NO130795B - - Google Patents
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- Publication number
- NO130795B NO130795B NO509669A NO509669A NO130795B NO 130795 B NO130795 B NO 130795B NO 509669 A NO509669 A NO 509669A NO 509669 A NO509669 A NO 509669A NO 130795 B NO130795 B NO 130795B
- Authority
- NO
- Norway
- Prior art keywords
- benzomorphan
- hydroxy
- dimethyl
- ethylenedioxy
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 16
- -1 ethylenedioxy Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 229940051805 benzomorphan derivative analgesics Drugs 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000012043 crude product Substances 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 239000012188 paraffin wax Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000012259 ether extract Substances 0.000 description 5
- 239000003350 kerosene Substances 0.000 description 5
- DXESFJJJWBHLJX-UHFFFAOYSA-N norcyclazocine Chemical compound C1C2=CC=C(O)C=C2C2(C)C(C)C1NCC2 DXESFJJJWBHLJX-UHFFFAOYSA-N 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 208000011580 syndromic disease Diseases 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000003533 narcotic effect Effects 0.000 description 3
- 239000007929 subcutaneous injection Substances 0.000 description 3
- 238000010254 subcutaneous injection Methods 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 2
- 229960005301 pentazocine Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QLNABPPQCYRTBQ-UHFFFAOYSA-N 2-(3-bromopropyl)-2-(4-fluorophenyl)-1,3-dioxolane Chemical compound C1=CC(F)=CC=C1C1(CCCBr)OCCO1 QLNABPPQCYRTBQ-UHFFFAOYSA-N 0.000 description 1
- GBTKQXADFUEFCI-UHFFFAOYSA-N 2-(3-chloropropyl)-2-(2,5-dimethylphenyl)-1,3-dioxolane Chemical compound CC1=CC=C(C)C(C2(CCCCl)OCCO2)=C1 GBTKQXADFUEFCI-UHFFFAOYSA-N 0.000 description 1
- FOWUXKOABSPDLH-UHFFFAOYSA-N 2-(3-chloropropyl)-2-(2-methoxyphenyl)-1,3-dioxolane Chemical compound COC1=C(C=CC=C1)C1(CCCCl)OCCO1 FOWUXKOABSPDLH-UHFFFAOYSA-N 0.000 description 1
- FXFDJSQOCVDXBX-UHFFFAOYSA-N 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane Chemical compound C1=CC(F)=CC=C1C1(CCCCl)OCCO1 FXFDJSQOCVDXBX-UHFFFAOYSA-N 0.000 description 1
- AZMRFTWGFYRHPA-UHFFFAOYSA-N 2-(3-chloropropyl)-2-(4-methoxyphenyl)-1,3-dioxolane Chemical compound C1=CC(OC)=CC=C1C1(CCCCl)OCCO1 AZMRFTWGFYRHPA-UHFFFAOYSA-N 0.000 description 1
- XETYSLNCJSBQCZ-UHFFFAOYSA-N 2-(3-chloropropyl)-2-(4-methylphenyl)-1,3-dioxolane Chemical compound C1=CC(C)=CC=C1C1(CCCCl)OCCO1 XETYSLNCJSBQCZ-UHFFFAOYSA-N 0.000 description 1
- XNRXOTHPVLKZQS-UHFFFAOYSA-N 2-(3-chloropropyl)-2-(4-methylsulfanylphenyl)-1,3-dioxolane Chemical compound CSC1=CC=C(C=C1)C1(CCCCl)OCCO1 XNRXOTHPVLKZQS-UHFFFAOYSA-N 0.000 description 1
- HLEMXSKEDMEZFX-UHFFFAOYSA-N 2-(4-chlorobutyl)-2-(4-methoxyphenyl)-1,3-dioxolane Chemical compound C1=CC(OC)=CC=C1C1(CCCCCl)OCCO1 HLEMXSKEDMEZFX-UHFFFAOYSA-N 0.000 description 1
- YBBZXBJCWJTFHQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(3-chloropropyl)-1,3-dioxolane Chemical compound C=1C=C(Cl)C=CC=1C1(CCCCl)OCCO1 YBBZXBJCWJTFHQ-UHFFFAOYSA-N 0.000 description 1
- GHEFQKHLHFXSBR-UHFFFAOYSA-N 4-chloro-1-phenylbutan-1-one Chemical compound ClCCCC(=O)C1=CC=CC=C1 GHEFQKHLHFXSBR-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- NSLKFRGZLUIUKO-QWRGUYRKSA-N 6,7-benzomorphan Chemical class C1C2=CC=CC=C2[C@H]2CCN[C@@H]1C2 NSLKFRGZLUIUKO-QWRGUYRKSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010024264 Lethargy Diseases 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000008896 Opium Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 1
- 206010038678 Respiratory depression Diseases 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
- 229920002472 Starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 101150038575 clpS gene Proteins 0.000 description 1
- 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 1
