UA79323C2 - Selected cgrp antagonists, method for production and use thereof as medicament - Google Patents

Info

Publication number

UA79323C2

UA79323C2 UAA200504872A UA2005004872A UA79323C2 UA 79323 C2 UA79323 C2 UA 79323C2 UA A200504872 A UAA200504872 A UA A200504872A UA 2005004872 A UA2005004872 A UA 2005004872A UA 79323 C2 UA79323 C2 UA 79323C2

Authority

UA

Ukraine

Prior art keywords

group

oxo

piperidin

amino

chloro

Prior art date

2002-10-25

Links

• Espacenet
• Global Dossier
• Discuss

• 238000004519 manufacturing process Methods 0.000 title abstract description 3
• 229940127597 CGRP antagonist Drugs 0.000 title abstract 2
• 239000003814 drug Substances 0.000 title abstract 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 151
• 239000000203 mixture Substances 0.000 claims abstract description 77
• 238000000034 method Methods 0.000 claims abstract description 64
• 150000003839 salts Chemical class 0.000 claims abstract description 57
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 16
• 150000004677 hydrates Chemical class 0.000 claims abstract description 6
• 150000007522 mineralic acids Chemical class 0.000 claims abstract description 4
• 150000007524 organic acids Chemical class 0.000 claims abstract description 4
• 235000005985 organic acids Nutrition 0.000 claims abstract description 4
• -1 phenylsulfonylimino group Chemical group 0.000 claims description 412
• 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 256
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 208
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 163
• NOSOEJSZWOKISI-UHFFFAOYSA-N butane-1,4-dione Chemical compound O=[C]CC[C]=O NOSOEJSZWOKISI-UHFFFAOYSA-N 0.000 claims description 151
• 238000006243 chemical reaction Methods 0.000 claims description 113
• 229910052757 nitrogen Inorganic materials 0.000 claims description 94
• DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 89
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 86
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 84
• 125000000217 alkyl group Chemical group 0.000 claims description 83
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 74
• 239000000460 chlorine Substances 0.000 claims description 62
• 125000003277 amino group Chemical group 0.000 claims description 60
• 229910052801 chlorine Inorganic materials 0.000 claims description 60
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 60
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 59
• 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 54
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 53
• 150000001408 amides Chemical class 0.000 claims description 51
• 229910052731 fluorine Inorganic materials 0.000 claims description 51
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 49
• 239000002253 acid Substances 0.000 claims description 48
• 125000001424 substituent group Chemical group 0.000 claims description 48
• 125000001153 fluoro group Chemical group F* 0.000 claims description 47
• 229910052799 carbon Inorganic materials 0.000 claims description 45
• 239000011737 fluorine Substances 0.000 claims description 45
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 44
• 150000001721 carbon Chemical group 0.000 claims description 41
• 125000004076 pyridyl group Chemical group 0.000 claims description 40
• AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims description 38
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
• 125000003282 alkyl amino group Chemical group 0.000 claims description 36
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 34
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 33
• 125000000623 heterocyclic group Chemical group 0.000 claims description 33
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 31
• 150000001412 amines Chemical class 0.000 claims description 31
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 31
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 30
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 28
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 28
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 27
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 27
• 229910052794 bromium Inorganic materials 0.000 claims description 26
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 25
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-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 25
• 229910052740 iodine Inorganic materials 0.000 claims description 25
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 25
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 25
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 23
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 22
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 22
• 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims description 22
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 21
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 21
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 20
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 19
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 125000001246 bromo group Chemical group Br* 0.000 claims description 16
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 16
• 125000001072 heteroaryl group Chemical group 0.000 claims description 16
• 125000001544 thienyl group Chemical group 0.000 claims description 16
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 16
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 14
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 14
• 238000005859 coupling reaction Methods 0.000 claims description 14
• 229920006395 saturated elastomer Polymers 0.000 claims description 14
• 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 13
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
• 230000015572 biosynthetic process Effects 0.000 claims description 12
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 12
• 239000011734 sodium Substances 0.000 claims description 12
• 230000003993 interaction Effects 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
• 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 11
• KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 10
• 239000005557 antagonist Substances 0.000 claims description 10
