BE566055A - - Google Patents
Info
- Publication number
- BE566055A BE566055A BE566055DA BE566055A BE 566055 A BE566055 A BE 566055A BE 566055D A BE566055D A BE 566055DA BE 566055 A BE566055 A BE 566055A
- Authority
- BE
- Belgium
- Prior art keywords
- amino
- bromobenzoxazole
- chloro
- preparation
- chlorobenzoxazole
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 26
- 239000011780 sodium chloride Substances 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 20
- -1 benzoxazole compound Chemical class 0.000 claims description 18
- QDMXVLGVKMTTIT-UHFFFAOYSA-N 6-chloro-1,3-benzoxazol-2-amine Chemical compound C1=C(Cl)C=C2OC(N)=NC2=C1 QDMXVLGVKMTTIT-UHFFFAOYSA-N 0.000 claims description 14
- APUYIVHTTCCVMF-UHFFFAOYSA-N 6-bromo-1,3-benzoxazol-2-amine Chemical compound C1=C(Br)C=C2OC(N)=NC2=C1 APUYIVHTTCCVMF-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- HMRSJGDFTOUVBW-UHFFFAOYSA-N 5-bromo-1,3-benzoxazol-2-amine Chemical compound BrC1=CC=C2OC(N)=NC2=C1 HMRSJGDFTOUVBW-UHFFFAOYSA-N 0.000 claims description 10
- JPBLHOJFMBOCAF-UHFFFAOYSA-N 1,3-benzoxazol-2-amine Chemical class C1=CC=C2OC(N)=NC2=C1 JPBLHOJFMBOCAF-UHFFFAOYSA-N 0.000 claims description 9
- PEEJUZZCANIEIL-UHFFFAOYSA-N 6-bromo-5-chloro-1,3-benzoxazol-2-amine Chemical compound ClC1=C(Br)C=C2OC(N)=NC2=C1 PEEJUZZCANIEIL-UHFFFAOYSA-N 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 8
- BCMCBBGGLRIHSE-UHFFFAOYSA-N Benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 7
- 208000006111 Contracture Diseases 0.000 claims description 7
- 206010062575 Muscle contracture Diseases 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- PGOGTWDYLFKOHI-UHFFFAOYSA-N 5-bromo-1,3-benzoxazole Chemical compound BrC1=CC=C2OC=NC2=C1 PGOGTWDYLFKOHI-UHFFFAOYSA-N 0.000 claims description 4
- ATDGTVJJHBUTRL-UHFFFAOYSA-N Cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- JJOOKXUUVWIARB-UHFFFAOYSA-N 6-chloro-1,3-benzoxazole Chemical compound ClC1=CC=C2N=COC2=C1 JJOOKXUUVWIARB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 3
- FZCQMIRJCGWWCL-UHFFFAOYSA-N 2-amino-5-chlorophenol Chemical compound NC1=CC=C(Cl)C=C1O FZCQMIRJCGWWCL-UHFFFAOYSA-N 0.000 claims description 2
- YXVFVHLEIBLKCA-UHFFFAOYSA-N 6-bromo-1,3-benzoxazole Chemical compound BrC1=CC=C2N=COC2=C1 YXVFVHLEIBLKCA-UHFFFAOYSA-N 0.000 claims description 2
- METCZKIWZIYCPW-UHFFFAOYSA-N 6-bromo-5-chloro-1,3-benzoxazole Chemical compound C1=C(Br)C(Cl)=CC2=C1OC=N2 METCZKIWZIYCPW-UHFFFAOYSA-N 0.000 claims description 2
- SEQRRWPVUWCNNO-UHFFFAOYSA-N OC1=C(C=CC(=C1)Cl)NC(=S)N Chemical compound OC1=C(C=CC(=C1)Cl)NC(=S)N SEQRRWPVUWCNNO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- DRQWUAAWZFIVTF-UHFFFAOYSA-N 2-amino-5-bromophenol Chemical compound NC1=CC=C(Br)C=C1O DRQWUAAWZFIVTF-UHFFFAOYSA-N 0.000 claims 1
- ZMSUVHHASUJZNH-UHFFFAOYSA-N 2-bromo-1,3-benzoxazole Chemical class C1=CC=C2OC(Br)=NC2=C1 ZMSUVHHASUJZNH-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004429 atoms Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- 229910052976 metal sulfide Inorganic materials 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 35
- 239000000243 solution Substances 0.000 description 23
- QMGVPVSNSZLJIA-FVWCLLPLSA-N Strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 230000028527 righting reflex Effects 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 11
- 229940066715 Pentylenetetrazole Drugs 0.000 description 11
- 241001279009 Strychnos toxifera Species 0.000 description 11
- 229960005152 pentetrazol Drugs 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 229960005453 strychnine Drugs 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 210000002027 Muscle, Skeletal Anatomy 0.000 description 9
