NO750341L - - Google Patents

Info

Publication number: NO750341L
Authority: NO; Norway
Prior art keywords: radical; carbon atoms; meanings; numbered; those
Prior art date: 1974-02-04

Application number

NO750341A

Other languages

English (en)

Norwegian (no)

Inventor

R H B Galt

R J Pearce

Original Assignee

Ici Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1974-02-04

Filing date

1975-02-03

Publication date

1975-09-01

1975-02-03 Application filed by Ici Ltd filed Critical Ici Ltd

1975-09-01 Publication of NO750341L publication Critical patent/NO750341L/no

Links

238000000034 method Methods 0.000 claims abstract description 45
238000002360 preparation method Methods 0.000 claims abstract description 40
-1 alkyl radical Chemical class 0.000 claims description 183
150000001875 compounds Chemical class 0.000 claims description 112
125000004432 carbon atom Chemical group C* 0.000 claims description 80
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 57
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 52
239000001257 hydrogen Substances 0.000 claims description 48
229910052739 hydrogen Inorganic materials 0.000 claims description 48
150000003254 radicals Chemical class 0.000 claims description 41
239000002253 acid Substances 0.000 claims description 22
239000000460 chlorine Substances 0.000 claims description 21
229910052801 chlorine Inorganic materials 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 17
125000005843 halogen group Chemical group 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 8
150000001450 anions Chemical class 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 6
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000006196 aroyl alkyl group Chemical group 0.000 claims description 3
239000012433 hydrogen halide Substances 0.000 claims description 3
229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
150000005840 aryl radicals Chemical class 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims 1
QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 abstract description 17
GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical class C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 abstract description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 86
239000000243 solution Substances 0.000 description 73
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 70
239000000203 mixture Substances 0.000 description 68
239000007858 starting material Substances 0.000 description 45
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
239000002904 solvent Substances 0.000 description 28
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 26
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 26
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
239000007787 solid Substances 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
239000003208 petroleum Substances 0.000 description 17
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000003085 diluting agent Substances 0.000 description 15
ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 14
238000010992 reflux Methods 0.000 description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
229910052731 fluorine Inorganic materials 0.000 description 13
239000011737 fluorine Substances 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 12
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 11
150000003732 xanthenes Chemical class 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
238000010438 heat treatment Methods 0.000 description 10
238000001953 recrystallisation Methods 0.000 description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
241000699670 Mus sp. Species 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
239000000730 antalgic agent Substances 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
239000012312 sodium hydride Substances 0.000 description 8
229910000104 sodium hydride Inorganic materials 0.000 description 8
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
238000000746 purification Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