• 238000010168 coupling process Methods 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 239000001301 oxygen Substances 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
• 125000002252 acyl group Chemical group 0.000 claims description 9
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 239000001257 hydrogen Substances 0.000 claims description 9
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 9
• 125000006239 protecting group Chemical group 0.000 claims description 9
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
• 229910052796 boron Inorganic materials 0.000 claims description 8
• 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 8
• 230000008878 coupling Effects 0.000 claims description 8
• MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 8
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
• 201000010099 disease Diseases 0.000 claims description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
• 239000012634 fragment Substances 0.000 claims description 8
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
• 229940126601 medicinal product Drugs 0.000 claims description 8
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
• 125000004434 sulfur atom Chemical group 0.000 claims description 8
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 8
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 7
• JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 7
• 208000019695 Migraine disease Diseases 0.000 claims description 7
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 7
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 7
• ALOCUZOKRULSAA-UHFFFAOYSA-N 1-methylpiperidin-4-amine Chemical compound CN1CCC(N)CC1 ALOCUZOKRULSAA-UHFFFAOYSA-N 0.000 claims description 6
• 206010019233 Headaches Diseases 0.000 claims description 6
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 239000000969 carrier Substances 0.000 claims description 6
• 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 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 claims description 6
• 239000002243 precursor Substances 0.000 claims description 6
• 150000003335 secondary amines Chemical class 0.000 claims description 6
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 5
• 208000027866 inflammatory disease Diseases 0.000 claims description 5
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
• 206010027599 migraine Diseases 0.000 claims description 5
• 150000003141 primary amines Chemical class 0.000 claims description 5
• 229910052708 sodium Inorganic materials 0.000 claims description 5
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
• 238000011282 treatment Methods 0.000 claims description 5
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 208000002193 Pain Diseases 0.000 claims description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 4
• 230000006378 damage Effects 0.000 claims description 4
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 230000000694 effects Effects 0.000 claims description 4
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 231100000869 headache Toxicity 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 4
• 230000005906 menstruation Effects 0.000 claims description 4
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 4
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 208000004296 neuralgia Diseases 0.000 claims description 4
• 208000021722 neuropathic pain Diseases 0.000 claims description 4
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
• 230000035939 shock Effects 0.000 claims description 4
• SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
• WVKZNHRMECGGGL-UHFFFAOYSA-N 1h-quinolin-2-one Chemical group C1=C=C[C]2NC(=O)C=CC2=C1 WVKZNHRMECGGGL-UHFFFAOYSA-N 0.000 claims description 3
• 206010060800 Hot flush Diseases 0.000 claims description 3
• 125000001931 aliphatic group Chemical group 0.000 claims description 3
• 125000003342 alkenyl group Chemical group 0.000 claims description 3
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
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• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
• 210000000214 mouth Anatomy 0.000 claims description 3
• 125000003431 oxalo group Chemical group 0.000 claims description 3
• BHJHVDDOCMGCDD-UHFFFAOYSA-N piperazin-1-ium-1-sulfonate Chemical compound OS(=O)(=O)N1CCNCC1 BHJHVDDOCMGCDD-UHFFFAOYSA-N 0.000 claims description 3
• 230000003449 preventive effect Effects 0.000 claims description 3
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• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
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• 208000007920 Neurogenic Inflammation Diseases 0.000 claims description 2
• 206010030247 Oestrogen deficiency Diseases 0.000 claims description 2
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
• 206010060862 Prostate cancer Diseases 0.000 claims description 2
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• 206010041303 Solar dermatitis Diseases 0.000 claims description 2
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
• 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims description 2
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• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
• WTVNFKVGGUWHQC-UHFFFAOYSA-N decane-2,4-dione Chemical compound CCCCCCC(=O)CC(C)=O WTVNFKVGGUWHQC-UHFFFAOYSA-N 0.000 claims description 2
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
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• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 230000004054 inflammatory process Effects 0.000 claims description 2
• 229960005181 morphine Drugs 0.000 claims description 2
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• 230000005855 radiation Effects 0.000 claims description 2
• 230000009885 systemic effect Effects 0.000 claims description 2
• 238000002560 therapeutic procedure Methods 0.000 claims description 2
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
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• 125000000524 functional group Chemical group 0.000 claims 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 2
• 239000011593 sulfur Substances 0.000 claims 2
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
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