Acyclic Patents (Class 564/240)
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Patent number: 5723133Abstract: A guanidine derivative represented by formula (1), (2), (3) or its acid addition salt and a production process thereof ##STR1## wherein each of A and B is a C.sub.2 -C.sub.8 alkylene, D is a single bond, --CO-- or a C.sub.1 -C.sub.5 alkylene, E is H, a lower alkyl or the like, m is 1 to 6, n is 0 to 6 and R.sup.1 is H, a lower alkyl or the like, l is 1 to 10 and G is H, --OH or the like and a skin cosmetic containing the same. It can exert excellent keratin layer softening effect continuously for a long period of time.Type: GrantFiled: July 26, 1995Date of Patent: March 3, 1998Assignee: Kao CorporationInventors: Minoru Nagai, Hiromitsu Kawada, Mayumi Tsuchiya, Seiji Yamasaki, Akira Yamamuro, Toshiya Ono
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Patent number: 5719187Abstract: Guanidine derivatives are provided useful for promoting growth, repair and regeneration of a neuronal axon and for treating neuropathies and myopathies. The compounds have the formula: ##STR1## wherein R.sub.1 is an isopropyl radical, a benzyl radical which is optionally substituted by one or more (C.sub.1 -C.sub.6)alkoxy radicals or a radical: ##STR2## R.sub.2, R.sub.3 and R.sub.Type: GrantFiled: June 7, 1995Date of Patent: February 17, 1998Assignee: Centre National De La Recherche Scientifique(CNRS)Inventors: Claude Thal, Catherine Quirosa-Guillou, Pierre Potier, Dolor Renko, Jean-Pierre Zanetta, Marie-Madeleine Portier, Monique Sensenbrenner, Janine Koenig, Herbert Koenig
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Patent number: 5696290Abstract: The present invention is the novel synthesis of sterically hindered penta-substituted guanidines by a process in which (1a) an isocyanate is reacted first with a di-substituted amine or (1b) a urea is reacted with two moles of a mono-substituted amine to form a tri-substituted urea followed by (2) treatment of the tri-substituted urea with an activating agent before reacting with a second di-substituted amine in the presence of a base.Type: GrantFiled: September 12, 1994Date of Patent: December 9, 1997Assignee: Monsanto CompanyInventors: Kenneth W. Ruettimann, William D. McGhee, A. John Solodar
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Patent number: 5637622Abstract: Tri- and tetra-substituted guanidines which exhibit a high binding affinity to phencyclidine (PCP) receptors and, more preferably, low affinity to the brain sigma receptors. These guanidine derivatives act as non-competitive inhibitors of glutamate induced responses of the NMDA receptor by acting as blockers for the ion channel of the NMDA receptor-ion channel complex. These compounds thus exert neuroprotective activity and are useful in the therapeutic treatment of neuronal loss in hypoxia, hypoglycemia, brain or spinal cord ischemia, and brain or spinal chord trauma as well as being useful for the treatment of epilepsy, Alzheimer's disease, Amyotrophic Lateral Sclerosis, Parkinson's disease, Huntington's disease, Down's Syndrome, Korsakoff's disease and other neurodegenerative disorders.Type: GrantFiled: May 22, 1995Date of Patent: June 10, 1997Assignee: State of Oregon, acting by and through the Oregon State Board of Higher Education, acting for and on behalf of the Oregon Health Sciences University and the University of OregonInventors: Eckard Weber, John F. W. Keana
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Patent number: 5612332Abstract: The present invention relates to compounds, compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises a di- or tri-aminoguanidine capable of inhibiting the formation of advanced glycosylation endproducts of target proteins. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.Type: GrantFiled: June 7, 1995Date of Patent: March 18, 1997Assignees: Alteon Inc., The Rockefeller UniversityInventors: Dilip R. Wagle, Peter C. Ulrich, Anthony Cerami
