PT88302B - Processo para a preparacao de novos derivados da oxima de 1,2,5,6-tetraidropidin-3-carboxaldeido - Google Patents

Processo para a preparacao de novos derivados da oxima de 1,2,5,6-tetraidropidin-3-carboxaldeido Download PDF

Info

Publication number: PT88302B
Authority: PT; Portugal
Prior art keywords: group; formula; product; process according; carbon atoms
Prior art date: 1987-08-21

Application number

PT88302A

Other languages

English (en)

Portuguese (pt)

Other versions

PT88302A (pt

Inventor

Emilio Toja

Fernando Barzaghi

Giulio Galliani

Carla Bonetti

Original Assignee

Roussel Uclaf

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.)

1987-08-21

Filing date

1988-08-19

Publication date

1995-03-31

1988-08-19 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1989-09-14 Publication of PT88302A publication Critical patent/PT88302A/pt

1995-03-31 Publication of PT88302B publication Critical patent/PT88302B/pt

Links

238000000034 method Methods 0.000 title claims description 39
-1 4-chlorophenyloxycarbonyl Chemical group 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 16
229910052500 inorganic mineral Inorganic materials 0.000 claims description 14
239000011707 mineral Substances 0.000 claims description 14
229920006395 saturated elastomer Polymers 0.000 claims description 13
150000007513 acids Chemical class 0.000 claims description 12
125000004417 unsaturated alkyl group Chemical group 0.000 claims description 11
150000002923 oximes Chemical class 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 7
125000004122 cyclic group Chemical group 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
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239000003814 drug Substances 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
235000005985 organic acids Nutrition 0.000 claims description 5
238000007083 alkoxycarbonylation reaction Methods 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 69
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
239000000047 product Substances 0.000 description 41
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
238000004458 analytical method Methods 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
KGXZDPHYHMCYQB-UHFFFAOYSA-N 1,2,3,6-tetrahydropyridine-5-carbaldehyde Chemical compound O=CC1=CCCNC1 KGXZDPHYHMCYQB-UHFFFAOYSA-N 0.000 description 9
239000003480 eluent Substances 0.000 description 9
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 7
238000003756 stirring Methods 0.000 description 7
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PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
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230000036760 body temperature Effects 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
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YIQBHPFHKPIDSO-UHFFFAOYSA-N n-methoxy-1-(1,2,3,6-tetrahydropyridin-5-yl)methanimine Chemical compound CON=CC1=CCCNC1 YIQBHPFHKPIDSO-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
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239000000460 chlorine Substances 0.000 description 2
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230000002631 hypothermal effect Effects 0.000 description 2
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239000008101 lactose Substances 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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125000001424 substituent group Chemical group 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
PNLZKVOKOVFGMZ-UHFFFAOYSA-N 1-adamantyl carbonofluoridate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)F)C3 PNLZKVOKOVFGMZ-UHFFFAOYSA-N 0.000 description 1
LVZPKYYPPLUECL-UHFFFAOYSA-N 1-chloro-4-(trichloromethyl)benzene Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C=C1 LVZPKYYPPLUECL-UHFFFAOYSA-N 0.000 description 1
NDSTWKKMYPBNTD-UHFFFAOYSA-N 1-ethyl-3,6-dihydro-2h-pyridine-5-carbaldehyde Chemical compound CCN1CCC=C(C=O)C1 NDSTWKKMYPBNTD-UHFFFAOYSA-N 0.000 description 1
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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 1
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239000008186 active pharmaceutical agent Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
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125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
239000000556 agonist Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
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RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
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RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
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229910052794 bromium Inorganic materials 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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238000006243 chemical reaction Methods 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
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125000006165 cyclic alkyl group Chemical group 0.000 description 1
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125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
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238000010494 dissociation reaction Methods 0.000 description 1
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229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
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239000004459 forage Substances 0.000 description 1
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AXOJRQLKMVSHHZ-UHFFFAOYSA-N methyl 1-methyl-1,2,3,6-tetrahydropyridin-1-ium-5-carboxylate;bromide Chemical compound Br.COC(=O)C1=CCCN(C)C1 AXOJRQLKMVSHHZ-UHFFFAOYSA-N 0.000 description 1
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239000003755 preservative agent Substances 0.000 description 1
QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-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
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239000011734 sodium Substances 0.000 description 1
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PYIHTIJNCRKDBV-UHFFFAOYSA-L trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;dichloride Chemical compound [Cl-].[Cl-].C[N+](C)(C)CCCCCC[N+](C)(C)C PYIHTIJNCRKDBV-UHFFFAOYSA-L 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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

