CA2644963A1 - Organic compounds - Google Patents
Organic compounds Download PDFInfo
- Publication number
- CA2644963A1 CA2644963A1 CA002644963A CA2644963A CA2644963A1 CA 2644963 A1 CA2644963 A1 CA 2644963A1 CA 002644963 A CA002644963 A CA 002644963A CA 2644963 A CA2644963 A CA 2644963A CA 2644963 A1 CA2644963 A1 CA 2644963A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- compound according
- optionally substituted
- heterocyclyl
- phenyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 150000002894 organic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 350
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 339
- -1 amino, hydroxy Chemical group 0.000 claims description 170
- 229910052739 hydrogen Inorganic materials 0.000 claims description 134
- 239000001257 hydrogen Substances 0.000 claims description 134
- 229910052736 halogen Inorganic materials 0.000 claims description 113
- 150000002367 halogens Chemical group 0.000 claims description 113
- 125000000623 heterocyclic group Chemical group 0.000 claims description 103
- 150000003839 salts Chemical class 0.000 claims description 97
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 88
- 239000000203 mixture Substances 0.000 claims description 86
- 125000001424 substituent group Chemical group 0.000 claims description 82
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 68
- 239000000651 prodrug Substances 0.000 claims description 60
- 229940002612 prodrug Drugs 0.000 claims description 60
- 125000004043 oxo group Chemical group O=* 0.000 claims description 57
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 40
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- 125000003003 spiro group Chemical group 0.000 claims description 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 29
- 125000002757 morpholinyl group Chemical group 0.000 claims description 27
- 125000003386 piperidinyl group Chemical group 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 22
- 125000002950 monocyclic group Chemical group 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 21
- 125000002883 imidazolyl group Chemical group 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 19
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 19
- 239000003112 inhibitor Substances 0.000 claims description 18
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 16
- 125000002619 bicyclic group Chemical group 0.000 claims description 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 14
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 14
- 125000002541 furyl group Chemical group 0.000 claims description 14
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 14
- 125000004193 piperazinyl group Chemical group 0.000 claims description 14
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 14
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 14
- 125000006579 5 or 6-membered monocyclic heterocycloalkyl group Chemical group 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000006581 9 or 10-membered bicyclic heterocycloalkyl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 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 description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 8
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 8
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 5
- 208000001132 Osteoporosis Diseases 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 208000017169 kidney disease Diseases 0.000 claims description 5
- 239000003446 ligand Substances 0.000 claims description 5
- 150000002632 lipids Chemical class 0.000 claims description 5
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 4
- 206010020880 Hypertrophy Diseases 0.000 claims description 4
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000004044 response Effects 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- 238000002054 transplantation Methods 0.000 claims description 4
- 108091005482 5-HT4 receptors Proteins 0.000 claims description 3
- 102100040214 Apolipoprotein(a) Human genes 0.000 claims description 3
- 101710115418 Apolipoprotein(a) Proteins 0.000 claims description 3
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 230000003579 anti-obesity Effects 0.000 claims description 3
- 229940125708 antidiabetic agent Drugs 0.000 claims description 3
- 239000003472 antidiabetic agent Substances 0.000 claims description 3
- 229940030600 antihypertensive agent Drugs 0.000 claims description 3
- 239000002220 antihypertensive agent Substances 0.000 claims description 3
- 239000003524 antilipemic agent Substances 0.000 claims description 3
- 239000002246 antineoplastic agent Substances 0.000 claims description 3
- 230000000949 anxiolytic effect Effects 0.000 claims description 3
- 206010003246 arthritis Diseases 0.000 claims description 3
- 230000001925 catabolic effect Effects 0.000 claims description 3
- 230000001906 cholesterol absorption Effects 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 3
- 229940127089 cytotoxic agent Drugs 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 3
- 230000004153 glucose metabolism Effects 0.000 claims description 3
- 230000003054 hormonal effect Effects 0.000 claims description 3
- 230000001771 impaired effect Effects 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- 230000004770 neurodegeneration Effects 0.000 claims description 3
- 230000000626 neurodegenerative effect Effects 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000932 sedative agent Substances 0.000 claims description 3
- 230000001624 sedative effect Effects 0.000 claims description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 3
- IKBKZGMPCYNSLU-RGVLZGJSSA-N tegaserod Chemical group C1=C(OC)C=C2C(/C=N/NC(=N)NCCCCC)=CNC2=C1 IKBKZGMPCYNSLU-RGVLZGJSSA-N 0.000 claims description 3
