US1915922A - Mothproofing - Google Patents
Mothproofing Download PDFInfo
- Publication number
- US1915922A US1915922A US519679A US51967931A US1915922A US 1915922 A US1915922 A US 1915922A US 519679 A US519679 A US 519679A US 51967931 A US51967931 A US 51967931A US 1915922 A US1915922 A US 1915922A
- Authority
- US
- United States
- Prior art keywords
- guanidine
- guanidines
- moth
- xylyl
- salt
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 9
- 150000002357 guanidines Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 6
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 6
- 229960004198 guanidine Drugs 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical class CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- -1 for example Chemical group 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- SQDYIZWEQGMDFO-UHFFFAOYSA-N 1,2-bis(2,3-dimethylphenyl)guanidine Chemical class CC1=CC=CC(NC(N)=NC=2C(=C(C)C=CC=2)C)=C1C SQDYIZWEQGMDFO-UHFFFAOYSA-N 0.000 description 2
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- FXQVBOJLSKRNLL-UHFFFAOYSA-N 1,2-bis(4-methylphenyl)guanidine Chemical compound C1=CC(C)=CC=C1NC(N)=NC1=CC=C(C)C=C1 FXQVBOJLSKRNLL-UHFFFAOYSA-N 0.000 description 1
- VEGSEUJMFASKPM-UHFFFAOYSA-N 1,2-dibenzylguanidine Chemical compound C=1C=CC=CC=1CNC(=N)NCC1=CC=CC=C1 VEGSEUJMFASKPM-UHFFFAOYSA-N 0.000 description 1
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 241000218652 Larix Species 0.000 description 1
- 235000005590 Larix decidua Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/907—Resistant against plant or animal attack
Definitions
- loids areusually applied as a salt of a fatty.
- This class of compounds consists guanidines of the formula-- 4 v RNH-O-NHR' I H i where R and R are aryl groups such as phe- Illustrative ofthe guanidines which we may use are di-xylyl guanidines. These may be made by the action of cyanogen chloride on the mixed xylidines. This reaction results in the formation of the guanidine hydrochloride from which the free guanidines may be separated. cost, the guanidines from the mixed 'xylidines are preferred, but if desired, the guanidine from a pure xylidine, for example, m-xylidine, may be used.
- guani dines may be used in the form of the salts of fatty'acids other than oleic, dissolved in other solvents or may be dissolved as the free base in. solvents.
- guanidines may be used instead of xyl l guanidines, for example, diphenyl guani ine, di-para-tolyl guanidine, di-benzyl guanidine, di-p-dimethyl anilino guanidine, a methyl a 7 diphenyl guanidine, di or napthyl guanidine and asymmetrical diphenyl guanidine, or mixtures thereof. These compounds are easily obtained, are non-volatile, stable to atmospheric conditions and are without toxic action to human beings when so used.
- mot -proofing material which comprises treating it with a composition containing a fatty acid salt of a di-aryl substituted guanidine.
- a moth-proofing composition comprisdi-ortho-tolyl guanidine,
- mothroofin composition comprisll.
- a moth-proofing composition a diinge, di-xyly gueni ine dissolved in on oriylfil substituted guemidme admixed with o & game solvent v or fatty acid.
- a mothroofing composition compris n witness whereof, we have hereunto subing o di-xyly gummdine salt of oleic acid scribed our memes this 25th day of February olissolved in an organic solvent. 1931.
- I Afibrous materiel cerrying e di-oryl LUDW'IG J. @HRJISTMANN. M substituted guenidine salt of e, fatty acid. DAVID W, JAYNE, Jo. 75
Description
of the di-aryl substituted nyl, tolyl, xylyl, etc.