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Patent number: 5559154Abstract: Tri- and tetra-substituted guanidines which exhibit a high binding affinity to phencyclidine (PCP) receptors and, more preferably, low affinity to the brain sigma receptors. These guanidine derivatives act as non-competitive inhibitors of glutamate induced responses of the NMDA receptor by acting as blockers for the ion channel of the NMDA receptor-ion channel complex. These compounds thus exert neuroprotective activity and are useful in the therapeutic treatment of neuronal loss in hypoxia, hypoglycemia, brain or spinal cord ischemia, and brain or spinal chord trauma as well as being useful for the treatment of epilepsy, Alzheimer's disease, Amyotrophic Lateral Sclerosis, Parkinson's disease, Huntington's disease, Down's Syndrome, Korsakoff's disease and other neurodegenerative disorders.Type: GrantFiled: August 11, 1993Date of Patent: September 24, 1996Assignees: Oregon State Board of Higher Education, Oregon Health Sciences University, University of OregonInventors: Eckard Weber, John F. W. Keana
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Patent number: 5556857Abstract: The present invention provides a disturbance-of-consciousness improving agent which is a highly effective and quick remedy and which can be administered orally. The disturbance-of-consciousness improving agent of the invention contains a sigma receptor agonist compound as an active ingredient.Type: GrantFiled: July 16, 1993Date of Patent: September 17, 1996Assignee: Otsuka Pharmaceutical Co., Ltd.Inventors: Yasuo Oshiro, Tatsuyoshi Tanaka, Tetsuro Kikuchi, Katsura Tottori
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Patent number: 5532413Abstract: An antimicrobial composition comprising the formula ##STR1## wherein R is an alkyl group having a distribution of carbon atoms from about eight to eighteen carbon atoms and wherein from about 40 to 60 weight % of the alkyl group having about twelve carbon atoms and wherein X is hydrogen or a halide is disclosed. The antimicrobial composition is storage stable below about 5.degree. C. and, further, preferably, also has a flash point above about 38.degree. C. A process for making this antimicrobial composition is disclosed resulting in an antimicrobial composition comprising from about 25 to 35 weight % of the alkyl guanidine halide salt of the above formula, from about 10 to 60 weight % of a solvent and from about 10 to 65 weight % water.Type: GrantFiled: January 6, 1995Date of Patent: July 2, 1996Assignee: Calgon CorporationInventors: Gary F. Matz, Paul F. Richardson
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Patent number: 5466878Abstract: A cosmetic composition for the first stage of a permanent deformation of the hair contains, in a cosmetically acceptable vehicle, as a reducing agent, an amino mercaptoalkylamide having the formula ##STR1## wherein A represents the divalent radical, --(CH.sub.2).sub.n -- wherein n is a whole number ranging from 2 to 5, or the divalent radical --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --, m is 0 or a whole number ranging from 1 to 4, and (i) when m is 0, R.sub.1 represents hydrogen, methyl, ethyl, isopropyl, isobutyl, 2-methyl butyl, benzyl, 4-amino butyl, 3-guanidino propyl, 2-methylthio ethyl, carboxymethyl or 2-carboxyethyl, and (ii) when m is a whole number from 1 to 4, R.sub.1 represents hydrogen or lower alkyl having 1-5 carbon atoms, and the salts of the compound of formula I.Type: GrantFiled: October 18, 1991Date of Patent: November 14, 1995Assignee: L'OrealInventors: Alex Junino, Gerard Malle
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Patent number: 5416238Abstract: Novel N.sup.G -protected or unprotected-L-argininal-dibutyl acetals (I) can be prepared from L-argininal derivatives (III) merely by reacting in an azeotropic solvent in the presence of p-toluenesulfonic acid. In the products (I), L-form amounts to more than 99%, without further optical resolution. The L-argininal acetals (I) are useful as starting materials for preparing peptidyl-L-argininal derivatives which can provide protease inhibitors or ligands used for affinity chromatography of various proteases.Type: GrantFiled: September 5, 1991Date of Patent: May 16, 1995Assignee: Nitto Boseki Co., Ltd.Inventors: Yoshihito Abe, Akio Hashimoto, Takeshi Nagasawa, Katsumasa Kuroiwa
