CA1114374A - 2-benzyl-perhydroazepins, process for their production and pharmaceutical products containing them - Google Patents

2-benzyl-perhydroazepins, process for their production and pharmaceutical products containing them

Info

Publication number: CA1114374A
Authority: CA; Canada
Prior art keywords: group; carbon atoms; benzyl; hydrogen; alkyl
Prior art date: 1977-04-29
Legal status (The legal status 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 status listed.): Expired

Application number

CA302,270A

Other languages

English (en)

French (fr)

Inventor

Klaus Eistetter

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Takeda GmbH

Original Assignee

Byk Gulden Lomberg Chemische Fabrik GmbH

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.)

1977-04-29

Filing date

1978-04-28

Publication date

1981-12-15

1977-04-29 Priority claimed from LU77229A external-priority patent/LU77229A1/xx

1978-04-28 Application filed by Byk Gulden Lomberg Chemische Fabrik GmbH filed Critical Byk Gulden Lomberg Chemische Fabrik GmbH

1981-12-15 Application granted granted Critical

1981-12-15 Publication of CA1114374A publication Critical patent/CA1114374A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 61
230000008569 process Effects 0.000 title claims abstract description 49
238000004519 manufacturing process Methods 0.000 title claims description 8
239000000825 pharmaceutical preparation Substances 0.000 title description 9
229940127557 pharmaceutical product Drugs 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 98
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 55
150000003839 salts Chemical class 0.000 claims abstract description 53
239000002253 acid Substances 0.000 claims abstract description 52
125000000217 alkyl group Chemical group 0.000 claims abstract description 33
GCXJNDWBSJHSGC-UHFFFAOYSA-N 2-benzylazepane Chemical class C=1C=CC=CC=1CC1CCCCCN1 GCXJNDWBSJHSGC-UHFFFAOYSA-N 0.000 claims abstract description 32
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 31
239000001257 hydrogen Substances 0.000 claims abstract description 28
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
125000003545 alkoxy group Chemical group 0.000 claims abstract description 25
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 25
125000003277 amino group Chemical group 0.000 claims abstract description 24
125000005843 halogen group Chemical group 0.000 claims abstract description 22
125000004423 acyloxy group Chemical group 0.000 claims abstract description 18
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 15
229930195733 hydrocarbon Natural products 0.000 claims abstract description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
238000002360 preparation method Methods 0.000 claims abstract description 13
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 11
125000001931 aliphatic group Chemical group 0.000 claims abstract description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 84
125000004432 carbon atom Chemical group C* 0.000 claims description 83
-1 amino compound Chemical class 0.000 claims description 82
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 46
239000002585 base Substances 0.000 claims description 27
230000000875 corresponding effect Effects 0.000 claims description 25
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
229940075930 picrate Drugs 0.000 claims description 10
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 claims description 10
230000009467 reduction Effects 0.000 claims description 10
OFYXLEPTLFZDDA-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]azepane Chemical compound C1=CC(Cl)=CC=C1CC1NCCCCC1 OFYXLEPTLFZDDA-UHFFFAOYSA-N 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
125000003884 phenylalkyl group Chemical group 0.000 claims description 9
125000004663 dialkyl amino group Chemical group 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
239000012458 free base Substances 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
DKJOAAJDBFGUTR-UHFFFAOYSA-N 4-(azepan-2-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CC1NCCCCC1 DKJOAAJDBFGUTR-UHFFFAOYSA-N 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
125000004442 acylamino group Chemical group 0.000 claims description 5
230000010933 acylation Effects 0.000 claims description 5
238000005917 acylation reaction Methods 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-N 0.000 claims description 4
KMOWEDQINJTXPV-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-1-methylazepane Chemical compound CN1CCCCCC1CC1=CC=C(Cl)C=C1 KMOWEDQINJTXPV-UHFFFAOYSA-N 0.000 claims description 4
HNNYKUXHEAYPLV-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-1-propan-2-ylazepane Chemical compound CC(C)N1CCCCCC1CC1=CC=C(Cl)C=C1 HNNYKUXHEAYPLV-UHFFFAOYSA-N 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
230000026030 halogenation Effects 0.000 claims description 4
238000005658 halogenation reaction Methods 0.000 claims description 4
229950000177 hibenzate Drugs 0.000 claims description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
230000003301 hydrolyzing effect Effects 0.000 claims description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
AADJTSUEBHJPCH-UHFFFAOYSA-N 2-benzyl-1-(cyclopropylmethyl)azepane Chemical compound C1CCCCC(CC=2C=CC=CC=2)N1CC1CC1 AADJTSUEBHJPCH-UHFFFAOYSA-N 0.000 claims description 3
239000005711 Benzoic acid Substances 0.000 claims description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 3
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 3
230000002152 alkylating effect Effects 0.000 claims description 3
229940050390 benzoate Drugs 0.000 claims description 3
238000006266 etherification reaction Methods 0.000 claims description 3
229940050411 fumarate Drugs 0.000 claims description 3
238000006396 nitration reaction Methods 0.000 claims description 3
238000007127 saponification reaction Methods 0.000 claims description 3
GJHWGNGCZORZRL-UHFFFAOYSA-N (2-benzylazepan-1-yl)-cyclopropylmethanone Chemical compound C1CCCCC(CC=2C=CC=CC=2)N1C(=O)C1CC1 GJHWGNGCZORZRL-UHFFFAOYSA-N 0.000 claims description 2
229950005627 embonate Drugs 0.000 claims description 2
238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
150000002828 nitro derivatives Chemical class 0.000 claims description 2
125000005236 alkanoylamino group Chemical group 0.000 claims 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 3
230000000911 decarboxylating effect Effects 0.000 claims 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
125000003342 alkenyl group Chemical group 0.000 claims 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
229940001468 citrate Drugs 0.000 claims 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
238000006722 reduction reaction Methods 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
LEWCHCNBHFXYJM-UHFFFAOYSA-N 1-benzyl-2-[(4-chlorophenyl)methyl]azepane Chemical compound C1=CC(Cl)=CC=C1CC1N(CC=2C=CC=CC=2)CCCCC1 LEWCHCNBHFXYJM-UHFFFAOYSA-N 0.000 claims 1
KXZKKNHRMVOPOQ-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-1-methylazepane Chemical compound CN1CCCCCC1CC1=CC=CC=C1Cl KXZKKNHRMVOPOQ-UHFFFAOYSA-N 0.000 claims 1
CKKDOKPKNOPPJM-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylidene]-1-methylazepane Chemical compound CN1CCCCCC1=CC1=CC=C(Cl)C=C1 CKKDOKPKNOPPJM-UHFFFAOYSA-N 0.000 claims 1
