SI9011006B - Novi 8-substituirani-2-aminotetralini - Google Patents
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- SI9011006B SI9011006B SI9011006A SI9011006A SI9011006B SI 9011006 B SI9011006 B SI 9011006B SI 9011006 A SI9011006 A SI 9011006A SI 9011006 A SI9011006 A SI 9011006A SI 9011006 B SI9011006 B SI 9011006B
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
- C07C211/42—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems with six-membered aromatic rings being part of the condensed ring systems
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P25/00—Drugs for disorders of the nervous system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- 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
- A61P25/26—Psychostimulants, e.g. nicotine, ***e
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/20—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C229/50—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms being part of the same condensed ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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Claims (14)
1 Patentni zahtevki 1. Spojina s formulo
v kateri so: Rje vodik ali metil, pod pogojem, daje Cj-metilni substituent v cis-konfiguraciji, Z je vodik ali halogen, Q je COR1 ali 5- ali 6-členski aril, ki lahko vsebuje 1 ali 2 heteroatoma izbrana izmed N, O ali S in ki je ali (i) v danem primeru substituiran z enim ali več substituenti, neodvisno izbranimi izmed halogena, CN, CF3, C^C^-alkila, C2-C6-alkenila ali nižjega alkoksi, ali je (ii) vezan preko dveh sosednjih ogljikovih atomov na arilni obroč, pri čemer je omenjeni arilni obroč v danem primeru substituiran z enim ali več substituenti, neodvisno izbranimi izmed halogena CN, CF3, C1-C6-alkila, C2-C6-alkenila ali nižjega alkoksi, R1 je C1-C6-alkil ali 5- ali 6-členski aromatski obroč, ki lahko vsebuje heteroatome izbrane izmed O in S in ki je ali (i) v danem primeru substituiran s substituenti neodvisno izbranimi izmed halogena, CF3, nižjega alkila ali nižjega alkoksi, ali pa je (ii) vezan preko dveh sosednjih ogljikovih atomov na benzenov obroč, pri čemer je benzenov obroč v danem primeru substituiran s substituenti, ki so neodvisno izbrani iz skupine, ki vsebuje halogen, CF3, nižji alkil ali nižji alkoksi, R2 je vodik ali Cj-C6-alkil, R3 je skupina Cj-C^alkil, -(CH2)a-R4, -CH2-CH=CH-(CH2)b-R4, -CH2-CsC-(CH2)b-R4, “(CHa)
-CH (CH2)to-R* X (ch2), 2 kjer je: a 1 do 5, b 0,1 ali 2, c 1, 2, 3 ali 4, d 2 ali 3, X O, S ali NR5, kjer je R5 vodik, cikloalkil, alkil, Cj-C6-alkil, v danem primeru substituiran s hidroksi, amino, alkilmino, dialkilamino, arilom, heteroarilom, aralkilom, alkoksikarbonilom, alkilsul-fonilom, fenilsulfonilom, tolilsulfonilom, benzilsulfonilom, formilom, karbamoilom ali sulfamoilom, R4 je vodik, halogen, CF3, CN ali skupina -OR6, -COOR7, -CONR8R9, -S02NR8R9, -SO R10, -NRllR12, m 7
ali -CH \ A
X kjer: imajo c, d in X zgoraj podane pomene, A je vodik, alkilsulfonil, fenilsulfonil, tolilsulfonil, benzilsulfonil, acil ali alkoksikar-bonil, R6 je vodik, alkil, alkenil, cikloalkil, aril, aralkil, acil, alkoksikarbonil, R7 je vodik, alkil, alkenil, aril ali aralkil, R8 in R9, ki sta enaka ali različna, sta vsak vodik, alkil, aril ali aralkil, R10 je alkil, cikloalkil, aril ali aralkil in je lahko arilni ostanek substituiran s halogenom, ciano, alkilom, alkoksi, trifluorometilom ali trifluorometoksi, m je 0,1 ali 2, R11 in R12, ki sta enaka ali različna, sta vsak vodik, alkil, aril ali aralkil in arilni ostanek je lahko substituiran s halogenom, ciano, alkilom, alkoksi ali trifluorometilom ali 3 R11 in R12 skupaj z atomom dušika tvorita obroč: I I h2c
<CH2>n
kjer je n 1 ali 2, R2 in R3 skupaj z atomom dušika tvorita obroč s formulo: (CH2), Y -N (ch2) 4 v kateri: imata c in d zgoraj podani pomen in Y je O, S ali skupina NR5 ali CH(CH2)e-NHR5, kjer: ima R5 zgoraj podani pomen in je e 0,1, 2, 3 ali 4, in njeni enantiomeri in njene fiziološko sprejemljive soli, pod pogojem, da Q ne sme biti nesubstituiran 2-pirolil, 2-oksazolil, 5-oksazolil ali 2-imidazolil.
