LU79767A1 - Nouveaux 9-hydroxyhexahydrodibenzo(b,d)pyranes,leurs derives substitues en position 1,leur procede de preparation et medicament les contenant - Google Patents

Nouveaux 9-hydroxyhexahydrodibenzo(b,d)pyranes,leurs derives substitues en position 1,leur procede de preparation et medicament les contenant Download PDF

Info

Publication number: LU79767A1
Authority: LU; Luxembourg
Prior art keywords: group; formula; ether; methyl; singlet
Prior art date: 1977-06-07

Application number

LU79767A

Other languages

English (en)

French (fr)

Inventor

M Johnson

L Melvin

Original Assignee

Pfizer

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.)

1977-06-07

Filing date

1978-06-05

Publication date

1980-01-22

1978-06-05 Application filed by Pfizer filed Critical Pfizer

1980-01-22 Publication of LU79767A1 publication Critical patent/LU79767A1/fr

Links

238000002360 preparation method Methods 0.000 title claims description 30
239000003814 drug Substances 0.000 title description 10
-1 carboxy, carbamyl Chemical group 0.000 claims description 138
150000001875 compounds Chemical class 0.000 claims description 129
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 112
238000000034 method Methods 0.000 claims description 57
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
230000009467 reduction Effects 0.000 claims description 20
238000006722 reduction reaction Methods 0.000 claims description 20
230000008569 process Effects 0.000 claims description 17
125000002947 alkylene group Chemical group 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 12
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 12
UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 10
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 10
125000002252 acyl group Chemical group 0.000 claims description 9
239000012279 sodium borohydride Substances 0.000 claims description 9
229910000033 sodium borohydride Inorganic materials 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 7
229910052744 lithium Inorganic materials 0.000 claims description 7
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
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 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
239000012285 osmium tetroxide Substances 0.000 claims description 4
229910000489 osmium tetroxide Inorganic materials 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
235000018185 Betula X alpestris Nutrition 0.000 claims description 3
235000018212 Betula X uliginosa Nutrition 0.000 claims description 3
238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
229910052987 metal hydride Inorganic materials 0.000 claims 2
150000004681 metal hydrides Chemical class 0.000 claims 2
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 claims 1
HWCXOGQEIVGTAM-UHFFFAOYSA-N 4-oxo-2,3-dihydrochromene-5-carbaldehyde Chemical compound O1CCC(=O)C2=C1C=CC=C2C=O HWCXOGQEIVGTAM-UHFFFAOYSA-N 0.000 claims 1
238000006027 Birch reduction reaction Methods 0.000 claims 1
150000008065 acid anhydrides Chemical class 0.000 claims 1
125000005042 acyloxymethyl group Chemical group 0.000 claims 1
125000005422 alkyl sulfonamido group Chemical group 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
230000006198 deformylation Effects 0.000 claims 1
238000006344 deformylation reaction Methods 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
BDDWSAASCFBVBK-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 BDDWSAASCFBVBK-UHFFFAOYSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 283
239000000203 mixture Substances 0.000 description 93
239000003921 oil Substances 0.000 description 87
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 74
239000000243 solution Substances 0.000 description 73
239000011541 reaction mixture Substances 0.000 description 65
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 47
239000000047 product Substances 0.000 description 47
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 39
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 38
229910052943 magnesium sulfate Inorganic materials 0.000 description 37
235000019341 magnesium sulphate Nutrition 0.000 description 37
239000000741 silica gel Substances 0.000 description 37
229910002027 silica gel Inorganic materials 0.000 description 37
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 33
238000002329 infrared spectrum Methods 0.000 description 31
238000001819 mass spectrum Methods 0.000 description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
239000012071 phase Substances 0.000 description 25
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 24
239000005977 Ethylene Substances 0.000 description 24
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 23
238000011282 treatment Methods 0.000 description 23
238000000605 extraction Methods 0.000 description 22
238000012360 testing method Methods 0.000 description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 21
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
239000000284 extract Substances 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
229910052799 carbon Inorganic materials 0.000 description 16
238000004587 chromatography analysis Methods 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 15
239000012074 organic phase Substances 0.000 description 15
MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
229910052739 hydrogen Inorganic materials 0.000 description 14
230000002829 reductive effect Effects 0.000 description 14
239000003795 chemical substances by application Substances 0.000 description 13
230000000694 effects Effects 0.000 description 13
239000007787 solid Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
239000000543 intermediate Substances 0.000 description 12
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 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 12
