IL110564A - Optically active 3-£3-(exo- bicyclo £2.2.1| heptyloxy)-4- methoxyphenyl|- pentandinitrile (or glutaramide) derivatives - Google Patents
Optically active 3-£3-(exo- bicyclo £2.2.1| heptyloxy)-4- methoxyphenyl|- pentandinitrile (or glutaramide) derivativesInfo
- Publication number
- IL110564A IL110564A IL110564A IL11056490A IL110564A IL 110564 A IL110564 A IL 110564A IL 110564 A IL110564 A IL 110564A IL 11056490 A IL11056490 A IL 11056490A IL 110564 A IL110564 A IL 110564A
- Authority
- IL
- Israel
- Prior art keywords
- bicyclo
- exo
- optically active
- hept
- methoxyphenyl
- Prior art date
Links
- RCCYSVYHULFYHE-UHFFFAOYSA-N pentanediamide Chemical class NC(=O)CCCC(N)=O RCCYSVYHULFYHE-UHFFFAOYSA-N 0.000 title description 2
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- 238000000034 method Methods 0.000 abstract description 19
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- 239000000543 intermediate Substances 0.000 abstract description 6
- 229940116369 pancreatic lipase Drugs 0.000 abstract description 6
- 230000008569 process Effects 0.000 abstract description 6
- 238000005809 transesterification reaction Methods 0.000 abstract description 6
- ZQTYQMYDIHMKQB-DSYKOEDSSA-N (1r,3r,4s)-bicyclo[2.2.1]heptan-3-ol Chemical compound C1C[C@@H]2[C@H](O)C[C@H]1C2 ZQTYQMYDIHMKQB-DSYKOEDSSA-N 0.000 abstract description 4
- 230000001404 mediated effect Effects 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 18
- -1 HEPTYLOXY Chemical class 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
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- 241001465754 Metazoa Species 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
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- 210000004072 lung Anatomy 0.000 description 6
- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 6
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- ZQTYQMYDIHMKQB-VQVTYTSYSA-N (1r,3s,4s)-bicyclo[2.2.1]heptan-3-ol Chemical compound C1C[C@@H]2[C@@H](O)C[C@H]1C2 ZQTYQMYDIHMKQB-VQVTYTSYSA-N 0.000 description 4
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- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000011534 wash buffer Substances 0.000 description 3
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical class CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 2
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 101000841267 Homo sapiens Long chain 3-hydroxyacyl-CoA dehydrogenase Proteins 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 102100029107 Long chain 3-hydroxyacyl-CoA dehydrogenase Human genes 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
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- ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 description 2
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- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 2
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- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 2
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
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- 229920002271 DEAE-Sepharose Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
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- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
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- RBIWXCXZWBFGAA-LLVKDONJSA-N [(2r)-octan-2-yl] butanoate Chemical compound CCCCCC[C@@H](C)OC(=O)CCC RBIWXCXZWBFGAA-LLVKDONJSA-N 0.000 description 1
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- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
- RIIWUGSYXOBDMC-UHFFFAOYSA-N benzene-1,2-diamine;hydron;dichloride Chemical compound Cl.Cl.NC1=CC=CC=C1N RIIWUGSYXOBDMC-UHFFFAOYSA-N 0.000 description 1
- OWMVSZAMULFTJU-UHFFFAOYSA-N bis-tris Chemical compound OCCN(CCO)C(CO)(CO)CO OWMVSZAMULFTJU-UHFFFAOYSA-N 0.000 description 1
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- ZQTYQMYDIHMKQB-UHFFFAOYSA-N exo-norborneol Chemical class C1CC2C(O)CC1C2 ZQTYQMYDIHMKQB-UHFFFAOYSA-N 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 210000004185 liver Anatomy 0.000 description 1
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- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- JJYKJUXBWFATTE-UHFFFAOYSA-N mosher's acid Chemical compound COC(C(O)=O)(C(F)(F)F)C1=CC=CC=C1 JJYKJUXBWFATTE-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/10—Oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Pulmonology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (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)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1989/005228 WO1991007501A1 (en) | 1989-11-13 | 1989-11-13 | Enzymatic resolution of endo-bicyclo[2.2.1]heptan-2-ol and derived pharmaceutical agents |
| IL9626190A IL96261A (en) | 1989-11-13 | 1990-11-06 | 5-(-3-[(2S)-exo-bicyclo [2.2.1]hept-2-yloxy]-4-methoxy-phenyl)-3,4,5,6-tetrahydropyrimidin-2(1H)-one and 5-3-[(2R)-exo-bicyclo [2.2.1]hept-2-yloxy]-4-methoxyphenyl)-3,4,5,6-tetrahydropyrimidin-2(1H)-one |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL110564A true IL110564A (en) | 1998-03-10 |
Family
ID=22215375
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL110564A IL110564A (en) | 1989-11-13 | 1990-11-06 | Optically active 3-£3-(exo- bicyclo £2.2.1| heptyloxy)-4- methoxyphenyl|- pentandinitrile (or glutaramide) derivatives |
| IL11056890A IL110568A (en) | 1989-11-13 | 1990-11-06 | Process for the preparation of optically active (2s)- or (2r)- endo-bicyclo [2.2.1] heptan-2-ol |
| IL9626190A IL96261A (en) | 1989-11-13 | 1990-11-06 | 5-(-3-[(2S)-exo-bicyclo [2.2.1]hept-2-yloxy]-4-methoxy-phenyl)-3,4,5,6-tetrahydropyrimidin-2(1H)-one and 5-3-[(2R)-exo-bicyclo [2.2.1]hept-2-yloxy]-4-methoxyphenyl)-3,4,5,6-tetrahydropyrimidin-2(1H)-one |
| IL11056494A IL110564A0 (en) | 1989-11-13 | 1994-08-04 | Intermediates eo endo-bicyclo [2.2.1] heptan-2-ol |
| IL11056894A IL110568A0 (en) | 1989-11-13 | 1994-08-04 | A process for the preparation of optically active (2s) - or (2r) - endo-bicyclo [2.2.1] heptan-2-ol |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL11056890A IL110568A (en) | 1989-11-13 | 1990-11-06 | Process for the preparation of optically active (2s)- or (2r)- endo-bicyclo [2.2.1] heptan-2-ol |
| IL9626190A IL96261A (en) | 1989-11-13 | 1990-11-06 | 5-(-3-[(2S)-exo-bicyclo [2.2.1]hept-2-yloxy]-4-methoxy-phenyl)-3,4,5,6-tetrahydropyrimidin-2(1H)-one and 5-3-[(2R)-exo-bicyclo [2.2.1]hept-2-yloxy]-4-methoxyphenyl)-3,4,5,6-tetrahydropyrimidin-2(1H)-one |
| IL11056494A IL110564A0 (en) | 1989-11-13 | 1994-08-04 | Intermediates eo endo-bicyclo [2.2.1] heptan-2-ol |
| IL11056894A IL110568A0 (en) | 1989-11-13 | 1994-08-04 | A process for the preparation of optically active (2s) - or (2r) - endo-bicyclo [2.2.1] heptan-2-ol |
Country Status (27)
| Country | Link |
|---|---|
| EP (2) | EP0428302B1 (de) |
| JP (1) | JPH06104661B2 (de) |
| KR (1) | KR930004654B1 (de) |
| CN (1) | CN1040423C (de) |
| AT (1) | ATE158577T1 (de) |
| AU (3) | AU633157B2 (de) |
| CA (1) | CA2029705C (de) |
| CZ (2) | CZ280006B6 (de) |
| DE (1) | DE69031487T2 (de) |
| DK (1) | DK0428302T3 (de) |
| EG (1) | EG19860A (de) |
| ES (1) | ES2107420T3 (de) |
| FI (1) | FI105106B (de) |
| GR (1) | GR3025196T3 (de) |
| HU (2) | HU220962B1 (de) |
| IE (2) | IE904059A1 (de) |
| IL (5) | IL110564A (de) |
| MY (1) | MY104517A (de) |
| NO (1) | NO304838B1 (de) |
| NZ (1) | NZ236037A (de) |
| PH (1) | PH30255A (de) |
| PL (4) | PL164457B1 (de) |
| PT (1) | PT95855B (de) |
| RU (1) | RU2104306C1 (de) |
| WO (1) | WO1991007501A1 (de) |
| YU (1) | YU48413B (de) |
| ZA (1) | ZA909044B (de) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ280006B6 (cs) * | 1989-11-13 | 1995-09-13 | Pfizer Inc. | Způsob přípravy opticky aktivního (2S) nebo (2R)-endobicyklo-2.2.1heptan-2-olu |
| US5124455A (en) * | 1990-08-08 | 1992-06-23 | American Home Products Corporation | Oxime-carbamates and oxime-carbonates as bronchodilators and anti-inflammatory agents |
| IE71647B1 (en) | 1991-01-28 | 1997-02-26 | Rhone Poulenc Rorer Ltd | Benzamide derivatives |
| US5459067A (en) * | 1991-12-06 | 1995-10-17 | Shionogi Seiyaku Kabushiki Kaisha | Method for producing optically active norborneol by ester hydrolysis |
| DK0672031T3 (da) * | 1992-12-02 | 2003-06-10 | Pfizer | Catecholdiethere som selektive PDE IV-inhibitorer |
| US5814651A (en) * | 1992-12-02 | 1998-09-29 | Pfizer Inc. | Catechol diethers as selective PDEIV inhibitors |
| JP3431204B2 (ja) * | 1993-04-22 | 2003-07-28 | 塩野義製薬株式会社 | ノルボルナン型エステル・ヒドロラーゼ |
| CN1041436C (zh) * | 1993-05-07 | 1998-12-30 | 佛山市制药一厂 | 一种稳定冯了性风湿跌打药酒的方法 |
| US5482944A (en) * | 1993-07-13 | 1996-01-09 | Pfizer Inc. | Pyrimidones and imidazolinones for treatment of shock |
| JPH1142095A (ja) * | 1997-07-25 | 1999-02-16 | Chisso Corp | 新規なオキソジシクロペンタジエンの製造方法 |
| KR100479019B1 (ko) * | 1998-05-22 | 2005-08-29 | 씨제이 주식회사 | 캐테콜히드라존유도체,이의제조방법및그를함유한약제학적조성물 |
| PL200923B1 (pl) | 1999-08-21 | 2009-02-27 | Nycomed Gmbh | Lek zawierający inhibitor PDE w połączeniu z agonistą receptoraß₂ -adrenergicznego oraz zastosowanie połączenia roflumilastu i salmeterolu |
| ES2274854T3 (es) * | 2000-05-08 | 2007-06-01 | Pfizer Products Inc. | Resolucion enzimatica de moduladores selectivos del receptor de estrogeno. |
| KR20040017246A (ko) | 2001-06-29 | 2004-02-26 | 니켄 가가쿠 가부시키가이샤 | 사이클로알케논 유도체 |
| ES2194588B1 (es) * | 2001-07-13 | 2004-10-16 | Astur Pharma S.A. | Precursores opticamente puros de paroxetina. |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| JP2006522151A (ja) | 2003-04-01 | 2006-09-28 | アプライド リサーチ システムズ エーアールエス ホールディング ナームロゼ フェンノートシャップ | 不妊症におけるホスホジエステラーゼ阻害剤 |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| WO2008151257A2 (en) | 2007-06-04 | 2008-12-11 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| ES2627848T3 (es) | 2008-06-04 | 2017-07-31 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| ES2624828T3 (es) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| MX357121B (es) | 2011-03-01 | 2018-06-27 | Synergy Pharmaceuticals Inc Star | Proceso de preparacion de agonistas c de guanilato ciclasa. |
| EP2958577A2 (de) | 2013-02-25 | 2015-12-30 | Synergy Pharmaceuticals Inc. | Guanylat-cyclase-rezeptoragonisten zur verwendung bei der darmreinigung |
| EP2968439A2 (de) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Zusammensetzungen zur behandlung von magen-darm-störungen |
| US9708367B2 (en) | 2013-03-15 | 2017-07-18 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase and their uses |
| PL3004138T3 (pl) | 2013-06-05 | 2024-07-29 | Bausch Health Ireland Limited | Ultra-oczyszczeni agoniści peptydowi cyklazy guanylanowej C, sposób ich uzyskiwania i ich zastosowanie |
| CA2920856C (en) | 2013-08-09 | 2026-03-03 | Ardelyx, Inc. | Ph modulating compounds for inhibiting gastrointestinal phosphate uptake |
| JP2022533251A (ja) | 2019-05-21 | 2022-07-21 | アルデリックス， インコーポレイテッド | 患者において血清リン酸塩を低下させるための組み合わせ |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4261995A (en) * | 1979-08-31 | 1981-04-14 | Syntex (U.S.A.) Inc. | 4-Phenyl-and 5-phenyl-1,4,5,6-tetrahydropyrimidine derivatives |
| US4732853A (en) * | 1984-11-21 | 1988-03-22 | President And Fellows Of Harvard College | Method of making chiral epoxy alcohols |
| HU215433B (hu) * | 1986-04-29 | 2000-05-28 | Pfizer Inc. | Eljárás új 2-oxo-5-fenil-pirimidin-származékok előállítására |
| CZ280006B6 (cs) * | 1989-11-13 | 1995-09-13 | Pfizer Inc. | Způsob přípravy opticky aktivního (2S) nebo (2R)-endobicyklo-2.2.1heptan-2-olu |
-
1989
- 1989-11-13 CZ CS921240A patent/CZ280006B6/cs not_active IP Right Cessation
- 1989-11-13 WO PCT/US1989/005228 patent/WO1991007501A1/en not_active Ceased
- 1989-11-13 HU HU9802988A patent/HU220962B1/hu not_active IP Right Cessation
- 1989-11-13 HU HUP9201587A patent/HU215441B/hu not_active IP Right Cessation
- 1989-11-13 RU SU5052372A patent/RU2104306C1/ru not_active IP Right Cessation
-
1990
- 1990-11-02 DE DE69031487T patent/DE69031487T2/de not_active Expired - Fee Related
- 1990-11-02 AT AT90312019T patent/ATE158577T1/de not_active IP Right Cessation
- 1990-11-02 ES ES90312019T patent/ES2107420T3/es not_active Expired - Lifetime
- 1990-11-02 EP EP90312019A patent/EP0428302B1/de not_active Expired - Lifetime
- 1990-11-02 DK DK90312019.4T patent/DK0428302T3/da active
- 1990-11-02 EP EP97103886A patent/EP0801135A1/de not_active Ceased
- 1990-11-06 IL IL110564A patent/IL110564A/en active IP Right Grant
- 1990-11-06 IL IL11056890A patent/IL110568A/en active IP Right Grant
- 1990-11-06 IL IL9626190A patent/IL96261A/en active IP Right Grant
- 1990-11-09 CA CA002029705A patent/CA2029705C/en not_active Expired - Fee Related
- 1990-11-11 EG EG67090A patent/EG19860A/xx active
- 1990-11-12 KR KR1019900018244A patent/KR930004654B1/ko not_active Expired - Fee Related
- 1990-11-12 PL PL90292070A patent/PL164457B1/pl unknown
- 1990-11-12 PL PL90292069A patent/PL164202B1/pl unknown
- 1990-11-12 YU YU214290A patent/YU48413B/sh unknown
- 1990-11-12 IE IE405990A patent/IE904059A1/en not_active IP Right Cessation
- 1990-11-12 PL PL90301764A patent/PL165132B1/pl unknown
- 1990-11-12 NZ NZ236037A patent/NZ236037A/en unknown
- 1990-11-12 MY MYPI90001992A patent/MY104517A/en unknown
- 1990-11-12 PL PL90287727A patent/PL164176B1/pl unknown
- 1990-11-12 ZA ZA909044A patent/ZA909044B/xx unknown
- 1990-11-12 CN CN90109076A patent/CN1040423C/zh not_active Expired - Fee Related
- 1990-11-12 PT PT95855A patent/PT95855B/pt not_active IP Right Cessation
- 1990-11-12 AU AU66535/90A patent/AU633157B2/en not_active Ceased
- 1990-11-12 IE IE19980174A patent/IE980174A1/en not_active IP Right Cessation
- 1990-11-13 CZ CS905609A patent/CZ280011B6/cs not_active IP Right Cessation
- 1990-11-13 JP JP2306942A patent/JPH06104661B2/ja not_active Expired - Fee Related
-
1992
- 1992-05-12 NO NO921876A patent/NO304838B1/no unknown
- 1992-05-12 FI FI922142A patent/FI105106B/fi not_active IP Right Cessation
-
1993
- 1993-01-22 AU AU31979/93A patent/AU645449B2/en not_active Ceased
- 1993-02-09 AU AU32920/93A patent/AU3292093A/en not_active Withdrawn
- 1993-10-12 PH PH47065A patent/PH30255A/en unknown
-
1994
- 1994-08-04 IL IL11056494A patent/IL110564A0/xx unknown
- 1994-08-04 IL IL11056894A patent/IL110568A0/xx unknown
-
1997
- 1997-10-29 GR GR970402831T patent/GR3025196T3/el unknown
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