ZA200209875B - 2-aminocarbonyl-9H-purine derivatives. - Google Patents
2-aminocarbonyl-9H-purine derivatives. Download PDFInfo
- Publication number
- ZA200209875B ZA200209875B ZA200209875A ZA200209875A ZA200209875B ZA 200209875 B ZA200209875 B ZA 200209875B ZA 200209875 A ZA200209875 A ZA 200209875A ZA 200209875 A ZA200209875 A ZA 200209875A ZA 200209875 B ZA200209875 B ZA 200209875B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- alkyl
- formula
- optionally substituted
- cycloalkyl
- Prior art date
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- BMHHQPYFORGXQA-UHFFFAOYSA-N 7h-purine-2-carboxamide Chemical class NC(=O)C1=NC=C2N=CNC2=N1 BMHHQPYFORGXQA-UHFFFAOYSA-N 0.000 title description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 216
- 125000000217 alkyl group Chemical group 0.000 claims description 93
- 150000001875 compounds Chemical class 0.000 claims description 91
- -1 homopiperidin-3-yl Chemical group 0.000 claims description 67
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 125000002947 alkylene group Chemical group 0.000 claims description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000012453 solvate Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
- 125000002393 azetidinyl group Chemical group 0.000 claims description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
- 201000004624 Dermatitis Diseases 0.000 claims description 6
- 208000007882 Gastritis Diseases 0.000 claims description 6
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 6
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 6
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 6
- 208000010668 atopic eczema Diseases 0.000 claims description 6
- 206010006451 bronchitis Diseases 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 208000000509 infertility Diseases 0.000 claims description 6
- 230000036512 infertility Effects 0.000 claims description 6
- 231100000535 infertility Toxicity 0.000 claims description 6
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000004263 tetrahydroisoquinolin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])C2=C([H])C([H])=C([H])C([H])=C2C1([H])* 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 101150051188 Adora2a gene Proteins 0.000 claims description 4
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 4
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 4
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 3
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 206010009137 Chronic sinusitis Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 3
- 206010012434 Dermatitis allergic Diseases 0.000 claims description 3
- 206010014561 Emphysema Diseases 0.000 claims description 3
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
- 206010063837 Reperfusion injury Diseases 0.000 claims description 3
- 206010040070 Septic Shock Diseases 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 201000008937 atopic dermatitis Diseases 0.000 claims description 3
- 201000009267 bronchiectasis Diseases 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 208000007451 chronic bronchitis Diseases 0.000 claims description 3
- 201000009151 chronic rhinitis Diseases 0.000 claims description 3
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
- 201000001881 impotence Diseases 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 3
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 3
- 229940044601 receptor agonist Drugs 0.000 claims description 3
- 239000000018 receptor agonist Substances 0.000 claims description 3
- 208000023504 respiratory system disease Diseases 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 206010039083 rhinitis Diseases 0.000 claims description 3
- 230000036303 septic shock Effects 0.000 claims description 3
- 230000029663 wound healing Effects 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 2
- 125000004273 azetidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 7
- 238000006243 chemical reaction Methods 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000005910 aminocarbonylation reaction Methods 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- RWJFUQDRQOIAAF-UHFFFAOYSA-N ethyl 6-(2,2-diphenylethylamino)-7h-purine-2-carboxylate Chemical compound C=12N=CNC2=NC(C(=O)OCC)=NC=1NCC(C=1C=CC=CC=1)C1=CC=CC=C1 RWJFUQDRQOIAAF-UHFFFAOYSA-N 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- CMJCEVKJYRZMIA-UHFFFAOYSA-M thallium(i) iodide Chemical compound [Tl]I CMJCEVKJYRZMIA-UHFFFAOYSA-M 0.000 claims 1
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 8
- 210000000440 neutrophil Anatomy 0.000 description 7
- 239000000556 agonist Substances 0.000 description 5
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 4
- 101000851058 Homo sapiens Neutrophil elastase Proteins 0.000 description 4
- 229960005305 adenosine Drugs 0.000 description 4
- 102000052502 human ELANE Human genes 0.000 description 4
- 108050000203 Adenosine receptors Proteins 0.000 description 3