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Patent number: 5403948Abstract: A compound of the formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom, or a halogen atom, a (C.sub.1 to C.sub.3)-alkyl group, a halo-(C.sub.1 to C.sub.3)-alkyl group, a (C.sub.1 to C.sub.6)-alkoxy group, a (C.sub.2 to C.sub.6)-alkynyloxy group, a (C.sub.2 to C.sub.6)-alkenyloxy group, a halo-(C.sub.2 to C.sub.6)-alkynyloxy group, a halo-(C.sub.2 to C.sub.6)-alkenyloxy group, a (C.sub.1 to C.sub.2)-alkylthio group, a halo-(C.sub.1 to C.sub.6)-alkoxy group, a halo-(C.sub.1 to C.sub.2)-alkylthio group, a phenoxy group, a (C.sub.1 to C.sub.3)-alkylcarboxy group, a halo-(C.sub.1 to C.sub.3)-alkylcarboxy group, a (C.sub.1 to C.sub.2)-alkoxy-(C.sub.1 to C.sub.2)-alkoxy group, a halo-(C.sub.1 to C.sub.2)-alkoxy-halo-(C.sub.2 to C.sub.3)-alkoxy group, a (C.sub.1 to C.sub.3)-alkylsulfonyloxy group, a halo-(C.sub.1 to C.sub.3)-alkylsulfonyloxy group, a cyano group, a (C.sub.1 to C.sub.3)-alkoxycarbonyl group or an aminomethyl group, at the ortho or meta position; R.sup.2 and R.sup.Type: GrantFiled: July 22, 1994Date of Patent: April 4, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Junichi Sato, Yuzuru Sanemitsu, Shinichi Kawamura
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Patent number: 5382668Abstract: This invention relates to intermediates and processes thereto, for the preparation of 5,6-dihydropyrro[2,3-d]pyrimidines which are useful for the treatment of susceptible neoplasms.Type: GrantFiled: November 23, 1993Date of Patent: January 17, 1995Assignee: Eli Lilly and CompanyInventors: Charles J. Barnett, Thomas M. Wilson
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Patent number: 5344846Abstract: Compositions and methods for the treatment of mammalian cells to inhibit cell growth, especially for inhibiting the proliferative cell growth associated with malignant and non-malignant disease, are provided. More particularly, a deoxyhypusine synthase inhibitor, typically, a mono- or bisguanyl diamine or polyamine, is administered to the cells.Also provided by this invention are diagnostic methods and kits for screening the cells of a patient to determine the effect of the deoxyhypusine synthase inhibitor on proliferation of the cells.Type: GrantFiled: December 30, 1992Date of Patent: September 6, 1994Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Judit Jakus, Myung H. Park, Edith C. Wolff, John E. Folk
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Patent number: 5336689Abstract: Tri- and tetra-substituted guanidines which exhibit a high binding affinity to phencyclidine (PCP) receptors and, more preferably, low affinity to the brain sigma receptors. These guanidine derivatives act as non-competitive inhibitors of glutamate induced responses of the NMDA receptor by acting as blockers for the ion channel of the NMDA receptor-ion channel complex. These compounds thus exert neuroprotective activity and are useful in the therapeutic treatment of neuronal loss in hypoxia, hypoglycemia, brain or spinal cord ischemia, and brain or spinal chord trauma as well as being useful for the treatment of epilepsy, Alzheimer's disease, Amyotrophic Lateral Sclerosis, Parkinson's disease, Huntington's disease, Down's Syndrome, Korsakoff's disease and other neurodegenerative disorders.Type: GrantFiled: August 11, 1993Date of Patent: August 9, 1994Assignee: State of Oregon, acting by and through the Oregon State Board of Higher Education, acting for and on behalf of the Oregon Health Sciences University and the University of OregonInventors: Eckard Weber, John F. W. Keana
