NL8100078A - Nieuwe 2-aminomethyl-6-halogeen-fenolen, alsmede werkwijzen voor het bereiden van deze fenolen en van geneesmiddelen die ze bevatten. - Google Patents
Nieuwe 2-aminomethyl-6-halogeen-fenolen, alsmede werkwijzen voor het bereiden van deze fenolen en van geneesmiddelen die ze bevatten. Download PDFInfo
- Publication number
- NL8100078A NL8100078A NL8100078A NL8100078A NL8100078A NL 8100078 A NL8100078 A NL 8100078A NL 8100078 A NL8100078 A NL 8100078A NL 8100078 A NL8100078 A NL 8100078A NL 8100078 A NL8100078 A NL 8100078A
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- Netherlands
- Prior art keywords
- substituents
- formula
- acid addition
- compounds
- hydrogen atom
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- 238000000034 method Methods 0.000 title claims description 29
- 150000002989 phenols Chemical class 0.000 title description 3
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 80
- 125000001424 substituent group Chemical group 0.000 claims description 75
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000012458 free base Substances 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 230000031709 bromination Effects 0.000 claims description 6
- 238000005893 bromination reaction Methods 0.000 claims description 6
- 229910052740 iodine Chemical group 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- DVRXQBVVJWNSFT-UHFFFAOYSA-N 6-(1-aminoethyl)-4-bromo-2,3-dihydro-1h-inden-5-ol Chemical compound BrC1=C(O)C(C(N)C)=CC2=C1CCC2 DVRXQBVVJWNSFT-UHFFFAOYSA-N 0.000 claims description 4
- -1 6-Aminomethyl-4-bromo-1,3-dimethylindan-ol Chemical compound 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- XVSLEJJCOJAXLT-UHFFFAOYSA-N 4-(aminomethyl)-6-bromo-1,1-diethyl-2,3-dihydroinden-5-ol Chemical compound C1=C(Br)C(O)=C(CN)C2=C1C(CC)(CC)CC2 XVSLEJJCOJAXLT-UHFFFAOYSA-N 0.000 claims description 2
- OHSNQRGFOIAQOI-UHFFFAOYSA-N 6-(1-aminoethyl)-4-iodo-2,3-dihydro-1H-inden-5-ol Chemical compound NC(C)C1=C(C(=C2CCCC2=C1)I)O OHSNQRGFOIAQOI-UHFFFAOYSA-N 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims 2
- KLTWVNBJFBNIIE-UHFFFAOYSA-N 6-(2-aminopropan-2-yl)-4-iodo-1,1-dimethyl-2,3-dihydroinden-5-ol Chemical compound NC(C)(C)C1=C(C(=C2CCC(C2=C1)(C)C)I)O KLTWVNBJFBNIIE-UHFFFAOYSA-N 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
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- 125000004429 atom Chemical group 0.000 claims 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
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- 239000000203 mixture Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
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- 238000002844 melting Methods 0.000 description 11
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 5
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- REJUADUBWMTPSU-UHFFFAOYSA-N 1,1-dimethyl-2,3-dihydroinden-5-ol Chemical compound OC1=CC=C2C(C)(C)CCC2=C1 REJUADUBWMTPSU-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- FGGDDHBBDLHADV-UHFFFAOYSA-N 6-bromo-1,1-dimethyl-2,3-dihydroinden-5-ol Chemical compound OC1=C(Br)C=C2C(C)(C)CCC2=C1 FGGDDHBBDLHADV-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000003276 anti-hypertensive effect Effects 0.000 description 3
