TW198721B - - Google Patents

Info

Publication number

TW198721B

TW198721B TW80105863A TW80105863A TW198721B TW 198721 B TW198721 B TW 198721B TW 80105863 A TW80105863 A TW 80105863A TW 80105863 A TW80105863 A TW 80105863A TW 198721 B TW198721 B TW 198721B

Authority

TW

Taiwan

Prior art keywords

alkyl

gas

group

hospital

methyl

Prior art date

1990-07-27

Links

• Espacenet
• Global Dossier
• Discuss

• -1 tetrapyridinyl Chemical group 0.000 claims description 458
• 239000007789 gas Substances 0.000 claims description 455
• 125000000217 alkyl group Chemical group 0.000 claims description 245
• 150000001875 compounds Chemical class 0.000 claims description 172
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 158
• 238000002360 preparation method Methods 0.000 claims description 148
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 131
• 150000003839 salts Chemical class 0.000 claims description 111
• 239000002253 acid Substances 0.000 claims description 105
• 238000011049 filling Methods 0.000 claims description 100
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 82
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 79
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 79
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 77
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 72
• 239000002904 solvent Substances 0.000 claims description 64
• 239000000203 mixture Substances 0.000 claims description 61
• 150000001412 amines Chemical class 0.000 claims description 57
• 238000006243 chemical reaction Methods 0.000 claims description 56
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 54
• 229910052739 hydrogen Inorganic materials 0.000 claims description 50
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 48
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 42
• 239000011593 sulfur Substances 0.000 claims description 38
• 229910052717 sulfur Inorganic materials 0.000 claims description 38
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 38
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 35
• KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 34
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 34
• 238000000034 method Methods 0.000 claims description 34
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 32
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
• 239000001257 hydrogen Substances 0.000 claims description 30
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 26
• 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 26
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 25
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 24
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 23
• VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 claims description 21
• BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 claims description 21
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 125000004076 pyridyl group Chemical group 0.000 claims description 19
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 18
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 17
• 238000010438 heat treatment Methods 0.000 claims description 17
• 208000004350 Strabismus Diseases 0.000 claims description 16
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 16
• 125000003118 aryl group Chemical group 0.000 claims description 16
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 16
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
• 150000002431 hydrogen Chemical class 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 15
• 125000004414 alkyl thio group Chemical group 0.000 claims description 14
• 239000007788 liquid Substances 0.000 claims description 14
• 125000006239 protecting group Chemical group 0.000 claims description 14
• 108090000790 Enzymes Proteins 0.000 claims description 13
• 102000004190 Enzymes Human genes 0.000 claims description 13
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 150000003973 alkyl amines Chemical class 0.000 claims description 13
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• 238000001816 cooling Methods 0.000 claims description 13
• 125000002393 azetidinyl group Chemical group 0.000 claims description 12
• 150000002466 imines Chemical class 0.000 claims description 11
• 238000002156 mixing Methods 0.000 claims description 11
• ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 11
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 10
• 125000003386 piperidinyl group Chemical group 0.000 claims description 10
• WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 9
• 230000002079 cooperative effect Effects 0.000 claims description 9
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 8
• 125000002252 acyl group Chemical group 0.000 claims description 8
• 239000004202 carbamide Substances 0.000 claims description 8
