CA1160227A - DERIVES DE .beta.-3-AMINO-N-NOR-TROPANES - Google Patents

DERIVES DE .beta.-3-AMINO-N-NOR-TROPANES

Info

Publication number: CA1160227A
Authority: CA; Canada
Prior art keywords: benzyl; formula; group; methyl; tropane
Prior art date: 1979-01-16
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

CA000409952A

Other languages

English (en)

Inventor

Philippe Dostert

Thierry Imbert

Bernard Bucher

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.)

Synthelabo SA

Original Assignee

Delalande SA

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.)

1979-01-16

Filing date

1982-08-23

Publication date

1984-01-10

1979-01-16 Priority claimed from FR7900971A external-priority patent/FR2446823A1/fr

1979-12-26 Priority claimed from FR7931656A external-priority patent/FR2476088A2/fr

1982-08-23 Application filed by Delalande SA filed Critical Delalande SA

1982-08-23 Priority to CA000409952A priority Critical patent/CA1160227A/fr

1984-01-10 Application granted granted Critical

1984-01-10 Publication of CA1160227A publication Critical patent/CA1160227A/fr

Status Expired legal-status Critical Current

Links

125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
150000001875 compounds Chemical class 0.000 claims description 27
238000000034 method Methods 0.000 claims description 18
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
-1 monosubstituted benzyl Chemical group 0.000 claims description 12
239000000460 chlorine Substances 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical group CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 5
239000012346 acetyl chloride Substances 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical group CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
238000010992 reflux Methods 0.000 claims description 4
125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
150000007530 organic bases Chemical class 0.000 claims description 3
150000002923 oximes Chemical class 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
GANBJDIOIDQSGI-UHFFFAOYSA-N 2-(chloromethyl)furan Chemical compound ClCC1=CC=CO1 GANBJDIOIDQSGI-UHFFFAOYSA-N 0.000 claims description 2
KKWWFYAKOFXBEY-UHFFFAOYSA-N 3-(chloromethyl)thiophene Chemical compound ClCC=1C=CSC=1 KKWWFYAKOFXBEY-UHFFFAOYSA-N 0.000 claims description 2
150000001805 chlorine compounds Chemical class 0.000 claims description 2
OMEGHMBBBTYRFT-UHFFFAOYSA-N chloromethylcyclohexane Chemical compound ClCC1CCCCC1 OMEGHMBBBTYRFT-UHFFFAOYSA-N 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims 11
239000001257 hydrogen Substances 0.000 claims 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
238000004519 manufacturing process Methods 0.000 claims 4
239000000126 substance Substances 0.000 claims 4
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 2
YZIFVWOCPGPNHB-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C(Cl)=C1 YZIFVWOCPGPNHB-UHFFFAOYSA-N 0.000 claims 1
KQFADYXPELMVHE-UHFFFAOYSA-N 2-chloro-3-methylthiophene Chemical compound CC=1C=CSC=1Cl KQFADYXPELMVHE-UHFFFAOYSA-N 0.000 claims 1
DGGKXQQCVPAUEA-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octane Chemical class C1CCC2CCC1N2 DGGKXQQCVPAUEA-UHFFFAOYSA-N 0.000 abstract description 5
239000000543 intermediate Substances 0.000 abstract description 4
238000002360 preparation method Methods 0.000 abstract description 4
235000013350 formula milk Nutrition 0.000 description 37
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
229940022682 acetone Drugs 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
125000003435 aroyl group Chemical group 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
125000001743 benzylic group Chemical group 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
229940072033 potash Drugs 0.000 description 2
235000015320 potassium carbonate Nutrition 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
IZXWCDITFDNEBY-UHFFFAOYSA-N 1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C=C1 IZXWCDITFDNEBY-UHFFFAOYSA-N 0.000 description 1
FUOHKPSBGLXIRL-UHFFFAOYSA-N 2-(chloromethyl)thiophene Chemical compound ClCC1=CC=CS1 FUOHKPSBGLXIRL-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
101100381997 Danio rerio tbc1d32 gene Proteins 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
150000000918 Europium Chemical class 0.000 description 1
229910052693 Europium Inorganic materials 0.000 description 1
101100381999 Mus musculus Tbc1d32 gene Proteins 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
GPLGAQQQNWMVMM-FCGWIEHOSA-N nerine Chemical compound C1C=C2CC(N(C)C)CC[C@]2(C)C2C1C1CCC3C(C)N(C)C[C@@]31CC2 GPLGAQQQNWMVMM-FCGWIEHOSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000409952A 1979-01-16 1982-08-23 DERIVES DE .beta.-3-AMINO-N-NOR-TROPANES Expired CA1160227A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000409952A CA1160227A (fr)	1979-01-16	1982-08-23	DERIVES DE .beta.-3-AMINO-N-NOR-TROPANES

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
FR7900971A FR2446823A1 (fr)	1979-01-16	1979-01-16	Nouveaux derives du nor-tropane, leur procede de preparation et leur application en therapeutique
FR79.00971		1979-01-16
FR79.31656		1979-12-26
FR7931656A FR2476088A2 (fr)	1979-01-16	1979-12-26	Nouveaux derives du nor-tropane, leur procede de preparation et leur application en therapeutique
CA343,219A CA1130286A (fr)	1979-01-16	1980-01-08	Derives de nor-tropane; methode de preparation et utilisation dans des agents therapeutiques
CA000409952A CA1160227A (fr)	1979-01-16	1982-08-23	DERIVES DE .beta.-3-AMINO-N-NOR-TROPANES

Publications (1)

Publication Number	Publication Date
CA1160227A true CA1160227A (fr)	1984-01-10

Family

ID=27426213

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000409952A Expired CA1160227A (fr)	1979-01-16	1982-08-23	DERIVES DE .beta.-3-AMINO-N-NOR-TROPANES

Country Status (1)

Country	Link
CA (1)	CA1160227A (fr)

1982
- 1982-08-23 CA CA000409952A patent/CA1160227A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-01-10	MKEX	Expiry

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US6087498A (en)	2000-07-11	Process for the preparation of unsymmetrical 4,6-bis(aryloxy) pyrimidine compounds
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CA1173442A (fr)	1984-08-28	Preparation de derives de n-pyrrolyl- pyridazineamine
JPH02255673A (ja)	1990-10-16	４―アリールオキシー１，３―ベンゾジオキソール類およびその製造方法
US5750714A (en)	1998-05-12	Process for the manufacture of related intermediates including cistofur