RU2021108990A - Boron containing PDE4 INHIBITORS - Google Patents
Boron containing PDE4 INHIBITORS Download PDFInfo
- Publication number
- RU2021108990A RU2021108990A RU2021108990A RU2021108990A RU2021108990A RU 2021108990 A RU2021108990 A RU 2021108990A RU 2021108990 A RU2021108990 A RU 2021108990A RU 2021108990 A RU2021108990 A RU 2021108990A RU 2021108990 A RU2021108990 A RU 2021108990A
- Authority
- RU
- Russia
- Prior art keywords
- oxaborolan
- alkyl
- methoxy
- pyridin
- alkoxy
- Prior art date
Links
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims 12
- 229910052796 boron Inorganic materials 0.000 title claims 12
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title 1
- -1 methyl- d 3 Chemical class 0.000 claims 285
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 152
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 100
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 54
- 125000001475 halogen functional group Chemical group 0.000 claims 40
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 31
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 25
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 24
- 239000011780 sodium chloride Substances 0.000 claims 24
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 21
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 18
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 18
- YZCKVEUIGOORGS-OUBTZVSYSA-N deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 18
- 229910052805 deuterium Inorganic materials 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 17
- 150000002367 halogens Chemical class 0.000 claims 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 16
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 9
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 201000004624 dermatitis Diseases 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- PBMFSQRYOILNGV-UHFFFAOYSA-N Pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 5
- 231100000406 dermatitis Toxicity 0.000 claims 5
- 239000003112 inhibitor Substances 0.000 claims 5
- 230000002401 inhibitory effect Effects 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 5
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims 4
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims 4
- 125000005108 alkenylthio group Chemical group 0.000 claims 4
- 125000005109 alkynylthio group Chemical group 0.000 claims 4
- 125000005110 aryl thio group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 4
- 125000005368 heteroarylthio group Chemical group 0.000 claims 4
- 125000005842 heteroatoms Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims 4
- 201000004681 psoriasis Diseases 0.000 claims 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 4
- 231100000080 dermatitis contact Toxicity 0.000 claims 3
- 206010012438 Dermatitis atopic Diseases 0.000 claims 2
- 206010012442 Dermatitis contact Diseases 0.000 claims 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- 206010024380 Leukoderma Diseases 0.000 claims 2
- 102000004311 Liver X Receptors Human genes 0.000 claims 2
- 108090000865 Liver X Receptors Proteins 0.000 claims 2
- 208000007256 Nevus Diseases 0.000 claims 2
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims 2
- 239000000556 agonist Substances 0.000 claims 2
- 201000008937 atopic dermatitis Diseases 0.000 claims 2
- 230000001684 chronic Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000002464 receptor antagonist Substances 0.000 claims 2
- BSUNTQCMCCQSQH-UHFFFAOYSA-N triazine Chemical group C1=CN=NN=C1.C1=CN=NN=C1 BSUNTQCMCCQSQH-UHFFFAOYSA-N 0.000 claims 2
- 206010000748 Acute febrile neutrophilic dermatosis Diseases 0.000 claims 1
- 208000002029 Allergic Contact Dermatitis Diseases 0.000 claims 1
- 208000004631 Alopecia Areata Diseases 0.000 claims 1
- 208000000594 Bullous Pemphigoid Diseases 0.000 claims 1
- 102100009787 CABIN1 Human genes 0.000 claims 1
- 108010066057 CABIN1 Proteins 0.000 claims 1
- 206010072757 Chronic spontaneous urticaria Diseases 0.000 claims 1
- 208000010247 Contact Dermatitis Diseases 0.000 claims 1
- 208000004921 Cutaneous Lupus Erythematosus Diseases 0.000 claims 1
- 208000005373 Dyshidrotic Eczema Diseases 0.000 claims 1