- 229960002876 tegaserod Drugs 0.000 claims description 3
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 claims description 3
- SLYRGJDSFOCAAI-UHFFFAOYSA-N 1,3-thiazolidin-2-one Chemical class O=C1NCCS1 SLYRGJDSFOCAAI-UHFFFAOYSA-N 0.000 claims description 2
- 108091005477 5-HT3 receptors Proteins 0.000 claims description 2
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 claims description 2
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 claims description 2
- UXOWGYHJODZGMF-QORCZRPOSA-N Aliskiren Chemical compound COCCCOC1=CC(C[C@@H](C[C@H](N)[C@@H](O)C[C@@H](C(C)C)C(=O)NCC(C)(C)C(N)=O)C(C)C)=CC=C1OC UXOWGYHJODZGMF-QORCZRPOSA-N 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 2
- 239000004072 C09CA03 - Valsartan Substances 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 208000032781 Diabetic cardiomyopathy Diseases 0.000 claims description 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 2
- 206010056438 Growth hormone deficiency Diseases 0.000 claims description 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 206010022489 Insulin Resistance Diseases 0.000 claims description 2
- 239000005517 L01XE01 - Imatinib Substances 0.000 claims description 2
- 208000007177 Left Ventricular Hypertrophy Diseases 0.000 claims description 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 2
- 206010027476 Metastases Diseases 0.000 claims description 2
- 206010033645 Pancreatitis Diseases 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 206010036049 Polycystic ovaries Diseases 0.000 claims description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 2
- 208000017442 Retinal disease Diseases 0.000 claims description 2
- 206010038923 Retinopathy Diseases 0.000 claims description 2
- 208000000924 Right ventricular hypertrophy Diseases 0.000 claims description 2
- 102000018692 Sulfonylurea Receptors Human genes 0.000 claims description 2
- 108010091821 Sulfonylurea Receptors Proteins 0.000 claims description 2
- 229940122388 Thrombin inhibitor Drugs 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- 229960002478 aldosterone Drugs 0.000 claims description 2
- 229960004601 aliskiren Drugs 0.000 claims description 2
- 210000001367 artery Anatomy 0.000 claims description 2
- 229940011871 estrogen Drugs 0.000 claims description 2
- 239000000262 estrogen Substances 0.000 claims description 2
- 208000007565 gingivitis Diseases 0.000 claims description 2
- 201000010066 hyperandrogenism Diseases 0.000 claims description 2
- 201000001421 hyperglycemia Diseases 0.000 claims description 2
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 2
- 230000001969 hypertrophic effect Effects 0.000 claims description 2
- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims description 2
- 229960002411 imatinib Drugs 0.000 claims description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 2
- 230000009401 metastasis Effects 0.000 claims description 2
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 2
- 229960003105 metformin Drugs 0.000 claims description 2
- 230000001537 neural effect Effects 0.000 claims description 2
- 201000001119 neuropathy Diseases 0.000 claims description 2
- 230000007823 neuropathy Effects 0.000 claims description 2
- 208000004235 neutropenia Diseases 0.000 claims description 2
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims description 2
- 229960001243 orlistat Drugs 0.000 claims description 2
- 230000002611 ovarian Effects 0.000 claims description 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 2
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- 239000000849 selective androgen receptor modulator Substances 0.000 claims description 2
- 239000000333 selective estrogen receptor modulator Substances 0.000 claims description 2
- 229940095743 selective estrogen receptor modulator Drugs 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 229960003604 testosterone Drugs 0.000 claims description 2
- 230000008719 thickening Effects 0.000 claims description 2
- 239000003868 thrombin inhibitor Substances 0.000 claims description 2
- 229960004699 valsartan Drugs 0.000 claims description 2
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 claims description 2
- 230000002792 vascular Effects 0.000 claims description 2
- 210000005166 vasculature Anatomy 0.000 claims description 2
- 229960001254 vildagliptin Drugs 0.000 claims description 2
- 102000005666 Apolipoprotein A-I Human genes 0.000 claims 1
- 108010059886 Apolipoprotein A-I Proteins 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 197
- 239000000243 solution Substances 0.000 description 152
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 109
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 99
- 125000003545 alkoxy group Chemical group 0.000 description 97
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 93
- 239000011541 reaction mixture Substances 0.000 description 90
- 229910001868 water Inorganic materials 0.000 description 84
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 78
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 71
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 64
- 239000007832 Na2SO4 Substances 0.000 description 63
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 63
- 229910052938 sodium sulfate Inorganic materials 0.000 description 63
- 235000011152 sodium sulphate Nutrition 0.000 description 63
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 56
- 239000007787 solid Substances 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 46
- 239000012044 organic layer Substances 0.000 description 40
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 39
- 229910000029 sodium carbonate Inorganic materials 0.000 description 39