- 239000002220 antihypertensive agent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
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- 229940079593 drug Drugs 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- YIAPLDFPUUJILH-UHFFFAOYSA-N indan-1-ol Chemical compound C1=CC=C2C(O)CCC2=C1 YIAPLDFPUUJILH-UHFFFAOYSA-N 0.000 description 3
- PEHSSTUGJUBZBI-UHFFFAOYSA-N indan-5-ol Chemical compound OC1=CC=C2CCCC2=C1 PEHSSTUGJUBZBI-UHFFFAOYSA-N 0.000 description 3
- 230000026045 iodination Effects 0.000 description 3
- 238000006192 iodination reaction Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- JAAJQSRLGAYGKZ-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-ol Chemical group C1=CC=C2C(O)CCCC2=C1 JAAJQSRLGAYGKZ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SKUARYJIZAZJMC-UHFFFAOYSA-N 1-(6-hydroxy-2,3-dihydro-1h-inden-5-yl)ethanone Chemical compound C1=C(O)C(C(=O)C)=CC2=C1CCC2 SKUARYJIZAZJMC-UHFFFAOYSA-N 0.000 description 2
- LPASIUQHYJEFSN-UHFFFAOYSA-N 4-(3-methoxyphenyl)-2-methylbutan-2-ol Chemical compound COC1=CC=CC(CCC(C)(C)O)=C1 LPASIUQHYJEFSN-UHFFFAOYSA-N 0.000 description 2
- RTQWXRRMEPPQOV-UHFFFAOYSA-N 4-(aminomethyl)-6-bromo-1,1-dimethyl-2,3-dihydroinden-5-ol Chemical compound C1=C(Br)C(O)=C(CN)C2=C1C(C)(C)CC2 RTQWXRRMEPPQOV-UHFFFAOYSA-N 0.000 description 2
- IANSGPOMUSLZAA-UHFFFAOYSA-N 6-(2-azidopropan-2-yl)-1,1-dimethyl-2,3-dihydroinden-5-ol Chemical compound N(=[N+]=[N-])C(C)(C)C1=C(C=C2CCC(C2=C1)(C)C)O IANSGPOMUSLZAA-UHFFFAOYSA-N 0.000 description 2
- ZAELBGKWWXXQLD-UHFFFAOYSA-N 6-(2-hydroxypropan-2-yl)-1,1-dimethyl-2,3-dihydroinden-5-ol Chemical compound OC(C)(C)C1=C(C=C2CCC(C2=C1)(C)C)O ZAELBGKWWXXQLD-UHFFFAOYSA-N 0.000 description 2
- HFGPHWPHGQMASW-UHFFFAOYSA-N 6-(aminomethyl)-4-bromo-1,1-dimethyl-2,3-dihydroinden-5-ol Chemical compound NCC1=C(C(=C2CCC(C2=C1)(C)C)Br)O HFGPHWPHGQMASW-UHFFFAOYSA-N 0.000 description 2
- WLYPZDDVVLYPDN-UHFFFAOYSA-N 6-ethanimidoyl-2,3-dihydro-1H-inden-5-ol Chemical compound N=C(C)C1=C(C=C2CCCC2=C1)O WLYPZDDVVLYPDN-UHFFFAOYSA-N 0.000 description 2
- DVIQJHKQDUMLBP-UHFFFAOYSA-N 6-methoxy-3,3-dimethyl-1,2-dihydroindene Chemical compound COC1=CC=C2C(C)(C)CCC2=C1 DVIQJHKQDUMLBP-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NDFLLQDPOKNBQT-UHFFFAOYSA-N N-[(6-bromo-5-hydroxy-1,1-dimethyl-2,3-dihydroinden-4-yl)methyl]-2-chloroacetamide Chemical compound BrC1=C(C(=C2CCC(C2=C1)(C)C)CNC(CCl)=O)O NDFLLQDPOKNBQT-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229940127088 antihypertensive drug Drugs 0.000 description 2
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- 230000000144 pharmacologic effect Effects 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000000054 salidiuretic effect Effects 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- UATJAMCFYCSHDP-UHFFFAOYSA-N 1,1-diethyl-2,3-dihydroinden-5-ol Chemical compound C(C)C1(CCC2=CC(=CC=C12)O)CC UATJAMCFYCSHDP-UHFFFAOYSA-N 0.000 description 1
