IE33576L - N, n'-alkylene bis (benzamides) - Google Patents
N, n'-alkylene bis (benzamides)Info
- Publication number
- IE33576L IE33576L IE691220A IE122069A IE33576L IE 33576 L IE33576 L IE 33576L IE 691220 A IE691220 A IE 691220A IE 122069 A IE122069 A IE 122069A IE 33576 L IE33576 L IE 33576L
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- bis
- acid
- alkylene
- compounds
- Prior art date
Links
- 229910052757 nitrogen Inorganic materials 0.000 title abstract 14
- 229940054066 benzamide antipsychotics Drugs 0.000 title abstract 3
- 150000003936 benzamides Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000002947 alkylene group Chemical group 0.000 abstract 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 3
- 239000005977 Ethylene Substances 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 125000004494 ethyl ester group Chemical group 0.000 abstract 3
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- CGEOYYBCLBIBLG-UHFFFAOYSA-N (4-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C(Cl)=O)C=C1 CGEOYYBCLBIBLG-UHFFFAOYSA-N 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- NTKSOQFMMSKDFG-UHFFFAOYSA-N 3,7-dimethyloctane-1,7-diamine Chemical compound NCCC(C)CCCC(C)(C)N NTKSOQFMMSKDFG-UHFFFAOYSA-N 0.000 abstract 1
- CMTCGCORWPJCOO-UHFFFAOYSA-N 3-(7-chlorohept-3-ynyl)-4-methylbenzenesulfonic acid Chemical compound CC1=C(C=C(C=C1)S(=O)(=O)O)CCC#CCCCCl CMTCGCORWPJCOO-UHFFFAOYSA-N 0.000 abstract 1
- VKPLPDIMEREJJF-UHFFFAOYSA-N 3-methoxybenzamide Chemical compound COC1=CC=CC(C(N)=O)=C1 VKPLPDIMEREJJF-UHFFFAOYSA-N 0.000 abstract 1
- -1 4 - oxoheptamethylene Chemical group 0.000 abstract 1
- SHSGDXCJYVZFTP-ZBJDZAJPSA-N 4-(1,1,2,2,2-pentadeuterioethoxy)benzoic acid Chemical compound [2H]C([2H])([2H])C([2H])([2H])OC1=CC=C(C(O)=O)C=C1 SHSGDXCJYVZFTP-ZBJDZAJPSA-N 0.000 abstract 1
- FXWBYMLSQLQXAR-UHFFFAOYSA-N 4-(2,2,2-trifluoroethoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OCC(F)(F)F)C=C1 FXWBYMLSQLQXAR-UHFFFAOYSA-N 0.000 abstract 1
- JLVZTADQJXHQLT-UHFFFAOYSA-N 4-(2,2-dichloroethenoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OC=C(Cl)Cl)C=C1 JLVZTADQJXHQLT-UHFFFAOYSA-N 0.000 abstract 1
- YBICPDGCVIUHNA-UHFFFAOYSA-N 4-(2-methoxyethoxy)benzoic acid Chemical compound COCCOC1=CC=C(C(O)=O)C=C1 YBICPDGCVIUHNA-UHFFFAOYSA-N 0.000 abstract 1
- ZEYHEAKUIGZSGI-FIBGUPNXSA-N 4-(trideuteriomethoxy)benzoic acid Chemical compound [2H]C([2H])([2H])OC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-FIBGUPNXSA-N 0.000 abstract 1
- GDBUZIKSJGRBJP-UHFFFAOYSA-N 4-acetoxy benzoic acid Chemical compound CC(=O)OC1=CC=C(C(O)=O)C=C1 GDBUZIKSJGRBJP-UHFFFAOYSA-N 0.000 abstract 1
- XLWQUESMILVIPR-UHFFFAOYSA-N 4-ethoxybenzoyl chloride Chemical compound CCOC1=CC=C(C(Cl)=O)C=C1 XLWQUESMILVIPR-UHFFFAOYSA-N 0.000 abstract 1
- PMZDWSGWYVHWMV-UHFFFAOYSA-N 4-methoxy-3,5-bis(phenylmethoxy)benzoic acid Chemical compound C1=C(C(O)=O)C=C(OCC=2C=CC=CC=2)C(OC)=C1OCC1=CC=CC=C1 PMZDWSGWYVHWMV-UHFFFAOYSA-N 0.000 abstract 1
- DYDWKSVZHZNBLO-UHFFFAOYSA-N 4-prop-2-enoxybenzoic acid Chemical compound OC(=O)C1=CC=C(OCC=C)C=C1 DYDWKSVZHZNBLO-UHFFFAOYSA-N 0.000 abstract 1
- WYTFPLYKDZJBTK-UHFFFAOYSA-N 7-chlorohept-3-yn-1-ol Chemical compound OCCC#CCCCCl WYTFPLYKDZJBTK-UHFFFAOYSA-N 0.000 abstract 1
- 206010020880 Hypertrophy Diseases 0.000 abstract 1
- 239000007983 Tris buffer Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000001919 adrenal effect Effects 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000003509 anti-fertility effect Effects 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- WIWYHCLUYHPVCL-UHFFFAOYSA-N hept-3-yne-1,7-diamine Chemical compound NCCCC#CCCN WIWYHCLUYHPVCL-UHFFFAOYSA-N 0.000 abstract 1