QZCGMTQRZMBKSX-UHFFFAOYSA-N 2-[(4-nitrophenyl)methyl]azepane Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1NCCCCC1 QZCGMTQRZMBKSX-UHFFFAOYSA-N 0.000 claims 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 claims 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 claims 1
SKRCZMMADFGCKM-UHFFFAOYSA-N 7-[(4-aminophenyl)methyl]azepan-2-one Chemical compound C1=CC(N)=CC=C1CC1NC(=O)CCCC1 SKRCZMMADFGCKM-UHFFFAOYSA-N 0.000 claims 1
QQNDLEWHQZWKGU-UHFFFAOYSA-N 7-[(4-chlorophenyl)methyl]-3,4,5,6-tetrahydro-2h-azepine Chemical compound C1=CC(Cl)=CC=C1CC1=NCCCCC1 QQNDLEWHQZWKGU-UHFFFAOYSA-N 0.000 claims 1
WBGFKUKHHSGYAP-UHFFFAOYSA-N 7-benzyl-3,4,5,6-tetrahydro-2h-azepine Chemical compound N=1CCCCCC=1CC1=CC=CC=C1 WBGFKUKHHSGYAP-UHFFFAOYSA-N 0.000 claims 1
235000010233 benzoic acid Nutrition 0.000 claims 1
230000002140 halogenating effect Effects 0.000 claims 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
230000000802 nitrating effect Effects 0.000 claims 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 claims 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 claims 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
239000003814 drug Substances 0.000 abstract description 10
125000003710 aryl alkyl group Chemical group 0.000 abstract description 9
241001465754 Metazoa Species 0.000 abstract description 6
239000000463 material Substances 0.000 abstract description 5
230000009471 action Effects 0.000 abstract description 4
230000000202 analgesic effect Effects 0.000 abstract description 4
239000008280 blood Substances 0.000 abstract description 4
230000036772 blood pressure Effects 0.000 abstract description 3
230000000638 stimulation Effects 0.000 abstract description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
235000002639 sodium chloride Nutrition 0.000 description 40
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
238000007792 addition Methods 0.000 description 32
239000000243 solution Substances 0.000 description 32
238000006243 chemical reaction Methods 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 29
239000003921 oil Substances 0.000 description 28
235000019198 oils Nutrition 0.000 description 28
235000019441 ethanol Nutrition 0.000 description 25
239000002904 solvent Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
229960004756 ethanol Drugs 0.000 description 20
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 17
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000001816 cooling Methods 0.000 description 14
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
235000011167 hydrochloric acid Nutrition 0.000 description 13
229960000443 hydrochloric acid Drugs 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
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 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
238000010992 reflux Methods 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
239000012442 inert solvent Substances 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
235000011181 potassium carbonates Nutrition 0.000 description 10
239000011734 sodium Substances 0.000 description 10
229910052708 sodium Inorganic materials 0.000 description 10
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
235000011121 sodium hydroxide Nutrition 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
239000012280 lithium aluminium hydride Substances 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
239000008194 pharmaceutical composition Substances 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
229960004132 diethyl ether Drugs 0.000 description 7
238000001035 drying Methods 0.000 description 7
239000000155 melt Substances 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 6
229910052697 platinum Inorganic materials 0.000 description 6
239000000047 product Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000454 talc Substances 0.000 description 6
235000012222 talc Nutrition 0.000 description 6
229910052623 talc Inorganic materials 0.000 description 6
238000011282 treatment Methods 0.000 description 6
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
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 5
229960000583 acetic acid Drugs 0.000 description 5
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
238000009835 boiling Methods 0.000 description 5
235000003599 food sweetener Nutrition 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
229960004592 isopropanol Drugs 0.000 description 5
239000011591 potassium Substances 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
239000003765 sweetening agent Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
DNXIQMQGKSQHPC-UHFFFAOYSA-N 7-methoxy-3,4,5,6-tetrahydro-2h-azepine Chemical compound COC1=NCCCCC1 DNXIQMQGKSQHPC-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
235000019759 Maize starch Nutrition 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical class N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 4
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HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
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NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940068917 polyethylene glycols Drugs 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229940072033 potash Drugs 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
229940093928 potassium nitrate Drugs 0.000 description 1
ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
208000037920 primary disease Diseases 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
229960005335 propanol Drugs 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
LZFIOSVZIQOVFW-UHFFFAOYSA-N propyl 2-hydroxybenzoate Chemical class CCCOC(=O)C1=CC=CC=C1O LZFIOSVZIQOVFW-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical compound OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
208000037921 secondary disease Diseases 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
235000020374 simple syrup Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
229960001462 sodium cyclamate Drugs 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
229940114926 stearate Drugs 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
229940086735 succinate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
AGHANLSBXUWXTB-UHFFFAOYSA-N tienilic acid Chemical compound ClC1=C(Cl)C(OCC(=O)O)=CC=C1C(=O)C1=CC=CS1 AGHANLSBXUWXTB-UHFFFAOYSA-N 0.000 description 1
229960000356 tienilic acid Drugs 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229950004288 tosilate Drugs 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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 to ring carbon atoms
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/04—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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 to ring carbon atoms
- C07D223/12—Nitrogen atoms not forming part of a nitro radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA302,270A 1977-04-29 1978-04-28 2-benzyl-perhydroazepins, process for their production and pharmaceutical products containing them Expired CA1114374A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
LU77229A LU77229A1 (es)	1977-04-29	1977-04-29
LU77.229		1977-04-29
DK339777A DK339777A (da)	1977-04-29	1977-07-27	Fremgangsmaade til fremstilling af 2-benzylperhydroazepiner
DK3397/77		1977-07-27