230000000202 analgesic effect Effects 0.000 description 6
229940035676 analgesics Drugs 0.000 description 6
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
239000002026 chloroform extract Substances 0.000 description 6
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 6
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 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 5
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 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000012259 ether extract Substances 0.000 description 5
239000002024 ethyl acetate extract Substances 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
239000008194 pharmaceutical composition Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
SCLKLDQSORNONN-UHFFFAOYSA-N 3-chloro-5-methoxyxanthen-9-one Chemical compound O1C2=CC(Cl)=CC=C2C(=O)C2=C1C(OC)=CC=C2 SCLKLDQSORNONN-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
239000002585 base Substances 0.000 description 4
OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 4
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000000725 suspension Substances 0.000 description 4
JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 4
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
JUXAVSAMVBLDKO-UHFFFAOYSA-N 1-(1-azabicyclo[2.2.2]octan-3-yl)-3-[3-(1h-indol-3-yl)-1-oxo-1-spiro[1,2-dihydroindene-3,4'-piperidine]-1'-ylpropan-2-yl]urea Chemical group C1N(CC2)CCC2C1NC(=O)NC(C(=O)N1CCC2(C3=CC=CC=C3CC2)CC1)CC1=CNC2=CC=CC=C12 JUXAVSAMVBLDKO-UHFFFAOYSA-N 0.000 description 3
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 3
RHDYQUZYHZWTCI-UHFFFAOYSA-N 1-methoxy-4-phenylbenzene Chemical compound C1=CC(OC)=CC=C1C1=CC=CC=C1 RHDYQUZYHZWTCI-UHFFFAOYSA-N 0.000 description 3
LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical compound C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
NAVNDSDOBFIUBJ-UHFFFAOYSA-N 4'-methoxyspiro[piperidine-4,9'-xanthene] Chemical compound COC1=CC=CC2=C1OC1=CC=CC=C1C21CCNCC1 NAVNDSDOBFIUBJ-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 3
229960004373 acetylcholine Drugs 0.000 description 3
230000036592 analgesia Effects 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
238000010828 elution Methods 0.000 description 3
229960001867 guaiacol Drugs 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 3
LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
229960005181 morphine Drugs 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920000137 polyphosphoric acid Polymers 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000376 reactant Substances 0.000 description 3
230000001624 sedative effect Effects 0.000 description 3
230000007306 turnover Effects 0.000 description 3
MSHMCQCISOKVCV-UHFFFAOYSA-N (1-benzylspiro[piperidine-4,9'-xanthene]-4'-yl) acetate;hydrochloride Chemical compound Cl.CC(=O)OC1=CC=CC2=C1OC1=CC=CC=C1C2(CC1)CCN1CC1=CC=CC=C1 MSHMCQCISOKVCV-UHFFFAOYSA-N 0.000 description 2
KZNJNBNZBSVEAK-UHFFFAOYSA-N (1-prop-2-ynylspiro[piperidine-4,9'-xanthene]-4'-yl) acetate;hydrochloride Chemical compound Cl.CC(=O)OC1=CC=CC2=C1OC1=CC=CC=C1C21CCN(CC#C)CC1 KZNJNBNZBSVEAK-UHFFFAOYSA-N 0.000 description 2
MYKPYKXCZZXINQ-UHFFFAOYSA-N 1-benzylspiro[piperidine-4,9'-xanthene]-4'-ol Chemical compound OC1=CC=CC2=C1OC1=CC=CC=C1C2(CC1)CCN1CC1=CC=CC=C1 MYKPYKXCZZXINQ-UHFFFAOYSA-N 0.000 description 2
ZXVKXGKPOOIFFF-UHFFFAOYSA-N 1-methoxy-9h-xanthene Chemical class O1C2=CC=CC=C2CC2=C1C=CC=C2OC ZXVKXGKPOOIFFF-UHFFFAOYSA-N 0.000 description 2
RVYVGPUXVJZGKV-UHFFFAOYSA-N 1-methylspiro[piperidine-4,9'-xanthene]-4'-ol Chemical compound C1CN(C)CCC21C1=CC=CC(O)=C1OC1=CC=CC=C12 RVYVGPUXVJZGKV-UHFFFAOYSA-N 0.000 description 2
JEPHIDNDPKYIDL-UHFFFAOYSA-N 1-methylspiro[piperidine-4,9'-xanthene];hydrochloride Chemical compound Cl.C1CN(C)CCC21C1=CC=CC=C1OC1=CC=CC=C12 JEPHIDNDPKYIDL-UHFFFAOYSA-N 0.000 description 2
QVTQYSFCFOGITD-UHFFFAOYSA-N 2,5-dichlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1Cl QVTQYSFCFOGITD-UHFFFAOYSA-N 0.000 description 2