PT88302A 1987-08-21 1988-08-19 Processo para a preparacao de novos derivados da oxima de 1,2,5,6-tetraidropidin-3-carboxaldeido PT88302B (pt)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT8721687A IT1222526B (it)	1987-08-21	1987-08-21	Derivati dell' ossima della 1,2,5,6-tetraidropiridin-3-carbossaldeide,loro procedimento di preparazione e loro impiego come sostanze medicinali

Publications (2)

Publication Number	Publication Date
PT88302A PT88302A (pt)	1989-09-14
PT88302B true PT88302B (pt)	1995-03-31

Family

ID=11185397

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PT88302A PT88302B (pt)	1987-08-21	1988-08-19	Processo para a preparacao de novos derivados da oxima de 1,2,5,6-tetraidropidin-3-carboxaldeido

Country Status (22)

Country	Link
US (1)	US4921868A (2)
EP (1)	EP0308283B1 (2)
JP (1)	JPH07107048B2 (2)
KR (1)	KR960014998B1 (2)
AT (1)	ATE71938T1 (2)
AU (1)	AU608643B2 (2)
CA (1)	CA1340987C (2)
DE (1)	DE3867986D1 (2)
DK (1)	DK457388A (2)
ES (1)	ES2038776T3 (2)
FI (1)	FI90070C (2)
GR (1)	GR3004249T3 (2)
HU (2)	HU201012B (2)
IE (1)	IE61537B1 (2)
IL (1)	IL87430A0 (2)
IT (1)	IT1222526B (2)
MX (1)	MX12707A (2)
NO (1)	NO174504B (2)
NZ (1)	NZ225902A (2)
PT (1)	PT88302B (2)
SU (1)	SU1681723A3 (2)
ZA (1)	ZA886131B (2)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5231107A (en) *	1987-08-21	1993-07-27	Roussel Uclaf	Derivatives of the oxime of 1,2,5,6-tetrahydropyridine 3-carboxaldehyde, the process for their preparation, their use as medicaments and the compositions containing them
PT90266B (pt) *	1988-04-15	1994-07-29	Beecham Group Plc	Processo para a preparacao de compostos azabiciclicos
SG48315A1 (en) *	1989-04-13	1998-04-17	Beecham Group Plc	Novel compounds
US5278170A (en) *	1989-04-13	1994-01-11	Beecham Group P.L.C.	Azabicylo oxime compounds
IT1240603B (it) *	1990-03-14	1993-12-17	Roussel Maestretti Spa	Derivati della 1,2,5,6-tetraidropiridina 3- carbossaldeide ossima, loro procedimento di preparazione e loro impiego come sostanza medicinale
IT1241138B (it) *	1990-05-15	1993-12-29	Roussel Pharma	Derivati dell'ossina della 1,2,5,6- tetraidropiridin-3-carbossaldeide,loro procedimento di preparazione e loro impiego come sostanze medicinali
WO1992003435A1 (en) *	1990-08-24	1992-03-05	Beecham Group Plc	Azabicyclic compounds, process and intermediates for their preparation and pharmaceutical compositions containing them
GB9019095D0 (en) *	1990-09-01	1990-10-17	Beecham Group Plc	Novel compounds
CA2093823A1 (en) *	1990-10-12	1992-04-13	Steven M. Bromidge	1,2,5,6-tetrahydropyridine oxime derivatives

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1258847A (fr) *	1960-02-12	1961-04-21	Ciba Geigy	Procédé de préparation de nouveaux dérivés pyridiniques, entre autres de l'oxime de la l-méthyl-3 ou 4-acétyl-1, 2, 5, 6-tétrahydropyridine
IL81610A (en) *	1986-02-27	1990-12-23	Roussel Uclaf	Derivatives of 1,2,5,6-tetrahydropyridin-3-carboxaldehyde oxime,their preparation and pharmaceutical compositions containing them
US4786648A (en) *	1986-12-08	1988-11-22	Warner-Lambert Company	O-substituted tetrahydropyridine oxime cholinergic agents
IT1203971B (it) *	1987-04-24	1989-02-23	Roussel Maestretti Spa	Derivati di 1,2,5,6-tetraidropiridina, loro procedimento di preparazione e loro applicazione come medicamenti

