisk A/S | Substituted imidazoles, their preparation and use |
| SE0004101D0 (sv) * | 2000-11-09 | 2000-11-09 | Pharmacia Ab | New use |
| US6576249B1 (en) * | 2000-11-13 | 2003-06-10 | El Gendler | Bone putty and method |
| PT2334672E (pt) | 2008-09-16 | 2014-01-02 | Proximagen Ltd | Compostos novos i |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002038153A1 (en) * | 2000-11-09 | 2002-05-16 | Biovitrum Ab | New use of 4, 5, 6, 7-tetrahydroimidazo-[4,5-c]pyridine derivatives |
Non-Patent Citations (1)
| Title |
|---|
| ARZNEIMITTEL-FORSCHUNG, 34(11), 1467-71 CODEN: ARZNAD; ISSN: 0004-4172, 1984, XP008114470, compound 13, the first paragraph of the left column of page 1468; entry 12 of table 3 * |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
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