MMCGAUQSMCINLI-UHFFFAOYSA-N 2-[2-chloro-5-methoxy-9-(2-methylsulfonyloxyethyl)xanthen-9-yl]ethyl methanesulfonate Chemical compound O1C2=CC=C(Cl)C=C2C(CCOS(C)(=O)=O)(CCOS(C)(=O)=O)C2=C1C(OC)=CC=C2 MMCGAUQSMCINLI-UHFFFAOYSA-N 0.000 description 2
PFPJRYOJPIYTFC-UHFFFAOYSA-N 2-[4-methoxy-9-(2-methylsulfonyloxyethyl)xanthen-9-yl]ethyl methanesulfonate Chemical compound O1C2=CC=CC=C2C(CCOS(C)(=O)=O)(CCOS(C)(=O)=O)C2=C1C(OC)=CC=C2 PFPJRYOJPIYTFC-UHFFFAOYSA-N 0.000 description 2
TVCPRQLFMOIQKW-UHFFFAOYSA-N 2-[9-(2-hydroxyethyl)xanthen-9-yl]ethanol Chemical compound C1=CC=C2C(CCO)(CCO)C3=CC=CC=C3OC2=C1 TVCPRQLFMOIQKW-UHFFFAOYSA-N 0.000 description 2
GFDINDJAJYXQTR-UHFFFAOYSA-N 2-[9-(2-methylsulfonyloxyethyl)xanthen-9-yl]ethyl methanesulfonate Chemical compound C1=CC=C2C(CCOS(=O)(=O)C)(CCOS(C)(=O)=O)C3=CC=CC=C3OC2=C1 GFDINDJAJYXQTR-UHFFFAOYSA-N 0.000 description 2
AMDUZZOYDBZDEA-UHFFFAOYSA-N 2-[9-(carboxymethyl)xanthen-9-yl]acetic acid Chemical compound C1=CC=C2C(CC(=O)O)(CC(O)=O)C3=CC=CC=C3OC2=C1 AMDUZZOYDBZDEA-UHFFFAOYSA-N 0.000 description 2
IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 2
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XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
230000003187 abdominal effect Effects 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229960001301 amobarbital Drugs 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
229960004782 chlordiazepoxide Drugs 0.000 description 1
ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
229960001076 chlorpromazine Drugs 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
JFWMYCVMQSLLOO-UHFFFAOYSA-N cyclobutanecarbonyl chloride Chemical compound ClC(=O)C1CCC1 JFWMYCVMQSLLOO-UHFFFAOYSA-N 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
MYTMXVHNEWBFAL-UHFFFAOYSA-L dipotassium;carbonate;hydrate Chemical compound O.[K+].[K+].[O-]C([O-])=O MYTMXVHNEWBFAL-UHFFFAOYSA-L 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000012458 free base Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000000262 haloalkenyl group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229960003878 haloperidol Drugs 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
229960001680 ibuprofen Drugs 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000007788 liquid Substances 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
FRKDEDBRSLDGIX-UHFFFAOYSA-N methanesulfonate;piperidin-1-ium Chemical compound CS([O-])(=O)=O.C1CC[NH2+]CC1 FRKDEDBRSLDGIX-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
229960002009 naproxen Drugs 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
230000003533 narcotic effect Effects 0.000 description 1
239000003176 neuroleptic agent Substances 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229960005489 paracetamol Drugs 0.000 description 1
239000004031 partial agonist Substances 0.000 description 1
210000004303 peritoneum Anatomy 0.000 description 1
229960000482 pethidine Drugs 0.000 description 1
229960003893 phenacetin Drugs 0.000 description 1
229940117803 phenethylamine Drugs 0.000 description 1
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
229960002695 phenobarbital Drugs 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
QBMBYVLWDZNKPS-UHFFFAOYSA-N phenyl spiro[piperidine-4,9'-xanthene]-1-carboxylate Chemical compound C1CC2(C3=CC=CC=C3OC3=CC=CC=C32)CCN1C(=O)OC1=CC=CC=C1 QBMBYVLWDZNKPS-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
WIKYUJGCLQQFNW-UHFFFAOYSA-N prochlorperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 WIKYUJGCLQQFNW-UHFFFAOYSA-N 0.000 description 1
229960003111 prochlorperazine Drugs 0.000 description 1
DITHIFQMPPCBCU-UHFFFAOYSA-N propa-1,2-diene Chemical compound [CH]=C=C DITHIFQMPPCBCU-UHFFFAOYSA-N 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
BZQUWQYNKQEWPG-UHFFFAOYSA-N spiro[oxane-4,9'-xanthene]-2,6-dione Chemical compound C1C(=O)OC(=O)CC21C1=CC=CC=C1OC1=CC=CC=C12 BZQUWQYNKQEWPG-UHFFFAOYSA-N 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 1
229960002324 trifluoperazine Drugs 0.000 description 1
229960000834 vinyl ether Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Saccharide Compounds (AREA)

