CS217955B2 - Method of making the new cis ev.trans 2-aminocyclohexac - Google Patents
Method of making the new cis ev.trans 2-aminocyclohexac Download PDFInfo
- Publication number
- CS217955B2 CS217955B2 CS359176A CS359176A CS217955B2 CS 217955 B2 CS217955 B2 CS 217955B2 CS 359176 A CS359176 A CS 359176A CS 359176 A CS359176 A CS 359176A CS 217955 B2 CS217955 B2 CS 217955B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acid
- ethanol
- formula
- trans
- cis
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 e.g. OH Chemical class 0.000 claims abstract description 41
- 239000002253 acid Substances 0.000 claims abstract description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 19
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- 239000002904 solvent Substances 0.000 claims description 17
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
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- 239000003795 chemical substances by application Substances 0.000 claims description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
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- 230000005494 condensation Effects 0.000 claims description 5
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
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- 238000002360 preparation method Methods 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
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- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
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- 239000011574 phosphorus Substances 0.000 claims description 2
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- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
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- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims 1
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- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Chemical class CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims 1
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- 125000003118 aryl group Chemical group 0.000 abstract 5
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- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
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- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
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- 150000004681 metal hydrides Chemical class 0.000 abstract 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SLZHLQUFNFXTHB-UHFFFAOYSA-M sodium;5-butan-2-yl-5-ethyl-2-sulfanylidenepyrimidin-3-ide-4,6-dione Chemical compound [Na+].CCC(C)C1(CC)C([O-])=NC(=S)NC1=O SLZHLQUFNFXTHB-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VMKIXWAFFVLJCK-UHFFFAOYSA-N tert-butyl 3-oxoazetidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC(=O)C1 VMKIXWAFFVLJCK-UHFFFAOYSA-N 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS78961A CS217956B2 (cs) | 1975-06-02 | 1978-02-14 | Způsob výroby nových cis popřípadě trans 2-aminocyklohexankarboxylových nebo cis popřípadě trans 2-aminocyklopentankarboxylových kyselin |
| CS78962A CS217957B2 (cs) | 1975-06-02 | 1978-02-14 | Způsob výroby nových cis popřípadě trans 2-aminocyklohexankarboxylových nebo cis popřípadě trans 2-aminocykIopentankarboxylových.kyselin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001580 HU177576B (en) | 1975-06-02 | 1975-06-02 | Process for preparing 2-amino-cyclohexane carboxylic acid,its amides and similar compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS217955B2 true CS217955B2 (en) | 1983-02-25 |
Family
ID=10994566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS359176A CS217955B2 (en) | 1975-06-02 | 1976-05-28 | Method of making the new cis ev.trans 2-aminocyclohexac |
Country Status (6)
| Country | Link |
|---|---|
| AT (2) | AT350518B (enrdf_load_stackoverflow) |
| CS (1) | CS217955B2 (enrdf_load_stackoverflow) |
| DE (1) | DE2624290A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2313023A1 (enrdf_load_stackoverflow) |
| HU (1) | HU177576B (enrdf_load_stackoverflow) |