2. Spojina po zahtevku 1, označena s tem, daje Q COR1, kjer je R1 CH3, C2HS, C3H7, C4H9, C5Hu, ciklopropil, metilciklopropil, ciklobutil, metilciklobutil.
3. Spojina po zahtevku 1, označena s tem, daje Q fenil, fluorofenil, tienil ali furanil.
4. Spojina po kateremkoli od zahtevkov 1 do 3, označena s tem, da je R3 skupina Cj-C6 alkih
5. Farmacevtski pripravek, označen s tem, da vsebuje kot aktivno sestavino spojino po kateremkoli od zahtevkov 1 do 4, njen enantiomer ali njeno farmacevtsko sprejemljivo soh
6. Spojina po kateremkoli od zahtevkov 1 do 4, njen enantiomer ali njena fiziološko sprejemljiva sol za uporabo v terapiji.
7. Spojina po zahtevku 6 za uporabo v zdravljenju depresije, vznemirjenosti, anoreksije, senilne demence, migrene, Alzheimerjeve bolezni, hipertenzije, ter-moregulacijskih in seksualnih motenj.
8. Spojina po zahtevku 6 za uporabo v zdravljenju bolečine.
9. Spojina po zahtevku 6 za uporabo v zdravljenju motenj kardiovaskularnega sistema.
10. Uporaba spojine po kateremkoli od zahtevkov 1 do 4 za proizvodnjo zdravila za zdravljenje motenj v centralnem živčnem sistemu, zlasti motenj posredovanih s 5-hidroksi-triptaminom. 5
11. Uporaba po zahtevku 10 za proizvodnjo zdravila za zdravljenje depresije, vznemirjenosti, anoreksije, senilne demence, migrene, Alzheimerjeve bolezni, ter-moregulacijskih in seksualnih motenj.
12. Uporaba po zahtevku 10 za proizvodnjo zdravila za zdravljenje bolečine.
13. Uporaba po zahtevku 10 za proizvodnjo zdravila za zdravljenje motenj v kardiovaskularnem sistemu.
14. Postopek za pripravo spojin s formulo I po zahtevku 1, označen s tem, da obsega: a) pretvorbo spojine s formulo (II):
v kateri je X odhodna skupina in so R, R2 in R3 kot je definirano pod formulo I, s pomočjo katalitskega ciklusa z uporabo ničvalentne prehodne kovine M°, ki jo podvržemo oksidativni adiciji na aril-x-vezi, obdelavo z ogljikovim monoksidom in nato transmetalacijo med R1 - M1, kjer je M1 kovina in je R1 kot je definiran pod formulo I in prvotno formiranim karboniliranim a-aril-kovina-x-kompleksom, da se tvori spojina s formulo I; b) reakcijo s pomočjo katalitskega ciklusa ob uporabi ničvalentne prehodne kovine M°, ki jo podvržemo oksidativni adiciji na R!-X, kjer je R1 kot je definiran pod formulo I in je X odhodna skupina, obdelavo z ogljikovim dioksidom in nato adicijo spojine s formulo (III):
v kateri so R, R2 in R3 kot je definirano pod formulo I in je M1 prehodna kovina, tako da se tvori spojina s formulo I; 6 c) pretvorbo spojine s formulo (II):
(IB) kjer je X odhodna skupina in so R, R1 2 in R3 kot je definirano pod formulo I, z reakcijo z ničvalentno prehodno kovino M° in s primernim arilnim substituentom, kot je trialkilarilstanan, tako da se tvori spojina s formulo IB; d) pretvorbo spojine s formulo (V):
v kateri je X takšna odhodna skupina, kot je trifluorometansulfonat, je Z halogen, so R, R2 in R3 definirani kot pod formulo I, z reakcijami, ki so opisane v postopkih a, b in c zgoraj, tako da se tvori spojina s formulo I; e) pretvorbo spojine s formulo IV:
R 2 v kateri so R, R2 in R3 kot je definirano pod formulo I, z obdelavo z organokovinskim reagentom in nato hidrolizo, tako da se tvori spojina s formulo I, nakar v danem primeru dobljeno bazo prevedemo v fiziološko sprejemljivo kislinsko adicijsko sol ali dobljeno sol prevedemo v bazo ali v drugačno fiziološko sprejemljivo kislinsko adicijsko sol in, v danem primeru, dobljeno zmes izomerov ločimo v čisti izomer. Za AB ASTRA: 1 ,'V'BUANA, ČOPOVA n 2 5
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE8901889A SE8901889D0 (sv) | 1989-05-26 | 1989-05-26 | Novel 8-substituted-2-aminotetralines |
YU100690A YU48830B (sh) | 1989-05-26 | 1990-05-23 | Novi 8-supstituisani-2-aminotetralini |
Publications (2)
Publication Number | Publication Date |
---|---|
SI9011006A SI9011006A (en) | 1997-12-31 |
SI9011006B true SI9011006B (sl) | 1998-12-31 |
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ID=20376074