Publications (1)

Publication Number	Publication Date
CA1114374A true CA1114374A (en)	1981-12-15

Family

ID=26067032

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA302,270A Expired CA1114374A (en)	1977-04-29	1978-04-28	2-benzyl-perhydroazepins, process for their production and pharmaceutical products containing them

Country Status (16)

Country	Link
JP (1)	JPS53135994A (es)
AU (1)	AU525198B2 (es)
CA (1)	CA1114374A (es)
DE (1)	DE2818995A1 (es)
ES (1)	ES469164A1 (es)
FI (1)	FI781338A7 (es)
FR (1)	FR2388797A1 (es)
GB (1)	GB1593223A (es)
GR (1)	GR62674B (es)
IE (1)	IE46629B1 (es)
IL (1)	IL54588A (es)
IT (1)	IT1094972B (es)
NL (1)	NL7804579A (es)
NO (1)	NO781530L (es)
NZ (1)	NZ187108A (es)
PT (1)	PT67966B (es)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5013759A (en) *	1985-06-10	1991-05-07	The Procter & Gamble Company	Compounds and compositions having anti-inflammatory and analgesic activity

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1466307A (fr) *	1964-08-18	1967-01-20	Thomae Gmbh Dr K	Procédé pour préparer des nouvelles aminocétones substituées