Patented June 21, 1933 PATENT OFFICE LUD'WIG J. OHBISTKANN, OF JERSEY CITY,
NEW; JERSEY, ASSIGNORS T0 AMERICAN ann'navm w. J'AYNE, m, or Emma,
CYAHAIID COIPANY, OF NEW YORK,
IOTHPBOOFING- Io Drawing.
loids areusually applied as a salt of a fatty.
acid dissolved in naphtha. The textile or garment to, be protected is saturated with this solution, the naphtha allowed to evaporate and the residue remaining serves as a repellent tc the insects. Many other sub-- stances have been proposed for this purpose. However, many of these compounds are rare chemicals and quite expensive. Cheapness and availability, as well as efiectiveness,are desired.
We have discovered a class of compounds which may be manufactured easily and cheaply and which are very efiective as moth repellents. This class of compounds consists guanidines of the formula-- 4 v RNH-O-NHR' I H i where R and R are aryl groups such as phe- Illustrative ofthe guanidines which we may use are di-xylyl guanidines. These may be made by the action of cyanogen chloride on the mixed xylidines. This reaction results in the formation of the guanidine hydrochloride from which the free guanidines may be separated. cost, the guanidines from the mixed 'xylidines are preferred, but if desired, the guanidine from a pure xylidine, for example, m-xylidine, may be used.
As an example of our parts of xylyl guanidine m'ercial mixed xylidines, acid, mix these together and stir into 250 arts of petroleum naphtha. This solution 1s then used for the im regnation of wool clothin a proportion 0 about 1 pound of invention we take 6 made from com- 4.7- parts of oleic resulting cloth is thus protecte From the standpoint of Application filed larch 2, 1931. Serial No. 518,679.
solution to 20 poimds to 49 pounds of wool. The naphtha is allowed to eva orate. The against the rava es of the insects.
It is obvious that the proportions used may be varied. Other solvents ma be used instead of petroleum naphtha. e ade of the petroleum naphtha may be varie to give any desired rate of evaporation. The guani dines may be used in the form of the salts of fatty'acids other than oleic, dissolved in other solvents or may be dissolved as the free base in. solvents. Other guanidines may be used instead of xyl l guanidines, for example, diphenyl guani ine, di-para-tolyl guanidine, di-benzyl guanidine, di-p-dimethyl anilino guanidine, a methyl a 7 diphenyl guanidine, di or napthyl guanidine and asymmetrical diphenyl guanidine, or mixtures thereof. These compounds are easily obtained, are non-volatile, stable to atmospheric conditions and are without toxic action to human beings when so used.
It will be obvious that our invention is susceptible of many other changes and variations in addition to those set forth, the scope of the invention only being limited by the appended claims.
We claim 1. The process of moth-proofing material which comprises treating it with a OOmPOBI- tion containing a fattyl acid salt of a substance having the fo owing general formulanNn-c-Nnw where R and R are aryl oups.
2. The process of mot -proofing material which comprises treating it with a composition containing a fatty acid salt of a di-aryl substituted guanidine.
3. The process of moth-p which comprises treating 1t guanidine.
4. The process which comprises tion containing a with a di-xylyl of moth-proofing material treating it with a com di-xylyl guanidine as t of oleic acid.
5. A moth-proofing composition comprisdi-ortho-tolyl guanidine,
roofing material masses in? e Meryl substitutecl guenidioe salt of 10. As a moth-proofing compmitioo e die ott acid dissolved in on orgenic solvent. xylylsubstituted guemidme.
