TW200840563A

TW200840563A - Combinations of nicotinic acid and derivatives thereof and sterol absorption inhibitor(S) and treatments for vascular indications

Combinations of nicotinic acid and derivatives thereof and sterol absorption inhibitor(S) and treatments for vascular indications Download PDF

Info

Publication number: TW200840563A
Authority: TW; Taiwan
Prior art keywords: group; alkyl; aryl; substituted; independently selected
Prior art date: 2001-01-26

Application number

TW097121244A

Other languages

English (en)

Chinese (zh)

Inventor

Kosoglou Teddy

Harry R Davis

Original Assignee

Schering Corp

Priority date

2001-01-26

Filing date

2002-01-25

Publication date

2008-10-16

2002-01-25 Application filed by Schering Corp filed Critical Schering Corp

2008-10-16 Publication of TW200840563A publication Critical patent/TW200840563A/zh

Links

239000003112 inhibitor Substances 0.000 title claims abstract description 109
238000010521 absorption reaction Methods 0.000 title claims abstract description 90
230000002792 vascular Effects 0.000 title claims abstract description 12
238000011282 treatment Methods 0.000 title claims description 31
229930182558 Sterol Natural products 0.000 title abstract description 5
235000003702 sterols Nutrition 0.000 title abstract description 5
150000003432 sterols Chemical class 0.000 title abstract description 4
229940083256 peripheral vasodilators nicotinic acid and derivative Drugs 0.000 title 1
-1 β -lactam sterol Chemical class 0.000 claims abstract description 186
239000000203 mixture Substances 0.000 claims abstract description 99
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims abstract description 60
235000001968 nicotinic acid Nutrition 0.000 claims abstract description 31
239000011664 nicotinic acid Substances 0.000 claims abstract description 31
229960003512 nicotinic acid Drugs 0.000 claims abstract description 30
208000008589 Obesity Diseases 0.000 claims abstract description 17
235000020824 obesity Nutrition 0.000 claims abstract description 17
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 16
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims description 655
125000003118 aryl group Chemical group 0.000 claims description 307
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 202
150000001875 compounds Chemical class 0.000 claims description 193
125000003545 alkoxy group Chemical group 0.000 claims description 164
229910052739 hydrogen Inorganic materials 0.000 claims description 154
239000001257 hydrogen Substances 0.000 claims description 136
229910052799 carbon Inorganic materials 0.000 claims description 124
125000001424 substituent group Chemical group 0.000 claims description 123
229910052736 halogen Inorganic materials 0.000 claims description 112
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 99
150000002367 halogens Chemical class 0.000 claims description 97
150000003839 salts Chemical class 0.000 claims description 93
239000002585 base Substances 0.000 claims description 91
239000012453 solvate Substances 0.000 claims description 79
125000001072 heteroaryl group Chemical group 0.000 claims description 70
150000002431 hydrogen Chemical class 0.000 claims description 67
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 55
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 53
239000000126 substance Substances 0.000 claims description 50
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 49
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 48
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 39
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
125000003107 substituted aryl group Chemical group 0.000 claims description 38
239000002253 acid Substances 0.000 claims description 37
125000004432 carbon atom Chemical group C* 0.000 claims description 35
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 34
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
125000002947 alkylene group Chemical group 0.000 claims description 32
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 31
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 28
229910052707 ruthenium Inorganic materials 0.000 claims description 28
CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 27
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 26
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 26
229910052757 nitrogen Inorganic materials 0.000 claims description 25
125000004076 pyridyl group Chemical group 0.000 claims description 25
125000003342 alkenyl group Chemical group 0.000 claims description 24
125000003226 pyrazolyl group Chemical group 0.000 claims description 23
125000003396 thiol group Chemical group [H]S* 0.000 claims description 23
125000000753 cycloalkyl group Chemical group 0.000 claims description 22