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Patent number: 5262568Abstract: Tri- and tetra-substituted guanidines which exhibit a high binding affinity to phencyclidine (PCP) receptors and, more preferably, low affinity to the brain sigma receptors. These guanidine derivatives act as non-competitive inhibitors of glutamate induced responses of the NMDA receptor by acting as blockers for the ion channel of the NMDA receptor-ion channel complex. These compounds thus exert neuroprotective activity and are useful in the therapeutic treatment of neuronal loss in hypoxia, hypoglycemia, brain or spinal cord ischemia, and brain or spinal chord trauma as well as being useful for the treatment of epilepsy, Alzheimer's disease, Amyotrophic Lateral Sclerosis, Parkinson's disease, Huntington's disease, Down's Syndrome, Korsakoff's disease and other neurodegenerative disorders.Type: GrantFiled: March 4, 1991Date of Patent: November 16, 1993Assignee: State of OregonInventors: Eckard Weber, John F. W. Keana
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Patent number: 5242947Abstract: Methods for regulating cation transport across cellular membranes possessing cation channels are provided. The cell membrane possessing a specific ion channel is exposed to a non-aromatic polyamine compound having a lysine- or arginine-based moiety (or a guanidine moiety) coupled to a straight chain polyamine.These polyamines as well as a method for regulating NMDA through a spermidine-like effect on NMDA receptors by exposing a cell membrane to selected polyamines are also provided.Type: GrantFiled: January 3, 1992Date of Patent: September 7, 1993Assignee: New York UniversityInventors: Bruce D. Cherksey, Rodolfo R. Llinas, Mutsuyuki Sugimori
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Patent number: 5196450Abstract: This invention relates to the use of .alpha.- halomethyl, .alpha.-acetylenic or .alpha.-allenic derivatives of arginine and agmatine, or their dehydro analogs, in the treatment of Chagas disease and Coccidiosis.Type: GrantFiled: September 30, 1991Date of Patent: March 23, 1993Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Albert Sjoerdsma, Peter P. McCann, Philippe Bey, Patrick J. Casara
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Patent number: 5196595Abstract: New perfluoroaminoether polymers and a process for preparing them which comprises copolymerizing fluorinated olefins with oxaziridines in the presence of ultra-violet radiations or of chemical initiators.Type: GrantFiled: April 28, 1992Date of Patent: March 23, 1993Assignee: Ausimont S.R.L.Inventors: Walter Navarrini, Darryl D. Desmarteau
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Patent number: 5082968Abstract: A method of preparing a hexaalkylguanidinium salt comprising contacting tetraalkylguanidine with an alkylating agent in the presence of at least one alkaline reagent, and optionally, a promoting amount of a phase transfer catalyst.Type: GrantFiled: November 1, 1990Date of Patent: January 21, 1992Assignee: General Electric CompanyInventor: Daniel J. Brunelle
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Patent number: 5059624Abstract: Guanidine derivatives of the following formulas (1) and (2): ##STR1## wherein: R.sup.1 is hydrogen or optionally substituted cinnamoyl,R.sup.2 is hydrogen, alkyl or alkenyl, with the proviso that R.sup.1 and R.sup.2 cannot be both hydrogen,n is an integer from 1 to 8, or: ##STR2## wherein R.sup.3 is truxinoyl or a truxilloyl each optionally substituted, andR.sup.2 and n are as defined above;pharmaceutical compositions containing such compounds and a process for their extraction and purification from plant material, in particular from Verbesina caracasana.Type: GrantFiled: February 24, 1989Date of Patent: October 22, 1991Assignee: Consiglio Nazionale Delle RicercheInventors: Giuliano D. Monache, Franco D. Monache, Marco Carmignani, Stella C. Bonnevaux, Romulo Espinal, Carlo De Luca, Bruno Botta
