CH624403A5 - Process for the preparation of piperidylidene derivatives - Google Patents
Process for the preparation of piperidylidene derivatives Download PDFInfo
- Publication number
- CH624403A5 CH624403A5 CH1432175A CH1432175A CH624403A5 CH 624403 A5 CH624403 A5 CH 624403A5 CH 1432175 A CH1432175 A CH 1432175A CH 1432175 A CH1432175 A CH 1432175A CH 624403 A5 CH624403 A5 CH 624403A5
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- acid
- mol
- xanthenylidene
- reacted
- Prior art date
Links
- -1 piperidylidene Chemical class 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 6
- 230000008569 process Effects 0.000 title claims description 6
- 238000010992 reflux Methods 0.000 claims description 19
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- NCYNKWQXFADUOZ-UHFFFAOYSA-N 1,1-dioxo-2,1$l^{6}-benzoxathiol-3-one Chemical compound C1=CC=C2C(=O)OS(=O)(=O)C2=C1 NCYNKWQXFADUOZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 235000019260 propionic acid Nutrition 0.000 claims description 7
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- JFRMYMMIJXLMBB-UHFFFAOYSA-N xanthydrol Chemical compound C1=CC=C2C(O)C3=CC=CC=C3OC2=C1 JFRMYMMIJXLMBB-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 5
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 5
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims description 4
- PRWJZNITVOUZBU-UHFFFAOYSA-N 2-chloroxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3OC2=C1 PRWJZNITVOUZBU-UHFFFAOYSA-N 0.000 claims description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- CAXBJKFBIPJTRB-UHFFFAOYSA-M [Cl-].CN1CCCCC1[Mg+] Chemical compound [Cl-].CN1CCCCC1[Mg+] CAXBJKFBIPJTRB-UHFFFAOYSA-M 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
- 239000000243 solution Substances 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
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- 239000007818 Grignard reagent Substances 0.000 description 4
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- 239000000969 carrier Substances 0.000 description 4
- 229960001076 chlorpromazine Drugs 0.000 description 4
- 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 4
- 150000004795 grignard reagents Chemical class 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 230000036285 pathological change Effects 0.000 description 4
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- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- OVZSYTCZMSZVHZ-UHFFFAOYSA-N 4-(2-bromoxanthen-9-ylidene)-1-methylpiperidine Chemical compound C1CN(C)CCC1=C1C2=CC(Br)=CC=C2OC2=CC=CC=C21 OVZSYTCZMSZVHZ-UHFFFAOYSA-N 0.000 description 3
- MYGXGCCFTPKWIH-UHFFFAOYSA-N 4-chloro-1-methylpiperidine Chemical compound CN1CCC(Cl)CC1 MYGXGCCFTPKWIH-UHFFFAOYSA-N 0.000 description 3
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- 229940005529 antipsychotics Drugs 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229960003638 dopamine Drugs 0.000 description 3
- 230000003291 dopaminomimetic effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
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- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- QTOOYVGXYKLUNG-UHFFFAOYSA-N 4-(2-chloroxanthen-9-ylidene)piperidine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2C1=C1CCNCC1 QTOOYVGXYKLUNG-UHFFFAOYSA-N 0.000 description 2
- JTGRTBCDDBKEQR-UHFFFAOYSA-N 4-(2-fluoroxanthen-9-ylidene)-1-methylpiperidine Chemical compound C1CN(C)CCC1=C1C2=CC(F)=CC=C2OC2=CC=CC=C21 JTGRTBCDDBKEQR-UHFFFAOYSA-N 0.000 description 2
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- 230000006399 behavior Effects 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
