Patents by Inventor Arto J. Karjalainen
Arto J. Karjalainen has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5559141Abstract: New 4(5)-imidazole derivatives of formula (Ia) and (Ib) wherein one of R.sub.1 and R.sub.2 is CN and the other one is H, CH.sub.3, OCH.sub.3, NO.sub.2, NH.sub.2, CN, CF.sub.3, CHF.sub.2, CH.sub.2 F or halogen; R' is H or (II) where R.sub.3 is H, CH.sub.3 or halogen; R.sub.4 is H and R.sub.5 is H or R.sub.4 and R.sub.5 together form a bond, n is 1 or 2 and y is 0 to 2, their stereoisomers and their non-toxic pharmaceutically acceptable acid addition salts exhibit selective aromatase inhibiting properties, compared with their desmolase inhibiting properties. The compounds of the invention are valuable in the treatment of estrogen dependent diseases, e.g. breast cancer or benign prostatic hyperplasia (BPH).Type: GrantFiled: May 9, 1994Date of Patent: September 24, 1996Assignee: Orion-yhtyma OyInventors: Arto J. Karjalainen, Marja-Liisa Sodervall, Arja M. Kalapudas, Reino O. Pelkonen, Aire M. Laine, Risto A. Lammintausta, Jarmo S. Salonen
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Patent number: 5498623Abstract: The invention provides compounds of the formula ##STR1## wherein Y is --CH.sub.2 -- or --CO--;R.sub.1 is F, Cl or OH; R.sub.2 is H, F or Cl; and R.sub.3 is H, CH.sub.3 or CH.sub.2 CH.sub.3, excluding 4-(5-chloro-2,3-dihydro-1H-inden-2-yl)-1H-imidazole and 4-(4-chloro-2,3-dihydro-1H-inden-2-yl)-1H-imidazole; and their non-toxic acid addition salts and mixtures thereof. Processes for the preparation of these compounds are described, as are pharmaceutical compositions comprising at least one of the compounds or its salt. The compounds and their non-toxic salts exhibit valuable pharmacological activity and are highly selective and long acting antagonists at .alpha..sub.2 -adrenoceptors. Their peroral bioavailability is good. The compounds are especially useful in the treatment of cognitive disorders.Type: GrantFiled: September 19, 1994Date of Patent: March 12, 1996Assignee: Orion-yhtyma OyInventors: Arto J. Karjalainen, Raimo E. Virtanen, Arja L. Karjalainen, Maire M. Eloranta, Jarmo S. Salonen, Hannu T. Sipila, Antti S. Haapalinna
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Patent number: 5491173Abstract: The invention provides novel compounds of the formula: ##STR1## wherein R.sub.1 and R.sub.2, which can be the same or different are H or OH, R.sub.3 is ##STR2## wherein R.sub.4 and R.sub.5, which can be the same or different are H or an alkyl group of 1 to 4 carbon atoms, and their non-toxic pharmaceutically acceptable salts and esters and mixtures thereof, which compounds include metabolites of toremifene and exhibit valuable pharmacological properties as oestrogenic, anti-oestrogenic, and progestanic agents.Type: GrantFiled: January 24, 1994Date of Patent: February 13, 1996Assignee: Orion-yhtyma OyInventors: Reijo J. Toivola, Arto J. Karjalainen, Kauko O. A. Kurkela, Marja-Liisa Soderwall, Lauri V. M. Kangas, Guillermo L. Blanco, Hannu K. Sundquist, Arja Kalapudas
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Patent number: 5439928Abstract: Novel 4(5)-imidazole derivatives of specified formula and their non-toxic salts possess selective aromatase inhibiting properties, which are valuable in the treatment of estrogen dependent diseases e.g. breast cancer.Type: GrantFiled: May 19, 1993Date of Patent: August 8, 1995Assignee: Orion-yhtyma OyInventors: Arto J. Karjalainen, Reino O. Pelkonen, Marja-Liisa Sodervall, Matti A. Lahde, Risto A. S. Lammintausta, Arja L. Karjalainen, Arja M. Kalapudas