125000003003 spiro group Chemical group 0.000 claims description 22
238000012360 testing method Methods 0.000 claims description 22
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 21
150000001721 carbon Chemical group 0.000 claims description 20
125000002757 morpholinyl group Chemical group 0.000 claims description 18
150000002191 fatty alcohols Chemical class 0.000 claims description 17
125000005843 halogen group Chemical group 0.000 claims description 17
RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 16
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
125000000168 pyrrolyl group Chemical group 0.000 claims description 16
239000011737 fluorine Substances 0.000 claims description 15
229910052731 fluorine Inorganic materials 0.000 claims description 15
125000002541 furyl group Chemical group 0.000 claims description 15
125000000842 isoxazolyl group Chemical group 0.000 claims description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
125000002883 imidazolyl group Chemical group 0.000 claims description 14
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 14
229920006395 saturated elastomer Polymers 0.000 claims description 14
210000004369 blood Anatomy 0.000 claims description 13
239000008280 blood Substances 0.000 claims description 13
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
239000008194 pharmaceutical composition Substances 0.000 claims description 13
125000003386 piperidinyl group Chemical group 0.000 claims description 13
125000004104 aryloxy group Chemical group 0.000 claims description 12
150000001540 azides Chemical class 0.000 claims description 12
150000004032 porphyrins Chemical class 0.000 claims description 12
241000219112 Cucumis Species 0.000 claims description 11
235000015510 Cucumis melo subsp melo Nutrition 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 11
FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
125000006612 decyloxy group Chemical group 0.000 claims description 11
125000004043 oxo group Chemical group O=* 0.000 claims description 11
244000269722 Thea sinensis Species 0.000 claims description 10
125000005055 alkyl alkoxy group Chemical group 0.000 claims description 10
125000003282 alkyl amino group Chemical group 0.000 claims description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 10
125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 9
125000000304 alkynyl group Chemical group 0.000 claims description 9
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
239000007789 gas Substances 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 8
206010036790 Productive cough Diseases 0.000 claims description 8
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
201000010099 disease Diseases 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 8
150000002632 lipids Chemical class 0.000 claims description 8
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical group 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 8
150000002923 oximes Chemical class 0.000 claims description 8
210000003802 sputum Anatomy 0.000 claims description 8
208000024794 sputum Diseases 0.000 claims description 8
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 7
150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
150000003973 alkyl amines Chemical class 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 7
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
229910052747 lanthanoid Inorganic materials 0.000 claims description 7
150000002602 lanthanoids Chemical class 0.000 claims description 7
125000001624 naphthyl group Chemical group 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
125000000335 thiazolyl group Chemical group 0.000 claims description 7
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
150000001413 amino acids Chemical class 0.000 claims description 6
125000002971 oxazolyl group Chemical group 0.000 claims description 6
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 5
125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 5
125000005336 allyloxy group Chemical group 0.000 claims description 5
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 5
125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 5
125000002837 carbocyclic group Chemical group 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
125000001725 pyrenyl group Chemical group 0.000 claims description 5
125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 claims description 5
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
KUEUWHJGRZKESU-UHFFFAOYSA-N Niceritrol Chemical compound C=1C=CN=CC=1C(=O)OCC(COC(=O)C=1C=NC=CC=1)(COC(=O)C=1C=NC=CC=1)COC(=O)C1=CC=CN=C1 KUEUWHJGRZKESU-UHFFFAOYSA-N 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
150000001336 alkenes Chemical class 0.000 claims description 4
125000000676 alkoxyimino group Chemical group 0.000 claims description 4