| YU (2) | YU129376A (enrdf_load_stackoverflow) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3125872A1 (de) * | 1981-07-01 | 1983-01-20 | Basf Ag, 6700 Ludwigshafen | Schiff-basen von aminocycloalkancarbonsaeureestern, verfahren zu ihrer herstellung sowie ihre verwendung als zwischenprodukte |
| EP0214009A3 (en) * | 1985-07-30 | 1989-01-11 | Merck & Co. Inc. | Enaminones as potential prodrugs of primary and secondary amines |
| GB8716278D0 (en) * | 1987-07-10 | 1987-08-19 | Fujisawa Pharmaceutical Co | Antimicrobial agent |
| DE4033415A1 (de) * | 1990-10-20 | 1992-04-23 | Bayer Ag | Antimikrobielle mittel sowie substituierte 2-cyclohexan-1-yl-amin-derivate und deren herstellung |
| AU673824B2 (en) * | 1992-05-29 | 1996-11-28 | Bayer Aktiengesellschaft | Cyclopentane- and -pentene-beta-amino acids |
| US6462076B2 (en) | 2000-06-14 | 2002-10-08 | Hoffmann-La Roche Inc. | Beta-amino acid nitrile derivatives as cathepsin K inhibitors |
| HUP0402344A2 (hu) | 2001-12-04 | 2005-02-28 | F. Hoffmann-La Roche Ag | Helyettesített 2-amino-cikloalkán-karboxamidok, felhasználásuk cisztein-proteáz-inhibitorként, eljárás az előállításukra és ezeket tartalmazó gyógyszerkészítmények |
| US6759428B2 (en) | 2001-12-04 | 2004-07-06 | Roche Palo Alto Llc | Indole nitriles |
| WO2004056744A1 (en) * | 2002-12-23 | 2004-07-08 | Janssen Pharmaceutica N.V. | Adamantyl acetamides as hydroxysteroid dehydrogenase inhibitors |
| EP1533295A1 (en) * | 2003-11-24 | 2005-05-25 | Newron Pharmaceuticals S.p.A. | Cyclopentyl Derivatives |
| AU2005240784C1 (en) | 2004-05-07 | 2011-12-22 | Janssen Pharmaceutica N.V. | Pyrrolidin-2-one and piperidin-2-one derivatives as 11-beta hydroxysteroid dehydrogenase inhibitors |
| BRPI0515121A (pt) | 2004-08-30 | 2008-07-08 | Janssen Pharmaceutica Nv | derivados da n-2 adamantil-2-fenóxi acetamida como inibidores da 11-beta hidroxiesteróide desidrogenase |
| US8563591B2 (en) | 2004-08-30 | 2013-10-22 | Janssen Pharmaceutica N.V. | Tricyclic lactam derivatives as 11-beta hydroxysteroid dehydrogenase inhibitors |
| DE602005017159D1 (de) | 2004-08-30 | 2009-11-26 | Janssen Pharmaceutica Nv | Oxysteroid-dehydrogenase-inhibitoren |
| RU2487195C2 (ru) | 2009-02-17 | 2013-07-10 | МАКЭЛИСТЭР ТЕКНОЛОДЖИЗ, ЭлЭлСи | Устройство и способ улавливания газа во время электролиза |
| US9040012B2 (en) | 2009-02-17 | 2015-05-26 | Mcalister Technologies, Llc | System and method for renewable resource production, for example, hydrogen production by microbial electrolysis, fermentation, and/or photosynthesis |
| RU2489523C2 (ru) | 2009-02-17 | 2013-08-10 | МАКЭЛИСТЭР ТЕКНОЛОДЖИЗ, ЭлЭлСи | Устройство и способ регулирования зародышеобразования во время электролиза |
| JP5411299B2 (ja) | 2009-02-17 | 2014-02-12 | マクアリスター テクノロジーズ エルエルシー | 電解セルおよびその使用方法 |
| US8075750B2 (en) | 2009-02-17 | 2011-12-13 | Mcalister Technologies, Llc | Electrolytic cell and method of use thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3510492A (en) * | 1968-05-13 | 1970-05-05 | Upjohn Co | 2-anilino and 2-anilinomethyl cycloalkylamines |
| US3647804A (en) * | 1970-02-27 | 1972-03-07 | Upjohn Co | Cycloalkanecarboxamides |
| US3770825A (en) * | 1970-12-07 | 1973-11-06 | Yeda Res & Dev | 2-substituted amino cycloalkylcarboxamides |
-
1975
- 1975-06-02 HU HUCI001580 patent/HU177576B/hu unknown
-
1976
- 1976-05-27 YU YU129376A patent/YU129376A/xx unknown
- 1976-05-28 CS CS359176A patent/CS217955B2/cs unknown
- 1976-05-31 DE DE19762624290 patent/DE2624290A1/de not_active Withdrawn
- 1976-05-31 AT AT395476A patent/AT350518B/de not_active IP Right Cessation
- 1976-06-02 FR FR7616648A patent/FR2313023A1/fr active Granted
-
1977
- 1977-08-24 AT AT612777A patent/AT346826B/de not_active IP Right Cessation
-
1982
- 1982-05-04 YU YU94982A patent/YU94982A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU177576B (en) | 1981-11-28 |
| ATA612777A (de) | 1978-04-15 |
| ATA395476A (de) | 1978-11-15 |
| AT350518B (de) | 1979-06-11 |
| YU94982A (en) | 1982-08-31 |
| YU129376A (en) | 1982-08-31 |
| DE2624290A1 (de) | 1977-04-14 |
| AT346826B (de) | 1978-11-27 |
| FR2313023B1 (enrdf_load_stackoverflow) | 1978-12-15 |
| FR2313023A1 (fr) | 1976-12-31 |
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