• 235000013877 carbamide Nutrition 0.000 claims description 8
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 8
• IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 7
• 239000005864 Sulphur Substances 0.000 claims description 7
• 150000001408 amides Chemical class 0.000 claims description 7
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 7
• 229940124530 sulfonamide Drugs 0.000 claims description 7
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• 238000009434 installation Methods 0.000 claims description 6
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
• 239000011259 mixed solution Substances 0.000 claims description 6
• 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 5
• 150000001336 alkenes Chemical class 0.000 claims description 5
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
• 125000002947 alkylene group Chemical group 0.000 claims description 5
• 125000006242 amine protecting group Chemical group 0.000 claims description 5
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 5
• FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 claims description 5
• 229960000623 carbamazepine Drugs 0.000 claims description 5
• 230000000694 effects Effects 0.000 claims description 5
• 125000002636 imidazolinyl group Chemical group 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 150000004032 porphyrins Chemical class 0.000 claims description 5
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
• 229910052704 radon Inorganic materials 0.000 claims description 5
• 230000004044 response Effects 0.000 claims description 5
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
• OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims description 4
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 4
• 230000002411 adverse Effects 0.000 claims description 4
• 150000001343 alkyl silanes Chemical class 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 230000033228 biological regulation Effects 0.000 claims description 4
• 150000007942 carboxylates Chemical class 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 150000003222 pyridines Chemical class 0.000 claims description 4
• SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 claims description 4
• 229910000077 silane Inorganic materials 0.000 claims description 4
• 239000008096 xylene Substances 0.000 claims description 4
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 3
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 3
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• 239000002168 alkylating agent Substances 0.000 claims description 3
• 229940100198 alkylating agent Drugs 0.000 claims description 3
• 239000000872 buffer Substances 0.000 claims description 3
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
• 235000019253 formic acid Nutrition 0.000 claims description 3
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
• 238000002309 gasification Methods 0.000 claims description 3
• 239000011521 glass Substances 0.000 claims description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
• 125000005968 oxazolinyl group Chemical group 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000006413 ring segment Chemical group 0.000 claims description 3
• 150000003456 sulfonamides Chemical class 0.000 claims description 3
• 238000003786 synthesis reaction Methods 0.000 claims description 3
• 150000003536 tetrazoles Chemical class 0.000 claims description 3
• PLCMVACJJSYDFV-UHFFFAOYSA-N 1,3-oxazole-2-carboxamide Chemical compound NC(=O)C1=NC=CO1 PLCMVACJJSYDFV-UHFFFAOYSA-N 0.000 claims description 2
• 235000007516 Chrysanthemum Nutrition 0.000 claims description 2
• 244000189548 Chrysanthemum x morifolium Species 0.000 claims description 2
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
• 239000003242 anti bacterial agent Substances 0.000 claims description 2
• 229910052786 argon Inorganic materials 0.000 claims description 2
• IWLBIFVMPLUHLK-UHFFFAOYSA-N azane;formaldehyde Chemical compound N.O=C IWLBIFVMPLUHLK-UHFFFAOYSA-N 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• 229940079593 drug Drugs 0.000 claims description 2
• 238000000605 extraction Methods 0.000 claims description 2
• 239000000796 flavoring agent Substances 0.000 claims description 2
• 150000004820 halides Chemical class 0.000 claims description 2
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004999 nitroaryl group Chemical group 0.000 claims 6
• 125000002883 imidazolyl group Chemical group 0.000 claims 5
• ZLHLYESIHSHXGM-UHFFFAOYSA-N 4,6-dimethyl-1h-imidazo[1,2-a]purin-9-one Chemical compound N=1C(C)=CN(C2=O)C=1N(C)C1=C2NC=N1 ZLHLYESIHSHXGM-UHFFFAOYSA-N 0.000 claims 3
• 229940088598 enzyme Drugs 0.000 claims 3
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
• 125000004429 atom Chemical group 0.000 claims 2
