JPS6324994B2 - - Google Patents
Info
- Publication number
- JPS6324994B2 JPS6324994B2 JP54168271A JP16827179A JPS6324994B2 JP S6324994 B2 JPS6324994 B2 JP S6324994B2 JP 54168271 A JP54168271 A JP 54168271A JP 16827179 A JP16827179 A JP 16827179A JP S6324994 B2 JPS6324994 B2 JP S6324994B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- guanidinomethylcyclohexanecarboxylic
- general formula
- trans
- vitamin
- 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
Links
- 239000002253 acid Substances 0.000 claims description 7
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical class OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 8
- JBRMEFWJFBHUKG-UHFFFAOYSA-N 4-[(diaminomethylideneamino)methyl]cyclohexane-1-carboxylic acid Chemical compound NC(N)=NCC1CCC(C(O)=O)CC1 JBRMEFWJFBHUKG-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229930003427 Vitamin E Natural products 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 4
- -1 inorganic acid salts Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 235000019165 vitamin E Nutrition 0.000 description 4
- 229940046009 vitamin E Drugs 0.000 description 4
- 239000011709 vitamin E Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000011718 vitamin C Substances 0.000 description 3
- QCVUPSYRZFNUBN-UHFFFAOYSA-N 4-[(diaminomethylideneamino)methyl]cyclohexane-1-carboxylic acid;hydrochloride Chemical compound Cl.NC(N)=NCC1CCC(C(O)=O)CC1 QCVUPSYRZFNUBN-UHFFFAOYSA-N 0.000 description 2
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 102000035195 Peptidases Human genes 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 108090000190 Thrombin Proteins 0.000 description 2
- 229930003268 Vitamin C Natural products 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229960004072 thrombin Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000002753 trypsin inhibitor Substances 0.000 description 2
- 235000019154 vitamin C Nutrition 0.000 description 2
- POXUQBFHDHCZAD-MHTLYPKNSA-N (2r)-2-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxy-2h-furan-5-one Chemical compound O1C(C)(C)OC[C@H]1[C@@H]1C(O)=C(O)C(=O)O1 POXUQBFHDHCZAD-MHTLYPKNSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 101710081722 Antitrypsin Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000001475 anti-trypsic effect Effects 0.000 description 1
- 239000004019 antithrombin Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
Landscapes
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16827179A JPS5692260A (en) | 1979-12-26 | 1979-12-26 | Cyclohexanecarboxylic ester and its preparation |
| AU62320/80A AU541738B2 (en) | 1979-09-20 | 1980-09-11 | Cyclohexane carboxylic acid derivatives |
| SE8006365A SE460667B (sv) | 1979-09-20 | 1980-09-11 | Cyklohexankarboxylsyraderivat, foerfarande foer framstaellning daerav samt naemnda derivat foer terapeutisk anvaendning |
| US06/186,849 US4348410A (en) | 1979-09-20 | 1980-09-15 | Cyclohexane carboxylic acid derivatives |
| DE19803035086 DE3035086A1 (de) | 1979-09-20 | 1980-09-17 | Cyclohexancarbonsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende mittel |
| GB8030183A GB2058773B (en) | 1979-09-20 | 1980-09-18 | Cyclohexane carboxylic acid derivatives |
| DK396880A DK163580C (da) | 1979-09-20 | 1980-09-19 | Analogifremgangsmaade til fremstilling af cyclohexancarboxylsyrederivater |
| AT0470680A AT375918B (de) | 1979-09-20 | 1980-09-19 | Verfahren zur herstellung von neuen estern der 4-guanidinomethyl-cyclohexancarbonsaeure |
| CH706480A CH646687A5 (fr) | 1979-09-20 | 1980-09-19 | Derives de l'acide cyclohexane carboxylique. |
| PH24606A PH17322A (en) | 1979-09-20 | 1980-09-19 | Cyclohexane carboxylic acid derivative |
| AR282590A AR227525A1 (es) | 1979-09-20 | 1980-09-19 | Procedimiento para obtener derivados de acidos ciclohexancarboxilicos |
| ES495175A ES8200643A1 (es) | 1979-09-20 | 1980-09-19 | Derivador del acido ciclohexano carboxilico |
| CA000360655A CA1142943A (en) | 1979-09-20 | 1980-09-19 | 4-guanidinomethylcyclohexane carboxylic acid compounds |
| HU230880A HU184828B (en) | 1979-09-20 | 1980-09-19 | Process for preparing cyclohexane-carboxylic acid derivatives |
| FR8020263A FR2472561B1 (fr) | 1979-09-20 | 1980-09-19 | Derives de l'acide 4-guanidinomethylcyclohexane carboxylique, leur procede de preparation et leur application en therapeutique |
| NL8005238A NL8005238A (nl) | 1979-09-20 | 1980-09-19 | Cyclohexaancarbonzuurderivaten. |
| IT68457/80A IT1129264B (it) | 1979-09-20 | 1980-09-19 | Derivati di acido cicloesancarbossilico particolarmente utili come antiulcera e procedimento per la loro preparazione |
| IN1071/CAL/80A IN151297B (no) | 1979-09-20 | 1980-09-20 | |
| MX867180A MX155236A (es) | 1979-09-20 | 1980-09-22 | Procedimiento para preparar un compuesto derivado del acido ciclohexano-carboxilico |
| BR8006052A BR8006052A (pt) | 1979-09-20 | 1980-09-23 | Processo para a preparacao de derivados de acido ciclo-hexano carboxilico |
| IN1514/CAL/82A IN155437B (no) | 1979-09-20 | 1982-12-31 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16827179A JPS5692260A (en) | 1979-12-26 | 1979-12-26 | Cyclohexanecarboxylic ester and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5692260A JPS5692260A (en) | 1981-07-25 |
| JPS6324994B2 true JPS6324994B2 (no) | 1988-05-23 |
Family
ID=15864917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16827179A Granted JPS5692260A (en) | 1979-09-20 | 1979-12-26 | Cyclohexanecarboxylic ester and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5692260A (no) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA852614B (en) * | 1985-05-17 | 1986-10-09 | Takeda Chemical Industries, Ltd. | Ascorbic acid ethers and their production |
| ES2214802T3 (es) | 1994-08-30 | 2004-09-16 | Nagase Chemtex Corporation | Intermedios para la preparacion de derivados de esteres de acido guanidinometilciclohexanocarboxilico. |
| DK0870500T3 (da) | 1995-12-22 | 2008-06-09 | Nagase Chemtex Corp | Anti-helicobacter polyri-middel |
-
1979
- 1979-12-26 JP JP16827179A patent/JPS5692260A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| JOURNAL.OF.MEDICINAL.CHEMISTRY.V15.N3 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5692260A (en) | 1981-07-25 |
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