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Patent number: 5292887Abstract: Compounds of the formula: ##STR1## wherein X is --CH.sub.2 -- or ##STR2## R.sub.1 is H, C.sub.1-5 -alkyl or benzyl, which can be substituted or unsubstitutedR.sub.2 is H, C.sub.1-4 -alkyl, OH or C.sub.1-3 -alkoxyR.sub.3 is H, CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3 or HalR.sub.4 is H, CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3 or Hal and Hal is halogen and non-toxic acid addition salts and mixtures thereof are highly selective antagonists at postsynaptic .alpha..sub.2 -adrenoceptors, and are especially useful in the treatment of diabetes.Type: GrantFiled: December 6, 1989Date of Patent: March 8, 1994Assignee: Farmos-yhtyma OyInventors: Arto J. Karjalainen, Raimo E. Virtanen, Arja L. Karjalainen
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Patent number: 5098923Abstract: Imidazole derivatives of the formula: ##STR1## wherein R.sub.1, R.sub.2, R'.sub.1 and R'.sub.2 which can be the same or different, are H, CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OH, CH.sub.2 OH, NH.sub.2 or halogen; R' if H or ##STR2## where R.sub.3 is H, CH.sub.3, or halogen; R.sub.4 is H and R.sub.5 is H or OH and R.sub.6 is H or OH or one of R.sub.5 and R.sub.6 is H and the other, together with R.sub.4, forms a bond and X and Y, which can be the same or different, are a bond, a straight C.sub.1-2 -alkyl or the corresponding alkenyl, and pharmaceutically acceptable salts thereof exhibit valuable pharmacological properties, especially aromatase inhibiting effects and are useful in the treatment of estrogen dependent diseases, e.g. breast cancer. Anti-mycotic and antifungal properties have also been found.Type: GrantFiled: September 27, 1990Date of Patent: March 24, 1992Assignee: Farmos-Yhtyma OyInventors: Arto J. Karjalainen, Lauri V. M. Kangas, Kauko O. A. Kurkela, Reino O. Pelkonen
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Patent number: 5026868Abstract: The invention provides 4(5)-substituted imidazole derivatives of formula ##STR1## and their acid addition salts, in which either X is --CH.sub.2 -- and R.sub.1 is --CN, --COOH, COO(lower alkyl), --CHO, --CO(lower alkyl), lower alkyl of 3 or 4 carbon atoms, lower alkenyl, or lower (hydroxy alkyl) or X is ##STR2## --C(:CH--R)-- or --CH(CH.sub.2 R)--, where R is hydrogen or lower alkyl, and R.sub.1 is lower alkyl, and R.sub.3 and R.sub.4 are each hydrogen, methyl, ethyl, methoxy, or halogen, and novel intermediates and processes for their preparation. These compounds, in particular when R.sub.1 is lower alkyl, lower alkenyl, or lower (hydroxy alkyl), possess valuable pharmacological properties and are useful especially as selective .alpha..sub.2 -receptor antagonists.Type: GrantFiled: November 6, 1989Date of Patent: June 25, 1991Assignee: Farmos-Yhtyma OyInventors: Arja L. Karjalainen, Arto J. Karjalainen
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Patent number: 4996225Type: GrantFiled: October 12, 1989Date of Patent: February 26, 1991Assignee: Farmos Group Ltd.Inventors: Reijo J. Toivola, Arto J. Karjalainen, Kauko O. A. Kurkela, Marja-Liisa Soderwall, Lauri V. M. Kangas, Guillermo L. Blanco, Hannu K. Sundquist
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Patent number: 4933359Abstract: The invention provides 4(5)-substituted imidazole derivatives of formula ##STR1## and their acid addition salts, in which either X is --CH.sub.2 -- and R.sub.1 is --CN, --COOH, COO(lower alkyl), --CHO, --CO(lower alkyl), lower alkyl or 3 or 5 carbon atoms, lower alkenyl, or lower (hydroxy alkyl) or X is ##STR2## --C(:CH--R)-- or --CH(CH.sub.2 R)--, where R is hydrogen or lower alkyl, and R.sub.1 is lower alkyl, and R.sub.3 and R.sub.4 are each hydrogen, methyl, ethyl, methoxy, or halogen, and novel intermediates and processes for their preparation. These compounds, in particular when R.sub.1 is lower alkyl, lower alkenyl, or lower (hydroxy alkyl), possess valuable pharmacological properties and are useful especially as selective .alpha..sub.2 -receptor antagonists.Type: GrantFiled: May 14, 1987Date of Patent: June 12, 1990Assignee: Farmos-Yhtyma OyInventors: Arja L. Karjalainen, Arto J. Karjalainen