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Patent number: 4970307Abstract: A process for formation of a base from a base precursor, which comprises decomposing the base precursor in the presence of a catalyst. The base precursor has the following formula (I) or (II):(R.sup.1 --C.tbd.C--CO.sub.2 H).sub.x .multidot.B (I)R.sup.2 (--C.tbd.C--CO.sub.2 H).sub.2 .multidot.B.sub.y (II)wherein R.sup.1 is a monovalent group selected from the group consisting of hydrogen, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, an aralkyl group, an acyl group, an alkoxycarbonyl group, carbamoyl, --CO.sub.2 M (M is an alkali metal) and --CO.sub.2 H.B, each of which may have one or more substituent groups; R.sup.Type: GrantFiled: August 13, 1987Date of Patent: November 13, 1990Assignee: Fuji Photo Film Co., Ltd.Inventors: Keiji Takeda, Jiro Tsukahara, Kozo Sato
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Patent number: 4886912Abstract: The present invention provides a cyanoguanidine derivative which is a precursor for the synthesis of N-cyano-N'-methyl-N"-[2-{(5-methyl-1H-imidazol-4-yl)methylthio}ethyl]-guan idine (Cimetidine) or its related compound, which has an action of controlling secretion of acid in the stomach based on the histamine H.sub.2 receptor antagonism and is valuable as a drug for treating gastric ulcer. This cyanoguanidine derivative is prepared by reacting other cyanoguanidine derivative with a halogenating agent.Type: GrantFiled: February 17, 1988Date of Patent: December 12, 1989Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Hiroaki Tan, Keiichi Yokoyama, Noriaki Kihara
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Patent number: 4749792Abstract: Analgesic activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein R.sub.1, R.sub.2 and R.sub.4 are each independently hydrogen, alkyl, carboxyalkyl, halosubstituted alkyl, hydroxyalkyl, aminoalkyl, mercaptoalkyl, alkylthioalkyl, (cycloalkyl)alkyl, (heteroaryl)alkyl, arylalkyl, carbamoylalkyl, guanidinylalkyl, or heteroaryl, and R.sub.3 is hydroxymethylene or carbonyl.Type: GrantFiled: September 26, 1984Date of Patent: June 7, 1988Assignee: E. R. Squibb & Sons, Inc.Inventors: Sesha I. Natarajan, Eric M. Gordon
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Patent number: 4628061Abstract: Novel compounds have a formula (I) ##STR1## wherein ##STR2## represents a bicyclo [2,2,1] hept-2Z-ene, bicyclo [2,2,1] heptane, 7-oxa-bicyclo [2,2,1] hept-2Z-ene, 7-oxa-bicyclo [2,2,1] heptane, bicyclo [2,2,2] oct-2Z-ene or bicyclo [2,2,2] octane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group ANR.sup.2 R, a 6,6-dimethyl-bicyclo [3,1,1] heptane substituted at the 2-position by the group R.sup.1 and at the 3-position by the group ANR.sup.2 R or at the 2-position by the group ANR.sup.2 R and at the 3-position by the group R.sup.1, a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R.sup.1 and at the 5-position by the group ANR.sup.2 R or a 1-hydroxycyclopentane substituted at the 2-position by the group R.sup.1 and at the 2-position by the group ANR.sup.2 R, R.sup.Type: GrantFiled: August 23, 1983Date of Patent: December 9, 1986Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 4471137Abstract: Compounds of the formula ##STR1## in which R.sub.1, R.sub.1 ', R.sub.2, R.sub.2 ' and R.sub.3 independently represent a C.sub.1-6 alkyl radical, in addition to which R.sub.3 may represent a hydrogen atom, the alkyl radicals together containing in all at least 8 carbon atoms, are provided for use as highly sterically hindered bases in chemical syntheses.Type: GrantFiled: July 14, 1982Date of Patent: September 11, 1984Assignee: Centre National de la Recherche Scientifique (CNRS)Inventors: Derek H. R. Barton, John D. Elliott, Stephan D. Gero
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Patent number: 4358613Abstract: Guanidines are one of the strongest organic bases and find applications where this property is needed, such as in phase transfer catalysis in the form of their substituted derivatives. Their use, however, has been hampered by their expensive nature due to the only mediocre yields in their preparation. The present invention provides a process for the preparation of substituted guanidines in high yields.Type: GrantFiled: March 16, 1981Date of Patent: November 9, 1982Assignee: General Electric CompanyInventor: Victor Mark