6. mothroofin composition comprisll. As a moth-proofing composition a diinge, di-xyly gueni ine dissolved in on oriylfil substituted guemidme admixed with o & game solvent v or fatty acid. 7. A mothroofing composition compris n witness whereof, we have hereunto subing o di-xyly gummdine salt of oleic acid scribed our memes this 25th day of February olissolved in an organic solvent. 1931. I 8. Afibrous materiel cerrying e di-oryl LUDW'IG J. @HRJISTMANN. M substituted guenidine salt of e, fatty acid. DAVID W, JAYNE, Jo. 75
9. fibrous materiel carrying e, di-xylyl guemolinea 15 v to l to so l 5 45 i no st m 5&5 312@ $359 tee
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US519679A US1915922A (en) | 1931-03-02 | 1931-03-02 | Mothproofing |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US519679A US1915922A (en) | 1931-03-02 | 1931-03-02 | Mothproofing |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1915922A true US1915922A (en) | 1933-06-27 |
Family
ID=24069324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US519679A Expired - Lifetime US1915922A (en) | 1931-03-02 | 1931-03-02 | Mothproofing |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1915922A (en) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3349099A (en) * | 1959-07-22 | 1967-10-24 | Ciba Geigy Corp | Aminoaryl-guanylhydrazones |
| US3492407A (en) * | 1965-11-09 | 1970-01-27 | Bayer Ag | Pest repelling compositions and methods of use |
| EP0155509A1 (en) * | 1984-02-24 | 1985-09-25 | Dainippon Ink And Chemicals, Inc. | Agricultural and horticultural guanidine-type fungicide and process for production thereof |
| US4709094A (en) * | 1986-07-10 | 1987-11-24 | 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 Oregon | Sigma brain receptor ligands and their use |
| US5262568A (en) * | 1990-03-02 | 1993-11-16 | State Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5312840A (en) * | 1986-07-10 | 1994-05-17 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US5336689A (en) * | 1990-03-02 | 1994-08-09 | 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 Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5385946A (en) * | 1986-07-10 | 1995-01-31 | 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 Oregon | Method for treating hypertension with disubstituted granidine compounds |
| US5403861A (en) * | 1991-02-08 | 1995-04-04 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
| US5574070A (en) * | 1990-05-25 | 1996-11-12 | 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 | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US5741661A (en) * | 1991-02-08 | 1998-04-21 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
| US5847006A (en) * | 1991-02-08 | 1998-12-08 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US5922772A (en) * | 1993-11-23 | 1999-07-13 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6143791A (en) * | 1994-02-03 | 2000-11-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US6147063A (en) * | 1993-05-27 | 2000-11-14 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6174924B1 (en) | 1994-02-03 | 2001-01-16 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US6251948B1 (en) | 1990-03-02 | 2001-06-26 | 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 Oregon | Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US6787569B1 (en) | 1994-02-03 | 2004-09-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US7351743B1 (en) | 1994-02-03 | 2008-04-01 | Wyeth | Therapeutic guanidines |
-
1931
- 1931-03-02 US US519679A patent/US1915922A/en not_active Expired - Lifetime
Cited By (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3349099A (en) * | 1959-07-22 | 1967-10-24 | Ciba Geigy Corp | Aminoaryl-guanylhydrazones |
| US3492407A (en) * | 1965-11-09 | 1970-01-27 | Bayer Ag | Pest repelling compositions and methods of use |
| EP0155509A1 (en) * | 1984-02-24 | 1985-09-25 | Dainippon Ink And Chemicals, Inc. | Agricultural and horticultural guanidine-type fungicide and process for production thereof |
| US4659739A (en) * | 1984-02-24 | 1987-04-21 | Dainippon Ink And Chemicals, Inc. | Agricultural and horticultural guanidine-type fungicide and process for production thereof |
| US5385946A (en) * | 1986-07-10 | 1995-01-31 | 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 Oregon | Method for treating hypertension with disubstituted granidine compounds |
| US5502255A (en) * | 1986-07-10 | 1996-03-26 | 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 Oregon | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US5312840A (en) * | 1986-07-10 | 1994-05-17 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US5604228A (en) * | 1986-07-10 | 1997-02-18 | 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 | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US4709094A (en) * | 1986-07-10 | 1987-11-24 | 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 Oregon | Sigma brain receptor ligands and their use |