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Patent number: 4910214Abstract: The separated d and l enantiomers of medetomidine and their salts are selective and potent .alpha..sub.2 -receptor agonists.Type: GrantFiled: July 15, 1988Date of Patent: March 20, 1990Assignee: Farmos Yhtyma OyInventors: Arto J. Karjalainen, Raimo E. Virtanen, Eino J. Savolainen
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Patent number: 4826864Abstract: Substituted imidazoles of the formula ##STR1## wherein R.sub.1 is H, an alkyl of 1 to 4 carbon atoms or --CH.sub.2 OH; R.sub.2 is H or CH.sub.3 ; R.sub.3 is ##STR2## and R.sub.4 is H; R.sub.5, R.sub.6 and R.sub.7 which can be the same or different, are H, --CH.sub.3 , --CH.sub.2 CH.sub.3, halogen, OH or --OCH.sub.3, or R.sub.5 is hydrogen and R.sub.6 and R.sub.7 together form an --O--CH.sub.2 --O--bridge between two adjacent carbon atoms in the phenyl group; provided thatwhen R.sub.1, R.sub.2 and R.sub.4 are all hydrogen, then R.sub.5, R.sub.6, R.sub.7 are not all simultaneously hydrogen;or non-toxic pharmaceutically acceptable acid addition salts thereof. The substituted imidazoles are useful as anti-hypertensives or anti-thrombotic agents or diuretics.Type: GrantFiled: January 11, 1988Date of Patent: May 2, 1989Assignee: Farmos Group Ltd.Inventors: Arto J. Karjalainen, Kauko O. A. Kurkela
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Patent number: 4696949Abstract: The invention provides novel compounds of the formula: ##STR1## wherein n is 0 to 4, R.sub.1 and R.sub.2, which can be the same or different are H, OH, alkoxy of 1 to 4 carbon atoms, benzyloxy or methoxymethoxy; R.sub.3 is H, OH, halogen, alkoxy of 1 to 4 carbon atoms, benzyloxy, methoxymethoxy, 2,3-dihydroxypropoxy or ##STR2## wherein m is 1 or 2, R.sub.6 and R.sub.7, which can be the same or different are H or an alkyl group of 1 to 4 carbon atoms, or ##STR3## can form an N-containing three-, four-, five- or six-membered heterocyclic ring; R.sub.4 is OH, F, Cl, Br, I, mesyloxy, tosyloxy, alkylcarbonyloxy of 1 to 4 C-atoms, formyloxy or CH.sub.2 R.sub.4 is replaced by CHO; R.sub.5 is H or OH; or R.sub.4 and R.sub.5 together form an --O-- bridge between the carbon atoms to which they are attached, and their non-toxic pharmaceutically acceptable salts and esters and mixtures thereof. Processes for the preparation of these compounds are described, and also novel pharmaceutical compositions containing them.Type: GrantFiled: January 29, 1986Date of Patent: September 29, 1987Assignee: Farmos Group Ltd.Inventors: Reijo J. Toivola, Arto J. Karjalainen, Kauko O. A. Kurkela, Marja-Liisa Soderwall, Lauri V. M. Kangas, Guillermo L. Blanco, Hannu K. Sunduiqst
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Patent number: 4689339Abstract: A process for the preparation of a substituted imidazole of the formula ##STR1## wherein X is --CH.sub.2 --, --CH.sub.2 CH.sub.2 -- or --O-- R.sub.1 is H, lower alkyl or lower alkenyl, OCH.sub.3 or OCH.sub.2 CH.sub.3, R.sub.2 is H, CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3 or OH, R.sub.3 is H, CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3 or Hal, R.sub.4 is H, CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3 or Hal, and Hal is halogen and their non-toxic acid addition salts exhibit valuable pharmacological activity and are useful especially as selective .alpha..sub.2 -receptor antagonists.Type: GrantFiled: November 21, 1985Date of Patent: August 25, 1987Assignee: Farmos Yhtyma oyInventors: Arto J. Karjalainen, Raimo E. Virtanen, Arja L. Karjalainen, Kauko O. A. Kurkela