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
239000000376 reactant Substances 0.000 description 11
238000010992 reflux Methods 0.000 description 11
239000002904 solvent Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
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 10
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
229910052700 potassium Inorganic materials 0.000 description 10
239000011591 potassium Substances 0.000 description 10
150000003839 salts Chemical class 0.000 description 10
239000011734 sodium Substances 0.000 description 10
239000000126 substance Substances 0.000 description 10
229920002554 vinyl polymer Polymers 0.000 description 10
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
125000006239 protecting group Chemical group 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
239000012312 sodium hydride Substances 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
241001465754 Metazoa Species 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
229940079593 drug Drugs 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 8
239000000725 suspension Substances 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
238000010828 elution Methods 0.000 description 7
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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241000699670 Mus sp. Species 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
150000001299 aldehydes Chemical group 0.000 description 6
125000003277 amino group Chemical group 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
239000000730 antalgic agent Substances 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
239000005457 ice water Substances 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
150000004702 methyl esters Chemical class 0.000 description 6
229960005181 morphine Drugs 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
230000003040 nociceptive effect Effects 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
238000002211 ultraviolet spectrum Methods 0.000 description 6
229910015900 BF3 Inorganic materials 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
235000019270 ammonium chloride Nutrition 0.000 description 5
230000000202 analgesic effect Effects 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
230000033001 locomotion Effects 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
125000004043 oxo group Chemical group O=* 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
230000009466 transformation Effects 0.000 description 5
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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241000699666 Mus <mouse, genus> Species 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 4
238000009903 catalytic hydrogenation reaction Methods 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
CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical group C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
210000002683 foot Anatomy 0.000 description 4
230000006870 function Effects 0.000 description 4
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
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238000004237 preparative chromatography Methods 0.000 description 4
125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 4
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GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
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MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical group FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 3
BEUDCHGZCTUAOG-UHFFFAOYSA-N 6h-benzo[c]chromene Chemical compound C1=CC=C2COC3=CC=CC=C3C2=C1 BEUDCHGZCTUAOG-UHFFFAOYSA-N 0.000 description 3
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QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
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229920002472 Starch Polymers 0.000 description 3
239000013543 active substance Substances 0.000 description 3
150000001335 aliphatic alkanes Chemical class 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
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FCQRKDSALKMOGU-UHFFFAOYSA-K rhodium(3+);triphenylphosphane;trichloride Chemical compound Cl[Rh](Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FCQRKDSALKMOGU-UHFFFAOYSA-K 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
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CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
238000005556 structure-activity relationship Methods 0.000 description 1
238000011421 subcutaneous treatment Methods 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
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239000005720 sucrose Substances 0.000 description 1
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IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
- C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
- 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
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pain & Pain Management (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)

LU79767A 1977-06-07 1978-06-05 Nouveaux 9-hydroxyhexahydrodibenzo(b,d)pyranes,leurs derives substitues en position 1,leur procede de preparation et medicament les contenant LU79767A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US80430677		1977-06-07
US05/804,306 US4118559A (en)	1977-06-07	1977-06-07	9-Hydroxyhexahydrodibenzo[O,d]pyrans, 1-substituted-9-hydroxyhexahydrodibenzo[b,d]pyrans and intermediates therefor

Publications (1)

Publication Number	Publication Date
LU79767A1 true LU79767A1 (fr)	1980-01-22

Family

ID=25188658

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU79767A LU79767A1 (fr)	1977-06-07	1978-06-05	Nouveaux 9-hydroxyhexahydrodibenzo(b,d)pyranes,leurs derives substitues en position 1,leur procede de preparation et medicament les contenant