- GDRJDUSGGPSMEI-UHFFFAOYSA-N heptane-1,4,7-triamine Chemical compound NCCCC(N)CCCN GDRJDUSGGPSMEI-UHFFFAOYSA-N 0.000 abstract 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- DZNQADWIXYJXIN-UHFFFAOYSA-N nonane-2,8-diamine Chemical compound CC(N)CCCCCC(C)N DZNQADWIXYJXIN-UHFFFAOYSA-N 0.000 abstract 1
- QXSAKPUBHTZHKW-UHFFFAOYSA-N para-hydroxybenzamide Natural products NC(=O)C1=CC=C(O)C=C1 QXSAKPUBHTZHKW-UHFFFAOYSA-N 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
- C07C317/40—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
- C07C323/42—Y being a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C391/00—Compounds containing selenium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
Abstract
1,257,199. N,N<SP>1</SP>-Alkylene bis-(benzamides). STERLING DRUG Inc. 14 Aug., 1969 [30 Aug., 1968], No. 40793/69. Heading C2C. Novel N,N<SP>1</SP>-alkylene bis-(benzamides) of the formulµ and where Q is C 1-6 alkyl, C 3-6 alkoxyalkyl, C 3-6 alkenyl, halo-C 1-6 alkyl, halo-C 2-6 alkenyl, C 3-6 cycloalkyl phenyl or BN-(C 1-6 alkyl), where BN is di-(C 1-6 alkyl) amino or a 5-7 membered saturated nitrogen containing monocyclic heterocyclic ring, R is H or C 1-6 alkyl, Y is C 5-12 alkylene, having at least 5 carbon atoms between its 2 connecting linkages, wherein a carbon atom of said alkylene more than 2 carbon atoms removed from the amide N atoms can be replaced by -O-, -S-, -S-S-, -Se- Se-, =SO, =SO 2 , =NH, =N-(C 1-6 alkyl), =N-(CO-phenyl-4-10-Q),=C=O, -CH = CH- or -C#C-, or Y is Y<SP>1</SP>-Z-Y<SP>11</SP>, where Y<SP>1</SP> is C 1-4 alkylene, Y<SP>11</SP> is a direct linkage ; or C 1-4 alkylene, Z is phenyl or C 3-6 cycloalkyl, and 'the benzene ring of the phenyl radical of Formula I is, if desired, further substituted by, for example, C 1-6 alkyl, C 1-6 alkoxy, halogen, benzyloxy or OH are prepared by reacting an amine of the formula RNH-Y-NHR with at least two molar equivalents of the appropriate benzoylating agents. In addition, compounds, formula I, in which the phenyl radical is substituted by OH may be obtained by hydrogenolysis of the corresponding benzyloxy substituted compounds, compounds in which Q is di-(C 1-6 alkyl) amino (C 1-6 alkyl) by reacting the corresponding compounds in which Q is OH with the appropriate di-.(C 1-6 alkyl) amino-(C 1-6 alkyl) halides, and compounds, in which the alkylene chain Y is interrupted by = C = 0, by hydrolysing the corresponding ethylene ketals. In comparative examples, N,N<SP>1</SP> - heptamethylene bis - (3 - methoxybenzamide, N,N<SP>1</SP>- heptamethylene bis (2 - methoxybenzamide), N,N<SP>1</SP> - heptamethylene bis - (4 - methylthiobenzamide) and N,N<SP>1</SP>-hexamethylene bis-(4-hydroxybenzamide) are made by reacting the appropriate amines with the corresponding acid chlorides or esters. N,N<SP>1</SP> - Heptamethylene bis - (4 - hydroxybenzamide) is obtained by hydrolysing N,N<SP>1</SP> - heptamethylene bis-(4-acetoxybenzamide) which is made by reacting 1,7-heptanediamine with 4-acetoxybenzoyl chloride. The following intermediates are also prepared: 4-trideuteromethoxy benzoic acid, acid chloride and ethyl ester thereof, 4-ethoxybenzoyl chloride, 4-acetoxybenzoic acid and acid chloride, 4 - (2,2,2 - trifluoroethoxy) benzoic acid, acid chloride and ethyl ester, 4-(2,2-dichlorovinyloxy) benzoic acid, acid chloride and ester, 4-allyloxybenzoic acid, acid chloride and ester, 3,5- dibenzyloxy - 4 - methoxy -benzoic acid, acid chloride and methyl ester, 4-pentadeuteroethoxybenzoic acid, acid chloride and ethyl ester, 2,8-nonanediamine, ethylene ketal of 1,4 - diamino - 4-heptanone, ethylene ketal of N,N<SP>1</SP> - (4 - oxoheptamethylene) bis - (phthalimide), 1,1,5 - trimethyl -1,7 - heptanediamine, N 1 - acetyl - 1,1,5 - trimethyl - 1,7 - heptanediamine, N,N<SP>1</SP> - dimethyl 1,7 - heptanediamine, N,N<SP>1</SP> - dibenzal - 1,7 - heptanediamine, and the dimethiodide thereof, 3-heptyne-1,7- diamine, 7 - chloro - 3 - heptyne - 1 - ol, 7-chloro- 3-heptyne-1-yl-4-toluene sulphonate, N,N<SP>1</SP>- (3 - heptyne-1,7 - diyl) bis - phthalimide, 1,4,7- heptane - triamine, N,N<SP>1</SP>N<SP>11</SP> - (1,4,7 - heptamethylene) tris - phthalamide, and 4 - (2- methoxyethoxy) benzoic acid Pharmaceutical compositions, suitable for oral or parenteral administration and having adrenal hypertrophy, antifertility and hypocholestremic activities, contain the above novel compounds and conventional pharmaceutically acceptable carriers.
[GB1257199A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75637368A | 1968-08-30 | 1968-08-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE33576L true IE33576L (en) | 1970-02-28 |
| IE33576B1 IE33576B1 (en) | 1974-08-21 |
Family
ID=25043187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1220/69A IE33576B1 (en) | 1968-08-30 | 1969-08-29 | Chemical compounds and their preparation |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS505181B1 (en) |
| AT (1) | AT299162B (en) |
| BE (1) | BE738084A (en) |
| BR (1) | BR6911910D0 (en) |
| CH (1) | CH511803A (en) |
| DE (1) | DE1943787A1 (en) |
| ES (1) | ES370985A1 (en) |
| FR (1) | FR2016691B1 (en) |
| GB (1) | GB1257199A (en) |
| IE (1) | IE33576B1 (en) |
| IL (1) | IL32881A (en) |
| NL (1) | NL6913186A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53105616U (en) * | 1977-01-27 | 1978-08-25 | ||
| JPS55144771U (en) * | 1979-04-05 | 1980-10-17 | ||
| US20230416181A1 (en) * | 2020-12-18 | 2023-12-28 | Dow Global Technologies Llc | Oxygenated solvent odorant removal composition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1320717A (en) * | 1959-10-08 | 1963-03-15 | Sterling Drug Inc | Process for the preparation of n, n'-di - [(halogenated lower alkanoyl)] aliphatic diamine derivatives |
-
1969
- 1969-08-14 GB GB1257199D patent/GB1257199A/en not_active Expired
- 1969-08-22 IL IL32881A patent/IL32881A/en unknown
- 1969-08-28 NL NL6913186A patent/NL6913186A/xx unknown
- 1969-08-28 DE DE19691943787 patent/DE1943787A1/en active Pending
- 1969-08-28 AT AT823469A patent/AT299162B/en not_active IP Right Cessation
- 1969-08-28 BE BE738084D patent/BE738084A/xx unknown
- 1969-08-28 CH CH1304369A patent/CH511803A/en not_active IP Right Cessation
- 1969-08-28 BR BR211910/69A patent/BR6911910D0/en unknown
- 1969-08-29 IE IE1220/69A patent/IE33576B1/en unknown
- 1969-08-29 ES ES370985A patent/ES370985A1/en not_active Expired
- 1969-08-29 FR FR6929702A patent/FR2016691B1/fr not_active Expired
- 1969-08-29 JP JP44068564A patent/JPS505181B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL32881A0 (en) | 1969-12-31 |
| BE738084A (en) | 1970-03-02 |
| AT299162B (en) | 1972-06-12 |
| IL32881A (en) | 1974-03-14 |
| CH511803A (en) | 1971-08-31 |
| BR6911910D0 (en) | 1973-01-04 |
| GB1257199A (en) | 1971-12-15 |
| NL6913186A (en) | 1970-03-03 |
| FR2016691A1 (en) | 1970-05-08 |
| JPS505181B1 (en) | 1975-02-28 |
| ES370985A1 (en) | 1971-08-01 |
| FR2016691B1 (en) | 1974-04-12 |
| IE33576B1 (en) | 1974-08-21 |
| DE1943787A1 (en) | 1970-03-05 |
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