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Patent number: 4684659Abstract: The invention provides compounds of the formula: ##STR1## wherein each of R.sub.1, R.sub.2 and R.sub.3, which can be the same or different, is hydrogen, chloro, bromo, fluoro, methyl, ethyl, methoxy, amino, hydroxy or nitro; R.sub.4 is hydrogen or alkyl of 1 to 7 carbon atoms; X is ##STR2## (R.sub.5 is hydrogen or hydroxy) and n is 1-4; and their non-toxic pharmaceutically acceptable acid addition salts. These compounds exhibit valuable pharmacological activity and are useful in the treatment of mammals, especially as anti-hypertensive agents. Furthermore, some of the compounds have proved to possess diuretic, .beta.-blocking activity and/or antithrombotic activity. The compounds may be made by a variety of methods and may be incorporated in pharmaceutical compositions also comprising a compatible pharmaceutically acceptable carrier.Type: GrantFiled: January 28, 1986Date of Patent: August 4, 1987Assignee: Farmos-Yhtyma OyInventors: Arto J. Karjalainen, Kauko O. A. Kurkela
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Patent number: 4670455Abstract: 4-[(.alpha.-Methyl)-2,3-dimethyl-benzyl]imidazole is useful as a veterinary sedative-analgetic agent, especially in small mammals.Type: GrantFiled: December 3, 1985Date of Patent: June 2, 1987Assignee: Farmos-Yhtyma OyInventors: Raimo E. Virtanen, Arto J. Karjalainen, Kauko O. A. Kurkela, Antti T. Vaha-Vahe, Outi M. Vainio-Kivinen
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Patent number: 4639464Abstract: The invention provides novel compounds of the formula: ##STR1## wherein R.sub.1 is H, an alkyl of 1 to 4 carbon atoms or --CH.sub.2 OH; R.sub.2 is H or CH.sub.3 ; R.sub.3 is --CH.sub.3, --CH.sub.2 CH.sub.3, --CH.sub.2 CH.sub.2 CH.sub.3, ##STR2## --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3, --CH.sub.2 CH.dbd.CH.sub.2, or ##STR3## and R.sub.4 is H or OH; or R.sub.3 and R.sub.4 together represent .dbd.CH.sub.2, .dbd.CH--CH.sub.3, .dbd.CH--CH.sub.2 --CH.sub.3, ##STR4## or .dbd.CH--CH.sub.2 CH.sub.2 CH.sub.3 ; X is ##STR5## R.sub.5, R.sub.6 and R.sub.7, which can be the same or different are H, --CH.sub.3, --CH.sub.2 CH.sub.3, halogen, OH or --OCH.sub.3 or R.sub.5 is hydrogen and R.sub.6 and R.sub.7 together form an --O--CH.sub.2 --O--bridge between two adjacent carbon atoms in the phenyl group; --CHR.sub.8 -- is --CH.sub.2 --, --CH(CH.sub.3)--, --CH(--CH.sub.2 CH.sub.3)--, --CH(--CH.sub.2 CH.sub.2 CH.sub.3)--, ##STR6## --CH(--CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3)-- or >C.dbd.CH.sub.2, >C.dbd.CH--CH.sub.3, >C.Type: GrantFiled: March 19, 1985Date of Patent: January 27, 1987Assignee: Farmos Group, Ltd.Inventors: Arto J. Karjalainen, Kauko O. A. Kurkela
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Patent number: 4568686Abstract: The invention provides compounds of the formula: ##STR1## wherein each of R.sub.1, R.sub.2 and R.sub.3, which can be the same or different, is hydrogen, chloro, bromo, fluoro, methyl, ethyl, methoxy, amino, hydroxy or nitro; R.sub.4 is hydrogen or alkyl of 1 to 7 carbons atoms; X is ##STR2## (R.sub.5 is hydrogen or hydroxy) and n is 1-4; and their non-toxic pharmaceutically acceptable acid additions salts. These compounds exhibit valuable pharmacological activity and are useful in the treatment of mammals, especially as anti-hypertensive agents. Furthermore, some of the compounds have proved to possess diuretic, .beta.-blocking activity and/or antithrombotic activity. The compounds may be made by a variety of methods and may be incorporated in pharmaceutical compositions also comprising a compatible pharmaceutically acceptable carrier.Type: GrantFiled: February 11, 1981Date of Patent: February 4, 1986Assignee: Farmos Yhtyma OyInventors: Arto J. Karjalainen, Kauko O. A. Kurkela