Country Status (10)

Country	Link
US (1)	US4118559A (ja)
JP (4)	JPS543075A (ja)
BE (1)	BE867858A (ja)
DE (1)	DE2824987A1 (ja)
DK (1)	DK251178A (ja)
FR (1)	FR2393801A1 (ja)
GB (2)	GB2067184B (ja)
IT (1)	IT1110481B (ja)
LU (1)	LU79767A1 (ja)
NL (1)	NL7806189A (ja)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4165323A (en) *	1977-06-07	1979-08-21	Pfizer Inc.	9-Hydroxyhexahydrodibenzo[b,d]pyrans, 1-substituted-9-hydroxyhexahydrodibenzo[b,d]pyrans and intermediates therefor
US4243674A (en) *	1978-06-12	1981-01-06	Pfizer Inc.	9-Hydroxydibenzo[b,d]pyrans and intermediates therefore
US4340737A (en) *	1979-05-29	1982-07-20	Pfizer Inc.	9-Hydroxyoctahydrobenzo[C]quinolines and intermediates therefor
US4405626A (en) *	1980-10-03	1983-09-20	Pfizer Inc.	9-Hydroxyoctahydrobenzo(c)quinolines analgesic compositions containing them and processes for producing analgesic with them
US4400385A (en) *	1980-10-03	1983-08-23	Pfizer Inc.	9-Hydroxyoctahydrobenzo [c]quinolines, analgesic compositions containing them and processes for producing analgesia with them
US4454144A (en) *	1982-06-21	1984-06-12	Pfizer Inc.	Substituted dibenzo[b,d]pyran analgesics
US4681954A (en) *	1985-10-07	1987-07-21	Pennwalt Corporation	7,8,9,10-tetrahydro-6-oxo-6H-dibenzo(b,d)pyranyloxy-propanes
US4647674A (en) *	1985-10-07	1987-03-03	Pennwalt Corporation	Bis-(dibenzo[b,d]pyranyloxy) propanes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4033845A (en) *	1975-11-20	1977-07-05	Warner-Lambert Company	[2-(4-Oxo-4H-1-benzopyran-2-yl)ethenyl]benzonitriles and benzoic acids

1977
- 1977-06-07 US US05/804,306 patent/US4118559A/en not_active Expired - Lifetime
1978
- 1978-06-05 LU LU79767A patent/LU79767A1/fr unknown
- 1978-06-06 IT IT24269/78A patent/IT1110481B/it active
- 1978-06-06 BE BE188351A patent/BE867858A/xx unknown
- 1978-06-06 GB GB8027390A patent/GB2067184B/en not_active Expired
- 1978-06-06 DK DK251178A patent/DK251178A/da unknown
- 1978-06-06 FR FR787816894A patent/FR2393801A1/fr active Granted
- 1978-06-06 GB GB7826430A patent/GB2000761B/en not_active Expired
- 1978-06-07 DE DE19782824987 patent/DE2824987A1/de not_active Withdrawn
- 1978-06-07 JP JP6872778A patent/JPS543075A/ja active Granted
- 1978-06-07 NL NL7806189A patent/NL7806189A/xx not_active Application Discontinuation
1979
- 1979-05-29 JP JP6671579A patent/JPS54163580A/ja active Pending
- 1979-05-29 JP JP6671779A patent/JPS54163581A/ja active Pending
- 1979-05-29 JP JP6671679A patent/JPS5511571A/ja active Pending

Also Published As

Publication number	Publication date
GB2000761B (en)	1982-05-26
IT7824269A0 (it)	1978-06-06
IT1110481B (it)	1985-12-23
JPS543075A (en)	1979-01-11
DE2824987A1 (de)	1978-12-14
GB2067184A (en)	1981-07-22
GB2067184B (en)	1982-08-11
FR2393801A1 (fr)	1979-01-05
FR2393801B1 (ja)	1980-11-07
JPS54163581A (en)	1979-12-26
DK251178A (da)	1978-12-08
GB2000761A (en)	1979-01-17
US4118559A (en)	1978-10-03
BE867858A (fr)	1978-12-06
JPS54163580A (en)	1979-12-26
JPS5735914B2 (ja)	1982-07-31
JPS5511571A (en)	1980-01-26
NL7806189A (nl)	1978-12-11