- 235000017550 sodium carbonate Nutrition 0.000 description 39
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 37
- 239000000460 chlorine Substances 0.000 description 33
- 238000004440 column chromatography Methods 0.000 description 33
- 238000010828 elution Methods 0.000 description 33
- 230000002441 reversible effect Effects 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 32
- 239000012071 phase Substances 0.000 description 32
- 238000002953 preparative HPLC Methods 0.000 description 32
- 239000003643 water by type Substances 0.000 description 32
- 229910052681 coesite Inorganic materials 0.000 description 31
- 229910052906 cristobalite Inorganic materials 0.000 description 31
- 239000000543 intermediate Substances 0.000 description 31
- 229910052682 stishovite Inorganic materials 0.000 description 31
- 229910052905 tridymite Inorganic materials 0.000 description 31
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 27
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 25
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 24
- 238000010992 reflux Methods 0.000 description 24
- 229910052731 fluorine Inorganic materials 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 21
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 20
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 20
- 239000011737 fluorine Substances 0.000 description 20
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 18
- 239000012267 brine Substances 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 17
- 238000000746 purification Methods 0.000 description 17
- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 description 16
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 description 16
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 16
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 16
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 15
- 229910052794 bromium Inorganic materials 0.000 description 15
- 238000007363 ring formation reaction Methods 0.000 description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 14
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 125000004188 dichlorophenyl group Chemical group 0.000 description 13
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| CR20220237A (es) | 2019-11-11 | 2022-08-05 | Incyte Corp | Sales y formas cristalinas de un inhibidor de pd-1/pd-l1 |
| US11780836B2 (en) | 2020-11-06 | 2023-10-10 | Incyte Corporation | Process of preparing a PD-1/PD-L1 inhibitor |
| AR124001A1 (es) | 2020-11-06 | 2023-02-01 | Incyte Corp | Proceso para fabricar un inhibidor pd-1 / pd-l1 y sales y formas cristalinas del mismo |
| WO2022099075A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Crystalline form of a pd-1/pd-l1 inhibitor |
Family Cites Families (12)
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|---|---|---|---|---|
| US5559158A (en) | 1993-10-01 | 1996-09-24 | Abbott Laboratories | Pharmaceutical composition |
| SE9500051D0 (sv) * | 1995-01-09 | 1995-01-09 | Frode Rise | Antioxidants, tissue- and/or neuroprotectants |
| GB2351081A (en) * | 1999-06-18 | 2000-12-20 | Lilly Forschung Gmbh | Pharmaceutically active imidazoline compounds and analogues thereof |
| ATE416175T1 (de) * | 2001-02-20 | 2008-12-15 | Astrazeneca Ab | 2-arylaminopyrimidine zur behandlung von mit gsk3 in zusammenhang stehenden erkrankungen |
| SE0100567D0 (sv) | 2001-02-20 | 2001-02-20 | Astrazeneca Ab | Compounds |
| EP1419163B9 (en) * | 2001-08-10 | 2005-11-09 | ALTANA Pharma AG | Tricyclic imidazopyridines |
| RU2293731C2 (ru) | 2002-02-13 | 2007-02-20 | Ф.Хоффманн-Ля Рош Аг | Производные пиридина и пиримидина, способы их получения (варианты), фармацевтическая композиция и применение |
| DE60302336T2 (de) | 2002-02-13 | 2006-08-03 | F. Hoffmann-La Roche Ag | Neue pyridin- und quinolin-derivate |
| MY139563A (en) * | 2002-09-04 | 2009-10-30 | Bristol Myers Squibb Co | Heterocyclic aromatic compounds useful as growth hormone secretagogues |
| WO2005118555A1 (en) | 2004-06-04 | 2005-12-15 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| GB0413605D0 (en) * | 2004-06-17 | 2004-07-21 | Addex Pharmaceuticals Sa | Novel compounds |
| WO2006019965A2 (en) | 2004-07-16 | 2006-02-23 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
-
2007
- 2007-03-29 WO PCT/EP2007/053064 patent/WO2007113226A1/en not_active Ceased
- 2007-03-29 EP EP07727536A patent/EP2004643A1/en not_active Withdrawn
- 2007-03-29 JP JP2009502104A patent/JP2009531390A/ja active Pending
- 2007-03-29 AU AU2007233709A patent/AU2007233709A1/en not_active Abandoned
- 2007-03-29 RU RU2008143179/04A patent/RU2008143179A/ru not_active Application Discontinuation
- 2007-03-29 KR KR1020087023759A patent/KR20080104351A/ko not_active Withdrawn
- 2007-03-29 CA CA002644963A patent/CA2644963A1/en not_active Abandoned
- 2007-03-29 BR BRPI0710110-4A patent/BRPI0710110A2/pt not_active IP Right Cessation
- 2007-03-29 CN CNA2007800112382A patent/CN101410397A/zh active Pending
- 2007-03-29 US US12/295,549 patent/US8097617B2/en not_active Expired - Fee Related
- 2007-03-29 MX MX2008012617A patent/MX2008012617A/es not_active Application Discontinuation
-
2011
- 2011-12-06 US US13/311,949 patent/US20120077787A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0710110A2 (pt) | 2011-08-02 |
| KR20080104351A (ko) | 2008-12-02 |
| US8097617B2 (en) | 2012-01-17 |
| WO2007113226A1 (en) | 2007-10-11 |
| CN101410397A (zh) | 2009-04-15 |
| EP2004643A1 (en) | 2008-12-24 |
| US20090253689A1 (en) | 2009-10-08 |
| JP2009531390A (ja) | 2009-09-03 |
| US20120077787A1 (en) | 2012-03-29 |
| AU2007233709A1 (en) | 2007-10-11 |
| RU2008143179A (ru) | 2010-05-10 |
| MX2008012617A (es) | 2008-10-10 |
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