- KTUYLBNYBGOMJW-UHFFFAOYSA-N 1-(6-hydroxy-3,3-dimethyl-1,2-dihydroinden-5-yl)ethanone Chemical compound C1=C(O)C(C(=O)C)=CC2=C1CCC2(C)C KTUYLBNYBGOMJW-UHFFFAOYSA-N 0.000 description 1
- TXNSZCSYBXHETP-UHFFFAOYSA-N 2-chloro-n-(hydroxymethyl)acetamide Chemical compound OCNC(=O)CCl TXNSZCSYBXHETP-UHFFFAOYSA-N 0.000 description 1
- DWZLOBDVNHOFHM-UHFFFAOYSA-N 3,3-dimethyl-1,2-dihydroinden-5-amine Chemical compound C1=C(N)C=C2C(C)(C)CCC2=C1 DWZLOBDVNHOFHM-UHFFFAOYSA-N 0.000 description 1
- BJJQJLOZWBZEGA-UHFFFAOYSA-N 3-Methoxybenzenepropanoic acid Chemical compound COC1=CC=CC(CCC(O)=O)=C1 BJJQJLOZWBZEGA-UHFFFAOYSA-N 0.000 description 1
- SCWNNOCLLOHZIG-UHFFFAOYSA-N 5,6,7,8-tetrahydro-1-naphthol Chemical compound C1CCCC2=C1C=CC=C2O SCWNNOCLLOHZIG-UHFFFAOYSA-N 0.000 description 1
- QABOLNFSGSPIFN-UHFFFAOYSA-N 6-(1-aminoethyl)-2,3-dihydro-1h-inden-5-ol Chemical compound C1=C(O)C(C(N)C)=CC2=C1CCC2 QABOLNFSGSPIFN-UHFFFAOYSA-N 0.000 description 1
- GXTBXCFGLOZMLW-UHFFFAOYSA-N 6-(1-aminoethyl)-4-bromo-1,1-dimethyl-2,3-dihydroinden-5-ol Chemical compound BrC1=C(O)C(C(N)C)=CC2=C1CCC2(C)C GXTBXCFGLOZMLW-UHFFFAOYSA-N 0.000 description 1
- ASAUSCGTEIPLPE-UHFFFAOYSA-N 6-(2-aminopropan-2-yl)-1,1-dimethyl-2,3-dihydroinden-5-ol Chemical compound C1=C(O)C(C(C)(N)C)=CC2=C1CCC2(C)C ASAUSCGTEIPLPE-UHFFFAOYSA-N 0.000 description 1
- DOEWFQKWXBYOSW-UHFFFAOYSA-N 6-(2-aminopropan-2-yl)-4-bromo-1,1-dimethyl-2,3-dihydroinden-5-ol Chemical compound NC(C)(C)C1=C(C(=C2CCC(C2=C1)(C)C)Br)O DOEWFQKWXBYOSW-UHFFFAOYSA-N 0.000 description 1
- YJKILAMZBAQTBC-UHFFFAOYSA-N 6-(aminomethyl)-1,1-dimethyl-2,3-dihydroinden-5-ol Chemical compound OC1=C(CN)C=C2C(C)(C)CCC2=C1 YJKILAMZBAQTBC-UHFFFAOYSA-N 0.000 description 1
- ASAAPDAIYYUUAL-UHFFFAOYSA-N 6-ethanimidoyl-1,1-dimethyl-2,3-dihydroinden-5-ol Chemical compound N=C(C)C1=C(C=C2CCC(C2=C1)(C)C)O ASAAPDAIYYUUAL-UHFFFAOYSA-N 0.000 description 1
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
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- KHSQXAZUIVMEHS-UHFFFAOYSA-N N-[(6-bromo-1,1-diethyl-5-hydroxy-2,3-dihydroinden-4-yl)methyl]-2-chloroacetamide Chemical compound BrC1=C(C(=C2CCC(C2=C1)(CC)CC)CNC(CCl)=O)O KHSQXAZUIVMEHS-UHFFFAOYSA-N 0.000 description 1
- DVRHIXWQICIPIO-UHFFFAOYSA-N NC(C)C1=C(C=C2CCC(C2=C1)(C)C)O Chemical compound NC(C)C1=C(C=C2CCC(C2=C1)(C)C)O DVRHIXWQICIPIO-UHFFFAOYSA-N 0.000 description 1
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- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
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- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
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- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic 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
- 125000003258 trimethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
-
- 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
- C07C37/045—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 by substitution of a group bound to the ring by nitrogen
-
- 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
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
-
- 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