229910052786 argon Inorganic materials 0.000 claims description 4
125000005605 benzo group Chemical group 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
125000002993 cycloalkylene group Chemical group 0.000 claims description 4
150000002576 ketones Chemical class 0.000 claims description 4
229960005181 morphine Drugs 0.000 claims description 4
229960000827 niceritrol Drugs 0.000 claims description 4
210000002966 serum Anatomy 0.000 claims description 4
208000019553 vascular disease Diseases 0.000 claims description 4
DJQOOSBJCLSSEY-UHFFFAOYSA-N Acipimox Chemical compound CC1=CN=C(C(O)=O)C=[N+]1[O-] DJQOOSBJCLSSEY-UHFFFAOYSA-N 0.000 claims description 3
241000237858 Gastropoda Species 0.000 claims description 3
229960003526 acipimox Drugs 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 3
KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
238000001354 calcination Methods 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
229910052762 osmium Inorganic materials 0.000 claims description 3
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
UTUIBVHZFWGLTH-UHFFFAOYSA-N 3-(1-methylpyrrolidin-2-yl)pyridine;pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1.CN1CCCC1C1=CC=CN=C1 UTUIBVHZFWGLTH-UHFFFAOYSA-N 0.000 claims description 2
125000000815 N-oxide group Chemical group 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
229960002715 nicotine Drugs 0.000 claims description 2
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 2
125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
230000002265 prevention Effects 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
210000003296 saliva Anatomy 0.000 claims description 2
239000002689 soil Substances 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
229910052727 yttrium Inorganic materials 0.000 claims description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
239000003610 charcoal Substances 0.000 claims 4
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
229960004552 nicofuranose Drugs 0.000 claims 3
FUWFSXZKBMCSKF-ZASNTINBSA-N nicofuranose Chemical compound C([C@]1(O)[C@H]([C@H](OC(=O)C=2C=NC=CC=2)[C@@H](COC(=O)C=2C=NC=CC=2)O1)OC(=O)C=1C=NC=CC=1)OC(=O)C1=CC=CN=C1 FUWFSXZKBMCSKF-ZASNTINBSA-N 0.000 claims 3
238000006467 substitution reaction Methods 0.000 claims 3
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
239000005864 Sulphur Substances 0.000 claims 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
125000005083 alkoxyalkoxy group Chemical group 0.000 claims 2
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims 2
125000005343 heterocyclic alkyl group Chemical group 0.000 claims 2
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims 2
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
125000001786 isothiazolyl group Chemical group 0.000 claims 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 2
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 2
WTFNSXYULBQCQV-UHFFFAOYSA-N $l^{1}-oxidanyloxymethane Chemical group CO[O] WTFNSXYULBQCQV-UHFFFAOYSA-N 0.000 claims 1
125000006732 (C1-C15) alkyl group Chemical group 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims 1
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
101100048447 Caenorhabditis elegans unc-4 gene Proteins 0.000 claims 1
244000294411 Mirabilis expansa Species 0.000 claims 1
235000015429 Mirabilis expansa Nutrition 0.000 claims 1
208000007256 Nevus Diseases 0.000 claims 1
NVNLLIYOARQCIX-MSHCCFNRSA-N Nisin Chemical compound N1C(=O)[C@@H](CC(C)C)NC(=O)C(=C)NC(=O)[C@@H]([C@H](C)CC)NC(=O)[C@@H](NC(=O)C(=C/C)/NC(=O)[C@H](N)[C@H](C)CC)CSC[C@@H]1C(=O)N[C@@H]1C(=O)N2CCC[C@@H]2C(=O)NCC(=O)N[C@@H](C(=O)N[C@H](CCCCN)C(=O)N[C@@H]2C(NCC(=O)N[C@H](C)C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCSC)C(=O)NCC(=O)N[C@H](CS[C@@H]2C)C(=O)N[C@H](CC(N)=O)C(=O)N[C@H](CCSC)C(=O)N[C@H](CCCCN)C(=O)N[C@@H]2C(N[C@H](C)C(=O)N[C@@H]3C(=O)N[C@@H](C(N[C@H](CC=4NC=NC=4)C(=O)N[C@H](CS[C@@H]3C)C(=O)N[C@H](CO)C(=O)N[C@H]([C@H](C)CC)C(=O)N[C@H](CC=3NC=NC=3)C(=O)N[C@H](C(C)C)C(=O)NC(=C)C(=O)N[C@H](CCCCN)C(O)=O)=O)CS[C@@H]2C)=O)=O)CS[C@@H]1C NVNLLIYOARQCIX-MSHCCFNRSA-N 0.000 claims 1
108010053775 Nisin Proteins 0.000 claims 1
229910006069 SO3H Inorganic materials 0.000 claims 1
244000180577 Sambucus australis Species 0.000 claims 1
235000018734 Sambucus australis Nutrition 0.000 claims 1
241000543375 Sideroxylon Species 0.000 claims 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
NLMBNVBBHYNBQY-UHFFFAOYSA-N [C].[Ru] Chemical group [C].[Ru] NLMBNVBBHYNBQY-UHFFFAOYSA-N 0.000 claims 1
MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
125000005577 anthracene group Chemical group 0.000 claims 1
125000003710 aryl alkyl group Chemical group 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims 1
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