SE448457B - Derivat av nor-tropan och granatan, deras framstelling och farmaceutiska komposition - Google Patents

Derivat av nor-tropan och granatan, deras framstelling och farmaceutiska komposition

Info

Publication number: SE448457B
Authority: SE; Sweden
Prior art keywords: formula; group; compounds; benzyl; combination
Prior art date: 1980-11-07

Application number

SE8106425A

Other languages

English (en)

Swedish (sv)

Other versions

SE8106425L (sv

Inventor

P Dostert

T Imbert

B Bucher

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.)

1980-11-07

Filing date

1981-10-30

Publication date

1987-02-23

1981-10-30 Application filed by Delalande Sa filed Critical Delalande Sa

1982-05-08 Publication of SE8106425L publication Critical patent/SE8106425L/xx

1987-02-23 Publication of SE448457B publication Critical patent/SE448457B/sv

Links

238000002360 preparation method Methods 0.000 title claims description 5
239000008194 pharmaceutical composition Substances 0.000 title claims description 3
DGGKXQQCVPAUEA-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octane Chemical class C1CCC2CCC1N2 DGGKXQQCVPAUEA-UHFFFAOYSA-N 0.000 title description 15
ODWVFJUVKLPMDM-UHFFFAOYSA-N 9-methyl-9-azabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1N2C ODWVFJUVKLPMDM-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 64
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
238000000034 method Methods 0.000 claims description 15
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
238000006482 condensation reaction Methods 0.000 claims description 3
230000003340 mental effect Effects 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
230000001079 digestive effect Effects 0.000 claims description 2
125000005905 mesyloxy group Chemical group 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims 2
229910052801 chlorine Inorganic materials 0.000 claims 2
125000004093 cyano group Chemical group *C#N 0.000 claims 2
125000005843 halogen group Chemical group 0.000 claims 2
150000003841 chloride salts Chemical class 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
239000000243 solution Substances 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
241000700159 Rattus Species 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
239000005711 Benzoic acid Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229960004046 apomorphine Drugs 0.000 description 6
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
-1 alkyl sulphate Chemical compound 0.000 description 5
235000010233 benzoic acid Nutrition 0.000 description 5
238000000921 elemental analysis Methods 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
241000699670 Mus sp. Species 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
206010047700 Vomiting Diseases 0.000 description 4
230000008485 antagonism Effects 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
239000000203 mixture Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
230000008673 vomiting Effects 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
230000000968 intestinal effect Effects 0.000 description 3
125000000896 monocarboxylic acid group Chemical group 0.000 description 3
239000000047 product Substances 0.000 description 3
210000002784 stomach Anatomy 0.000 description 3
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical group 0.000 description 2
230000006399 behavior Effects 0.000 description 2
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
210000002249 digestive system Anatomy 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
230000000506 psychotropic effect Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
XLRPYZSEQKXZAA-OCAPTIKFSA-N tropane Chemical group C1CC[C@H]2CC[C@@H]1N2C XLRPYZSEQKXZAA-OCAPTIKFSA-N 0.000 description 2
229930004006 tropane Natural products 0.000 description 2
SKYZYDSNJIOXRL-BTQNPOSSSA-N (6ar)-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol;hydrochloride Chemical compound Cl.C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 SKYZYDSNJIOXRL-BTQNPOSSSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
GLUPJFHPBAJZJS-UHFFFAOYSA-N 2,3-diethoxybenzoic acid Chemical compound CCOC1=CC=CC(C(O)=O)=C1OCC GLUPJFHPBAJZJS-UHFFFAOYSA-N 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
241000219991 Lythraceae Species 0.000 description 1
235000014360 Punica granatum Nutrition 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000003474 anti-emetic effect Effects 0.000 description 1
239000000729 antidote Substances 0.000 description 1
229960003990 apomorphine hydrochloride Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000011324 bead Substances 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
201000006549 dyspepsia Diseases 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000037406 food intake Effects 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000009533 lab test Methods 0.000 description 1
150000002641 lithium Chemical class 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
210000004303 peritoneum Anatomy 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100000816 toxic dose Toxicity 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/14—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing 9-azabicyclo [3.3.1] nonane ring systems, e.g. granatane, 2-aza-adamantane; Cyclic acetals thereof

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Anesthesiology (AREA)
Hospice & Palliative Care (AREA)
Otolaryngology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SE8106425A 1980-11-07 1981-10-30 Derivat av nor-tropan och granatan, deras framstelling och farmaceutiska komposition SE448457B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8023785A FR2493848B2 (fr)	1980-11-07	1980-11-07	Nouveaux derives des nor-tropane et granatane, leur procede de preparation et leur application en therapeutique

Publications (2)

Publication Number	Publication Date
SE8106425L SE8106425L (sv)	1982-05-08
SE448457B true SE448457B (sv)	1987-02-23

Family

ID=9247763

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8106425A SE448457B (sv)	1980-11-07	1981-10-30	Derivat av nor-tropan och granatan, deras framstelling och farmaceutiska komposition

Country Status (15)

Country	Link
US (1)	US4434170A (fr)
JP (1)	JPS57108090A (fr)
BE (1)	BE890962R (fr)
CA (1)	CA1209574A (fr)
CH (1)	CH651561A5 (fr)
DE (1)	DE3144183A1 (fr)
ES (1)	ES8301979A2 (fr)
FR (1)	FR2493848B2 (fr)
GB (1)	GB2088364B (fr)
GR (1)	GR75112B (fr)
IT (1)	IT1140040B (fr)
LU (1)	LU83737A7 (fr)
NL (1)	NL8105042A (fr)
SE (1)	SE448457B (fr)
ZA (1)	ZA817675B (fr)

Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2440946A2 (fr) *	1978-01-20	1980-06-06	Ile De France	Nouveaux benzamides heterocycliques substitues, leurs procedes de preparation et leur application comme modificateurs du comportement
DE3268378D1 (en) *	1981-06-17	1986-02-20	Beecham Group Plc	Alkylthio derivatives of azabicyclobenzamides, their preparation and pharmaceutical compositions
DE3275296D1 (en) *	1981-10-01	1987-03-05	Beecham Group Plc	Azabicyclo-(3,3,1)-nonylbenzamide derivatives, processes for their preparation, and pharmaceutical compositions containing them
EP0083737A1 (fr) *	1981-12-15	1983-07-20	Beecham Group Plc	N-azabicycloalcan benzamides, procédé de préparation et les compositions pharmaceutiques les contenant
FR2531083B1 (fr) *	1982-06-29	1986-11-28	Sandoz Sa	Nouveaux derives de la piperidine, leur preparation et leur utilisation comme medicaments
CA1244028A (fr) *	1983-04-14	1988-11-01	Hans Maag	Derives de pyrimidine
FR2546169B1 (fr) *	1983-05-20	1986-03-21	Delalande Sa	N-oxydes de derives aminocycliques, leur procede de preparation et leur application en therapeutique
FR2548666A1 (fr) *	1983-07-08	1985-01-11	Delalande Sa	Nouveaux derives du nor-tropane et du granatane, leur procede de preparation et leur application en therapeutique
DE3429830A1 (de) *	1983-08-26	1985-03-07	Sandoz-Patent-GmbH, 7850 Lörrach	Automatische carbonsaeure- und sulfonsaeureester oder -amide
DE3445377A1 (de) *	1983-12-23	1985-07-04	Sandoz-Patent-GmbH, 7850 Lörrach	Carbocylische und heterocyclische carbonsaeureester und -amide von ueberbrueckten und nicht ueberbrueckten cyclischen stickstoffhaltigen aminen oder alkoholen
EP0189002B1 (fr) *	1984-12-20	1993-03-03	Sandoz Ag	Traitement de maladies gastro-intestinales utilisant des 5-HT3 antagonistes
EP0385517B1 (fr) *	1985-03-14	1993-04-14	BEECHAM GROUP plc	Médicaments pour le traitement du vomissement
GB8516371D0 (en) *	1985-06-28	1985-07-31	Beecham Group Plc	Compounds
HU202108B (en) *	1986-07-30	1991-02-28	Sandoz Ag	Process for producing pharmaceutical compositions containing serotonine antqgonistic derivatives of indol-carboxylic acid or imidazolyl-methyl-carbazol
US5374637A (en) *	1989-03-22	1994-12-20	Janssen Pharmaceutica N.V.	N-(3-hydroxy-4-piperidinyl)(dihydrobenzofuran, dihydro-2H-benzopyran or dihydrobenzodioxin)carboxamide derivatives
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1980
- 1980-11-07 FR FR8023785A patent/FR2493848B2/fr not_active Expired
1981
- 1981-10-23 CH CH6772/81A patent/CH651561A5/fr not_active IP Right Cessation
- 1981-10-29 GR GR66378A patent/GR75112B/el unknown
- 1981-10-30 SE SE8106425A patent/SE448457B/sv not_active IP Right Cessation
- 1981-11-03 IT IT24835/81A patent/IT1140040B/it active
- 1981-11-03 BE BE0/206420A patent/BE890962R/fr not_active IP Right Cessation
- 1981-11-04 US US06/318,244 patent/US4434170A/en not_active Expired - Lifetime
- 1981-11-04 GB GB8133254A patent/GB2088364B/en not_active Expired
- 1981-11-05 LU LU83737A patent/LU83737A7/fr unknown
- 1981-11-05 CA CA000389504A patent/CA1209574A/fr not_active Expired
- 1981-11-05 ES ES507394A patent/ES8301979A2/es not_active Expired
- 1981-11-06 ZA ZA817675A patent/ZA817675B/xx unknown
- 1981-11-06 DE DE19813144183 patent/DE3144183A1/de active Granted
- 1981-11-07 JP JP56178920A patent/JPS57108090A/ja active Granted
- 1981-11-07 NL NL8105042A patent/NL8105042A/nl not_active Application Discontinuation

Also Published As

Publication number	Publication date
CH651561A5 (fr)	1985-09-30
FR2493848B2 (fr)	1986-05-16
GB2088364A (en)	1982-06-09
DE3144183A1 (de)	1982-08-12
ES507394A0 (es)	1983-02-01
NL8105042A (nl)	1982-06-01
IT8124835A0 (it)	1981-11-03
IT1140040B (it)	1986-09-24
CA1209574A (fr)	1986-08-12
GR75112B (fr)	1984-07-13
ZA817675B (en)	1982-10-27
FR2493848A2 (fr)	1982-05-14
ES8301979A2 (es)	1983-02-01
US4434170A (en)	1984-02-28
GB2088364B (en)	1984-10-31
JPS57108090A (en)	1982-07-05
BE890962R (fr)	1982-05-03
SE8106425L (sv)	1982-05-08
JPS6344753B2 (fr)	1988-09-06
DE3144183C2 (fr)	1992-01-23
LU83737A7 (fr)	1983-09-01

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