1987
- 1987-08-21 IT IT8721687A patent/IT1222526B/it active
1988
- 1988-08-08 NO NO883521A patent/NO174504B/no unknown
- 1988-08-12 IL IL8887430A patent/IL87430A0/xx not_active IP Right Cessation
- 1988-08-16 DK DK457388A patent/DK457388A/da not_active Application Discontinuation
- 1988-08-17 MX MX1270788A patent/MX12707A/es unknown
- 1988-08-18 JP JP63203962A patent/JPH07107048B2/ja not_active Expired - Fee Related
- 1988-08-18 ZA ZA886131A patent/ZA886131B/xx unknown
- 1988-08-19 AU AU21100/88A patent/AU608643B2/en not_active Ceased
- 1988-08-19 FI FI883869A patent/FI90070C/fi not_active IP Right Cessation
- 1988-08-19 SU SU4356622A patent/SU1681723A3/ru active
- 1988-08-19 HU HU884414A patent/HU201012B/hu not_active IP Right Cessation
- 1988-08-19 EP EP88402128A patent/EP0308283B1/fr not_active Expired - Lifetime
- 1988-08-19 IE IE253888A patent/IE61537B1/en not_active IP Right Cessation
- 1988-08-19 AT AT88402128T patent/ATE71938T1/de not_active IP Right Cessation
- 1988-08-19 CA CA000575166A patent/CA1340987C/fr not_active Expired - Fee Related
- 1988-08-19 PT PT88302A patent/PT88302B/pt not_active IP Right Cessation
- 1988-08-19 ES ES198888402128T patent/ES2038776T3/es not_active Expired - Lifetime
- 1988-08-19 DE DE8888402128T patent/DE3867986D1/de not_active Expired - Fee Related
- 1988-08-22 US US07/234,632 patent/US4921868A/en not_active Expired - Fee Related
- 1988-08-22 KR KR1019880010676A patent/KR960014998B1/ko not_active Expired - Fee Related
- 1988-08-22 NZ NZ225902A patent/NZ225902A/xx unknown
1992
- 1992-04-02 GR GR910402203T patent/GR3004249T3/el unknown
1995
- 1995-06-29 HU HU95P/P00578P patent/HU211913A9/hu unknown

Also Published As

Publication number	Publication date
DK457388D0 (da)	1988-08-16
IT8721687A0 (it)	1987-08-21
IE61537B1 (en)	1994-11-16
KR960014998B1 (ko)	1996-10-23
EP0308283A1 (fr)	1989-03-22
NO883521L (no)	1989-02-22
FI90070B (fi)	1993-09-15
AU608643B2 (en)	1991-04-11
JPS6468356A (en)	1989-03-14
KR890003692A (ko)	1989-04-17
FI90070C (fi)	1993-12-27
GR3004249T3 (2)	1993-03-31
CA1340987C (fr)	2000-05-09
MX12707A (es)	1993-10-01
ATE71938T1 (de)	1992-02-15
NO174504B (no)	1994-02-07
NO174504C (2)	1994-05-18
HU201012B (en)	1990-09-28
JPH07107048B2 (ja)	1995-11-15
IL87430A0 (en)	1989-01-31
HU211913A9 (en)	1996-01-29
NZ225902A (en)	1990-06-26
DK457388A (da)	1989-02-22
PT88302A (pt)	1989-09-14
HUT49328A (en)	1989-09-28
IE882538L (en)	1989-02-21
NO883521D0 (no)	1988-08-08
EP0308283B1 (fr)	1992-01-22
IT1222526B (it)	1990-09-05
FI883869A7 (fi)	1989-02-22
FI883869A0 (fi)	1988-08-19
DE3867986D1 (de)	1992-03-05
US4921868A (en)	1990-05-01
AU2110088A (en)	1989-02-23
ZA886131B (en)	1989-10-25
ES2038776T3 (es)	1993-08-01
SU1681723A3 (ru)	1991-09-30