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SI9011006A SI9011006B (sl) | 1989-05-26 | 1990-05-23 | Novi 8-substituirani-2-aminotetralini |
Country Status (41)
Country | Link |
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US (1) | US5635537A (sl) |
EP (1) | EP0399982B1 (sl) |
JP (1) | JP2818692B2 (sl) |
KR (1) | KR100193981B1 (sl) |
CN (1) | CN1023399C (sl) |
AT (1) | ATE129696T1 (sl) |
AU (1) | AU644081B2 (sl) |
CA (1) | CA2032498C (sl) |
CY (1) | CY1989A (sl) |
CZ (1) | CZ286038B6 (sl) |
DD (1) | DD298909A5 (sl) |
DE (1) | DE69023274T2 (sl) |
DK (1) | DK0399982T3 (sl) |
DZ (1) | DZ1417A1 (sl) |
ES (1) | ES2078962T3 (sl) |
FI (1) | FI114151B (sl) |
GR (1) | GR3018566T3 (sl) |
HK (1) | HK55697A (sl) |
HR (1) | HRP920622B1 (sl) |
HU (2) | HUT58685A (sl) |
IE (1) | IE75057B1 (sl) |
IL (1) | IL94428A (sl) |
IS (1) | IS1663B (sl) |
JO (1) | JO1617B1 (sl) |
LT (1) | LT3966B (sl) |
LV (2) | LV10243B (sl) |
MX (1) | MX20842A (sl) |
NO (1) | NO176603C (sl) |
NZ (1) | NZ233724A (sl) |
PH (1) | PH31110A (sl) |
PL (2) | PL165166B1 (sl) |
PT (1) | PT94163B (sl) |
RU (1) | RU2093507C1 (sl) |
SA (1) | SA90100274B1 (sl) |
SE (1) | SE8901889D0 (sl) |
SI (1) | SI9011006B (sl) |
SK (1) | SK280731B6 (sl) |
UA (1) | UA40562C2 (sl) |
WO (1) | WO1990014330A1 (sl) |
YU (1) | YU48830B (sl) |
ZA (1) | ZA903801B (sl) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HUT61719A (en) * | 1989-05-31 | 1993-03-01 | Upjohn Co | Process for producing 2-aminotetraline derivatives and pharmaceutical compositions comprising such compounds |
CA2048846A1 (en) * | 1990-08-15 | 1992-02-16 | Craig Steven Hoechstetter | Ring-substituted 2-amino-1,2,3,4-tetrahydronaphthalenes, 3-aminochromanes, and aminothiochromanes |
US5643784A (en) * | 1990-12-04 | 1997-07-01 | H, Lundbeck A/S | Indan derivatives |
ES2102456T3 (es) * | 1991-02-08 | 1997-08-01 | Lilly Co Eli | 3-amino-1,2,3,4-tetrahidronaftalenos sustituidos en el anillo. |
US5244911A (en) * | 1991-03-28 | 1993-09-14 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz(cd)indoles and pharmaceutical use thereof |
US5244912A (en) * | 1991-03-28 | 1993-09-14 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz(cd)indoles and pharmaceutical use thereof |
US5665744A (en) * | 1991-03-28 | 1997-09-09 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2A,3,4,5-hexahydrobenzn [cd] indoles |
US5347013A (en) * | 1991-03-28 | 1994-09-13 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz[cd]indoles |
NZ243065A (en) * | 1991-06-13 | 1995-07-26 | Lundbeck & Co As H | Piperidine derivatives and pharmaceutical compositions |
SE9103745D0 (sv) * | 1991-12-18 | 1991-12-18 | Wikstroem Haakan | Aryl-triflates and related compounds |
DK78692D0 (da) * | 1992-06-12 | 1992-06-12 | Lundbeck & Co As H | Dimere piperidin- og piperazinderivater |
SE9301732D0 (sv) * | 1993-05-18 | 1993-05-18 | Haakan Wilhelm Wikstroem | New centrally acting 5-,6-,7-, and 8-substituted sulphone esters of n-monosubstituted 2-aminotetralins |
WO1996015099A1 (en) * | 1994-11-09 | 1996-05-23 | Novo Nordisk A/S | Heterocyclic compounds, their preparation and use |
GB9509156D0 (en) | 1995-05-05 | 1995-06-28 | Sandoz Ltd | Organic compounds |
WO2007081542A2 (en) * | 2006-01-06 | 2007-07-19 | Sepracor Inc. | Tetralone-based monoamine reuptake inhibitors |
BR112023017490A2 (pt) | 2021-03-17 | 2023-11-07 | Receptos Llc | Métodos de tratamento de dermatite atópica com anticorpos anti il-13 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
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DE2752659A1 (de) * | 1976-12-07 | 1978-06-08 | Sandoz Ag | Neue tetralinderivate, ihre herstellung und verwendung |
US4247907A (en) * | 1978-11-27 | 1981-01-27 | International Business Machines Corporation | Method and apparatus for typing characters and optically readable binary representations thereof on same page |
SE8004002L (sv) * | 1980-05-29 | 1981-11-30 | Arvidsson Folke Lars Erik | Terapeutiskt anvendbara tetralinderivat |