| US5478863A (en) * | 1986-07-10 | 1995-12-26 | State Of Oregon, Oregon Health Sciences University Of Oregon | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US6251948B1 (en) | 1990-03-02 | 2001-06-26 | 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 Oregon | Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5262568A (en) * | 1990-03-02 | 1993-11-16 | State Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5559154A (en) * | 1990-03-02 | 1996-09-24 | Oregon State Board Of Higher Education | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5336689A (en) * | 1990-03-02 | 1994-08-09 | 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 Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5798390A (en) * | 1990-03-02 | 1998-08-25 | 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 Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5767162A (en) * | 1990-03-02 | 1998-06-16 | 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 Oregon | Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5637622A (en) * | 1990-03-02 | 1997-06-10 | 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 Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| US5574070A (en) * | 1990-05-25 | 1996-11-12 | 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 | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US5677348A (en) * | 1991-02-08 | 1997-10-14 | Cambridge Neuroscience, Inc. | Substituted aminoguanidines and methods of use thereof |
| US5741661A (en) * | 1991-02-08 | 1998-04-21 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
| US5670519A (en) * | 1991-02-08 | 1997-09-23 | Cambridge Neuroscience, Inc. | Acenaphthyl-substituted guanidines and methods of use thereof |
| US5672608A (en) * | 1991-02-08 | 1997-09-30 | Cambridge Neuroscience, Inc. | Acenaphthyl substituted guanidines and methods of use thereof |
| US5637623A (en) * | 1991-02-08 | 1997-06-10 | Cambridge Neuroscience, Inc. | Substituted adamantyl guanidines and methods of use there of |
| US5681861A (en) * | 1991-02-08 | 1997-10-28 | Cambridge Neuroscience, Inc. | Aminoguanidines and methods of use of same |
| US5686495A (en) * | 1991-02-08 | 1997-11-11 | Cambridge Neuroscience, Inc. | Substituted hydrazinedicarboximidamides and methods of use thereof |
| US6071969A (en) * | 1991-02-08 | 2000-06-06 | Cambridge Neuroscience, Inc. | Substituted aminoguanidines and methods of use thereof |
| US5622968A (en) * | 1991-02-08 | 1997-04-22 | Cambridge Neuroscience, Inc. | Acenaphthyl substituted guanidines and methods of use thereof |
| US5614630A (en) * | 1991-02-08 | 1997-03-25 | Cambridge Neuroscience, Inc. | Acenaphthyl substituted guanidines and methods of use thereof |
| US5837737A (en) * | 1991-02-08 | 1998-11-17 | Cambridge Neuroscience, Inc. | Hydrazinedicarboximidamide compounds and pharmaceutical composition comprising same |
| US5847006A (en) * | 1991-02-08 | 1998-12-08 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US5403861A (en) * | 1991-02-08 | 1995-04-04 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
| US5652269A (en) * | 1991-02-08 | 1997-07-29 | Cambridge Neuroscience, Inc. | Substituted hydrazinecarboximidamides and methods of use thereof |
| US6153604A (en) * | 1993-05-27 | 2000-11-28 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6147063A (en) * | 1993-05-27 | 2000-11-14 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US5955507A (en) * | 1993-11-23 | 1999-09-21 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6013675A (en) * | 1993-11-23 | 2000-01-11 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6156741A (en) * | 1993-11-23 | 2000-12-05 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US5922772A (en) * | 1993-11-23 | 1999-07-13 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6143791A (en) * | 1994-02-03 | 2000-11-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US6174924B1 (en) | 1994-02-03 | 2001-01-16 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US6288123B1 (en) | 1994-02-03 | 2001-09-11 | Cambridge Neurosciences, Inc. | Therapeutic guanidines |
| US6787569B1 (en) | 1994-02-03 | 2004-09-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US20070265348A1 (en) * | 1994-02-03 | 2007-11-15 | Scion Pharmaceuticals, Inc, A Delaware Corporation | Therapeutic guanidines |
| US7351743B1 (en) | 1994-02-03 | 2008-04-01 | Wyeth | Therapeutic guanidines |
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