- 102000009346 Adenosine receptors Human genes 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 101150007969 ADORA1 gene Proteins 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 2
- 150000003212 purines Chemical class 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
- 108010041368 Adenosine A2 Receptors Proteins 0.000 description 1
- 102000000506 Adenosine A2 Receptors Human genes 0.000 description 1
- 102000007471 Adenosine A2A receptor Human genes 0.000 description 1
- 108010085277 Adenosine A2A receptor Proteins 0.000 description 1
- 102000007470 Adenosine A2B Receptor Human genes 0.000 description 1
- 108010085273 Adenosine A2B receptor Proteins 0.000 description 1
- 108010060261 Adenosine A3 Receptor Proteins 0.000 description 1
- 102000008161 Adenosine A3 Receptor Human genes 0.000 description 1
- 101150078577 Adora2b gene Proteins 0.000 description 1
- YZXBAPSDXZZRGB-DOFZRALJSA-M Arachidonate Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O YZXBAPSDXZZRGB-DOFZRALJSA-M 0.000 description 1
- 101000783751 Homo sapiens Adenosine receptor A2a Proteins 0.000 description 1
- 208000004852 Lung Injury Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010069363 Traumatic lung injury Diseases 0.000 description 1
- 102000030621 adenylate cyclase Human genes 0.000 description 1
- 108060000200 adenylate cyclase Proteins 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229940114078 arachidonate Drugs 0.000 description 1
- 210000003651 basophil Anatomy 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000021164 cell adhesion Effects 0.000 description 1
- 239000002975 chemoattractant Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 210000003979 eosinophil Anatomy 0.000 description 1
- 230000023266 generation of precursor metabolites and energy Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- 102000055905 human ADORA2A Human genes 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 1
- 231100000515 lung injury Toxicity 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000011242 neutrophil chemotaxis Effects 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 239000003642 reactive oxygen metabolite Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0014048A GB0014048D0 (en) | 2000-06-06 | 2000-06-06 | Purine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200209875B true ZA200209875B (en) | 2003-12-05 |
Family
ID=9893285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200209875A ZA200209875B (en) | 2000-06-06 | 2002-12-05 | 2-aminocarbonyl-9H-purine derivatives. |
Country Status (15)
| Country | Link |
|---|---|
| CN (1) | CN100374454C (es) |
| AP (1) | AP2001002179A0 (es) |
| CR (1) | CR6829A (es) |
| DO (1) | DOP2001000182A (es) |
| EC (1) | ECSP024370A (es) |
| GB (2) | GB0014048D0 (es) |
| GE (1) | GEP20053513B (es) |
| GT (1) | GT200100105A (es) |
| IL (1) | IL152783A (es) |
| MY (1) | MY128457A (es) |
| PE (1) | PE20020065A1 (es) |
| SV (1) | SV2002000477A (es) |
| TN (1) | TNSN01083A1 (es) |
| YU (1) | YU82302A (es) |
| ZA (1) | ZA200209875B (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105481861B (zh) * | 2014-09-19 | 2018-04-17 | 北京普禄德医药科技有限公司 | 一种血小板聚集抑制剂及其制备方法和用途 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9914526A (pt) * | 1998-10-16 | 2001-07-03 | Pfizer | Derivados de adenina |
-
2000
- 2000-06-06 GB GB0014048A patent/GB0014048D0/en not_active Ceased
- 2000-07-25 GB GB0018246A patent/GB0018246D0/en not_active Ceased
-
2001
- 2001-05-30 MY MYPI20012561 patent/MY128457A/en unknown
- 2001-05-31 AP APAP/P/2001/002179A patent/AP2001002179A0/en unknown
- 2001-06-01 DO DO2001000182A patent/DOP2001000182A/es unknown
- 2001-06-05 PE PE2001000520A patent/PE20020065A1/es not_active Application Discontinuation
- 2001-06-05 GT GT200100105A patent/GT200100105A/es unknown
- 2001-06-05 GE GEAP2001004973 patent/GEP20053513B/en unknown
- 2001-06-05 TN TNTNSN01083A patent/TNSN01083A1/fr unknown
- 2001-06-05 YU YU82302A patent/YU82302A/sh unknown
- 2001-06-05 CN CNB2006100045883A patent/CN100374454C/zh not_active Expired - Fee Related
- 2001-06-05 SV SV2001000477A patent/SV2002000477A/es not_active Application Discontinuation
-
2002
- 2002-11-11 IL IL152783A patent/IL152783A/en not_active IP Right Cessation
- 2002-11-22 CR CR6829A patent/CR6829A/es not_active Application Discontinuation
- 2002-12-02 EC ECSP024370 patent/ECSP024370A/es unknown
- 2002-12-05 ZA ZA200209875A patent/ZA200209875B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CR6829A (es) | 2004-03-11 |
| SV2002000477A (es) | 2002-10-24 |
| GEP20053513B (en) | 2005-05-10 |
| AP2001002179A0 (en) | 2002-11-30 |
| GB0018246D0 (en) | 2000-09-13 |
| TNSN01083A1 (fr) | 2005-11-10 |
| MY128457A (en) | 2007-02-28 |
| ECSP024370A (es) | 2003-03-10 |
| PE20020065A1 (es) | 2002-02-12 |
| CN1810822A (zh) | 2006-08-02 |
| DOP2001000182A (es) | 2002-08-30 |
| GB0014048D0 (en) | 2000-08-02 |
| YU82302A (sh) | 2005-11-28 |
| GT200100105A (es) | 2002-01-31 |
| IL152783A (en) | 2008-11-26 |
| CN100374454C (zh) | 2008-03-12 |
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