NO750341A 1974-02-04 1975-02-03 NO750341L (es)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB501674*[A GB1447583A (en)	1974-02-04	1974-02-04	Xanthene derivatives

Publications (1)

Publication Number	Publication Date
NO750341L true NO750341L (es)	1975-09-01

Family

ID=9788165

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO750341A NO750341L (es)	1974-02-04	1975-02-03

Country Status (22)

Country	Link
US (2)	US4001419A (es)
JP (1)	JPS50112374A (es)
AT (1)	AT340417B (es)
AU (1)	AU7725375A (es)
BE (1)	BE825129A (es)
CS (1)	CS188938B2 (es)
DD (1)	DD118283A5 (es)
DE (1)	DE2504643A1 (es)
DK (1)	DK37675A (es)
ES (1)	ES434431A1 (es)
FI (1)	FI750302A (es)
FR (1)	FR2259606B1 (es)
GB (1)	GB1447583A (es)
IL (1)	IL46440A (es)
IN (1)	IN140039B (es)
LU (1)	LU71791A1 (es)
NL (1)	NL7501090A (es)
NO (1)	NO750341L (es)
PL (1)	PL97223B1 (es)
SE (1)	SE7501159L (es)
SU (1)	SU581869A3 (es)
ZA (1)	ZA75165B (es)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4198417A (en) *	1979-01-10	1980-04-15	American Hoechst Corporation	Phenoxyphenylpiperidines
US4198420A (en) *	1979-01-10	1980-04-15	American Hoechst Corporation	Spiro[dibenz(b,f)thiepin-piperidine]s
US4198419A (en) *	1979-01-10	1980-04-15	American Hoechst Corporation	Phenylthiophenylpiperidines
US4198418A (en) *	1979-01-10	1980-04-15	American Hoechst Corporation	Spiro[dibenz(b,f)oxepin-piperidine]s
EP0141962A1 (en) *	1983-09-15	1985-05-22	The Hilton - Davis Chemical Company	Hydrazine derivatives of fluorans and use thereof in electrochromic recording systems
US5149830A (en) *	1990-02-23	1992-09-22	Steadfast, Inc.	Substituted xanthene compounds
US7014925B2 (en) *	2003-04-29	2006-03-21	Canon Kabushiki Kaisha	Heterogeneous spiro compounds in organic light emitting device elements
DE102004017398A1 (de) *	2004-04-05	2005-10-20	Clariant Internat Ltd Muttenz	Fluorierte Xanthene und ihre Verwendung in Flüssigkristallmischungen
JP2010100573A (ja) *	2008-10-24	2010-05-06	Sumitomo Chemical Co Ltd	キサンテン誘導体及び該誘導体を含有する熱可塑性ポリマー組成物
WO2013126816A1 (en) *	2012-02-23	2013-08-29	Oregon State Board Of Higher Education On Behalf Of Portland State University	Selective detection of thiols
AR094667A1 (es)	2013-01-31	2015-08-19	Vertex Pharma	Piridonamidas como moduladores de canales de sodio

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3048595A (en) *	1960-11-14	1962-08-07	Smith Kline French Lab	Spiro derivatives of thiazanthenes and xanthenes
US3652558A (en) *	1969-04-21	1972-03-28	Robins Co Inc A H	Spiro condensed aromatic compounds
BE758919A (fr) *	1969-11-15	1971-05-13	Merck Patent Gmbh	Spiro-composes

1974
- 1974-02-04 GB GB501674*[A patent/GB1447583A/en not_active Expired
1975
- 1975-01-09 US US05/539,742 patent/US4001419A/en not_active Expired - Lifetime
- 1975-01-09 ZA ZA00750165A patent/ZA75165B/xx unknown
- 1975-01-13 AU AU77253/75A patent/AU7725375A/en not_active Expired
- 1975-01-13 IN IN78/CAL/75A patent/IN140039B/en unknown
- 1975-01-15 IL IL46440A patent/IL46440A/en unknown
- 1975-01-30 NL NL7501090A patent/NL7501090A/xx not_active Application Discontinuation
- 1975-02-01 PL PL1975192104A patent/PL97223B1/pl unknown
- 1975-02-03 NO NO750341A patent/NO750341L/no unknown
- 1975-02-03 BE BE153012A patent/BE825129A/xx unknown
- 1975-02-03 AT AT77375A patent/AT340417B/de not_active IP Right Cessation
- 1975-02-03 LU LU71791A patent/LU71791A1/xx unknown
- 1975-02-03 FR FR7503263A patent/FR2259606B1/fr not_active Expired
- 1975-02-04 DE DE19752504643 patent/DE2504643A1/de not_active Ceased
- 1975-02-04 DD DD183991A patent/DD118283A5/xx unknown
- 1975-02-04 DK DK37675*#A patent/DK37675A/da unknown
- 1975-02-04 CS CS75718A patent/CS188938B2/cs unknown
- 1975-02-04 FI FI750302A patent/FI750302A/fi not_active Application Discontinuation
- 1975-02-04 JP JP50014763A patent/JPS50112374A/ja active Pending
- 1975-02-04 ES ES434431A patent/ES434431A1/es not_active Expired
- 1975-06-05 SE SE7501159A patent/SE7501159L/xx unknown
- 1975-12-25 SU SU7502302642A patent/SU581869A3/ru active
1976
- 1976-10-14 US US05/732,293 patent/US4268514A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
IL46440A0 (en)	1975-04-25
DE2504643A1 (de)	1975-08-07
GB1447583A (en)	1976-08-25
FI750302A (es)	1975-08-05
FR2259606B1 (es)	1980-01-25
US4268514A (en)	1981-05-19
BE825129A (fr)	1975-08-04
AU7725375A (en)	1976-07-15
DK37675A (es)	1975-09-29
US4001419A (en)	1977-01-04
FR2259606A1 (es)	1975-08-29
JPS50112374A (es)	1975-09-03
CS188938B2 (en)	1979-03-30
SE7501159L (es)	1975-08-05
DD118283A5 (es)	1976-02-20
NL7501090A (nl)	1975-08-06
IN140039B (es)	1976-09-04
LU71791A1 (es)	1976-08-19
PL97223B1 (pl)	1978-02-28
ATA77375A (de)	1977-04-15
ES434431A1 (es)	1977-03-16
AT340417B (de)	1977-12-12
ZA75165B (en)	1976-01-28
SU581869A3 (ru)	1977-11-25
IL46440A (en)	1977-11-30