Legal Events

Date	Code	Title	Description
1995-03-31	FG3A	Patent granted, date of granting	Effective date: 19940908
2000-01-31	PC3A	Transfer or assignment	Free format text: 19991011 HOECHST MARION ROUSSEL FR
2000-01-31	PD3A	Change of proprietorship	Owner name: ROUSSEL UCLAF Effective date: 19991011
2000-01-31	TE3A	Change of address (patent)	Owner name: ROUSSEL UCLAF Effective date: 19991011
2003-03-31	PC3A	Transfer or assignment	Free format text: AVENTIS PHARMA S.A. FR Effective date: 20030110
2004-06-30	MM3A	Annulment or lapse	Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 20040331

Publication	Publication Date	Title
HK29797A (en)	1997-03-21	1,2,5,6-tetrahydropyridine-3-carboxaldehyde oxime derivatives, process for their preparation, compositions containing them and their use as medicines
JPS6323186B2 (2)	1988-05-16
JPS6049192B2 (ja)	1985-10-31	新規置換ベンズアミド、その製造方法及びこれを有効成分とする向精神薬
JPH0132823B2 (2)	1989-07-10
BRPI0709644A2 (pt)	2011-07-19	sal, processo para a preparação de um sal, solução aquosa, uso de um sal, composição famacêutica, processo para a preparação de uma composição farmacêutica, e, produto
CH636839A5 (de)	1983-06-30	4-(2-oxo-1-cycloalkylidenmethyl)-phenylessigsaeurederivate, sowie verfahren zu deren herstellung und pharmazeutisch zulaessige salze solcher verbindungen.
US5015655A (en)	1991-05-14	1-azabicycloalkane derivatives, their preparation process and their use as medicaments
PT87290B (pt)	1992-08-31	Processo para a preparacao de novos derivados da 1,2,5,6-tetrahidropiridina e dos seus sais e de composicoes farmaceuticas que os contem
JPS6135189B2 (2)	1986-08-12
CA1338494C (fr)	1996-07-30	Derives de l'oxime du 1,2,5,6-tetrahydropyridine, leur procede de preparation, leur application comme medicaments et les compositions les renfermant
JPS5939405B2 (ja)	1984-09-22	獣医用鎮痛剤
HUE031676T2 (en)	2017-07-28	An effective medicine for neuropathic pain
KR960014998B1 (ko)	1996-10-23	1,2,5,6-테트라히드로피리딘-3-카르복스알데히드의 옥심유도체, 이들의 제조방법, 약제로서의 이들의 용도 및 이들을 함유하는 조성물
HU181147B (en)	1983-06-28	Process for preparing substituted heterocyclin phenoxamines
DK149133B (da)	1986-02-10	Analogifremgangsmaade til fremstilling af 2-(4-(diphenylmethylen)- l-piperidinyl)- eddikesyrer eller farmaceutisk acceptable salte heraf
NO147150B (no)	1982-11-01	Analogifremgangsmaate ved fremstilling av terapeutisk aktive piperidiner.
US4285943A (en)	1981-08-25	Novel pharmaceutical compositions incorporating an aryltrifluoroethanol
US4528299A (en)	1985-07-09	1-(2,3-Dimethyl-4-methoxyphenyl)-2-methyl-3-(1-pyrrolidinyl)-1-propanone and anti-spastic use thereof
JPH01203361A (ja)	1989-08-16	新規の３―ピぺリジンカルバルデヒドのオキシムの誘導体、それらの製造方法及びそれらの薬剤としての使用
US4233304A (en)	1980-11-11	Pyridoxine derivatives
HU186492B (en)	1985-08-28	Process for producing phenthanol-mine derivatives
HU192876B (en)	1987-07-28	Process for producing 5,10-dihydro-11h-dibenzo/b,e//1,4/ diazepin-11-one derivatives substitutes at the 5 position and pharmaceutical compositions containing them
US4196206A (en)	1980-04-01	Pyridyl-piperazine derivative with anti-arrythmic effect
IE58497B1 (en)	1993-10-06	New process for the preparation of derivatives of 4h-1, 2,4-triazole, the new triazoles so obtained, their use as medicaments and the pharmaceutical compositions containing them
HU209930B (en)	1994-12-28	Process for producing of 2-mercapto-2-(1-isoquinolylidene)-acetonitrile derivatives and pharmaceutical compositions comprising them