- 230000035492 administration Effects 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000001990 intravenous administration Methods 0.000 description 7
- JWDYCNIAQWPBHD-UHFFFAOYSA-N Mephenesin Chemical compound CC1=CC=CC=C1OCC(O)CO JWDYCNIAQWPBHD-UHFFFAOYSA-N 0.000 description 6
- 210000003205 Muscles Anatomy 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 231100000636 lethal dose Toxicity 0.000 description 6
- 229960003861 mephenesin Drugs 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000003610 charcoal Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 210000002356 Skeleton Anatomy 0.000 description 4
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 4
- 230000001773 anti-convulsant Effects 0.000 description 4
- 239000001961 anticonvulsive agent Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 4
- 231100000486 side effect Toxicity 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000003179 convulsant agent Substances 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000007928 intraperitoneal injection Substances 0.000 description 3
- 230000003389 potentiating Effects 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 3
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- JHRIPENGTGSNPJ-UHFFFAOYSA-N 2-amino-4-bromophenol Chemical compound NC1=CC(Br)=CC=C1O JHRIPENGTGSNPJ-UHFFFAOYSA-N 0.000 description 2
- KFMHMAZWTFMXFM-UHFFFAOYSA-N 2-amino-5-bromo-4-chlorophenol Chemical compound NC1=CC(Cl)=C(Br)C=C1O KFMHMAZWTFMXFM-UHFFFAOYSA-N 0.000 description 2
- 208000008035 Back Pain Diseases 0.000 description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N Barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
- 210000000988 Bone and Bones Anatomy 0.000 description 2
- 210000003169 Central Nervous System Anatomy 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L Copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 241000699800 Cricetinae Species 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 206010021118 Hypotonia Diseases 0.000 description 2
- GUBGYTABKSRVRQ-UUNJERMWSA-N Lactose Natural products O([C@@H]1[C@H](O)[C@H](O)[C@H](O)O[C@@H]1CO)[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 GUBGYTABKSRVRQ-UUNJERMWSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- MNWBNISUBARLIT-UHFFFAOYSA-N Sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- YGCODSQDUUUKIV-UHFFFAOYSA-N Zoxazolamine Chemical compound ClC1=CC=C2OC(N)=NC2=C1 YGCODSQDUUUKIV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 150000003851 azoles Chemical class 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 230000002045 lasting Effects 0.000 description 2
- 229910000464 lead oxide Inorganic materials 0.000 description 2
- 238000011068 load Methods 0.000 description 2
- 230000036640 muscle relaxation Effects 0.000 description 2
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 230000000946 synaptic Effects 0.000 description 2
- MFCVASZUOWEOHT-LURJTMIESA-N (2S)-2-amino-4-propylsulfanylbutanoic acid Chemical compound CCCSCC[C@H](N)C(O)=O MFCVASZUOWEOHT-LURJTMIESA-N 0.000 description 1
- ZZZPLAFVUUMOLF-UHFFFAOYSA-N (4-bromo-2-hydroxyphenyl)thiourea Chemical compound NC(=S)NC1=CC=C(Br)C=C1O ZZZPLAFVUUMOLF-UHFFFAOYSA-N 0.000 description 1
- DBYCBIAALHOCBS-UHFFFAOYSA-N (5-bromo-2-hydroxyphenyl)thiourea Chemical compound NC(=S)NC1=CC(Br)=CC=C1O DBYCBIAALHOCBS-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N 1,4-Butanediol, dimethanesulfonate Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- LVVQTPZQNHQLOM-UHFFFAOYSA-N 2,6-dichloro-1,3-benzoxazole Chemical compound C1=C(Cl)C=C2OC(Cl)=NC2=C1 LVVQTPZQNHQLOM-UHFFFAOYSA-N 0.000 description 1