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- YVUQSNJEYSNKRX-UHFFFAOYSA-N pimozide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC(N2C(NC3=CC=CC=C32)=O)CC1 YVUQSNJEYSNKRX-UHFFFAOYSA-N 0.000 description 2
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- FOAXQGRSEHPVEN-UHFFFAOYSA-N 2-(2h-benzo[d][1]benzoxepin-1-ylidene)piperidine Chemical compound N1CCCCC1=C1C(C=2C(=CC=CC=2)C=CO2)=C2C=CC1 FOAXQGRSEHPVEN-UHFFFAOYSA-N 0.000 description 1
- FNROCHFTHIONLL-UHFFFAOYSA-N 2-(9h-thioxanthen-10-ylidene)piperidine Chemical class N1CCCCC1=S1C2=CC=CC=C2CC2=CC=CC=C21 FNROCHFTHIONLL-UHFFFAOYSA-N 0.000 description 1
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- LFDHQGUYWJNDRH-UHFFFAOYSA-N 2-bromo-9-(1-methylpiperidin-4-yl)xanthen-9-ol Chemical compound C1CN(C)CCC1C1(O)C2=CC(Br)=CC=C2OC2=CC=CC=C21 LFDHQGUYWJNDRH-UHFFFAOYSA-N 0.000 description 1
- DYQUGFRRGGOYCA-UHFFFAOYSA-N 2-bromoxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Br)=CC=C3OC2=C1 DYQUGFRRGGOYCA-UHFFFAOYSA-N 0.000 description 1
- VKOJCXWEBUNAGY-UHFFFAOYSA-N 2-chloro-9-(1-methylpiperidin-4-yl)xanthen-9-ol Chemical compound C1CN(C)CCC1C1(O)C2=CC(Cl)=CC=C2OC2=CC=CC=C21 VKOJCXWEBUNAGY-UHFFFAOYSA-N 0.000 description 1
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- 239000005711 Benzoic acid Substances 0.000 description 1
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- 241000220225 Malus Species 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
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- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 230000000768 catecholaminergic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000001962 neuropharmacologic effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000001144 postural effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 210000003523 substantia nigra Anatomy 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 229960002324 trifluoperazine Drugs 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
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes 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 9
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52121674A | 1974-11-06 | 1974-11-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH624403A5 true CH624403A5 (en) | 1981-07-31 |
Family
ID=24075868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1432175A CH624403A5 (en) | 1974-11-06 | 1975-11-05 | Process for the preparation of piperidylidene derivatives |
Country Status (17)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2357251A1 (fr) * | 1976-07-09 | 1978-02-03 | Merck & Co Inc | 1-methyl-4-(2-carboxy-1-thioxanthan-9-ylidene)-piperidine |
| US4073912A (en) * | 1976-10-12 | 1978-02-14 | Smithkline Corporation | Piperidylidene derivatives of benzo-fused xanthenes, thioxanthenes and dibenzoxepins and antipsychotic use thereof |
| US4089961A (en) * | 1976-11-08 | 1978-05-16 | Smithkline Corporation | Antipsychotically useful quinolizidylidene derivatives of xanthenes, thioxanthenes and dibenzoxepins |
| NZ189108A (en) * | 1977-12-29 | 1982-02-23 | Kefalas As | 2-methylthio-6-fluoro-9-(1-methyl-4-piperidylidene)-thioxanthene and pharmaceutical compositions intermediate 2-methylthio-6-fluoro-9-(1-methyl-4-piperidyl)-thioxanthen-9-ol |
| US4777177A (en) * | 1984-10-19 | 1988-10-11 | Ciba-Geigy Corporation | Pesticidal thioxanthen-9-ylidenepiperidines |
| US5250681A (en) * | 1988-06-02 | 1993-10-05 | Ajinomoto Co., Inc. | Piperidine derivatives and hypotensives containing the same |
| CA2004211A1 (en) * | 1988-11-30 | 1990-05-31 | Masataka Syoji | Piperidine derivatives and hyportensives containing the same |
| EP1306376A1 (en) * | 2001-10-25 | 2003-05-02 | Biofrontera Pharmaceuticals AG | Derivatives of 4-(thio- or selenoxanthene-9-ylidene)-piperidine or acridine and its use as a selective 5-HT2B receptor antagonist |
