NO130234B - - Google Patents
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- Publication number
- NO130234B NO130234B NO01824/69A NO182469A NO130234B NO 130234 B NO130234 B NO 130234B NO 01824/69 A NO01824/69 A NO 01824/69A NO 182469 A NO182469 A NO 182469A NO 130234 B NO130234 B NO 130234B
- Authority
- NO
- Norway
- Prior art keywords
- formula
- ene
- diene
- lower alkyl
- methyl
- Prior art date
Links
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229960003387 progesterone Drugs 0.000 description 2
- 239000000186 progesterone Substances 0.000 description 2
- 239000000583 progesterone congener Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000001833 anti-estrogenic effect Effects 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 230000002254 contraceptive effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- -1 steroid oxazolines Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0036—Nitrogen-containing hetero ring
- C07J71/0057—Nitrogen and oxygen
- C07J71/0068—Nitrogen and oxygen at position 16(17)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO366273A NO131132C (pt) | 1968-05-03 | 1973-09-19 | |
| NO366173A NO131029C (pt) | 1968-05-03 | 1973-09-19 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1602868 | 1968-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO130234B true NO130234B (pt) | 1974-07-29 |
Family
ID=11148454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO01824/69A NO130234B (pt) | 1968-05-03 | 1969-05-02 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3641007A (pt) |
| JP (2) | JPS4831109B1 (pt) |
| AT (3) | AT298693B (pt) |
| BE (1) | BE732116A (pt) |
| BR (1) | BR6908512D0 (pt) |
| CH (1) | CH502330A (pt) |
| DE (1) | DE1921462C3 (pt) |
| DK (3) | DK125736B (pt) |
| ES (3) | ES366737A1 (pt) |
| FI (3) | FI46254C (pt) |
| FR (1) | FR2007755A1 (pt) |
| GB (1) | GB1264222A (pt) |
| LU (1) | LU58511A1 (pt) |
| NL (1) | NL146384B (pt) |
| NO (1) | NO130234B (pt) |
| SE (3) | SE351635B (pt) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5767269U (pt) * | 1980-10-09 | 1982-04-22 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1482237A (fr) * | 1965-04-22 | 1967-05-26 | Lepetit Spa | Procédé pour la préparation de stéroïde-[17alpha, 16alpha-d] oxazolines |
-
1969
- 1969-04-23 NL NL696906302A patent/NL146384B/xx unknown
- 1969-04-25 DK DK228469AA patent/DK125736B/da unknown
- 1969-04-25 BE BE732116D patent/BE732116A/xx unknown
- 1969-04-26 DE DE1921462A patent/DE1921462C3/de not_active Expired
- 1969-04-28 LU LU58511D patent/LU58511A1/xx unknown
- 1969-04-30 FR FR6913816A patent/FR2007755A1/fr not_active Withdrawn
- 1969-05-01 US US821150A patent/US3641007A/en not_active Expired - Lifetime
- 1969-05-02 GB GB1264222D patent/GB1264222A/en not_active Expired
- 1969-05-02 SE SE06252/69A patent/SE351635B/xx unknown
- 1969-05-02 SE SE15180/71A patent/SE366034B/xx unknown
- 1969-05-02 AT AT141970A patent/AT298693B/de not_active IP Right Cessation
- 1969-05-02 AT AT142070A patent/AT298694B/de not_active IP Right Cessation
- 1969-05-02 NO NO01824/69A patent/NO130234B/no unknown
- 1969-05-02 CH CH674069A patent/CH502330A/fr not_active IP Right Cessation
- 1969-05-02 SE SE15179/71A patent/SE366033B/xx unknown
- 1969-05-02 AT AT426269A patent/AT290744B/de not_active IP Right Cessation
- 1969-05-02 BR BR208512/69A patent/BR6908512D0/pt unknown
- 1969-05-02 FI FI691289A patent/FI46254C/fi active
- 1969-05-03 ES ES366737A patent/ES366737A1/es not_active Expired
- 1969-05-23 ES ES367584A patent/ES367584A1/es not_active Expired
- 1969-05-23 ES ES367585A patent/ES367585A1/es not_active Expired
-
1970
- 1970-12-14 DK DK633170AA patent/DK125644B/da unknown
- 1970-12-14 DK DK633270AA patent/DK123936B/da unknown
-
1971
- 1971-04-14 JP JP46023779A patent/JPS4831109B1/ja active Pending
- 1971-12-29 FI FI713712A patent/FI46725C/fi active
- 1971-12-29 FI FI713713A patent/FI46375C/fi active
-
1973
- 1973-04-19 JP JP48043774A patent/JPS4910507B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1264222A (pt) | 1972-02-16 |
| NL6906302A (pt) | 1969-11-05 |
| BE732116A (pt) | 1969-10-01 |
| CH502330A (fr) | 1971-01-31 |
| JPS4831109B1 (pt) | 1973-09-26 |
| JPS4910507B1 (pt) | 1974-03-11 |
| NL146384B (nl) | 1975-07-15 |
| SE366034B (pt) | 1974-04-08 |
| FI46725B (pt) | 1973-02-28 |
| SE351635B (pt) | 1972-12-04 |
| ES366737A1 (es) | 1971-03-16 |
| LU58511A1 (pt) | 1969-07-25 |
| FI46254C (fi) | 1973-02-12 |
| ES367585A1 (es) | 1971-04-01 |
| FI46254B (pt) | 1972-10-31 |
| ES367584A1 (es) | 1971-04-01 |
| FI46725C (fi) | 1973-06-11 |
| AT290744B (de) | 1971-06-11 |
| DE1921462B2 (de) | 1973-04-19 |
| AT298693B (de) | 1972-05-25 |
| AT298694B (de) | 1972-05-25 |
| DE1921462C3 (de) | 1973-11-08 |
| DK123936B (da) | 1972-08-21 |
| FR2007755A1 (pt) | 1970-01-09 |
| US3641007A (en) | 1972-02-08 |
| SE366033B (pt) | 1974-04-08 |
| DK125736B (da) | 1973-04-30 |
| FI46375C (fi) | 1973-03-12 |
| FI46375B (pt) | 1972-11-30 |
| DE1921462A1 (de) | 1970-09-17 |
| DK125644B (da) | 1973-03-19 |
| BR6908512D0 (pt) | 1973-02-08 |
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