ZA200200966B - Method for preparing cyclohexane carboxylic acids. - Google Patents
Method for preparing cyclohexane carboxylic acids. Download PDFInfo
- Publication number
- ZA200200966B ZA200200966B ZA200200966A ZA200200966A ZA200200966B ZA 200200966 B ZA200200966 B ZA 200200966B ZA 200200966 A ZA200200966 A ZA 200200966A ZA 200200966 A ZA200200966 A ZA 200200966A ZA 200200966 B ZA200200966 B ZA 200200966B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- compound
- galkyl
- halo
- methoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 150000005378 cyclohexanecarboxylic acids Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- -1 3- cyclopentyloxy Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000005690 diesters Chemical class 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 230000000911 decarboxylating effect Effects 0.000 claims description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000002346 iodo group Chemical group I* 0.000 claims description 3
- REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000005907 alkyl ester group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical group [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims 2
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000005490 tosylate group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical class OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 210000000440 neutrophil Anatomy 0.000 description 2
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 2
- ISEJXQAAWBXLGB-UHFFFAOYSA-N 1-cyanocyclohexane-1-carboxylic acid Chemical class OC(=O)C1(C#N)CCCCC1 ISEJXQAAWBXLGB-UHFFFAOYSA-N 0.000 description 1
- KJZWYCAIEUYAIW-UHFFFAOYSA-N 4-cyanocyclohexane-1-carboxylic acid Chemical class OC(=O)C1CCC(C#N)CC1 KJZWYCAIEUYAIW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 208000003714 Bronchopulmonary Sequestration Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000021878 Congenital pulmonary sequestration Diseases 0.000 description 1
- 206010015866 Extravasation Diseases 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 206010059160 Pulmonary sequestration Diseases 0.000 description 1
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 1
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002497 edematous effect Effects 0.000 description 1
- 230000036251 extravasation Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000011242 neutrophil chemotaxis Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0212—Face masks
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/733—Alginic acid; Salts thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/24—Thermal properties
- A61K2800/242—Exothermic; Self-heating; Heating sensation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14757899P | 1999-08-06 | 1999-08-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200200966B true ZA200200966B (en) | 2002-10-30 |
Family
ID=22522131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200200966A ZA200200966B (en) | 1999-08-06 | 2002-02-04 | Method for preparing cyclohexane carboxylic acids. |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6296840B1 (es) |
| EP (1) | EP1200388A4 (es) |
| JP (1) | JP2003506427A (es) |
| KR (1) | KR20020025212A (es) |
| CN (1) | CN1192017C (es) |
| AR (1) | AR031221A1 (es) |
| AU (1) | AU774567B2 (es) |
| BR (1) | BR0013026A (es) |
| CA (1) | CA2381011A1 (es) |
| CO (1) | CO5180573A1 (es) |
| CZ (1) | CZ2002427A3 (es) |
| EC (1) | ECSP003600A (es) |
| HK (1) | HK1047079A1 (es) |
| HU (1) | HUP0202458A3 (es) |
| IL (2) | IL147366A0 (es) |
| MX (1) | MXPA02001338A (es) |
| MY (1) | MY123552A (es) |
| NO (1) | NO20020560L (es) |
| NZ (1) | NZ516406A (es) |
| PE (1) | PE20010483A1 (es) |
| PL (1) | PL353352A1 (es) |
| TR (1) | TR200200308T2 (es) |
| TW (1) | TW584624B (es) |
| WO (1) | WO2001010817A1 (es) |
| ZA (1) | ZA200200966B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040161435A1 (en) * | 2003-02-14 | 2004-08-19 | Gupta Shyam K. | Skin Firming Anti-Aging Cosmetic Mask Compositions |
| US20070148111A1 (en) * | 2005-12-22 | 2007-06-28 | Remy Simpson | Peel off synthetic body paint |
| US20070148112A1 (en) * | 2005-12-28 | 2007-06-28 | Avon Products, Inc. | Foaming, color-changing topical composition and method of imparting a cosmetic effect |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2398575A (en) * | 1946-04-16 | Theib manufacture | ||
| US4014995A (en) * | 1973-09-19 | 1977-03-29 | The Quaker Oats Company | Cosmetics containing finely divided oat flour |
| US4965071A (en) * | 1988-10-19 | 1990-10-23 | The Gillette Company | Wrinkle masking composition of sodium polystyrene sulfonate and process for use |
| NZ251092A (en) * | 1992-04-02 | 1996-12-20 | Smithkline Beecham Corp | 4-cyano-cyclohexane derivatives; medicaments; used in treating asthma |
| US5567420A (en) * | 1994-11-16 | 1996-10-22 | Mceleney; John | Lotion which is temporarily colored upon application |
| US5618850A (en) * | 1995-03-09 | 1997-04-08 | Focal, Inc. | Hydroxy-acid cosmetics |
-
2000
- 2000-08-02 EC EC2000003600A patent/ECSP003600A/es unknown
- 2000-08-02 US US09/631,366 patent/US6296840B1/en not_active Expired - Fee Related
- 2000-08-03 AR ARP000104010A patent/AR031221A1/es not_active Application Discontinuation
- 2000-08-03 CO CO00058244A patent/CO5180573A1/es not_active Application Discontinuation
- 2000-08-04 EP EP00952559A patent/EP1200388A4/en not_active Withdrawn
- 2000-08-04 CA CA002381011A patent/CA2381011A1/en not_active Abandoned
- 2000-08-04 JP JP2001515284A patent/JP2003506427A/ja not_active Withdrawn
- 2000-08-04 IL IL14736600A patent/IL147366A0/xx active IP Right Grant
- 2000-08-04 HU HU0202458A patent/HUP0202458A3/hu unknown
- 2000-08-04 TR TR2002/00308T patent/TR200200308T2/xx unknown
- 2000-08-04 BR BR0013026-5A patent/BR0013026A/pt not_active IP Right Cessation
- 2000-08-04 CN CNB00811112XA patent/CN1192017C/zh not_active Expired - Fee Related
- 2000-08-04 AU AU65233/00A patent/AU774567B2/en not_active Ceased
- 2000-08-04 MX MXPA02001338A patent/MXPA02001338A/es active IP Right Grant
- 2000-08-04 WO PCT/US2000/021434 patent/WO2001010817A1/en not_active Application Discontinuation
- 2000-08-04 MY MYPI20003570 patent/MY123552A/en unknown
- 2000-08-04 PL PL00353352A patent/PL353352A1/xx not_active Application Discontinuation
- 2000-08-04 KR KR1020027001573A patent/KR20020025212A/ko not_active Application Discontinuation
- 2000-08-04 NZ NZ516406A patent/NZ516406A/xx unknown
- 2000-08-04 CZ CZ2002427A patent/CZ2002427A3/cs unknown
- 2000-08-07 PE PE2000000798A patent/PE20010483A1/es not_active Application Discontinuation
- 2000-08-25 TW TW089115652A patent/TW584624B/zh not_active IP Right Cessation
-
2001
- 2001-12-27 IL IL147366A patent/IL147366A/en not_active IP Right Cessation
-
2002
- 2002-02-04 ZA ZA200200966A patent/ZA200200966B/en unknown
- 2002-02-05 NO NO20020560A patent/NO20020560L/no not_active Application Discontinuation
- 2002-09-27 HK HK02107177.8A patent/HK1047079A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1200388A4 (en) | 2004-12-29 |
| AU774567B2 (en) | 2004-07-01 |
| NZ516406A (en) | 2004-02-27 |
| IL147366A0 (en) | 2002-08-14 |
| CZ2002427A3 (cs) | 2002-06-12 |
| CN1192017C (zh) | 2005-03-09 |
| KR20020025212A (ko) | 2002-04-03 |
| EP1200388A1 (en) | 2002-05-02 |
| JP2003506427A (ja) | 2003-02-18 |
| CA2381011A1 (en) | 2001-02-15 |
| CN1367774A (zh) | 2002-09-04 |
| PL353352A1 (en) | 2003-11-17 |
| HUP0202458A2 (hu) | 2002-11-28 |
| IL147366A (en) | 2006-08-20 |
| AU6523300A (en) | 2001-03-05 |
| HUP0202458A3 (en) | 2003-11-28 |
| PE20010483A1 (es) | 2001-06-15 |
| US6296840B1 (en) | 2001-10-02 |
| TR200200308T2 (tr) | 2002-06-21 |
| BR0013026A (pt) | 2002-04-16 |
| MXPA02001338A (es) | 2002-07-22 |
| ECSP003600A (es) | 2002-03-25 |
| CO5180573A1 (es) | 2002-07-30 |
| AR031221A1 (es) | 2003-09-17 |
| HK1047079A1 (zh) | 2003-02-07 |
| TW584624B (en) | 2004-04-21 |
| NO20020560D0 (no) | 2002-02-05 |
| MY123552A (en) | 2006-05-31 |
| WO2001010817A1 (en) | 2001-02-15 |
| NO20020560L (no) | 2002-02-05 |
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