- BBVQDWDBTWSGHQ-UHFFFAOYSA-N 2-chloro-1,3-benzoxazole Chemical compound C1=CC=C2OC(Cl)=NC2=C1 BBVQDWDBTWSGHQ-UHFFFAOYSA-N 0.000 description 1
- VUBMEOPJYRVAOB-UHFFFAOYSA-N 5-bromo-1,3-benzoxazol-2-amine;hydrochloride Chemical compound Cl.BrC1=CC=C2OC(N)=NC2=C1 VUBMEOPJYRVAOB-UHFFFAOYSA-N 0.000 description 1
- AVVSRALHGMVQQW-UHFFFAOYSA-N 5-chloro-1,3-benzothiazol-2-amine Chemical compound ClC1=CC=C2SC(N)=NC2=C1 AVVSRALHGMVQQW-UHFFFAOYSA-N 0.000 description 1
- CVUOUWOUOAYBNN-UHFFFAOYSA-N 5-chloro-1-benzofuran-2-amine Chemical compound ClC1=CC=C2OC(N)=CC2=C1 CVUOUWOUOAYBNN-UHFFFAOYSA-N 0.000 description 1
- AVNWFOCOHFPYJN-UHFFFAOYSA-N 6-chloro-1,3-benzoxazol-2-amine;hydrochloride Chemical compound Cl.C1=C(Cl)C=C2OC(N)=NC2=C1 AVNWFOCOHFPYJN-UHFFFAOYSA-N 0.000 description 1
- PZZYQPZGQPZBDN-UHFFFAOYSA-N Aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 229940063834 Carboxymethylcellulose Sodium Drugs 0.000 description 1
- 206010008129 Cerebral palsy Diseases 0.000 description 1
- NIRZFCUFVURYJG-UHFFFAOYSA-N Cl.NC=1OC2=C(N1)C=CC(=C2)Br Chemical compound Cl.NC=1OC2=C(N1)C=CC(=C2)Br NIRZFCUFVURYJG-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N Cyanogen Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 208000010228 Erectile Dysfunction Diseases 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 208000008930 Low Back Pain Diseases 0.000 description 1
- 101710028361 MARVELD2 Proteins 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010061536 Parkinson's disease Diseases 0.000 description 1
- 206010072736 Rheumatic disease Diseases 0.000 description 1
- 206010039424 Salivary hypersecretion Diseases 0.000 description 1
- 208000010040 Sprains and Strains Diseases 0.000 description 1
- 241000282890 Sus Species 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-M camphorsulfonate anion Chemical compound C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-M 0.000 description 1
- 229920003123 carboxymethyl cellulose sodium Polymers 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 230000000515 cyanogenic Effects 0.000 description 1
- 230000002939 deleterious Effects 0.000 description 1
- 230000000994 depressed Effects 0.000 description 1
- 230000003001 depressive Effects 0.000 description 1
- 201000009910 diseases by infectious agent Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 230000001622 hypnogenic Effects 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000012501 relaxation of skeletal muscle Effects 0.000 description 1
- 230000000552 rheumatic Effects 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- SQMCFUSVGSBKFK-UHFFFAOYSA-M sodium;5-(cyclohexen-1-yl)-1,5-dimethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].O=C1N(C)C(=O)[N-]C(=O)C1(C)C1=CCCCC1 SQMCFUSVGSBKFK-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 201000002661 spondylitis Diseases 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-M stearate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000001052 transient Effects 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE566055A true BE566055A (pl) |
Family
ID=186338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE566055D BE566055A (pl) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE566055A (pl) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1288607B (de) * | 1961-07-14 | 1969-02-06 | Albert Ag Chem Werke | Verfahren zur Herstellung von Benzoxazolderivaten |
-
0
- BE BE566055D patent/BE566055A/fr unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1288607B (de) * | 1961-07-14 | 1969-02-06 | Albert Ag Chem Werke | Verfahren zur Herstellung von Benzoxazolderivaten |
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