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Patent number: 4556677Abstract: The invention provides novel compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, hydroxy, alkoxy of 1 to 4 carbon atoms, benzyloxy, allyloxy, 2,3-epoxypropoxy, methoxymethoxy, ethoxymethoxy, or 2,3-dihydroxypropoxy or ##STR2## wherein one of R.sub.5 and R.sub.6 is hydrogen or R.sub.5 and R.sub.6 are alkyl groups of 1-4 carbon atoms which may be the same or different, or the --NR.sub.5 R.sub.6 group stands for a nitrogen containing 5 to 7 membered heterocyclic radical and m is 1 or 2; R.sub.2 is an alkyl of 1 to 4 carbon atoms or ##STR3## wherein R.sub.7 has the same meanings as R.sub.1 except that R.sub.7 and R.sub.1 cannot simultaneously be the same; R.sub.3 is an alkyl of 2 to 4 carbon atoms, cyclopentyl or hydroxy-cyclopentyl; R.sub.4 is hydrogen or hydroxy; and n is 0 to 3, provided that when R.sub.4 is hydrogen, then R.sub.2 and R.sub.Type: GrantFiled: October 26, 1982Date of Patent: December 3, 1985Assignee: Farmos Group Ltd.Inventors: Marja-Liisa Sodervall, Kauko O. A. Kurkela, Arto J. Karjalainen, Reijo J. Toivola, Lauri V. M. Kangas, Guillermo L. Blanco
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Patent number: 4544664Abstract: The invention provides novel compounds of the formula: ##STR1## wherein the various substituents are defined herein below. Processes for the preparation of these compounds are described, as are novel pharmaceutical compositions comprising at least one of the compounds of their salts. The compounds and their non-toxic salts exhibit valuable pharmacological activity and are useful in the treatment of mammals, especially as antihypertensive agents. Furthermore, some of the compounds have proved to possess antithrombotic and diuretic activity. Antimycotic and antifungal properties have also been found.Type: GrantFiled: July 7, 1982Date of Patent: October 1, 1985Assignee: Farmos Group, Ltd.Inventors: Arto J. Karjalainen, Kauko O. A. Kurkela
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Patent number: RE32400Abstract: Compounds of the formula: ##STR1## wherein each of R.sub.1, R.sub.2 and R.sub.3, which can be the same or different, is hydrogen, chloro, bromo, fluoro, methyl, ethyl, methoxy, amino, hydroxy or nitro; R.sub.4 is hydrogen or alkyl or 1 to 7 carbon atoms; R.sub.5 is hydrogen or a straight or branched alkyl group of 1 to 5 carbon atoms or a phenyl group; and R.sub.6 is hydrogen or an alkyl group of 1 to 7 carbon atoms or a substituted or unsubstituted benzyl, X is --CH.sub.2 --, --CHOH-- or --CH.dbd.CH-- and n is 0-4; provided that R.sub.5 and R.sub.6 are simultaneously hydrogen only when n is 4 and X is --CH.dbd.CH--; and their non-toxic pharmaceutically acceptable acid addition salts and mixtures thereof exhibit valuable pharmacological activity and are useful in the treatment of mammals, especially as antithrombotic agents. Furthermore, some of the compounds have proved to possess antihypertensive or .beta.-blocking activity. Antimicrobial and antifungal properties have also been found.Type: GrantFiled: July 30, 1985Date of Patent: April 14, 1987Assignee: Farmos Yhtyma OyInventors: Arto J. Karjalainen, Kauko O. A. Kurkela