1978
- 1978-04-26 ES ES469164A patent/ES469164A1/es not_active Expired
- 1978-04-26 GR GR56095A patent/GR62674B/el unknown
- 1978-04-27 IL IL54588A patent/IL54588A/xx unknown
- 1978-04-28 IE IE851/78A patent/IE46629B1/en unknown
- 1978-04-28 GB GB16992/78A patent/GB1593223A/en not_active Expired
- 1978-04-28 NL NL7804579A patent/NL7804579A/xx not_active Application Discontinuation
- 1978-04-28 IT IT22842/78A patent/IT1094972B/it active
- 1978-04-28 CA CA302,270A patent/CA1114374A/en not_active Expired
- 1978-04-28 NO NO781530A patent/NO781530L/no unknown
- 1978-04-28 NZ NZ187108A patent/NZ187108A/xx unknown
- 1978-04-28 AU AU35551/78A patent/AU525198B2/en not_active Expired
- 1978-04-28 PT PT67966A patent/PT67966B/pt unknown
- 1978-04-28 JP JP5021778A patent/JPS53135994A/ja active Pending
- 1978-04-28 FI FI781338A patent/FI781338A7/fi not_active Application Discontinuation
- 1978-04-28 FR FR7812619A patent/FR2388797A1/fr active Granted
- 1978-04-29 DE DE19782818995 patent/DE2818995A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
AU3555178A (en)	1979-11-01
NZ187108A (en)	1979-12-11
GB1593223A (en)	1981-07-15
IE46629B1 (en)	1983-08-10
FI781338A7 (fi)	1978-10-30
PT67966B (de)	1979-11-14
DE2818995A1 (de)	1978-11-02
IT7822842A0 (it)	1978-04-28
IL54588A0 (en)	1978-07-31
AU525198B2 (en)	1982-10-28
FR2388797A1 (fr)	1978-11-24
IT1094972B (it)	1985-08-10
ES469164A1 (es)	1979-09-16
NL7804579A (nl)	1978-10-31
NO781530L (no)	1978-10-31
IL54588A (en)	1982-05-31
PT67966A (de)	1978-05-01
IE780851L (en)	1978-10-29
GR62674B (en)	1979-05-22
FR2388797B1 (es)	1980-10-31
JPS53135994A (en)	1978-11-28

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CA1147733A (en)	1983-06-07	4-phenoxypiperidines, process for their preparation, their use and medicaments containing them
US4133881A (en)	1979-01-09	Azetidinyl acetonitrile and acetamide antiarrhythmia compositions and methods
US4166120A (en)	1979-08-28	Analgesic and tranquilizing benzoylpropyl-spiro[dihydrobenzofuran]piperidines and pyrrolidines
US4279918A (en)	1981-07-21	2-(Nuclearly-substituted)benzylpyrrolidines
US4107074A (en)	1978-08-15	Process for preparing aminoalkylpyrrolobenzoxazalkanes
EP0707570B1 (en)	1998-05-06	Isoquinoline derivatives as therapeutic agents
IE49945B1 (en)	1986-01-08	Production of methylene-cycloamines
CA1114374A (en)	1981-12-15	2-benzyl-perhydroazepins, process for their production and pharmaceutical products containing them
US4430335A (en)	1984-02-07	Substituted 1-azaspiro[4,5]decanes and their analgesic compositions
KR100433609B1 (ko)	2004-05-31	트리사이클릭 벤조[ｅ]이소인돌 및 벤조[ｈ]이소퀴놀린
IE50015B1 (en)	1986-01-22	3-methyleneazetidine derivatives
US4254135A (en)	1981-03-03	3-Amino-4-hydroxypyrrolidines
US4221788A (en)	1980-09-09	2-(Optionally-substituted)benzylperhydroazepines for analgesia and lowering blood pressure
US4622336A (en)	1986-11-11	3,3-dialkyl-and 3,3-alkylene-indoline derivatives, processes for their production and pharmaceutical compositions comprising them
US3729465A (en)	1973-04-24	Hexahydroazepines
US4169095A (en)	1979-09-25	Process for preparing aminoalkylpyrrolobenzoxazalkanes
US4169094A (en)	1979-09-25	Process for preparing aminoalkylpyrrolobenzoxazalkanes
US4874761A (en)	1989-10-17	4-arylcarbonyl-1-[(4-morpholinyl)-lower-alkyl]-1H-indoles
AU596494B2 (en)	1990-05-03	1-((4-morpholinyl)alkyl)-1h-indoles useful as analgesics and preparation thereof
US2513698A (en)	1950-07-04	2 (3) benxofuranone derivatives and methods of making them
US4287212A (en)	1981-09-01	2-Aryl-1,2-dialkylcycloalkylamines
AU763834B2 (en)	2003-07-31	Novel 2,3,3A,4,9,9A hexahydro-8-hydroxy-1H-benz(F)indoles, method for the production thereof, and their use as medicaments
US4409145A (en)	1983-10-11	Process for preparing 4-phenyl-1,3-benzodiazepines
USRE29828E (en)	1978-11-07	1-Substituted-3-amidopyrrolidines

Legal Events

Date	Code	Title	Description
1998-12-15	MKEX	Expiry