- C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- 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
- C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
-
- 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
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- 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
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH26780 | 1980-01-14 | ||
| CH26780 | 1980-01-14 | ||
| CH748380 | 1980-10-07 | ||
| CH748380 | 1980-10-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8100078A true NL8100078A (nl) | 1981-08-17 |
Family
ID=25684084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8100078A NL8100078A (nl) | 1980-01-14 | 1981-01-09 | Nieuwe 2-aminomethyl-6-halogeen-fenolen, alsmede werkwijzen voor het bereiden van deze fenolen en van geneesmiddelen die ze bevatten. |
Country Status (11)
| Country | Link |
|---|---|
| AU (1) | AU6618081A (de) |
| DE (1) | DE3100592A1 (de) |
| DK (1) | DK13781A (de) |
| FR (1) | FR2473512A1 (de) |
| GB (1) | GB2067195A (de) |
| IL (1) | IL61894A0 (de) |
| IT (1) | IT1142256B (de) |
| NL (1) | NL8100078A (de) |
| PT (1) | PT72338B (de) |
| SE (1) | SE8100122L (de) |
| WO (1) | WO1981002012A1 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4583344A (en) * | 1984-06-06 | 1986-04-22 | Butler Delica M | Simulated thatched roofing |
| GB8812342D0 (en) * | 1988-05-25 | 1988-06-29 | Ici America Inc | Bicyclic compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6049183B2 (ja) * | 1977-12-29 | 1985-10-31 | 小野薬品工業株式会社 | 2−アミノメチルフェノ−ル誘導体 |
| WO1980000561A1 (fr) * | 1978-09-06 | 1980-04-03 | Sandoz Ag | Derives de l'(alpha)-alcoyle-o-oxy-benzylamine, leur preparation et remedes les contenant |
| NZ193729A (en) * | 1979-05-28 | 1982-03-30 | Ciba Geigy Ag | Substituted phenols medicinal preparations |
-
1981
- 1981-01-09 NL NL8100078A patent/NL8100078A/nl not_active Application Discontinuation
- 1981-01-10 DE DE19813100592 patent/DE3100592A1/de not_active Withdrawn
- 1981-01-12 IL IL61894A patent/IL61894A0/xx unknown
- 1981-01-12 PT PT72338A patent/PT72338B/pt unknown
- 1981-01-12 GB GB8100803A patent/GB2067195A/en not_active Withdrawn
- 1981-01-12 SE SE8100122A patent/SE8100122L/xx not_active Application Discontinuation
- 1981-01-13 DK DK13781A patent/DK13781A/da not_active Application Discontinuation
- 1981-01-13 AU AU66180/81A patent/AU6618081A/en not_active Abandoned
- 1981-01-13 WO PCT/CH1981/000004 patent/WO1981002012A1/de not_active Ceased
- 1981-01-14 IT IT47569/81A patent/IT1142256B/it active
- 1981-01-14 FR FR8100542A patent/FR2473512A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| SE8100122L (sv) | 1981-07-15 |
| FR2473512A1 (fr) | 1981-07-17 |
| IT8147569A0 (it) | 1981-01-14 |
| DK13781A (da) | 1981-07-15 |
| PT72338A (en) | 1981-02-01 |
| AU6618081A (en) | 1981-07-23 |
| GB2067195A (en) | 1981-07-22 |
| IL61894A0 (en) | 1981-02-27 |
| DE3100592A1 (de) | 1981-12-03 |
| IT1142256B (it) | 1986-10-08 |
| PT72338B (en) | 1982-04-05 |
| WO1981002012A1 (fr) | 1981-07-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed |