JPS5944340A - メタノプロスタサイクリン誘導体の光学活性結晶性アミン塩およびその製法 - Google Patents
メタノプロスタサイクリン誘導体の光学活性結晶性アミン塩およびその製法Info
- Publication number
- JPS5944340A JPS5944340A JP15520582A JP15520582A JPS5944340A JP S5944340 A JPS5944340 A JP S5944340A JP 15520582 A JP15520582 A JP 15520582A JP 15520582 A JP15520582 A JP 15520582A JP S5944340 A JPS5944340 A JP S5944340A
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- formula
- atom
- mixture
- 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.)
- Granted
Links
- -1 amine salt Chemical class 0.000 title description 50
- 230000003287 optical effect Effects 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract description 5
- 229920000166 polytrimethylene carbonate Polymers 0.000 abstract description 5
- 208000007536 Thrombosis Diseases 0.000 abstract description 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 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 4
- 239000007788 liquid Substances 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229940035437 1,3-propanediol Drugs 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000006042 4-hexenyl group Chemical group 0.000 description 3
- 125000006043 5-hexenyl group Chemical group 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013040 bath agent Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000006053 2-methyl-3-pentenyl group Chemical group 0.000 description 2
- 125000006024 2-pentenyl group Chemical group 0.000 description 2
- 125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006055 1-methyl-4-pentenyl group Chemical group 0.000 description 1
- DALSOYJDNXEMSN-UHFFFAOYSA-N 2,3-dichlorofuran Chemical compound ClC=1C=COC=1Cl DALSOYJDNXEMSN-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZBJJDYGJCNTNTH-UHFFFAOYSA-N Betahistine mesilate Chemical group CS(O)(=O)=O.CS(O)(=O)=O.CNCCC1=CC=CC=N1 ZBJJDYGJCNTNTH-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 101150096839 Fcmr gene Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- ITBNJCVIFHSKRL-UHFFFAOYSA-N {[5-(5-nitro-2-furyl)-1,3,4-oxadiazol-2-yl]thio}acetic acid Chemical compound O1C(SCC(=O)O)=NN=C1C1=CC=C([N+]([O-])=O)O1 ITBNJCVIFHSKRL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15520582A JPS5944340A (ja) | 1982-09-08 | 1982-09-08 | メタノプロスタサイクリン誘導体の光学活性結晶性アミン塩およびその製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15520582A JPS5944340A (ja) | 1982-09-08 | 1982-09-08 | メタノプロスタサイクリン誘導体の光学活性結晶性アミン塩およびその製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5944340A true JPS5944340A (ja) | 1984-03-12 |
| JPH039891B2 JPH039891B2 (enrdf_load_stackoverflow) | 1991-02-12 |
Family
ID=15600795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15520582A Granted JPS5944340A (ja) | 1982-09-08 | 1982-09-08 | メタノプロスタサイクリン誘導体の光学活性結晶性アミン塩およびその製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5944340A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6130554A (ja) * | 1984-07-23 | 1986-02-12 | Ono Pharmaceut Co Ltd | プロスタグランジン類似化合物のある特定の立体配置を有する異性体及びそれらを有効成分として含有する治療剤 |
| JPH01104270A (ja) * | 1987-07-14 | 1989-04-21 | Sankyo Co Ltd | 抗血栓性医用材料 |
| JP2011506599A (ja) * | 2007-12-17 | 2011-03-03 | ユナイテッド セラピューティクス コーポレーション | リモジュリンの活性成分であるトレプロスチニルを製造する改良方法 |
| US9593061B2 (en) | 2014-10-20 | 2017-03-14 | United Therapeutics Corporation | Synthesis of intermediates for producing prostacyclin derivatives |
-
1982
- 1982-09-08 JP JP15520582A patent/JPS5944340A/ja active Granted
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6130554A (ja) * | 1984-07-23 | 1986-02-12 | Ono Pharmaceut Co Ltd | プロスタグランジン類似化合物のある特定の立体配置を有する異性体及びそれらを有効成分として含有する治療剤 |
| JPH01104270A (ja) * | 1987-07-14 | 1989-04-21 | Sankyo Co Ltd | 抗血栓性医用材料 |
| US10322099B2 (en) | 2007-12-17 | 2019-06-18 | United Therapeutics Corporation | Process to prepare treprostinil, the active ingredient in remodulin® |
| US8748657B2 (en) | 2007-12-17 | 2014-06-10 | United Therapeutics Corporation | Process to prepare treprostinil |
| US9156786B2 (en) | 2007-12-17 | 2015-10-13 | United Therapeutics Corporation | Process to prepare treprostinil, the active ingredient in remodulin® |
| US9593066B2 (en) | 2007-12-17 | 2017-03-14 | United Therapeutics Corporation | Process to prepare treprostinil, the active ingredient in remodulin® |
| US9604901B2 (en) | 2007-12-17 | 2017-03-28 | United Therapeutics Corporation | Process to prepare treprostinil, the active ingredient in Remodulin® |
| JP2011506599A (ja) * | 2007-12-17 | 2011-03-03 | ユナイテッド セラピューティクス コーポレーション | リモジュリンの活性成分であるトレプロスチニルを製造する改良方法 |
| US10478410B2 (en) | 2007-12-17 | 2019-11-19 | United Therapeutics Corporation | Process to prepare treprostinil, the active ingredient in Remodulin® |
| US10548863B2 (en) | 2007-12-17 | 2020-02-04 | United Therapeutics Corporation | Process to prepare treprostinil, the active ingredient in Remodulin® |
| US11723887B2 (en) | 2007-12-17 | 2023-08-15 | United Therapeutics Corporation | Process to prepare treprostinil, the active ingredient in Remodulin® |
| US9593061B2 (en) | 2014-10-20 | 2017-03-14 | United Therapeutics Corporation | Synthesis of intermediates for producing prostacyclin derivatives |
| US10196342B2 (en) | 2014-10-20 | 2019-02-05 | United Therapeutics Corporation | Synthesis of intermediates for producing prostacyclin derivatives |
| US10774027B2 (en) | 2014-10-20 | 2020-09-15 | United Therapeutics Corporation | Synthesis of intermediates for producing prostacyclin derivatives |
| US11225452B2 (en) | 2014-10-20 | 2022-01-18 | United Therapeutics Corporation | Synthesis of intermediates for producing prostacyclin derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH039891B2 (enrdf_load_stackoverflow) | 1991-02-12 |
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