- 229960004126 codeine Drugs 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000001335 demethylating effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 230000002964 excitative effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229960001027 opium Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 238000000746 purification Methods 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
- 230000004044 response Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 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
- 230000008673 vomiting Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/26—Benzomorphans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9627168 | 1968-12-26 | ||
| JP9627068 | 1968-12-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO130795B true NO130795B (xx) | 1974-11-04 |
| NO130795C NO130795C (xx) | 1975-02-12 |
Family
ID=26437491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO509669A NO130795C (xx) | 1968-12-26 | 1969-12-23 |
Country Status (16)
| Country | Link |
|---|---|
| AT (1) | AT293414B (xx) |
| BE (1) | BE743733A (xx) |
| BR (1) | BR6915175D0 (xx) |
| CH (1) | CH525893A (xx) |
| CS (1) | CS161100B2 (xx) |
| DE (1) | DE1962442C3 (xx) |
| DK (1) | DK132755C (xx) |
| ES (1) | ES374901A1 (xx) |
| FI (1) | FI51349C (xx) |
| FR (1) | FR2027126B1 (xx) |
| GB (1) | GB1276719A (xx) |
| NL (1) | NL160252C (xx) |
| NO (1) | NO130795C (xx) |
| PL (1) | PL80422B1 (xx) |
| SE (1) | SE363328B (xx) |
| YU (1) | YU34123B (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3776914A (en) * | 1970-01-27 | 1973-12-04 | Sumitomo Chemical Co | 5-phenylbenzomorphan derivatives and salts thereof |
| DE2114511C3 (de) * | 1970-04-06 | 1979-05-10 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | 2-Alkyl-6,7-benzomorphane, Verfahren zu ihrer Herstellung und ihre Weiterverarbeitung zu 2-BenzoaIkyl-6,7-benzomorphanen |
| NO137441C (no) * | 1970-06-10 | 1978-03-01 | Sumitomo Chemical Co | Fremgangsmaate for fremstilling av 2-substituerte 6,7-benzomorfanderivater og salter derav |
| CH581624A5 (xx) * | 1970-08-14 | 1976-11-15 | Sumitomo Chemical Co |
-
1969
- 1969-12-10 GB GB6033069A patent/GB1276719A/en not_active Expired
- 1969-12-12 DE DE19691962442 patent/DE1962442C3/de not_active Expired
- 1969-12-15 BR BR21517569A patent/BR6915175D0/pt unknown
- 1969-12-22 FI FI371569A patent/FI51349C/fi active
- 1969-12-22 FR FR6944394A patent/FR2027126B1/fr not_active Expired
- 1969-12-23 AT AT1201669A patent/AT293414B/de not_active IP Right Cessation
- 1969-12-23 NO NO509669A patent/NO130795C/no unknown
- 1969-12-23 SE SE1793469A patent/SE363328B/xx unknown
- 1969-12-23 CS CS848369A patent/CS161100B2/cs unknown
- 1969-12-23 DK DK684069A patent/DK132755C/da not_active IP Right Cessation
- 1969-12-24 CH CH1928769A patent/CH525893A/de not_active IP Right Cessation
- 1969-12-24 ES ES374901A patent/ES374901A1/es not_active Expired
- 1969-12-24 NL NL6919358A patent/NL160252C/xx not_active IP Right Cessation
- 1969-12-24 PL PL13778869A patent/PL80422B1/pl unknown
- 1969-12-24 BE BE743733D patent/BE743733A/xx not_active IP Right Cessation
- 1969-12-25 YU YU321969A patent/YU34123B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES374901A1 (es) | 1972-04-01 |
| GB1276719A (en) | 1972-06-07 |
| YU321969A (en) | 1978-05-15 |
| FR2027126A1 (xx) | 1970-09-25 |
| DK132755C (da) | 1976-07-12 |
| BR6915175D0 (pt) | 1973-02-08 |
| NL6919358A (xx) | 1970-06-30 |
| DK132755B (da) | 1976-02-02 |
| YU34123B (en) | 1978-12-31 |
| CS161100B2 (xx) | 1975-05-04 |
| CH525893A (de) | 1972-07-31 |
| FR2027126B1 (xx) | 1973-08-10 |
| NL160252C (nl) | 1979-10-15 |
| DE1962442A1 (de) | 1970-11-26 |
| AT293414B (de) | 1971-10-11 |
| DE1962442B2 (de) | 1978-04-27 |
| NL160252B (nl) | 1979-05-15 |
| FI51349B (xx) | 1976-08-31 |
| PL80422B1 (en) | 1975-08-30 |
| NO130795C (xx) | 1975-02-12 |
| SE363328B (xx) | 1974-01-14 |
| DE1962442C3 (de) | 1979-01-11 |
| BE743733A (xx) | 1970-05-28 |
| FI51349C (fi) | 1976-12-10 |
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