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Patent number: 4339459Abstract: Guanidiunium salts of the formula 1 ##STR1## in which R.sub.1 and R.sub.2 are identical or different and denote alkyl, 2-hydroxyalkyl or alkenyl each having from 8 to 18 carbon atoms, or C.sub.8 -C.sub.18 alkoxypropyl, m and n are 2 or 3, a is a number from 1 to 4 and A denotes an anion, process for their manufacture and their use as microbiocidal agents.Type: GrantFiled: December 15, 1980Date of Patent: July 13, 1982Assignee: Hoechst AktiengesellschaftInventors: Helmut Diery, Wolfgang Wagemann, Hans-Walter Bucking, Martin Hille, Karl H. Wallhausser
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Patent number: 4333929Abstract: A compound of formula (II) or a pharmaceutically acceptable acid addition salt thereof ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and each represents C.sub.1-6 alkyl; R.sup.5 represents hydrogen or C.sub.1-6 alkyl; R.sup.6 represents C.sub.1-6 alkyl, phenyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl, and C.sub.1-6 alkoxy; or benzyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.1-6 alkoxy; or R.sup.5 and R.sup.6 together represent the remaining members of a 5- or 6-membered ring optionally containing an oxygen, sulphur or additional nitrogen atom and being optionally substituted with C.sub.1-6 alkyl, carboxy or C.sub.1-6 alkoxycarbonyl; and R.sup.7 represents C.sub.1-6 alkyl, phenyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.1-6 alkoxy; or benzyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.Type: GrantFiled: January 19, 1981Date of Patent: June 8, 1982Assignee: Beecham Group LimitedInventor: Barrie C. C. Cantello
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Patent number: 4276421Abstract: Particular Syn (--NHCH.sub.3) geometrical isomers of cyano-guanidines are disclosed as new compounds having activity as histamine antagonists useful in the treatment of gastric and duodenal ulcers.Type: GrantFiled: November 15, 1979Date of Patent: June 30, 1981Assignee: Societe de Recherches et de Syntheses Organiques S.A.Inventor: Pierre Baudet
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Patent number: 4271190Abstract: Guanidinium salts having the formula ##STR1## wherein R.sup.1 and R.sup.2 are linear alkyl residues,X is an anion, andn is 1 or 2,which possess excellent microbicidal properties, particularly against organisms which have become resistant against other active materials. Methods for preparation of the compounds and solutions containing same are disclosed.Type: GrantFiled: April 17, 1980Date of Patent: June 2, 1981Assignee: Th. Goldschmidt AGInventors: Gunter Bertelmann, Ulrich Holtschmidt, Arnold Laqua
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Patent number: 4267374Abstract: Novel compounds of the formula ##STR1## wherein A is methylene, ethylene or ethylidene; R.sub.1 is --C.tbd.CH or --CH.dbd.CH.sub.2 ; R.sub.2 is hydrogen or COR wherein R is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, --NR.sub.4 R.sub.5 wherein each of R.sub.4 and R.sub.5 is hydrogen or a straight or branched lower alkyl group of from 1 to 4 carbon atoms or ##STR2## wherein R.sub.6 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.a is hydrogen, ##STR3## alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched or ##STR4## wherein R.sub.7 is selected from hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl and p-hydroxybenzyl; and R.sub.b has the same meaning as defined for R.sub.a except R.sub.b is not ##STR5## and R.sub.a and R.sub.Type: GrantFiled: June 25, 1979Date of Patent: May 12, 1981Assignee: Merrell Toraude et CompagnieInventors: Brian W. Metcalf, Michel Jung, Charles Danzin