• JAXRDWMKVWMNNM-UHFFFAOYSA-N 1,3-oxazole-2-carboximidamide Chemical compound NC(=N)C1=NC=CO1 JAXRDWMKVWMNNM-UHFFFAOYSA-N 0.000 claims 1
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
• OPFNZHIUHJBGEW-UHFFFAOYSA-N 1-hydroxyimidazole Chemical compound ON1C=CN=C1 OPFNZHIUHJBGEW-UHFFFAOYSA-N 0.000 claims 1
• QUYPSOKUBYENRV-UHFFFAOYSA-N 1h-pyrazole;pyridine Chemical compound C=1C=NNC=1.C1=CC=NC=C1 QUYPSOKUBYENRV-UHFFFAOYSA-N 0.000 claims 1
• XJLITJHUQRBWPN-UHFFFAOYSA-N 2-acetamidoacetic acid;4-[2-(4-carbamimidoylphenyl)iminohydrazinyl]benzenecarboximidamide Chemical compound CC(=O)NCC(O)=O.C1=CC(C(=N)N)=CC=C1NN=NC1=CC=C(C(N)=N)C=C1 XJLITJHUQRBWPN-UHFFFAOYSA-N 0.000 claims 1
• UUNIOFWUJYBVGQ-UHFFFAOYSA-N 2-amino-4-(3,4-dimethoxyphenyl)-10-fluoro-4,5,6,7-tetrahydrobenzo[1,2]cyclohepta[6,7-d]pyran-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1C(C#N)=C(N)OC2=C1CCCC1=CC=C(F)C=C12 UUNIOFWUJYBVGQ-UHFFFAOYSA-N 0.000 claims 1
• KFHRMMHGGBCRIV-UHFFFAOYSA-N 2-azaniumyl-4-methoxybutanoate Chemical compound COCCC(N)C(O)=O KFHRMMHGGBCRIV-UHFFFAOYSA-N 0.000 claims 1
• VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical group C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims 1
• DSNMXOQYTGRZBC-UHFFFAOYSA-N 2h-pyridin-1-ium 1-oxide Chemical compound O=[N+]1CC=CC=C1 DSNMXOQYTGRZBC-UHFFFAOYSA-N 0.000 claims 1
• NKKBOUBMVAAJAF-UHFFFAOYSA-N 3-[[2-methoxyethyl(prop-2-enyl)amino]methyl]-2-methyl-1,1-dioxothieno[3,2-e]thiazine-6-sulfonamide Chemical compound O=S1(=O)N(C)C(CN(CC=C)CCOC)=CC2=C1SC(S(N)(=O)=O)=C2 NKKBOUBMVAAJAF-UHFFFAOYSA-N 0.000 claims 1
• CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims 1
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
• 241000605422 Asparagus asparagoides Species 0.000 claims 1
• ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 1
• 241000272165 Charadriidae Species 0.000 claims 1
• 241000233866 Fungi Species 0.000 claims 1
• 239000005562 Glyphosate Substances 0.000 claims 1
• LRUUNMYPIBZBQH-UHFFFAOYSA-N Methazole Chemical compound O=C1N(C)C(=O)ON1C1=CC=C(Cl)C(Cl)=C1 LRUUNMYPIBZBQH-UHFFFAOYSA-N 0.000 claims 1
• 102000016943 Muramidase Human genes 0.000 claims 1
• 108010014251 Muramidase Proteins 0.000 claims 1
• 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 claims 1
• 244000062793 Sorghum vulgare Species 0.000 claims 1
• MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical group CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 claims 1
• 241000009298 Trigla lyra Species 0.000 claims 1
• 150000001298 alcohols Chemical class 0.000 claims 1
• 150000004705 aldimines Chemical group 0.000 claims 1
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
• 125000005277 alkyl imino group Chemical group 0.000 claims 1
• 125000004647 alkyl sulfenyl group Chemical group 0.000 claims 1
• 125000004419 alkynylene group Chemical group 0.000 claims 1
• BCDGQXUMWHRQCB-UHFFFAOYSA-N aminoacetone Chemical compound CC(=O)CN BCDGQXUMWHRQCB-UHFFFAOYSA-N 0.000 claims 1
• 150000003927 aminopyridines Chemical class 0.000 claims 1
• 229940000489 arsenate Drugs 0.000 claims 1
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 1
• 230000015572 biosynthetic process Effects 0.000 claims 1
• 150000001924 cycloalkanes Chemical class 0.000 claims 1
• NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims 1
• 230000002950 deficient Effects 0.000 claims 1
• RDYMFSUJUZBWLH-UHFFFAOYSA-N endosulfan Chemical compound C12COS(=O)OCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl RDYMFSUJUZBWLH-UHFFFAOYSA-N 0.000 claims 1
• 235000019634 flavors Nutrition 0.000 claims 1
• XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims 1
• 229940097068 glyphosate Drugs 0.000 claims 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 claims 1
• 229960000274 lysozyme Drugs 0.000 claims 1
• 235000010335 lysozyme Nutrition 0.000 claims 1
• 239000004325 lysozyme Substances 0.000 claims 1
• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims 1
• MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims 1
• 235000019713 millet Nutrition 0.000 claims 1
• 235000019645 odor Nutrition 0.000 claims 1
• USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 1
• RWDURXMYEQKULO-UHFFFAOYSA-N pyridine;pyrimidine Chemical class C1=CC=NC=C1.C1=CC=NC=C1.C1=CN=CN=C1 RWDURXMYEQKULO-UHFFFAOYSA-N 0.000 claims 1
• JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
• 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
• 229910052705 radium Inorganic materials 0.000 claims 1
• HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 claims 1
• 230000013707 sensory perception of sound Effects 0.000 claims 1
• 241000894007 species Species 0.000 claims 1
• 229960005404 sulfamethoxazole Drugs 0.000 claims 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
• GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 claims 1
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• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1