- 206010014989 Epidermolysis bullosa Diseases 0.000 claims 1
- 206010015278 Erythrodermic psoriasis Diseases 0.000 claims 1
- 210000000744 Eyelids Anatomy 0.000 claims 1
- 101700021558 GATA3 Proteins 0.000 claims 1
- 206010018797 Guttate psoriasis Diseases 0.000 claims 1
- 206010058898 Hand dermatitis Diseases 0.000 claims 1
- 208000002557 Hidradenitis Diseases 0.000 claims 1
- 102100016185 IRAK4 Human genes 0.000 claims 1
- 101700044314 IRAK4 Proteins 0.000 claims 1
- 208000001875 Irritant Dermatitis Diseases 0.000 claims 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N Isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N Isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- 206010066295 Keratosis pilaris Diseases 0.000 claims 1
- 208000007820 Lichen Sclerosus et Atrophicus Diseases 0.000 claims 1
- 206010024434 Lichen sclerosus Diseases 0.000 claims 1
- 206010025135 Lupus erythematosus Diseases 0.000 claims 1
- 206010027145 Melanocytic naevus Diseases 0.000 claims 1
- 206010028703 Nail psoriasis Diseases 0.000 claims 1
- 102100007288 PTGDR2 Human genes 0.000 claims 1
- 101710013017 PTGDR2 Proteins 0.000 claims 1
- 108060002038 Pde4 Proteins 0.000 claims 1
- 206010034277 Pemphigoid Diseases 0.000 claims 1
- 241000721454 Pemphigus Species 0.000 claims 1
- 208000009675 Perioral Dermatitis Diseases 0.000 claims 1
- 206010036229 Post inflammatory pigmentation change Diseases 0.000 claims 1
- 206010037162 Psoriatic arthropathy Diseases 0.000 claims 1
- 206010037575 Pustular psoriasis Diseases 0.000 claims 1
- 241001303601 Rosacea Species 0.000 claims 1
- 208000008742 Seborrheic Dermatitis Diseases 0.000 claims 1
- 208000010265 Sweet Syndrome Diseases 0.000 claims 1
- 239000004012 Tofacitinib Substances 0.000 claims 1
- 206010046751 Urticaria physical Diseases 0.000 claims 1
- 206010046736 Urticarias Diseases 0.000 claims 1
- 208000001445 Uveomeningoencephalitic Syndrome Diseases 0.000 claims 1
- 206010047642 Vitiligo Diseases 0.000 claims 1
- 206010047680 Vogt-Koyanagi-Harada syndrome Diseases 0.000 claims 1
- 208000010484 Vulvovaginitis Diseases 0.000 claims 1
- 206010048222 Xerosis Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000003042 antagnostic Effects 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003601 chymase inhibitor Substances 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 201000001981 dermatomyositis Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940079593 drugs Drugs 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N furane Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 201000007162 hidradenitis suppurativa Diseases 0.000 claims 1
- 239000003396 histamine H4 receptor antagonist Substances 0.000 claims 1
- 201000011486 lichen planus Diseases 0.000 claims 1
- 201000009053 neurodermatitis Diseases 0.000 claims 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutic aid Substances 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 201000002881 physical urticaria Diseases 0.000 claims 1
- 201000001263 psoriatic arthritis Diseases 0.000 claims 1
- KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
- 150000004508 retinoic acid derivatives Chemical class 0.000 claims 1
- 201000004700 rosacea Diseases 0.000 claims 1
- 230000002269 spontaneous Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
- UJLAWZDWDVHWOW-YPMHNXCESA-N tofacitinib Chemical compound C[C@@H]1CCN(C(=O)CC#N)C[C@@H]1N(C)C1=NC=NC2=C1C=CN2 UJLAWZDWDVHWOW-YPMHNXCESA-N 0.000 claims 1
- 229960001350 tofacitinib Drugs 0.000 claims 1
- 230000000699 topical Effects 0.000 claims 1
- 150000003852 triazoles Chemical group 0.000 claims 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 claims 1
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 claims 1
- 229940121358 tyrosine kinase inhibitors Drugs 0.000 claims 1
- 231100001002 xerosis Toxicity 0.000 claims 1
Claims (438)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US62/741,868 | 2018-10-05 | ||
US62/889,599 | 2019-08-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
RU2021108990A true RU2021108990A (en) | 2022-11-14 |
RU2793936C2 RU2793936C2 (en) | 2023-04-10 |
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