IL65501A (en) * | 1981-05-08 | 1986-04-29 | Astra Laekemedel Ab | 1-alkyl-2-aminotetralin derivatives,process for their preparation and pharmaceutical compositions containing them |
DE3479314D1 (en) * | 1984-05-22 | 1989-09-14 | Nelson Res & Dev | Substituted 2-aminotetralins and processes for synthesis |
ATE38029T1 (de) * | 1985-06-26 | 1988-11-15 | Smithkline Beckman Corp | Benz-trisubstituierte 2-aminotetraline. |
IL79323A (en) * | 1985-07-10 | 1990-03-19 | Sanofi Sa | Phenylethanolaminotetralines,their preparation and pharmaceutical compositions containing them |
DE3718317A1 (de) * | 1986-12-10 | 1988-06-16 | Bayer Ag | Substituierte basische 2-aminotetraline |
DE3719924A1 (de) * | 1986-12-22 | 1988-06-30 | Bayer Ag | 8-substituierte 2-aminotetraline |
CA2026775C (en) * | 1989-01-09 | 1998-04-07 | Per Arvid Emil Carlsson | Halo substituted aminotetralins |
HUT61719A (en) * | 1989-05-31 | 1993-03-01 | Upjohn Co | Process for producing 2-aminotetraline derivatives and pharmaceutical compositions comprising such compounds |
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1989
- 1989-05-26 SE SE8901889A patent/SE8901889D0/xx unknown
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1990
- 1990-05-17 IL IL9442890A patent/IL94428A/en not_active IP Right Cessation
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- 1990-05-23 DK DK90850209.9T patent/DK0399982T3/da active
- 1990-05-23 ES ES90850209T patent/ES2078962T3/es not_active Expired - Lifetime
- 1990-05-23 DZ DZ900088A patent/DZ1417A1/fr active
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- 1990-05-23 AT AT90850209T patent/ATE129696T1/de not_active IP Right Cessation
- 1990-05-23 AU AU58185/90A patent/AU644081B2/en not_active Expired
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- 1990-05-23 WO PCT/SE1990/000351 patent/WO1990014330A1/en active IP Right Grant
- 1990-05-23 KR KR1019910700092A patent/KR100193981B1/ko not_active IP Right Cessation
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- 1990-05-23 CA CA002032498A patent/CA2032498C/en not_active Expired - Lifetime
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- 1990-05-23 UA UA4894777A patent/UA40562C2/uk unknown
- 1990-05-23 SI SI9011006A patent/SI9011006B/sl unknown
- 1990-05-23 DE DE69023274T patent/DE69023274T2/de not_active Expired - Lifetime
- 1990-05-23 RU SU904894777A patent/RU2093507C1/ru active
- 1990-05-24 PL PL90285330A patent/PL165166B1/pl unknown
- 1990-05-24 PL PL90300984A patent/PL164245B1/pl unknown
- 1990-05-25 PT PT94163A patent/PT94163B/pt not_active IP Right Cessation
- 1990-05-25 SK SK2560-90A patent/SK280731B6/sk not_active IP Right Cessation
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- 1990-05-25 CZ CS902560A patent/CZ286038B6/cs not_active IP Right Cessation
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- 1990-05-26 JO JO19901617A patent/JO1617B1/en active
- 1990-05-26 CN CN90103956A patent/CN1023399C/zh not_active Expired - Lifetime
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1991
- 1991-01-25 NO NO910310A patent/NO176603C/no not_active IP Right Cessation
- 1991-01-25 FI FI910381A patent/FI114151B/fi active
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1992
- 1992-09-30 HR HRP-1006/90A patent/HRP920622B1/xx not_active IP Right Cessation
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1993
- 1993-03-18 US US08/033,013 patent/US5635537A/en not_active Expired - Lifetime
- 1993-06-30 LV LVP-93-869A patent/LV10243B/xx unknown
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1995
- 1995-06-30 HU HU95P/P00719P patent/HU211880A9/hu unknown
- 1995-12-29 GR GR950403703T patent/GR3018566T3/el unknown
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1996
- 1996-11-01 LV LVP-96-420A patent/LV11736B/en unknown
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1997
- 1997-05-01 HK HK55697A patent/HK55697A/xx not_active IP Right Cessation
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