NO130256B - - Google Patents
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- Publication number
- NO130256B NO130256B NO02166/72A NO216672A NO130256B NO 130256 B NO130256 B NO 130256B NO 02166/72 A NO02166/72 A NO 02166/72A NO 216672 A NO216672 A NO 216672A NO 130256 B NO130256 B NO 130256B
- Authority
- NO
- Norway
- Prior art keywords
- progesterone
- acetoxy
- hydroxy
- acid
- acyloxy
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 229960003387 progesterone Drugs 0.000 claims description 23
- 239000000186 progesterone Substances 0.000 claims description 23
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
- 229960000583 acetic acid Drugs 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 239000012362 glacial acetic acid Substances 0.000 claims description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 9
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 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 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 2
- 238000006735 epoxidation reaction Methods 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000002211 ultraviolet spectrum Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- DXNJBNPIVVOILB-QCGOMIHKSA-N (8s,9s,10r,13s,14s,17s)-17-acetyl-4-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=C(O)C(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 DXNJBNPIVVOILB-QCGOMIHKSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- VTHUYJIXSMGYOQ-KOORYGTMSA-N 17-hydroxyprogesterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 VTHUYJIXSMGYOQ-KOORYGTMSA-N 0.000 description 1
- ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- 208000008899 Habitual abortion Diseases 0.000 description 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- 208000035175 Oligomenorrhea Diseases 0.000 description 1
- 206010030295 Oligomenorrhoea Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 235000013832 Valeriana officinalis Nutrition 0.000 description 1
- 244000126014 Valeriana officinalis Species 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 230000002513 anti-ovulatory effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229960002899 hydroxyprogesterone Drugs 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04R—LOUDSPEAKERS, MICROPHONES, GRAMOPHONE PICK-UPS OR LIKE ACOUSTIC ELECTROMECHANICAL TRANSDUCERS; DEAF-AID SETS; PUBLIC ADDRESS SYSTEMS
- H04R1/00—Details of transducers, loudspeakers or microphones
- H04R1/20—Arrangements for obtaining desired frequency or directional characteristics
- H04R1/32—Arrangements for obtaining desired frequency or directional characteristics for obtaining desired directional characteristic only
- H04R1/34—Arrangements for obtaining desired frequency or directional characteristics for obtaining desired directional characteristic only by using a single transducer with sound reflecting, diffracting, directing or guiding means
- H04R1/38—Arrangements for obtaining desired frequency or directional characteristics for obtaining desired directional characteristic only by using a single transducer with sound reflecting, diffracting, directing or guiding means in which sound waves act upon both sides of a diaphragm and incorporating acoustic phase-shifting means, e.g. pressure-gradient microphone
Landscapes
- Health & Medical Sciences (AREA)
- Otolaryngology (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Acoustics & Sound (AREA)
- Signal Processing (AREA)
- Building Environments (AREA)
- Electrostatic, Electromagnetic, Magneto- Strictive, And Variable-Resistance Transducers (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2130887 | 1971-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO130256B true NO130256B (enrdf_load_stackoverflow) | 1974-07-29 |
Family
ID=5811444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO02166/72A NO130256B (enrdf_load_stackoverflow) | 1971-06-22 | 1972-06-16 |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE784997A (enrdf_load_stackoverflow) |
| CH (1) | CH547048A (enrdf_load_stackoverflow) |
| DE (1) | DE2130887B1 (enrdf_load_stackoverflow) |
| ES (1) | ES404091A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2143320A1 (enrdf_load_stackoverflow) |
| IT (1) | IT965841B (enrdf_load_stackoverflow) |
| NL (1) | NL7208049A (enrdf_load_stackoverflow) |
| NO (1) | NO130256B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2531299B1 (fr) * | 1982-08-02 | 1986-07-18 | Depaepe Sa Henri | Transducteur acousto-electrique, notamment pour microphone piezoelectrique |
| DE3807251A1 (de) * | 1988-03-05 | 1989-09-14 | Sennheiser Electronic | Kapazitiver schallwandler |
-
1971
- 1971-06-22 DE DE19712130887D patent/DE2130887B1/de active Pending
-
1972
- 1972-05-17 CH CH734072A patent/CH547048A/xx not_active IP Right Cessation
- 1972-06-13 NL NL7208049A patent/NL7208049A/xx unknown
- 1972-06-16 NO NO02166/72A patent/NO130256B/no unknown
- 1972-06-16 BE BE784997A patent/BE784997A/xx unknown
- 1972-06-20 IT IT51028/72A patent/IT965841B/it active
- 1972-06-21 ES ES404091A patent/ES404091A1/es not_active Expired
- 1972-06-22 FR FR7222625A patent/FR2143320A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ES404091A1 (es) | 1975-05-16 |
| DE2130887B1 (de) | 1972-09-07 |
| IT965841B (it) | 1974-02-11 |
| NL7208049A (enrdf_load_stackoverflow) | 1972-12-28 |
| BE784997A (fr) | 1972-10-16 |
| CH547048A (de) | 1974-03-15 |
| FR2143320A1 (enrdf_load_stackoverflow) | 1973-02-02 |
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