| US7060711B2 (en) | 2001-10-25 | 2006-06-13 | Biofrontera Bioscience Gmbh | Derivatives of 4-(thio- or selenoxanthene-9-ylidene)-piperidine or acridine and its use as a selective 5-HT2B receptor antagonist |
| UA86024C2 (ru) | 2003-06-27 | 2009-03-25 | Янссен Фармацевтика Н.В. | Трициклические дельта-опиоидные модуляторы |
| KR20080027216A (ko) | 2004-08-05 | 2008-03-26 | 얀센 파마슈티카 엔.브이. | 트리사이클릭 δ-오피오이드 조절자 |
| CA2591963A1 (en) | 2004-12-22 | 2006-06-29 | Janssen Pharmaceutica N.V. | Tricyclic o-opioid modulators |
| US20060135522A1 (en) * | 2004-12-22 | 2006-06-22 | Carson John R | Tricyclic delta-opioid modulators |
| MX2007007627A (es) | 2004-12-22 | 2008-01-28 | Johnson & Johnson | Moduladores delta-opioides triciclicos. |
| KR20070104380A (ko) | 2005-01-06 | 2007-10-25 | 얀센 파마슈티카 엔.브이. | 트리사이클릭 δ-오피오이드 조절제 |
| BRPI0611885A2 (pt) | 2005-06-16 | 2010-10-05 | Janssen Pharmaceutica Nv | moduladores opióides tricìclicos |
| EP2067777B1 (en) * | 2006-09-29 | 2013-08-14 | Nippon Zoki Pharmaceutical Co., Ltd. | Oxepin derivative |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL260070A (enrdf_load_stackoverflow) * | 1960-02-25 | |||
| NL283292A (enrdf_load_stackoverflow) * | 1961-09-29 | |||
| DE1670118A1 (de) * | 1966-07-22 | 1970-11-05 | Boehringer Mannheim Gmbh | Verfahren zur Herstellung neuer Derivate des 6,11-Dihydro-dibenz[b,e]oxepins und ihrer Salze |
| US3470188A (en) * | 1967-01-05 | 1969-09-30 | Smithkline Corp | 9-cycloalkyl-lower alkyl-piperidylidene derivatives of xanthenes and thioxanthenes |
| JPS5018478A (enrdf_load_stackoverflow) * | 1973-05-17 | 1975-02-26 |
-
1975
- 1975-10-16 ZA ZA00756550A patent/ZA756550B/xx unknown
- 1975-10-31 AU AU86247/75A patent/AU498298B2/en not_active Expired
- 1975-10-31 CA CA238,781A patent/CA1055945A/en not_active Expired
- 1975-11-02 IL IL48400A patent/IL48400A/xx unknown
- 1975-11-03 HU HU75SI1494A patent/HU174639B/hu not_active IP Right Cessation
- 1975-11-03 NZ NZ179139A patent/NZ179139A/xx unknown
- 1975-11-03 PH PH17733A patent/PH12158A/en unknown
- 1975-11-04 LU LU73714A patent/LU73714A1/xx unknown
- 1975-11-04 FR FR7533631A patent/FR2290202A1/fr active Granted
- 1975-11-04 DK DK495775AA patent/DK139429B/da not_active IP Right Cessation
- 1975-11-04 IE IE2398/75A patent/IE42137B1/en unknown
- 1975-11-04 BE BE161500A patent/BE835224A/xx not_active IP Right Cessation
- 1975-11-05 CH CH1432175A patent/CH624403A5/de not_active IP Right Cessation
- 1975-11-05 NL NL7512974A patent/NL7512974A/xx not_active Application Discontinuation
- 1975-11-05 JP JP50133564A patent/JPS5826754B2/ja not_active Expired
- 1975-11-05 ES ES442357A patent/ES442357A1/es not_active Expired
- 1975-11-06 DE DE19752549841 patent/DE2549841A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5170768A (enrdf_load_stackoverflow) | 1976-06-18 |
| IL48400A0 (en) | 1976-01-30 |
| AU8624775A (en) | 1977-05-05 |
| IE42137L (en) | 1976-05-06 |
| CA1055945A (en) | 1979-06-05 |
| DK139429B (da) | 1979-02-19 |
| FR2290202B1 (enrdf_load_stackoverflow) | 1980-05-23 |
| ES442357A1 (es) | 1977-04-01 |
| DE2549841A1 (de) | 1976-05-13 |
| LU73714A1 (enrdf_load_stackoverflow) | 1976-06-11 |
| IE42137B1 (en) | 1980-06-04 |
| BE835224A (fr) | 1976-05-04 |
| AU498298B2 (en) | 1979-03-01 |
| ZA756550B (en) | 1976-09-29 |
| JPS5826754B2 (ja) | 1983-06-04 |
| HU174639B (hu) | 1980-02-28 |
| PH12158A (en) | 1978-11-10 |
| FR2290202A1 (fr) | 1976-06-04 |
| DK495775A (enrdf_load_stackoverflow) | 1976-05-07 |
| DK139429C (enrdf_load_stackoverflow) | 1979-08-06 |
| NL7512974A (nl) | 1976-05-10 |
| DE2549841C2 (enrdf_load_stackoverflow) | 1988-07-07 |
| IL48400A (en) | 1979-01-31 |
| NZ179139A (en) | 1978-04-28 |
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