Publication	Publication Date	Title
CH635813A5 (fr)	1983-04-29	1,9-dihydroxyoctahydrophenanthrenes et medicament les contenant.
LU79824A1 (fr)	1980-01-22	Nouveaux hexahydro-1-hydroxy-9-hydroxymethyl-6h-dibenzo-(b,d)pyranes substitues en position 3,leur procede de preparation et composition pharmaceutique les contenant
EP0001534B1 (fr)	1981-08-12	Nouveaux dérivés du pyrrole, leur procédé de préparation et leurs applications en thérapeutique
FR2498601A1 (fr)	1982-07-30	Nouveaux chromannes substitues utiles notamment comme anti-inflammatoires
FR2554817A1 (fr)	1985-05-17	Nouveaux derives de la vinyl-6 furo-(3,4-c)-pyridine ainsi que leur procede de preparation
CH621785A5 (ja)	1981-02-27
EP0012643A2 (fr)	1980-06-25	Dérivés de la phényl-1 (pipéridyl-4)-3 propanone-1, procédés pour leur préparation, et médicaments les contenant
CH638187A5 (fr)	1983-09-15	3-(2-hydroxy-4(substituant)-phenyl)-azacycloalcanes et medicament les contenant.
CH635812A5 (fr)	1983-04-29	Cycloalcanones et cycloalcanols substitues en position 3 par un groupe 2-hydroxyphenyle substitue en position 4 et composition pharmaceutique les contenant.
LU79767A1 (fr)	1980-01-22	Nouveaux 9-hydroxyhexahydrodibenzo(b,d)pyranes,leurs derives substitues en position 1,leur procede de preparation et medicament les contenant
FR2629820A1 (fr)	1989-10-13	Medicaments a base d'enantiomeres de la furo(3,4-c)pyridine
CA2000091A1 (fr)	1990-04-04	Derives de la benzoxazolinone, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent
EP0022408A1 (fr)	1981-01-14	Nouveaux dérivés de l'alpha-phényl 2-pyrrolidineméthanol et leurs sels, procédé de préparation, application à titre de médicaments et compositions les renfermant
LU82420A1 (fr)	1982-01-20	Nouveaux derives de la 5 h-furanone-2 et de la 3 h-dihydrofuranone-2,leur procede de preparation et leur application en therapeutique
BE1008622A3 (fr)	1996-06-04	Derives de l'epi-epibatidine.
US4151179A (en)	1979-04-24	2-(4H-1-Benzopyran-6-yl)propionic acids
BE854655A (fr)	1977-11-16	9-hydroxyhexahydrobenzo (c) quinoleines et intermediaires de synthese
CH626881A5 (en)	1981-12-15	Process for the preparation of new octahydrobenzo[c]quinolines
EP0078765B1 (fr)	1986-02-26	Dérivés de p-acylaminophénol à effet thérapeutique, procédé pour leur préparation, et composition à effet thérapeutique contenant lesdits dérivés à titre d'ingrédients pharmacologiquement actifs
FR2518992A1 (fr)	1983-07-01	Nouveaux derives aminoalcoxy aromatiques, leur procede de preparation et leur application en therapeutique
CH622790A5 (en)	1981-04-30	Process for the preparation of dibenzopyranones
US4013692A (en)	1977-03-22	Certain 3-phenyl-benzofuran lower alkanoic acids and esters thereof
LU86052A1 (fr)	1986-02-18	Nouveau procede de preparation des derives de la furo-(3,4-c)-pyridine substitues en position 6
BE884145R (fr)	1981-01-05	Composes indoliques nouveaux
FR2595359A1 (fr)	1987-09-11	Nouveaux derives du benzo(4, 5)cyclohepta(1,2-b)thiophene, leur preparation et leur utilisation comme medicaments