Publication	Publication Date	Title
US3856967A (en)	1974-12-24	Novel indoles in the treatment of pain
OA11820A (en)	2005-08-17	Functionalized heterocycles as chemokine receptor modulators.
NO750341L (es)	1975-09-01
US3070606A (en)	1962-12-25	Xchxn
EP0937715B1 (en)	2005-06-01	Tetrahydrobenzindole compounds
NO129043B (es)	1974-02-18
CA2316388C (en)	2009-09-08	Tetrahydrobenzindole derivative
NO161619B (no)	1989-05-29	Analogifremgangsmaate for fremstilling av terapeutisk aktive substituerte 5,11-dihydro-6-dibenz(b,e)-azepin-6-on-derivater.
NO163504B (no)	1990-02-26	Ekspansjonsbolt, samt denne kombinert med en gjenget trekkbolt.
JPS6021994B2 (ja)	1985-05-30	置換されたチエノベンゼンジアゼピノン、その酸付加塩、その製法及びこれを含有する胃腸薬
NZ202299A (en)	1985-11-08	Benzofuranone derivatives and pharmaceutical compositions
NO163099B (no)	1989-12-27	Analogifremgangsmaate for fremstilling av terapeutisk aktive benzodiazepin-6-on-derivater.
Huckle et al.	1971	4-Amino-2, 3, 4, 5-tetrahydro-1-benzoxepin-5-ols, 4-amino-2, 3, 4, 5-tetrahydro-1-benzothiepin-5-ols, and related compounds
US4001418A (en)	1977-01-04	1'-substituted-thioxanthene-9-spiro-4'-piperidine derivatives and the 10-oxides and 10,10-dioxides thereof
US4061774A (en)	1977-12-06	Halogenated amino methyl adamantane derivatives
WO2001085732A1 (fr)	2001-11-15	Derives de pyridobenzodiazine et procedes de preparation de ces derives
NO120476B (es)	1970-10-26
US3936459A (en)	1976-02-03	1',4'-Dihydro-1-methyl-spiro [piperidine and pyrrolidine-2,3'(2'H)quinoline]-2'-one compounds
JPS6341388B2 (es)	1988-08-17
US3583997A (en)	1971-06-08	Benzothiopyrano(2,3-c)pyridines
EP0002512B1 (en)	1984-02-22	Imino-bridged benzocycloheptapyridines, process for their preparation and pharmaceutical composition thereof
US3979513A (en)	1976-09-07	1'-Substituted-9,10-dihydroanthracene-9-spiro-4'-piperidine derivatives
US3740406A (en)	1973-06-19	Dihydro-3(4-hydroxy-1-(di or tri-substituted phenethyl) - 4 - piperidyl)-2-(3h)furanone
US3635991A (en)	1972-01-18	8-(2 - 2 - substituted-3-indolyl)ethyl) - 2- lower - alkyl - 2 8 - diazospiro(4 5)1 3-decanediones
NO144099B (no)	1981-03-16	Dyse for maskinell flammehoevling av enkelte defekter paa overflaten til et metallegeme